Patent US4861783A successfully refreshed from Google Patents.
US4861783A
Expired / Lapsed
US
⏱️ 0.0 years remaining
4-quinoline carboxylic acid derivatives useful for treating skin and muco-epithelial diseases
Assignee: Bristol Myers Squibb Pharma Co
•
Filing: 1988-04-26
•
Granted: 1989-08-29
•
Expires: 2008-04-26
Abstract
Abstract Phenylquinolinecarboxylic acids and derivatives thereof, such as 2-(2 min -Fluoro-1,1 min -biphenyl-4-yl)-6-fluoro-3-methyl-4-quinolinecarboxylic acid, or a sodium or potassium salt thereof, are useful for the treatment of skin and muco-epithelial diseases.
Inventors
- 👤 Neil R. Ackerman
- 👤 Richard R. Harris
- 👤 Scott E. Loveless
- 👤 Russel H. Neubauer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 16:36
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/33; A61K31/395; A61K31/435; A61K31/47; A61P; A61P1/00; A61P17/00; A61P37/00; A61P37/08; C; C07; C07D; C07D215/00; C07D215/02; C07D215/16; C07D215/48; C07D215/50; C07D215/52; Y; Y02; Y02A; Y02A50/00; Y02A50/30
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
315 words
A method of treating a skin or mucoepithelial disease in a mammal selected from the group consisting of psoriasis, lichen planas, chronic eczema, icthyosis, pityriasis and chronic uticaria comprising administering to the mammal an efficaceous amount of a compound having the formula: ##STR9## wherein ##STR10## R 1 is CH 3 C 2 (CH 3 )CH, alkyl of 5-12 carbon atoms, cyclohexyl, ##STR11## when R is ##STR12## R 1 can be in addition alkyl of 3-4 carbon atoms; R 2 is ##STR13## R 3 is H, alkoxy of 1-3 carbon atoms, or alkyl of 1-2 carbon atoms; R 4 is CO 2 H or CO 2 R 11 ; R 5 , R 6 , R 7 and R 8 are independently H, F, Cl, Br, I, CH 3 , CF 3 , SCH 3 or CH 2 CH 3 , at least two of R 5 , R 6 , R 7 and R 8 being H; R 9 and R 9A are independently H or alkyl of 1 to 3 carbon atoms; R 11 is (CH 2 ) 2-4 NR 9 R 9A ; W, Y and Z are independently H, F, Cl, Br, alkyl of 1-5 carbon atomns, NO 2 , OH, CF 3 or OCH 3 ; m is 0 or 1; or a pharmaceutically suitable salt thereof; with the following provisos: (1) R 5 , R 6 and R 7 cannot all be H; (2) when R 4 is CO 2 CH 2 CH 2 N(CH 3 ) 2 , R 6 is CH 2 CH 3 , or R 7 is Cl, R 1 cannot be cyclohexyl; (3) when R 1 is cyclohexyl and R 3 is H, R 6 must be Cl or F, but R 6 and R 8 cannot both be Cl; and (4) when R 6 is CH 3 , then R 7 cannot be Cl.
Claim 2
Independent Claim
315 words
A method of treating a skin or mucoepithelial disease in a mammal selected from the group consisting of psoriasis, lichen planas, chronic eczema, icthyosis, pityriasis and chronic uticaria comprising administering to the mammal an efficaceous amount of a compound having the formula: ##STR9## wherein ##STR10## R 1 is CH 3 C 2 (CH 3 )CH, alkyl of 5-12 carbon atoms, cyclohexyl, ##STR11## when R is ##STR12## R 1 can be in addition alkyl of 3-4 carbon atoms; R 2 is ##STR13## R 3 is H, alkoxy of 1-3 carbon atoms, or alkyl of 1-2 carbon atoms; R 4 is CO 2 H or CO 2 R 11 ; R 5 , R 6 , R 7 and R 8 are independently H, F, Cl, Br, I, CH 3 , CF 3 , SCH 3 or CH 2 CH 3 , at least two of R 5 , R 6 , R 7 and R 8 being H; R 9 and R 9A are independently H or alkyl of 1 to 3 carbon atoms; R 11 is (CH 2 ) 2-4 NR 9 R 9A ; W, Y and Z are independently H, F, Cl, Br, alkyl of 1-5 carbon atomns, NO 2 , OH, CF 3 or OCH 3 ; m is 0 or 1; or a pharmaceutically suitable salt thereof; with the following provisos: (1) R 5 , R 6 and R 7 cannot all be H; (2) when R 4 is CO 2 CH 2 CH 2 N(CH 3 ) 2 , R 6 is CH 2 CH 3 , or R 7 is Cl, R 1 cannot be cyclohexyl; (3) when R 1 is cyclohexyl and R 3 is H, R 6 must be Cl or F, but R 6 and R 8 cannot both be Cl; and (4) when R 6 is CH 3 , then R 7 cannot be Cl.
Claim 3
Dependent Claim
188 words
The method of claim 1 wherein the compound has the formula: ##STR14## wherein R 1 is cyclohexyl; phenyl; phenyl substituted with one halogen; alkyl of 1-5 carbon atomsd or CF 3 ; phenoxy; or phenoxy substituted with one halogen or alkyl of 1-5 carbon atoms; R 3 is H or alkyl of 1-2 carbon atoms; R 4 is CO 2 H, a sodium or potassium salt thereof; or CO 2 R 11 ; R 5 and R 6 are independently H, halogen, CH 3 or CF 3 ; R 7 and R 8 are independently H or halogen; R 11 is (CH 2 ) 2-4 NR 9 R 9A ; and R 9 and R 9A are independently alkyl of 1 to 3 carbon atoms, or a pharmaceutically suitable salt thereof; provided that R 5 , R 6 and R 7 cannot all be H and that when R 1 is cyclohexyl and R 3 is H, R 6 must be Cl or F, but R 6 and R 8 cannot both be Cl, and when R 6 is CH 3 , then R 7 cannot be Cl.
Claim 4
Dependent Claim
152 words
The method of claim 1 wherein the compound has the formula: ##STR15## wherein R 1 is cyclohexyl, ##STR16## R 3 is H or alkyl of 1-2 carbon atoms; R 4 is CO 2 H, a sodium or potassium salt thereof, or CO 2 R 11 ; R 5 and R 6 are independently H, halogen or CF 3 provided that both R 5 and R 6 are not hydrogen; R 11 is (CH 2 ) 2-4 NR 9 R 9A ; and R 9 and R 9A are independently alkyl of 1 to 3 carbon atoms, and W and Z are independently H, halogen, alkyl of 1-5 carbon atoms or CF 3 ; provided that when R 1 is phenyl or phenoxy, and R 5 is H, then R 6 cannot be Br; and that when R 1 is cyclohexyl and R 3 is H, R 6 must be Cl or F.
Claim 5
Dependent Claim
15 words
The method of claim 1 wherein the compound is 2-(1,1'-biphenyl-4-yl)-6-fluoro-3-methyl-4-quinolinecarboxylic acid, sodium or potassium salt.
Claim 6
Dependent Claim
15 words
The method of claim 1 wherein the compound is 6-fluoro-3-methyl-2-(4-phenoxyphenyl)-4-quinoline-carboxylic acid, sodium or potassium salt.
Claim 7
Dependent Claim
15 words
The method of claim 1 wherein the compound is 2-(4'-bromo-1,1'-biphenyl-4-yl)-6-fluoro-3-methyl-4-quinolinecarboxylic acid, sodium or potassium salt.
Claim 8
Dependent Claim
15 words
The method of claim 1 wherein the compound is 2-(2'-fluoro-1,1'-biphenyl-4-yl)-6-fluoro-3-methyl-4-quinolinecarboxylic acid, sodium or potassium salt.
Claim 9
Dependent Claim
15 words
The method of claim 1 wherein the compound is 2-(1,1'-biphenyl-4-yl)-5-chloro-3-methyl-4-quinolinecarboxylic acid, sodium or potassium salt.
Claim 10
Dependent Claim
16 words
The method of claim 1 wherein the compound is administered in combination with a steroid drug.
Claim 11
Dependent Claim
325 words
A topical pharmaceutical composition in the form of an ointment, cream or gel consisting essentially of a carrier suitable for topical formulation and a topically efficaceous amount of a compound having the formula: ##STR17## wherein ##STR18## R 1 is cyclohexyl, ##STR19## when R is ##STR20## R 1 can be in addition alkyl of 3-4 carbon atoms; R 2 is ##STR21## R 3 is H, alkoxy of 1-3 carbon atoms, or alkyl of 1-2 carbon atoms; R 4 is CO 2 H or CO 2 R 11 ; R 5 , R 6 , R 7 and R 8 are independently H, F, Cl, Br, I, CH 3 , CF 3 , SCH 3 or CH 2 CH 3 , at least two of R 5 , R 6 , R 7 and R 8 being H; R 9 and R 9A are independently H or alkyl of 1 to 3 carbon atoms; R 11 is (CH 2 ) 2-4 NR 9 R 9A ; W, Y, and Z are independently H, F, Cl, Br, alkyl of 1-5 carbon atoms, NO 2 , OH, CF 3 or OCH 3 ; m is 0 or 1; or a pharmaceutically suitable salt thereof; with the following provisos: (1) when R 4 is CO 2 H, R 1 or R 2 is phenyl and R 5 , R 7 and R 8 are H, R 6 cannot be Br; (2) R 5 , R 6 and R 7 cannot all be H; (3) when R 1 is CO 2 CH 2 CH 2 N(CH 3 ) 2 , R 6 is CH 2 CH 3 , or R 7 is Cl, R 1 cannot be cyclohexyl; and (4) when R 1 is cyclohexyl and R 3 is H, R 6 must be Cl or F, but R 6 and R 8 cannot both be Cl; and (5) when R 6 is CH 3 , R 7 cannot be Cl.
Claim 12
Dependent Claim
325 words
A topical pharmaceutical composition in the form of an ointment, cream or gel consisting essentially of a carrier suitable for topical formulation and a topically efficaceous amount of a compound having the formula: ##STR17## wherein ##STR18## R 1 is cyclohexyl, ##STR19## when R is ##STR20## R 1 can be in addition alkyl of 3-4 carbon atoms; R 2 is ##STR21## R 3 is H, alkoxy of 1-3 carbon atoms, or alkyl of 1-2 carbon atoms; R 4 is CO 2 H or CO 2 R 11 ; R 5 , R 6 , R 7 and R 8 are independently H, F, Cl, Br, I, CH 3 , CF 3 , SCH 3 or CH 2 CH 3 , at least two of R 5 , R 6 , R 7 and R 8 being H; R 9 and R 9A are independently H or alkyl of 1 to 3 carbon atoms; R 11 is (CH 2 ) 2-4 NR 9 R 9A ; W, Y, and Z are independently H, F, Cl, Br, alkyl of 1-5 carbon atoms, NO 2 , OH, CF 3 or OCH 3 ; m is 0 or 1; or a pharmaceutically suitable salt thereof; with the following provisos: (1) when R 4 is CO 2 H, R 1 or R 2 is phenyl and R 5 , R 7 and R 8 are H, R 6 cannot be Br; (2) R 5 , R 6 and R 7 cannot all be H; (3) when R 1 is CO 2 CH 2 CH 2 N(CH 3 ) 2 , R 6 is CH 2 CH 3 , or R 7 is Cl, R 1 cannot be cyclohexyl; and (4) when R 1 is cyclohexyl and R 3 is H, R 6 must be Cl or F, but R 6 and R 8 cannot both be Cl; and (5) when R 6 is CH 3 , R 7 cannot be Cl.
Claim 13
Dependent Claim
188 words
The topical composition of claim 10 wherein the compound has the formula: ##STR22## wherein R 1 is cyclohexyl; phenyl; phenyl substituted with one halogen; alkyl of 1.5 carbon atoms CF 3 ; phenoxy; or phenoxy substituted with one halogen or alkyl of 1-5 carbon atoms; R 3 is H or alkyl of 1-2 carbon atoms; R 4 is CO 2 H, a sodium or potassium salt thereof; or CO 2 R 11 ; R 5 and R 6 are independently H, halogen, CH 3 or CF 3 ; R 7 and R 8 are independently H or halogen; R 11 is (CH 2 ) 2-4 NR 9 R 9A ; and R 9 and R 9A are independently alkyl of 1 to 3 carbon atoms, or a pharmaceutically suitable salt thereof; provided that R 5 , R 6 and R 7 cannot all be H and that when R 1 is cyclohexyl and R 3 is H, R 6 must be Cl or F, but R 6 and R 8 cannot both be Cl, and when R 6 is CH 3 , then R 7 cannot be Cl.
Claim 14
Dependent Claim
153 words
The topical composition of claim 10 wherein the compound has the formula: ##STR23## wherein R 1 is cyclohexyl, ##STR24## R 3 is H or alkyl of 1-2 carbon atoms; R 4 is CO 2 H, a sodium or potassium salt thereof, or CO 2 R 11 ; R 5 and R 6 are independently H, halogen or CF 3 provided that both R 5 and R 6 are not hydrogen; R 11 is (CH 2 ) 2-4 NR 9 R 9A ; and R 9 and R 9A are independently alkyl of 1 to 3 carbon atoms, and W and Z are independently H, halogen, alkyl of 1-5 carbon atoms or CF 3 ; provided that when R 1 is phenyl or phenoxy, and R 5 is H, then R 6 cannot be Br; and that when R 1 is cyclohexyl and R 3 is H, R 6 must be Cl or F.
Claim 15
Dependent Claim
16 words
The topical composition of claim 10 wherein the compound is 2-(1,1'-biphenyl-4-yl-6-fluoro-3-methyl-4-quinoline-carboxylic acid, sodium or potassium salt.
Claim 16
Dependent Claim
16 words
The topical composition of claim 10 wherein the compound is 6-fluoro-3-methyl-2-(4-phenoxyphenyl)-4-quinoline-carboxylic acid, sodium or potassium salt.
Claim 17
Dependent Claim
16 words
The topical composition of claim 10 wherein the compound is 2-(4'-bromo-1,1'-biphenyl-4-yl)-6-fluoro-3-methyl-4-quinoline-carboxylic acid, sodium or potassium salt.
Claim 18
Dependent Claim
16 words
The topical composition of claim 10 wherein the compound is 2-(2'-fluoro-1,1'-biphenyl-4-yl)-6-fluoro-3-methyl-4-quinoline-carboxylic acid, sodium or potassium salt.
Claim 19
Dependent Claim
16 words
The topical composition of claim 10 wherein the compound is 2-(1,1'-biphenyl-4-yl)-5-chloro-3-methyl-4-quinolinecarboxylic acid, sodium or potassium salt.
Claim 20
Dependent Claim
17 words
The topical composition of claim 10 wherein the compound is present in combination with a steroid drug.
References Cited (Backward Citations)
US4680299A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1992-08-28 | 1993-02-27 | 1993-08-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-08-28 | 1997-02-27 | 1997-08-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-08-28 | 2001-02-27 | 2001-08-29 | $7700.00 | Window Closed / Lapsed |