WO2001081328A3 - Thiazolidinedione analogues and their use for the treatment of diabetes - Google Patents

Thiazolidinedione analogues and their use for the treatment of diabetes Download PDF

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Publication number
WO2001081328A3
WO2001081328A3 PCT/US2001/013131 US0113131W WO0181328A3 WO 2001081328 A3 WO2001081328 A3 WO 2001081328A3 US 0113131 W US0113131 W US 0113131W WO 0181328 A3 WO0181328 A3 WO 0181328A3
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WO
WIPO (PCT)
Prior art keywords
diabetes
compounds
treatment
designed
metabolized
Prior art date
Application number
PCT/US2001/013131
Other languages
French (fr)
Other versions
WO2001081328A2 (en
Inventor
Pascal Druzgala
Peter G Milner
Jurg R Pfister
Original Assignee
Aryx Therapeutics
Pascal Druzgala
Peter G Milner
Jurg R Pfister
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 Aryx Therapeutics, Pascal Druzgala, Peter G Milner, Jurg R Pfister filed Critical Aryx Therapeutics
Priority to JP2001578420A priority Critical patent/JP2003531200A/en
Priority to AU2001259130A priority patent/AU2001259130A1/en
Priority to CA002402123A priority patent/CA2402123A1/en
Priority to EP01932617A priority patent/EP1276730A2/en
Publication of WO2001081328A2 publication Critical patent/WO2001081328A2/en
Publication of WO2001081328A3 publication Critical patent/WO2001081328A3/en

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    • 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
    • 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
    • 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
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more 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
    • C07D261/12—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
    • C07D277/34—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
    • 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
    • C07D413/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • 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
    • 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
    • C07D417/12—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 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
    • C07J—STEROIDS
    • C07J3/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Diabetes (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Steroid Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Medicines Containing Plant Substances (AREA)

Abstract

The subject invention provides pharmaceutical compounds useful in the treatment of Type II diabetes. These compounds are advantageous because they are readily metabolized by the metabolic drug detoxification systems. Particularly, thiazolidinedione analogs that have been designed to include esters within the structure of the compounds are provided. This invention is also drawn to methods of treating disorders, such as diabetes, comprising the administration of therapeutically effective compositions comprising compounds that have been designed to be metabolized by serum or intracellular hydrolases and esterases. Pharmaceutical compositions of the ester-containing thiazolidinedione analogs are also taught.
PCT/US2001/013131 2000-04-24 2001-04-24 Thiazolidinedione analogues and their use for the treatment of diabetes WO2001081328A2 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP2001578420A JP2003531200A (en) 2000-04-24 2001-04-24 Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis
AU2001259130A AU2001259130A1 (en) 2000-04-24 2001-04-24 Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis
CA002402123A CA2402123A1 (en) 2000-04-24 2001-04-24 Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis
EP01932617A EP1276730A2 (en) 2000-04-24 2001-04-24 Thiazolidinedione analogues and their use for the treatment of diabetes

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US19914600P 2000-04-24 2000-04-24
US60/199,146 2000-04-24
US28198201P 2001-04-06 2001-04-06
US60/281,982 2001-04-06

Publications (2)

Publication Number Publication Date
WO2001081328A2 WO2001081328A2 (en) 2001-11-01
WO2001081328A3 true WO2001081328A3 (en) 2002-02-21

Family

ID=26894508

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2001/013131 WO2001081328A2 (en) 2000-04-24 2001-04-24 Thiazolidinedione analogues and their use for the treatment of diabetes

Country Status (5)

Country Link
EP (1) EP1276730A2 (en)
JP (1) JP2003531200A (en)
AU (1) AU2001259130A1 (en)
CA (1) CA2402123A1 (en)
WO (1) WO2001081328A2 (en)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6768008B2 (en) 2000-04-24 2004-07-27 Aryx Therapeutics Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis
US6680387B2 (en) 2000-04-24 2004-01-20 Aryx Therapeutics Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis
US6784199B2 (en) 2000-09-21 2004-08-31 Aryx Therapeutics Isoxazolidine compounds useful in the treatment of diabetes, hyperlipidemia, and atherosclerosis in mammals
US6958355B2 (en) 2000-04-24 2005-10-25 Aryx Therapeutics, Inc. Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis
WO2004009527A1 (en) 2002-07-19 2004-01-29 Aryx Therapeutics Materials and methods for treating hypercholesterolemia
FR2856060A1 (en) * 2003-06-12 2004-12-17 Centre Nat Rech Scient Protecting groups cleavable by serum albumin, comprising new or known 4-substituted isoxazole or isothiazole derivatives, useful e.g. in prodrugs, prohormones or serum albumin determination reagents
US7566732B2 (en) 2003-10-28 2009-07-28 Rigel Pharmaceuticals, Inc. Rhodanine compositions for use as antiviral agents
NL2010010C2 (en) 2012-12-19 2014-06-23 Sulfateq B V Compounds for protection of cells.
CN104306373B (en) * 2014-09-29 2017-08-08 中国科学院成都生物研究所 A kind of application of oxazolyl phenyl class compound in the medicine for preparing treating cancer
PL3762368T3 (en) 2018-03-08 2022-06-06 Incyte Corporation Aminopyrazine diol compounds as pi3k-y inhibitors
WO2020010003A1 (en) 2018-07-02 2020-01-09 Incyte Corporation AMINOPYRAZINE DERIVATIVES AS PI3K-γ INHIBITORS

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0528734A1 (en) * 1991-08-20 1993-02-24 Adir Et Compagnie Thiazolidin-2,4-dione derivatives, process for their preparation and pharmaceutical compositions containing them
EP0549365A1 (en) * 1991-12-26 1993-06-30 Sankyo Company Limited Thiazolidine compounds, their preparation and their therapeutic uses
JPH09165371A (en) * 1995-10-09 1997-06-24 Sankyo Co Ltd Medicine containing heterocyclic compound
WO1997032863A1 (en) * 1996-03-08 1997-09-12 Torii Pharmaceutical Co., Ltd. Thiazolidine-2,4-dione derivatives
JPH09301963A (en) * 1996-05-17 1997-11-25 Kyorin Pharmaceut Co Ltd N-benzyldioxothiazolidinylbenzamide derivative and production thereof
EP0848004A1 (en) * 1995-07-31 1998-06-17 Shionogi & Co., Ltd. Pyrrolidine derivatives having phospholipase a2 inhibitory activity
WO2001002377A1 (en) * 1999-07-01 2001-01-11 Geron Corporation Telomerase inhibitors and methods of their use

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0528734A1 (en) * 1991-08-20 1993-02-24 Adir Et Compagnie Thiazolidin-2,4-dione derivatives, process for their preparation and pharmaceutical compositions containing them
EP0549365A1 (en) * 1991-12-26 1993-06-30 Sankyo Company Limited Thiazolidine compounds, their preparation and their therapeutic uses
EP0848004A1 (en) * 1995-07-31 1998-06-17 Shionogi & Co., Ltd. Pyrrolidine derivatives having phospholipase a2 inhibitory activity
JPH09165371A (en) * 1995-10-09 1997-06-24 Sankyo Co Ltd Medicine containing heterocyclic compound
WO1997032863A1 (en) * 1996-03-08 1997-09-12 Torii Pharmaceutical Co., Ltd. Thiazolidine-2,4-dione derivatives
JPH09301963A (en) * 1996-05-17 1997-11-25 Kyorin Pharmaceut Co Ltd N-benzyldioxothiazolidinylbenzamide derivative and production thereof
WO2001002377A1 (en) * 1999-07-01 2001-01-11 Geron Corporation Telomerase inhibitors and methods of their use

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; XP002181181, Database accession no. 128:13261 *
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; XP002181182, Database accession no. 127:161819 *
KLETZIEN R F ET AL: "Enhancement of adipocyte differentiation by an insulin-sensitizing agent", MOLECULAR PHARMACOLOGY, vol. 41, no. 2, 1 February 1992 (1992-02-01), pages 393 - 398, XP002081233 *
SOHDA T ET AL: "Studies on antidiabetic agents. II. Synthesis of 5-[4-(1-methylcyclohexylmethoxy)-benzyl] thiazolidine-2,4-dione (ADD-3878) and its derivatives", CHEMICAL AND PHARMACEUTICAL BULLETIN, vol. 30, no. 10, 1982, pages 3580 - 3600, XP002042079 *
UNANGST P C ET AL: "Synthesis and biological evaluation of 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxy phenyl]methylene]oxazoles, -thiazoles, and -imidazoles: Novel dual 5-lipoxygenase and cyclooxygenase inhibitors with antiinflammatory activity", JOURNAL OF MEDICINAL CHEMISTRY, vol. 37, no. 2, 1994, pages 322 - 328, XP002127023 *

Also Published As

Publication number Publication date
JP2003531200A (en) 2003-10-21
AU2001259130A1 (en) 2001-11-07
EP1276730A2 (en) 2003-01-22
WO2001081328A2 (en) 2001-11-01
CA2402123A1 (en) 2001-11-01

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