PL238120B1 - 1'-Palmitoyl-2'-(3,7,11,15-tetramethyl-3-vinyl hexadecyl)-sn-glycero-3'-phosphocholine and method for obtaining it - Google Patents
1'-Palmitoyl-2'-(3,7,11,15-tetramethyl-3-vinyl hexadecyl)-sn-glycero-3'-phosphocholine and method for obtaining it Download PDFInfo
- Publication number
- PL238120B1 PL238120B1 PL419067(22)20161011A PL41906716A PL238120B1 PL 238120 B1 PL238120 B1 PL 238120B1 PL 41906716 A PL41906716 A PL 41906716A PL 238120 B1 PL238120 B1 PL 238120B1
- Authority
- PL
- Poland
- Prior art keywords
- tetramethyl
- phosphocholine
- glycero
- palmitoyl
- vinylhexadecanoyl
- Prior art date
Links
Abstract
Zgłoszenie dotyczy 1'-palmitoilo-2'-(3,7,11,15-tetrametylo-3-winyloheksadecylo)-sn-glicero-3'-fosfocholiny, o wzorze 1, przedstawionym na rysunku oraz sposobu jej otrzymywania na drodze estryfikacji 1-palmitoilo-sn-glicero-3-fosfocholiny kwasem 3,7,11,15-tetrametylo-3-winyloheksadekanowym z udziałem czynnika sprzęgającego, jakim jest N,N' dicykloheksylokarbodiimid oraz w obecności 4-dimetyloaminopirydyny w środowisku bezwodnego chlorku metylenu lub chloroformu. Fosfolipid ten może znaleźć zastosowanie w przemyśle farmaceutycznym jako prolek w terapii chorób nowotworowych.The application concerns 1'-palmitoyl-2'-(3,7,11,15-tetramethyl-3-vinylhexadecyl)-sn-glycero-3'-phosphocholine, of the formula 1, shown in the figure, and the method of its preparation by esterification 1 -palmitoyl-sn-glycero-3-phosphocholine with 3,7,11,15-tetramethyl-3-vinylhexadecanoic acid with the participation of the coupling agent, which is N,N' dicyclohexylcarbodiimide and in the presence of 4-dimethylaminopyridine in anhydrous methylene chloride or chloroform. This phospholipid can be used in the pharmaceutical industry as a prodrug in the treatment of cancer.
Description
Opis wynalazkuDescription of the invention
Przedmiotem wynalazku jest 1 ’-palmitoilo-2’-(3,7,11,15-tetrametylo-3-winyloheksadekanoilo)-sn-glicero-3’-fosfocholina o wzorze 1, przedstawionym na rysunku.The subject of the invention is 1'-palmitoyl-2 '- (3,7,11,15-tetramethyl-3-vinylhexadecanoyl) -sn-glycero-3'-phosphocholine of the formula 1, shown in the drawing.
Przedmiotem wynalazku jest także sposób otrzymywania 1 ’-palmitoilo-2’-(3,7,11,15-tetrametylo-3-winyloheksadekanoilo)-sn-glicero-3’-fosfocholiny o wzorze 1.The invention also relates to a method for the preparation of 1 '-palmitoyl-2' - (3,7,11,15-tetramethyl-3-vinylhexadecanoyl) -sn-glycero-3'-phosphocholine of formula 1.
Z opisu zgłoszenia P.418655 znany jest sposób otrzymywania kwasu 3,7,11,15-tetrametylo-3-winyloheksadekanowego oraz jego aktywność antyproliferacyjna w stosunku do komórek nowotworowych białaczki linii MV4-11. Z opisu wynalazku P.418942 znany jest fosfolipid zawierający kwas 3,7,11,15-tetrametylo-3-winyloheksadekanowy wbudowany jednocześnie w pozycje sn-1 i sn-2. Nie jest znana w literaturze pochodna glicerofosfocholiny zawierająca w swojej strukturze cząsteczkę kwasu palmitynowego w pozycji sn-1 i cząsteczkę kwasu 3,7,11,15-tetrametylo-3-winyloheksadekanowego w pozycji sn-2.From the description of the application P.418655 there is known a method for the preparation of 3,7,11,15-tetramethyl-3-vinylhexadecanoic acid and its antiproliferative activity against neoplastic cells of the MV4-11 leukemia line. From the description of the invention, P.418942, there is known a phospholipid containing 3,7,11,15-tetramethyl-3-vinylhexadecanoic acid simultaneously incorporated into the sn-1 and sn-2 positions. There is no known in the literature a derivative of glycerophosphocholine containing in its structure a palmitic acid molecule in the sn-1 position and a 3,7,11,15-tetramethyl-3-vinylhexadecanoic acid molecule in the sn-2 position.
Istotą wynalazku jest fosfolipidowa pochodna kwasu 3,7,11,15-tetrametylo-3-winyloheksadekanowego, którą jest 1’-palmitoilo-2’-(3,7,11,15-tetrametylo-3-winyloheksadekanoilo)-sn-glicero-3’-fosfocholina.The essence of the invention is the phospholipid derivative of 3,7,11,15-tetramethyl-3-vinylhexadecanoic acid, which is 1'-palmitoyl-2 '- (3,7,11,15-tetramethyl-3-vinylhexadecanoyl) -sn-glycero- 3'-phosphocholine.
Istota sposobu, według wynalazku polega na tym, że do mieszaniny 1-palmitoilo-sn-glicero-3-fosfocholiny, kwasu 3,7,11,15-tetrametylo-3-winyloheksadekanowego i 4-dimetylo-aminopirydyny rozpuszczonych w rozpuszczalniku organicznym, dodaje się N,N'-dicykloheksylokarbodiimid rozpuszczony w rozpuszczalniku organicznym, po czym miesza się przez co najmniej 1 dobę. Następnie mieszaninę poreakcyjną odsącza się pod zmniejszonym ciśnieniem, a do przesączu dodaje się żywicę jonowymienną w formie H+ i miesza przez co najmniej 30 minut a żywicę jonowymienną odsącza się, natomiast rozpuszczalnik odparowuje się pod zmniejszonym ciśnieniem. Surowy produkt, którym jest 1’-palmitoilo-2’-(3,7,11,15-tetrametylo-3-winyloheksadekanoilo)-sn-glicero-3’-fosfocholina oczyszcza się za pomocą chromatografii kolumnowej na żelu krzemionkowym.The essence of the method according to the invention consists in adding to the mixture of 1-palmitoyl-sn-glycero-3-phosphocholine, 3,7,11,15-tetramethyl-3-vinylhexadecanoic acid and 4-dimethylaminopyridine dissolved in an organic solvent N, N'-dicyclohexylcarbodiimide dissolved in an organic solvent is then stirred for at least 1 day. The reaction mixture was then filtered off under reduced pressure, an ion exchange resin in H + form was added to the filtrate and stirred for at least 30 minutes, the ion exchange resin was filtered off, and the solvent was evaporated under reduced pressure. The crude product which is 1'-palmitoyl-2 '- (3,7,11,15-tetramethyl-3-vinylhexadecanoyl) -sn-glycero-3'-phosphocholine is purified by silica gel column chromatography.
Korzystnie jest, gdy proces estryfikacji prowadzi się w temperaturze od 18 do 55°C.Preferably, the esterification process is carried out at a temperature of 18 to 55 ° C.
Korzystnie jest, gdy jako rozpuszczalnik w reakcji estryfikacji stosuje się bezwodny chlorek metylenu lub bezwodny chloroform.Preferably, anhydrous methylene chloride or anhydrous chloroform is used as the esterification solvent.
Zasadniczą zaletą wynalazku jest otrzymanie z dużą wydajnością i wysoką czystością 1’-palmitoilo-2’-(3,7,11,15-tetrametylo-3-winyloheksadekanoilo-sn-glicero-3’-fosfocholiny o wzorze 1.The main advantage of the invention is obtaining with high yield and high purity 1'-palmitoyl-2 '- (3,7,11,15-tetramethyl-3-vinylhexadecanoyl-sn-glycero-3'-phosphocholine of formula 1.
Wynalazek jest bliżej objaśniony w przykładzie wykonania.The invention is explained in more detail in an exemplary embodiment.
P r z y k ł a d 1P r z k ł a d 1
Do roztworu osuszonej 1-palmitoilo-sn-glicero-3-fosfocholiny (150 mg, 0.302 mmol) rozpuszczonej w bezwodnym chlorku metylenu (CH2CI2, 1 cm3) dodaje się kwas 3,7,11,15-tetrametylo-3-winyloheksadekanowy (205 mg, 0.604 mmol), 4-dimetyloaminopirydynę (DMAP) (74 mg, 0.604 mmol) rozpuszczoną w 3 cm3 bezwodnego chlorku metylenu oraz N,N'-dicykloheksylokarbodiimidu (DCC) (268 mg, 1.3 mmol) rozpuszczony w 5 cm3 bezwodnego chlorku metylenu. Zawiesinę miesza się intensywnie w temperaturze 40°C w atmosferze N2 przez 72 godziny. Po tym czasie mieszaninę poreakcyjną odsącza się pod zmniejszonym ciśnieniem na lejku Schotta, a do przesączu dodaje się żywicę jonowymienną w formie H+ i miesza przez 30 minut. Następnie żywicę jonowymienną odsącza się, a rozpuszczalnik odparowuje się pod zmniejszonym ciśnieniem. Surowy produkt oczyszcza się za pomocą chromatografii kolumnowej na żelu krzemionkowym stosując jako eluent mieszaninę rozpuszczalników CHCl3:MeOH:H2O, 65:25:4 (v/v/v). Otrzymuje się 205 mg (0.154 mmol) 1’-palmitoilo-2’-(3,7,11,15-tetrametylo-3-winyloheksadekanoilo)-sn-glicero-3’-fosfocholinę z wydajnością 51% w postaci mazistej substancji o czystości >99% (wg HPLC).To a dried solution of 1-palmitoyl-sn-glycero-3-phosphocholine (150 mg, 0.302 mmol) dissolved in dry methylene chloride (CH2Cl2, 1 cm 3) was added acid 3,7,11,15-tetramethyl-3-winyloheksadekanowy ( 205 mg, 0.604 mmol), 4-dimethylaminopyridine (DMAP) (74 mg, 0.604 mmol) dissolved in 3 cm 3 of anhydrous methylene chloride and N, N'-dicyclohexylcarbodiimide (DCC) (268 mg, 1.3 mmol) dissolved in 5 cm 3 anhydrous methylene chloride. The suspension is stirred vigorously at 40 ° C under N2 for 72 hours. After this time, the reaction mixture was filtered under reduced pressure on a Schott funnel, and an ion-exchange resin in H + form was added to the filtrate and stirred for 30 minutes. The ion exchange resin is then filtered off and the solvent is evaporated off under reduced pressure. The crude product was purified by column chromatography on silica gel using a solvent mixture of CHCl3: MeOH: H2O 65: 25: 4 (v / v / v) as the eluent. 205 mg (0.154 mmol) of 1'-palmitoyl-2 '- (3,7,11,15-tetramethyl-3-vinylhexadecanoyl) -sn-glycero-3'-phosphocholine are obtained with a yield of 51% as a greasy substance of purity > 99% (by HPLC).
Dane spektroskopowe otrzymanego związku są następujące:The spectroscopic data of the obtained compound are as follows:
1H NMR (600 MHz, CDCI3/CD3OD 2:1 (v/v)), δ: 0.60-0.65 (m, 18H, CH3-20, CH3-20 (B), CH3-21 (A), CH3-21 (B), CH3(CH2)13CH2C(O) (A), CH^(CH2)i3CH2C(O) (B)), 0.63 (d, J = 6.6 Hz, 12H, CH3-16 (A), CH3-16 (B), CH3-22 (A), CH3-22 (B)), 0.88 (s, 6H, CH3-19 (A), CH3-19 (B)), 0.83-1.13 (four m, 88H, CH2-4 (A), CH2-4 (B), CH2-5 (A), CH2-5 (B), CH2-6 (A), CH2-6 (B), CH2-8 (A), CH2-8 (B), CH2-9 (A), CH2-9 (B), CH2-10 (A), CH2-10 (B), CH2-12 (A), CH2-12 (B), CH2-13 (A), CH2-13 (B), CH2-14 (A), CH2-14 (B), H-7 (A), H-7 (B), H-11 (A), H-11 (B), CH3(CH2)i2CH2CH2C(O) (A), CH3(CH)i2CH2CH2C(O) (B)), 1.29 (m, 2H, H-15 (A), H-15 (B)), 1.36-1.38 (m, 2H, CH3(CH2)i2CH2CH2C(O) (A), CH3(CH2)i2CH2CH2C(O) (B)), 2.06-2.15 (dwa m, 8H, CH2-2 (A), CH2-2 (B), CH3(CH2)i3CH2C(O) (A), CH3(CH2)i3CH2C(O) (B)), 2.99 (s, 18H, -N(CH3)3 (A), -N(CH3)3 (B)), 3.37-3.41 (m, 4H, CH2-3 (A), CH2-3 (B)), 3.75-3.77 (m, 4H, CH2-3' (A), CH2-3' (B)), 3.88-3.91 (m, 2H, jeden z CH2-1' (A), jeden z CH2-1' (B), 4.00-4.06 (m, 4H, CH2-a (A), CH2-a (B)), 4.16 (m, 2H, jeden z CH2-1' (A), jeden z CH2-1' (B)), 4.69-4.73 (dwa d, J= 18.0 Hz,1H NMR (600 MHz, CDCl3 / CD3OD 2: 1 (v / v)), δ: 0.60-0.65 (m, 18H, CH3-20, CH3-20 (B), CH3-21 (A), CH3-21 (B), CH3 (CH2) 13CH2C (O) (A), CH2 (CH2) and 3CH2C (O) (B)), 0.63 (d, J = 6.6 Hz, 12H, CH3-16 (A), CH3- 16 (B), CH3-22 (A), CH3-22 (B)), 0.88 (s, 6H, CH3-19 (A), CH3-19 (B)), 0.83-1.13 (four m, 88H, CH2-4 (A), CH2-4 (B), CH2-5 (A), CH2-5 (B), CH2-6 (A), CH2-6 (B), CH2-8 (A), CH2 -8 (B), CH2-9 (A), CH2-9 (B), CH2-10 (A), CH2-10 (B), CH2-12 (A), CH2-12 (B), CH2- 13 (A), CH2-13 (B), CH2-14 (A), CH2-14 (B), H-7 (A), H-7 (B), H-11 (A), H-11 (B), CH3 (CH2) i2CH2CH2C (O) (A), CH3 (CH) i2CH2CH2C (O) (B)), 1.29 (m, 2H, H-15 (A), H-15 (B)), 1.36-1.38 (m, 2H, CH3 (CH2) i2CH2CH2C (O) (A), CH3 (CH2) i2CH2CH2C (O) (B)), 2.06-2.15 (two m, 8H, CH2-2 (A), CH2 -2 (B), CH3 (CH2) i3CH2C (O) (A), CH3 (CH2) i3CH2C (O) (B)), 2.99 (s, 18H, -N (CH3) 3 (A), -N ( CH3) 3 (B)), 3.37-3.41 (m, 4H, CH2-3 (A), CH2-3 (B)), 3.75-3.77 (m, 4H, CH2-3 '(A), CH2-3 '(B)), 3.88-3.91 (m, 2H, one of CH2-1' (A), one of CH2-1 '(B), 4.00-4.06 (m, 4H, CH2-a (A), CH2 -a (B)), 4.16 (m, 2H, one from CH2-1 '(A), one from CH2-1' (B)), 4.69-4.73 (two d, J = 18.0 Hz,
PL 238 120 B1PL 238 120 B1
2H, jeden z CH2-I8 (A), jeden z CH2-I8 (B)), 4.76-4.79 (dwa d, J = 10.2 Hz, 2H, H, jeden z CH2-I8 (A), jeden z CH2-18 (B)), 4.97 (m, 2H, H-2' (A), H-2' (B)), 5.55 (m, 2H, H-17 (A), H-17 (B));2H, one of CH2-I8 (A), one of CH2-I8 (B)), 4.76-4.79 (two d, J = 10.2 Hz, 2H, H, one of CH2-I8 (A), one of CH2- 18 (B)), 4.97 (m, 2H, H-2 '(A), H-2' (B)), 5.55 (m, 2H, H-17 (A), H-17 (B));
13C NMR (151 MHz, CDCI3/CD3OD 2:1 (v/v)), δ: 13.51, 13.53 (CH3(CH2)i3CH2C(O) (A), 13 C NMR (151 MHz, CDCl3 / CD3OD 2: 1 (v / v)), δ: 13.51, 13.53 (CH3 (CH2) i3CH2C (O) (A),
CH3(CH2)13CH2C(O) (B)), 19.08, 19.14, 19.22, 22.07, 22.16 (C-20 (A), C-20 (B), C-21 (A), C-21 (B), (C-16 (A), C-16 (B), C-22 (A), C-22 (B), (C-19 (A), C-19 (B)), 21.11, 21.13, 22.25, 22.42, 22.44, 22.51, 24.06, 24.39, 24.40, 24.43, 24.47, 28.75, 28.90, 28.94, 29.10, 29.24, 29.28, 36.87, 36.98, 36.99, 37.04, 37.06, 37.28, 37.37, 38.83, 38.84, 38.91,38.93, 40.93 (C-4 (A), C-4 (B), C-5 (A), C-5 (B), C-6 (A), C-6 (B), C-8 (A), C-8 (B), C-9 (A), C-9 (B), C-10 (A), C-10 (B), C-12 (A), C-12 (B), C-13 (A), C-13 (B), C-14 (A), C-14 (B), CH3(CH2)12CH2CH2C(O) (A), CH3(CH2)i2CH2CH2C(O) (B), 27.56 (C-15 (A), C-15 (B)), 31.52, 32.37, 32.38 (C-7 (A), C-7 (B), C-11 (A), C-11 (B)), 33.69 (CH3(CH2)i3CH2C(O) (A), CH3(CH2)13CH2C(O) (B)), 38.97 (C-3 (A), C-3 (B)), 44.73, 44.79 (C-2 (A), C-2 (B)), 53.73 (-N(CH3)3 (A), -N(CH3)3 (B)), 58.81 (d, J = 4.2 Hz, C-α (A), C-a (B)), 62.42 (C-1' (A), C-1’ (B)), 63.34 (d, J = 5.3 Hz, C-3' (A), C-3' (B)), 66.03 (m, C-β (A), C-β (B)), 69.80 (d, J = 8.0 Hz, C-2'(A), C-2'(B)), 111.71 (C-18 (A), C-18 (B)), 145.02 (C-17 (A), C-17 (B)), 171.06 (C-1 (A), C-1 (B)), 173.59 (CH3(CH2)i3CH2C(O) (A), CH3(CH2)13CH2C(O) (B));CH3 (CH2) 13CH2C (O) (B)), 08/19, 19.14, 19.22, 07.22, 22.16 (C-20 (A), C-20 (B), C-21 (A), C-21 (B) , (C-16 (A), C-16 (B), C-22 (A), C-22 (B), (C-19 (A), C-19 (B)), 21.11, 21.13, 22.25, 22.42, 22.44, 22.51, 24.06, 24.39, 24.40, 24.43, 24.47, 28.75, 28.90, 28.94, 29.10, 29.24, 29.28, 36.87, 36.98, 36.99, 37.04, 37.06, 37.28, 37.37, 38.83, 38.84, 38.91, 38.93, 40.93 (C-4 (A), C-4 (B), C-5 (A), C-5 (B), C-6 (A), C-6 (B), C-8 ( A), C-8 (B), C-9 (A), C-9 (B), C-10 (A), C-10 (B), C-12 (A), C-12 (B ), C-13 (A), C-13 (B), C-14 (A), C-14 (B), CH3 (CH2) 12CH2CH2C (O) (A), CH3 (CH2) and 2CH2CH2C (O) (B), 27.56 (C-15 (A), C-15 (B)), 31.52, 32.37, 32.38 (C-7 (A), C-7 (B), C-11 (A), C- 11 (B)), 33.69 (CH3 (CH2) i3CH2C (O) (A), CH3 (CH2) 13CH2C (O) (B)), 38.97 (C-3 (A), C-3 (B)), 44.73, 44.79 (C-2 (A), C-2 (B)), 53.73 (-N (CH3) 3 (A), -N (CH3) 3 (B)), 58.81 (d, J = 4.2 Hz , C-α (A), Ca (B)), 62.42 (C-1 '(A), C-1' (B)), 63.34 (d, J = 5.3 Hz, C-3 '(A), C-3 '(B)), 66.03 (m, C-β (A), C-β (B)), 69.80 (d, J = 8.0 Hz, C-2' (A), C-2 '( B)), 111.71 (C-18 (A), C-18 (B)), 145.02 (C-17 (A), C-17 (B)), 171.06 (C-1 (A), C-1 (B)), 173.59 (CH3 (CH2) and 3CH2C (O) (A), CH3 (CH2) 13CH2C (O) (B));
31P NMR (243 MHz, CDCI3/CD3OD 2:1 (v/v)), δ: -0.91; 31 P NMR (243 MHz, CDCl3 / CD3OD 2: 1 (v / v)) δ: -0.91;
(a, β) - oznacza sygnały pochodzące od choliny(a, β) - indicates choline-derived signals
P r z y k ł a d 2P r z k ł a d 2
Postępuje się tak jak w przykładzie 1 z tym, że jako rozpuszczalnik w reakcji estryfikacji stosuje się bezwodny chloroform. Otrzymuje się w ten sposób 1’-palmitoilo-2’-(3,7,11,15-tetrametylo-3-winyloheksadekanoilo)-sn-glicero-3’-fosfocholinę z wydajnością 50% w postaci mazistej substancji o czystości >98% (wg HPLC).The procedure is as in Example 1, except that anhydrous chloroform is used as the esterification solvent. 1'-palmitoyl-2 '- (3,7,11,15-tetramethyl-3-vinylhexadecanoyl) -sn-glycero-3'-phosphocholine is thus obtained with a yield of 50% as a greasy substance with a purity> 98% (by HPLC).
Claims (5)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL419067(22)20161011A PL238120B1 (en) | 2016-10-11 | 2016-10-11 | 1'-Palmitoyl-2'-(3,7,11,15-tetramethyl-3-vinyl hexadecyl)-sn-glycero-3'-phosphocholine and method for obtaining it |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL419067(22)20161011A PL238120B1 (en) | 2016-10-11 | 2016-10-11 | 1'-Palmitoyl-2'-(3,7,11,15-tetramethyl-3-vinyl hexadecyl)-sn-glycero-3'-phosphocholine and method for obtaining it |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL419067A1 PL419067A1 (en) | 2017-06-19 |
| PL238120B1 true PL238120B1 (en) | 2021-07-05 |
Family
ID=59061649
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL419067(22)20161011A PL238120B1 (en) | 2016-10-11 | 2016-10-11 | 1'-Palmitoyl-2'-(3,7,11,15-tetramethyl-3-vinyl hexadecyl)-sn-glycero-3'-phosphocholine and method for obtaining it |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL238120B1 (en) |
-
2016
- 2016-10-11 PL PL419067(22)20161011A patent/PL238120B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL419067A1 (en) | 2017-06-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Shi et al. | Synthesis and tumor cell growth inhibitory activity of biotinylated annonaceous acetogenins | |
| ES2533710T3 (en) | Process for the preparation of morpholinyl anthracycline derivatives | |
| EP2223929A1 (en) | Gambogic glycoside derivatives and analogs, the preparation and the application thereof | |
| Kłobucki et al. | Syntheses and antiproliferative activities of novel phosphatidylcholines containing dehydroepiandrosterone moieties | |
| PL238120B1 (en) | 1'-Palmitoyl-2'-(3,7,11,15-tetramethyl-3-vinyl hexadecyl)-sn-glycero-3'-phosphocholine and method for obtaining it | |
| ES2395895T3 (en) | Triazolo-epothilones | |
| RU2169149C2 (en) | Compounds with camptothecin structure, methods of their synthesis, pharmaceutical compositions | |
| PL228423B1 (en) | 1'-(3,7,11,15-Tetramethyl-3-vinylhexadecyl)-2'-hydroxy-sn-glycero-3'-phosphatidylcholine and method for obtaining it | |
| KR101478758B1 (en) | Halogenated dideoxy saccharide derivatives, preparation method and use thereof | |
| CN101792477B (en) | Acetyl ursolic acid acylate triethanolamine monoester with anti-cancer activity and preparation method thereof | |
| PL231814B1 (en) | 1'Palmitoyl-2'-(3,7,11-trimethyl-3-vinyldodec-6,10-dienylo)-sn-glycero-3'-phosphocholine and method for obtaining it | |
| PL231815B1 (en) | 1'-Palmitoyl-2'-[2-(2''-butylidene-1'',3'',3''-trimethyl)cyclohexyl]acetyl-sn-glycero-3'-phosphocholine and method for obtaining it | |
| PL231816B1 (en) | 1'Palmitoyl-2'-(3,7-Dimethyl-3-vinylocta-6-enyl)-sn-glycero-3'-phosphocholine and method for obtaining it | |
| PL229269B1 (en) | 1'2'-Di[(3,7,11,15-tetramethyl-3-vinylhexadecyl]-sn-glycero-3'-phosphocholine and method for obtaining it | |
| PL216420B1 (en) | New betulin diesters and process for the preparation thereof | |
| PL236558B1 (en) | 1'-(3,7,11,15-Tetramethyl-3-vinyl hexadecyl)-2'-palmitoyl-sn-glycero-3'-phosphocholine and method for obtaining it | |
| DE2647395C2 (en) | Process for the preparation of esters of glycerophosphocholine | |
| PL228425B1 (en) | 1'-(3,7,11-Trimethyl-3-vinyldodeca-6,10-dienyl)-2'-palmitoyl-sn-glycero-3'-phosphfocholine and method for obtaining it | |
| PL228424B1 (en) | 1'-(3,7-Dimethyl-3-vinylocta-6-enyl)-2'-palmitoyl-sn-glycero-3'-phosphocholine and method for obtaining it | |
| PL228426B1 (en) | 1'-{2-[(2''E)-2''-Butylidene-1'',3'',3''trimethyl]cyclohexyl}acetyl-2'-palmitoyl-sn-glycero-3'-phosphocholine and method for obtaining it | |
| PL238119B1 (en) | 1'2'-Di[3,7,11-trimethyl-3-vinyldodeca-6,10-dienyl]-sn-glycero-3'-phosphocholine and method for obtaining 1'2'-di[3,7,11-trimethyl-3-vinyldodeca-6,10-dienyl]-sn-glycero-3'-phosphocholine | |
| KR101535883B1 (en) | Pectenotoxin-2 derivative, and anticancer agent containing the same | |
| CN114437102B (en) | Novel rubescensin derivative with 6-hydroxy group removed, preparation method and medical application thereof | |
| Gruszecka-Kowalik et al. | Free-radical reactions of retronecine and heliotridine derivatives. The synthesis of (-)-supinidine | |
| PL230423B1 (en) | 1'2'-Di-[3,7-dimethyl-3-vinylocta-6-enyl]-sn-glycero-3'-phosphocholine and method for obtaining 1',2'-di-[3,7-dimethyl-3-vinylocta-6-enyl]-sn-glycero-3'-phosphocholine |