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1. 发明授权

US4800044A Intermediates for the production of 1,2-dithiolan acid (thioctic acid) 失效
标题翻译：用于生产1,2-二硫戊酸（硫辛酸）的中间体
公开(公告)号：US4800044A
公开(公告)日：1989-01-24
申请号：US73820
申请日：1987-07-15
申请人： Guenes Giray , Klaus Huthmacher , Axel Kleemann , Thomas Lied
发明人： Guenes Giray , Klaus Huthmacher , Axel Kleemann , Thomas Lied
IPC分类号： C07C323/52 , A61K31/385 , A61P1/16 , A61P25/00 , C07C67/00 , C07C313/00 , C07C319/06 , C07C319/14 , C07C319/20 , C07C323/22 , C07C327/22 , C07D339/04 , C07C149/40
CPC分类号： C07D339/04 , C07C323/00
摘要： Compounds of forumla XII ##STR1## wherein R.sub.1 is hydrogen and R.sub.2 is phenyl or benzyl are useful as intermediates in the preparation of 1,2-dithiolane-3-pentanoic acid (D,L-thioctic acid) of formula IX ##STR2##
摘要翻译：其中R 1是氢和R 2是苯基或苄基的化合物可用作制备式IX的1,2-二硫戊环-3-戊酸（D，L-硫辛酸）的中间体九，

2. 发明授权

US4966732A Process for the production of 1,2-dithiolan-3-pentanoic acid (thioctic acid) and 8-hydrocarbylthio-6-oxooctanoic acid 失效
标题翻译：生产1,2-二硫戊环-3-戊酸（硫辛酸）和8-烃基硫代-6-氧代辛酸的方法
公开(公告)号：US4966732A
公开(公告)日：1990-10-30
申请号：US73584
申请日：1987-07-15
申请人： Guenes Giray , Klaus Huthmacher , Axel Kleemann , Thomas Lied
发明人： Guenes Giray , Klaus Huthmacher , Axel Kleemann , Thomas Lied
IPC分类号： C07C323/52 , A61K31/385 , A61P1/16 , A61P25/00 , C07C67/00 , C07C313/00 , C07C319/06 , C07C319/14 , C07C319/20 , C07C323/22 , C07C327/22 , C07D339/04
CPC分类号： C07D339/04 , C07C323/00
摘要： 1,2-Dithiolane-3-pentanoic acid (D,L-thioctic acid) of the formula ##STR1## is prepared by a process comprising (a) reacting a 2-(3-alkylthiopropionyl)-cyclopentanone-1 of the formula ##STR2## where R is a C.sub.1 -C.sub.4 alkyl, phenyl or benzyl in aqueous alkaline solution at a temperature of about 20.degree. C. to about 90.degree. C. to form the corresponding carboxylic acid of formula VI ##STR3## (b) reacting the compound of formula VI with an alkyl mercaptan at a temperature between -20.degree. C. and 0.degree. C. to form the corresponding thioketal of formula VII ##STR4## (c) reacting the compound of formula VII with sodium in liquid ammonia at temperature temperture between -60.degree. C. and -10.degree. C. to form the 6,8-dimercaptooctanic acid of formual VIII ##STR5## (d) reacting the 6,8-dimercaptooctanoic acid of formula VIII in alkaline solution with an iron (III) salt and oxygen to form the 1,2-dithiolane-3-pentanoic acid of formula IX, or in place of steps (a) through (c) reacting an acid of formula XII ##STR6## where R.sub.1 and R.sub.2 are hydrogen, C.sub.1 -C.sub.4 -alkyl, phenyl or benzyl, with the proviso that both R.sub.1 and R.sub.2 cannot be benzyl, with sodium in liquid ammonia at a temperature between -60.degree. C. and -10.degree. C. to form the corresponding 6,8-dimercaptooctanoic acid of formula VIII. The compounds of formulae VI, VII, XII are new.

3. 发明授权

US4705867A Process for the production of 1,2-dithiolan-3-pentanoic acid (thioctic acid) and intermediate compounds therefor 失效
标题翻译：生产1,2-二硫戊环-3-戊酸（硫辛酸）及其中间体化合物的方法
公开(公告)号：US4705867A
公开(公告)日：1987-11-10
申请号：US848212
申请日：1986-04-04
申请人： Guenes Giray , Klaus Huthmacher , Axel Kleemann , Thomas Lied
发明人： Guenes Giray , Klaus Huthmacher , Axel Kleemann , Thomas Lied
IPC分类号： C07C323/52 , A61K31/385 , A61P1/16 , A61P25/00 , C07C67/00 , C07C313/00 , C07C319/06 , C07C319/14 , C07C319/20 , C07C323/22 , C07C327/22 , C07D339/04
CPC分类号： C07D339/04 , C07C323/00
摘要： 1,2-Dithiolane-3-pentanoic acid (D,L-thioctic acid) of the formula ##STR1## is prepared by a process comprising (a) reacting a 2-(3-alkylthiopropionyl)-cyclopentanone-1 of the formula ##STR2## where R is a C.sub.1 -C.sub.4 alkyl, phenyl or benzyl in aqueous alkaline solution at a temperature of about 20.degree. C. to about 90.degree. C. to form the corresponding carboxylic acid of formula VI ##STR3## (b) reacting the compound of formula VI with an alkyl mercaptan at a temperature between -20.degree. C. and 0.degree. C. to form the corresponding thioketal of formula VII ##STR4## (c) reacting the compound of formula VII with sodium in liquid ammonia at a temperature between -60.degree. C. and -10.degree. C. to form the 6,8-dimercaptooctanoic acid of formula VIII ##STR5## (d) reacting the 6,8-dimercaptooctanoic acid of formula VIII in alkaline solution with an iron (III) salt and oxygen to form the 1,2-dithiolane-3-pentanoic acid of formula IX, or in place of steps (a) through (c) reacting an acid of formula XII ##STR6## where R.sub.1 and R.sub.2 are hydrogen, C.sub.1 -C.sub.4 -alkyl, phenyl or benzyl, with the proviso that both R.sub.1 and R.sub.2 cannot be benzyl, with sodium in liquid ammonia at a temperature between -60.degree. C. and -10.degree. C. to form the corresponding 6,8-dimercaptooctanoic acid of formula VIII. The compounds of formulae VI, VII, XII are new.
摘要翻译：式（IX）的1,2-二硫戊环-3-戊酸（D，L-硫辛酸）是通过以下方法制备的，该方法包括：（a）使式（I）的2-（3-烷硫基丙酰基） - 环戊酮-1 V，其中R是在约20℃至约90℃的温度下在碱性水溶液中的C 1 -C 4烷基，苯基或苄基，以形成相应的式VI的羧酸）使式Ⅵ化合物与烷基硫醇在-20℃至0℃之间的温度下反应，形成相应的式Ⅶ的缩酮醛Ⅶ（c）使式Ⅶ化合物与液体中的钠反应在-60℃至-10℃的温度下加入氨以形成式VIII的6,8-二巯基辛酸VIII（d）使式VIII的6,8-二巯基辛酸在碱性溶液中与铁（III）盐和氧气以形成式IX的1,2-二硫戊环-3-戊酸，或代替步骤（a）至（c）使式XI的酸其中R 1和R 2是氢，C 1 -C 4 - 烷基，苯基或苄基，条件是R 1和R 2不能是苄基，钠在液氨中在-60℃和-60℃之间， 10℃，形成相应的式VIII的6,8-二巯基辛酸。式VI，VII，XII的化合物是新的。

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