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US 5,710,288 AGranted
1,3-benzodioxole and 1,2-dialkoxybenzene derivatives as ocular hypotensive agents
AssigneeAllergan, Inc.
InventorsRobert M. Burk, David F. Woodward
Life of this patent
Estimating the term…
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.
Claims15
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.
5 more elements
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.
4 more elements
Dependencies are inferred from the claim text.