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Alkyl phospholipid derivatives with reduced cytotoxicity and uses thereof

A technology of alkyl phospholipids and derivatives, applied in medical preparations containing active ingredients, organic active ingredients, antiviral agents, etc., can solve problems such as long courses of treatment and serious side effects

Inactive Publication Date: 2009-01-07
AETERNA ZENTARIS GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0027] However, the alkylphospholipid derivatives and their use known in the prior art do show inherent disadvantages
In particular, standard pharmaceutical agents (APL and others) against bacterial, fungal, protozoan and / or viral diseases imply several disadvantages such as resistance of the targeted microorganisms, severe side effects caused by the high toxicity of the administered compounds and long course of treatment

Method used

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  • Alkyl phospholipid derivatives with reduced cytotoxicity and uses thereof
  • Alkyl phospholipid derivatives with reduced cytotoxicity and uses thereof
  • Alkyl phospholipid derivatives with reduced cytotoxicity and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0865] Example 1: Compound 1

[0866] 1-Benzyl-1-methyl-piperidin-4-yl phosphate hexadecyl ester

[0867] After methylation of 1-benzyl-piperidin-4-ol according to general method 2, 3.1 g were obtained starting from cetyl-1-ol and 1-benzyl-piperidin-4-ol according to general method 4 ( 6%) compound 1.

[0868]1 H-NMR (600MHz, CDCl 3 -d1, 300K): δ=7.59 (2H, d), 7.47-7.40 (3H, m), 4.78 (2H, broad peak-s), 4.55 (1H, broad peak-s), 3.86-3.77 (4H, m), 3.56 (2H, d), 3.13 (3H, s), 2.27 (2H, d), 2.13 (2H, t), 1.57 (2H, quintet), 1.31-1.18 (26H, m), 0.88 (3H,t)ppm

[0869] ESI-MS: Found: m / z 510.4 [M+H], Calculated: 510.7 g / mol

Embodiment 2

[0870] Example 2: Compound 2

[0871] Cetyl phosphate 2-(1-methyl-piperidin-1-yl)-ethyl ester

[0872] After methylation of 2-piperidin-1-yl-ethanol according to general method 2, 5.8 g (13% ) Compound 2.

[0873] 1 H-NMR (600MHz, CDCl 3 -d1, 300K): δ=4.33 (2H, broad peak-s), 3.89-3.81 (4H, m), 3.70 (2H, m), 3.57-3.53 (2H, m), 3.37 (3H, s), 1.93-1.86 (4H, m), 1.74-1.68 (2H, m), 1.59 (2H, quintet), 1.35-1.19 (26H, m), 0.88 (3H, s) ppm

[0874] ESI-MS: Found: m / z 448.3 [M+H], Calculated: 448.6 g / mol

Embodiment 3

[0875] Example 3: Compound 3

[0876] 2-(1-Aza-bicyclo[2.2.2]oct-1-yl)-ethyl hexadecyl phosphate

[0877] After alkylation of chinuclidine according to general method 1, 2,0 g (5%) of compound 3 were obtained according to general method 4 starting from cetyl-1-ol and 1-(2-hydroxy-ethyl)-chinuclidine.

[0878] 1 H-NMR (600MHz, CDCl 3 -d1, 300K): δ=4.29 (2H, broad peak-s), 3.84 (2H, q), 3.73 (8H, m), 2.17 (1H, m), 1.60 (2H, quintet), 1.34- 1.22(26H, m), 0.88(3H, t)ppm

[0879] ESI-MS: Found: m / z 460.5 [M+H], Calculated: 460.7 g / mol

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Abstract

The present invention provides novel alkyl phospholipid derivatives with reduced cytotoxicity that are useful for treating various diseases and / or pathophysiological conditions in mammals, preferably humans, that are caused by microorganisms, in particular bacteria, fungi, protozoa and / or viruses. Such alkyl phospholipids can be employed as single drugs or in the course of combination therapies and can also be used for the treatment of tumors.

Description

technical field [0001] The present invention relates to novel alkylphospholipid derivatives with reduced cytotoxicity for the treatment of various diseases and / or pathophysiological conditions in mammals caused by microorganisms, especially bacteria, fungi, protozoa, and / or viruses. Said alkylphospholipids can be used as a single drug or in combination therapy, said alkylphospholipids also display antineoplastic properties. Background technique [0002] Alkylphospholipids (APLs), as a species of substance, have been known for decades to possess properties and exhibit biological activities that can be advantageously exploited for the treatment of various medical indications. [0003] For example, in Drugs of Today, Vol. 34, Suppl. F, 1998, a review of the different actions and uses of alkylphosphocholines is given. [0004] Additional literature on alkylphospholipids, their various uses, and associated indications, including various standard of care, includes the literature ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/661A61K31/675A61K31/683A61K31/685A61P31/04A61P31/06A61P31/00A61P31/08A61P31/10A61P31/12A61P31/14A61P31/16A61P31/18A61P31/20A61P31/22
CPCA61K31/675A61P31/00A61P31/04A61P31/06A61P31/08A61P31/10A61P31/12A61P31/14A61P31/16A61P31/18A61P31/20A61P31/22Y02A50/30
Inventor D·佩里苏M·彼得拉斯J·恩格尔
Owner AETERNA ZENTARIS GMBH
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