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US4963556A
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Choline esters as absorption-enhancing agents for drug delivery through mucous membranes of the nasal, buccal, sublingual and vaginal cavities
Assignee: Merck and Co Inc
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Filing: 1989-04-20
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Granted: 1990-10-16
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Expires: 2009-04-20
Abstract
Abstract Choline esters are used as drug absorption enhancing agents for drugs which are poorly absorbed from the nasal, oral, and vaginal cavities.
Inventors
- 👤 Jose Alexander
- 👤 Joseph A. Fix
- 👤 A. J. Repta
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 15:49
CPC Classifications
A; A61; A61K; A61K47/00; A61K47/06; A61K47/16; A61K47/18; A61K47/186
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
119 words
A pharmaceutical composition for enhancing nasal, buccal, sublingual and vaginal absorption of a formulation comprising a therapeutically effective dosage amount of an antiviral drug and a choline ester absorption enhancing agent of the formula: [(CH.sub.3).sub.3 N.sup.+ CH.sub.2 CH .sub.2 OR]X.sup.- wherein R is saturated acyl (C 2 -C 20 ), acyl (C 2 -C 20 ) with 1 to 6 double bonds, hydroxyacyl (C 2 -C 20 ) with 1 to 3 hydroxy groups, ketoacyl (C 4 -C 20 ), unsaturated hydroxyacyl (C 5 -C 20 ), alkylaroyl (C 7 -C 20 ) arylacyl (C 7 -C 20 ), alkylaroyl (C 7 -C 20 ) or carbalkoxyacyl (C 5 -C 20 ) and X is a pharmaceutically acceptable counterion.
Claim 2
Dependent Claim
119 words
A pharmaceutical composition for enhancing nasal, buccal, sublingual and vaginal absorption of a formulation comprising a therapeutically effective dosage amount of an antiviral drug and a choline ester absorption enhancing agent of the formula: [(CH.sub.3).sub.3 N.sup.+ CH.sub.2 CH .sub.2 OR]X.sup.- wherein R is saturated acyl (C 2 -C 20 ), acyl (C 2 -C 20 ) with 1 to 6 double bonds, hydroxyacyl (C 2 -C 20 ) with 1 to 3 hydroxy groups, ketoacyl (C 4 -C 20 ), unsaturated hydroxyacyl (C 5 -C 20 ), alkylaroyl (C 7 -C 20 ) arylacyl (C 7 -C 20 ), alkylaroyl (C 7 -C 20 ) or carbalkoxyacyl (C 5 -C 20 ) and X is a pharmaceutically acceptable counterion.
Claim 3
Dependent Claim
52 words
The composition of claim 1, wherein said antiviral drug is selected from the group consisting of cytarabine, acyclovir, floxuridine, ribavirin, vidiarabine, idoxuridine and trifluridine and said enchancing agent is selected from the group consisting of hexanoylcholine, decanoylcholine, lauroylcholine, octanoylcholine, myristoylcholine, palmitoylcholine, stearoylcholine, 2-hexenoylcholine, 9-decenoylcholine, 9-hexadecenoylcholine, α-linoleoylcholine, 6-keto-decanoylcholine, 12-hydroxy-12-octadecanoyl -choline, ω-ethoxycarbonyloctanoylcholine and 2-hydroxypalmitoylcholine.
Claim 4
Dependent Claim
19 words
The composition of claim 2, wherein said antiviral drugs is acyclovir and said enhancing agent is palmitoylcholine or lauroylcholine.
Claim 5
Dependent Claim
11 words
The composition of claim 3, wherein said enhancing agent is palmitoylcholine.
Claim 6
Independent Claim
129 words
A method of enhancing the rate of absorption of an antiviral drug administered to the nasal, buccal, sublingual or vaginal cavity, which comprises administering a composition comprising a therapeutically effective dosage amount of said drug and a choline ester absorption enhancing agent of the formula: [(CH.sub.3).sub.3 N.sup.+ CH.sub.2 CH.sub.2 OR]X.sup.- wherein R is saturated acyl (C x -C 20 ), acyl (C 2 -C 20 ) with 1 to 6 double bonds, hydroxyacyl (C 2 -C 20 ) with 1 to 3 hydroxy groups, ketoacyl (C 4 -C 20 ), unsaturated hydroxyacyl (C 5 -C 20 ), carboxyacyl (C 4 -C 20 ), arylacyl (C 7 -C 20 ), alkylaroyl (C 7 -C 20 ) or carbalkoxyacyl (C 5 -C 20 ) and X is a pharmaceutically acceptable counterion.
Claim 7
Independent Claim
129 words
A method of enhancing the rate of absorption of an antiviral drug administered to the nasal, buccal, sublingual or vaginal cavity, which comprises administering a composition comprising a therapeutically effective dosage amount of said drug and a choline ester absorption enhancing agent of the formula: [(CH.sub.3).sub.3 N.sup.+ CH.sub.2 CH.sub.2 OR]X.sup.- wherein R is saturated acyl (C x -C 20 ), acyl (C 2 -C 20 ) with 1 to 6 double bonds, hydroxyacyl (C 2 -C 20 ) with 1 to 3 hydroxy groups, ketoacyl (C 4 -C 20 ), unsaturated hydroxyacyl (C 5 -C 20 ), carboxyacyl (C 4 -C 20 ), arylacyl (C 7 -C 20 ), alkylaroyl (C 7 -C 20 ) or carbalkoxyacyl (C 5 -C 20 ) and X is a pharmaceutically acceptable counterion.
Claim 8
Dependent Claim
53 words
The method of claim 5, wherein said antiviral drug said is selected from the group consisting of cytarabine, acycloir, floxuridine, rebavirinm vidarabine, idoxuridine and trifluridine and said enhancing agent is selected from the group consisting of hexanoylcholine, lauroylcholine, octanoylcholine, decanoylcholine, myristoylcholine, palmitoylcholine, stearoylcholine, 2-hexenoylcholine, 9-decenoylcholine, lauroylcholine, 2-hydroxymyristoylcholine, 6-keto-decanoylcholine, 12-hydroxy-12-octadecenoylcholine, ω-ethoyxcarbonyloctanoylcholine and 2-hydroxy palmitoylcholine.
Claim 9
Dependent Claim
23 words
The method of claim 6, wherein said antiviral is acyclovir and said enhancing agent is hexanoylcholine, octanoylcholine, decanoylcholine, lauroylcholine, myristoylcholine, palmitoylcholine or stearoylcholine.
Claim 10
Dependent Claim
15 words
The method of claim 7, wherein said enhancing agent is palmitoylcholine, lauroylcholine, myristoylcholine or stearoylcholine.
Claim 11
Dependent Claim
10 words
The composition of claim 1 further comprising pharmaceutically acceptable excipients.
Claim 12
Dependent Claim
11 words
The method of claim 8, wherein said enhancing agent is palmitoylcarnitine.
References Cited (Backward Citations)
US4851391A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1993-10-15 | 1994-04-16 | 1994-10-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-10-15 | 1998-04-16 | 1998-10-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-10-15 | 2002-04-16 | 2002-10-16 | $7700.00 | Window Closed / Lapsed |