JP2008510763A - ピリミジン誘導体 - Google Patents
ピリミジン誘導体 Download PDFInfo
- Publication number
- JP2008510763A JP2008510763A JP2007528754A JP2007528754A JP2008510763A JP 2008510763 A JP2008510763 A JP 2008510763A JP 2007528754 A JP2007528754 A JP 2007528754A JP 2007528754 A JP2007528754 A JP 2007528754A JP 2008510763 A JP2008510763 A JP 2008510763A
- 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
Links
- 150000003230 pyrimidines Chemical class 0.000 title abstract description 4
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title abstract description 3
- 238000000034 method Methods 0.000 claims abstract description 51
- 238000002360 preparation method Methods 0.000 claims abstract description 29
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
- 239000003814 drug Substances 0.000 claims abstract description 10
- 230000008569 process Effects 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 130
- 150000001875 compounds Chemical class 0.000 claims description 121
- -1 1,2,2,6,6-pentamethyl-piperidin-4-yloxy Chemical group 0.000 claims description 111
- 229910052739 hydrogen Inorganic materials 0.000 claims description 69
- 125000000623 heterocyclic group Chemical group 0.000 claims description 68
- 239000001257 hydrogen Substances 0.000 claims description 68
- 125000003545 alkoxy group Chemical group 0.000 claims description 51
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 49
- 150000003839 salts Chemical class 0.000 claims description 39
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 27
- 150000001408 amides Chemical class 0.000 claims description 25
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 24
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 24
- 201000010099 disease Diseases 0.000 claims description 20
- 125000006413 ring segment Chemical group 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 17
- 239000004480 active ingredient Substances 0.000 claims description 14
- 125000003282 alkyl amino group Chemical group 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 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 description 9
- 230000005764 inhibitory process Effects 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 8
- 230000001613 neoplastic effect Effects 0.000 claims description 8
- 230000002265 prevention Effects 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 230000002062 proliferating effect Effects 0.000 claims description 7
- 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 description 6
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 6
- 208000026310 Breast neoplasm Diseases 0.000 claims description 6
- WMMGZLDLOZGCCF-UHFFFAOYSA-N 3-[[5-chloro-4-[2-(2-methylpropylsulfamoyl)anilino]pyrimidin-2-yl]amino]-4-methoxybenzamide Chemical compound COC1=CC=C(C(N)=O)C=C1NC1=NC=C(Cl)C(NC=2C(=CC=CC=2)S(=O)(=O)NCC(C)C)=N1 WMMGZLDLOZGCCF-UHFFFAOYSA-N 0.000 claims description 5
- RBNIGSMSNORUAO-UHFFFAOYSA-N 5-chloro-2-n-(2-methoxy-4-morpholin-4-ylphenyl)-4-n-(2-piperazin-1-ylsulfonylphenyl)pyrimidine-2,4-diamine Chemical compound COC1=CC(N2CCOCC2)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1S(=O)(=O)N1CCNCC1 RBNIGSMSNORUAO-UHFFFAOYSA-N 0.000 claims description 5
- IFYVVWPOUKNORV-UHFFFAOYSA-N 5-chloro-2-n-(2-methoxy-4-morpholin-4-ylphenyl)-4-n-[2-(2h-tetrazol-5-yl)phenyl]pyrimidine-2,4-diamine Chemical compound COC1=CC(N2CCOCC2)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1C=1N=NNN=1 IFYVVWPOUKNORV-UHFFFAOYSA-N 0.000 claims description 5
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 5
- 229940088679 drug related substance Drugs 0.000 claims description 5
- 208000026278 immune system disease Diseases 0.000 claims description 5
- 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 description 4
- 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 description 4
- LBRVPGIXMBALBV-UHFFFAOYSA-N 2-[[5-chloro-2-[2-ethoxy-4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]amino]-n-propan-2-ylbenzenesulfonamide Chemical compound CCOC1=CC(N2CCN(C)CC2)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1S(=O)(=O)NC(C)C LBRVPGIXMBALBV-UHFFFAOYSA-N 0.000 claims description 4
- BWJNPIJUMOBXIX-UHFFFAOYSA-N 4-[[5-chloro-4-[2-(2-methylpropylsulfamoyl)anilino]pyrimidin-2-yl]amino]-3-methoxy-n-methylbenzamide Chemical compound COC1=CC(C(=O)NC)=CC=C1NC1=NC=C(Cl)C(NC=2C(=CC=CC=2)S(=O)(=O)NCC(C)C)=N1 BWJNPIJUMOBXIX-UHFFFAOYSA-N 0.000 claims description 4
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- JCGLVTFJKQWQLM-UHFFFAOYSA-N 5-chloro-2-n-[4-[4-(4-ethylpiperazin-1-yl)piperidin-1-yl]-2-methoxyphenyl]-4-n-(2-propan-2-ylsulfonylphenyl)pyrimidine-2,4-diamine Chemical compound C1CN(CC)CCN1C1CCN(C=2C=C(OC)C(NC=3N=C(NC=4C(=CC=CC=4)S(=O)(=O)C(C)C)C(Cl)=CN=3)=CC=2)CC1 JCGLVTFJKQWQLM-UHFFFAOYSA-N 0.000 claims description 4
- 241001024304 Mino Species 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
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- 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 description 3
- 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 description 3
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- 2005-08-26 CA CA002577251A patent/CA2577251A1/en not_active Abandoned
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| JP2011524411A (ja) * | 2008-06-17 | 2011-09-01 | アストラゼネカ アクチボラグ | ピリジン化合物 |
| JP2014500295A (ja) * | 2010-12-21 | 2014-01-09 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Igf1r受容体阻害薬としてのオキシインドールピリミジン |
| JP2014504646A (ja) * | 2011-02-02 | 2014-02-24 | アイアールエム・リミテッド・ライアビリティ・カンパニー | Alk阻害剤の使用方法 |
| JP2015528440A (ja) * | 2012-08-10 | 2015-09-28 | コーリア リサーチ インスティテュート オブ ケミカル テクノロジー | N2,n4−ビス(4−(ピペラジン−1−イル)フェニル)ピリミジン−2,4−ジアミン誘導体又は薬学的に許容されるその塩、及び有効成分としてこの誘導体又は塩を含有する癌を予防又は処置するための組成物 |
| JP2015535266A (ja) * | 2012-11-06 | 2015-12-10 | シャンハイ フォチョン ファーマシューティカル カンパニー リミテッド | Alkキナーゼ阻害剤 |
| JP2018119003A (ja) * | 2012-11-06 | 2018-08-02 | シャンハイ フォチョン ファーマシューティカル カンパニー リミテッド | Alkキナーゼ阻害剤 |
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| JP2017504653A (ja) * | 2014-01-31 | 2017-02-09 | ダナ−ファーバー キャンサー インスティテュート, インコーポレイテッド | ジアミノピリミジンベンゼンスルホン誘導体およびその使用 |
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| US10913752B2 (en) | 2015-11-25 | 2021-02-09 | Dana-Farber Cancer Institute, Inc. | Bivalent bromodomain inhibitors and uses thereof |
| JP2024502175A (ja) * | 2021-01-07 | 2024-01-17 | オンタリオ・インスティテュート・フォー・キャンサー・リサーチ(オーアイシーアール) | Nuakキナーゼの阻害剤としてのイソインドリノンアミノピリミジン化合物、その組成物及び使用 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2005276582B2 (en) | 2009-07-16 |
| WO2006021454A3 (en) | 2006-05-04 |
| KR20070054223A (ko) | 2007-05-28 |
| CN101048386A (zh) | 2007-10-03 |
| TNSN07075A1 (en) | 2008-06-02 |
| NO20071593L (no) | 2007-05-22 |
| WO2006021454A2 (en) | 2006-03-02 |
| RU2007110950A (ru) | 2008-10-10 |
| ZA200701406B (en) | 2008-08-27 |
| MA28824B1 (fr) | 2007-08-01 |
| TW200621729A (en) | 2006-07-01 |
| AU2005276582A1 (en) | 2006-03-02 |
| MX2007002254A (es) | 2007-04-20 |
| EP1784392A2 (en) | 2007-05-16 |
| US20090131436A1 (en) | 2009-05-21 |
| RU2401260C2 (ru) | 2010-10-10 |
| IL181433A0 (en) | 2007-07-04 |
| AR054081A1 (es) | 2007-06-06 |
| BRPI0514681A (pt) | 2008-06-17 |
| ECSP077271A (es) | 2007-03-29 |
| CA2577251A1 (en) | 2006-03-02 |
| GT200500237A (es) | 2006-03-29 |
| GB0419161D0 (en) | 2004-09-29 |
| PE20060622A1 (es) | 2006-08-14 |
| HRP20070076A2 (en) | 2007-07-31 |
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