# US 4,394,384 A · Aminothiazole cycloalkenyloxyimino acetamido cephem derivatives

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- Number: US 4,394,384 A
- Document ID: US4394384A
- Status: Granted
- Kind: A
- Application number: 06/183,167
- Filed: 1980-09-02
- Granted: 1983-07-19
- Earliest claimed: 1979-09-03
- Assignees: Fujisawa Pharmaceutical Co., Ltd.
- Inventors: Takao Takaya; Hisashi Takasugi; Masayoshi Murata; Akiteru Yoshioka
- Web page: https://patentgrep.com/patent/US4394384A

## CPC

- C07D 209/48: with oxygen atoms in positions 1 and 3, e.g. phthalimide
- C07D 213/79: Acids; Esters
- 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
- Y02P 20/55: Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

The invention relates to new cephem compounds of high antimicrobial activity, the new cephem compounds comprising aminothiazole cycloalkenyloxyimino acetamido cephem derivatives.

## Claims

### Claim 1

A cephem compound of the formula: ##STR14## wherein R.sup.1 is amino or a protected amino group;
R.sup.2 is cyclopentenyl or cyclohexenyl;
R.sup.3 is carboxy or a protected carboxy group;
R.sup.4 is a group of the formula:
--CH.sub.2 --R.sup.4a
wherein R.sup.4a is lower alkanoyloxy or thiadiazolylthio; and
R.sup.5 is hydrogen or lower alkyl; and pharmaceutically acceptable salts thereof.

### Claim 2 (depends on 1)

The compound of claim 1 wherein:
R.sup.1 is amino or acylamino;
R.sup.3 is carboxy or esterified carboxy; and
R.sup.4 is a group of the formula:
--CH.sub.2 --R.sup.4a
wherein R.sup.4a is lower alkanoyloxy or thiadiazolylthio.

### Claim 3 (depends on 2)

The compound of claim 2, which is syn isomer.

### Claim 4 (depends on 3)

The compound of claim 3, wherein
R.sup.1 is amino;
R.sup.2 is cyclopentenyl or cyclohexenyl;
R.sup.3 is carboxy;
R.sup.4a is lower alkanoyloxy; and
R.sup.5 is hydrogen.

### Claim 5 (depends on 4)

The compound of claim 4, which is 7-[2-(2-cyclopenten-1-yl)oxyimino-2-(2-aminothiazol-4-yl)acetamido]cephalo sporanic acid (syn isomer).

### Claim 6 (depends on 4)

The compound of claim 4 which is 7-[2-(2-cyclohexen-1-yl)oxyimino-2-(2-aminothiazol-4-yl)acetamido]cephalos poranic acid (syn isomer).

### Claim 7 (depends on 3)

The compound of claim 3, wherein
R.sup.1 is amino;
R.sup.3 is carboxy;
R.sup.4a is thiadiazolylthio, and
R.sup.5 is hydrogen.

### Claim 8 (depends on 7)

The compound of claim 7, which is 7-[2-(2-cyclopenten-1-yl)oxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(1,3 ,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer).

### Claim 9 (depends on 7)

The compound of claim 7, which is 7-[2-cyclohexen-1-yl)oxyimino-2-[2-aminothiazol-4-yl)acetamido]-3-(1,3,4-t hiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer).

### Claim 10 (depends on 3)

The compound of claim 3, wherein
R.sup.1 is lower alkanoylamino or halogen substituted lower alkanoylamino; and
R.sup.3 is carboxy or ar(lower)alkoxycarbonyl.

### Claim 11 (depends on 1)

A pharmaceutical composition comprising an effective amount of a compound of claim 1 or pharmaceutically acceptable salt thereof in association with a pharmaceutically acceptable, substantially non-toxic carrier or excipient.