OA12976A - Pyrrolopyrimidine derivatives. - Google Patents

Info

Publication number

OA12976A

OA12976A OA1200500187A OA1200500187A OA12976A OA 12976 A OA12976 A OA 12976A OA 1200500187 A OA1200500187 A OA 1200500187A OA 1200500187 A OA1200500187 A OA 1200500187A OA 12976 A OA12976 A OA 12976A

Authority

OA

OAPI

Prior art keywords

phenyl

amino

pyrrolo

pyrimidine

carbonyl

Prior art date

2002-12-19

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• 150000004944 pyrrolopyrimidines Chemical class 0.000 title description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 305
• 238000000034 method Methods 0.000 claims abstract description 167
• 229940002612 prodrug Drugs 0.000 claims abstract description 41
• 239000000651 prodrug Substances 0.000 claims abstract description 41
• 241000124008 Mammalia Species 0.000 claims abstract description 24
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 21
• 230000003463 hyperproliferative effect Effects 0.000 claims abstract description 11
• 239000004202 carbamide Substances 0.000 claims description 108
• 125000000217 alkyl group Chemical group 0.000 claims description 93
• 125000005843 halogen group Chemical group 0.000 claims description 57
• 125000003118 aryl group Chemical group 0.000 claims description 55
• 125000000623 heterocyclic group Chemical group 0.000 claims description 46
• -1 anti- métabolites Substances 0.000 claims description 42
• 206010028980 Neoplasm Diseases 0.000 claims description 39
• 239000003112 inhibitor Substances 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
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 29
• 125000001072 heteroaryl group Chemical group 0.000 claims description 26
• 201000011510 cancer Diseases 0.000 claims description 25
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 23
• 230000002159 abnormal effect Effects 0.000 claims description 22
• 229910052739 hydrogen Inorganic materials 0.000 claims description 22
• 230000010261 cell growth Effects 0.000 claims description 19
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 17
• 125000003545 alkoxy group Chemical group 0.000 claims description 17
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 17
• 125000002252 acyl group Chemical group 0.000 claims description 15
• 125000001424 substituent group Chemical group 0.000 claims description 14
• 239000002253 acid Substances 0.000 claims description 13
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 13
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 13
• 102000004190 Enzymes Human genes 0.000 claims description 12
• 108090000790 Enzymes Proteins 0.000 claims description 12
• CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 11
• 230000012010 growth Effects 0.000 claims description 9
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
• 239000003102 growth factor Substances 0.000 claims description 8
• 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 7
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
• 229910052757 nitrogen Inorganic materials 0.000 claims description 7
• 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
• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 6
• 239000001301 oxygen Substances 0.000 claims description 6
• 239000004037 angiogenesis inhibitor Substances 0.000 claims description 5
• 125000004169 (C1-C6) alkyl group Chemical group 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
• 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
• LVKYWGHBTMCTGO-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(3-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=CC(F)=C1 LVKYWGHBTMCTGO-UHFFFAOYSA-N 0.000 claims description 4
• LMPLJSJKSQJGEE-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(3-methylsulfanylphenyl)urea Chemical compound CSC1=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 LMPLJSJKSQJGEE-UHFFFAOYSA-N 0.000 claims description 4
• QRWBSACLFSVZEF-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(4-ethoxyphenyl)urea Chemical compound C1=CC(OCC)=CC=C1NC(=O)NC1=CC=CC(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)=C1 QRWBSACLFSVZEF-UHFFFAOYSA-N 0.000 claims description 4
• FTTLMJBTSSQACU-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(4-propan-2-ylphenyl)urea Chemical compound C1=CC(C(C)C)=CC=C1NC(=O)NC1=CC=CC(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)=C1 FTTLMJBTSSQACU-UHFFFAOYSA-N 0.000 claims description 4
• UCQIBRXGBNSFKA-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(5-fluoro-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(F)=CC=C1C UCQIBRXGBNSFKA-UHFFFAOYSA-N 0.000 claims description 4
• CIFHHRMGJLNMEQ-UHFFFAOYSA-N 1-[5-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-methoxyphenyl]-3-(2-fluoro-5-methylphenyl)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)=CC=C1F CIFHHRMGJLNMEQ-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• 229940123587 Cell cycle inhibitor Drugs 0.000 claims description 4
• 239000002168 alkylating agent Substances 0.000 claims description 4
• 229940100198 alkylating agent Drugs 0.000 claims description 4
• 230000002280 anti-androgenic effect Effects 0.000 claims description 4
• 230000003388 anti-hormonal effect Effects 0.000 claims description 4
• 239000000051 antiandrogen Substances 0.000 claims description 4
• 229940030495 antiandrogen sex hormone and modulator of the genital system Drugs 0.000 claims description 4
• WHMQOZBSVULDGM-UHFFFAOYSA-N methyl 4-[[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]carbamoylamino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)NC1=CC=CC(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)=C1 WHMQOZBSVULDGM-UHFFFAOYSA-N 0.000 claims description 4
• BNOXPWUUMZUSJJ-UHFFFAOYSA-N n-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-chlorophenyl]-3-chloro-4-methylbenzenesulfonamide Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1Cl)=CC=CC=1NS(=O)(=O)C1=CC=C(C)C(Cl)=C1 BNOXPWUUMZUSJJ-UHFFFAOYSA-N 0.000 claims description 4
• OKWYOZTUNJGJTJ-UHFFFAOYSA-N n-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-methylphenyl]-3-chloro-4-fluorobenzenesulfonamide Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1C)=CC=CC=1NS(=O)(=O)C1=CC=C(F)C(Cl)=C1 OKWYOZTUNJGJTJ-UHFFFAOYSA-N 0.000 claims description 4
• PZQISBSZHDGVDJ-UHFFFAOYSA-N n-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-2,4-dichloro-5-methylbenzenesulfonamide Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NS(=O)(=O)C1=CC(C)=C(Cl)C=C1Cl PZQISBSZHDGVDJ-UHFFFAOYSA-N 0.000 claims description 4
• LENJRZSMTWEGHS-UHFFFAOYSA-N n-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-4-butoxybenzenesulfonamide Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)NC1=CC=CC(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)=C1 LENJRZSMTWEGHS-UHFFFAOYSA-N 0.000 claims description 4
• BALVVIKBOOKCQS-UHFFFAOYSA-N n-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-5-chloro-2-methoxybenzenesulfonamide Chemical compound COC1=CC=C(Cl)C=C1S(=O)(=O)NC1=CC=CC(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)=C1 BALVVIKBOOKCQS-UHFFFAOYSA-N 0.000 claims description 4
• JPEDMDMNODQZIV-UHFFFAOYSA-N n-[5-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-fluorophenyl]-2,4-dichlorobenzenesulfonamide 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(Cl)C=C1Cl JPEDMDMNODQZIV-UHFFFAOYSA-N 0.000 claims description 4
• YSCYVUYHNGFVMD-UHFFFAOYSA-N n-[5-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-methoxyphenyl]-2-chloro-4-fluorobenzenesulfonamide Chemical compound COC1=CC=C(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)C=C1NS(=O)(=O)C1=CC=C(F)C=C1Cl YSCYVUYHNGFVMD-UHFFFAOYSA-N 0.000 claims description 4
• 230000008569 process Effects 0.000 claims description 4
• ANHIVJBWMLUKHH-UHFFFAOYSA-N (3-aminophenyl)-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidin-5-yl)methanone Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C1=CC=CC(N)=C1 ANHIVJBWMLUKHH-UHFFFAOYSA-N 0.000 claims description 3
• PLODYPCIUFWXSN-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-4-chlorophenyl]-3-(4-chlorophenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C(=CC=1)Cl)=CC=1NC(=O)NC1=CC=C(Cl)C=C1 PLODYPCIUFWXSN-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• GTYWJSQMWRYEOY-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(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=C1 GTYWJSQMWRYEOY-UHFFFAOYSA-N 0.000 claims description 3
• WRDBKJMACQYBFZ-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(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=C1 WRDBKJMACQYBFZ-UHFFFAOYSA-N 0.000 claims description 3
• SJJZDMLQNNOAJO-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-(4-methylsulfanylphenyl)urea Chemical compound C1=CC(SC)=CC=C1NC(=O)NC1=CC=CC(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)=C1 SJJZDMLQNNOAJO-UHFFFAOYSA-N 0.000 claims description 3
• VEZCJYLOEWLZNM-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-cyclohexylurea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=CC=1NC(=O)NC1CCCCC1 VEZCJYLOEWLZNM-UHFFFAOYSA-N 0.000 claims description 3
• ZIIUTFLNEYPNIZ-UHFFFAOYSA-N 1-[3-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)phenyl]-3-propan-2-ylurea Chemical compound CC(C)NC(=O)NC1=CC=CC(C(=O)C=2C3=C(N)N=CN=C3N(C(C)C)C=2)=C1 ZIIUTFLNEYPNIZ-UHFFFAOYSA-N 0.000 claims description 3
• SUQWIWWBMQLMER-UHFFFAOYSA-N 1-[5-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-chlorophenyl]-3-(3,5-dichlorophenyl)urea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=C(Cl)C=1NC(=O)NC1=CC(Cl)=CC(Cl)=C1 SUQWIWWBMQLMER-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• WOBPWTKMWKMHSJ-UHFFFAOYSA-N 1-[5-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-methoxyphenyl]-3-(2-chlorophenyl)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=CC=C1Cl WOBPWTKMWKMHSJ-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• OPSIYOLKNZFXRY-UHFFFAOYSA-N 1-[5-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-methoxyphenyl]-3-(3-cyanophenyl)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=CC(C#N)=C1 OPSIYOLKNZFXRY-UHFFFAOYSA-N 0.000 claims description 3
• VUZYXRDZUGCHNQ-UHFFFAOYSA-N 1-[5-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-methoxyphenyl]-3-(3-fluoro-4-methylphenyl)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(F)=C1 VUZYXRDZUGCHNQ-UHFFFAOYSA-N 0.000 claims description 3
• MGFHAMRNPOLMJC-UHFFFAOYSA-N 1-[5-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-methylphenyl]-3-(3,5-dichlorophenyl)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(Cl)=CC(Cl)=C1 MGFHAMRNPOLMJC-UHFFFAOYSA-N 0.000 claims description 3
• KRLRJBRHGFXYSL-UHFFFAOYSA-N 1-[5-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-methylphenyl]-3-(3-chlorophenyl)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=CC(Cl)=C1 KRLRJBRHGFXYSL-UHFFFAOYSA-N 0.000 claims description 3
• SGDBOTFOCXARCG-UHFFFAOYSA-N 1-[5-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-methylphenyl]-3-(3-methylphenyl)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=CC(C)=C1 SGDBOTFOCXARCG-UHFFFAOYSA-N 0.000 claims description 3
• CVYCHVMVWVKCGV-UHFFFAOYSA-N 1-[5-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-methylphenyl]-3-cyclohexylurea Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(=O)C(C=1)=CC=C(C)C=1NC(=O)NC1CCCCC1 CVYCHVMVWVKCGV-UHFFFAOYSA-N 0.000 claims description 3
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
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