# US 4,396,618 A · Alkyloximes of 7-amino-thiazolyl-acetamido-cephalosporanic acids

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- Number: US 4,396,618 A
- Document ID: US4396618A
- Status: Granted
- Kind: A
- Application number: 06/094,196
- Filed: 1979-11-14
- Granted: 1983-08-02
- Earliest claimed: 1976-03-25
- Assignees: Roussel Uclaf
- Inventors: Rene Heymes; Andre Lutz
- Web page: https://patentgrep.com/patent/US4396618A

## CPC

- C07D 277/20: having two or three double bonds between ring members or between ring members and non-ring members
- A61P 31/04: Antibacterial agents
- C07D 277/38: Nitrogen atoms
- C07D 277/587: with aliphatic hydrocarbon radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms, said aliphatic radicals being substituted in the alpha-position to the ring by a hetero atom, e.g. [IMAGE cpc-sch-C07D-1029.gif] with m >= 0, Z being a singly or a doubly bound hetero atom
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Novel alkyloximes of 7-amino-thiazolyl-acetamide-cephalosporanic acids of the formula ##STR1## wherein R is selected from the group consisting of alkyl of 1 to 5 carbon atoms, cycloalkyl of 3 to 5 carbon atoms and --CH.sub.2 --SR', R' is selected from the group consisting of acyl of an alkanoic acid of 2 to 4 carbon atoms, 1-methyl-tetrazolyl and 2-methyl-1,3,4-thiadiazolyl, R.sub.1 is selected from the group consisting of hydrogen and a group easily removeable by acid hydrolysis or hydrogenolysis, R.sub.2 is selected from the group consisting of alkyl of 1 to 4 carbon atoms and alkenyl and alkynyl of 2 to 4 carbon atoms, A is selected from the group consisting of hydrogen, an alkali metal cation, an equivalent of an alkaline earth metal or magnesium, an organic amine base cation and an ester group easily removeable by acid hydrolysis or hydrogenolysis with the proviso that when R.sub.1 is hydrogen, A is not an ester group easily removeable by hydrogenolysis or acid hydrolysis and the wavy line means that OR.sub.2 is in one or the other of the two possible syn or anti isomeric positions having a very good antibiotic activity and novel processes and intermediates for their preparation.

## Claims

### Claim 1

A compound of the formula ##STR24## wherein R is selected from the group consisting of alkyl of 1 to 5 carbon atoms and cycloalkyl of 3 to 5 carbon atoms, R.sub.1 is hydrogen, R.sub.2 is selected from the group consisting of 1 to 4 carbon atoms and alkenyl and alkynyl of 2 to 4 carbon atoms, A is selected from the group consisting of hydrogen, an alkali metal cation, or equivalent of an alkaline earth metal or magnesium and an organic amine base cation and OR.sub.2 is in the syn position.

### Claim 2 (depends on 1)

A compound of claim 1 wherein R.sub.2 is methyl, A is hydrogen and R is selected from the group consisting of methyl and isopropyl.

### Claim 3 (depends on 1)

A compound of claim 1 which is syn isomer of 7-[{2-(2-amino-4-thiazolyl)-2-methoxyiminoacetyl}amino]-3-isopropyl-ceph-3 -eme-4-carboxylic acid.

### Claim 4 (depends on 1)

A compound of claim 1 which is syn isomer of 7-[{2-(2-amino-4-thiazolyl)-2-methoxyiminoacetyl}amino]-3-methyl-ceph-3-em e-4-carboxylic acid.

### Claim 5 (depends on 1)

An antibiotic composition comprising an antibiotically effective amount of at least one compound of claim 1 and an inert pharmaceutical carrier.

### Claim 6 (depends on 1)

A method of treating bacterial infections in warm-blooded animals comprising administering to warm-blooded animals an antibiotically effective amount of at least one compound of claim 1.

### Claim 7 (depends on 6)

The method of claim 6 wherein the compound is syn isomer of 7-[{2-(2-amino-4-thiazolyl)-2-methoxyiminoacetyl}amino]-3-isopropyl-ceph-3 -eme-4-carboxylic acid.

### Claim 8 (depends on 6)

The method of claim 6 wherein the compound of syn isomer of 7-[{2-(2-amino-4-thiazolyl)-2-methoxyiminoacetyl}amino]-3-methyl-ceph-3-em e-4-carboxylic acid.