# US 4,088,695 A · Cyclopentanone derivatives

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- Number: US 4,088,695 A
- Document ID: US4088695A
- Status: Granted
- Kind: A
- Application number: 05/543,552
- Filed: 1975-01-23
- Granted: 1978-05-09
- Earliest claimed: 1974-01-26
- Assignees: May & Baker Limited
- Inventors: Michael P. L. Caton; Edward C. J. Coffee; Gordon L. Watkins
- Web page: https://patentgrep.com/patent/US4088695A

## CPC

- C07D 317/72: spiro-condensed with carbocyclic rings
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07C 405/0025: {containing keto groups}
- C07D 309/12: only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
- C07F 9/54: Quaternary phosphonium compounds
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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

Cyclopentane derivatives of the formula: ##STR1## wherein R.sup.1 represents hydrogen or a carboxylic acyl group, and either (I) R.sup.2 represents a group of the formula: --CR.sup.3 R.sup.4 R.sup.5 II (wherein R.sup.3 and R.sup.4 represent hydrogen or alkyl, and R.sup.5 represents hydrogen, or alkyl, alkoxy, cycloalkyl or adamantyl, or R.sup.5 represents alkyl substituted by alkoxy, or by cycloalkyl or by adamantyl, or the group --CR.sup.3 R.sup.4 R.sup.5 together forms a cycloalkyl or adamantyl group), X represents trans-vinylene or ethylene and Y represents carbonyl or a group of the formula: ##STR2## wherein R.sup.6 represents hydrogen or alkyl, and R.sup.7 represents hydrogen or a carboxylic acyl group, or else (ii) R.sup.2 represents a group of the formula: --A-Z-R.sup.8 IV (wherein A represents alkylene, Z represents a direct bond or oxygen or sulphur, and R.sup.8 represents an aryl or heterocyclyl group which may be substituted by one or more of halogen, alkyl, alkoxy and trihalomethyl), X in formula I represents ethylene or trans-vinylene and Y in formula I represents carbonyl or a group of formula III, or else (iii) R.sup.2 represents a group R.sup.8 and X and Y in formula I represent simultaneously ethylene and carbonyl, trans-vinylene and carbonyl, or ethylene and --CH(OR.sup.7)-- groups respectively. The compounds are new and possess pharmacological properties similar to those of prostaglandins.

## Claims

### Claim 1

A cyclopentane derivative of the formula: ##STR12## wherein R.sup.1 is hydrogen, alkanoyl of 1 to 4 carbon atoms, or benzoyl, A is alkylene of 1 to 12 carbon atoms, Z is a direct bond or oxygen or sulphur, X is ethylene or trans-vinylene, Y is carbonyl or ##STR13## where R.sup.6 is hydrogen or alkyl of 1 to 4 carbon atoms and R.sup.7 is hydrogen, alkanoyl of 1 to 4 carbon atoms, or benzoyl, and R.sup.8 is phenyl or naphthyl which is unsubstituted or substituted by halogen, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, or trihalomethyl.

### Claim 2 (depends on 1)

A cyclopentane derivative according to claim 1 wherein A is alkylene of 1 to 7 carbon atoms.

### Claim 3 (depends on 1)

A cyclopentane derivative according to claim 1 wherein A is methylene, Z is oxygen and R.sup.8 is phenyl.

### Claim 4 (depends on 1)

A cyclopentane derivative according to claim 1 wherein Y represents a group of the formula: ##STR14## wherein R.sup.6 represents methyl and R.sup.7 is as defined in claim 1.

### Claim 5 (depends on 1)

A cyclopentane derivative according to claim 1 wherein R.sup.8 represents phenyl.

### Claim 6 (depends on 1)

A cyclopentane derivative according to claim 1 in which the group attached to the 8-position of the cyclopentane ring of formula I depicted in claim 1 is in alpha configuration and the group attached to the 12-position of the cyclopentane ring is in beta-configuration.

### Claim 7 (depends on 1)

A cyclopentane derivative according to claim 1 which is 7-[2-(3-hydroxy-4-phenoxybut-1-enyl)-5-oxocyclopentyl]heptanol.

### Claim 8 (depends on 1)

A cyclopentane derivative according to claim 1 which is 7-[2-(3-hydroxy-3-methyl-4-phenoxybut-1-enyl)-5-oxocyclopentyl]heptanol.

### Claim 9 (depends on 1)

A cyclopentane derivative according to claim 1 which is 7-[5-(3-oxo-6-phenylhex-1-enyl)-2-oxocyclopentyl]heptanol.

### Claim 10 (depends on 1)

A cyclopentane derivative according to claim 1 which is 7-[5-(3-oxo-5-phenylpent-1-enyl)-2-oxocyclopentyl]heptanol.

### Claim 11 (depends on 1)

A cyclopentane derivative according to claim 1 which is 7-[5-(3-oxo-4-phenylbut-1-enyl)-2-oxocyclopentyl]heptanol.

### Claim 12 (depends on 1)

A cyclopentane derivative according to claim 1 which is 7-{5-[3-oxo-4-(2-phenylethyl)oct-1-enyl]-2-oxocyclopentyl}heptanol.