EA035349B1 - ЗАМЕЩЕННЫЕ ПИРИМИДИНОВЫЕ ОБРАТНЫЕ ИНГИБИТОРЫ Bmi-1 - Google Patents

Info

Publication number

EA035349B1

EA035349B1 EA201890142A EA201890142A EA035349B1 EA 035349 B1 EA035349 B1 EA 035349B1 EA 201890142 A EA201890142 A EA 201890142A EA 201890142 A EA201890142 A EA 201890142A EA 035349 B1 EA035349 B1 EA 035349B1

Authority

EA

Eurasian Patent Office

Prior art keywords

fluoro

diamine

benzimidazol

methyl

pyrimidin

Prior art date

2012-11-21

Links

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• 101100058550 Mus musculus Bmi1 gene Proteins 0.000 title claims abstract description 195
• 239000003112 inhibitor Substances 0.000 title description 20
• 230000002441 reversible effect Effects 0.000 title description 4
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 449
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 181
• 201000011510 cancer Diseases 0.000 claims abstract description 120
• 230000001404 mediated effect Effects 0.000 claims abstract description 46
• -1 1H-benzimidazolyl Chemical group 0.000 claims description 590
• 125000000217 alkyl group Chemical group 0.000 claims description 249
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 53
• 229910052736 halogen Inorganic materials 0.000 claims description 51
• 125000003545 alkoxy group Chemical group 0.000 claims description 49
• 150000002367 halogens Chemical class 0.000 claims description 49
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 43
• 125000001424 substituent group Chemical group 0.000 claims description 42
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 37
• MISVBCMQSJUHMH-UHFFFAOYSA-N pyrimidine-4,6-diamine Chemical compound NC1=CC(N)=NC=N1 MISVBCMQSJUHMH-UHFFFAOYSA-N 0.000 claims description 32
• 238000011282 treatment Methods 0.000 claims description 32
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
• 239000008194 pharmaceutical composition Substances 0.000 claims description 26
• 125000004414 alkyl thio group Chemical group 0.000 claims description 22
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 21
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
• 125000003342 alkenyl group Chemical group 0.000 claims description 18
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 18
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 17
• 239000002246 antineoplastic agent Substances 0.000 claims description 17
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
• 230000002401 inhibitory effect Effects 0.000 claims description 16
• 239000003814 drug Substances 0.000 claims description 15
• 229940127089 cytotoxic agent Drugs 0.000 claims description 14
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 11
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 10
• 229910052757 nitrogen Inorganic materials 0.000 claims description 10
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 10
• SIYIEJHEMHWDMZ-UHFFFAOYSA-N 2-(4-methylphenyl)pyrimidine-4,6-diamine Chemical compound C1=CC(C)=CC=C1C1=NC(N)=CC(N)=N1 SIYIEJHEMHWDMZ-UHFFFAOYSA-N 0.000 claims description 9
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
• UQTDYCJEMJXGHA-UHFFFAOYSA-N 2-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound NC1=CC(N)=NC(C=2C=CC(=CC=2)C(F)(F)F)=N1 UQTDYCJEMJXGHA-UHFFFAOYSA-N 0.000 claims description 8
• 150000001204 N-oxides Chemical class 0.000 claims description 8
• KMZNRYRZJJJUKT-UHFFFAOYSA-N 2-(4-methoxyphenyl)pyrimidine-4,6-diamine Chemical compound C1=CC(OC)=CC=C1C1=NC(N)=CC(N)=N1 KMZNRYRZJJJUKT-UHFFFAOYSA-N 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 5
• SRRMBKTXOKLLES-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]pyrimidine-4,6-diamine Chemical compound FC(OC1=CC=C(C=C1)C1=NC(=CC(=N1)N)N)(F)F SRRMBKTXOKLLES-UHFFFAOYSA-N 0.000 claims description 4
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
• JZEFXPLZEMNPKI-UHFFFAOYSA-N 1-[4-amino-5-fluoro-6-(4-methylanilino)pyrimidin-2-yl]-2-methylbenzimidazole-5-carbonitrile Chemical compound CC1=NC2=CC(C#N)=CC=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(C)C=C1 JZEFXPLZEMNPKI-UHFFFAOYSA-N 0.000 claims description 3
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• IMVUGEHYYZLOCF-UHFFFAOYSA-N 4-n-(4-chlorophenyl)-5-fluoro-2-(2-methylbenzimidazol-1-yl)pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC=CC=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(Cl)C=C1 IMVUGEHYYZLOCF-UHFFFAOYSA-N 0.000 claims 2
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