US4711903A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Phenolic thioethers as inhibitors of 5-lipoxygenase
Assignee: GD Searle LLC
•
Filing: 1986-01-31
•
Granted: 1987-12-08
•
Expires: 2006-01-31
Abstract
Abstract The compounds of the present invention comprise substituted phenolic thioethers represented by the formula: ##STR1## wherein: R 1 and R 2 are the same or different and independently represent tert-alkyl or phenyl; A represents methylene or methylene substituted by alkyl, dialkyl or hydroxy, provided that when A includes hydroxymethylene, the hydroxymethylene group is not adjacent to a heteroatom; B represents sulfur, sulfoxide, sulfone, oxygen, --NH-- or nitrogen substituted by alkyl, phenyl, benzyl, substituted phenyl or substituted benzyl; C represents methylene or methylene substituted by alkyl; R 3 represents CO 2 H, CO 2 -alkyl or a tetrazole group; m is 0 or 1, n is 2, 3 or 4 and p is 1, 2 or 3; amd the pharmaceutically acceptable salts thereof. The compounds of the present invention are specific inhibitors of 5-lipoxygenase and, therefore, are useful in the treatment of local and systemic inflammation, allergy and hypersensitivity reactions and other disorders in which agents formed in the 5-lipoxygenase metabolic pathway are involved.
Inventors
- 👤 Richard A. Mueller
- 👤 Richard A. Partis
- 👤 James R. Deason
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 15:32
CPC Classifications
C; C07; C07D; C07D257/00; C07D257/02; C07D257/04; C07C; C07C317/00; C07C317/44; C07C323/00; C07C323/10; C07C323/18; C07C323/20; C07C323/22; C07C323/23; C07C323/24; C07C323/25; C07C323/50; C07C323/51; C07C323/52; C07C323/64; C07C323/65; C07C327/00; C07C327/20; C07C327/22; C07C331/00; C07C331/02; C07C331/10
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
207 words
A compound of the formula: ##STR53## or a pharmaceutically acceptable salt thereof wherein R 1 and R 2 are the same or different and independently represent tert-alkyl or phenyl; A represents methylene or methylene substituted by alkyl, dialkyl or hydroxy, provided that when A includes hydroxymethylene, the hydroxymethylene group is not adjacent to a heteroatom; B represents sulfur, sulfoxide, sulfone, oxygen, --NH-- or nitrogen substituted by alkyl, phenyl, benzyl, phenyl substituted by one or two substituents which may be the same or different and are independently selected from the group consisting of halogen, C 1 -C 6 alkyl, hydroxy, C 1 -C 6 -alkoxy, acetoxy, carboxylic acid and C 1 -C 6 alkyl esters thereof, nitro or phenyl or benzyl substituted by one or two substituents which may be the same or different and are independently selected from the group consisting of halogen, C 1 -C 6 alkyl, hydroxy, C 1 -C 6 alkoxy, acetoxy, carboxylic acid and C 1 -C 6 alkyl esters thereof, nitro or phenyl; C represents methylene or methylene substituted by alkyl; R 3 represents CO 2 H, CO 2 -alkyl, or a tetrazole group; m is 0 or 1, n is 2, 3, or 4 and p is 1, 2, or 3.
Claim 2
Dependent Claim
207 words
A compound of the formula: ##STR53## or a pharmaceutically acceptable salt thereof wherein R 1 and R 2 are the same or different and independently represent tert-alkyl or phenyl; A represents methylene or methylene substituted by alkyl, dialkyl or hydroxy, provided that when A includes hydroxymethylene, the hydroxymethylene group is not adjacent to a heteroatom; B represents sulfur, sulfoxide, sulfone, oxygen, --NH-- or nitrogen substituted by alkyl, phenyl, benzyl, phenyl substituted by one or two substituents which may be the same or different and are independently selected from the group consisting of halogen, C 1 -C 6 alkyl, hydroxy, C 1 -C 6 -alkoxy, acetoxy, carboxylic acid and C 1 -C 6 alkyl esters thereof, nitro or phenyl or benzyl substituted by one or two substituents which may be the same or different and are independently selected from the group consisting of halogen, C 1 -C 6 alkyl, hydroxy, C 1 -C 6 alkoxy, acetoxy, carboxylic acid and C 1 -C 6 alkyl esters thereof, nitro or phenyl; C represents methylene or methylene substituted by alkyl; R 3 represents CO 2 H, CO 2 -alkyl, or a tetrazole group; m is 0 or 1, n is 2, 3, or 4 and p is 1, 2, or 3.
Claim 3
Dependent Claim
15 words
A compound according to claim 1 wherein R 1 and R 2 are both tert-alkyl.
Claim 4
Dependent Claim
11 words
A compound according to claim 2 wherein said tert-alkyl is tert-butyl.
Claim 5
Dependent Claim
15 words
A compound according to claim 1 wherein R 1 and R 2 are both phenyl.
Claim 6
Dependent Claim
21 words
A compound according to claim 1 wherein (A) n is --CH 2 --CH 2 -- or --CH 2 --CH(OH)--CH 2 --.
Claim 7
Dependent Claim
13 words
A compound according to claim 1 wherein B is sulfur, sulfoxide or sulfone.
Claim 8
Dependent Claim
23 words
A compound according to claim 1 wherein B is oxygen, --NH-- or nitrogen substituted by alkyl, phenyl, benzyl, substituted phenyl or substituted benzyl.
Claim 9
Dependent Claim
12 words
A compound according to claim 1 wherein C is --CH 2 --.
Claim 10
Dependent Claim
13 words
A compound according to claim 1 wherein R 3 is --CO 2 H.
Claim 11
Dependent Claim
14 words
A compound according to claim 1 wherein said compound is of the formula: ##STR54##
Claim 12
Dependent Claim
28 words
A pharmaceutical composition for the treatment of inflammation and allergy conditions comprising a therapeutically effective amount of a compound according to claim 1 and a pharmaceutically acceptable carrier.
Claim 13
Dependent Claim
11 words
A pharmaceutical composition according to claim 11 adapted for oral administration.
Claim 14
Dependent Claim
11 words
A pharmaceutical composition according to claim 11 adapted for aerosol administration.
Claim 15
Dependent Claim
11 words
A pharmaceutical composition according to claim 11 adapted for parenteral administration.
Claim 16
Dependent Claim
14 words
A pharmaceutical composition according to claim 14 wherein said parenteral administration is intravenous administration.
Claim 17
Dependent Claim
29 words
A method of eliciting an anti-inflammatory or anti-allergic effect in a mammal in need thereof comprising administering thereto a therapeutically effective amount of a compound according to claim 1.
Claim 18
Dependent Claim
25 words
A method of treating asthma in a mammal in need thereof comprising administering thereto a therapeutically effective amount of a compound according to claim 1.
Claim 19
Dependent Claim
27 words
A method of treating proliferative skin disorders in a mammal in need thereof comprising administering thereto a therapeutically effective amount of a compound according to claim 1.
Claim 20
Dependent Claim
12 words
A method according to claim 15 wherein said compound is administered topically.
Claim 21
Dependent Claim
25 words
A method of inhibiting 5-lipoxygenase in a mammal in need thereof comprising administering thereto a therapeutically effective amount of a compound according to claim 1.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-12-07 | 1991-06-08 | 1991-12-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-12-07 | 1995-06-08 | 1995-12-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-12-07 | 1999-06-08 | 1999-12-08 | $7700.00 | Window Closed / Lapsed |