# US 5,350,860 A · Bicyclic compounds

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- Number: US 5,350,860 A
- Document ID: US5350860A
- Status: Granted
- Kind: A
- Application number: 08/005,611
- Filed: 1993-01-19
- Granted: 1994-09-27
- Earliest claimed: 1992-01-31
- Assignees: Santen Pharmaceutical Co., Ltd.
- Inventors: Shiro Mita; Yoichi Kawashima; Ken-ichi Fujimura; Hiroshi Suhara; Masahiro Okamoto
- Web page: https://patentgrep.com/patent/US5350860A

## CPC

- C07D 495/08: Bridged systems
- A61P 37/00: Drugs for immunological or allergic disorders
- A61P 37/02: Immunomodulators
- A61P 37/04: Immunostimulants
- A61P 37/06: Immunosuppressants, e.g. drugs for graft rejection
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

A compound of the formula [I]. ##STR1## The compounds of this invention has excellent thymulin-line activities and expected to be useful for treatment of various diseases such as immunodeficiency and autoimmune diseases.

## Claims

### Claim 1

A compound of the formula [I] and pharmaceutically acceptable salts thereof, ##STR9## wherein R.sup.1 and R.sup.2 are the same or different and each is hydrogen or a straight or branched chain alkyl having 1 to 6 carbon atoms;
R.sup.3 and R.sup.4 are the same or different and each is hydrogen, a straight or branched chain alkyl having 1 to 6 carbon atoms, carboxy or lower alkoxycarbonyl;
R.sup.5 is hydrogen or straight or branched chain alkyl having 1 to 6 carbon atoms;
X is oxygen or NR.sup.6 ;
R.sup.6 is hydrogen, lower alkyl, lower alkoxy, phenyl lower alkyl or phenyl lower alkoxy, and the said lower alkyl can be substituted by carboxy, lower alkoxycarbonyl, amino, lower alkylamino, lower alkoxycarbonylamino or phenyl lower alkylamino, and the phenyl ring of the said phenyl lower alkyl, phenyl lower alkoxy or phenyl lower alkylamino can be substituted by lower alkyl, lower alkoxy, fluorine, chlorine, bromine, iodine, carboxy or lower alkoxycarbonyl wherein each lower alkyl is a straight or branched alkyl having 1 to 6 carbon atoms, and each lower alkoxy is a straight or branched alkoxy having 1 to 6 carbon atoms;
A is straight or branched alkylene having 1 to 6 carbon atoms,
n is 0 to 1.

### Claim 2 (depends on 1)

The compound as in claim 1 wherein X is oxygen, R.sup.5 is hydrogen and n is 1.

### Claim 3 (depends on 1)

The compound as in claim 1 wherein X is oxygen and n is 0.

### Claim 4 (depends on 1)

The compound as in claim 1 wherein X is NR.sup.6, R.sup.5 is hydrogen and n is 1.

### Claim 5 (depends on 1)

The compound as in claim 1 wherein X is NR.sup.6 and n is 0.

### Claim 6

(6,6-dimethyl-9-oxo)-3,5-dithia-8-oxabicyclo[5,2,1]decane.

### Claim 7

(6,6-dimethyl-9-oxo)-3,5-dithia-8-azabicyclo[5,2,1]decane.

### Claim 8

(5,5-dimethyl-8-oxo)-3,4-dithia-7-oxabicyclo[4,2,1]nonane.

### Claim 9

(5,5-dimethyl-8-oxo)-3,4-dithia-7-azabicyclo[4,2,1]nonane.

### Claim 10

A pharmaceutical composition comprising a compound of the formula [I] or pharmaceutically acceptable salts thereof and a pharmaceutically acceptable ingredient.

### Claim 11 (depends on 1)

The compound of claim 1 selected from the group consisting of
(9-oxo)-3,5-dithia-8-oxabicyclo]5,2,1]decane,
(2-methyl-9-oxo)-3,5-dithia-8-oxabicyclo[5,2,1]decane,
(10-methyl-9-oxo)-3,5-dithia-8-oxabicyclo[5,2,1]decane and
(10-oxo)-3,5-dithia-9-oxabicyclo[6,2,1]undecane.

### Claim 12 (depends on 1)

The compound of claim 1 selected from the group consisting of
(8-benzyl-9-oxo)-3,5-dithia-8-azabicyclo[5,2,1]decane,
[8-(4-carboxyphenylmethyl)-6,6-dimethyl-9-oxo]-3,5-dithia-8-azabicyclo [5,2,1]decane,
(8-carboxymethyl-6,6-dimethyl-9-oxo)-3,5-dithia-8-azabicyclo[5,2,1]decane,
(2-methyl-9-oxo)-3,5-dithia-8-azabicyclo[5,2,1]decane,
(10-methyl-9-oxo)-3,5-dithia-8-azabicyclo[5,2,1]decane,
(8-isopropyl-9-oxo)-3,5-dithia-8-azabicyclo[5,2,1]decane,
[6,6-dimethyl-8-(5-tert-butoxycarbonylaminopentyl)-9-oxo]-3,5-dithia-8-azab icyclo [5,2,1]decane,
[6,6-dimethyl-8-(5-aminopentyl)-9-oxo]-3,5-dithia-8-azabicyclo [5,2,1]decane and
(6,6-dimethyl-10-oxo)-3,5-dithia-9-azabicyclo[6,2,1]undecane.

### Claim 13 (depends on 1)

The compound of claim 1 selected from the group consisting of
(8-oxo)-3,4-dithia-7-oxabicyclo[4,2,1]nonane,
(2-methyl-8-oxo)-3,4-dithia-7-oxabicyclo[4,2,1]nonane,
(9-methyl-8-oxo)-3,4-dithia-7-oxabicyclo[4,2,1]nonane and
(9-oxo)-3,4-dithia-8-oxabicyclo[5,2,1]decane.

### Claim 14 (depends on 1)

The compound of claim 1 selected from the group consisting of
(7-benzyl-8-oxo)-3,4-dithia-7-azabicyclo[4,2,1]nonane,
[7-(4-carboxyphenylmetnyl)-5,5-dimethyl-8-oxo]-3,4-dithia-7-azabicyclo [4,2,1]nonane,
(7-carboxymethyl-5,5-dimethyl-8-oxo)-3,4-dithia-7-azabicyclo[4,2,1]nonane,
(2-methyl-8-oxo)-3,4-dithia-7-azabicyclo[4,2,1]nonane,
(9-methyl-8-oxo)-3,4-dithia-7-azabicyclo[4,2,1]nonane,
(7-isopropyl-8-oxo)-3,4-dithia-7-azabicyclo[4,2,1]nonane,
[5,5-dimethyl-7-(5-tert-butoxycarbonylaminopentyl)-8-oxo]-3,4-dithia-7-azab icyclo [4,2,1]nonane,
[5,5-dimethyl-7-(5-aminopentyl)-8-oxo]-3,4-dithia-7-azabicyclo [4,2,1]nonane and
(5,5-dimethyl-9-oxo)-3,4-dithia-8-azabicyclo[5,2,1]decane.

### Claim 15 (depends on 10)

The pharmaceutical composition of claim 10 wherein said compound of formula [I] is
(6,6-dimethyl-9-oxo)-3,5-dithia-8-oxabicyclo[5,2,1]decane,
(6,6-dimethyl-9-oxo)-3,5-dithia-8-azabicyclo[5,2,1]decane,
(5,5-dimethyl-8-oxo)-3,4-dithia-7-oxabicyclo[4,2,1]nonane or
(5,5-dimethyl-8-oxo)-3,4-dithia-7-azabicyclo[4,2,1]nonane.