US5599819A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Acetylenes disubstituted with a thienyl or furyl group and a 2-substituted chromanyl, thiochromanyl or 1,2,3,4 - tetrahydroquinolinyl group having retinoid-like activity
Assignee: Allergan Inc
•
Filing: 1995-06-02
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Granted: 1997-02-04
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Expires: 2015-06-02
Abstract
Abstract Retinoid-like activity is exhibited by compounds of the formula ##STR1## where X is NR'; where R' is hydrogen or lower alkyl; R 1 , R 2 and R 3 are hydrogen or lower alkyl; R 4 and R 5 are hydrogen or lower alkyl with the proviso that R 4 and R 5 cannot both be hydrogen, A is thienyl, furyl; n is 0-5, and B is H, --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH 2 OH or an ether or ester derivative, or --CHO or an acetal derivative, or --COR 1 or a ketal derivative where R 1 is --(CH 2 ) m CH 3 where m is 0-4, or a pharmaceutically acceptable salt thereof.
Inventors
- 👤 Roshantha A. S. Chandraratna
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 11:41
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/06; C07D405/00; C07D405/02; C07D405/06; C07D409/00; C07D409/02; C07D409/06
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
222 words
Compounds of the formula ##STR9## where X is NR', where R' is hydrogen or lower alkyl; R 1 , R 2 and R 3 are hydrogen or lower alkyl; R 4 and R 5 are hydrogen or lower alkyl with the proviso that R 4 and R 5 both are not hydrogen; n is an integer from 0 to 5; A is thienyl or furyl, and B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR 8 , COONR 9 R 10 , --CH 2 OH, CH 2 OR 11 , CH 2 OCOR 11 , CHO, CH(OR 12 ) 2 , CHOR 13 O, --COR", CR"(OR 12 ) 2 , or CR"OR 13 O, where R" is an alkyl group having 1 to 5 carbons, cycloalkyl having 3 to 5 carbons or alkenyl group having 2 to 5 carbons, R 8 is an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R 8 is phenyl or lower alkylphenyl, R 9 and R 10 independently are hydrogen, an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or phenyl or lower alkylphenyl, R 11 is lower alkyl, phenyl or lower alkylphenyl, R 12 is lower alkyl, R 13 is divalent alkyl radical of 2-5 carbons.
Claim 2
Dependent Claim
222 words
Compounds of the formula ##STR9## where X is NR', where R' is hydrogen or lower alkyl; R 1 , R 2 and R 3 are hydrogen or lower alkyl; R 4 and R 5 are hydrogen or lower alkyl with the proviso that R 4 and R 5 both are not hydrogen; n is an integer from 0 to 5; A is thienyl or furyl, and B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR 8 , COONR 9 R 10 , --CH 2 OH, CH 2 OR 11 , CH 2 OCOR 11 , CHO, CH(OR 12 ) 2 , CHOR 13 O, --COR", CR"(OR 12 ) 2 , or CR"OR 13 O, where R" is an alkyl group having 1 to 5 carbons, cycloalkyl having 3 to 5 carbons or alkenyl group having 2 to 5 carbons, R 8 is an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R 8 is phenyl or lower alkylphenyl, R 9 and R 10 independently are hydrogen, an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or phenyl or lower alkylphenyl, R 11 is lower alkyl, phenyl or lower alkylphenyl, R 12 is lower alkyl, R 13 is divalent alkyl radical of 2-5 carbons.
Claim 3
Dependent Claim
15 words
Compounds of claim 1 where A is thienyl, and n is 0, 1, or 2.
Claim 4
Dependent Claim
8 words
Compounds of claim 2 where n is O.
Claim 5
Dependent Claim
22 words
Compounds of claim 2 where B is COOH or a pharmaceutically acceptable salt thereof, COOR 8 or COONR 9 R 10 .
Claim 6
Dependent Claim
11 words
Compounds of claim 2 where R 3 is hydrogen or methyl.
Claim 7
Dependent Claim
16 words
Compounds of claim 2 where R 4 is the same alkyl group as R 5 .
Claim 8
Dependent Claim
15 words
Compounds of claim 1 where A is furyl and n is 0, 1 or 2.
Claim 9
Dependent Claim
8 words
Compounds of claim 7 where n is 0.
Claim 10
Dependent Claim
22 words
Compounds of claim 7 where B is COOH or a pharmaceutically acceptable salt thereof, COOR 8 or COONR 9 R 10 .
Claim 11
Dependent Claim
11 words
Compounds of claim 7 where R 3 is hydrogen or methyl.
Claim 12
Dependent Claim
16 words
Compounds of claim 7 where R 4 is the same alkyl group as R 5 .
Claim 13
Dependent Claim
57 words
A pharmaceutical composition comprising a therapeutically effective amount of one or more compounds set forth in claim 1 for the treatment of acne, Darier's disease, psoriasis, icthyoisis, eczema, atopic dermatitis, epithelial cancers, arthritic diseases, immunological disorders, dry eye syndrome, for promoting wound healing and reversing sun damage to the skin, the composition including a pharmaceutically acceptable excipient.
Claim 14
Dependent Claim
40 words
A pharmaceutical composition as set forth in claim 12, said composition being useful for treating skin disorders selected from the group consisting of acne, Darier's disease, psoriasis, icthyoisis, eczema, atopic dermatitis and sun damage to the skin, in a mammal.
Claim 15
Dependent Claim
56 words
A method for treating skin disorders selected from the group consisting of acne, Darier's disease, psoriasis, icthyoisis, eczema, atopic dermatitis and sun damage to the skin, in a mammal which method comprises administering alone or in conjunction with a pharmaceutically acceptable excipient, a therapeutically effective amount of one or more compounds set forth in claim 1.
Claim 16
Dependent Claim
12 words
The method of claim 14 used for treating psoriasis in a mammal.
Claim 17
Dependent Claim
8 words
Compounds of claim 1 where A is thienyl.
Claim 18
Dependent Claim
8 words
Compounds of claim 1 where A is furyl.
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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) | 2000-02-04 | 2000-08-05 | 2001-02-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2004-02-04 | 2004-08-05 | 2005-02-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2008-02-04 | 2008-08-05 | 2009-02-04 | $7700.00 | Window Closed / Lapsed |