HRP20030360A2 - Benzodiazepine derivatives as gaba a receptor modulators - Google Patents
Benzodiazepine derivatives as gaba a receptor modulators Download PDFInfo
- Publication number
- HRP20030360A2 HRP20030360A2 HR20030360A HRP20030360A HRP20030360A2 HR P20030360 A2 HRP20030360 A2 HR P20030360A2 HR 20030360 A HR20030360 A HR 20030360A HR P20030360 A HRP20030360 A HR P20030360A HR P20030360 A2 HRP20030360 A2 HR P20030360A2
- Authority
- HR
- Croatia
- Prior art keywords
- triazolo
- imidazo
- benzodiazepine
- ethyl
- carboxylate
- Prior art date
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- 102000004300 GABA-A Receptors Human genes 0.000 title description 14
- 108090000839 GABA-A Receptors Proteins 0.000 title description 14
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 title 1
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 title 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 119
- 150000001875 compounds Chemical class 0.000 claims description 100
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical compound N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 claims description 59
- 238000000034 method Methods 0.000 claims description 33
- -1 C1-7-alkoxy Chemical group 0.000 claims description 25
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 150000002367 halogens Chemical group 0.000 claims description 11
- 229940049706 benzodiazepine Drugs 0.000 claims description 10
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims description 10
- 150000001557 benzodiazepines Chemical class 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
- 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 claims description 3
- 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 claims description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
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- 208000010877 cognitive disease Diseases 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
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- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 9
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
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- 150000007942 carboxylates Chemical class 0.000 claims 1
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- XZBIXDPGRMLSTC-UHFFFAOYSA-N formohydrazide Chemical compound NNC=O XZBIXDPGRMLSTC-UHFFFAOYSA-N 0.000 description 8
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
-
- 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
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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| EP00124332 | 2000-11-16 | ||
| PCT/EP2001/012887 WO2002040487A2 (en) | 2000-11-16 | 2001-11-08 | Benzodiazepine derivatives as gaba a receptor modulators |
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| JP4616770B2 (ja) * | 2003-06-19 | 2011-01-19 | 第一三共株式会社 | 選択的なアミノ置換基導入法 |
| ES2515092T3 (es) | 2003-12-11 | 2014-10-29 | Sunovion Pharmaceuticals Inc. | Combinación de un sedante y un modulador neurotransmisor y métodos de mejorar la calidad del sueño y de tratar la depresión |
| CA2577060A1 (en) | 2004-08-13 | 2006-02-23 | Amgen Inc. | Substituted benzofused heterocycles |
| EP1809297B1 (en) * | 2004-10-12 | 2008-07-30 | F. Hoffmann-Roche AG | Imidazo[1,5a]triazolo[1,5d]benzodiazepine derivatives for the treatment of cognitive disorders |
| WO2006045430A1 (en) | 2004-10-20 | 2006-05-04 | F. Hoffmann-La Roche Ag | Imidazo-benzodiazepine derivatives |
| WO2006045429A1 (en) * | 2004-10-20 | 2006-05-04 | F. Hoffmann-La Roche Ag | Halogen substituted benzodiazepine derivatives |
| BRPI0515800A (pt) | 2004-12-14 | 2008-08-05 | Hoffmann La Roche | imidazo-benzodiazepinas tetracìclicas como moduladores de receptores de gaba |
| US8510055B2 (en) | 2005-08-03 | 2013-08-13 | The Johns Hopkins University | Methods for characterizing and treating cognitive impairment in aging and disease |
| WO2007019312A2 (en) * | 2005-08-03 | 2007-02-15 | The Johns Hopkins University | Methods for characterizing and treating cognitive impairment in aging and disease |
| CN101287738B (zh) * | 2005-10-11 | 2011-08-10 | 弗·哈夫曼-拉罗切有限公司 | 咪唑并苯并二氮杂*衍生物 |
| CA2625210A1 (en) * | 2005-10-31 | 2007-05-10 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| WO2009139916A1 (en) * | 2008-05-16 | 2009-11-19 | Synta Pharmaceuticals Corp. | Tricyclic triazole compounds that modulate hsp90 activity |
| MX2011005119A (es) * | 2008-11-18 | 2011-05-30 | Hoffmann La Roche | Alquilciclohexileteres de dihidrotetraazabenzoazulenos. |
| NZ592076A (en) * | 2008-11-28 | 2012-06-29 | Hoffmann La Roche | Arylcyclohexylethers of dihydrotetraazabenzoazulenes for use as vasopressin via receptor antagonists |
| CU20090172A6 (es) | 2009-10-09 | 2011-10-05 | Facultad De Quimica Universidad De La Habana | Sistemas tricíclicos y tetracíclicos con actividad sobre el sistema nervioso central y vascular |
| WO2012068161A1 (en) | 2010-11-15 | 2012-05-24 | Agenebio, Inc. | Pyridazine derivatives, compositions and methods for treating cognitive impairment |
| US20150374705A1 (en) | 2012-02-14 | 2015-12-31 | Shanghai Institues for Biological Sciences | Substances for treatment or relief of pain |
| EP2897963A4 (en) * | 2012-09-21 | 2016-03-30 | Uwm Res Foundation Inc | NOVEL GABAA AGONISTS AND METHODS OF USING THEM TO CONTROL BRONCHIC HYPER-REACTION AND INFLAMMATION DURING ASTHMA |
| EP3083569B1 (en) | 2013-12-20 | 2022-01-26 | Agenebio, Inc. | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
| CN108026107B (zh) | 2015-06-19 | 2021-07-30 | 艾吉因生物股份有限公司 | 用于治疗认知损害的苯并二氮杂环庚三烯衍生物、组合物和方法 |
| US10059718B2 (en) * | 2016-01-04 | 2018-08-28 | Tabomedex Biosciences, LLC | Fused quadracyclic compounds, compositions and uses thereof |
| US10973479B2 (en) | 2016-05-16 | 2021-04-13 | Canon Medical Systems Corporation | X-ray diagnosis apparatus, X-ray diagnosis apparatus controlling method, and X-ray diagnosis system |
| BR112019012821A2 (pt) | 2016-12-19 | 2019-11-26 | Agenebio Inc | derivados de benzodiazepina, composições e métodos para o tratamento do comprometimento cognitivo |
| US20180170941A1 (en) * | 2016-12-19 | 2018-06-21 | Agenebio, Inc. | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
| KR102512548B1 (ko) | 2017-12-22 | 2023-03-22 | 삼성디스플레이 주식회사 | 유기 전계 발광 소자 및 유기 전계 발광 소자용 함질소 화합물 |
| CA3104478A1 (en) | 2018-06-19 | 2019-12-26 | Agenebio, Inc. | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
| KR102151969B1 (ko) * | 2019-12-11 | 2020-09-04 | 주식회사 지투비 | 투과도 가변창의 제조방법 및 그에 의해 제조된 투과도 가변창 |
| CN112979658B (zh) * | 2021-02-22 | 2022-05-31 | 南湖实验室 | 一种氟马西尼的制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK174086D0 (da) | 1986-04-16 | 1986-04-16 | Ferrosan As | Nye benzodiazepinderivater samt fremgangsmaade til fremstilling af samme |
| TW201311B (hu) * | 1991-06-17 | 1993-03-01 | Hoffmann La Roche |
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