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US5094783A
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Retinoid compounds
Assignee: UAB Research Foundation
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Filing: 1990-06-29
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Granted: 1992-03-10
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Expires: 2010-06-29
Abstract
Abstract Retinoid compounds with bioactive properties and their synthesis are described. The compounds are useful as chemopreventive or cancer-treating agents and dermatological agents. The novel retinoids are members of either of the two general structures: <IMAGE> (I) or <IMAGE> (II) wherein X is CO2H or CH2OH; and in formula (I), R1 and R2 are each hydrogen, a C1-4 alkyl, a C1-4 alkoxy, or R1 and R2 taken together form a 5- to 7-membered cycloalkyl or cycloalkenyl ring; and in formula (II), R1 and R2 are each hydrogen, a C1-4 alkyl, a C1-4 alkenyl or a C1-4 alkoxy, or R2 and R3 taken together form a 5- to 7-membered cycloalkyl or cycloalkenyl with R1 and R4 being a hydrogen atom, a C1-4 alkyl, a C1-4 alkenyl or a C1-4 alkoxy.
Inventors
- 👤 Donald D. Muccio
- 👤 Wayne J. Brouillette
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 20:04
CPC Classifications
C; C07; C07C; C07C403/00; C07C403/20; C07C403/06; C07C403/08; C07C57/00; C07C57/26; C07C2601/00; C07C2601/12; C07C2601/16
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
82 words
A compound according to general structure (I): ##STR13## wherein R 1 and R 2 are independently selected from the group consisting of a hydrogen atom, a C 1-4 alkyl group, a C 1-4 alkenyl group and a C 1-4 alkoxy group; or R 1 and R 2 taken together form a 5- to 7-membered cycloalkyl or a 6-membered cycloalkenyl ring; and X is a member selected from the group consisting of a CO 2 H group and a CH 2 OH group.
Claim 2
Dependent Claim
82 words
A compound according to general structure (I): ##STR13## wherein R 1 and R 2 are independently selected from the group consisting of a hydrogen atom, a C 1-4 alkyl group, a C 1-4 alkenyl group and a C 1-4 alkoxy group; or R 1 and R 2 taken together form a 5- to 7-membered cycloalkyl or a 6-membered cycloalkenyl ring; and X is a member selected from the group consisting of a CO 2 H group and a CH 2 OH group.
Claim 3
Dependent Claim
68 words
A compound as recited in claim 1, wherein R 1 is selected from the group consisting of a hydrogen atom, a methyl group, an ethyl group and a n-propyl group, and R 2 is selected from the group consisting of a hydrogen atom, a methyl group, an ethyl group, an isopropyl group and a tert-butyl group; or R 1 and R 2 taken together form a cyclohexene ring.
Claim 4
Dependent Claim
149 words
A compound as recited in claim 2, wherein R 1 is a hydrogen atom and R 2 is a hydrogen atom, R 1 is a hydrogen atom and R 2 is a methyl group, R 1 is a methyl group and R 2 is a hydrogen atom, R 1 is a methyl group and R 2 is a methyl group, R 1 is a methyl group and R 2 is an ethyl group, R 1 is an ethyl group and R 2 is a methyl group, R 1 is a methyl group and R 2 is an group, R 1 is a methyl group and R 2 is a tert-butyl group, R 1 is an ethyl group and R 2 is a tert-butyl group, R 1 is a n-propyl group and R 2 is an isopropyl group, or R 1 and R 2 taken together form a cyclohexene ring.
Claim 5
Dependent Claim
15 words
A compound as recited in claim 3, wherein X is a CO 2 H group.
Claim 6
Dependent Claim
15 words
A compound as recited in claim 3, wherein X is a CH 2 OH group.
Claim 7
Dependent Claim
85 words
A compound as recited in claim 3, wherein R 1 is a methyl group and R 2 is an isopropyl group, R 1 is an ethyl group and R 2 is an isopropyl group, R 1 is a methyl group and R 2 is a tert-butyl group, R 1 is an ethyl group and R 2 is a tert-butyl group, R 1 is a n-propyl group and R 2 is an isopropyl group, or R 1 and R 2 taken together form a cyclohexene ring.
Claim 8
Dependent Claim
15 words
A compound as recited in claim 6, wherein X is a CO 2 H group.
Claim 9
Dependent Claim
15 words
A compound as recited in claim 6, wherein X is a CH 2 OH group.
Claim 10
Dependent Claim
17 words
A compound as recited in claim 1, which is the 13Z isomer of said general structure (I).
Claim 11
Dependent Claim
21 words
A compound as recited in claim 9, wherein R 1 is a methyl group and R 2 is an isopropyl group.
Claim 12
Dependent Claim
15 words
A compound as recited in claim 10, wherein X is a CO 2 H group.
Claim 13
Dependent Claim
17 words
A compound as recited in claim 1, which is the all-E isomer of said general structure (I).
Claim 14
Dependent Claim
21 words
A compound as recited in claim 12, wherein R 1 is a methyl group and R 2 is an isopropyl group.
Claim 15
Dependent Claim
15 words
A compound as recited in claim 13, wherein X is a CO 2 H group.
Claim 16
Dependent Claim
120 words
A compound according to formula (II): ##STR14## wherein R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of a hydrogen atom, a C 1-4 alkyl group, a C 1-4 alkenyl group and a C 1-4 alkoxy group; or R 2 and R 3 taken together form a 5- to 7-membered cycloalkyl or cycloalkenyl a 6-membered ring and R 1 and R 4 are independently selected from the group consisting of a hydrogen atom, a C 1-4 alkyl group, a C 1-4 alkenyl group and a C 1-4 alkoxy group; and X is a member selected from the group consisting of a CO 2 H group and a CH 2 OH group.
Claim 17
Dependent Claim
120 words
A compound according to formula (II): ##STR14## wherein R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of a hydrogen atom, a C 1-4 alkyl group, a C 1-4 alkenyl group and a C 1-4 alkoxy group; or R 2 and R 3 taken together form a 5- to 7-membered cycloalkyl or cycloalkenyl a 6-membered ring and R 1 and R 4 are independently selected from the group consisting of a hydrogen atom, a C 1-4 alkyl group, a C 1-4 alkenyl group and a C 1-4 alkoxy group; and X is a member selected from the group consisting of a CO 2 H group and a CH 2 OH group.
Claim 18
Dependent Claim
113 words
A compound as recited in claim 15, wherein R 1 is a member selected from the group consisting of a hydrogen atom and a methyl group, R 2 is a member selected from the group consisting of a hydrogen atom, a methyl group, an ethyl group and an n-propyl group, R 3 is a member selected from the group consisting of a hydrogen atom, a methyl group, and an ethyl group, and R 4 is a member selected from the group consisting of a hydrogen atom and a methyl group; or R 2 and R 3 taken together form a cyclohexene ring and R 1 and R 4 are each a methyl group.
Claim 19
Dependent Claim
306 words
A compound as recited in claim 16, wherein R 1 is a hydrogen atom, R 2 is a hydrogen atom, R 3 is a hydrogen atom and R 4 is a hydrogen atom; R 1 is a hydrogen atom, R 2 is a hydrogen atom, R 3 is a hydrogen atom and R 4 is a methyl group; R 1 is a hydrogen atom, R 2 is a hydrogen atom, R 3 is a methyl group and R 4 is a hydrogen atom; R 1 is a hydrogen atom, R 2 is a hydrogen atom, R 3 is a methyl group and R 4 is a methyl group; R 1 is a hydrogen atom, R 2 is a methyl group, R 3 is a methyl group and R 4 is a methyl group; R 1 is a methyl group, R 2 is a methyl group, R 3 is a hydrogen atom and R 4 is a methyl group; R 1 is a methyl group, R 2 is an ethyl group, R.sub. 3 is a hydrogen atom and R 4 is a methyl group; R 1 is a methyl group, R 2 is a n-propyl group, R 3 is a hydrogen atom and R 4 is a methyl group; R 1 is a methyl group, R 2 is a methyl group, R 3 is a methyl group and R 4 is a methyl group; R 1 is a methyl group, R 2 is an ethyl group, R 3 is a methyl group and R 4 is an ethyl group; R 1 is a methyl group, R 2 is a methyl group, R 3 is an ethyl group and R 4 is a methyl group; or R 2 and R 3 taken together form a cyclohexene ring and R 1 and R 4 are each a methyl group.
References Cited (Backward Citations)
No citation records indexed.
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