# US 4,380,512 A · 2.beta.-Chloromethyl-2.alpha.-methylpenam-3.alpha.-carboxylic acid sulfone and salts and esters thereof

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- Number: US 4,380,512 A
- Document ID: US4380512A
- Status: Granted
- Kind: A
- Application number: 06/271,744
- Filed: 1981-06-08
- Granted: 1983-04-19
- Earliest claimed: 1980-01-21
- Assignees: Bristol-Myers Company
- Inventors: William J. Gottstein
- Web page: https://patentgrep.com/patent/US4380512A

## CPC

- C07D 499/00: Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula: [IMAGE cpc-sch-C07D-0992.gif] , e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

2.beta.-Chloromethyl-2.alpha.-methylpenam-3.alpha.-carboxylic acid sulfone and salts and esters thereof were synthesized and found to be potent inhibitors of .beta.-lactamases.

## Claims

### Claim 1

The acid having the formula ##STR68## or a pharmaceutically acceptable salt of said acid or an ester of said acid having the formula ##STR69## wherein R is phenacyl, acetoxymethyl, pivaloyloxymethyl, .alpha.-acetoxyethyl, .alpha.-acetoxybenzyl, .alpha.-pivaloyloxyethyl, 3-phthalidyl, 5-indanyl, methoxymethyl, benzoyloxymethyl, .alpha.-ethylbutyryloxymethyl, propionyloxymethyl, valeryloxymethyl, isobutyryloxymethyl, 6-[(R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3 .2.0]heptane-2-carbonyloxymethyl or 6-[(R)-2-amino-2-p-hydroxyphenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-aza bicyclo[3.2.0]heptane-2-carbonyloxymethyl.

### Claim 2

The acid having the formula ##STR70##

### Claim 3 (depends on 2)

A pharmaceutically acceptable salt of the acid of claim 2.

### Claim 4 (depends on 2)

The sodium salt of the acid of claim 2.

### Claim 5 (depends on 2)

The potassium salt of the acid of claim 2.

### Claim 6 (depends on 2)

The ammonium salt of the acid of claim 2.

### Claim 7

An ester having the formula ##STR71## wherein R is phenacyl, acetoxymethyl, pivaloyloxymethyl, .alpha.-acetoxyethyl, .alpha.-acetoxybenzyl, .alpha.-pivaloyloxyethyl, 3-phthalidyl, 5-indanyl, methoxymethyl, benzoyloxymethyl, .alpha.-ethylbutyryloxymethyl, propionyloxymethyl, valeryloxymethyl, isobutyryloxymethyl, 6-[(R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3 .2.0]heptane-2-carbonyloxymethyl or 6-[(R)-2-amino-2-p-hydroxyphenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-aza bicyclo[3.2.0]heptane-2-carbonyloxymethyl.

### Claim 8 (depends on 7)

The ester of claim 7 wherein R is acetoxymethyl.

### Claim 9 (depends on 7)

The ester of claim 7 wherein R is pivaloyloxymethyl.

### Claim 10 (depends on 7)

The ester of claim 7 wherein R is 3-phthalidyl.

### Claim 11 (depends on 7)

The ester of claim 7 wherein R is 5-indanyl.

### Claim 12 (depends on 7)

The ester of claim 7 wherein R is methoxymethyl.

### Claim 13 (depends on 7)

The ester of claim 7 wherein R is phenacyl.

### Claim 14 (depends on 7)

The ester of claim 7 wherein R is 6-[(R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3 .2.0]heptane-2-carbonyloxymethyl.

### Claim 15 (depends on 7)

The ester of claim 7 wherein R is 6-[(R)-2-amino-2-p-hydroxyphenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-aza bicyclo[3.2.0]heptane-2-carbonyloxymethyl.

### Claim 16

The ester having the formula ##STR72##

### Claim 17

The ester having the formula ##STR73##