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US4686235A
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Substituted cinnamyl-2,3-dihydrobenzofuran and analogs useful as anti-inflammatory agents
Assignee: Merck and Co Inc
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Filing: 1985-08-12
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Granted: 1987-08-11
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Expires: 2005-08-12
Abstract
Abstract Substituted cinnamyl-2,3-dihydrobenzofurans and analogs were prepared from the nucleophlic substitution of a cinnamylhalide with a 2,3-dihydrobenzofuran anion or an analog thereof. These compounds were found to be potent topical anti-inflammatory agents.
Inventors
- 👤 Michael N. Chang
- 👤 Norman P. Jensen
- 👤 Milton L. Hammond
- 👤 Robert A. Zambias
- 👤 John McDonald
- 👤 Kathleen M. Rupprecht
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 16:11
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/77; C07D307/78; C07D307/79; C07C; C07C255/00; C07C43/00; C07C43/02; C07C43/20; C07C43/225; C07C43/23; C07C45/00; C07C45/61; C07C45/67; C07C45/68; C07C47/00; C07C47/52; C07C47/575; C07C49/00; C07C49/20; C07C49/24; C07C49/245; C07C49/248; C07C49/76; C07C49/82; C07C49/835; C07C49/84; C07D311/00; C07D311/02; C07D311/04; C07D311/58
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
125 words
A compound of formula (II) ##STR5## wherein R is (a) COOR 2 wherein R 2 is H or C 1-6 alkyl; (b) loweralkoxy; (c) haloloweralkylcarbonyl; (d) halo; (e) loweralkanoyl; (f) lowerhaloalkyl; (g) hydroxyloweralkyl; or (h) cyano; A is phenyl substituted with (R 1 )q wherein when there are more than one R 1 (q>1) R 1 can be the same or different from each other and is (1) hydrogen; (2) halo; (3) loweralkoxy; (4) lower alkylthio; (5) lower alkyl sulfinyl; (6) lower alkyl sulfonyl; (7) unsubstituted or substituted phenylloweralkyl; (8) loweralkyl; (9) loweralkenyl; (10) lower alkanoyl; (11) haloloweralkyl; (12) --COOH; (13) aryl; (14) aryloxy; (15) cyano; (16) hydroxyloweralkyl; (17) halo loweralkanoyl; or (18) loweralkanoyloxy; q is 0 to 5; and m is 1 to 3.
Claim 2
Dependent Claim
125 words
A compound of formula (II) ##STR5## wherein R is (a) COOR 2 wherein R 2 is H or C 1-6 alkyl; (b) loweralkoxy; (c) haloloweralkylcarbonyl; (d) halo; (e) loweralkanoyl; (f) lowerhaloalkyl; (g) hydroxyloweralkyl; or (h) cyano; A is phenyl substituted with (R 1 )q wherein when there are more than one R 1 (q>1) R 1 can be the same or different from each other and is (1) hydrogen; (2) halo; (3) loweralkoxy; (4) lower alkylthio; (5) lower alkyl sulfinyl; (6) lower alkyl sulfonyl; (7) unsubstituted or substituted phenylloweralkyl; (8) loweralkyl; (9) loweralkenyl; (10) lower alkanoyl; (11) haloloweralkyl; (12) --COOH; (13) aryl; (14) aryloxy; (15) cyano; (16) hydroxyloweralkyl; (17) halo loweralkanoyl; or (18) loweralkanoyloxy; q is 0 to 5; and m is 1 to 3.
Claim 3
Dependent Claim
24 words
The compound of claim 1 which is (a) 2-(m-methoxycinnamyl)-4-methoxyphenol; (b) 2-(o-bromocinnamyl)-4-methoxyphenol; (c) 2-(o-formylcinnamyl)-4-methoxyphenol; (d) 2-(o-hydroxymethylcinnamyl)-4-methoxyphenol; (e) 2-(p-fluorocinnamyl)-4-methoxyphenol; (f) 2-(o-fluorocinnamyl)-4-methoxyphenol; (g) 2-(3,4-dimethoxycinnamyl)-4-methoxyphenol; or (h) 2-(p-methylthiocinnamyl)-4-methoxyphenol.
Claim 4
Dependent Claim
8 words
The compound of claim 1 which is 2-(o-hydroxymethylcinnamyl)-4-methoxyphenol.
Claim 5
Dependent Claim
141 words
A pharmaceutical composition for treating topical inflammation comprising a pharmaceutical carrier and an effective amount of a compound of formula (II); ##STR6## wherein R is (a) COOR 2 wherein R 2 is H or C 1-6 alkyl; (b) loweralkoxy; (c) haloloweralkylcarbonyl; (d) halo; (e) loweralkanoyl; (f) lowerhaloalkyl; (g) hydroxyloweralkyl; or (h) cyano; A is phenyl substituted with (R 1 )q wherein when there are more than one R 1 (q>1) R 1 can be the same or different from each other and is (1) hydrogen; (2) halo; (3) loweralkoxy; (4) lower alkylthio; (5) lower alkyl sulfinyl; (6) lower alkyl sulfonyl; (7) unsubstituted or substituted phenylloweralkyl; (8) loweralkyl; (9) loweralkenyl; (10) lower alkanoyl; (11) haloloweralkyl; (12) --COOH; (13) aryl; (14) aryloxy; (15) cyano; (16) hydroxyloweralkyl; (17) halo loweralkanoyl; or (18) loweralkanoyloxy; q is 0 to 5; and m is 1 to 3.
Claim 6
Dependent Claim
141 words
A pharmaceutical composition for treating topical inflammation comprising a pharmaceutical carrier and an effective amount of a compound of formula (II); ##STR6## wherein R is (a) COOR 2 wherein R 2 is H or C 1-6 alkyl; (b) loweralkoxy; (c) haloloweralkylcarbonyl; (d) halo; (e) loweralkanoyl; (f) lowerhaloalkyl; (g) hydroxyloweralkyl; or (h) cyano; A is phenyl substituted with (R 1 )q wherein when there are more than one R 1 (q>1) R 1 can be the same or different from each other and is (1) hydrogen; (2) halo; (3) loweralkoxy; (4) lower alkylthio; (5) lower alkyl sulfinyl; (6) lower alkyl sulfonyl; (7) unsubstituted or substituted phenylloweralkyl; (8) loweralkyl; (9) loweralkenyl; (10) lower alkanoyl; (11) haloloweralkyl; (12) --COOH; (13) aryl; (14) aryloxy; (15) cyano; (16) hydroxyloweralkyl; (17) halo loweralkanoyl; or (18) loweralkanoyloxy; q is 0 to 5; and m is 1 to 3.
Claim 7
Dependent Claim
27 words
The composition of claim 4 wherein the active compound is (a) 2-(m-methoxycinnamyl)-4-methoxyphenol; (b) 2-(o-bromocinnamyl)-4-methoxyphenol; (c) 2-(o-formylcinnamyl)-4-methoxyphenol; (d) 2-(o-hydroxymethylcinnamyl)-4-methoxyphenol; (e) 2-(p-fluorocinnamyl)-4-methoxyphenol; (f) 2-(o-fluorocinnamyl)-4-methoxyphenol; (g) 2-(3,4-dimethoxycinnamyl)-4-methoxyphenol; or (h) 2-(p-methylthiocinnamyl)-4-methoxyphenol.
Claim 8
Dependent Claim
18 words
The composition of claim 4 wherein the active compound is the compound of claim 2 which is 2-(o-hydroxymethylcinnamyl)-4-methoxyphenol.
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) | 1990-08-10 | 1991-02-09 | 1991-08-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-08-10 | 1995-02-09 | 1995-08-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-08-10 | 1999-02-09 | 1999-08-11 | $7700.00 | Window Closed / Lapsed |