# US 4,395,411 A · Pyrimidinyl cephalosporanic acid derivatives and pharmaceutical compositions

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 4,395,411 A
- Document ID: US4395411A
- Status: Granted
- Kind: A
- Application number: 06/213,684
- Filed: 1980-12-05
- Granted: 1983-07-26
- Earliest claimed: 1977-11-14
- Assignees: Fujisawa Pharmaceutical Co., Ltd.
- Inventors: Takashi Kamiya; Tsutomu Teraji; Yoshiharu Nakai; Kazuo Sakane; Jiro Goto
- Web page: https://patentgrep.com/patent/US4395411A

## CPC

- C07D 213/73: Unsubstituted amino or imino radicals
- A61P 31/04: Antibacterial agents
- C07D 213/75: Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
- C07D 213/79: Acids; Esters
- C07D 213/80: in position 3
- C07D 239/42: One nitrogen atom (nitro radicals C07D239/30)
- C07D 239/47: One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
- C07F 7/10: containing nitrogen {having a Si-N linkage}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

This invention relates to novel 7-pyrimidinyl and pyridinyl acetamido cephem derivatives of high antibacterial activity.

## Claims

### Claim 1

A compound of the formula: ##STR15## wherein R.sup.1 is a group of the formula: ##STR16## in which R.sub.a.sup.1 is hydrogen, amino or a protected amino group, R.sub.b.sup.1 and R.sub.c.sup.1 are each hydrogen, halogen, lower alkoxy, phenylthio, tolylthio, xylylthio, mesitylthio or naphthylthio,
R.sup.2 is hydrogen or lower alkoxy,
R.sup.3 is hydrogen or lower alkyl,
R.sup.4 is hydrogen, halogen, carbamoyloxymethyl, lower alkyl, lower alkoxy, lower alkanoyloxymethyl or lower alkanoylthiomethyl,
R.sup.5 is carboxy or a protected carboxy group, and
X is a group of the formula: ##STR17## in which R.sup.6 is hydrogen, lower alkyl, mono to trihalo (lower) alkyl, lower alkenyl, lower alkynyl, phenyl, tolyl, xylyl, cumenyl, naphthyl, phenyl (lower) alkyl, mono or dihalo (lower) alkanoyl, or lower alkoxy, and non-toxic, pharmaceutically acceptable salts thereof.

### Claim 2 (depends on 1)

A compound of claim 1, wherein
R.sup.1 is a group of the formula: ##STR18## in which R.sub.a.sup.1 is hydrogen, amino or acylamino,
R.sub.b.sup.1 and R.sub.c.sup.1 are each hydrogen, halogen, lower alkoxy or phenylthio,
R.sup.2 is hydrogen or lower alkoxy,
R.sup.3 is hydrogen or lower alkyl,
R.sup.4 is hydrogen, halogen, carbamoyloxymethyl, lower alkyl, lower alkoxy, lower alkanoyloxymethyl, or lower alkanoylthiomethyl,
R.sup.5 is carboxy or an esterified carboxy group, and
X a group of the formula: ##STR19## in which R.sup.6 is hydrogen, lower alkyl, trihalo(lower)alkyl, lower alkenyl, lower alkynyl, phenyl or phenyl(lower)alkyl.

### Claim 3 (depends on 2, 3)

A compound of claim 2, wherein
R.sup.1 is a group of the formula: ##STR20## in which R.sub.a.sup.1 is hydrogen, amino, lower alkanoyl or trihalo(lower)alkanoyl,
R.sub.b.sup.1 and R.sub.c.sup.1 are each hydrogen, halogen, lower alkoxy or phenylthio,
R.sup.2 is hydrogen or lower alkoxy,
R.sup.3 is hydrogen or lower alkyl,
R.sup.4 is hydrogen, halogen, carbamoyloxymethyl, lower alkyl, lower alkoxy, lower alkanoyloxymethyl, or lower alkanoylthiomethyl
R.sup.5 is carboxy, nitrophenyl(lower)alkoxycarbonyl or diphenyl(lower)alkoxycarbonyl, and
X is a group of the formula: ##STR21## in which R.sup.6 is hydrogen, lower alkyl, trihalo(lower)alkyl, lower alkenyl, lower alkynyl, phenyl or phenyl(lower)alkyl, in which R.sup.6 is as defined in claim 3.

### Claim 4 (depends on 3)

A compound of claim 3,
wherein
R.sup.1 is a group of the formula: ##STR22## in which R.sub.c.sup.1 is hydrogen, halogen, lower alkoxy or phenylthio and
R.sup.2 is hydrogen.

### Claim 5 (depends on 4)

A compound of claim 4, wherein R.sup.5 is carboxy.

### Claim 6 (depends on 5)

A compound of claim 5, wherein
R.sub.c.sup.1 is hydrogen, chloro, methoxy or phenylthio,
R.sup.3 is hydrogen or methyl,
R.sup.4 is hydrogen, chloro, carbamoyloxymethyl, methyl, acetoxymethyl, or acetylthiomethyl, and
R.sup.6 is methyl, ethyl, propyl, allyl, benzyl or phenyl.

### Claim 7 (depends on 6)

A compound of claim 6, which is 7-[2-(4-aminopyrimidin-2-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxyli c acid (syn isomer).

### Claim 8 (depends on 6)

A compound of claim 6, which is 7-[2-(4-aminopyrimidin-2-yl)-2-methoxyiminoacetamido]-2-methyl-3-cephem-4- carboxylic acid (syn isomer).

### Claim 9 (depends on 6)

A compound of claim 6, which is 7-[2-(4-aminopyrimidin-2-yl)-2-methoxyiminoacetamido]cephalosporanic acid (syn isomer).

### Claim 10 (depends on 6)

A compound of claim 6, which is 7-[2-(4-aminopyrimidin-2-yl)-2-methoxyiminoacetamido]-3-carbamoyloxymethyl -3-cephem-4-carboxylic acid (syn isomer).

### Claim 11 (depends on 3)

A compound of claim 3, wherein
R.sup.1 is a group of the formula: ##STR23## in which R.sub.a.sup.1 is lower alkanoylamino, and
R.sup.2 is hydrogen.

### Claim 12 (depends on 11)

A compound of claim 11, wherein
R.sub.a.sup.1 is formamido,
R.sup.3 is hydrogen,
R.sup.4 is acetoxymethyl,
R.sup.5 is carboxy and
R.sup.6 is methyl, ethyl, propyl, allyl or benzyl.

### Claim 13 (depends on 3)

A compound of claim 3, wherein
R.sup.1 is a group of the formula: ##STR24## in which R.sub.a.sup.1 is lower alkanoyl amino and R.sub.c.sup.1 is hydrogen or halogen, and
R.sup.2 is hydrogen.

### Claim 14 (depends on 13)

A compound of claim 13, wherein
R.sub.a.sup.1 is formamido,
R.sub.c.sup.1 is hydrogen or chloro,
R.sup.3 is hydrogen,
R.sup.5 is carboxy and
R.sup.6 is methyl.

### Claim 15 (depends on 1)

An anti-bacterial pharmaceutical composition comprising, as an active ingredient, an effective amount of the compound of claim 1, in association with a non-toxic, pharmaceutically acceptable carrier or excipient.

### Claim 16 (depends on 1)

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