CA2073126A1 - Preparation of alkylphosphocholines - Google Patents
Preparation of alkylphosphocholinesInfo
- Publication number
- CA2073126A1 CA2073126A1 CA002073126A CA2073126A CA2073126A1 CA 2073126 A1 CA2073126 A1 CA 2073126A1 CA 002073126 A CA002073126 A CA 002073126A CA 2073126 A CA2073126 A CA 2073126A CA 2073126 A1 CA2073126 A1 CA 2073126A1
- Authority
- CA
- Canada
- Prior art keywords
- exchanger
- ion
- alkylphosphocholine
- solution
- purification
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000002360 preparation method Methods 0.000 title abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 2
- 150000001298 alcohols Chemical class 0.000 abstract 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 2
- 150000005690 diesters Chemical class 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- 238000000746 purification Methods 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- 239000004381 Choline salt Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 235000019417 choline salt Nutrition 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000003248 quinolines Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Health & Medical Sciences (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Steroid Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Abstract
A process for the preparation of C14 - C18 alkyl-phosphocholines comprises reacting an n-alkanol having a chain length of C14 to C18 with phosphorus oxychloride in a single reaction vessel. The product obtained is reacted with a choline salt in the presence of a basic substance, without isolation and purification, in an inert solvent, to form a corresponding phosphoric acid diester chloride. The phosphoric acid diester chloride is hydrolyzed to obtain the alkylphosphocholine. Purification of C14 - C18 alkylphosphocholines is performed by adding to a solution of an alkylphosphocholine, in a solvent selected from the group consisting of anhydrous alcohols with 1 to 5 carbon atoms, water and any mixture of said alcohols with or without water, a mixed-bed ion-exchanger, or successively or simultaneously at least one ion-exchanger selected from the group consisting of an acid ion-exchanger and a basic ion-exchanger. The solution and the ion-exchanger are stirred together, and the solution is separated from the ion-exchanger to recover purified alkylphosphocholine.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4122127 | 1991-07-04 | ||
| DEP4122127.3 | 1991-07-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2073126A1 true CA2073126A1 (en) | 1993-01-05 |
| CA2073126C CA2073126C (en) | 2001-09-04 |
Family
ID=6435410
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002073126A Expired - Lifetime CA2073126C (en) | 1991-07-04 | 1992-07-03 | Preparation of alkylphosphocholines |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0521297B1 (en) |
| JP (1) | JP3171279B2 (en) |
| CN (1) | CN1034941C (en) |
| AT (1) | ATE158295T1 (en) |
| AU (2) | AU652646B2 (en) |
| CA (1) | CA2073126C (en) |
| DE (2) | DE59208905D1 (en) |
| DK (1) | DK0521297T3 (en) |
| EG (1) | EG20551A (en) |
| ES (1) | ES2108715T3 (en) |
| FI (1) | FI107260B (en) |
| GR (1) | GR3025490T3 (en) |
| HU (1) | HU219243B (en) |
| IE (1) | IE80555B1 (en) |
| IL (1) | IL102379A (en) |
| NO (2) | NO304232B1 (en) |
| PL (1) | PL169571B1 (en) |
| SG (1) | SG47844A1 (en) |
| ZA (1) | ZA924980B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE59205998D1 (en) * | 1991-07-04 | 1996-05-23 | Asta Medica Ag | Medicament with antineoplastic activity containing octadecyl- [2- (N-methylpiperidino) ethyl] phosphate as active ingredient and process for its preparation |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0050327B1 (en) * | 1980-10-21 | 1984-06-20 | Roche Diagnostics GmbH | Phospholipids that contain sulphur, process for their preparation and medicines containing these compounds |
| JPS60184092A (en) * | 1984-03-01 | 1985-09-19 | Kao Corp | Phosphoric ester and its preparation |
| IE59778B1 (en) * | 1985-12-04 | 1994-04-06 | Max Planck Gesellschaft | Medicament with anti-tumour action containing hexadecylphosphocholine |
| EP0336142A3 (en) * | 1988-04-04 | 1991-04-24 | American Cyanamid Company | Novel antagonists of platelet activating factor |
| IT1229238B (en) * | 1989-05-08 | 1991-07-26 | Istituto Chemioterapico | PROCEDURE FOR THE PREPARATION OF L-ALPHA-GLYCERYLPHOSPHORYLCHOLINE AND ALPHA-GLYCERYLPHOSPHORYLETHANOLAMINE. |
-
1992
- 1992-05-26 DK DK92108826.6T patent/DK0521297T3/en active
- 1992-05-26 AT AT92108826T patent/ATE158295T1/en active
- 1992-05-26 DE DE59208905T patent/DE59208905D1/en not_active Expired - Lifetime
- 1992-05-26 EP EP92108826A patent/EP0521297B1/en not_active Expired - Lifetime
- 1992-05-26 SG SG1996004669A patent/SG47844A1/en unknown
- 1992-05-26 ES ES92108826T patent/ES2108715T3/en not_active Expired - Lifetime
- 1992-06-25 DE DE4220852A patent/DE4220852C2/en not_active Expired - Lifetime
- 1992-07-01 EG EG34492A patent/EG20551A/en active
- 1992-07-02 NO NO922612A patent/NO304232B1/en not_active IP Right Cessation
- 1992-07-02 PL PL92295129A patent/PL169571B1/en unknown
- 1992-07-02 IL IL10237992A patent/IL102379A/en not_active IP Right Cessation
- 1992-07-03 FI FI923087A patent/FI107260B/en not_active IP Right Cessation
- 1992-07-03 JP JP17691392A patent/JP3171279B2/en not_active Expired - Lifetime
- 1992-07-03 AU AU19441/92A patent/AU652646B2/en not_active Expired
- 1992-07-03 CA CA002073126A patent/CA2073126C/en not_active Expired - Lifetime
- 1992-07-03 CN CN92105432A patent/CN1034941C/en not_active Expired - Lifetime
- 1992-07-03 HU HU9202233A patent/HU219243B/en unknown
- 1992-07-03 IE IE922182A patent/IE80555B1/en not_active IP Right Cessation
- 1992-07-03 ZA ZA924980A patent/ZA924980B/en unknown
-
1994
- 1994-06-29 AU AU66059/94A patent/AU663259B2/en not_active Expired
-
1997
- 1997-11-26 GR GR970403139T patent/GR3025490T3/en unknown
-
1998
- 1998-04-17 NO NO981742A patent/NO304316B1/en not_active IP Right Cessation
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |