# US 4,399,135 A · Oxacephalosporins and anti-bacterial composition containing same

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- Number: US 4,399,135 A
- Document ID: US4399135A
- Status: Granted
- Kind: A
- Application number: 06/322,962
- Filed: 1981-11-19
- Granted: 1983-08-16
- Earliest claimed: 1980-11-20
- Assignees: Rhone-Poulenc Industries
- Inventors: Daniel Farge; Pierre L. Roy; Claude Moutonnier; Bernard Plau; Jean-Francois Peyronel
- Web page: https://patentgrep.com/patent/US4399135A

## CPC

- C07D 505/00: Heterocyclic compounds containing 5-oxa-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula: [IMAGE cpc-sch-C07D-0995.gif] , e.g. oxacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- A61P 31/04: Antibacterial agents
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

New oxacephalosporins of the general formula (I), in which R is optionally N-oxidised pyridyl, pyrimidin-2-yl, substituted pyridazin-3-yl, 5,6-dioxo-1,4,5,6-tetrahydro-1,2,4-triazin-3-yl substituted in the 4-position, substituted 1-alkyl-1,3,4-triazol-5-yl or 1,2,4-triazol-5-yl, 5,6-dioxo-1,4,5,6-tetrahydro-1,2,4-triazin-3-yl substituted in the 1-position, 5,6-dioxo-1,4,5,6-tetrahydro-1,2,4-triazin-3-yl substituted in the 2-position, substituted or unsubstituted 2-alkyl-2,5-dihydro-5-oxo-1,2,4-triazin-3-yl, 1-amino-1,2-dihydro-2-oxo-pyrimidin-4-yl, substituted 1,3,4-thiadiazol-5-yl or tetrazol-5-yl substituted in the 1-position, R' is a substituted 2-(2-aminothiazol-4-yl)-acetyl radical or an .alpha.-carboxyarylacetyl radical and R" is a hydrogen atom or a methoxy radical in the 7.alpha.-position, and also their salts, their preparation and the medicaments in which they are present. ##STR1##

## Claims

### Claim 1

A oxacephalosporin of the general formula: ##STR28## in which the symbol R is chosen from amongst: (1) optionally N-oxidised pyrid-2-yl, pyrid-3-yl or pyrid-4-yl,
(2) pyrimidin-2-yl,
(3) 6-methylpyridazin-3-yl-1-oxide,
(4) 5,6-dioxo-1,4,5,6-tetrahydro-1,2,4-triazin-3-yl substituted in the 4-position by
(a) an alkyl radical containing 1 or 2 carbon atoms, which is optionally substituted by an alkoxy, alkylthio or formyl radical,
(b) an allyl, 2,3-dihydroxypropyl, 1,3-dihydroxyprop-2-yl or 2-formyl-2-hydroxyethyl radical, or
(c) an alkyl radical containing 2 or 3 carbon atoms, which is substituted by hydroxyl, carbamoyloxy, acyloxy or acylamino (the acyl portions of which are unsubstituted or substituted by amino), alkylsulphonylamino, ureido, alkylureido or dialkylureido,
(5) 5,6-dioxo-1,4,5,6-tetrahydro-1,2,4-triazin-3-yl substituted in the 1-position, or 5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl substituted in the 2-position, by an alkyl radical containing 1 or 2 carbon atoms, which is optionally substituted by a formyl radical,
(6) 2-alkyl-2,5-dihydro-5-oxo-1,2,4-triazin-3-yl optionally substituted in the 6-position by an alkyl or alkoxy radical, the alkyl portions and radicals of which contain 1 or 2 carbon atoms,
(7) 1-amino-1,2-dihydro-2-oxopyrimidin-4-yl,
(8) 1,3,4-thiadiazol-5-yl substituted by alkyl, dialkylaminoalkyl or acylaminoalkyl,
(9) tetrazol-5-yl substituted in the 1-position by
(a) an alkyl radical containing 1 or 2 carbon atoms, which is optionally substituted by a formyl radical,
(b) an alkyl radical containing 2 or 3 carbon atoms, which is substituted by hydroxyl, acylamino or dialkylamino, or
(c) a 2,3-dihydroxypropyl or 1,3-dihydroxyprop-2-yl radical, or
(10) (a) 1-alkyl-1,2,4-triazol-5-yl optionally substituted in the 3-position by an alkoxycarbonyl radical, the alkyl and alkoxy radicals of which contain 1 or 2 carbon atoms, or
(b) 1-alkyl-1,3,4-triazol-5-yl,
the symbol R' represents a radical of the general formula: ##STR29## in which R.degree. is a hydrogen atom, an alkyl radical, a vinyl radical or a carboxyalkyl radical represented by the general formula: ##STR30## in which the radicals R.sup.a and R.sup.b, which are identical or different, represent hydrogen atoms or alkyl radicals, or together form an alkylene radical containing 2 or 3 carbon atoms, or R' represents an .alpha.-carboxyarylacetyl radical in which aryl is a phenyl radical (optionally substituted by a p-hydroxy radical) or a thien-2-yl or thien-3-yl radical, and the symbol R" represents a hydrogen atom or a methoxy radical in the 7.alpha.-position, it being understood that, unless otherwise mentioned, the abovementioned alkyl or acyl radicals and portions are linear or branched and contain 1 to 4 carbon atoms, in its E or Z forms and mixtures thereof, if appropriate in its syn or anti forms or mixtures thereof, and also its pharmaceutically acceptable metal salts, its addition salts with pharmaceutically acceptable nitrogen-containing bases and, its addition salts with pharmaceutically acceptable acids.

### Claim 2 (depends on 1)

A product according to claim 1, in which the symbol R is a 5,6-dioxo-4-formylalkyl-1,4,5,6-tetrahydro-1,2,4-triazin-3-yl or 2-alkyl-1,3,4-thiadiazol-5-yl radical, the symbol R' is a radical of the general formula (II) in which R.degree. is an alkyl radical, and the symbol R" is a hydrogen atom, in its syn or anti forms and E or Z forms or mixtures thereof, and also its metal salts, its addition salts with nitrogen-containing bases and its addition salts with acids.

### Claim 3

The E form of the syn isomer of 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-2-carboxy-3-[2-(2-meth yl-1,3,4-thiadiazol-5-yl)-thiovinyl]-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-e ne.

### Claim 4

The E form of the syn isiomer of 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-2-carboxy-3-{2-[5,6-di oxo-4-(2-oxoethyl)-1,4,5,6-tetrahydro-1,2,4-triazin-3-yl]-thiovinyl}-8-oxo- 5-oxa-1-azabicyclo[4.2.0]oct-2-ene.

### Claim 5 (depends on 1)

A pharmaceutical antibacterial composition which contains an antibacterial amount of at least one product according to claim 1, in association with one or more compatible and pharmaceutically acceptable diluents or adjuvants.