KR20110086750A - 7-히드록시-벤조이미다졸-4-일-메타논 유도체를 포함하는 당원 합성효소 키나아제-3베타 저해제 - Google Patents
7-히드록시-벤조이미다졸-4-일-메타논 유도체를 포함하는 당원 합성효소 키나아제-3베타 저해제 Download PDFInfo
- Publication number
- KR20110086750A KR20110086750A KR1020117014051A KR20117014051A KR20110086750A KR 20110086750 A KR20110086750 A KR 20110086750A KR 1020117014051 A KR1020117014051 A KR 1020117014051A KR 20117014051 A KR20117014051 A KR 20117014051A KR 20110086750 A KR20110086750 A KR 20110086750A
- Authority
- KR
- South Korea
- Prior art keywords
- benzo
- imidazole
- hydroxy
- carboxamide
- thiophen
- 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.)
- Withdrawn
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- 239000003112 inhibitor Substances 0.000 title claims abstract description 20
- GGRAFBSODPLTOT-UHFFFAOYSA-N 7-hydroxy-1h-benzimidazole-4-carbaldehyde Chemical class OC1=CC=C(C=O)C2=C1N=CN2 GGRAFBSODPLTOT-UHFFFAOYSA-N 0.000 title abstract 2
- 229930182470 glycoside Natural products 0.000 title 1
- 150000002338 glycosides Chemical class 0.000 title 1
- 108010051975 Glycogen Synthase Kinase 3 beta Proteins 0.000 claims abstract description 52
- 102000019058 Glycogen Synthase Kinase 3 beta Human genes 0.000 claims abstract description 52
- -1 nitro, cyano, amino Chemical group 0.000 claims description 214
- 150000001875 compounds Chemical class 0.000 claims description 53
- 238000000034 method Methods 0.000 claims description 33
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 28
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 27
- 201000010099 disease Diseases 0.000 claims description 25
- 230000001419 dependent effect Effects 0.000 claims description 20
- 239000008194 pharmaceutical composition Substances 0.000 claims description 19
- 208000024827 Alzheimer disease Diseases 0.000 claims description 17
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 17
- 206010026749 Mania Diseases 0.000 claims description 16
- 208000019695 Migraine disease Diseases 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 206010027599 migraine Diseases 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 11
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 239000012453 solvate Substances 0.000 claims description 8
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
- WVKPYYLOFMTDHB-UHFFFAOYSA-N 2-norbornyl radical Chemical group C1CC2[CH]CC1C2 WVKPYYLOFMTDHB-UHFFFAOYSA-N 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 5
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 5
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 5
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims description 4
- 150000004677 hydrates Chemical class 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 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 description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 3
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 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 description 2
- 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 description 2
- HTUPKTNEAWAZLK-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanyl)-7-hydroxy-n-piperidin-3-yl-1h-benzimidazole-4-carboxamide Chemical compound C1=2N=C(C3C4CCC(C4)C3)NC=2C(O)=CC=C1C(=O)NC1CCCNC1 HTUPKTNEAWAZLK-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- DSUNIVRRAJRRDJ-UHFFFAOYSA-N 7-hydroxy-n-(4-hydroxycyclohexyl)-2-thiophen-2-yl-1h-benzimidazole-4-carboxamide Chemical compound C1CC(O)CCC1NC(=O)C1=CC=C(O)C2=C1N=C(C=1SC=CC=1)N2 DSUNIVRRAJRRDJ-UHFFFAOYSA-N 0.000 claims description 2
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- 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 description 2
- 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 description 2
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- 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 description 2
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical group C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
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- 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 description 2
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Classifications
-
- 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
-
- 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
- A61K31/435—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
-
- 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
-
- 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
-
- 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
-
- 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
- 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
-
- 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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11654308P | 2008-11-20 | 2008-11-20 | |
| US61/116,543 | 2008-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20110086750A true KR20110086750A (ko) | 2011-07-29 |
Family
ID=42197956
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020117014051A Withdrawn KR20110086750A (ko) | 2008-11-20 | 2009-09-29 | 7-히드록시-벤조이미다졸-4-일-메타논 유도체를 포함하는 당원 합성효소 키나아제-3베타 저해제 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US20110301146A1 (enExample) |
| EP (1) | EP2358365A4 (enExample) |
| JP (1) | JP2012509249A (enExample) |
| KR (1) | KR20110086750A (enExample) |
| CN (1) | CN102292083A (enExample) |
| AU (1) | AU2009318719A1 (enExample) |
| BR (1) | BRPI0920959A2 (enExample) |
| CA (1) | CA2744012A1 (enExample) |
| CO (1) | CO6361935A2 (enExample) |
| IL (1) | IL212704A0 (enExample) |
| MX (1) | MX2011005369A (enExample) |
| RU (1) | RU2011124960A (enExample) |
| SG (1) | SG171761A1 (enExample) |
| WO (1) | WO2010058512A1 (enExample) |
| ZA (1) | ZA201104487B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010014794A1 (en) * | 2008-07-30 | 2010-02-04 | Oncotherapy Science, Inc. | Benzoimidazole derivatives and glycogen synthase kinase-3 beta inhibitors containing the same |
| 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 |
| CN114072407A (zh) | 2019-04-02 | 2022-02-18 | 阿里戈斯治疗公司 | 靶向prmt5的化合物 |
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 |
| CA2741988A1 (en) * | 2008-10-30 | 2010-05-06 | Oncotherapy Science, Inc. | 7-hydroxy-benzoimidazole-4-yl-methanone derivatives and pbk inhibitors containing the same |
-
2009
- 2009-09-29 MX MX2011005369A patent/MX2011005369A/es unknown
- 2009-09-29 US US13/129,361 patent/US20110301146A1/en not_active Abandoned
- 2009-09-29 CA CA2744012A patent/CA2744012A1/en not_active Abandoned
- 2009-09-29 EP EP09827294A patent/EP2358365A4/en not_active Withdrawn
- 2009-09-29 RU RU2011124960/04A patent/RU2011124960A/ru unknown
- 2009-09-29 JP JP2011522179A patent/JP2012509249A/ja not_active Withdrawn
- 2009-09-29 WO PCT/JP2009/004975 patent/WO2010058512A1/en not_active Ceased
- 2009-09-29 SG SG2011036282A patent/SG171761A1/en unknown
- 2009-09-29 KR KR1020117014051A patent/KR20110086750A/ko not_active Withdrawn
- 2009-09-29 BR BRPI0920959A patent/BRPI0920959A2/pt not_active IP Right Cessation
- 2009-09-29 CN CN2009801549899A patent/CN102292083A/zh not_active Withdrawn
- 2009-09-29 AU AU2009318719A patent/AU2009318719A1/en not_active Withdrawn
-
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 |
|---|---|
| RU2011124960A (ru) | 2012-12-27 |
| JP2012509249A (ja) | 2012-04-19 |
| SG171761A1 (en) | 2011-07-28 |
| BRPI0920959A2 (pt) | 2017-07-11 |
| CA2744012A1 (en) | 2010-05-27 |
| ZA201104487B (en) | 2012-03-28 |
| CO6361935A2 (es) | 2012-01-20 |
| IL212704A0 (en) | 2011-07-31 |
| MX2011005369A (es) | 2011-06-20 |
| US20110301146A1 (en) | 2011-12-08 |
| EP2358365A1 (en) | 2011-08-24 |
| WO2010058512A1 (en) | 2010-05-27 |
| AU2009318719A1 (en) | 2011-06-30 |
| EP2358365A4 (en) | 2012-05-30 |
| CN102292083A (zh) | 2011-12-21 |
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Legal Events
| Date | Code | Title | Description |
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| PA0105 | International application |
Patent event date: 20110617 Patent event code: PA01051R01D Comment text: International Patent Application |
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| PG1501 | Laying open of application | ||
| PC1202 | Submission of document of withdrawal before decision of registration |
Comment text: [Withdrawal of Procedure relating to Patent, etc.] Withdrawal (Abandonment) Patent event code: PC12021R01D Patent event date: 20120511 |
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| WITB | Written withdrawal of application |