EP1165529A1 - Procede de preparation de derives de thiazolidine - Google Patents

Procede de preparation de derives de thiazolidine

Info

Publication number
EP1165529A1
EP1165529A1 EP00909666A EP00909666A EP1165529A1 EP 1165529 A1 EP1165529 A1 EP 1165529A1 EP 00909666 A EP00909666 A EP 00909666A EP 00909666 A EP00909666 A EP 00909666A EP 1165529 A1 EP1165529 A1 EP 1165529A1
Authority
EP
European Patent Office
Prior art keywords
compound
formula
preparation
mixture
added
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Withdrawn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
EP00909666A
Other languages
German (de)
English (en)
Inventor
Itsuo Fukui Research Institute OKUMOTO
Nobuyuki Minase R.I. Ono Pharm Co Ltd NAKAMURA
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.)
Ono Pharmaceutical Co Ltd
Original Assignee
Ono Pharmaceutical Co 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 Ono Pharmaceutical Co Ltd filed Critical Ono Pharmaceutical Co Ltd
Publication of EP1165529A1 publication Critical patent/EP1165529A1/fr
Withdrawn legal-status Critical Current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
    • 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

Definitions

  • the present invention relates to a process for the preparation of thiazolidine derivatives . More particularly, the present invention relates to a process for the preparation of a compound of formula ( I )
  • thiazolidine derivatives including a compound of formula ( I ) reduce blood sugar level and therefore are useful for the treatment of non-insulin dependent diabetes mellitus.
  • many methods for the preparation of thiazolidine derivatives are illustrated. Thereamong some of methods for the preparation of a compound of formula ( I ) are extracted in the following reaction scheme 1 and 2.
  • D ring is
  • A is C2-6 alkylene and X is halogen.
  • R 1 is alkyl and the other symbols are as defined above.
  • the present inventors investigated energetically in order to improve the problem, so that the present inventors found that in the presence of ammonia addition of an alkali metal increased the yield very much and completed the invention.
  • the present invention relates to a process for the preparation of a compound of formula (I)
  • A is C2-6 alkylene.), consisting of subjecting to reaction a compound of formula (II)
  • reaction of preparing a compound of formula ( I ) from a compound of formula (II) and a compound of formula (V) is, for example, carried out by subjecting to reaction a compound of formula (II) and a compound of formula (V) in the presence of liquid ammonia, using an alkali metal (lithium, sodium etc.
  • a compound of formula (II) which is used as a starting material in the above reaction is known and it is , for example , prepared according to the above reaction scheme 1.
  • Cl-4 alkyl is methyl, ethyl, propyl, butyl and isomers thereof.
  • C2-6 alkylene is ethylene, propylene, tetramethylene, pentamethylene, hexamethylene and isomers thereof.
  • halogen is fluorine, chlorine, bromine and iodine.
  • D ring is preferably
  • A is preferably C2-3 alkylene.
  • the present invention gives an excellent method in the preparation of a compound of formula ( I ) which is a target compound.
  • the method of the present invention gives a compound of formula ( I ) in about two or three times as high yield as the previously known method (i.e. A compound of formula ( I ) is given about 60-90% yield by the present method; about 20-30% yield by the previous method. ) .
  • the method of the present invention is more excellent than the previous method and is suitable for industrial mass synthesis.
  • the solvents in parentheses show the developing or eluting solvents and the ratios of the solvents used are by volume in chromatographic separations .
  • the crystal that appeared was gathered and washed by water and ethanol successively, dried under reduced pressure to give a crude crystal.
  • the crude crystal was dissolved in ethanol under refluxing condition.
  • activated carbon To the mixture was added activated carbon.
  • the mixture was stirred at the same temperature and filtrated with heating.
  • the filtrate was stirred at ambient temperature for 5 hours.
  • the crystal that appeared was filtered off and was dried under reduced pressure to give the compound of the present invention (303 g, 75% yield) having the following physical data.
  • the aqueous layer was acidified by adding cone, hydrochloric acid and the mixture was extracted with ethyl acetate.
  • the organic layer was washed by 2N hydrochloric acid, dried over anhydrous magnesium sulfate and was concentrated under reduced pressure.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé de préparation d'un composé de thiazolidine représenté par la formule (I) (dans laquelle le cycle D est (i) (R représentant un hydrogène, un alkyle en C1-4, un halogène ou un cyano) ou (ii) et A représente un alkylène en C2-6). Le procédé selon la présente invention permet d'obtenir un composé de la formule (I) avec un rendement plus élevé que par le procédé antérieur.
EP00909666A 1999-03-18 2000-03-16 Procede de preparation de derives de thiazolidine Withdrawn EP1165529A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP7351999 1999-03-18
JP7351999 1999-03-18
PCT/JP2000/001595 WO2000055146A1 (fr) 1999-03-18 2000-03-16 Procede de preparation de derives de thiazolidine

Publications (1)

Publication Number Publication Date
EP1165529A1 true EP1165529A1 (fr) 2002-01-02

Family

ID=13520586

Family Applications (1)

Application Number Title Priority Date Filing Date
EP00909666A Withdrawn EP1165529A1 (fr) 1999-03-18 2000-03-16 Procede de preparation de derives de thiazolidine

Country Status (12)

Country Link
EP (1) EP1165529A1 (fr)
KR (1) KR20010112328A (fr)
CN (1) CN1350526A (fr)
AU (1) AU3192400A (fr)
BR (1) BR0009079A (fr)
CA (1) CA2368146A1 (fr)
HU (1) HUP0200585A3 (fr)
NO (1) NO20014451L (fr)
NZ (1) NZ514177A (fr)
TR (1) TR200102689T2 (fr)
WO (1) WO2000055146A1 (fr)
ZA (1) ZA200107603B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2012212393B2 (en) 2011-02-02 2015-06-11 Bionomics Limited Positive allosteric modulators of the alpha 7 nicotinic acetylcholine receptor and uses thereof.

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8919417D0 (en) * 1989-08-25 1989-10-11 Beecham Group Plc Novel compounds
FR2749583B1 (fr) * 1996-06-07 1998-08-21 Lipha Nouveaux derives de thiazolidine -2,4- dione substitues, leurs procedes d'obtention et les compositions pharmaceutiques en renfermant

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0055146A1 *

Also Published As

Publication number Publication date
AU3192400A (en) 2000-10-04
HUP0200585A2 (en) 2002-06-29
HUP0200585A3 (en) 2004-07-28
KR20010112328A (ko) 2001-12-20
TR200102689T2 (tr) 2002-01-21
WO2000055146A1 (fr) 2000-09-21
NO20014451D0 (no) 2001-09-13
NZ514177A (en) 2003-04-29
CA2368146A1 (fr) 2000-09-21
CN1350526A (zh) 2002-05-22
BR0009079A (pt) 2002-01-02
NO20014451L (no) 2001-11-12
ZA200107603B (en) 2003-02-26

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