JP2008510763A5 - - Google Patents
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- JP2008510763A5 JP2008510763A5 JP2007528754A JP2007528754A JP2008510763A5 JP 2008510763 A5 JP2008510763 A5 JP 2008510763A5 JP 2007528754 A JP2007528754 A JP 2007528754A JP 2007528754 A JP2007528754 A JP 2007528754A JP 2008510763 A5 JP2008510763 A5 JP 2008510763A5
- Authority
- JP
- Japan
- Prior art keywords
- ylamino
- methoxy
- pyrimidin
- phenylamino
- methyl
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims description 56
- 125000000623 heterocyclic group Chemical group 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 35
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 14
- 125000006413 ring segment Chemical group 0.000 claims description 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
- 125000003282 alkyl amino group Chemical group 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
- 241001024304 Mino Species 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims 16
- 150000001408 amides Chemical class 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 5
- 238000000034 method Methods 0.000 claims 4
- 208000026278 immune system disease Diseases 0.000 claims 3
- 230000001613 neoplastic effect Effects 0.000 claims 3
- XZYWSQJGDNNNTA-UHFFFAOYSA-N 2-[[5-bromo-2-(2-methoxy-5-morpholin-4-ylanilino)pyrimidin-4-yl]amino]-n,n-dimethylbenzenesulfonamide Chemical compound COC1=CC=C(N2CCOCC2)C=C1NC(N=1)=NC=C(Br)C=1NC1=CC=CC=C1S(=O)(=O)N(C)C XZYWSQJGDNNNTA-UHFFFAOYSA-N 0.000 claims 2
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229940088679 drug related substance Drugs 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 230000002062 proliferating effect Effects 0.000 claims 2
- QNZSRUNDCIMEQW-HHHXNRCGSA-N (3r)-1-[4-[[5-chloro-4-[(2-methyl-3-oxo-1h-isoindol-4-yl)amino]pyrimidin-2-yl]amino]-3-methoxyphenyl]-3-methylpiperidine-3-carboxamide Chemical compound C=1C=C(NC=2N=C(NC=3C=4C(=O)N(C)CC=4C=CC=3)C(Cl)=CN=2)C(OC)=CC=1N1CCC[C@@](C)(C(N)=O)C1 QNZSRUNDCIMEQW-HHHXNRCGSA-N 0.000 claims 1
- NIDGJESNBXPTJZ-AREMUKBSSA-N (3r)-1-[4-[[5-chloro-4-[2-(methylcarbamoyl)anilino]pyrimidin-2-yl]amino]-3-methoxyphenyl]-3-methylpiperidine-3-carboxamide Chemical compound CNC(=O)C1=CC=CC=C1NC1=NC(NC=2C(=CC(=CC=2)N2C[C@@](C)(CCC2)C(N)=O)OC)=NC=C1Cl NIDGJESNBXPTJZ-AREMUKBSSA-N 0.000 claims 1
- QNZSRUNDCIMEQW-MHZLTWQESA-N (3s)-1-[4-[[5-chloro-4-[(2-methyl-3-oxo-1h-isoindol-4-yl)amino]pyrimidin-2-yl]amino]-3-methoxyphenyl]-3-methylpiperidine-3-carboxamide Chemical compound C=1C=C(NC=2N=C(NC=3C=4C(=O)N(C)CC=4C=CC=3)C(Cl)=CN=2)C(OC)=CC=1N1CCC[C@](C)(C(N)=O)C1 QNZSRUNDCIMEQW-MHZLTWQESA-N 0.000 claims 1
- NIDGJESNBXPTJZ-SANMLTNESA-N (3s)-1-[4-[[5-chloro-4-[2-(methylcarbamoyl)anilino]pyrimidin-2-yl]amino]-3-methoxyphenyl]-3-methylpiperidine-3-carboxamide Chemical compound CNC(=O)C1=CC=CC=C1NC1=NC(NC=2C(=CC(=CC=2)N2C[C@](C)(CCC2)C(N)=O)OC)=NC=C1Cl NIDGJESNBXPTJZ-SANMLTNESA-N 0.000 claims 1
- -1 1,2,2,6,6-pentamethyl-piperidin-4-yloxy Chemical group 0.000 claims 1
- QNZSRUNDCIMEQW-UHFFFAOYSA-N 1-[4-[[5-chloro-4-[(2-methyl-3-oxo-1h-isoindol-4-yl)amino]pyrimidin-2-yl]amino]-3-methoxyphenyl]-3-methylpiperidine-3-carboxamide Chemical compound C=1C=C(NC=2N=C(NC=3C=4C(=O)N(C)CC=4C=CC=3)C(Cl)=CN=2)C(OC)=CC=1N1CCCC(C)(C(N)=O)C1 QNZSRUNDCIMEQW-UHFFFAOYSA-N 0.000 claims 1
- ZMRTULLVSRWTIK-UHFFFAOYSA-N 1-[4-[[5-chloro-4-[(2-methyl-3-oxo-1h-isoindol-4-yl)amino]pyrimidin-2-yl]amino]-3-methoxyphenyl]piperidine-3-carboxamide Chemical compound C=1C=C(NC=2N=C(NC=3C=4C(=O)N(C)CC=4C=CC=3)C(Cl)=CN=2)C(OC)=CC=1N1CCCC(C(N)=O)C1 ZMRTULLVSRWTIK-UHFFFAOYSA-N 0.000 claims 1
- HRLQTDYPYJAQKB-UHFFFAOYSA-N 1-[4-[[5-chloro-4-[(2-methyl-3-oxo-1h-isoindol-4-yl)amino]pyrimidin-2-yl]amino]-3-methoxyphenyl]piperidine-4-carboxamide Chemical compound C=1C=C(NC=2N=C(NC=3C=4C(=O)N(C)CC=4C=CC=3)C(Cl)=CN=2)C(OC)=CC=1N1CCC(C(N)=O)CC1 HRLQTDYPYJAQKB-UHFFFAOYSA-N 0.000 claims 1
- SSMJKMUSHJBJIT-UHFFFAOYSA-N 1-[4-[[5-chloro-4-[2-(2-methylpropylsulfamoyl)anilino]pyrimidin-2-yl]amino]-3-methoxyphenyl]-3-methylpiperidine-3-carboxamide Chemical compound COC1=CC(N2CC(C)(CCC2)C(N)=O)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1S(=O)(=O)NCC(C)C SSMJKMUSHJBJIT-UHFFFAOYSA-N 0.000 claims 1
- PRYRRVRTLNGSJO-UHFFFAOYSA-N 1-[4-[[5-chloro-4-[2-(2-methylpropylsulfamoyl)anilino]pyrimidin-2-yl]amino]-3-methoxyphenyl]piperidine-4-carboxamide Chemical compound COC1=CC(N2CCC(CC2)C(N)=O)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1S(=O)(=O)NCC(C)C PRYRRVRTLNGSJO-UHFFFAOYSA-N 0.000 claims 1
- NIDGJESNBXPTJZ-UHFFFAOYSA-N 1-[4-[[5-chloro-4-[2-(methylcarbamoyl)anilino]pyrimidin-2-yl]amino]-3-methoxyphenyl]-3-methylpiperidine-3-carboxamide Chemical compound CNC(=O)C1=CC=CC=C1NC1=NC(NC=2C(=CC(=CC=2)N2CC(C)(CCC2)C(N)=O)OC)=NC=C1Cl NIDGJESNBXPTJZ-UHFFFAOYSA-N 0.000 claims 1
- BSAXWMSAVVOOHO-UHFFFAOYSA-N 2,2-dioxo-1,5-dihydroimidazo[4,5-c][1,2,6]thiadiazin-4-one Chemical compound O=C1NS(=O)(=O)NC2=C1NC=N2 BSAXWMSAVVOOHO-UHFFFAOYSA-N 0.000 claims 1
- VGNZWQKJQOQQDO-UHFFFAOYSA-N 2-(2-methoxy-4-morpholin-4-ylphenyl)-1H-pyrimidine-2,4-diamine Chemical compound COC1=C(C=CC(=C1)N1CCOCC1)C1(NC=CC(=N1)N)N VGNZWQKJQOQQDO-UHFFFAOYSA-N 0.000 claims 1
- YGIKNSYRWWYNEM-UHFFFAOYSA-N 2-[2-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl]-1H-pyrimidine-2,4-diamine Chemical compound COC1=CC(N2CCC(CC2)N2CCN(C)CC2)=CC=C1C1(N)NC=CC(N)=N1 YGIKNSYRWWYNEM-UHFFFAOYSA-N 0.000 claims 1
- ZCHNJFUSZJSLQX-UHFFFAOYSA-N 2-[[5-bromo-2-(2,4-dimethoxy-5-morpholin-4-ylanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC=C1NC1=NC(NC=2C(=CC(OC)=C(N3CCOCC3)C=2)OC)=NC=C1Br ZCHNJFUSZJSLQX-UHFFFAOYSA-N 0.000 claims 1
- PCPYKCXGYNSQDW-UHFFFAOYSA-N 2-[[5-bromo-2-(2,4-dimethoxy-5-morpholin-4-ylanilino)pyrimidin-4-yl]amino]-n-propan-2-ylbenzenesulfonamide Chemical compound COC1=CC(OC)=C(N2CCOCC2)C=C1NC(N=1)=NC=C(Br)C=1NC1=CC=CC=C1S(=O)(=O)NC(C)C PCPYKCXGYNSQDW-UHFFFAOYSA-N 0.000 claims 1
- JPOWYEVZJLBENT-UHFFFAOYSA-N 2-[[5-bromo-2-(2,5-dimethoxy-4-morpholin-4-ylanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC=C1NC1=NC(NC=2C(=CC(=C(OC)C=2)N2CCOCC2)OC)=NC=C1Br JPOWYEVZJLBENT-UHFFFAOYSA-N 0.000 claims 1
- YBQXFJXKEHAULY-UHFFFAOYSA-N 2-[[5-bromo-2-(2-methoxy-5-morpholin-4-ylanilino)pyrimidin-4-yl]amino]-n-propan-2-ylbenzenesulfonamide Chemical compound COC1=CC=C(N2CCOCC2)C=C1NC(N=1)=NC=C(Br)C=1NC1=CC=CC=C1S(=O)(=O)NC(C)C YBQXFJXKEHAULY-UHFFFAOYSA-N 0.000 claims 1
- DLTCCPJCILRITC-UHFFFAOYSA-N 2-[[5-bromo-2-(2-methoxy-5-piperidin-1-ylanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC=C1NC1=NC(NC=2C(=CC=C(C=2)N2CCCCC2)OC)=NC=C1Br DLTCCPJCILRITC-UHFFFAOYSA-N 0.000 claims 1
- LCPYQOSIVUZMTL-UHFFFAOYSA-N 2-[[5-bromo-2-(2-methoxy-5-piperidin-1-ylanilino)pyrimidin-4-yl]amino]-n-propan-2-ylbenzenesulfonamide Chemical compound COC1=CC=C(N2CCCCC2)C=C1NC(N=1)=NC=C(Br)C=1NC1=CC=CC=C1S(=O)(=O)NC(C)C LCPYQOSIVUZMTL-UHFFFAOYSA-N 0.000 claims 1
- XSXSLHFJXLBSAI-UHFFFAOYSA-N 2-[[5-bromo-2-(4-fluoro-2-methoxy-5-morpholin-4-ylanilino)pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC=C1NC1=NC(NC=2C(=CC(F)=C(N3CCOCC3)C=2)OC)=NC=C1Br XSXSLHFJXLBSAI-UHFFFAOYSA-N 0.000 claims 1
- SGFZYDWNVCEVJU-UHFFFAOYSA-N 2-[[5-bromo-2-[(7-methoxy-4-methyl-3-oxo-1,4-benzoxazin-6-yl)amino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC=C1NC1=NC(NC=2C(=CC=3OCC(=O)N(C)C=3C=2)OC)=NC=C1Br SGFZYDWNVCEVJU-UHFFFAOYSA-N 0.000 claims 1
- UWGHABCNOXARNC-UHFFFAOYSA-N 2-[[5-bromo-2-[2,4-dimethoxy-5-(2-morpholin-4-ylethoxy)anilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC=C1NC1=NC(NC=2C(=CC(OC)=C(OCCN3CCOCC3)C=2)OC)=NC=C1Br UWGHABCNOXARNC-UHFFFAOYSA-N 0.000 claims 1
- MEDZUBFZDSXJAC-UHFFFAOYSA-N 2-[[5-bromo-2-[2-methoxy-5-(1-methylpiperidin-4-yl)oxyanilino]pyrimidin-4-yl]amino]-n-propan-2-ylbenzenesulfonamide Chemical compound C1=C(NC=2N=C(NC=3C(=CC=CC=3)S(=O)(=O)NC(C)C)C(Br)=CN=2)C(OC)=CC=C1OC1CCN(C)CC1 MEDZUBFZDSXJAC-UHFFFAOYSA-N 0.000 claims 1
- ITKGHUPAYWHBIP-UHFFFAOYSA-N 2-[[5-bromo-2-[2-methoxy-5-(1-propan-2-ylpiperidin-4-yl)oxyanilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC=C1NC1=NC(NC=2C(=CC=C(OC3CCN(CC3)C(C)C)C=2)OC)=NC=C1Br ITKGHUPAYWHBIP-UHFFFAOYSA-N 0.000 claims 1
- XLZBPRVOHGJWAJ-UHFFFAOYSA-N 2-[[5-bromo-2-[2-methoxy-5-(1-propan-2-ylpiperidin-4-yl)oxyanilino]pyrimidin-4-yl]amino]-n-propan-2-ylbenzenesulfonamide Chemical compound C1=C(NC=2N=C(NC=3C(=CC=CC=3)S(=O)(=O)NC(C)C)C(Br)=CN=2)C(OC)=CC=C1OC1CCN(C(C)C)CC1 XLZBPRVOHGJWAJ-UHFFFAOYSA-N 0.000 claims 1
- YOTZCSJSLZPECF-UHFFFAOYSA-N 2-[[5-bromo-2-[2-methoxy-5-(2-morpholin-4-ylethoxy)anilino]pyrimidin-4-yl]amino]-n,n-dimethylbenzenesulfonamide Chemical compound C1=C(NC=2N=C(NC=3C(=CC=CC=3)S(=O)(=O)N(C)C)C(Br)=CN=2)C(OC)=CC=C1OCCN1CCOCC1 YOTZCSJSLZPECF-UHFFFAOYSA-N 0.000 claims 1
- BCYMTKQQVMDBNP-UHFFFAOYSA-N 2-[[5-bromo-2-[2-methoxy-5-(2-morpholin-4-ylethoxy)anilino]pyrimidin-4-yl]amino]-n-propan-2-ylbenzenesulfonamide Chemical compound C1=C(NC=2N=C(NC=3C(=CC=CC=3)S(=O)(=O)NC(C)C)C(Br)=CN=2)C(OC)=CC=C1OCCN1CCOCC1 BCYMTKQQVMDBNP-UHFFFAOYSA-N 0.000 claims 1
- JJEBJAFGKXTQHS-UHFFFAOYSA-N 2-[[5-bromo-2-[2-methoxy-5-(2-piperidin-1-ylethoxy)anilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC=C1NC1=NC(NC=2C(=CC=C(OCCN3CCCCC3)C=2)OC)=NC=C1Br JJEBJAFGKXTQHS-UHFFFAOYSA-N 0.000 claims 1
- NREPZYCCHRXIMV-UHFFFAOYSA-N 2-[[5-bromo-2-[2-methoxy-5-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]amino]-n-propan-2-ylbenzenesulfonamide Chemical compound COC1=CC=C(N2CCN(C)CC2)C=C1NC(N=1)=NC=C(Br)C=1NC1=CC=CC=C1S(=O)(=O)NC(C)C NREPZYCCHRXIMV-UHFFFAOYSA-N 0.000 claims 1
- WEOPBMCHEOLQJO-UHFFFAOYSA-N 2-[[5-bromo-2-[2-methoxy-5-(4-morpholin-4-ylpiperidin-1-yl)anilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC=C1NC1=NC(NC=2C(=CC=C(C=2)N2CCC(CC2)N2CCOCC2)OC)=NC=C1Br WEOPBMCHEOLQJO-UHFFFAOYSA-N 0.000 claims 1
- NMLYDTMONIHLGL-UHFFFAOYSA-N 2-[[5-bromo-2-[2-methoxy-5-(4-morpholin-4-ylpiperidin-1-yl)anilino]pyrimidin-4-yl]amino]-n-propan-2-ylbenzenesulfonamide Chemical compound COC1=CC=C(N2CCC(CC2)N2CCOCC2)C=C1NC(N=1)=NC=C(Br)C=1NC1=CC=CC=C1S(=O)(=O)NC(C)C NMLYDTMONIHLGL-UHFFFAOYSA-N 0.000 claims 1
- BQKXLUBHBKXGFL-UHFFFAOYSA-N 2-[[5-bromo-2-[2-methoxy-5-(4-piperidin-1-ylpiperidin-1-yl)anilino]pyrimidin-4-yl]amino]-n-propan-2-ylbenzenesulfonamide Chemical compound COC1=CC=C(N2CCC(CC2)N2CCCCC2)C=C1NC(N=1)=NC=C(Br)C=1NC1=CC=CC=C1S(=O)(=O)NC(C)C BQKXLUBHBKXGFL-UHFFFAOYSA-N 0.000 claims 1
- WBZMQZPBJXOQBL-UHFFFAOYSA-N 2-[[5-bromo-2-[2-methoxy-5-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]anilino]pyrimidin-4-yl]amino]-n,n-dimethylbenzenesulfonamide Chemical compound COC1=CC=C(N2CCC(CC2)N2CCN(C)CC2)C=C1NC(N=1)=NC=C(Br)C=1NC1=CC=CC=C1S(=O)(=O)N(C)C WBZMQZPBJXOQBL-UHFFFAOYSA-N 0.000 claims 1
- KNFGKRUZBFUTFB-UHFFFAOYSA-N 2-[[5-bromo-2-[2-methoxy-5-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]anilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC=C1NC1=NC(NC=2C(=CC=C(C=2)N2CCC(CC2)N2CCN(C)CC2)OC)=NC=C1Br KNFGKRUZBFUTFB-UHFFFAOYSA-N 0.000 claims 1
- JSDVQDPZXCMQDL-UHFFFAOYSA-N 2-[[5-bromo-2-[2-methoxy-5-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]anilino]pyrimidin-4-yl]amino]-n-propan-2-ylbenzenesulfonamide Chemical compound COC1=CC=C(N2CCC(CC2)N2CCN(C)CC2)C=C1NC(N=1)=NC=C(Br)C=1NC1=CC=CC=C1S(=O)(=O)NC(C)C JSDVQDPZXCMQDL-UHFFFAOYSA-N 0.000 claims 1
- AGZKTTMKEHBTCY-INIZCTEOSA-N 2-[[5-bromo-2-[2-methoxy-5-[[(2s)-1-methylpyrrolidin-2-yl]methoxy]anilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC=C1NC1=NC(NC=2C(=CC=C(OC[C@H]3N(CCC3)C)C=2)OC)=NC=C1Br AGZKTTMKEHBTCY-INIZCTEOSA-N 0.000 claims 1
- MTAXVMSPLTYQDA-UHFFFAOYSA-N 2-[[5-bromo-2-[5-(4-hydroxypiperidin-1-yl)-2-methoxyanilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC=C1NC1=NC(NC=2C(=CC=C(C=2)N2CCC(O)CC2)OC)=NC=C1Br MTAXVMSPLTYQDA-UHFFFAOYSA-N 0.000 claims 1
- MUZJZFBDMABTNL-UHFFFAOYSA-N 2-[[5-bromo-2-[5-(4-hydroxypiperidin-1-yl)-2-methoxyanilino]pyrimidin-4-yl]amino]-n-propan-2-ylbenzenesulfonamide Chemical compound COC1=CC=C(N2CCC(O)CC2)C=C1NC(N=1)=NC=C(Br)C=1NC1=CC=CC=C1S(=O)(=O)NC(C)C MUZJZFBDMABTNL-UHFFFAOYSA-N 0.000 claims 1
- OXWWVQIXMROYLT-UHFFFAOYSA-N 2-[[5-bromo-2-[5-[2-(4-hydroxypiperidin-1-yl)ethoxy]-2-methoxyanilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC=C1NC1=NC(NC=2C(=CC=C(OCCN3CCC(O)CC3)C=2)OC)=NC=C1Br OXWWVQIXMROYLT-UHFFFAOYSA-N 0.000 claims 1
- FOODYKIABZLSCE-UHFFFAOYSA-N 2-[[5-bromo-2-[5-[3-(dimethylamino)pyrrolidin-1-yl]-2-methoxyanilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC=C1NC1=NC(NC=2C(=CC=C(C=2)N2CC(CC2)N(C)C)OC)=NC=C1Br FOODYKIABZLSCE-UHFFFAOYSA-N 0.000 claims 1
- WWRSLSFQDJKUAL-UHFFFAOYSA-N 2-[[5-bromo-2-[5-[3-(dimethylamino)pyrrolidin-1-yl]-2-methoxyanilino]pyrimidin-4-yl]amino]-n-propan-2-ylbenzenesulfonamide Chemical compound COC1=CC=C(N2CC(CC2)N(C)C)C=C1NC(N=1)=NC=C(Br)C=1NC1=CC=CC=C1S(=O)(=O)NC(C)C WWRSLSFQDJKUAL-UHFFFAOYSA-N 0.000 claims 1
- VBOFRRPQWRDUBS-UHFFFAOYSA-N 2-[[5-chloro-2-(2-methoxy-4-morpholin-4-ylanilino)pyrimidin-4-yl]amino]-5-(4-hydroxypiperidin-1-yl)-n-methylbenzamide Chemical compound CNC(=O)C1=CC(N2CCC(O)CC2)=CC=C1NC(C(=CN=1)Cl)=NC=1NC(C(=C1)OC)=CC=C1N1CCOCC1 VBOFRRPQWRDUBS-UHFFFAOYSA-N 0.000 claims 1
- GUQUCLOOXRBTBR-NRFANRHFSA-N 2-[[5-chloro-2-(2-methoxy-4-morpholin-4-ylanilino)pyrimidin-4-yl]amino]-5-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-n-methylbenzamide Chemical compound CNC(=O)C1=CC(N2C[C@H](CC2)N(C)C)=CC=C1NC(C(=CN=1)Cl)=NC=1NC(C(=C1)OC)=CC=C1N1CCOCC1 GUQUCLOOXRBTBR-NRFANRHFSA-N 0.000 claims 1
- BJSYJIMZQJENEB-UHFFFAOYSA-N 2-[[5-chloro-2-(2-methoxy-4-morpholin-4-ylanilino)pyrimidin-4-yl]amino]-n-(2,2-dimethylpropyl)benzenesulfonamide Chemical compound COC1=CC(N2CCOCC2)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1S(=O)(=O)NCC(C)(C)C BJSYJIMZQJENEB-UHFFFAOYSA-N 0.000 claims 1
- LHOIBMDNIPXEGW-UHFFFAOYSA-N 2-[[5-chloro-2-(2-methoxy-4-morpholin-4-ylanilino)pyrimidin-4-yl]amino]-n-(2-ethoxyethyl)benzenesulfonamide Chemical compound CCOCCNS(=O)(=O)C1=CC=CC=C1NC1=NC(NC=2C(=CC(=CC=2)N2CCOCC2)OC)=NC=C1Cl LHOIBMDNIPXEGW-UHFFFAOYSA-N 0.000 claims 1
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| GB0004890D0 (en) * | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
| WO2003030909A1 (en) * | 2001-09-25 | 2003-04-17 | Bayer Pharmaceuticals Corporation | 2- and 4-aminopyrimidines n-substtituded by a bicyclic ring for use as kinase inhibitors in the treatment of cancer |
| GB0206215D0 (en) * | 2002-03-15 | 2002-05-01 | Novartis Ag | Organic compounds |
| AU2003231231A1 (en) * | 2002-05-06 | 2003-11-11 | Bayer Pharmaceuticals Corporation | Pyridinyl amino pyrimidine derivatives useful for treating hyper-proliferative disorders |
| GB0305929D0 (en) * | 2003-03-14 | 2003-04-23 | Novartis Ag | Organic compounds |
| PT2287156E (pt) * | 2003-08-15 | 2013-08-26 | Novartis Ag | 2,4-di(fenilamino)-pirimidinas úteis no tratamento de doenças neoplásicas, desordens inflamatórias e do sistema imunitário |
| CA2538413A1 (en) * | 2003-09-18 | 2005-03-24 | Novartis Ag | 2,4-di (phenylamino) pyrimidines useful in the treatment of proliferative disorders |
| GB0419160D0 (en) * | 2004-08-27 | 2004-09-29 | Novartis Ag | Organic compounds |
-
2004
- 2004-08-27 GB GBGB0419161.5A patent/GB0419161D0/en not_active Ceased
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- 2005-08-26 HR HR20070076A patent/HRP20070076A2/xx not_active Application Discontinuation
- 2005-08-26 RU RU2007110950/04A patent/RU2401260C2/ru not_active IP Right Cessation
- 2005-08-26 BR BRPI0514681-0A patent/BRPI0514681A/pt not_active IP Right Cessation
- 2005-08-26 CN CNA2005800368883A patent/CN101048386A/zh active Pending
- 2005-08-26 US US11/574,019 patent/US20090131436A1/en not_active Abandoned
- 2005-08-26 JP JP2007528754A patent/JP2008510763A/ja active Pending
- 2005-08-26 EP EP05776772A patent/EP1784392A2/en not_active Withdrawn
- 2005-08-26 WO PCT/EP2005/009251 patent/WO2006021454A2/en not_active Ceased
- 2005-08-26 KR KR1020077006800A patent/KR20070054223A/ko not_active Ceased
- 2005-08-26 AU AU2005276582A patent/AU2005276582B2/en not_active Ceased
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- 2005-08-26 CA CA002577251A patent/CA2577251A1/en not_active Abandoned
- 2005-08-26 TW TW094129176A patent/TW200621729A/zh unknown
- 2005-08-26 MX MX2007002254A patent/MX2007002254A/es active IP Right Grant
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