Patent US1663809A successfully refreshed from Google Patents.
Patent US5407937A successfully refreshed from Google Patents.
US5407937A
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US
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Acetylenes disubstituted with a heteroaromatic group and a 2-substituted chromanyl, thiochromanyl or 1,2,3,4-tetrahydro-quinolinyl group having retinoid-like activity
Assignee: Allergan Inc
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Filing: 1993-10-27
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Granted: 1995-04-18
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Expires: 2013-10-27
Abstract
Abstract Retinoid-like activity is exhibited by compounds of the formula ##STR1## where X is S, O or 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 pyridazinyl, pyrimidinyl, pyrazinyl; 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
2026-10-30 05:43
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: 16
Claim 1
Independent Claim
218 words
Compounds of the formula ##STR9## where X is S, O, or 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 selected from a group consisting of pyrimidinyl, 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, cycloalkyl or alkenyl group having 1 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
218 words
Compounds of the formula ##STR9## where X is S, O, or 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 selected from a group consisting of pyrimidinyl, 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, cycloalkyl or alkenyl group having 1 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
8 words
Compounds of claim 1 where X is S.
Claim 4
Dependent Claim
11 words
Compounds of claim 2 where n is 0, 1, or 2.
Claim 5
Dependent Claim
8 words
Compounds of claim 3 where n is O.
Claim 6
Dependent Claim
22 words
Compounds of claim 3 where B is COOH or a pharmaceutically acceptable salt thereof, COOR 8 or COONR 9 R 10 .
Claim 7
Dependent Claim
11 words
Compounds of claim 3 where R 3 is hydrogen or methyl.
Claim 8
Dependent Claim
16 words
Compounds of claim 3 where R 4 is the same alkyl group as R 5 .
Claim 9
Dependent Claim
8 words
Compounds of claim 1 where X is O.
Claim 10
Dependent Claim
11 words
Compounds of claim 8 where n is 0, 1 or 2.
Claim 11
Dependent Claim
8 words
Compounds of claim 9 where n is O.
Claim 12
Dependent Claim
22 words
Compounds of claim 9 where B is COOH or a pharmaceutically acceptable salt thereof, COOR 8 or COONR 9 R 10 .
Claim 13
Dependent Claim
11 words
Compounds of claim 9 where R 3 is hydrogen or methyl.
Claim 14
Dependent Claim
16 words
Compounds of claim 9 where R 4 is the same alkyl group as R 5 .
Claim 15
Dependent Claim
58 words
A pharmaceutical composition comprising one or more compounds set forth in claim 1 in an amount effective for treating the conditions selected from acne, Darier's disease, psoriasis, icthyosis, excema, atopic dermatitis, epithelial cancer, immunological disorders, dry eye syndrome and for promoting wound healing and reversing effects of sun damage to skin, the composition including a pharmaceutically acceptable excipient.
Claim 16
Dependent Claim
49 words
A pharmaceutical composition as set forth in claim 14, said composition containing an effective amount of one or more compounds set forth in claim 14, the composition being useful for treating skin disorders selected from acne, Darier's disease, psoriasis, icthyosis, excema, atopic dermatitis, and epithelial cancer in a mammal.
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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) | 1998-04-17 | 1998-10-17 | 1999-04-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2002-04-17 | 2002-10-17 | 2003-04-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2006-04-17 | 2006-10-17 | 2007-04-18 | $7700.00 | Window Closed / Lapsed |