# US 4,400,382 A · Thiazoloquinoxalin-1,4-diones for treating allergy

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- Number: US 4,400,382 A
- Document ID: US4400382A
- Status: Granted
- Kind: A
- Application number: 06/244,361
- Filed: 1981-03-16
- Granted: 1983-08-23
- Earliest claimed: 1980-05-09
- Assignees: USV Pharmaceutical Corporation
- Inventors: Richard E. Brown; Vassil St. Georgiev; Philip Kropp; Bernard Loev
- Web page: https://patentgrep.com/patent/US4400382A

## CPC

- C07D 471/04: Ortho-condensed systems
- C07D 241/44: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D 471/14: Ortho-condensed systems
- C07D 487/04: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

New triazoloquinoxalin-1,4-diones are described as well as the use thereof as anti-allergenic agents.

## Claims

### Claim 1

An anti-allergic compound of the formula: ##STR13## wherein, X and X.sup.1 are S or O and may be the same or different;
each of R.sub.1 and R.sub.2 is hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkenyl, C.sub.1 -C.sub.10 alkynyl, cyclo C.sub.3 -C.sub.10 alkyl, C.sub.6 -C.sub.10 aryl, C.sub.6 -C.sub.10 ar C.sub.1 -C.sub.10 alkyl, sulfonamido, halogen, C.sub.1 -C.sub.10 alkoxy, C.sub.1 -C.sub.10 alkenyloxy, C.sub.1 -C.sub.10 alkynyloxy, cyano, hydroxy, nitro, amino, C.sub.1 -C.sub.10 alkylamino, C.sub.1 -C.sub.10 alkanoylamino, carb C.sub.1 -C.sub.10 alkoxyamino, methanesulfonyl, carboxy, carb C.sub.1 -C.sub.10 alkoxy, trihalomethyl, or taken together, methylenedioxy;
each of R.sub.3 and R.sub.4 is hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkenyl, C.sub.1 -C.sub.10 alkynyl, C.sub.6 -C.sub.10 aryl, C.sub.6 -C.sub.10 ar C.sub.1 -C.sub.10 alkyl, cyclo C.sub.3 -C.sub.10 alkyl, cyclo C.sub.3 -C.sub.10 alkyl CH.sub.2 -, or carba C.sub.1 -C.sub.10 alkoxy; and
pharmaceutically-acceptable acid addition salts thereof, and
where R.sub.4 is hydrogen, the alkali and alkaline-earth metal salts thereof.

### Claim 2 (depends on 1)

A pharmaceutical composition for use as an antiallergic agent, said composition containing a therapeutically effective amount of a compound according to claim 1.

### Claim 3

An anti-allergic compound of the formula: ##STR14## wherein, each of R.sub.1 and R.sub.2 is hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkenyl, C.sub.1 -C.sub.10 alkynyl, cyclo C.sub.3 -C.sub.10 alkyl, C.sub.6 -C.sub.10 aryl, C.sub.6 -C.sub.10 ar C.sub.1 -C.sub.10 alkyl, sulfonamido, halogen, C.sub.1 -C.sub.10 alkoxy, C.sub.1 -C.sub.10 alkenyloxy, C.sub.1 -C.sub.10 alkynyloxy, cyano, hydroxy, nitro, amino, C.sub.1 -C.sub.10 alkylamino, C.sub.1 -C.sub.10 alkanoylamino, carb C.sub.1 -C.sub.10 alkoxyamino, methanesulfonyl, carboxy, carb C.sub.1 -C.sub.10 alkoxy, trihalomethyl, or taken together, methylenedioxy; and
each of R.sub.3 and R.sub.4 is hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkenyl, C.sub.1 -C.sub.10 alkynyl, C.sub.6 -C.sub.10 aryl, C.sub.6 -C.sub.10 ar C.sub.1 -C.sub.10 alkyl, cyclo C.sub.3 -C.sub.10 alkyl, cyclo C.sub.3 -C.sub.10 alkyl CH.sub.2 --, or carb C.sub.1 -C.sub.10 alkoxy;
pharmaceutically-acceptable acid addition salts thereof, and
where R.sub.4 is hydrogen, the alkali and alkaline-earth metal salts thereof.

### Claim 4 (depends on 3)

A compound according to claim 3 wherein R.sub.1 and R.sub.2 are hydrogen.

### Claim 5 (depends on 3)

A compound according to claim 3 wherein R.sub.3 is methyl.

### Claim 6 (depends on 5)

A compound according to claim 5 wherein R.sub.4 is hydrogen.

### Claim 7 (depends on 5)

A compound according to claim 5 wherein R.sub.4 is acetyl.

### Claim 8 (depends on 3)

A compound according to claim 3 wherein R.sub.1 is hydrogen, R.sub.2 is 8-trifluoromethyl, R.sub.3 is methyl, and R.sub.4 is hydrogen.

### Claim 9 (depends on 3)

A compound according to claim 3 wherein R.sub.1 is hydrogen, R.sub.2 is hydrogen, R.sub.3 is methyl, and R.sub.4 is hydrogen.

### Claim 10 (depends on 3)

A compound according to claim 3 wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are hydrogen.

### Claim 11 (depends on 3)

A compound according to claim 3 wherein R.sub.1 is hydrogen, R.sub.2 is 8-chlorine, R.sub.3 is methyl, and R.sub.4 is hydrogen.

### Claim 12 (depends on 3)

A compound according to claim 3 wherein R.sub.1 is hydrogen, R.sub.2 is hydrogen, R.sub.3 is methyl, and R.sub.4 is carbethoxy.

### Claim 13 (depends on 3)

A compound according to claim 3 wherein R.sub.1 is hydrogen, R.sub.2 is 8-carbomethoxy, R.sub.3 is methyl, and R.sub.4 is hydrogen.

### Claim 14 (depends on 3)

A compound according to claim 3 wherein R.sub.1 is hydrogen, R.sub.2 is 6-methyl, R.sub.3 is methyl, and R.sub.4 is hydrogen.

### Claim 15 (depends on 3)

A compound according to claim 3 wherein R.sub.1 is 7-chlorine, R.sub.2 is hydrogen, R.sub.3 is n-propyl, and R.sub.4 is hydrogen.

### Claim 16 (depends on 3)

A compound according to claim 3 wherein R.sub.1, R.sub.2 and R.sub.4 are each hydrogen and R.sub.3 is n-propyl.

### Claim 17 (depends on 3)

A compound according to claim 3 wherein R.sub.1 is 7-chloro, R.sub.2 and R.sub.4 are hydrogen, and R.sub.3 is methyl.