# US 4,400,393 A · Novel bicyclooctane compounds

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- Number: US 4,400,393 A
- Document ID: US4400393A
- Status: Granted
- Kind: A
- Application number: 06/246,938
- Filed: 1981-03-24
- Granted: 1983-08-23
- Earliest claimed: 1980-04-11
- Assignees: Sumitomo Chemical Company, Limited
- Inventors: Shunsuke Sami; Akihiko Sugie; Keiichi Ono; Hajime Kawakami; Atsuyuki Kojima; Junki Katsube
- Web page: https://patentgrep.com/patent/US4400393A

## CPC

- C07F 9/4018: {Esters of cycloaliphatic acids}
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C07C 45/59: in five-membered rings (from ozonides C07C45/40)
- C07C 45/71: being hydroxy groups
- C07C 49/743: having unsaturation outside the rings, e.g. humulones, lupulones
- C07C 59/46: containing rings other than six-membered aromatic rings
- C07C 59/66: the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C 405/0083: {which is only ortho or peri condensed, e.g. carbacyclins}
- C07D 317/72: spiro-condensed with carbocyclic rings
- Y02P 20/55: Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

A novel bicyclooctane derivative represented by the formula: ##STR1## wherein R.sub.1 is hydrogen or C.sub.1-4 alkyl, X is ethylene or vinylene, and Y.sub.1 and Y.sub.2 are independently hydrogen or a hydroxyl-protecting group, or a pharmaceutically acceptable salt of said compound in which R.sub.1 is hydrogen. Said compound and pharmaceutically acceptable salt are chemically stable, have platelet anti-aggregation activity without undesirable pharmacological actions and exhibit the duration of high biological activity.

## Claims

### Claim 1

A compound of the formula: ##STR14## wherein R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl, X is ethylene or vinylene and Y.sub.1 and Y.sub.2 are each, independently of one another, hydrogen or a hydroxyl-protecting group selected from the group consisting of silyl, acetal, alkyl, aralkyl, C.sub.2 -C.sub.6 alkanoyl, and aroyl; or a pharmaceutically acceptable salt of such a compound wherein R.sub.1 is hydrogen.

### Claim 2 (depends on 1)

The compound according to claim 1, wherein each of Y.sub.1 and Y.sub.2 is hydrogen.

### Claim 3 (depends on 1)

The compound according to claim 1, wherein Y.sub.1 and Y.sub.2 are each selected from the group consisting of C.sub.2 -C.sub.6 alkanoyl and aroyl, independently of one another.

### Claim 4 (depends on 3)

The compound according to claim 3, wherein Y.sub.1 and Y.sub.2 are each C.sub.2 -C.sub.6 alkanoyl independently of one another.

### Claim 5 (depends on 1)

A compound of the formula: ##STR15## wherein R.sub.1, Y.sub.1 and Y.sub.2 are each as defined in claim 1.

### Claim 6 (depends on 5)

The compound according to claim 5, wherein each of Y.sub.1 and Y.sub.2 is hydrogen.

### Claim 7 (depends on 5)

The compound according to claim 5, wherein Y.sub.1 and Y.sub.2 are each selected from the group consisting of C.sub.2 -C.sub.6 alkanoyl and aroyl, independently of one another.

### Claim 8 (depends on 7)

The compound according to claim 7, wherein Y.sub.1 and Y.sub.2 are each C.sub.2 -C.sub.6 alkanoyl independently of one another.

### Claim 9

2.beta.-[3'-(1-adamantyl)-3'.alpha.-hydroxy-trans-1'- propenyl]-3.alpha.-hydroxy-7-(4"-carboxy-1"E-butylidene)-cis-bicyclo[3,3,0] octane, and its stereoisomers (3'.beta. and/or 1"Z).

### Claim 10

2.beta.-[3'-(1-adamantyl)-3'.alpha.-hydroxy-tran s-1'-propenyl]-3.alpha.-hydroxy-7-(4"-methoxycarbonyl-1"E-butylidene)-cis-b icyclo[3,3,0]octane, and its stereoisomers (3'.beta. and/or 1"Z).

### Claim 11

2.beta.-[3'-(1-adamantyl)-3'.alpha.-hydroxypropyl]-3.alpha.-h ydroxy-7-(4"-carboxy-1"E-butylidene)-cis-bicyclo[3,3,0]octane, and its stereoisomers (3'.beta. and/or 1"Z).

### Claim 12

2.beta.-[3'-(1-adamantyl)-3'.alph a.-hydroxy-trans-1'-propenyl]-3.alpha.-acetoxy-7-(4"-methoxycarbonyl-1"E-bu tylidene)-cis-bicyclo[3,3,0]octane and its stereoisomers (3'.beta. and/or 1"Z).

### Claim 13

2. beta.-[3'-(1-adamantyl)-3'.alpha.-acetoxy-trans-1'-propenyl]-3.alpha.-aceto xy-7-(4"-methoxycarbonyl-1"E-butylidene)-cis-bicyclo[3,3,0]octane and its stereoisomers (3'.beta. and/or 1"Z).

### Claim 14

2.beta.-[3'-(1-adamantyl)-3'.alph a.-acetoxy-trans-1'-propentyl]-3.alpha.-acetoxy-7-(4"-carboxy-1"E-butyliden e)-cis-bicyclo[3,3,0]octane and its stereoisomers (3'.beta. and/or 1"Z).

### Claim 15 (depends on 1)

A pharmaceutically acceptable salt of a compound as claimed in claim 1, wherein R.sub.1 is hydrogen.

### Claim 16 (depends on 2)

A pharmaceutical composition for the treatment or prevention of thrombosis comprising an anti-thrombotic effective amount of a compound as defined in claim 2 and a pharmaceutically acceptable carrier or diluent.

### Claim 17 (depends on 2)

A process for treating or preventing thrombosis comprising administering to a patient an anti-thrombotic effective amount of a compound as defined in claim 2.

### Claim 18 (depends on 1)

A compound according to claim 1 wherein Y.sub.1 and Y.sub.2 are selected from the group consisting of trimethylsilyl, dimethyl tert.-butylsilyl, dimethylisopropylsilyl, dimethylethylsilyl, 2-tetrahydropyranyl, 2-tetrahydrofuranyl, 1-ethoxyethyl, 2-methoxy-2-propyl, 2-methoxyethoxymethyl, methyl, benzyl, C.sub.2 -C.sub.6 alkanoyl, benzoyl, p-phenyl benzoyl and naphthoyl.

### Claim 19 (depends on 3)

A compound according to claim 3 wherein Y.sub.1 and Y.sub.2 are selected from the group consisting of C.sub.2 -C.sub.6 alkanoyl, benzoyl, p-phenyl benzoyl and naphthoyl.

### Claim 20 (depends on 5)

A compound according to claim 5 wherein Y.sub.1 and Y.sub.2 are selected from the group consisting of trimethylsilyl, dimethyl tert.-butylsilyl, dimethylisopropylsilyl, dimethylethylsilyl, 2-tetrahydropyranyl, 2-tetrahydrofuranyl, 1-ethoxyethyl, 2-methoxy-2-propyl, 2-methoxyethoxymethyl, methyl, benzyl, C.sub.2 -C.sub.6 alkanoyl, benzoyl, p-phenyl benzoyl and naphthoyl.

### Claim 21 (depends on 7)

A compound according to claim 7 wherein Y.sub.1 and Y.sub.2 are selected from the group consisting of C.sub.2 -C.sub.6 alkanoyl, benzoyl, p-phenyl benzoyl and naphthoyl.