Method of manufacturing substance gm-95

Details Method of manufacturing substance gm-95 Method of manufacturing substance gm-95

C - Chemistry, Metallurgy

07

D

C07D 498/22 (2006.01) A61K 31/424 (2006.01) A61K 31/429 (2006.01) A61P 35/00 (2006.01) C07D 513/22 (2006.01) C07D 263/34 (2006.01)

Patent

CA 2436942

A method of manufacturing substance GM-95 having general formula [I], comprising (a) deprotecting a macrocyclic compound having general formula [II] (wherein, R1's are the same or different and each represents a lower alkyl group, and R2 represents a thiol protecting group) by removing acetal protecting groups (the R1's) thereof, and forming an oxazole ring through an intramolecular cyclization reaction between produced formyl group and an amide group, and (b) deprotecting a resulting macrocyclic compound having general formula [III] (wherein, R2 is as mentioned above) by removing the thiol protecting group (R2) thereof, and forming a thiazoline ring through an intramolecular cyclization reaction between a thiol group thus produced and an amide group.

L'invention concerne un procédé destiné à la préparation d'une substance GM-95 [I], consistant (a) à débloquer un composé cyclique représenté par la formule générale [II] (dans laquelle les R<1> représentent chacun un alkyle inférieur et R<2> représente un groupe de protection thiol) pour transformer le groupe acétal en groupe formyle par enlèvement des groupes de protection (R<1>) et à faire réagir le groupe formyle avec le groupe amido par cyclisation intramoléculaire pour former un noyau oxazole, et (b) à débloquer le composé cyclique obtenu représenté par la formule générale [III] pour enlever le groupe de protection thiol (R<2>) et à faire réagir le groupe thiol résultant avec le groupe amido par cyclisation intramoléculaire pour former un noyau thiazoline.

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