# US 5,710,288 A · 1,3-benzodioxole and 1,2-dialkoxybenzene derivatives as ocular hypotensive agents

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- Number: US 5,710,288 A
- Document ID: US5710288A
- Status: Granted
- Kind: A
- Application number: 08/646,697
- Filed: 1996-05-03
- Granted: 1998-01-20
- Earliest claimed: 1993-04-21
- Assignees: Allergan, Inc.
- Inventors: Robert M. Burk; David F. Woodward
- Web page: https://patentgrep.com/patent/US5710288A

## CPC

- C07C 43/23: containing hydroxy or O-metal groups
- C07C 59/64: containing six-membered aromatic rings
- C07C 69/734: Ethers
- C07D 317/54: Radicals substituted by oxygen atoms
- C07D 317/60: Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Compounds of the formula ##STR1## where the symbols have the meaning defined in the specification, are capable of lowering intraocular pressure in the eye of a mammal.

## Claims

### Claim 1

A compound of the formula ##STR9## where W is (CH.sub.2). where n is 1 or 2;
m is an integer between 1 and 8;
R.sub.1 is COOH or a pharmaceutically acceptable salt thereof, COOR.sub.4, CONR.sub.5 R.sub.6, CONR.sub.5 SO.sub.2 R.sub.7,CH.sub.2 OH, CH.sub.2 OR.sub.7, CH.sub.2 O--COR.sub.7, CH.sub.2 O--CONR.sub.5 R.sub.7, CH.sub.2 OCOOR.sub.7, CH.sub.2 NR.sub.5 R.sub.6, CH.sub.2 NR.sub.5 COR.sub.7, CHO, CH(OR.sub.8).sub.2, CH(OR.sub.9 O), --COR.sub.10, CR.sub.10 (OR.sub.8).sub.2, or CR.sub.10 (OR.sub.9 O), where R.sub.4 is an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R.sub.4 is phenyl or lower alkylphenyl, R.sub.5 and R.sub.6 independently are hydrogen, an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or phenyl or lower alkylphenyl, R.sub.7 is alkyl of 1 to 10 carbons, phenyl or lower alkylphenyl, R.sub.8 is lower alkyl, and R.sub.9 is divalent alkyl radical of 2-5 carbons, R.sub.10 is an alkyl or cycloalkyl containing 1 to 5 carbons;
R.sub.2 is H, COR.sub.7, R.sub.7, CO--OR.sub.7, CO--NR.sub.2 R.sub.7, PO(OH)OR.sub.7, PO(OR.sub.7).sub.2, POR.sub.7 OH, or POR.sub.7 (OR.sub.7);
R.sub.3 is HETEROCYCLIC--(R.sub.11).sub.p, where HETEROCYCLIC is a 5 or six-membered heterocyclic ring containing 1 or 2 heteroatoms selected from N, S, and O;
R.sub.11 is independently lower alkyl of 1-6 carbons, halogen, fluoro-substituted lower alkyl of 1-6 carbons, C.tbd.N, NO.sub.2, SO.sub.2 R.sub.12, COOH, COOR.sub.12, CONH.sub.2, CONHR.sub.12, CON(R.sub.12).sub.2, or CO--R.sub.12 ;
p is an integer between 1-3,
r is an integer between 1-5, and
R.sub.12 is lower alkyl of 1-6 carbons.

### Claim 2 (depends on 1)

A compound of claim 1 wherein W represents (CH.sub.2).sub.n and n is 1.

### Claim 3 (depends on 1)

A compound of claim 1 wherein W represents lower alkyl groups attached to each oxygen.

### Claim 4 (depends on 1)

A compound of claim 1 wherein m is 4.

### Claim 5 (depends on 1)

A compound of claim 1 wherein R.sub.1 is COOH, COOR.sub.4 or CH.sub.2 OH.

### Claim 6 (depends on 1)

A compound of claim 1 wherein r is 2.

### Claim 7 (depends on 1)

A compound of claim 1 wherein R.sub.3 is HETEROCYCLIC--(R.sub.11).sub.p, where HETEROCYCLIC is a divalent radical of thiophene, furan, thiazole or oxazole.

### Claim 8 (depends on 1)

A compound of claim 1 where p is 1, and R.sub.11 is CH.sub.3, halogen or trifluoromethyl.

### Claim 9 (depends on 1)

A compound of claim 1 wherein R.sub.2 is H or COR.sub.7 wherein R, is lower alkyl.

### Claim 10

A compound of the formula ##STR10## wherein m is an integer between 1 and 8;
R.sub.1 is COOH or a pharmaceutically acceptable salt thereof, COOR.sub.4, CONR.sub.5 R.sub.6, CONR.sub.5 SO.sub.2 R.sub.7,CH.sub.2 OH, CH.sub.2 OR.sub.7, CH.sub.2 O--COR.sub.7, CH.sub.2 O--CONR.sub.5 R.sub.7, CH.sub.2 OCOOR.sub.7, CH.sub.2 NH.sub.2, CH.sub.2 NR.sub.5 R.sub.6, CH.sub.2 NR.sub.5 COR.sub.7, where R.sub.4 is an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R.sub.4 is phenyl or lower alkylphenyl, R.sub.5 and R.sub.6 independently are hydrogen, an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or phenyl or lower alkylphenyl, R.sub.7 is alkyl of 1 to 10 carbons, phenyl or lower alkylphenyl;
R.sub.2 is H, COR.sub.7, R.sub.7, CO--OR.sub.7, CO--NR.sub.5,R.sub.7, PO(OH)OR.sub.7, PO(OR.sub.7).sub.2, POR.sub.7 OH, or POR.sub.7 (OR.sub.7);
R.sub.3 is HETEROCYCLIC-(R.sub.11).sub.p, where HETEROCYCLIC is selected from furan and thiophene;
R.sub.11 is independently lower alkyl of 1-6 carbons, halogen, fluoro-substituted lower alkyl of 1-6 carbons, C.tbd.N, NO.sub.2, SO.sub.2 R.sub.12, COOH, COOR.sub.12, CONH.sub.2, CONHR.sub.12, CON(R.sub.12).sub.2, or CO--R.sub.12 ;
p is an integer between 1-3,
r is an integer between 1-5, and
R.sub.12 is lower alkyl of 1-6 carbons.

### Claim 11 (depends on 10)

A compound of claim 10 wherein r is 2.

### Claim 12 (depends on 11)

A compound of claim 11 wherein m is 4.

### Claim 13 (depends on 12)

A compound of claim 12 wherein R.sub.1 is CO.sub.2 CH.sub.3, CO.sub.2 H or CH.sub.2 OH.

### Claim 14 (depends on 13)

A compound of claim 13 wherein p is 1.

### Claim 15 (depends on 14)

A compound of claim 14 wherein R.sub.11 is selected from CH.sub.3, halogen and CF.sub.3.