JP5824517B2 - 二環性化合物 - Google Patents
二環性化合物 Download PDFInfo
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- JP5824517B2 JP5824517B2 JP2013524677A JP2013524677A JP5824517B2 JP 5824517 B2 JP5824517 B2 JP 5824517B2 JP 2013524677 A JP2013524677 A JP 2013524677A JP 2013524677 A JP2013524677 A JP 2013524677A JP 5824517 B2 JP5824517 B2 JP 5824517B2
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- -1 Bicyclic compound Chemical class 0.000 title description 290
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- 125000001424 substituent group Chemical group 0.000 claims description 224
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- 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
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- 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
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- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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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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- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D405/04—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
- 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
- C07D417/02—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 two hetero rings
- C07D417/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Endocrinology (AREA)
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- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Neurology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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| Application Number | Priority Date | Filing Date | Title |
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| JP2013524677A JP5824517B2 (ja) | 2010-11-30 | 2011-11-29 | 二環性化合物 |
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| PCT/JP2011/078010 WO2012074126A1 (en) | 2010-11-30 | 2011-11-29 | Bicyclic compound |
| JP2013524677A JP5824517B2 (ja) | 2010-11-30 | 2011-11-29 | 二環性化合物 |
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Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201206911A (en) | 2010-04-27 | 2012-02-16 | Takeda Pharmaceutical | Bicyclic compound |
| CA2853221A1 (en) | 2011-10-24 | 2013-05-02 | Tohru Yamashita | Bicyclic compound |
| WO2014088983A1 (en) | 2012-12-07 | 2014-06-12 | Merck Sharp & Dohme Corp. | Regioselective n-2 arylation of indazoles |
| PL403149A1 (pl) * | 2013-03-14 | 2014-09-15 | Celon Pharma Spółka Akcyjna | Nowe związki pochodne pirazolilobenzo[d]imidazolu |
| HK1221411A1 (zh) * | 2013-05-10 | 2017-06-02 | Gilead Apollo, Inc. | Acc抑制剂和其用途 |
| CN105358143B (zh) | 2013-05-10 | 2019-01-22 | 吉利德阿波罗公司 | Acc抑制剂和其用途 |
| HK1221420A1 (zh) | 2013-05-10 | 2017-06-02 | Gilead Apollo, Inc. | Acc抑制剂和其用途 |
| KR20160007598A (ko) | 2013-05-10 | 2016-01-20 | 님버스 아폴로, 인코포레이티드 | Acc 억제제 및 이의 용도 |
| HK1217448A1 (zh) | 2013-09-12 | 2017-01-13 | 辉瑞大药厂 | 乙酰辅酶a羧化酶抑制剂用於治疗寻常痤疮的用途 |
| US10011609B2 (en) | 2013-11-14 | 2018-07-03 | Cadila Healthcare Limited | Heterocyclic compounds |
| MY195016A (en) | 2014-08-04 | 2023-01-03 | Nuevolution As | Optionally Fused Heterocyclyl-Substituted Derivatives of Pyrimidine Useful for The Treatment of Inflammatory, Metabolic, Oncologic and Autoimmune Diseases |
| CN104193731B (zh) * | 2014-08-27 | 2017-03-15 | 广东东阳光药业有限公司 | 一种脲取代联苯类化合物及其组合物及用途 |
| US10479802B2 (en) | 2014-08-29 | 2019-11-19 | Chdi Foundation, Inc. | Probes for imaging huntingtin protein |
| JP2016079168A (ja) * | 2014-10-17 | 2016-05-16 | 塩野義製薬株式会社 | ９員縮合環誘導体 |
| CN104447725B (zh) * | 2014-10-22 | 2018-02-02 | 浙江大学 | 一种手性含亚胺吡啶噁唑啉的化合物及其制备方法 |
| US9586949B2 (en) | 2015-02-09 | 2017-03-07 | Incyte Corporation | Aza-heteroaryl compounds as PI3K-gamma inhibitors |
| DK3355699T3 (da) | 2015-09-29 | 2021-06-07 | Onco Therapy Science Inc | Bicyklisk forbindelse og anvendelse deraf til inhibering af suv39h2 |
| CN105601626A (zh) * | 2015-11-04 | 2016-05-25 | 浙江大学 | 一种含2-取代噁唑啉衍生物的制备方法 |
| TWI744256B (zh) | 2015-11-06 | 2021-11-01 | 美商英塞特公司 | 作為ＰＩ３Ｋ-γ抑制劑之雜環化合物 |
| AR107293A1 (es) | 2016-01-05 | 2018-04-18 | Incyte Corp | COMPUESTOS DE PIRIDINA Y PIRIDIMINA COMO INHIBIDORES DE PI3K-g |
| US10138248B2 (en) | 2016-06-24 | 2018-11-27 | Incyte Corporation | Substituted imidazo[2,1-f][1,2,4]triazines, substituted imidazo[1,2-a]pyridines, substituted imidazo[1,2-b]pyridazines and substituted imidazo[1,2-a]pyrazines as PI3K-γ inhibitors |
| CA3060715C (en) | 2017-04-24 | 2024-10-01 | Tesaro, Inc. | PROCESSES FOR MANUFACTURING NIRAPARIB |
| MD3697789T2 (ro) | 2017-10-18 | 2022-02-28 | Incyte Corp | Derivați imidazol condensați substituiți cu grupări hidroxi terțiare ca inhibitori PI3K-GAMA |
| CR20250050A (es) | 2018-09-05 | 2025-03-19 | Incyte Corp | Formas cristalinas de un inhibidor de fosfoinositida 3–quinasa (pi3k) (divisional 2021-0165) |
| US11447479B2 (en) | 2019-12-20 | 2022-09-20 | Nuevolution A/S | Compounds active towards nuclear receptors |
| TWI872177B (zh) | 2019-12-20 | 2025-02-11 | 丹麥商紐韋盧森公司 | 對核受體具有活性之化合物 |
| US11613532B2 (en) | 2020-03-31 | 2023-03-28 | Nuevolution A/S | Compounds active towards nuclear receptors |
| MX2022012260A (es) | 2020-03-31 | 2022-11-30 | Nuevolution As | Compuestos activos frente a receptores nucleares. |
| EP4434520A4 (en) | 2021-11-19 | 2025-10-29 | Shionogi & Co | PHARMACEUTICAL PRODUCT FOR THE TREATMENT OF HEART DISEASE OR SKELETAL MUSCLE DISEASE |
| AR129265A1 (es) | 2022-05-12 | 2024-08-07 | Syngenta Crop Protection Ag | Compuestos de alcoxi-heteroaril-carboxamida o tioamida |
| WO2024033374A1 (en) | 2022-08-11 | 2024-02-15 | Syngenta Crop Protection Ag | Novel arylcarboxamide or arylthioamide compounds |
| WO2024126650A1 (en) | 2022-12-15 | 2024-06-20 | Syngenta Crop Protection Ag | Novel bicyclic-carboxamide compounds useful as pesticides |
Family Cites Families (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU6944296A (en) | 1995-09-13 | 1997-04-01 | Takeda Chemical Industries Ltd. | Benzoxazepine compounds, their production and use as lipid lowering agents |
| JP2002501503A (ja) * | 1997-04-30 | 2002-01-15 | イーライ・リリー・アンド・カンパニー | 抗血栓症剤 |
| AR035016A1 (es) | 1999-08-25 | 2004-04-14 | Takeda Chemical Industries Ltd | Composicion de azol promotor de produccion/secrecion de neurotrofina, compuesto prodroga del mismo, composicion farmaceutica que lo comprende y uso del mismo para preparar esta ultima. |
| EP1285651B1 (en) | 2000-04-28 | 2010-09-01 | Takeda Pharmaceutical Company Limited | Melanin concentrating hormone antagonists |
| WO2001087834A1 (en) | 2000-05-16 | 2001-11-22 | Takeda Chemical Industries, Ltd. | Melanin-concentrating hormone antagonist |
| EP1302462A4 (en) | 2000-07-17 | 2007-07-18 | Takeda Pharmaceutical | SULFONATE DERIVATIVES, PROCESS FOR PRODUCTION AND USE THEREOF |
| DK1542997T3 (da) * | 2002-07-24 | 2012-06-25 | Dermira Canada Inc | Pyrazolylbenzothiazolderivater og deres anvendelse som terapeutiske midler |
| CA2504511A1 (en) | 2002-11-01 | 2004-05-13 | Takeda Pharmaceutical Company Limited | Agent for preventing or treating neuropathy |
| EP1559422B1 (en) | 2002-11-08 | 2014-04-30 | Takeda Pharmaceutical Company Limited | Receptor function controlling agent |
| EP1564213A4 (en) | 2002-11-22 | 2009-05-27 | Takeda Pharmaceutical | IMIDAZOLE DERIVATIVE, METHOD FOR THE PRODUCTION AND USE THEREOF |
| WO2004106276A1 (ja) | 2003-05-30 | 2004-12-09 | Takeda Pharmaceutical Company Limited | 縮合環化合物 |
| US7534887B2 (en) | 2003-09-30 | 2009-05-19 | Takeda Pharmaceutical Company Limited | Thiazoline derivative and use of the same |
| CA2550012A1 (en) | 2003-12-17 | 2005-06-30 | Takeda Pharmaceutical Company Limited | Urea derivative, process for producing the same and use |
| RU2006126978A (ru) | 2003-12-25 | 2008-01-27 | Такеда Фармасьютикал Компани Лимитед (Jp) | Производные 3-(4-бензилоксифенил)пропановой кислоты |
| JP4855777B2 (ja) | 2003-12-26 | 2012-01-18 | 武田薬品工業株式会社 | フェニルプロパン酸誘導体 |
| WO2005087710A1 (ja) | 2004-03-15 | 2005-09-22 | Takeda Pharmaceutical Company Limited | アミノフェニルプロパン酸誘導体 |
| JP4859665B2 (ja) | 2004-03-30 | 2012-01-25 | 武田薬品工業株式会社 | アルコキシフェニルプロパン酸誘導体 |
| TWI396686B (zh) | 2004-05-21 | 2013-05-21 | Takeda Pharmaceutical | 環狀醯胺衍生物、以及其製品和用法 |
| JP5094394B2 (ja) | 2005-04-20 | 2012-12-12 | 武田薬品工業株式会社 | 縮合複素環化合物 |
| WO2007013694A1 (ja) | 2005-07-29 | 2007-02-01 | Takeda Pharmaceutical Company Limited | フェノキシアルカン酸化合物 |
| WO2007013689A1 (ja) | 2005-07-29 | 2007-02-01 | Takeda Pharmaceutical Company Limited | シクロプロパンカルボン酸化合物 |
| PE20070338A1 (es) | 2005-08-10 | 2007-04-16 | Takeda Pharmaceutical | Derivados heterociclicos como agentes terapeuticos para diabetes |
| JP2007063225A (ja) | 2005-09-01 | 2007-03-15 | Takeda Chem Ind Ltd | イミダゾピリジン化合物 |
| JP5291471B2 (ja) * | 2006-02-15 | 2013-09-18 | アボット・ラボラトリーズ | 新規なアセチル−ＣｏＡカルボキシラーゼ（ＡＣＣ）阻害薬およびこれらの糖尿病、肥満および代謝症候群における使用 |
| RS53230B (sr) | 2006-06-27 | 2014-08-29 | Takeda Pharmaceutical Company Limited | Kondenzovana ciklična jedinjenja kao modulatori gpr40 receptora |
| JP5306818B2 (ja) | 2006-10-18 | 2013-10-02 | 武田薬品工業株式会社 | 縮合複素環化合物 |
| AU2007310064B2 (en) | 2006-10-19 | 2013-03-28 | Takeda Pharmaceutical Company Limited | Indole compound |
| WO2008093639A1 (ja) | 2007-01-29 | 2008-08-07 | Takeda Pharmaceutical Company Limited | ピラゾール化合物 |
| MX2009008103A (es) | 2007-02-09 | 2009-08-18 | Takeda Pharmaceutical | Compuestos anulares fusionados como agonistas parciales de prar-gamma. |
| JPWO2008136428A1 (ja) | 2007-04-27 | 2010-07-29 | 武田薬品工業株式会社 | 含窒素５員複素環化合物 |
| EP2157859A4 (en) | 2007-06-19 | 2011-01-12 | Takeda Pharmaceutical | INDAZOL COMPOUNDS FOR THE ACTIVATION OF GLUCCOKINASE |
| JP5535931B2 (ja) * | 2008-10-27 | 2014-07-02 | 武田薬品工業株式会社 | 二環性化合物 |
| US8927576B2 (en) * | 2009-04-06 | 2015-01-06 | PTC Therpeutics, Inc. | HCV inhibitor and therapeutic agent combinations |
| TW201206911A (en) | 2010-04-27 | 2012-02-16 | Takeda Pharmaceutical | Bicyclic compound |
| WO2012108478A1 (ja) | 2011-02-09 | 2012-08-16 | 武田薬品工業株式会社 | 単環化合物 |
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- 2011-11-29 KR KR1020137016850A patent/KR20140001965A/ko not_active Withdrawn
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- 2011-11-29 UY UY0001033756A patent/UY33756A/es not_active Application Discontinuation
- 2011-11-29 CA CA2819400A patent/CA2819400A1/en not_active Abandoned
- 2011-11-29 MX MX2013006113A patent/MX2013006113A/es not_active Application Discontinuation
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- 2013-06-05 MA MA35965A patent/MA34713B1/fr unknown
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- 2013-06-24 CO CO13149620A patent/CO6751239A2/es not_active Application Discontinuation
- 2013-06-25 EC ECSP13012719 patent/ECSP13012719A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CL2013001520A1 (es) | 2013-10-18 |
| MA34713B1 (fr) | 2013-12-03 |
| WO2012074126A1 (en) | 2012-06-07 |
| PH12013501099A1 (en) | 2013-07-08 |
| ECSP13012719A (es) | 2013-12-31 |
| BR112013013417A2 (pt) | 2019-09-24 |
| EA201390794A1 (ru) | 2013-11-29 |
| ES2536319T3 (es) | 2015-05-22 |
| US20120142714A1 (en) | 2012-06-07 |
| AU2011337565A2 (en) | 2013-07-11 |
| CO6751239A2 (es) | 2013-09-16 |
| AU2011337565A1 (en) | 2013-07-11 |
| CR20130281A (es) | 2013-10-07 |
| US8729102B2 (en) | 2014-05-20 |
| EP2649062A1 (en) | 2013-10-16 |
| WO2012074126A9 (en) | 2013-06-06 |
| CN103347872A (zh) | 2013-10-09 |
| MX2013006113A (es) | 2013-11-01 |
| PE20140161A1 (es) | 2014-02-19 |
| SG190925A1 (en) | 2013-07-31 |
| UY33756A (es) | 2012-06-29 |
| CN103347872B (zh) | 2014-12-24 |
| DOP2013000118A (es) | 2013-09-30 |
| CA2819400A1 (en) | 2012-06-07 |
| EP2649062B1 (en) | 2015-04-08 |
| KR20140001965A (ko) | 2014-01-07 |
| AR084032A1 (es) | 2013-04-17 |
| JP2013545718A (ja) | 2013-12-26 |
| TW201242951A (en) | 2012-11-01 |
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