ANALOGIFOERFARANDE FOER FRAMSTAELLNING AV ETT PENAMDERIVAT ANVAENDBART SAOSOM ETT ANTIBAKTERISKT MEDEL

摘要

1481600 Penicillin derivatives PFIZER Inc 8 Oct 1974 [17 Oct 1973 12 March 1974] 43620/74 Heading C2C [Also in Division C3] The invention comprises compounds of the formula and salts thereof, where R x is an amino or substituted amino group, which substituted amino group is R1-NH-, (R5)1-NH-, or Ry is a tetrazolyl group of the formula or a precursor for a tetrazolyl group of the formula and R2 or R3 is hydrogen trialkylsilyl having 1-4 carbon atoms in each of said alkyl groups, alkanoyloxymethyl having from three to eight carbon atoms, 1 - (alkanoyl oxy)ethyl having from four to nine carbon atoms, phthalidyl or a tetrazolylpenam nitrogen protecting group removable from specific compound of said formula; Hal is Cl or Br, R1 is an acyl group of an organic carboxylic acid; (R5)1 is an amino protecting group other than an acyl group, R8 is phenyl, 1,4-cyclohexadienyl, 3-sydnonyl, thienyl, furyl, pyridyl, thiazolyl, isothiazolyl, tetrazolyl, triazolyl, imidazolyl, pyrazolyl, substituted phenyl, substituted thienyl, substituted furyl, substituted pyridyl, substituted thiazolyl, substituted isothiazolyl, substituted triazolyl, substituted imidazolyl or substituted pyrazolyl, each substituted moiety being substituted by up to two of fluoro, chloro, bromo, hydroxy, alkyl having from one to six carbon atoms, alkoxy having from one to six carbon atoms or alkylthio having from one to six carbon atoms; R9 and R10 are hydrogen, methyl or ethyl; R12 and R13 are each alkyl having from one to six carbon atoms, or taken together with the nitrogen atom to which they are attached form a pyrrolidino, morpholino, piperidino or azacyloheptan-l-yl group, and G1 is a tetrazolyl penam nitrogen protecting group or a group readily convertible to a tetrazolyl penam protecting group and providing that when Ry is a precursor for a tetrazolyl group R x must be (R5)1-NH. The compounds may be prepared by (a) converting a -COOH group at 3-position of a precursor into a group Ry by known methods, (b) acylating an amino group at a 6- position of the penam structure with an acylating agent by known methods to form a grouping for R x of R1NH-.