RU2263112C2 - ПРОИЗВОДНЫЕ ДИГИДРОБЕНЗО[b][1,4]ДИАЗЕПИН-2-ОНА В КАЧЕСТВЕ АНТАГОНИСТОВ MGLUR2 II - Google Patents

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Publication number

RU2263112C2

RU2263112C2 RU2003130637/04A RU2003130637A RU2263112C2 RU 2263112 C2 RU2263112 C2 RU 2263112C2 RU 2003130637/04 A RU2003130637/04 A RU 2003130637/04A RU 2003130637 A RU2003130637 A RU 2003130637A RU 2263112 C2 RU2263112 C2 RU 2263112C2

Authority

RU

Russia

Prior art keywords

phenyl

diazepin

dihydrobenzo

tert

mmol

Prior art date

2001-04-12

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• 239000005557 antagonist Substances 0.000 title claims abstract description 6
• 102100036837 Metabotropic glutamate receptor 2 Human genes 0.000 title description 8
• 101150016175 Grm2 gene Proteins 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 797
• -1 pyrrole-1-yl Chemical group 0.000 claims abstract description 432
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 77
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 59
• 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 42
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 31
• 150000003839 salts Chemical class 0.000 claims abstract description 20
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 16
• 229910052731 fluorine Inorganic materials 0.000 claims abstract description 15
• 239000011737 fluorine Substances 0.000 claims abstract description 14
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 12
• 239000003814 drug Substances 0.000 claims abstract description 10
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 7
• 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 7
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 3
• 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 3
• 229910052801 chlorine Inorganic materials 0.000 claims abstract 2
• 125000003545 alkoxy group Chemical group 0.000 claims description 46
• 229910052736 halogen Inorganic materials 0.000 claims description 15
• 150000002367 halogens Chemical class 0.000 claims description 15
• 229940079593 drug Drugs 0.000 claims description 9
• 125000001424 substituent group Chemical group 0.000 claims description 9
• 125000004414 alkyl thio group Chemical group 0.000 claims description 7
• AZIZBYRGIGKTLW-UHFFFAOYSA-N 1,4-diazepin-2-one Chemical compound O=C1C=NC=CC=N1 AZIZBYRGIGKTLW-UHFFFAOYSA-N 0.000 claims description 5
• 230000001154 acute effect Effects 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
• 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 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 4
• 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 4
• 208000012902 Nervous system disease Diseases 0.000 claims description 4
• 208000025966 Neurological disease Diseases 0.000 claims description 4
• 208000028017 Psychotic disease Diseases 0.000 claims description 4
• 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
• 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
• 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
• 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
• 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
• JXWKOMRRAURYHF-UHFFFAOYSA-N 8-chloro-4-[3-[4-(hydroxymethyl)-1,3-thiazol-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)=CS1 JXWKOMRRAURYHF-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
• 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
• 208000024827 Alzheimer disease Diseases 0.000 claims description 3
• 208000028698 Cognitive impairment Diseases 0.000 claims description 3
• 208000010877 cognitive disease Diseases 0.000 claims description 3
• 206010027175 memory impairment Diseases 0.000 claims description 3
• 201000000980 schizophrenia Diseases 0.000 claims description 3
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
• 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
• 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 2
• 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 2
• LLYJKBFHJSMZAX-UHFFFAOYSA-N 4-[7-(cyclopropylmethylamino)-2-oxo-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=C1NCC1CC1 LLYJKBFHJSMZAX-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
• 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 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
• 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 2
• 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 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
• WHTNPSQCYHTFRC-UHFFFAOYSA-N 8-chloro-4-[3-[4-(hydroxymethyl)-1,3-thiazol-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)=CS1 WHTNPSQCYHTFRC-UHFFFAOYSA-N 0.000 claims description 2
• ADOSEGKIEQRXKL-UHFFFAOYSA-N 8-chloro-4-[3-[4-(hydroxymethyl)-1,3-thiazol-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)=CS1 ADOSEGKIEQRXKL-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• JPOWMXAAAODWDG-UHFFFAOYSA-N 8-chloro-7-[ethyl(methyl)amino]-4-[3-[4-(hydroxymethyl)-1,3-oxazol-2-yl]phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(Cl)C(N(C)CC)=CC=2N=C1C(C=1)=CC=CC=1C1=NC(CO)=CO1 JPOWMXAAAODWDG-UHFFFAOYSA-N 0.000 claims description 2
• MDZRWNNRILAEHU-UHFFFAOYSA-N 8-chloro-7-[ethyl(methyl)amino]-4-[3-[4-(hydroxymethyl)-1,3-thiazol-2-yl]phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(Cl)C(N(C)CC)=CC=2N=C1C(C=1)=CC=CC=1C1=NC(CO)=CS1 MDZRWNNRILAEHU-UHFFFAOYSA-N 0.000 claims description 2
• KMRCILAGDOXKQR-UHFFFAOYSA-N 8-chloro-7-[methyl(2-methylpropyl)amino]-4-[3-(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=1N1C=CN=N1 KMRCILAGDOXKQR-UHFFFAOYSA-N 0.000 claims description 2
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• 108020003175 receptors Proteins 0.000 description 4
• 238000010992 reflux Methods 0.000 description 4
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• ODCCJTMPMUFERV-UHFFFAOYSA-N ditert-butyl carbonate Chemical compound CC(C)(C)OC(=O)OC(C)(C)C ODCCJTMPMUFERV-UHFFFAOYSA-N 0.000 description 3
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• FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 3
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• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
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• ULHKMSVNVCQHHX-UHFFFAOYSA-N methyl 3-(2,5-dimethyl-1,3-thiazol-4-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C2=C(SC(C)=N2)C)=C1 ULHKMSVNVCQHHX-UHFFFAOYSA-N 0.000 description 3
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• MUNULOKWRWVZEA-UHFFFAOYSA-N methyl 3-(2-propan-2-yl-1h-imidazol-5-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C=2NC(=NC=2)C(C)C)=C1 MUNULOKWRWVZEA-UHFFFAOYSA-N 0.000 description 3
• XFYPJAPDFKSOIC-UHFFFAOYSA-N methyl 3-(5-methyl-1,3-oxazol-4-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C2=C(OC=N2)C)=C1 XFYPJAPDFKSOIC-UHFFFAOYSA-N 0.000 description 3
• NSUKZHPOWCPFRY-UHFFFAOYSA-N methyl 3-[2-methyl-5-(oxan-2-yloxymethyl)-1,3-thiazol-4-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C2=C(SC(C)=N2)COC2OCCCC2)=C1 NSUKZHPOWCPFRY-UHFFFAOYSA-N 0.000 description 3
• GCRVOUCLHCAJSR-UHFFFAOYSA-N methyl 3-[4-(hydroxymethyl)-1,3-thiazol-2-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C=2SC=C(CO)N=2)=C1 GCRVOUCLHCAJSR-UHFFFAOYSA-N 0.000 description 3
• BZCDVQIEADVFMX-UHFFFAOYSA-N methyl 3-[4-(oxan-2-yloxymethyl)-5-propyl-1,3-thiazol-2-yl]benzoate Chemical compound CCCC=1SC(C=2C=C(C=CC=2)C(=O)OC)=NC=1COC1CCCCO1 BZCDVQIEADVFMX-UHFFFAOYSA-N 0.000 description 3
• NQKXNYZEOCIKRN-UHFFFAOYSA-N methyl 3-[5-(2-hydroxyethyl)-1,3,4-oxadiazol-2-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C=2OC(CCO)=NN=2)=C1 NQKXNYZEOCIKRN-UHFFFAOYSA-N 0.000 description 3
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• FBHMSRURHJEWJJ-UHFFFAOYSA-N methyl 3-[5-(bromomethyl)-2-methyl-1,3-thiazol-4-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C2=C(SC(C)=N2)CBr)=C1 FBHMSRURHJEWJJ-UHFFFAOYSA-N 0.000 description 3
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• MNGVEOFABSEVKT-UHFFFAOYSA-N methyl 3-[3-methyl-4-(oxan-2-yloxymethyl)-1,2-oxazol-5-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C2=C(C(C)=NO2)COC2OCCCC2)=C1 MNGVEOFABSEVKT-UHFFFAOYSA-N 0.000 description 1
• RJMQKNVGFXRGTN-UHFFFAOYSA-N methyl 3-[4-(chloromethyl)-1,3-oxazol-2-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C=2OC=C(CCl)N=2)=C1 RJMQKNVGFXRGTN-UHFFFAOYSA-N 0.000 description 1
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