# US 4,400,379 A · Cephem compounds

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- Number: US 4,400,379 A
- Document ID: US4400379A
- Status: Granted
- Kind: A
- Application number: 06/302,681
- Filed: 1981-09-15
- Granted: 1983-08-23
- 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/US4400379A

## 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.2 is an aliphatic hydrocarbon residue substituted with halogen, carboxy or esterified carboxy, R.sup.4 is halogen or a group of the formula: --O--R.sup.7, in which R.sup.7 is lower alkyl, R.sup.5 is carboxy or functionally modified carboxy and R.sup.6 is amino or protected amino, and pharmaceutically acceptable salt thereof, processes for making the compounds, pharmaceutical compositions containing them and their use to treat infectious diseases.

## Claims

### Claim 1

A syn compound of the formula: ##STR37## wherein R.sup.2 is aliphatic hydrocarbon substituted with halogen, carboxy or esterified carboxy,
R.sup.4 is halogen or a group of the formula: --O--R.sup.7, in which R.sup.7 is lower alkyl,
R.sup.5 is carboxy or carboxy modified to a group from which carboxy may be regenerated and
R.sup.6 is amino or protected amino, and pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

The compound of the claim 1, wherein
R.sup.2 is halogen substituted(lower)alkyl
R.sup.4 is halogen and
R.sup.5 is carboxy or esterified carboxy.

### Claim 3 (depends on 2)

The compound of the claim 2, wherein R.sup.6 is amino or lower alkanamido.

### Claim 4 (depends on 3)

The compound of the claim 3, wherein
R.sup.2 is trihalo(lower)alkyl, and
R.sup.5 is carboxy or substituted benzyloxycarbonyl.

### Claim 5 (depends on 4)

The compound of the claim 4, which is
7-[2-(2-aminothiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)acetamido]-3-chlor o-3-cephem-4-carboxylic acid (syn isomer) or its hydrochloride.

### Claim 6 (depends on 4)

The compound of the claim 4, which is 7-[2-(2-formamidothiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)acetamido]-3- chloro-3-cephem-4-carboxylic acid (syn isomer) or its p-nitrobenzyl ester.

### Claim 7 (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 8 (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.

### Claim 9 (depends on 1)

The compound of claim 1 wherein
R.sup.2 is (A) halogen substituted lower alkyl, halogen substituted lower alkenyl, halogen substituted lower alkynyl, or halogen substituted lower cycloalkyl, or (B) carboxy lower alkyl, carboxy lower alkenyl, carboxy lower alkynyl, or carboxy lower cycloalkyl, or (C) a lower alkyl ester of (B), and
R.sup.5 is carboxy, carboxy ester or carboxamide.

### Claim 10 (depends on 3)

The compound of claim 3 wherein
R.sup.2 is chloromethyl, bromomethyl, iodomethyl, fluoromethyl, trichloromethyl, trifluoromethyl, 2-chloroethyl, 1,2-dichloroethyl, 2,2,3-trifluorethyl, 3-chloropropyl, 4-iodobutyl, 5-fluoropentyl, 6-bromohexyl, 3-fluoroallyl, 3-chloropropargyl or 4-fluorocyclohexyl, and
R.sup.5 is carboxy.