JP2016504290A5 - - Google Patents
Download PDFInfo
- 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
Links
- 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
- MMOFTBKEKDFCLK-UHFFFAOYSA-N 2-(4,6-difluoro-2-methylbenzimidazol-1-yl)-5-fluoro-4-n-[4-(trifluoromethyl)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(C(F)(F)F)C=C1 MMOFTBKEKDFCLK-UHFFFAOYSA-N 0.000 claims description 2
- NYTXPVHSKFGRTD-UHFFFAOYSA-N 2-(5,6-difluoro-2-methylbenzimidazol-1-yl)-4-n-[3-fluoro-4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC(F)=C(F)C=C2N1C(N=1)=NC(N)=CC=1NC1=CC=C(C(F)(F)F)C(F)=C1 NYTXPVHSKFGRTD-UHFFFAOYSA-N 0.000 claims description 2
- USGPPZYVPLYVHZ-UHFFFAOYSA-N 2-(5,6-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)=C(F)C=C3N=C2C)=NC(N)=C1F USGPPZYVPLYVHZ-UHFFFAOYSA-N 0.000 claims description 2
- TYXJEKPMTZDYOM-UHFFFAOYSA-N 2-(5,6-difluoro-2-methylbenzimidazol-1-yl)-5-fluoro-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC(F)=C(F)C=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(C(F)(F)F)C=C1 TYXJEKPMTZDYOM-UHFFFAOYSA-N 0.000 claims description 2
- CUOWJRCANYJXAW-UHFFFAOYSA-N 2-(5,7-difluoro-2-methylbenzimidazol-1-yl)-5-fluoro-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC(F)=CC(F)=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(C(F)(F)F)C=C1 CUOWJRCANYJXAW-UHFFFAOYSA-N 0.000 claims description 2
- WITMAZXNDHBRQG-UHFFFAOYSA-N 2-(5-chloro-2-methylbenzimidazol-1-yl)-4-n-[3-fluoro-4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC(Cl)=CC=C2N1C(N=1)=NC(N)=CC=1NC1=CC=C(C(F)(F)F)C(F)=C1 WITMAZXNDHBRQG-UHFFFAOYSA-N 0.000 claims description 2
- GSLHLSQSTNAUDI-UHFFFAOYSA-N 2-(5-chloro-2-methylbenzimidazol-1-yl)-4-n-[4-(difluoromethoxy)phenyl]-5-fluoropyrimidine-4,6-diamine Chemical compound CC1=NC2=CC(Cl)=CC=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(OC(F)F)C=C1 GSLHLSQSTNAUDI-UHFFFAOYSA-N 0.000 claims description 2
- WDCLEYPIKDXQQR-UHFFFAOYSA-N 2-(5-chloro-2-methylbenzimidazol-1-yl)-5-fluoro-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC(Cl)=CC=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(C(F)(F)F)C=C1 WDCLEYPIKDXQQR-UHFFFAOYSA-N 0.000 claims description 2
- QEKISZCIPMIENB-UHFFFAOYSA-N 2-(6-amino-2-methylbenzimidazol-1-yl)-4-n-[4-(difluoromethoxy)phenyl]-5-fluoropyrimidine-4,6-diamine Chemical compound CC1=NC2=CC=C(N)C=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(OC(F)F)C=C1 QEKISZCIPMIENB-UHFFFAOYSA-N 0.000 claims description 2
- NFMRRBGTCRGCDG-UHFFFAOYSA-N 2-(6-amino-2-methylbenzimidazol-1-yl)-5-fluoro-4-n-(4-methoxyphenyl)pyrimidine-4,6-diamine Chemical compound C1=CC(OC)=CC=C1NC1=NC(N2C3=CC(N)=CC=C3N=C2C)=NC(N)=C1F NFMRRBGTCRGCDG-UHFFFAOYSA-N 0.000 claims description 2
- WFTKUFBLJMVQFO-UHFFFAOYSA-N 2-(6-amino-2-methylbenzimidazol-1-yl)-5-fluoro-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC=C(N)C=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(C(F)(F)F)C=C1 WFTKUFBLJMVQFO-UHFFFAOYSA-N 0.000 claims description 2
- LHGYAPQIPCDEBD-UHFFFAOYSA-N 2-(6-bromo-2-methylbenzimidazol-1-yl)-4-N-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine 2-(2,6-dimethylbenzimidazol-1-yl)-4-N-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CC1=NC2=C(N1C1=NC(=CC(=N1)NC1=CC=C(C=C1)C(F)(F)F)N)C=C(C=C2)C.BrC=2C=CC1=C(N(C(=N1)C)C1=NC(=CC(=N1)NC1=CC=C(C=C1)C(F)(F)F)N)C2 LHGYAPQIPCDEBD-UHFFFAOYSA-N 0.000 claims description 2
- XTBWDHNJMIFTJS-UHFFFAOYSA-N 2-(6-chloro-2-ethylimidazo[4,5-b]pyridin-1-yl)-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CCC1=NC2=NC=C(Cl)C=C2N1C(N=1)=NC(N)=CC=1NC1=CC=C(C(F)(F)F)C=C1 XTBWDHNJMIFTJS-UHFFFAOYSA-N 0.000 claims description 2
- TXIGDXPTDUISKY-UHFFFAOYSA-N 2-(6-chloro-2-methylbenzimidazol-1-yl)-4-n-[3-fluoro-4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC=C(Cl)C=C2N1C(N=1)=NC(N)=CC=1NC1=CC=C(C(F)(F)F)C(F)=C1 TXIGDXPTDUISKY-UHFFFAOYSA-N 0.000 claims description 2
- BIIYJNPDTOMLQX-UHFFFAOYSA-N 2-(6-chloro-2-methylbenzimidazol-1-yl)-4-n-[4-(difluoromethoxy)phenyl]pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC=C(Cl)C=C2N1C(N=1)=NC(N)=CC=1NC1=CC=C(OC(F)F)C=C1 BIIYJNPDTOMLQX-UHFFFAOYSA-N 0.000 claims description 2
- HJSMDCOHNGLPGL-UHFFFAOYSA-N 2-(6-chloro-2-methylbenzimidazol-1-yl)-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC=C(Cl)C=C2N1C(N=1)=NC(N)=CC=1NC1=CC=C(C(F)(F)F)C=C1 HJSMDCOHNGLPGL-UHFFFAOYSA-N 0.000 claims description 2
- GFUIMNDLNMZGOS-UHFFFAOYSA-N 2-(6-chloro-2-methylbenzimidazol-1-yl)-5-fluoro-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC=C(Cl)C=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(C(F)(F)F)C=C1 GFUIMNDLNMZGOS-UHFFFAOYSA-N 0.000 claims description 2
- HLIIRDRPNCAAIF-UHFFFAOYSA-N 2-(6-chloro-2-methylimidazo[4,5-b]pyridin-1-yl)-4-n-[4-(difluoromethoxy)phenyl]-5-fluoropyrimidine-4,6-diamine Chemical compound CC1=NC2=NC=C(Cl)C=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(OC(F)F)C=C1 HLIIRDRPNCAAIF-UHFFFAOYSA-N 0.000 claims description 2
- PMJCHWSVFICFKJ-UHFFFAOYSA-N 2-(6-chloro-2-methylimidazo[4,5-b]pyridin-1-yl)-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CC1=NC2=NC=C(Cl)C=C2N1C(N=1)=NC(N)=CC=1NC1=CC=C(C(F)(F)F)C=C1 PMJCHWSVFICFKJ-UHFFFAOYSA-N 0.000 claims description 2
- RCWRRMPHCVFIQD-UHFFFAOYSA-N 2-(6-chloro-2-methylimidazo[4,5-b]pyridin-1-yl)-5-fluoro-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CC1=NC2=NC=C(Cl)C=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(C(F)(F)F)C=C1 RCWRRMPHCVFIQD-UHFFFAOYSA-N 0.000 claims description 2
- ONMNPQPRTVNFIA-UHFFFAOYSA-N 2-(6-ethenyl-2-methylbenzimidazol-1-yl)-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC=C(C=C)C=C2N1C(N=1)=NC(N)=CC=1NC1=CC=C(C(F)(F)F)C=C1 ONMNPQPRTVNFIA-UHFFFAOYSA-N 0.000 claims description 2
- QAQPUSKDGSRCMG-UHFFFAOYSA-N 2-(6-ethyl-2-methylbenzimidazol-1-yl)-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound C12=CC(CC)=CC=C2N=C(C)N1C(N=1)=NC(N)=CC=1NC1=CC=C(C(F)(F)F)C=C1 QAQPUSKDGSRCMG-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- HGCRTLVHBXIHCR-UHFFFAOYSA-N 2-[2-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl]-n-[4-(trifluoromethyl)phenyl]pyrimidin-4-amine Chemical compound FC(F)(F)C=1N=C2C=NC=CN2C=1C(N=1)=NC=CC=1NC1=CC=C(C(F)(F)F)C=C1 HGCRTLVHBXIHCR-UHFFFAOYSA-N 0.000 claims description 2
- ABVXKMVWFPHUQR-UHFFFAOYSA-N 2-[2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound N=1C(C=2N3C=CC=CC3=NC=2C(F)(F)F)=NC(N)=CC=1NC1=CC=C(C(F)(F)F)C=C1 ABVXKMVWFPHUQR-UHFFFAOYSA-N 0.000 claims description 2
- XUIOTUDFMMUDTM-UHFFFAOYSA-N 2-[2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]-n-[4-(trifluoromethyl)phenyl]pyrimidin-4-amine Chemical compound FC(F)(F)C=1N=C2C=CC=CN2C=1C(N=1)=NC=CC=1NC1=CC=C(C(F)(F)F)C=C1 XUIOTUDFMMUDTM-UHFFFAOYSA-N 0.000 claims description 2
- HMDRNSWYMYNHLG-UHFFFAOYSA-N 2-[2-methyl-6-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]-n-[4-(trifluoromethyl)phenyl]pyrimidin-4-amine Chemical compound CC=1N=C2C=CC(C(F)(F)F)=CN2C=1C(N=1)=NC=CC=1NC1=CC=C(C(F)(F)F)C=C1 HMDRNSWYMYNHLG-UHFFFAOYSA-N 0.000 claims description 2
- ZCQUQCOBNADELD-UHFFFAOYSA-N 2-[5-chloro-1-methyl-2-(trifluoromethyl)indol-3-yl]-n-(4-methoxyphenyl)pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1NC1=CC=NC(C=2C3=CC(Cl)=CC=C3N(C)C=2C(F)(F)F)=N1 ZCQUQCOBNADELD-UHFFFAOYSA-N 0.000 claims description 2
- QFVLJQDOODQYKJ-UHFFFAOYSA-N 2-[5-chloro-1-methyl-2-(trifluoromethyl)indol-3-yl]-n-[4-(difluoromethoxy)phenyl]pyrimidin-4-amine Chemical compound C12=CC(Cl)=CC=C2N(C)C(C(F)(F)F)=C1C(N=1)=NC=CC=1NC1=CC=C(OC(F)F)C=C1 QFVLJQDOODQYKJ-UHFFFAOYSA-N 0.000 claims description 2
- FMYXFGFBTZSHEL-UHFFFAOYSA-N 2-[6-bromo-2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]-n-(4-methoxyphenyl)pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1NC1=CC=NC(C=2N3C=C(Br)C=CC3=NC=2C(F)(F)F)=N1 FMYXFGFBTZSHEL-UHFFFAOYSA-N 0.000 claims description 2
- SSESMQZHKWCEAE-UHFFFAOYSA-N 2-[6-chloro-2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]-n-[4-(difluoromethoxy)phenyl]pyrimidin-4-amine Chemical compound C1=CC(OC(F)F)=CC=C1NC1=CC=NC(C=2N3C=C(Cl)C=CC3=NC=2C(F)(F)F)=N1 SSESMQZHKWCEAE-UHFFFAOYSA-N 0.000 claims description 2
- LCZQVVFCWNPZPC-UHFFFAOYSA-N 2-[6-chloro-2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]-n-[4-(trifluoromethoxy)phenyl]pyrimidin-4-amine Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC1=CC=NC(C=2N3C=C(Cl)C=CC3=NC=2C(F)(F)F)=N1 LCZQVVFCWNPZPC-UHFFFAOYSA-N 0.000 claims description 2
- RIAWOSVAWZATSE-UHFFFAOYSA-N 2-[6-chloro-2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]-n-[4-(trifluoromethyl)phenyl]pyrimidin-4-amine Chemical compound FC(F)(F)C=1N=C2C=CC(Cl)=CN2C=1C(N=1)=NC=CC=1NC1=CC=C(C(F)(F)F)C=C1 RIAWOSVAWZATSE-UHFFFAOYSA-N 0.000 claims description 2
- QZWKZGZDNYFXGG-UHFFFAOYSA-N 2-[6-fluoro-2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]-n-(4-methoxyphenyl)pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1NC1=CC=NC(C=2N3C=C(F)C=CC3=NC=2C(F)(F)F)=N1 QZWKZGZDNYFXGG-UHFFFAOYSA-N 0.000 claims description 2
- KFWNXHXPKGBGTM-UHFFFAOYSA-N 2-[6-fluoro-2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]-n-(4-methylphenyl)pyrimidin-4-amine Chemical compound C1=CC(C)=CC=C1NC1=CC=NC(C=2N3C=C(F)C=CC3=NC=2C(F)(F)F)=N1 KFWNXHXPKGBGTM-UHFFFAOYSA-N 0.000 claims description 2
- LTXVRASLHBVMOE-UHFFFAOYSA-N 2-[6-fluoro-2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]-n-[4-(trifluoromethyl)phenyl]pyrimidin-4-amine Chemical compound N12C=C(F)C=CC2=NC(C(F)(F)F)=C1C(N=1)=NC=CC=1NC1=CC=C(C(F)(F)F)C=C1 LTXVRASLHBVMOE-UHFFFAOYSA-N 0.000 claims description 2
- VAFXJUBTHBKXDK-UHFFFAOYSA-N 2-[6-methoxy-2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]-n-[4-(trifluoromethoxy)phenyl]pyrimidin-4-amine Chemical compound N12C=C(OC)C=CC2=NC(C(F)(F)F)=C1C(N=1)=NC=CC=1NC1=CC=C(OC(F)(F)F)C=C1 VAFXJUBTHBKXDK-UHFFFAOYSA-N 0.000 claims description 2
- AWISRGVJUNZTGO-UHFFFAOYSA-N 2-[6-methoxy-2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]-n-[4-(trifluoromethyl)phenyl]pyrimidin-4-amine Chemical compound N12C=C(OC)C=CC2=NC(C(F)(F)F)=C1C(N=1)=NC=CC=1NC1=CC=C(C(F)(F)F)C=C1 AWISRGVJUNZTGO-UHFFFAOYSA-N 0.000 claims description 2
- IADDLYPJGNFBMR-UHFFFAOYSA-N 2-[[2-(2-methylbenzimidazol-1-yl)-6-[4-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]ethanol Chemical compound CC1=NC2=CC=CC=C2N1C(N=1)=NC(NCCO)=CC=1NC1=CC=C(C(F)(F)F)C=C1 IADDLYPJGNFBMR-UHFFFAOYSA-N 0.000 claims description 2
- IBGIGNXUYIDKBD-UHFFFAOYSA-N 2-[[2-(4,6-difluoro-2-methylbenzimidazol-1-yl)-6-[4-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]ethanol Chemical compound CC1=NC2=C(F)C=C(F)C=C2N1C(N=1)=NC(NCCO)=CC=1NC1=CC=C(C(F)(F)F)C=C1 IBGIGNXUYIDKBD-UHFFFAOYSA-N 0.000 claims description 2
- PSZKDZGRGIRMLM-UHFFFAOYSA-N 2-[[6-[4-(difluoromethoxy)anilino]-2-(2-methylbenzimidazol-1-yl)pyrimidin-4-yl]amino]ethanol Chemical compound CC1=NC2=CC=CC=C2N1C(N=1)=NC(NCCO)=CC=1NC1=CC=C(OC(F)F)C=C1 PSZKDZGRGIRMLM-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
- JNYJIRDGMLJAQG-UHFFFAOYSA-N 3-[4-amino-5-fluoro-6-[4-(trifluoromethyl)anilino]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(F)(F)F)C=C1 JNYJIRDGMLJAQG-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- LADKQJJNDCTOMT-UHFFFAOYSA-N 4-N-(2,2-difluoro-1,3-benzodioxol-5-yl)-2-(6-fluoro-2-methylbenzimidazol-1-yl)pyrimidine-4,6-diamine 2-(2-ethylbenzimidazol-1-yl)-5-fluoro-4-N-(4-methylphenyl)pyrimidine-4,6-diamine Chemical compound C(C)C1=NC2=C(N1C1=NC(=C(C(=N1)NC1=CC=C(C=C1)C)F)N)C=CC=C2.FC2(OC1=C(O2)C=CC(=C1)NC1=NC(=NC(=C1)N)N1C(=NC2=C1C=C(C=C2)F)C)F LADKQJJNDCTOMT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- NPWPKBBAJYJTBJ-UHFFFAOYSA-N 4-n-(1,3-benzodioxol-5-yl)-2-(4,6-difluoro-2-methylbenzimidazol-1-yl)-5-fluoropyrimidine-4,6-diamine Chemical compound C1=C2OCOC2=CC(NC=2C(F)=C(N)N=C(N=2)N2C3=CC(F)=CC(F)=C3N=C2C)=C1 NPWPKBBAJYJTBJ-UHFFFAOYSA-N 0.000 claims description 2
- OTHOLRUOZVNYIH-UHFFFAOYSA-N 4-n-(1,3-benzodioxol-5-yl)-5-fluoro-2-(6-methoxy-2-methylbenzimidazol-1-yl)pyrimidine-4,6-diamine Chemical compound C1=C2OCOC2=CC(NC=2C(F)=C(N)N=C(N=2)N2C(C)=NC3=CC=C(C=C32)OC)=C1 OTHOLRUOZVNYIH-UHFFFAOYSA-N 0.000 claims description 2
- FVXHKQSNYOSLOK-UHFFFAOYSA-N 4-n-(4-chloro-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(Cl)C(F)=C1 FVXHKQSNYOSLOK-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
- XKHIQNJDEOIPCY-UHFFFAOYSA-N 4-n-(4-chlorophenyl)-5-fluoro-2-(2-methylbenzimidazol-1-yl)pyrimidine-4,6-diamine;5-fluoro-4-n-(4-methoxyphenyl)-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.C1=CC(OC)=CC=C1NC1=NC(N2C3=CC=CC=C3N=C2C)=NC(N)=C1F XKHIQNJDEOIPCY-UHFFFAOYSA-N 0.000 claims description 2
- PANFRBRWYUKDON-UHFFFAOYSA-N 4-n-(4-chlorophenyl)-5-fluoro-2-(6-fluoro-2-methylbenzimidazol-1-yl)pyrimidine-4,6-diamine;5-fluoro-2-(6-fluoro-2-methylbenzimidazol-1-yl)-4-n-(4-methylphenyl)pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC=C(F)C=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(C)C=C1.CC1=NC2=CC=C(F)C=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(Cl)C=C1 PANFRBRWYUKDON-UHFFFAOYSA-N 0.000 claims description 2
- PZWVJIDJYURBSD-UHFFFAOYSA-N 4-n-(4-chlorophenyl)-5-fluoro-2-(6-fluoro-2-methylimidazo[1,2-a]pyridin-3-yl)pyrimidine-4,6-diamine Chemical compound CC=1N=C2C=CC(F)=CN2C=1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(Cl)C=C1 PZWVJIDJYURBSD-UHFFFAOYSA-N 0.000 claims description 2
- UBZDXQQGRKBHCP-UHFFFAOYSA-N 4-n-(4-chlorophenyl)-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(Cl)C=C1 UBZDXQQGRKBHCP-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
- MLEJRNHNEBIJQP-UHFFFAOYSA-N 4-n-[3-fluoro-4-(trifluoromethyl)phenyl]-2-(2-methylbenzimidazol-1-yl)pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC=CC=C2N1C(N=1)=NC(N)=CC=1NC1=CC=C(C(F)(F)F)C(F)=C1 MLEJRNHNEBIJQP-UHFFFAOYSA-N 0.000 claims description 2
- JBYQGJUEFJNLQB-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)-3-fluorophenyl]-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(F)=C1 JBYQGJUEFJNLQB-UHFFFAOYSA-N 0.000 claims description 2
- FAMKYJRTSMTPOT-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)-3-fluorophenyl]-2-(2-ethyl-6-fluorobenzimidazol-1-yl)pyrimidine-4,6-diamine Chemical compound CCC1=NC2=CC=C(F)C=C2N1C(N=1)=NC(N)=CC=1NC1=CC=C(OC(F)F)C(F)=C1 FAMKYJRTSMTPOT-UHFFFAOYSA-N 0.000 claims description 2
- VIIODKYUHUQOTI-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)-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(OC(F)F)C(F)=C1 VIIODKYUHUQOTI-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
- WKQKEKDXOPCYRC-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)-3-fluorophenyl]-2-(5,6-difluoro-2-methylbenzimidazol-1-yl)pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC(F)=C(F)C=C2N1C(N=1)=NC(N)=CC=1NC1=CC=C(OC(F)F)C(F)=C1 WKQKEKDXOPCYRC-UHFFFAOYSA-N 0.000 claims description 2
- QFCNPANJZVRAJE-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)-3-fluorophenyl]-2-(6-fluoro-2-methylbenzimidazol-1-yl)pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC=C(F)C=C2N1C(N=1)=NC(N)=CC=1NC1=CC=C(OC(F)F)C(F)=C1 QFCNPANJZVRAJE-UHFFFAOYSA-N 0.000 claims description 2
- JIMPXKNSHXLJAW-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)-3-fluorophenyl]-5-fluoro-2-(2,6,8-trimethylimidazo[1,2-a]pyrazin-3-yl)pyrimidine-4,6-diamine Chemical compound CC=1N=C2C(C)=NC(C)=CN2C=1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(OC(F)F)C(F)=C1 JIMPXKNSHXLJAW-UHFFFAOYSA-N 0.000 claims description 2
- XCINULITTUKURC-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)-3-fluorophenyl]-5-fluoro-2-(2-methylimidazo[1,2-a]pyridin-3-yl)pyrimidine-4,6-diamine Chemical compound CC=1N=C2C=CC=CN2C=1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(OC(F)F)C(F)=C1 XCINULITTUKURC-UHFFFAOYSA-N 0.000 claims description 2
- MXQGLUIZBAUBGA-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)-3-fluorophenyl]-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(F)=C1 MXQGLUIZBAUBGA-UHFFFAOYSA-N 0.000 claims description 2
- 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 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
- OSFIPAFSHUOLIS-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)phenyl]-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=C1 OSFIPAFSHUOLIS-UHFFFAOYSA-N 0.000 claims description 2
- SXBFUXDGQDHUKU-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)phenyl]-2-(2-ethyl-5-fluorobenzimidazol-1-yl)-5-fluoropyrimidine-4,6-diamine Chemical compound CCC1=NC2=CC(F)=CC=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(OC(F)F)C=C1 SXBFUXDGQDHUKU-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
- YEGULBHTVJTZKW-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)phenyl]-2-(2-ethyl-6-fluorobenzimidazol-1-yl)-5-fluoropyrimidine-4,6-diamine Chemical compound CCC1=NC2=CC=C(F)C=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(OC(F)F)C=C1 YEGULBHTVJTZKW-UHFFFAOYSA-N 0.000 claims description 2
- SZHKKJCRYDBHNF-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)phenyl]-2-(2-ethyl-6-fluorobenzimidazol-1-yl)pyrimidine-4,6-diamine Chemical compound CCC1=NC2=CC=C(F)C=C2N1C(N=1)=NC(N)=CC=1NC1=CC=C(OC(F)F)C=C1 SZHKKJCRYDBHNF-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
- LDECFTIXFXBIPB-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)phenyl]-2-(5,6-difluoro-2-methylbenzimidazol-1-yl)pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC(F)=C(F)C=C2N1C(N=1)=NC(N)=CC=1NC1=CC=C(OC(F)F)C=C1 LDECFTIXFXBIPB-UHFFFAOYSA-N 0.000 claims description 2
- TXRJMYTVXRUGTI-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)phenyl]-2-(6-fluoro-2-methylbenzimidazol-1-yl)pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC=C(F)C=C2N1C(N=1)=NC(N)=CC=1NC1=CC=C(OC(F)F)C=C1 TXRJMYTVXRUGTI-UHFFFAOYSA-N 0.000 claims description 2
- FGCFFIFOKJQAHW-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)phenyl]-2-(6-fluoro-2-methylimidazo[1,2-a]pyridin-3-yl)pyrimidine-4,6-diamine Chemical compound CC=1N=C2C=CC(F)=CN2C=1C(N=1)=NC(N)=CC=1NC1=CC=C(OC(F)F)C=C1 FGCFFIFOKJQAHW-UHFFFAOYSA-N 0.000 claims description 2
- KOIXIABGYDXHCE-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)phenyl]-2-[2-(1-methylcyclopropyl)benzimidazol-1-yl]pyrimidine-4,6-diamine Chemical compound N=1C2=CC=CC=C2N(C=2N=C(NC=3C=CC(OC(F)F)=CC=3)C=C(N)N=2)C=1C1(C)CC1 KOIXIABGYDXHCE-UHFFFAOYSA-N 0.000 claims description 2
- LZDVUNDJVSINAM-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)phenyl]-2-[2-(difluoromethyl)-6-fluorobenzimidazol-1-yl]pyrimidine-4,6-diamine Chemical compound N=1C(N2C3=CC(F)=CC=C3N=C2C(F)F)=NC(N)=CC=1NC1=CC=C(OC(F)F)C=C1 LZDVUNDJVSINAM-UHFFFAOYSA-N 0.000 claims description 2
- IBWNXYJHXSKBGF-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)phenyl]-2-[2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidine-4,6-diamine Chemical compound N=1C(C=2N3C=CC=CC3=NC=2C(F)(F)F)=NC(N)=CC=1NC1=CC=C(OC(F)F)C=C1 IBWNXYJHXSKBGF-UHFFFAOYSA-N 0.000 claims description 2
- HYGIKPZWKPXWEJ-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)phenyl]-5-fluoro-2-(2,6,8-trimethylimidazo[1,2-a]pyrazin-3-yl)pyrimidine-4,6-diamine Chemical compound CC=1N=C2C(C)=NC(C)=CN2C=1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(OC(F)F)C=C1 HYGIKPZWKPXWEJ-UHFFFAOYSA-N 0.000 claims description 2
- HSDFCHLVPYNTMT-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)phenyl]-5-fluoro-2-(2-methyl-6-nitrobenzimidazol-1-yl)pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC=C([N+]([O-])=O)C=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(OC(F)F)C=C1 HSDFCHLVPYNTMT-UHFFFAOYSA-N 0.000 claims description 2
- YSZKHVKQHPAPQQ-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)phenyl]-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=C1 YSZKHVKQHPAPQQ-UHFFFAOYSA-N 0.000 claims description 2
- UKJQZVAEURPUIL-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)phenyl]-5-fluoro-2-(2-methylimidazo[1,2-a]pyridin-3-yl)pyrimidine-4,6-diamine Chemical compound CC=1N=C2C=CC=CN2C=1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(OC(F)F)C=C1 UKJQZVAEURPUIL-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
- PPCADDPUTXGKPU-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)phenyl]-5-fluoro-2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)pyrimidine-4,6-diamine Chemical compound CC1=NN2C=CC=CC2=C1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(OC(F)F)C=C1 PPCADDPUTXGKPU-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
- 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 2
- BHCYZQAMCOXETI-UHFFFAOYSA-N 4-n-[4-(dimethylamino)phenyl]-2-(2-methylbenzimidazol-1-yl)pyrimidine-4,6-diamine;5-fluoro-2-(2-methylbenzimidazol-1-yl)-4-n-(4-methylphenyl)pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC=CC=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(C)C=C1.C1=CC(N(C)C)=CC=C1NC1=CC(N)=NC(N2C3=CC=CC=C3N=C2C)=N1 BHCYZQAMCOXETI-UHFFFAOYSA-N 0.000 claims description 2
- XRVYFSOHPFWNNN-UHFFFAOYSA-N 4-n-[4-(trifluoromethyl)phenyl]-2-(2,5,6-trimethylbenzimidazol-1-yl)pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC(C)=C(C)C=C2N1C(N=1)=NC(N)=CC=1NC1=CC=C(C(F)(F)F)C=C1 XRVYFSOHPFWNNN-UHFFFAOYSA-N 0.000 claims description 2
- KRPKFTLPCRSRPC-UHFFFAOYSA-N 5-chloro-2-(2-ethylbenzimidazol-1-yl)-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CCC1=NC2=CC=CC=C2N1C(N=1)=NC(N)=C(Cl)C=1NC1=CC=C(C(F)(F)F)C=C1 KRPKFTLPCRSRPC-UHFFFAOYSA-N 0.000 claims description 2
- ZTMDMDZUVBFLHF-UHFFFAOYSA-N 5-chloro-2-(2-methylbenzimidazol-1-yl)-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC=CC=C2N1C(N=1)=NC(N)=C(Cl)C=1NC1=CC=C(C(F)(F)F)C=C1 ZTMDMDZUVBFLHF-UHFFFAOYSA-N 0.000 claims description 2
- KMUCCEQQBNEBOG-UHFFFAOYSA-N 5-chloro-4-n-[4-(difluoromethoxy)phenyl]-2-(2-ethylbenzimidazol-1-yl)pyrimidine-4,6-diamine Chemical compound CCC1=NC2=CC=CC=C2N1C(N=1)=NC(N)=C(Cl)C=1NC1=CC=C(OC(F)F)C=C1 KMUCCEQQBNEBOG-UHFFFAOYSA-N 0.000 claims description 2
- LHBNBNGBTMLDML-UHFFFAOYSA-N 5-chloro-N-(4-methylphenyl)-2-[2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-4-amine N-(4-methoxyphenyl)-2-[2-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl]pyrimidin-4-amine Chemical compound COC1=CC=C(C=C1)NC1=NC(=NC=C1)C1=C(N=C2N1C=CN=C2)C(F)(F)F.ClC=2C(=NC(=NC2)C2=C(N=C1N2C=CC=C1)C(F)(F)F)NC1=CC=C(C=C1)C LHBNBNGBTMLDML-UHFFFAOYSA-N 0.000 claims description 2
- ZRZOQIFKQBPEII-UHFFFAOYSA-N 5-fluoro-2-(2-methyl-6-nitrobenzimidazol-1-yl)-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC=C([N+]([O-])=O)C=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(C(F)(F)F)C=C1 ZRZOQIFKQBPEII-UHFFFAOYSA-N 0.000 claims description 2
- UYXXEZJUXGHMQH-UHFFFAOYSA-N 5-fluoro-2-(2-methylbenzimidazol-1-yl)-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC=CC=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(C(F)(F)F)C=C1 UYXXEZJUXGHMQH-UHFFFAOYSA-N 0.000 claims description 2
- SPJWHRBEQIAYCD-UHFFFAOYSA-N 5-fluoro-2-(2-methylimidazo[1,2-a]pyridin-3-yl)-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CC=1N=C2C=CC=CN2C=1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(C(F)(F)F)C=C1 SPJWHRBEQIAYCD-UHFFFAOYSA-N 0.000 claims description 2
- DNYLVOFGOQZJAP-UHFFFAOYSA-N 5-fluoro-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)=C(F)C=1NC1=CC=C(C(F)(F)F)C=C1 DNYLVOFGOQZJAP-UHFFFAOYSA-N 0.000 claims description 2
- DXTOIQHKNSNXDP-UHFFFAOYSA-N 5-fluoro-2-(5-fluoro-2-methylbenzimidazol-1-yl)-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC(F)=CC=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(C(F)(F)F)C=C1 DXTOIQHKNSNXDP-UHFFFAOYSA-N 0.000 claims description 2
- SGRWYWLNQUUTOM-UHFFFAOYSA-N 5-fluoro-2-(6-fluoro-2-methylbenzimidazol-1-yl)-4-n-(4-methoxyphenyl)pyrimidine-4,6-diamine Chemical compound C1=CC(OC)=CC=C1NC1=NC(N2C3=CC(F)=CC=C3N=C2C)=NC(N)=C1F SGRWYWLNQUUTOM-UHFFFAOYSA-N 0.000 claims description 2
- LOOYMJVHKCMLCS-UHFFFAOYSA-N 5-fluoro-2-(6-fluoro-2-methylbenzimidazol-1-yl)-4-n-[4-(trifluoromethoxy)phenyl]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)F)C=C1 LOOYMJVHKCMLCS-UHFFFAOYSA-N 0.000 claims description 2
- TWLWOOPCEXYVBE-UHFFFAOYSA-N 5-fluoro-2-(6-fluoro-2-methylbenzimidazol-1-yl)-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC=C(F)C=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(C(F)(F)F)C=C1 TWLWOOPCEXYVBE-UHFFFAOYSA-N 0.000 claims description 2
- MZDQBDVWRILKJW-UHFFFAOYSA-N 5-fluoro-2-(6-fluoro-2-methylbenzimidazol-1-yl)-4-n-[6-(trifluoromethyl)pyridin-3-yl]pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC=C(F)C=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(C(F)(F)F)N=C1 MZDQBDVWRILKJW-UHFFFAOYSA-N 0.000 claims description 2
- GNJWDKYSGXPRAU-UHFFFAOYSA-N 5-fluoro-2-(6-fluoro-2-methylimidazo[1,2-a]pyridin-3-yl)-4-n-(4-methoxyphenyl)pyrimidine-4,6-diamine Chemical compound C1=CC(OC)=CC=C1NC1=NC(C=2N3C=C(F)C=CC3=NC=2C)=NC(N)=C1F GNJWDKYSGXPRAU-UHFFFAOYSA-N 0.000 claims description 2
- BONXSHDUNVHXFI-UHFFFAOYSA-N 5-fluoro-2-(6-fluoro-2-methylimidazo[1,2-a]pyridin-3-yl)-4-n-(4-methylphenyl)pyrimidine-4,6-diamine Chemical compound CC=1N=C2C=CC(F)=CN2C=1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(C)C=C1 BONXSHDUNVHXFI-UHFFFAOYSA-N 0.000 claims description 2
- IOMXJUSZYGCGHT-UHFFFAOYSA-N 5-fluoro-2-(6-methoxy-2-methylbenzimidazol-1-yl)-4-n-[4-(trifluoromethoxy)phenyl]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)F)C=C1 IOMXJUSZYGCGHT-UHFFFAOYSA-N 0.000 claims description 2
- QMFJALQDYJMASJ-UHFFFAOYSA-N 5-fluoro-2-(6-methoxy-2-methylbenzimidazol-1-yl)-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound C12=CC(OC)=CC=C2N=C(C)N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(C(F)(F)F)C=C1 QMFJALQDYJMASJ-UHFFFAOYSA-N 0.000 claims description 2
- QIRVGNMVLVKHSJ-UHFFFAOYSA-N 5-fluoro-2-[2-(methoxymethyl)benzimidazol-1-yl]-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound COCC1=NC2=CC=CC=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(C(F)(F)F)C=C1 QIRVGNMVLVKHSJ-UHFFFAOYSA-N 0.000 claims description 2
- KVDCLFKKOMKPMJ-UHFFFAOYSA-N 5-fluoro-2-[6-fluoro-2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound FC=1C(N)=NC(C=2N3C=C(F)C=CC3=NC=2C(F)(F)F)=NC=1NC1=CC=C(C(F)(F)F)C=C1 KVDCLFKKOMKPMJ-UHFFFAOYSA-N 0.000 claims description 2
- BKYUQWLCZBLBGF-UHFFFAOYSA-N 5-fluoro-4-n-(4-methoxyphenyl)-2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)pyrimidine-4,6-diamine Chemical compound C1=CC(OC)=CC=C1NC1=NC(C2=C3C=CC=CN3N=C2C)=NC(N)=C1F BKYUQWLCZBLBGF-UHFFFAOYSA-N 0.000 claims description 2
- AWFLXGFPBGZGII-UHFFFAOYSA-N 5-fluoro-4-n-[4-(trifluoromethyl)phenyl]-2-(2,6,8-trimethylimidazo[1,2-a]pyrazin-3-yl)pyrimidine-4,6-diamine Chemical compound CC=1N=C2C(C)=NC(C)=CN2C=1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(C(F)(F)F)C=C1 AWFLXGFPBGZGII-UHFFFAOYSA-N 0.000 claims description 2
- GJGRNSGICYUXDW-UHFFFAOYSA-N 5-fluoro-n-(4-methylphenyl)-2-[2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-4-amine Chemical compound C1=CC(C)=CC=C1NC1=NC(C=2N3C=CC=CC3=NC=2C(F)(F)F)=NC=C1F GJGRNSGICYUXDW-UHFFFAOYSA-N 0.000 claims description 2
- DBXROTSVQBURKY-UHFFFAOYSA-N 5-methyl-2-(2-methylbenzimidazol-1-yl)-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC=CC=C2N1C(N=1)=NC(N)=C(C)C=1NC1=CC=C(C(F)(F)F)C=C1 DBXROTSVQBURKY-UHFFFAOYSA-N 0.000 claims description 2
- GVZWNZUPLWETCC-UHFFFAOYSA-N C(C)C1=NC2=C(N1C1=NC(=CC(=N1)NC1=CC=C(C=C1)C(F)(F)F)N)C=CC=C2.FC(C2=NC1=C(N2C2=NC(=CC(=N2)NC2=CC=C(C=C2)C(F)(F)F)N)C=CC=C1)F Chemical compound C(C)C1=NC2=C(N1C1=NC(=CC(=N1)NC1=CC=C(C=C1)C(F)(F)F)N)C=CC=C2.FC(C2=NC1=C(N2C2=NC(=CC(=N2)NC2=CC=C(C=C2)C(F)(F)F)N)C=CC=C1)F GVZWNZUPLWETCC-UHFFFAOYSA-N 0.000 claims description 2
- MCYGWCNGXCMSMZ-UHFFFAOYSA-N C1(CC1)C1=NC2=C(N1C1=NC(=C(C(=N1)NC1=CC=C(C=C1)C)F)N)C=CC=C2.ClC2=C(C=C(C=C2)NC2=NC(=NC(=C2F)N)N2C(=NC1=C2C=CC=C1)CC)F Chemical compound C1(CC1)C1=NC2=C(N1C1=NC(=C(C(=N1)NC1=CC=C(C=C1)C)F)N)C=CC=C2.ClC2=C(C=C(C=C2)NC2=NC(=NC(=C2F)N)N2C(=NC1=C2C=CC=C1)CC)F MCYGWCNGXCMSMZ-UHFFFAOYSA-N 0.000 claims description 2
- GDFYHWJJCNDOLP-UHFFFAOYSA-N CC1(CC1)C1=NC2=C(N1C1=NC(=CC(=N1)NC1=CC=C(C=C1)C(F)(F)F)N)C=CC=C2 Chemical compound CC1(CC1)C1=NC2=C(N1C1=NC(=CC(=N1)NC1=CC=C(C=C1)C(F)(F)F)N)C=CC=C2 GDFYHWJJCNDOLP-UHFFFAOYSA-N 0.000 claims description 2
- DHXVICCOZIKTDW-UHFFFAOYSA-N CC1=CC=C(C=C1)NC1=NC(=NC=C1)C1=C(N=C2N1C=CN=C2)C(F)(F)F.FC(OC2=CC=C(C=C2)NC2=NC(=NC=C2)N2C(=NC1=C2C=CC=C1)C)F Chemical compound CC1=CC=C(C=C1)NC1=NC(=NC=C1)C1=C(N=C2N1C=CN=C2)C(F)(F)F.FC(OC2=CC=C(C=C2)NC2=NC(=NC=C2)N2C(=NC1=C2C=CC=C1)C)F DHXVICCOZIKTDW-UHFFFAOYSA-N 0.000 claims description 2
- LZFHDMVPTPCHGC-UHFFFAOYSA-N CC1=NC2=C(N1C1=NC(=CC(=N1)NC1=CC=C(C=C1)[N+](=O)[O-])N)C=CC=C2.NC2=CC(=NC(=N2)N2C(=NC1=C2C=CC=C1)C)NC1=CC=C(C#N)C=C1 Chemical compound CC1=NC2=C(N1C1=NC(=CC(=N1)NC1=CC=C(C=C1)[N+](=O)[O-])N)C=CC=C2.NC2=CC(=NC(=N2)N2C(=NC1=C2C=CC=C1)C)NC1=CC=C(C#N)C=C1 LZFHDMVPTPCHGC-UHFFFAOYSA-N 0.000 claims description 2
- ULLLDJRLWCGDGV-UHFFFAOYSA-N CC=1N=C2N(C=CC=C2)C1C1=NC=CC(=N1)NC1=CC=CC=C1.ClC1=CC=C(C=C1)NC1=NC(=NC=C1)C1=C(N=C2N1C=CC=C2)C Chemical compound CC=1N=C2N(C=CC=C2)C1C1=NC=CC(=N1)NC1=CC=CC=C1.ClC1=CC=C(C=C1)NC1=NC(=NC=C1)C1=C(N=C2N1C=CC=C2)C ULLLDJRLWCGDGV-UHFFFAOYSA-N 0.000 claims description 2
- FALKPOQMMLMNTB-UHFFFAOYSA-N CN(C1=CC=C(C=C1)NC1=NC(=NC(=C1)N)N1C(=NC2=C1C=C(C=C2)F)C)C.FC=2C=CC1=C(N(C(=N1)C)C1=NC(=CC(=N1)NC1=CC=C(C=C1)OC)N)C2 Chemical compound CN(C1=CC=C(C=C1)NC1=NC(=NC(=C1)N)N1C(=NC2=C1C=C(C=C2)F)C)C.FC=2C=CC1=C(N(C(=N1)C)C1=NC(=CC(=N1)NC1=CC=C(C=C1)OC)N)C2 FALKPOQMMLMNTB-UHFFFAOYSA-N 0.000 claims description 2
- JLMCUFGTJIAUDO-UHFFFAOYSA-N COC1=CC=C(C=C1)NC1=NC(=NC(=C1)N)N1C(=NC2=C1C=CC=C2)C.CC2=NC1=C(N2C2=NC(=CC(=N2)NC2=CC=C(C=C2)C)N)C=CC=C1 Chemical compound COC1=CC=C(C=C1)NC1=NC(=NC(=C1)N)N1C(=NC2=C1C=CC=C2)C.CC2=NC1=C(N2C2=NC(=CC(=N2)NC2=CC=C(C=C2)C)N)C=CC=C1 JLMCUFGTJIAUDO-UHFFFAOYSA-N 0.000 claims description 2
- ASAFPUKUUZELJN-UHFFFAOYSA-N COCC1=NC2=C(N1C1=NC(=CC(=N1)NC1=CC=C(C=C1)C(F)(F)F)N)C=CC=C2 Chemical compound COCC1=NC2=C(N1C1=NC(=CC(=N1)NC1=CC=C(C=C1)C(F)(F)F)N)C=CC=C2 ASAFPUKUUZELJN-UHFFFAOYSA-N 0.000 claims description 2
- BAZFDUMNSHDMNF-UHFFFAOYSA-N ClC1=C(C=C(C=C1)NC1=NC(=NC(=C1F)N)N1C(=NC2=C1C=CC=C2)C2CC2)F.ClC2=CC=C(C=C2)NC2=NC(=NC(=C2F)N)N2C(=NC1=C2C=CC=C1)C1CC1 Chemical compound ClC1=C(C=C(C=C1)NC1=NC(=NC(=C1F)N)N1C(=NC2=C1C=CC=C2)C2CC2)F.ClC2=CC=C(C=C2)NC2=NC(=NC(=C2F)N)N2C(=NC1=C2C=CC=C1)C1CC1 BAZFDUMNSHDMNF-UHFFFAOYSA-N 0.000 claims description 2
- ZRAVQDBWXJKXOU-UHFFFAOYSA-N ClC1=CC=C(C=C1)NC1=NC(=NC(=C1)N)N1C(=NC2=C1C=CC=C2)C.COC2=CC=C(C=N2)NC2=NC(=NC(=C2)N)N2C(=NC1=C2C=CC=C1)C Chemical compound ClC1=CC=C(C=C1)NC1=NC(=NC(=C1)N)N1C(=NC2=C1C=CC=C2)C.COC2=CC=C(C=N2)NC2=NC(=NC(=C2)N)N2C(=NC1=C2C=CC=C1)C ZRAVQDBWXJKXOU-UHFFFAOYSA-N 0.000 claims description 2
- JRBMNOZWABERNS-UHFFFAOYSA-N ClC1=CC=C(C=C1)NC1=NC(=NC(=C1F)N)N1C(=NC2=C1C=C(C(=C2)F)F)C Chemical compound ClC1=CC=C(C=C1)NC1=NC(=NC(=C1F)N)N1C(=NC2=C1C=C(C(=C2)F)F)C JRBMNOZWABERNS-UHFFFAOYSA-N 0.000 claims description 2
- ODOAYWBJDZUIEL-UHFFFAOYSA-N ClC1=CC=C(C=C1)NC1=NC(=NC(=C1F)N)N1C(=NC2=C1C=CC=C2)CC.O2COC1=C2C=CC(=C1)NC1=NC(=NC(=C1F)N)N1C(=NC2=C1C=CC=C2)CC Chemical compound ClC1=CC=C(C=C1)NC1=NC(=NC(=C1F)N)N1C(=NC2=C1C=CC=C2)CC.O2COC1=C2C=CC(=C1)NC1=NC(=NC(=C1F)N)N1C(=NC2=C1C=CC=C2)CC ODOAYWBJDZUIEL-UHFFFAOYSA-N 0.000 claims description 2
- NSULYAPJFIAQMQ-UHFFFAOYSA-N ClC=1C=C(C=CC1)NC1=NC(=NC(=C1F)N)N1C(=NC2=C1C=C(C=C2)F)C.FC=2C(=NC(=NC2N)N2C(=NC1=C2C=C(C=C1)F)C)NC1=CC(=CC=C1)OC Chemical compound ClC=1C=C(C=CC1)NC1=NC(=NC(=C1F)N)N1C(=NC2=C1C=C(C=C2)F)C.FC=2C(=NC(=NC2N)N2C(=NC1=C2C=C(C=C1)F)C)NC1=CC(=CC=C1)OC NSULYAPJFIAQMQ-UHFFFAOYSA-N 0.000 claims description 2
- PAZSUMRGDKVNMG-UHFFFAOYSA-N ClC=1C=C2C(=NC1)N=C(N2C2=NC(=C(C(=N2)NC2=CC(=C(C=C2)OC(F)F)F)F)N)C Chemical compound ClC=1C=C2C(=NC1)N=C(N2C2=NC(=C(C(=N2)NC2=CC(=C(C=C2)OC(F)F)F)F)N)C PAZSUMRGDKVNMG-UHFFFAOYSA-N 0.000 claims description 2
- BIIRZOCMQXRDKQ-UHFFFAOYSA-N FC(OC1=C(C=C(C=C1)NC1=NC(=NC(=C1)N)N1C(=NC2=C1C=CC=C2)CC)F)F.FC(OC2=CC=C(C=C2)NC2=NC(=NC(=C2)N)N2C(=NC1=C2C=CC=C1)CC)F Chemical compound FC(OC1=C(C=C(C=C1)NC1=NC(=NC(=C1)N)N1C(=NC2=C1C=CC=C2)CC)F)F.FC(OC2=CC=C(C=C2)NC2=NC(=NC(=C2)N)N2C(=NC1=C2C=CC=C1)CC)F BIIRZOCMQXRDKQ-UHFFFAOYSA-N 0.000 claims description 2
- NJTCTRFKKSAUMU-UHFFFAOYSA-N FC(OC1=CC=C(C=C1)NC1=NC(=NC(=C1F)N)N1C(=NC2=C1C=CC=C2)COC)F Chemical compound FC(OC1=CC=C(C=C1)NC1=NC(=NC(=C1F)N)N1C(=NC2=C1C=CC=C2)COC)F NJTCTRFKKSAUMU-UHFFFAOYSA-N 0.000 claims description 2
- ZJSSCSXMNDMOLS-UHFFFAOYSA-N FC1=CC2=C(N(C(=N2)C)C2=NC(=C(C(=N2)NC2=CC=C(C=C2)C)F)N)C=C1F.BrC1=CC=C(C=C1)NC1=NC(=NC(=C1)N)N1C(=NC2=C1C=CC=C2)C Chemical compound FC1=CC2=C(N(C(=N2)C)C2=NC(=C(C(=N2)NC2=CC=C(C=C2)C)F)N)C=C1F.BrC1=CC=C(C=C1)NC1=NC(=NC(=C1)N)N1C(=NC2=C1C=CC=C2)C ZJSSCSXMNDMOLS-UHFFFAOYSA-N 0.000 claims description 2
- YRFWSUFIXBGLNP-UHFFFAOYSA-N FC1=CC2=C(N(C(=N2)C)C2=NC(=CC(=N2)NC2=CC=C(C=C2)C(F)(F)F)N)C=C1F.CC1=NC2=C(N1C1=NC(=CC(=N1)NC1=CC=C(C=C1)C(F)(F)F)N)C=CC=C2 Chemical compound FC1=CC2=C(N(C(=N2)C)C2=NC(=CC(=N2)NC2=CC=C(C=C2)C(F)(F)F)N)C=C1F.CC1=NC2=C(N1C1=NC(=CC(=N1)NC1=CC=C(C=C1)C(F)(F)F)N)C=CC=C2 YRFWSUFIXBGLNP-UHFFFAOYSA-N 0.000 claims description 2
- NTZWANXBHCJQEQ-UHFFFAOYSA-N FC=1C(=NC(=NC1N)N1C(=NC2=C1C=CC(=C2)F)C)NC2=CC=C(C=C2)OC(F)(F)F Chemical compound FC=1C(=NC(=NC1N)N1C(=NC2=C1C=CC(=C2)F)C)NC2=CC=C(C=C2)OC(F)(F)F NTZWANXBHCJQEQ-UHFFFAOYSA-N 0.000 claims description 2
- UQTFSMRMCZINPR-UHFFFAOYSA-N FC=1C(=NC(=NC1N)N1C(=NC2=C1C=CC(=C2)F)C)NC2=CC=C(C=C2)OC.FC=2C(=NC(=NC2N)N2C(=NC1=C2C=CC(=C1)F)C)NC1=CC=C(C=C1)C Chemical compound FC=1C(=NC(=NC1N)N1C(=NC2=C1C=CC(=C2)F)C)NC2=CC=C(C=C2)OC.FC=2C(=NC(=NC2N)N2C(=NC1=C2C=CC(=C1)F)C)NC1=CC=C(C=C1)C UQTFSMRMCZINPR-UHFFFAOYSA-N 0.000 claims description 2
- XPJKJOYHJIFRMM-UHFFFAOYSA-N FC=1C(=NC(=NC1N)N1C(=NC2=C1C=CC=C2)COC)NC2=CC=C(C=C2)OC.FC=2C(=NC(=NC2N)N2C(=NC1=C2C=CC=C1)COC)NC1=CC=C(C=C1)C Chemical compound FC=1C(=NC(=NC1N)N1C(=NC2=C1C=CC=C2)COC)NC2=CC=C(C=C2)OC.FC=2C(=NC(=NC2N)N2C(=NC1=C2C=CC=C1)COC)NC1=CC=C(C=C1)C XPJKJOYHJIFRMM-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- MUVWORCWAMURTA-UHFFFAOYSA-N FC=1C=C(C=CC1OC)NC1=NC(=NC(=C1)N)N1C(=NC2=C1C=CC=C2)C.FC2(OC1=C(O2)C=CC(=C1)NC1=NC(=NC(=C1)N)N1C(=NC2=C1C=CC=C2)C)F Chemical compound FC=1C=C(C=CC1OC)NC1=NC(=NC(=C1)N)N1C(=NC2=C1C=CC=C2)C.FC2(OC1=C(O2)C=CC(=C1)NC1=NC(=NC(=C1)N)N1C(=NC2=C1C=CC=C2)C)F MUVWORCWAMURTA-UHFFFAOYSA-N 0.000 claims description 2
- BACSOUPZROAAEY-UHFFFAOYSA-N FC=1C=CC2=C(N(C(=N2)C)C2=NC(=CC(=N2)NC2=CC(=CC=C2)C)N)C1.ClC1=C(C=C(C=C1)NC1=NC(=NC(=C1)N)N1C(=NC2=C1C=C(C=C2)F)C)F Chemical compound FC=1C=CC2=C(N(C(=N2)C)C2=NC(=CC(=N2)NC2=CC(=CC=C2)C)N)C1.ClC1=C(C=C(C=C1)NC1=NC(=NC(=C1)N)N1C(=NC2=C1C=C(C=C2)F)C)F BACSOUPZROAAEY-UHFFFAOYSA-N 0.000 claims description 2
- YPLCXXDUFHDETQ-UHFFFAOYSA-N FC=1C=CC2=C(N(C(=N2)C)C2=NC(=CC(=N2)NC2=CC=C(C=C2)C(F)(F)F)N)C1.FC(C1=CC=C(C=C1)NC1=NC(=NC(=C1)N)C=1C(=NN(C1C)C)C)(F)F Chemical compound FC=1C=CC2=C(N(C(=N2)C)C2=NC(=CC(=N2)NC2=CC=C(C=C2)C(F)(F)F)N)C1.FC(C1=CC=C(C=C1)NC1=NC(=NC(=C1)N)C=1C(=NN(C1C)C)C)(F)F YPLCXXDUFHDETQ-UHFFFAOYSA-N 0.000 claims description 2
- YGKVQBYLUUKSAJ-UHFFFAOYSA-N FC=1C=CC2=C(N(C(=N2)C)C2=NC(=CC(=N2)NC2=CC=C(C=C2)C)N)C1.ClC1=CC=C(C=C1)NC1=NC(=NC(=C1)N)N1C(=NC2=C1C=C(C=C2)F)C Chemical compound FC=1C=CC2=C(N(C(=N2)C)C2=NC(=CC(=N2)NC2=CC=C(C=C2)C)N)C1.ClC1=CC=C(C=C1)NC1=NC(=NC(=C1)N)N1C(=NC2=C1C=C(C=C2)F)C YGKVQBYLUUKSAJ-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- ZTWDCOGOJBOJED-UHFFFAOYSA-N N-(1,3-benzodioxol-5-yl)-2-[2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-4-amine 2-(6-fluoro-2-phenylimidazo[1,2-a]pyridin-3-yl)-N-(4-methylphenyl)pyrimidin-4-amine Chemical compound O1COC2=C1C=CC(=C2)NC2=NC(=NC=C2)C2=C(N=C1N2C=CC=C1)C(F)(F)F.FC=1C=CC=2N(C1)C(=C(N2)C2=CC=CC=C2)C2=NC=CC(=N2)NC2=CC=C(C=C2)C ZTWDCOGOJBOJED-UHFFFAOYSA-N 0.000 claims description 2
- JZCKULJSVZCWNO-UHFFFAOYSA-N N-(3-chloro-4-methylphenyl)-2-[2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-4-amine N-(4-ethoxyphenyl)-2-[2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-4-amine Chemical compound C(C)OC1=CC=C(C=C1)NC1=NC(=NC=C1)C1=C(N=C2N1C=CC=C2)C(F)(F)F.ClC=2C=C(C=CC2C)NC2=NC(=NC=C2)C2=C(N=C1N2C=CC=C1)C(F)(F)F JZCKULJSVZCWNO-UHFFFAOYSA-N 0.000 claims description 2
- VPVCMNOYJXQNBC-UHFFFAOYSA-N N-(4-bromophenyl)-2-[5-chloro-1-methyl-2-(trifluoromethyl)indol-3-yl]pyrimidin-4-amine N-(4-bromophenyl)-2-(6-fluoro-2-phenylimidazo[1,2-a]pyridin-3-yl)pyrimidin-4-amine Chemical compound BrC1=CC=C(C=C1)NC1=NC(=NC=C1)C1=C(N=C2N1C=C(C=C2)F)C2=CC=CC=C2.BrC2=CC=C(C=C2)NC2=NC(=NC=C2)C2=C(N(C1=CC=C(C=C21)Cl)C)C(F)(F)F VPVCMNOYJXQNBC-UHFFFAOYSA-N 0.000 claims description 2
- YYTWWNLIKRPNBV-UHFFFAOYSA-N N-(4-methoxyphenyl)-2-(2-methylimidazo[1,2-a]pyridin-3-yl)pyrimidin-4-amine 2-(2-methylimidazo[1,2-a]pyridin-3-yl)-N-[4-(trifluoromethyl)phenyl]pyrimidin-4-amine Chemical compound COC1=CC=C(C=C1)NC1=NC(=NC=C1)C1=C(N=C2N1C=CC=C2)C.CC=2N=C1N(C=CC=C1)C2C2=NC=CC(=N2)NC2=CC=C(C=C2)C(F)(F)F YYTWWNLIKRPNBV-UHFFFAOYSA-N 0.000 claims description 2
- IPNVDRMKIKVNCG-UHFFFAOYSA-N N-[4-(difluoromethoxy)phenyl]-2-[2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-4-amine N-(4-methoxyphenyl)-2-[2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-4-amine Chemical compound COC1=CC=C(C=C1)NC1=NC(=NC=C1)C1=C(N=C2N1C=CC=C2)C(F)(F)F.FC(OC2=CC=C(C=C2)NC2=NC(=NC=C2)C2=C(N=C1N2C=CC=C1)C(F)(F)F)F IPNVDRMKIKVNCG-UHFFFAOYSA-N 0.000 claims description 2
- MHZQKDXKXONSFX-UHFFFAOYSA-N O1CCOC2=C1C=CC(=C2)NC2=NC(=NC=C2)C2=C(N=C1N2C=CC=C1)C.COC1=CC=C(C=C1)NC1=NC(=NC=C1)N1C(=NC2=C1C=CC=C2)C Chemical compound O1CCOC2=C1C=CC(=C2)NC2=NC(=NC=C2)C2=C(N=C1N2C=CC=C1)C.COC1=CC=C(C=C1)NC1=NC(=NC=C1)N1C(=NC2=C1C=CC=C2)C MHZQKDXKXONSFX-UHFFFAOYSA-N 0.000 claims description 2
- QRDVQQUSCCPXEZ-UHFFFAOYSA-N O1COC2=C1C=CC(=C2)NC2=NC(=NC(=C2)N)N2C(=NC1=C2C=CC=C1)C.FC=1C(=NC(=NC1N)N1C(=NC2=C1C=CC=C2)C)NC2=CC=C(C=C2)OC(F)(F)F Chemical compound O1COC2=C1C=CC(=C2)NC2=NC(=NC(=C2)N)N2C(=NC1=C2C=CC=C1)C.FC=1C(=NC(=NC1N)N1C(=NC2=C1C=CC=C2)C)NC2=CC=C(C=C2)OC(F)(F)F QRDVQQUSCCPXEZ-UHFFFAOYSA-N 0.000 claims description 2
- BOZKLTDEHJEFOY-UHFFFAOYSA-N O1COC2=C1C=CC(=C2)NC2=NC(=NC(=C2F)N)N2C(=NC1=C2C=CC=C1)C.NC1=C(C(=NC(=N1)N1C(=NC2=C1C=CC=C2)C)NC2=CC=C(C#N)C=C2)F Chemical compound O1COC2=C1C=CC(=C2)NC2=NC(=NC(=C2F)N)N2C(=NC1=C2C=CC=C1)C.NC1=C(C(=NC(=N1)N1C(=NC2=C1C=CC=C2)C)NC2=CC=C(C#N)C=C2)F BOZKLTDEHJEFOY-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
- WMAUYKBSGFPVBV-UHFFFAOYSA-N [3-[4-amino-6-[4-(trifluoromethyl)anilino]pyrimidin-2-yl]-6-fluoroimidazo[1,2-a]pyridin-2-yl]methanol Chemical compound N=1C(C=2N3C=C(F)C=CC3=NC=2CO)=NC(N)=CC=1NC1=CC=C(C(F)(F)F)C=C1 WMAUYKBSGFPVBV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 2
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- ODWNYTMYRGETSI-UHFFFAOYSA-N n-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-[2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-4-amine Chemical compound O1CCOC2=CC(NC=3C=CN=C(N=3)C=3N4C=CC=CC4=NC=3C(F)(F)F)=CC=C21 ODWNYTMYRGETSI-UHFFFAOYSA-N 0.000 claims description 2
- PIJSEAMGYSSDTB-UHFFFAOYSA-N n-(4-bromophenyl)-2-[2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-4-amine Chemical compound FC(F)(F)C=1N=C2C=CC=CN2C=1C(N=1)=NC=CC=1NC1=CC=C(Br)C=C1 PIJSEAMGYSSDTB-UHFFFAOYSA-N 0.000 claims description 2
- GVAZKGIQOVJCID-UHFFFAOYSA-N n-(4-bromophenyl)-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(Br)C=C1 GVAZKGIQOVJCID-UHFFFAOYSA-N 0.000 claims description 2
- QYAPNGLJIWHOAU-UHFFFAOYSA-N n-(4-bromophenyl)-2-[6-chloro-2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-4-amine Chemical compound FC(F)(F)C=1N=C2C=CC(Cl)=CN2C=1C(N=1)=NC=CC=1NC1=CC=C(Br)C=C1 QYAPNGLJIWHOAU-UHFFFAOYSA-N 0.000 claims description 2
- LJUCQRSAGOGDGE-UHFFFAOYSA-N n-(4-chlorophenyl)-2-[2-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl]pyrimidin-4-amine Chemical compound FC(F)(F)C=1N=C2C=NC=CN2C=1C(N=1)=NC=CC=1NC1=CC=C(Cl)C=C1 LJUCQRSAGOGDGE-UHFFFAOYSA-N 0.000 claims description 2
- LTZJRXPWFJEIGR-UHFFFAOYSA-N n-(4-chlorophenyl)-2-[6-chloro-2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-4-amine Chemical compound FC(F)(F)C=1N=C2C=CC(Cl)=CN2C=1C(N=1)=NC=CC=1NC1=CC=C(Cl)C=C1 LTZJRXPWFJEIGR-UHFFFAOYSA-N 0.000 claims description 2
- IRVGQPHSSXIPLW-UHFFFAOYSA-N n-(4-methoxyphenyl)-2-[6-methoxy-2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1NC1=CC=NC(C=2N3C=C(OC)C=CC3=NC=2C(F)(F)F)=N1 IRVGQPHSSXIPLW-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- NRGAXCLUNNBVKC-UHFFFAOYSA-N n-(4-propan-2-ylphenyl)-2-[2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-4-amine Chemical compound C1=CC(C(C)C)=CC=C1NC1=CC=NC(C=2N3C=CC=CC3=NC=2C(F)(F)F)=N1 NRGAXCLUNNBVKC-UHFFFAOYSA-N 0.000 claims description 2
- ZWSABTRUKBCJTH-UHFFFAOYSA-N n-(6-methoxypyridin-3-yl)-2-[2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-4-amine Chemical compound C1=NC(OC)=CC=C1NC1=CC=NC(C=2N3C=CC=CC3=NC=2C(F)(F)F)=N1 ZWSABTRUKBCJTH-UHFFFAOYSA-N 0.000 claims description 2
- OSVFBZGITOSJBZ-UHFFFAOYSA-N n-[4-(difluoromethoxy)phenyl]-2-[2-(trifluoromethyl)imidazo[1,2-a]pyrazin-3-yl]pyrimidin-4-amine Chemical compound C1=CC(OC(F)F)=CC=C1NC1=CC=NC(C=2N3C=CN=CC3=NC=2C(F)(F)F)=N1 OSVFBZGITOSJBZ-UHFFFAOYSA-N 0.000 claims description 2
- ONWBCCCZGUHQAW-UHFFFAOYSA-N n-[4-(difluoromethoxy)phenyl]-2-[6-fluoro-2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-4-amine Chemical compound C1=CC(OC(F)F)=CC=C1NC1=CC=NC(C=2N3C=C(F)C=CC3=NC=2C(F)(F)F)=N1 ONWBCCCZGUHQAW-UHFFFAOYSA-N 0.000 claims description 2
- OVWHSMWPDQTIEU-UHFFFAOYSA-N n-[4-(difluoromethoxy)phenyl]-2-[6-methoxy-2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-4-amine Chemical compound N12C=C(OC)C=CC2=NC(C(F)(F)F)=C1C(N=1)=NC=CC=1NC1=CC=C(OC(F)F)C=C1 OVWHSMWPDQTIEU-UHFFFAOYSA-N 0.000 claims description 2
- QJWJYDAZIJZGPI-UHFFFAOYSA-N n-[4-(trifluoromethyl)phenyl]-2-[2-(trifluoromethyl)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-4-amine Chemical compound FC(F)(F)C1=NN2C=CC=CC2=C1C(N=1)=NC=CC=1NC1=CC=C(C(F)(F)F)C=C1 QJWJYDAZIJZGPI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 229940088710 antibiotic agent Drugs 0.000 claims 2
- 229940125715 antihistaminic agent Drugs 0.000 claims 2
- 229940033495 antimalarials Drugs 0.000 claims 2
- 229940037128 systemic glucocorticoids Drugs 0.000 claims 2
- 125000000676 alkoxyimino group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 238000000034 method Methods 0.000 description 12
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 2
- 230000001387 anti-histamine Effects 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000008177 pharmaceutical agent Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- APVFMNXXRUHCGS-UHFFFAOYSA-N COC(C=CC(C1=CN=C(C2=C(C(F)(F)F)N=C3N2C=CC=C3)N=C1N)=C1)=C1Cl Chemical compound COC(C=CC(C1=CN=C(C2=C(C(F)(F)F)N=C3N2C=CC=C3)N=C1N)=C1)=C1Cl APVFMNXXRUHCGS-UHFFFAOYSA-N 0.000 description 1
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 1
- LEZHUUSEVLDJLZ-UHFFFAOYSA-N n-(3-fluoro-4-methoxyphenyl)-2-[2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-4-amine Chemical compound C1=C(F)C(OC)=CC=C1NC1=CC=NC(C=2N3C=CC=CC3=NC=2C(F)(F)F)=N1 LEZHUUSEVLDJLZ-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261728907P | 2012-11-21 | 2012-11-21 | |
| US61/728,907 | 2012-11-21 | ||
| PCT/US2013/071132 WO2014081906A2 (en) | 2012-11-21 | 2013-11-21 | Substituted reverse pyrimidine bmi-1 inhibitors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018183173A Division JP6617186B2 (ja) | 2012-11-21 | 2018-09-28 | 置換逆ピリミジンＢｍｉ−１阻害剤 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016504290A JP2016504290A (ja) | 2016-02-12 |
| JP2016504290A5 true JP2016504290A5 (enExample) | 2017-01-05 |
| JP6412503B2 JP6412503B2 (ja) | 2018-10-24 |
Family
ID=50776672
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015544124A Active JP6412503B2 (ja) | 2012-11-21 | 2013-11-21 | 置換逆ピリミジンＢｍｉ−１阻害剤 |
| JP2018183173A Active JP6617186B2 (ja) | 2012-11-21 | 2018-09-28 | 置換逆ピリミジンＢｍｉ−１阻害剤 |
| JP2019203706A Expired - Fee Related JP6918898B2 (ja) | 2012-11-21 | 2019-11-11 | 置換逆ピリミジンＢｍｉ−１阻害剤 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018183173A Active JP6617186B2 (ja) | 2012-11-21 | 2018-09-28 | 置換逆ピリミジンＢｍｉ−１阻害剤 |
| JP2019203706A Expired - Fee Related JP6918898B2 (ja) | 2012-11-21 | 2019-11-11 | 置換逆ピリミジンＢｍｉ−１阻害剤 |
Country Status (32)
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6412503B2 (ja) * | 2012-11-21 | 2018-10-24 | 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 | 置換逆ピリミジンＢｍｉ−１阻害剤 |
| WO2015003360A2 (en) | 2013-07-11 | 2015-01-15 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and their methods of use |
| US10376510B2 (en) * | 2013-07-11 | 2019-08-13 | Agios Pharmaceuticals, Inc. | 2,4- or 4,6-diaminopyrimidine compounds as IDH2 mutants inhibitors for the treatment of cancer |
| WO2015003355A2 (en) | 2013-07-11 | 2015-01-15 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and their methods of use |
| KR102232595B1 (ko) | 2013-08-30 | 2021-03-26 | 피티씨 테라퓨틱스, 인크. | 치환된 피리미딘 bmi-1 저해제 |
| EP3071553A4 (en) | 2013-11-21 | 2017-08-02 | PTC Therapeutics, Inc. | Substituted pyridine and pyrazine bmi-1 inhibitors |
| CN108351862B (zh) | 2015-08-11 | 2023-08-22 | 科格诺亚公司 | 利用人工智能和用户输入来确定发育进展的方法和装置 |
| US10851082B2 (en) | 2015-10-28 | 2020-12-01 | Northwestern University | Substituted aromatic n-heterocyclic compounds as inhibitors of mitogen-activated protein kinase interacting kinase 1 (MNK1) and 2 (MNK2) |
| US11972336B2 (en) | 2015-12-18 | 2024-04-30 | Cognoa, Inc. | Machine learning platform and system for data analysis |
| CA3010615C (en) * | 2016-01-14 | 2024-02-20 | Beth Israel Deaconess Medical Center, Inc. | Mast-cell modulators and uses thereof |
| WO2018090009A1 (en) | 2016-11-14 | 2018-05-17 | Cognoa, Inc. | Methods and apparatus for evaluating developmental conditions and providing control over coverage and reliability |
| WO2018148365A1 (en) * | 2017-02-09 | 2018-08-16 | Cognoa, Inc. | Platform and system for digital personalized medicine |
| KR20200035292A (ko) | 2017-08-01 | 2020-04-02 | 피티씨 테라퓨틱스, 인크. | 혈액 암 치료에 사용하기 위한 dhodh 억제제 |
| EP3564235A1 (en) * | 2018-05-03 | 2019-11-06 | Northwestern University | Substituted aromatic n-heterocyclic compounds as inhibitors of mitogen-activated protein kinase interacting kinase 1 (mnk1) and 2 (mnk2) |
| JP2021535198A (ja) * | 2018-08-17 | 2021-12-16 | 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 | 膵臓癌を治療する方法 |
| 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 |
| MX2021010398A (es) * | 2019-02-28 | 2022-01-18 | Ptc Therapeutics Inc | Metodo para tratar un mieloma multiple. |
| MX2021010906A (es) * | 2019-03-11 | 2021-10-01 | Ptc Therapeutics Inc | Forma de un compuesto que tiene biodisponibilidad mejorada y formulaciones de las mismas. |
| AU2020248351B2 (en) | 2019-03-22 | 2025-09-25 | Cognoa, Inc. | Personalized digital therapy methods and devices |
| EA202192349A1 (ru) * | 2019-03-27 | 2022-02-01 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | Комбинации, пригодные в способе лечения саркомы |
| JP2022527925A (ja) * | 2019-04-02 | 2022-06-07 | ヒノバ ファーマシューティカルズ インコーポレイテッド | 芳香族アミン系化合物と、該化合物のａｒおよびｂｒｄ４二重阻害剤ならびに調節剤の製造における使用 |
| CA3153086A1 (en) | 2019-09-06 | 2021-03-11 | Cognoa, Inc. | Methods, systems, and devices for the diagnosis of behavioral disorders, developmental delays, and neurologic impairments |
| US12245355B2 (en) | 2021-02-19 | 2025-03-04 | Mevion Medical Systems, Inc. | Gantry for a particle therapy system |
| US20240120050A1 (en) * | 2022-10-07 | 2024-04-11 | Insight Direct Usa, Inc. | Machine learning method for predicting a health outcome of a patient using video and audio analytics |
Family Cites Families (80)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH593266A5 (enExample) | 1973-09-20 | 1977-11-30 | Delalande Sa | |
| AU688087B2 (en) | 1994-08-13 | 1998-03-05 | Yuhan Corporation | Novel pyrimidine derivatives and processes for the preparation thereof |
| IN188411B (enExample) | 1997-03-27 | 2002-09-21 | Yuhan Corp | |
| KR100272471B1 (ko) | 1998-11-17 | 2000-11-15 | 김선진 | 신규의 피리미딘 유도체 및 그의 제조방법 |
| GB9905075D0 (en) * | 1999-03-06 | 1999-04-28 | Zeneca Ltd | Chemical compounds |
| AU5636900A (en) | 1999-06-30 | 2001-01-31 | Merck & Co., Inc. | Src kinase inhibitor compounds |
| GB9919778D0 (en) | 1999-08-21 | 1999-10-27 | Zeneca Ltd | Chemical compounds |
| JP2003511378A (ja) | 1999-10-07 | 2003-03-25 | アムジエン・インコーポレーテツド | トリアジン系キナーゼ阻害薬 |
| AU7922900A (en) | 1999-10-27 | 2001-05-08 | Novartis Ag | Thiazole and imidazo (4,5-b) pyridine compounds and their pharmaceutical use |
| HUP0301117A3 (en) | 2000-02-17 | 2004-01-28 | Amgen Inc Thousand Oaks | Imidazole derivatives kinase inhibitors, their use, process for their preparation and pharmaceutical compositions containing them |
| AU2001242629B2 (en) | 2000-03-29 | 2005-08-11 | Cyclacel Limited | 2-substituted 4-heteroaryl-pyrimidines and their use in the treatment of proliferative disorders |
| ES2266258T3 (es) | 2000-09-15 | 2007-03-01 | Vertex Pharmaceuticals Incorporated | Compuestos de pirazol utiles como inhibidores de proteina cinasas. |
| AU9458401A (en) | 2000-09-20 | 2002-04-02 | Ortho Mcneil Pharm Inc | Pyrazine derivatives as modulators of tyrosine kinases |
| US6716851B2 (en) * | 2000-12-12 | 2004-04-06 | Cytovia, Inc. | Substituted 2-aryl-4-arylaminopyrimidines and analogs as activators or caspases and inducers of apoptosis and the use thereof |
| AU2002228922A1 (en) * | 2000-12-12 | 2002-06-24 | Cytovia, Inc. | Substituted 2-aryl-4-arylaminopyrimidines and analogs as activators of caspases and inducers of apoptosis and the use thereof |
| WO2002048148A2 (en) | 2000-12-15 | 2002-06-20 | Glaxo Group Limited | Pyrazolopyridine derivatives |
| GB0103926D0 (en) | 2001-02-17 | 2001-04-04 | Astrazeneca Ab | Chemical compounds |
| BR0207096A (pt) | 2001-02-20 | 2004-01-20 | Astrazeneca Ab | Uso de um composto, compostos, formulação farmacêutica, e, método de tratamento e/ou profilaxia de condições associadas com a inibição de glicogênio sintase quinase-3 |
| US20030165873A1 (en) | 2001-03-02 | 2003-09-04 | Come Jon H. | Three hybrid assay system |
| CA2450555A1 (en) | 2001-06-25 | 2003-01-03 | Merck & Co., Inc. | (pyrimidyl)(phenyl)substituted fused heteroaryl p38 inhibiting and pkg kinase inhibiting compounds |
| US6689778B2 (en) | 2001-07-03 | 2004-02-10 | Vertex Pharmaceuticals Incorporated | Inhibitors of Src and Lck protein kinases |
| WO2003011837A1 (en) | 2001-08-01 | 2003-02-13 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| AU2003212634A1 (en) * | 2002-03-11 | 2003-09-22 | Zetiq Technologies Ltd. | Compounds useful in the treatment of cancer |
| CA2486187C (en) | 2002-05-23 | 2013-02-19 | Cytopia Pty Ltd. | Kinase inhibitors |
| US7494997B2 (en) | 2002-06-28 | 2009-02-24 | Nippon Shinyaku Co., Ltd. | Amide derivative |
| GB0215844D0 (en) | 2002-07-09 | 2002-08-14 | Novartis Ag | Organic compounds |
| WO2004007407A2 (en) * | 2002-07-11 | 2004-01-22 | Fluorous Technologies Incorporated | Fluorous tagging and scavenging reactants and methods of synthesis and use thereof |
| US20040110821A1 (en) * | 2002-08-07 | 2004-06-10 | Konkel Michael J. | GAL3 receptor antagonists for the treatment of affective disorders |
| UA80296C2 (en) | 2002-09-06 | 2007-09-10 | Biogen Inc | Imidazolopyridines and methods of making and using the same |
| AU2003301302A1 (en) | 2002-10-15 | 2004-05-04 | Smithkline Beecham Corporation | Pyradazine compounds as gsk-3 inhibitors |
| US7169781B2 (en) | 2003-10-17 | 2007-01-30 | Hoffmann-La Roche Inc. | Imidazole derivatives and their use as pharmaceutical agents |
| US20080207613A1 (en) | 2004-01-12 | 2008-08-28 | Cytopia Research Pty Ltd | Selective Kinase Inhibitors |
| JP2007520558A (ja) | 2004-02-04 | 2007-07-26 | スミスクライン・ビーチャム・コーポレイション | キナーゼ阻害剤として有用なピリミジノン化合物 |
| US7507826B2 (en) * | 2004-03-30 | 2009-03-24 | Vertex Pharmaceuticals Incorporated | Azaindoles useful as inhibitors of JAK and other protein kinases |
| JP2006045119A (ja) | 2004-08-04 | 2006-02-16 | Toray Ind Inc | ピラジン誘導体及びそれを有効成分とする腎炎治療薬 |
| US7855205B2 (en) | 2004-10-29 | 2010-12-21 | Janssen Pharmaceutica Nv | Pyrimidinyl substituted fused-pyrrolyl compounds useful in treating kinase disorders |
| EP1854793A4 (en) | 2005-02-28 | 2011-01-26 | Japan Tobacco Inc | NEW AMINOPYRIDEIN COMPOUND WITH SYK-HEMDERING EFFECT |
| WO2006099231A1 (en) | 2005-03-10 | 2006-09-21 | Bayer Pharmaceuticals Corporation | Pyrimidine derivatives for treatment of hyperproliferative disorders |
| US20080039450A1 (en) | 2006-06-22 | 2008-02-14 | Jensen Annika J | Compounds |
| CN101516873A (zh) * | 2006-10-03 | 2009-08-26 | 神经研究公司 | 用作钾通道调节剂的吲唑基衍生物 |
| AU2007304195A1 (en) | 2006-10-03 | 2008-04-10 | Neurosearch A/S | Indazolyl derivatives useful as potassium channel modulating agents |
| ES2383370T3 (es) | 2006-10-19 | 2012-06-20 | Signal Pharmaceuticals Llc | Compuestos de heteroarilo, sus composiciones y uso de los mismos como inhibidores de proteína quinasa |
| WO2008079933A2 (en) | 2006-12-22 | 2008-07-03 | Novartis Ag | Heteroaryl-heteroaryl compounds as cdk inhibitors for the treatment of cancer, inflammation and viral infections |
| TW200902010A (en) | 2007-01-26 | 2009-01-16 | Smithkline Beecham Corp | Anthranilamide inhibitors of aurora kinase |
| EP2121633A2 (en) | 2007-02-12 | 2009-11-25 | Merck & Co., Inc. | Piperazine derivatives for treatment of ad and related conditions |
| WO2008132502A1 (en) | 2007-04-25 | 2008-11-06 | Astrazeneca Ab | Pyrazolyl-amino-substituted pyrimidines and their use for the treatment of cancer |
| GB0714573D0 (en) | 2007-07-26 | 2007-09-05 | Imp Innovations Ltd | Marker gene |
| WO2009037247A1 (en) | 2007-09-17 | 2009-03-26 | Neurosearch A/S | Pyrazine derivatives and their use as potassium channel modulators |
| MX2010005300A (es) | 2007-11-16 | 2010-06-25 | Incyte Corp | 4-pirazolil-n-arilpirimidin-2-aminas y 4-pirazolil-n-heteroarilpir imidin-2-aminas como inhibidores de cinasas janus. |
| JP2011506303A (ja) | 2007-12-07 | 2011-03-03 | ノバルティス アーゲー | ピラゾール誘導体およびサイクリン依存性キナーゼの阻害剤としてのその使用 |
| DE102008005493A1 (de) | 2008-01-22 | 2009-07-23 | Merck Patent Gmbh | 4-(Pyrrolo[2,3-c] pyridine-3-yl)-pyrimidin-2-yl-amin-derivate |
| GB0801416D0 (en) | 2008-01-25 | 2008-03-05 | Piramed Ltd | Pharmaceutical compounds |
| JP2011518219A (ja) | 2008-04-22 | 2011-06-23 | ポートラ ファーマシューティカルズ， インコーポレイテッド | タンパク質キナーゼの阻害剤 |
| ES2605815T3 (es) * | 2008-07-01 | 2017-03-16 | Ptc Therapeutics, Inc. | Moduladores de la expresión de la proteína Bmi-1 |
| JP5576370B2 (ja) | 2008-08-06 | 2014-08-20 | ファイザー・インク | Ｃｈｋ−１阻害剤としての６置換２−ヘテロシクリルアミノピラジン化合物 |
| CN102177154A (zh) * | 2008-09-02 | 2011-09-07 | 神经研究公司 | 吡唑基-嘧啶衍生物及其作为钾通道调节剂的应用 |
| WO2010061903A1 (ja) * | 2008-11-27 | 2010-06-03 | 塩野義製薬株式会社 | Pi3k阻害活性を有するピリミジン誘導体およびピリジン誘導体 |
| WO2010092962A1 (ja) | 2009-02-12 | 2010-08-19 | アステラス製薬株式会社 | へテロ環誘導体 |
| AU2010229468A1 (en) | 2009-03-27 | 2011-10-13 | Vetdc, Inc. | Pyrimidinyl and 1,3,5-triazinyl benzimidazole sulfonamides and their use in cancer therapy |
| EP2435435B1 (en) | 2009-05-27 | 2014-01-29 | AbbVie Inc. | Pyrimidine inhibitors of kinase activity |
| WO2010144416A1 (en) | 2009-06-08 | 2010-12-16 | Gaeta Federico C A | SUBSTITUTED PYRAZOLO [1,5-a] PYRIDINE COMPOUNDS HAVING MULTI-TARGET ACTIVITY |
| DK2442809T3 (en) | 2009-06-17 | 2016-12-19 | Vertex Pharma | Inhibitors of the replication of influenza virus |
| US8486939B2 (en) | 2009-07-07 | 2013-07-16 | Pathway Therapeutics Inc. | Pyrimidinyl and 1,3,5-triazinyl benzimidazoles and their use in cancer therapy |
| JP2012533553A (ja) | 2009-07-15 | 2012-12-27 | アボット・ラボラトリーズ | ピロロピリジン系キナーゼ阻害薬 |
| EP2454262B1 (en) | 2009-07-15 | 2014-05-14 | Abbott Laboratories | Pyrrolopyrazine inhibitors of kinases |
| JP2011136925A (ja) | 2009-12-28 | 2011-07-14 | Dainippon Sumitomo Pharma Co Ltd | 含窒素二環性化合物 |
| TWI523852B (zh) | 2010-01-12 | 2016-03-01 | Ａｂ科學公司 | 經取代之唑衍生物、含彼之組合物及其用途 |
| UY33213A (es) | 2010-02-18 | 2011-09-30 | Almirall Sa | Derivados de pirazol como inhibidores de jak |
| ES2365960B1 (es) | 2010-03-31 | 2012-06-04 | Palobiofarma, S.L | Nuevos antagonistas de los receptores de adenosina. |
| KR101788903B1 (ko) * | 2010-08-19 | 2017-10-23 | 에프. 호프만-라 로슈 아게 | 체세포의 유도된 재프로그래밍된 신경 줄기 세포 (ｉｒｎｓｃｓ) 로의 전환 |
| CA2812081A1 (en) | 2010-09-13 | 2012-03-22 | Novartis Ag | Triazine-oxadiazoles |
| WO2012050884A2 (en) | 2010-09-28 | 2012-04-19 | President And Fellows Of Harvard College | Cardiac glycosides are potent inhibitors of interferon-beta gene expression |
| US9090593B2 (en) * | 2010-12-09 | 2015-07-28 | Amgen Inc. | Bicyclic compounds as Pim inhibitors |
| CN103402997B (zh) | 2011-02-25 | 2015-08-26 | 柳韩洋行 | 二氨基嘧啶衍生物及其制备方法 |
| ES2698847T3 (es) * | 2011-07-07 | 2019-02-06 | Merck Patent Gmbh | Azaheterociclos sustituidos para el tratamiento del cáncer |
| UY35148A (es) | 2012-11-21 | 2014-05-30 | Amgen Inc | Immunoglobulinas heterodiméricas |
| JP6412503B2 (ja) | 2012-11-21 | 2018-10-24 | 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 | 置換逆ピリミジンＢｍｉ−１阻害剤 |
| US9695228B2 (en) | 2012-11-21 | 2017-07-04 | Janssen Biotech, Inc. | EGFR and c-Met fibronectin type III domain binding molecules |
| JP2016514670A (ja) | 2013-03-15 | 2016-05-23 | シナジー ファーマシューティカルズ インコーポレイテッド | 他の薬物と組み合わせたグアニル酸シクラーゼ受容体アゴニスト |
| MX2021010906A (es) * | 2019-03-11 | 2021-10-01 | Ptc Therapeutics Inc | Forma de un compuesto que tiene biodisponibilidad mejorada y formulaciones de las mismas. |
-
2013
- 2013-11-21 JP JP2015544124A patent/JP6412503B2/ja active Active
- 2013-11-21 SG SG10201600149VA patent/SG10201600149VA/en unknown
- 2013-11-21 PE PE2015000665A patent/PE20151413A1/es unknown
- 2013-11-21 TW TW102142555A patent/TWI623531B/zh not_active IP Right Cessation
- 2013-11-21 KR KR1020227002513A patent/KR102455889B1/ko active Active
- 2013-11-21 AU AU2013348009A patent/AU2013348009C1/en active Active
- 2013-11-21 KR KR1020217020963A patent/KR102356487B1/ko active Active
- 2013-11-21 WO PCT/US2013/071132 patent/WO2014081906A2/en not_active Ceased
- 2013-11-21 UA UAA201505533A patent/UA118094C2/uk unknown
- 2013-11-21 SG SG11201503982XA patent/SG11201503982XA/en unknown
- 2013-11-21 CN CN202010080540.0A patent/CN111423417B/zh active Active
- 2013-11-21 EA EA201590992A patent/EA031405B1/ru unknown
- 2013-11-21 DK DK13857326.6T patent/DK2922828T3/da active
- 2013-11-21 CU CU2015000053A patent/CU24387B1/es unknown
- 2013-11-21 BR BR112015011760-0A patent/BR112015011760B1/pt active IP Right Grant
- 2013-11-21 CA CA2892045A patent/CA2892045C/en active Active
- 2013-11-21 US US14/443,911 patent/US10428050B2/en active Active
- 2013-11-21 KR KR1020227035587A patent/KR20220143164A/ko not_active Ceased
- 2013-11-21 HK HK16103069.2A patent/HK1215032A1/zh unknown
- 2013-11-21 NZ NZ74660713A patent/NZ746607A/en unknown
- 2013-11-21 AR ARP130104300A patent/AR093579A1/es active IP Right Grant
- 2013-11-21 EP EP13857326.6A patent/EP2922828B1/en active Active
- 2013-11-21 KR KR1020157016184A patent/KR102275676B1/ko not_active Expired - Fee Related
- 2013-11-21 MX MX2015006469A patent/MX385385B/es unknown
- 2013-11-21 NZ NZ70890913A patent/NZ708909A/en unknown
- 2013-11-21 PT PT138573266T patent/PT2922828T/pt unknown
- 2013-11-21 EA EA201890142A patent/EA035349B1/ru not_active IP Right Cessation
- 2013-11-21 MA MA38208A patent/MA38208B1/fr unknown
- 2013-11-21 PH PH1/2015/501130A patent/PH12015501130B1/en unknown
- 2013-11-21 ES ES13857326T patent/ES2821529T3/es active Active
- 2013-11-21 CN CN201380070973.6A patent/CN104918919A/zh active Pending
- 2013-11-21 PL PL13857326T patent/PL2922828T3/pl unknown
-
2015
- 2015-05-18 IL IL238871A patent/IL238871B/en active IP Right Grant
- 2015-05-20 CL CL2015001377A patent/CL2015001377A1/es unknown
- 2015-05-21 EC ECIEPI201519948A patent/ECSP15019948A/es unknown
- 2015-05-21 SA SA517381847A patent/SA517381847B1/ar unknown
- 2015-05-21 MX MX2021009892A patent/MX2021009892A/es unknown
- 2015-05-21 NI NI201500072A patent/NI201500072A/es unknown
- 2015-05-22 ZA ZA2015/03642A patent/ZA201503642B/en unknown
- 2015-06-05 CR CR20150294A patent/CR20150294A/es unknown
-
2018
- 2018-09-28 JP JP2018183173A patent/JP6617186B2/ja active Active
-
2019
- 2019-03-10 IL IL265253A patent/IL265253A/en unknown
- 2019-09-26 US US16/583,442 patent/US11180483B2/en not_active Expired - Fee Related
- 2019-11-11 JP JP2019203706A patent/JP6918898B2/ja not_active Expired - Fee Related
-
2021
- 2021-11-10 US US17/523,480 patent/US20220064150A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2016529292A5 (enExample) | ||
| US11135201B2 (en) | Compositions to improve the therapeutic benefit of bisantrene and analogs and derivatives thereof | |
| JP7696443B2 (ja) | Ｅｇｆｒ変異を有するがんを処置するためのアミノ置換ヘテロ環類 | |
| JP6728321B2 (ja) | 置換ピリミジンＢｍｉ−１阻害剤 | |
| US10421761B2 (en) | Compounds for kinase modulation, and indications therefor | |
| DK2935248T3 (en) | RELATIONS AND PROCEDURE FOR CHINESE MODULATION AND INDICATIONS THEREOF | |
| US9771369B2 (en) | Compounds and methods for kinase modulation, and indications therefor | |
| JP5815558B2 (ja) | キナーゼ調節のための化合物及び方法ならびにそれらの適応症 | |
| JP2015511224A5 (enExample) | ||
| JP2015517988A5 (enExample) | ||
| JP2022500402A5 (enExample) | ||
| NZ607060A (en) | Substituted imidazoquinoline derivatives as kinase inhibitors | |
| JP2016504290A (ja) | 置換逆ピリミジンＢｍｉ−１阻害剤 | |
| JP2014526526A5 (enExample) | ||
| JP2024529485A (ja) | イミダゾ［１，２－ｂ］ピリダジニル化合物及びその使用 | |
| WO2018195471A1 (en) | Syk inhibitors in combination with hypomethylating agents |