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classificationCPCInventive http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07F7-0834
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filingDate 1973-11-12-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 1976-04-07-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber GB-1431327-A
titleOfInvention Cephalosporins and methods of production
abstract 1431327 Cephalosporins AMERICAN HOME PRODUCTS CORP 12 Nov 1973 [29 Nov 1972] 52383/73 Addition to 1266544 Heading C2C [Also in Division C3] Acylated cephalosporins substantially free of #<SP>2</SP> isomers may be obtained by acylation, in presence of a weak base, e.g. dimethylaniline or quinoline, followed by hydrolysis, of a "silenated" derivative of the Formula (I) wherein R<SP>1</SP> is H, alkyl, ary or aralkyl, R<SP>2</SP> is alkyl, aryl or aralkyl, R<SP>3</SP> is H or -OOC.CH 3 , R<SP>a</SP> is H or an acyl residue of an organic carboxylic or sulphonic acid, W is H or -SiR<SP>1</SP>R<SP>2</SP>X, where X is halogen, m and p are 0 or 1 and are equal, n is 1-2 and Y is halogen or a group (III) with the provisos that (1) when m = p = 0, n>1, (2) when n>1, the residues A recur in random head-to-head and head-to-tail disposition, and (3) when n is 1, W is H, and Y is a group (III), R<SP>a</SP> is H. They are prepared by adding to previously mixed 7-aminocephalosporanic acid (ACA) of 7-aminodesacetoxycephalosporanic acid (ADCA) and a dihalosilane R<SP>1</SP>R<SP>2</SP>SiX 2 in an inert organic solvent not more than 2 equivalents per mole of silane of an acid acceptor: this procedure avoids isomerization of the double bond from the 3 to the 2 position. The product depends on the ratios of base to silane and of silane to ACA or ADCA, which may be in the ranges 1 : 1 to 2 : 1 and 1 : 2 to 2 : 1 respectively. In the examples Et 3 N, Et 2 NH or anhydrous NH 3 solution is added to mixtures of Me 2 SiCl 2 and ACA or ADCA in CH 2 Cl 2 or CH 3 CN, in molar ratios 2 : 1 : 1. The products are reconverted to ACA or ADCA by addition to water, or are acylated with thienylacetyl chloride or phenylglycyl chloride hydrochloride in the presence of N,N-dimethylaniline then treated with water to give "cephalothin", "cephaloglycin" and "cephalexin".
priorityDate 1972-11-29-04:00^^<http://www.w3.org/2001/XMLSchema#date>
type http://data.epo.org/linked-data/def/patent/Publication

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