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EP0299758A2
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Compositions for enhancing the cutaneous penetration of pharmacologically active agents
Assignee: University of California Berkeley
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Filing: 1988-07-14
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Granted: —
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Expires: 2008-07-14
Abstract
Abstract Method and compositions for enhancing the cutaneous penetration of topically or transdermally delivered pharmacologically active agents. The compositions include various urethane compounds as permeation enhancers, the urethane compounds formed from reaction of a monomeric organic diisocyanate with a hydroxy- or hydroxy/alkoxy-terminated linear polyalkylene glycol or polyether
Inventors
- 👤 Samuel Chess
- 👤 Jerry L. Mccullough
- 👤 Gerald D. Weinstein
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-05 17:49
CPC Classifications
A; A61; A61K; A61K9/00; A61K9/0012; A61K9/0014; A61K47/00; A61K47/06; A61K47/16; A61K47/18; C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/48; C08G18/4825; C08G18/4833
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
107 words
A permeation enhancing compound having the formula: wherein: R is an alkylene or alkenylene radical containing from one to about 20 carbon atoms, or a cycloalkylene or a cycloalkenylene radical containing from about 5 to about 10 carbon atoms, or a mononuclear or fused ring arylene radical containing from about 6 to about 10 carbon atoms; R¹ is the same or different alkylene or alkenylene radical; R² is hydrogen or a lower alkyl group; m is a number in the range of 0 and 6 inclusive; and n is an integer selected so as to provide the enhancer with a molecular weight of at least about 200.
Claim 2
Dependent Claim
107 words
A permeation enhancing compound having the formula: wherein: R is an alkylene or alkenylene radical containing from one to about 20 carbon atoms, or a cycloalkylene or a cycloalkenylene radical containing from about 5 to about 10 carbon atoms, or a mononuclear or fused ring arylene radical containing from about 6 to about 10 carbon atoms; R¹ is the same or different alkylene or alkenylene radical; R² is hydrogen or a lower alkyl group; m is a number in the range of 0 and 6 inclusive; and n is an integer selected so as to provide the enhancer with a molecular weight of at least about 200.
Claim 3
Dependent Claim
17 words
A compound according to claim 1 wherein m is in the range of 0 to 3 inclusive.
Claim 4
Dependent Claim
10 words
A compound according to claim 2, wherein m is 0.
Claim 5
Dependent Claim
30 words
A compound according to any one of the preceding claims wherein n is selected so as to give a molecular weight in the range of from about 250 to 2200.
Claim 6
Dependent Claim
30 words
A compound according to any one of claims 1 to 3, wherein each n is selected to provide each polyoxyethylene moiety (-O-CH₂CH₂-) n with a molecular weight of about 500.
Claim 7
Independent Claim
142 words
A method of making a permeation enhancing compound, comprising reacting a monomeric organic diisocyanate represented by the formula (III): O=C=N--R--N=C=O (III) wherein R is an alkylene or alkenylene radical containing from one to about 20 carbon atoms, or a cycloalkylene or cycloalkenylene radical containing from about 5 to about 10 carbon atoms, or a mononuclear or fused ring arylene radical containing from about 6 to about 10 carbon atoms, with a hydroxy- or hydroxy/alkoxy-terminated linear polyalkylene glycol or polyether having the formula (II): R²(O-R¹) n -O-R² (II) wherein R¹ is the same or different alkylene or alkenylene radical, R² is hydrogen or a lower alkyl group, and n is an integer selected so as to provide the enhancer with a molecular weight in the range of about 200 to 13,000, and wherein the mole ratio of (III) to (II) is about 2:1.
Claim 8
Independent Claim
142 words
A method of making a permeation enhancing compound, comprising reacting a monomeric organic diisocyanate represented by the formula (III): O=C=N--R--N=C=O (III) wherein R is an alkylene or alkenylene radical containing from one to about 20 carbon atoms, or a cycloalkylene or cycloalkenylene radical containing from about 5 to about 10 carbon atoms, or a mononuclear or fused ring arylene radical containing from about 6 to about 10 carbon atoms, with a hydroxy- or hydroxy/alkoxy-terminated linear polyalkylene glycol or polyether having the formula (II): R²(O-R¹) n -O-R² (II) wherein R¹ is the same or different alkylene or alkenylene radical, R² is hydrogen or a lower alkyl group, and n is an integer selected so as to provide the enhancer with a molecular weight in the range of about 200 to 13,000, and wherein the mole ratio of (III) to (II) is about 2:1.
Claim 9
Dependent Claim
18 words
A method according to claim 6, wherein the reaction is carried out in the presence of a catalyst.
Claim 10
Dependent Claim
22 words
A method according to claim 6 or 7, wherein the reaction is carried out at a temperature of at least about 100°F.
Claim 11
Dependent Claim
20 words
A method according to claim 8, wherein the reaction is carried out at a temperature of at least about 150°F.
Claim 12
Independent Claim
26 words
A method according to any one of claims 6 to 9, wherein a compound as defined in any one of claims 2 to 5 is prepared.
Claim 13
Dependent Claim
62 words
A composition for achieving enhanced cutaneous penetration of a dermally applied pharmacologically active agent, comprising: (a) a therapeutically effective amount of a pharmacologically active agent; and (b) an amount of a permeation enhancer effective to enhance the cutaneous penetration of the pharmacologically active agent, the enhancer being a compound of formula I as defined in any one of claims 1 to 5.
Claim 14
Dependent Claim
14 words
A composition according to claim 11, wherein the composition further contains a topical carrier.
Claim 15
Dependent Claim
14 words
A composition according to claim 12, wherein the topical carrier comprises water and alcohol.
Claim 16
Dependent Claim
25 words
A composition according to claim 13, wherein the topical carrier comprises about 30 wt%, about 45 wt% alcohol, and about 25 wt% of the enhancer.
Claim 17
Dependent Claim
19 words
A composition according to claim 13 or 14, wherein the alcohol is selected from isopropanol, ethanol and mixtures thereof.
Claim 18
Dependent Claim
31 words
A composition according to any one of claims 11 to 15, wherein the enhancer is present in an amount of from about 5 wt% to about 90 wt% of the composition.
Claim 19
Dependent Claim
26 words
A composition according to claim 16, wherein the enhancer is present in an amount of from about 5 wt% to about 25 wt% of the composition.
Claim 20
Independent Claim
31 words
A method for enhancing the cutaneous penetration of a pharmacologically active agent, comprising applying to skin or other epithelial tissue a composition according to any one of claims 11 to 17.
Claim 21
Independent Claim
28 words
A method for moisturizing skin, comprising applying to skin surface a composition containing a compound of formula I as defined in any one of claims 1 to 5.
Claim 22
Dependent Claim
14 words
A method according to claim 19, wherein the composition further contains a topical carrier.
Claim 23
Dependent Claim
15 words
A method according to claim 20, wherein the topical carrier comprises water and an alcohol.
Claim 24
Dependent Claim
17 words
A method according to claim 21, wherein the alcohol is selected from isopropanol, ethanol and mixtures thereof.
Claim 25
Independent Claim
31 words
A method according to any one of claims 19 to 22 wherein the compound is present in an amount of from about 5 wt% to about 25 wt% of the composition.
Claim 26
Dependent Claim
25 words
A method according to claim 23, wherein the compound is present in an amount of from 5 wt% to about 25 wt% of the composition.
References Cited (Backward Citations)
No citation records indexed.
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