US4544668A
Expired / Lapsed
US
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Compounds and compositions useful for producing analgesia
Assignee: Procter and Gamble Co
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Filing: 1983-07-14
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Granted: 1985-10-01
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Expires: 2003-07-14
Abstract
Abstract Methylenealkanamide compounds, and pharmaceutically-acceptable salts thereof, of the formula: ##STR1## wherein X is O or S; R is straight or branched methylene substituted alkane having from 11 to 23 carbon atoms; R 1 is H, OH, or OCH 3 ; R 2 is OH or a short-chain ester; and wherein at least one of R 1 and R 2 is OH or OCH 3 . Compositions, useful for producing analgesia in humans or lower animals, comprise a safe and effective amount of: a methylenealkanamide, pharmaceutically-acceptable salts thereof, or mixtures thereof; and a pharmaceutically-acceptable carrier. Preferably, these methylenealkanamides are N-vanillyl-methylenealkanamides. Methods of treatment, comprising administering a safe and effective amount of these methylenealkanamides, pharmaceutically-acceptable salts thereof, or mixtures thereof, include methods of parenteral, oral and topical administration.
Inventors
- 👤 John M. Janusz
- 👤 Brian L. Buckwalter
- 👤 Thomas R. LaHann
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 19:13
CPC Classifications
C; C07; C07C; C07C51/00; C07C51/09; A; A61; A61P; A61P25/00; A61P25/02; A61P25/04; C07C51/58; C07C51/60
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
64 words
Methylenealkanamide compounds, and pharmaceutically-acceptable salts thereof, of the formula: ##STR5## wherein X is O or S; R is straight or branched, methylene-substituted alkane having from 11 to 23 carbon atoms; R 1 is H, OH or OCH 3 ; R 2 is OH, or a short-chain ester; and wherein at least one of R 1 and R 2 is OH or OCH 3 .
Claim 2
Dependent Claim
64 words
Methylenealkanamide compounds, and pharmaceutically-acceptable salts thereof, of the formula: ##STR5## wherein X is O or S; R is straight or branched, methylene-substituted alkane having from 11 to 23 carbon atoms; R 1 is H, OH or OCH 3 ; R 2 is OH, or a short-chain ester; and wherein at least one of R 1 and R 2 is OH or OCH 3 .
Claim 3
Dependent Claim
21 words
Methylenealkanamide compounds, and pharmaceutically-acceptable salts thereof, according to claim 1, wherein R 1 is OCH 3 and R 2 is OH.
Claim 4
Dependent Claim
17 words
Methylenealkanamide compounds, and pharmaceutically-acceptable salts thereof, according to claim 1, wherein R 2 is a short-chain ester.
Claim 5
Dependent Claim
16 words
Methylenealkanamide compound, and pharmaceutically acceptable salts thereof, according to claim 2, wherein said methylenealkanamide is 9-methylene-N-vanillyl-octadecanamide.
Claim 6
Dependent Claim
91 words
A composition for producing analgesia in humans or lower animals, comprising: (a) a safe and effective amount of a methylenealkanamide compound or pharmaceutically-acceptable salt thereof, or mixtures thereof, of the formula: ##STR6## wherein X is O or S, R is straight or branched, methylene-substituted alkane having from 11 to 23 carbon atoms, R 1 is H, OH, or OCH 3 , R 2 is OH or a chort-chain ester, and wherein at least one of R 1 and R 2 is OH or OCH 3 ; and (b) a pharmaceutically-acceptable carrier.
Claim 7
Dependent Claim
91 words
A composition for producing analgesia in humans or lower animals, comprising: (a) a safe and effective amount of a methylenealkanamide compound or pharmaceutically-acceptable salt thereof, or mixtures thereof, of the formula: ##STR6## wherein X is O or S, R is straight or branched, methylene-substituted alkane having from 11 to 23 carbon atoms, R 1 is H, OH, or OCH 3 , R 2 is OH or a chort-chain ester, and wherein at least one of R 1 and R 2 is OH or OCH 3 ; and (b) a pharmaceutically-acceptable carrier.
Claim 8
Dependent Claim
21 words
A composition, according to claim 5, wherein R is straight or branched, methylene-substituted alkane having from 16 to 21 carbon atoms.
Claim 9
Dependent Claim
17 words
A composition, according to claim 5, wherein R 1 is OCH 3 and R 2 is OH.
Claim 10
Dependent Claim
13 words
A composition, according to claim 5, wherein R 2 is a short-chain ester.
Claim 11
Dependent Claim
27 words
A composition, according to claim 5, comprising a pharmaceutically-acceptable salt of said methylenealkanamide compound, selected from the group consisting of sodium, potassium, calcium, magnesium, and ammonium salts.
Claim 12
Dependent Claim
20 words
A composition, according to claim 6, for parenteral administration, comprising at least about 90%, by weight, of said pharmaceutically-acceptable carrier.
Claim 13
Dependent Claim
21 words
A composition, according to claim 6, for oral administration, comprising from aout 25% to about 50%, by weight, of said methylenealkanamide.
Claim 14
Dependent Claim
19 words
A composition, according to claim 7, for producing analgesia in humans or lower animals, wherein said methylenealkanamide is 9-methylene-N-vanillyl-octadecanamide.
Claim 15
Dependent Claim
11 words
A composition, according to claim 8, wherein said methylenealkanamide is 9-methylene-N-[(4-acetoxy-3-methoxyphenyl)methyl]octadecanamide.
Claim 16
Independent Claim
93 words
A method for producing analgesia in humans or lower animals, which comprises administering to said human or lower animal a safe and effective amount of a methylenealkanamide compound or pharmaceutically-acceptable salt thereof, or mixtures thereof, of the formula: ##STR7## wherein X is O or S; R is straight or branched, methylene-substituted alkane having from 11 to 23 carbon atoms; R 1 is H, OH, or OCH 3 ; R 2 is OH or a short-chain ester; and wherein at least one of R 1 and R 2 is OH or OCH 3 .
Claim 17
Independent Claim
93 words
A method for producing analgesia in humans or lower animals, which comprises administering to said human or lower animal a safe and effective amount of a methylenealkanamide compound or pharmaceutically-acceptable salt thereof, or mixtures thereof, of the formula: ##STR7## wherein X is O or S; R is straight or branched, methylene-substituted alkane having from 11 to 23 carbon atoms; R 1 is H, OH, or OCH 3 ; R 2 is OH or a short-chain ester; and wherein at least one of R 1 and R 2 is OH or OCH 3 .
Claim 18
Dependent Claim
25 words
A method, according to claim 14, wherein R of said methylenealkanamide compound is straight or branched, methylene-substituted alkane having from 16 to 21 carbon atoms.
References Cited (Backward Citations)
FR1336388A
Cited
US3268582A
Cited
BE626897A
Cited
US3621043A
Cited
US3741999A
Cited
US3558500A
Cited
US3920523A
Cited
US3888893A
Cited
US3816484A
Cited
US3803185A
Cited
US3897428A
Cited
US4238508A
Cited
US4313958A
Cited
US4401663A
Cited
JPS6139413A
Cited
JPS6147752A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-09-30 | 1989-04-01 | 1989-10-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-09-30 | 1993-04-01 | 1993-10-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-09-30 | 1997-04-01 | 1997-10-01 | $7700.00 | Window Closed / Lapsed |