Phospholipid derivatives of valproic acid and mixtures thereof

A derivative, the technology of valproic acid, is applied in the field of bipolar cell disease and pain, migraine, and epilepsy, and can solve the unmet long-term needs of antiepileptic drugs, etc.

Inactive Publication Date: 2006-05-17
迪-药品有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] Despite continuous efforts in this field, there is as yet an unmet long-felt need for an antiepileptic agent with improved pharmacokinetic properties and an overall superior efficacy index

Method used

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  • Phospholipid derivatives of valproic acid and mixtures thereof
  • Phospholipid derivatives of valproic acid and mixtures thereof
  • Phospholipid derivatives of valproic acid and mixtures thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0054] Example 1: Synthesis of DP-VPA

[0055] The synthesis of the DP-VPA is a two-stage process. The first stage is aimed at the preparation of valproic anhydride, ie by heating valproic acid in a solution of acetic anhydride in the presence of the catalyst pyridine. In the second stage, DP-VPA is prepared by means of the reaction between valproic anhydride and lysolecithin. The reaction is carried out in valproic anhydride solution at 90-100°C under the catalysis of 4-dimethylaminopyridine.

[0056] The extraction and purification of the product obtained is carried out in four steps. The first stage of purification involves extraction of unreacted valproic anhydride, valproic acid and catalyst (4-aminopyridine) with acetone. The crude product obtained is precipitated from solution and isolated in a second stage. The solid product obtained is washed to remove residual compounds in the third stage. Finally, the product was recrystallized several times from acetone / ethano...

example 2

[0063] Example 2: C16 / C 18 -Synthesis of DP-VPA

[0064] C 16 / C 18 - A mixture of DP-VPA was prepared following the same procedure as described in Example 1 for the preparation of DP-VPA. The difference is that, in the case of mixture compositions, in the interaction of valproic anhydride with lyso-lecithin obtained from soybeans and saturated by hydrogenation (S VPC-3 from the company Lipoid, Ludwigshafen ,Germany).

example 3

[0065] Example 3: Analysis of DP-VPA Compounds

[0066] For C synthesized in Example 2 as described above 16 / C 18 - The DP-VPA mixture was subjected to analytical assays to identify and demonstrate its structure. 1-palmitoyl-2-valproyl-sn-glyceryl-3-phosphatidylcholine (C 16 -DP-VPA) and 1-stearoyl-2-valproyl-sn-glyceryl-3-phosphatidylcholine (C 18 The analytical results of the product of -DP-VPA) are given below.

[0067] mass spectrometry

[0068] The mass of the protonated DP-VPA molecule determined by ESI(+) is C 16 - 622.4 to 622.8 for DP-VPA; and C 18 -DP-VPA is 650.4 to 650.8. This agrees well with the calculated molecular weight values.

[0069] Elemental analysis

[0070] Press M.H. 2 0 Calculated values: C60.93%; H10.25%; N2.11%; P4.66% (M according to the content).

[0071] The average values ​​determined were C60.72%; H10.58%; N2.09%; P4.56%.

[0072] These values ​​agree well with the calculated values.

[0073] Thin layer chromatography (TLC) analy...

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Abstract

The present invention relates to a compound, ie, a phospholipid derivative of valproic acid, a composition comprising the compound and its application for treating epilepsy, migraine, bipolar cell disease and pain.

Description

technical field [0001] The present invention relates to a compound, ie, a phospholipid derivative of valproic acid, a composition comprising the compound and its application for treating epilepsy, migraine, bipolar cell disease and pain. Background technique [0002] Epilepsy is a neurological disorder characterized by paroxysmal transient disturbances in electrical brain activity. Seizures can be localized or focal, limited to a specific location in the brain, or generalized, causing abnormal activity along the entire brain. Brain dysfunction during seizures can manifest as mental and sensory disturbances, eg, amnesia, hallucinations, states of déjà vu, motor abnormalities such as convulsions or generalized spasms, or loss of consciousness. In extreme cases, epilepsy can degenerate into a potentially life-threatening epilepticus condition (DeLorenzo et al., J. Clin. Neurophysiol. (1995) 12:316-325). [0003] Valproic acid (VPA) and its sodium salt (sodium valproate, NaVPA...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/683A61K31/19A61K31/685A61K31/352A61P25/00A61P25/06A61P25/08C07F9/02C07F9/10
CPCA61K31/19A61K31/352C07F9/10A61K47/544A61P25/00A61P25/06A61P25/08A61K31/66
Inventor A·科扎克
Owner 迪-药品有限公司
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