# US 3,933,822 A · Azapurinones

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- Number: US 3,933,822 A
- Document ID: US3933822A
- Status: Granted
- Kind: A
- Application number: 05/478,387
- Filed: 1974-06-11
- Granted: 1976-01-20
- Earliest claimed: 1973-06-12
- Assignees: May & Baker Limited
- Inventors: Barbara Joyce Broughton; Bryan John Large; Stuart Malcolm Marshall; David Lord Pain; Kenneth Robert Harry Wooldridge
- Web page: https://patentgrep.com/patent/US3933822A

## CPC

- C07D 487/04: Ortho-condensed systems
- C07D 471/04: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

8-Azapurin-6-ones substituted in the 2-position by a phenyl group carrying in a meta-position a sulphamoyl substituent, and also a hydroxy, alkoxy or alkylthio substituent para with respect to the said sulphamoyl grouping, and pharmaceutically acceptable salts thereof, possess pharmacological properties useful in the treatment of allergic respiratory disorders, for example allergic bronchial asthma.

## Claims

### Claim 1

An 8-azapurin-6-one derivative of the formula: ##SPC7## 40/14
wherein R.sup.1 represents hydroxy, or alkoxy or alkylthio each containing 1 to 10 carbon atoms, R.sup.2 represents hydrogen, alkyl of 1 to 10 carbon atoms, alkyl of 1 to 10 carbon atoms carrying one or more substituents selected from the group consisting of hydroxy and phenyl, cycloalkyl containing 3 to 8 carbon atoms, phenyl, or phenyl carrying one or more substituents selected from the group consisting of alkyl or alkoxy each containing 1 to 6 carbon atoms, halogen, nitro and trifluoromethyl, R.sup.3 represents hydrogen, alkyl of 1 to 10 carbon atoms, or alkyl of 1 to 10 carbon atoms carrying one or more substituents selected from the group consisting of hydroxy and phenyl, or cycloalkyl containing 3 to 8 carbon atoms, and R.sup.4 represents hydrogen, methyl or ethyl, or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

An 8-azapurin-6-one derivative according to claim 1 wherein R.sup.1 represents hydroxy, or alkoxy or alkylthio each containing 1 to 10 carbon atoms, R.sup.2 and R.sup.3 each represent hydrogen, alkyl of 1 to 10 carbon atoms, or alkyl of 1 to 10 carbon atoms carrying one or more hydroxy groups, and R.sup.4 represents hydrogen, or a pharmaceutically acceptable salt thereof.

### Claim 3 (depends on 1)

An 8-azapurin-6-one derivative according to claim 1 wherein R.sup.1 represents propoxy, R.sup.2 represents phenyl, or phenyl carrying one or more substituents selected from the group consisting of alkyl or alkoxy each containing 1 to 6 carbon atoms, halogen, nitro and trifluoromethyl, R.sup.3 represents hydrogen, alkyl of 1 to 10 carbon atoms, or alkyl of 1 to 10 carbon atoms carrying one or more substituents selected from the group consisting of hydroxy and phenyl, or cycloalkyl containing 3 to 8 carbon atoms, and R.sup.4 represents hydrogen, methyl or ethyl, or a pharmaceutically acceptable salt thereof.

### Claim 4 (depends on 1)

An 8-azapurin-6-one derivative according to claim 1 wherein R.sup.1 represents alkoxy containing 1 to 3 carbon atoms, or a pharmaceutically acceptable salt thereof.

### Claim 5 (depends on 1)

An 8-azapurin-6-one derivative according to claim 1 wherein R.sup.1 represents propoxy, R.sup.2 represents alkyl containing 1 to 10 carbon atoms, R.sup.3 represents alkyl containing 1 to 4 carbon atoms, and R.sup.4 represents hydrogen, methyl or ethyl or a pharmaceutically acceptable salt thereof.

### Claim 6 (depends on 5)

An 8-azapurin-6-one derivative according to claim 5 wherein one or both of the alkyl groups represented by R.sup.2 and R.sup.3 is branched-chain alkyl.

### Claim 7 (depends on 1)

The azapurinone according to claim 1 which is 8-aza-2-(5-N,N-dimethylsulphamoyl-2-propoxyphenyl)purin-6-one, or a pharmaceutically acceptable salt thereof.

### Claim 8 (depends on 1)

The azapurinone according to claim 1 which is 8-aza-2-(5-N,N-diethylsulphamoyl-2-propoxyphenyl)purin-6-one, or a pharmaceutically acceptable salt thereof.

### Claim 9 (depends on 1)

The azapurinone according to claim 1 which is 8-aza-2-(5-N,N-dipropylsulphamoyl-2-propoxyphenyl)purin-6-one, or a pharmaceutically acceptable salt thereof.

### Claim 10 (depends on 1)

The azapurinone according to claim 1 which is 8-aza-2-(5-N-isopropyl-N-methylsulphamoyl-2-propoxyphenyl)-purin-6-one, or a pharmaceutically acceptable salt thereof.

### Claim 11 (depends on 1)

The azapurinone according to claim 1 which is 8-aza-2-(5-N-phenylsulphamoyl-2-propoxyphenyl)purin-6-one, or a pharmaceutically acceptable salt thereof.

### Claim 12 (depends on 1)

The azapurinone according to claim 1 which is 8-aza-2-(5-N-cyclohexyl-N-methylsulphamoyl-2-propoxyphenyl)-purin-6-one, or a pharmaceutically acceptable salt thereof.

### Claim 13 (depends on 1)

An azapurinone derivative according to claim 1 selected from the group consisting of 8-aza-2-(5-N-methylsulphamoyl-2-propoxyphenyl)purin-6-one, 8-aza-2-(2-propoxy-5-sulphamoylphenyl)purin-6-one, 8-aza-2-(5-N-t-butylsulphamoyl-2-propoxyphenyl)purin-6-one, 8-aza-2-(5-N-ethylsulphamoyl-2-propoxyphenyl)purin-6-one, 8-aza-2-[5-(N-2-hydroxyethyl-N-methylsulphamoyl)-2-propoxyphenyl]purin-6-o ne, N-[3-(8-aza-6-oxopurin-2-yl)-4-propoxybenzenesulphonyl]-1-deoxy-1-methylam inoglucitol, N-[3-(8-aza-6-oxopurin-2-yl)-4-propoxybenzenesulphonyl]-1-amino-1-deoxyglu citol, 8-aza-2-(5-N-hexylsulphamoyl-2-propoxyphenyl)purin-6-one, 8-aza-2-(5-N-butyl-N-methylsulphamoyl-2-propoxyphenyl)purin-6-one, 8-aza-2-(5-N-benzyl-N-methylsulphamoyl-2-propoxyphenyl)purin-6-one, 8-aza-2-(5-N,N-dimethylsulphamoyl-2-methoxyphenyl)purin-6-one, 8-aza-2-(5-N-isopropylsulphamoyl-2-methoxyphenyl)purin-6-one, 8-aza-2-(5-N-t-butysulphamoyl-2-methoxyphenyl)purin-6-one, 8-aza-2-(5-N-isopropyl-N-methylsulphamoyl-2-methoxyphenyl)purin-6-one, 8-aza-2-(5-N-benzylsulphamoyl-2-propoxyphenyl)purin-6-one, 8-aza-2-(5-N-methyl-N-phenylsulphamoyl-2-propoxyphenyl)purin-6-one, 8-aza-2-[5-N-(2-methoxyphenyl)sulphamoyl-2-propoxyphenyl]-purin-6-one, 8-aza-2-[5-N-(3-methoxyphenyl)sulphamoyl-2-propoxyphenyl]purin-6-one, 8-aza-2-[5-N-(4-methoxyphenyl)-sulphamoyl-2-propoxyphenyl]purin-6-one, 8-aza-2-[5-N-(3-trifluoromethylphenyl)sulphamoyl-2-propoxyphenyl]purin-6-o ne, 8-aza-2-(5-N,N-dihexylsulphamoyl-2-propoxyphenyl)-purin-6-one, 8-aza-2-(4-methyl-5-N-methylsulphamoyl-2-propoxyphenyl)purin-6-one, 8-aza-2-(4-methyl-5-N,N-dimethylsulphamoyl-2-propoxyphenyl)purin-6-one, 8-aza-2-(4-methyl-2-propoxy-5-sulphamoylphenyl)purin-6-one, 8-aza-2-(5-N-t-butylsulphamoyl-4-methyl-2-propoxyphenyl)-purin-6-one, 8-aza-2-(5-N-ethyl-N-isopropylsulphamoyl-2-propoxyphenyl)purin-6-one, 8-aza-2-(5-N-sec.-butyl-N-methylsulphamoyl-2-propoxyphenyl)purin-6-one, 8-aza-2-(5-N-isopropylsulphamoyl-2-propoxyphenyl)purin-6-one, 8-aza-2-[5-N-(2,6-dimethylphenyl)sulphamoyl-2-propoxyphenyl]purin-6-one, 8-aza-2-[5-N-(4-chlorophenyl)sulphamoyl-2-propoxyphenyl]purin-6-one, 8-aza-2-[5-(4-nitrophenyl)-sulphamoyl-2-propoxyphenyl]purin-6-one, and a pharmaceutically acceptable salt thereof.