ES2246012T3 - Derivados de dihidro benzo(b) (1,4)diacepin-2-ona como antagonistas de mglur2 ii. - Google Patents

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Publication number

ES2246012T3

ES2246012T3 ES02737911T ES02737911T ES2246012T3 ES 2246012 T3 ES2246012 T3 ES 2246012T3 ES 02737911 T ES02737911 T ES 02737911T ES 02737911 T ES02737911 T ES 02737911T ES 2246012 T3 ES2246012 T3 ES 2246012T3

Authority

ES

Spain

Prior art keywords

phenyl

methyl

acid

amino

tert

Prior art date

2001-04-12

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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• 102100036837 Metabotropic glutamate receptor 2 Human genes 0.000 title description 5
• 101150016175 Grm2 gene Proteins 0.000 title 1
• -1 pyrrole -1-yl Chemical group 0.000 claims abstract description 849
• 150000001875 compounds Chemical class 0.000 claims abstract description 531
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 38
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 34
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 26
• 150000003839 salts Chemical class 0.000 claims abstract description 21
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 17
• 150000002367 halogens Chemical group 0.000 claims abstract description 16
• 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 13
• 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 12
• 125000001424 substituent group Chemical group 0.000 claims abstract description 11
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 10
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
• 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 5
• 239000002253 acid Substances 0.000 claims description 681
• 238000000034 method Methods 0.000 claims description 566
• 239000000460 chlorine Substances 0.000 claims description 118
• 238000006243 chemical reaction Methods 0.000 claims description 70
• 238000002360 preparation method Methods 0.000 claims description 22
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
• 239000003814 drug Substances 0.000 claims description 11
• 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 11
• 229940079593 drug Drugs 0.000 claims description 9
• 230000001154 acute effect Effects 0.000 claims description 7
• 125000004414 alkyl thio group Chemical group 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• 238000002483 medication Methods 0.000 claims description 6
• 208000028017 Psychotic disease Diseases 0.000 claims description 5
• 230000001684 chronic effect Effects 0.000 claims description 5
• 239000001257 hydrogen Substances 0.000 claims description 5
• 229910052739 hydrogen Inorganic materials 0.000 claims description 5
• 230000002265 prevention Effects 0.000 claims description 5
• 230000008569 process Effects 0.000 claims description 5
• 229910052801 chlorine Inorganic materials 0.000 claims description 4
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
• 201000000980 schizophrenia Diseases 0.000 claims description 4
• DJMZLSQXQSZBAN-UHFFFAOYSA-N 4-[2-oxo-7-(2,2,2-trifluoroethoxy)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-4-yl]pyridine-2-carbonitrile Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(OCC(F)(F)F)=CC=2N=C1C1=CC=NC(C#N)=C1 DJMZLSQXQSZBAN-UHFFFAOYSA-N 0.000 claims description 3
• GBRPDPUYJNPHFW-UHFFFAOYSA-N 4-[2-oxo-7-pyrrolidin-1-yl-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-4-yl]pyridine-2-carbonitrile Chemical compound FC(F)(F)C1=CC=2NC(=O)CC(C=3C=C(N=CC=3)C#N)=NC=2C=C1N1CCCC1 GBRPDPUYJNPHFW-UHFFFAOYSA-N 0.000 claims description 3
• ASXHDONHHPHYRD-UHFFFAOYSA-N 4-[3-(3-methyl-1,2-oxazol-5-yl)phenyl]-2-oxo-7-piperidin-1-yl-1,3-dihydro-1,5-benzodiazepine-8-carbonitrile Chemical compound O1N=C(C)C=C1C1=CC=CC(C=2CC(=O)NC3=CC(=C(N4CCCCC4)C=C3N=2)C#N)=C1 ASXHDONHHPHYRD-UHFFFAOYSA-N 0.000 claims description 3
• LGGCNWMQSRYKEK-UHFFFAOYSA-N 4-[3-(3-methyl-1,2-oxazol-5-yl)phenyl]-7-[methyl(propan-2-yl)amino]-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(C)C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC(C)=NO1 LGGCNWMQSRYKEK-UHFFFAOYSA-N 0.000 claims description 3
• OWPXWLMWINGIJA-UHFFFAOYSA-N 4-[3-(3-methyl-1,2-oxazol-5-yl)phenyl]-7-[methyl(propyl)amino]-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=CC(C)=NO1 OWPXWLMWINGIJA-UHFFFAOYSA-N 0.000 claims description 3
• MOZPRFSXXYUWQA-UHFFFAOYSA-N 4-[3-[5-(azetidin-1-ylmethyl)triazol-1-yl]phenyl]-8-chloro-7-[methyl(2-methylpropyl)amino]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(Cl)C(N(C)CC(C)C)=CC=2N=C1C(C=1)=CC=CC=1N1N=NC=C1CN1CCC1 MOZPRFSXXYUWQA-UHFFFAOYSA-N 0.000 claims description 3
• AKNWSIBZOBQZRO-UHFFFAOYSA-N 4-[3-[5-(azetidin-1-ylmethyl)triazol-1-yl]phenyl]-8-chloro-7-[methyl(propan-2-yl)amino]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(Cl)C(N(C)C(C)C)=CC=2N=C1C(C=1)=CC=CC=1N1N=NC=C1CN1CCC1 AKNWSIBZOBQZRO-UHFFFAOYSA-N 0.000 claims description 3
• RMBIAVCOZGNTCG-UHFFFAOYSA-N 4-[3-[5-[(cyclopropylmethylamino)methyl]triazol-1-yl]phenyl]-8-methyl-7-[methyl(2-methylpropyl)amino]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C)C(N(C)CC(C)C)=CC=2N=C1C(C=1)=CC=CC=1N1N=NC=C1CNCC1CC1 RMBIAVCOZGNTCG-UHFFFAOYSA-N 0.000 claims description 3
• QPHLWEQWHSMTNX-UHFFFAOYSA-N 4-[7-[cyclopropyl(methyl)amino]-2-oxo-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-4-yl]pyridine-2-carbonitrile Chemical compound C=1C=2N=C(C=3C=C(N=CC=3)C#N)CC(=O)NC=2C=C(C(F)(F)F)C=1N(C)C1CC1 QPHLWEQWHSMTNX-UHFFFAOYSA-N 0.000 claims description 3
• CZLWEHDNIPKFTN-UHFFFAOYSA-N 4-[7-[cyclopropylmethyl(methyl)amino]-2-oxo-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-4-yl]pyridine-2-carbonitrile Chemical compound C=1C=2N=C(C=3C=C(N=CC=3)C#N)CC(=O)NC=2C=C(C(F)(F)F)C=1N(C)CC1CC1 CZLWEHDNIPKFTN-UHFFFAOYSA-N 0.000 claims description 3
• VYNUPTPNOCSSBJ-UHFFFAOYSA-N 7-(diethylamino)-4-[3-(3-methyl-1,2-oxazol-5-yl)phenyl]-2-oxo-1,3-dihydro-1,5-benzodiazepine-8-carbonitrile Chemical compound C1C(=O)NC=2C=C(C#N)C(N(CC)CC)=CC=2N=C1C(C=1)=CC=CC=1C1=CC(C)=NO1 VYNUPTPNOCSSBJ-UHFFFAOYSA-N 0.000 claims description 3
• DDDRVKGHRFVCSK-UHFFFAOYSA-N 7-(dimethylamino)-4-(3-imidazol-1-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=1N1C=CN=C1 DDDRVKGHRFVCSK-UHFFFAOYSA-N 0.000 claims description 3
• UYLWLBKJGHXHEJ-UHFFFAOYSA-N 7-(dimethylamino)-4-[3-(2-methylpyrazol-3-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=NN1C UYLWLBKJGHXHEJ-UHFFFAOYSA-N 0.000 claims description 3
• ZZVIUNYEAUAGMT-UHFFFAOYSA-N 7-(dimethylamino)-4-[3-(3-methyl-1,2-oxazol-5-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(C)=NO1 ZZVIUNYEAUAGMT-UHFFFAOYSA-N 0.000 claims description 3
• AKHVLIYLESRYKL-UHFFFAOYSA-N 7-(dimethylamino)-8-(2-phenylethynyl)-4-[3-(triazol-1-yl)phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound CN(C)C1=CC=2N=C(C=3C=C(C=CC=3)N3N=NC=C3)CC(=O)NC=2C=C1C#CC1=CC=CC=C1 AKHVLIYLESRYKL-UHFFFAOYSA-N 0.000 claims description 3
• OHWFEQKMVFNWLV-UHFFFAOYSA-N 7-(dimethylamino)-8-methyl-4-[3-(3-methyl-1,2-oxazol-5-yl)phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C)C(N(C)C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC(C)=NO1 OHWFEQKMVFNWLV-UHFFFAOYSA-N 0.000 claims description 3
• HAAZRBAMJKYOAA-UHFFFAOYSA-N 7-[ethyl(methyl)amino]-8-methyl-4-[3-(3-methyl-1,2-oxazol-5-yl)phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C)C(N(C)CC)=CC=2N=C1C(C=1)=CC=CC=1C1=CC(C)=NO1 HAAZRBAMJKYOAA-UHFFFAOYSA-N 0.000 claims description 3
• NXJBMLLXZBHSHA-UHFFFAOYSA-N 7-[methyl(2-methylpropyl)amino]-4-[3-(3-methyl-1,2-oxazol-5-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)CC(C)C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC(C)=NO1 NXJBMLLXZBHSHA-UHFFFAOYSA-N 0.000 claims description 3
• HWPJVWXJTPQBEF-UHFFFAOYSA-N 7-[methyl(2-methylpropyl)amino]-4-[3-[5-[[methyl(propan-2-yl)amino]methyl]triazol-1-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)CC(C)C)=CC=2N=C1C(C=1)=CC=CC=1N1N=NC=C1CN(C)C(C)C HWPJVWXJTPQBEF-UHFFFAOYSA-N 0.000 claims description 3
• GGCLCUPVAHZUHM-UHFFFAOYSA-N 7-[methyl(propan-2-yl)amino]-4-[3-[5-(pyrrolidin-1-ylmethyl)triazol-1-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(C)C)=CC=2N=C1C(C=1)=CC=CC=1N1N=NC=C1CN1CCCC1 GGCLCUPVAHZUHM-UHFFFAOYSA-N 0.000 claims description 3
• OGFPVPFGOGJHSX-UHFFFAOYSA-N 8-(2-fluorophenyl)-4-[3-(triazol-1-yl)phenyl]-7-(2,2,2-trifluoroethoxy)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound FC1=CC=CC=C1C(C(=C1)OCC(F)(F)F)=CC2=C1N=C(C=1C=C(C=CC=1)N1N=NC=C1)CC(=O)N2 OGFPVPFGOGJHSX-UHFFFAOYSA-N 0.000 claims description 3
• PFXSUPYIBPKVQN-UHFFFAOYSA-N 8-chloro-4-[3-(3-methyl-1,2-oxazol-5-yl)phenyl]-7-(2-methylpropylamino)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(Cl)C(NCC(C)C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC(C)=NO1 PFXSUPYIBPKVQN-UHFFFAOYSA-N 0.000 claims description 3
• VGCFBGKWKFNEIC-UHFFFAOYSA-N 8-chloro-4-[3-[5-[(dimethylamino)methyl]triazol-1-yl]phenyl]-7-[methyl(2-methylpropyl)amino]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(Cl)C(N(C)CC(C)C)=CC=2N=C1C(C=1)=CC=CC=1N1N=NC=C1CN(C)C VGCFBGKWKFNEIC-UHFFFAOYSA-N 0.000 claims description 3
• GZPCGGQMFQCOJG-UHFFFAOYSA-N 8-chloro-4-[3-[5-[[methyl(2-methylpropyl)amino]methyl]triazol-1-yl]phenyl]-7-[methyl(propan-2-yl)amino]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound CC(C)CN(C)CC1=CN=NN1C1=CC=CC(C=2CC(=O)NC3=CC(Cl)=C(N(C)C(C)C)C=C3N=2)=C1 GZPCGGQMFQCOJG-UHFFFAOYSA-N 0.000 claims description 3
• SOYNHYRIQYZWGC-UHFFFAOYSA-N 8-chloro-7-[methyl(2-methylpropyl)amino]-4-[3-[5-(piperidin-1-ylmethyl)triazol-1-yl]phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(Cl)C(N(C)CC(C)C)=CC=2N=C1C(C=1)=CC=CC=1N1N=NC=C1CN1CCCCC1 SOYNHYRIQYZWGC-UHFFFAOYSA-N 0.000 claims description 3
• DHDNESILTRMMAB-UHFFFAOYSA-N 8-chloro-7-[methyl(2-methylpropyl)amino]-4-[3-[5-(pyrrolidin-1-ylmethyl)triazol-1-yl]phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(Cl)C(N(C)CC(C)C)=CC=2N=C1C(C=1)=CC=CC=1N1N=NC=C1CN1CCCC1 DHDNESILTRMMAB-UHFFFAOYSA-N 0.000 claims description 3
• SAVDHCKDKXITDB-UHFFFAOYSA-N 8-chloro-7-[methyl(propan-2-yl)amino]-4-[3-[5-(pyrrolidin-1-ylmethyl)triazol-1-yl]phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(Cl)C(N(C)C(C)C)=CC=2N=C1C(C=1)=CC=CC=1N1N=NC=C1CN1CCCC1 SAVDHCKDKXITDB-UHFFFAOYSA-N 0.000 claims description 3
• VHBNDJVFQOPHQL-UHFFFAOYSA-N 8-chloro-7-[methyl(propan-2-yl)amino]-4-[3-[5-[[methyl(propan-2-yl)amino]methyl]triazol-1-yl]phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound CC(C)N(C)CC1=CN=NN1C1=CC=CC(C=2CC(=O)NC3=CC(Cl)=C(N(C)C(C)C)C=C3N=2)=C1 VHBNDJVFQOPHQL-UHFFFAOYSA-N 0.000 claims description 3
• YTKAPOCJJREWCQ-UHFFFAOYSA-N 8-chloro-7-[methyl(propyl)amino]-4-[3-[5-(pyrrolidin-1-ylmethyl)triazol-1-yl]phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(Cl)C(N(C)CCC)=CC=2N=C1C(C=1)=CC=CC=1N1N=NC=C1CN1CCCC1 YTKAPOCJJREWCQ-UHFFFAOYSA-N 0.000 claims description 3
• QBSNFNKYIAYAHP-UHFFFAOYSA-N 8-methyl-7-[methyl(2-methylpropyl)amino]-4-[3-(3-methyl-1,2-oxazol-5-yl)phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C)C(N(C)CC(C)C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC(C)=NO1 QBSNFNKYIAYAHP-UHFFFAOYSA-N 0.000 claims description 3
• PUMGQYZLUWHXDO-UHFFFAOYSA-N 8-methyl-7-[methyl(2-methylpropyl)amino]-4-[3-[5-(pyrrolidin-1-ylmethyl)triazol-1-yl]phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C)C(N(C)CC(C)C)=CC=2N=C1C(C=1)=CC=CC=1N1N=NC=C1CN1CCCC1 PUMGQYZLUWHXDO-UHFFFAOYSA-N 0.000 claims description 3
• 208000024827 Alzheimer disease Diseases 0.000 claims description 3
• 208000026139 Memory disease Diseases 0.000 claims description 3
• 208000012902 Nervous system disease Diseases 0.000 claims description 3
• 208000025966 Neurological disease Diseases 0.000 claims description 3
• 125000003277 amino group Chemical group 0.000 claims description 3
• 208000010877 cognitive disease Diseases 0.000 claims description 3
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• SLZWQLBLGIMSRX-UHFFFAOYSA-N 4-(3-imidazol-1-ylphenyl)-7-(2-methylpropylamino)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(NCC(C)C)=CC=2N=C1C(C=1)=CC=CC=1N1C=CN=C1 SLZWQLBLGIMSRX-UHFFFAOYSA-N 0.000 claims description 2
• QVWATQZHVALIAI-UHFFFAOYSA-N 4-[3-[4-(hydroxymethyl)-1,3-thiazol-2-yl]phenyl]-7-[methyl(propyl)amino]-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=NC(CO)=CS1 QVWATQZHVALIAI-UHFFFAOYSA-N 0.000 claims description 2
• KGBAJRRLCNCMNT-UHFFFAOYSA-N 4-[3-[5-(hydroxymethyl)-1,3,4-thiadiazol-2-yl]phenyl]-7-[methyl(propyl)amino]-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=NN=C(CO)S1 KGBAJRRLCNCMNT-UHFFFAOYSA-N 0.000 claims description 2
• MMFHASXGTDQSPH-UHFFFAOYSA-N 4-[7-[methyl(propan-2-yl)amino]-2-oxo-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-4-yl]pyridine-2-carbonitrile Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(N(C)C(C)C)=CC=2N=C1C1=CC=NC(C#N)=C1 MMFHASXGTDQSPH-UHFFFAOYSA-N 0.000 claims description 2
• VAQIGIYSLWNPSM-UHFFFAOYSA-N 7-(dimethylamino)-4-[3-[4-(hydroxymethyl)-1,3-oxazol-2-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=NC(CO)=CO1 VAQIGIYSLWNPSM-UHFFFAOYSA-N 0.000 claims description 2
• UXWOBRYNOZWNRK-UHFFFAOYSA-N 7-(dimethylamino)-4-[3-[4-(hydroxymethyl)-1,3-thiazol-2-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=NC(CO)=CS1 UXWOBRYNOZWNRK-UHFFFAOYSA-N 0.000 claims description 2
• GKGGRNXTYYJBPH-UHFFFAOYSA-N 7-[methyl(2-methylpropyl)amino]-4-[3-(triazol-1-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)CC(C)C)=CC=2N=C1C(C=1)=CC=CC=1N1C=CN=N1 GKGGRNXTYYJBPH-UHFFFAOYSA-N 0.000 claims description 2
• JHMOJYCUDSVXIH-UHFFFAOYSA-N 7-[methyl(propyl)amino]-4-[3-(triazol-1-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)CCC)=CC=2N=C1C(C=1)=CC=CC=1N1C=CN=N1 JHMOJYCUDSVXIH-UHFFFAOYSA-N 0.000 claims description 2
• PKAGRYFXAAQOOC-UHFFFAOYSA-N 8-chloro-4-(3-imidazol-1-ylphenyl)-7-(2-methylpropylamino)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(Cl)C(NCC(C)C)=CC=2N=C1C(C=1)=CC=CC=1N1C=CN=C1 PKAGRYFXAAQOOC-UHFFFAOYSA-N 0.000 claims description 2
• BMMSJPYGKWFQKH-UHFFFAOYSA-N 8-chloro-4-[3-(3-methyl-1,2-oxazol-5-yl)phenyl]-7-(propan-2-ylamino)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(Cl)C(NC(C)C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC(C)=NO1 BMMSJPYGKWFQKH-UHFFFAOYSA-N 0.000 claims description 2
• NGCNTLZHOWWZPG-UHFFFAOYSA-N 8-chloro-4-[3-[4-(hydroxymethyl)-1,3-oxazol-2-yl]phenyl]-7-[methyl(2-methylpropyl)amino]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(Cl)C(N(C)CC(C)C)=CC=2N=C1C(C=1)=CC=CC=1C1=NC(CO)=CO1 NGCNTLZHOWWZPG-UHFFFAOYSA-N 0.000 claims description 2
• CWRWLBCLNIXFEP-UHFFFAOYSA-N 8-chloro-4-[3-[4-(hydroxymethyl)-1,3-oxazol-2-yl]phenyl]-7-[methyl(propan-2-yl)amino]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(Cl)C(N(C)C(C)C)=CC=2N=C1C(C=1)=CC=CC=1C1=NC(CO)=CO1 CWRWLBCLNIXFEP-UHFFFAOYSA-N 0.000 claims description 2
• FNVVDXIMWWBIRY-UHFFFAOYSA-N 8-chloro-4-[3-[4-(hydroxymethyl)-1,3-oxazol-2-yl]phenyl]-7-[methyl(propyl)amino]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(Cl)C(N(C)CCC)=CC=2N=C1C(C=1)=CC=CC=1C1=NC(CO)=CO1 FNVVDXIMWWBIRY-UHFFFAOYSA-N 0.000 claims description 2
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