RU2435759C2 - Производные бензимидазолов и их применение для модуляции гамка-рецепторного комплекса - Google Patents
Производные бензимидазолов и их применение для модуляции гамка-рецепторного комплекса Download PDFInfo
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- RU2435759C2 RU2435759C2 RU2008129868/04A RU2008129868A RU2435759C2 RU 2435759 C2 RU2435759 C2 RU 2435759C2 RU 2008129868/04 A RU2008129868/04 A RU 2008129868/04A RU 2008129868 A RU2008129868 A RU 2008129868A RU 2435759 C2 RU2435759 C2 RU 2435759C2
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- Prior art keywords
- isomers
- receptor complex
- pharmaceutically acceptable
- compound according
- mixture
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- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title abstract 3
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title abstract 3
- 102000027484 GABAA receptors Human genes 0.000 title 1
- 108091008681 GABAA receptors Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 9
- 239000000203 mixture Substances 0.000 claims abstract 6
- 150000003839 salts Chemical class 0.000 claims abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 4
- 239000001257 hydrogen Substances 0.000 claims abstract 4
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 3
- 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
- 238000000034 method Methods 0.000 claims abstract 2
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims 10
- OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 claims 5
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- KPKWNVBNNSAKLP-CYBMUJFWSA-N (1r)-1-[1-[3-(2-fluoropyridin-3-yl)phenyl]benzimidazol-5-yl]ethanol Chemical compound C1=NC2=CC([C@H](O)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CN=C1F KPKWNVBNNSAKLP-CYBMUJFWSA-N 0.000 claims 1
- KPKWNVBNNSAKLP-ZDUSSCGKSA-N (1s)-1-[1-[3-(2-fluoropyridin-3-yl)phenyl]benzimidazol-5-yl]ethanol Chemical compound C1=NC2=CC([C@@H](O)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CN=C1F KPKWNVBNNSAKLP-ZDUSSCGKSA-N 0.000 claims 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 1
- IAYHUMJVDOMXNP-UHFFFAOYSA-N 2-[1-[3-(2-chloropyridin-3-yl)phenyl]benzimidazol-5-yl]propan-2-ol Chemical compound C1=NC2=CC(C(C)(O)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CN=C1Cl IAYHUMJVDOMXNP-UHFFFAOYSA-N 0.000 claims 1
- YUXCRCCATFXYCX-UHFFFAOYSA-N 2-[1-[3-(2-fluoropyridin-3-yl)phenyl]benzimidazol-5-yl]propan-2-ol Chemical compound C1=NC2=CC(C(C)(O)C)=CC=C2N1C(C=1)=CC=CC=1C1=CC=CN=C1F YUXCRCCATFXYCX-UHFFFAOYSA-N 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
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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
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
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- A61P25/08—Antiepileptics; Anticonvulsants
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A61P25/20—Hypnotics; Sedatives
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- A—HUMAN NECESSITIES
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- A61P25/22—Anxiolytics
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- A—HUMAN NECESSITIES
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- 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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- 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
- C07D401/10—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 carbon chain containing aromatic rings
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- 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
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
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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
- C07D403/10—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 carbon chain containing aromatic rings
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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
- C07D403/14—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 three or more hetero rings
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- 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
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- 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
- C07D405/10—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 linked by a carbon chain containing aromatic rings
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- 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
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- 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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Diabetes (AREA)
- Psychiatry (AREA)
- Immunology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Hospice & Palliative Care (AREA)
- Addiction (AREA)
- Anesthesiology (AREA)
- Gynecology & Obstetrics (AREA)
- Transplantation (AREA)
- Nutrition Science (AREA)
- Rheumatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Otolaryngology (AREA)
- Emergency Medicine (AREA)
- Pregnancy & Childbirth (AREA)
- Cardiology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US78527806P | 2006-03-24 | 2006-03-24 | |
| DKPA200600426 | 2006-03-24 | ||
| US60/785,278 | 2006-03-24 | ||
| DKPA200600426 | 2006-03-24 | ||
| DKPA200601327 | 2006-10-12 | ||
| DKPA200601327 | 2006-10-12 | ||
| US85128406P | 2006-10-13 | 2006-10-13 | |
| US60/851,284 | 2006-10-13 | ||
| PCT/EP2007/052766 WO2007110374A1 (en) | 2006-03-24 | 2007-03-22 | Benzimidazole derivatives and their use for modulating the gabaa receptor complex |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2008129868A RU2008129868A (ru) | 2010-04-27 |
| RU2435759C2 true RU2435759C2 (ru) | 2011-12-10 |
Family
ID=39456294
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2008129868/04A RU2435759C2 (ru) | 2006-03-24 | 2007-03-22 | Производные бензимидазолов и их применение для модуляции гамка-рецепторного комплекса |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US7902230B2 (https=) |
| EP (2) | EP2319837B1 (https=) |
| JP (1) | JP5260489B2 (https=) |
| KR (1) | KR20080111097A (https=) |
| CN (1) | CN101384559B (https=) |
| AR (1) | AR060084A1 (https=) |
| AT (1) | ATE486856T1 (https=) |
| AU (1) | AU2007229502B2 (https=) |
| BR (1) | BRPI0710203A2 (https=) |
| CA (1) | CA2647252A1 (https=) |
| CY (1) | CY1111603T1 (https=) |
| DE (1) | DE602007010261D1 (https=) |
| DK (1) | DK2001855T3 (https=) |
| ES (1) | ES2355163T3 (https=) |
| HR (1) | HRP20100616T1 (https=) |
| IL (1) | IL192297A (https=) |
| MX (1) | MX2008010885A (https=) |
| MY (1) | MY149855A (https=) |
| NO (1) | NO20084481L (https=) |
| NZ (1) | NZ569438A (https=) |
| PL (1) | PL2001855T3 (https=) |
| PT (1) | PT2001855E (https=) |
| RU (1) | RU2435759C2 (https=) |
| SI (1) | SI2001855T1 (https=) |
| TW (1) | TWI391381B (https=) |
| WO (1) | WO2007110374A1 (https=) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2006233894A1 (en) | 2005-04-13 | 2006-10-19 | Neurosearch A/S | Benzimidazole derivatives and their use for modulating the GABAA receptor complex |
| CA2632395A1 (en) | 2005-12-05 | 2007-06-14 | Neurosearch A/S | Benzimidazole derivatives and their use for modulating the gabaa receptor complex |
| TWI391381B (zh) * | 2006-03-24 | 2013-04-01 | Neurosearch As | 新穎的苯并咪唑衍生物、含有其之醫藥組成物、及其於製造藥物之用途 |
| JP2011507905A (ja) * | 2007-12-21 | 2011-03-10 | ワイス・エルエルシー | ベンズイミダゾール化合物 |
| WO2010055133A1 (en) * | 2008-11-14 | 2010-05-20 | Neurosearch A/S | Benzimidazole derivatives and their use for modulating the gabaa receptor complex |
| TW201029987A (en) * | 2008-11-14 | 2010-08-16 | Neurosearch As | Novel compounds |
| WO2010055129A1 (en) * | 2008-11-14 | 2010-05-20 | Neurosearch A/S | Benzimidazole derivatives and their use for modulating the gabaa receptor complex |
| WO2010055130A1 (en) * | 2008-11-14 | 2010-05-20 | Neurosearch A/S | Benzimidazole derivatives and their use for modulating the gabaa receptor complex |
| TW201029986A (en) * | 2008-11-14 | 2010-08-16 | Neurosearch As | Novel compounds |
| TW201029989A (en) * | 2008-11-14 | 2010-08-16 | Neurosearch As | Novel compounds |
| WO2011047315A1 (en) | 2009-10-15 | 2011-04-21 | Concert Pharmaceuticals, Inc. | Subsitituted benzimidazoles |
| JP5947465B2 (ja) * | 2012-10-01 | 2016-07-06 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | Ｃｎｓ活性剤としてのベンズイミダゾール類 |
| CN107445845A (zh) * | 2017-08-24 | 2017-12-08 | 重庆沃肯精细化工有限公司 | 一种合成氯法齐明关键中间体n‑(4‑氯苯基)‑1，2‑苯二胺的方法 |
| WO2019154257A1 (zh) * | 2018-02-11 | 2019-08-15 | 江苏豪森药业集团有限公司 | 一种甾族类衍生物调节剂及其制备方法和应用 |
| BR112021004661A2 (pt) * | 2018-09-13 | 2021-06-01 | Saniona A/S | composto, composição farmacêutica, método para tratamento de dor neuropática e/ou prurido, e, uso do composto |
| KR102219563B1 (ko) * | 2019-02-15 | 2021-02-24 | 에스티팜 주식회사 | 페나진 유도체 제조를 위한 중간체 및 그의 제조방법 |
| CN120267677A (zh) * | 2019-10-23 | 2025-07-08 | 纽罗塞克医疗公司 | 用gabaa受体调节剂的癫痫状况的治疗 |
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| CN116693555B (zh) * | 2022-02-25 | 2025-07-04 | 上海赛默罗生物科技有限公司 | 咪唑并哒嗪类衍生物、其制备方法、药物组合物和用途 |
| WO2025141131A1 (en) | 2023-12-27 | 2025-07-03 | Saniona A/S | A gabaa receptor ligand and the use thereof in medicine, in particular in the treatment of epilepsy |
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