JP2016504290A5 - - Google Patents
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- Publication number
- JP2016504290A5 JP2016504290A5 JP2015544124A JP2015544124A JP2016504290A5 JP 2016504290 A5 JP2016504290 A5 JP 2016504290A5 JP 2015544124 A JP2015544124 A JP 2015544124A JP 2015544124 A JP2015544124 A JP 2015544124A JP 2016504290 A5 JP2016504290 A5 JP 2016504290A5
- Authority
- JP
- Japan
- Prior art keywords
- diamine
- fluoro
- benzimidazol
- pyrimidine
- phenyl
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims description 98
- -1 hydroxyl-amino Chemical group 0.000 claims description 98
- 150000001875 compounds Chemical class 0.000 claims description 56
- 101100058550 Mus musculus Bmi1 gene Proteins 0.000 claims description 44
- 125000003282 alkyl amino group Chemical group 0.000 claims description 31
- 206010028980 Neoplasm Diseases 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 201000011510 cancer Diseases 0.000 claims description 20
- 210000004027 cell Anatomy 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 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 13
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 230000001404 mediated effect Effects 0.000 claims description 12
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 239000003242 anti bacterial agent Substances 0.000 claims description 8
- 239000002246 antineoplastic agent Substances 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 210000000130 stem cell Anatomy 0.000 claims description 8
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 7
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 6
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims description 4
- 150000001204 N-oxides Chemical class 0.000 claims description 4
- 102000004243 Tubulin Human genes 0.000 claims description 4
- 108090000704 Tubulin Proteins 0.000 claims description 4
- 239000003470 adrenal cortex hormone Substances 0.000 claims description 4
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 4
- 239000004037 angiogenesis inhibitor Substances 0.000 claims description 4
- 239000000730 antalgic agent Substances 0.000 claims description 4
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 4
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 4
- 230000001028 anti-proliverative effect Effects 0.000 claims description 4
- 239000000739 antihistaminic agent Substances 0.000 claims description 4
- 239000003430 antimalarial agent Substances 0.000 claims description 4
- 239000003443 antiviral agent Substances 0.000 claims description 4
- 125000001769 aryl amino group Chemical group 0.000 claims description 4
- 229940124748 beta 2 agonist Drugs 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- 239000003124 biologic agent Substances 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 239000013522 chelant Substances 0.000 claims description 4
- 239000000812 cholinergic antagonist Substances 0.000 claims description 4
- 229940127089 cytotoxic agent Drugs 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 239000003862 glucocorticoid Substances 0.000 claims description 4
- 229940125697 hormonal agent Drugs 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 239000002955 immunomodulating agent Substances 0.000 claims description 4
- 229940121354 immunomodulator Drugs 0.000 claims description 4
- 230000002584 immunomodulator Effects 0.000 claims description 4
- 239000003199 leukotriene receptor blocking agent Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 4
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 238000001959 radiotherapy Methods 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- 239000002294 steroidal antiinflammatory agent Substances 0.000 claims description 4
- 150000003431 steroids Chemical class 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 210000004881 tumor cell Anatomy 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 230000000155 isotopic effect Effects 0.000 claims description 3
- 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
- QWNRBKAXMKABIG-UHFFFAOYSA-N 1-[4-amino-5-fluoro-6-[4-(trifluoromethyl)anilino]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(F)(F)F)C=C1 QWNRBKAXMKABIG-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- ICKOCYPNSXNVBG-UHFFFAOYSA-N 2-(2-cyclopropyl-4-fluorobenzimidazol-1-yl)-4-n-[4-(difluoromethoxy)-3-fluorophenyl]-5-fluoropyrimidine-4,6-diamine Chemical compound FC=1C(N)=NC(N2C3=CC=CC(F)=C3N=C2C2CC2)=NC=1NC1=CC=C(OC(F)F)C(F)=C1 ICKOCYPNSXNVBG-UHFFFAOYSA-N 0.000 claims description 2
- VMNHDKPGHLJLJG-UHFFFAOYSA-N 2-(2-cyclopropyl-4-fluorobenzimidazol-1-yl)-4-n-[4-(difluoromethoxy)phenyl]-5-fluoropyrimidine-4,6-diamine Chemical compound FC=1C(N)=NC(N2C3=CC=CC(F)=C3N=C2C2CC2)=NC=1NC1=CC=C(OC(F)F)C=C1 VMNHDKPGHLJLJG-UHFFFAOYSA-N 0.000 claims description 2
- WKKKIRDLPBGOBE-UHFFFAOYSA-N 2-(2-cyclopropyl-4-fluorobenzimidazol-1-yl)-5-fluoro-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound FC=1C(N)=NC(N2C3=CC=CC(F)=C3N=C2C2CC2)=NC=1NC1=CC=C(C(F)(F)F)C=C1 WKKKIRDLPBGOBE-UHFFFAOYSA-N 0.000 claims description 2
- YAEPLAMQAZXVIF-UHFFFAOYSA-N 2-(2-cyclopropyl-5-fluorobenzimidazol-1-yl)-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound N=1C(N2C3=CC=C(F)C=C3N=C2C2CC2)=NC(N)=CC=1NC1=CC=C(C(F)(F)F)C=C1 YAEPLAMQAZXVIF-UHFFFAOYSA-N 0.000 claims description 2
- LQBXWUVRFKLMGL-UHFFFAOYSA-N 2-(2-cyclopropyl-6-fluorobenzimidazol-1-yl)-4-n-[4-(difluoromethoxy)-3-fluorophenyl]pyrimidine-4,6-diamine Chemical compound N=1C(N2C3=CC(F)=CC=C3N=C2C2CC2)=NC(N)=CC=1NC1=CC=C(OC(F)F)C(F)=C1 LQBXWUVRFKLMGL-UHFFFAOYSA-N 0.000 claims description 2
- SGTURXOUZJDSMP-UHFFFAOYSA-N 2-(2-cyclopropyl-6-fluorobenzimidazol-1-yl)-4-n-[4-(difluoromethoxy)phenyl]pyrimidine-4,6-diamine Chemical compound N=1C(N2C3=CC(F)=CC=C3N=C2C2CC2)=NC(N)=CC=1NC1=CC=C(OC(F)F)C=C1 SGTURXOUZJDSMP-UHFFFAOYSA-N 0.000 claims description 2
- VOSMLAJLYBUGQH-UHFFFAOYSA-N 2-(2-cyclopropyl-6-fluorobenzimidazol-1-yl)-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound N=1C(N2C3=CC(F)=CC=C3N=C2C2CC2)=NC(N)=CC=1NC1=CC=C(C(F)(F)F)C=C1 VOSMLAJLYBUGQH-UHFFFAOYSA-N 0.000 claims description 2
- SBRWGWHCZYSLDM-UHFFFAOYSA-N 2-(2-cyclopropyl-6-fluoroimidazo[1,2-a]pyridin-3-yl)-4-n-[4-(difluoromethoxy)-3-fluorophenyl]pyrimidine-4,6-diamine Chemical compound N=1C(C=2N3C=C(F)C=CC3=NC=2C2CC2)=NC(N)=CC=1NC1=CC=C(OC(F)F)C(F)=C1 SBRWGWHCZYSLDM-UHFFFAOYSA-N 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
- CZSBOJMFWKNNKD-UHFFFAOYSA-N 2-(2-cyclopropyl-6-fluoroimidazo[4,5-b]pyridin-1-yl)-4-n-[4-(difluoromethoxy)phenyl]pyrimidine-4,6-diamine Chemical compound N=1C(N2C3=CC(F)=CN=C3N=C2C2CC2)=NC(N)=CC=1NC1=CC=C(OC(F)F)C=C1 CZSBOJMFWKNNKD-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- JFSDSKVNJAGOGR-UHFFFAOYSA-N 2-(2-cyclopropyl-6-fluoroimidazo[4,5-b]pyridin-1-yl)-5-fluoro-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound FC=1C(N)=NC(N2C3=CC(F)=CN=C3N=C2C2CC2)=NC=1NC1=CC=C(C(F)(F)F)C=C1 JFSDSKVNJAGOGR-UHFFFAOYSA-N 0.000 claims description 2
- ZLMCCSNCGLUUAE-UHFFFAOYSA-N 2-(2-cyclopropylbenzimidazol-1-yl)-4-n-[4-(difluoromethoxy)-3-fluorophenyl]-5-fluoropyrimidine-4,6-diamine Chemical compound FC=1C(N)=NC(N2C3=CC=CC=C3N=C2C2CC2)=NC=1NC1=CC=C(OC(F)F)C(F)=C1 ZLMCCSNCGLUUAE-UHFFFAOYSA-N 0.000 claims description 2
- MLIPWIKBNZPYFI-UHFFFAOYSA-N 2-(2-cyclopropylbenzimidazol-1-yl)-4-n-[4-(difluoromethoxy)phenyl]-5-fluoropyrimidine-4,6-diamine Chemical compound FC=1C(N)=NC(N2C3=CC=CC=C3N=C2C2CC2)=NC=1NC1=CC=C(OC(F)F)C=C1 MLIPWIKBNZPYFI-UHFFFAOYSA-N 0.000 claims description 2
- UOJKFQNUSKEWAT-UHFFFAOYSA-N 2-(2-cyclopropylbenzimidazol-1-yl)-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound N=1C(N2C3=CC=CC=C3N=C2C2CC2)=NC(N)=CC=1NC1=CC=C(C(F)(F)F)C=C1 UOJKFQNUSKEWAT-UHFFFAOYSA-N 0.000 claims description 2
- AUIOXUNJCKKPBR-UHFFFAOYSA-N 2-(2-cyclopropylbenzimidazol-1-yl)-5-fluoro-4-n-(4-methoxyphenyl)pyrimidine-4,6-diamine Chemical compound C1=CC(OC)=CC=C1NC1=NC(N2C3=CC=CC=C3N=C2C2CC2)=NC(N)=C1F AUIOXUNJCKKPBR-UHFFFAOYSA-N 0.000 claims description 2
- OFSLVNGAXLKRKR-UHFFFAOYSA-N 2-(2-cyclopropylbenzimidazol-1-yl)-5-fluoro-4-n-[4-(trifluoromethoxy)phenyl]pyrimidine-4,6-diamine Chemical compound FC=1C(N)=NC(N2C3=CC=CC=C3N=C2C2CC2)=NC=1NC1=CC=C(OC(F)(F)F)C=C1 OFSLVNGAXLKRKR-UHFFFAOYSA-N 0.000 claims description 2
- HUKMRMGDMVPNJP-UHFFFAOYSA-N 2-(2-cyclopropylbenzimidazol-1-yl)-5-fluoro-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound FC=1C(N)=NC(N2C3=CC=CC=C3N=C2C2CC2)=NC=1NC1=CC=C(C(F)(F)F)C=C1 HUKMRMGDMVPNJP-UHFFFAOYSA-N 0.000 claims description 2
- WQDGKMFCKOBUKG-UHFFFAOYSA-N 2-(2-cyclopropylpyrazolo[1,5-a]pyridin-3-yl)-4-n-[4-(difluoromethoxy)phenyl]-5-fluoropyrimidine-4,6-diamine Chemical compound FC=1C(N)=NC(C2=C3C=CC=CN3N=C2C2CC2)=NC=1NC1=CC=C(OC(F)F)C=C1 WQDGKMFCKOBUKG-UHFFFAOYSA-N 0.000 claims description 2
- WXPKBICAEZEHFD-UHFFFAOYSA-N 2-(2-ethyl-4,6-difluorobenzimidazol-1-yl)-5-fluoro-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CCC1=NC2=C(F)C=C(F)C=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(C(F)(F)F)C=C1 WXPKBICAEZEHFD-UHFFFAOYSA-N 0.000 claims description 2
- QTHHFSYDYHUWEU-UHFFFAOYSA-N 2-(2-ethyl-5-fluorobenzimidazol-1-yl)-5-fluoro-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CCC1=NC2=CC(F)=CC=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(C(F)(F)F)C=C1 QTHHFSYDYHUWEU-UHFFFAOYSA-N 0.000 claims description 2
- BFOAUWGCMCYGTI-UHFFFAOYSA-N 2-(2-ethyl-5-fluoropyrazolo[1,5-a]pyridin-3-yl)-5-fluoro-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CCC1=NN2C=CC(F)=CC2=C1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(C(F)(F)F)C=C1 BFOAUWGCMCYGTI-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- MJFMGIUOZPWGKF-UHFFFAOYSA-N 2-(2-ethyl-6-fluorobenzimidazol-1-yl)-5-fluoro-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CCC1=NC2=CC=C(F)C=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(C(F)(F)F)C=C1 MJFMGIUOZPWGKF-UHFFFAOYSA-N 0.000 claims description 2
- LIGYYKKUMCDZHW-UHFFFAOYSA-N 2-(2-ethylbenzimidazol-1-yl)-5-fluoro-4-N-(4-methoxyphenyl)pyrimidine-4,6-diamine 2-(2-ethylbenzimidazol-1-yl)-5-fluoro-4-N-[4-(trifluoromethoxy)phenyl]pyrimidine-4,6-diamine Chemical compound C(C)C1=NC2=C(N1C1=NC(=C(C(=N1)NC1=CC=C(C=C1)OC(F)(F)F)F)N)C=CC=C2.C(C)C2=NC1=C(N2C2=NC(=C(C(=N2)NC2=CC=C(C=C2)OC)F)N)C=CC=C1 LIGYYKKUMCDZHW-UHFFFAOYSA-N 0.000 claims description 2
- RPCVLWZRRGSYKE-UHFFFAOYSA-N 2-(2-ethylbenzimidazol-1-yl)-5-fluoro-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CCC1=NC2=CC=CC=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(C(F)(F)F)C=C1 RPCVLWZRRGSYKE-UHFFFAOYSA-N 0.000 claims description 2
- NFVXSOIDHDDAOP-UHFFFAOYSA-N 2-(2-methylbenzimidazol-1-yl)-4-n-(4-methylsulfanylphenyl)pyrimidine-4,6-diamine Chemical compound C1=CC(SC)=CC=C1NC1=CC(N)=NC(N2C3=CC=CC=C3N=C2C)=N1 NFVXSOIDHDDAOP-UHFFFAOYSA-N 0.000 claims description 2
- VCIBXBYUWPNQSY-UHFFFAOYSA-N 2-(2-methylbenzimidazol-1-yl)-4-n-[4-(trifluoromethoxy)phenyl]pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC=CC=C2N1C(N=1)=NC(N)=CC=1NC1=CC=C(OC(F)(F)F)C=C1 VCIBXBYUWPNQSY-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- AMVNCIDWFCDCNE-UHFFFAOYSA-N 2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CC1=NN2C=CC=CC2=C1C(N=1)=NC(N)=CC=1NC1=CC=C(C(F)(F)F)C=C1 AMVNCIDWFCDCNE-UHFFFAOYSA-N 0.000 claims description 2
- ODZCUCTVBDTFGQ-UHFFFAOYSA-N 2-(2-methylsulfanylbenzimidazol-1-yl)-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CSC1=NC2=CC=CC=C2N1C(N=1)=NC(N)=CC=1NC1=CC=C(C(F)(F)F)C=C1 ODZCUCTVBDTFGQ-UHFFFAOYSA-N 0.000 claims description 2
- MPNZQASOWIZAEH-UHFFFAOYSA-N 2-(2-propan-2-ylbenzimidazol-1-yl)-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CC(C)C1=NC2=CC=CC=C2N1C(N=1)=NC(N)=CC=1NC1=CC=C(C(F)(F)F)C=C1 MPNZQASOWIZAEH-UHFFFAOYSA-N 0.000 claims description 2
- WDFUZSVUZYOBKR-UHFFFAOYSA-N 2-(4,6-difluoro-2-methylbenzimidazol-1-yl)-4-n-[3-fluoro-4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CC1=NC2=C(F)C=C(F)C=C2N1C(N=1)=NC(N)=CC=1NC1=CC=C(C(F)(F)F)C(F)=C1 WDFUZSVUZYOBKR-UHFFFAOYSA-N 0.000 claims description 2
- SPPJDASVYCZLHV-UHFFFAOYSA-N 2-(4,6-difluoro-2-methylbenzimidazol-1-yl)-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CC1=NC2=C(F)C=C(F)C=C2N1C(N=1)=NC(N)=CC=1NC1=CC=C(C(F)(F)F)C=C1 SPPJDASVYCZLHV-UHFFFAOYSA-N 0.000 claims description 2
- IMFIKEVUZDKFCK-UHFFFAOYSA-N 2-(4,6-difluoro-2-methylbenzimidazol-1-yl)-5-fluoro-4-n-(4-methoxyphenyl)pyrimidine-4,6-diamine Chemical compound C1=CC(OC)=CC=C1NC1=NC(N2C3=CC(F)=CC(F)=C3N=C2C)=NC(N)=C1F IMFIKEVUZDKFCK-UHFFFAOYSA-N 0.000 claims description 2
- IKOHBXWYJCAUPJ-UHFFFAOYSA-N 2-(4,6-difluoro-2-methylbenzimidazol-1-yl)-5-fluoro-4-n-(4-methylphenyl)pyrimidine-4,6-diamine Chemical compound CC1=NC2=C(F)C=C(F)C=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(C)C=C1 IKOHBXWYJCAUPJ-UHFFFAOYSA-N 0.000 claims description 2
- HVXYQSYBMZNXQV-UHFFFAOYSA-N 2-(4,6-difluoro-2-methylbenzimidazol-1-yl)-5-fluoro-4-n-[4-(trifluoromethoxy)phenyl]pyrimidine-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)F)C=C1 HVXYQSYBMZNXQV-UHFFFAOYSA-N 0.000 claims description 2
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| CN109988172B (zh) * | 2019-01-10 | 2020-09-29 | 石家庄学院 | 一种吡唑并[1,5-a]嘧啶类杂环化合物及衍生物的合成方法 |
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