US4593120A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Naphthalene anti-psoriatic agents
Assignee: Syntex USA LLC
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Filing: 1983-12-22
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Granted: 1986-06-03
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Expires: 2003-12-22
Abstract
Abstract Psoriasis in mammals is relieved by topically administering naphthalenes of the formula: <IMAGE> (I) wherein: R1 and R2 are the same and are lower alkoxy, lower alkylthio, optionally substituted phenoxy or optionally substituted phenylthio, R3 is lower alkyl, lower alkoxy, or halo and m is 0, 1 or 2 or R3 is optionally substituted phenyl, optionally substituted phenyl lower alkyl, optionally substituted phenyl lower alkoxy, amino, lower alkylamino, lower dialkylamino, cyano, or S(O)n R wherein R is lower alkyl; optionally substituted phenyl; optionally substituted phenyl lower alkyl; or optionally substituted heterocyclic aryl of three to nine ring atoms containing one or two heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and the pharmaceutically acceptable acid addition salts thereof; and m is 1 and n is 0, 1 or 2; and W is alkyl of one to seven carbon atoms, optionally substituted phenyl or optionally substituted benzyl.
Inventors
- 👤 Gordon H. Jones
- 👤 Michael C. Venuti
- 👤 John M. Young
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 09:44
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/62; C07D213/70; A; A61; A61P; A61P17/00; A61P29/00; C07C; C07C205/00; C07C205/45; C07C205/46; C07C205/47; C07C205/48; C07C255/00; C07C255/49; C07C255/57; C07C317/00; C07C323/00; C07C45/00; C07C45/61; C07C45/63; C07C46/00; C07C46/02; C07C50/00; C07C50/24; C07C50/26; C07C50/32; C07C69/00; C07C69/017; C07D213/89
Claims Analysis
Total Claims: 34
Claim 1
Independent Claim
289 words
A composition in a form suitable for topical administration for treating the condition of psoriasis which composition comprises a pharmaceutically acceptable, non-toxic carrier and a psoriasis relieving amount of a compound of the formula ##STR10## wherein: R 1 and R 2 are the same and are lower alkoxy of one to six carbon atoms, lower alkylthio of one to six carbon atoms, phenoxy or phenylthio optionally substituted by one or two lower alkyl of one to four carbon atoms, lower alkoxy of one to four carbon atoms or halo; R 3 is lower alkyl of one to six carbon atoms, lower alkoxy of one to six carbon atoms, or halo and m is 0, 1 or 2 or R 3 is optionally substituted phenyl, optionally substituted phenyl lower alkyl, optionally substituted phenyl lower alkoxy, amino, lower alkylamino, lower dialkylamino, cyano, or S(O) n R wherein R is lower alkyl of one to six carbon atoms; optionally substituted phenyl; optionally substituted phenyl lower alkyl; or heterocyclic aryl of three to nine ring atoms containing one or two heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur wherein the heterocyclic aryl is optionally substituted by one or more substituents selected from the group consisting of lower alkyl, lower alkoxy, halo and cyano and the pharmaceutically acceptable acid addition salts thereof; and m is 1 and n is 0, 1 or 2; and W is alkyl of one to seven carbon atoms, phenyl or benzyl optionally substituted by one or two lower alkyl of one to four carbon atoms, lower alkoxy of one to four carbon atoms or halo; with the proviso that when R 1 and R 2 are alkoxy or alkylthio and W is alkyl, m is 2.
Claim 2
Dependent Claim
289 words
A composition in a form suitable for topical administration for treating the condition of psoriasis which composition comprises a pharmaceutically acceptable, non-toxic carrier and a psoriasis relieving amount of a compound of the formula ##STR10## wherein: R 1 and R 2 are the same and are lower alkoxy of one to six carbon atoms, lower alkylthio of one to six carbon atoms, phenoxy or phenylthio optionally substituted by one or two lower alkyl of one to four carbon atoms, lower alkoxy of one to four carbon atoms or halo; R 3 is lower alkyl of one to six carbon atoms, lower alkoxy of one to six carbon atoms, or halo and m is 0, 1 or 2 or R 3 is optionally substituted phenyl, optionally substituted phenyl lower alkyl, optionally substituted phenyl lower alkoxy, amino, lower alkylamino, lower dialkylamino, cyano, or S(O) n R wherein R is lower alkyl of one to six carbon atoms; optionally substituted phenyl; optionally substituted phenyl lower alkyl; or heterocyclic aryl of three to nine ring atoms containing one or two heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur wherein the heterocyclic aryl is optionally substituted by one or more substituents selected from the group consisting of lower alkyl, lower alkoxy, halo and cyano and the pharmaceutically acceptable acid addition salts thereof; and m is 1 and n is 0, 1 or 2; and W is alkyl of one to seven carbon atoms, phenyl or benzyl optionally substituted by one or two lower alkyl of one to four carbon atoms, lower alkoxy of one to four carbon atoms or halo; with the proviso that when R 1 and R 2 are alkoxy or alkylthio and W is alkyl, m is 2.
Claim 3
Dependent Claim
9 words
The composition of claim 1 wherein m is 2.
Claim 4
Dependent Claim
35 words
The composition according to claim 1 wherein the compound is ##STR11## wherein R 1 , R 2 , R 3 , and W are as defined in claim 1 and m is 0 or 1.
Claim 5
Dependent Claim
15 words
The composition of claim 3 wherein W is alkyl of one to seven carbon atoms.
Claim 6
Dependent Claim
44 words
The composition according to claim 4 wherein R 1 and R 2 are the same and are phenoxy or phenylthio optionally substituted by one or more lower alkyl of one to four carbon atoms, lower alkoxy of one to four carbon atoms or halo.
Claim 7
Dependent Claim
35 words
The composition of claim 3 wherein W is phenyl or benzyl optionally substituted by one or two lower alkyl of one to four carbon atoms, lower alkoxy of one to four carbon atoms or halo.
Claim 8
Dependent Claim
33 words
The composition of claim 6 wherein R 1 and R 2 are the same and are lower alkoxy of one to six carbon atoms of lower alkylthio of one to six carbon atoms.
Claim 9
Dependent Claim
43 words
The composition of claim 6 wherein R 1 and R 2 are the same and are phenoxy or phenylthio optionally substituted by one or two lower alkyl of one to four carbon atoms, lower alkoxy of one to four carbon atoms or halo.
Claim 10
Independent Claim
275 words
A method of treating psoriasis in mammals which comprises applying an effective amount of a compound of the formula ##STR12## wherein: R 1 and R 2 are the same and are lower alkoxy of one to six carbon atoms, lower alkylthio of one to six carbon atoms, phenoxy or phenylthio optionally substituted by one or two lower carbon atoms or halo; R 3 is lower alkyl of one to six carbon atoms, lower alkoxy of one to six carbon atoms, or halo and m is 0, 1 or 2 or R 3 is optionally substituted phenyl, optionally substituted phenyl lower alkyl, optionally substituted phenyl lower alkoxy lower alkoxy, amino, lower alkylamino, lower dialkylamino, cyano, or S(O) n R wherein R is lower alkyl of one to six carbon atoms; optionally substituted phyenyl; optionally substituted phenyl lower alkyl; or heterocyclic aryl of three to nine ring atoms containing one or two heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur wherein the heterocyclic aryl is optionally substituted by one or more substitutents selected form the group consisting of lower alkyl, lower alkoxy, halo and cyano and the pharmaceutically acceptable acid addition salts thereof; and m is 1 and n is 0, 1 or 2; and W is alkyl of one to seven carbon atoms, phenyl of benzyl optionally substituted by one or two lower alkyl of one to four carbon atoms, lower alkoxy of one to four carbon atoms or alkyl of one to four carbon atoms, lower alkoxy of one to four halo; with the proviso that when R 1 and R 2 alkoxy or alkylthio and W is alkyl, m is 2.
Claim 11
Independent Claim
275 words
A method of treating psoriasis in mammals which comprises applying an effective amount of a compound of the formula ##STR12## wherein: R 1 and R 2 are the same and are lower alkoxy of one to six carbon atoms, lower alkylthio of one to six carbon atoms, phenoxy or phenylthio optionally substituted by one or two lower carbon atoms or halo; R 3 is lower alkyl of one to six carbon atoms, lower alkoxy of one to six carbon atoms, or halo and m is 0, 1 or 2 or R 3 is optionally substituted phenyl, optionally substituted phenyl lower alkyl, optionally substituted phenyl lower alkoxy lower alkoxy, amino, lower alkylamino, lower dialkylamino, cyano, or S(O) n R wherein R is lower alkyl of one to six carbon atoms; optionally substituted phyenyl; optionally substituted phenyl lower alkyl; or heterocyclic aryl of three to nine ring atoms containing one or two heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur wherein the heterocyclic aryl is optionally substituted by one or more substitutents selected form the group consisting of lower alkyl, lower alkoxy, halo and cyano and the pharmaceutically acceptable acid addition salts thereof; and m is 1 and n is 0, 1 or 2; and W is alkyl of one to seven carbon atoms, phenyl of benzyl optionally substituted by one or two lower alkyl of one to four carbon atoms, lower alkoxy of one to four carbon atoms or alkyl of one to four carbon atoms, lower alkoxy of one to four halo; with the proviso that when R 1 and R 2 alkoxy or alkylthio and W is alkyl, m is 2.
Claim 12
Dependent Claim
9 words
The method of claim 9 wherein m is 2.
Claim 13
Dependent Claim
15 words
The method of claim 9 wherein W is alkyl of one to seven carbon atoms
Claim 14
Dependent Claim
43 words
The method of claim 11 wherein R 1 and R 2 are the same and are phenoxy or phenylthio optionally substituted by one or more lower alkyl of one to four carbon atoms, lower alkoxy of one to four carbon atoms or halo.
Claim 15
Dependent Claim
35 words
The method of claim 9 wherein W is phenyl or benzyl optionally substituted by one or two lower alkyl of one to four carbon atoms, lower alkoxy of one to four carbon atoms or halo.
Claim 16
Dependent Claim
33 words
The method of claim 13 wherein R 1 and R 2 are the same and are lower alkoxy of one to six carbon atoms or lower alkylthio of one to six carbon atoms.
Claim 17
Dependent Claim
43 words
The method of claim 13 wherein R 1 and R 2 are the same and are phenoxy or phenylthio optionally substituted by one or two lower alkyl of one to four carbon atoms, lower alkoxy of one to four carbon atoms or halo.
Claim 18
Dependent Claim
256 words
A compound of the formula ##STR13## wherein: R 1 and R 2 are the same and are lower alkoxy of one to six carbon atoms, lower alkylthio of one to six carbon atoms, phenoxy or phenylthio optionally substituted by one or two lower alkyl of one to four carbon atoms, lower alkoxy or one to four carbon atoms or halo; R 3 is lower alkyl of one to six carbon atoms, lower alkoxy of one to six carbon atoms, or halo and m is 0, 1 or 2 or optionally substituted phenyl, optionally substituted phenyl lower alkyl, optionally substituted phenyl lower alkoxy, amino, lower alkylamino, lower dialkylamino, cyano, or S(O) n R wherein R is lower aklyl of one to six carbon atoms; optionally substituted phenyl; optionally substituted phenyl lower alkyl; or heterocyclic aryl of three to nine ring atoms containing one or two heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur wherein the heterocyclic aryl is optionally substituted by one or more substitutents selected from the group consisting of lower alkyl, lower alkoxy, halo and cyano and the pharmaceutically acceptable acid addition salts thereof; and m is 1 and n is 0, 1 or 2; and is alkyl of one to seven carbon atoms, phenyl or benzyl optionally substituted by one or two lower alkyl of one to four carbon atoms, lower alkoxy of one to four carbon atoms or halo; with the proviso that when R 1 and R 2 are alkoxy or alkylthio and W is alkyl, m is 2.
Claim 19
Dependent Claim
256 words
A compound of the formula ##STR13## wherein: R 1 and R 2 are the same and are lower alkoxy of one to six carbon atoms, lower alkylthio of one to six carbon atoms, phenoxy or phenylthio optionally substituted by one or two lower alkyl of one to four carbon atoms, lower alkoxy or one to four carbon atoms or halo; R 3 is lower alkyl of one to six carbon atoms, lower alkoxy of one to six carbon atoms, or halo and m is 0, 1 or 2 or optionally substituted phenyl, optionally substituted phenyl lower alkyl, optionally substituted phenyl lower alkoxy, amino, lower alkylamino, lower dialkylamino, cyano, or S(O) n R wherein R is lower aklyl of one to six carbon atoms; optionally substituted phenyl; optionally substituted phenyl lower alkyl; or heterocyclic aryl of three to nine ring atoms containing one or two heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur wherein the heterocyclic aryl is optionally substituted by one or more substitutents selected from the group consisting of lower alkyl, lower alkoxy, halo and cyano and the pharmaceutically acceptable acid addition salts thereof; and m is 1 and n is 0, 1 or 2; and is alkyl of one to seven carbon atoms, phenyl or benzyl optionally substituted by one or two lower alkyl of one to four carbon atoms, lower alkoxy of one to four carbon atoms or halo; with the proviso that when R 1 and R 2 are alkoxy or alkylthio and W is alkyl, m is 2.
Claim 20
Dependent Claim
9 words
The compound of claim 16 wherein m is 2.
Claim 21
Dependent Claim
32 words
A compound of claim 16 of the formula ##STR14## wherein R 1 , R 2 , R 3 and W are as defined in claim 16 and m is 0 or 1.
Claim 22
Dependent Claim
26 words
The compound according to claim 18 wherein R 3 is selected from the group consisting of halo, cyano, and alkoxy of one to four carbon atoms.
Claim 23
Dependent Claim
24 words
The compound according to claim 19 wherein R 3 is selected from the group consisting of fluoro, chloro and bromo and m is 1.
Claim 24
Dependent Claim
11 words
The compound according to claim 18 wherein R 3 is cyano.
Claim 25
Dependent Claim
15 words
The compound of claim 20 wherein W is alkyl of one to seven carbon atoms.
Claim 26
Dependent Claim
43 words
A compound of claim 22 wherein R 1 and R 2 are the same and are phenoxy or phenylthio optionally substituted by one or two lower alkyl of one to four carbon atoms, lower alkoxy of one to four carbon atoms or halo.
Claim 27
Dependent Claim
9 words
The compound of claim 23 which is 6-chloro 2,3-diphenoxy-1,4-diacetyloxynaphthalene.
Claim 28
Dependent Claim
8 words
The compound of claim 23 which is 6-chloro-2,3-diphenoxy-1,4-di-n-propanoyloxynaphthalene.
Claim 29
Dependent Claim
8 words
The compound of claim 23 which is 6-chloro-2,3-diphenoxy-1,4-di-n-butanoyloxynaphthalene.
Claim 30
Dependent Claim
35 words
The compound of claim 20 wherein W is phenyl or benzyl optionally substituted by one or two lower alkyl of one to four carbon atoms, lower alkoxy of one to four carbon atoms or halo.
Claim 31
Dependent Claim
33 words
The compound of claim 27 wherein R 1 and R 2 are the same and are lower alkoxy of one to six carbon atoms or lower alkylthio of one to six carbon atoms.
Claim 32
Dependent Claim
8 words
The compound of claim 28 which is 6-chloro-2,3-dimethoxy-1,4-dibenzoyloxynaphthalene.
Claim 33
Dependent Claim
43 words
The compound of claim 27 wherein R 1 and R 2 are the same and are phenoxy or phenylthio optionally substituted by one or two lower alkyl of one to four carbon atoms, lower alkoxy of one to four carbon atoms or halo.
Claim 34
Dependent Claim
8 words
The compound of claim 30 which is 6-chloro-2,3-diphenoxy-1,4-dibenzoyloxynaphthalene.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-06-02 | 1989-12-02 | 1990-06-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-06-02 | 1993-12-02 | 1994-06-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-06-02 | 1997-12-02 | 1998-06-03 | $7700.00 | Window Closed / Lapsed |