# US 4,399,133 A · Cephem compounds

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- Number: US 4,399,133 A
- Document ID: US4399133A
- Status: Granted
- Kind: A
- Application number: 06/302,613
- Filed: 1981-09-15
- Granted: 1983-08-16
- Earliest claimed: 1977-03-14
- Assignees: Fujisawa Pharmaceutical Co., Ltd.
- Inventors: Takao Takaya; Hisashi Takasugi; Kiyoshi Tsuji; Toshiyuki Chiba
- Web page: https://patentgrep.com/patent/US4399133A

## CPC

- C07D 277/20: having two or three double bonds between ring members or between ring members and non-ring members
- C07D 285/06: 1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
- C07D 501/20: 7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The invention relates particularly to syn compounds of the formula: ##STR1## wherein R.sup.1 is thiadiazolyl, R.sup.2 is hydrogen or an aliphatic hydrocarbon residue which may be substituted with halogen, carboxy or esterified carboxy and R.sup.5 is carboxy or functionally modified carboxy, and pharmaceutically acceptable salt thereof, processes for making them, pharmaceutical compositions containing them and their use in treating infectious diseases.

## Claims

### Claim 1

A syn compound of the formula: ##STR37## wherein R.sup.1 is thiadiazolyl,
R.sup.2 is hydrogen or aliphatic hydrocarbon which may be substituted with halogen, carboxy or esterified carboxy and
R.sup.5 is carboxy or carboxy modified to a group from which carboxy may be regenerated, and pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

The compound of the claim 1, wherein R.sup.2 is lower alkyl, and R.sup.5 is carboxy or esterified carboxy.

### Claim 3 (depends on 2)

The compound of the claim 2, which is
7-[2-(1,2,3-thiadiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer).

### Claim 4 (depends on 2)

The compound of the claim 2, wherein
R.sup.5 is substituted benzyloxycarbonyl.

### Claim 5 (depends on 4)

The compound of the claim 4, which is
p-nitrobenzyl 7-[2-(1,2,3-thiadiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxyla te (syn isomer).

### Claim 6 (depends on 1)

A pharmaceutical composition comprising, as an effective ingredient, the compound of claim 1, in association with a pharmaceutically acceptable, substantially nontoxic carrier or excipient.

### Claim 7 (depends on 1)

A method for treating an infectious disease caused by pathogens, which comprises administering the compound of claim 1 to infected human being or animals.