HRP20050560A2 - Pyrrolopyrimidine derivatives - Google Patents
Pyrrolopyrimidine derivatives Download PDFInfo
- Publication number
- HRP20050560A2 HRP20050560A2 HR20050560A HRP20050560A HRP20050560A2 HR P20050560 A2 HRP20050560 A2 HR P20050560A2 HR 20050560 A HR20050560 A HR 20050560A HR P20050560 A HRP20050560 A HR P20050560A HR P20050560 A2 HRP20050560 A2 HR P20050560A2
- Authority
- HR
- Croatia
- Prior art keywords
- pyrrolo
- amino
- pyrimidine
- carbonyl
- isopropyl
- Prior art date
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- 150000004944 pyrrolopyrimidines Chemical class 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 281
- 238000000034 method Methods 0.000 claims abstract description 138
- 150000003839 salts Chemical class 0.000 claims abstract description 59
- 229940002612 prodrug Drugs 0.000 claims abstract description 43
- 239000000651 prodrug Substances 0.000 claims abstract description 43
- 241000124008 Mammalia Species 0.000 claims abstract description 33
- 230000003463 hyperproliferative effect Effects 0.000 claims abstract description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 82
- 125000003118 aryl group Chemical group 0.000 claims description 57
- 125000000623 heterocyclic group Chemical group 0.000 claims description 54
- 229910052736 halogen Inorganic materials 0.000 claims description 45
- 150000002367 halogens Chemical class 0.000 claims description 45
- -1 [3-(4-amino-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]amide 2-phenylethenesulfonic acid Chemical compound 0.000 claims description 44
- 125000001072 heteroaryl group Chemical group 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 206010028980 Neoplasm Diseases 0.000 claims description 32
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 31
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 30
- 230000002159 abnormal effect Effects 0.000 claims description 29
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 29
- 239000003112 inhibitor Substances 0.000 claims description 29
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 26
- 201000011510 cancer Diseases 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 25
- 230000010261 cell growth Effects 0.000 claims description 24
- 239000012453 solvate Substances 0.000 claims description 24
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 14
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 13
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 13
- 125000006823 (C1-C6) acyl group Chemical group 0.000 claims description 11
- 102000004190 Enzymes Human genes 0.000 claims description 11
- 108090000790 Enzymes Proteins 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 11
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- VFCRSIORGUNNGT-UHFFFAOYSA-N 1-[5-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-methoxyphenyl]-3-(2,4-dichlorophenyl)urea Chemical compound COC1=CC=C(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)C=C1NC(=O)NC1=CC=C(Cl)C=C1Cl VFCRSIORGUNNGT-UHFFFAOYSA-N 0.000 claims description 9
- GYOBORHBLFKMOX-UHFFFAOYSA-N 1-[5-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-methoxyphenyl]-3-(3,5-difluorophenyl)urea Chemical compound COC1=CC=C(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)C=C1NC(=O)NC1=CC(F)=CC(F)=C1 GYOBORHBLFKMOX-UHFFFAOYSA-N 0.000 claims description 8
- 239000003102 growth factor Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- ADPWOQHEGMITGH-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(4-chloro-2-methylphenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=C(Cl)C=C1C ADPWOQHEGMITGH-UHFFFAOYSA-N 0.000 claims description 5
- BAABCALYOOIAEM-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(4-chlorophenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=C(Cl)C=C1 BAABCALYOOIAEM-UHFFFAOYSA-N 0.000 claims description 5
- KURTXTCSRFPGBN-UHFFFAOYSA-N 1-[5-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-fluorophenyl]-3-(2-chlorophenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=C(F)C=1NC(=O)NC1=CC=CC=C1Cl KURTXTCSRFPGBN-UHFFFAOYSA-N 0.000 claims description 5
- GQIANKOKVCCNQL-UHFFFAOYSA-N 1-[5-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-methoxyphenyl]-3-(3,5-dichlorophenyl)urea Chemical compound COC1=CC=C(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)C=C1NC(=O)NC1=CC(Cl)=CC(Cl)=C1 GQIANKOKVCCNQL-UHFFFAOYSA-N 0.000 claims description 5
- ZHCOXZXXZQWVEQ-UHFFFAOYSA-N 1-[5-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-methylphenyl]-3-(3,5-difluorophenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=C(C)C=1NC(=O)NC1=CC(F)=CC(F)=C1 ZHCOXZXXZQWVEQ-UHFFFAOYSA-N 0.000 claims description 5
- 239000004037 angiogenesis inhibitor Substances 0.000 claims description 5
- 230000000340 anti-metabolite Effects 0.000 claims description 5
- 239000002256 antimetabolite Substances 0.000 claims description 5
- 229940100197 antimetabolite Drugs 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- KDSFZKNPNHONQY-UHFFFAOYSA-N n-[5-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-chlorophenyl]-3,5-dichlorobenzenesulfonamide Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=C(Cl)C=1NS(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 KDSFZKNPNHONQY-UHFFFAOYSA-N 0.000 claims description 5
- JLBWFGVAZAYDLA-UHFFFAOYSA-N n-[5-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-chlorophenyl]-3,5-difluorobenzenesulfonamide Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=C(Cl)C=1NS(=O)(=O)C1=CC(F)=CC(F)=C1 JLBWFGVAZAYDLA-UHFFFAOYSA-N 0.000 claims description 5
- PZBJNYHJHSTBTR-UHFFFAOYSA-N n-[5-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-chlorophenyl]-3-chloro-4-fluorobenzenesulfonamide Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C(Cl)=C1 PZBJNYHJHSTBTR-UHFFFAOYSA-N 0.000 claims description 5
- OZLGCSCPIWUCCX-UHFFFAOYSA-N n-[5-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-fluorophenyl]-3-chloro-4-fluorobenzenesulfonamide Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=C(F)C=1NS(=O)(=O)C1=CC=C(F)C(Cl)=C1 OZLGCSCPIWUCCX-UHFFFAOYSA-N 0.000 claims description 5
- DVFNVIJMQKEZBR-UHFFFAOYSA-N 1-(3-acetylphenyl)-3-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=CC(C(C)=O)=C1 DVFNVIJMQKEZBR-UHFFFAOYSA-N 0.000 claims description 4
- OCLIERUCMRGVQI-UHFFFAOYSA-N 1-(4-acetylphenyl)-3-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=C(C(C)=O)C=C1 OCLIERUCMRGVQI-UHFFFAOYSA-N 0.000 claims description 4
- GGTZCRQJBIPUOR-UHFFFAOYSA-N 1-(4-acetylphenyl)-3-[5-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-methoxyphenyl]urea Chemical compound COC1=CC=C(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)C=C1NC(=O)NC1=CC=C(C(C)=O)C=C1 GGTZCRQJBIPUOR-UHFFFAOYSA-N 0.000 claims description 4
- CDHGVGXTWWQIHH-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-methylphenyl]-3-(2-chlorophenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1C)=CC=CC=1NC(=O)NC1=CC=CC=C1Cl CDHGVGXTWWQIHH-UHFFFAOYSA-N 0.000 claims description 4
- UKJZUGUHHIRELO-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-methylphenyl]-3-(3,5-difluorophenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1C)=CC=CC=1NC(=O)NC1=CC(F)=CC(F)=C1 UKJZUGUHHIRELO-UHFFFAOYSA-N 0.000 claims description 4
- RAFGILVSTGRONX-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(2,3-dimethylphenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=CC(C)=C1C RAFGILVSTGRONX-UHFFFAOYSA-N 0.000 claims description 4
- JKVSTGKNPUTWGN-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(2,4-difluorophenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=C(F)C=C1F JKVSTGKNPUTWGN-UHFFFAOYSA-N 0.000 claims description 4
- RFMCFLFBAXWLLB-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(2,4-dimethylphenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=C(C)C=C1C RFMCFLFBAXWLLB-UHFFFAOYSA-N 0.000 claims description 4
- XEAZAZGALAURME-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(2,5-difluorophenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC(F)=CC=C1F XEAZAZGALAURME-UHFFFAOYSA-N 0.000 claims description 4
- KBKFCUQHOUSYMQ-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(2,5-dimethylphenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC(C)=CC=C1C KBKFCUQHOUSYMQ-UHFFFAOYSA-N 0.000 claims description 4
- NBBUFLANDGOPCL-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(2-chloro-5-methylphenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC(C)=CC=C1Cl NBBUFLANDGOPCL-UHFFFAOYSA-N 0.000 claims description 4
- AMVHAASGKCIUQB-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(2-chlorophenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=CC=C1Cl AMVHAASGKCIUQB-UHFFFAOYSA-N 0.000 claims description 4
- KKSRDMXVGCCJHZ-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(2-ethoxyphenyl)urea Chemical compound CCOC1=CC=CC=C1NC(=O)NC1=CC=CC(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)=C1 KKSRDMXVGCCJHZ-UHFFFAOYSA-N 0.000 claims description 4
- VKCTUAXXHDUJDB-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(2-ethylphenyl)urea Chemical compound CCC1=CC=CC=C1NC(=O)NC1=CC=CC(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)=C1 VKCTUAXXHDUJDB-UHFFFAOYSA-N 0.000 claims description 4
- NBIMLOJSKMKITL-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(2-fluoro-5-methylphenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC(C)=CC=C1F NBIMLOJSKMKITL-UHFFFAOYSA-N 0.000 claims description 4
- JIJYZDRUGWAJLR-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(2-methoxy-5-methylphenyl)urea Chemical compound COC1=CC=C(C)C=C1NC(=O)NC1=CC=CC(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)=C1 JIJYZDRUGWAJLR-UHFFFAOYSA-N 0.000 claims description 4
- RQMZRLYFCRPRFD-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(2-methoxyphenyl)urea Chemical compound COC1=CC=CC=C1NC(=O)NC1=CC=CC(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)=C1 RQMZRLYFCRPRFD-UHFFFAOYSA-N 0.000 claims description 4
- JBUBDZWVWCZRIL-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(2-methylphenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=CC=C1C JBUBDZWVWCZRIL-UHFFFAOYSA-N 0.000 claims description 4
- RMJGHPYGPLGATQ-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(2-methylsulfanylphenyl)urea Chemical compound CSC1=CC=CC=C1NC(=O)NC1=CC=CC(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)=C1 RMJGHPYGPLGATQ-UHFFFAOYSA-N 0.000 claims description 4
- OKIYGPJGNGRUON-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(2-propan-2-ylphenyl)urea Chemical compound CC(C)C1=CC=CC=C1NC(=O)NC1=CC=CC(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)=C1 OKIYGPJGNGRUON-UHFFFAOYSA-N 0.000 claims description 4
- JYCUGYRJLXPLAT-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(3,4-difluorophenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=C(F)C(F)=C1 JYCUGYRJLXPLAT-UHFFFAOYSA-N 0.000 claims description 4
- QLYNTQDQIVHXTE-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(3,4-dimethylphenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=C(C)C(C)=C1 QLYNTQDQIVHXTE-UHFFFAOYSA-N 0.000 claims description 4
- WNEMZNISAXMTIC-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(3,5-difluorophenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC(F)=CC(F)=C1 WNEMZNISAXMTIC-UHFFFAOYSA-N 0.000 claims description 4
- VIHASRDIYKOXOV-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(3,5-dimethylphenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC(C)=CC(C)=C1 VIHASRDIYKOXOV-UHFFFAOYSA-N 0.000 claims description 4
- BZPLHCRPMWZHDC-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(3-chloro-2-methylphenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=CC(Cl)=C1C BZPLHCRPMWZHDC-UHFFFAOYSA-N 0.000 claims description 4
- KYBGGDWRMYOBSA-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(3-chloro-4-fluorophenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=C(F)C(Cl)=C1 KYBGGDWRMYOBSA-UHFFFAOYSA-N 0.000 claims description 4
- IWFLSIKPCXNDFT-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(3-chloro-4-methylphenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=C(C)C(Cl)=C1 IWFLSIKPCXNDFT-UHFFFAOYSA-N 0.000 claims description 4
- RPHMAQJLRVWQLQ-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(3-chlorophenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=CC(Cl)=C1 RPHMAQJLRVWQLQ-UHFFFAOYSA-N 0.000 claims description 4
- MRILIBUNFXYMJN-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(3-cyanophenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=CC(C#N)=C1 MRILIBUNFXYMJN-UHFFFAOYSA-N 0.000 claims description 4
- LZCUQYXWFGDIRP-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(3-ethylphenyl)urea Chemical compound CCC1=CC=CC(NC(=O)NC=2C=C(C=CC=2)C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)=C1 LZCUQYXWFGDIRP-UHFFFAOYSA-N 0.000 claims description 4
- NNZKAYJSMIOWLC-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(3-fluoro-4-methylphenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=C(C)C(F)=C1 NNZKAYJSMIOWLC-UHFFFAOYSA-N 0.000 claims description 4
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- JUVPBXIDIGBFKY-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(3-methylphenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1=CC=CC(C)=C1 JUVPBXIDIGBFKY-UHFFFAOYSA-N 0.000 claims description 4
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Classifications
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
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- Chemical & Material Sciences (AREA)
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- Heart & Thoracic Surgery (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
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PCT/IB2003/005841 WO2004056830A1 (en) | 2002-12-19 | 2003-12-08 | Pyrrolopyrimidine derivatives |
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EP (1) | EP1578751B1 (nl) |
JP (1) | JP4057013B2 (nl) |
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CN (1) | CN1726218A (nl) |
AP (1) | AP2005003342A0 (nl) |
AR (1) | AR042509A1 (nl) |
AT (1) | ATE512965T1 (nl) |
AU (1) | AU2003286317A1 (nl) |
BR (1) | BR0317524A (nl) |
CA (1) | CA2510853C (nl) |
EA (1) | EA200500814A1 (nl) |
EC (1) | ECSP055867A (nl) |
ES (1) | ES2364649T3 (nl) |
GT (1) | GT200300289A (nl) |
HN (1) | HN2003000416A (nl) |
HR (1) | HRP20050560A2 (nl) |
IS (1) | IS7872A (nl) |
MA (1) | MA27568A1 (nl) |
MX (1) | MXPA05006793A (nl) |
NL (1) | NL1025068C2 (nl) |
NO (1) | NO20052802L (nl) |
NZ (1) | NZ540456A (nl) |
OA (1) | OA12976A (nl) |
PA (1) | PA8591701A1 (nl) |
PE (1) | PE20040914A1 (nl) |
PL (1) | PL377774A1 (nl) |
RS (1) | RS20050469A (nl) |
TN (1) | TNSN05165A1 (nl) |
TW (1) | TW200423939A (nl) |
UA (1) | UA80171C2 (nl) |
UY (1) | UY28132A1 (nl) |
WO (1) | WO2004056830A1 (nl) |
ZA (1) | ZA200504440B (nl) |
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AU2004282219C1 (en) * | 2003-10-15 | 2009-12-17 | Osi Pharmaceuticals, Inc. | Imidazo [1, 5 - a] pyrazine tyrosine kinase inhibitors |
JP2007511596A (ja) | 2003-11-17 | 2007-05-10 | ファイザー・プロダクツ・インク | 癌の治療において有用なピロロピリミジン化合物 |
SG163576A1 (en) | 2004-04-02 | 2010-08-30 | Osi Pharm Inc | 6,6-bicyclic ring substituted heterobicyclic protein kinase inhibitors |
CA2566160C (en) * | 2004-05-27 | 2011-01-18 | Pfizer Products Inc. | Pyrrolopyrimidine derivatives useful in cancer treatment |
AR053090A1 (es) * | 2004-07-20 | 2007-04-25 | Osi Pharm Inc | Imidazotriazinas como inhibidores de proteina quinasas y su uso para la preparacion de medicamentos |
WO2006076592A1 (en) | 2005-01-14 | 2006-07-20 | Cgi Pharmaceuticals, Inc. | 1,3 substituted diaryl ureas as modulators of kinase activity |
US20070287719A1 (en) * | 2005-03-11 | 2007-12-13 | Pfizer Inc | Salts, Prodrugs and Formulations of 1-[5-(4-Amino-7-Isopropyl-7H-Pyrrolo[2,3-D]Pyrimidine-5-Carbonyl)-2-Methoxy-Phenyl]-3-(2,4-Dichloro-Phenyl)-Urea |
WO2007024294A2 (en) | 2005-05-03 | 2007-03-01 | Cgi Pharmaceuticals, Inc. | Certain substituted ureas, as modulators of kinase activity |
US7795248B2 (en) | 2005-05-18 | 2010-09-14 | Abbott Laboratories, Inc. | Substituted 7,8-dihydro-1H-pyrimido[4,5-B][1,4]diazepin-4-amines are novel kinase inhibitors |
DE102005037499A1 (de) * | 2005-08-09 | 2007-02-15 | Merck Patent Gmbh | Pyrazolderivate |
US20070049592A1 (en) * | 2005-08-22 | 2007-03-01 | Geuns-Meyer Stephanie D | Bis-aryl urea compounds and methods of use |
ES2332423T3 (es) * | 2005-10-28 | 2010-02-04 | Irm Llc | Compuestos y composiciones como inhibidores de proteina quinasas. |
SI1951724T1 (sl) * | 2005-11-17 | 2011-09-30 | Osi Pharmaceuticals Llc | Kondenzirani biciklični mTOR inhibitorji |
US20070135387A1 (en) * | 2005-12-08 | 2007-06-14 | Michaelides Michael R | Inhibitors of protein kinases |
WO2007066189A2 (en) * | 2005-12-09 | 2007-06-14 | Pfizer Products Inc. | Salts, prodrugs and formulations of 1-[5-(4-amino-7-isopropyl-7h-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-methoxy-phenyl]-3-(2,4-dichloro-phenyl)-urea |
US8575164B2 (en) * | 2005-12-19 | 2013-11-05 | OSI Pharmaceuticals, LLC | Combination cancer therapy |
JP2009520028A (ja) * | 2005-12-19 | 2009-05-21 | オーエスアイ・ファーマスーティカルズ・インコーポレーテッド | Igfr抑制剤および抗癌剤の併用 |
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