# US 4,396,620 A · Cephalosporin quinolinium betaines

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- Number: US 4,396,620 A
- Document ID: US4396620A
- Status: Granted
- Kind: A
- Application number: 06/300,131
- Filed: 1981-09-08
- Granted: 1983-08-02
- Earliest claimed: 1981-09-08
- Assignees: Eli Lilly and Company
- Inventors: William H. W. Lunn
- Web page: https://patentgrep.com/patent/US4396620A

## CPC

- C07D 501/46: with the 7-amino radical acylated by carboxylic acids containing hetero rings
- A61P 31/04: Antibacterial agents
- C07D 501/16: with a double bond between positions 2 and 3
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Broad spectrum cephalosporin antibiotics represented by the formula ##STR1## wherein R' is a heterocyclic, eg. 2-aminothizol-4-yl or 5-amino-1,2,4-thiadiazol-3-yl; R" is C.sub.1 -C.sub.4 alkyl, a carboxy-substituted alkyl or cycloalkyl group, or an N-substituted carbamoyl group; and R.sub.1 and R.sub.2 represent substituent groups, eg. amino, hydroxy, halogen, carboxy, carbamoyl, alkyl, alkylamino, sulfo, and sulfonamido; and formulations of the antibiotics are provided. The antibiotics are useful in a method for treating bacterial infections.

## Claims

### Claim 1

A compound of the formula ##STR21## wherein R is formyl, or an acyl group of the formula ##STR22## wherein R' is a 5- or 6-membered heterocyclic ring of the formulas ##STR23## R" is C.sub.1 -C.sub.4 alkyl, a carboxy-substituted alkyl, or carboxy-substituted cycloalkyl group of the formula ##STR24## wherein n is 0-3, a and b when taken separately are independently hydrogen or C.sub.1 -C.sub.3 alkyl, or when taken together with the carbon to which they are attached form a C.sub.3 -C.sub.7 carbocyclic ring; R'" is hydroxy, C.sub.1 -C.sub.4 alkoxy, amino, and when R'" is hydroxy a carboxy-protecting group; R.sub.1 and R.sub.2 independently are hydrogen, amino, C.sub.1 -C.sub.4 alkylamino, di-(C.sub.1 -C.sub.4 alkyl)amino, or hydroxy; provided that one of R.sub.1 or R.sub.2 is other than hydrogen; and the pharmaceutically acceptable, non-toxic salts thereof.

### Claim 2 (depends on 1)

The compound of claim 1 wherein R is an acyl group of the formula ##STR25##

### Claim 3 (depends on 2)

The compound of claim 2 wherein R" is a carboxy-substituted alkyl or cycloalkyl group of the formula ##STR26##

### Claim 4 (depends on 2)

The compound of claim 2 wherein R" is C.sub.1 -C.sub.4 alkyl.

### Claim 5 (depends on 4)

The compound of claim 4 wherein either R.sub.1 or R.sub.2 is amino.

### Claim 6 (depends on 5)

The compound of claim 5, said compound being syn-7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-(5-aminoquinolin ium-1-ylmethyl)-3-cephem-4-carboxylate.

### Claim 7 (depends on 5)

The compound of claim 5, said compound being syn-7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-(3-aminoquinolin ium-1-ylmethyl)-3-cephem-4-carboxylate.

### Claim 8 (depends on 5)

The compound of claim 5, said compound being syn-7-[2-(2-aminoquinolinium-1-ylmethyl)-2-methoxyiminoacetamido]-3-(7-ami noquinolinium-1-yl-methyl)-3-cephem-4-carboxylate.

### Claim 9 (depends on 4)

The compound of claim 4 wherein either R.sub.1 or R.sub.2 is hydroxy.

### Claim 10 (depends on 9)

The compound of claim 9, said compound being syn-7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-(5-hydroxyquinol inium-1-ylmethyl)-3-cephem-4-carboxylate.

### Claim 11 (depends on 9)

The compound of claim 9, said compound being syn-7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-(6-hydroxyquinol inium-1-ylmethyl)-3-cephem-4-carboxylate.

### Claim 12 (depends on 9)

The compound of claim 9, said compound being syn-7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-(7-hydroxyquinol inium-1-ylmethyl)-3-cephem-4-carboxylate.

### Claim 13 (depends on 1)

The compound of claim 1 wherein R is formyl.

### Claim 14 (depends on 2)

A pharmaceutical formulation comprising a therapeutically effective amount of an antibiotic compound of claim 2 or a pharmaceutically acceptable non-toxic salt thereof wherein R is acyl and a pharmaceutically acceptable diluent.

### Claim 15 (depends on 14)

The formulation of claim 14 wherein either R.sub.1 or R.sub.2 is amino.

### Claim 16 (depends on 14)

The formulation of claim 14 wherein either R.sub.1 or R.sub.2 is hydroxy.

### Claim 17 (depends on 2)

A method for treating bacterial infections in a mammal which comprises administering in a dose of between about 100 mg. to about 2 g. of an antibiotic compound of claim 2 or a pharmaceutically acceptable salt thereof.

### Claim 18 (depends on 17)

The method of claim 17 where in the compound administered either R.sub.1 or R.sub.2 is amino.

### Claim 19 (depends on 17)

The method of claim 17 where in the compound administered either R.sub.1 or R.sub.2 is hydroxy.