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US5677323A Expired / Lapsed US ⏱️ 0.0 years remaining

Acetylenes disubstituted with a heteroaromatic group and a 2-substituted chromanyl, thiochromanyl or 1, 2, 3, 4, -tetrahydroquinolinyl group having retinoid-like activity

Assignee: Allergan Inc
•
Filing: 1996-10-29
•
Granted: 1997-10-14
•
Expires: 2016-10-29
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Abstract

Abstract Retinoid-like activity is exhibited by compounds of the formula ##STR1## where X is S, O; 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, oxazolyl; 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 05:48
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 203 words
Compounds of the formula ##STR9## where X is S or O; 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 oxazolyl, 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 203 words
Compounds of the formula ##STR9## where X is S or O; 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 oxazolyl, 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 0.
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 20 words
A pharmaceutical composition comprising one or more compounds set forth in claim 1 the composition including a pharmaceutically acceptable excipient.
Claim 16
Dependent Claim 20 words
A pharmaceutical composition as set forth in claim 14, said composition being useful for treating skin disorders in a mammal.
Claim 17
Dependent Claim 36 words
A method for treating skin disorders 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 18
Dependent Claim 12 words
The method of claim 16 used for treating psoriasis 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) 2000-10-13 2001-04-14 2001-10-14 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 2004-10-13 2005-04-14 2005-10-14 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2008-10-13 2009-04-14 2009-10-14 $7700.00 Window Closed / Lapsed

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