YU45719B - Postopek za pripravo mešano substituiranih enantiomerno čistih 1,2-diacil-sn-gli cero-3-fosfoholinov in 1,2-di-acil-sn-glicero-3-fosfoetanolaminov - Google Patents
Postopek za pripravo mešano substituiranih enantiomerno čistih 1,2-diacil-sn-gli cero-3-fosfoholinov in 1,2-di-acil-sn-glicero-3-fosfoetanolaminovInfo
- Publication number
- YU45719B YU45719B YU81585A YU81585A YU45719B YU 45719 B YU45719 B YU 45719B YU 81585 A YU81585 A YU 81585A YU 81585 A YU81585 A YU 81585A YU 45719 B YU45719 B YU 45719B
- Authority
- YU
- Yugoslavia
- Prior art keywords
- glycero
- diacyl
- phosphocholines
- preparation
- phosfoethanolamines
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 title 1
- 230000008569 process Effects 0.000 title 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 3
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- JZNWSCPGTDBMEW-YFKPBYRVSA-N sn-glycero-3-phosphoethanolamine Chemical compound NCCO[P@@](O)(=O)OC[C@@H](O)CO JZNWSCPGTDBMEW-YFKPBYRVSA-N 0.000 abstract 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 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
-
- 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
- C07F9/10—Phosphatides, e.g. lecithin
-
- 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)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Hydrogenated Pyridines (AREA)
- Epoxy Resins (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
POSTOPEK ZA PRIPRAVO MESANO SUBSTITUIRANIH ENANTIOMERNO CISTIH 1,2-DIACIL-SN-GLI CERO-3-FOSFOHOLINOV IN 1,2-DI-ACIL-SN-GLICERO-3-FOSFOETANOLAMINOV, s splosno formulo: v kateri so R1, R2, R3 enaki in pomenijo vsakic bodisi 3 atome vodika ali tri metilne skupine, R4 in R5 sta razlicna in pomenita neodvisno drug od drugega nesubstituiran ali s halogenom, metoksi ali trifluorometilom enkrat ali veckrat substituiran, nerazvejen ali razvejen C1 do C18- alkilni ali enkrat ali veckrat nenasicen C18 do C20 -alkenilni ostanek, oznace n s tem, da trifenilmetilni cerivat sn-glicero-3-fosfoholina ali sn-glicero-3-fosfoetanolamina s splosno formulo v kateri T pomeni nesubstituirano trifenilmetilno skupino in so ostanki R1', R2', R3', bodisi enaki in stoje vsakic za metilno skupino, bodisi razlicni, pri cemer v tem primeru pomenita dva od ostankov R1', R2' in R3', vedno vodik in tretji ostanek predstavlja nesubstituirano ali sC1 do C6-alkilom, C1 do C6-alkoksi ali halogenom enkrat ali veckrat substituirano trifenilmetilno skupino, aciliramo z anhidrodom ali azolidom karboksilne kiseline, s splosno formulo R4COOH v molskem razmerju 1:1,3 do 1:11,4 v prisotnosti dimetilsulfoksida, kloroforma, metilenklorida ali tetrahidrofurana ali njihovih mesanic kot topila in kovinskega natrija, piridina ali dimetilaminopiridina kot sredstva za vezanje kisline pri temperaturi od sobne temperature do 30 C v spojino s splosno formulo pri cemer so T, R1', R2', R3' definirani kot v formuli II in ima R4 v formuli I navedeni pomen, nakar iz dobljene spojine s splosno formulo III odcepimo z ucinkovanjem borovega trifluoroda v metilenkloridu kot topilu pri -5 C do +5 C 1-0-trifenilmetilno skupino ob tvorbi 2-acil-sn-glicero-3-fosfoholina ali 2-acil-sn-glicero-3-fosfo-(N-trifenilmetil)-etanolamina s splosno formulo v kateri imajo R1', R2', R3' in R4 zgoraj navedeni pomen, in spojino s splosno formulo IV dalje aciliramo s presnovo, z anhidridom karboksilne kisline s splosno formulo R5COOH v molskem razmerju od 1:2,2 do 1:6,2 v kloroformu ali metilenkloridu kot topilu v prisotnosti dimetilamino-piridina pri 18 do 25 C v 1,2-diacil-sn-glicero-3-fosfoholin ali 1,2-diacil-sn-glicero-3-fosfo-(N-trifenilmetil)-etanolamin s splosno formulo pri cemer so R1', R2', R3' definirani kot v formuli II, R4 in R5 imata v formuli I navedeni pomen, nakar dobljeno spojino s splosno formulo Ia, v kateri pomeni eden od ostankov R1', R2' in R3' trifenilmetilno skupino in oba ostala ostanka pomenita vodik, prevedemo z ucinkovanjem trifluoroocetne kisline, v danem primeru v metilenkloridu, pri temperaturi 0 C v spojino s splosno formulo I, v kateri pomenijo ostanki R1, R2 in R3 vodik.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT0159084A AT383130B (de) | 1984-05-15 | 1984-05-15 | Verfahren zur herstellung von an c1 und c2 verschieden substituierten phosphatidylcholinen und phosphatidylethanolaminen ueber die neuen verbindungen 1-0-tritylglycerophosphocholin beziehungsweise (1-0,n-ditrityl)-glycerophosphoethanolamin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| YU81585A YU81585A (en) | 1987-10-31 |
| YU45719B true YU45719B (sh) | 1992-07-20 |
Family
ID=3516711
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| YU81585A YU45719B (sh) | 1984-05-15 | 1985-05-15 | Postopek za pripravo mešano substituiranih enantiomerno čistih 1,2-diacil-sn-gli cero-3-fosfoholinov in 1,2-di-acil-sn-glicero-3-fosfoetanolaminov |
| YU81685A YU45720B (sh) | 1984-05-15 | 1985-05-15 | POSTOPEK ZA PRIPRAVO NOVIH TRIFENILMETILNIH DERIVATOV Sn-GLICERO-3-FOSFOHOLINA IN SN-GLICERO-3-FOSFOETANOLAMINA |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| YU81685A YU45720B (sh) | 1984-05-15 | 1985-05-15 | POSTOPEK ZA PRIPRAVO NOVIH TRIFENILMETILNIH DERIVATOV Sn-GLICERO-3-FOSFOHOLINA IN SN-GLICERO-3-FOSFOETANOLAMINA |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US4622180A (sh) |
| EP (1) | EP0161519B1 (sh) |
| JP (1) | JPS60252490A (sh) |
| KR (1) | KR920009556B1 (sh) |
| CN (1) | CN1014791B (sh) |
| AT (2) | AT383130B (sh) |
| AU (1) | AU565316B2 (sh) |
| BR (1) | BR8502293A (sh) |
| CA (1) | CA1244462A (sh) |
| DD (2) | DD245668A1 (sh) |
| DE (1) | DE3563533D1 (sh) |
| DK (2) | DK167441C (sh) |
| ES (2) | ES8603899A1 (sh) |
| FI (1) | FI77663C (sh) |
| HU (2) | HU199486B (sh) |
| IE (1) | IE58511B1 (sh) |
| IL (1) | IL75133A (sh) |
| NO (1) | NO163100C (sh) |
| NZ (1) | NZ212067A (sh) |
| PH (2) | PH21831A (sh) |
| SU (2) | SU1422999A3 (sh) |
| TR (1) | TR22204A (sh) |
| YU (2) | YU45719B (sh) |
| ZA (1) | ZA853697B (sh) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT383130B (de) * | 1984-05-15 | 1987-05-25 | Chemie Linz Ag | Verfahren zur herstellung von an c1 und c2 verschieden substituierten phosphatidylcholinen und phosphatidylethanolaminen ueber die neuen verbindungen 1-0-tritylglycerophosphocholin beziehungsweise (1-0,n-ditrityl)-glycerophosphoethanolamin |
| DE3638687A1 (de) * | 1986-11-13 | 1988-05-19 | Lentia Gmbh | Einstufiges verfahren zur herstellung von gemischt substituierten 1,2-di-acyl-sn-glycero-3-phosphocholinen |
| AT388165B (de) * | 1986-12-10 | 1989-05-10 | Chemie Linz Ag | Einstufiges verfahren zur herstellung von gemischt substituierten 1,2-di-acyl-sn-glycero-3- phosphocholinen |
| JP2657486B2 (ja) * | 1987-02-20 | 1997-09-24 | 花王株式会社 | 洗浄剤組成物 |
| US5144045A (en) * | 1990-11-13 | 1992-09-01 | American Cyanamid Company | Phosphocholine derivative inhibitors of phospholipase A2 |
| US5698537A (en) * | 1996-06-18 | 1997-12-16 | Clarion Pharmaceuticals Inc. | Method of lowering the viscosity of mucus |
| US6838452B2 (en) * | 2000-11-24 | 2005-01-04 | Vascular Biogenics Ltd. | Methods employing and compositions containing defined oxidized phospholipids for prevention and treatment of atherosclerosis |
| WO2005018632A1 (en) * | 2003-08-18 | 2005-03-03 | Btg International Limited | Treatment of neurodegenerative conditions |
| US7807847B2 (en) | 2004-07-09 | 2010-10-05 | Vascular Biogenics Ltd. | Process for the preparation of oxidized phospholipids |
| GB0425932D0 (en) * | 2004-11-25 | 2004-12-29 | Btg Int Ltd | Structured phospholipids |
| GB0504362D0 (en) | 2005-03-02 | 2005-04-06 | Btg Int Ltd | Cytokine modulators |
| US9006217B2 (en) | 2007-01-09 | 2015-04-14 | Vascular Biogenics Ltd. | High-purity phospholipids |
| US8569529B2 (en) | 2007-01-09 | 2013-10-29 | Vascular Biogenics Ltd. | High-purity phospholipids |
| JP5752599B2 (ja) * | 2008-11-06 | 2015-07-22 | ヴァスキュラー バイオジェニックス リミテッド | 酸化脂質化合物およびその使用 |
| CN104017019A (zh) * | 2014-06-12 | 2014-09-03 | 东南大学 | 一种氮芥-甘油磷脂酰胆碱化合物的合成方法 |
| US9771385B2 (en) | 2014-11-26 | 2017-09-26 | Vascular Biogenics Ltd. | Oxidized lipids |
| EP3223824B1 (en) | 2014-11-26 | 2021-01-06 | Vascular Biogenics Ltd. | Oxidized lipids and treatment or prevention of fibrosis |
| CZ308596B6 (cs) * | 2017-04-03 | 2020-12-23 | Ústav molekulární genetiky AV ČR, v. v. i. | Deriváty fosfolipidů a jejich použití jako léčiva |
| PL232663B1 (pl) * | 2017-06-30 | 2019-07-31 | Univ Przyrodniczy We Wroclawiu | Fosfatydylocholiny oraz sposób ich otrzymywania |
| PL232298B1 (pl) * | 2017-06-30 | 2019-06-28 | Univ Przyrodniczy We Wroclawiu | Sposób otrzymywania fosfatydylocholiny zawierającej ibuprofen w pozycji sn-1 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2820893C2 (de) * | 1978-05-12 | 1986-02-20 | A. Nattermann & Cie GmbH, 5000 Köln | Strukturanaloga von natürlichen Phospholipiden und Verfahren zur Herstellung dieser Verbindungen |
| IT1123187B (it) * | 1979-09-17 | 1986-04-30 | Lpb Ist Farm | Processo per la preparazione di l-alfa-glicerilfosforilcolina |
| DE3130867A1 (de) * | 1981-08-04 | 1983-02-24 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V., 3400 Göttingen | Zwischenprodukte zur herstellung von glycerinderivaten |
| AT383130B (de) * | 1984-05-15 | 1987-05-25 | Chemie Linz Ag | Verfahren zur herstellung von an c1 und c2 verschieden substituierten phosphatidylcholinen und phosphatidylethanolaminen ueber die neuen verbindungen 1-0-tritylglycerophosphocholin beziehungsweise (1-0,n-ditrityl)-glycerophosphoethanolamin |
-
1984
- 1984-05-15 AT AT0159084A patent/AT383130B/de not_active IP Right Cessation
-
1985
- 1985-04-19 DE DE8585104662T patent/DE3563533D1/de not_active Expired
- 1985-04-19 EP EP85104662A patent/EP0161519B1/de not_active Expired
- 1985-04-19 AT AT85104662T patent/ATE35416T1/de not_active IP Right Cessation
- 1985-05-07 FI FI851781A patent/FI77663C/fi not_active IP Right Cessation
- 1985-05-07 IE IE113685A patent/IE58511B1/en not_active IP Right Cessation
- 1985-05-08 IL IL75133A patent/IL75133A/xx unknown
- 1985-05-09 CA CA000481204A patent/CA1244462A/en not_active Expired
- 1985-05-13 US US06/733,619 patent/US4622180A/en not_active Expired - Lifetime
- 1985-05-13 PH PH32256A patent/PH21831A/en unknown
- 1985-05-14 ES ES543146A patent/ES8603899A1/es not_active Expired
- 1985-05-14 NZ NZ212067A patent/NZ212067A/xx unknown
- 1985-05-14 HU HU851813A patent/HU199486B/hu not_active IP Right Cessation
- 1985-05-14 HU HU895132A patent/HU203555B/hu not_active IP Right Cessation
- 1985-05-14 DD DD85276325A patent/DD245668A1/de not_active IP Right Cessation
- 1985-05-14 NO NO851928A patent/NO163100C/no unknown
- 1985-05-14 SU SU853898601A patent/SU1422999A3/ru active
- 1985-05-14 ES ES543147A patent/ES543147A0/es active Granted
- 1985-05-14 DK DK212185A patent/DK167441C/da not_active IP Right Cessation
- 1985-05-14 KR KR1019850003277A patent/KR920009556B1/ko not_active IP Right Cessation
- 1985-05-14 DD DD85276324A patent/DD233130A1/de not_active IP Right Cessation
- 1985-05-14 AU AU42448/85A patent/AU565316B2/en not_active Ceased
- 1985-05-14 SU SU853896546A patent/SU1400511A3/ru active
- 1985-05-15 YU YU81585A patent/YU45719B/sh unknown
- 1985-05-15 ZA ZA853697A patent/ZA853697B/xx unknown
- 1985-05-15 JP JP60101644A patent/JPS60252490A/ja active Granted
- 1985-05-15 YU YU81685A patent/YU45720B/sh unknown
- 1985-05-15 TR TR22204A patent/TR22204A/xx unknown
- 1985-05-15 BR BR8502293A patent/BR8502293A/pt not_active IP Right Cessation
- 1985-06-11 CN CN85104463A patent/CN1014791B/zh not_active Expired
-
1986
- 1986-07-29 US US06/891,515 patent/US4717512A/en not_active Expired - Lifetime
-
1987
- 1987-07-06 PH PH35499A patent/PH23978A/en unknown
-
1992
- 1992-08-03 DK DK098192A patent/DK98192A/da not_active Application Discontinuation
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