JP2011518158A5 - - Google Patents
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- Publication number
- JP2011518158A5 JP2011518158A5 JP2011505034A JP2011505034A JP2011518158A5 JP 2011518158 A5 JP2011518158 A5 JP 2011518158A5 JP 2011505034 A JP2011505034 A JP 2011505034A JP 2011505034 A JP2011505034 A JP 2011505034A JP 2011518158 A5 JP2011518158 A5 JP 2011518158A5
- Authority
- JP
- Japan
- Prior art keywords
- carboxamide
- pyrimidine
- phenylamino
- cyclopropylamino
- ylamino
- 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.)
- Granted
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- 101150110875 Syk gene Proteins 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 11
- 210000004027 cell Anatomy 0.000 claims description 10
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 6
- 108091000080 Phosphotransferase Proteins 0.000 claims description 5
- 102000020233 phosphotransferase Human genes 0.000 claims description 5
- 102000042838 JAK family Human genes 0.000 claims description 3
- 108091082332 JAK family Proteins 0.000 claims description 3
- 210000003719 b-lymphocyte Anatomy 0.000 claims description 3
- -1 amino, hydroxy Chemical group 0.000 claims 152
- 125000006317 cyclopropyl amino group Chemical group 0.000 claims 87
- 125000006311 cyclobutyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 42
- 125000000217 alkyl group Chemical group 0.000 claims 22
- 125000003545 alkoxy group Chemical group 0.000 claims 20
- 150000003839 salts Chemical class 0.000 claims 20
- 125000000623 heterocyclic group Chemical group 0.000 claims 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 14
- 125000001424 substituent group Chemical group 0.000 claims 13
- 125000001475 halogen functional group Chemical group 0.000 claims 11
- 125000001072 heteroaryl group Chemical group 0.000 claims 11
- QDXGKRWDQCEABB-UHFFFAOYSA-N pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=CN=C1 QDXGKRWDQCEABB-UHFFFAOYSA-N 0.000 claims 11
- 125000002947 alkylene group Chemical group 0.000 claims 10
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 9
- 125000004043 oxo group Chemical group O=* 0.000 claims 9
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 claims 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 3
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 230000001404 mediated effect Effects 0.000 claims 3
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 208000028622 Immune thrombocytopenia Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000005605 benzo group Chemical group 0.000 claims 2
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000005169 cycloalkylcarbonylamino group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 230000002062 proliferating effect Effects 0.000 claims 2
- JKRJYAKPRGBXGS-UHFFFAOYSA-N 1-[4-[[5-carbamoyl-4-(cyclopropylamino)pyrimidin-2-yl]amino]phenyl]piperidine-4-carboxylic acid Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1N1CCC(C(O)=O)CC1 JKRJYAKPRGBXGS-UHFFFAOYSA-N 0.000 claims 1
- PSSHWNRPVJAAGC-UHFFFAOYSA-N 2-[4-(4-acetyl-2-carbamoylpiperazin-1-yl)anilino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound NC(=O)C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 PSSHWNRPVJAAGC-UHFFFAOYSA-N 0.000 claims 1
- WWFWIKFEJIUUSW-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(2,2,2-trifluoroethylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCC(F)(F)F)=N1 WWFWIKFEJIUUSW-UHFFFAOYSA-N 0.000 claims 1
- ACHNIWMUTPBTEZ-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(2-methoxyethylamino)pyrimidine-5-carboxamide Chemical compound C1=C(C(N)=O)C(NCCOC)=NC(NC=2C=CC(=CC=2)N2CCN(CC2)C(C)=O)=N1 ACHNIWMUTPBTEZ-UHFFFAOYSA-N 0.000 claims 1
- FJUKIPMCEFHCDC-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(3-methoxyanilino)pyrimidine-5-carboxamide Chemical compound COC1=CC=CC(NC=2C(=CN=C(NC=3C=CC(=CC=3)N3CCN(CC3)C(C)=O)N=2)C(N)=O)=C1 FJUKIPMCEFHCDC-UHFFFAOYSA-N 0.000 claims 1
- HWEJHLLMTLRJPQ-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(3-methoxypropylamino)pyrimidine-5-carboxamide Chemical compound C1=C(C(N)=O)C(NCCCOC)=NC(NC=2C=CC(=CC=2)N2CCN(CC2)C(C)=O)=N1 HWEJHLLMTLRJPQ-UHFFFAOYSA-N 0.000 claims 1
- NUUXTUXBJCQMFL-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(3-methylanilino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC=2C=C(C)C=CC=2)=N1 NUUXTUXBJCQMFL-UHFFFAOYSA-N 0.000 claims 1
- OOLHGIXQKHOIBU-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(benzylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCC=2C=CC=CC=2)=N1 OOLHGIXQKHOIBU-UHFFFAOYSA-N 0.000 claims 1
- GQFDCZJGRAIYDY-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(butylamino)pyrimidine-5-carboxamide Chemical compound C1=C(C(N)=O)C(NCCCC)=NC(NC=2C=CC(=CC=2)N2CCN(CC2)C(C)=O)=N1 GQFDCZJGRAIYDY-UHFFFAOYSA-N 0.000 claims 1
- ODOCPUAAXZORNM-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(cyanomethylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCC#N)=N1 ODOCPUAAXZORNM-UHFFFAOYSA-N 0.000 claims 1
- PWUNLPDAMZWBHF-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(cyclopentylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CCCC2)=N1 PWUNLPDAMZWBHF-UHFFFAOYSA-N 0.000 claims 1
- YMYMCGLMYUMRBN-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 YMYMCGLMYUMRBN-UHFFFAOYSA-N 0.000 claims 1
- SDBNKIOAJQBUQZ-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(cyclopropylmethylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCC2CC2)=N1 SDBNKIOAJQBUQZ-UHFFFAOYSA-N 0.000 claims 1
- CSMVRSJEKXAWIG-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(ethylamino)pyrimidine-5-carboxamide Chemical compound C1=C(C(N)=O)C(NCC)=NC(NC=2C=CC(=CC=2)N2CCN(CC2)C(C)=O)=N1 CSMVRSJEKXAWIG-UHFFFAOYSA-N 0.000 claims 1
- WSUQOCVWNARVBD-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(methylamino)pyrimidine-5-carboxamide Chemical compound C1=C(C(N)=O)C(NC)=NC(NC=2C=CC(=CC=2)N2CCN(CC2)C(C)=O)=N1 WSUQOCVWNARVBD-UHFFFAOYSA-N 0.000 claims 1
- NWSQMSSJOTZBLY-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(piperidin-3-ylmethylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCC2CNCCC2)=N1 NWSQMSSJOTZBLY-UHFFFAOYSA-N 0.000 claims 1
- NDQROJWWYNXXBY-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(piperidin-4-ylmethylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCC2CCNCC2)=N1 NDQROJWWYNXXBY-UHFFFAOYSA-N 0.000 claims 1
- LEHYLXBIKVDZLA-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(prop-2-ynylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCC#C)=N1 LEHYLXBIKVDZLA-UHFFFAOYSA-N 0.000 claims 1
- SVRYVBWAMMJFJT-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(propan-2-ylamino)pyrimidine-5-carboxamide Chemical compound C1=C(C(N)=O)C(NC(C)C)=NC(NC=2C=CC(=CC=2)N2CCN(CC2)C(C)=O)=N1 SVRYVBWAMMJFJT-UHFFFAOYSA-N 0.000 claims 1
- HHQGTMZTKZVVHN-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(tert-butylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC(C)(C)C)=N1 HHQGTMZTKZVVHN-UHFFFAOYSA-N 0.000 claims 1
- DIQRQHSVKYZYQJ-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-[(1-acetylpiperidin-4-yl)methylamino]pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCC1CNC1=NC(NC=2C=CC(=CC=2)N2CCN(CC2)C(C)=O)=NC=C1C(N)=O DIQRQHSVKYZYQJ-UHFFFAOYSA-N 0.000 claims 1
- NXFKIKCJNBVJNC-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-[(1-carbamoylpiperidin-4-yl)methylamino]pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCC2CCN(CC2)C(N)=O)=N1 NXFKIKCJNBVJNC-UHFFFAOYSA-N 0.000 claims 1
- FWTKFNAIEAOLFF-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-[(1-methylpiperidin-4-yl)methylamino]pyrimidine-5-carboxamide Chemical compound C1CN(C)CCC1CNC1=NC(NC=2C=CC(=CC=2)N2CCN(CC2)C(C)=O)=NC=C1C(N)=O FWTKFNAIEAOLFF-UHFFFAOYSA-N 0.000 claims 1
- VCHOHJKMTRVCPL-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-[(2-oxo-3,4-dihydro-1h-quinolin-6-yl)amino]pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC=2C=C3CCC(=O)NC3=CC=2)=N1 VCHOHJKMTRVCPL-UHFFFAOYSA-N 0.000 claims 1
- AIXZFNJDQBLOAN-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-[(4-amino-4-oxobutyl)amino]pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCCCC(N)=O)=N1 AIXZFNJDQBLOAN-UHFFFAOYSA-N 0.000 claims 1
- GYAKYIBOCULXFI-KRWDZBQOSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-[[(1s)-1-phenylethyl]amino]pyrimidine-5-carboxamide Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(C(=CN=1)C(N)=O)=NC=1NC(C=C1)=CC=C1N1CCN(C(C)=O)CC1 GYAKYIBOCULXFI-KRWDZBQOSA-N 0.000 claims 1
- RKBLDEARFOBJNW-UHFFFAOYSA-N 4-(cyclobutylamino)-2-(imidazo[1,2-a]pyridin-6-ylamino)pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=C(NC2=CN3C=CN=C3C=C2)N=C1NC1CCC1 RKBLDEARFOBJNW-UHFFFAOYSA-N 0.000 claims 1
- JKWQBSBQOZCQNS-UHFFFAOYSA-N 4-(cyclopropylamino)-2-(imidazo[1,2-a]pyridin-6-ylamino)pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=C(NC2=CN3C=CN=C3C=C2)N=C1NC1CC1 JKWQBSBQOZCQNS-UHFFFAOYSA-N 0.000 claims 1
- LPBGPDKSWUGPBT-UHFFFAOYSA-N 4-(cyclopropylamino)-2-(quinolin-6-ylamino)pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=C(NC=2C=C3C=CC=NC3=CC=2)N=C1NC1CC1 LPBGPDKSWUGPBT-UHFFFAOYSA-N 0.000 claims 1
- VCFNFSZYMKUDDS-UHFFFAOYSA-N 4-(cyclopropylamino)-2-(quinoxalin-6-ylamino)pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=C(NC=2C=C3N=CC=NC3=CC=2)N=C1NC1CC1 VCFNFSZYMKUDDS-UHFFFAOYSA-N 0.000 claims 1
- RGOZWVYEQRUTTA-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-(3,3-difluoropyrrolidin-1-yl)anilino]pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1N1CCC(F)(F)C1 RGOZWVYEQRUTTA-UHFFFAOYSA-N 0.000 claims 1
- BGLPECHZZQDNCD-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-(4-ethylsulfonylpiperazin-1-yl)anilino]pyrimidine-5-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 BGLPECHZZQDNCD-UHFFFAOYSA-N 0.000 claims 1
- FVLPJFPAEKKUPP-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-(4-methylsulfonyl-1,4-diazepan-1-yl)anilino]pyrimidine-5-carboxamide Chemical compound C1CN(S(=O)(=O)C)CCCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 FVLPJFPAEKKUPP-UHFFFAOYSA-N 0.000 claims 1
- TZUPESZOLNEHAJ-UHFFFAOYSA-N 4-[(1-methylindol-4-yl)amino]-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]pyrimidine-5-carboxamide Chemical compound C1=CC=C2N(C)C=CC2=C1NC(C(=CN=1)C(N)=O)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 TZUPESZOLNEHAJ-UHFFFAOYSA-N 0.000 claims 1
- 208000004476 Acute Coronary Syndrome Diseases 0.000 claims 1
- 206010002383 Angina Pectoris Diseases 0.000 claims 1
- 208000003343 Antiphospholipid Syndrome Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 206010056370 Congestive cardiomyopathy Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 201000010046 Dilated cardiomyopathy Diseases 0.000 claims 1
- 208000002250 Hematologic Neoplasms Diseases 0.000 claims 1
- 206010062506 Heparin-induced thrombocytopenia Diseases 0.000 claims 1
- 206010020751 Hypersensitivity Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 208000014767 Myeloproliferative disease Diseases 0.000 claims 1
- 201000007224 Myeloproliferative neoplasm Diseases 0.000 claims 1
- SIYVXIIUIKCKLS-UHFFFAOYSA-N N'-[4-(4-acetylpiperazin-1-yl)phenyl]pyrimidine-5-carbohydrazide Chemical compound N1=CN=CC(=C1)C(=O)NNC1=CC=C(C=C1)N1CCN(CC1)C(C)=O SIYVXIIUIKCKLS-UHFFFAOYSA-N 0.000 claims 1
- 208000021386 Sjogren Syndrome Diseases 0.000 claims 1
- 208000007536 Thrombosis Diseases 0.000 claims 1
- 208000035868 Vascular inflammations Diseases 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000004442 acylamino group Chemical group 0.000 claims 1
- 125000004694 alkoxyaminocarbonyl group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000006361 alkylene amino carbonyl group Chemical group 0.000 claims 1
- 125000006356 alkylene carbonyl group Chemical group 0.000 claims 1
- 230000007815 allergy Effects 0.000 claims 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 208000020832 chronic kidney disease Diseases 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims 1
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000028208 end stage renal disease Diseases 0.000 claims 1
- 201000000523 end stage renal failure Diseases 0.000 claims 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 201000005787 hematologic cancer Diseases 0.000 claims 1
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims 1
- 208000007475 hemolytic anemia Diseases 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 206010025135 lupus erythematosus Diseases 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 238000004806 packaging method and process Methods 0.000 claims 1
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims 1
- 208000003476 primary myelofibrosis Diseases 0.000 claims 1
- 208000037803 restenosis Diseases 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 208000007056 sickle cell anemia Diseases 0.000 claims 1
- 230000019491 signal transduction Effects 0.000 claims 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 description 10
- 239000003112 inhibitor Substances 0.000 description 5
- 102000003952 Caspase 3 Human genes 0.000 description 2
- 108090000397 Caspase 3 Proteins 0.000 description 2
- 108090000978 Interleukin-4 Proteins 0.000 description 2
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- 230000006907 apoptotic process Effects 0.000 description 2
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- 230000000638 stimulation Effects 0.000 description 2
- 102100035634 B-cell linker protein Human genes 0.000 description 1
- 238000012413 Fluorescence activated cell sorting analysis Methods 0.000 description 1
- 101000803266 Homo sapiens B-cell linker protein Proteins 0.000 description 1
- 101001055085 Homo sapiens Mitogen-activated protein kinase kinase kinase 9 Proteins 0.000 description 1
- 101000997832 Homo sapiens Tyrosine-protein kinase JAK2 Proteins 0.000 description 1
- 101000934996 Homo sapiens Tyrosine-protein kinase JAK3 Proteins 0.000 description 1
- 229940122245 Janus kinase inhibitor Drugs 0.000 description 1
- 102100026909 Mitogen-activated protein kinase kinase kinase 9 Human genes 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 102000001253 Protein Kinase Human genes 0.000 description 1
- 102100033444 Tyrosine-protein kinase JAK2 Human genes 0.000 description 1
- 102100025387 Tyrosine-protein kinase JAK3 Human genes 0.000 description 1
- 230000005754 cellular signaling Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000684 flow cytometry Methods 0.000 description 1
- 238000000021 kinase assay Methods 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
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| JP4529685B2 (ja) * | 2002-06-28 | 2010-08-25 | アステラス製薬株式会社 | ジアミノピリミジンカルボキサミド誘導体 |
| WO2008009458A1 (en) * | 2006-07-21 | 2008-01-24 | Novartis Ag | 2, 4 -di (arylaminio) -pyrimidine-5-carboxamide compounds as jak kinases inhibitors |
| AR076550A1 (es) * | 2009-05-06 | 2011-06-22 | Portola Pharm Inc | Inhibidores de la janus tirosina kinasa (jak) |
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2009
- 2009-04-16 EP EP09755219.4A patent/EP2321283B1/en active Active
- 2009-04-16 JP JP2011505034A patent/JP5705720B2/ja active Active
- 2009-04-16 WO PCT/US2009/002420 patent/WO2009145856A1/en not_active Ceased
- 2009-04-16 CA CA2960692A patent/CA2960692C/en active Active
- 2009-04-16 EA EA201001619A patent/EA024109B1/ru not_active IP Right Cessation
- 2009-04-16 HR HRP20161310TT patent/HRP20161310T1/hr unknown
- 2009-04-16 CN CN200980122631.8A patent/CN102066340B/zh active Active
- 2009-04-16 KR KR1020107025540A patent/KR101623997B1/ko active Active
- 2009-04-16 CA CA2723205A patent/CA2723205C/en active Active
- 2009-04-16 MY MYPI2010004846A patent/MY155639A/en unknown
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2010
- 2010-10-15 SV SV2010003706A patent/SV2010003706A/es unknown
- 2010-10-15 DO DO2010000310A patent/DOP2010000310A/es unknown
- 2010-10-15 HN HN2010002119A patent/HN2010002119A/es unknown
- 2010-11-01 MA MA33300A patent/MA32280B1/fr unknown
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2014
- 2014-10-31 JP JP2014223491A patent/JP2015078194A/ja active Pending
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