US5013744A
Expired / Lapsed
US
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Acetylenes disubstituted with a pyridinyl group and a substituted phenyl group having retinoid like activity
Assignee: Allergan Inc
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Filing: 1989-12-29
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Granted: 1991-05-07
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Expires: 2009-12-29
Abstract
Abstract Retinold like activity is exhibited by compounds of the formula ##STR1## where R 1 -R 3 independently are hydrogen, lower alkyl, cycloalkyl or lower alkenyl, A and B independently are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, SR 4 or OR 4 where R 4 is lower alkyl, cycloalkyl or lower alkenyl; Y is pyridyl; E is lower alkenyl, lower alkynyl, lower cycloalkyl, lower branched chain alkyl, or is characterized by the formula (CH 2 ) n where n is 0-5, and Z is H, OH, OR 5 , OCOR 5 , --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH 2 OH, CH 2 OR 6 , CH 2 OCOR 6 , or --CHO, CH(OR 7 ) 2 , CHOR 8 O, or COR 9 , CR 9 (OR 7 ) 2 , CR 9 OR 8 O where R 5 is lower alkyl, phenyl or lower alkylphenyl, R 6 is lower alkyl, phenyl or lower alkylphenyl, R 7 is lower alkyl, R 8 is a divalent alkyl radical of 2-5 carbons, and R 9 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
2026-11-02 01:21
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/78; C07D213/79; C07D213/80; A; A61; A61P; A61P1/00; A61P17/00
Claims Analysis
Total Claims: 48
Claim 1
Independent Claim
185 words
A compound of the formula ##STR16## wherein R 1 -R 3 independently are hydrogen, lower alkyl, cycloalkyl or lower alkenyl, A and B independently are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, SR 4 or OR 4 where R 4 is lower alkyl, cycloalkyl or lower alkenyl; Y is pyridyl; E is divalent lower alkenyl, lower alkynyl, lower cycloalkyl, lower branched chain alkyl, or is characterized by the formula (CH 2 ) n where n is 0-5, and Z is H, OH, OR 5 , OCOR 5 , --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH 2 OH, CH 2 OR 6 , CH 2 OCOR 6 , or --CHO, CH(OR 7 ) 2 , CHOR 8 O, or COR 9 or CR 9 (OR 7 ) 2 , CR 9 OR 8 O where R 5 is lower alkyl, phenyl or lower alkylphenyl, R 6 is lower alkyl, phenyl or lower alkylphenyl, R 7 is lower alkyl, R 8 is a divalent alkyl radical of 2-5 carbons, and R 9 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons.
Claim 2
Dependent Claim
185 words
A compound of the formula ##STR16## wherein R 1 -R 3 independently are hydrogen, lower alkyl, cycloalkyl or lower alkenyl, A and B independently are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, SR 4 or OR 4 where R 4 is lower alkyl, cycloalkyl or lower alkenyl; Y is pyridyl; E is divalent lower alkenyl, lower alkynyl, lower cycloalkyl, lower branched chain alkyl, or is characterized by the formula (CH 2 ) n where n is 0-5, and Z is H, OH, OR 5 , OCOR 5 , --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH 2 OH, CH 2 OR 6 , CH 2 OCOR 6 , or --CHO, CH(OR 7 ) 2 , CHOR 8 O, or COR 9 or CR 9 (OR 7 ) 2 , CR 9 OR 8 O where R 5 is lower alkyl, phenyl or lower alkylphenyl, R 6 is lower alkyl, phenyl or lower alkylphenyl, R 7 is lower alkyl, R 8 is a divalent alkyl radical of 2-5 carbons, and R 9 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons.
Claim 3
Dependent Claim
18 words
A compound of claim 1 wherein A and B independently are hydrogen, lower alkyl, cycloalkyl, or lower alkenyl.
Claim 4
Dependent Claim
16 words
A compound of claim 2 wherein one of the A and B groups is lower alkyl.
Claim 5
Dependent Claim
13 words
A compound of claim 3 wherein R 1 -R 3 all are hydrogen.
Claim 6
Dependent Claim
21 words
A compound of claim 2 wherein E is characterized by the formula (CH 2 ) n , where n is 0-5.
Claim 7
Dependent Claim
18 words
A compound of claim 2 wherein Z is --COOH or a pharmaceutically acceptable salt, ester or amide thereof.
Claim 8
Dependent Claim
12 words
A compound of claim 6 wherein Z is a carboxylic acid ester.
Claim 9
Dependent Claim
26 words
A compound of claim 1 wherein one of the A and B groups is SR 4 where R 4 is lower alkyl, cycloalkyl or lower alkenyl.
Claim 10
Dependent Claim
13 words
A compound of claim 8 wherein R 1 -R 3 all are hydrogen.
Claim 11
Dependent Claim
20 words
A compound of claim 8 wherein E is characterized by the formula (CH 2 ) n where n is 0-5.
Claim 12
Dependent Claim
18 words
A compound of claim 8 wherein Z is --COOH or a pharmaceutically acceptable salt, ester or amide thereof.
Claim 13
Dependent Claim
11 words
A compound of claim 11 wherein Z is carboxylic acid ester.
Claim 14
Dependent Claim
22 words
A pharmaceutical composition comprising an effective amount of a compound set forth in claim 1, in combination with a pharmaceutically acceptable excipient.
Claim 15
Dependent Claim
132 words
A compound of the formula ##STR17## wherein A and B and R 1 -R 3 independently are hydrogen, lower alkyl, cycloalkyl or lower alkenyl, with the proviso that one of A and B is not hydrogen; n is 0-6; and Z is H, --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH 2 OH, CH 2 OR 6 , CH 2 OCOR 6 , or --CHO, CH(OR 7 ) 2 , CHOR 8 O, or --COR 9 , CR 9 (OR 7 ) 2 , CR 9 OR 8 O where R 6 is lower alkyl, phenyl or lower alkylphenyl, R 7 is lower alkyl, R 8 is a divalent alkyl radical of 2-5 carbons, and R 9 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons.
Claim 16
Dependent Claim
132 words
A compound of the formula ##STR17## wherein A and B and R 1 -R 3 independently are hydrogen, lower alkyl, cycloalkyl or lower alkenyl, with the proviso that one of A and B is not hydrogen; n is 0-6; and Z is H, --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH 2 OH, CH 2 OR 6 , CH 2 OCOR 6 , or --CHO, CH(OR 7 ) 2 , CHOR 8 O, or --COR 9 , CR 9 (OR 7 ) 2 , CR 9 OR 8 O where R 6 is lower alkyl, phenyl or lower alkylphenyl, R 7 is lower alkyl, R 8 is a divalent alkyl radical of 2-5 carbons, and R 9 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons.
Claim 17
Dependent Claim
18 words
A compound of claim 14 wherein Z is COOR 10 where R 10 is hydrogen or lower alkyl.
Claim 18
Dependent Claim
9 words
A compound of claim 14 wherein n is zero.
Claim 19
Dependent Claim
37 words
A compound of claim 14 wherein the ethynyl group is attached to the 2 position of the pyridine nucleus and the (CH 2 ) n -Z group is attached to the 5 position of the pyridine nucleus.
Claim 20
Dependent Claim
23 words
A compound of claim 14 wherein one of A and B is a branched chain lower alkyl group and the other is hydrogen.
Claim 21
Dependent Claim
153 words
A compound of the Formula ##STR18## wherein R 1 -R 3 independently are hydrogen, lower alkyl, cycloalkyl or lower alkenyl, A and B independently are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, or SR 4 where R 4 is lower alkyl, cycloalkyl or lower alkenyl, with the proviso that one of A and B is SR 4 ; n is 0-6; and Z is H, --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH 2 OH, CH 2 OR 6 , CH 2 OCOR 6 , or --CHO, CH(OR 7 ) 2 , CHOR 8 O, or --COR 9 , CR 9 (OR 7 ) 2 , CR 9 OR 8 O where R 6 is lower alkyl, phenyl or lower alkylphenyl, R 7 is lower alkyl, R 8 is a divalent alkyl radical of 2-5 carbons, and R 9 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons.
Claim 22
Dependent Claim
153 words
A compound of the Formula ##STR18## wherein R 1 -R 3 independently are hydrogen, lower alkyl, cycloalkyl or lower alkenyl, A and B independently are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, or SR 4 where R 4 is lower alkyl, cycloalkyl or lower alkenyl, with the proviso that one of A and B is SR 4 ; n is 0-6; and Z is H, --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH 2 OH, CH 2 OR 6 , CH 2 OCOR 6 , or --CHO, CH(OR 7 ) 2 , CHOR 8 O, or --COR 9 , CR 9 (OR 7 ) 2 , CR 9 OR 8 O where R 6 is lower alkyl, phenyl or lower alkylphenyl, R 7 is lower alkyl, R 8 is a divalent alkyl radical of 2-5 carbons, and R 9 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons.
Claim 23
Dependent Claim
18 words
A compound of claim 19 wherein Z is COOR 10 where R 10 is hydrogen or lower alkyl.
Claim 24
Dependent Claim
9 words
A compound of claim 19 wherein n is zero.
Claim 25
Dependent Claim
37 words
A compound of claim 19 wherein the ethynyl group is attached to the 2 position of the pyridine nucleus and the (CH 2 ) n -Z group is attached to the 5 position of the pyridine nucleus.
Claim 26
Dependent Claim
34 words
A compound of claim 19 wherein one of A and B is characterized by the formula SR 4 where R 4 is branched chain lower alkyl or lower alkenyl, and the other is hydrogen.
Claim 27
Dependent Claim
36 words
A compound of the Formula ##STR19## 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 10 is lower alkyl.
Claim 28
Dependent Claim
36 words
A compound of the Formula ##STR19## 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 10 is lower alkyl.
Claim 29
Dependent Claim
14 words
A compound of claim 24 wherein A is hydrogen and B is tertiary butyl.
Claim 30
Dependent Claim
10 words
The compound of claim 25 wherein R 10 is ethyl.
Claim 31
Dependent Claim
10 words
The compound of claim 25 wherein R 10 is hydrogen.
Claim 32
Dependent Claim
14 words
A compound of claim 24 wherein B is hydrogen and A is tertiary butyl.
Claim 33
Dependent Claim
10 words
The compound of claim 28 wherein R 10 is ethyl.
Claim 34
Dependent Claim
10 words
The compound of claim 28 wherein R 10 is hydrogen.
Claim 35
Dependent Claim
13 words
A compound of claim 24 wherein A is hydrogen and B is 4-methylpentyl.
Claim 36
Dependent Claim
10 words
The compound of claim 31 wherein R 10 is ethyl.
Claim 37
Dependent Claim
10 words
The compound of claim 31 wherein R 10 is hydrogen.
Claim 38
Dependent Claim
50 words
A compound of the Formula ##STR20## wherein A and B independently are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, or SR 4 where R 4 is lower alkyl, cycloalkyl or lower alkenyl, with the proviso that one of A and B is SR 4 , and R 10 is lower alkyl.
Claim 39
Dependent Claim
50 words
A compound of the Formula ##STR20## wherein A and B independently are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, or SR 4 where R 4 is lower alkyl, cycloalkyl or lower alkenyl, with the proviso that one of A and B is SR 4 , and R 10 is lower alkyl.
Claim 40
Dependent Claim
20 words
A compound of claim 34 wherein A is hydrogen and B is SR 4 where R 4 is tertiary butyl.
Claim 41
Dependent Claim
10 words
The compound of claim 35 wherein R 10 is ethyl.
Claim 42
Dependent Claim
10 words
The compound of claim 35 wherein R 10 is hydrogen.
Claim 43
Dependent Claim
20 words
A compound of claim 34 wherein B is hydrogen and A is SR 4 where R 4 is tertiary butyl.
Claim 44
Dependent Claim
10 words
The compound of claim 38 wherein R 10 is ethyl.
Claim 45
Dependent Claim
10 words
The compound of claim 38 wherein R 10 is hydrogen.
Claim 46
Dependent Claim
19 words
A compound of claim 34 wherein A is hydrogen and B is SR 4 where R 4 is 3-methyl-2-butenyl.
Claim 47
Dependent Claim
10 words
The compound of claim 41 wherein R 10 is ethyl.
Claim 48
Dependent Claim
10 words
The compound of claim 41 wherein R 10 is hydrogen.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1994-05-06 | 1994-11-05 | 1995-05-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1998-05-06 | 1998-11-05 | 1999-05-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2002-05-06 | 2002-11-05 | 2003-05-07 | $7700.00 | Window Closed / Lapsed |