CA2598087C - 5-[4-(4-(2-amino-2 methoxycarbonylethyl)phenoxy)benzilidene]thiazolidin-2,4-dione derivatives and related compounds for reducing glucose, cholesterol and triglyceride levels in plasma - Google Patents

5-[4-(4-(2-amino-2 methoxycarbonylethyl)phenoxy)benzilidene]thiazolidin-2,4-dione derivatives and related compounds for reducing glucose, cholesterol and triglyceride levels in plasma Download PDF

Info

Publication number
CA2598087C
CA2598087C CA2598087A CA2598087A CA2598087C CA 2598087 C CA2598087 C CA 2598087C CA 2598087 A CA2598087 A CA 2598087A CA 2598087 A CA2598087 A CA 2598087A CA 2598087 C CA2598087 C CA 2598087C
Authority
CA
Canada
Prior art keywords
compound according
amino
thiazolidin
phenyl
compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
CA2598087A
Other languages
English (en)
French (fr)
Other versions
CA2598087A1 (en
Inventor
Bishwajit Nag
Abhijeet Nag
Debendranath Dey
Shiv Kumar Agarwal
Partha Neogi
Gaddam Om Reddy
Sangamesh Badiger
Gajendra Singh
Surendra Kumar Pandey
Santhanagopalan Chithra
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bexel Pharmaceuticals Inc
Original Assignee
Bexel Pharmaceuticals Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bexel Pharmaceuticals Inc filed Critical Bexel Pharmaceuticals Inc
Publication of CA2598087A1 publication Critical patent/CA2598087A1/en
Application granted granted Critical
Publication of CA2598087C publication Critical patent/CA2598087C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • 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
    • A61K31/41—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
    • A61K31/4164—1,3-Diazoles
    • 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
    • A61K31/41—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
    • A61K31/42—Oxazoles
    • A61K31/421—1,3-Oxazoles, e.g. pemoline, trimethadione
    • 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
    • A61K31/41—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
    • A61K31/425—Thiazoles
    • A61K31/426—1,3-Thiazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • 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
    • A61P3/06—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
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • 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
    • 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
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/34—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/36—Sulfur atoms

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Diabetes (AREA)
  • Immunology (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Urology & Nephrology (AREA)
  • Endocrinology (AREA)
  • Transplantation (AREA)
  • Vascular Medicine (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Ophthalmology & Optometry (AREA)
  • Child & Adolescent Psychology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Emergency Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
CA2598087A 2005-02-17 2006-02-17 5-[4-(4-(2-amino-2 methoxycarbonylethyl)phenoxy)benzilidene]thiazolidin-2,4-dione derivatives and related compounds for reducing glucose, cholesterol and triglyceride levels in plasma Expired - Fee Related CA2598087C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
IN347DE2005 2005-02-17
IN347/DEL/2005 2005-02-17
US11/096,718 2005-03-31
US11/096,718 US7521465B2 (en) 2003-01-17 2005-03-31 Diphenyl ether derivatives
PCT/US2006/005846 WO2006089225A1 (en) 2005-02-17 2006-02-17 5- [4- (4- (2 -amino- 2 -methoxycarbonylethyl) phenoxy) benzilidene] thiazolidin-2 , 4-dion e derivatives and related compounds for reducing glucose, cholesterol and triglyceride levels in plasma

Publications (2)

Publication Number Publication Date
CA2598087A1 CA2598087A1 (en) 2006-08-24
CA2598087C true CA2598087C (en) 2014-05-27

Family

ID=36570583

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2598087A Expired - Fee Related CA2598087C (en) 2005-02-17 2006-02-17 5-[4-(4-(2-amino-2 methoxycarbonylethyl)phenoxy)benzilidene]thiazolidin-2,4-dione derivatives and related compounds for reducing glucose, cholesterol and triglyceride levels in plasma

Country Status (9)

Country Link
US (1) US7521465B2 (enExample)
EP (1) EP1848700B1 (enExample)
JP (1) JP5134974B2 (enExample)
KR (1) KR20070105364A (enExample)
CA (1) CA2598087C (enExample)
ES (1) ES2566337T3 (enExample)
HU (1) HUE028882T2 (enExample)
PL (1) PL1848700T3 (enExample)
WO (1) WO2006089225A1 (enExample)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9969980B2 (en) * 2001-09-21 2018-05-15 Garnet Biotherapeutics Cell populations which co-express CD49c and CD90
US9969977B2 (en) * 2002-09-20 2018-05-15 Garnet Biotherapeutics Cell populations which co-express CD49c and CD90
US7521465B2 (en) 2003-01-17 2009-04-21 Bexel Pharmaceuticals, Inc. Diphenyl ether derivatives
US7781464B2 (en) * 2003-01-17 2010-08-24 Bexel Pharmaceuticals, Inc. Heterocyclic diphenyl ethers
US7087576B2 (en) * 2003-10-07 2006-08-08 Bexel Pharmaceuticals, Inc. Dipeptide phenyl ethers
KR100814109B1 (ko) 2006-01-09 2008-03-14 한국생명공학연구원 로다닌 유도체, 이의 제조방법 및 이를 유효성분으로함유하는 약학적 조성물
US7989480B2 (en) * 2006-08-04 2011-08-02 Decode Genetics Ehf Aryl amino acid derivatives as inhibitors for treating inflammation
US20090069313A1 (en) * 2007-09-06 2009-03-12 Orchid Research Laboratories Ltd. Novel MAO-A inhibitors
ATE536347T1 (de) 2008-05-20 2011-12-15 Merck Sharp & Dohme Effiziente herstellung heterologer proteine unter verwendung von mannosyltransferaseinhibitoren
US20140187594A1 (en) 2010-07-28 2014-07-03 Orchid Chemicals And Pharmaceuticals Ltd Diphenyl ether compounds for the treatment of liver, lung disorders, diabetic complications and cardiovascular diseases
WO2012153775A1 (ja) 2011-05-10 2012-11-15 国立大学法人神戸大学 Ras機能阻害作用を有するチオキソチアゾリジン誘導体
EP4029859A1 (en) 2014-11-21 2022-07-20 Bsim Therapeutics, S.A. 2-oxothiazolidin-4-one derivatives active as transthyretin ligands and uses thereof
TW202019923A (zh) * 2018-07-16 2020-06-01 義大利商吉斯藥品公司 作為Rho-激酶抑制劑之酪胺酸醯胺衍生物

Family Cites Families (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0228168A (ja) * 1988-04-14 1990-01-30 Sankyo Co Ltd チアゾール誘導体
US20020049240A1 (en) 1994-12-19 2002-04-25 Beecham Group P.1.C. Novel compounds
US5166137A (en) 1991-03-27 1992-11-24 Nobipols Forskningsstiftelse Guluronic acid polymers and use of same for inhibition of cytokine production
US5441971A (en) 1991-04-11 1995-08-15 The Upjohn Company Thiazolidinedione derivatives, production and use thereof
TW268952B (enExample) 1993-02-26 1996-01-21 Takeda Pharm Industry Co Ltd
US5527546A (en) 1994-08-10 1996-06-18 Bayer Corporation Human interleukin 6 inhibitor
ATE271128T1 (de) 1995-05-11 2004-07-15 Applied Research Systems Inhibitoren der il-6 aktivitaet
TW577875B (en) 1997-01-31 2004-03-01 Shionogi & Co Pyrrolidine derivatives with inhibitory activity for phospholipase A2
US6331633B1 (en) 1998-05-08 2001-12-18 Calyx Therapeutics Inc. Heterocyclic analogs of diphenylethylene compounds
US6699896B1 (en) 1998-05-12 2004-03-02 Wyeth Oxazole-aryl-carboxylic acids useful in the treatment of insulin resistance and hyperglycemia
EP1082323A2 (en) 1998-06-05 2001-03-14 AstraZeneca UK Limited Oxazolidinone derivatives, process for their preparation and pharmaceutical compositions containing them
WO2000000194A1 (en) 1998-06-27 2000-01-06 Photogenesis, Inc. Ophthalmic uses of ppargamma agonists and ppargamma antagonists
EP1108713A4 (en) 1998-08-27 2006-04-05 Ono Pharmaceutical Co CARBOXYLENE DERIVATIVES AND MEDICAMENTS CONTAINING THEM AS AN ACTIVE COMPONENT
HUP0200996A3 (en) 1999-04-07 2003-01-28 Sankyo Company Ltd Chuo Ku Amine derivatives, pharmaceutical compositions containing them and their use
HRP20010795A2 (en) 1999-04-28 2003-02-28 Aventis Pharma Gmbh Di-aryl acid derivatives as ppar receptor ligands
TWI284533B (en) 1999-05-24 2007-08-01 Sankyo Co Pharmaceutical composition for treating hyperglycemia, impaired glucose tolerance, diabetes complications and for improving insulin resistant
ID29875A (id) 1999-07-01 2001-10-18 Geron Corp Cs Penghambat-penghambat telomerase dan metode penggunaannya
US6730687B1 (en) 1999-08-23 2004-05-04 Kyorin Pharmaceutical Co., Ltd. Substituted benzylthiazolidine-2, 4-dione derivatives
CN1384825A (zh) * 1999-08-31 2002-12-11 马克西亚药品公司 亚苄基-噻唑烷二酮及其类似物以及它们在治疗糖尿病中的应用
JP2001199888A (ja) 2000-01-24 2001-07-24 Fujimoto Brothers:Kk 糖尿病治療剤
JP2001308814A (ja) 2000-04-19 2001-11-02 Hitachi Ltd フレーム構成自動識別通信装置
DE60115132T2 (de) 2000-04-21 2006-07-06 Pfizer Products Inc., Groton Thyroid-Rezeptorliganden
US6620830B2 (en) 2000-04-21 2003-09-16 Pfizer, Inc. Thyroid receptor ligands
US6680387B2 (en) 2000-04-24 2004-01-20 Aryx Therapeutics Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis
US6525202B2 (en) * 2000-07-17 2003-02-25 Wyeth Cyclic amine phenyl beta-3 adrenergic receptor agonists
ATE363278T1 (de) 2001-09-14 2007-06-15 Novo Nordisk As Neue liganden für die hisb10 zn2+ stellen des insulin-hexamers in der r-konformation
JP2005513026A (ja) * 2001-11-15 2005-05-12 インサイト サン ディエゴ インコーポレイテッド 高コレステロール血症、異脂肪血症および他の代謝障害;癌、および他の疾患を治療するn−置換複素環
US7521465B2 (en) 2003-01-17 2009-04-21 Bexel Pharmaceuticals, Inc. Diphenyl ether derivatives
US6794401B2 (en) 2003-01-17 2004-09-21 Bexel Pharmaceuticals, Inc. Amino acid phenoxy ethers
JP2007523842A (ja) 2003-03-11 2007-08-23 ノボ ノルディスク アクティーゼルスカブ 酸安定化されたインスリンを含有する薬学的製剤
US7087576B2 (en) 2003-10-07 2006-08-08 Bexel Pharmaceuticals, Inc. Dipeptide phenyl ethers

Also Published As

Publication number Publication date
EP1848700B1 (en) 2015-12-30
US7521465B2 (en) 2009-04-21
CA2598087A1 (en) 2006-08-24
US20050288341A1 (en) 2005-12-29
WO2006089225A1 (en) 2006-08-24
JP5134974B2 (ja) 2013-01-30
PL1848700T3 (pl) 2016-08-31
HUE028882T2 (en) 2017-01-30
JP2008530242A (ja) 2008-08-07
ES2566337T3 (es) 2016-04-12
EP1848700A1 (en) 2007-10-31
KR20070105364A (ko) 2007-10-30

Similar Documents

Publication Publication Date Title
US7521465B2 (en) Diphenyl ether derivatives
US20110123495A1 (en) Derivatives of pyridone and use thereof
CA2642650C (en) Novel heterocyclic diphenyl ethers
US7521466B2 (en) Dipeptide phenyl ethers
CA2513496C (en) Amino acid phenoxy ethers
US20080319031A1 (en) Novel Tyrosine Derivatives
CN101160296A (zh) 用于降低血浆中葡萄糖、胆固醇和甘油三酸酯水平的5-[4-(4-(2-氨基-2-甲氧基羰基乙基)苯氧基)亚苄基]噻唑烷-2,4-二酮衍生物和相关化合物
WO1992014730A1 (fr) Derive de thiazolidine-2,4-dione, sel dudit derive et leur production
KR20080099871A (ko) 신규의 헤테로싸이클릭 싸이클로알킬 유도체, 이의 제조 방법 및 이를 포함하는 약제학적 조성물
ZA200506527B (en) Amino acid phenoxy ethers

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20200217