ES2294264T3 - Derivados de hidrobenzodiazepin-2-ona para el tratamiento de transtornos neurologicos. - Google Patents

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Publication number

ES2294264T3

ES2294264T3 ES03702549T ES03702549T ES2294264T3 ES 2294264 T3 ES2294264 T3 ES 2294264T3 ES 03702549 T ES03702549 T ES 03702549T ES 03702549 T ES03702549 T ES 03702549T ES 2294264 T3 ES2294264 T3 ES 2294264T3

Authority

ES

Spain

Prior art keywords

phenyl

pyridin

tert

methyl

butyl

Prior art date

2002-02-06

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.)

Expired - Lifetime

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• 208000012902 Nervous system disease Diseases 0.000 title description 4
• 208000025966 Neurological disease Diseases 0.000 title description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 592
• -1 pyrrole-1-yl Chemical group 0.000 claims abstract description 237
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 52
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 41
• 239000001257 hydrogen Substances 0.000 claims abstract description 35
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 35
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 34
• 150000002367 halogens Chemical class 0.000 claims abstract description 32
• 125000001424 substituent group Chemical group 0.000 claims abstract description 22
• 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 19
• 125000004428 fluoroalkoxy group Chemical group 0.000 claims abstract description 17
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 16
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 15
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 15
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims abstract description 5
• 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 abstract description 5
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
• 238000000034 method Methods 0.000 claims description 686
• 239000002253 acid Substances 0.000 claims description 50
• 150000002431 hydrogen Chemical group 0.000 claims description 25
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
• 150000003839 salts Chemical class 0.000 claims description 22
• 125000003709 fluoroalkyl group Chemical group 0.000 claims description 20
• 125000003282 alkyl amino group Chemical group 0.000 claims description 19
• 238000002360 preparation method Methods 0.000 claims description 18
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
• 239000003814 drug Substances 0.000 claims description 11
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 10
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
• 229940079593 drug Drugs 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 230000001684 chronic effect Effects 0.000 claims description 7
• 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
• 125000005191 hydroxyalkylamino group Chemical group 0.000 claims description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
• 208000028017 Psychotic disease Diseases 0.000 claims description 5
• 230000001154 acute effect Effects 0.000 claims description 5
• 125000003277 amino group Chemical group 0.000 claims description 5
• 230000002265 prevention Effects 0.000 claims description 5
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
• 230000008569 process Effects 0.000 claims description 5
• 208000024827 Alzheimer disease Diseases 0.000 claims description 4
• 208000010877 cognitive disease Diseases 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims description 4
• 201000000980 schizophrenia Diseases 0.000 claims description 4
• 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 3
• 230000001351 cycling effect Effects 0.000 claims description 3
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
• 238000002483 medication Methods 0.000 claims description 3
• 230000000926 neurological effect Effects 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
• XFCBAUSXXGLTIP-UHFFFAOYSA-N 4-(3-pyridin-3-ylphenyl)-7-(2,2,2-trifluoroethoxy)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(OCC(F)(F)F)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=CN=C1 XFCBAUSXXGLTIP-UHFFFAOYSA-N 0.000 claims description 2
• NBKPYZLFZCYJJE-UHFFFAOYSA-N 4-(3-pyridin-4-ylphenyl)-7-(2,2,2-trifluoroethoxy)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(OCC(F)(F)F)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NC=C1 NBKPYZLFZCYJJE-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
• UVNQIBJKZJJBQK-UHFFFAOYSA-N 4-[3-(2,6-dimethylpyridin-4-yl)phenyl]-7-ethyl-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(C)=NC(C)=C1 UVNQIBJKZJJBQK-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
• CLEXCUYVRGOQCW-UHFFFAOYSA-N 4-[3-(2,6-dimethylpyridin-4-yl)phenyl]-8-methyl-7-(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)=C(C=C3N=2)C(F)(F)F)=C1 CLEXCUYVRGOQCW-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
• XRLZWRIHQVVACZ-UHFFFAOYSA-N 4-[3-(2-methylpyridin-4-yl)phenyl]-8-(trifluoromethoxy)-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(OC(F)(F)F)=CC=C3N=2)=C1 XRLZWRIHQVVACZ-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
• 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
• QHWRKFWOOXWYMW-UHFFFAOYSA-N 8-(2-fluorophenyl)-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(=CC=C3N=2)C=2C(=CC=CC=2)F)=C1 QHWRKFWOOXWYMW-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
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• 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
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