Ophthalmic pharmaceutical compositions and methods for treating ocular inflammation

1. An ophthalmic pharmaceutical composition comprising a pharmaceutically acceptable ophthalmic carrier and about 0.001 nanograms per milliliter to 1.0 milligrams per milliliter of a 4-aminoquinoline compound of formula I:

wherein A is

, (C(R 3 )(R 4 )) n ;

or

A is

or (C 5 C 6 )-cycloalkylene; n is 1–4;

or

A is an alkyl of 1 through 5 carbon atoms substituted by a dialkylamino group of which each alkyl radical contains 1 through 4 carbon atoms, phenyl, or phenyl substituted by one or more radicals selected from carboxy and hydroxy and alkyl radicals of 1 through 4 carbon atoms and R 9 is hydrogen or halogen; and R 10 is halogen or trifluoromethyl;

and

R 1 to R 6 are hydrogen or in which one or two of R 1 to R 6 are independently selected from alkyl and the other substituents are hydrogen; R 7 and R 8 are independently selected from alkyl, alkenyl or aralkyl, or together with the N atom signify pyrrolidine or piperidine, either or both of which may be substituted by alkyl; and n=0 or 1; or

wherein R 1 and R 3 are tri- or tetramethylene; R 2 and R 4 to R 6 are hydrogen; n=0; and R 7 and R 8 are defined as above; or

wherein R 1 and R 7 are methylene or dimethylene and n=1, or

R 3 and R 7 are di- or trimethylene and n=0, or

R 3 and R 7 are di- or trimethylene and n=1, or

R 3 and R 7 are tri- or tetramethylene and n=0, or

R 5 and R 7 are tri- or tetramethylene and n=1, or

R 1 and R 5 are di- or tri-methylene and n=1, and the remaining substituents are hydrogen, except R 8 which is selected from alkyl, alkenyl or alkynyl; or

wherein R 3 and R 5 are tri- or tetramethylene and n=1; R 1 , R 2 , R 4 and R 6 are hydrogen; and R 7 and R 8 are selected from alkyl, alkenyl or aralkyl or together with the N atom are pyrrolidine or piperidine, either or both of which may be substituted by alkyl;

R 9 is hydrogen or halogen; and R 10 is halogen or trifluoromethyl;

R 11 is a hydrogen atom or an alkyl radical (1–5 carbon atoms); or

R 7 is hydrogen and R 8 is (CH 2 ) p -B and p is 1–3;

B is aryl selected from phenyl, phenyl mono-, di-, or tri-substituted by substituent from the group consisting of halogen, hydroxy, lower alkyl, lower alkoxy, trifluoromethyl, cyano, di-lower alkylamino or their N-oxides, phenyloxy, phenyl, and methylsuphanyl, naphthyl, benzo[1,3]dioxol, or monocyclic aromatic heterocycle with 1 or 2 heteroatoms selected from N and O;

and

R 9 is hydrogen or halogen; and R 10 is halogen or trifluoromethyl;

as well as pharmaceutically acceptable salts of basic compounds of formula I.