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1. (WO2002030919) SYNTHESIS OF R(+)$g(a)-LIPOIC ACID
Latest bibliographic data on file with the International Bureau   

Pub. No.:    WO/2002/030919    International Application No.:    PCT/EP2001/011576
Publication Date: 18.04.2002 International Filing Date: 08.10.2001
Chapter 2 Demand Filed:    07.05.2002    
C07D 339/04 (2006.01)
Applicants: LABORATORIO CHIMICO INTERNAZIONALE S.P.A. [IT/IT]; Via Salvini, 10, I-20122 Milano (IT) (For All Designated States Except US).
VILLANI, Flavio [IT/IT]; (IT) (For US Only).
NARDI, Antonio [IT/IT]; (IT) (For US Only).
SALVI, Annibale [IT/IT]; (IT) (For US Only).
FALABELLA, Giovanna [IT/IT]; (IT) (For US Only)
Inventors: VILLANI, Flavio; (IT).
NARDI, Antonio; (IT).
SALVI, Annibale; (IT).
FALABELLA, Giovanna; (IT)
Agent: GERVASI, Gemma; c/o Notarbartolo & Gervasi, Corso di Porta Vittoria, 9, I-20122 Milan (IT)
Priority Data:
MI00A002188 10.10.2000 IT
Abstract: front page image
(EN)Process for the synthesis of R(+)$g(a)-lipoic acid comprising the following stages: a) Salifying of racemic 6,8-halo-octanoic acid with S(-)$g(a)-methylbenzylamine; b) separation by filtration of the crystallized diastereoisomeric salt of R(+)6,8-di-halo-octanoic acid-S(-)$g(a)-methylbenzylamine; c) purification by re-crystallization of the diastereoisomeric salt of R(+)6,8-di-halo-octanoic acid-S(-)$g(a)-methylbenzylamine; d) separation of the diastereoisomeric salt to obtain R(+)6,8-di-halo-octanoic acid by reation of said salt with strong mineral acids in an aqueous solution with a dilution between 2 and 10% by weight; e) esterification of R(+)6,8-di-halo-octanoic acid to obtain the corresponding alkyl ester; f) reaction of the alkyl ester of R(+)6,8-di-halo-octanoic acid in an organic solvent with an aqueous solution of alkali disulfide in presence of a compound for phase transfer catalysis; g) hydolysis of the ester of R(+)$g(a)-lipoic acid.
(FR)L'invention concerne un procédé de synthèse d'acide lipoïque R(+)$g(a) comportant les étapes suivantes : a) la salification d'acide 6,8-halo-octanoïque racémique au moyen de S(-)$g(a)- méthylbenzylamine; b) la séparation par filtrage du sel diastéréoisomérique cristallisé de méthylbenzylamine d'acide 6,8-di-halo-octanoïque S(-)$g(a R(+) c) la purification par recristallisation de sel diastéréoisomérique de méthylbenzylamine d'acide 6,8-di-halo-octanoïque S(-)$g(a R(+); d) la séparation du sel diastéréoisomérique en vue d'obtenir l'acide 6,8-di-halo-octanoïque R(+) par réaction dudit sel avec des acides minéraux forts dans une solution aqueuse présentant une dilution comprise entre 2 et 10 % par poids; e) l'estérification d'acide 6,8-di-halo-octanoïque R(+) en vue d'obtenir l'ester alkyle correspondant; f) la réaction de l'ester alkyle d'acide 6,8-di-halo-octanoïque R(+) dans un solvant organique par une solution aqueuse de disulfure alcalin en présence d'un composant permettant la catalyse de transfert de phase; g) l'hydrolyse de l'ester de l'acide lipoïque R(+)$g(a).
Designated States: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NO, NZ, PH, PL, PT, RO, RU, SD, SE, SG, SI, SK, SL, TJ, TM, TR, TT, TZ, UA, UG, US, UZ, VN, YU, ZA, ZW.
African Regional Intellectual Property Organization (GH, GM, KE, LS, MW, MZ, SD, SL, SZ, TZ, UG, ZW)
Eurasian Patent Organization (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM)
European Patent Office (AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE, TR)
African Intellectual Property Organization (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG).
Publication Language: English (EN)
Filing Language: English (EN)