US4466981A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Naphthalene anti-psoriatic agents
Assignee: Syntex USA LLC
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Filing: 1982-10-27
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Granted: 1984-08-21
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Expires: 2002-10-27
Abstract
Abstract Psoriasis in mammals is relieved by topically administering naphthalenes of the formula: ##STR1## wherein: R 1 and R 2 are lower alkoxy or lower alkylthio; R 3 is hydrogen, lower alkyl, lower alkoxy, optionally substituted phenyl, optionally substituted phenyl lower alkyl, optionally substituted phenyl lower alkoxy, amino, lower alkylamino, lower dialkylamino, halo, 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 n is 0, 1 or 2; and W is alkyl of one to seven carbon atoms.
Inventors
- 👤 Gordon H. Jones
- 👤 Michael C. Venuti
- 👤 John M. Young
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 13:45
CPC Classifications
C; C07; C07C; C07C69/00; C07C69/02; C07C69/12; C07C69/16; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/62; C07D213/70; A; A61; A61P; A61P17/00; A61P33/00; C07C205/00; C07C205/45; C07C205/46; C07C205/47; C07C205/48; C07C255/00; C07C317/00; C07C323/00; C07C45/00; C07C45/61; C07C45/63; C07C46/00; C07C46/02; C07C50/00; C07C50/24; C07C50/26; C07C50/32; C07C69/62; C07C69/63; C07D213/89
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
282 words
A composition in a form suitable for topical administration for relieving the condition of psoriasis which 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 lower alkoxy of one to six carbon atoms or lower alkylthio of one to six carbon atoms; R 3 is hydrogen, lower alkyl of one to six carbon atoms, lower alkoxy of one to six carbon atoms, phenyl optionally substituted by one or more lower alkyl, lower alkoxy, halo, lower acyl, lower acyloxy, cyano, nitro or lower acylamino, phenyl lower alkyl optionally substituted by one or more lower alkyl, lower alkoxy, halo, lower acyl, lower acyloxy, cyano, nitro or lower acylamino, phenyl lower alkoxy optionally substituted by one or more lower alkyl, lower alkoxy, halo, lower acyl, lower acyloxy, cyano, nitro or lower acylamino, amino, lower alkylamino, lower dialkylamino, halo, cyano, or S(O) n R wherein R is lower alkyl of one to six carbon atoms; phenyl optionally substituted by one or more lower alkyl, lower alkoxy, halo, lower acyl, lower acyloxy, cyano, nitro or lower acylamino; phenyl lower alkyl optionally substituted by one or more lower alkyl, lower alkoxy, halo, lower acyl, lower acyloxy, cyano, nitro or lower acylamino; or heterocyclic aryl selected from the group consisting of thiapyranyl, benzothiapyranyl, furyl, pyrrolyl, imidazolyl, pyrazolyl, pyridinyl, pyrimidinyl, indolyl, quinolinyl and indazolyl 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 n is 0, 1 or 2; and W is alkyl of one to seven carbon atoms.
Claim 2
Dependent Claim
282 words
A composition in a form suitable for topical administration for relieving the condition of psoriasis which 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 lower alkoxy of one to six carbon atoms or lower alkylthio of one to six carbon atoms; R 3 is hydrogen, lower alkyl of one to six carbon atoms, lower alkoxy of one to six carbon atoms, phenyl optionally substituted by one or more lower alkyl, lower alkoxy, halo, lower acyl, lower acyloxy, cyano, nitro or lower acylamino, phenyl lower alkyl optionally substituted by one or more lower alkyl, lower alkoxy, halo, lower acyl, lower acyloxy, cyano, nitro or lower acylamino, phenyl lower alkoxy optionally substituted by one or more lower alkyl, lower alkoxy, halo, lower acyl, lower acyloxy, cyano, nitro or lower acylamino, amino, lower alkylamino, lower dialkylamino, halo, cyano, or S(O) n R wherein R is lower alkyl of one to six carbon atoms; phenyl optionally substituted by one or more lower alkyl, lower alkoxy, halo, lower acyl, lower acyloxy, cyano, nitro or lower acylamino; phenyl lower alkyl optionally substituted by one or more lower alkyl, lower alkoxy, halo, lower acyl, lower acyloxy, cyano, nitro or lower acylamino; or heterocyclic aryl selected from the group consisting of thiapyranyl, benzothiapyranyl, furyl, pyrrolyl, imidazolyl, pyrazolyl, pyridinyl, pyrimidinyl, indolyl, quinolinyl and indazolyl 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 n is 0, 1 or 2; and W is alkyl of one to seven carbon atoms.
Claim 3
Dependent Claim
29 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.
Claim 4
Dependent Claim
21 words
The composition according to claim 2 wherein R 1 and R 2 are lower alkoxy of one to six carbon atoms.
Claim 5
Dependent Claim
27 words
The composition according to claim 3 wherein R 3 is selected from the group consisting of hydrogen, halo, cyano, and alkoxy of one to four carbon atoms.
Claim 6
Dependent Claim
21 words
The composition according to claim 4 wherein R 3 is selected from the group consisting of hydrogen, fluoro, chloro and bromo.
Claim 7
Dependent Claim
11 words
The composition according to claim 4 wherein R 3 is cyano.
Claim 8
Dependent Claim
11 words
The composition according to claim 5 wherein the compound is 2,3-dimethoxy-1,4-acetyloxynaphthalene.
Claim 9
Dependent Claim
11 words
The composition according to claim 5 wherein the compound is 6-bromo-2,3-dimethoxy-1,4-acetyloxynaphthalene.
Claim 10
Dependent Claim
10 words
The composition of claim 5 wherein the compound is 6-chloro-2,3-dimethoxy-1,4-acetyloxynaphthalene.
Claim 11
Dependent Claim
10 words
A composition of claim 5 wherein the compound is 6-chloro-2,3-di-n-butoxy-1,4-acetyloxynaphthalene.
Claim 12
Dependent Claim
21 words
The composition according to claim 2 wherein R 1 and R 2 are lower alkylthio of one to six carbon atoms.
Claim 13
Independent Claim
268 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 lower alkoxy of one to six carbon atoms or lower alkylthio of one to six carbon atoms; R 3 is hydrogen, lower alkyl of one to six carbon atoms, lower alkoxy of one to six carbon atoms, phenyl optionally substituted by one or more lower alkyl, lower alkoxy, halo, lower acyl, lower acyloxy, cyano, nitro or lower acylamino, phenyl lower alkyl optionally substituted by one or more lower alkyl, lower alkoxy, halo, lower acyl, lower acyloxy, cyano, nitro or lower acylamino, phenyl lower alkoxy optionally substituted by one or more lower alkyl, lower alkoxy, halo, lower acyl, lower acyloxy, cyano, nitro or lower acylamino, amino, lower alkylamino, lower dialkylamino, halo, cyano, or S(O) n R wherein R is lower alkyl of one to six carbon atoms; phenyl optionally substituted by one or more lower alkyl, lower alkoxy, halo, lower acyl, lower acyloxy, cyano, nitro or lower acylamino; phenyl lower alkyl optionally substituted by one or more lower alkyl, lower alkoxy, halo, lower acyl, lower acyloxy, cyano, nitro or lower acylamino; or heterocyclic aryl selected from the group consisting of thiapyranyl, benzothiapyranyl, furyl, pyrrolyl, imidazolyl, pyrazolyl, pyridinyl, pyrimidinyl, indolyl, quinolinyl and indazolyl 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 n is 0, 1 or 2; and W is alkyl of one to seven carbon atoms.
Claim 14
Independent Claim
268 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 lower alkoxy of one to six carbon atoms or lower alkylthio of one to six carbon atoms; R 3 is hydrogen, lower alkyl of one to six carbon atoms, lower alkoxy of one to six carbon atoms, phenyl optionally substituted by one or more lower alkyl, lower alkoxy, halo, lower acyl, lower acyloxy, cyano, nitro or lower acylamino, phenyl lower alkyl optionally substituted by one or more lower alkyl, lower alkoxy, halo, lower acyl, lower acyloxy, cyano, nitro or lower acylamino, phenyl lower alkoxy optionally substituted by one or more lower alkyl, lower alkoxy, halo, lower acyl, lower acyloxy, cyano, nitro or lower acylamino, amino, lower alkylamino, lower dialkylamino, halo, cyano, or S(O) n R wherein R is lower alkyl of one to six carbon atoms; phenyl optionally substituted by one or more lower alkyl, lower alkoxy, halo, lower acyl, lower acyloxy, cyano, nitro or lower acylamino; phenyl lower alkyl optionally substituted by one or more lower alkyl, lower alkoxy, halo, lower acyl, lower acyloxy, cyano, nitro or lower acylamino; or heterocyclic aryl selected from the group consisting of thiapyranyl, benzothiapyranyl, furyl, pyrrolyl, imidazolyl, pyrazolyl, pyridinyl, pyrimidinyl, indolyl, quinolinyl and indazolyl 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 n is 0, 1 or 2; and W is alkyl of one to seven carbon atoms.
Claim 15
Dependent Claim
21 words
A method according to claim 12 wherein R 1 and R 2 are lower alkoxy of one to six carbon atoms.
Claim 16
Dependent Claim
21 words
A method according to claim 12 wherein R 1 and R 2 are lower alkylthio of one to six carbon atoms.
Claim 17
Dependent Claim
275 words
A compound of the formula ##STR13## wherein: R 1 and R 2 are lower alkoxy of one to six carbon atoms or lower alkylthio of one to six carbon atoms; R 3 is hydrogen, lower alkyl of one to six carbon atoms, lower alkoxy of one to six carbon atoms, phenyl optionally substituted by one or more lower alkyl, lower alkoxy, halo, lower acyl, lower acyloxy, cyano, nitro or lower acylamino, phenyl lower alkyl optionally substituted by one or more lower alkyl, lower alkoxy, halo, lower acyl, lower acyloxy, cyano, nitro or lower acylamino, phenyl lower alkoxy optionally substituted by one or more lower alkyl, lower alkoxy, halo, lower acyl, lower acyloxy, cyano, nitro or lower acylamino, amino, lower alkylamino, lower dialkylamino, halo, cyano, or S(O) n R wherein R is lower alkyl of one to six carbon atoms; phenyl optionally substituted by one or more lower alkyl, lower alkoxy, halo, lower acyl, lower acyloxy, cyano, nitro or lower acylamino; phenyl lower alkyl optionally substituted by one or more lower alkyl, lower alkoxy, halo, lower acyl, lower acyloxy, cyano, nitro or lower acylamino; or heterocyclic aryl selected from the group consisting of thiapyranyl, benzothiapyranyl, furyl, pyrrolyl, imidazolyl, pyrazolyl, pyridinyl, pyrimidinyl, indolyl, quinolinyl and indazolyl 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 n is 0, 1 or 2; and W is alkyl of one to seven carbon atoms; with the proviso that R 3 is not hydrogen when R 1 and R 2 are methoxy and W is methyl.
Claim 18
Dependent Claim
275 words
A compound of the formula ##STR13## wherein: R 1 and R 2 are lower alkoxy of one to six carbon atoms or lower alkylthio of one to six carbon atoms; R 3 is hydrogen, lower alkyl of one to six carbon atoms, lower alkoxy of one to six carbon atoms, phenyl optionally substituted by one or more lower alkyl, lower alkoxy, halo, lower acyl, lower acyloxy, cyano, nitro or lower acylamino, phenyl lower alkyl optionally substituted by one or more lower alkyl, lower alkoxy, halo, lower acyl, lower acyloxy, cyano, nitro or lower acylamino, phenyl lower alkoxy optionally substituted by one or more lower alkyl, lower alkoxy, halo, lower acyl, lower acyloxy, cyano, nitro or lower acylamino, amino, lower alkylamino, lower dialkylamino, halo, cyano, or S(O) n R wherein R is lower alkyl of one to six carbon atoms; phenyl optionally substituted by one or more lower alkyl, lower alkoxy, halo, lower acyl, lower acyloxy, cyano, nitro or lower acylamino; phenyl lower alkyl optionally substituted by one or more lower alkyl, lower alkoxy, halo, lower acyl, lower acyloxy, cyano, nitro or lower acylamino; or heterocyclic aryl selected from the group consisting of thiapyranyl, benzothiapyranyl, furyl, pyrrolyl, imidazolyl, pyrazolyl, pyridinyl, pyrimidinyl, indolyl, quinolinyl and indazolyl 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 n is 0, 1 or 2; and W is alkyl of one to seven carbon atoms; with the proviso that R 3 is not hydrogen when R 1 and R 2 are methoxy and W is methyl.
Claim 19
Dependent Claim
26 words
A compound of claim 15 of the formula ##STR14## wherein R 1 , R 2 , R 3 and W are as defined in claim 15.
Claim 20
Dependent Claim
20 words
A compound of claim 16 wherein R 1 and R 2 are lower alkoxy of one to six carbon atoms.
Claim 21
Dependent Claim
19 words
A compound of claim 17 wherein R 3 is selected from the group consisting of fluoro, chloro and bromo.
Claim 22
Dependent Claim
10 words
A compound of claim 17 wherein R 3 is cyano.
Claim 23
Dependent Claim
8 words
A compound of claim 18 which is 6-chloro-2,3-dimethoxy-1,4-acetyloxynaphthalene.
Claim 24
Dependent Claim
8 words
A compound of claim 18 which is 6-chloro-2,3-di-n-butoxy-1,4-acetyloxynaphthalene.
Claim 25
Dependent Claim
20 words
A compound of claim 16 wherein R 1 and R 2 are lower alkylthio of one to six carbon atoms.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-08-21 | 1988-02-20 | 1988-08-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-08-21 | 1992-02-20 | 1992-08-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-08-21 | 1996-02-20 | 1996-08-21 | $7700.00 | Window Closed / Lapsed |