Patent EP0394111B1 successfully refreshed from Google Patents.
EP0394111B1
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Lipopolyamines, their preparation and use
Assignee: Centre National de la Recherche Scientifique
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Filing: 1990-04-13
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Granted: 1997-06-04
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Expires: 2010-04-13
Abstract
Abstract Intermediate compounds useful for producing transfecting lipopolyamines, comprising: <IMAGE> wherein m is an integer between 2 and 6 inclusive, wherein n is an integer between 2 and 5 inclusive, wherein R5 represents a hydrogen atom or a carboxyl radical but no more than one R5 represents a carboxyl, the values of m in the different fragments (CH)m may be identical or different, and wherein the symbol Z R5 represent a group protecting the amine function.
Inventors
- 👤 Jean-Paul Behr
- 👤 Jean-Philippe Loeffler
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-05 22:07
CPC Classifications
C; C07; C07C; C07C237/00; C07C237/02; C07C237/22; A; A61; A61K; A61K47/00; A61K47/50; A61K47/51; A61K47/54; A61K47/543; A61K47/544; C07C237/04; C07C237/06; C07C271/00; C07C271/06; C07C271/08; C07C271/10; C07C271/22; C07F; C07F9/00; C07F9/02; C07F9/06; C07F9/08; C07F9/09; C07F9/10
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
231 words
New lipopolyamine in the D, L or DL form, characterized in that it corresponds to the general formula: in which: - n is an integer between 1 and 5 inclusive, - m is an integer between 2 and 6 inclusive, - R represents a hydrogen atom or a radical of general formula: in which R 1 and R 2 , which are identical or different, each represent a saturated C p H 2p+2 or unsaturated C p H 2p or C p H 2p-2 aliphatic radical, p being an integer between 12 and 22 inclusive, and R' represents a hydrogen atom or an alkyl radical containing 1 to 4 carbon atoms, optionally substituted by a phenyl radical, or a radical of general formula: in which X represents a methylene group or a carbonyl group and R 3 and R 4 , which are identical or different, each represent a saturated C p' H 2p'+2 or unsaturated C p ,H 2p' or C p' H 2p'-2 aliphatic radical, p' being an integer between 11 and 21 inclusive, it being understood that: - whatever the values of m and n, one and only one of the symbols R represents a radical of general formula (II) or (III) - when n is between 2 and 5, the values of m in the different fragments may be identical or different, as well as its salts.
Claim 2
Dependent Claim
95 words
New lipopolyamine according to Claim 1, characterized in that n is equal to 3 and the values of m in the fragments are identical or different and represent 3 or 4 and R represents either a radical of general formula (II) in which R 1 and R 2 each represent an alkyl radical containing 11 to 22 carbon atoms and R' represents a hydrogen atom or a radical of general formula (III) in which R 3 -X- and R 4 -X- each represent an alkanoyl radical containing 12 to 22 carbon atoms, and its salts.
Claim 3
Dependent Claim
2 words
Dioctadecylamide 5-carboxyspermylglycine.
Claim 4
Dependent Claim
2 words
Dipalmitoylphosphatidylethanolamine 5-carboxyspermylamide.
Claim 5
Dependent Claim
173 words
Process for the preparation of a lipopolyamine according to Claim 1 for which R represents a radical of general formula (II), characterized in that a product of general formula: in which R 1 , R 2 and R' are defined as in Claim 1, is reacted with a product of general formula: in which m and n are defined as in Claim 1, R 5 represents a hydrogen atom or a carboxyl radical and the symbols Z represent a group for protecting the amine functional group, it being understood that: - whatever the values of m and n, one and only one of the symbols R 5 represents a carboxyl radical - when n is between 2 and 5, the values of m for the different fragments may be identical or different, in the presence of a diimide in an inert organic solvent chosen from halogenated aliphatic hydrocarbons, and then the protecting groups Z are replaced by a hydrogen atom, and the product obtained is isolated optionally in the form of a salt.
Claim 6
Dependent Claim
125 words
Process for the preparation of a lipopolyamine according to Claim 1 for which R represents a radical of general formula (III), characterized in that a product of general formula: in which R 3 , R 4 and X are defined as in Claim 1, is reacted with an ester with the N-hydroxysuccinimide of the product of general formula: in which m, n, R 5 and Z are defined as in Claim 5, the procedure being carried out in an organic solvent chosen from chlorinated aliphatic hydrocarbons and alcohols in the presence of an organic base chosen from the tertiary amines, and then the protecting groups Z are replaced by a hydrogen atom, and the product obtained is isolated optionally in the form of a salt.
Claim 7
Dependent Claim
69 words
Use of a lipopolyamine according to one of Claims 1 to 4 for the transfection of eukaryotic cells, characterized in that a dilute aqueous solution of a product according to one of Claims 1 to 4 is mixed in a suitable medium with a dilute aqueous solution of oligonucleotide or plasmid DNA and then the transfectant mixture is brought into contact with a suspension of cells to be transfected.
Claim 8
Dependent Claim
15 words
Use according to Claim 7, characterized in that primary cultures or cell lines are transfected.
Claim 9
Dependent Claim
26 words
Ethanolic solution of a product according to one of Claims 1 to 4, for carrying out the transfection according to either of Claims 7 and 8.
Claim 10
Dependent Claim
26 words
Aqueous solution of a product according to one of Claims 1 to 4, for carrying out the transfection according to either of Claims 7 and 8.
Claim 11
Dependent Claim
87 words
Compound of general formula: in which n is an integer between 2 and 5 inclusive, m is an integer between 2 and 6 inclusive, R 5 represents a hydrogen atom or a carboxyl radical and the symbols Z represent a group for protecting the amine functional group, it being understood that: - whatever the values of m and n, one and only one of the symbols R 5 represents a carboxyl radical, and - the values of m for the different fragments may be identical or different.
References Cited (Backward Citations)
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