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Medical phospholipid compound and medical composition and application thereof

A technology of phospholipid compounds and compositions, applied in the field of medicine, can solve problems such as drug resistance, achieve strong drug efficacy, improve efficiency, and excellent anti-tumor activity

Inactive Publication Date: 2019-07-19
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, these drugs are also resistant to

Method used

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  • Medical phospholipid compound and medical composition and application thereof
  • Medical phospholipid compound and medical composition and application thereof
  • Medical phospholipid compound and medical composition and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087] Stearic acid (or palmitic acid, lauric acid)-sn-2-mercaptopropionic acid (or undecanoic acid) glycerophosphocholine, stearic acid (or palmitic acid, lauric acid)-sn-2-hydroxyethyldi Synthesis of Thiopropionic Acid (or Undecanoic Acid) Glycerophosphocholine

[0088] The general synthesis procedure is as follows: an appropriate amount of trityl (trt) protected mercaptopropionic acid (or undecanoic acid), stearic acid (or lauric acid, palmitic acid,) lysophospholipids is dissolved in dimethylsulfoxide, added Catalytic amounts of DCC and DMAP were stirred at room temperature for 12 hours. After the reaction was completed, it was precipitated with ether, washed with distilled water, extracted with dichloromethane, and the organic phase was dried with magnesium sulfate. After concentration, it is separated by column chromatography to obtain stearic acid (or palmitic acid, lauric acid)-sn-2-trt-mercaptopropionic acid (or undecanoic acid) glycerophosphocholine. Deprotection w...

Embodiment 2

[0091] Synthesis of stearic acid-sn-2-paclitaxel-7-carboxylate ethyl dithiopropionate glycerophosphocholine (route see figure 1 )

[0092] (1) 2'-OH protection of paclitaxel (2'-TBDMS-PTX)

[0093] Add 0.6g of paclitaxel, 0.5g of imidazole, and 30mL of DMF into a 100mL round bottom flask, stir to dissolve. 1.2 g of tert-butyldimethylchlorosilane was slowly added dropwise thereto, and after 20 minutes of completion of the dropwise addition, the reaction was continued at room temperature for 12 hours. After the reaction was completed, 100 mL of dichloromethane was added for extraction and fully washed with deionized water. The organic phase was dried over anhydrous magnesium sulfate and concentrated by rotary evaporation. The product was purified by column chromatography to obtain 0.62 g of white solid 2'-tert-butyldimethylsiloxane-paclitaxel (2'-TBDMS-PTX), with a yield of 95%.

[0094] 1 H NMR (500MHz, CDCl 3 ):δ0.46(s,6H,Si(CH 3 ) 2 ),0.83(s,9H,tert-butyl),1.17(s,3H,H...

Embodiment 3

[0100] Synthesis of stearic acid-sn-2-camptothecin formate ethyl dithiopropionate glycerophosphocholine (route see figure 2 )

[0101] 0.53g of camptothecin and 0.20g of triphosgene (BTC) were mixed uniformly in 100mL of anhydrous dichloromethane. Under a nitrogen atmosphere, 0.30 g of DMAP in dichloromethane solution was slowly added dropwise, and the reaction was stirred at room temperature for 2 h. Add 0.50 g of stearic acid-sn-2-hydroxyethyldithiopropanoic acid glycerophosphocholine to the above system at one time, and react overnight. Afterwards, the crude product, MgSO 4 The organic phase was dried and concentrated. The product was purified by column chromatography to obtain 0.35 g of the product stearic acid-sn-2-camptothecin formate ethyl dithiopropionyl glycerophosphocholine as a yellow solid.

[0102] 1 H NMR (500MHz, CD3OD:CDCl 3 1:1):δ8.06-7.42(5H,m),6.74(1H,s),4.75-4.64(3H,m),4.46-4.22(6H,d),3.97-3.77(4H,d), 3.43 (2H, t), 3.30 (9H, s), 2.95-2.25 (6H, m), ...

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Abstract

The invention discloses a medical phospholipid compound and a medical composition and application thereof. The phospholipid compound is a compound as shown in the following general formula (1) or pharmaceutically acceptable salt prepared from the compound as shown in the general formula (1) and counterions; and in the formula (1), m is a positive integer from 2-10, n is a positive integer from 5-10, X is a medicine, and L is 2-aminoethyl cations and 2-trimethylamine ethyl cations. The medical composition comprises the medical phospholipid compound, or the medical phospholipid compound and a pharmaceutically acceptable carrier. The application of the medical phospholipid compound to preparation of antitumor medicines lies in that the medical phospholipid compound or the pharmaceutically acceptable salt thereof, and the pharmaceutically acceptable carrier are prepared into a medicament. The medical phospholipid compound and liposome nanometer particles thereof can be used as a liquid preparation, a solid preparation, a semisolid preparation, a sterilizing preparation and a sterile preparation, and liposomes can be formed under a water-phase system.

Description

technical field [0001] The invention relates to a drug phospholipid compound with antitumor effect, its pharmaceutical composition and application, and relates to the technical field of medicine. Background technique [0002] Liposome is an important drug carrier, which can be loaded with various drugs for controlled release. Hydrophobic drugs are usually in the lipid bilayer of liposomes. But medicine is easy to seep out from liposome, affects the performance of drug effect. Combining drug molecules into the phospholipid molecular structure through covalent bonds constitutes a prodrug, which can avoid drug leakage. Combining drugs with lysophospholipids through ester bonds is another solution, but the degradation of ester bonds is slow, and it is difficult for drugs to be released quickly. [0003] The patent (ZL201510598251.9) uses an easily degradable disulfide bond to link two drug molecules with glycerophosphocholine. Disulfide bonds can release drugs quickly, but b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/54A61K47/58A61K31/337A61K31/4745A61P35/00
CPCA61K47/544A61K47/58A61P35/00A61K31/337A61K31/4745
Inventor 李新松何伟
Owner SOUTHEAST UNIV
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