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Patent US5324840A successfully refreshed from Google Patents.
US5324840A
Expired / Lapsed
US
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Method of treatment with compounds having retinoid-like activity and reduced skin toxicity and lacking teratogenic effects
Assignee: Allergan Inc
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Filing: 1992-06-11
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Granted: 1994-06-28
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Expires: 2012-06-11
Abstract
Abstract Compounds that provide non-teratogenic effects and lack irritation to the skin are shown in the formula below where the partially drawn ring signifies an aromatic ring which may be carbocyclic or heteroaromatic, 6-membered or 5-membered, and may be condensed with another ring. R 1 is lower alkyl, Cl, Br, or I, R 2 is H, lower alkyl, Cl, Br, or I, and R 3 is lower alkyl, Cl, Br, I, or is an ether, thioether, ester, thioester, amine or substituted amine group. ##STR1##
Inventors
- 👤 Roshantha A. S. Chandraratna
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 10:15
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/78; C07D213/79; C07D213/80; A; A61; A61P; A61P17/00; A61P27/00; A61P29/00; A61P3/00; A61P3/02; A61P3/06; A61P35/00; A61P37/00; A61P37/02; A61P9/00; A61P9/10; C07D307/00; C07D307/02; C07D307/34; C07D307/56; C07D307/68; C07D311/00; C07D311/02; C07D311/74; C07D333/00; C07D333/02; C07D333/04; C07D333/26; C07D333/38
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
304 words
A compound of the formula ##STR18## where R 1 is lower alkyl, Cl, Br, or I; R 2 is H, lower alkyl, Cl, Br, or I; R 3 is lower alkyl, Cl, Br, I, OR11, SR 11 , OCOR 11 , SCOR11, NH 2 , NHR 11 , N(R 11 ) 2 , NHCOR 11 , or NR 11 --COR 11 ; R 5 and R 6 independently are H, lower alkyl, Cl, Br, I, lower alkoxy or lower thioalkoxy of 1 to 6 carbons; A is (CH 2 ) n where n is 0-5, lower branched chain alkyl having 3 to 6 carbons, cycloalkyl having 3 to 6 carbons, alkenyl having 2 to 6 carbons and 1 or 2 double bonds, alkynyl having 2 to 6 carbons and 1 or 2 triple bonds; B is COOH or a pharmaceutically acceptable salt thereof, COOR 8 , CONR9R 10 , --CH 2 OH, CH 2 OR 11 , CH 2 OCOR 11 , CHO, CH(OR 12 ) 2 , CHOR 13 O, --COR 7 , CR 7 (OR 12 ) 2 , or CR 7 OR 13 O, where R 7 is an alkyl, cycloalkyl or alkenyl group containing 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 alkyl of 1 to 10 carbons, phenyl or lower alkylphenyl, R 12 is lower alkyl, and R 13 is divalent alkyl radical of 2-5 carbons; R 20 is independently H or lower alkyl, and Y 1 is thienyl, furyl or pyridyl.
Claim 2
Dependent Claim
304 words
A compound of the formula ##STR18## where R 1 is lower alkyl, Cl, Br, or I; R 2 is H, lower alkyl, Cl, Br, or I; R 3 is lower alkyl, Cl, Br, I, OR11, SR 11 , OCOR 11 , SCOR11, NH 2 , NHR 11 , N(R 11 ) 2 , NHCOR 11 , or NR 11 --COR 11 ; R 5 and R 6 independently are H, lower alkyl, Cl, Br, I, lower alkoxy or lower thioalkoxy of 1 to 6 carbons; A is (CH 2 ) n where n is 0-5, lower branched chain alkyl having 3 to 6 carbons, cycloalkyl having 3 to 6 carbons, alkenyl having 2 to 6 carbons and 1 or 2 double bonds, alkynyl having 2 to 6 carbons and 1 or 2 triple bonds; B is COOH or a pharmaceutically acceptable salt thereof, COOR 8 , CONR9R 10 , --CH 2 OH, CH 2 OR 11 , CH 2 OCOR 11 , CHO, CH(OR 12 ) 2 , CHOR 13 O, --COR 7 , CR 7 (OR 12 ) 2 , or CR 7 OR 13 O, where R 7 is an alkyl, cycloalkyl or alkenyl group containing 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 alkyl of 1 to 10 carbons, phenyl or lower alkylphenyl, R 12 is lower alkyl, and R 13 is divalent alkyl radical of 2-5 carbons; R 20 is independently H or lower alkyl, and Y 1 is thienyl, furyl or pyridyl.
Claim 3
Dependent Claim
10 words
A compound of claim 1 wherein R 20 is methyl.
Claim 4
Dependent Claim
16 words
A compound of claim 1 wherein R 2 , R 5 and R 6 are hydrogen.
Claim 5
Dependent Claim
10 words
A compound of claim 1 wherein R 1 is methyl.
Claim 6
Dependent Claim
13 words
A compound of claim 1 wherein R 3 is methyl, Cl or Br.
Claim 7
Dependent Claim
22 words
A compound of claim 1 wherein A is (CH 2 ) n , n=0 and B is COOH or COOR 8 .
Claim 8
Dependent Claim
47 words
A compound of claim 6 wherein Y 1 is thienyl, R 1 , R 3 and R 20 are methyl, R 2 , R 5 and R 6 are hydrogen and A is (CH 2 ) n , n=0 and B is COOH or COOR 8 .
Claim 9
Dependent Claim
49 words
A compound of claim 6 wherein Y 1 is furyl, R 1 , R 3 and R 20 are methyl, R 2 , R 5 and R 6 are hydrogen and A is (CH 2 ) n , n=0 and B is COOH or COOC 2 H 5 .
Claim 10
Dependent Claim
49 words
A compound of claim 6 wherein Y 1 is pyridyl, R 1 , R 3 and R 20 are methyl, R 2 , R 5 and R 6 are hydrogen and A is (CH 2 ) n , n=0 and B is COOH or COOC 2 H 5 .
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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) | 1997-06-27 | 1997-12-27 | 1998-06-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2001-06-27 | 2001-12-27 | 2002-06-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2005-06-27 | 2005-12-27 | 2006-06-28 | $7700.00 | Window Closed / Lapsed |