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US 6,552,084 B2Granted
Hydroxyeicosatetraenoic acid analogs and methods of their use in treating dry eye disorders
AssigneeAlcon Universal Ltd.
InventorsPeter G. Klimko, Mark R. Hellberg, John R. Falck, Raymond E. Conrow
Life of this patent
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Abstract
Hydroxyeicosatetraenoic acid analogs and methods of their use in treating dry eye disorders are disclosed.
Claims24
A composition for the treatment of dry eye in humans comprising a pharmaceutically acceptable carrier and a pharmaceutically effective amount of one or more compounds of the following formula I:
- n-C5H11—Y—A—CH2—R1 I
- wherein:
- R1 is CO2R, CONR2R3, CH2OR4, CH2NR5R6, CH2N3, CH2Hal, CH2NO2, CH2SR20, COSR21, or 2,3,4,5-tetrazol-1-yl, where:
- R is H or a pharmaceutically acceptable cation, or CO2R forms a pharmaceutically acceptable ester moiety;
- NR2R3, NR5R6 are the same or different and comprise a free or functionally modified amino group;
- OR4 comprises a free or functionally modified hydroxy group;
- Hal is F, Cl, Br, or I;
- R20 is H, alkyl, acyl;
- R21 is H or a pharmaceutically acceptable cation, or COSR21 forms a pharmaceutically acceptable thioester moiety;
- A is L1—A1—L2, L1—A2—L2, L3—A2—L4, or L5—A2—L3;
- A1 is CH2CH2;
- A2is
- L1 is CH2—B—D;
- B and D are the same or different and are CH2CH2, CH═CH, or C≡C;
- L2 is CH2—K—CH2CH2;
- K is CH2CH2, CH═CH, or C≡C;
- L3 is CH2CH2CH2, CH2CH═CH, CH2C≡C, CH═CHCH2, C≡CCH2, or CH═C═CH;
- L4 is X—CH2CH2;
- X is CH2CH2CH═CH, CH2CH2C≡C, CH2CH2CH2CH2, CH2CH═CHCH2, CH2C≡CCH2, CH═CHCH2CH2, C≡CCH2CH2, CH2CH═C═CH, or CH═C═CHCH2;
- L5 is CH2CH2—B—D;
- and
- Y is C(O) (i.e. a carbonyl group) or Y is
- wherein R9O constitutes a free or functionally modified hydroxy group.
20 more elements
A method for the treatment of dry eye or other disorders requiring the wetting of the eye in mammals comprising administering to an affected eye, a pharmaceutically effective amount of one or more compounds according to formula I:
- n-C5H11—Y—A—CH2—R1 I
- wherein:
- R1 is CO2R, CONR2R3, CH2OR4, CH2NR5R6, CH2N3, CH2Hal, CH2NO2, CH2SR20, COSR21, or 2,3,4,5-tetrazol-1-yl, where:
- R is H or a pharmaceutically acceptable cation, or CO2R forms a pharmaceutically acceptable ester moiety;
- NR2R3, NR5R6 are the same or different and comprise a free or functionally modified amino group;
- OR4 comprises a free or functionally modified hydroxy group;
- Hal is F, Cl, Br, or I;
- R20 is H, alkyl, acyl;
- R21 is H or a pharmaceutically acceptable cation, or COSR21 forms a pharmaceutically acceptable thioester moiety;
- A is L1—A1—L2, L1—A2—L2, L3—A2—L4, or L5—A2—L3;
- A1 is CH2CH2;
- A2 is
- L1 is CH2—B—D;
- B and D are the same or different and are CH2CH2, CH═CH, or C≡C;
- L2 is CH2—K—CH2CH2;
- K is CH2CH2, CH═CH, or C≡C;
- L3 is CH2CH2CH2, CH2CH═CH, CH2C≡C, CH═CHCH2, C≡CCH2, or CH═C═CH;
- L4 is X—CH2CH2;
- X is CH2CH2CH═CH, CH2CH2C≡C, CH2CH2CH2CH2, CH2CH═CHCH2, CH2C≡CCH2, CH═CHCH2CH2, C≡CCH2CH2, CH2CH═C═CH, or CH═C═CHCH2;
- L5 is CH2CH2—B—D;
- and
- Y is C(O) (i.e. a carbonyl group) or Y is
- wherein R9O constitutes a free or functionally modified hydroxy group.
20 more elements
A compound of formula I:
- n-C5H11—Y—A—CH2—R1 I
- wherein:
- R1 is CO2R, CONR2R3, CH2OR4, CH2NR5R6, CH2N3, CH2Hal, CH2NO2, CH2SR20, COSR21, or 2,3,4,5-tetrazol-1-yl, where:
- R is H or a pharmaceutically acceptable cation, or CO2R forms a pharmaceutically acceptable ester moiety;
- NR2R3, NR5R6 are the same or different and comprise a free or functionally modified amino group;
- OR4 comprises a free or functionally modified hydroxy group;
- Hal is F, Cl, Br, or I;
- R20 is H, alkyl, acyl;
- R21 is H or a pharmaceutically acceptable cation, or COSR21 forms a pharmaceutically acceptable thioester moiety;
- A is L1—A2—L2, L3—A2—L4, or L5—A2—L3;
- A2 is
- L1 is CH2—B—D;
- B and D are the same or different and are CH2CH2, CH═CH, or C≡C;
- L2 is CH2—K—CH2CH2;
- K is CH2CH2, CH═CH, or C≡C;
- L3 is CH2CH2CH2, CH2CH═CH, CH2C≡C, CH═CHCH2, C≡CCH2, or CH═C═CH;
- L4 is X—CH2CH2;
- X is CH2CH2CH═CH, CH2CH2C≡C, CH2CH2CH2CH2, CH2CH═CHCH2, CH2C≡CCH2, CH═CHCH2CH2, C≡CCH2CH2, CH2CH═C═CH, or CH═C═CHCH2;
- L5 is CH2CH2—B—D;
- and
- Y is C(O) (i.e. a carbonyl group) or Y is
- wherein R9O constitutes a free or functionally modified hydroxy group.
19 more elements
Dependencies are inferred from the claim text.