RU2478099C2 - Производные 2-аза-бицикло[3.3.0]октана - Google Patents
Производные 2-аза-бицикло[3.3.0]октана Download PDFInfo
- Publication number
- RU2478099C2 RU2478099C2 RU2010106854/04A RU2010106854A RU2478099C2 RU 2478099 C2 RU2478099 C2 RU 2478099C2 RU 2010106854/04 A RU2010106854/04 A RU 2010106854/04A RU 2010106854 A RU2010106854 A RU 2010106854A RU 2478099 C2 RU2478099 C2 RU 2478099C2
- Authority
- RU
- Russia
- Prior art keywords
- carboxylic acid
- azabicyclo
- amide
- carbonyl
- octan
- Prior art date
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- ADKDJHASTPQGEO-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydrocyclopenta[b]pyrrole Chemical class C1CNC2CCCC21 ADKDJHASTPQGEO-UHFFFAOYSA-N 0.000 title abstract description 10
- -1 benzoisoxazolyl group Chemical group 0.000 claims abstract description 54
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 27
- 150000002367 halogens Chemical class 0.000 claims abstract description 27
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 21
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 125000000335 thiazolyl group Chemical group 0.000 claims abstract description 7
- 230000000694 effects Effects 0.000 claims abstract description 5
- XCUAIINAJCDIPM-XVFCMESISA-N N(4)-hydroxycytidine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=NO)C=C1 XCUAIINAJCDIPM-XVFCMESISA-N 0.000 claims abstract description 3
- 229940123730 Orexin receptor antagonist Drugs 0.000 claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims description 54
- 125000001424 substituent group Chemical group 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 229910052799 carbon Inorganic materials 0.000 claims description 31
- 208000019116 sleep disease Diseases 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 5
- CHDSHBWEGSCEDX-UHFFFAOYSA-N 2,3-dihydro-1-benzofuran-4-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=C1CCO2 CHDSHBWEGSCEDX-UHFFFAOYSA-N 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
- LJZNNVINQVABLC-JBACZVJFSA-N C1(CC1)C=1SC(=C(N1)C(=O)N1[C@H]2CCC[C@H]2C[C@H]1CC1=CC=CC2=C1C(=NO2)C(=O)N)C2=CC=CC=C2 Chemical compound C1(CC1)C=1SC(=C(N1)C(=O)N1[C@H]2CCC[C@H]2C[C@H]1CC1=CC=CC2=C1C(=NO2)C(=O)N)C2=CC=CC=C2 LJZNNVINQVABLC-JBACZVJFSA-N 0.000 claims description 2
- NMECYMRCJJLFGF-VSZGBHKWSA-N C1(CC1)C=1SC(=C(N1)C(=O)N1[C@H]2CCC[C@H]2C[C@H]1CC1OC=2C(C1)=C(C=CC2)C(=O)N)C2=CC=CC=C2 Chemical compound C1(CC1)C=1SC(=C(N1)C(=O)N1[C@H]2CCC[C@H]2C[C@H]1CC1OC=2C(C1)=C(C=CC2)C(=O)N)C2=CC=CC=C2 NMECYMRCJJLFGF-VSZGBHKWSA-N 0.000 claims description 2
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- DOTCHYMEKCDVKK-LRQRDZAKSA-N n-[[(2s,3as,6as)-1-[5-(3-chlorophenyl)-2-methyl-1,3-thiazole-4-carbonyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]pyrrol-2-yl]methyl]-1,2-benzoxazole-3-carboxamide Chemical compound S1C(C)=NC(C(=O)N2[C@H]3CCC[C@H]3C[C@H]2CNC(=O)C=2C3=CC=CC=C3ON=2)=C1C1=CC=CC(Cl)=C1 DOTCHYMEKCDVKK-LRQRDZAKSA-N 0.000 claims description 2
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Classifications
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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
- C07D413/12—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 linked by a chain containing hetero atoms as chain links
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- A—HUMAN NECESSITIES
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- 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
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- 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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- A—HUMAN NECESSITIES
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- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
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- A—HUMAN NECESSITIES
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
-
- 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
- C07D405/12—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 chain containing hetero atoms as chain links
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Diabetes (AREA)
- Addiction (AREA)
- Anesthesiology (AREA)
- Hospice & Palliative Care (AREA)
- Child & Adolescent Psychology (AREA)
- Pain & Pain Management (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Psychology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| IB2007052991 | 2007-07-27 | ||
| IBPCT/IB2007/052991 | 2007-07-27 | ||
| PCT/IB2008/052989 WO2009016564A2 (en) | 2007-07-27 | 2008-07-25 | 2-aza-bicyclo[3.3.0]octane derivatives |
Publications (2)
| Publication Number | Publication Date |
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| RU2010106854A RU2010106854A (ru) | 2011-09-10 |
| RU2478099C2 true RU2478099C2 (ru) | 2013-03-27 |
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| EP (1) | EP2183246A2 (enExample) |
| JP (1) | JP2010534647A (enExample) |
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| CA (1) | CA2693820A1 (enExample) |
| MA (1) | MA31593B1 (enExample) |
| NZ (1) | NZ583487A (enExample) |
| RU (1) | RU2478099C2 (enExample) |
| WO (1) | WO2009016564A2 (enExample) |
| ZA (1) | ZA201001434B (enExample) |
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| TW200823227A (en) * | 2006-09-29 | 2008-06-01 | Actelion Pharmaceuticals Ltd | 3-aza-bicyclo[3.1.0]hexane derivatives |
| ATE496043T1 (de) | 2006-12-01 | 2011-02-15 | Actelion Pharmaceuticals Ltd | 3-heteroaryl (amino bzw. amido)-1- (biphenyl bzw. phenylthiazolyl) carbonylpiperdinderivate als orexinrezeptor-inhibitoren |
| TW200833328A (en) * | 2006-12-28 | 2008-08-16 | Actelion Pharmaceuticals Ltd | 2-aza-bicyclo[3.1.0]hexane derivatives |
| CL2008000836A1 (es) * | 2007-03-26 | 2008-11-07 | Actelion Pharmaceuticals Ltd | Compuestos derivados de tiazolidina, antagonistas del receptor de orexina; composicion farmaceutica que los comprende; y su uso en el tratamiento de neurosis emocional, depresion grave, trastornos psicoticos, alzheimer, parkinson, dolor, entre otras. |
| JP2010528007A (ja) | 2007-05-23 | 2010-08-19 | メルク・シャープ・エンド・ドーム・コーポレイション | シクロプロピルピロリジンオレキシン受容体アンタゴニスト |
| ES2371514T3 (es) * | 2007-07-03 | 2012-01-04 | Actelion Pharmaceuticals Ltd. | Compuestos de 3-aza-biciclo[3.3.0]octano. |
| US8288411B2 (en) * | 2007-09-24 | 2012-10-16 | Actelion Pharmaceuticals Ltd. | Pyrrolidines and piperidines as orexin receptor antagonists |
| CN101965343A (zh) * | 2008-02-21 | 2011-02-02 | 埃科特莱茵药品有限公司 | 2-氮杂-双环[2.2.1]庚烷衍生物 |
| WO2009133522A1 (en) * | 2008-04-30 | 2009-11-05 | Actelion Pharmaceuticals Ltd | Piperidine and pyrrolidine compounds |
| BRPI0920183A2 (pt) * | 2008-10-14 | 2018-05-22 | Actelion Pharmaceuticals Ltd | derivados de fenetilamida e seus analogos heterociclicos |
| MX2012004753A (es) | 2009-10-23 | 2012-09-07 | Janssen Pharmaceutica Nv | Octahidropirrolo[3,4-c]pirrolos disustituidos como moduladores del receptor de orexina. |
| MX2012006909A (es) * | 2009-12-29 | 2012-07-10 | Suven Life Sciences Ltd | LIGANDOS DEL RECEPTOR NICOTINICO NEURONAL A4ß2 DE ACETILCOLINA. |
| PH12012501556A1 (en) | 2009-12-30 | 2012-10-22 | Arqule Inc | Substituted naphthalenyl-pyrimidine compounds |
| RU2014136339A (ru) | 2012-02-07 | 2016-03-27 | Иолас Терапьютикс, Инк. | Замещенные пролины/пиперидины как антагонисты орексиновых рецепторов |
| US9440982B2 (en) | 2012-02-07 | 2016-09-13 | Eolas Therapeutics, Inc. | Substituted prolines/piperidines as orexin receptor antagonists |
| ITMI20120424A1 (it) | 2012-03-19 | 2013-09-20 | Rottapharm Spa | Composti chimici |
| PT2855453T (pt) | 2012-06-04 | 2017-03-09 | Actelion Pharmaceuticals Ltd | Derivados de benzimidazol-prolina |
| WO2014057435A1 (en) | 2012-10-10 | 2014-04-17 | Actelion Pharmaceuticals Ltd | Orexin receptor antagonists which are [ortho bi (hetero )aryl]-[2-(meta bi (hetero )aryl)-pyrrolidin-1-yl]-methanone derivatives |
| EP2970241A1 (en) | 2013-03-12 | 2016-01-20 | Actelion Pharmaceuticals Ltd. | Azetidine amide derivatives as orexin receptor antagonists |
| PL3077389T3 (pl) | 2013-12-03 | 2018-03-30 | Idorsia Pharmaceuticals Ltd | KRYSTALICZNA POSTAĆ (S)-(2-(6-CHLORO-7-METYLO-1H-BENZO[D]lMIDAZOL-2-ILO)- 2-METYLOPIROLIDYN-1-YLO)(5-METOKSY-2-(2H-1,2,3-TRIAZOL-2-ILO)FENYLO)METANONU I JEJ ZASTOSOWANIE JAKO ANTAGONISTY RECEPTORA OREKSYNY |
| UA119151C2 (uk) | 2013-12-03 | 2019-05-10 | Ідорсія Фармасьютікалз Лтд | КРИСТАЛІЧНА СОЛЬОВА ФОРМА (S)-(2-(6-ХЛОР-7-МЕТИЛ-1H-БЕНЗО[d]ІМІДАЗОЛ-2-ІЛ)-2-МЕТИЛПІРОЛІДИН-1-ІЛ)(5-МЕТОКСИ-2-(2H-1,2,3-ТРИАЗОЛ-2-ІЛ)ФЕНІЛ)МЕТАНОНУ ЯК АНТАГОНІСТ ОРЕКСИНОВОГО РЕЦЕПТОРА |
| UA116053C2 (uk) | 2013-12-04 | 2018-01-25 | Ідорсія Фармасьютікалз Лтд | Застосування похідних бензоімідазолу-проліну |
| EP3180332B1 (en) | 2014-08-13 | 2021-10-27 | Eolas Therapeutics Inc. | Difluoropyrrolidines as orexin receptor modulators |
| KR102738491B1 (ko) | 2016-02-12 | 2024-12-03 | 아스트라제네카 아베 | 오렉신 수용체 조정제로서의 할로-치환된 피페리딘 |
| RS63296B1 (sr) | 2016-03-10 | 2022-07-29 | Janssen Pharmaceutica Nv | Metode lečenja depresije korišćenjem antagonista receptora oreksin-2 |
| US20190151304A1 (en) | 2016-05-10 | 2019-05-23 | Inserm (Institut National De La Santé Et De La Rechercjae Médicale | Methods and pharmaceutical compositions for the treatment of autoimmune inflammatory |
| GB201618181D0 (en) | 2016-10-27 | 2016-12-14 | J Banks & Co Ltd | Slide turn door assembly and support mechanism therefor |
| WO2020007964A1 (en) | 2018-07-05 | 2020-01-09 | Idorsia Pharmaceuticals Ltd | 2-(2-azabicyclo[3.1.0]hexan-1-yl)-1h-benzimidazole derivatives |
| WO2020099511A1 (en) | 2018-11-14 | 2020-05-22 | Idorsia Pharmaceuticals Ltd | Benzimidazole-2-methyl-morpholine derivatives |
| US12497362B2 (en) | 2020-08-18 | 2025-12-16 | Merck Sharp & Dohme Llc | Cyclopentapyrrole orexin receptor agonists |
| TW202400149A (zh) | 2022-05-13 | 2024-01-01 | 瑞士商愛杜西亞製藥有限公司 | 經噻唑并芳基-甲基取代之環狀肼-n-甲醯胺衍生物 |
| WO2025224168A1 (en) | 2024-04-24 | 2025-10-30 | Idorsia Pharmaceuticals Ltd | Aryl sulfone and sulfanone derivatives as orexin receptor modulators |
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| RU2135503C1 (ru) * | 1992-06-19 | 1999-08-27 | Басф Акциенгезельшафт | N-замещенные производные 3-азабицикло (3.2.0)гептана или их соли с физиологически совместимыми кислотами |
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| WO1995029922A1 (en) | 1994-04-29 | 1995-11-09 | Pharmacia & Upjohn Company | Methanol derivatives for treatment of retroviral infections especially hiv infections |
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| GB0115862D0 (en) | 2001-06-28 | 2001-08-22 | Smithkline Beecham Plc | Compounds |
| GB0124463D0 (en) | 2001-10-11 | 2001-12-05 | Smithkline Beecham Plc | Compounds |
| GB0127145D0 (en) | 2001-11-10 | 2002-01-02 | Smithkline Beecham | Compounds |
| GB0130335D0 (en) | 2001-12-19 | 2002-02-06 | Smithkline Beecham Plc | Compounds |
| GB0130393D0 (en) | 2001-12-19 | 2002-02-06 | Smithkline Beecham Plc | Compounds |
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| PL210065B1 (pl) | 2002-09-25 | 2011-11-30 | Memory Pharm Corp | Związki indazole, benzotiazole i benzoizotiazole, kompozycje farmaceutyczne je zawierające oraz zastosowanie związków |
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| CA2560741C (en) | 2004-03-25 | 2013-08-06 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, and preparation and uses thereof |
| US20060014733A1 (en) | 2004-07-19 | 2006-01-19 | Pfizer Inc | Histamine-3 agonists and antagonists |
| TW200823227A (en) | 2006-09-29 | 2008-06-01 | Actelion Pharmaceuticals Ltd | 3-aza-bicyclo[3.1.0]hexane derivatives |
| ATE496043T1 (de) | 2006-12-01 | 2011-02-15 | Actelion Pharmaceuticals Ltd | 3-heteroaryl (amino bzw. amido)-1- (biphenyl bzw. phenylthiazolyl) carbonylpiperdinderivate als orexinrezeptor-inhibitoren |
| CL2008000836A1 (es) | 2007-03-26 | 2008-11-07 | Actelion Pharmaceuticals Ltd | Compuestos derivados de tiazolidina, antagonistas del receptor de orexina; composicion farmaceutica que los comprende; y su uso en el tratamiento de neurosis emocional, depresion grave, trastornos psicoticos, alzheimer, parkinson, dolor, entre otras. |
| DE602008002934D1 (de) | 2007-05-14 | 2010-11-18 | Actelion Pharmaceuticals Ltd | 2-cyclopropylthiazolderivate |
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| WO2009080533A1 (en) | 2007-12-21 | 2009-07-02 | F. Hoffmann-La Roche Ag | Heteroaryl derivatives as orexin receptor antagonists |
| CN101965343A (zh) | 2008-02-21 | 2011-02-02 | 埃科特莱茵药品有限公司 | 2-氮杂-双环[2.2.1]庚烷衍生物 |
| WO2009133522A1 (en) | 2008-04-30 | 2009-11-05 | Actelion Pharmaceuticals Ltd | Piperidine and pyrrolidine compounds |
| JP2011520966A (ja) | 2008-05-22 | 2011-07-21 | メルク・シャープ・エンド・ドーム・コーポレイション | オレキシン受容体アンタゴニストの調製のための方法 |
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2008
- 2008-07-25 CN CN200880100389XA patent/CN101874028B/zh not_active Expired - Fee Related
- 2008-07-25 NZ NZ583487A patent/NZ583487A/en not_active IP Right Cessation
- 2008-07-25 BR BRPI0814593-8A2A patent/BRPI0814593A2/pt not_active IP Right Cessation
- 2008-07-25 CA CA2693820A patent/CA2693820A1/en not_active Abandoned
- 2008-07-25 WO PCT/IB2008/052989 patent/WO2009016564A2/en not_active Ceased
- 2008-07-25 US US12/670,823 patent/US8288429B2/en not_active Expired - Fee Related
- 2008-07-25 AU AU2008281399A patent/AU2008281399A1/en not_active Abandoned
- 2008-07-25 RU RU2010106854/04A patent/RU2478099C2/ru not_active IP Right Cessation
- 2008-07-25 EP EP08789443A patent/EP2183246A2/en not_active Withdrawn
- 2008-07-25 JP JP2010517536A patent/JP2010534647A/ja active Pending
- 2008-07-25 KR KR1020107004524A patent/KR20100046047A/ko not_active Withdrawn
-
2010
- 2010-02-05 MA MA32589A patent/MA31593B1/fr unknown
- 2010-02-26 ZA ZA2010/01434A patent/ZA201001434B/en unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1676451A3 (ru) * | 1987-09-23 | 1991-09-07 | Иституто Де Анджели С.П.А. (Фирма) | Способ получени производных бензимидазола в виде смеси изомеров или индивидуальных изомеров в свободном виде или в виде их физиологически приемлемых солей |
| RU2135503C1 (ru) * | 1992-06-19 | 1999-08-27 | Басф Акциенгезельшафт | N-замещенные производные 3-азабицикло (3.2.0)гептана или их соли с физиологически совместимыми кислотами |
Also Published As
| Publication number | Publication date |
|---|---|
| MA31593B1 (fr) | 2010-08-02 |
| CN101874028A (zh) | 2010-10-27 |
| NZ583487A (en) | 2011-09-30 |
| ZA201001434B (en) | 2013-08-28 |
| RU2010106854A (ru) | 2011-09-10 |
| US8288429B2 (en) | 2012-10-16 |
| CA2693820A1 (en) | 2009-02-05 |
| US20110009461A1 (en) | 2011-01-13 |
| WO2009016564A2 (en) | 2009-02-05 |
| BRPI0814593A2 (pt) | 2015-01-20 |
| JP2010534647A (ja) | 2010-11-11 |
| KR20100046047A (ko) | 2010-05-04 |
| CN101874028B (zh) | 2012-11-14 |
| EP2183246A2 (en) | 2010-05-12 |
| AU2008281399A1 (en) | 2009-02-05 |
| WO2009016564A3 (en) | 2009-03-26 |
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