RU2011124960A - Ингибиторы гликогенсинтаза-киназы 3-бета, содержащие производные 7-гидроксибензоимидазол-4-илметанова - Google Patents
Ингибиторы гликогенсинтаза-киназы 3-бета, содержащие производные 7-гидроксибензоимидазол-4-илметанова Download PDFInfo
- Publication number
- RU2011124960A RU2011124960A RU2011124960/04A RU2011124960A RU2011124960A RU 2011124960 A RU2011124960 A RU 2011124960A RU 2011124960/04 A RU2011124960/04 A RU 2011124960/04A RU 2011124960 A RU2011124960 A RU 2011124960A RU 2011124960 A RU2011124960 A RU 2011124960A
- Authority
- RU
- Russia
- Prior art keywords
- benzo
- hydroxy
- imidazole
- carboxamide
- piperidin
- Prior art date
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- 108091007911 GSKs Proteins 0.000 title 1
- 102000004103 Glycogen Synthase Kinases Human genes 0.000 title 1
- 229940043355 kinase inhibitor Drugs 0.000 title 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 title 1
- 108010051975 Glycogen Synthase Kinase 3 beta Proteins 0.000 claims abstract 20
- 102100038104 Glycogen synthase kinase-3 beta Human genes 0.000 claims abstract 20
- 239000003112 inhibitor Substances 0.000 claims abstract 20
- -1 furan-2- silt Chemical group 0.000 claims abstract 11
- 125000001424 substituent group Chemical group 0.000 claims abstract 6
- 150000001875 compounds Chemical group 0.000 claims abstract 5
- WVKPYYLOFMTDHB-UHFFFAOYSA-N 2-norbornyl radical Chemical group C1CC2[CH]CC1C2 WVKPYYLOFMTDHB-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims abstract 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract 4
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract 3
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims abstract 3
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims abstract 2
- 150000001408 amides Chemical class 0.000 claims abstract 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 2
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims abstract 2
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- 150000002367 halogens Chemical class 0.000 claims abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 2
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract 2
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims abstract 2
- 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims abstract 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 2
- 239000012453 solvate Substances 0.000 claims abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
- 230000001419 dependent effect Effects 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- ZBNZAJFNDPPMDT-UHFFFAOYSA-N 1h-imidazole-5-carboxamide Chemical compound NC(=O)C1=CNC=N1 ZBNZAJFNDPPMDT-UHFFFAOYSA-N 0.000 claims 2
- FHHUOFULEQWBBV-UHFFFAOYSA-N (7-hydroxy-2-thiophen-2-yl-1h-benzimidazol-4-yl)-piperazin-1-ylmethanone Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1C(=O)N1CCNCC1 FHHUOFULEQWBBV-UHFFFAOYSA-N 0.000 claims 1
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 1
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 1
- PQOKBQCVPUXWDC-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanyl)-7-hydroxy-n-(piperidin-3-ylmethyl)-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C3C4CCC(C4)C3)NC=2C(O)=CC=C1C(=O)NCC1CCCNC1 PQOKBQCVPUXWDC-UHFFFAOYSA-N 0.000 claims 1
- HTUPKTNEAWAZLK-WRSKWOSUSA-N 2-(3-bicyclo[2.2.1]heptanyl)-7-hydroxy-n-[(3s)-piperidin-3-yl]-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C3C4CCC(C4)C3)NC=2C(O)=CC=C1C(=O)N[C@H]1CCCNC1 HTUPKTNEAWAZLK-WRSKWOSUSA-N 0.000 claims 1
- MVEAHJYWRFCHHJ-VIFPVBQESA-N 2-(5-bromothiophen-2-yl)-7-hydroxy-n-[(3s)-piperidin-3-yl]-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC(Br)=CC=3)NC=2C(O)=CC=C1C(=O)N[C@H]1CCCNC1 MVEAHJYWRFCHHJ-VIFPVBQESA-N 0.000 claims 1
- VNAZLEQAHPPEOM-UHFFFAOYSA-N 2-cyclopentyl-7-hydroxy-n-(piperidin-2-ylmethyl)-1h-benzimidazole-4-carboxamide Chemical compound C1=2NC(C3CCCC3)=NC=2C(O)=CC=C1C(=O)NCC1CCCCN1 VNAZLEQAHPPEOM-UHFFFAOYSA-N 0.000 claims 1
- DQLLQCMTQCCTEP-UHFFFAOYSA-N 2-cyclopentyl-7-hydroxy-n-(piperidin-3-ylmethyl)-1h-benzimidazole-4-carboxamide Chemical compound C1=2NC(C3CCCC3)=NC=2C(O)=CC=C1C(=O)NCC1CCCNC1 DQLLQCMTQCCTEP-UHFFFAOYSA-N 0.000 claims 1
- DMMFTUBCYQBWJG-LBPRGKRZSA-N 2-cyclopentyl-7-hydroxy-n-[(3s)-piperidin-3-yl]-1h-benzimidazole-4-carboxamide Chemical compound C1=2NC(C3CCCC3)=NC=2C(O)=CC=C1C(=O)N[C@H]1CCCNC1 DMMFTUBCYQBWJG-LBPRGKRZSA-N 0.000 claims 1
- NUIBNWKZKSUNBU-UHFFFAOYSA-N 2-cyclopropyl-7-hydroxy-n-(1-methylpiperidin-3-yl)-1h-benzimidazole-4-carboxamide Chemical compound C1N(C)CCCC1NC(=O)C1=CC=C(O)C2=C1NC(C1CC1)=N2 NUIBNWKZKSUNBU-UHFFFAOYSA-N 0.000 claims 1
- JQLOJXHUSKTZSN-UHFFFAOYSA-N 2-cyclopropyl-7-hydroxy-n-(piperidin-2-ylmethyl)-1h-benzimidazole-4-carboxamide Chemical compound C1=2NC(C3CC3)=NC=2C(O)=CC=C1C(=O)NCC1CCCCN1 JQLOJXHUSKTZSN-UHFFFAOYSA-N 0.000 claims 1
- VCFNQZLCDVKCQD-UHFFFAOYSA-N 2-cyclopropyl-7-hydroxy-n-(piperidin-3-ylmethyl)-1h-benzimidazole-4-carboxamide Chemical compound C1=2NC(C3CC3)=NC=2C(O)=CC=C1C(=O)NCC1CCCNC1 VCFNQZLCDVKCQD-UHFFFAOYSA-N 0.000 claims 1
- FOPKNXVYPWDCPH-UHFFFAOYSA-N 2-cyclopropyl-7-hydroxy-n-(piperidin-4-ylmethyl)-1h-benzimidazole-4-carboxamide Chemical compound C1=2NC(C3CC3)=NC=2C(O)=CC=C1C(=O)NCC1CCNCC1 FOPKNXVYPWDCPH-UHFFFAOYSA-N 0.000 claims 1
- VLDJPBYBKMFSBJ-JTQLQIEISA-N 2-cyclopropyl-7-hydroxy-n-[(3s)-piperidin-3-yl]-1h-benzimidazole-4-carboxamide Chemical compound C1=2NC(C3CC3)=NC=2C(O)=CC=C1C(=O)N[C@H]1CCCNC1 VLDJPBYBKMFSBJ-JTQLQIEISA-N 0.000 claims 1
- VLDJPBYBKMFSBJ-UHFFFAOYSA-N 2-cyclopropyl-7-hydroxy-n-piperidin-3-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2NC(C3CC3)=NC=2C(O)=CC=C1C(=O)NC1CCCNC1 VLDJPBYBKMFSBJ-UHFFFAOYSA-N 0.000 claims 1
- QWNYPKVETAWYSZ-UHFFFAOYSA-N 2-cyclopropyl-7-hydroxy-n-piperidin-4-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2NC(C3CC3)=NC=2C(O)=CC=C1C(=O)NC1CCNCC1 QWNYPKVETAWYSZ-UHFFFAOYSA-N 0.000 claims 1
- NEXCLKRXESRENY-UHFFFAOYSA-N 2-cyclopropyl-7-hydroxy-n-pyrrolidin-3-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2NC(C3CC3)=NC=2C(O)=CC=C1C(=O)NC1CCNC1 NEXCLKRXESRENY-UHFFFAOYSA-N 0.000 claims 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- AMFHAOZWFGPCHS-UHFFFAOYSA-N 4-[(7-hydroxy-2-thiophen-2-yl-1h-benzimidazole-4-carbonyl)amino]cyclohexane-1-carboxylic acid Chemical compound C1CC(C(=O)O)CCC1NC(=O)C1=CC=C(O)C2=C1N=C(C=1SC=CC=1)N2 AMFHAOZWFGPCHS-UHFFFAOYSA-N 0.000 claims 1
- CWBZXCZNEOPRCN-ZDUSSCGKSA-N 7-hydroxy-2-(5-piperazin-1-ylthiophen-2-yl)-n-[(3s)-piperidin-3-yl]-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC(=CC=3)N3CCNCC3)NC=2C(O)=CC=C1C(=O)N[C@H]1CCCNC1 CWBZXCZNEOPRCN-ZDUSSCGKSA-N 0.000 claims 1
- HHWUJDYTPHLTIF-UHFFFAOYSA-N 7-hydroxy-2-phenyl-n-(piperidin-2-ylmethyl)-1h-benzimidazole-4-carboxamide Chemical compound C1=2NC(C=3C=CC=CC=3)=NC=2C(O)=CC=C1C(=O)NCC1CCCCN1 HHWUJDYTPHLTIF-UHFFFAOYSA-N 0.000 claims 1
- QUHAKLIRTFIRPF-UHFFFAOYSA-N 7-hydroxy-2-phenyl-n-(piperidin-3-ylmethyl)-1h-benzimidazole-4-carboxamide Chemical compound C1=2NC(C=3C=CC=CC=3)=NC=2C(O)=CC=C1C(=O)NCC1CCCNC1 QUHAKLIRTFIRPF-UHFFFAOYSA-N 0.000 claims 1
- HCOYOZKRGRMGIL-ZDUSSCGKSA-N 7-hydroxy-2-phenyl-n-[(3s)-piperidin-3-yl]-1h-benzimidazole-4-carboxamide Chemical compound C1=2NC(C=3C=CC=CC=3)=NC=2C(O)=CC=C1C(=O)N[C@H]1CCCNC1 HCOYOZKRGRMGIL-ZDUSSCGKSA-N 0.000 claims 1
- UHYZCMYXHGAMGC-UHFFFAOYSA-N 7-hydroxy-n-(1-methylpiperidin-3-yl)-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1N(C)CCCC1NC(=O)C1=CC=C(O)C2=C1N=C(C=1SC=CC=1)N2 UHYZCMYXHGAMGC-UHFFFAOYSA-N 0.000 claims 1
- LRQSKLNGWMJWMJ-UHFFFAOYSA-N 7-hydroxy-n-(2-piperazin-1-ylethyl)-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1C(=O)NCCN1CCNCC1 LRQSKLNGWMJWMJ-UHFFFAOYSA-N 0.000 claims 1
- VYRHSZRZVBIDCD-UHFFFAOYSA-N 7-hydroxy-n-(piperidin-2-ylmethyl)-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1C(=O)NCC1CCCCN1 VYRHSZRZVBIDCD-UHFFFAOYSA-N 0.000 claims 1
- MTCFCASJWUBVGX-UHFFFAOYSA-N 7-hydroxy-n-(piperidin-3-ylmethyl)-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1C(=O)NCC1CCCNC1 MTCFCASJWUBVGX-UHFFFAOYSA-N 0.000 claims 1
- DLNUWZOWSGXCKJ-UHFFFAOYSA-N 7-hydroxy-n-(piperidin-4-ylmethyl)-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1C(=O)NCC1CCNCC1 DLNUWZOWSGXCKJ-UHFFFAOYSA-N 0.000 claims 1
- NJKUDKWJZPVSAI-UHFFFAOYSA-N 7-hydroxy-n-(pyrrolidin-3-ylmethyl)-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1C(=O)NCC1CCNC1 NJKUDKWJZPVSAI-UHFFFAOYSA-N 0.000 claims 1
- LJPSIRPRIUNDAT-SNVBAGLBSA-N 7-hydroxy-n-[(3r)-piperidin-3-yl]-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1C(=O)N[C@@H]1CCCNC1 LJPSIRPRIUNDAT-SNVBAGLBSA-N 0.000 claims 1
- FMCDOLBSRBSVDW-NSHDSACASA-N 7-hydroxy-n-[(3s)-piperidin-3-yl]-2-(thiophen-2-ylmethyl)-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(CC=3SC=CC=3)NC=2C(O)=CC=C1C(=O)N[C@H]1CCCNC1 FMCDOLBSRBSVDW-NSHDSACASA-N 0.000 claims 1
- LJPSIRPRIUNDAT-JTQLQIEISA-N 7-hydroxy-n-[(3s)-piperidin-3-yl]-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1C(=O)N[C@H]1CCCNC1 LJPSIRPRIUNDAT-JTQLQIEISA-N 0.000 claims 1
- FQTGTVOVVRVTMG-GFCCVEGCSA-N 7-hydroxy-n-[[(3r)-piperidin-3-yl]methyl]-2-(thiophen-2-ylmethyl)-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(CC=3SC=CC=3)NC=2C(O)=CC=C1C(=O)NC[C@@H]1CCCNC1 FQTGTVOVVRVTMG-GFCCVEGCSA-N 0.000 claims 1
- FQTGTVOVVRVTMG-LBPRGKRZSA-N 7-hydroxy-n-[[(3s)-piperidin-3-yl]methyl]-2-(thiophen-2-ylmethyl)-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(CC=3SC=CC=3)NC=2C(O)=CC=C1C(=O)NC[C@H]1CCCNC1 FQTGTVOVVRVTMG-LBPRGKRZSA-N 0.000 claims 1
- LJPSIRPRIUNDAT-UHFFFAOYSA-N 7-hydroxy-n-piperidin-3-yl-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1C(=O)NC1CCCNC1 LJPSIRPRIUNDAT-UHFFFAOYSA-N 0.000 claims 1
- ITBAAQYBVUPCCT-UHFFFAOYSA-N 7-hydroxy-n-piperidin-4-yl-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1C(=O)NC1CCNCC1 ITBAAQYBVUPCCT-UHFFFAOYSA-N 0.000 claims 1
- WTHXQDHNQUSBSY-UHFFFAOYSA-N 7-hydroxy-n-pyrrolidin-3-yl-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C=3SC=CC=3)NC=2C(O)=CC=C1C(=O)NC1CCNC1 WTHXQDHNQUSBSY-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 206010026749 Mania Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- BDQDMSCHKZKLRF-UHFFFAOYSA-N N1C=2C(O)=CC=C(C(=O)NNC34CC5CC(CC(C5)C3)C4)C=2N=C1C1=CC=CS1 Chemical compound N1C=2C(O)=CC=C(C(=O)NNC34CC5CC(CC(C5)C3)C4)C=2N=C1C1=CC=CS1 BDQDMSCHKZKLRF-UHFFFAOYSA-N 0.000 claims 1
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- DVUCVNMXULPINP-UHFFFAOYSA-N n'-(1-adamantyl)-2-(3-bicyclo[2.2.1]heptanyl)-7-hydroxy-1h-benzimidazole-4-carbohydrazide Chemical compound C1C(C2)CC(C3)CC2CC13NNC(=O)C1=CC=C(O)C2=C1N=C(C1C3CCC(C3)C1)N2 DVUCVNMXULPINP-UHFFFAOYSA-N 0.000 claims 1
- FLSNBMIFUBTWCA-UHFFFAOYSA-N n-(3-aminocyclohexyl)-2-(3-bicyclo[2.2.1]heptanyl)-7-hydroxy-1h-benzimidazole-4-carboxamide Chemical compound C1C(N)CCCC1NC(=O)C1=CC=C(O)C2=C1N=C(C1C3CCC(C3)C1)N2 FLSNBMIFUBTWCA-UHFFFAOYSA-N 0.000 claims 1
- KADSEBMOTREHLE-UHFFFAOYSA-N n-(4-aminocyclohexyl)-7-hydroxy-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1CC(N)CCC1NC(=O)C1=CC=C(O)C2=C1N=C(C=1SC=CC=1)N2 KADSEBMOTREHLE-UHFFFAOYSA-N 0.000 claims 1
- LGKPKPRXQJVEDQ-UHFFFAOYSA-N n-(azetidin-3-ylmethyl)-2-cyclopropyl-7-hydroxy-1h-benzimidazole-4-carboxamide Chemical compound C1=2NC(C3CC3)=NC=2C(O)=CC=C1C(=O)NCC1CNC1 LGKPKPRXQJVEDQ-UHFFFAOYSA-N 0.000 claims 1
- QOQKTKZYZAUZTA-UHFFFAOYSA-N n-(azetidin-3-ylmethyl)-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)NCC1CNC1 QOQKTKZYZAUZTA-UHFFFAOYSA-N 0.000 claims 1
- MRGFHHVXSDCNRD-UHFFFAOYSA-N n-[(4-aminocyclohexyl)methyl]-2-(3-bicyclo[2.2.1]heptanyl)-7-hydroxy-1h-benzimidazole-4-carboxamide Chemical compound C1CC(N)CCC1CNC(=O)C1=CC=C(O)C2=C1N=C(C1C3CCC(C3)C1)N2 MRGFHHVXSDCNRD-UHFFFAOYSA-N 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- OFVZXLPLXYMCFA-LBPRGKRZSA-N tert-butyl (3s)-3-[[2-(5-bromothiophen-2-yl)-7-hydroxy-1h-benzimidazole-4-carbonyl]amino]piperidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC[C@@H]1NC(=O)C1=CC=C(O)C2=C1N=C(C=1SC(Br)=CC=1)N2 OFVZXLPLXYMCFA-LBPRGKRZSA-N 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
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
-
- 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
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/06—Antimigraine agents
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- 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
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- 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
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- 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
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- 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
- C07D235/08—Radicals containing only hydrogen and carbon atoms
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- 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
- C07D409/06—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 linked by a carbon chain containing only aliphatic carbon atoms
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- 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
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- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
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- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11654308P | 2008-11-20 | 2008-11-20 | |
| US61/116,543 | 2008-11-20 | ||
| PCT/JP2009/004975 WO2010058512A1 (en) | 2008-11-20 | 2009-09-29 | Glycogen synthase kinase-3 beta inhibitors containing 7-hydroxy-benzoimidazole-4-yl-methanone derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2011124960A true RU2011124960A (ru) | 2012-12-27 |
Family
ID=42197956
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2011124960/04A RU2011124960A (ru) | 2008-11-20 | 2009-09-29 | Ингибиторы гликогенсинтаза-киназы 3-бета, содержащие производные 7-гидроксибензоимидазол-4-илметанова |
Country Status (15)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102170785A (zh) * | 2008-07-30 | 2011-08-31 | 肿瘤疗法科学股份有限公司 | 苯并咪唑衍生物和含有其的糖原合酶激酶-3β抑制剂 |
| 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 |
| CA3134613A1 (en) | 2019-04-02 | 2020-10-08 | Aligos Therapeutics, Inc. | Compounds targeting prmt5 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004065370A1 (en) * | 2003-01-23 | 2004-08-05 | Crystalgenomics, Inc. | Glycogen synthase kinase 3beta inhibitor, composition and process for the preparation thereof |
| TWI372050B (en) * | 2003-07-03 | 2012-09-11 | Astex Therapeutics Ltd | (morpholin-4-ylmethyl-1h-benzimidazol-2-yl)-1h-pyrazoles |
| CN102271514A (zh) * | 2008-10-30 | 2011-12-07 | 肿瘤疗法科学股份有限公司 | 7-羟基-苯并咪唑-4-基-甲酮衍生物以及包含其的pbk抑制剂 |
-
2009
- 2009-09-29 KR KR1020117014051A patent/KR20110086750A/ko not_active Withdrawn
- 2009-09-29 SG SG2011036282A patent/SG171761A1/en unknown
- 2009-09-29 CN CN2009801549899A patent/CN102292083A/zh not_active Withdrawn
- 2009-09-29 EP EP09827294A patent/EP2358365A4/en not_active Withdrawn
- 2009-09-29 BR BRPI0920959A patent/BRPI0920959A2/pt not_active IP Right Cessation
- 2009-09-29 JP JP2011522179A patent/JP2012509249A/ja not_active Withdrawn
- 2009-09-29 RU RU2011124960/04A patent/RU2011124960A/ru unknown
- 2009-09-29 US US13/129,361 patent/US20110301146A1/en not_active Abandoned
- 2009-09-29 AU AU2009318719A patent/AU2009318719A1/en not_active Withdrawn
- 2009-09-29 MX MX2011005369A patent/MX2011005369A/es unknown
- 2009-09-29 WO PCT/JP2009/004975 patent/WO2010058512A1/en not_active Ceased
- 2009-09-29 CA CA2744012A patent/CA2744012A1/en not_active Abandoned
-
2011
- 2011-05-05 IL IL212704A patent/IL212704A0/en unknown
- 2011-05-19 CO CO11061830A patent/CO6361935A2/es not_active Application Discontinuation
- 2011-06-17 ZA ZA2011/04487A patent/ZA201104487B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20110086750A (ko) | 2011-07-29 |
| JP2012509249A (ja) | 2012-04-19 |
| SG171761A1 (en) | 2011-07-28 |
| MX2011005369A (es) | 2011-06-20 |
| ZA201104487B (en) | 2012-03-28 |
| CA2744012A1 (en) | 2010-05-27 |
| EP2358365A1 (en) | 2011-08-24 |
| US20110301146A1 (en) | 2011-12-08 |
| IL212704A0 (en) | 2011-07-31 |
| CO6361935A2 (es) | 2012-01-20 |
| BRPI0920959A2 (pt) | 2017-07-11 |
| AU2009318719A1 (en) | 2011-06-30 |
| CN102292083A (zh) | 2011-12-21 |
| EP2358365A4 (en) | 2012-05-30 |
| WO2010058512A1 (en) | 2010-05-27 |
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