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US5049386A
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N-ω,(ω-1)-dialkyloxy)- and N-(ω,(ω-1)-dialkenyloxy)Alk-1-YL-N,N,N-tetrasubstituted ammonium lipids and uses therefor
Assignee: Syntex USA LLC
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Filing: 1990-05-15
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Granted: 1991-09-17
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Expires: 2010-05-15
Abstract
Abstract This invention relates to compounds of the formula <IMAGE> I or an optical isomer thereof wherein R1 and R2 are the same or different and are an alkyl or alkenyl group of 6 to 24 carbon atoms; R3, R4 and R5 are the same or different and are alkyl of 1 to 8 carbon atoms, aryl, aralkyl of 7 to 11 carbon atoms, or when two or three of R3, R4, and R5 are taken together to form quinuclidino, piperidino, pyrrolidino, or morpholino; n is 1 to 8; and X is a pharmaceutically acceptable anion.
Inventors
- 👤 Deborah A. Eppstein
- 👤 Philip L. Felgner
- 👤 Thomas R. Gadek
- 👤 Gordon H. Jones
- 👤 Richard B. Roman
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 22:41
CPC Classifications
C; C07; C07D; C07D453/00; C07D453/02; A; A61; A61K; A61K47/00; A61K47/06; A61K47/16; A61K47/18; A61K47/186; A61K9/00; A61K9/0012; A61K9/0014; A61K9/0019; A61K9/10; A61K9/127; A61K9/1271; A61K9/1272; C12; C12N; C12N15/00; C12N15/09; C12N15/87; C12N15/88
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
179 words
A method for the transdermal, topical or ocular delivery of a drug to the skin or to a mucous membrane of a human or animal subject, comprising the steps of: (1) forming a liposome comprising a therapeutically effective amount of a drug and a compound of Formula I: ##STR8## or an optical isomer thereof, wherein R 1 and R 2 are the same or different and are an alkyl or alkenyl group of 6 to 24 carbon atoms; R 3 , R 4 and R 5 are such that: (i) they are the same or different and are each alkyl of 1 to 8 carbon atoms, aryl, or aralkyl of 7 to 11 carbon atoms, or (ii) two taken together form pyrrolidino, piperidino, or morpholino, and the third is alkyl of 1 to 8 carbon atoms, aryl, or aralkyl of 7 to 11 carbon atoms, or (iii) all three together form quinuclidino; n is 1 to 8; and X is a pharmaceutically acceptable anion; and (2) applying the liposome to the skin or a mucous membrane of said subject.
Claim 2
Independent Claim
179 words
A method for the transdermal, topical or ocular delivery of a drug to the skin or to a mucous membrane of a human or animal subject, comprising the steps of: (1) forming a liposome comprising a therapeutically effective amount of a drug and a compound of Formula I: ##STR8## or an optical isomer thereof, wherein R 1 and R 2 are the same or different and are an alkyl or alkenyl group of 6 to 24 carbon atoms; R 3 , R 4 and R 5 are such that: (i) they are the same or different and are each alkyl of 1 to 8 carbon atoms, aryl, or aralkyl of 7 to 11 carbon atoms, or (ii) two taken together form pyrrolidino, piperidino, or morpholino, and the third is alkyl of 1 to 8 carbon atoms, aryl, or aralkyl of 7 to 11 carbon atoms, or (iii) all three together form quinuclidino; n is 1 to 8; and X is a pharmaceutically acceptable anion; and (2) applying the liposome to the skin or a mucous membrane of said subject.
Claim 3
Independent Claim
162 words
A method for the transdermal, topical or ocular delivery of a polyanion, comprising the steps of: (1) forming a polyanion-liposome complex comprising a polyanion and a compound of Formula I ##STR9## or an optical isomer thereof, wherein R 1 and R 2 are the same or different and are an alkyl or alkenyl group of 6 to 24 carbon atoms; R 3 , R 4 and R 5 are such that: (i) they are the same or different and are each alkyl of 1 to 8 carbon atoms, aryl, aralkyl of 7 to 11 carbon atoms, or (ii) two taken together form pyrrolidino, piperidino, or morpholino, and the third is alkyl of 1 to 8 carbon atoms, aryl, or aralkyl of 7 to 11 carbon atoms, or (iii) all three together from quinuclidino; n is 1 to 8; and X is a pharmaceutically acceptable anion; and (2) applying the complex to the skin or mucous membrane of a subject in need thereof.
Claim 4
Independent Claim
162 words
A method for the transdermal, topical or ocular delivery of a polyanion, comprising the steps of: (1) forming a polyanion-liposome complex comprising a polyanion and a compound of Formula I ##STR9## or an optical isomer thereof, wherein R 1 and R 2 are the same or different and are an alkyl or alkenyl group of 6 to 24 carbon atoms; R 3 , R 4 and R 5 are such that: (i) they are the same or different and are each alkyl of 1 to 8 carbon atoms, aryl, aralkyl of 7 to 11 carbon atoms, or (ii) two taken together form pyrrolidino, piperidino, or morpholino, and the third is alkyl of 1 to 8 carbon atoms, aryl, or aralkyl of 7 to 11 carbon atoms, or (iii) all three together from quinuclidino; n is 1 to 8; and X is a pharmaceutically acceptable anion; and (2) applying the complex to the skin or mucous membrane of a subject in need thereof.
Claim 5
Dependent Claim
46 words
The method of claim 1 wherein R 1 and R 2 are the same and are alkyl of 10 to 20 carbon atoms, R 3 , R 4 and R 5 are methyl or ethyl, n is 1 to 4 and X is a halide ion.
Claim 6
Dependent Claim
9 words
The method of claim 3 wherein n is 1.
Claim 7
Dependent Claim
20 words
The method of claim 4 wherein the lipid of Formula I is (±) N-(2,3-di-(9-(Z)-octadecenyloxy))-prop-1-yl,N,N,N-trimethylammonium chloride or an optical isomer thereof.
Claim 8
Dependent Claim
46 words
The method of claim 2 wherein R 1 and R 2 are the same and are alkyl of 10 to 20 carbon atoms, R 3 , R 4 and R 5 are methyl or ethyl, n is 1 to 4 and X is a halide ion.
Claim 9
Dependent Claim
9 words
The method of claim 6 wherein n is 1.
Claim 10
Dependent Claim
20 words
The method of claim 7 wherein the lipid of Formula I is (±) N-(2,3-di-(9-(Z)-octadecenyloxy))-prop-1-yl,N,N,N-trimethylammonium chloride or an optical isomer thereof.
References Cited (Backward Citations)
No citation records indexed.
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| 3.5 Years (Year 4) | 1994-09-16 | 1995-03-18 | 1995-09-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1998-09-16 | 1999-03-18 | 1999-09-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2002-09-16 | 2003-03-18 | 2003-09-17 | $7700.00 | Window Closed / Lapsed |