Cephalosporins

Details Cephalosporins Cephalosporins

1990-10-31

1993-09-07

Rizzo, Nicholas S.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

540222, C07D50134, A61K 31545

Patent

active

052430430

DESCRIPTION:

BRIEF SUMMARY
OBJECTS OF THE INVENTION

It is an object of the invention to provide the novel compounds of formula I' and their non-toxic, pharmaceutically acceptable acid addition salts and a novel process for their preparation.
It is another object of the invention to provide novel antibiotic compositions and to provide a novel method of combatting bacterial infections in warm-blooded animals.
These and other objects and advantages of the invention will become obvious from the following detailed description.


THE INVENTION

The novel compounds of the invention are selected from the group consisting of the syn isomers of 3-alkoxymethyl or 3-alkylthiomethyl-7-[2-(2-amino-4-thiazolyl)-2-oximino-acetamido]cephalosp oranic acid compounds of the formula ##STR2## wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 6 carbon atoms, alkenyl and alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, acyl of an organic carboxylic acid of 1 to 18 carbon atoms and alkoxy carbonyl of 2 to 6 carbon atoms, A is selected from the group consisting of hydrogen, alkali metal, alkaline earth metal, --NH.sub.4, magnesium, non-toxic, pharmaceutically acceptable organic amine and an easily cleavable ester group, Ra is selected from the group consisting of alkyl of 1 to 6 carbon atoms optionally interrupted with a heteroatom, alkenyl and alkynyl of 2 to 6 carbon atoms and optionally substituted aralkyl of 7 to 12 carbon atoms, n is 0,1 or 2, X' is selected from the group consisting of oxygen and sulfur optionally oxidized to sulfoxide or sulfone and their non-toxic, pharmaceutically acceptable acid addition salts.
Among the preferred compounds of the invention are the syn isomers of compounds of the formula ##STR3## wherein A, n and R have the above definition X is selected from the group consisting of oxygen and sulfur and Ra is selected from the group consisting of alkyl of 1 to 6 carbon atoms, alkenyl and alkynyl of 2 to 6 carbon atoms and optionally substituted aralkyl of 7 to 12 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts.
Examples of suitable groups of R are (a) alkyl of 1 to 6 carbon atoms such as methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert.-butyl, pentyl, isopentyl, sec-pentyl, tert.-pentyl, neo-pentyl, hexyl, isohexyl, sec-hexyl and tert.-hexyl (b) alkenyl of 2 to 6 carbon atoms such as vinyl, allyl, 1-propenyl, butenyl, pentenyl and hexenyl, (c) alkynyl of 2 to 6 carbon atoms such as ethynyl, propargyl and butynyl, (d) cycloalkyl of 3 to 6 carbon atoms such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl and (e) acyl of an organic carboxylic acid of 1 to 18 carbon atoms such as acetyl, propionyl, butyryl, valeryl, hexanoyl, acryloyl, crotonoyl, benzyol, carbamoyl and alkoxycarbonyl such as methoxycarbonyl and ethoxycarbonyl.
The above groups a to d and certain groups of e are optionally substituted with at least one member of the group consisting of carboxyl optionally salified or esterified; alkoxycarbonyl of 2 to 6 carbon atoms such as methoxycarbonyl and ethoxycarbonyl; carbamoyl; dimethylcarbomyl; amino; dialkylamino of 1 to 6 carbon atoms such as dimethylamino and diethylamino; alkylamino of 1 to 6 carbon atoms such as methylamino; halogen such as chlorine, bromine and iodine; alkoxy of 1 to 6 carbon atoms such as methoxy, ethoxy and propoxy; alkylthio of 1 to 6 carbon atoms as methylthio and ethylthio; aryl such as phenyl; aryl heterocyclic such as tetrazolyl; arylthio such as optionally substituted phenylthio; arylheterocyclicthio such as tetrazolylthio and thiadiazolylthio optionally substituted with alkyl of 1 to 6 carbon atoms such as methyl. The groups of d) and some of e) may be substituted with alkyl as defined in a.
Examples of A are hydrogen; alkali metals such as sodium, potassium and lithium; alkaline earth metals such as calcium; magnesium; --NH.sub.4 ; and non-toxic, pharmaceutically acceptable organic amines such as methylamine, propylamine, trimethylamine, diethylamine, triethylamine, N,N-dimethyl-ethanolamine, tris-(hyd

REFERENCES:
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patent: 4201779 (1980-05-01), Bormann et al.
patent: 4483855 (1984-11-01), Nakav et al.
patent: 4973684 (1990-11-01), Ochiai et al.
patent: 4992431 (1991-02-01), Heymes et al.

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