CA2877469A1 - Substituted picolinamide kinase inhibitors - Google Patents
Substituted picolinamide kinase inhibitors Download PDFInfo
- Publication number
- CA2877469A1 CA2877469A1 CA2877469A CA2877469A CA2877469A1 CA 2877469 A1 CA2877469 A1 CA 2877469A1 CA 2877469 A CA2877469 A CA 2877469A CA 2877469 A CA2877469 A CA 2877469A CA 2877469 A1 CA2877469 A1 CA 2877469A1
- Authority
- CA
- Canada
- Prior art keywords
- ylamino
- group
- picolinamide
- compound
- 8alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical class NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 title claims abstract description 51
- 229940043355 kinase inhibitor Drugs 0.000 title description 3
- 239000003757 phosphotransferase inhibitor Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 188
- 230000000694 effects Effects 0.000 claims abstract description 45
- 238000000034 method Methods 0.000 claims abstract description 40
- 230000001404 mediated effect Effects 0.000 claims abstract description 23
- 108010016672 Syk Kinase Proteins 0.000 claims abstract description 14
- 102000000551 Syk Kinase Human genes 0.000 claims abstract description 14
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims description 96
- -1 C2-8alkenyl Chemical group 0.000 claims description 70
- 150000003839 salts Chemical class 0.000 claims description 59
- 125000000217 alkyl group Chemical group 0.000 claims description 57
- 125000005842 heteroatom Chemical group 0.000 claims description 53
- 125000000623 heterocyclic group Chemical group 0.000 claims description 45
- 210000004027 cell Anatomy 0.000 claims description 37
- 229910052757 nitrogen Inorganic materials 0.000 claims description 37
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 35
- 125000003118 aryl group Chemical group 0.000 claims description 33
- 125000005843 halogen group Chemical group 0.000 claims description 32
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 210000003719 b-lymphocyte Anatomy 0.000 claims description 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 24
- 229910052717 sulfur Inorganic materials 0.000 claims description 24
- 208000035475 disorder Diseases 0.000 claims description 22
- 125000002950 monocyclic group Chemical group 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 14
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 13
- 201000010099 disease Diseases 0.000 claims description 13
- 125000004429 atom Chemical group 0.000 claims description 12
- 208000037803 restenosis Diseases 0.000 claims description 10
- 230000019491 signal transduction Effects 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 206010025323 Lymphomas Diseases 0.000 claims description 6
- 208000032839 leukemia Diseases 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 208000023275 Autoimmune disease Diseases 0.000 claims description 5
- 206010020751 Hypersensitivity Diseases 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
- 208000028622 Immune thrombocytopenia Diseases 0.000 claims description 4
- 208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 claims description 4
- 208000007536 Thrombosis Diseases 0.000 claims description 4
- 230000007815 allergy Effects 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 206010025135 lupus erythematosus Diseases 0.000 claims description 4
- 201000006417 multiple sclerosis Diseases 0.000 claims description 4
- 208000010125 myocardial infarction Diseases 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 206010062506 Heparin-induced thrombocytopenia Diseases 0.000 claims description 3
- 201000004681 Psoriasis Diseases 0.000 claims description 3
- 208000026935 allergic disease Diseases 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 230000002062 proliferating effect Effects 0.000 claims description 3
- OPQCLRKBSMLBSY-NWDGAFQWSA-N 5-[[(1r,2s)-2-aminocyclohexyl]amino]-3-[(3-methyl-1,2-oxazol-5-yl)amino]pyridine-2-carboxamide Chemical compound O1N=C(C)C=C1NC1=CC(N[C@H]2[C@H](CCCC2)N)=CN=C1C(N)=O OPQCLRKBSMLBSY-NWDGAFQWSA-N 0.000 claims description 2
- BVFVCLXRPIFKAG-SSDOTTSWSA-N 5-[[(2r)-1-amino-1-oxopropan-2-yl]amino]-3-[(3-methyl-1,2-thiazol-5-yl)amino]pyridine-2-carboxamide Chemical compound NC(=O)[C@@H](C)NC1=CN=C(C(N)=O)C(NC=2SN=C(C)C=2)=C1 BVFVCLXRPIFKAG-SSDOTTSWSA-N 0.000 claims description 2
- QQDHWFMYRXZHLS-QGZVFWFLSA-N 5-[[(2r)-1-amino-4,4-dimethyl-1-oxopentan-2-yl]amino]-3-[(8-fluoroquinolin-6-yl)amino]pyridine-2-carboxamide Chemical compound CC(C)(C)C[C@H](C(N)=O)NC1=CN=C(C(N)=O)C(NC=2C=C3C=CC=NC3=C(F)C=2)=C1 QQDHWFMYRXZHLS-QGZVFWFLSA-N 0.000 claims description 2
- 125000003627 8 membered carbocyclic group Chemical group 0.000 claims description 2
- 208000004476 Acute Coronary Syndrome Diseases 0.000 claims description 2
- 206010002388 Angina unstable Diseases 0.000 claims description 2
- 208000003343 Antiphospholipid Syndrome Diseases 0.000 claims description 2
- 201000001320 Atherosclerosis Diseases 0.000 claims description 2
- 206010056370 Congestive cardiomyopathy Diseases 0.000 claims description 2
- 201000010046 Dilated cardiomyopathy Diseases 0.000 claims description 2
- 208000002250 Hematologic Neoplasms Diseases 0.000 claims description 2
- 208000007814 Unstable Angina Diseases 0.000 claims description 2
- 208000035868 Vascular inflammations Diseases 0.000 claims description 2
- 208000007475 hemolytic anemia Diseases 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 201000004332 intermediate coronary syndrome Diseases 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 208000007056 sickle cell anemia Diseases 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 25
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
- UDRJNGSEWSPSKU-UHFFFAOYSA-N 5-[(1-carbamoylcyclopropyl)amino]-3-[(3-methyl-1,2-thiazol-5-yl)amino]pyridine-2-carboxamide Chemical compound S1N=C(C)C=C1NC1=CC(NC2(CC2)C(N)=O)=CN=C1C(N)=O UDRJNGSEWSPSKU-UHFFFAOYSA-N 0.000 claims 1
- LDLOQQWFMKONNU-OAHLLOKOSA-N 5-[[(1r)-2-amino-2-oxo-1-phenylethyl]amino]-3-[(3-methyl-1,2-thiazol-5-yl)amino]pyridine-2-carboxamide Chemical compound S1N=C(C)C=C1NC1=CC(N[C@@H](C(N)=O)C=2C=CC=CC=2)=CN=C1C(N)=O LDLOQQWFMKONNU-OAHLLOKOSA-N 0.000 claims 1
- OTLJSORUAVYKCM-QMTHXVAHSA-N 5-[[(1r,2r)-2-amino-3,3-difluorocyclohexyl]amino]-3-[(3-methyl-1,2-thiazol-5-yl)amino]pyridine-2-carboxamide Chemical compound S1N=C(C)C=C1NC1=CC(N[C@H]2[C@H](C(F)(F)CCC2)N)=CN=C1C(N)=O OTLJSORUAVYKCM-QMTHXVAHSA-N 0.000 claims 1
- KOPYNQXMZSJHKT-NWDGAFQWSA-N 5-[[(1r,2s)-2-aminocyclohexyl]amino]-3-(1,2-thiazol-4-ylamino)pyridine-2-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=CN=C(C(N)=O)C(NC2=CSN=C2)=C1 KOPYNQXMZSJHKT-NWDGAFQWSA-N 0.000 claims 1
- XJUWFPGPJSFMKA-ZWKOTPCHSA-N 5-[[(1r,2s)-2-aminocyclohexyl]amino]-3-(isoquinolin-6-ylamino)pyridine-2-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=CN=C(C(N)=O)C(NC=2C=C3C=CN=CC3=CC=2)=C1 XJUWFPGPJSFMKA-ZWKOTPCHSA-N 0.000 claims 1
- GIPVWUDYOWOMIC-ZWKOTPCHSA-N 5-[[(1r,2s)-2-aminocyclohexyl]amino]-3-(isoquinolin-7-ylamino)pyridine-2-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=CN=C(C(N)=O)C(NC=2C=C3C=NC=CC3=CC=2)=C1 GIPVWUDYOWOMIC-ZWKOTPCHSA-N 0.000 claims 1
- GQUJXGRSHCGNLZ-UONOGXRCSA-N 5-[[(1r,2s)-2-aminocyclohexyl]amino]-3-(pyrazolo[1,5-a]pyridin-3-ylamino)pyridine-2-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=CN=C(C(N)=O)C(NC2=C3C=CC=CN3N=C2)=C1 GQUJXGRSHCGNLZ-UONOGXRCSA-N 0.000 claims 1
- ZAHFUSJPHALHOW-FUHWJXTLSA-N 5-[[(1r,2s)-2-aminocyclohexyl]amino]-3-(quinolin-3-ylamino)pyridine-2-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=CN=C(C(N)=O)C(NC=2C=C3C=CC=CC3=NC=2)=C1 ZAHFUSJPHALHOW-FUHWJXTLSA-N 0.000 claims 1
- ZZSHVZDSWOELCI-DLBZAZTESA-N 5-[[(1r,2s)-2-aminocyclohexyl]amino]-3-(quinolin-7-ylamino)pyridine-2-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=CN=C(C(N)=O)C(NC=2C=C3N=CC=CC3=CC=2)=C1 ZZSHVZDSWOELCI-DLBZAZTESA-N 0.000 claims 1
- QHBQHOHSLDETLQ-QWHCGFSZSA-N 5-[[(1r,2s)-2-aminocyclohexyl]amino]-3-[(1-methylpyrazol-4-yl)amino]pyridine-2-carboxamide Chemical compound C1=NN(C)C=C1NC1=CC(N[C@H]2[C@H](CCCC2)N)=CN=C1C(N)=O QHBQHOHSLDETLQ-QWHCGFSZSA-N 0.000 claims 1
- JCUSMLCCHUUIMO-QWHCGFSZSA-N 5-[[(1r,2s)-2-aminocyclohexyl]amino]-3-[(3-cyclopropyl-1,2-oxazol-5-yl)amino]pyridine-2-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=CN=C(C(N)=O)C(NC=2ON=C(C=2)C2CC2)=C1 JCUSMLCCHUUIMO-QWHCGFSZSA-N 0.000 claims 1
- OIVQEUWKSNBNMH-QWHCGFSZSA-N 5-[[(1r,2s)-2-aminocyclohexyl]amino]-3-[(3-ethyl-1,2-oxazol-5-yl)amino]pyridine-2-carboxamide Chemical compound O1N=C(CC)C=C1NC1=CC(N[C@H]2[C@H](CCCC2)N)=CN=C1C(N)=O OIVQEUWKSNBNMH-QWHCGFSZSA-N 0.000 claims 1
- RCHXGVBYMSHAQS-NWDGAFQWSA-N 5-[[(1r,2s)-2-aminocyclohexyl]amino]-3-[(3-methyl-1,2-thiazol-5-yl)amino]pyridine-2-carboxamide Chemical compound S1N=C(C)C=C1NC1=CC(N[C@H]2[C@H](CCCC2)N)=CN=C1C(N)=O RCHXGVBYMSHAQS-NWDGAFQWSA-N 0.000 claims 1
- QVSKRQQTCFJIRK-QWHCGFSZSA-N 5-[[(1r,2s)-2-aminocyclohexyl]amino]-3-[(3-propan-2-yl-1,2-oxazol-5-yl)amino]pyridine-2-carboxamide Chemical compound O1N=C(C(C)C)C=C1NC1=CC(N[C@H]2[C@H](CCCC2)N)=CN=C1C(N)=O QVSKRQQTCFJIRK-QWHCGFSZSA-N 0.000 claims 1
- JUMYGQHPGADODR-LSDHHAIUSA-N 5-[[(1r,2s)-2-aminocyclohexyl]amino]-3-[(3-pyridin-3-yl-1,2-oxazol-5-yl)amino]pyridine-2-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=CN=C(C(N)=O)C(NC=2ON=C(C=2)C=2C=NC=CC=2)=C1 JUMYGQHPGADODR-LSDHHAIUSA-N 0.000 claims 1
- GJWUQNRYYWWYGB-LSDHHAIUSA-N 5-[[(1r,2s)-2-aminocyclohexyl]amino]-3-[(3-pyridin-4-yl-1,2-oxazol-5-yl)amino]pyridine-2-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=CN=C(C(N)=O)C(NC=2ON=C(C=2)C=2C=CN=CC=2)=C1 GJWUQNRYYWWYGB-LSDHHAIUSA-N 0.000 claims 1
- XDDASCKVGFFJJS-DLBZAZTESA-N 5-[[(1r,2s)-2-aminocyclohexyl]amino]-3-[3-(1,3-oxazol-2-yl)anilino]pyridine-2-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=CN=C(C(N)=O)C(NC=2C=C(C=CC=2)C=2OC=CN=2)=C1 XDDASCKVGFFJJS-DLBZAZTESA-N 0.000 claims 1
- TUIJGSWIBLLOMH-DLBZAZTESA-N 5-[[(1r,2s)-2-aminocyclohexyl]amino]-3-[3-(triazol-2-yl)anilino]pyridine-2-carboxamide Chemical compound N[C@H]1CCCC[C@H]1NC1=CN=C(C(N)=O)C(NC=2C=C(C=CC=2)N2N=CC=N2)=C1 TUIJGSWIBLLOMH-DLBZAZTESA-N 0.000 claims 1
- FTAIOQAIKBHARB-GFCCVEGCSA-N 5-[[(2r)-1-amino-1-oxobutan-2-yl]amino]-3-(1,5-naphthyridin-3-ylamino)pyridine-2-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=CN=C(C(N)=O)C(NC=2C=C3N=CC=CC3=NC=2)=C1 FTAIOQAIKBHARB-GFCCVEGCSA-N 0.000 claims 1
- VKZQPQCNFHZOQT-SECBINFHSA-N 5-[[(2r)-1-amino-1-oxobutan-2-yl]amino]-3-[(3-methyl-1,2-thiazol-5-yl)amino]pyridine-2-carboxamide Chemical compound CC[C@H](C(N)=O)NC1=CN=C(C(N)=O)C(NC=2SN=C(C)C=2)=C1 VKZQPQCNFHZOQT-SECBINFHSA-N 0.000 claims 1
- YEUSJTIETZTSKI-HNNXBMFYSA-N 5-[[(2r)-1-amino-3,3-dimethyl-1-oxobutan-2-yl]amino]-3-[(3-cyclopropyl-1,2-thiazol-5-yl)amino]pyridine-2-carboxamide Chemical compound CC(C)(C)[C@H](C(N)=O)NC1=CN=C(C(N)=O)C(NC=2SN=C(C=2)C2CC2)=C1 YEUSJTIETZTSKI-HNNXBMFYSA-N 0.000 claims 1
- RTDMAPFXKCDGPZ-OAHLLOKOSA-N 5-[[(2r)-1-amino-3-cyclohexyl-1-oxopropan-2-yl]amino]-3-[(3-methyl-1,2-thiazol-5-yl)amino]pyridine-2-carboxamide Chemical compound S1N=C(C)C=C1NC1=CC(N[C@H](CC2CCCCC2)C(N)=O)=CN=C1C(N)=O RTDMAPFXKCDGPZ-OAHLLOKOSA-N 0.000 claims 1
- GBOLLXIGUKLNJY-GFCCVEGCSA-N 5-[[(2r)-1-amino-3-cyclopropyl-1-oxopropan-2-yl]amino]-3-[(3-methyl-1,2-thiazol-5-yl)amino]pyridine-2-carboxamide Chemical compound S1N=C(C)C=C1NC1=CC(N[C@H](CC2CC2)C(N)=O)=CN=C1C(N)=O GBOLLXIGUKLNJY-GFCCVEGCSA-N 0.000 claims 1
- ZKJPJSLHASNORD-SNVBAGLBSA-N 5-[[(2r)-1-amino-3-methoxy-1-oxopropan-2-yl]amino]-3-[(3-methyl-1,2-thiazol-5-yl)amino]pyridine-2-carboxamide Chemical compound COC[C@H](C(N)=O)NC1=CN=C(C(N)=O)C(NC=2SN=C(C)C=2)=C1 ZKJPJSLHASNORD-SNVBAGLBSA-N 0.000 claims 1
- QXNHXZHZVBVJSL-CQSZACIVSA-N 5-[[(2r)-1-amino-3-methyl-1-oxobutan-2-yl]amino]-3-[(3-cyclopropyl-1,2-oxazol-5-yl)amino]pyridine-2-carboxamide Chemical compound CC(C)[C@H](C(N)=O)NC1=CN=C(C(N)=O)C(NC=2ON=C(C=2)C2CC2)=C1 QXNHXZHZVBVJSL-CQSZACIVSA-N 0.000 claims 1
- JTPNADIROXAVFS-CYBMUJFWSA-N 5-[[(2r)-1-amino-3-methyl-1-oxobutan-2-yl]amino]-3-[(3-ethyl-1,2-thiazol-5-yl)amino]pyridine-2-carboxamide Chemical compound S1N=C(CC)C=C1NC1=CC(N[C@H](C(C)C)C(N)=O)=CN=C1C(N)=O JTPNADIROXAVFS-CYBMUJFWSA-N 0.000 claims 1
- JIYFGMWHXSQZIW-GFCCVEGCSA-N 5-[[(2r)-1-amino-3-methyl-1-oxobutan-2-yl]amino]-3-[(3-methyl-1,2-thiazol-5-yl)amino]pyridine-2-carboxamide Chemical compound CC(C)[C@H](C(N)=O)NC1=CN=C(C(N)=O)C(NC=2SN=C(C)C=2)=C1 JIYFGMWHXSQZIW-GFCCVEGCSA-N 0.000 claims 1
- QXIPUPJFZVXSDT-OAHLLOKOSA-N 5-[[(2r)-1-amino-4,4,4-trifluoro-1-oxobutan-2-yl]amino]-3-(quinolin-7-ylamino)pyridine-2-carboxamide Chemical compound FC(F)(F)C[C@H](C(=O)N)NC1=CN=C(C(N)=O)C(NC=2C=C3N=CC=CC3=CC=2)=C1 QXIPUPJFZVXSDT-OAHLLOKOSA-N 0.000 claims 1
- LTELLRCFLXHAQN-SECBINFHSA-N 5-[[(2r)-1-amino-4,4,4-trifluoro-1-oxobutan-2-yl]amino]-3-[(3-methyl-1,2-thiazol-5-yl)amino]pyridine-2-carboxamide Chemical compound S1N=C(C)C=C1NC1=CC(N[C@H](CC(F)(F)F)C(N)=O)=CN=C1C(N)=O LTELLRCFLXHAQN-SECBINFHSA-N 0.000 claims 1
- MTPWIQADQDYKBS-GOSISDBHSA-N 5-[[(2r)-1-amino-4,4-dimethyl-1-oxopentan-2-yl]amino]-3-(quinolin-7-ylamino)pyridine-2-carboxamide Chemical compound CC(C)(C)C[C@H](C(N)=O)NC1=CN=C(C(N)=O)C(NC=2C=C3N=CC=CC3=CC=2)=C1 MTPWIQADQDYKBS-GOSISDBHSA-N 0.000 claims 1
- MOXZMMMJEZODAC-GOSISDBHSA-N 5-[[(2r)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-3-(isoquinolin-6-ylamino)pyridine-2-carboxamide Chemical compound CC(C)C[C@H](C(N)=O)NC1=CN=C(C(N)=O)C(NC=2C=C3C=CN=CC3=CC=2)=C1 MOXZMMMJEZODAC-GOSISDBHSA-N 0.000 claims 1
- CLRCHWOXIVAQIN-GOSISDBHSA-N 5-[[(2r)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-3-(isoquinolin-7-ylamino)pyridine-2-carboxamide Chemical compound CC(C)C[C@H](C(N)=O)NC1=CN=C(C(N)=O)C(NC=2C=C3C=NC=CC3=CC=2)=C1 CLRCHWOXIVAQIN-GOSISDBHSA-N 0.000 claims 1
- FMXDFJYXCNDVCP-GOSISDBHSA-N 5-[[(2r)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-3-(quinolin-3-ylamino)pyridine-2-carboxamide Chemical compound CC(C)C[C@H](C(N)=O)NC1=CN=C(C(N)=O)C(NC=2C=C3C=CC=CC3=NC=2)=C1 FMXDFJYXCNDVCP-GOSISDBHSA-N 0.000 claims 1
- WUVPDZVGNHLOFF-GOSISDBHSA-N 5-[[(2r)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-3-(quinolin-6-ylamino)pyridine-2-carboxamide Chemical compound CC(C)C[C@H](C(N)=O)NC1=CN=C(C(N)=O)C(NC=2C=C3C=CC=NC3=CC=2)=C1 WUVPDZVGNHLOFF-GOSISDBHSA-N 0.000 claims 1
- RNSAITKLIMHEKQ-GOSISDBHSA-N 5-[[(2r)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-3-(quinolin-7-ylamino)pyridine-2-carboxamide Chemical compound CC(C)C[C@H](C(N)=O)NC1=CN=C(C(N)=O)C(NC=2C=C3N=CC=CC3=CC=2)=C1 RNSAITKLIMHEKQ-GOSISDBHSA-N 0.000 claims 1
- SKJLGEHBLIREKZ-GFCCVEGCSA-N 5-[[(2r)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-3-[(3-methyl-1,2-thiazol-5-yl)amino]pyridine-2-carboxamide Chemical compound CC(C)C[C@H](C(N)=O)NC1=CN=C(C(N)=O)C(NC=2SN=C(C)C=2)=C1 SKJLGEHBLIREKZ-GFCCVEGCSA-N 0.000 claims 1
- UOTLABFUTQVVRM-QGZVFWFLSA-N 5-[[(2r)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-3-[(3-phenyl-1,2-oxazol-5-yl)amino]pyridine-2-carboxamide Chemical compound CC(C)C[C@H](C(N)=O)NC1=CN=C(C(N)=O)C(NC=2ON=C(C=2)C=2C=CC=CC=2)=C1 UOTLABFUTQVVRM-QGZVFWFLSA-N 0.000 claims 1
- BTPQIFDHQPULAD-MRXNPFEDSA-N 5-[[(2r)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-3-[(3-pyridin-4-yl-1,2-oxazol-5-yl)amino]pyridine-2-carboxamide Chemical compound CC(C)C[C@H](C(N)=O)NC1=CN=C(C(N)=O)C(NC=2ON=C(C=2)C=2C=CN=CC=2)=C1 BTPQIFDHQPULAD-MRXNPFEDSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261663510P | 2012-06-22 | 2012-06-22 | |
| US61/663,510 | 2012-06-22 | ||
| US13/841,867 US20140113931A1 (en) | 2012-06-22 | 2013-03-15 | Substituted picolinamide kinase inhibitors |
| US13/841,867 | 2013-03-15 | ||
| PCT/US2013/045987 WO2013192046A2 (en) | 2012-06-22 | 2013-06-14 | Substituted picolinamide kinase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2877469A1 true CA2877469A1 (en) | 2013-12-27 |
Family
ID=49769665
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2877469A Abandoned CA2877469A1 (en) | 2012-06-22 | 2013-06-14 | Substituted picolinamide kinase inhibitors |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20140113931A1 (OSRAM) |
| EP (1) | EP2863905A4 (OSRAM) |
| JP (1) | JP2015523996A (OSRAM) |
| CN (1) | CN104602681A (OSRAM) |
| AU (1) | AU2013277473A1 (OSRAM) |
| CA (1) | CA2877469A1 (OSRAM) |
| HK (1) | HK1209316A1 (OSRAM) |
| IL (1) | IL235935A0 (OSRAM) |
| SG (1) | SG11201408074VA (OSRAM) |
| WO (1) | WO2013192046A2 (OSRAM) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3077388A1 (en) | 2013-12-05 | 2016-10-12 | Pharmacyclics, LLC | Inhibitors of bruton's tyrosine kinase |
| MA42623A (fr) * | 2015-06-02 | 2018-06-20 | Pharmacyclics Llc | Inhibiteurs de la tyrosine kinase de bruton |
| CA3122354A1 (en) | 2018-12-17 | 2020-06-25 | Tolremo Therapeutics Ag | Heterocyclic derivatives, pharmaceutical compositions and their use in the treatment, amelioration or prevention of cancer |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU5107900A (en) * | 1999-06-09 | 2000-12-28 | Yamanouchi Pharmaceutical Co., Ltd. | Novel heterocyclic carboxamide derivatives |
| KR20100132550A (ko) * | 2008-04-16 | 2010-12-17 | 포톨라 파마슈티컬스, 인코포레이티드 | ｓｙｋ 또는 ＪＡＫ 키나제 억제제로서의 ２,６－디아미노-피리미딘－５－일－카르복스아미드 |
| ES2632220T3 (es) * | 2009-06-15 | 2017-09-11 | Rigel Pharmaceuticals, Inc. | Inhibidores de moléculas pequeñas de tirosina cinasa del bazo (SYK) |
| CA2816219C (en) * | 2010-11-01 | 2019-10-29 | Portola Pharmaceuticals, Inc. | Nicotinamides as syk modulators |
| EP2665711A1 (en) * | 2011-01-21 | 2013-11-27 | Abbvie Inc. | Picolinamide inhibitors of kinases |
| EP2763976B1 (en) * | 2011-10-05 | 2016-05-18 | Merck Sharp & Dohme Corp. | 2-pyridyl carboxamide-containing spleen tyrosine kinase (syk) inhibitors |
| WO2014153280A1 (en) * | 2013-03-22 | 2014-09-25 | Merck Sharp & Dohme Corp. | 2-pyridyl carboxamide-containing spleen tyrosine kinase (syk) inhibitors |
-
2013
- 2013-03-15 US US13/841,867 patent/US20140113931A1/en not_active Abandoned
- 2013-06-14 EP EP13807089.1A patent/EP2863905A4/en not_active Withdrawn
- 2013-06-14 SG SG11201408074VA patent/SG11201408074VA/en unknown
- 2013-06-14 CN CN201380042757.0A patent/CN104602681A/zh active Pending
- 2013-06-14 AU AU2013277473A patent/AU2013277473A1/en not_active Abandoned
- 2013-06-14 JP JP2015518468A patent/JP2015523996A/ja active Pending
- 2013-06-14 CA CA2877469A patent/CA2877469A1/en not_active Abandoned
- 2013-06-14 WO PCT/US2013/045987 patent/WO2013192046A2/en not_active Ceased
- 2013-06-14 HK HK15109941.4A patent/HK1209316A1/xx unknown
-
2014
- 2014-11-27 IL IL235935A patent/IL235935A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2015523996A (ja) | 2015-08-20 |
| IL235935A0 (en) | 2015-01-29 |
| HK1209316A1 (en) | 2016-04-01 |
| US20140113931A1 (en) | 2014-04-24 |
| EP2863905A2 (en) | 2015-04-29 |
| WO2013192046A2 (en) | 2013-12-27 |
| EP2863905A4 (en) | 2015-12-16 |
| CN104602681A (zh) | 2015-05-06 |
| WO2013192046A3 (en) | 2014-02-27 |
| SG11201408074VA (en) | 2015-01-29 |
| AU2013277473A1 (en) | 2015-02-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20180614 |