US5202471A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Alkyl, alkoxy and thioalkoxy substituted diphenyl acetylenes having retinoid like activity
Assignee: Allergan Inc
•
Filing: 1990-02-06
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Granted: 1993-04-13
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Expires: 2010-02-06
Abstract
Abstract Retinoid like activity is exhibited by compounds of the formula ##STR1## where R 1 -R 4 independently are hydrogen, lower alkyl, cycloalkyl or lower alkenyl, A and B independently are hydrogen, lower alkyl cycloalkyl, lower alkenyl, SR* or OR* where R* is lower alkyl, cycloalkyl or lower alkenyl; Y is lower alkenyl, lower alkynyl, lower cycloalkyl, lower branched chain alkyl or (CH 2 ) n where n is 0-6; and Z 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' or a ketal derivative where R' is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons.
Inventors
- 👤 Roshantha A. S. Chandraratna
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 08:44
CPC Classifications
C; C07; C07C; C07C25/00; C07C25/02; C07C15/00; C07C15/40; C07C15/42; C07C15/48; C07C323/00; C07C323/01; C07C323/09; C07C323/50; C07C323/62; C07C45/00; C07C45/45; C07C45/46; C07C45/61; C07C45/67; C07C45/68; C07C49/00; C07C49/76; C07C49/794; C07C49/80; C07C49/807; C07C63/00; C07C63/66; C07C69/00; C07C69/76; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/0803; C07F7/0805; C07F7/081
Claims Analysis
Total Claims: 53
Claim 1
Independent Claim
92 words
Compounds of the formula ##STR16## wherein R 1 -R 4 independently are hydrogen, lower alkyl, cycloalkyl or lower alkenyl, A and B independently are hydrogen, tertiary butyl, 4-methylpentyl, 1,1,4-trimethylpentyl, cycloalkyl, lower alkenyl, or OR * where R * is lower brach chained alkyl, cycloalkyl or lower alkenyl with the proviso that one of A and B is not hydrogen; Y is lower alkenyl, lower alkynyl lower cycloalkyl, lower branched chain alkyl, or (CH 2 ) n where n is 0-6; and Z is --C))H or a pharmaceutically acceptable salt, or ester thereof.
Claim 2
Dependent Claim
92 words
Compounds of the formula ##STR16## wherein R 1 -R 4 independently are hydrogen, lower alkyl, cycloalkyl or lower alkenyl, A and B independently are hydrogen, tertiary butyl, 4-methylpentyl, 1,1,4-trimethylpentyl, cycloalkyl, lower alkenyl, or OR * where R * is lower brach chained alkyl, cycloalkyl or lower alkenyl with the proviso that one of A and B is not hydrogen; Y is lower alkenyl, lower alkynyl lower cycloalkyl, lower branched chain alkyl, or (CH 2 ) n where n is 0-6; and Z is --C))H or a pharmaceutically acceptable salt, or ester thereof.
Claim 3
Dependent Claim
19 words
Compounds of claim 1 wherein A and B independently are hydrogen, lower branch chained alkyl, cycloalkyl, or lower alkenyl.
Claim 4
Dependent Claim
12 words
Compounds of claim 2 wherein R 1 -R 4 all are hydrogen.
Claim 5
Dependent Claim
11 words
Compounds of claim 2 wherein Z is a carboxylic acid ester.
Claim 6
Dependent Claim
14 words
Compounds of claim 2 wherein Z is COOH or a pharmaceutically acceptable salt thereof.
Claim 7
Dependent Claim
89 words
Compounds of the formula ##STR17## wherein R 1 -R 4 independently are hydrogen, lower alkyl, cycloalkyl or lower alkenyl, A and B independently are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, SR * and OR * and one of the A and B groups is SR * where R * is lower alkyl, cycloalkyl or lower alkenyl, Y is lower alkenyl, lower alkynyl lower cycloalkyl, lower branched chain alkyl, or (CH 2 ) n where n is 0-6; and Z is --COOH or a pharmaceutically acceptable salt, or ester thereof.
Claim 8
Dependent Claim
89 words
Compounds of the formula ##STR17## wherein R 1 -R 4 independently are hydrogen, lower alkyl, cycloalkyl or lower alkenyl, A and B independently are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, SR * and OR * and one of the A and B groups is SR * where R * is lower alkyl, cycloalkyl or lower alkenyl, Y is lower alkenyl, lower alkynyl lower cycloalkyl, lower branched chain alkyl, or (CH 2 ) n where n is 0-6; and Z is --COOH or a pharmaceutically acceptable salt, or ester thereof.
Claim 9
Dependent Claim
12 words
Compounds of claim 6 wherein R 1 -R 4 all are hydrogen.
Claim 10
Dependent Claim
19 words
Compounds of claim 6 wherein Y is characterized by the formula (CH 2 ) n where n is 0-6.
Claim 11
Dependent Claim
10 words
Compounds of claim 8 wherein Z is carboxylic acid ester.
Claim 12
Dependent Claim
20 words
A compound set forth in claim 1, comprised in and admixed with a pharmaceutical composition including a pharmaceutically acceptable excipient.
Claim 13
Dependent Claim
32 words
A compound set forth in claim 1, comprised in and admixed with a pharmaceutical composition as set forth in claim 10, said composition being useful for treating skin disorders in a mammal.
Claim 14
Dependent Claim
52 words
Compounds of the formula ##STR18## wherein A and B and R 1 -R 4 independently are hydrogen, tertiary butyl, 4-methylpentyl, 1,1,4-trimethylpentyl, cycloalkyl or lower alkenyl, with the proviso that one of A and B is not hydrogen; n is 0-6; and Z is --COOH or a pharmaceutically acceptable salt, or ester thereof.
Claim 15
Dependent Claim
52 words
Compounds of the formula ##STR18## wherein A and B and R 1 -R 4 independently are hydrogen, tertiary butyl, 4-methylpentyl, 1,1,4-trimethylpentyl, cycloalkyl or lower alkenyl, with the proviso that one of A and B is not hydrogen; n is 0-6; and Z is --COOH or a pharmaceutically acceptable salt, or ester thereof.
Claim 16
Dependent Claim
17 words
Compounds of claim 12 wherein Z is COOR * where R * is hydrogen or lower alkyl.
Claim 17
Dependent Claim
8 words
Compounds of claim 12 wherein n is zero.
Claim 18
Dependent Claim
28 words
Compounds of claim 12 wherein the ethynyl and the (CH 2 ) n -Z groups are attached, respectively, to the 1 and 4 positions of the benzene nucleus.
Claim 19
Dependent Claim
22 words
Compounds of claim 12 wherein one of A and B is a branched chain lower alkyl group and the other is hydrogen.
Claim 20
Dependent Claim
71 words
Compounds of the formula ##STR19## wherein R 1 -R 4 independently are hydrogen, lower alkyl, cycloalkyl or lower alkenyl, A and B independently are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, or SR * where R * is lower alkyl, cycloalkyl or lower alkenyl, with the proviso that one of A and B is SR * ; n is 0-6; and Z is --COOH or a pharmaceutically acceptable salt, or ester thereof.
Claim 21
Dependent Claim
71 words
Compounds of the formula ##STR19## wherein R 1 -R 4 independently are hydrogen, lower alkyl, cycloalkyl or lower alkenyl, A and B independently are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, or SR * where R * is lower alkyl, cycloalkyl or lower alkenyl, with the proviso that one of A and B is SR * ; n is 0-6; and Z is --COOH or a pharmaceutically acceptable salt, or ester thereof.
Claim 22
Dependent Claim
17 words
Compounds of claim 17 wherein Z is COOR ** where R ** is hydrogen or lower alkyl.
Claim 23
Dependent Claim
8 words
Compounds of claim 17 wherein n is zero.
Claim 24
Dependent Claim
28 words
Compounds of claim 17 wherein the ethynyl and the (CH 2 ) n -Z groups are attached, respectively, to the 1 and 4 positions of the benzene nucleus.
Claim 25
Dependent Claim
62 words
Compounds of the formula ##STR20## wherein R 1 -R 4 independently are hydrogen, lower alkyl, cycloalkyl or lower alkenyl, one of A and B is characterized by the formula SR * where R * is branched chain lower alkyl or lower alkenyl, and the other is hydrogen, n is 0-6; and Z is --COOH or a pharmaceutically acceptable salt, or ester thereof.
Claim 26
Dependent Claim
62 words
Compounds of the formula ##STR20## wherein R 1 -R 4 independently are hydrogen, lower alkyl, cycloalkyl or lower alkenyl, one of A and B is characterized by the formula SR * where R * is branched chain lower alkyl or lower alkenyl, and the other is hydrogen, n is 0-6; and Z is --COOH or a pharmaceutically acceptable salt, or ester thereof.
Claim 27
Dependent Claim
37 words
Compounds of the formula ##STR21## wherein A and B are hydrogen, lower alkyl, cycloalkyl or lower alkenyl, with the proviso that one of A and B is not hydrogen, and R * is H or lower alkyl.
Claim 28
Dependent Claim
37 words
Compounds of the formula ##STR21## wherein A and B are hydrogen, lower alkyl, cycloalkyl or lower alkenyl, with the proviso that one of A and B is not hydrogen, and R * is H or lower alkyl.
Claim 29
Dependent Claim
13 words
Compounds of claim 22 wherein A is hydrogen and B is tertiary butyl.
Claim 30
Dependent Claim
10 words
The compound of claim 23 wherein R * is ethyl.
Claim 31
Dependent Claim
10 words
The compound of claim 23 wherein R * is hydrogen.
Claim 32
Dependent Claim
13 words
Compounds of claim 26 wherein B is hydrogen and A is tertiary butyl.
Claim 33
Dependent Claim
10 words
The compound of claim 26 wherein R * is ethyl.
Claim 34
Dependent Claim
10 words
The compound of claim 26 wherein R * is hydrogen.
Claim 35
Dependent Claim
12 words
Compounds of claim 26 wherein A is hydrogen and B is 4-methylpentyl.
Claim 36
Dependent Claim
10 words
The compound of claim 29 wherein R * is ethyl.
Claim 37
Dependent Claim
10 words
The compound of claim 29 wherein R * is hydrogen.
Claim 38
Dependent Claim
12 words
Compounds of claim 22 wherein A is hydrogen and B is 1,1,4-trimethylpentyl.
Claim 39
Dependent Claim
10 words
The compound of claim 32 wherein R * is ethyl.
Claim 40
Dependent Claim
10 words
The compound of claim 32 wherein R * is hydrogen.
Claim 41
Dependent Claim
51 words
The compounds of the formula ##STR22## wherein A and B independently are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, or SR * where R * is lower alkyl cycloalkyl or lower alkenyl, with the proviso that one of A and B is SR * and R ** is H or lower alkyl.
Claim 42
Dependent Claim
51 words
The compounds of the formula ##STR22## wherein A and B independently are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, or SR * where R * is lower alkyl cycloalkyl or lower alkenyl, with the proviso that one of A and B is SR * and R ** is H or lower alkyl.
Claim 43
Dependent Claim
19 words
Compounds of claim 35 wherein A is hydrogen and B is SR * where R * is tertiary butyl.
Claim 44
Dependent Claim
10 words
The compound of claim 36 wherein R ** is ethyl.
Claim 45
Dependent Claim
10 words
The compound of claim 36 wherein R ** is hydrogen.
Claim 46
Dependent Claim
19 words
Compounds of claim 35 wherein B is hydrogen and A is SR * where R * is tertiary butyl.
Claim 47
Dependent Claim
10 words
The compound of claim 39 wherein R II is ethyl.
Claim 48
Dependent Claim
10 words
The compound of claim 39 wherein R ** is hydrogen.
Claim 49
Dependent Claim
19 words
The compounds of claim 35 wherein A is hydrogen and B is SR * where R * is 3-methyl-2-butenyl.
Claim 50
Dependent Claim
10 words
The compound of claim 42 wherein R ** is ethyl.
Claim 51
Dependent Claim
10 words
The compound of claim 42 wherein R ** is hydrogen.
Claim 52
Dependent Claim
16 words
A pharmaceutical composition comprising a compound set forth in claim 6, and a pharmaceutically acceptable excipient.
Claim 53
Dependent Claim
27 words
A pharmaceutical composition comprising a compound set forth in claim 6, and a pharmaceutically acceptable excipient, said composition being useful for treating skin disorders in a mammal.
References Cited (Backward Citations)
EP0130795A2
Cited
DE3434946A1
Cited
EP0176034B1
Cited
EP0217354A1
Cited
US4739098A
Cited
US4810804A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1996-04-12 | 1996-10-12 | 1997-04-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2000-04-12 | 2000-10-12 | 2001-04-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2004-04-12 | 2004-10-12 | 2005-04-13 | $7700.00 | Window Closed / Lapsed |