US5602135A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Phenyl or heteroaryl and tetrahydronaphthyl substituted diene compounds having retinoid like biological activity
Assignee: Allergan Inc
•
Filing: 1995-06-02
•
Granted: 1997-02-11
•
Expires: 2015-06-02
Abstract
Abstract Compounds of Formula 1 ##STR1## wherein m is 1-4; R 1 -R 4 independently are hydrogen, lower alkyl of 1 to 6 carbons, Cl, Br, or I; R 5 is hydrogen, lower alkyl of 1 to 6 carbons, Cl, Br, I, lower alkoxy or lower thioalkoxy of 1-6 carbons; R 6 is hydrogen, lower alkyl, Cl, Br, I, OR 11 , SR 11 , OCOR 11 , SCOR 11 , NH2, NHR 11 , N(R 11 ) 2 , NHCOR 11 OR NR 11 --COR 11 ; R 20 is independently hydrogen or lower alkyl; Y is an aromatic group such as phenyl or naphthyl, or a heteroaryl group selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl and oxazolyl; A is (CH 2 ) n where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds; B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR 8 , CONR 9 R 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 5-10 carbons, or phenyl or lower aklylphenyl, R 11 is lower alkyl, phenyl or lower alkylphenyl, R 12 is lower alkyl, and R 13 is divalent alkyl radical of 2-5 carbons, have retinoid like biological activity. In the compounds of the invention the A-B and the butadiene groups are attached to adjacent aromatic carbons of the Y moiety.
Inventors
- 👤 Roshantha A. Chandraratna
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 10:43
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/54; C07F9/5428; A; A61; A61P; A61P3/00; A61P3/02; A61P43/00; C07C; C07C17/00; C07C17/093; C07C17/16; C07C45/00; C07C45/27; C07C45/29; C07C45/45; C07C45/46; C07C49/00; C07C49/76; C07C49/782; C07C49/792; C07C63/00; C07C63/66; C07C69/00; C07C69/76; C07D; C07D307/00; C07D307/02; C07D307/04; C07D307/18; C07D307/22; C07D307/34; C07D307/56; C07D307/68; C07D333/00; C07D333/02; C07D333/04; C07D333/26; C07D333/38
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
323 words
A compound of the formula ##STR6## wherein m is 1-4; R 1 -R 4 independently are hydrogen, lower alkyl of 1 to 6 carbons, Cl, Br, or I; R 5 is hydrogen, lower alkyl of 1 to 6 carbons, Cl, Br, I, lower alkoxy or lower thioalkoxy of 1-6 carbons; R 6 is hydrogen, lower alkyl, Cl, Br, I, OR 11 , SR 11 , OCOR 11 , SCOR 11 , NH2, NHR 11 , N(R 11 ) 2 , NHCOR 11 OR NR 11 ---COR 11 ; R 20 is independently hydrogen or lower alkyl; Y is a heteroaryl group selected from the group consisting of pyridyl pyridazinyl, pyrimidinyl and pyrazinyl; A is (CH 2 ) n where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds; B is COOH or a pharmaceutically acceptable salt thereof, COOR 8 , CONR 9 R 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 5-10 carbons, or phenyl or lower aklylphenyl, R 11 is lower alkyl, phenyl or lower alkylphenyl, R12 is lower alkyl, and R 13 is divalent alkyl radical of 2-5 carbons, with the proviso that the diene and A-B moieties are attached to adjacent carbon atoms of the heteroaryl group symbolized by Y.
Claim 2
Dependent Claim
323 words
A compound of the formula ##STR6## wherein m is 1-4; R 1 -R 4 independently are hydrogen, lower alkyl of 1 to 6 carbons, Cl, Br, or I; R 5 is hydrogen, lower alkyl of 1 to 6 carbons, Cl, Br, I, lower alkoxy or lower thioalkoxy of 1-6 carbons; R 6 is hydrogen, lower alkyl, Cl, Br, I, OR 11 , SR 11 , OCOR 11 , SCOR 11 , NH2, NHR 11 , N(R 11 ) 2 , NHCOR 11 OR NR 11 ---COR 11 ; R 20 is independently hydrogen or lower alkyl; Y is a heteroaryl group selected from the group consisting of pyridyl pyridazinyl, pyrimidinyl and pyrazinyl; A is (CH 2 ) n where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds; B is COOH or a pharmaceutically acceptable salt thereof, COOR 8 , CONR 9 R 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 5-10 carbons, or phenyl or lower aklylphenyl, R 11 is lower alkyl, phenyl or lower alkylphenyl, R12 is lower alkyl, and R 13 is divalent alkyl radical of 2-5 carbons, with the proviso that the diene and A-B moieties are attached to adjacent carbon atoms of the heteroaryl group symbolized by Y.
Claim 3
Dependent Claim
11 words
A compound in accordance with claim 1 wherein Y is pyridyl.
Claim 4
Dependent Claim
14 words
A compound in accordance with claim 1 wherein R 1 is H or methyl.
Claim 5
Dependent Claim
20 words
A compound in accordance with claim 1 wherein R 2 , R 3 and R 4 are H or methyl.
Claim 6
Dependent Claim
12 words
A compound in accordance with claim 1 wherein R 5 is H.
Claim 7
Dependent Claim
14 words
A compound in accordance with claim 1 wherein R 6 is hydrogen or methyl.
Claim 8
Dependent Claim
11 words
A compound in accordance with claim 1 wherein m is 2.
Claim 9
Dependent Claim
14 words
A compound in accordance with claim 1 wherein R 20 is H or methyl.
Claim 10
Dependent Claim
37 words
A compound in accordance with claim 1 where the A-B group is (CH 2 ) n --COOH, (CH 2 ) n --COOR 8 or (CH 2 ) n --CONR 9 R 10 , and n is 0.
Claim 11
Dependent Claim
68 words
A compound in accordance with claim 1 wherein m is 2, R 1 , R 2 , R 3 , R 4 , R 6 and R 20 are H or methyl, R 5 is H, Y is pyridyl, the A-B group is (CH 2 ) n --COOH, (CH 2 ) n --COOR 8 or (CH 2 ) n --CONR 9 R 10 , and n is 0.
Claim 12
Dependent Claim
95 words
A method of treating a disease or condition of a mammal which is susceptible to treatment by a retinoid-like compound, with a pharmaceutical composition containing an effective amount of a compound in accordance with claim 1 said disease or condition being selected from dermatoses, Darier's disease, psoriasis, icthyosis, eczema, atopic dermatitis, malignant hyperproliferative diseases, artherosclerosis and restenosis resulting from neointiural hyperproliferation, endometrial hyperplasia, benign prostatic hypertrophy, proliferative vitreal retirropathy and dysplasias, autoimmune diseases, immunological disorders, chronic inflammatory diseases, diseases associated with lipid metabolism and transport, wound healing, dry eye syndrome and sun damage to skin.
References Cited (Backward Citations)
US4096341A
Cited
US4326055A
Cited
US4391731A
Cited
DE3316932A1
Cited
EP0098591A1
Cited
US4456618A
Cited
US4526787A
Cited
EP0130795A2
Cited
WO1985000806A1
Cited
WO1985004652A1
Cited
US4826984A
Cited
US4695649A
Cited
DE3524199A1
Cited
EP0170105A2
Cited
US4723028A
Cited
US4740519A
Cited
EP0176032A2
Cited
EP0176034A2
Cited
EP0176033A2
Cited
GB2164938A
Cited
US4826969A
Cited
DE3602473A1
Cited
DE3708060A1
Cited
US4855320A
Cited
GB2190378A
Cited
DE3715955A1
Cited
EP0253302A2
Cited
US4876349A
Cited
US4739098A
Cited
EP0272921A1
Cited
US4927947A
Cited
EP0284288A1
Cited
US5264578A
Cited
US5380877A
Cited
US5354752A
Cited
US5348972A
Cited
US5234926A
Cited
US4810804A
Cited
EP0303915A2
Cited
EP0315071A2
Cited
US5231113A
Cited
US5130335A
Cited
US4895868A
Cited
US5015658A
Cited
EP0350846A2
Cited
US5037825A
Cited
US5089509A
Cited
US4992468A
Cited
US5068252A
Cited
US5272156A
Cited
US4980369A
Cited
US5407937A
Cited
US5162546A
Cited
US5399561A
Cited
US5183827A
Cited
US5278318A
Cited
US5023341A
Cited
US5053523A
Cited
US5248777A
Cited
US5045551A
Cited
US5005550A
Cited
US5414007A
Cited
US5264456A
Cited
US5175185A
Cited
US5013744A
Cited
US5013744B1
Cited
US5349105A
Cited
US5202471A
Cited
WO1991016051A1
Cited
WO1992006948A1
Cited
US5346915A
Cited
US5134159A
Cited
US5348975A
Cited
US5346895A
Cited
US5324744A
Cited
US5326898A
Cited
US5391753A
Cited
US5434173A
Cited
US5324840A
Cited
US5399586A
Cited
US5344959A
Cited
US5426118A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 2000-02-11 | 2000-08-12 | 2001-02-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2004-02-11 | 2004-08-12 | 2005-02-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2008-02-11 | 2008-08-12 | 2009-02-11 | $7700.00 | Window Closed / Lapsed |