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Patent code US9657009

Compile Data Set for Download or QSAR
Found 168 hits of Enzyme Inhibition Constant Data   
Target/Host
(Institution)
LigandTarget/Host
Links
Ligand
Links
Trg + Lig
Links
Ki
nM
ΔG°
kJ/mole
IC50
nM
Kd
nM
EC50/IC50
nM
koff
s-1
kon
M-1s-1
pHTemp
°C
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283950
PNG
(US10023562, Example 142 | US9657009, 142)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2F)C#N)cc1Nc1ccc(cc1)C(N)=O
Show InChI InChI=1S/C24H23F2N7O3/c1-24(2,36)19(26)12-31-23(35)16-11-29-20(33-22-17(25)7-13(9-27)10-30-22)8-18(16)32-15-5-3-14(4-6-15)21(28)34/h3-8,10-11,19,36H,12H2,1-2H3,(H2,28,34)(H,31,35)(H2,29,30,32,33)/t19-/m1/s1
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n/an/a 1.20n/an/an/an/an/an/a



Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM310026
PNG
(US9657009, 29)
Show SMILES CC(C)NC(=O)N[C@H](C)CCNC(=O)c1cnc(Nc2ncc(cc2F)C#N)cc1NC(C)C
Show InChI InChI=1S/C23H31FN8O2/c1-13(2)29-19-9-20(32-21-18(24)8-16(10-25)11-28-21)27-12-17(19)22(33)26-7-6-15(5)31-23(34)30-14(3)4/h8-9,11-15H,6-7H2,1-5H3,(H,26,33)(H2,30,31,34)(H2,27,28,29,32)/t15-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283883
PNG
(US10023562, Example 75 | US9657009, 75)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2Cl)C#N)cc1Nc1ncc(s1)C(C)(C)O
Show InChI InChI=1S/C23H25ClFN7O3S/c1-22(2,34)16(25)10-29-20(33)13-9-27-18(32-19-14(24)5-12(7-26)8-28-19)6-15(13)31-21-30-11-17(36-21)23(3,4)35/h5-6,8-9,11,16,34-35H,10H2,1-4H3,(H,29,33)(H2,27,28,30,31,32)/t16-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283958
PNG
(US10023562, Example 150 | US9657009, 150)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2Cl)C#N)cc1N[C@H]1CC[C@](C)(O)CC1
Show InChI InChI=1S/C24H30ClFN6O3/c1-23(2,34)19(26)13-30-22(33)16-12-28-20(32-21-17(25)8-14(10-27)11-29-21)9-18(16)31-15-4-6-24(3,35)7-5-15/h8-9,11-12,15,19,34-35H,4-7,13H2,1-3H3,(H,30,33)(H2,28,29,31,32)/t15-,19-,24-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM310025
PNG
(US9657009, 28)
Show SMILES CC(C)Nc1cc(Nc2ncc(cc2Cl)C#N)ncc1C(=O)NCC[C@@H](C)NC(C)=O
Show InChI InChI=1S/C21H26ClN7O2/c1-12(2)27-18-8-19(29-20-17(22)7-15(9-23)10-26-20)25-11-16(18)21(31)24-6-5-13(3)28-14(4)30/h7-8,10-13H,5-6H2,1-4H3,(H,24,31)(H,28,30)(H2,25,26,27,29)/t13-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283878
PNG
(US10023562, Example 70 | US10023562, Example 71 | ...)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2Cl)C#N)cc1NC1CCCC1F
Show InChI InChI=1S/C22H25ClF2N6O2/c1-22(2,33)18(25)11-29-21(32)13-10-27-19(7-17(13)30-16-5-3-4-15(16)24)31-20-14(23)6-12(8-26)9-28-20/h6-7,9-10,15-16,18,33H,3-5,11H2,1-2H3,(H,29,32)(H2,27,28,30,31)/t15?,16?,18-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283892
PNG
(US10023562, Example 84 | US9657009, 84)
Show SMILES CC(C)Nc1cc(Nc2ncc(Cl)cc2Cl)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C19H24Cl2FN5O2/c1-10(2)26-14-6-16(27-17-13(21)5-11(20)7-24-17)23-8-12(14)18(28)25-9-15(22)19(3,4)29/h5-8,10,15,29H,9H2,1-4H3,(H,25,28)(H2,23,24,26,27)/t15-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283865
PNG
(US10023562, Example 157 | US10023562, Example 158 ...)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2Cl)C#N)cc1NC1CCC(F)C1
Show InChI InChI=1S/C22H25ClF2N6O2/c1-22(2,33)18(25)11-29-21(32)15-10-27-19(7-17(15)30-14-4-3-13(24)6-14)31-20-16(23)5-12(8-26)9-28-20/h5,7,9-10,13-14,18,33H,3-4,6,11H2,1-2H3,(H,29,32)(H2,27,28,30,31)/t13?,14?,18-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283877
PNG
(US10023562, Example 69 | US9657009, 69)
Show SMILES CNC(=O)N[C@H](C)CCNC(=O)c1cnc(Nc2ncc(cn2)C#N)cc1NC(C)C
Show InChI InChI=1S/C20H27N9O2/c1-12(2)27-16-7-17(29-19-25-9-14(8-21)10-26-19)24-11-15(16)18(30)23-6-5-13(3)28-20(31)22-4/h7,9-13H,5-6H2,1-4H3,(H,23,30)(H2,22,28,31)(H2,24,25,26,27,29)/t13-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM50040797
PNG
(CHEMBL3353191 | US10023562, Example 14 | US9657009...)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2Cl)C#N)cc1NC1CC1
Show InChI InChI=1S/C20H22ClFN6O2/c1-20(2,30)16(22)10-26-19(29)13-9-24-17(6-15(13)27-12-3-4-12)28-18-14(21)5-11(7-23)8-25-18/h5-6,8-9,12,16,30H,3-4,10H2,1-2H3,(H,26,29)(H2,24,25,27,28)/t16-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283865
PNG
(US10023562, Example 157 | US10023562, Example 158 ...)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2Cl)C#N)cc1NC1CCC(F)C1
Show InChI InChI=1S/C22H25ClF2N6O2/c1-22(2,33)18(25)11-29-21(32)15-10-27-19(7-17(15)30-14-4-3-13(24)6-14)31-20-16(23)5-12(8-26)9-28-20/h5,7,9-10,13-14,18,33H,3-4,6,11H2,1-2H3,(H,29,32)(H2,27,28,30,31)/t13?,14?,18-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM50040798
PNG
(CHEMBL3353190 | US10023562, Example 12 | US9657009...)
Show SMILES CC(C)Nc1cc(Nc2ncc(cc2Cl)C#N)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C20H24ClFN6O2/c1-11(2)27-15-6-17(28-18-14(21)5-12(7-23)8-25-18)24-9-13(15)19(29)26-10-16(22)20(3,4)30/h5-6,8-9,11,16,30H,10H2,1-4H3,(H,26,29)(H2,24,25,27,28)/t16-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283855
PNG
(US10023562, Example 47 | US9657009, 47)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2F)C#N)cc1NC1CC1
Show InChI InChI=1S/C20H22F2N6O2/c1-20(2,30)16(22)10-26-19(29)13-9-24-17(6-15(13)27-12-3-4-12)28-18-14(21)5-11(7-23)8-25-18/h5-6,8-9,12,16,30H,3-4,10H2,1-2H3,(H,26,29)(H2,24,25,27,28)/t16-/m1/s1
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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM309997
PNG
(6-((5-Cyano-2-pyridinyl)amino)-N-((2R)-2-fluoro-3-...)
Show SMILES CC(C)Nc1cc(Nc2ccc(cn2)C#N)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C20H25FN6O2/c1-12(2)26-15-7-18(27-17-6-5-13(8-22)9-23-17)24-10-14(15)19(28)25-11-16(21)20(3,4)29/h5-7,9-10,12,16,29H,11H2,1-4H3,(H,25,28)(H2,23,24,26,27)/t16-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283865
PNG
(US10023562, Example 157 | US10023562, Example 158 ...)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2Cl)C#N)cc1NC1CCC(F)C1
Show InChI InChI=1S/C22H25ClF2N6O2/c1-22(2,33)18(25)11-29-21(32)15-10-27-19(7-17(15)30-14-4-3-13(24)6-14)31-20-16(23)5-12(8-26)9-28-20/h5,7,9-10,13-14,18,33H,3-4,6,11H2,1-2H3,(H,29,32)(H2,27,28,30,31)/t13?,14?,18-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283819
PNG
(US10023562, Example 13 | US9657009, 13)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2Cl)C#N)cc1NC1CCOCC1
Show InChI InChI=1S/C22H26ClFN6O3/c1-22(2,32)18(24)12-28-21(31)15-11-26-19(8-17(15)29-14-3-5-33-6-4-14)30-20-16(23)7-13(9-25)10-27-20/h7-8,10-11,14,18,32H,3-6,12H2,1-2H3,(H,28,31)(H2,26,27,29,30)/t18-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283865
PNG
(US10023562, Example 157 | US10023562, Example 158 ...)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2Cl)C#N)cc1NC1CCC(F)C1
Show InChI InChI=1S/C22H25ClF2N6O2/c1-22(2,33)18(25)11-29-21(32)15-10-27-19(7-17(15)30-14-4-3-13(24)6-14)31-20-16(23)5-12(8-26)9-28-20/h5,7,9-10,13-14,18,33H,3-4,6,11H2,1-2H3,(H,29,32)(H2,27,28,30,31)/t13?,14?,18-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283890
PNG
(US10023562, Example 114 | US10023562, Example 115 ...)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2F)C#N)cc1NC1CCC(F)C1
Show InChI InChI=1S/C22H25F3N6O2/c1-22(2,33)18(25)11-29-21(32)15-10-27-19(7-17(15)30-14-4-3-13(23)6-14)31-20-16(24)5-12(8-26)9-28-20/h5,7,9-10,13-14,18,33H,3-4,6,11H2,1-2H3,(H,29,32)(H2,27,28,30,31)/t13?,14?,18-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283970
PNG
(US10023562, Example 162 | US9657009, 162)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2Cl)C#N)cc1Nc1cccc(c1)C#N
Show InChI InChI=1S/C24H21ClFN7O2/c1-24(2,35)20(26)13-31-23(34)17-12-29-21(33-22-18(25)7-15(10-28)11-30-22)8-19(17)32-16-5-3-4-14(6-16)9-27/h3-8,11-12,20,35H,13H2,1-2H3,(H,31,34)(H2,29,30,32,33)/t20-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283876
PNG
(US10023562, Example 68 | US9657009, 68)
Show SMILES CNC(=O)N[C@H](C)CCNC(=O)c1cnc(Nc2ncc(cc2Cl)C#N)cc1NC(C)C
Show InChI InChI=1S/C21H27ClN8O2/c1-12(2)28-17-8-18(30-19-16(22)7-14(9-23)10-27-19)26-11-15(17)20(31)25-6-5-13(3)29-21(32)24-4/h7-8,10-13H,5-6H2,1-4H3,(H,25,31)(H2,24,29,32)(H2,26,27,28,30)/t13-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283878
PNG
(US10023562, Example 70 | US10023562, Example 71 | ...)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2Cl)C#N)cc1NC1CCCC1F
Show InChI InChI=1S/C22H25ClF2N6O2/c1-22(2,33)18(25)11-29-21(32)13-10-27-19(7-17(13)30-16-5-3-4-15(16)24)31-20-14(23)6-12(8-26)9-28-20/h6-7,9-10,15-16,18,33H,3-5,11H2,1-2H3,(H,29,32)(H2,27,28,30,31)/t15?,16?,18-/m1/s1
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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283878
PNG
(US10023562, Example 70 | US10023562, Example 71 | ...)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2Cl)C#N)cc1NC1CCCC1F
Show InChI InChI=1S/C22H25ClF2N6O2/c1-22(2,33)18(25)11-29-21(32)13-10-27-19(7-17(13)30-16-5-3-4-15(16)24)31-20-14(23)6-12(8-26)9-28-20/h6-7,9-10,15-16,18,33H,3-5,11H2,1-2H3,(H,29,32)(H2,27,28,30,31)/t15?,16?,18-/m1/s1
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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283924
PNG
(US10023562, Example 116 | US9657009, 116)
Show SMILES CC(C)NC(=O)[C@H]1CC[C@@H](CC1)NC(=O)c1cnc(Nc2ncc(cc2F)C#N)cc1NC(C)C
Show InChI InChI=1S/C25H32FN7O2/c1-14(2)30-21-10-22(33-23-20(26)9-16(11-27)12-29-23)28-13-19(21)25(35)32-18-7-5-17(6-8-18)24(34)31-15(3)4/h9-10,12-15,17-18H,5-8H2,1-4H3,(H,31,34)(H,32,35)(H2,28,29,30,33)/t17-,18-
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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283934
PNG
(US10023562, Example 126 | US9657009, 126)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2F)C#N)cc1NCC(F)(F)C(C)(C)O
Show InChI InChI=1S/C22H26F4N6O3/c1-20(2,34)16(24)10-30-19(33)13-9-28-17(32-18-14(23)5-12(7-27)8-29-18)6-15(13)31-11-22(25,26)21(3,4)35/h5-6,8-9,16,34-35H,10-11H2,1-4H3,(H,30,33)(H2,28,29,31,32)/t16-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283873
PNG
(US10023562, Example 65 | US9657009, 65)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2Cl)C#N)cc1NCC(F)(F)F
Show InChI InChI=1S/C19H19ClF4N6O2/c1-18(2,32)14(21)8-28-17(31)11-7-26-15(4-13(11)29-9-19(22,23)24)30-16-12(20)3-10(5-25)6-27-16/h3-4,6-7,14,32H,8-9H2,1-2H3,(H,28,31)(H2,26,27,29,30)/t14-/m1/s1
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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283951
PNG
(US10023562, Example 143 | US9657009, 143)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2Cl)C#N)cc1Nc1cccc(c1)C(N)=O
Show InChI InChI=1S/C24H23ClFN7O3/c1-24(2,36)19(26)12-31-23(35)16-11-29-20(33-22-17(25)6-13(9-27)10-30-22)8-18(16)32-15-5-3-4-14(7-15)21(28)34/h3-8,10-11,19,36H,12H2,1-2H3,(H2,28,34)(H,31,35)(H2,29,30,32,33)/t19-/m1/s1
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US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283887
PNG
(US10023562, Example 79 | US9657009, 79)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2Cl)C#N)cc1NC1CCOCC1F
Show InChI InChI=1S/C22H25ClF2N6O3/c1-22(2,33)18(25)10-29-21(32)13-9-27-19(31-20-14(23)5-12(7-26)8-28-20)6-17(13)30-16-3-4-34-11-15(16)24/h5-6,8-9,15-16,18,33H,3-4,10-11H2,1-2H3,(H,29,32)(H2,27,28,30,31)/t15?,16?,18-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283890
PNG
(US10023562, Example 114 | US10023562, Example 115 ...)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2F)C#N)cc1NC1CCC(F)C1
Show InChI InChI=1S/C22H25F3N6O2/c1-22(2,33)18(25)11-29-21(32)15-10-27-19(7-17(15)30-14-4-3-13(23)6-14)31-20-16(24)5-12(8-26)9-28-20/h5,7,9-10,13-14,18,33H,3-4,6,11H2,1-2H3,(H,29,32)(H2,27,28,30,31)/t13?,14?,18-/m1/s1
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Bristol-Myers Squibb Company

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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283957
PNG
(US10023562, Example 149 | US9657009, 149)
Show SMILES CS(=O)(=O)[C@H]1CC[C@@H](CC1)NC(=O)c1cnc(Nc2ncc(cc2Cl)C#N)cc1NC1CCOCC1
Show InChI InChI=1S/C24H29ClN6O4S/c1-36(33,34)18-4-2-16(3-5-18)30-24(32)19-14-27-22(11-21(19)29-17-6-8-35-9-7-17)31-23-20(25)10-15(12-26)13-28-23/h10-11,13-14,16-18H,2-9H2,1H3,(H,30,32)(H2,27,28,29,31)/t16-,18-
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283857
PNG
(US10023562, Example 49 | US9657009, 49)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2F)C#N)cc1NC1CCOCC1
Show InChI InChI=1S/C22H26F2N6O3/c1-22(2,32)18(24)12-28-21(31)15-11-26-19(8-17(15)29-14-3-5-33-6-4-14)30-20-16(23)7-13(9-25)10-27-20/h7-8,10-11,14,18,32H,3-6,12H2,1-2H3,(H,28,31)(H2,26,27,29,30)/t18-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283872
PNG
(US10023562, Example 64 | US9657009, 64)
Show SMILES CC(C)Nc1cc(Nc2ncc(cc2F)C#N)ncc1C(=O)NCC[C@@H](C)NC(C)=O
Show InChI InChI=1S/C21H26FN7O2/c1-12(2)27-18-8-19(29-20-17(22)7-15(9-23)10-26-20)25-11-16(18)21(31)24-6-5-13(3)28-14(4)30/h7-8,10-13H,5-6H2,1-4H3,(H,24,31)(H,28,30)(H2,25,26,27,29)/t13-/m1/s1
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US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283878
PNG
(US10023562, Example 70 | US10023562, Example 71 | ...)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2Cl)C#N)cc1NC1CCCC1F
Show InChI InChI=1S/C22H25ClF2N6O2/c1-22(2,33)18(25)11-29-21(32)13-10-27-19(7-17(13)30-16-5-3-4-15(16)24)31-20-14(23)6-12(8-26)9-28-20/h6-7,9-10,15-16,18,33H,3-5,11H2,1-2H3,(H,29,32)(H2,27,28,30,31)/t15?,16?,18-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283941
PNG
(US10023562, Example 133 | US9657009, 133)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2F)C#N)cc1NC12CCC(O)(CC1)C2
Show InChI InChI=1S/C24H28F2N6O3/c1-22(2,34)18(26)12-30-21(33)15-11-28-19(31-20-16(25)7-14(9-27)10-29-20)8-17(15)32-23-3-5-24(35,13-23)6-4-23/h7-8,10-11,18,34-35H,3-6,12-13H2,1-2H3,(H,30,33)(H2,28,29,31,32)/t18-,23?,24?/m1/s1
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Bristol-Myers Squibb Company

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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283844
PNG
(US10023562, Example 36 | US9657009, 37)
Show SMILES COC(C)(C)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2F)C#N)cc1NC(C)C
Show InChI InChI=1S/C21H26F2N6O2/c1-12(2)28-16-7-18(29-19-15(22)6-13(8-24)9-26-19)25-10-14(16)20(30)27-11-17(23)21(3,4)31-5/h6-7,9-10,12,17H,11H2,1-5H3,(H,27,30)(H2,25,26,28,29)/t17-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283959
PNG
(US10023562, Example 151 | US9657009, 151)
Show SMILES CS(=O)(=O)[C@H]1CC[C@@H](CC1)NC(=O)c1cnc(Nc2ncc(cc2Cl)C#N)cc1NC1CC1
Show InChI InChI=1S/C22H25ClN6O3S/c1-33(31,32)16-6-4-15(5-7-16)28-22(30)17-12-25-20(9-19(17)27-14-2-3-14)29-21-18(23)8-13(10-24)11-26-21/h8-9,11-12,14-16H,2-7H2,1H3,(H,28,30)(H2,25,26,27,29)/t15-,16-
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Bristol-Myers Squibb Company

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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283944
PNG
(US10023562, Example 136 | US9657009, 136)
Show SMILES CC(C)Nc1cc(Nc2ncc(C#N)c(N)n2)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C19H25FN8O2/c1-10(2)26-13-5-15(27-18-25-7-11(6-21)16(22)28-18)23-8-12(13)17(29)24-9-14(20)19(3,4)30/h5,7-8,10,14,30H,9H2,1-4H3,(H,24,29)(H4,22,23,25,26,27,28)/t14-/m1/s1
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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283930
PNG
(US10023562, Example 122 | US9657009, 122)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2F)C#N)cc1Nc1cccc(CO)c1
Show InChI InChI=1S/C24H24F2N6O3/c1-24(2,35)20(26)12-30-23(34)17-11-28-21(32-22-18(25)7-15(9-27)10-29-22)8-19(17)31-16-5-3-4-14(6-16)13-33/h3-8,10-11,20,33,35H,12-13H2,1-2H3,(H,30,34)(H2,28,29,31,32)/t20-/m1/s1
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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283956
PNG
(US10023562, Example 148 | US9657009, 148)
Show SMILES Cn1nnnc1-c1ccc(Nc2cc(Nc3ncc(cc3Cl)C#N)ncc2C(=O)NC[C@@H](F)C(C)(C)O)cc1
Show InChI InChI=1S/C25H24ClFN10O2/c1-25(2,39)20(27)13-31-24(38)17-12-29-21(33-22-18(26)8-14(10-28)11-30-22)9-19(17)32-16-6-4-15(5-7-16)23-34-35-36-37(23)3/h4-9,11-12,20,39H,13H2,1-3H3,(H,31,38)(H2,29,30,32,33)/t20-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283824
PNG
(US10023562, Example 18 | US9657009, 18)
Show SMILES CNC(=O)[C@H]1CC[C@@H](CC1)NC(=O)c1cnc(Nc2ncc(cc2F)C#N)cc1NC(C)C
Show InChI InChI=1S/C23H28FN7O2/c1-13(2)29-19-9-20(31-21-18(24)8-14(10-25)11-28-21)27-12-17(19)23(33)30-16-6-4-15(5-7-16)22(32)26-3/h8-9,11-13,15-16H,4-7H2,1-3H3,(H,26,32)(H,30,33)(H2,27,28,29,31)/t15-,16-
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283898
PNG
(US10023562, Example 90 | US9657009, 90)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2Cl)C#N)cc1NC12CC(C1)C2
Show InChI InChI=1S/C22H24ClFN6O2/c1-21(2,32)17(24)11-28-20(31)14-10-26-18(4-16(14)30-22-5-13(6-22)7-22)29-19-15(23)3-12(8-25)9-27-19/h3-4,9-10,13,17,32H,5-7,11H2,1-2H3,(H,28,31)(H2,26,27,29,30)/t13?,17-,22?/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283946
PNG
(US10023562, Example 138 | US9657009, 138)
Show SMILES CCCNc1cc(Nc2ncc(cc2Cl)C#N)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C20H24ClFN6O2/c1-4-5-24-15-7-17(28-18-14(21)6-12(8-23)9-26-18)25-10-13(15)19(29)27-11-16(22)20(2,3)30/h6-7,9-10,16,30H,4-5,11H2,1-3H3,(H,27,29)(H2,24,25,26,28)/t16-/m1/s1
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Bristol-Myers Squibb Company

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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283864
PNG
(US10023562, Example 56 | US10023562, Example 86 | ...)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cn2)C#N)cc1NC1CCC(F)C1
Show InChI InChI=1S/C21H25F2N7O2/c1-21(2,32)17(23)11-26-19(31)15-10-25-18(30-20-27-8-12(7-24)9-28-20)6-16(15)29-14-4-3-13(22)5-14/h6,8-10,13-14,17,32H,3-5,11H2,1-2H3,(H,26,31)(H2,25,27,28,29,30)/t13?,14?,17-/m1/s1
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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM50040795
PNG
(CHEMBL3353193 | US10023562, Example 123 | US965700...)
Show SMILES CC(C)Nc1cc(Nc2ncc(Cl)cc2F)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C19H24ClF2N5O2/c1-10(2)26-14-6-16(27-17-13(21)5-11(20)7-24-17)23-8-12(14)18(28)25-9-15(22)19(3,4)29/h5-8,10,15,29H,9H2,1-4H3,(H,25,28)(H2,23,24,26,27)/t15-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283933
PNG
(US10023562, Example 125 | US9657009, 125)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2F)C#N)cc1Nc1cccc(O)c1
Show InChI InChI=1S/C23H22F2N6O3/c1-23(2,34)19(25)12-29-22(33)16-11-27-20(31-21-17(24)6-13(9-26)10-28-21)8-18(16)30-14-4-3-5-15(32)7-14/h3-8,10-11,19,32,34H,12H2,1-2H3,(H,29,33)(H2,27,28,30,31)/t19-/m1/s1
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Bristol-Myers Squibb Company

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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM50040796
PNG
(CHEMBL3353192 | US10023562, Example 85 | US9657009...)
Show SMILES CC(C)Nc1cc(Nc2ncc(cc2C)C#N)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C21H27FN6O2/c1-12(2)27-16-7-18(28-19-13(3)6-14(8-23)9-25-19)24-10-15(16)20(29)26-11-17(22)21(4,5)30/h6-7,9-10,12,17,30H,11H2,1-5H3,(H,26,29)(H2,24,25,27,28)/t17-/m1/s1
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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283884
PNG
(US10023562, Example 76 | US10023562, Example 78 | ...)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2Cl)C#N)cc1NC1CCCC1O
Show InChI InChI=1S/C22H26ClFN6O3/c1-22(2,33)18(24)11-28-21(32)13-10-26-19(7-16(13)29-15-4-3-5-17(15)31)30-20-14(23)6-12(8-25)9-27-20/h6-7,9-10,15,17-18,31,33H,3-5,11H2,1-2H3,(H,28,32)(H2,26,27,29,30)/t15?,17?,18-/m1/s1
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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283871
PNG
(US10023562, Example 63 | US9657009, 63)
Show SMILES CC(C)Nc1cc(Nc2ccc(C#N)c(C)n2)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C21H27FN6O2/c1-12(2)26-16-8-19(28-18-7-6-14(9-23)13(3)27-18)24-10-15(16)20(29)25-11-17(22)21(4,5)30/h6-8,10,12,17,30H,11H2,1-5H3,(H,25,29)(H2,24,26,27,28)/t17-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM310037
PNG
(US9657009, 39)
Show SMILES C[C@@H](CF)Nc1cc(Nc2ncc(cc2Cl)C#N)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C20H23ClF2N6O2/c1-11(6-22)28-15-5-17(29-18-14(21)4-12(7-24)8-26-18)25-9-13(15)19(30)27-10-16(23)20(2,3)31/h4-5,8-9,11,16,31H,6,10H2,1-3H3,(H,27,30)(H2,25,26,28,29)/t11-,16+/m0/s1
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Bristol-Myers Squibb Company

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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283925
PNG
(US10023562, Example 117 | US9657009, 117)
Show SMILES CCC(O)(CC)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cn2)C#N)cc1NC(C)C
Show InChI InChI=1S/C21H28FN7O2/c1-5-21(31,6-2)17(22)12-25-19(30)15-11-24-18(7-16(15)28-13(3)4)29-20-26-9-14(8-23)10-27-20/h7,9-11,13,17,31H,5-6,12H2,1-4H3,(H,25,30)(H2,24,26,27,28,29)/t17-/m1/s1
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Bristol-Myers Squibb Company

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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283874
PNG
(US10023562, Example 66 | US9657009, 66)
Show SMILES CCNc1cc(Nc2ncc(cc2F)C#N)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C19H22F2N6O2/c1-4-23-14-6-16(27-17-13(20)5-11(7-22)8-25-17)24-9-12(14)18(28)26-10-15(21)19(2,3)29/h5-6,8-9,15,29H,4,10H2,1-3H3,(H,26,28)(H2,23,24,25,27)/t15-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283844
PNG
(US10023562, Example 36 | US9657009, 37)
Show SMILES COC(C)(C)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2F)C#N)cc1NC(C)C
Show InChI InChI=1S/C21H26F2N6O2/c1-12(2)28-16-7-18(29-19-15(22)6-13(8-24)9-26-19)25-10-14(16)20(30)27-11-17(23)21(3,4)31-5/h6-7,9-10,12,17H,11H2,1-5H3,(H,27,30)(H2,25,26,28,29)/t17-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283938
PNG
(US10023562, Example 130 | US9657009, 130)
Show SMILES COc1cccc(Nc2cc(Nc3ncc(cc3F)C#N)ncc2C(=O)NC[C@@H](F)C(C)(C)O)c1
Show InChI InChI=1S/C24H24F2N6O3/c1-24(2,34)20(26)13-30-23(33)17-12-28-21(32-22-18(25)7-14(10-27)11-29-22)9-19(17)31-15-5-4-6-16(8-15)35-3/h4-9,11-12,20,34H,13H2,1-3H3,(H,30,33)(H2,28,29,31,32)/t20-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283910
PNG
(US10023562, Example 102 | US9657009, 102)
Show SMILES CC(C)Nc1cc(Nc2ncc(cc2Cl)C#N)ncc1C(=O)NC1CCC(CC1)C(C)(C)O
Show InChI InChI=1S/C24H31ClN6O2/c1-14(2)29-20-10-21(31-22-19(25)9-15(11-26)12-28-22)27-13-18(20)23(32)30-17-7-5-16(6-8-17)24(3,4)33/h9-10,12-14,16-17,33H,5-8H2,1-4H3,(H,30,32)(H2,27,28,29,31)
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283945
PNG
(US10023562, Example 137 | US9657009, 137)
Show SMILES CC(C)Nc1cc(Nc2ncc(cc2F)C#N)ncc1C(=O)N[C@H]1CC[C@@H](CC1)C(C)(C)O
Show InChI InChI=1S/C24H31FN6O2/c1-14(2)29-20-10-21(31-22-19(25)9-15(11-26)12-28-22)27-13-18(20)23(32)30-17-7-5-16(6-8-17)24(3,4)33/h9-10,12-14,16-17,33H,5-8H2,1-4H3,(H,30,32)(H2,27,28,29,31)/t16-,17-
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Bristol-Myers Squibb Company

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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283907
PNG
(US10023562, Example 99 | US9657009, 99)
Show SMILES CCC(C)Nc1cc(Nc2ncc(cn2)C#N)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C20H26FN7O2/c1-5-12(2)27-15-6-17(28-19-25-8-13(7-22)9-26-19)23-10-14(15)18(29)24-11-16(21)20(3,4)30/h6,8-10,12,16,30H,5,11H2,1-4H3,(H,24,29)(H2,23,25,26,27,28)/t12?,16-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283963
PNG
(US10023562, Example 155 | US9657009, 155)
Show SMILES CC(C)CNc1cc(Nc2ncc(cc2Cl)C#N)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C21H26ClFN6O2/c1-12(2)8-25-16-6-18(29-19-15(22)5-13(7-24)9-27-19)26-10-14(16)20(30)28-11-17(23)21(3,4)31/h5-6,9-10,12,17,31H,8,11H2,1-4H3,(H,28,30)(H2,25,26,27,29)/t17-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283899
PNG
(US10023562, Example 91 | US9657009, 91)
Show SMILES C[C@@H](CO)Nc1cc(Nc2ncc(cc2F)C#N)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C20H24F2N6O3/c1-11(10-29)27-15-5-17(28-18-14(21)4-12(6-23)7-25-18)24-8-13(15)19(30)26-9-16(22)20(2,3)31/h4-5,7-8,11,16,29,31H,9-10H2,1-3H3,(H,26,30)(H2,24,25,27,28)/t11-,16+/m0/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283952
PNG
(US10023562, Example 144 | US10023562, Example 145 ...)
Show SMILES CC(C)Nc1cc(Nc2ncc(cc2F)C#N)ncc1C(=O)NC1CC[C@@H](CC1)C(C)(O)C1CC1
Show InChI InChI=1S/C26H33FN6O2/c1-15(2)31-22-11-23(33-24-21(27)10-16(12-28)13-30-24)29-14-20(22)25(34)32-19-8-6-18(7-9-19)26(3,35)17-4-5-17/h10-11,13-15,17-19,35H,4-9H2,1-3H3,(H,32,34)(H2,29,30,31,33)/t18-,19?,26?
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283846
PNG
(US10023562, Example 38 | US9657009, 38)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2Cl)C(N)=O)cc1NC1CCC(F)C1
Show InChI InChI=1S/C22H27ClF2N6O3/c1-22(2,34)17(25)10-29-21(33)14-9-27-18(7-16(14)30-13-4-3-12(24)6-13)31-20-15(23)5-11(8-28-20)19(26)32/h5,7-9,12-13,17,34H,3-4,6,10H2,1-2H3,(H2,26,32)(H,29,33)(H2,27,28,30,31)/t12?,13?,17-/m1/s1
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US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283890
PNG
(US10023562, Example 114 | US10023562, Example 115 ...)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2F)C#N)cc1NC1CCC(F)C1
Show InChI InChI=1S/C22H25F3N6O2/c1-22(2,33)18(25)11-29-21(32)15-10-27-19(7-17(15)30-14-4-3-13(23)6-14)31-20-16(24)5-12(8-26)9-28-20/h5,7,9-10,13-14,18,33H,3-4,6,11H2,1-2H3,(H,29,32)(H2,27,28,30,31)/t13?,14?,18-/m1/s1
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US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283926
PNG
(US10023562, Example 118 | US9657009, 118)
Show SMILES CC(C)Nc1cc(Nc2ncc(cc2F)C#N)ncc1C(=O)N[C@H]1CC[C@@H](CC1)C(=O)NC1CC1
Show InChI InChI=1S/C25H30FN7O2/c1-14(2)30-21-10-22(33-23-20(26)9-15(11-27)12-29-23)28-13-19(21)25(35)32-17-5-3-16(4-6-17)24(34)31-18-7-8-18/h9-10,12-14,16-18H,3-8H2,1-2H3,(H,31,34)(H,32,35)(H2,28,29,30,33)/t16-,17-
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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283936
PNG
(US10023562, Example 128 | US9657009, 128)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2F)C#N)cc1Nc1cccc(c1)S(N)(=O)=O
Show InChI InChI=1S/C23H23F2N7O4S/c1-23(2,34)19(25)12-30-22(33)16-11-28-20(32-21-17(24)6-13(9-26)10-29-21)8-18(16)31-14-4-3-5-15(7-14)37(27,35)36/h3-8,10-11,19,34H,12H2,1-2H3,(H,30,33)(H2,27,35,36)(H2,28,29,31,32)/t19-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283859
PNG
(US10023562, Example 51 | US9657009, 51)
Show SMILES CCNc1cc(Nc2ncc(cc2Cl)C#N)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C19H22ClFN6O2/c1-4-23-14-6-16(27-17-13(20)5-11(7-22)8-25-17)24-9-12(14)18(28)26-10-15(21)19(2,3)29/h5-6,8-9,15,29H,4,10H2,1-3H3,(H,26,28)(H2,23,24,25,27)/t15-/m1/s1
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Bristol-Myers Squibb Company

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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM310028
PNG
(US9657009, 31)
Show SMILES CC(C)Nc1cc(Nc2ccc(cn2)C#N)ncc1C(=O)NC1CCC(O)(CC1)c1ccnn1C
Show InChI InChI=1S/C25H30N8O2/c1-16(2)30-20-12-23(32-22-5-4-17(13-26)14-27-22)28-15-19(20)24(34)31-18-6-9-25(35,10-7-18)21-8-11-29-33(21)3/h4-5,8,11-12,14-16,18,35H,6-7,9-10H2,1-3H3,(H,31,34)(H2,27,28,30,32)
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283825
PNG
(US10023562, Example 19 | US9657009, 19)
Show SMILES CC(C)Nc1cc(Nc2ncc(cc2F)C#N)ncc1C(=O)N[C@H]1CC[C@@H](CC1)NC(C)=O
Show InChI InChI=1S/C23H28FN7O2/c1-13(2)28-20-9-21(31-22-19(24)8-15(10-25)11-27-22)26-12-18(20)23(33)30-17-6-4-16(5-7-17)29-14(3)32/h8-9,11-13,16-17H,4-7H2,1-3H3,(H,29,32)(H,30,33)(H2,26,27,28,31)/t16-,17-
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US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283864
PNG
(US10023562, Example 56 | US10023562, Example 86 | ...)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cn2)C#N)cc1NC1CCC(F)C1
Show InChI InChI=1S/C21H25F2N7O2/c1-21(2,32)17(23)11-26-19(31)15-10-25-18(30-20-27-8-12(7-24)9-28-20)6-16(15)29-14-4-3-13(22)5-14/h6,8-10,13-14,17,32H,3-5,11H2,1-2H3,(H,26,31)(H2,25,27,28,29,30)/t13?,14?,17-/m1/s1
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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283833
PNG
(US10023562, Example 26 | US9657009, 26)
Show SMILES CC(C)Nc1cc(Nc2ccnc(n2)N2CCC(F)C2)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C22H31F2N7O2/c1-13(2)28-16-9-19(26-10-15(16)20(32)27-11-17(24)22(3,4)33)29-18-5-7-25-21(30-18)31-8-6-14(23)12-31/h5,7,9-10,13-14,17,33H,6,8,11-12H2,1-4H3,(H,27,32)(H2,25,26,28,29,30)/t14?,17-/m1/s1
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US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283862
PNG
(US10023562, Example 54 | US10023562, Example 55 | ...)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cn2)C#N)cc1N[C@H]1CCC[C@@H]1F
Show InChI InChI=1S/C21H25F2N7O2/c1-21(2,32)17(23)11-26-19(31)13-10-25-18(30-20-27-8-12(7-24)9-28-20)6-16(13)29-15-5-3-4-14(15)22/h6,8-10,14-15,17,32H,3-5,11H2,1-2H3,(H,26,31)(H2,25,27,28,29,30)/t14-,15-,17+/m0/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283864
PNG
(US10023562, Example 56 | US10023562, Example 86 | ...)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cn2)C#N)cc1NC1CCC(F)C1
Show InChI InChI=1S/C21H25F2N7O2/c1-21(2,32)17(23)11-26-19(31)15-10-25-18(30-20-27-8-12(7-24)9-28-20)6-16(15)29-14-4-3-13(22)5-14/h6,8-10,13-14,17,32H,3-5,11H2,1-2H3,(H,26,31)(H2,25,27,28,29,30)/t13?,14?,17-/m1/s1
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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283962
PNG
(US10023562, Example 154 | US9657009, 154)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(C#N)c(N)n2)cc1NC1CC1
Show InChI InChI=1S/C19H23FN8O2/c1-19(2,30)14(20)9-24-17(29)12-8-23-15(5-13(12)26-11-3-4-11)27-18-25-7-10(6-21)16(22)28-18/h5,7-8,11,14,30H,3-4,9H2,1-2H3,(H,24,29)(H4,22,23,25,26,27,28)/t14-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283821
PNG
(US10023562, Example 15 | US9657009, 15)
Show SMILES CC(C)Nc1cc(Nc2ncc(cc2Cl)C#N)ncc1C(=O)N[C@H]1CC[C@@H](CC1)NC(C)=O
Show InChI InChI=1S/C23H28ClN7O2/c1-13(2)28-20-9-21(31-22-19(24)8-15(10-25)11-27-22)26-12-18(20)23(33)30-17-6-4-16(5-7-17)29-14(3)32/h8-9,11-13,16-17H,4-7H2,1-3H3,(H,29,32)(H,30,33)(H2,26,27,28,31)/t16-,17-
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283942
PNG
(US10023562, Example 134 | US9657009, 134)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2F)C#N)cc1Nc1cccc(NS(C)(=O)=O)c1
Show InChI InChI=1S/C24H25F2N7O4S/c1-24(2,35)20(26)13-30-23(34)17-12-28-21(32-22-18(25)7-14(10-27)11-29-22)9-19(17)31-15-5-4-6-16(8-15)33-38(3,36)37/h4-9,11-12,20,33,35H,13H2,1-3H3,(H,30,34)(H2,28,29,31,32)/t20-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283960
PNG
(US10023562, Example 152 | US9657009, 152)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2Cl)C#N)cc1N[C@H]1CC[C@@](C)(O)CC1
Show InChI InChI=1S/C24H30ClFN6O3/c1-23(2,34)19(26)13-30-22(33)16-12-28-20(32-21-17(25)8-14(10-27)11-29-21)9-18(16)31-15-4-6-24(3,35)7-5-15/h8-9,11-12,15,19,34-35H,4-7,13H2,1-3H3,(H,30,33)(H2,28,29,31,32)/t15-,19-,24+/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283911
PNG
(US10023562, Example 103 | US9657009, 103)
Show SMILES CC(C)(F)CNc1cc(Nc2ncc(cc2Cl)C#N)ncc1C(=O)NC1CCC(CC1)C(C)(C)O
Show InChI InChI=1S/C25H32ClFN6O2/c1-24(2,27)14-31-20-10-21(33-22-19(26)9-15(11-28)12-30-22)29-13-18(20)23(34)32-17-7-5-16(6-8-17)25(3,4)35/h9-10,12-13,16-17,35H,5-8,14H2,1-4H3,(H,32,34)(H2,29,30,31,33)
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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283905
PNG
(US10023562, Example 97 | US9657009, 98)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2F)C#N)cc1NC1CCCOC1
Show InChI InChI=1S/C22H26F2N6O3/c1-22(2,32)18(24)11-28-21(31)15-10-26-19(7-17(15)29-14-4-3-5-33-12-14)30-20-16(23)6-13(8-25)9-27-20/h6-7,9-10,14,18,32H,3-5,11-12H2,1-2H3,(H,28,31)(H2,26,27,29,30)/t14?,18-/m1/s1
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US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM50040794
PNG
(CHEMBL3353194 | US9657009, 22)
Show SMILES CC(C)Nc1cc(Nc2ncc(cn2)C#N)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C19H24FN7O2/c1-11(2)26-14-5-16(27-18-24-7-12(6-21)8-25-18)22-9-13(14)17(28)23-10-15(20)19(3,4)29/h5,7-9,11,15,29H,10H2,1-4H3,(H,23,28)(H2,22,24,25,26,27)/t15-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283864
PNG
(US10023562, Example 56 | US10023562, Example 86 | ...)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cn2)C#N)cc1NC1CCC(F)C1
Show InChI InChI=1S/C21H25F2N7O2/c1-21(2,32)17(23)11-26-19(31)15-10-25-18(30-20-27-8-12(7-24)9-28-20)6-16(15)29-14-4-3-13(22)5-14/h6,8-10,13-14,17,32H,3-5,11H2,1-2H3,(H,26,31)(H2,25,27,28,29,30)/t13?,14?,17-/m1/s1
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US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283913
PNG
(US10023562, Example 105 | US9657009, 105)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncncc2Cl)cc1NC1CC1
Show InChI InChI=1S/C18H22ClFN6O2/c1-18(2,28)14(20)8-23-17(27)11-6-22-15(5-13(11)25-10-3-4-10)26-16-12(19)7-21-9-24-16/h5-7,9-10,14,28H,3-4,8H2,1-2H3,(H,23,27)(H2,21,22,24,25,26)/t14-/m1/s1
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US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283812
PNG
(US10023562, Example 6 | US9657009, 6)
Show SMILES CC(C)Nc1cc(Nc2ccc(cn2)C#N)ncc1C(=O)N[C@H]1CC[C@@H](CC1)C(=O)NC1CC1
Show InChI InChI=1S/C25H31N7O2/c1-15(2)29-21-11-23(32-22-10-3-16(12-26)13-27-22)28-14-20(21)25(34)31-18-6-4-17(5-7-18)24(33)30-19-8-9-19/h3,10-11,13-15,17-19H,4-9H2,1-2H3,(H,30,33)(H,31,34)(H2,27,28,29,32)/t17-,18-
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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283909
PNG
(US10023562, Example 101 | US9657009, 101)
Show SMILES C[C@@H](CO)Nc1cc(Nc2ncc(cn2)C#N)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C19H24FN7O3/c1-11(10-28)26-14-4-16(27-18-24-6-12(5-21)7-25-18)22-8-13(14)17(29)23-9-15(20)19(2,3)30/h4,6-8,11,15,28,30H,9-10H2,1-3H3,(H,23,29)(H2,22,24,25,26,27)/t11-,15+/m0/s1
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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283811
PNG
(US10023562, Example 5 | US9657009, 5)
Show SMILES CNC(=O)[C@H]1CC[C@@H](CC1)NC(=O)c1cnc(Nc2ccc(cn2)C#N)cc1NC(C)C
Show InChI InChI=1S/C23H29N7O2/c1-14(2)28-19-10-21(30-20-9-4-15(11-24)12-26-20)27-13-18(19)23(32)29-17-7-5-16(6-8-17)22(31)25-3/h4,9-10,12-14,16-17H,5-8H2,1-3H3,(H,25,31)(H,29,32)(H2,26,27,28,30)/t16-,17-
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US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283961
PNG
(US10023562, Example 153 | US9657009, 153)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2Cl)C#N)cc1Nc1ccc2ncsc2c1
Show InChI InChI=1S/C24H21ClFN7O2S/c1-24(2,35)20(26)11-30-23(34)15-10-28-21(33-22-16(25)5-13(8-27)9-29-22)7-18(15)32-14-3-4-17-19(6-14)36-12-31-17/h3-7,9-10,12,20,35H,11H2,1-2H3,(H,30,34)(H2,28,29,32,33)/t20-/m1/s1
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US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283932
PNG
(US10023562, Example 124 | US9657009, 124)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(Cl)cc2F)cc1NC1CC1
Show InChI InChI=1S/C19H22ClF2N5O2/c1-19(2,29)15(22)9-25-18(28)12-8-23-16(6-14(12)26-11-3-4-11)27-17-13(21)5-10(20)7-24-17/h5-8,11,15,29H,3-4,9H2,1-2H3,(H,25,28)(H2,23,24,26,27)/t15-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283967
PNG
(US10023562, Example 159 | US10023562, Example 160 ...)
Show SMILES CC(F)[C@@H](C)Nc1cc(Nc2ncc(cc2Cl)C#N)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C21H25ClF2N6O2/c1-11(23)12(2)29-16-6-18(30-19-15(22)5-13(7-25)8-27-19)26-9-14(16)20(31)28-10-17(24)21(3,4)32/h5-6,8-9,11-12,17,32H,10H2,1-4H3,(H,28,31)(H2,26,27,29,30)/t11?,12-,17-/m1/s1
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US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283862
PNG
(US10023562, Example 54 | US10023562, Example 55 | ...)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cn2)C#N)cc1N[C@H]1CCC[C@@H]1F
Show InChI InChI=1S/C21H25F2N7O2/c1-21(2,32)17(23)11-26-19(31)13-10-25-18(30-20-27-8-12(7-24)9-28-20)6-16(13)29-15-5-3-4-14(15)22/h6,8-10,14-15,17,32H,3-5,11H2,1-2H3,(H,26,31)(H2,25,27,28,29,30)/t14-,15-,17+/m0/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283947
PNG
(US10023562, Example 139 | US9657009, 139)
Show SMILES CCCNc1cc(Nc2ncc(cc2F)C#N)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C20H24F2N6O2/c1-4-5-24-15-7-17(28-18-14(21)6-12(8-23)9-26-18)25-10-13(15)19(29)27-11-16(22)20(2,3)30/h6-7,9-10,16,30H,4-5,11H2,1-3H3,(H,27,29)(H2,24,25,26,28)/t16-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283943
PNG
(US10023562, Example 135 | US9657009, 135)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2F)C#N)cc1Nc1cccc(c1)C(N)=O
Show InChI InChI=1S/C24H23F2N7O3/c1-24(2,36)19(26)12-31-23(35)16-11-29-20(33-22-17(25)6-13(9-27)10-30-22)8-18(16)32-15-5-3-4-14(7-15)21(28)34/h3-8,10-11,19,36H,12H2,1-2H3,(H2,28,34)(H,31,35)(H2,29,30,32,33)/t19-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM310024
PNG
(6-((5-Cyano-6-((3S)-3-hydroxy-1-pyrrolidinyl)-2-py...)
Show SMILES CC(C)Nc1cc(Nc2ccc(C#N)c(n2)N2CC[C@@H](O)C2)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C24H32FN7O3/c1-14(2)29-18-9-21(27-11-17(18)23(34)28-12-19(25)24(3,4)35)30-20-6-5-15(10-26)22(31-20)32-8-7-16(33)13-32/h5-6,9,11,14,16,19,33,35H,7-8,12-13H2,1-4H3,(H,28,34)(H2,27,29,30,31)/t16-,19-/m1/s1
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Bristol-Myers Squibb Company

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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283842
PNG
(US10023562, Example 34 | US9657009, 34)
Show SMILES CC(C)Nc1cc(Nc2ncc(C#N)c(NC(C)=O)n2)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C21H27FN8O3/c1-11(2)27-15-6-17(24-9-14(15)19(32)25-10-16(22)21(4,5)33)29-20-26-8-13(7-23)18(30-20)28-12(3)31/h6,8-9,11,16,33H,10H2,1-5H3,(H,25,32)(H3,24,26,27,28,29,30,31)/t16-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283977
PNG
(US10023562, Example 168 | US9657009, 168)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2Cl)C#N)cc1Nc1ccc(cc1)-n1cccn1
Show InChI InChI=1S/C26H24ClFN8O2/c1-26(2,38)22(28)15-32-25(37)19-14-30-23(35-24-20(27)10-16(12-29)13-31-24)11-21(19)34-17-4-6-18(7-5-17)36-9-3-8-33-36/h3-11,13-14,22,38H,15H2,1-2H3,(H,32,37)(H2,30,31,34,35)/t22-/m1/s1
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Bristol-Myers Squibb Company

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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283822
PNG
(US10023562, Example 16 | US9657009, 16)
Show SMILES CNC(=O)[C@H]1CC[C@@H](CC1)NC(=O)c1cnc(Nc2ncc(cc2Cl)C#N)cc1NC(C)C
Show InChI InChI=1S/C23H28ClN7O2/c1-13(2)29-19-9-20(31-21-18(24)8-14(10-25)11-28-21)27-12-17(19)23(33)30-16-6-4-15(5-7-16)22(32)26-3/h8-9,11-13,15-16H,4-7H2,1-3H3,(H,26,32)(H,30,33)(H2,27,28,29,31)/t15-,16-
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Bristol-Myers Squibb Company

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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283884
PNG
(US10023562, Example 76 | US10023562, Example 78 | ...)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2Cl)C#N)cc1NC1CCCC1O
Show InChI InChI=1S/C22H26ClFN6O3/c1-22(2,33)18(24)11-28-21(32)13-10-26-19(7-16(13)29-15-4-3-5-17(15)31)30-20-14(23)6-12(8-25)9-27-20/h6-7,9-10,15,17-18,31,33H,3-5,11H2,1-2H3,(H,28,32)(H2,26,27,29,30)/t15?,17?,18-/m1/s1
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Bristol-Myers Squibb Company

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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283848
PNG
(US10023562, Example 40 | US9657009, 40)
Show SMILES CC(C)Nc1cc(Nc2ncc(C#N)c(NC(C)C)n2)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C22H31FN8O2/c1-12(2)28-16-7-18(25-10-15(16)20(32)26-11-17(23)22(5,6)33)30-21-27-9-14(8-24)19(31-21)29-13(3)4/h7,9-10,12-13,17,33H,11H2,1-6H3,(H,26,32)(H3,25,27,28,29,30,31)/t17-/m1/s1
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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283929
PNG
(US10023562, Example 121 | US9657009, 121)
Show SMILES CC(C)Nc1cc(Nc2ncc(cc2F)C#N)ncc1C(=O)NCCc1ccc(cc1)S(N)(=O)=O
Show InChI InChI=1S/C23H24FN7O3S/c1-14(2)30-20-10-21(31-22-19(24)9-16(11-25)12-29-22)28-13-18(20)23(32)27-8-7-15-3-5-17(6-4-15)35(26,33)34/h3-6,9-10,12-14H,7-8H2,1-2H3,(H,27,32)(H2,26,33,34)(H2,28,29,30,31)
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n/an/a 6.60n/an/an/an/an/an/a



Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283868
PNG
(US10023562, Example 60 | US9657009, 60)
Show SMILES CNC(=O)[C@H]1CC[C@@H](CC1)NC(=O)c1cnc(Nc2ncc(cc2Cl)C#N)cc1NC1CC1
Show InChI InChI=1S/C23H26ClN7O2/c1-26-22(32)14-2-4-16(5-3-14)30-23(33)17-12-27-20(9-19(17)29-15-6-7-15)31-21-18(24)8-13(10-25)11-28-21/h8-9,11-12,14-16H,2-7H2,1H3,(H,26,32)(H,30,33)(H2,27,28,29,31)/t14-,16-
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n/an/a 6.70n/an/an/an/an/an/a



Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283860
PNG
(US10023562, Example 52 | US9657009, 52)
Show SMILES CC(C)Nc1cc(Nc2ncncc2Cl)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C18H24ClFN6O2/c1-10(2)25-13-5-15(26-16-12(19)7-21-9-24-16)22-6-11(13)17(27)23-8-14(20)18(3,4)28/h5-7,9-10,14,28H,8H2,1-4H3,(H,23,27)(H2,21,22,24,25,26)/t14-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283888
PNG
(US10023562, Example 80 | US9657009, 80)
Show SMILES CC(C)Nc1cc(Nc2ncc(F)cc2F)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C19H24F3N5O2/c1-10(2)26-14-6-16(27-17-13(21)5-11(20)7-24-17)23-8-12(14)18(28)25-9-15(22)19(3,4)29/h5-8,10,15,29H,9H2,1-4H3,(H,25,28)(H2,23,24,26,27)/t15-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283889
PNG
(US10023562, Example 81 | US9657009, 81)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ccc(Cl)cn2)cc1NC1CC1
Show InChI InChI=1S/C19H23ClFN5O2/c1-19(2,28)15(21)10-24-18(27)13-9-23-17(7-14(13)25-12-4-5-12)26-16-6-3-11(20)8-22-16/h3,6-9,12,15,28H,4-5,10H2,1-2H3,(H,24,27)(H2,22,23,25,26)/t15-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283903
PNG
(US10023562, Example 95 | US9657009, 95)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncncc2Cl)cc1NC1CCOCC1
Show InChI InChI=1S/C20H26ClFN6O3/c1-20(2,30)16(22)10-25-19(29)13-8-24-17(28-18-14(21)9-23-11-26-18)7-15(13)27-12-3-5-31-6-4-12/h7-9,11-12,16,30H,3-6,10H2,1-2H3,(H,25,29)(H2,23,24,26,27,28)/t16-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283875
PNG
(US10023562, Example 67 | US9657009, 67)
Show SMILES CC(=O)N[C@H]1CC[C@@H](CC1)NC(=O)c1cnc(Nc2ncc(cc2Cl)C#N)cc1NC1CC1
Show InChI InChI=1S/C23H26ClN7O2/c1-13(32)28-15-2-6-17(7-3-15)30-23(33)18-12-26-21(9-20(18)29-16-4-5-16)31-22-19(24)8-14(10-25)11-27-22/h8-9,11-12,15-17H,2-7H2,1H3,(H,28,32)(H,30,33)(H2,26,27,29,31)/t15-,17-
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283891
PNG
(US10023562, Example 83 | US9657009, 83)
Show SMILES CC(=O)N[C@H]1CC[C@@H](CC1)NC(=O)c1cnc(Nc2ncc(cc2F)C#N)cc1NC1CC1
Show InChI InChI=1S/C23H26FN7O2/c1-13(32)28-15-2-6-17(7-3-15)30-23(33)18-12-26-21(9-20(18)29-16-4-5-16)31-22-19(24)8-14(10-25)11-27-22/h8-9,11-12,15-17H,2-7H2,1H3,(H,28,32)(H,30,33)(H2,26,27,29,31)/t15-,17-
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283948
PNG
(US10023562, Example 140 | US9657009, 140)
Show SMILES CC(C)CCNc1cc(Nc2ncc(cc2Cl)C#N)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C22H28ClFN6O2/c1-13(2)5-6-26-17-8-19(30-20-16(23)7-14(9-25)10-28-20)27-11-15(17)21(31)29-12-18(24)22(3,4)32/h7-8,10-11,13,18,32H,5-6,12H2,1-4H3,(H,29,31)(H2,26,27,28,30)/t18-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283815
PNG
(US10023562, Example 9 | US9657009, 9)
Show SMILES CC(C)Nc1cc(Nc2ccc(cn2)C#N)ncc1C(=O)N[C@H]1CC[C@@H](CC1)NC(C)=O
Show InChI InChI=1S/C23H29N7O2/c1-14(2)27-20-10-22(30-21-9-4-16(11-24)12-25-21)26-13-19(20)23(32)29-18-7-5-17(6-8-18)28-15(3)31/h4,9-10,12-14,17-18H,5-8H2,1-3H3,(H,28,31)(H,29,32)(H2,25,26,27,30)/t17-,18-
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283867
PNG
(US10023562, Example 59 | US9657009, 59)
Show SMILES CNC(=O)[C@H]1CC[C@@H](CC1)NC(=O)c1cnc(Nc2ncc(cc2F)C#N)cc1NC1CC1
Show InChI InChI=1S/C23H26FN7O2/c1-26-22(32)14-2-4-16(5-3-14)30-23(33)17-12-27-20(9-19(17)29-15-6-7-15)31-21-18(24)8-13(10-25)11-28-21/h8-9,11-12,14-16H,2-7H2,1H3,(H,26,32)(H,30,33)(H2,27,28,29,31)/t14-,16-
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283853
PNG
(US10023562, Example 45 | US9657009, 45)
Show SMILES CC(C)Nc1cc(Nc2ccc(=O)[nH]n2)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C18H25FN6O3/c1-10(2)22-12-7-15(23-14-5-6-16(26)25-24-14)20-8-11(12)17(27)21-9-13(19)18(3,4)28/h5-8,10,13,28H,9H2,1-4H3,(H,21,27)(H,25,26)(H2,20,22,23,24)/t13-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283905
PNG
(US10023562, Example 97 | US9657009, 98)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2F)C#N)cc1NC1CCCOC1
Show InChI InChI=1S/C22H26F2N6O3/c1-22(2,32)18(24)11-28-21(31)15-10-26-19(7-17(15)29-14-4-3-5-33-12-14)30-20-16(23)6-13(8-25)9-27-20/h6-7,9-10,14,18,32H,3-5,11-12H2,1-2H3,(H,28,31)(H2,26,27,29,30)/t14?,18-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283885
PNG
(US10023562, Example 77 | US9657009, 77)
Show SMILES CC(=O)N[C@H]1CC[C@@H](CC1)NC(=O)c1cnc(Nc2ncc(cc2Cl)C#N)cc1NC1CCOCC1
Show InChI InChI=1S/C25H30ClN7O3/c1-15(34)30-17-2-4-18(5-3-17)32-25(35)20-14-28-23(11-22(20)31-19-6-8-36-9-7-19)33-24-21(26)10-16(12-27)13-29-24/h10-11,13-14,17-19H,2-9H2,1H3,(H,30,34)(H,32,35)(H2,28,29,31,33)/t17-,18-
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM310042
PNG
(US9657009, 44)
Show SMILES CC(C)Nc1cc(Nc2ncc(cc2F)C#N)ncc1C(=O)NC1CCC(CC1)[C@@](C)(O)C1CC1
Show InChI InChI=1S/C26H33FN6O2/c1-15(2)31-22-11-23(33-24-21(27)10-16(12-28)13-30-24)29-14-20(22)25(34)32-19-8-6-18(7-9-19)26(3,35)17-4-5-17/h10-11,13-15,17-19,35H,4-9H2,1-3H3,(H,32,34)(H2,29,30,31,33)/t18?,19?,26-/m0/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283952
PNG
(US10023562, Example 144 | US10023562, Example 145 ...)
Show SMILES CC(C)Nc1cc(Nc2ncc(cc2F)C#N)ncc1C(=O)NC1CC[C@@H](CC1)C(C)(O)C1CC1
Show InChI InChI=1S/C26H33FN6O2/c1-15(2)31-22-11-23(33-24-21(27)10-16(12-28)13-30-24)29-14-20(22)25(34)32-19-8-6-18(7-9-19)26(3,35)17-4-5-17/h10-11,13-15,17-19,35H,4-9H2,1-3H3,(H,32,34)(H2,29,30,31,33)/t18-,19?,26?
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM310162
PNG
(US9657009, 164)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2F)C#N)cc1NC1COC1
Show InChI InChI=1S/C20H22F2N6O3/c1-20(2,30)16(22)8-26-19(29)13-7-24-17(4-15(13)27-12-9-31-10-12)28-18-14(21)3-11(5-23)6-25-18/h3-4,6-7,12,16,30H,8-10H2,1-2H3,(H,26,29)(H2,24,25,27,28)/t16-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283861
PNG
(US10023562, Example 53 | US9657009, 53)
Show SMILES CC(C)Nc1cc(Nc2ncncc2F)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C18H24F2N6O2/c1-10(2)25-13-5-15(26-16-12(19)7-21-9-24-16)22-6-11(13)17(27)23-8-14(20)18(3,4)28/h5-7,9-10,14,28H,8H2,1-4H3,(H,23,27)(H2,21,22,24,25,26)/t14-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM310164
PNG
(US9657009, 166)
Show SMILES CC(C)Nc1cc(Nc2ncc(cc2F)C#N)ncc1C(=O)NC1CCC(O)(CC1)c1ccnn1C
Show InChI InChI=1S/C25H29FN8O2/c1-15(2)31-20-11-22(33-23-19(26)10-16(12-27)13-29-23)28-14-18(20)24(35)32-17-4-7-25(36,8-5-17)21-6-9-30-34(21)3/h6,9-11,13-15,17,36H,4-5,7-8H2,1-3H3,(H,32,35)(H2,28,29,31,33)
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283869
PNG
(US10023562, Example 61 | US9657009, 61)
Show SMILES CNC(=O)[C@H]1CC[C@@H](CC1)NC(=O)c1cnc(Nc2ncc(cc2F)C#N)cc1NC1CCOCC1
Show InChI InChI=1S/C25H30FN7O3/c1-28-24(34)16-2-4-17(5-3-16)32-25(35)19-14-29-22(11-21(19)31-18-6-8-36-9-7-18)33-23-20(26)10-15(12-27)13-30-23/h10-11,13-14,16-18H,2-9H2,1H3,(H,28,34)(H,32,35)(H2,29,30,31,33)/t16-,17-
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283954
PNG
(US10023562, Example 146 | US9657009, 146)
Show SMILES Cn1nnnc1-c1cccc(Nc2cc(Nc3ncc(cc3Cl)C#N)ncc2C(=O)NC[C@@H](F)C(C)(C)O)c1
Show InChI InChI=1S/C25H24ClFN10O2/c1-25(2,39)20(27)13-31-24(38)17-12-29-21(33-22-18(26)7-14(10-28)11-30-22)9-19(17)32-16-6-4-5-15(8-16)23-34-35-36-37(23)3/h4-9,11-12,20,39H,13H2,1-3H3,(H,31,38)(H2,29,30,32,33)/t20-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283912
PNG
(US10023562, Example 104 | US9657009, 104)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2Cl)C#N)cc1NC1CCCCC1O
Show InChI InChI=1S/C23H28ClFN6O3/c1-23(2,34)19(25)12-29-22(33)14-11-27-20(31-21-15(24)7-13(9-26)10-28-21)8-17(14)30-16-5-3-4-6-18(16)32/h7-8,10-11,16,18-19,32,34H,3-6,12H2,1-2H3,(H,29,33)(H2,27,28,30,31)/t16?,18?,19-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283964
PNG
(US10023562, Example 156 | US9657009, 156)
Show SMILES CC(C)Nc1cc(Nc2ncc(cc2Cl)C#N)ncc1C(=O)NC[C@H](F)C(C)(C)O
Show InChI InChI=1S/C20H24ClFN6O2/c1-11(2)27-15-6-17(28-18-14(21)5-12(7-23)8-25-18)24-9-13(15)19(29)26-10-16(22)20(3,4)30/h5-6,8-9,11,16,30H,10H2,1-4H3,(H,26,29)(H2,24,25,27,28)/t16-/m0/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283916
PNG
(US10023562, Example 108 | US9657009, 108)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(F)cc2F)cc1NC1CCOCC1F
Show InChI InChI=1S/C21H25F4N5O3/c1-21(2,32)17(25)9-28-20(31)12-8-26-18(30-19-13(23)5-11(22)7-27-19)6-16(12)29-15-3-4-33-10-14(15)24/h5-8,14-15,17,32H,3-4,9-10H2,1-2H3,(H,28,31)(H2,26,27,29,30)/t14?,15?,17-/m1/s1
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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283915
PNG
(US10023562, Example 107 | US9657009, 107)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cn2)C#N)cc1N[C@H]1CCC[C@H]1F
Show InChI InChI=1S/C21H25F2N7O2/c1-21(2,32)17(23)11-26-19(31)13-10-25-18(30-20-27-8-12(7-24)9-28-20)6-16(13)29-15-5-3-4-14(15)22/h6,8-10,14-15,17,32H,3-5,11H2,1-2H3,(H,26,31)(H2,25,27,28,29,30)/t14-,15+,17-/m1/s1
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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283856
PNG
(US10023562, Example 48 | US9657009, 48)
Show SMILES CC(C)(O)CNc1cc(Nc2ncc(cc2Cl)C#N)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C21H26ClFN6O3/c1-20(2,31)11-28-15-6-17(29-18-14(22)5-12(7-24)8-26-18)25-9-13(15)19(30)27-10-16(23)21(3,4)32/h5-6,8-9,16,31-32H,10-11H2,1-4H3,(H,27,30)(H2,25,26,28,29)/t16-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM310027
PNG
(US9657009, 30)
Show SMILES CCNC(=O)[C@H]1CC[C@@H](CC1)NC(=O)c1cnc(Nc2ncc(cc2F)C#N)cc1NC(C)C
Show InChI InChI=1S/C24H30FN7O2/c1-4-27-23(33)16-5-7-17(8-6-16)31-24(34)18-13-28-21(10-20(18)30-14(2)3)32-22-19(25)9-15(11-26)12-29-22/h9-10,12-14,16-17H,4-8H2,1-3H3,(H,27,33)(H,31,34)(H2,28,29,30,32)/t16-,17-
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283858
PNG
(US10023562, Example 50 | US9657009, 50)
Show SMILES C[C@@H](CO)Nc1cc(Nc2ncc(cc2Cl)C#N)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C20H24ClFN6O3/c1-11(10-29)27-15-5-17(28-18-14(21)4-12(6-23)7-25-18)24-8-13(15)19(30)26-9-16(22)20(2,3)31/h4-5,7-8,11,16,29,31H,9-10H2,1-3H3,(H,26,30)(H2,24,25,27,28)/t11-,16+/m0/s1
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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283823
PNG
(US10023562, Example 129 | US10023562, Example 17 |...)
Show SMILES CC(C)Nc1cc(Nc2ncc(cc2F)C#N)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C20H24F2N6O2/c1-11(2)27-15-6-17(28-18-14(21)5-12(7-23)8-25-18)24-9-13(15)19(29)26-10-16(22)20(3,4)30/h5-6,8-9,11,16,30H,10H2,1-4H3,(H,26,29)(H2,24,25,27,28)/t16-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283967
PNG
(US10023562, Example 159 | US10023562, Example 160 ...)
Show SMILES CC(F)[C@@H](C)Nc1cc(Nc2ncc(cc2Cl)C#N)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C21H25ClF2N6O2/c1-11(23)12(2)29-16-6-18(30-19-15(22)5-13(7-25)8-27-19)26-9-14(16)20(31)28-10-17(24)21(3,4)32/h5-6,8-9,11-12,17,32H,10H2,1-4H3,(H,28,31)(H2,26,27,29,30)/t11?,12-,17-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283832
PNG
(US10023562, Example 25 | US9657009, 25)
Show SMILES CC(C)Nc1cc(Nc2ccnc(NC3CCCOC3)n2)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C23H34FN7O3/c1-14(2)28-17-10-20(26-11-16(17)21(32)27-12-18(24)23(3,4)33)30-19-7-8-25-22(31-19)29-15-6-5-9-34-13-15/h7-8,10-11,14-15,18,33H,5-6,9,12-13H2,1-4H3,(H,27,32)(H3,25,26,28,29,30,31)/t15?,18-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283949
PNG
(US10023562, Example 141 | US9657009, 141)
Show SMILES CC(C)CCNc1cc(Nc2ncc(cc2F)C#N)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C22H28F2N6O2/c1-13(2)5-6-26-17-8-19(30-20-16(23)7-14(9-25)10-28-20)27-11-15(17)21(31)29-12-18(24)22(3,4)32/h7-8,10-11,13,18,32H,5-6,12H2,1-4H3,(H,29,31)(H2,26,27,28,30)/t18-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283840
PNG
(US10023562, Example 33 | US9657009, 33)
Show SMILES CC(C)Nc1cc(Nc2ncc(cc2F)C#N)ncc1C(=O)N[C@H]1CC[C@@H](CC1)S(C)(=O)=O
Show InChI InChI=1S/C22H27FN6O3S/c1-13(2)27-19-9-20(29-21-18(23)8-14(10-24)11-26-21)25-12-17(19)22(30)28-15-4-6-16(7-5-15)33(3,31)32/h8-9,11-13,15-16H,4-7H2,1-3H3,(H,28,30)(H2,25,26,27,29)/t15-,16-
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Bristol-Myers Squibb Company

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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283971
PNG
(US10023562, Example 163 | US9657009, 163)
Show SMILES CC(Nc1cc(Nc2ncc(cn2)C#N)ncc1C(=O)NC[C@@H](F)C(C)(C)O)C1CC1
Show InChI InChI=1S/C21H26FN7O2/c1-12(14-4-5-14)28-16-6-18(29-20-26-8-13(7-23)9-27-20)24-10-15(16)19(30)25-11-17(22)21(2,3)31/h6,8-10,12,14,17,31H,4-5,11H2,1-3H3,(H,25,30)(H2,24,26,27,28,29)/t12?,17-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM310000
PNG
(US9657009, 4)
Show SMILES CCNc1cc(Nc2ccc(cn2)C#N)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C19H23FN6O2/c1-4-22-14-7-17(26-16-6-5-12(8-21)9-23-16)24-10-13(14)18(27)25-11-15(20)19(2,3)28/h5-7,9-10,15,28H,4,11H2,1-3H3,(H,25,27)(H2,22,23,24,26)/t15-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283866
PNG
(US10023562, Example 58 | US9657009, 58)
Show SMILES CCNc1cc(Nc2ncc(cn2)C#N)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C18H22FN7O2/c1-4-21-13-5-15(26-17-24-7-11(6-20)8-25-17)22-9-12(13)16(27)23-10-14(19)18(2,3)28/h5,7-9,14,28H,4,10H2,1-3H3,(H,23,27)(H2,21,22,24,25,26)/t14-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283813
PNG
(US10023562, Example 7 | US9657009, 7)
Show SMILES CC(C)Nc1cc(Nc2ccc(cn2)C#N)ncc1C(=O)N[C@H]1CC[C@@H](CC1)C(=O)N[C@H]1C[C@H]1F
Show InChI InChI=1S/C25H30FN7O2/c1-14(2)30-20-10-23(33-22-8-3-15(11-27)12-28-22)29-13-18(20)25(35)31-17-6-4-16(5-7-17)24(34)32-21-9-19(21)26/h3,8,10,12-14,16-17,19,21H,4-7,9H2,1-2H3,(H,31,35)(H,32,34)(H2,28,29,30,33)/t16-,17-,19-,21+/m1/s1
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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283880
PNG
(US10023562, Example 72 | US9657009, 72)
Show SMILES CCn1ncc(Nc2cc(NC(C)C)c(cn2)C(=O)NC[C@@H](F)C(C)(C)O)n1
Show InChI InChI=1S/C18H28FN7O2/c1-6-26-22-10-16(25-26)24-15-7-13(23-11(2)3)12(8-20-15)17(27)21-9-14(19)18(4,5)28/h7-8,10-11,14,28H,6,9H2,1-5H3,(H,21,27)(H2,20,23,24,25)/t14-/m1/s1
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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283927
PNG
(US10023562, Example 119 | US9657009, 119)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2F)C#N)cc1NC12CC3CC(CC(C3)C1)C2
Show InChI InChI=1S/C27H32F2N6O2/c1-26(2,37)22(29)14-33-25(36)19-13-31-23(34-24-20(28)6-18(11-30)12-32-24)7-21(19)35-27-8-15-3-16(9-27)5-17(4-15)10-27/h6-7,12-13,15-17,22,37H,3-5,8-10,14H2,1-2H3,(H,33,36)(H2,31,32,34,35)/t15?,16?,17?,22-,27?/m1/s1
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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283939
PNG
(US10023562, Example 131 | US9657009, 131)
Show SMILES CC(C)Nc1cc(Nc2ccnc(N)n2)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C18H26FN7O2/c1-10(2)24-12-7-15(25-14-5-6-21-17(20)26-14)22-8-11(12)16(27)23-9-13(19)18(3,4)28/h5-8,10,13,28H,9H2,1-4H3,(H,23,27)(H4,20,21,22,24,25,26)/t13-/m1/s1
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n/an/a 10.6n/an/an/an/an/an/a



Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM310041
PNG
(US9657009, 43)
Show SMILES CC(C)(O)C(F)(F)CNC(=O)c1cnc(Nc2ncc(cc2Cl)C#N)cc1NC1CC1
Show InChI InChI=1S/C20H21ClF2N6O2/c1-19(2,31)20(22,23)10-27-18(30)13-9-25-16(6-15(13)28-12-3-4-12)29-17-14(21)5-11(7-24)8-26-17/h5-6,8-9,12,31H,3-4,10H2,1-2H3,(H,27,30)(H2,25,26,28,29)
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283920
PNG
(US10023562, Example 112 | US9657009, 112)
Show SMILES COc1cnc(Nc2cc(NC3CCC3)c(cn2)C(=O)NC[C@@H](F)C(C)(C)O)nc1
Show InChI InChI=1S/C20H27FN6O3/c1-20(2,29)16(21)11-23-18(28)14-10-22-17(7-15(14)26-12-5-4-6-12)27-19-24-8-13(30-3)9-25-19/h7-10,12,16,29H,4-6,11H2,1-3H3,(H,23,28)(H2,22,24,25,26,27)/t16-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM310021
PNG
(6-((2-(Cyclopropylamino)-4-pyrimidinyl)amino)-N-((...)
Show SMILES CC(C)Nc1cc(Nc2ccnc(NC3CC3)n2)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C21H30FN7O2/c1-12(2)26-15-9-18(28-17-7-8-23-20(29-17)27-13-5-6-13)24-10-14(15)19(30)25-11-16(22)21(3,4)31/h7-10,12-13,16,31H,5-6,11H2,1-4H3,(H,25,30)(H3,23,24,26,27,28,29)/t16-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283817
PNG
(US10023562, Example 11 | US9657009, 11)
Show SMILES CC(=O)N[C@H]1CC[C@@H](CC1)NC(=O)c1cnc(Nc2ccc(cn2)C#N)cc1NC1CCOCC1F
Show InChI InChI=1S/C25H30FN7O3/c1-15(34)30-17-3-5-18(6-4-17)31-25(35)19-13-29-24(33-23-7-2-16(11-27)12-28-23)10-22(19)32-21-8-9-36-14-20(21)26/h2,7,10,12-13,17-18,20-21H,3-6,8-9,14H2,1H3,(H,30,34)(H,31,35)(H2,28,29,32,33)/t17-,18-,20?,21?
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283904
PNG
(US10023562, Example 96 | US9657009, 96)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncncc2Cl)cc1NC1CCCOC1
Show InChI InChI=1S/C20H26ClFN6O3/c1-20(2,30)16(22)9-25-19(29)13-7-24-17(28-18-14(21)8-23-11-26-18)6-15(13)27-12-4-3-5-31-10-12/h6-8,11-12,16,30H,3-5,9-10H2,1-2H3,(H,25,29)(H2,23,24,26,27,28)/t12?,16-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283974
PNG
(US10023562, Example 165 | US9657009, 165)
Show SMILES COC(=O)N[C@H]1CC[C@@H](CC1)NC(=O)c1cnc(Nc2ncc(cc2F)C#N)cc1NC(C)C
Show InChI InChI=1S/C23H28FN7O3/c1-13(2)28-19-9-20(31-21-18(24)8-14(10-25)11-27-21)26-12-17(19)22(32)29-15-4-6-16(7-5-15)30-23(33)34-3/h8-9,11-13,15-16H,4-7H2,1-3H3,(H,29,32)(H,30,33)(H2,26,27,28,31)/t15-,16-
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283826
PNG
(N-((2R)-2-Fluoro-3-hydroxy-3-methylbutyl)-4-(isopr...)
Show SMILES CC(C)Nc1cc(Nc2ccncn2)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C18H25FN6O2/c1-11(2)24-13-7-16(25-15-5-6-20-10-23-15)21-8-12(13)17(26)22-9-14(19)18(3,4)27/h5-8,10-11,14,27H,9H2,1-4H3,(H,22,26)(H2,20,21,23,24,25)/t14-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283919
PNG
(US10023562, Example 111 | US9657009, 111)
Show SMILES CC(C)Nc1cc(Nc2ncc(O)cn2)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C18H25FN6O3/c1-10(2)24-13-5-15(25-17-22-6-11(26)7-23-17)20-8-12(13)16(27)21-9-14(19)18(3,4)28/h5-8,10,14,26,28H,9H2,1-4H3,(H,21,27)(H2,20,22,23,24,25)/t14-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283902
PNG
(US10023562, Example 94 | US9657009, 94)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncncc2F)cc1NC1CC1
Show InChI InChI=1S/C18H22F2N6O2/c1-18(2,28)14(20)8-23-17(27)11-6-22-15(5-13(11)25-10-3-4-10)26-16-12(19)7-21-9-24-16/h5-7,9-10,14,28H,3-4,8H2,1-2H3,(H,23,27)(H2,21,22,24,25,26)/t14-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283955
PNG
(US10023562, Example 147 | US9657009, 147)
Show SMILES Cn1nnnc1-c1ccc(Nc2cc(Nc3ncc(cn3)C#N)ncc2C(=O)NC[C@@H](F)C(C)(C)O)cc1
Show InChI InChI=1S/C24H24FN11O2/c1-24(2,38)19(25)13-28-22(37)17-12-27-20(32-23-29-10-14(9-26)11-30-23)8-18(17)31-16-6-4-15(5-7-16)21-33-34-35-36(21)3/h4-8,10-12,19,38H,13H2,1-3H3,(H,28,37)(H2,27,29,30,31,32)/t19-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM310029
PNG
(US9657009, 32)
Show SMILES CS[C@H]1CC[C@@H](CC1)NC(=O)c1cnc(Nc2ncc(cc2F)C#N)cc1NC(C)C
Show InChI InChI=1S/C22H27FN6OS/c1-13(2)27-19-9-20(29-21-18(23)8-14(10-24)11-26-21)25-12-17(19)22(30)28-15-4-6-16(31-3)7-5-15/h8-9,11-13,15-16H,4-7H2,1-3H3,(H,28,30)(H2,25,26,27,29)/t15-,16-
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283928
PNG
(US10023562, Example 120 | US9657009, 120)
Show SMILES COCCCNC(=O)c1cnc(Nc2ncc(cc2Cl)C#N)cc1NC(C)C
Show InChI InChI=1S/C19H23ClN6O2/c1-12(2)25-16-8-17(26-18-15(20)7-13(9-21)10-24-18)23-11-14(16)19(27)22-5-4-6-28-3/h7-8,10-12H,4-6H2,1-3H3,(H,22,27)(H2,23,24,25,26)
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM310032
PNG
(US9657009, 35)
Show SMILES COC[C@H](F)CNC(=O)c1cnc(Nc2ncc(cc2F)C#N)cc1NC(C)C
Show InChI InChI=1S/C19H22F2N6O2/c1-11(2)26-16-5-17(27-18-15(21)4-12(6-22)7-24-18)23-9-14(16)19(28)25-8-13(20)10-29-3/h4-5,7,9,11,13H,8,10H2,1-3H3,(H,25,28)(H2,23,24,26,27)/t13-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283900
PNG
(US10023562, Example 92 | US9657009, 92)
Show SMILES CC(C)Nc1cc(Nc2ncc(cc2Cl)C#N)ncc1C(=O)N[C@H]1CC[C@H](O)CC1
Show InChI InChI=1S/C21H25ClN6O2/c1-12(2)26-18-8-19(28-20-17(22)7-13(9-23)10-25-20)24-11-16(18)21(30)27-14-3-5-15(29)6-4-14/h7-8,10-12,14-15,29H,3-6H2,1-2H3,(H,27,30)(H2,24,25,26,28)/t14-,15-
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM310165
PNG
(US9657009, 167)
Show SMILES CC(C)Nc1cc(Nc2ncc(cc2F)C#N)ncc1C(=O)NC1CCC(O)(CC1)c1nccs1
Show InChI InChI=1S/C24H26FN7O2S/c1-14(2)30-19-10-20(32-21-18(25)9-15(11-26)12-29-21)28-13-17(19)22(33)31-16-3-5-24(34,6-4-16)23-27-7-8-35-23/h7-10,12-14,16,34H,3-6H2,1-2H3,(H,31,33)(H2,28,29,30,32)
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283940
PNG
(US10023562, Example 132 | US9657009, 132)
Show SMILES CC(C)Nc1cc(Nc2ncncc2N)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C18H26FN7O2/c1-10(2)25-13-5-15(26-16-12(20)7-21-9-24-16)22-6-11(13)17(27)23-8-14(19)18(3,4)28/h5-7,9-10,14,28H,8,20H2,1-4H3,(H,23,27)(H2,21,22,24,25,26)/t14-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283828
PNG
(4-(Cyclopropylamino)-N-((2R)-2-fluoro-3-hydroxy-3-...)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ccncn2)cc1NC1CC1
Show InChI InChI=1S/C18H23FN6O2/c1-18(2,27)14(19)9-22-17(26)12-8-21-16(7-13(12)24-11-3-4-11)25-15-5-6-20-10-23-15/h5-8,10-11,14,27H,3-4,9H2,1-2H3,(H,22,26)(H2,20,21,23,24,25)/t14-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283917
PNG
(US10023562, Example 109 | US10023562, Example 110 ...)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(F)cc2F)cc1NC1CCCOC1
Show InChI InChI=1S/C21H26F3N5O3/c1-21(2,31)17(24)10-27-20(30)14-9-25-18(29-19-15(23)6-12(22)8-26-19)7-16(14)28-13-4-3-5-32-11-13/h6-9,13,17,31H,3-5,10-11H2,1-2H3,(H,27,30)(H2,25,26,28,29)/t13?,17-/m1/s1
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Bristol-Myers Squibb Company

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Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283816
PNG
(US10023562, Example 10 | US9657009, 10)
Show SMILES CC(=O)N[C@H]1CC[C@@H](CC1)NC(=O)c1cnc(Nc2ccc(cn2)C#N)cc1NC1CCC1
Show InChI InChI=1S/C24H29N7O2/c1-15(32)28-18-6-8-19(9-7-18)30-24(33)20-14-27-23(11-21(20)29-17-3-2-4-17)31-22-10-5-16(12-25)13-26-22/h5,10-11,13-14,17-19H,2-4,6-9H2,1H3,(H,28,32)(H,30,33)(H2,26,27,29,31)/t18-,19-
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283897
PNG
(US10023562, Example 89 | US9657009, 89)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(F)cc2F)cc1NC1CC1
Show InChI InChI=1S/C19H22F3N5O2/c1-19(2,29)15(22)9-25-18(28)12-8-23-16(6-14(12)26-11-3-4-11)27-17-13(21)5-10(20)7-24-17/h5-8,11,15,29H,3-4,9H2,1-2H3,(H,25,28)(H2,23,24,26,27)/t15-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283850
PNG
(US10023562, Example 42 | US9657009, 42)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2nc(OC3CCNCC3)ncc2Cl)cc1NC1CC1
Show InChI InChI=1S/C23H31ClFN7O3/c1-23(2,34)18(25)12-28-21(33)15-10-27-19(9-17(15)30-13-3-4-13)31-20-16(24)11-29-22(32-20)35-14-5-7-26-8-6-14/h9-11,13-14,18,26,34H,3-8,12H2,1-2H3,(H,28,33)(H2,27,29,30,31,32)/t18-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283809
PNG
(US10023562, Example 3 | US10023562, Example 4 | US...)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ccc(cn2)C#N)cc1NCC(F)(F)F
Show InChI InChI=1S/C19H20F4N6O2/c1-18(2,31)14(20)9-27-17(30)12-8-26-16(5-13(12)28-10-19(21,22)23)29-15-4-3-11(6-24)7-25-15/h3-5,7-8,14,31H,9-10H2,1-2H3,(H,27,30)(H2,25,26,28,29)/t14-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283935
PNG
(US10023562, Example 127 | US9657009, 127)
Show SMILES CC(C)Nc1cc(Nc2ncc(cc2F)C#N)ncc1C(=O)NCCCOC(C)(C)C
Show InChI InChI=1S/C22H29FN6O2/c1-14(2)28-18-10-19(29-20-17(23)9-15(11-24)12-27-20)26-13-16(18)21(30)25-7-6-8-31-22(3,4)5/h9-10,12-14H,6-8H2,1-5H3,(H,25,30)(H2,26,27,28,29)
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283969
PNG
(US10023562, Example 161 | US9657009, 161)
Show SMILES CS(=O)(=O)[C@H]1CC[C@@H](CC1)NC(=O)c1cnc(Nc2ncc(cc2F)C#N)cc1Nc1cccc(c1)C(N)=O
Show InChI InChI=1S/C26H26FN7O4S/c1-39(37,38)19-7-5-17(6-8-19)33-26(36)20-14-30-23(34-25-21(27)9-15(12-28)13-31-25)11-22(20)32-18-4-2-3-16(10-18)24(29)35/h2-4,9-11,13-14,17,19H,5-8H2,1H3,(H2,29,35)(H,33,36)(H2,30,31,32,34)/t17-,19-
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283917
PNG
(US10023562, Example 109 | US10023562, Example 110 ...)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2ncc(F)cc2F)cc1NC1CCCOC1
Show InChI InChI=1S/C21H26F3N5O3/c1-21(2,31)17(24)10-27-20(30)14-9-25-18(29-19-15(23)6-12(22)8-26-19)7-16(14)28-13-4-3-5-32-11-13/h6-9,13,17,31H,3-5,10-11H2,1-2H3,(H,27,30)(H2,25,26,28,29)/t13?,17-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM310127
PNG
(US9657009, 129)
Show SMILES CC(C)Nc1cc(Nc2ncc(C)cc2F)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C20H27F2N5O2/c1-11(2)26-15-7-17(27-18-14(21)6-12(3)8-24-18)23-9-13(15)19(28)25-10-16(22)20(4,5)29/h6-9,11,16,29H,10H2,1-5H3,(H,25,28)(H2,23,24,26,27)/t16-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283914
PNG
(US10023562, Example 106 | US9657009, 106)
Show SMILES CC(C)Nc1cc(Nc2ncncc2Cl)ncc1C(=O)N[C@H]1CC[C@@H](CC1)NC(C)=O
Show InChI InChI=1S/C21H28ClN7O2/c1-12(2)26-18-8-19(29-20-17(22)10-23-11-25-20)24-9-16(18)21(31)28-15-6-4-14(5-7-15)27-13(3)30/h8-12,14-15H,4-7H2,1-3H3,(H,27,30)(H,28,31)(H2,23,24,25,26,29)/t14-,15-
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283854
PNG
(US10023562, Example 46 | US9657009, 46)
Show SMILES CC(C)(F)CNc1cc(Nc2ncc(cc2Cl)C#N)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C21H25ClF2N6O2/c1-20(2,24)11-29-15-6-17(30-18-14(22)5-12(7-25)8-27-18)26-9-13(15)19(31)28-10-16(23)21(3,4)32/h5-6,8-9,16,32H,10-11H2,1-4H3,(H,28,31)(H2,26,27,29,30)/t16-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283921
PNG
(US10023562, Example 113 | US9657009, 113)
Show SMILES CC(C)Nc1cc(Nc2ncc(C)cn2)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C19H27FN6O2/c1-11(2)25-14-6-16(26-18-23-7-12(3)8-24-18)21-9-13(14)17(27)22-10-15(20)19(4,5)28/h6-9,11,15,28H,10H2,1-5H3,(H,22,27)(H2,21,23,24,25,26)/t15-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283908
PNG
(US10023562, Example 100 | US9657009, 100)
Show SMILES C[C@H](CO)Nc1cc(Nc2ncc(F)cc2F)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C19H24F3N5O3/c1-10(9-28)26-14-5-16(27-17-13(21)4-11(20)6-24-17)23-7-12(14)18(29)25-8-15(22)19(2,3)30/h4-7,10,15,28,30H,8-9H2,1-3H3,(H,25,29)(H2,23,24,26,27)/t10-,15-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283901
PNG
(US10023562, Example 93 | US9657009, 93)
Show SMILES COC(=O)Cn1cc(Cl)c(Nc2cc(NC(C)C)c(cn2)C(=O)NC[C@@H](F)C(C)(C)O)n1
Show InChI InChI=1S/C20H28ClFN6O4/c1-11(2)25-14-6-16(26-18-13(21)9-28(27-18)10-17(29)32-5)23-7-12(14)19(30)24-8-15(22)20(3,4)31/h6-7,9,11,15,31H,8,10H2,1-5H3,(H,24,30)(H2,23,25,26,27)/t15-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM310039
PNG
(US9657009, 41)
Show SMILES CC(C)Nc1cc(Nc2nc(OC3CCNCC3)ncc2Cl)ncc1C(=O)NC[C@@H](F)C(C)(C)O
Show InChI InChI=1S/C23H33ClFN7O3/c1-13(2)30-17-9-19(27-10-15(17)21(33)28-12-18(25)23(3,4)34)31-20-16(24)11-29-22(32-20)35-14-5-7-26-8-6-14/h9-11,13-14,18,26,34H,5-8,12H2,1-4H3,(H,28,33)(H2,27,29,30,31,32)/t18-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283830
PNG
(4-(Cyclopropylamino)-N-((2R)-2-fluoro-3-hydroxy-3-...)
Show SMILES CC(C)(O)[C@H](F)CNC(=O)c1cnc(Nc2csc(n2)-c2cccnc2)cc1NC1CC1
Show InChI InChI=1S/C22H25FN6O2S/c1-22(2,31)17(23)11-26-20(30)15-10-25-18(8-16(15)27-14-5-6-14)28-19-12-32-21(29-19)13-4-3-7-24-9-13/h3-4,7-10,12,14,17,31H,5-6,11H2,1-2H3,(H,26,30)(H2,25,27,28)/t17-/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM283814
PNG
(US10023562, Example 8 | US9657009, 8)
Show SMILES CC(C)Nc1cc(Nc2ccc(cn2)C#N)ncc1C(=O)NC1CCN(CC1)C(C)=O
Show InChI InChI=1S/C22H27N7O2/c1-14(2)26-19-10-21(28-20-5-4-16(11-23)12-24-20)25-13-18(19)22(31)27-17-6-8-29(9-7-17)15(3)30/h4-5,10,12-14,17H,6-9H2,1-3H3,(H,27,31)(H2,24,25,26,28)
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
Interleukin-1 receptor-associated kinase 4


(Homo sapiens (Human))
BDBM309996
PNG
(6-((5-Cyano-2-pyridinyl)amino)-4-(((1S,2S)-2,3-dih...)
Show SMILES CNC(=O)c1cnc(Nc2ccc(cn2)C#N)cc1N[C@H]([C@H](O)CO)c1ccccc1
Show InChI InChI=1S/C22H22N6O3/c1-24-22(31)16-12-26-20(28-19-8-7-14(10-23)11-25-19)9-17(16)27-21(18(30)13-29)15-5-3-2-4-6-15/h2-9,11-12,18,21,29-30H,13H2,1H3,(H,24,31)(H2,25,26,27,28)/t18-,21+/m1/s1
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Bristol-Myers Squibb Company

US Patent


Assay Description
The assays were performed in U-bottom 384-well plates. The final assay volume was 30 μL prepared from 15 μL additions of enzyme and substra...


US Patent US9657009 (2017)

More data for this
Ligand-Target Pair
* indicates data uncertainty>20%