WO1985004170A1 - Thiazolidinedione derivatives, process for their preparation, and medicinal composition containing same - Google Patents

Thiazolidinedione derivatives, process for their preparation, and medicinal composition containing same Download PDF

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Publication number
WO1985004170A1
WO1985004170A1 PCT/JP1984/000117 JP8400117W WO8504170A1 WO 1985004170 A1 WO1985004170 A1 WO 1985004170A1 JP 8400117 W JP8400117 W JP 8400117W WO 8504170 A1 WO8504170 A1 WO 8504170A1
Authority
WO
WIPO (PCT)
Prior art keywords
thiazolidinedione
compound
ethoxy
acid
methyl
Prior art date
Application number
PCT/JP1984/000117
Other languages
English (en)
French (fr)
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/JP1984/000117 priority Critical patent/WO1985004170A1/ja
Priority to PCT/JP1984/000445 priority patent/WO1985004171A1/ja
Priority to US06/711,536 priority patent/US4582839A/en
Priority to JP60041584A priority patent/JPS60208980A/ja
Priority to EP85301895A priority patent/EP0155845A1/en
Priority to CA000476976A priority patent/CA1263961A/en
Publication of WO1985004170A1 publication Critical patent/WO1985004170A1/ja

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
    • 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

Definitions

  • Thiazolidinedione tsuba conductor method for producing the same, and pharmaceutical composition containing the same
  • the present invention relates to a novel thiazolidinedione derivative having excellent blood sugar and blood lipid lowering effects, a method for producing the same, and a pharmaceutical composition comprising the same.
  • ⁇ Holeurea compounds are used.
  • biguanide compounds cause lactic acidosis and are therefore rarely used at present, and phororerea compounds have potent hypoglycemic activity, but often cause severe hypoglycemia. , Care must be taken in use.
  • the present inventors have found a novel thiazolidinedione derivative having an excellent blood serum and blood lipid lowering action.
  • the present invention is a.
  • H 1 and !! 2 are the same or different and represent hydrogen or a lower alkyl group
  • R 3 represents hydrogen or an acyl group
  • n represents 0 or 1.
  • R 1 , !! 2 and n have the same meanings as above.
  • R 4 is hydrogen or a group
  • R 5 is hydrogen or a lower group
  • X is a halogen atom
  • n is n Indicates 0 or 1, respectively. Is reacted with thiourea to give
  • a — a pharmaceutical composition comprising a thiazolidine conductor represented by formula (I) or a salt thereof,
  • Formula (I), (2) and (Summer) Medium Rl as the low-Hi key group represented by R 2, for example methylcarbamoyl, E Ji, Burobi, I, knobs port bi, butyrate etc. carbon atoms 1 Among them, those having 4 to 3 carbon atoms are preferred, and those having 1 to 3 carbon atoms are preferable, and these may be substituted at any position of the pyridine ring.
  • Examples of the acyl group represented by R 3 include, for example,
  • O PI ⁇ There are 1 to 8 carbon ash groups such as dibutyl, brobion! /, Butyric, isobutyryl, penzoi W, and toy *.
  • Examples of the ash group represented by R 4 include the same as the ash group represented by.
  • Examples of the lower aki group represented by R 1 include the same as the lower aki group represented by R 1 .
  • Examples of the halogen atom represented by 3C include chlorine, bromine and iodine.
  • the four thiazolidinedione compounds represented by the formula (I) are amphoteric compounds having an acidic nitrogen in the thiazolidine ring and a basic nitrogen in the viridine ⁇ , and have both ⁇ salt and base ⁇ .
  • the boundary of the thiazolidinedione conductor (I) is as a salt such as hydrochloride, hydrogen bromide completion, sulfuric acid, phosphoric acid, methansulfone, etc.
  • Organic plants such as acid salts, salt, malt salt, maleic acid, fumanore salt, succinic acid, tartaric acid, malic acid, etc.
  • Metal salts such as lithium salt, aluminum-palladium salt, magnesium salt, and casium are listed.
  • thiazolidinedione-conductor represented by formula (I) according to the present invention and the thiazolidinedione-conductor include the following compounds.
  • the reaction between the compound represented by the general formula () and thiourea is usually carried out with a class of alcohols (eg, methanoic, ethano, * ropano; W, 2-propanol, butano, isobbutano; u, 2-methyl) It is carried out in any solvent such as toki ⁇ ethanol, dimethyl sulphoxide and suholane.
  • the degree of reversal is usually 2 to 180, preferably 60 to 150.
  • the amount of thiourea used is 1-2 mol per 1 mol of the compound (S). In this reaction, hydrogen halide is by-produced with the progress of the reaction.
  • a dehydrating agent such as sodium phosphate or potassium acetate may be added to carry out the reaction.
  • the acid stabilizer is generally used in an amount of 1 to 1.5 moles per mole of the compound (H).
  • Such anti-FS! The compound (an is produced and, if desired, can be isolated; however, the compound may be directly led to the next hydrolysis step without (().
  • the hydrolysis of the compound ( ⁇ ) is usually performed in a suitable solvent in the presence of water and a mineral acid.
  • the solvent include those used for the reaction between the compound (2) and thiourea.
  • the mineral acid include hydrochloric acid, hydrobromic acid, sulfuric acid and the like.
  • the amount of the mineral acid to be used is ⁇ 1 to 10 mol, preferably ⁇ 12 to 3 mol per mol of the compound ().
  • the amount of water to be added depends on compound (I) It is usually a large surplus for l. This reaction is usually performed under heating or heating.
  • the reaction temperature is usually 60 to 150 watts.
  • the heating time is usually several hours to over ten hours.
  • the hydroxy form (]) may be subjected to the following Aich reaction as necessary.
  • the acylation reaction of the hydroxyl form () is usually carried out by reacting an acylating agent in an appropriate solvent in the presence of a 3 ⁇ 4 group.
  • the solvent include yeast esters, esthetics, for example, aromatic hydrocarbons such as benzene, toluene, and xylene, and ethers, such as acetic acid, diisobromo, etc./ether, tetrahydrofuran, and dioxane.
  • ketones such as acetone and methetic ketone-such as dichloromethane, chloromethane, carbon tetrachloride, chlorinated hydrocarbons, and dimethyformamide.
  • the facilitating agent include gi, g, umami, araliphatic, and aromatic sai anhydrides and halides.
  • the aliphatic power is, for example, vinegar ⁇ , brobion.
  • Carbon such as ,, ⁇ acid, iso ⁇ ⁇ , completed Yoshikusa, completed Iso Yoshikusa, hexane ⁇
  • the aromatic aromatic carbons are, for example, charcoal cords 8 to 9 such as Hua-vinegar sai and the ferrocarbons, and the aromatic carbons are, for example, benzoic acid, Paramethyi benzoic acid such as those having 7 to 8 carbon atoms, and further on these aromatic rings, for example, halogens (eg, fluorene, chlorine, bromine, etc.), akoxy (eg, methoxy, ethoxy, etc.) , Trifluoromethyl group and the like may be substituted.
  • halogens eg, fluorene, chlorine, bromine, etc.
  • akoxy eg, methoxy, ethoxy, etc.
  • Trifluoromethyl group and the like may be substituted.
  • the amount of the acylating agent to be used is usually 1 to 1 mol of the hydroxy form (I '). 10 3 ⁇ 4 ⁇ Preferably, it is 1-2.
  • the azo group include viridin and thietamine, such as, for example, sodium carbonate * potassium carbonate * sodium bicarbonate, potassium hydrogen carbonate, carbonic acid, and hydrogen peroxide.
  • the base is usually used in an equimolar amount or in excess of the acylated compound.
  • pyridine When pyridine is used as the group, a large excess amount of pyridine is used.] It can also serve as a solvent. This reaction is generally carried out at a temperature of from 20 t to 40, and the reaction time is usually from 10 minutes to 24 hours.
  • a compound in which R 3 is an ash group in the killing formula (I) [may also be referred to as a lower alcohol form ((')] can be obtained.
  • the thiazolidinedione derivative (I) is necessary]. It can also be reacted with an acid or a sulfonic group according to a conventional method and led to the boundary.
  • the thiazolidinedione thus obtained and the thiazolidinedione are obtained by known means of separation and purification, for example, by using concentrated pestle, is, solvent extraction, crystallization, recrystallization, dissolution, chromatography and the like. can do.
  • thiazolidinedione hypoconductor (I) and its salt are useful for treating hyperlipidemia and diabetes in humans and their complications.
  • the method of administration is usually orally used, for example, as pills, capsules, powders, granules, etc., but in some cases it can be given non-periodically as injections, suppositories, or pellets.
  • ⁇ ⁇ 5 J ⁇ i ⁇ is usually administered orally (X 0 1 -1 o ⁇ z ⁇ 3 ⁇ 4 parenterally, or lipolipidemic) per adult per day.
  • ⁇ 55 to 10 When used as an agent for the treatment of infectious diseases, ⁇ 55 to 10 can be administered orally and ⁇ ⁇ to i ⁇ 3 ⁇ 4? ⁇ ⁇ can be administered non-radially per adult per day. It is desirable to administer this amount once a day or two to four times a week.
  • the starting compound ( ⁇ ) of the present invention can be produced, for example, by the following method.
  • R 1, R 2 and X are as defined above der]
  • the oxidation reaction of compound (W) to compound (V) is achieved by reacting compound (IV) with hydrogen peroxide or an organic peracid! ? Can be easily done.
  • organic peracids include, for example, formic acid, peroxide, pertriprostatic, perbenzoic acid, m-chloroperbenzoic acid, and the like. It can be performed according to the method.
  • the assimilation reaction from (V) to chemical ⁇ 5 (IT) is achieved by reacting the chemical with ⁇ J (V)!
  • the reaction is usually performed with anhydrous or halide
  • the hydrolysis reaction from compound (H) to compound (IT) can be performed by a usual method using sodium hydroxide or potassium hydroxide.
  • reaction from compound (w) to compound (W) is achieved by combining compound (g) with compound 01> in the presence of sodium hydride! ) Done.
  • This reaction can be carried out at a temperature of 10 t to 20 watts in a solution of dimethiformamide, titro- drofuran, or the like.
  • the reaction from the compound (3 ⁇ 4!) To the compound () is carried out by catalytic reduction of the compound (W) using, for example, palladium carbon as a catalyst in a conventional manner.
  • compound () is diazotized in the presence of hydrogen halide.
  • HX acrylic acid or its esthetics
  • a copper catalyst eg, oxidative oxidation
  • the reaction is carried out under the condition of copper, copper oxide, copper chloride, cupric chloride, ferrous bromide, cupric bromide, etc.
  • the reaction from the compound ⁇ ( ⁇ ) to the compound (3T) is performed by converting the compound 3 ⁇ 48 (IT) into a compound. This reaction can be carried out in the same manner as in the method for converting the compound (V) into a compound.
  • kink Gin (1 0, poured into water was stirred for 8 hours a mixture of anhydrous ⁇ (0.1 at room temperature, and extracted with ⁇ acid Echiru. Gun ⁇ E Chi layer was washed with water, dried (MgSO 4) the solvent And the residue is removed
  • mice Hypoglycemic and lipid-lowering effects in mice
  • the test compound was mixed with powdered feed (CE-2, CLEA Japan) (005%) and freely mixed with KKA mice (male, 8-: L0 week old, 15 mice). Water was given ad libitum during this period, blood was collected from the bacterium, blood was collected by the glucose assay, and plasma triglyceride levels were determined by the fistula method! By using Cleantech TG-S kit (Chatron)]. Each value was shown as a reduction rate () with respect to the drug non-administration group.
  • Compound Hypoglycemic action Lipid-lowering action
  • novel thiazolidinedione derivative (I) according to the present invention has an excellent blood and blood lipid-returning effect, and is useful as a pharmaceutical such as a therapeutic agent for diuresis and a therapeutic agent for hyperlipidemia.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Diabetes (AREA)
  • General Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
PCT/JP1984/000117 1984-03-21 1984-03-21 Thiazolidinedione derivatives, process for their preparation, and medicinal composition containing same WO1985004170A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
PCT/JP1984/000117 WO1985004170A1 (en) 1984-03-21 1984-03-21 Thiazolidinedione derivatives, process for their preparation, and medicinal composition containing same
PCT/JP1984/000445 WO1985004171A1 (en) 1984-03-21 1984-09-14 Thiazolidinedione derivatives, process for their preparation, and medicinal compositions containing same
US06/711,536 US4582839A (en) 1984-03-21 1984-09-21 2,4-thiazolidinediones
JP60041584A JPS60208980A (ja) 1984-03-21 1985-03-01 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
EP85301895A EP0155845A1 (en) 1984-03-21 1985-03-19 Thiazolidinedione derivatives, their production and use
CA000476976A CA1263961A (en) 1984-03-21 1985-03-20 5-¬4-(2 pyridylalkoxy)benzyl|-2,4- thiazolidinedione compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/JP1984/000117 WO1985004170A1 (en) 1984-03-21 1984-03-21 Thiazolidinedione derivatives, process for their preparation, and medicinal composition containing same

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WO1985004170A1 true WO1985004170A1 (en) 1985-09-26

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PCT/JP1984/000445 WO1985004171A1 (en) 1984-03-21 1984-09-14 Thiazolidinedione derivatives, process for their preparation, and medicinal compositions containing same

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WO (2) WO1985004170A1 (enrdf_load_stackoverflow)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010105048A1 (en) * 2009-03-12 2010-09-16 Metabolic Solutions Development Company 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

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4891216A (en) * 1987-04-14 1990-01-02 Alcide Corporation Disinfecting compositions and methods therefor
US5183823A (en) 1991-04-11 1993-02-02 Takeda Chemical Industries, Ltd. Pyridine n-oxide compounds which are useful as hypoglycemic and hypolipidemic agents
FR2680512B1 (fr) * 1991-08-20 1995-01-20 Adir Nouveaux derives de 2,4-thiazolidinedione, leur procede de preparation et les compositions pharmaceutiques qui les contiennent.
JP2009530293A (ja) * 2006-03-16 2009-08-27 メタボリック ソリューションズ ディベロップメント カンパニー チアゾリジンジオン類似体およびグルココルチコイドアゴニストの併用療法
PL2902026T3 (pl) * 2006-03-16 2018-03-30 Metabolic Solutions Development Company Llc Analogi tiazolidynodionu do leczenia choroby metabolicznej pośredniczonej przez zapalenie
PL2001469T3 (pl) * 2006-03-16 2012-10-31 Metabolic Solutions Dev Co Llc Analogi tiazolidynodionu

Citations (1)

* 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

Patent Citations (1)

* 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

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Chemical Abstracts, Vol. 98, No. 15, Abstract No. 98 : 125945S; & Chem. Pharm. Bull. 1982, 30(10), 3580-600 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010105048A1 (en) * 2009-03-12 2010-09-16 Metabolic Solutions Development Company 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
US9126959B2 (en) 2009-12-15 2015-09-08 Metabolic Solutions Development Company, Llc PPAR-sparing thiazolidinedione salts for the treatment of metabolic diseases

Also Published As

Publication number Publication date
JPH0570633B2 (enrdf_load_stackoverflow) 1993-10-05
WO1985004171A1 (en) 1985-09-26
JPS60208980A (ja) 1985-10-21

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