WO1986002073A1 - Derives de thiazolidinedione, procede de preparation et composition pharmaceutique les contenant - Google Patents

Derives de thiazolidinedione, procede de preparation et composition pharmaceutique les contenant Download PDF

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Publication number
WO1986002073A1
WO1986002073A1 PCT/JP1984/000466 JP8400466W WO8602073A1 WO 1986002073 A1 WO1986002073 A1 WO 1986002073A1 JP 8400466 W JP8400466 W JP 8400466W WO 8602073 A1 WO8602073 A1 WO 8602073A1
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WO
WIPO (PCT)
Prior art keywords
compound
reaction
formula
hydrogen
methyl
Prior art date
Application number
PCT/JP1984/000466
Other languages
English (en)
Japanese (ja)
Inventor
Kanji Meguro
Takeshi Fujita
Original Assignee
Takeda Chemical Industries, Ltd.
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 Takeda Chemical Industries, Ltd. filed Critical Takeda Chemical Industries, Ltd.
Priority to PCT/JP1984/000466 priority Critical patent/WO1986002073A1/fr
Priority to ZA857448A priority patent/ZA857448B/xx
Priority to CN85107870.2A priority patent/CN1003445B/zh
Priority to AR30172685A priority patent/AR240673A1/es
Priority to KR1019850007158A priority patent/KR920002131B1/ko
Priority to JP60216050A priority patent/JPS6185372A/ja
Priority to DK444685A priority patent/DK444685A/da
Priority to AU48176/85A priority patent/AU583537B2/en
Priority to FI853796A priority patent/FI81097C/fi
Priority to HU853828A priority patent/HU194199B/hu
Priority to GR852389A priority patent/GR852389B/el
Priority to CA000492072A priority patent/CA1263655A/fr
Priority to SU853966456A priority patent/SU1496634A3/ru
Priority to PT81235A priority patent/PT81235B/pt
Priority to NO853902A priority patent/NO157896C/no
Priority to ES547507A priority patent/ES8706150A1/es
Priority to EP85307084A priority patent/EP0177353B1/fr
Priority to US06/783,628 priority patent/US4725610A/en
Priority to AT85307084T priority patent/ATE51869T1/de
Priority to DE8585307084T priority patent/DE3577092D1/de
Publication of WO1986002073A1 publication Critical patent/WO1986002073A1/fr
Priority to ES554559A priority patent/ES8801256A1/es

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Classifications

    • 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
    • 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
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon 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
    • C07D277/22—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/24—Radicals substituted by 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
    • C07D277/22—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • 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

Definitions

  • composition comprising it
  • the present invention relates to a novel thiazolidinedione derivative having an excellent blood glucose and blood lipid lowering effect, a method for producing the same, and a pharmaceutical composition containing the same.
  • the present invention is a.
  • a pharmaceutical composition comprising a thiazolidinedione derivative represented by the general formula (I) or a salt thereof.
  • the hydrocarbon residue represented by R 1 is an aliphatic hydrocarbon residue, an alicyclic hydrocarbon residue, an alicyclic hydrocarbon residue.
  • the aliphatic hydrocarbon residues include methyl, ethynole, propynole, isopropynole, butyl, and isobutyl.
  • Saturated aliphatic hydrocarbon residue having 1 to 8 carbon atoms for example, ethenyl , 1-probenyl, 2-probenyl, 1-butenyl, 2-buteninole, 3-1-butenyl, 2-methinole 1, 1-pentinole, 1-penteninole, 2-penteninole, 3-pen 1-hexeninole, 3-hexeninole, 3,4-hexeninole, 5-hexeninole, 1-heptininole, 1-octeninole, etyninole, 1-propynole , 1 butyninole, 2 butyninole, 3 butyninole, 1 pentinole, 2 pentinole, 3 pentinole, 4 pentinole, 1 hexinole, 31 hexinole, 2 hexinole, 2, (4) Hexazidinyl, (5) hexynyl, (1) heptyny
  • cyclopropinolemethinole those having 4 to 9 carbon atoms, for example, cyclopropinolemethinole, cyclopropinoleetinole, buttocinolemethinole, syruppentinolemethine / le, 2-cyclopenteninolemethinole, 3 — Cyclopenteninolemethinole, cyclohexinolemethinole, 2-cyclohexeninolemethinole, 3-cyclohexeninolemethinole, cyclohexene Xinoleethynole, cyclohexynolepropynole, cycloheptinolemethyl, cycloheptylethyl, etc.
  • araliphatic hydrocarbon residue examples include, for example, benzyl, phenethyl, 1-phenylethyl, phenylpropynole 2-phenylpropyne, 1- Phenylyl alkynole with 9 carbon atoms, such as phenylpropyl, naphthinolemethinole, naichi naphthinoleethyl, naphthinoleethyl, ⁇ -naphthylmethinole, / 3-naphthylethyl, etc.
  • aromatic hydrocarbon residue examples include phenyl and naphthyl (-naphthyl, ⁇ -naphthyl).
  • the heterocyclic residue represented by R 1 is a 5- or 6-membered ring containing 1 or 3 selected from N, 0, and S in addition to carbon as a ring-constituting atom, and is a group bonded through carbon. Specific examples include chenyl (2-phenyl, 3-phenyl), frills (2-furyl, 3-furyl), pyridyl (2-pyridyl, 3-pyridyl).
  • the hydrocarbon residue and heterocyclic residue represented by R 1 may have a substituent at any position.
  • R 1 contains an aliphatic group, or:
  • 1 is a saturated heterocyclic group, a lower quinole group having 1 to 3 carbon atoms (eg, methyl, ethyl, propyl) is present on the ring (including the N atom). , Isopropyl).
  • R 1 contains an aromatic hydrocarbon group, or when R 1 is a heteroaromatic group, the ring (including the hetero atom) has 1 to 4 identical or different substituents on the ring.
  • substituents examples include halogen (fluorine, chlorine, bromine, iodine), hydroxy, cyano, trifluoromethinole, and lower alkoxy (eg, methoxy, ethoxy, prooxy, isopropoxy). , Butoxy, but having 1 to 4 carbon atoms), lower alkyl (eg, methyl, ethyl, propyl, isopropyl, butynole, etc.)
  • lower anorecoxy carbonyl eg, methoxycarbonyl
  • Ethoxycarbonyl Ethoxycarbonyl
  • Proho. Xylcarbonyl etc.
  • lower alkynolethio eg, methylthio, ethylthio, propylthio, isopropylthio, etc., having 1 to 3 carbon atoms.
  • Examples of the lower alkyl group represented by R 2 include those having 1 to 5 carbon atoms, such as methyl, ethyl, butyl pinole, isopropyl, butyl, isobutynole, sec-butyl, t-butynole, and pentyl. Those having from 4 to 4 carbon atoms are preferred, and those having from 3 to 3 carbon atoms are most preferred.
  • This alkynole group may have a hydroxyl group at an arbitrary position, but is preferably in the 9th and 9th positions.
  • the halogen represented by Y in the general formula (II :) includes chlorine, bromine and iodine.
  • the thiazolidinedione derivative represented by the general formula (I) has an acidic nitrogen in the thiazolidine ring, and thus forms a salt with a base.
  • base salts include, for example, metal salts such as sodium salt, potassium salt, aluminum salt, magnesium salt, and canoleshium salt.
  • the hydrolysis reaction of the compound represented by the formula (I) is usually carried out in a suitable solvent in the presence of water and a mineral acid.
  • Solvents usually include alcohols (eg, methanol, ethanol, propanol, 21-propanol, butanol, isobutanol, 2-methoxyethanol, etc.), dimethyl sulfoxide , Sulfolane, dioxane, dinotoxyethane and the like.
  • the mineral acid include hydrochloric acid, hydrobromic acid, sulfuric acid and the like.
  • the amount of the mineral acid used is 0.1 to 10 mol, preferably 0 to 1 mol of the compound (III). Two to three models.
  • the amount of water to be added is usually a large excess in relation to the mole of the compound (II).
  • This reaction is usually performed with heating or heating, and the reaction temperature is usually 60 to 150 ° C.
  • the heating time is usually several hours to several tens of hours.
  • Such solvents include dimethylformamide, dimethylsulfoxide, sulfolane, tetrahydrofuran, and dimethoxetane
  • the bases include sodium hydride, lithium hydride, sodium amide, and sodium amide.
  • Lithium methoxide, sodium ethoxide, and potassium 71-butoxide are examples of each.
  • This condensation reaction is usually 0.
  • the reaction is carried out at C to 120 ° C, preferably at 20 ° C to 100 ° C, and the reaction time is usually 0.5 to 5 hours.
  • R 2 is an alkyl group having a hydroxyl group at the ⁇ position, it can be produced, for example, by the following method.
  • This reaction proceeds easily by refluxing in a solvent such as carbon tetrachloride or chloroform, and the amount of the radio-initiator used is usually ( ⁇ )
  • the generated ⁇ -halogeno form [V) is necessary]]]] Isolation and purification, or isolation
  • a solvent such as carbon tetrachloride or chloroform
  • the reaction temperature is 20%. From 3 ⁇ 4 to ⁇ 00, the reaction time is 0.5 to 10 hours.
  • the thiazolidinedione derivative (I) and its salt obtained in this manner can be separated and purified by known separation and purification means such as concentration, concentration under reduced pressure, solvent extraction, crystallization, crystallization, phase transfer, and chromatography.
  • the compounds (I) and salts thereof of the present invention have excellent blood glucose and blood lipid lowering effects on mammals (eg, mice, rats, dogs, cats, monkeys, horses, and humans), and have toxicity. Low acute and subacute toxicity. Therefore, the thiazolidinedione derivative (I) and its salt are useful for treating hyperlipidemia, diabetes and their complications in humans.
  • the starting compound (H) of the present invention can be produced, for example, by the following method]).
  • This reaction can be carried out in a solvent such as dimethylformamide or tetrahydrofuran at- ⁇ O; Then, the reaction from compound (H) to compound (K) is carried out by catalytic reduction of compound () by, for example, palladium carbon as a catalyst.)) Or by a conventional method using zinc or iron and sulfuric acid. It can be done easily.
  • Compound () may be isolated as a pure product, or may be subjected to the reaction of the next step without isolation and purification.
  • compound (K) is diazotized in the presence of hydrohalic acid (HY), and acrylic acid or its ester (X) is reacted with a copper catalyst (eg, The reaction is performed in the presence of cuprous oxide, cupric oxide, cuprous chloride, cupric chloride, cuprous bromide, cupric bromide, and the like. Due to the so-called Meerwein arylation reaction]).
  • Compound (XI) is chromatography -? By the like] can also child purification may be subjected to the reaction of the isolated and purified to Kotorukutsugi step ⁇ (I) can be produced by reacting compound (XI) with thiourea.
  • This reaction is usually performed with alcohols (eg, methanol, ethanol, prono, methanol, 2-propanol, butanol, isobutanol, 2-methoxyethanol, etc.). It is carried out in a solvent such as dimethylsulfoxide and sulfolane.
  • the reaction temperature is usually from 20 ° C to 180 ° C, preferably from 60 ° C to 150 ° C.
  • the amount of thiourea used is ⁇ to 2 mol per 1 mol of the compound ().
  • hydrogen halide is by-produced as the reaction proceeds, but the reaction may be carried out in the presence of sodium acetate or acetic acid steam to capture this.
  • reaction of condensing compound (I) with compound GOD to form a compound (3D is usually performed in a solvent such as dimethinolefo ⁇ remamide, tetrahydrofuran, acetone, methinoleethylketone, or a base in a solvent (eg, carbonate).
  • a solvent such as dimethinolefo ⁇ remamide, tetrahydrofuran, acetone, methinoleethylketone, or a base in a solvent (eg, carbonate).
  • the reaction can be performed at 0 ° C to 150 ° C in the presence of sodium and carbon dioxide (XI is then hydrolyzed to compound (K).
  • Hydrochloric acid, hydrobromic acid, sulfuric acid, etc. or alkaline hydroxide (eg, sodium hydroxide, potassium hydroxide, etc.).
  • the condensation reaction between compound (and compound on) can be carried out in the same manner as in the reaction between compound (n) and compound (M).
  • step 5 2) Dissolve the oil (20.5 da) obtained in 1) in acetone (100) »)-methanol (10Ow) and add 47HBr7 (45 ⁇ ). Then, in step 5, a water (10) solution of iTaWO 2 (4.8) was added dropwise in the following. After stirring at 5 ° C for 15 minutes, methyl acrylate (: 33) was added and the mixture was heated to 38 ° C. A small amount of cuprous oxide (29) was added while stirring the mixture vigorously. After stirring until the generation of nitrogen gas was completed, the reaction solution was concentrated under reduced pressure. The residue was made basic with aqueous ammonia and extracted with ethyl acetate.
  • Test compound was added to powder feed (c c-2, CLEA Japan) at 0. 0 ⁇ -mice (male, 8 to 10 weeks old, 5 mice per group) were fed ad libitum for 4 days. During this time, they were given freely. Blood was collected from the orbital vein and blood levels were measured by the dalco-soxidase method]) and plasma triglycerides ( ⁇
  • novel thiazolidinedione derivative (I) and a salt thereof according to the present invention have an excellent hypoglycemic and blood lipid lowering action and are useful as pharmaceuticals for treating diabetes and hyperlipidemia.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

Dérivés de thiazolidinedione représentés par la formule générale (I), où R1 représente l'hydrogène ou un hydrocarbure éventuellement substitué ou résidu hétérocyclique, R2 représente l'hydrogène ou un groupe alkyl éventuellement substitué par un hydroxy, X représente l'oxygène ou le soufre, m vaut 0 ou 1, et n représente un nombre entier entre 1 et 3. Ces nouveaux composés ainsi que leurs sels réduisent efficacement les niveaux de sucre et de lipides dans le sang, et sont donc utiles dans le traitement du diabète et de l'hyperlipémie.
PCT/JP1984/000466 1984-10-03 1984-10-03 Derives de thiazolidinedione, procede de preparation et composition pharmaceutique les contenant WO1986002073A1 (fr)

Priority Applications (21)

Application Number Priority Date Filing Date Title
PCT/JP1984/000466 WO1986002073A1 (fr) 1984-10-03 1984-10-03 Derives de thiazolidinedione, procede de preparation et composition pharmaceutique les contenant
ZA857448A ZA857448B (en) 1984-10-03 1985-09-26 Thiazolidinedione derivatives,their production and use
CN85107870.2A CN1003445B (zh) 1984-10-03 1985-09-26 噻唑烷二酮衍生物，其制备方法和用途
AR30172685A AR240673A1 (es) 1984-10-03 1985-09-26 Procedimiento para preparar derivados de tiazolidin-2,4-diona y sus sales de acidos farmaceuticamente aceptables
KR1019850007158A KR920002131B1 (ko) 1984-10-03 1985-09-27 타아졸리딘디온 유도체의 제조방법
JP60216050A JPS6185372A (ja) 1984-10-03 1985-09-27 チアゾリジンジオン誘導体、その製造法およびそれを含んでなる糖尿病または高脂血症治療剤
DK444685A DK444685A (da) 1984-10-03 1985-10-01 Tiazolidindionderivater, farmaceutiske praeparater indeholdende dem ogfremgangsmaader til fremstilling deraf
AU48176/85A AU583537B2 (en) 1984-10-03 1985-10-01 Thiazolidinedione derivatives, their production and use
FI853796A FI81097C (fi) 1984-10-03 1985-10-01 Foerfarande foer framstaellning av nya terapeutiskt verksamma tiazolidindionderivat.
HU853828A HU194199B (en) 1984-10-03 1985-10-02 Process for producing new thiazolidinedione derivatives and pharmaceutical compositions containing them as active agents
GR852389A GR852389B (fr) 1984-10-03 1985-10-02
CA000492072A CA1263655A (fr) 1984-10-03 1985-10-02 Derives de thiazolidinedione; preparation et utilisation
SU853966456A SU1496634A3 (ru) 1984-10-03 1985-10-02 Способ получени производных тиазолидиндиона или их натриевых солей
PT81235A PT81235B (pt) 1984-10-03 1985-10-02 Processo para a preparacao de derivados de tiazolidinadiona e de composicoes farmaceuticas que os contem
NO853902A NO157896C (no) 1984-10-03 1985-10-02 Analogifremgangsmaate for fremstilling av terapeutisk virksomme tiazolidindion-derivater.
ES547507A ES8706150A1 (es) 1984-10-03 1985-10-02 Un procedimiento para producir un derivado de tiazolidina- diona
EP85307084A EP0177353B1 (fr) 1984-10-03 1985-10-03 Dérivés de thiazolidinedione, leur préparation et leur utilisation
US06/783,628 US4725610A (en) 1984-10-03 1985-10-03 Thiazolidinedione derivatives, their production and use
AT85307084T ATE51869T1 (de) 1984-10-03 1985-10-03 Thiazolidindionderivate, ihre herstellung und anwendung.
DE8585307084T DE3577092D1 (de) 1984-10-03 1985-10-03 Thiazolidindionderivate, ihre herstellung und anwendung.
ES554559A ES8801256A1 (es) 1984-10-03 1986-04-30 Un procedimiento para producir derivados de tiazolidindiona

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/JP1984/000466 WO1986002073A1 (fr) 1984-10-03 1984-10-03 Derives de thiazolidinedione, procede de preparation et composition pharmaceutique les contenant

Publications (1)

Publication Number Publication Date
WO1986002073A1 true WO1986002073A1 (fr) 1986-04-10

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PCT/JP1984/000466 WO1986002073A1 (fr) 1984-10-03 1984-10-03 Derives de thiazolidinedione, procede de preparation et composition pharmaceutique les contenant

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HU (1) HU194199B (fr)
SU (1) SU1496634A3 (fr)
WO (1) WO1986002073A1 (fr)
ZA (1) ZA857448B (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1988009661A1 (fr) * 1987-06-10 1988-12-15 Pfizer Inc. Derives d'oxazolidine-2-one a usage d'agents hypoglycemiques
US8067450B2 (en) 2007-09-14 2011-11-29 Metabolic Solutions Development Company Thiazolidinedione analogues for the treatment of metabolic diseases
US8304441B2 (en) 2007-09-14 2012-11-06 Metabolic Solutions Development Company, Llc Thiazolidinedione analogues for the treatment of metabolic diseases
US8389556B2 (en) 2006-03-16 2013-03-05 Metabolic Soultions Development Company, LLC Thiazolidinedione analogues
US8629159B2 (en) 2006-03-16 2014-01-14 Metabolic Solutions Development Company, Llc Thiazolidinedione analogues
US8912335B2 (en) 2009-12-15 2014-12-16 Metabolic Solutions Development Company, Llc PPAR-sparing thiazolidinedione salts for the treatment of metabolic diseases

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5522636A (en) * 1978-08-04 1980-02-18 Takeda Chem Ind Ltd Thiazoliding derivative
JPS5697277A (en) * 1980-01-07 1981-08-05 Takeda Chem Ind Ltd Thiazolidine derivative
JPS58118577A (ja) * 1982-01-07 1983-07-14 Takeda Chem Ind Ltd チアゾリジン誘導体
JPS5948471A (ja) * 1982-09-10 1984-03-19 Takeda Chem Ind Ltd チアゾリジン誘導体

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5522636A (en) * 1978-08-04 1980-02-18 Takeda Chem Ind Ltd Thiazoliding derivative
JPS5697277A (en) * 1980-01-07 1981-08-05 Takeda Chem Ind Ltd Thiazolidine derivative
JPS58118577A (ja) * 1982-01-07 1983-07-14 Takeda Chem Ind Ltd チアゾリジン誘導体
JPS5948471A (ja) * 1982-09-10 1984-03-19 Takeda Chem Ind Ltd チアゾリジン誘導体

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1988009661A1 (fr) * 1987-06-10 1988-12-15 Pfizer Inc. Derives d'oxazolidine-2-one a usage d'agents hypoglycemiques
US4968707A (en) * 1987-06-10 1990-11-06 Pfizer Inc. Oxazolidin-2-one derivatives as hypoglycemic agents
US8389556B2 (en) 2006-03-16 2013-03-05 Metabolic Soultions Development Company, LLC Thiazolidinedione analogues
US8629159B2 (en) 2006-03-16 2014-01-14 Metabolic Solutions Development Company, Llc Thiazolidinedione analogues
US8067450B2 (en) 2007-09-14 2011-11-29 Metabolic Solutions Development Company Thiazolidinedione analogues for the treatment of metabolic diseases
US8304441B2 (en) 2007-09-14 2012-11-06 Metabolic Solutions Development Company, Llc Thiazolidinedione analogues for the treatment of metabolic diseases
US8912335B2 (en) 2009-12-15 2014-12-16 Metabolic Solutions Development Company, Llc PPAR-sparing thiazolidinedione salts for the treatment of metabolic diseases
US9126959B2 (en) 2009-12-15 2015-09-08 Metabolic Solutions Development Company, Llc PPAR-sparing thiazolidinedione salts for the treatment of metabolic diseases

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HU194199B (en) 1988-01-28
SU1496634A3 (ru) 1989-07-23
HUT39439A (en) 1986-09-29
ZA857448B (en) 1987-05-27

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