Method for producing bis-penicillanoyloxy-alkanes

Details Method for producing bis-penicillanoyloxy-alkanes Method for producing bis-penicillanoyloxy-alkanes

C - Chemistry, Metallurgy

07

D

260/100, 260/18,

C07D 499/00 (2006.01) C07D 209/44 (2006.01) C07D 209/52 (2006.01) C07D 221/20 (2006.01) C07D 281/06 (2006.01) C07D 295/067 (2006.01) C07D 295/194 (2006.01)

Patent

CA 1112239

ABSTRACT OF THE DISCLOSURE Processes are provided for producing novel esters and salts thereof with certain pharmaceutically acceptable acids, e.g. non-toxic strong inorganic acids or organic acids. The novel compounds have the formula Image I in which R1 and R2 represent the same or different substituents, and each represents hydrogen or lower alkyl; A represents a carbon chain having from 5 to 8 carbon atoms, a carbon chain having 5 to 8 carbon atoms in which an oxygen atom is substituted for a methylene group, a carbon atom chain having 5 to 8 carbon atoms in which a sulphur atom is substituted for a methylene group, or the grouping Image represents a bicyclic system containing from 5 to 10 carbon atoms, or a bicyclic system containing from 4 to 9 carbon atoms, or a bicyclic system containing from 4 co 9 carbon atoms in which an oxygen atom is substitu- ted for a methylene group, or a bicyclic system containing from 4 to 9 carbon atoms in which a sulphur atom is substituted for a methylene group, or the grouping Image represents a spirocyclic system containing from 7 to 10 carbon atoms; and R3 represnts hydrogen, lower alkyl selected from methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl tert-butyl, pentyl, neopentyl and hexyl and the corresponding isomers, and halogen substituted lower alkyl selected from chloromethyl, trichloromethyl, trifluoromethyl and 2,2,2- trichloroethyl and similar radical, and unsubstituted aryl and aralkyl, the aryl part of which is selected from phenyl, 2-fluorophenyl, 3-fluoro- phenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,6-dichlorophenyl, 2,4,6-trichlorophenyl, 2-hydroxyphenyl, 3-hydroxyphenyl, 4-hydroxyphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 4-ethoxyphenyl, 4-isopropyloxyphenyl, 2-tolyl, 3-tolyl, 4-tolyl, 1-naphthyl, and 2-naphthyl. These compounds are valuable in human and veterinary prac- tice and are absorded efficiently when given orally and are non-toxic when given parenterally. After the absorption the esters are converted to the corresponding penicillanic acids by enzymatic hydrolysis. Furthermore, these esters and the salts specified above are chemically more stable than the corresponding free acids. A specific example of such ester is bis(6- [(hexahydro-azepin-1-yl)-methyleneamino]-penicillanoyloxy)-methane.

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