TWI623531B - 經取代反向嘧啶ｂｍｉ－１抑制劑 - Google Patents

Info

Publication number

TWI623531B

TWI623531B TW102142555A TW102142555A TWI623531B TW I623531 B TWI623531 B TW I623531B TW 102142555 A TW102142555 A TW 102142555A TW 102142555 A TW102142555 A TW 102142555A TW I623531 B TWI623531 B TW I623531B

Authority

TW

Taiwan

Prior art keywords

diamine

pyrimidine

fluoro

benzimidazol

methyl

Prior art date

2012-11-21

Links

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• Global Dossier
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• 101100058550 Mus musculus Bmi1 gene Proteins 0.000 title claims abstract description 200
• 230000002441 reversible effect Effects 0.000 title abstract description 6
• 239000003112 inhibitor Substances 0.000 title description 23
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title 1
• -1 pyrimidine compound Chemical class 0.000 claims abstract description 504
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 196
• 201000011510 cancer Diseases 0.000 claims abstract description 114
• 230000001404 mediated effect Effects 0.000 claims abstract description 52
• 150000001875 compounds Chemical class 0.000 claims description 457
• 125000000217 alkyl group Chemical group 0.000 claims description 279
• 125000001072 heteroaryl group Chemical group 0.000 claims description 93
• 239000000203 mixture Substances 0.000 claims description 89
• 210000004027 cell Anatomy 0.000 claims description 84
• 125000003282 alkyl amino group Chemical group 0.000 claims description 69
• 125000003545 alkoxy group Chemical group 0.000 claims description 60
• 239000003795 chemical substances by application Substances 0.000 claims description 55
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 53
• 210000000130 stem cell Anatomy 0.000 claims description 52
• 125000005843 halogen group Chemical group 0.000 claims description 50
• 150000003839 salts Chemical class 0.000 claims description 43
• 125000003118 aryl group Chemical group 0.000 claims description 35
• 125000000623 heterocyclic group Chemical group 0.000 claims description 35
• 150000001412 amines Chemical class 0.000 claims description 32
• 125000001424 substituent group Chemical group 0.000 claims description 32
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 27
• 239000008194 pharmaceutical composition Substances 0.000 claims description 26
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 26
• 239000002253 acid Substances 0.000 claims description 25
• 125000003342 alkenyl group Chemical group 0.000 claims description 23
• 125000004414 alkyl thio group Chemical group 0.000 claims description 22
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 21
• 150000002148 esters Chemical class 0.000 claims description 21
• 210000004881 tumor cell Anatomy 0.000 claims description 21
• 125000000304 alkynyl group Chemical group 0.000 claims description 19
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
• 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 18
• 125000004076 pyridyl group Chemical group 0.000 claims description 18
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 17
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
• 229910052739 hydrogen Inorganic materials 0.000 claims description 16
• 239000001257 hydrogen Substances 0.000 claims description 16
• 238000011282 treatment Methods 0.000 claims description 16
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 15
• 239000002246 antineoplastic agent Substances 0.000 claims description 15
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 14
• RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 12
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 11
• 230000001028 anti-proliverative effect Effects 0.000 claims description 11
• 125000001769 aryl amino group Chemical group 0.000 claims description 11
• 239000013078 crystal Substances 0.000 claims description 11
• 125000001041 indolyl group Chemical group 0.000 claims description 11
• 230000002401 inhibitory effect Effects 0.000 claims description 11
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
• 238000001959 radiotherapy Methods 0.000 claims description 10
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 9
• 229940121363 anti-inflammatory agent Drugs 0.000 claims description 9
• 239000002260 anti-inflammatory agent Substances 0.000 claims description 9
• 239000003814 drug Substances 0.000 claims description 9
• 239000012458 free base Substances 0.000 claims description 9
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
• 239000004037 angiogenesis inhibitor Substances 0.000 claims description 8
• 239000003242 anti bacterial agent Substances 0.000 claims description 8
• 125000002619 bicyclic group Chemical group 0.000 claims description 8
• 239000002955 immunomodulating agent Substances 0.000 claims description 8
• 229940121354 immunomodulator Drugs 0.000 claims description 8
• 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 8
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 7
• 239000003246 corticosteroid Substances 0.000 claims description 7
• 229960001334 corticosteroids Drugs 0.000 claims description 7
• 125000005946 imidazo[1,2-a]pyridyl group Chemical group 0.000 claims description 7
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 7
• 150000001204 N-oxides Chemical class 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
• 238000006467 substitution reaction Methods 0.000 claims description 6
• 125000002252 acyl group Chemical group 0.000 claims description 5
• 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 5
• 229940100198 alkylating agent Drugs 0.000 claims description 5
• 239000002168 alkylating agent Substances 0.000 claims description 5
• 229940088710 antibiotic agent Drugs 0.000 claims description 5
• 239000003443 antiviral agent Substances 0.000 claims description 5
• 229940124748 beta 2 agonist Drugs 0.000 claims description 5
• 239000011230 binding agent Substances 0.000 claims description 5
• 125000004432 carbon atom Chemical group C* 0.000 claims description 5
• 239000000812 cholinergic antagonist Substances 0.000 claims description 5
• 239000003862 glucocorticoid Substances 0.000 claims description 5
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
• 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 229940037128 systemic glucocorticoids Drugs 0.000 claims description 5
• 102000004243 Tubulin Human genes 0.000 claims description 4
• 108090000704 Tubulin Proteins 0.000 claims description 4
• 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 4
• 125000003277 amino group Chemical group 0.000 claims description 4
• 229940035676 analgesics Drugs 0.000 claims description 4
• 239000000730 antalgic agent Substances 0.000 claims description 4
• 229940125715 antihistaminic agent Drugs 0.000 claims description 4
• 239000000739 antihistaminic agent Substances 0.000 claims description 4
• 239000003430 antimalarial agent Substances 0.000 claims description 4
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 4
• 239000003124 biologic agent Substances 0.000 claims description 4
• 229940088597 hormone Drugs 0.000 claims description 4
• 239000005556 hormone Substances 0.000 claims description 4
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 4
• 239000003199 leukotriene receptor blocking agent Substances 0.000 claims description 4
• 239000001301 oxygen Substances 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• 230000003637 steroidlike Effects 0.000 claims description 4
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
• WRFKCROHHVRHNR-UHFFFAOYSA-N 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)=CC=1NC1=CC=C(C(F)(F)F)C=C1 WRFKCROHHVRHNR-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
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
• KOMIQUBLFZGKSA-UHFFFAOYSA-N n-(3-chloro-4-methoxyphenyl)-2-[2-(trifluoromethyl)benzimidazol-1-yl]pyrimidin-4-amine Chemical compound C1=C(Cl)C(OC)=CC=C1NC1=CC=NC(N2C3=CC=CC=C3N=C2C(F)(F)F)=N1 KOMIQUBLFZGKSA-UHFFFAOYSA-N 0.000 claims description 2
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 25
• MISVBCMQSJUHMH-UHFFFAOYSA-N pyrimidine-4,6-diamine Chemical compound NC1=CC(N)=NC=N1 MISVBCMQSJUHMH-UHFFFAOYSA-N 0.000 claims 17
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 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 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 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 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 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 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 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 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 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 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 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 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 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 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 2
• YOSSXOXUALILSR-UHFFFAOYSA-N 2-(6-fluoro-2-methylimidazo[1,2-a]pyrimidin-3-yl)-4-n-[4-(trifluoromethyl)phenyl]pyrimidine-4,6-diamine Chemical compound CC=1N=C2N=CC(F)=CN2C=1C(N=1)=NC(N)=CC=1NC1=CC=C(C(F)(F)F)C=C1 YOSSXOXUALILSR-UHFFFAOYSA-N 0.000 claims 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 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 2
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 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 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 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 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 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 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 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 2
• 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 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 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 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 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 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 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 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 2
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