JP5749272B2 - 糖尿病処置のために有用なｈｓｌ阻害剤としてのスピロ−縮合シクロヘキサン誘導体 - Google Patents

糖尿病処置のために有用なｈｓｌ阻害剤としてのスピロ−縮合シクロヘキサン誘導体 Download PDF

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JP5749272B2
JP5749272B2 JP2012533604A JP2012533604A JP5749272B2 JP 5749272 B2 JP5749272 B2 JP 5749272B2 JP 2012533604 A JP2012533604 A JP 2012533604A JP 2012533604 A JP2012533604 A JP 2012533604A JP 5749272 B2 JP5749272 B2 JP 5749272B2
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spiro
aza
hydroxy
phenyl
decan
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JP2013507421A (ja
Inventor
アッカーマン，ジャン
ブルッガー，シュテファン
コンテ，オーレリア
フンツィカー，ダニエル
ナイトハルト，ヴェルナー
ネッテコフェン，マティアス
シュルツ−ガーシュ，ターニャ
ウェルトハイマー，スタンレー
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F Hoffmann La Roche AG
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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
    • C07D209/54—Spiro-condensed
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • 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
    • 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
    • A61P3/06—Antihyperlipidemics
    • 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
    • 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
    • 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
    • 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
    • C07D401/06—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 only aliphatic carbon atoms
    • 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
    • C07D401/12—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 chain containing hetero atoms as chain links
    • 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
    • C07D403/12—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 chain containing hetero atoms as chain links
    • 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
    • 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
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Diabetes (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Epidemiology (AREA)
  • Endocrinology (AREA)
  • Emergency Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Vascular Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
JP2012533604A 2009-10-15 2010-10-12 糖尿病処置のために有用なｈｓｌ阻害剤としてのスピロ−縮合シクロヘキサン誘導体 Expired - Fee Related JP5749272B2 (ja)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP09173178 2009-10-15
EP09173178.6 2009-10-15
PCT/EP2010/065232 WO2011045292A1 (en) 2009-10-15 2010-10-12 Spiro-condensed cyclohexane derivatives as hsl inhibitors useful for the treatment of diabetes

Publications (2)

Publication Number Publication Date
JP2013507421A JP2013507421A (ja) 2013-03-04
JP5749272B2 true JP5749272B2 (ja) 2015-07-15

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JP2012533604A Expired - Fee Related JP5749272B2 (ja) 2009-10-15 2010-10-12 糖尿病処置のために有用なｈｓｌ阻害剤としてのスピロ−縮合シクロヘキサン誘導体

Country Status (20)

Country Link
US (1) US8440710B2 (enExample)
EP (1) EP2488493B1 (enExample)
JP (1) JP5749272B2 (enExample)
KR (1) KR101576328B1 (enExample)
CN (1) CN102858743B (enExample)
AR (1) AR078619A1 (enExample)
AU (1) AU2010305859A1 (enExample)
BR (1) BR112012008962A2 (enExample)
CA (1) CA2776457A1 (enExample)
CL (1) CL2012000937A1 (enExample)
ES (1) ES2538005T3 (enExample)
IL (1) IL218958A0 (enExample)
IN (1) IN2012DN03337A (enExample)
MX (1) MX2012004311A (enExample)
PE (1) PE20121732A1 (enExample)
PH (1) PH12012500630A1 (enExample)
RU (1) RU2607080C2 (enExample)
TW (1) TW201118068A (enExample)
WO (1) WO2011045292A1 (enExample)
ZA (1) ZA201202613B (enExample)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014508178A (ja) * 2011-03-16 2014-04-03 エフ．ホフマン−ラ ロシュ アーゲー 糖尿病治療のためのｈｓｌ阻害剤としてのｓｅｃ−ヒドロキシシクロヘキシル誘導体
JP2014508179A (ja) * 2011-03-17 2014-04-03 エフ．ホフマン−ラ ロシュ アーゲー 新規なアザスピロデカノン化合物
JP2014509620A (ja) * 2011-03-25 2014-04-21 エフ．ホフマン−ラ ロシュ アーゲー Ｈｓｌ阻害剤としての新規なアザスピロデカノン化合物

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SG184767A1 (en) 2009-03-23 2012-10-30 Glenmark Pharmaceuticals Sa Furopyrimidinedione derivatives as trpa1 modulators
US8097634B2 (en) * 2010-04-15 2012-01-17 Hoffmann-La Roche Inc. Azacyclic derivatives
CN103319395B (zh) * 2013-04-08 2014-09-24 武汉罗化科技有限公司 一种4-氟靛红的工业化制备方法及其产品
WO2015103756A1 (en) 2014-01-09 2015-07-16 Merck Sharp & Dohme Corp. Inhibitors of the renal outer medullary potassium channel
UY36060A (es) 2014-04-02 2015-10-30 Bayer Pharma AG Compuestos de azol sustituidos con amida
PE20201170A1 (es) 2017-11-01 2020-10-28 Bristol Myers Squibb Co Compuestos biciclicos en puente como moduladores del receptor farnesoide x
BR112020008157A2 (pt) 2017-11-01 2020-10-06 Bristol-Myers Squibb Company compostos espirocíclicos como moduladores do receptor farnesoide x
KR102731925B1 (ko) 2017-11-01 2024-11-18 브리스톨-마이어스 스큅 컴퍼니 파르네소이드 x 수용체 조정제로서의 멀티시클릭 화합물
WO2019089670A1 (en) 2017-11-01 2019-05-09 Bristol-Myers Squibb Company Alkene compounds as farnesoid x receptor modulators
AU2018360575A1 (en) 2017-11-01 2020-06-18 Bristol-Myers Squibb Company Alkene spirocyclic compounds as farnesoid X receptor modulators
CN109369354B (zh) * 2018-12-15 2021-07-09 浦拉司科技（上海）有限责任公司 一种4,4,4-三氟丁醇的合成方法
WO2020168149A1 (en) 2019-02-15 2020-08-20 Bristol-Myers Squibb Company Substituted amide compounds useful as farnesoid x receptor modulators
EP3924329A2 (en) 2019-02-15 2021-12-22 Bristol-Myers Squibb Company Substituted amide compounds useful as farnesoid x receptor modulators
AR118050A1 (es) 2019-02-15 2021-09-15 Bristol Myers Squibb Co Compuestos bicíclicos sustituidos como moduladores del receptor farnesoide x
CA3129619A1 (en) 2019-02-15 2020-08-20 Bristol-Myers Squibb Company Substituted amide compounds useful as farnesoid x receptor modulators
CN117567380B (zh) * 2023-11-17 2025-10-17 广东药科大学附属第一医院 三唑类hsl抑制剂、制备方法及其用途

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10247680B4 (de) * 2002-10-12 2005-09-01 Aventis Pharma Deutschland Gmbh Neue bicyclische Inhibitoren der Hormon Sensitiven Lipase
US7320992B2 (en) 2003-08-25 2008-01-22 Amgen Inc. Substituted 2,3-dihydro-1h-isoindol-1-one derivatives and methods of use
AU2004303609A1 (en) 2003-12-16 2005-07-07 Pfizer Products Inc. Pyrido[2,3-d]pyrimidine-2,4-diamines as PDE 2 inhibitors
FR2870538B1 (fr) * 2004-05-19 2006-07-14 Servier Lab Nouveaux derives de pyrrolidines et de thiazolidines, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
WO2007103719A2 (en) 2006-03-03 2007-09-13 Incyte Corporation MODULATORS OF 11-β HYDROXYL STEROID DEHYDROGENASE TYPE 1, PHARMACEUTICAL COMPOSITIONS THEREOF, AND METHODS OF USING THE SAME
PL2021337T3 (pl) * 2006-04-25 2010-06-30 Lilly Co Eli Inhibitory dehydrogenazy 11-beta-hydroksysteroidowej typu 1
WO2007127763A2 (en) 2006-04-25 2007-11-08 Eli Lilly And Company Inhibitors of 11-beta-hydroxysteroid dehydrogenase 1
GB0705656D0 (en) 2007-03-23 2007-05-02 Addex Pharmaceuticals Sa Novel compounds E1

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014508178A (ja) * 2011-03-16 2014-04-03 エフ．ホフマン−ラ ロシュ アーゲー 糖尿病治療のためのｈｓｌ阻害剤としてのｓｅｃ−ヒドロキシシクロヘキシル誘導体
JP2014508179A (ja) * 2011-03-17 2014-04-03 エフ．ホフマン−ラ ロシュ アーゲー 新規なアザスピロデカノン化合物
JP2014509620A (ja) * 2011-03-25 2014-04-21 エフ．ホフマン−ラ ロシュ アーゲー Ｈｓｌ阻害剤としての新規なアザスピロデカノン化合物

Also Published As

Publication number Publication date
EP2488493A1 (en) 2012-08-22
HK1179957A1 (en) 2013-10-11
RU2012119706A (ru) 2013-11-20
RU2607080C2 (ru) 2017-01-10
US8440710B2 (en) 2013-05-14
WO2011045292A1 (en) 2011-04-21
IL218958A0 (en) 2012-06-28
JP2013507421A (ja) 2013-03-04
AU2010305859A1 (en) 2012-06-07
US20110092512A1 (en) 2011-04-21
CN102858743A (zh) 2013-01-02
CL2012000937A1 (es) 2012-09-14
EP2488493B1 (en) 2015-04-15
MX2012004311A (es) 2012-04-30
KR20120074304A (ko) 2012-07-05
IN2012DN03337A (enExample) 2015-10-23
PH12012500630A1 (en) 2012-10-22
BR112012008962A2 (pt) 2019-09-24
CN102858743B (zh) 2015-06-10
PE20121732A1 (es) 2012-12-28
AR078619A1 (es) 2011-11-23
ZA201202613B (en) 2013-01-30
ES2538005T3 (es) 2015-06-16
KR101576328B1 (ko) 2015-12-10
TW201118068A (en) 2011-06-01
CA2776457A1 (en) 2011-04-21

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