PL414175A1 - 1-Acyl-2-succinyl-dehydroepiandrosterone-sn-glycero-3-phosphocholine and method for obtaining 1-Acyl-2-succinyl-dehydroepiandrosterone-sn-glycero-3-phosphocholine - Google Patents
1-Acyl-2-succinyl-dehydroepiandrosterone-sn-glycero-3-phosphocholine and method for obtaining 1-Acyl-2-succinyl-dehydroepiandrosterone-sn-glycero-3-phosphocholineInfo
- Publication number
- PL414175A1 PL414175A1 PL414175A PL41417515A PL414175A1 PL 414175 A1 PL414175 A1 PL 414175A1 PL 414175 A PL414175 A PL 414175A PL 41417515 A PL41417515 A PL 41417515A PL 414175 A1 PL414175 A1 PL 414175A1
- Authority
- PL
- Poland
- Prior art keywords
- phosphocholine
- acyl
- dehydroepiandrosterone
- succinyl
- glycero
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- FMGSKLZLMKYGDP-UHFFFAOYSA-N Dehydroepiandrosterone Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CC=C21 FMGSKLZLMKYGDP-UHFFFAOYSA-N 0.000 abstract 2
- FMGSKLZLMKYGDP-USOAJAOKSA-N dehydroepiandrosterone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 FMGSKLZLMKYGDP-USOAJAOKSA-N 0.000 abstract 2
- 229960002847 prasterone Drugs 0.000 abstract 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 abstract 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 abstract 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 238000004440 column chromatography Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000002537 cosmetic Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- YHHSONZFOIEMCP-UHFFFAOYSA-O phosphocholine Chemical compound C[N+](C)(C)CCOP(O)(O)=O YHHSONZFOIEMCP-UHFFFAOYSA-O 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Landscapes
- Cosmetics (AREA)
- Steroid Compounds (AREA)
Abstract
Przedmiotem zgłoszenia jest 1-acylo-2-bursztynylodehydroepiandrosteron-sn-glicero-3-fosfocholina o wzorze 1 oraz sposób jej otrzymywania. Sposób otrzymywania polega na tym, że do mieszaniny zawierającej osuszoną 1-acylo-2-lizo-sn-glicero-3-fosfocholinę, rozpuszczoną w bezwodnym chlorku metylenu albo chloroformie, osuszony monobursztynian dehydroepiandrosteronu w ilości co najmniej równomolowej w stosunku do fosfocholiny oraz katalityczną ilość 4-(N,N-dimetyloamino)pirydyny, dodaje się N,N -dicykloheksylokarbodiimid, w ilości będącej co najmniej dwukrotnym nadmiarem molowym w stosunku do monobursztynianu dehydroepiandrosteronu, rozpuszczony w jednym z wyżej wymienionych rozpuszczalników, po czym całość miesza się przez co najmniej 48 godzin, a produkt, którym jest 1-acylo-2-bursztynylodehydroepiandrosteron-sn-glicero-3-fosfocholina o wzorze 1, oczyszcza się za pomocą chromatografii kolumnowej. Związki te mogą znaleźć zastosowanie w przemyśle farmaceutycznym lub kosmetycznym.The subject of the application is 1-acyl-2-succinyl dihydroepiandrosterone-sn-glycerol-3-phosphocholine of formula 1 and the method of its preparation. The method of preparation consists in the fact that to a mixture containing dried 1-acyl-2-lyso-sn-glycerol-3-phosphocholine, dissolved in anhydrous methylene chloride or chloroform, dried dehydroepiandrosterone monosuccinate in an amount at least equimolar to phosphocholine and a catalytic amount 4- (N, N-dimethylamino) pyridine, N, N-dicyclohexylcarbodiimide is added, in an amount that is at least a double molar excess relative to dehydroepiandrosterone monosuccinate, dissolved in one of the above-mentioned solvents, and then the whole is mixed for at least 48 hours, and the product, which is 1-acyl-2-succinyl dihydroepiandrosterone-sn-glycero-3-phosphocholine of formula 1, is purified by column chromatography. These compounds can be used in the pharmaceutical or cosmetics industry.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL414175A PL228390B1 (en) | 2015-09-28 | 2015-09-28 | 1-Acyl-2-succinyl-dehydroepiandrosterone-sn-glycero-3-phosphocholine and method for obtaining 1-Acyl-2-succinyl-dehydroepiandrosterone-sn-glycero-3-phosphocholine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL414175A PL228390B1 (en) | 2015-09-28 | 2015-09-28 | 1-Acyl-2-succinyl-dehydroepiandrosterone-sn-glycero-3-phosphocholine and method for obtaining 1-Acyl-2-succinyl-dehydroepiandrosterone-sn-glycero-3-phosphocholine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL414175A1 true PL414175A1 (en) | 2017-04-10 |
| PL228390B1 PL228390B1 (en) | 2018-03-30 |
Family
ID=58463534
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL414175A PL228390B1 (en) | 2015-09-28 | 2015-09-28 | 1-Acyl-2-succinyl-dehydroepiandrosterone-sn-glycero-3-phosphocholine and method for obtaining 1-Acyl-2-succinyl-dehydroepiandrosterone-sn-glycero-3-phosphocholine |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL228390B1 (en) |
-
2015
- 2015-09-28 PL PL414175A patent/PL228390B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL228390B1 (en) | 2018-03-30 |
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