HRP20040678A2 - Dihydrobenzodiazepin-2-one derivatives for the treatment of neurological disorders - Google Patents

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Publication number

HRP20040678A2

HRP20040678A2 HR20040678A HRP20040678A HRP20040678A2 HR P20040678 A2 HRP20040678 A2 HR P20040678A2 HR 20040678 A HR20040678 A HR 20040678A HR P20040678 A HRP20040678 A HR P20040678A HR P20040678 A2 HRP20040678 A2 HR P20040678A2

Authority

HR

Croatia

Prior art keywords

phenyl

tert

pyridin

mmol

butyl ester

Prior art date

2002-02-06

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• 208000012902 Nervous system disease Diseases 0.000 title claims description 6
• 208000025966 Neurological disease Diseases 0.000 title claims description 6
• 238000000034 method Methods 0.000 claims description 638
• 150000001875 compounds Chemical class 0.000 claims description 552
• -1 pyrrole-1-yl Chemical group 0.000 claims description 158
• 239000002253 acid Substances 0.000 claims description 94
• 125000000217 alkyl group Chemical group 0.000 claims description 77
• 125000003545 alkoxy group Chemical group 0.000 claims description 52
• 238000006243 chemical reaction Methods 0.000 claims description 43
• 125000003282 alkyl amino group Chemical group 0.000 claims description 33
• 229910052736 halogen Inorganic materials 0.000 claims description 30
• 239000001257 hydrogen Substances 0.000 claims description 28
• 229910052739 hydrogen Inorganic materials 0.000 claims description 28
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 26
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
• 150000003839 salts Chemical class 0.000 claims description 22
• 238000002360 preparation method Methods 0.000 claims description 19
• 125000001424 substituent group Chemical group 0.000 claims description 19
• 125000001153 fluoro group Chemical group F* 0.000 claims description 18
• 150000002367 halogens Chemical group 0.000 claims description 18
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 12
• 125000004414 alkyl thio group Chemical group 0.000 claims description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 9
• 229940079593 drug Drugs 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 8
• 238000004519 manufacturing process Methods 0.000 claims description 8
• 230000008569 process Effects 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 230000001154 acute effect Effects 0.000 claims description 6
• ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims description 6
• 125000003277 amino group Chemical group 0.000 claims description 5
• 230000001684 chronic effect Effects 0.000 claims description 5
• 238000007363 ring formation reaction Methods 0.000 claims description 5
• QWFYXUVFCJKYON-UHFFFAOYSA-N 8-chloro-4-(3-pyridin-4-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC2=CC(Cl)=CC=C2N=C1C(C=1)=CC=CC=1C1=CC=NC=C1 QWFYXUVFCJKYON-UHFFFAOYSA-N 0.000 claims description 4
• 208000024827 Alzheimer disease Diseases 0.000 claims description 4
• 208000026139 Memory disease Diseases 0.000 claims description 4
• 208000028017 Psychotic disease Diseases 0.000 claims description 4
• 125000003342 alkenyl group Chemical group 0.000 claims description 4
• 208000010877 cognitive disease Diseases 0.000 claims description 4
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
• LYTVXCQQTLUEQR-UHFFFAOYSA-N ro4491533 Chemical compound CC1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=C(C)C=C3N=2)C(F)(F)F)=C1 LYTVXCQQTLUEQR-UHFFFAOYSA-N 0.000 claims description 4
• 201000000980 schizophrenia Diseases 0.000 claims description 4
• AZIZBYRGIGKTLW-UHFFFAOYSA-N 1,4-diazepin-2-one Chemical compound O=C1C=NC=CC=N1 AZIZBYRGIGKTLW-UHFFFAOYSA-N 0.000 claims description 3
• 238000010511 deprotection reaction Methods 0.000 claims description 3
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
• XTQHVAXLUHGINO-UHFFFAOYSA-N 4-(3-pyridin-3-ylphenyl)-7-(2,2,2-trifluoroethoxy)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound N=1C2=CC(OCC(F)(F)F)=CC=C2NC(=O)CC=1C(C=1)=CC=CC=1C1=CC=CN=C1 XTQHVAXLUHGINO-UHFFFAOYSA-N 0.000 claims description 2
• YJNILYRQRSSTPP-UHFFFAOYSA-N 4-(3-pyridin-3-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC2=CC(C(F)(F)F)=CC=C2N=C1C(C=1)=CC=CC=1C1=CC=CN=C1 YJNILYRQRSSTPP-UHFFFAOYSA-N 0.000 claims description 2
• JYTRCRINABXASK-UHFFFAOYSA-N 4-(3-pyridin-4-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC2=CC(C(F)(F)F)=CC=C2N=C1C(C=1)=CC=CC=1C1=CC=NC=C1 JYTRCRINABXASK-UHFFFAOYSA-N 0.000 claims description 2
• PXNOUTUNFINTTA-UHFFFAOYSA-N 4-[3-(2,6-dimethylpyridin-4-yl)phenyl]-7-(2,2,2-trifluoroethoxy)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound CC1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=C(OCC(F)(F)F)C=C3N=2)C(F)(F)F)=C1 PXNOUTUNFINTTA-UHFFFAOYSA-N 0.000 claims description 2
• GGCAJGPNBPIIQA-UHFFFAOYSA-N 4-[3-(2,6-dimethylpyridin-4-yl)phenyl]-7-ethoxy-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(OCC)=CC=2N=C1C(C=1)=CC=CC=1C1=CC(C)=NC(C)=C1 GGCAJGPNBPIIQA-UHFFFAOYSA-N 0.000 claims description 2
• PQWNWLVSPGJPAF-UHFFFAOYSA-N 4-[3-(2,6-dimethylpyridin-4-yl)phenyl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound CC1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=CC=C3N=2)C(F)(F)F)=C1 PQWNWLVSPGJPAF-UHFFFAOYSA-N 0.000 claims description 2
• CHTAULFZQPVWNJ-UHFFFAOYSA-N 4-[3-(2-ethylpyridin-4-yl)phenyl]-7-methyl-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(CC)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=C(C)C=C3N=2)C(F)(F)F)=C1 CHTAULFZQPVWNJ-UHFFFAOYSA-N 0.000 claims description 2
• DFWDFOZNVALGES-UHFFFAOYSA-N 4-[3-(2-methylpyridin-4-yl)phenyl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=CC=C3N=2)C(F)(F)F)=C1 DFWDFOZNVALGES-UHFFFAOYSA-N 0.000 claims description 2
• PBXFRAFAGCEVSF-UHFFFAOYSA-N 4-[3-(6-cyclopropylpyridin-3-yl)phenyl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC2=CC(C(F)(F)F)=CC=C2N=C1C(C=1)=CC=CC=1C(C=N1)=CC=C1C1CC1 PBXFRAFAGCEVSF-UHFFFAOYSA-N 0.000 claims description 2
• MTRZSMDLMJKFMC-UHFFFAOYSA-N 4-[3-(6-methylpyrimidin-4-yl)phenyl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=CC=C3N=2)C(F)(F)F)=N1 MTRZSMDLMJKFMC-UHFFFAOYSA-N 0.000 claims description 2
• XUPVYWSSTOVIOJ-UHFFFAOYSA-N 4-[3-[2-(hydroxymethyl)pyridin-4-yl]phenyl]-7-methyl-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NC(CO)=C1 XUPVYWSSTOVIOJ-UHFFFAOYSA-N 0.000 claims description 2
• CUBHTWLIWFXCKK-UHFFFAOYSA-N 7,8-dichloro-4-(3-pyridin-3-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound N=1C=2C=C(Cl)C(Cl)=CC=2NC(=O)CC=1C(C=1)=CC=CC=1C1=CC=CN=C1 CUBHTWLIWFXCKK-UHFFFAOYSA-N 0.000 claims description 2
• VMEZSFFCHLCBBK-UHFFFAOYSA-N 7,8-dichloro-4-(3-pyridin-4-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound N=1C=2C=C(Cl)C(Cl)=CC=2NC(=O)CC=1C(C=1)=CC=CC=1C1=CC=NC=C1 VMEZSFFCHLCBBK-UHFFFAOYSA-N 0.000 claims description 2
• HXTQTHUBKDBECJ-UHFFFAOYSA-N 7,8-dichloro-4-[3-(2,6-dimethylpyridin-4-yl)phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound CC1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(Cl)=C(Cl)C=C3N=2)=C1 HXTQTHUBKDBECJ-UHFFFAOYSA-N 0.000 claims description 2
• CMLVJJVYIVBZNH-UHFFFAOYSA-N 7,8-dichloro-4-[3-(2-methylpyridin-4-yl)phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(Cl)=C(Cl)C=C3N=2)=C1 CMLVJJVYIVBZNH-UHFFFAOYSA-N 0.000 claims description 2
• BAXARIOGPJRTLH-UHFFFAOYSA-N 7-(cyclopropylmethoxy)-4-[3-(2-methylpyridin-4-yl)phenyl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=C(OCC4CC4)C=C3N=2)C(F)(F)F)=C1 BAXARIOGPJRTLH-UHFFFAOYSA-N 0.000 claims description 2
• DZCFLWXSUXKAJI-UHFFFAOYSA-N 7-(dimethylamino)-4-(3-pyridin-3-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(N(C)C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=CN=C1 DZCFLWXSUXKAJI-UHFFFAOYSA-N 0.000 claims description 2
• YQKASQGOPRPMLH-UHFFFAOYSA-N 7-(dimethylamino)-4-(3-pyridin-4-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(N(C)C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NC=C1 YQKASQGOPRPMLH-UHFFFAOYSA-N 0.000 claims description 2
• CCOJJDFNFUBNKN-UHFFFAOYSA-N 7-(dimethylamino)-4-[3-(2-methylpyridin-4-yl)phenyl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(N(C)C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NC(C)=C1 CCOJJDFNFUBNKN-UHFFFAOYSA-N 0.000 claims description 2
• GXQISOFEZQYHPI-UHFFFAOYSA-N 7-[methyl(propyl)amino]-4-(3-pyrazin-2-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(N(C)CCC)=CC=2N=C1C(C=1)=CC=CC=1C1=CN=CC=N1 GXQISOFEZQYHPI-UHFFFAOYSA-N 0.000 claims description 2
• OPUCFSUMZCYZKN-UHFFFAOYSA-N 7-chloro-4-(3-pyridin-4-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound N=1C=2C=C(Cl)C(C(F)(F)F)=CC=2NC(=O)CC=1C(C=1)=CC=CC=1C1=CC=NC=C1 OPUCFSUMZCYZKN-UHFFFAOYSA-N 0.000 claims description 2
• AHDAHZZDQMCLJT-UHFFFAOYSA-N 7-chloro-4-[3-(2,6-dimethylpyridin-4-yl)phenyl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound CC1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=C(Cl)C=C3N=2)C(F)(F)F)=C1 AHDAHZZDQMCLJT-UHFFFAOYSA-N 0.000 claims description 2
• RHZYZFRVSNAAOL-UHFFFAOYSA-N 7-ethoxy-4-(3-pyridin-3-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(OCC)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=CN=C1 RHZYZFRVSNAAOL-UHFFFAOYSA-N 0.000 claims description 2
• QFBDRSIFOKYSDY-UHFFFAOYSA-N 7-ethoxy-4-(3-pyridin-4-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(OCC)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NC=C1 QFBDRSIFOKYSDY-UHFFFAOYSA-N 0.000 claims description 2
• QCDLBZFFNJYTAV-UHFFFAOYSA-N 7-ethyl-4-[3-(2-methylpyridin-4-yl)phenyl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(CC)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NC(C)=C1 QCDLBZFFNJYTAV-UHFFFAOYSA-N 0.000 claims description 2
• XJKJJKMFTRWVGB-UHFFFAOYSA-N 7-methoxy-4-(3-pyridin-3-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(OC)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=CN=C1 XJKJJKMFTRWVGB-UHFFFAOYSA-N 0.000 claims description 2
• BUKFBCKSABZLLT-UHFFFAOYSA-N 7-methyl-4-(2-pyridin-3-ylpyridin-4-yl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(C)=CC=2N=C1C(C=1)=CC=NC=1C1=CC=CN=C1 BUKFBCKSABZLLT-UHFFFAOYSA-N 0.000 claims description 2
• JNFNUQBEVWFFJC-UHFFFAOYSA-N 7-methyl-4-(3-pyrazin-2-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(C)=CC=2N=C1C(C=1)=CC=CC=1C1=CN=CC=N1 JNFNUQBEVWFFJC-UHFFFAOYSA-N 0.000 claims description 2
• OQTSPIQICMTNOL-UHFFFAOYSA-N 7-methyl-4-(3-pyridazin-4-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NN=C1 OQTSPIQICMTNOL-UHFFFAOYSA-N 0.000 claims description 2
• WLGXHFREMLNUDH-UHFFFAOYSA-N 7-methyl-4-(3-pyridin-3-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=CN=C1 WLGXHFREMLNUDH-UHFFFAOYSA-N 0.000 claims description 2
• ZYGZDPKEZBLAHD-UHFFFAOYSA-N 7-methyl-4-(3-pyridin-4-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NC=C1 ZYGZDPKEZBLAHD-UHFFFAOYSA-N 0.000 claims description 2
• IWRBJKPPNKZIAC-UHFFFAOYSA-N 7-methyl-4-[2-(2-methylpyridin-4-yl)pyridin-4-yl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2N=CC=C(C=2)C=2CC(=O)NC3=CC(=C(C)C=C3N=2)C(F)(F)F)=C1 IWRBJKPPNKZIAC-UHFFFAOYSA-N 0.000 claims description 2
• ZTMGYWMZJBHXBD-UHFFFAOYSA-N 7-methyl-4-[3-(2-methylpyridin-4-yl)phenyl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=C(C)C=C3N=2)C(F)(F)F)=C1 ZTMGYWMZJBHXBD-UHFFFAOYSA-N 0.000 claims description 2
• NZWUYDARLBVUAZ-UHFFFAOYSA-N 8-(2-fluorophenyl)-4-(3-pyridin-3-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound FC1=CC=CC=C1C1=CC=C(N=C(CC(=O)N2)C=3C=C(C=CC=3)C=3C=NC=CC=3)C2=C1 NZWUYDARLBVUAZ-UHFFFAOYSA-N 0.000 claims description 2
• DEOUQGPUEWWMNC-UHFFFAOYSA-N 8-(2-fluorophenyl)-4-(3-pyridin-4-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound FC1=CC=CC=C1C1=CC=C(N=C(CC(=O)N2)C=3C=C(C=CC=3)C=3C=CN=CC=3)C2=C1 DEOUQGPUEWWMNC-UHFFFAOYSA-N 0.000 claims description 2
• VBTRNVBPGJSEAM-UHFFFAOYSA-N 8-(2-fluorophenyl)-4-(3-pyrimidin-5-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound FC1=CC=CC=C1C1=CC=C(N=C(CC(=O)N2)C=3C=C(C=CC=3)C=3C=NC=NC=3)C2=C1 VBTRNVBPGJSEAM-UHFFFAOYSA-N 0.000 claims description 2
• LKVQKLAWCNGKSL-UHFFFAOYSA-N 8-(2-fluorophenyl)-4-[3-(2-methylpyridin-4-yl)phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=CC=C3N=2)C=2C(=CC=CC=2)F)=C1 LKVQKLAWCNGKSL-UHFFFAOYSA-N 0.000 claims description 2
• PQMAJJWGJPOQQE-UHFFFAOYSA-N 8-chloro-4-(3-pyridin-3-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC2=CC(Cl)=CC=C2N=C1C(C=1)=CC=CC=1C1=CC=CN=C1 PQMAJJWGJPOQQE-UHFFFAOYSA-N 0.000 claims description 2
• RRJHUDLALLDKRL-UHFFFAOYSA-N 8-chloro-4-[3-(2,6-dimethylpyridin-4-yl)phenyl]-7-methyl-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound CC1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(Cl)=C(C)C=C3N=2)=C1 RRJHUDLALLDKRL-UHFFFAOYSA-N 0.000 claims description 2
• JLXAVOQTRVUYKG-UHFFFAOYSA-N 8-chloro-4-[3-(2-methylpyridin-3-yl)phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound CC1=NC=CC=C1C1=CC=CC(C=2CC(=O)NC3=CC(Cl)=CC=C3N=2)=C1 JLXAVOQTRVUYKG-UHFFFAOYSA-N 0.000 claims description 2
• PRPOBZJPAWDSGQ-UHFFFAOYSA-N 8-chloro-4-[3-(2-methylpyridin-4-yl)phenyl]-7-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(Cl)=C(C=C3N=2)C(F)(F)F)=C1 PRPOBZJPAWDSGQ-UHFFFAOYSA-N 0.000 claims description 2
• VOUQMUWKUYFRJK-UHFFFAOYSA-N 8-chloro-4-[3-(6-methylpyridin-3-yl)phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC=C1C1=CC=CC(C=2CC(=O)NC3=CC(Cl)=CC=C3N=2)=C1 VOUQMUWKUYFRJK-UHFFFAOYSA-N 0.000 claims description 2
• HRSCABPISYBZJE-UHFFFAOYSA-N 8-chloro-7-methyl-4-(3-pyrazin-2-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(Cl)C(C)=CC=2N=C1C(C=1)=CC=CC=1C1=CN=CC=N1 HRSCABPISYBZJE-UHFFFAOYSA-N 0.000 claims description 2
• ITPMBZMJFFOBBB-UHFFFAOYSA-N 8-chloro-7-methyl-4-(3-pyridazin-4-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(Cl)C(C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NN=C1 ITPMBZMJFFOBBB-UHFFFAOYSA-N 0.000 claims description 2
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• MOROTUNSYIQVSH-UHFFFAOYSA-N methyl 3-(2,6-dimethylpyridin-4-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C=2C=C(C)N=C(C)C=2)=C1 MOROTUNSYIQVSH-UHFFFAOYSA-N 0.000 description 1
• QHVUAQWSFHGQSS-UHFFFAOYSA-N methyl 3-(2-amino-6-methylpyrimidin-4-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C=2N=C(N)N=C(C)C=2)=C1 QHVUAQWSFHGQSS-UHFFFAOYSA-N 0.000 description 1
• LEKLAXUYPKSYOU-UHFFFAOYSA-N methyl 3-(2-aminopyrimidin-4-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C=2N=C(N)N=CC=2)=C1 LEKLAXUYPKSYOU-UHFFFAOYSA-N 0.000 description 1
• QDWVBIOMVCNXCM-UHFFFAOYSA-N methyl 3-(2-methylpyridin-3-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C=2C(=NC=CC=2)C)=C1 QDWVBIOMVCNXCM-UHFFFAOYSA-N 0.000 description 1
• JNZREOLYWJGVGK-UHFFFAOYSA-N methyl 3-(2-methylpyrimidin-4-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C=2N=C(C)N=CC=2)=C1 JNZREOLYWJGVGK-UHFFFAOYSA-N 0.000 description 1
• BNJAKNOEMIPOET-UHFFFAOYSA-N methyl 3-(3-methyl-1,2,4-triazin-6-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C=2N=NC(C)=NC=2)=C1 BNJAKNOEMIPOET-UHFFFAOYSA-N 0.000 description 1
• ILLWHUXRPCCWQN-UHFFFAOYSA-N methyl 3-(3-oxobutanoyl)benzoate Chemical compound COC(=O)C1=CC=CC(C(=O)CC(C)=O)=C1 ILLWHUXRPCCWQN-UHFFFAOYSA-N 0.000 description 1
• MJXHWGZUDXWAKC-UHFFFAOYSA-N methyl 3-(5,6-dimethyl-1,2,4-triazin-3-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C=2N=C(C)C(C)=NN=2)=C1 MJXHWGZUDXWAKC-UHFFFAOYSA-N 0.000 description 1
• XYYUHALYKYLVPL-UHFFFAOYSA-N methyl 3-(6-cyanopyridin-3-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C=2C=NC(=CC=2)C#N)=C1 XYYUHALYKYLVPL-UHFFFAOYSA-N 0.000 description 1
• KBFWJKJSQVKEPX-UHFFFAOYSA-N methyl 3-(6-methoxypyridazin-3-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C=2N=NC(OC)=CC=2)=C1 KBFWJKJSQVKEPX-UHFFFAOYSA-N 0.000 description 1
• GTLIWFAEWCMGRX-UHFFFAOYSA-N methyl 3-(6-methylpyridazin-3-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C=2N=NC(C)=CC=2)=C1 GTLIWFAEWCMGRX-UHFFFAOYSA-N 0.000 description 1
• HWQAEDWFEPDMOX-UHFFFAOYSA-N methyl 3-(6-methylpyridin-3-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C=2C=NC(C)=CC=2)=C1 HWQAEDWFEPDMOX-UHFFFAOYSA-N 0.000 description 1
• OYPDZZQTVXZYBI-UHFFFAOYSA-N methyl 3-(6-methylpyrimidin-4-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C=2N=CN=C(C)C=2)=C1 OYPDZZQTVXZYBI-UHFFFAOYSA-N 0.000 description 1
• MEXYDEMLZDRPMD-UHFFFAOYSA-N methyl 3-[2-(2-methoxyethylamino)-6-methylpyrimidin-4-yl]benzoate Chemical compound COCCNC1=NC(C)=CC(C=2C=C(C=CC=2)C(=O)OC)=N1 MEXYDEMLZDRPMD-UHFFFAOYSA-N 0.000 description 1
• KYFWIAFEEMFUHM-UHFFFAOYSA-N methyl 3-[2-(acetyloxymethyl)-6-methylpyridin-4-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C=2C=C(COC(C)=O)N=C(C)C=2)=C1 KYFWIAFEEMFUHM-UHFFFAOYSA-N 0.000 description 1
• SFCOEBBIVJLZHE-UHFFFAOYSA-N methyl 3-[2-(acetyloxymethyl)pyridin-4-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C=2C=C(COC(C)=O)N=CC=2)=C1 SFCOEBBIVJLZHE-UHFFFAOYSA-N 0.000 description 1
• WFHIGNDVSVSHMV-UHFFFAOYSA-N methyl 3-[2-(dimethylamino)-6-methylpyrimidin-4-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C=2N=C(N=C(C)C=2)N(C)C)=C1 WFHIGNDVSVSHMV-UHFFFAOYSA-N 0.000 description 1
• DPKFMXPSGWFMNF-UHFFFAOYSA-N methyl 3-[2-(hydroxymethyl)pyridin-4-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C=2C=C(CO)N=CC=2)=C1 DPKFMXPSGWFMNF-UHFFFAOYSA-N 0.000 description 1
• BQEJDUQRPNKRJQ-UHFFFAOYSA-N methyl 3-[2-methyl-6-(oxan-2-yloxymethyl)pyridin-4-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C=2C=C(COC3OCCCC3)N=C(C)C=2)=C1 BQEJDUQRPNKRJQ-UHFFFAOYSA-N 0.000 description 1
• HQEWXXXBMQMFGM-UHFFFAOYSA-N methyl 3-[6-(2-methoxyethylamino)pyrimidin-4-yl]benzoate Chemical compound C1=NC(NCCOC)=CC(C=2C=C(C=CC=2)C(=O)OC)=N1 HQEWXXXBMQMFGM-UHFFFAOYSA-N 0.000 description 1
• DDGIMUOQGSBPPV-UHFFFAOYSA-N methyl 3-[6-(methylamino)pyrimidin-4-yl]benzoate Chemical compound C1=NC(NC)=CC(C=2C=C(C=CC=2)C(=O)OC)=N1 DDGIMUOQGSBPPV-UHFFFAOYSA-N 0.000 description 1
• FOCFAZDUCUHPMH-UHFFFAOYSA-N methyl 3-[6-methyl-2-(methylamino)pyrimidin-4-yl]benzoate Chemical compound CNC1=NC(C)=CC(C=2C=C(C=CC=2)C(=O)OC)=N1 FOCFAZDUCUHPMH-UHFFFAOYSA-N 0.000 description 1
• MXLYAEPCQSMXEM-UHFFFAOYSA-N methyl 3-[6-methyl-2-[2-(oxan-2-yloxy)ethylamino]pyrimidin-4-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C=2N=C(NCCOC3OCCCC3)N=C(C)C=2)=C1 MXLYAEPCQSMXEM-UHFFFAOYSA-N 0.000 description 1
• DGMXBVBBCRYAMC-UHFFFAOYSA-N methyl 3-pyridazin-3-ylbenzoate Chemical compound COC(=O)C1=CC=CC(C=2N=NC=CC=2)=C1 DGMXBVBBCRYAMC-UHFFFAOYSA-N 0.000 description 1
• IOJFNHUNCBUINL-UHFFFAOYSA-N methyl 3-pyrimidin-2-ylbenzoate Chemical compound COC(=O)C1=CC=CC(C=2N=CC=CN=2)=C1 IOJFNHUNCBUINL-UHFFFAOYSA-N 0.000 description 1
• IUJPGEFKXSUZTK-UHFFFAOYSA-N methyl 3-pyrimidin-4-ylbenzoate Chemical compound COC(=O)C1=CC=CC(C=2N=CN=CC=2)=C1 IUJPGEFKXSUZTK-UHFFFAOYSA-N 0.000 description 1
• JUHDUIDUEUEQND-UHFFFAOYSA-N methylium Chemical compound [CH3+] JUHDUIDUEUEQND-UHFFFAOYSA-N 0.000 description 1
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
• DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
• IXWBEJQARFKXJY-UHFFFAOYSA-N n-(diacetamidomethyl)acetamide Chemical compound CC(=O)NC(NC(C)=O)NC(C)=O IXWBEJQARFKXJY-UHFFFAOYSA-N 0.000 description 1
• HNPCDFJZADHNHD-UHFFFAOYSA-N n-(diformamidomethyl)formamide Chemical compound O=CNC(NC=O)NC=O HNPCDFJZADHNHD-UHFFFAOYSA-N 0.000 description 1
• MSWBHPCGEQZSGS-UHFFFAOYSA-N n-[4-methyl-2-nitro-3-(trifluoromethyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(C)C(C(F)(F)F)=C1[N+]([O-])=O MSWBHPCGEQZSGS-UHFFFAOYSA-N 0.000 description 1
• YCWKZLXTHMGYAO-UHFFFAOYSA-N n-methylcyclopropanamine;hydrochloride Chemical compound Cl.CNC1CC1 YCWKZLXTHMGYAO-UHFFFAOYSA-N 0.000 description 1
• VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical class [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
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• 230000009871 nonspecific binding Effects 0.000 description 1
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• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
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• XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
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