Method for manufacturing tertiary amino group-containing lipid

Patent metadata

Field	Value
Publication number	US-9371271-B2
Application number	US-201314412546-A
Country	US
Kind code	B2
Filing date	Jun 21, 2013
Priority date	Jul 2, 2012
Publication date	Jun 21, 2016
Grant date	Jun 21, 2016

Abstract

In production of a cationic lipid having at least one methylene group sandwiched between adjacent two cis form double bonds in the molecule, isomerization from a cis form to a trans form is suppressed.
A compound represented by the following formula (I):

R 1 —X  (I)

(in Formula, R 1 represents a hydrocarbon group having at least one methylene group sandwiched between adjacent two cis form double bonds in the molecule and having the carbon number of 8 to 24 and X represents a releasing group) is reacted with (B) a compound having at least one of each of tertiary amino group and hydroxyl group in the molecule in a saturated hydrocarbon solvent having the carbon number of 5 to 10 in the presence of an alkali catalyst.

First claim

The invention claimed is:

1. A method for manufacturing a tertiary amino group-containing lipid, comprising:
reacting
(A) a compound represented by Formula (I) described below
R 1 −X  ( 1 )

in Formula, R 1 represents a hydrocarbon group having at least one methylene group sandwiched between adjacent two cis form double bonds in the molecule and having the carbon number of 8 to 24 and X represents a functional group which is released by reaction with a hydroxyl group in the compound having at least one of each of tertiary amino groups and hydroxyl group, so as to form an ether bond and (B) a compound having at least one of each of tertiary amino group and hydroxyl group in the molecule in a saturated hydrocarbon solvent having a carbon number of 5 to 10 in the presence of an alkali catalyst,
wherein the compound having at least one of each of tertiary amino group and hydroxyl group in the molecule of the item (B) is selected from the compound represented by Formula (II-1) described below

in Formula, Z represents a divalent to octavalent hydrocarbon group having the carbon number of 1 to 8,which may be in a straight chain, branched, or cyclic shape, k 1 satisfies 1 ≦k 1 ≦7,k 2 satisfies 1 ≦k 2 ≦3, 2≦k 1 +k 2 ≦8 is satisfied, and Y is one of functional groups represented by the following structures,

R 2 and R 3 represent independently a straight chain, branched, or cyclic hydrocarbon group having the carbon number of 1 to 8, and W represents O or NR 4 ; R 4 represents an alkyl group having the carbon number of 1 to 3
and the compound represented by Formula (II-2) described below

in Formula, m represents 1 to 4,R 5 represents a straight chain or branched alkyl group having the carbon number of 1 to 4 or—(CH 2 ) n —OH; and n represents 1 to 4.

2. The method according to claim 1 , wherein the saturated hydrocarbon solvent is hexane or methylcyclohexane.

3. The method according to claim 1 , wherein R 1 is a linoleyl group.

4. The method according to claim 2 , wherein R 1 is a linoleyl group.

5. The method according to claim 1 , wherein X is a methane sulfonate group (—OSO 2 CH 3 ).

6. The method according to claim 2 , wherein X is a methane sulfonate group (—OSO 2 CH 3 ).

7. The method according to claim 3 , wherein X is a methane sulfonate group (—OSO 2 CH 3 ).

8. The method according to claim 4 , wherein X is a methane sulfonate group (—OSO 2 CH 3 ).

9. The method according to claim 1 , wherein the alkali catalyst is potassium hydroxide.

10. The method according to claim 2 , wherein the alkali catalyst is potassium hydroxide.

11. The method according to claim 3 , wherein the alkali catalyst is potassium hydroxide.

12. The method according to claim 4 , wherein the alkali catalyst is potassium hydroxide.

Assignees

• Nof Corp

Inventors

• Kubo Kazuhiro
• Tange Kota
• Ohta Masaki

Classifications

• C07C213/06 Primary

  from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups · CPC title

• C07C217/28

  having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines · CPC title

• C07D295/08

  substituted by singly bound oxygen or sulfur atoms · CPC title