CA2732280A1 - Benzoimidazole derivatives and glycogen synthase kinase-3 beta inhibitors containing the same - Google Patents
Benzoimidazole derivatives and glycogen synthase kinase-3 beta inhibitors containing the same Download PDFInfo
- Publication number
- CA2732280A1 CA2732280A1 CA2732280A CA2732280A CA2732280A1 CA 2732280 A1 CA2732280 A1 CA 2732280A1 CA 2732280 A CA2732280 A CA 2732280A CA 2732280 A CA2732280 A CA 2732280A CA 2732280 A1 CA2732280 A1 CA 2732280A1
- Authority
- CA
- Canada
- Prior art keywords
- benzo
- imidazole
- hydroxy
- thiophen
- carboxamide
- Prior art date
- 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.)
- Abandoned
Links
- 102000019058 Glycogen Synthase Kinase 3 beta Human genes 0.000 title claims abstract description 21
- 108010051975 Glycogen Synthase Kinase 3 beta Proteins 0.000 title claims abstract description 21
- 239000003112 inhibitor Substances 0.000 title claims abstract description 10
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical class C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 123
- 238000000034 method Methods 0.000 claims description 108
- -1 p-toluenesulfonylamino Chemical group 0.000 claims description 104
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 59
- ZBNZAJFNDPPMDT-UHFFFAOYSA-N 1h-imidazole-5-carboxamide Chemical compound NC(=O)C1=CNC=N1 ZBNZAJFNDPPMDT-UHFFFAOYSA-N 0.000 claims description 54
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 36
- 125000001424 substituent group Chemical group 0.000 claims description 30
- 239000012453 solvate Substances 0.000 claims description 28
- 125000005842 heteroatom Chemical group 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 150000001408 amides Chemical class 0.000 claims description 18
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 18
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 15
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 14
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 13
- 150000001412 amines Chemical class 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 10
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 10
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- 125000005974 C6-C14 arylcarbonyl group Chemical group 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 7
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- UVKHHBRUBXLKTP-QPJJXVBHSA-N (e)-3-(1h-imidazol-5-yl)-n-(7-methoxy-2-thiophen-2-yl-1h-benzimidazol-4-yl)prop-2-enamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(OC)=CC=C1NC(=O)\C=C\C1=CN=CN1 UVKHHBRUBXLKTP-QPJJXVBHSA-N 0.000 claims description 5
- KMTNZCAGMPTVOX-UHFFFAOYSA-N 7-hydroxy-2-thiophen-2-yl-1h-benzimidazole-4-carboxylic acid Chemical compound N1C=2C(C(=O)O)=CC=C(O)C=2N=C1C1=CC=CS1 KMTNZCAGMPTVOX-UHFFFAOYSA-N 0.000 claims description 5
- 208000024827 Alzheimer disease Diseases 0.000 claims description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 5
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 5
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims description 5
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 4
- 206010026749 Mania Diseases 0.000 claims description 4
- 208000019695 Migraine disease Diseases 0.000 claims description 4
- 150000001409 amidines Chemical class 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
- 206010027599 migraine Diseases 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- MZHSZYCOVLPFLX-UHFFFAOYSA-N 1-(2-cyclopropyl-7-hydroxy-1h-benzimidazol-4-yl)-3-(4-hydroxyphenyl)urea Chemical compound C1=CC(O)=CC=C1NC(=O)NC1=CC=C(O)C2=C1N=C(C1CC1)N2 MZHSZYCOVLPFLX-UHFFFAOYSA-N 0.000 claims description 3
- HVIMPUISPMUNPS-UHFFFAOYSA-N 2-cyclopropyl-7-hydroxy-n-[2-(4-sulfamoylphenyl)ethyl]-1h-benzimidazole-4-carboxamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CCNC(=O)C1=CC=C(O)C2=C1NC(C1CC1)=N2 HVIMPUISPMUNPS-UHFFFAOYSA-N 0.000 claims description 3
- BBIVHOWFUCOWKO-UHFFFAOYSA-N 7-hydroxy-n-[2-(4-nitrophenoxy)ethyl]-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1C(=O)NCCOC1=CC=C([N+]([O-])=O)C=C1 BBIVHOWFUCOWKO-UHFFFAOYSA-N 0.000 claims description 3
- GOPDFXUMARJJEA-UHFFFAOYSA-N amino(nitro)azanide Chemical compound N[N-][N+]([O-])=O GOPDFXUMARJJEA-UHFFFAOYSA-N 0.000 claims description 3
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- TWGFJXFYAIVMSD-LBPRGKRZSA-N methyl (2s)-2-[(7-hydroxy-2-thiophen-2-yl-1h-benzimidazole-4-carbonyl)amino]-3-(1h-imidazol-5-yl)propanoate Chemical compound C([C@@H](C(=O)OC)NC(=O)C=1C=2N=C(NC=2C(O)=CC=1)C=1SC=CC=1)C1=CN=CN1 TWGFJXFYAIVMSD-LBPRGKRZSA-N 0.000 claims description 3
- UQBQUPKEQYLNEP-KRWDZBQOSA-N methyl (2s)-2-[(7-hydroxy-2-thiophen-2-yl-1h-benzimidazole-4-carbonyl)amino]-3-(1h-indol-3-yl)propanoate Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)OC)C(=O)C(C=1N=2)=CC=C(O)C=1NC=2C1=CC=CS1 UQBQUPKEQYLNEP-KRWDZBQOSA-N 0.000 claims description 3
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 3
- VSWOMRSVSRDHTQ-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-7-hydroxy-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound N=1C=2C(C(=O)NCCN(C)C)=CC=C(O)C=2NC=1C1=CC=CS1 VSWOMRSVSRDHTQ-UHFFFAOYSA-N 0.000 claims description 3
- HCDYZIZXEZAMPG-UHFFFAOYSA-N n-[5-hydroxy-2-(piperidin-3-ylcarbamoyl)phenyl]thiophene-2-carboxamide Chemical compound C=1C=CSC=1C(=O)NC1=CC(O)=CC=C1C(=O)NC1CCCNC1 HCDYZIZXEZAMPG-UHFFFAOYSA-N 0.000 claims description 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- ZUVFATUZMPMHOH-NSHDSACASA-N (2s)-2-[(7-hydroxy-2-thiophen-2-yl-1h-benzimidazole-4-carbonyl)amino]-3-(1h-imidazol-5-yl)propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C=1C=2N=C(NC=2C(O)=CC=1)C=1SC=CC=1)C1=CN=CN1 ZUVFATUZMPMHOH-NSHDSACASA-N 0.000 claims description 2
- MUVKYWUUGPEPCZ-INIZCTEOSA-N (2s)-2-[(7-hydroxy-2-thiophen-2-yl-1h-benzimidazole-4-carbonyl)amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(C=1N=2)=CC=C(O)C=1NC=2C1=CC=CS1 MUVKYWUUGPEPCZ-INIZCTEOSA-N 0.000 claims description 2
- WEPGUFPFXZWBCK-UHFFFAOYSA-N 2-(furan-2-yl)-7-hydroxy-n-(1,3-thiazol-2-yl)-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3OC=CC=3)NC=2C(O)=CC=C1C(=O)NC1=NC=CS1 WEPGUFPFXZWBCK-UHFFFAOYSA-N 0.000 claims description 2
- SBZNOMSJFLVNDA-UHFFFAOYSA-N 2-(furan-2-yl)-7-hydroxy-n-(2-phenylethyl)-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3OC=CC=3)NC=2C(O)=CC=C1C(=O)NCCC1=CC=CC=C1 SBZNOMSJFLVNDA-UHFFFAOYSA-N 0.000 claims description 2
- SKWUVECPMONQGU-UHFFFAOYSA-N 2-(furan-2-yl)-7-hydroxy-n-phenyl-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3OC=CC=3)NC=2C(O)=CC=C1C(=O)NC1=CC=CC=C1 SKWUVECPMONQGU-UHFFFAOYSA-N 0.000 claims description 2
- CUPJXQFPTJBZOZ-UHFFFAOYSA-N 2-cyclopentyl-7-hydroxy-n-[2-(4-hydroxyphenyl)ethyl]-1h-benzimidazole-4-carboxamide Chemical compound C1=CC(O)=CC=C1CCNC(=O)C1=CC=C(O)C2=C1NC(C1CCCC1)=N2 CUPJXQFPTJBZOZ-UHFFFAOYSA-N 0.000 claims description 2
- MXQIXJJYQFBVJN-UHFFFAOYSA-N 2-cyclopropyl-n-(2,3-dihydroxypropyl)-7-hydroxy-1h-benzimidazole-4-carboxamide Chemical compound N1C=2C(C(=O)NCC(O)CO)=CC=C(O)C=2N=C1C1CC1 MXQIXJJYQFBVJN-UHFFFAOYSA-N 0.000 claims description 2
- HHGDSAWNMROJTC-UHFFFAOYSA-N 2-cyclopropyl-n-[2-(4-fluorophenyl)ethyl]-7-hydroxy-1h-benzimidazole-4-carboxamide Chemical compound C1=2NC(C3CC3)=NC=2C(O)=CC=C1C(=O)NCCC1=CC=C(F)C=C1 HHGDSAWNMROJTC-UHFFFAOYSA-N 0.000 claims description 2
- KSMCYMNDVNDOEW-UHFFFAOYSA-N 7-fluoro-n-[2-(1h-imidazol-5-yl)ethyl]-2-thiophen-2-yl-3h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(F)=CC=C1C(=O)NCCC1=CN=CN1 KSMCYMNDVNDOEW-UHFFFAOYSA-N 0.000 claims description 2
- VLBUEFFYBHGVQX-UHFFFAOYSA-N 7-hydroxy-2-phenyl-n-(2-phenylethyl)-1h-benzimidazole-4-carboxamide Chemical compound C1=2NC(C=3C=CC=CC=3)=NC=2C(O)=CC=C1C(=O)NCCC1=CC=CC=C1 VLBUEFFYBHGVQX-UHFFFAOYSA-N 0.000 claims description 2
- JPQBWJWUGVSDBA-UHFFFAOYSA-N 7-hydroxy-2-thiophen-2-yl-3h-benzimidazole-5-carboxamide Chemical compound N=1C2=CC(C(=O)N)=CC(O)=C2NC=1C1=CC=CS1 JPQBWJWUGVSDBA-UHFFFAOYSA-N 0.000 claims description 2
- NZBRUYFITVWYNU-UHFFFAOYSA-N 7-hydroxy-2-thiophen-2-yl-n-(2-thiophen-2-ylethyl)-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1C(=O)NCCC1=CC=CS1 NZBRUYFITVWYNU-UHFFFAOYSA-N 0.000 claims description 2
- BMDGRFFORKPVDW-UHFFFAOYSA-N 7-hydroxy-n-(1,3-thiazol-2-yl)-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1C(=O)NC1=NC=CS1 BMDGRFFORKPVDW-UHFFFAOYSA-N 0.000 claims description 2
- RQWPXWYHCDTLCQ-UHFFFAOYSA-N 7-hydroxy-n-(3-imidazol-1-ylpropyl)-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1C(=O)NCCCN1C=CN=C1 RQWPXWYHCDTLCQ-UHFFFAOYSA-N 0.000 claims description 2
- AOUOLQCMFOELTQ-CYBMUJFWSA-N 7-hydroxy-n-[(2s)-1-hydroxy-3,3-dimethylbutan-2-yl]-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound N=1C=2C(C(=O)N[C@H](CO)C(C)(C)C)=CC=C(O)C=2NC=1C1=CC=CS1 AOUOLQCMFOELTQ-CYBMUJFWSA-N 0.000 claims description 2
- KPMGOOQJFZUQKN-UHFFFAOYSA-N 7-hydroxy-n-[(4-sulfamoylphenyl)methyl]-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CNC(=O)C1=CC=C(O)C2=C1N=C(C=1SC=CC=1)N2 KPMGOOQJFZUQKN-UHFFFAOYSA-N 0.000 claims description 2
- BTRMVOSUMNXHFE-UHFFFAOYSA-N 7-hydroxy-n-[2-(1h-imidazol-2-yl)ethyl]-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1C(=O)NCCC1=NC=CN1 BTRMVOSUMNXHFE-UHFFFAOYSA-N 0.000 claims description 2
- KIBQEHLLMWSGFX-UHFFFAOYSA-N 7-hydroxy-n-[2-(1h-imidazol-5-yl)ethyl]-1h-indole-3-carboxamide Chemical compound C=1NC=2C(O)=CC=CC=2C=1C(=O)NCCC1=CN=CN1 KIBQEHLLMWSGFX-UHFFFAOYSA-N 0.000 claims description 2
- UHNVSGAVJLZCOT-UHFFFAOYSA-N 7-hydroxy-n-[2-(1h-imidazol-5-yl)ethyl]-2-thiophen-2-yl-3h-benzimidazole-5-carboxamide Chemical compound N1C=2C(O)=CC(C(=O)NCCC=3NC=NC=3)=CC=2N=C1C1=CC=CS1 UHNVSGAVJLZCOT-UHFFFAOYSA-N 0.000 claims description 2
- MROBEFRBDYTTSK-UHFFFAOYSA-N 7-hydroxy-n-[2-(4-hydroxyphenyl)ethyl]-2-phenyl-1h-benzimidazole-4-carboxamide Chemical compound C1=CC(O)=CC=C1CCNC(=O)C1=CC=C(O)C2=C1NC(C=1C=CC=CC=1)=N2 MROBEFRBDYTTSK-UHFFFAOYSA-N 0.000 claims description 2
- FLPCFXRGUFUVHJ-UHFFFAOYSA-N 7-hydroxy-n-[2-(4-sulfamoylphenyl)ethyl]-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CCNC(=O)C1=CC=C(O)C2=C1N=C(C=1SC=CC=1)N2 FLPCFXRGUFUVHJ-UHFFFAOYSA-N 0.000 claims description 2
- FUGLJOSMSYGJAU-UHFFFAOYSA-N 7-hydroxy-n-[2-(pyridin-4-ylsulfonylamino)ethyl]-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1C(=O)NCCNS(=O)(=O)C1=CC=NC=C1 FUGLJOSMSYGJAU-UHFFFAOYSA-N 0.000 claims description 2
- LOVNJIKQQJSSDK-UHFFFAOYSA-N 7-hydroxy-n-[3-(2-hydroxyethylamino)propyl]-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound N=1C=2C(C(=O)NCCCNCCO)=CC=C(O)C=2NC=1C1=CC=CS1 LOVNJIKQQJSSDK-UHFFFAOYSA-N 0.000 claims description 2
- QJHCQFHTMOZFOW-UHFFFAOYSA-N 7-hydroxy-n-[3-(propan-2-ylamino)propyl]-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound N=1C=2C(C(=O)NCCCNC(C)C)=CC=C(O)C=2NC=1C1=CC=CS1 QJHCQFHTMOZFOW-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 claims description 2
- NCFOCOFBHNWJDC-UHFFFAOYSA-N methyl 3-hydroxy-2-[(7-hydroxy-2-thiophen-2-yl-1h-benzimidazole-4-carbonyl)amino]propanoate Chemical compound N=1C=2C(C(=O)NC(CO)C(=O)OC)=CC=C(O)C=2NC=1C1=CC=CS1 NCFOCOFBHNWJDC-UHFFFAOYSA-N 0.000 claims description 2
- HZQOAXBFUCEICD-UHFFFAOYSA-N n-(2-acetamidoethyl)-7-hydroxy-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound N=1C=2C(C(=O)NCCNC(=O)C)=CC=C(O)C=2NC=1C1=CC=CS1 HZQOAXBFUCEICD-UHFFFAOYSA-N 0.000 claims description 2
- COKWCLRPCPQRHW-UHFFFAOYSA-N n-(2-cyclopropyl-7-hydroxy-1h-benzimidazol-4-yl)-2-(4-hydroxyphenyl)acetamide Chemical compound C1=CC(O)=CC=C1CC(=O)NC1=CC=C(O)C2=C1N=C(C1CC1)N2 COKWCLRPCPQRHW-UHFFFAOYSA-N 0.000 claims description 2
- MVIYVSVLUFCKPM-UHFFFAOYSA-N n-(7-hydroxy-2-thiophen-2-yl-1h-benzimidazol-4-yl)-3-(1h-imidazol-5-yl)propanamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1NC(=O)CCC1=CN=CN1 MVIYVSVLUFCKPM-UHFFFAOYSA-N 0.000 claims description 2
- KAXYSAVZDDUQAY-UHFFFAOYSA-N n-[(2,4-difluorophenyl)methyl]-7-hydroxy-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1C(=O)NCC1=CC=C(F)C=C1F KAXYSAVZDDUQAY-UHFFFAOYSA-N 0.000 claims description 2
- CYEZNUPYHKNUEM-UHFFFAOYSA-N n-[2-(4-aminophenyl)ethyl]-2-cyclopentyl-7-hydroxy-1h-benzimidazole-4-carboxamide Chemical compound C1=CC(N)=CC=C1CCNC(=O)C1=CC=C(O)C2=C1NC(C1CCCC1)=N2 CYEZNUPYHKNUEM-UHFFFAOYSA-N 0.000 claims description 2
- QSMNQEMSVXJRQS-UHFFFAOYSA-N n-[2-(4-aminophenyl)ethyl]-7-hydroxy-2-phenyl-1h-benzimidazole-4-carboxamide Chemical compound C1=CC(N)=CC=C1CCNC(=O)C1=CC=C(O)C2=C1NC(C=1C=CC=CC=1)=N2 QSMNQEMSVXJRQS-UHFFFAOYSA-N 0.000 claims description 2
- VDMPWEXEHQWQKM-UHFFFAOYSA-N n-[2-(4-fluorophenyl)ethyl]-7-hydroxy-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1C(=O)NCCC1=CC=C(F)C=C1 VDMPWEXEHQWQKM-UHFFFAOYSA-N 0.000 claims description 2
- BDRBZSPAJPBMKA-UHFFFAOYSA-N n-[2-(5-carbamoylpyridin-2-yl)oxyethyl]-7-hydroxy-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound N1=CC(C(=O)N)=CC=C1OCCNC(=O)C1=CC=C(O)C2=C1N=C(C=1SC=CC=1)N2 BDRBZSPAJPBMKA-UHFFFAOYSA-N 0.000 claims description 2
- PNYYRFDFEXVEPN-UHFFFAOYSA-N n-[2-(benzenesulfonamido)ethyl]-7-hydroxy-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1C(=O)NCCNS(=O)(=O)C1=CC=CC=C1 PNYYRFDFEXVEPN-UHFFFAOYSA-N 0.000 claims description 2
- NGQAEUFCTRTCCT-UHFFFAOYSA-N n-[2-[(5-acetamidopyridin-2-yl)amino]ethyl]-7-hydroxy-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound N1=CC(NC(=O)C)=CC=C1NCCNC(=O)C1=CC=C(O)C2=C1N=C(C=1SC=CC=1)N2 NGQAEUFCTRTCCT-UHFFFAOYSA-N 0.000 claims description 2
- DWOUPRLHBBTUHD-UHFFFAOYSA-N n-[2-hydroxy-5-[2-(1h-imidazol-5-yl)ethylcarbamoyl]phenyl]thiophene-2-carboxamide Chemical compound OC1=CC=C(C(=O)NCCC=2NC=NC=2)C=C1NC(=O)C1=CC=CS1 DWOUPRLHBBTUHD-UHFFFAOYSA-N 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims 10
- 229910052717 sulfur Inorganic materials 0.000 claims 10
- 230000008878 coupling Effects 0.000 claims 7
- 238000010168 coupling process Methods 0.000 claims 7
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- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 229940071264 lithium citrate Drugs 0.000 description 1
- WJSIUCDMWSDDCE-UHFFFAOYSA-K lithium citrate (anhydrous) Chemical compound [Li+].[Li+].[Li+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O WJSIUCDMWSDDCE-UHFFFAOYSA-K 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 208000024714 major depressive disease Diseases 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
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- 229940099690 malic acid Drugs 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
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- 239000002609 medium Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- KCUNTYMNJVXYKZ-JTQLQIEISA-N methyl (2s)-2-amino-3-(1h-indol-3-yl)propanoate Chemical compound C1=CC=C2C(C[C@H](N)C(=O)OC)=CNC2=C1 KCUNTYMNJVXYKZ-JTQLQIEISA-N 0.000 description 1
- NTNUDYROPUKXNA-UHFFFAOYSA-N methyl 2-(triphenyl-$l^{5}-phosphanylidene)acetate Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OC)C1=CC=CC=C1 NTNUDYROPUKXNA-UHFFFAOYSA-N 0.000 description 1
- ANSUDRATXSJBLY-UHFFFAOYSA-N methyl 2-amino-3-hydroxypropanoate Chemical compound COC(=O)C(N)CO ANSUDRATXSJBLY-UHFFFAOYSA-N 0.000 description 1
- SIPPUXPIJXLNKR-UHFFFAOYSA-N methyl 3-(4-hydroxyphenyl)-2-[(7-hydroxy-2-thiophen-2-yl-1h-benzimidazole-4-carbonyl)amino]propanoate Chemical compound C=1C=C(O)C=2NC(C=3SC=CC=3)=NC=2C=1C(=O)NC(C(=O)OC)CC1=CC=C(O)C=C1 SIPPUXPIJXLNKR-UHFFFAOYSA-N 0.000 description 1
- UMDBYBUACBGSNK-UHFFFAOYSA-N methyl 3-[[amino(thiophen-2-yl)methylidene]amino]-4-methoxybenzoate Chemical compound COC(=O)C1=CC=C(OC)C(NC(=N)C=2SC=CC=2)=C1 UMDBYBUACBGSNK-UHFFFAOYSA-N 0.000 description 1
- ABELEDYNIKPYTP-UHFFFAOYSA-N methyl 3-amino-4-fluorobenzoate Chemical compound COC(=O)C1=CC=C(F)C(N)=C1 ABELEDYNIKPYTP-UHFFFAOYSA-N 0.000 description 1
- DJLFOMMCQBAMAA-UHFFFAOYSA-N methyl 4-amino-3-methoxybenzoate Chemical compound COC(=O)C1=CC=C(N)C(OC)=C1 DJLFOMMCQBAMAA-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
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- 125000002757 morpholinyl group Chemical group 0.000 description 1
- ODHSPTHLPCXPTL-UHFFFAOYSA-N n'-(5-nitropyridin-2-yl)ethane-1,2-diamine Chemical compound NCCNC1=CC=C([N+]([O-])=O)C=N1 ODHSPTHLPCXPTL-UHFFFAOYSA-N 0.000 description 1
- KFDIDIIKNMZLRZ-UHFFFAOYSA-N n'-propan-2-ylpropane-1,3-diamine Chemical compound CC(C)NCCCN KFDIDIIKNMZLRZ-UHFFFAOYSA-N 0.000 description 1
- TYHXIJJQIJKFSO-UHFFFAOYSA-N n'-pyridin-2-ylethane-1,2-diamine Chemical compound NCCNC1=CC=CC=N1 TYHXIJJQIJKFSO-UHFFFAOYSA-N 0.000 description 1
- MWEBCGQFQBAAJP-UHFFFAOYSA-N n-(2-aminoethyl)-4-chlorobenzenesulfonamide Chemical compound NCCNS(=O)(=O)C1=CC=C(Cl)C=C1 MWEBCGQFQBAAJP-UHFFFAOYSA-N 0.000 description 1
- IYTURFXZHKVZGN-UHFFFAOYSA-N n-(2-aminoethyl)-4-chlorobenzenesulfonamide;hydrochloride Chemical compound Cl.NCCNS(=O)(=O)C1=CC=C(Cl)C=C1 IYTURFXZHKVZGN-UHFFFAOYSA-N 0.000 description 1
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- DAKZISABEDGGSV-UHFFFAOYSA-N n-(2-aminoethyl)acetamide Chemical compound CC(=O)NCCN DAKZISABEDGGSV-UHFFFAOYSA-N 0.000 description 1
- BCGXHHYBXMQECD-UHFFFAOYSA-N n-(2-aminoethyl)benzamide;hydrochloride Chemical compound Cl.NCCNC(=O)C1=CC=CC=C1 BCGXHHYBXMQECD-UHFFFAOYSA-N 0.000 description 1
- JVFJSUCEQDCCAH-UHFFFAOYSA-N n-(2-aminoethyl)benzenesulfonamide Chemical compound NCCNS(=O)(=O)C1=CC=CC=C1 JVFJSUCEQDCCAH-UHFFFAOYSA-N 0.000 description 1
- NTENADQOAWUTOH-UHFFFAOYSA-N n-(2-aminoethyl)benzenesulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NCCNS(=O)(=O)C1=CC=CC=C1 NTENADQOAWUTOH-UHFFFAOYSA-N 0.000 description 1
- KXBXVEGOHACSKW-UHFFFAOYSA-N n-(2-aminoethyl)pyridine-4-sulfonamide Chemical compound NCCNS(=O)(=O)C1=CC=NC=C1 KXBXVEGOHACSKW-UHFFFAOYSA-N 0.000 description 1
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- LTGRYMCRXRFVCZ-UHFFFAOYSA-N n-(2-hydroxyethyl)-7-methoxy-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound N1C=2C(OC)=CC=C(C(=O)NCCO)C=2N=C1C1=CC=CS1 LTGRYMCRXRFVCZ-UHFFFAOYSA-N 0.000 description 1
- JHMDPDAKHZMBFU-UHFFFAOYSA-N n-(4-methoxyphenyl)carbamoyl chloride Chemical compound COC1=CC=C(NC(Cl)=O)C=C1 JHMDPDAKHZMBFU-UHFFFAOYSA-N 0.000 description 1
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- IOOARBMSXOAWLS-UHFFFAOYSA-N n-[(3,4-dihydroxyphenyl)methyl]-7-hydroxy-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=C(O)C(O)=CC=C1CNC(=O)C1=CC=C(O)C2=C1N=C(C=1SC=CC=1)N2 IOOARBMSXOAWLS-UHFFFAOYSA-N 0.000 description 1
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- JOHGYBMIJBITFP-UHFFFAOYSA-N n-[2-[(4-chlorophenyl)sulfonylamino]ethyl]-7-hydroxy-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1C(=O)NCCNS(=O)(=O)C1=CC=C(Cl)C=C1 JOHGYBMIJBITFP-UHFFFAOYSA-N 0.000 description 1
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- YIRIHJCPYLRLBV-UHFFFAOYSA-N n-[3-(1h-imidazol-2-yl)propyl]-7-methoxy-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(OC)=CC=C1C(=O)NCCCC1=NC=CN1 YIRIHJCPYLRLBV-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000005185 naphthylcarbonyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 125000005146 naphthylsulfonyl group Chemical group C1(=CC=CC2=CC=CC=C12)S(=O)(=O)* 0.000 description 1
- 210000003061 neural cell Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
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- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
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- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
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- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
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- NHMOJCOXIZRTRR-UHFFFAOYSA-N pyridine-4-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=NC=C1 NHMOJCOXIZRTRR-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000011535 reaction buffer Substances 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012056 semi-solid material Substances 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000012058 sterile packaged powder Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- 239000005720 sucrose Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
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- 125000006253 t-butylcarbonyl group Chemical group [H]C([H])([H])C(C(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- LSDBSWXWUNOJKJ-UHFFFAOYSA-N tert-butyl 3-[(2-amino-4-methoxybenzoyl)amino]piperidine-1-carboxylate Chemical compound NC1=CC(OC)=CC=C1C(=O)NC1CN(C(=O)OC(C)(C)C)CCC1 LSDBSWXWUNOJKJ-UHFFFAOYSA-N 0.000 description 1
- AKQXKEBCONUWCL-UHFFFAOYSA-N tert-butyl 3-aminopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC(N)C1 AKQXKEBCONUWCL-UHFFFAOYSA-N 0.000 description 1
- XDJCYKMWJCYQJM-UHFFFAOYSA-N tert-butyl n-(3-hydroxypropyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCCO XDJCYKMWJCYQJM-UHFFFAOYSA-N 0.000 description 1
- JZSSQQFLTWLZEM-UHFFFAOYSA-N tert-butyl n-[2-(4,5-dihydro-1h-imidazol-2-yl)ethyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCC1=NCCN1 JZSSQQFLTWLZEM-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000005302 thiazolylmethyl group Chemical group [H]C1=C([H])N=C(S1)C([H])([H])* 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
- LOIYMIARKYCTBW-OWOJBTEDSA-N trans-urocanic acid Chemical compound OC(=O)\C=C\C1=CNC=N1 LOIYMIARKYCTBW-OWOJBTEDSA-N 0.000 description 1
- 125000005500 uronium group Chemical group 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Diabetes (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8477008P | 2008-07-30 | 2008-07-30 | |
| US61/084,770 | 2008-07-30 | ||
| PCT/US2009/052225 WO2010014794A1 (en) | 2008-07-30 | 2009-07-30 | Benzoimidazole derivatives and glycogen synthase kinase-3 beta inhibitors containing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2732280A1 true CA2732280A1 (en) | 2010-02-04 |
Family
ID=41610727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2732280A Abandoned CA2732280A1 (en) | 2008-07-30 | 2009-07-30 | Benzoimidazole derivatives and glycogen synthase kinase-3 beta inhibitors containing the same |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US20110190351A1 (https=) |
| EP (1) | EP2309855A4 (https=) |
| JP (1) | JP2011529903A (https=) |
| KR (1) | KR20110040958A (https=) |
| CN (1) | CN102170785A (https=) |
| AU (1) | AU2009276548A1 (https=) |
| BR (1) | BRPI0916726A2 (https=) |
| CA (1) | CA2732280A1 (https=) |
| CO (1) | CO6351688A2 (https=) |
| IL (1) | IL210863A0 (https=) |
| MX (1) | MX2011001170A (https=) |
| RU (1) | RU2011107227A (https=) |
| WO (1) | WO2010014794A1 (https=) |
| ZA (1) | ZA201101160B (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009158118A2 (en) | 2008-05-30 | 2009-12-30 | University Of Notre Dame Du Lac | Anti-bacterial agents from benzo[d]heterocyclic scaffolds for prevention and treatment of multidrug resistant bacteria |
| CN101619058A (zh) * | 2009-01-08 | 2010-01-06 | 上海交通大学 | 一种苯并咪唑-4-酰胺型衍生物 |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| PE20161064A1 (es) * | 2013-12-12 | 2016-10-28 | Univ Tsukuba | Derivado de sulfonamida o sales de adicion de acido farmaceuticamente aceptables del mismo |
| CN105461722B (zh) * | 2014-09-04 | 2019-05-10 | 欣凯医药化工中间体（上海）有限公司 | 一种脱氮嘌呤类化合物及其衍生物及其制备方法和应用 |
| WO2016133160A1 (ja) * | 2015-02-19 | 2016-08-25 | 国立大学法人筑波大学 | スルホンアミド誘導体またはその薬学的に許容される酸付加塩 |
| AU2021359129A1 (en) * | 2020-10-16 | 2023-06-01 | Proxygen Gmbh | Heterocyclic cullin ring ubiquitin ligase compounds and uses thereof |
| WO2024014851A1 (ko) * | 2022-07-12 | 2024-01-18 | 주식회사 넥스트젠바이오사이언스 | Hif-1 단백질 억제제로서의 신규한 퓨린 유도체 화합물 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0178413A1 (en) * | 1984-08-17 | 1986-04-23 | Beecham Group Plc | Benzimidazoles |
| FR2699816B1 (fr) * | 1992-12-30 | 1995-03-03 | Oreal | Compositions tinctoriales pour fibres kératiniques à base de paraphénylènediamines, de métaphénylènediamines et de dérivés du benzimidazole, et procédé de teinture les mettant en Óoeuvre. |
| US7064215B2 (en) * | 2001-07-03 | 2006-06-20 | Chiron Corporation | Indazole benzimidazole compounds |
| WO2003066629A2 (en) * | 2002-02-06 | 2003-08-14 | Vertex Pharmaceuticals Incorporated | Heteroaryl compounds useful as inhibitors of gsk-3 |
| KR100791252B1 (ko) * | 2003-01-23 | 2008-01-03 | 크리스탈지노믹스(주) | 글리코겐 합성효소 키나아제 3β 활성 억제제, 이의제조방법 및 이를 유효성분으로 함유하는 약학 조성물 |
| BRPI0919977A2 (pt) * | 2008-10-30 | 2015-08-25 | Oncotherapy Science Inc | Derivados de 7-hidróxi-benzoimidazol-4-il-metanona e inibidores de pbk contendo os mesmos |
| JP2012509249A (ja) * | 2008-11-20 | 2012-04-19 | オンコセラピー・サイエンス株式会社 | ７−ヒドロキシ−ベンゾイミダゾール−４−イル−メタノン誘導体を含むグリコーゲン合成酵素キナーゼ−３ベータ阻害剤 |
-
2009
- 2009-07-30 AU AU2009276548A patent/AU2009276548A1/en not_active Withdrawn
- 2009-07-30 WO PCT/US2009/052225 patent/WO2010014794A1/en not_active Ceased
- 2009-07-30 CN CN2009801387112A patent/CN102170785A/zh not_active Withdrawn
- 2009-07-30 BR BRPI0916726A patent/BRPI0916726A2/pt not_active IP Right Cessation
- 2009-07-30 JP JP2011521313A patent/JP2011529903A/ja not_active Withdrawn
- 2009-07-30 MX MX2011001170A patent/MX2011001170A/es unknown
- 2009-07-30 CA CA2732280A patent/CA2732280A1/en not_active Abandoned
- 2009-07-30 EP EP09803582A patent/EP2309855A4/en active Pending
- 2009-07-30 KR KR1020117004602A patent/KR20110040958A/ko not_active Withdrawn
- 2009-07-30 US US13/056,591 patent/US20110190351A1/en not_active Abandoned
- 2009-07-30 RU RU2011107227/13A patent/RU2011107227A/ru not_active Application Discontinuation
-
2011
- 2011-01-25 IL IL210863A patent/IL210863A0/en unknown
- 2011-02-08 CO CO11014386A patent/CO6351688A2/es not_active Application Discontinuation
- 2011-02-14 ZA ZA2011/01160A patent/ZA201101160B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RU2011107227A (ru) | 2012-09-10 |
| JP2011529903A (ja) | 2011-12-15 |
| ZA201101160B (en) | 2011-10-26 |
| CN102170785A (zh) | 2011-08-31 |
| MX2011001170A (es) | 2011-04-05 |
| US20110190351A1 (en) | 2011-08-04 |
| IL210863A0 (en) | 2011-04-28 |
| KR20110040958A (ko) | 2011-04-20 |
| CO6351688A2 (es) | 2011-12-20 |
| EP2309855A4 (en) | 2012-06-27 |
| EP2309855A1 (en) | 2011-04-20 |
| WO2010014794A1 (en) | 2010-02-04 |
| BRPI0916726A2 (pt) | 2017-07-04 |
| AU2009276548A1 (en) | 2010-02-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20130730 |