EA031405B1 - Замещенные пиримидиновые обратные ингибиторы bmi-1 - Google Patents

Info

Publication number

EA031405B1

EA031405B1 EA201590992A EA201590992A EA031405B1 EA 031405 B1 EA031405 B1 EA 031405B1 EA 201590992 A EA201590992 A EA 201590992A EA 201590992 A EA201590992 A EA 201590992A EA 031405 B1 EA031405 B1 EA 031405B1

Authority

EA

Eurasian Patent Office

Prior art keywords

diamine

pyrimidine

fluoro

benzimidazol

phenyl

Prior art date

2012-11-21

Links

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• Global Dossier
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• 239000003112 inhibitor Substances 0.000 title description 22
• 230000002441 reversible effect Effects 0.000 title description 4
• 101100058548 Felis catus BMI1 gene Proteins 0.000 title description 3
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title description 3
• 101100058550 Mus musculus Bmi1 gene Proteins 0.000 claims abstract description 197
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 184
• 201000011510 cancer Diseases 0.000 claims abstract description 120
• 230000001404 mediated effect Effects 0.000 claims abstract description 51
• -1 1H-benzimidazolyl Chemical group 0.000 claims description 421
• 150000001875 compounds Chemical class 0.000 claims description 381
• 125000000217 alkyl group Chemical group 0.000 claims description 100
• 210000004027 cell Anatomy 0.000 claims description 76
• MISVBCMQSJUHMH-UHFFFAOYSA-N pyrimidine-4,6-diamine Chemical compound NC1=CC(N)=NC=N1 MISVBCMQSJUHMH-UHFFFAOYSA-N 0.000 claims description 73
• 238000000034 method Methods 0.000 claims description 68
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 67
• 239000003795 chemical substances by application Substances 0.000 claims description 55
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 54
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 46
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 41
• 239000002904 solvent Substances 0.000 claims description 39
• 210000000130 stem cell Anatomy 0.000 claims description 39
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 28
• 125000001424 substituent group Chemical group 0.000 claims description 26
• 125000001072 heteroaryl group Chemical group 0.000 claims description 25
• 210000004881 tumor cell Anatomy 0.000 claims description 25
• OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims description 23
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
• 125000003545 alkoxy group Chemical group 0.000 claims description 19
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 19
• 239000002246 antineoplastic agent Substances 0.000 claims description 16
• 229910052736 halogen Inorganic materials 0.000 claims description 15
• 150000002367 halogens Chemical group 0.000 claims description 14
• 229940127089 cytotoxic agent Drugs 0.000 claims description 13
• 230000002401 inhibitory effect Effects 0.000 claims description 13
• 230000004083 survival effect Effects 0.000 claims description 12
• 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 11
• 125000004435 hydrogen atom Chemical group [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
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 10
• 125000004432 carbon atom Chemical group C* 0.000 claims description 9
• 229910052739 hydrogen Inorganic materials 0.000 claims description 9
• 239000001257 hydrogen Substances 0.000 claims description 9
• 125000004076 pyridyl group Chemical group 0.000 claims description 9
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
• 125000003342 alkenyl group Chemical group 0.000 claims description 8
• 150000001412 amines Chemical class 0.000 claims description 7
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 7
• BPEGJWRSRHCHSN-UHFFFAOYSA-N Temozolomide Chemical compound O=C1N(C)N=NC2=C(C(N)=O)N=CN21 BPEGJWRSRHCHSN-UHFFFAOYSA-N 0.000 claims description 6
• 125000004414 alkyl thio group Chemical group 0.000 claims description 6
• 125000001041 indolyl group Chemical group 0.000 claims description 6
• 229960004964 temozolomide Drugs 0.000 claims description 6
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 5
• 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 4
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• RKPRGADWAAEATC-UHFFFAOYSA-N 1-[4-amino-6-(4-chloroanilino)-5-fluoropyrimidin-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(Cl)C=C1 RKPRGADWAAEATC-UHFFFAOYSA-N 0.000 claims description 3
• YOZYMVHGOMKWHA-UHFFFAOYSA-N 1-[4-amino-6-[4-(difluoromethoxy)anilino]-5-fluoropyrimidin-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(OC(F)F)C=C1 YOZYMVHGOMKWHA-UHFFFAOYSA-N 0.000 claims description 3
• SNYDQRUIJGKYSR-UHFFFAOYSA-N 2-(2-cyclopropyl-6-fluoroimidazo[4,5-b]pyridin-1-yl)-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound N=1C(N2C3=CC(F)=CN=C3N=C2C2CC2)=NC(N)=CC=1NC1=CC=C(C(F)(F)F)C=C1 SNYDQRUIJGKYSR-UHFFFAOYSA-N 0.000 claims description 3
• SYZVRWFZRXPOBU-UHFFFAOYSA-N 2-(2-ethyl-6-fluorobenzimidazol-1-yl)-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CCC1=NC2=CC=C(F)C=C2N1C(N=1)=NC(N)=CC=1NC1=CC=C(C(F)(F)F)C=C1 SYZVRWFZRXPOBU-UHFFFAOYSA-N 0.000 claims description 3
• OTCSQWDROJGFCG-UHFFFAOYSA-N 2-(2-methylimidazo[4,5-b]pyridin-1-yl)-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CC1=NC2=NC=CC=C2N1C(N=1)=NC(N)=CC=1NC1=CC=C(C(F)(F)F)C=C1 OTCSQWDROJGFCG-UHFFFAOYSA-N 0.000 claims description 3
• JQNWPGQMXITTAF-UHFFFAOYSA-N 2-(6-fluoro-2-methylimidazo[4,5-b]pyridin-1-yl)-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CC1=NC2=NC=C(F)C=C2N1C(N=1)=NC(N)=CC=1NC1=CC=C(C(F)(F)F)C=C1 JQNWPGQMXITTAF-UHFFFAOYSA-N 0.000 claims description 3
• ZVWFPHGCPFSOJS-UHFFFAOYSA-N 2-imidazo[1,2-a]pyridin-3-yl-n-[4-(trifluoromethyl)phenyl]pyrimidin-4-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=CC=NC(C=2N3C=CC=CC3=NC=2)=N1 ZVWFPHGCPFSOJS-UHFFFAOYSA-N 0.000 claims description 3
• QJVLZNRNFLBQHK-UHFFFAOYSA-N 3-[4-amino-6-[4-(difluoromethoxy)anilino]-5-fluoropyrimidin-2-yl]-2-methylbenzimidazole-5-carbonitrile Chemical compound CC1=NC2=CC=C(C#N)C=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(OC(F)F)C=C1 QJVLZNRNFLBQHK-UHFFFAOYSA-N 0.000 claims description 3
• WHFGWVYLOBCVPL-UHFFFAOYSA-N 4-[[6-amino-5-fluoro-2-(2-methylbenzimidazol-1-yl)pyrimidin-4-yl]amino]benzonitrile Chemical compound CC1=NC2=CC=CC=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(C#N)C=C1 WHFGWVYLOBCVPL-UHFFFAOYSA-N 0.000 claims description 3
• JYIBQJNMMZOWNV-UHFFFAOYSA-N 4-[[6-amino-5-fluoro-2-(6-fluoro-2-methylbenzimidazol-1-yl)pyrimidin-4-yl]amino]benzonitrile Chemical compound CC1=NC2=CC=C(F)C=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(C#N)C=C1 JYIBQJNMMZOWNV-UHFFFAOYSA-N 0.000 claims description 3
• QPORTJYLGOENII-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)-3-fluorophenyl]-5-fluoro-2-(4-fluoro-2-methylbenzimidazol-1-yl)pyrimidine-4,6-diamine Chemical compound CC1=NC2=C(F)C=CC=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(OC(F)F)C(F)=C1 QPORTJYLGOENII-UHFFFAOYSA-N 0.000 claims description 3
• JNQCJNFMFPUFIV-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)phenyl]-5-fluoro-2-(6-methoxy-2-methylbenzimidazol-1-yl)pyrimidine-4,6-diamine Chemical compound C12=CC(OC)=CC=C2N=C(C)N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(OC(F)F)C=C1 JNQCJNFMFPUFIV-UHFFFAOYSA-N 0.000 claims description 3
• JXSKHZIAKGMOTN-UHFFFAOYSA-N 5,6-difluoro-2-methyl-1h-benzimidazole Chemical compound FC1=C(F)C=C2NC(C)=NC2=C1 JXSKHZIAKGMOTN-UHFFFAOYSA-N 0.000 claims description 3
• KSTQQADVJQZULT-UHFFFAOYSA-N FC=1C(=NC(=NC1N)N1C(=NC2=NC=CC=C21)C)NC2=CC=C(C=C2)C(F)(F)F Chemical compound FC=1C(=NC(=NC1N)N1C(=NC2=NC=CC=C21)C)NC2=CC=C(C=C2)C(F)(F)F KSTQQADVJQZULT-UHFFFAOYSA-N 0.000 claims description 3
• QVVDQKAXRBUFFB-UHFFFAOYSA-N n-(3-chloro-4-methoxyphenyl)-2-[2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-4-amine Chemical compound C1=C(Cl)C(OC)=CC=C1NC1=CC=NC(C=2N3C=CC=CC3=NC=2C(F)(F)F)=N1 QVVDQKAXRBUFFB-UHFFFAOYSA-N 0.000 claims description 3
• QRSVQZKCGOKNMV-UHFFFAOYSA-N n-(4-methylphenyl)-2-[2-methyl-6-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-4-amine Chemical compound CC=1N=C2C=CC(C(F)(F)F)=CN2C=1C(N=1)=NC=CC=1NC1=CC=C(C)C=C1 QRSVQZKCGOKNMV-UHFFFAOYSA-N 0.000 claims description 3
• CRALZQILSLIULB-UHFFFAOYSA-N 1-[4-amino-5-fluoro-6-(4-methoxyanilino)pyrimidin-2-yl]-2-methylbenzimidazole-5-carbonitrile Chemical compound C1=CC(OC)=CC=C1NC1=NC(N2C3=CC=C(C=C3N=C2C)C#N)=NC(N)=C1F CRALZQILSLIULB-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims description 2
• QMRUWLFJRUMHQQ-UHFFFAOYSA-N 2-(2-cyclopropyl-6-fluoroimidazo[4,5-b]pyridin-1-yl)-4-n-[4-(difluoromethoxy)phenyl]-5-fluoropyrimidine-4,6-diamine Chemical compound FC=1C(N)=NC(N2C3=CC(F)=CN=C3N=C2C2CC2)=NC=1NC1=CC=C(OC(F)F)C=C1 QMRUWLFJRUMHQQ-UHFFFAOYSA-N 0.000 claims description 2
• HDUNBWWCCZWPSW-UHFFFAOYSA-N 3-[4-amino-5-fluoro-6-(4-methoxyanilino)pyrimidin-2-yl]-2-methylbenzimidazole-5-carbonitrile Chemical compound C1=CC(OC)=CC=C1NC1=NC(N2C3=CC(=CC=C3N=C2C)C#N)=NC(N)=C1F HDUNBWWCCZWPSW-UHFFFAOYSA-N 0.000 claims description 2
• IQQSHMVVOXOAFZ-UHFFFAOYSA-N 3-[4-amino-5-fluoro-6-(4-methylanilino)pyrimidin-2-yl]-2-methylbenzimidazole-5-carbonitrile Chemical compound CC1=NC2=CC=C(C#N)C=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(C)C=C1 IQQSHMVVOXOAFZ-UHFFFAOYSA-N 0.000 claims description 2
• GJMVQNGXFKXZSB-UHFFFAOYSA-N 4-[[6-amino-2-(2-methylbenzimidazol-1-yl)pyrimidin-4-yl]amino]benzonitrile Chemical compound CC1=NC2=CC=CC=C2N1C(N=1)=NC(N)=CC=1NC1=CC=C(C#N)C=C1 GJMVQNGXFKXZSB-UHFFFAOYSA-N 0.000 claims description 2
• FUOQVPJSMHJUBZ-UHFFFAOYSA-N 4-n-(1,3-benzodioxol-5-yl)-2-(2-ethylbenzimidazol-1-yl)-5-fluoropyrimidine-4,6-diamine Chemical compound C1=C2OCOC2=CC(NC=2C(F)=C(N)N=C(N=2)N2C3=CC=CC=C3N=C2CC)=C1 FUOQVPJSMHJUBZ-UHFFFAOYSA-N 0.000 claims description 2
• KUBNHQKCMQMYNJ-UHFFFAOYSA-N 4-n-(3-fluoro-4-methoxyphenyl)-2-(2-methylbenzimidazol-1-yl)pyrimidine-4,6-diamine Chemical compound C1=C(F)C(OC)=CC=C1NC1=CC(N)=NC(N2C3=CC=CC=C3N=C2C)=N1 KUBNHQKCMQMYNJ-UHFFFAOYSA-N 0.000 claims description 2
• FTKYBISNKVDOOV-UHFFFAOYSA-N 4-n-(4-chloro-3-fluorophenyl)-2-(2-ethylbenzimidazol-1-yl)-5-fluoropyrimidine-4,6-diamine Chemical compound CCC1=NC2=CC=CC=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(Cl)C(F)=C1 FTKYBISNKVDOOV-UHFFFAOYSA-N 0.000 claims description 2
• DKBXAFMQCYSPAV-UHFFFAOYSA-N 4-n-(4-chlorophenyl)-2-(2-cyclopropylbenzimidazol-1-yl)-5-fluoropyrimidine-4,6-diamine Chemical compound FC=1C(N)=NC(N2C3=CC=CC=C3N=C2C2CC2)=NC=1NC1=CC=C(Cl)C=C1 DKBXAFMQCYSPAV-UHFFFAOYSA-N 0.000 claims description 2
• JOGHAGASWBJPDO-UHFFFAOYSA-N 4-n-(4-chlorophenyl)-2-(2-ethylbenzimidazol-1-yl)-5-fluoropyrimidine-4,6-diamine Chemical compound CCC1=NC2=CC=CC=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(Cl)C=C1 JOGHAGASWBJPDO-UHFFFAOYSA-N 0.000 claims description 2
• VAABNOYEIHLZGX-UHFFFAOYSA-N 4-n-(4-chlorophenyl)-2-(4,6-difluoro-2-methylbenzimidazol-1-yl)-5-fluoropyrimidine-4,6-diamine Chemical compound CC1=NC2=C(F)C=C(F)C=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(Cl)C=C1 VAABNOYEIHLZGX-UHFFFAOYSA-N 0.000 claims description 2
• NNEQTNBXFBFCBX-UHFFFAOYSA-N 4-n-(4-chlorophenyl)-5-fluoro-2-[2-(methoxymethyl)benzimidazol-1-yl]pyrimidine-4,6-diamine Chemical compound COCC1=NC2=CC=CC=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(Cl)C=C1 NNEQTNBXFBFCBX-UHFFFAOYSA-N 0.000 claims description 2
• HPHVGFRGRUBLHM-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)-3-fluorophenyl]-2-(2-ethyl-4,6-difluorobenzimidazol-1-yl)-5-fluoropyrimidine-4,6-diamine Chemical compound CCC1=NC2=C(F)C=C(F)C=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(OC(F)F)C(F)=C1 HPHVGFRGRUBLHM-UHFFFAOYSA-N 0.000 claims description 2
• MGQZHQPYSYMOMA-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)-3-fluorophenyl]-2-(4,6-difluoro-2-methylbenzimidazol-1-yl)-5-fluoropyrimidine-4,6-diamine Chemical compound CC1=NC2=C(F)C=C(F)C=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(OC(F)F)C(F)=C1 MGQZHQPYSYMOMA-UHFFFAOYSA-N 0.000 claims description 2
• WABPIFCXKSDGCY-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)-3-fluorophenyl]-2-(5,6-difluoro-2-methylbenzimidazol-1-yl)-5-fluoropyrimidine-4,6-diamine Chemical compound CC1=NC2=CC(F)=C(F)C=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(OC(F)F)C(F)=C1 WABPIFCXKSDGCY-UHFFFAOYSA-N 0.000 claims description 2
• HBGUFSZUWIQQEA-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)-3-fluorophenyl]-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(OC(F)F)C(F)=C1 HBGUFSZUWIQQEA-UHFFFAOYSA-N 0.000 claims description 2
• UXVYBGXFUZOMJA-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)-3-fluorophenyl]-5-fluoro-2-(5-fluoro-2-methylbenzimidazol-1-yl)pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC(F)=CC=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(OC(F)F)C(F)=C1 UXVYBGXFUZOMJA-UHFFFAOYSA-N 0.000 claims description 2
• GRDHSDHOQMFEPZ-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)-3-fluorophenyl]-5-fluoro-2-(6-fluoro-2-methylbenzimidazol-1-yl)pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC=C(F)C=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(OC(F)F)C(F)=C1 GRDHSDHOQMFEPZ-UHFFFAOYSA-N 0.000 claims description 2
• VKYQYDNTFBKTAN-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)phenyl]-2-(2-ethyl-5-fluoropyrazolo[1,5-a]pyridin-3-yl)-5-fluoropyrimidine-4,6-diamine Chemical compound CCC1=NN2C=CC(F)=CC2=C1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(OC(F)F)C=C1 VKYQYDNTFBKTAN-UHFFFAOYSA-N 0.000 claims description 2
• KXCVLZCDBIEXRL-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)phenyl]-2-(2-ethylbenzimidazol-1-yl)-5-fluoropyrimidine-4,6-diamine Chemical compound CCC1=NC2=CC=CC=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(OC(F)F)C=C1 KXCVLZCDBIEXRL-UHFFFAOYSA-N 0.000 claims description 2
• RVJAJAQKQAHBAM-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)phenyl]-2-(5,6-difluoro-2-methylbenzimidazol-1-yl)-5-fluoropyrimidine-4,6-diamine Chemical compound CC1=NC2=CC(F)=C(F)C=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(OC(F)F)C=C1 RVJAJAQKQAHBAM-UHFFFAOYSA-N 0.000 claims description 2
• CAOWQPZSBSVKRI-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)phenyl]-5-fluoro-2-(2-methylimidazo[4,5-b]pyridin-1-yl)pyrimidine-4,6-diamine Chemical compound CC1=NC2=NC=CC=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(OC(F)F)C=C1 CAOWQPZSBSVKRI-UHFFFAOYSA-N 0.000 claims description 2
• QHRHRWJJBXZVGK-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)phenyl]-5-fluoro-2-(4-fluoro-2-methylbenzimidazol-1-yl)pyrimidine-4,6-diamine Chemical compound CC1=NC2=C(F)C=CC=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(OC(F)F)C=C1 QHRHRWJJBXZVGK-UHFFFAOYSA-N 0.000 claims description 2
• IPAPOGNVWQIELZ-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)phenyl]-5-fluoro-2-(5-fluoro-2-methylbenzimidazol-1-yl)pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC(F)=CC=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(OC(F)F)C=C1 IPAPOGNVWQIELZ-UHFFFAOYSA-N 0.000 claims description 2
• DTXKNPZCFQVYSH-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)phenyl]-5-fluoro-2-(6-fluoro-2-methylbenzimidazol-1-yl)pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC=C(F)C=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(OC(F)F)C=C1 DTXKNPZCFQVYSH-UHFFFAOYSA-N 0.000 claims description 2
• RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 2
• QZHGNWZETKVWGT-UHFFFAOYSA-N [3-[4-amino-6-[4-(difluoromethoxy)anilino]-5-fluoropyrimidin-2-yl]-5-fluoropyrazolo[1,5-a]pyridin-2-yl]methanol Chemical compound FC=1C(N)=NC(C2=C3C=C(F)C=CN3N=C2CO)=NC=1NC1=CC=C(OC(F)F)C=C1 QZHGNWZETKVWGT-UHFFFAOYSA-N 0.000 claims description 2
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