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    ACYL DERIVATIVES
    10.
    发明专利
    ACYL DERIVATIVES 未知

    公开(公告)号：ZA728924B

    公开(公告)日：1973-09-26

    申请号：ZA728924

    申请日：1972-12-18

    Applicant: HOFFMANN LA ROCHE

    Inventor： FURLENMEIER A ,  VOGLER K ,  LANZ P ,  QUITT P

    IPC: C07D207/32 ,  C07D207/327 ,  C07D209/18 ,  C07D213/55 ,  C07D257/04 ,  C07D307/54 ,  C07D333/24 ,  C07D499/00 ,  C07D499/60 ,  C07D

    Abstract: 1353578 Penicillins F HOFFMANN-LA ROCHE & CO AG 11 Jan 1973 [12 Jan 1972] 1605/73 Headings C2A and C2C Novel penicillins having the general Formula (I) and salts thereof, wherein T is a C 2-5 alkyl group and R is a furyl, pyrrolyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, pyridyl, pyrimidinyl, tetrazolyl or indolyl group, which groups R can be substituted by halogen, C 1-3 alkyl, C 1-3 alkoxy or C 1-3 alkylthio, are prepared by N-acylating 6- aminopenicillanic acid (having the carboxyl group protected) with an acid of Formula (II) wherein T and R have the aforesaid meanings, or with an N-acylating functional derivative thereof, and cleaving off the carboxyl-protecting group. The carboxyl group may be protected by saltformation or esterification. Functional derivatives of the acid (II) are, e.g. halides, azides, anhydrides, reactive esters and active amides. When the acid itself is used, a condensing agent such as dicyclohexylcarbodiimide is preferably present. The reaction is usually performed in an inert solvent. The acids of Formula (II) above, which are said to be novel, are prepared by reacting an acid of Formula (V) with the benzyl or tert. butyl ester of a compound of Formula IV in the presence of benzenesulphonyl chloride or phosgene, R and T having the aforesaid meanings, to give an ester of Formula (III) wherein B is a benzyl- or tert.butyl-protected carboxyl group and then cleaving off the protecting group, e.g. by hydrogenation or treatment with a strong acid respectively, to give the desired acid (II). The latter may be converted to the corresponding acid chloride with thionyl chloride. Examples are given for preparing the following acids (II): (R)-2-[(2-isopropyl-2H- tetrazol - 5 - yl)acetoxy] - isocaproic acid; (R)-2- [(2-thienyl)acetoxy]isocaproic acid; and (R)-2-[(3- indolyl)acetoxy]isocaproic acid. Pharmaceutical compositions having antibiotic activity against Gram-positive and -negative bacteria comprise a penicillin of Formula (I) hereinbefore or a salt or hydrate thereof, in association with a compatible pharmaceutical carrier.

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