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US4130571A
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Process for preparing 1,2-diacyl-3-glycerylphosphorylcholines
Assignee: Azwell Inc
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Filing: 1976-01-26
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Granted: 1978-12-19
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Expires: 1996-01-26
Abstract
Abstract Improved process for preparing 1,2-diacyl-3-glycerylphosphorylcholines, wherein the diacyl groups are, different or the same, a residue of a saturated or unsaturated fatty acid, particularly one of the acyl groups being a residue of a highly unsaturated fatty acid or being a residue of a saturated or unsaturated fatty acid labelled with an isotope, which comprises acylating a glyceryl-phosphorylcholine or monoacyl derivative thereof or the salt thereof with an acylating agent (e.g. 1-acylimidazole or 4-acyl-3-phenyl-1,2,4-oxadiazol-5-one) in the presence of a catalyst (e.g. an alkali salt of a nitrogen-containing 5-membered heterocyclic compound or sodium oxide).
Inventors
- 👤 Tadashi Nakajima
- 👤 Yasuji Soda
- 👤 Kenichi Kashima
- 👤 Haruyoshi Kudoh
- 👤 Akira Miyamoto
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 16:45
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/06; C07F9/08; C07F9/09; C07F9/10
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
94 words
A process for preparing a 1,2-diacyl-3-glycerylphosphorylcholine of the formula: ##STR5## wherein R and R' are the same and are each a residue of a saturated fatty acid having 10 to 22 carbon atoms or an unsaturated fatty acid having 14 to 20 carbon atoms, which comprises acylating glyceryl-phosphorylcholine or a cadmium chloride salt thereof with an acylating agent selected from the group consisting of 1-acylimidazole and 4-acyl-3-phenyl-1,2,4-oxadiazol-5-one in the presence of a catalyst selected from the group consisting of an alkali salt of a nitrogen-containing 5-membered heterocyclic compound and sodium oxide in anhydrous tetrahydrofuran.
Claim 2
Dependent Claim
94 words
A process for preparing a 1,2-diacyl-3-glycerylphosphorylcholine of the formula: ##STR5## wherein R and R' are the same and are each a residue of a saturated fatty acid having 10 to 22 carbon atoms or an unsaturated fatty acid having 14 to 20 carbon atoms, which comprises acylating glyceryl-phosphorylcholine or a cadmium chloride salt thereof with an acylating agent selected from the group consisting of 1-acylimidazole and 4-acyl-3-phenyl-1,2,4-oxadiazol-5-one in the presence of a catalyst selected from the group consisting of an alkali salt of a nitrogen-containing 5-membered heterocyclic compound and sodium oxide in anhydrous tetrahydrofuran.
Claim 3
Dependent Claim
43 words
The process according to claim 1, wherein the acylating agent is a 1-acylimidazole, in which the acyl group is a residue of a saturated fatty acid having 10 to 22 carbon atoms or an unsaturated fatty acid having 14 to 20 carbon atoms.
Claim 4
Dependent Claim
40 words
The process according to claim 2, wherein the acyl group of the 1-acylimidazole is a residue of an unsaturated fatty acid selected from the group consisting of myristoleic acid, palmitoleic acid, oleic acid, linoleic acid, linolenic acid and arachidonic acid.
Claim 5
Dependent Claim
29 words
The process according to claim 2, wherein the acyl group of the 1-acylimidazole is labelled with an isotope selected from the group consisting of 14 C and 3 H.
Claim 6
Dependent Claim
28 words
The process according to claim 1, wherein the catalyst is a member selected from the group consisting of imidazole sodium salt, triazole sodium salt and benzimidazole sodium salt.
Claim 7
Dependent Claim
143 words
A process for preparing a 1,2-diacyl-3-glycerylphosphorylchlorine of the formula: ##STR6## wherein R and R' are different from each other and are each a residue of a saturated fatty acid having 10 to 22 carbon atoms or an unsaturated fatty acid having 14 to 20 carbon atoms, which comprises acylating a 1-monoacyl-3-glycerylphosphorylcholine of the formula: ##STR7## wherein R is a residue of a saturated fatty acid having 10 to 22 carbon atoms or an unsaturated fatty acid having 14 to 20 carbon atoms or a cadmium chloride salt thereof with an acylating agent selected from the group consisting of 1-acylimidazole and 4-acyl-3-phenyl-1,2,4-oxadiozol-5-one wherein the acyl group is a residue of a saturated fatty acid having 10 to 22 carbon atoms or an unsaturated fatty acid having 14 to 20 carbon atoms in the presence of imidazole sodium salt in anhydrous tetrahydrofuran at room temperature.
Claim 8
Dependent Claim
143 words
A process for preparing a 1,2-diacyl-3-glycerylphosphorylchlorine of the formula: ##STR6## wherein R and R' are different from each other and are each a residue of a saturated fatty acid having 10 to 22 carbon atoms or an unsaturated fatty acid having 14 to 20 carbon atoms, which comprises acylating a 1-monoacyl-3-glycerylphosphorylcholine of the formula: ##STR7## wherein R is a residue of a saturated fatty acid having 10 to 22 carbon atoms or an unsaturated fatty acid having 14 to 20 carbon atoms or a cadmium chloride salt thereof with an acylating agent selected from the group consisting of 1-acylimidazole and 4-acyl-3-phenyl-1,2,4-oxadiozol-5-one wherein the acyl group is a residue of a saturated fatty acid having 10 to 22 carbon atoms or an unsaturated fatty acid having 14 to 20 carbon atoms in the presence of imidazole sodium salt in anhydrous tetrahydrofuran at room temperature.
Claim 9
Dependent Claim
28 words
The process according to claim 6, whrein the R group is the formula (III) is a residue of a saturated fatty acid having 10 to 22 carbon atoms.
Claim 10
Dependent Claim
28 words
The process according to claim 6, wherein the R group in the formula (III) is a residue of an unsaturated fatty acid having 14 to 20 carbon atoms.
Claim 11
Dependent Claim
33 words
The process according to claim 8, wherein the unsaturated fatty acid is a member selected from the group consisting of myristoleic acid, palmitoleic acid, oleic acid, linoleic acid, linolenic acid and arachidonic acid.
Claim 12
Dependent Claim
28 words
The process according to claim 6, wherein the acyl group of the acylating agent is a residue of a saturated fatty acid having 10 to 22 carbon atoms.
Claim 13
Dependent Claim
26 words
The process according to claim 10, wherein the acyl group is labelled with an isotope selected from the group consisting of 14 C or 3 H.
Claim 14
Dependent Claim
28 words
The process according to claim 6, wherein the acyl group of the acylating agent is a residue of an unsaturated fatty acid having 14 to 20 carbon atoms.
Claim 15
Dependent Claim
33 words
The process according to claim 12, wherein the unsaturated fatty acid is a member selected from the group consisting of myristoleic acid, palmitoleic acid, oleic acid, linoleic acid, linolenic acid and arachiodonic acid.
Claim 16
Dependent Claim
30 words
The process according to claim 12, wherein the acyl group of the acylating agent is labelled with an isotope selected from the group consisting of 14 C and 3 H.
Claim 17
Dependent Claim
143 words
A process for preparing a 1,2-diacyl-3-glycerylphosphorylcholine of the formula: ##STR8## wherein R and R' are different from each other and are each a residue of a saturated fatty acid having 10 to 22 carbon atoms or an unsaturated fatty acid having 14 to 20 carbon atoms, which comprises acylating a 2-monoacyl-3-gylcerylphosphorylchlorine of the formula: ##STR9## wherein R' is a residue of a saturated fatty acid having 10 to 22 carbon atoms or an unsaturated fatty acid having 14 to 20 carbon atoms or a cadmium chloride salt thereof with an acylating agent selected from the group consisting of 1-acylimidazole and 4-acyl-3-phenyl-1,2,4-oxadiazol-5-one wherein the acyl group is a residue of a saturated fatty acid having 10 to 22 carbon atoms or an unsaturated fatty acid having 14 to 20 carbon atoms in the presence of imidazole sodium salt in anhydrous tetrahydrofuran at room temperature.
Claim 18
Dependent Claim
143 words
A process for preparing a 1,2-diacyl-3-glycerylphosphorylcholine of the formula: ##STR8## wherein R and R' are different from each other and are each a residue of a saturated fatty acid having 10 to 22 carbon atoms or an unsaturated fatty acid having 14 to 20 carbon atoms, which comprises acylating a 2-monoacyl-3-gylcerylphosphorylchlorine of the formula: ##STR9## wherein R' is a residue of a saturated fatty acid having 10 to 22 carbon atoms or an unsaturated fatty acid having 14 to 20 carbon atoms or a cadmium chloride salt thereof with an acylating agent selected from the group consisting of 1-acylimidazole and 4-acyl-3-phenyl-1,2,4-oxadiazol-5-one wherein the acyl group is a residue of a saturated fatty acid having 10 to 22 carbon atoms or an unsaturated fatty acid having 14 to 20 carbon atoms in the presence of imidazole sodium salt in anhydrous tetrahydrofuran at room temperature.
Claim 19
Dependent Claim
27 words
The process according to claim 15, wherein the R' group in the formula is a residue of a saturated fatty acid having 10 to 22 carbon atoms.
Claim 20
Dependent Claim
27 words
The process according to claim 15, wherein the R' group in the formula is a residue of an unsaturated fatty acid having 14 to 20 carbon atoms.
Claim 21
Dependent Claim
33 words
The process according to claim 17, wherein the unsaturated fatty acid is a member selected from the group consisting of myristoleic acid, palmitoleic acid, oleic acid, linoleic acid, linolenic acid and arachidonic acid.
Claim 22
Dependent Claim
28 words
The process according to claim 15, wherein the acyl group of the acylating agent is a residue of a saturated fatty acid having 10 to 22 carbon atoms.
Claim 23
Dependent Claim
26 words
The process according to claim 19, wherein the acyl group is labelled with an isotope selected from the group consisting of 14 C or 3 H.
Claim 24
Dependent Claim
28 words
The process according to claim 15, wherein the acyl group of the acylating agent is a residue of an unsaturated fatty acid having 14 to 20 carbon atoms.
Claim 25
Dependent Claim
33 words
The process according to claim 21, wherein the unsaturated fatty acid is a member selected from the group consisting of myristoleic acid, palmitoleic acid, oleic acid, linoleic acid, linolenic acid and arachidonic acid.
Claim 26
Dependent Claim
30 words
The process according to claim 21, wherein the acyl group of the acylating agent is labelled with an isotope selected from the group consisting of 14 C and 3 H.
References Cited (Backward Citations)
US3270084A
Cited
US3592829A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-12-18 | 1982-06-19 | 1982-12-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-12-18 | 1986-06-19 | 1986-12-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-12-18 | 1990-06-19 | 1990-12-19 | $7700.00 | Window Closed / Lapsed |