DE60217147T2 - Lactamderivate zur verwendung als humane 11cby rezeptorantagonisten - Google Patents
Lactamderivate zur verwendung als humane 11cby rezeptorantagonisten Download PDFInfo
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- DE60217147T2 DE60217147T2 DE60217147T DE60217147T DE60217147T2 DE 60217147 T2 DE60217147 T2 DE 60217147T2 DE 60217147 T DE60217147 T DE 60217147T DE 60217147 T DE60217147 T DE 60217147T DE 60217147 T2 DE60217147 T2 DE 60217147T2
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- phenyl
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Classifications
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- 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
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
- C07D239/91—Oxygen atoms with aryl or aralkyl radicals attached in position 2 or 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
- C07D239/96—Two oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/10—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D257/12—Six-membered rings having four nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Diabetes (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Anesthesiology (AREA)
- Rheumatology (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Indole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0124627.1A GB0124627D0 (en) | 2001-10-15 | 2001-10-15 | Novel compounds |
| GB0124627 | 2001-10-15 | ||
| PCT/US2002/032740 WO2003033480A1 (en) | 2001-10-15 | 2002-10-15 | Lactam derivatives as antagonists for human 11cby receptors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60217147D1 DE60217147D1 (de) | 2007-02-08 |
| DE60217147T2 true DE60217147T2 (de) | 2007-10-31 |
Family
ID=9923785
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60217147T Expired - Fee Related DE60217147T2 (de) | 2001-10-15 | 2002-10-15 | Lactamderivate zur verwendung als humane 11cby rezeptorantagonisten |
| DE60218721T Expired - Fee Related DE60218721T2 (de) | 2001-10-15 | 2002-10-15 | Pyrimidione als Melanin-konzentrierenden Hormonrezeptor 1 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60218721T Expired - Fee Related DE60218721T2 (de) | 2001-10-15 | 2002-10-15 | Pyrimidione als Melanin-konzentrierenden Hormonrezeptor 1 |
Country Status (21)
| Country | Link |
|---|---|
| EP (2) | EP1436267B1 (enExample) |
| JP (2) | JP2005508966A (enExample) |
| KR (2) | KR20040045833A (enExample) |
| CN (2) | CN1571774A (enExample) |
| AT (2) | ATE356119T1 (enExample) |
| BR (2) | BR0213040A (enExample) |
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Families Citing this family (92)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR037429A1 (es) | 2001-11-26 | 2004-11-10 | Schering Corp | Derivados de piperidina antagonistas de la mch, composiciones farmaceuticas, un proceso para su elaboracion y el uso de dichos derivados, solos o en combinacion, para la fabricacion de un medicamento para tratamiento de la obesidad y de trastornos del snc |
| CA2468015A1 (en) | 2001-11-27 | 2003-06-05 | Merck & Co., Inc. | 2-aminoquinoline compounds |
| DE10238865A1 (de) * | 2002-08-24 | 2004-03-11 | Boehringer Ingelheim International Gmbh | Neue Carbonsäureamid-Verbindungen mit MCH-antagonistischer Wirkung, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| US7351719B2 (en) | 2002-10-31 | 2008-04-01 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Amide compounds having MCH-antagonistic activity and medicaments comprising these compounds |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| JP2006522812A (ja) * | 2003-04-11 | 2006-10-05 | スミスクライン ビーチャム コーポレーション | 複素環ｍｃｈｒ１アンタゴニスト |
| AU2004265189B2 (en) * | 2003-08-15 | 2010-03-04 | Banyu Pharmaceutical Co., Ltd. | Imidazopyridine derivatives |
| KR100747042B1 (ko) * | 2003-08-19 | 2007-08-07 | 솔젠트 (주) | 신물질６-메틸-３-펜에틸-３,４-디히드로-１ｈ-큐나졸린-２-티온,이의 제조방법 및 이를 유효성분으로 포함하는 미백 효능조성물 |
| WO2005042541A1 (en) * | 2003-10-23 | 2005-05-12 | Glaxo Group Limited | 3-(4-aminophenyl) thienopyrimid-4-one derivatives as mch r1 antagonists for the treatment of obesity, diabetes, depression and anxiety |
| US7592373B2 (en) | 2003-12-23 | 2009-09-22 | Boehringer Ingelheim International Gmbh | Amide compounds with MCH antagonistic activity and medicaments comprising these compounds |
| UA83416C2 (en) * | 2004-02-13 | 2008-07-10 | Баниу Фармасьютикал Ко., Лтд. | Fused ring 4-oxopyrimidine derivative |
| DE102004010893A1 (de) * | 2004-03-06 | 2005-09-22 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue ß-Ketoamid-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel |
| US7605176B2 (en) | 2004-03-06 | 2009-10-20 | Boehringer Ingelheim International Gmbh | β-ketoamide compounds with MCH antagonistic activity |
| US20080125403A1 (en) | 2004-04-02 | 2008-05-29 | Merck & Co., Inc. | Method of Treating Men with Metabolic and Anthropometric Disorders |
| US7524862B2 (en) | 2004-04-14 | 2009-04-28 | Boehringer Ingelheim International Gmbh | Alkyne compounds with MCH antagonistic activity and medicaments comprising these compounds |
| DE102004017934A1 (de) | 2004-04-14 | 2005-11-03 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Alkin-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel |
| US7902356B2 (en) | 2004-12-17 | 2011-03-08 | Eli Lilly And Company | Thiazolopyridinone derivates as MCH receptor antagonists |
| CN101155788A (zh) * | 2005-02-14 | 2008-04-02 | 万有制药株式会社 | 4(3h)-喹唑啉酮衍生物的晶体 |
| WO2006118320A1 (ja) | 2005-04-28 | 2006-11-09 | Takeda Pharmaceutical Company Limited | チエノピリミドン化合物 |
| WO2007011286A1 (en) * | 2005-07-15 | 2007-01-25 | Astrazeneca Ab | Therapeutic agents |
| ES2434946T3 (es) * | 2005-08-31 | 2013-12-18 | Celgene Corporation | Compuestos de isoindol imida y composiciones que los comprenden y métodos para usarlo |
| RU2418803C2 (ru) * | 2005-10-19 | 2011-05-20 | Киссеи Фармасьютикал Ко., Лтд. | Конденсированное гетероциклическое производное, содержащая его лечебная композиция и ее применение в медицине |
| US7745447B2 (en) * | 2005-10-26 | 2010-06-29 | Bristol-Myers Squibb Company | Substituted thieno[3,2-D]pyrimidines as non-basic melanin concentrating hormone receptor-1 antagonists |
| US8618115B2 (en) | 2005-10-26 | 2013-12-31 | Bristol-Myers Squibb Company | Substituted thieno[3,2-d]pyrimidinones as MCHR1 antagonists and methods for using them |
| ES2412007T3 (es) | 2005-12-21 | 2013-07-09 | Janssen Pharmaceutica, N.V. | Derivados de pirazinona sustituida novedosos para uso en enfermedades mediadas por MCH-1 |
| US7553836B2 (en) | 2006-02-06 | 2009-06-30 | Bristol-Myers Squibb Company | Melanin concentrating hormone receptor-1 antagonists |
| CN101384605A (zh) | 2006-02-15 | 2009-03-11 | 塞诺菲-安万特股份有限公司 | 新的氨基醇取代的芳基噻吩并嘧啶酮、其制备方法以及其作为药物的用途 |
| BRPI0707869A2 (pt) * | 2006-02-15 | 2011-05-10 | Sanofi Aventis | ariltienopirimidinonas substituÍdas com azaciclil, processo para a sua preparaÇço e seus usos como medicamentos |
| DE602007011897D1 (de) | 2006-02-15 | 2011-02-24 | Sanofi Aventis | Neue aminoalkohol-substituierte aryldihydroisochinolinone, herstellungsverfahren und ihre verwendung als medikamente |
| AU2007214709A1 (en) * | 2006-02-15 | 2007-08-23 | Sanofi-Aventis | Azacyclyl-substituted aryldihydroisoquinolinones, process for their preparation and their use as medicaments |
| WO2007142217A1 (ja) * | 2006-06-07 | 2007-12-13 | Banyu Pharmaceutical Co., Ltd. | １－フェニルピリドン誘導体 |
| WO2007146759A2 (en) | 2006-06-08 | 2007-12-21 | Eli Lilly And Company | Novel mch receptor antagonists |
| CA2652385A1 (en) * | 2006-06-08 | 2007-12-21 | Eli Lilly And Company | Novel mch receptor antagonists |
| BRPI0715160A2 (pt) | 2006-08-08 | 2013-06-11 | Sanofi Aventis | imidazolidina-2,4-dionas substituÍdas por arilamimoaril-alquil-, processo para preparÁ-las, medicamentos compeendendo estes compostos, e seu uso |
| EP2121703A4 (en) * | 2006-08-18 | 2011-12-28 | Astrazeneca Ab | THIENOPYRIMIDIN-4-ON- AND THIENOPYRIDAZIN-7-ONDERIVATES AS MCH-RL ANTAGONISTS |
| JP5290192B2 (ja) | 2006-12-05 | 2013-09-18 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | Ｍｃｈ−１に媒介される疾患における使用のための新規な置換されたジアザ−スピロ−ピリジノン誘導体 |
| KR20090082484A (ko) * | 2006-12-14 | 2009-07-30 | 일라이 릴리 앤드 캄파니 | 5-[4-(아제티딘-3-일옥시)-페닐]-2-페닐-5ｈ-티아졸로[5,4-ｃ]피리딘-4-온 유도체 및 ｍｃｈ 수용체 길항제로서의 이들의 용도 |
| NZ578096A (en) | 2007-01-10 | 2011-11-25 | Albany Molecular Res Inc | 5-pyridinone substituted indazoles |
| JP2010525077A (ja) | 2007-04-25 | 2010-07-22 | ブリストル−マイヤーズ スクイブ カンパニー | 非塩基性メラニン凝集ホルモン受容体−１アンタゴニスト |
| MX2009013293A (es) | 2007-06-04 | 2010-02-15 | Synergy Pharmaceuticals Inc | Agonistas de guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros trastornos. |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| DE102007028925A1 (de) | 2007-06-22 | 2008-12-24 | Saltigo Gmbh | Verfahren zur Herstellung von 2-Phenoxyacetalen und den daraus korrespondierenden 2-Phenoxycarbaldehyden |
| ES2382982T3 (es) | 2007-07-21 | 2012-06-15 | Albany Molecular Research, Inc. | Indazoles sustituidos con 5-piridinona y composiciones farmacéuticas de los mismos |
| WO2009072581A1 (ja) * | 2007-12-05 | 2009-06-11 | Aska Pharmaceutical Co., Ltd. | ラクタム化合物又はその塩及びｐｐａｒ活性化剤 |
| PE20091928A1 (es) * | 2008-05-29 | 2009-12-31 | Bristol Myers Squibb Co | Tienopirimidinas hidroxisustituidas como antagonistas de receptor-1 de hormona concentradora de melanina no basicos |
| EP2810951B1 (en) | 2008-06-04 | 2017-03-15 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| WO2010003624A2 (en) | 2008-07-09 | 2010-01-14 | Sanofi-Aventis | Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof |
| CA2730603C (en) | 2008-07-16 | 2019-09-24 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| EP2348857B1 (en) | 2008-10-22 | 2016-02-24 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| JP5557845B2 (ja) | 2008-10-31 | 2014-07-23 | メルク・シャープ・アンド・ドーム・コーポレーション | 糖尿病用剤として有用な新規環状ベンゾイミダゾール誘導体 |
| WO2010068601A1 (en) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof |
| CA2689707A1 (en) | 2009-11-16 | 2011-05-16 | Jean-Simon Diallo | Identification of the novel small molecule viral sensitizer vse1 using high-throughput screening |
| DK2470552T3 (en) | 2009-08-26 | 2014-02-17 | Sanofi Sa | NOVEL, CRYSTALLINE, heteroaromatic FLUORGLYCOSIDHYDRATER, MEDICINES COVERING THESE COMPOUNDS AND THEIR USE |
| AU2011218830B2 (en) | 2010-02-25 | 2014-07-24 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| WO2012036233A1 (ja) * | 2010-09-17 | 2012-03-22 | 塩野義製薬株式会社 | メラニン凝集ホルモン受容体アンタゴニスト活性を有する縮合へテロ環誘導体 |
| MX348131B (es) | 2011-02-25 | 2017-05-26 | Merck Sharp & Dohme | Novedosos derivados de azabencimidazol ciclico utiles como agentes antidiabeticos. |
| EP2766349B1 (de) | 2011-03-08 | 2016-06-01 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| WO2012120058A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit benzyl- oder heteromethylengruppen substituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120050A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8809325B2 (en) | 2011-03-08 | 2014-08-19 | Sanofi | Benzyl-oxathiazine derivatives substituted with adamantane and noradamantane, medicaments containing said compounds and use thereof |
| US8710050B2 (en) | 2011-03-08 | 2014-04-29 | Sanofi | Di and tri- substituted oxathiazine derivatives, method for the production, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| EP2683704B1 (de) | 2011-03-08 | 2014-12-17 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120056A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Tetrasubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120054A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683703B1 (de) | 2011-03-08 | 2015-05-27 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| KR101236188B1 (ko) * | 2011-03-10 | 2013-02-22 | 한국화학연구원 | 신규한 피롤로피리디논 유도체 및 그의 ｍｃｈ 수용체-1 관련 질환에 대한 치료학적 용도 |
| HUP1100241A3 (en) | 2011-05-06 | 2013-12-30 | Richter Gedeon Nyrt | Oxetane substituted pyrimidones |
| NO3175985T3 (enExample) | 2011-07-01 | 2018-04-28 | ||
| TWI622583B (zh) | 2011-07-01 | 2018-05-01 | 基利科學股份有限公司 | 作為離子通道調節劑之稠合雜環化合物 |
| WO2014022528A1 (en) | 2012-08-02 | 2014-02-06 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| WO2014130608A1 (en) | 2013-02-22 | 2014-08-28 | Merck Sharp & Dohme Corp. | Antidiabetic bicyclic compounds |
| WO2014139388A1 (en) | 2013-03-14 | 2014-09-18 | Merck Sharp & Dohme Corp. | Novel indole derivatives useful as anti-diabetic agents |
| JP2016514670A (ja) | 2013-03-15 | 2016-05-23 | シナジー ファーマシューティカルズ インコーポレイテッド | 他の薬物と組み合わせたグアニル酸シクラーゼ受容体アゴニスト |
| JP2016514671A (ja) | 2013-03-15 | 2016-05-23 | シナジー ファーマシューティカルズ インコーポレイテッド | グアニル酸シクラーゼのアゴニストおよびその使用 |
| EA201592263A1 (ru) | 2013-06-05 | 2016-05-31 | Синерджи Фармасьютикалз, Инк. | Ультрачистые агонисты гуанилатциклазы c, способ их получения и использования |
| WO2015051496A1 (en) | 2013-10-08 | 2015-04-16 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| BR112016028404A2 (pt) | 2014-06-05 | 2018-07-03 | Bayer Cropscience Aktiengesellschaft | compostos bicíclicos como pesticidas |
| JP7114076B2 (ja) | 2015-12-22 | 2022-08-08 | シャイ・セラピューティクス・エルエルシー | がん及び炎症性疾患の処置のための化合物 |
| EP3497089B1 (de) * | 2016-08-12 | 2020-07-29 | Bayer CropScience Aktiengesellschaft | Verfahren zur herstellung von 4-substituierten 2,3-dihydro-1-benzofuranderivaten durch zyklisierung von 2-(2-diazonium-6-substituierten-phenyl)ethanol salzen |
| EP3509588B1 (en) | 2016-09-12 | 2023-06-07 | Integral Health,Inc. | Bicyclic compounds useful as gpr120 modulators |
| KR102537985B1 (ko) | 2016-09-12 | 2023-05-30 | 인테그랄 헬스 인코퍼레이티드 | Gpr120 조정제로서 유용한 단환형 화합물 |
| US11072602B2 (en) | 2016-12-06 | 2021-07-27 | Merck Sharp & Dohme Corp. | Antidiabetic heterocyclic compounds |
| EP3558298B1 (en) | 2016-12-20 | 2026-03-11 | Merck Sharp & Dohme LLC | Antidiabetic spirochroman compounds |
| CA3066939A1 (en) | 2017-06-21 | 2018-12-27 | SHY Therapeutics LLC | Compounds that interact with the ras superfamily for the treatment of cancers, inflammatory diseases, rasopathies, and fibrotic disease |
| AR112840A1 (es) | 2017-09-29 | 2019-12-18 | Bayer Ag | 3- fenilquinazolin-4(3h)-onas sustituidas y sus usos |
| WO2019063708A1 (en) | 2017-09-29 | 2019-04-04 | Bayer Aktiengesellschaft | SUBSTITUTED 3-PHENYLQUINAZOLIN-4 (3H) -ONES AND USES THEREOF |
| EP3898609A1 (en) | 2018-12-19 | 2021-10-27 | Shy Therapeutics LLC | Compounds that interact with the ras superfamily for the treatment of cancers, inflammatory diseases, rasopathies, and fibrotic disease |
| CN110563730B (zh) * | 2019-07-29 | 2022-03-25 | 江苏理工学院 | 高纯度n10-三氟乙酰蝶酸的制备方法 |
| EP4204418A1 (en) | 2020-08-28 | 2023-07-05 | Arvinas Operations, Inc. | Rapidly accelerating fibrosarcoma protein degrading compounds and associated methods of use |
| CN113651800B (zh) * | 2021-09-07 | 2022-08-19 | 山东铂源药业股份有限公司 | 一种甲磺酸奥希替尼的制备方法 |
| EP4584258A1 (en) | 2022-09-07 | 2025-07-16 | Arvinas Operations, Inc. | Rapidly accelerated fibrosarcoma (raf) degrading compounds and associated methods of use |
Family Cites Families (3)
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|---|---|---|---|---|
| PL137227B2 (en) * | 1984-03-28 | 1986-05-31 | Univ Lodzki | Process for preparing novel n-/dialkylaminoalkoxyphenyl/-imides of tetrahydrophtalic acids |
| DE69723869T2 (de) * | 1996-12-31 | 2004-04-22 | Dr. Reddy's Laboratories Ltd. | Heterozyklische verbindungen, verfahren zu ihrer herstellung, pharmazeutische zusammensetzungen die diese enthalten und ihre anwendung in der behandlung von diabetis und verwandten krankheiten |
| US7115750B1 (en) * | 1999-09-20 | 2006-10-03 | Takeda Pharmaceutical Company Limited | Melanin concentrating hormone antagonist |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8381 | Inventor (new situation) |
Inventor name: ARMSTRONG, ANNE, SULA, CAMBRIDGE, CAMBRIDGESHI, GB Inventor name: HAMPRECHT, WOLFGANG, DIETER, 37135 VERONA, IT Inventor name: JONES, MARTIN, HARLOW, ESSEX CM 19 5AW, GB Inventor name: WITTY, RICHARD, DAVID, HARLOW, ESSEX CM 19 5AW, GB Inventor name: AL-BARAZANJI, A., KAMAL, RESEARCH TRIANGLE PAR, US Inventor name: TADAYYON, MOHAMMAD, ST. ANDREW STREET, HERTFOR, GB |
|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |