US5451605A
Expired / Lapsed
US
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1,2-epoxycyclohexanyl and bicyclic aromatic substituted ethyne compounds having retinoid-like biological activity
Assignee: Allergan Inc
•
Filing: 1993-12-30
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Granted: 1995-09-19
•
Expires: 2013-12-30
Abstract
Abstract Compounds of the formula ##STR1## where R 1 -R 5 are hydrogen, lower alkyl of 1-6 carbons, or halogen; 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 alkylphenyl, 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, and Z is ##STR2## wherein R 6 is hydrogen, lower alkyl of 1-6 carbons, or halogen, R 6 can be attached to any available position on the Z group, and m is an integer between 0 to 4, have retinoid-like biological activity.
Inventors
- 👤 Roshantha A. Chandraratna
- 👤 Richard L. Beard
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 06:36
CPC Classifications
C; C07; C07D; C07D405/00; C07D405/02; C07D405/06; A; A61; A61P; A61P17/00; A61P35/00; C07D303/00; C07D303/02; C07D303/38; C07D303/40; C07D407/00; C07D407/02; C07D407/06; C07D409/00; C07D409/02; C07D409/06
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
254 words
A compound of the formula ##STR8## where R 1 -R 5 are hydrogen, lower alkyl of 1-6 carbons, or halogen; 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 alkylphenyl, 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, and Z is selected from the groups: ##STR9## wherein R 6 is hydrogen, lower alkyl of 1-6 carbons, or halogen, R 6 can be attached to any available position on the Z group, and m is an integer between 0 to 4.
Claim 2
Dependent Claim
254 words
A compound of the formula ##STR8## where R 1 -R 5 are hydrogen, lower alkyl of 1-6 carbons, or halogen; 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 alkylphenyl, 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, and Z is selected from the groups: ##STR9## wherein R 6 is hydrogen, lower alkyl of 1-6 carbons, or halogen, R 6 can be attached to any available position on the Z group, and m is an integer between 0 to 4.
Claim 3
Dependent Claim
16 words
A compound of claim 1 wherein A is (CH 2 ) n and n is 0.
Claim 4
Dependent Claim
21 words
A compound of claim 1 wherein B is COOH or a pharmaceutically acceptable salt thereof, or B is COOR 8 .
Claim 5
Dependent Claim
13 words
A compound of claim 1 where R 1 and R 2 are methyl.
Claim 6
Dependent Claim
10 words
A compound of claim 1 where R 5 is methyl.
Claim 7
Dependent Claim
11 words
A compound of claim 1 where Z is a naphthalene radical.
Claim 8
Dependent Claim
13 words
A compound of claim 1 where R 3 and R 4 are hydrogen.
Claim 9
Dependent Claim
20 words
A compound of claim 1 where the R 5 group is attached to the 2-position of the 1,2-epoxy cyclohexane nucleus.
Claim 10
Dependent Claim
20 words
A compound of claim 1 wherein Z is selected from a group consisting of divalent naphthalene, benzothiophene and benzofuran nucleus.
Claim 11
Dependent Claim
22 words
A pharmaceutical composition comprising a pharmaceutically acceptable excipient and one or more compounds set forth in claim 1 as the active ingredient.
Claim 12
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 13
Dependent Claim
12 words
A method of claim 11 used for treating psoriasis in a mammal.
Claim 14
Dependent Claim
238 words
A compound of the formula ##STR10## where R 1 -R 5 are hydrogen, lower alkyl of 1-6 carbons, or halogen; 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 alkylphenyl, 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; R 6 is hydrogen, lower alkyl of 1-6 carbons, or halogen, and m is an integer between 0 to 4, or a pharmaceutically acceptable salt thereof.
Claim 15
Dependent Claim
238 words
A compound of the formula ##STR10## where R 1 -R 5 are hydrogen, lower alkyl of 1-6 carbons, or halogen; 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 alkylphenyl, 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; R 6 is hydrogen, lower alkyl of 1-6 carbons, or halogen, and m is an integer between 0 to 4, or a pharmaceutically acceptable salt thereof.
Claim 16
Dependent Claim
45 words
A compound of claim 13 where the A-B group represents (CH 2 ) n --COOH or pharmaceutically acceptable salt thereof, or (CH 2 ) n --COOR 8 or (CH 2 ) n --CONR 9 R 10 , and where n is 0, 1, or 2.
Claim 17
Dependent Claim
14 words
A compound of claim 13 where the R 1 and R 2 are methyl.
Claim 18
Dependent Claim
15 words
A compound of claim 13 where the R 3 and R 4 groups are hydrogen.
Claim 19
Dependent Claim
10 words
A compound of claim 13 where R 5 is methyl.
Claim 20
Dependent Claim
20 words
A compound of the formula ##STR11## where R 8 is hydrogen or lower alkyl, or a pharmaceutically acceptable salt thereof.
Claim 21
Dependent Claim
20 words
A compound of the formula ##STR11## where R 8 is hydrogen or lower alkyl, or a pharmaceutically acceptable salt thereof.
Claim 22
Dependent Claim
16 words
The compound of claim 18 where R 8 is hydrogen, or a pharmaceutically acceptable salt thereof.
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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) | 1998-09-18 | 1999-03-20 | 1999-09-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2002-09-18 | 2003-03-20 | 2003-09-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2006-09-18 | 2007-03-20 | 2007-09-19 | $7700.00 | Window Closed / Lapsed |