JP2011518219A5 - - Google Patents
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- Publication number
- JP2011518219A5 JP2011518219A5 JP2011506293A JP2011506293A JP2011518219A5 JP 2011518219 A5 JP2011518219 A5 JP 2011518219A5 JP 2011506293 A JP2011506293 A JP 2011506293A JP 2011506293 A JP2011506293 A JP 2011506293A JP 2011518219 A5 JP2011518219 A5 JP 2011518219A5
- Authority
- JP
- Japan
- Prior art keywords
- ylamino
- alkylene
- pyrrolo
- pyrimidin
- amino
- 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.)
- Withdrawn
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- 125000002947 alkylene group Chemical group 0.000 claims 108
- -1 amino, hydroxy Chemical group 0.000 claims 60
- 125000003545 alkoxy group Chemical group 0.000 claims 42
- 125000000217 alkyl group Chemical group 0.000 claims 42
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 40
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 37
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 30
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 27
- 229910052799 carbon Inorganic materials 0.000 claims 25
- 125000000623 heterocyclic group Chemical group 0.000 claims 25
- 125000003118 aryl group Chemical group 0.000 claims 20
- 125000001475 halogen functional group Chemical group 0.000 claims 20
- 229910052739 hydrogen Inorganic materials 0.000 claims 20
- 125000004043 oxo group Chemical group O=* 0.000 claims 18
- 125000001072 heteroaryl group Chemical group 0.000 claims 17
- 150000003839 salts Chemical class 0.000 claims 17
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims 16
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 15
- 125000001424 substituent group Chemical group 0.000 claims 15
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 11
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 8
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 8
- 125000004076 pyridyl group Chemical group 0.000 claims 8
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 6
- 125000006356 alkylene carbonyl group Chemical group 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 4
- 125000003282 alkyl amino group Chemical group 0.000 claims 4
- 125000005237 alkyleneamino group Chemical group 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- VPQNMDJVVNHZTD-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-[4-(aminomethyl)piperidin-1-yl]-7h-pyrrolo[2,3-d]pyrimidine-5-carbonitrile Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC(N2CCC(CN)CC2)=C(C(=CN2)C#N)C2=N1 VPQNMDJVVNHZTD-UHFFFAOYSA-N 0.000 claims 3
- 102000042838 JAK family Human genes 0.000 claims 3
- 125000005001 aminoaryl group Chemical group 0.000 claims 3
- 210000004027 cell Anatomy 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 208000007056 sickle cell anemia Diseases 0.000 claims 3
- MFMUWALWYSDAIX-INIZCTEOSA-N (3s)-1-[2-(4-piperazin-1-ylanilino)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]pyrrolidin-3-ol Chemical compound C1[C@@H](O)CCN1C1=NC(NC=2C=CC(=CC=2)N2CCNCC2)=NC2=C1C=CN2 MFMUWALWYSDAIX-INIZCTEOSA-N 0.000 claims 2
- ISPIWMLOLHWBJV-UHFFFAOYSA-N 1-[2-(4-piperazin-1-ylanilino)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]piperidine-3-carboxamide Chemical compound C1C(C(=O)N)CCCN1C1=NC(NC=2C=CC(=CC=2)N2CCNCC2)=NC2=C1C=CN2 ISPIWMLOLHWBJV-UHFFFAOYSA-N 0.000 claims 2
- DSBLPCYZGDBXSG-UHFFFAOYSA-N 1-[2-(4-piperazin-1-ylanilino)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]piperidine-4-carboxamide Chemical compound C1CC(C(=O)N)CCN1C1=NC(NC=2C=CC(=CC=2)N2CCNCC2)=NC2=C1C=CN2 DSBLPCYZGDBXSG-UHFFFAOYSA-N 0.000 claims 2
- ITBJIOFDMUDQPI-UHFFFAOYSA-N 1-[2-[4-(4-acetylpiperazin-1-yl)anilino]-5-fluoropyrimidin-4-yl]piperidine-3-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(F)C(N2CC(CCC2)C(N)=O)=N1 ITBJIOFDMUDQPI-UHFFFAOYSA-N 0.000 claims 2
- BKSBYMLCXXKXNA-UHFFFAOYSA-N 1-[2-[4-(4-acetylpiperazin-1-yl)anilino]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]piperidine-3-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC(N2CC(CCC2)C(N)=O)=C(C=CN2)C2=N1 BKSBYMLCXXKXNA-UHFFFAOYSA-N 0.000 claims 2
- QORZSWGMEPAGEF-UHFFFAOYSA-N 1-[2-[4-(4-acetylpiperazin-1-yl)anilino]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]piperidine-4-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC(N2CCC(CC2)C(N)=O)=C(C=CN2)C2=N1 QORZSWGMEPAGEF-UHFFFAOYSA-N 0.000 claims 2
- KLNYWORCDSBKLN-UHFFFAOYSA-N 1-[4-[4-[(4-piperidin-1-yl-7h-pyrrolo[2,3-d]pyrimidin-2-yl)amino]phenyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC(N2CCCCC2)=C(C=CN2)C2=N1 KLNYWORCDSBKLN-UHFFFAOYSA-N 0.000 claims 2
- XQNOAAQTRVPEJY-UHFFFAOYSA-N 1-[4-[4-[(4-pyrrolidin-1-yl-7h-pyrrolo[2,3-d]pyrimidin-2-yl)amino]phenyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC(N2CCCC2)=C(C=CN2)C2=N1 XQNOAAQTRVPEJY-UHFFFAOYSA-N 0.000 claims 2
- IMBSTVSBJXHUBW-SFHVURJKSA-N 1-[4-[4-[[4-[(3s)-3-hydroxypyrrolidin-1-yl]-7h-pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC(N2C[C@@H](O)CC2)=C(C=CN2)C2=N1 IMBSTVSBJXHUBW-SFHVURJKSA-N 0.000 claims 2
- UTOCZLMILKVPEA-UHFFFAOYSA-N 1-[4-[4-[[4-[2-(aminomethyl)piperidin-1-yl]-5-fluoropyrimidin-2-yl]amino]phenyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(F)C(N2C(CCCC2)CN)=N1 UTOCZLMILKVPEA-UHFFFAOYSA-N 0.000 claims 2
- AMHCKXVMDFGYGX-UHFFFAOYSA-N 1-[4-[4-[[4-[4-(aminomethyl)piperidin-1-yl]-5-fluoropyrimidin-2-yl]amino]phenyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(F)C(N2CCC(CN)CC2)=N1 AMHCKXVMDFGYGX-UHFFFAOYSA-N 0.000 claims 2
- NSCXCHDGMQTJCY-UHFFFAOYSA-N 1-[4-[4-[[4-[4-(aminomethyl)piperidin-1-yl]-7h-pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC(N2CCC(CN)CC2)=C(C=CN2)C2=N1 NSCXCHDGMQTJCY-UHFFFAOYSA-N 0.000 claims 2
- IFHNDWIKIZOFSN-UHFFFAOYSA-N 1-[4-[4-[[6-[4-(aminomethyl)piperidin-1-yl]-7h-purin-2-yl]amino]phenyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC(N2CCC(CN)CC2)=C(N=CN2)C2=N1 IFHNDWIKIZOFSN-UHFFFAOYSA-N 0.000 claims 2
- QNDRJTWJOGGLGW-UHFFFAOYSA-N 1-[5-fluoro-2-(1h-indazol-6-ylamino)pyrimidin-4-yl]piperidine-3-carboxamide Chemical compound C1C(C(=O)N)CCCN1C1=NC(NC=2C=C3NN=CC3=CC=2)=NC=C1F QNDRJTWJOGGLGW-UHFFFAOYSA-N 0.000 claims 2
- VMVVFAMYFKESAL-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-[4-(aminomethyl)piperidin-1-yl]pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(N2CCC(CN)CC2)=N1 VMVVFAMYFKESAL-UHFFFAOYSA-N 0.000 claims 2
- WSHBDAVXQWKPGV-UHFFFAOYSA-N 4-[4-(aminomethyl)piperidin-1-yl]-5-fluoro-n-(3,4,5-trimethoxyphenyl)pyrimidin-2-amine Chemical compound COC1=C(OC)C(OC)=CC(NC=2N=C(C(F)=CN=2)N2CCC(CN)CC2)=C1 WSHBDAVXQWKPGV-UHFFFAOYSA-N 0.000 claims 2
- AIOJJUROCPYRGY-UHFFFAOYSA-N 4-[4-(aminomethyl)piperidin-1-yl]-n-(4-piperazin-1-ylphenyl)-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1CC(CN)CCN1C1=NC(NC=2C=CC(=CC=2)N2CCNCC2)=NC2=C1C=CN2 AIOJJUROCPYRGY-UHFFFAOYSA-N 0.000 claims 2
- CJZAKNKOVZAWIW-UHFFFAOYSA-N 6-[[4-[4-(aminomethyl)piperidin-1-yl]-5-fluoropyrimidin-2-yl]amino]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1CC(CN)CCN1C1=NC(NC=2C=C3CCC(=O)NC3=CC=2)=NC=C1F CJZAKNKOVZAWIW-UHFFFAOYSA-N 0.000 claims 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 2
- 208000002903 Thalassemia Diseases 0.000 claims 2
- 125000006361 alkylene amino carbonyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 208000019622 heart disease Diseases 0.000 claims 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- XZZALAYXCNVFOZ-UHFFFAOYSA-N methyl n-[4-[[4-(cyclobutylamino)-7h-pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]-n-methylcarbamate Chemical compound C1=CC(N(C)C(=O)OC)=CC=C1NC1=NC(NC2CCC2)=C(C=CN2)C2=N1 XZZALAYXCNVFOZ-UHFFFAOYSA-N 0.000 claims 2
- RTPBRAGXGHSNGI-UHFFFAOYSA-N n-(4-piperazin-1-ylphenyl)-4-piperidin-1-yl-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1CCCCN1C1=NC(NC=2C=CC(=CC=2)N2CCNCC2)=NC2=C1C=CN2 RTPBRAGXGHSNGI-UHFFFAOYSA-N 0.000 claims 2
- LGSSRXTZRZRCGP-UHFFFAOYSA-N n-(4-piperazin-1-ylphenyl)-4-pyrrolidin-1-yl-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound C1CCCN1C1=NC(NC=2C=CC(=CC=2)N2CCNCC2)=NC2=C1C=CN2 LGSSRXTZRZRCGP-UHFFFAOYSA-N 0.000 claims 2
- HQXXUQWPFMATCL-UHFFFAOYSA-N n-[4-[2-(aminomethyl)piperidin-1-yl]-5-fluoropyrimidin-2-yl]-1h-indazol-6-amine Chemical compound NCC1CCCCN1C1=NC(NC=2C=C3NN=CC3=CC=2)=NC=C1F HQXXUQWPFMATCL-UHFFFAOYSA-N 0.000 claims 2
- LUQJBQPCCBQITJ-UHFFFAOYSA-N n-[4-[4-(aminomethyl)piperidin-1-yl]-5-fluoropyrimidin-2-yl]-1h-indazol-6-amine Chemical compound C1CC(CN)CCN1C1=NC(NC=2C=C3NN=CC3=CC=2)=NC=C1F LUQJBQPCCBQITJ-UHFFFAOYSA-N 0.000 claims 2
- SMQOSQSCUMJLTB-UHFFFAOYSA-N n-[4-[[4-[4-(aminomethyl)piperidin-1-yl]-5-fluoropyrimidin-2-yl]amino]phenyl]-n-methylacetamide Chemical compound C1=CC(N(C(C)=O)C)=CC=C1NC1=NC=C(F)C(N2CCC(CN)CC2)=N1 SMQOSQSCUMJLTB-UHFFFAOYSA-N 0.000 claims 2
- IKMBLWLVMKDJOW-UHFFFAOYSA-N tert-butyl n-[[1-[2-(4-carbamoylanilino)-5-fluoropyrimidin-4-yl]piperidin-4-yl]methyl]carbamate Chemical compound C1CC(CNC(=O)OC(C)(C)C)CCN1C1=NC(NC=2C=CC(=CC=2)C(N)=O)=NC=C1F IKMBLWLVMKDJOW-UHFFFAOYSA-N 0.000 claims 2
- RJPFULDFMSGSPC-UHFFFAOYSA-N tert-butyl n-[[1-[2-[4-[acetyl(methyl)amino]anilino]-5-fluoropyrimidin-4-yl]piperidin-4-yl]methyl]carbamate Chemical compound C1=CC(N(C(C)=O)C)=CC=C1NC1=NC=C(F)C(N2CCC(CNC(=O)OC(C)(C)C)CC2)=N1 RJPFULDFMSGSPC-UHFFFAOYSA-N 0.000 claims 2
- TWGVBXWKYXJGIH-UHFFFAOYSA-N tert-butyl n-[[1-[5-fluoro-2-(1h-indazol-6-ylamino)pyrimidin-4-yl]piperidin-2-yl]methyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC1CCCCN1C1=NC(NC=2C=C3NN=CC3=CC=2)=NC=C1F TWGVBXWKYXJGIH-UHFFFAOYSA-N 0.000 claims 2
- DTZXUJSOKGXUCS-CYBMUJFWSA-N (2r)-2-[[2-(4-piperazin-1-ylanilino)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]propan-1-ol Chemical compound N=1C=2NC=CC=2C(N[C@@H](CO)C)=NC=1NC(C=C1)=CC=C1N1CCNCC1 DTZXUJSOKGXUCS-CYBMUJFWSA-N 0.000 claims 1
- DTZXUJSOKGXUCS-ZDUSSCGKSA-N (2s)-2-[[2-(4-piperazin-1-ylanilino)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]propan-1-ol Chemical compound N=1C=2NC=CC=2C(N[C@H](CO)C)=NC=1NC(C=C1)=CC=C1N1CCNCC1 DTZXUJSOKGXUCS-ZDUSSCGKSA-N 0.000 claims 1
- 125000006636 (C3-C8) cycloalkylcarbonyl group Chemical group 0.000 claims 1
- XZGJAHQTUQUDGB-UHFFFAOYSA-N 1-[2-(4-piperazin-1-ylanilino)-7h-purin-6-yl]piperidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CCCN1C1=NC(NC=2C=CC(=CC=2)N2CCNCC2)=NC2=C1N=CN2 XZGJAHQTUQUDGB-UHFFFAOYSA-N 0.000 claims 1
- QKXBGQYQXGMLCG-UHFFFAOYSA-N 1-[2-[4-(4-acetylpiperazin-1-yl)anilino]-7h-purin-6-yl]piperidine-3-carboxylic acid Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC(N2CC(CCC2)C(O)=O)=C(N=CN2)C2=N1 QKXBGQYQXGMLCG-UHFFFAOYSA-N 0.000 claims 1
- XNQDTXPMUWEHIU-UHFFFAOYSA-N 1-[4-(cyclopropylamino)-2-(1h-indazol-6-ylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]ethanone Chemical compound C=12C(C(=O)C)=CNC2=NC(NC=2C=C3NN=CC3=CC=2)=NC=1NC1CC1 XNQDTXPMUWEHIU-UHFFFAOYSA-N 0.000 claims 1
- YPPGEPDDWNRUCU-UHFFFAOYSA-N 1-[4-[4-[(5-fluoro-4-piperazin-1-ylpyrimidin-2-yl)amino]phenyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(F)C(N2CCNCC2)=N1 YPPGEPDDWNRUCU-UHFFFAOYSA-N 0.000 claims 1
- UTBMAXNCUMKDHF-UHFFFAOYSA-N 1-[4-[4-[[4-(2-methoxyethylamino)-7h-pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]piperazin-1-yl]ethanone Chemical compound N=1C=2NC=CC=2C(NCCOC)=NC=1NC(C=C1)=CC=C1N1CCN(C(C)=O)CC1 UTBMAXNCUMKDHF-UHFFFAOYSA-N 0.000 claims 1
- PRVQGVFQRVRVNF-UHFFFAOYSA-N 1-[4-[4-[[4-(4-aminopiperidin-1-yl)-5-fluoropyrimidin-2-yl]amino]phenyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(F)C(N2CCC(N)CC2)=N1 PRVQGVFQRVRVNF-UHFFFAOYSA-N 0.000 claims 1
- ZNOASPNIGDFOQH-UHFFFAOYSA-N 1-[4-[4-[[4-(cyclopropylamino)-5-pyridin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC(NC2CC2)=C(C(=CN2)C=3C=CN=CC=3)C2=N1 ZNOASPNIGDFOQH-UHFFFAOYSA-N 0.000 claims 1
- PSFSHWDADXKQTD-UHFFFAOYSA-N 1-[4-[4-[[4-(methylamino)-5-pyridin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]piperazin-1-yl]ethanone Chemical compound N=1C=2NC=C(C=3C=CN=CC=3)C=2C(NC)=NC=1NC(C=C1)=CC=C1N1CCN(C(C)=O)CC1 PSFSHWDADXKQTD-UHFFFAOYSA-N 0.000 claims 1
- XJTYNCJATWFGOR-UHFFFAOYSA-N 1-[4-[4-[[4-(piperidin-4-ylmethylamino)-5-pyridin-4-yl-7h-pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC(NCC2CCNCC2)=C(C(=CN2)C=3C=CN=CC=3)C2=N1 XJTYNCJATWFGOR-UHFFFAOYSA-N 0.000 claims 1
- MFSDUZLYAOQMHU-KRWDZBQOSA-N 1-[4-[4-[[4-[(3s)-3-aminopiperidin-1-yl]-7h-pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC(N2C[C@@H](N)CCC2)=C(C=CN2)C2=N1 MFSDUZLYAOQMHU-KRWDZBQOSA-N 0.000 claims 1
- PFQZSZKQBYZRGW-UHFFFAOYSA-N 1-[4-[4-[[4-[(4-aminocyclohexyl)amino]-7h-pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC(NC2CCC(N)CC2)=C(C=CN2)C2=N1 PFQZSZKQBYZRGW-UHFFFAOYSA-N 0.000 claims 1
- AXPRUMVDNQHMHM-UHFFFAOYSA-N 1-[4-[4-[[4-[4-(aminomethyl)piperidin-1-yl]-5-chloropyrimidin-2-yl]amino]phenyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(Cl)C(N2CCC(CN)CC2)=N1 AXPRUMVDNQHMHM-UHFFFAOYSA-N 0.000 claims 1
- WVGLLIMUMJTKGE-CQSZACIVSA-N 1-[4-[4-[[4-[[(2r)-1-hydroxypropan-2-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]piperazin-1-yl]ethanone Chemical compound N=1C=2NC=CC=2C(N[C@@H](CO)C)=NC=1NC(C=C1)=CC=C1N1CCN(C(C)=O)CC1 WVGLLIMUMJTKGE-CQSZACIVSA-N 0.000 claims 1
- WVGLLIMUMJTKGE-AWEZNQCLSA-N 1-[4-[4-[[4-[[(2s)-1-hydroxypropan-2-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]piperazin-1-yl]ethanone Chemical compound N=1C=2NC=CC=2C(N[C@H](CO)C)=NC=1NC(C=C1)=CC=C1N1CCN(C(C)=O)CC1 WVGLLIMUMJTKGE-AWEZNQCLSA-N 0.000 claims 1
- KCWJGNYVKTXHCU-UHFFFAOYSA-N 1-[4-[4-[[5-fluoro-4-[4-(hydroxymethyl)piperidin-1-yl]pyrimidin-2-yl]amino]phenyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(F)C(N2CCC(CO)CC2)=N1 KCWJGNYVKTXHCU-UHFFFAOYSA-N 0.000 claims 1
- JTHRAEIOHKMUAR-UHFFFAOYSA-N 1-[4-[[4-(cyclobutylamino)-7h-pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]piperidin-4-ol Chemical compound C1CC(O)CCN1C(C=C1)=CC=C1NC1=NC(NC2CCC2)=C(C=CN2)C2=N1 JTHRAEIOHKMUAR-UHFFFAOYSA-N 0.000 claims 1
- DHKNMIIKOXMEOH-UHFFFAOYSA-N 1-[4-[[4-(cyclobutylamino)-7h-pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]sulfonylpiperidin-4-ol Chemical compound C1CC(O)CCN1S(=O)(=O)C(C=C1)=CC=C1NC1=NC(NC2CCC2)=C(C=CN2)C2=N1 DHKNMIIKOXMEOH-UHFFFAOYSA-N 0.000 claims 1
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-
2009
- 2009-04-22 US US12/386,848 patent/US8258144B2/en active Active
- 2009-04-22 EP EP09734422.0A patent/EP2271631B1/en active Active
- 2009-04-22 CA CA2723185A patent/CA2723185A1/en not_active Abandoned
- 2009-04-22 CN CN2013100825419A patent/CN103224497A/zh active Pending
- 2009-04-22 WO PCT/US2009/002512 patent/WO2009131687A2/en not_active Ceased
- 2009-04-22 JP JP2011506293A patent/JP2011518219A/ja not_active Withdrawn
- 2009-04-22 BR BRPI0910668A patent/BRPI0910668A2/pt not_active IP Right Cessation
- 2009-04-22 NZ NZ588830A patent/NZ588830A/xx not_active IP Right Cessation
- 2009-04-22 AU AU2009238590A patent/AU2009238590A1/en not_active Abandoned
- 2009-04-22 CN CN2009801223945A patent/CN102066338A/zh active Pending
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2010
- 2010-10-14 IL IL208719A patent/IL208719A0/en unknown
-
2012
- 2012-06-20 US US13/528,709 patent/US9139581B2/en active Active
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