# US 5,352,792 A · Thioalkylthio cephalosporin derivatives

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- Number: US 5,352,792 A
- Document ID: US5352792A
- Status: Granted
- Kind: A
- Application number: 08/025,628
- Filed: 1993-03-02
- Granted: 1994-10-04
- Earliest claimed: 1990-07-19
- Assignees: Shionogi & Co., Ltd.
- Inventors: Tadatoshi Kubota; Masaharu Kume
- Web page: https://patentgrep.com/patent/US5352792A

## CPC

- C07D 249/04: 1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- A61P 31/00: Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P 31/04: Antibacterial agents
- C07D 501/00: Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula: [IMAGE cpc-sch-C07D-0993.gif] , e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- Y02P 20/55: Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

A novel thioalkylthio cephalosporin antibiotic compound of formula I: ##STR1## wherein Acyl is C.sub.1 -C.sub.12 acyl; Het is optionally substituted monocyclic heteroaromatic group containing one or more hetero atoms; R.sup.1 is a single bond or C.sub.1 -C.sub.4 alkylene; R.sub.2 is a straight or branched C.sub.1 -C.sub.4 alkylene; X is a sulfur atom or sulfoxide group; and Y is a hydrogen atom or methoxy group, or a pharmaceutically acceptable salt or an amino-, carboxy- and/or hydroxy-protected derivative thereof, a formulation containing the same and a method for treating bacterial infections.

## Claims

### Claim 1

A compound selected from the group consisting of:
AcSR.sup.2 SR.sup.1 Het and HalR.sup.2 SR.sup.1 Het wherein Ac is C.sub.1 -C.sub.12 acyl; Hal is halogen; R.sup.1 is a single bond or C.sub.1 -C.sub.4 alkylene; and R.sup.2 is a straight or branched C.sub.1 -C.sub.4 alkylene; Het is 1, 2, 3-triazol-4-yl, or a derivative which is optionally protected at a nitrogen atom by one or more protecting groups selected from C1-C8 alkyl, C7-C19 aralkyl; C1-C8 alkylthio; C6-C12 arylthio; C5-C8 cycloalkylidene; C2-C12 alkoxycarbonyl the alkyl of which is cyclic or acyclic, substituted or unsubstituted and is selected from the group consisting of methyl, ethyl, propyl, cyclopropylmethyl, cyclopropylethyl, isopropyl, butyl, isobutyl, pentyl, hexyl, trichloroethyl, pyridylmethyl, cyclopentyl or cyclohexyl; C8-C19 aralkoxycarbonyl the aralkyl of which is benzyl, benzhydryl or nitrobenzyl, C7-C15 aroyl; C3-C9 trialkylsilyl; C3-C9 alkoxydialkylsilyl; and an acid capable of forming acid addition salt.

### Claim 2 (depends on 1)

The compound as claimed in claim 1 where R.sup.1 is a single bond.

### Claim 3 (depends on 1)

The compound as claimed in claim 1 wherein R.sup.2 is methylene.

### Claim 4 (depends on 1)

The compound as claimed in claim 1 wherein R.sup.2 is ethylidene.

### Claim 5 (depends on 1)

The compound as claimed in claim 1 wherein Ac is acetyl.

### Claim 6 (depends on 1)

The compound as claimed in claim 1 wherein Ac is benzoyl.

### Claim 7 (depends on 1)

The compound as claimed in claim 1 wherein Hal is chloro.