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Patent US4544669A successfully refreshed from Google Patents.
US4544669A
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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 Alkadienamide compounds, and pharmaceutically-acceptable salts thereof, of the formula: <IMAGE> wherein X is O or S; R is straight or branched diene having from 11 to 23 carbon atoms; R1 is H, OH, or OCH3; R2 is OH or a short-chain ester; and wherein at least one of R1 and R2 is OH or OCH3. Compositions, useful for producing analgesia in humans or lower animals, comprise a safe and effective amount of: an alkadienamide, pharmaceutically-acceptable salts thereof, or mixtures thereof; and a pharmaceutically-acceptable carrier. Preferably, these alkadienamides are N-vanillyl-alkadienamides. Methods of treatment, comprising administering a safe and effective amount of these alkadienamides, pharmaceutically-acceptable salts thereof, or mixtures thereof, include methods of parenteral, oral, and topical administration.
Inventors
- 👤 Thomas R. LaHann
- 👤 John M. Janusz
- 👤 Brian L. Buckwalter
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 19:25
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/16; A61K31/165; A61P; A61P25/00; A61P25/04; C; C07; C07C; C07C233/00; C07C233/01; C07C233/16
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
73 words
Alkadienamide compounds, and pharmaceutically-acceptable salts thereof, of the formula: ##STR6## wherein X is 0 or S; R is straight or branched diene having from 11 to 23 carbon atoms, the stereochemistry of said diene being ZE, EZ, or EE; 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
73 words
Alkadienamide compounds, and pharmaceutically-acceptable salts thereof, of the formula: ##STR6## wherein X is 0 or S; R is straight or branched diene having from 11 to 23 carbon atoms, the stereochemistry of said diene being ZE, EZ, or EE; 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
Alkadienamide 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
Alkadienamide compounds, and pharmaceutically-acceptable salts thereof, according to claim 1, wherein R 2 is a shortchain ester.
Claim 5
Dependent Claim
22 words
Alkadienamide compounds, and pharmaceutically-acceptable salts thereof, according to claim 2, selected from the group consisting of N-vanillyl-(Z,E)-9,12-octadecadienamide, N-vanillyl-(E,E)-9,12-octadecadienamide, N-vanillyl-(Z,E)-9,11-octadecadienamide, N-vanillyl-(E,E)-10,13-nonadecadienamide, and N-vanillyl-(E,E-11,14-eicosadienamide.
Claim 6
Dependent Claim
16 words
The alkadienamide compound and pharmaceutically-acceptable salts thereof, according to claim 3, wherein said alkadienamide is N-[(4-acetoxy-3-methoxyphenyl)methyl]-(E,E)-9,12-octadecadienamide.
Claim 7
Dependent Claim
8 words
The alkadienamide compound N-vanillyl-(Z,Z)-11,14-eicosadienamide, and pharmaceutically-acceptable salts thereof.
Claim 8
Dependent Claim
8 words
The alkadienamide compound N-vanillyl-(Z,Z)-11,14-eicosadienamide, and pharmaceutically-acceptable salts thereof.
Claim 9
Dependent Claim
90 words
A composition for producing analgesia in humans or lower animals, comprising: (a) a safe and effective amount of an alkadienamide compound or pharmaceutically-acceptable salt thereof, or mixtures thereof, of the formula: ##STR7## wherein X is 0 or S, R is straight or branched diene 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 ; and (b) a pharmaceutically-acceptable carrier.
Claim 10
Dependent Claim
90 words
A composition for producing analgesia in humans or lower animals, comprising: (a) a safe and effective amount of an alkadienamide compound or pharmaceutically-acceptable salt thereof, or mixtures thereof, of the formula: ##STR7## wherein X is 0 or S, R is straight or branched diene 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 ; and (b) a pharmaceutically-acceptable carrier.
Claim 11
Dependent Claim
20 words
A composition, according to claim 7, wherein R is straight or branched diene having from 16 to 21 carbon atoms.
Claim 12
Dependent Claim
17 words
A composition, according to claim 7, wherein R 1 is OCH 3 and R 2 is OH.
Claim 13
Dependent Claim
13 words
A composition, according to claim 7, wherein R 2 is a shortchain ester.
Claim 14
Dependent Claim
27 words
A composition, according to claim 7, comprising a pharmaceutically-acceptable salt of said alkadienamide compound, selected from the group consisting of sodium, potassium, calcium, magnesium, and ammonium salts.
Claim 15
Dependent Claim
20 words
A composition, according to claim 8, for parenteral administration, comprising at least about 90%, by weight, of said pharmaceutically-acceptable carrier.
Claim 16
Dependent Claim
21 words
A composition, according to claim 8, for oral administration, comprising from about 25% to about 50%, by weight, of said alkadienamide.
Claim 17
Dependent Claim
32 words
A composition, according to claim 9, wherein said alkadienamide compound is selected from the group consisting of N-vanillyl-(Z,Z)-9,12-octadecadienamide, N-vanillyl-(Z,E)-9,12-octadecadienamide, N-vanillyl-(E,E)-9,12-octadecadienamide, N-vanillyl-(Z,E)-9,11-octadecadienamide, N-vanillyl-(E,E)-10,13-nonadecadienamide, N-vanillyl-(Z,Z)-11,14-eicosadienamide, and N-vanillyl-(E,E)-11,14-eicosadienamide, and pharmaceutically-acceptable salts thereof and mixtures thereof.
Claim 18
Dependent Claim
12 words
A composition, according to claim 10, wherein said alkadienamide compound is N-[(4-acetoxy-3-methoxyphenyl)methyl]-(E,E)-9,12-octadecadienamide.
Claim 19
Dependent Claim
12 words
A composition, according to claim 14, wherein said alkadienamide compound is N-vanillyl-(E,E)-9,12-octadecadienamide.
Claim 20
Independent Claim
92 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 an alkadienamide compound or pharmaceutically-acceptable salt thereof, or mixtures thereof, of the formula: ##STR8## wherein X is 0 or S; R is straight or branched diene 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 21
Independent Claim
92 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 an alkadienamide compound or pharmaceutically-acceptable salt thereof, or mixtures thereof, of the formula: ##STR8## wherein X is 0 or S; R is straight or branched diene 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 22
Dependent Claim
24 words
A method, according to claim 17 wherein R of said alkadienamide compound is straight or branched diene having from 16 to 21 carbon atoms.
Claim 23
Dependent Claim
32 words
A method, according to claim 18 wherein said alkadienamide compound is selected from the group consisting of N-vanillyl-(Z,Z)-9,12-octadecadienamide, N-vanillyl-(Z,E)-9,12-octadecadienamide, N-vanillyl-(E,E)-9,12-octadecadienamide, N-vanillyl-(Z,E)-9,11-octadecadienamide, N-vanillyl-(E,E)-10,13-nonadecadienamide, N-vanillyl-(Z,Z)-11,14-eicosadienamide, N-vanillyl-(E,E)-11,14-eicosadienamide, N-[(4-acetoxy-3-methoxyphenyl)methyl]-(E,E)-9,12-octadecadienamide, and pharmaceutically-acceptable salts thereof and mixtures thereof.
Claim 24
Dependent Claim
12 words
A method, according to claim 18, wherein said alkadienamide is administered intramuscularly.
Claim 25
Dependent Claim
20 words
A method, according to claim 18, for producing analgesia in humans or lower animals, wherein said alkadienamide is administered orally.
Claim 26
Dependent Claim
20 words
A method, according to claim 18, for producing analgesia in humans or lower animals, wherein said alkadienamide is administered topically.
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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 |