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1. WO2005026110 - OPTICALLY ACTIVE 3,3'-DITHIOBIS(2-AMINO-2­METHYLPROPIONIC ACID) DERIVATIVE AND PROCESS FOR PRODUCING OPTICALLY ACTIVE 2-AMINO-3-MERCAPTO-2-METHYL­PROPIONIC ACID DERIVATIVE

Publication Number WO/2005/026110
Publication Date 24.03.2005
International Application No. PCT/JP2004/012157
International Filing Date 18.08.2004
IPC
C07C 319/06 2006.1
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
319Preparation of thiols, sulfides, hydropolysulfides or polysulfides
02of thiols
06from sulfides, hydropolysulfides or polysulfides
C07C 323/58 2006.1
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
323Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
50containing thio groups and carboxyl groups bound to the same carbon skeleton
51having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
57the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
58with amino groups bound to the carbon skeleton
CPC
C07B 2200/07
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
2200Indexing scheme relating to specific properties of organic compounds
07Optical isomers
C07C 319/06
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
319Preparation of thiols, sulfides, hydropolysulfides or polysulfides
02of thiols
06from sulfides, hydropolysulfides or polysulfides
C07C 323/58
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
323Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
50containing thio groups and carboxyl groups bound to the same carbon skeleton
51having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
57the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
58with amino groups bound to the carbon skeleton
C07D 233/76
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
233Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
54having two double bonds between ring members or between ring members and non-ring members
66with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
72Two oxygen atoms, e.g. hydantoin
76with substituted hydrocarbon radicals attached to the third ring carbon atom
C07D 403/12
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
403Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
02containing two hetero rings
12linked by a chain containing hetero atoms as chain links
C12P 11/00
CCHEMISTRY; METALLURGY
12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
PFERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
11Preparation of sulfur-containing organic compounds
Applicants
  • 株式会社カネカ KANEKA CORPORATION [JP]/[JP] (AllExceptUS)
  • 松本 慎吾 MATSUMOTO, Shingo [JP]/[JP] (UsOnly)
  • 村尾 博 MURAO, Hiroshi [JP]/[JP] (UsOnly)
  • 山口 貴生 YAMAGUCHI, Takao [JP]/[JP] (UsOnly)
  • 泉田 将司 IZUMIDA, Masashi [JP]/[JP] (UsOnly)
  • 上田 恭義 UEDA, Yasuyoshi [JP]/[JP] (UsOnly)
Inventors
  • 松本 慎吾 MATSUMOTO, Shingo
  • 村尾 博 MURAO, Hiroshi
  • 山口 貴生 YAMAGUCHI, Takao
  • 泉田 将司 IZUMIDA, Masashi
  • 上田 恭義 UEDA, Yasuyoshi
Common Representative
  • KANEKA CORPORATION
Priority Data
2003-31740209.09.2003JP
Publication Language Japanese (ja)
Filing Language Japanese (JA)
Designated States
Title
(EN) OPTICALLY ACTIVE 3,3'-DITHIOBIS(2-AMINO-2­METHYLPROPIONIC ACID) DERIVATIVE AND PROCESS FOR PRODUCING OPTICALLY ACTIVE 2-AMINO-3-MERCAPTO-2-METHYL­PROPIONIC ACID DERIVATIVE
(FR) DERIVE OPTIQUEMENT ACTIF DE 3,3-DITHIOBIS (ACIDE 2-AMINO-2-METHLYPROPIONIQUE) ET PROCEDE DE PRODUCTION D'UN DERIVE OPTIQUEMENT ACTIF D'ACIDE 2-AMINO-3-MERCAPTO-2-METHYL-PROPIONIQUE
(JA) 光学活性3,3’-ジチオビス(2-アミノ-2-メチルプロピオン酸)誘導体、並びに、光学活性2-アミノ-3-メルカプト-2-メチルプロピオン酸誘導体の製造方法
Abstract
(EN) A useful novel intermediate and a novel synthesis method which enable an optically active (R)- or (S)-2-amino-3-mercapto-2-methylpropionic acid derivative or a salt thereof which each is useful as an intermediate for medicines, etc. to be synthesized while highly inhibiting the inclusion of various impurities. A process is provided in which an optically active (R)- or (S)-2-amino-3-mercapto-2-methyl­propionic acid derivative or a salt thereof each having a high purity can be easily and efficiently produced on an industrial scale. The process, which is for producing a 2-amino-3-mercapto-2-methylpropionic acid derivative or a salt thereof each having a high purity, is characterized in that a high-purity, optically active 3,3'-dithiobis(2-amino-2­methylpropionic acid) derivative from which impurities have been removed is used as an intermediate and the sulfur-sulfur bond of this intermediate is reductively cleaved to convert the derivative into the corresponding optically active 2-amino-3-mercapto-2-methylpropionic acid derivative without generating by-product impurities difficult to remove.
(FR) La présente invention se rapporte à un nouveau composé intermédiaire utile et à un nouveau procédé de synthèse permettant la synthèse d'un dérivé optiquement actif d'acide (R)- ou (S)-2-amino-3-mercapto-2-méthylpropionique ou d'un sel de ce dérivé, qui sont chacun utiles en tant qu'intermédiaire pour la production de médicaments, etc., tout en inhibant fortement l'inclusion de diverses impuretés. L'invention concerne un procédé dans lequel il est possible de produire facilement et efficacement, à une échelle industrielle, un dérivé optiquement actif d'acide (R)- ou (S)-2-amino-3-mercapto-2-méthyl-propionique ou un sel de ce dérivé, le dérivé et le sel présentant tous deux une grande pureté. Ce procédé, qui est conçu pour la production d'un dérivé ou d'un sel de 2-amino-3-mercapto-2-méthylpropionique doté chacun d'une grande pureté, se caractérise en ce qu'un dérivé optiquement actif, de grande pureté, de 3,3'-dithiobis(acide 2-amino-2-méthylpropionique) duquel les impuretés ont été retirées, est utilisé en tant qu'intermédiaire, et la liaison soufre-soufre de cet intermédiaire est coupée par réduction aux fins de la conversion du dérivé dans ledit dérivé correspondant optiquement actif d'acide 2-amino-3-mercapto-2-méthylpropionique, sans génération d'impuretés dérivées difficiles à supprimer.
(JA) 医薬品等の中間体として有用な光学活性なR体又はS体の2−アミノ−3−メルカプト−2−メチルプロピオン酸誘導体又はその塩を各種不純物の混入を高度に抑制し得る、有用な新規製造中間体および新規合成法を開発し、工業的生産規模において簡便且つ効率的に、高純度の光学活性なR体又はS体の2−アミノ−3−メルカプト−2−メチルプロピオン酸誘導体又はその塩を製造する方法を提供する。不純物を除去した高純度の光学活性3,3'−ジチオビス(2−アミノ−2−メチルプロピオン酸)誘導体を製造中間体とし、この中間体の硫黄−硫黄結合を還元的に開裂して、除去困難な不純物を副生させることなく、対応する光学活性2−アミノ−3−メルカプト−2−メチルプロピオン酸誘導体に変換することを特徴とする、高純度の2−アミノ−3−メルカプト−2−メチルプロピオン酸誘導体又はその塩の製造方法である。
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