AU2013348009C1 - Substituted reverse pyrimidine Bmi-1 inhibitors - Google Patents

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Publication number

AU2013348009C1

AU2013348009C1 AU2013348009A AU2013348009A AU2013348009C1 AU 2013348009 C1 AU2013348009 C1 AU 2013348009C1 AU 2013348009 A AU2013348009 A AU 2013348009A AU 2013348009 A AU2013348009 A AU 2013348009A AU 2013348009 C1 AU2013348009 C1 AU 2013348009C1

Authority

AU

Australia

Prior art keywords

pyrimidine

benzimidazol

fluoro

diamine

phenyl

Prior art date

2012-11-21

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.)

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• 101100058550 Mus musculus Bmi1 gene Proteins 0.000 title claims abstract description 217
• 230000002441 reversible effect Effects 0.000 title abstract description 7
• 239000003112 inhibitor Substances 0.000 title description 22
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title description 2
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 196
• 201000011510 cancer Diseases 0.000 claims abstract description 123
• 238000000034 method Methods 0.000 claims abstract description 67
• 230000001404 mediated effect Effects 0.000 claims abstract description 57
• 150000001875 compounds Chemical class 0.000 claims description 454
• -1 C1 -salkyl Chemical group 0.000 claims description 299
• PZURVUQVDFSJJO-UHFFFAOYSA-N pyrimidine-4,6-diamine Chemical compound NC1=CC(N)=N[C]=N1 PZURVUQVDFSJJO-UHFFFAOYSA-N 0.000 claims description 226
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 214
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 199
• 125000001072 heteroaryl group Chemical group 0.000 claims description 101
• OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims description 85
• 210000004027 cell Anatomy 0.000 claims description 81
• 239000003795 chemical substances by application Substances 0.000 claims description 58
• 125000001424 substituent group Chemical group 0.000 claims description 57
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 56
• 125000005843 halogen group Chemical group 0.000 claims description 55
• 125000004076 pyridyl group Chemical group 0.000 claims description 50
• 210000000130 stem cell Anatomy 0.000 claims description 50
• 150000003839 salts Chemical class 0.000 claims description 46
• 125000003118 aryl group Chemical group 0.000 claims description 40
• 125000000623 heterocyclic group Chemical group 0.000 claims description 36
• 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 33
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
• 239000008194 pharmaceutical composition Substances 0.000 claims description 27
• 239000012453 solvate Substances 0.000 claims description 27
• 239000002253 acid Substances 0.000 claims description 22
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
• 150000002148 esters Chemical class 0.000 claims description 20
• 210000004881 tumor cell Anatomy 0.000 claims description 20
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
• 230000002401 inhibitory effect Effects 0.000 claims description 19
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 19
• 239000002246 antineoplastic agent Substances 0.000 claims description 18
• 239000003814 drug Substances 0.000 claims description 18
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 17
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 17
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 17
• 229910052739 hydrogen Inorganic materials 0.000 claims description 17
• 239000001257 hydrogen Substances 0.000 claims description 17
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 17
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 15
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 14
• 125000001769 aryl amino group Chemical group 0.000 claims description 13
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
• 229940127089 cytotoxic agent Drugs 0.000 claims description 13
• 239000012458 free base Substances 0.000 claims description 13
• 230000001028 anti-proliverative effect Effects 0.000 claims description 11
• 230000002519 immonomodulatory effect Effects 0.000 claims description 11
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 11
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 11
• 150000001204 N-oxides Chemical class 0.000 claims description 10
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 10
• 239000003242 anti bacterial agent Substances 0.000 claims description 10
• 229940121363 anti-inflammatory agent Drugs 0.000 claims description 10
• 239000002260 anti-inflammatory agent Substances 0.000 claims description 10
• UVNXNSUKKOLFBM-UHFFFAOYSA-N imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=CSC2=NC=CN21 UVNXNSUKKOLFBM-UHFFFAOYSA-N 0.000 claims description 10
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 10
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 10
• 238000004519 manufacturing process Methods 0.000 claims description 9
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
• 239000004037 angiogenesis inhibitor Substances 0.000 claims description 8
• 229910052757 nitrogen Inorganic materials 0.000 claims description 8
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 8
• 125000004432 carbon atom Chemical group C* 0.000 claims description 7
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
• 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 7
• 125000000335 thiazolyl group Chemical group 0.000 claims description 7
• 229940088710 antibiotic agent Drugs 0.000 claims description 6
• 239000013522 chelant Substances 0.000 claims description 6
• 230000003637 steroidlike Effects 0.000 claims description 6
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
• 229940100198 alkylating agent Drugs 0.000 claims description 5
• 239000002168 alkylating agent Substances 0.000 claims description 5
• 239000003443 antiviral agent Substances 0.000 claims description 5
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 5
• 239000011230 binding agent Substances 0.000 claims description 5
• 239000000812 cholinergic antagonist Substances 0.000 claims description 5
• 239000003862 glucocorticoid Substances 0.000 claims description 5
• 229940037128 systemic glucocorticoids Drugs 0.000 claims description 5
• 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 4
• BZVWXAAVWBFZMW-UHFFFAOYSA-N 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)=CC=1NC1=CC=C(C(F)(F)F)C=C1 BZVWXAAVWBFZMW-UHFFFAOYSA-N 0.000 claims description 4
• XRBJDNPHEGJDQG-UHFFFAOYSA-N 2-(5-chloro-2-methylbenzimidazol-1-yl)-4-n-[4-(difluoromethoxy)phenyl]pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC(Cl)=CC=C2N1C(N=1)=NC(N)=CC=1NC1=CC=C(OC(F)F)C=C1 XRBJDNPHEGJDQG-UHFFFAOYSA-N 0.000 claims description 4
• 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims description 4
• 108090000704 Tubulin Proteins 0.000 claims description 4
• 102000004243 Tubulin Human genes 0.000 claims description 4
• 239000000739 antihistaminic agent Substances 0.000 claims description 4
• 229940125715 antihistaminic agent Drugs 0.000 claims description 4
• 239000003430 antimalarial agent Substances 0.000 claims description 4
• 125000005605 benzo group Chemical group 0.000 claims description 4
• 239000003124 biologic agent Substances 0.000 claims description 4
• 229940125697 hormonal agent Drugs 0.000 claims description 4
• 239000003199 leukotriene receptor blocking agent Substances 0.000 claims description 4
• 125000004043 oxo group Chemical group O=* 0.000 claims description 4
• 229940124641 pain reliever Drugs 0.000 claims description 4
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• SNYDQRUIJGKYSR-UHFFFAOYSA-N 2-(2-cyclopropyl-6-fluoroimidazo[4,5-b]pyridin-1-yl)-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound N=1C(N2C3=CC(F)=CN=C3N=C2C2CC2)=NC(N)=CC=1NC1=CC=C(C(F)(F)F)C=C1 SNYDQRUIJGKYSR-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 3
• YTEOEXHZZFBIQA-UHFFFAOYSA-N 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)=CC=1NC1=CC=C(C(F)(F)F)C=C1 YTEOEXHZZFBIQA-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• JQNWPGQMXITTAF-UHFFFAOYSA-N 2-(6-fluoro-2-methylimidazo[4,5-b]pyridin-1-yl)-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CC1=NC2=NC=C(F)C=C2N1C(N=1)=NC(N)=CC=1NC1=CC=C(C(F)(F)F)C=C1 JQNWPGQMXITTAF-UHFFFAOYSA-N 0.000 claims description 3
• SHZDNSYMABFZIW-UHFFFAOYSA-N 4-n-(4-chloro-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(Cl)C(F)=C1 SHZDNSYMABFZIW-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• HPHVGFRGRUBLHM-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)-3-fluorophenyl]-2-(2-ethyl-4,6-difluorobenzimidazol-1-yl)-5-fluoropyrimidine-4,6-diamine Chemical compound CCC1=NC2=C(F)C=C(F)C=C2N1C(N=1)=NC(N)=C(F)C=1NC1=CC=C(OC(F)F)C(F)=C1 HPHVGFRGRUBLHM-UHFFFAOYSA-N 0.000 claims description 3
• POVHYBIHXONPCN-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)-3-fluorophenyl]-2-(2-methylbenzimidazol-1-yl)pyrimidine-4,6-diamine Chemical compound CC1=NC2=CC=CC=C2N1C(N=1)=NC(N)=CC=1NC1=CC=C(OC(F)F)C(F)=C1 POVHYBIHXONPCN-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 3
• LZPYKSXNEGPLEO-UHFFFAOYSA-N 4-n-[4-(difluoromethoxy)phenyl]-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=C1 LZPYKSXNEGPLEO-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• DSCHTNNPZWSKCI-UHFFFAOYSA-N C1(CC1)C1=NC2=C(N1C1=NC(=C(C(=N1)NC1=CC=C(C=C1)OC(F)(F)F)F)N)C=CC=C2.C2(CC2)C2=NC1=C(N2C2=NC(=C(C(=N2)NC2=CC=C(C=C2)OC)F)N)C=CC=C1 Chemical compound C1(CC1)C1=NC2=C(N1C1=NC(=C(C(=N1)NC1=CC=C(C=C1)OC(F)(F)F)F)N)C=CC=C2.C2(CC2)C2=NC1=C(N2C2=NC(=C(C(=N2)NC2=CC=C(C=C2)OC)F)N)C=CC=C1 DSCHTNNPZWSKCI-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• KSTQQADVJQZULT-UHFFFAOYSA-N FC=1C(=NC(=NC1N)N1C(=NC2=NC=CC=C21)C)NC2=CC=C(C=C2)C(F)(F)F Chemical compound FC=1C(=NC(=NC1N)N1C(=NC2=NC=CC=C21)C)NC2=CC=C(C=C2)C(F)(F)F KSTQQADVJQZULT-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 239000003470 adrenal cortex hormone Substances 0.000 claims description 3
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
• 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
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