EP1360179A2 - Verfahren zur herstellung von thiazolidindion-derivaten oder von oxazolidindion-derivaten - Google Patents

Verfahren zur herstellung von thiazolidindion-derivaten oder von oxazolidindion-derivaten

Info

Publication number
EP1360179A2
EP1360179A2 EP02704834A EP02704834A EP1360179A2 EP 1360179 A2 EP1360179 A2 EP 1360179A2 EP 02704834 A EP02704834 A EP 02704834A EP 02704834 A EP02704834 A EP 02704834A EP 1360179 A2 EP1360179 A2 EP 1360179A2
Authority
EP
European Patent Office
Prior art keywords
pph
formula
compound
formic acid
transition metal
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.)
Withdrawn
Application number
EP02704834A
Other languages
English (en)
French (fr)
Inventor
Michel Bulliard
Yvon Derrien
Tony Pintus
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.)
Zach System SA
Original Assignee
PPG Sipsy SAS
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
Priority claimed from FR0102010A external-priority patent/FR2820741A1/fr
Application filed by PPG Sipsy SAS filed Critical PPG Sipsy SAS
Publication of EP1360179A2 publication Critical patent/EP1360179A2/de
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • C07D263/34—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 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
    • C07D263/44—Two oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
    • C07D233/78—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/96—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • 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
    • 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

Definitions

  • the present invention relates to a new process for the preparation of compounds derived from thiazolidinedione, oxazolidinedione or hydantoin of formula (I) from the following compounds of formula (II):
  • - Q represents an oxygen atom, a sulfur atom
  • - Ql represents an oxygen atom or a sulfur atom
  • Ri and R2 identical or different, represent a hydrogen atom, a C ⁇ o alkyl chain; cycloalkyl, alkylaryl, arylalkyl; said alkyl, cycloalkyl, alkylaryl or arylalkyl groups being optionally substituted by an alkyl, an alkoxy or aryloxy, a halogen, a hydroxy, a sulfino, a sulfonyl, an amino such as NH 2 , NHR 3 , N (R 3 ) 2 , with R3 representing an alkyl, an alkoxy or an alkylcarbonyl.
  • the compounds derived from thiazolidinedione, oxazolidinedione or hydantoin of formula (I) are known as synthetic intermediates for the preparation of pharmaceutical active ingredients or as pharmaceutical active ingredients such as, for example, pioglitazone, rosiglitazone , troglitazone, ciglitazone.
  • the process according to the invention has the advantages of preparing said compounds of formula (I) by generating few impurities, of obtaining a total conversion rate, of eliminating the use of large quantity of solvent, of being selective and easily isolate the product of formula (I).
  • the method according to the present invention therefore makes it possible to reduce the financial costs of industrial production of the compounds of formula (I).
  • a subject of the present invention is therefore a process for the preparation of a compound derived from thiazolidinedione, oxazolidinedione or hydantoin of formula (I) from a compound of formula (II) below:
  • the catalyst based on transition metal used either in the hydrogen transfer reaction or in the hydrogenation reaction, is chosen from a homogeneous or heterogeneous catalyst.
  • transition metal catalysts said to be heterogeneous, supported or not, mention is made of Pt, Pt / C, Pt (0) 2 , Pd, Pd / C, Pd / CaC0 3 , Pd / Si0 2 , Pd / BaC0 3 , Pd (OH) 2 / C, Ir, Ir / C, Ru, Ru / C, Rh, Raney Ni, Fe.
  • a secondary solvent is advantageously chosen from water, a hydrocarbon such as hexane, heptane, octane, nonane, decane, benzene, toluene and xylene, an ether such as tetrahydrofuran, dioxane , dimethoxyethane, diisopropyl ether and diethylene glycol dimethyl ether, an ester such as ethyl acetate, butyl acetate and ethyl propionate, a ketone such as acetone, diisopropyl ketone, methylisobutyl ketone, ethyl ethyl ketone and acetyl acetone, an alcohol such as methanol, ethanol, n-propanol, isopropanol, butanol, isobutanol, and meth
  • a preferred form of implementation of the process for the preparation of compounds of formula (I) by a hydrogenation reaction according to the invention comprises the treatment of the compound of formula (II), in the presence of formic acid and a catalyst, under the following operating conditions:
  • a preferred form of implementation of the process for the preparation of compounds of formula (I) by a hydrogen transfer reaction according to the invention comprises the treatment of the compound of formula (II), in the presence of formic acid and d 'A catalyst, preferably under the following operating conditions:
  • reaction time of between 0.5 and 40 hours.
  • Example 1 Preparation of the compound; [(ethyl-5-pyridyl-2-) ethoxy-4-] benzyl ⁇ -5-thiazolidine-2,4-dione-2,4 according to a hydrogenation reaction.
  • reaction medium is cooled to room temperature (20-25 ° C).
  • the catalyst is filtered and rinsed with 60 ml of formic acid.
  • the filtrate is concentrated under vacuum at 40 ° C to 40 ml. 80 ml of water and 60 ml of formic acid are added to the concentrate. The pH value of the solution is equal to 0.93. 101 g of a solution of
  • the crude product is washed in ethanol as follows.
  • the product is dissolved in 172 ml of ethanol, the mixture is refluxed for 30 min, cooled to 10 ° C and the product is filtered.
  • Example 2 Preparation of the compound; ⁇ [(ethyl-5-pyridyl-2-) ethoxy-4-1benzyl> -5-thiazolidine-2, 4-dione-2, 4 according to a hydrogen transfer reaction by homogeneous catalysis.
  • Example 3 Compound preparation; ⁇ [(ethyl-5-pyridyl-2-) ethoxy-4-lbenzyl> -5-thiazolidine-2,4-dione-2,4 according to a hydrogen transfer reaction by heterogeneous catalysis.
  • the solution is heated to reflux for 5 hours.
  • the HPLC profile of the reaction medium indicates a transformation rate of 78%.
  • the medium is concentrated to 5 ml.
  • Example 4 Compound preparation; -f [(ethyl-5-pyridyl-2-) ethoxy-4-1benzyl> -5-thiazolidine-2,4-dione-2,4 according to a hydrogen transfer reaction by heterogeneous catalysis.
  • the solution is heated to reflux (105 ° C) for 21 hours.
  • the HPLC profile of the reaction medium indicates a conversion rate of 66%.
  • the medium is concentrated to 5 ml.
  • Example 5 Preparation of the compound: -ff (ethyl-5-pyridyl-2-) ethoxy-4-] benzyl> -5-thiazolidine-2, 4-dione-2, 4 according to a hydrogen transfer reaction by heterogeneous catalysis. Under nitrogen, in a 0.5 1 flask are introduced 20 g of ⁇ [(ethyl-5-pyridyl-2-) ethoxy-4-] benzylylidene ⁇ -5-thiazolidine-2, 4-dione-2, 4, 0.6 g of Pt (0) 2 (2.5% platinum / substrate) and 200 ml of 99% formic acid. The solution is heated to the temperature of 84
  • the HPLC profile of the reaction medium indicates a conversion rate of 98.3% into the product formed.
  • reaction medium is filtered and the filtrate is concentrated to 40 ml.
  • the product is filtered.
  • the product is purified by repasting in ethanol.
  • the solution is heated to the temperature of 80-85 ° C for 19 hours 30 minutes.
  • the HPLC profile of the reaction medium indicates a conversion rate of 98.4% into the product formed.
  • Example 7 Preparation of the compound: -f [(ethyl-5-pyridyl-2-) ethoxy-4-1benzyl> -5-thiazolidine-2,4-dione-2,4 according to a hydrogen transfer reaction by heterogeneous catalysis. Under nitrogen, in a 100 ml tetracol are introduced 5 g of ⁇ [(ethyl-5-pyridyl-2-) ethoxy-4-] benzylylidene ⁇ -5-thiazolidine-2, 4-dione-2, 4, 0.203 g of Pt (0) 2 (3.4% platinum / substrate) and 50 ml of 99% formic acid. The solution is heated to the temperature of 80-
  • the HPLC profile of the reaction medium indicates a conversion rate of 98% into the product formed.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
EP02704834A 2001-02-14 2002-02-14 Verfahren zur herstellung von thiazolidindion-derivaten oder von oxazolidindion-derivaten Withdrawn EP1360179A2 (de)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
FR0102010A FR2820741A1 (fr) 2001-02-14 2001-02-14 Procede de preparation de composes derives de thiazolidinedione, d'oxazolidinedione ou d'hydantoine
FR0102010 2001-02-14
FR0105206A FR2820742B1 (fr) 2001-02-14 2001-04-17 Procede de preparation de composes derives de thiazolidinedione, d'oxazolidinedione ou d'hydantoine
FR0105206 2001-04-17
PCT/FR2002/000571 WO2002064577A2 (fr) 2001-02-14 2002-02-14 Procede de preparation de composes derives de thiazolidinedione, d'oxazolidinedione

Publications (1)

Publication Number Publication Date
EP1360179A2 true EP1360179A2 (de) 2003-11-12

Family

ID=26212876

Family Applications (1)

Application Number Title Priority Date Filing Date
EP02704834A Withdrawn EP1360179A2 (de) 2001-02-14 2002-02-14 Verfahren zur herstellung von thiazolidindion-derivaten oder von oxazolidindion-derivaten

Country Status (13)

Country Link
US (1) US6849741B2 (de)
EP (1) EP1360179A2 (de)
JP (1) JP2004520401A (de)
KR (1) KR100856140B1 (de)
CN (1) CN1491218A (de)
AU (1) AU2002238645A1 (de)
BR (1) BR0206967A (de)
CA (1) CA2438105A1 (de)
FR (1) FR2820742B1 (de)
IL (1) IL157101A0 (de)
MX (1) MXPA03007263A (de)
RU (1) RU2003127720A (de)
WO (1) WO2002064577A2 (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005514390A (ja) * 2001-12-20 2005-05-19 テバ ファーマシューティカル インダストリーズ リミティド チアゾリジンジオン系糖尿病治療薬前駆体の水素化
CZ297347B6 (cs) * 2004-09-21 2006-11-15 Zentiva, A. S. Zpusob prípravy rosiglitazonu
EP1903042A3 (de) * 2006-09-22 2008-05-28 Cadila Pharmaceuticals Limited Ein verbessertes Verfahren zur Hydrierung von Zusammensetzungen aus 5-(substitutiertem Benzyliden) 2,4- Thiazolidin-Dion, um das entsprechende ( +/- ) 5- (substituierte Benzyl) 2,4-Thiazolidin-Dion zu erzeugen

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4812570A (en) * 1986-07-24 1989-03-14 Takeda Chemical Industries, Ltd. Method for producing thiazolidinedione derivatives
DE69132713D1 (de) * 1990-04-27 2001-10-11 Sankyo Co Benzylidenthiazolidinderivate, ihre Herstellung und ihre Anwendung als Lipidperoxid-Inhibitoren
JP2766730B2 (ja) * 1991-12-20 1998-06-18 ジ・アップジョン・カンパニー 置換５‐メチレン‐チアゾリジンジオンの還元方法
JP3163361B2 (ja) * 1992-03-12 2001-05-08 味の素株式会社 ５−アルキルヒダントイン誘導体の製造法
US5399632A (en) * 1992-09-30 1995-03-21 Exxon Research & Engineering Co. Hydrogenation process for unsaturated homo and copolymers
JPH06199808A (ja) * 1993-01-04 1994-07-19 Ajinomoto Co Inc ５−シクロヘキシルメチルヒダントイン誘導体の製造方法およびその製造中間体
JPH08277279A (ja) * 1995-04-05 1996-10-22 Nitto Chem Ind Co Ltd ベンジルチアゾリジンジオン誘導体の製造方法
US5952509A (en) * 1996-06-27 1999-09-14 Takeda Chemical Industries, Ltd. Production of benzaldehyde compounds
UY24886A1 (es) * 1997-02-18 2001-08-27 Smithkline Beecham Plc Tiazolidindiona
DE19711616A1 (de) * 1997-03-20 1998-09-24 Boehringer Mannheim Gmbh Verbessertes Verfahren zur Herstellung von Thiazolidindionen
JP4084501B2 (ja) * 1999-07-01 2008-04-30 三井化学株式会社 α−メルカプトカルボン酸およびその製造方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO02064577A2 *

Also Published As

Publication number Publication date
US20040059121A1 (en) 2004-03-25
WO2002064577A2 (fr) 2002-08-22
BR0206967A (pt) 2004-03-09
FR2820742A1 (fr) 2002-08-16
KR20030082594A (ko) 2003-10-22
RU2003127720A (ru) 2005-03-20
CN1491218A (zh) 2004-04-21
AU2002238645A1 (en) 2002-08-28
MXPA03007263A (es) 2005-02-14
KR100856140B1 (ko) 2008-09-03
US6849741B2 (en) 2005-02-01
WO2002064577A3 (fr) 2003-01-03
FR2820742B1 (fr) 2005-03-11
IL157101A0 (en) 2004-02-08
CA2438105A1 (fr) 2002-08-22
JP2004520401A (ja) 2004-07-08

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Inventor name: PINTUS, TONY

Inventor name: DERRIEN, YVON

Inventor name: BULLIARD, MICHEL,SYNKEM FOURNIER PHARMA

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