US5006550A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Chroman esters of phenols and benzoic acids having retinoid-like activity
Assignee: Allergan Inc
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Filing: 1989-12-29
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Granted: 1991-04-09
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Expires: 2009-12-29
Abstract
Abstract Retinoid like activity is exhibited by compounds of the formula ##STR1## wherein the R 1 -R 7 groups are independently H or straight chain or branched chain lower alkyl or cycloalkyl of 1 to 6 carbons; X symbolizes an ester or thioester linkage, Y is cycloalkyl or branched chain alkyl of 1 to 6 carbons or is (CH 2 ) where n is an integer between 0 to 6 or is an alkenyl group of 2 to 6 carbons, or an alkynyl group of 2 to 6 carbons; and Z is H, OH, OR', OCOR', --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 6 carbons, or a phenylalkyl, phenyl or substituted phenyl group.
Inventors
- 👤 Roshantha A. S. Chandraratna
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 07:51
CPC Classifications
C; C07; C07D; C07D311/00; C07D311/02; C07D311/04; C07D311/58; A; A61; A61P; A61P17/00
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
171 words
A compound of the formula ##STR14## wherein the R 1 -R 7 groups are independently H or straight chain lower alkyl group of 1 to 6 carbons or branched chain lower alkyl or cycloalkyl groups of 3 to 6 carbons; X is --COO--; Y is cycloalkyl or branched chain alkyl group of 3 to 6 carbons, or is (CH 2 ) n where n is an integer between 0 to 6, and Z is H, OH, OR', OCOR', --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH 2 OH --CH 2 OR', CH 2 OCOR', or --CHO CH(OR 8 ) 2 , CHOR 9 O, or --COR' or CR'(OR 8 ) 2 , or CR'OR 9 O where R' is an alkyl group containing 1 to 6 carbons, cycloalkyl group containing 3 to 6 carbons, or alkenyl group containing 2 to 6 carbons, or a phenylalkyl, or phenyl group and where R 8 is lower alkyl, and R 9 is a divalent alkyl radical of 2 to 5 carbons.
Claim 2
Dependent Claim
171 words
A compound of the formula ##STR14## wherein the R 1 -R 7 groups are independently H or straight chain lower alkyl group of 1 to 6 carbons or branched chain lower alkyl or cycloalkyl groups of 3 to 6 carbons; X is --COO--; Y is cycloalkyl or branched chain alkyl group of 3 to 6 carbons, or is (CH 2 ) n where n is an integer between 0 to 6, and Z is H, OH, OR', OCOR', --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH 2 OH --CH 2 OR', CH 2 OCOR', or --CHO CH(OR 8 ) 2 , CHOR 9 O, or --COR' or CR'(OR 8 ) 2 , or CR'OR 9 O where R' is an alkyl group containing 1 to 6 carbons, cycloalkyl group containing 3 to 6 carbons, or alkenyl group containing 2 to 6 carbons, or a phenylalkyl, or phenyl group and where R 8 is lower alkyl, and R 9 is a divalent alkyl radical of 2 to 5 carbons.
Claim 3
Dependent Claim
16 words
A compound of claim 1 where Y is (CH 2 ) n and n is zero.
Claim 4
Dependent Claim
14 words
A compound of claim 2 where Z is COOR* wherein R* is lower alkyl.
Claim 5
Dependent Claim
22 words
A compound of claim 2 wherein R 1 and R 2 are methyl, R 3 R 4 and R 5 are hydrogen.
Claim 6
Dependent Claim
17 words
A compound of claim 4 wherein R 6 is attached to the 7-position of the chroman nucleus.
Claim 7
Dependent Claim
22 words
A compound of claim 2 wherein R 3 and R 4 are methyl, R 1 R 2 and R 5 are hydrogen.
Claim 8
Dependent Claim
17 words
A compound of claim 6 wherein R 6 is attached to the 7-position of the chroman nucleus.
Claim 9
Dependent Claim
20 words
A compound of claim 2 wherein R 1 , R 2 , R 3 , and R 4 are methyl.
Claim 10
Dependent Claim
17 words
A compound of claim 8 wherein R 6 is attached to the 7-position of the chroman nucleus.
Claim 11
Dependent Claim
22 words
One or more compounds set forth in claim 1, comprised in and admixed with a pharmaceutical composition including a pharmaceutically acceptable excipient.
Claim 12
Dependent Claim
77 words
A compound of the formula ##STR15## wherein the R 1 -R 7 groups are independently H or straight chain alkyl group of 1 to 6 carbons or branched chain lower alkyl or cycloalkyl groups of 3 to 6 carbons; n is an integer between 0 to 6, and R 10 is OR* where R* is H, lower alkyl, or R 10 is N(R**) 2 where R** independently is H or lower alkyl, phenyl or lower alkyl phenyl.
Claim 13
Dependent Claim
77 words
A compound of the formula ##STR15## wherein the R 1 -R 7 groups are independently H or straight chain alkyl group of 1 to 6 carbons or branched chain lower alkyl or cycloalkyl groups of 3 to 6 carbons; n is an integer between 0 to 6, and R 10 is OR* where R* is H, lower alkyl, or R 10 is N(R**) 2 where R** independently is H or lower alkyl, phenyl or lower alkyl phenyl.
Claim 14
Dependent Claim
9 words
A compound of claim 11 wherein n is zero.
Claim 15
Dependent Claim
18 words
A compound of claim 11 wherein R 1 -R 4 groups are independently H or CH 3 .
Claim 16
Dependent Claim
22 words
One or more compounds set forth in claim 11, comprised in and admixed with a pharmaceutical composition including a pharmaceutically acceptable excipient.
Claim 17
Dependent Claim
60 words
A compound of the formula ##STR16## wherein the R 1 -R 4 groups are independently H or CH 3 , the R 5 -R 6 groups are independently H or lower alkyl of 1-6 carbons, and R 10 is OR* where R* is H, lower alkyl, or R 10 is N(R**) 2 where R** independently is H or lower alkyl.
Claim 18
Dependent Claim
60 words
A compound of the formula ##STR16## wherein the R 1 -R 4 groups are independently H or CH 3 , the R 5 -R 6 groups are independently H or lower alkyl of 1-6 carbons, and R 10 is OR* where R* is H, lower alkyl, or R 10 is N(R**) 2 where R** independently is H or lower alkyl.
Claim 19
Dependent Claim
25 words
A compound of claim 15 wherein R 1 and R 2 both are CH 3 , and R 3 and R 4 both are H.
Claim 20
Dependent Claim
17 words
A compound of claim 16 wherein R 6 is H and R* is H or lower alkyl.
Claim 21
Dependent Claim
24 words
A compound of claim 15 wherein R 1 and R 2 both are H, and R 3 and R 4 are CH 3 .
Claim 22
Dependent Claim
17 words
A compound of claim 18 wherein R 6 is H and R* is H or lower alkyl.
Claim 23
Dependent Claim
13 words
A compound of claim 15 wherein R 1 -R 4 all are methyl.
Claim 24
Dependent Claim
34 words
A compound of claim 20 wherein R 5 is H, R 6 is H or methyl and R* is H or lower alkyl, or pharmaceutically acceptable salt of the compound where R* is H.
Claim 25
Dependent Claim
10 words
A compound of claim 21 wherein R 6 is H.
Claim 26
Dependent Claim
9 words
The compound of claim 22 wherein R* is ethyl.
Claim 27
Dependent Claim
14 words
The compound of claim 22 wherein R* is hydrogen, or pharmaceutically acceptable salt thereof.
Claim 28
Dependent Claim
10 words
A compound of claim 21 wherein R 6 is methyl.
Claim 29
Dependent Claim
9 words
The compound of claim 25 wherein R* is ethyl.
Claim 30
Dependent Claim
14 words
The compound of claim 25 wherein R* is hydrogen or pharmaceutically acceptable salt thereof.
Claim 31
Dependent Claim
22 words
One or more compounds set forth in claim 15, comprised in and admixed with a pharmaceutical composition including a pharmaceutically acceptable excipient.
References Cited (Backward Citations)
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