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 |
| AU2020209767B2 (en) * | 2019-01-15 | 2025-03-06 | Ptc Therapeutics, Inc. | Method for treating an acute myeloid leukemia |
| CN113710670A (zh) * | 2019-02-28 | 2021-11-26 | Ptc医疗公司 | 治疗多发性骨髓瘤的方法 |
| JP2022524424A (ja) * | 2019-03-11 | 2022-05-02 | ピーティーシー セラピューティクス， インコーポレイテッド | 向上したバイオアベイラビリティを有する化合物形態及びその製剤 |
| CN113873935B (zh) | 2019-03-22 | 2024-11-22 | 科格诺亚公司 | 个性化数字化治疗方法和装置 |
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