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A process for preparing N-acylated lysophosphatidylcholine compounds and a pharmaceutical composition for treatment of metabolic bone disease comprising said compounds

A technology of phosphatidylcholine and composition, which is applied in the field of preparation of N-acyl lysophosphatidylcholine compound and the pharmaceutical composition containing this compound for treating metabolic bone disease, which can solve the lack of sufficient research on efficacy and side effects And other issues

Inactive Publication Date: 2005-04-20
EWHA UNIV IND COLLABORATION FOUND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, there are vitamin D preparations such as calcitonin, but there is still a lack of sufficient research on their efficacy and side effects

Method used

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  • A process for preparing N-acylated lysophosphatidylcholine compounds and a pharmaceutical composition for treatment of metabolic bone disease comprising said compounds
  • A process for preparing N-acylated lysophosphatidylcholine compounds and a pharmaceutical composition for treatment of metabolic bone disease comprising said compounds
  • A process for preparing N-acylated lysophosphatidylcholine compounds and a pharmaceutical composition for treatment of metabolic bone disease comprising said compounds

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Experimental program
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Effect test

preparation example Construction

[0063] When the production method of the present invention is applied, techniques commonly used in the art can be used for specific reaction conditions.

[0064] The typical method of generating methyl ester hydrochloride from amino acid is to react with methanol saturated with hydrochloric acid, weaken the nucleophilicity of the amino group, and selectively methylate the carboxyl group. React L-serine with methanol saturated with hydrochloric acid for 2 hours at room temperature, and recrystallize with ether / methanol to obtain serine methyl ester hydrochloride.

[0065] The amide conjugation reaction is carried out by activating the carboxyl group with an appropriate peptide bond conjugating reagent. In particular, L-serine methyl ester hydrochloride is a primary ammonia, which is much more reactive than secondary ammonia. Therefore, using relatively cheap 1,3-dicyclohexylcarbodiimide as the peptide bond-binding reagent, the synthesis yield is also high. At this point, the ...

Embodiment 1

[0077] [Example 1] Synthesis of N-stearyl-o-phosphatidylcholine-L-serine methyl ester (CHJ-0011)

[0078] (1) Synthesis of L-serine methyl ester hydrochloride

[0079] 47.7mmol of L-serine was dissolved in 476ml of methanol, saturated with hydrochloric acid and reacted at room temperature for 2 hours. After recovering the solvent, recrystallize with methanol and ether to obtain the target compound L-serine methyl ester hydrochloride (yield: 98%, melting point: 161-162°C, [α]25D=+3.4 (c 2.0, MeOH)). The structures of the synthesized compounds were confirmed by FTIR, 1H-NMR and 13C-NMR.

[0080] FTIR (KBr, cm-1): 3349 O-H absorption peak, 2943 sp3 C-H absorption peak, 1749 ester carbonyl absorption peak

[0081] 1H NMR (CD3OD): δ4.07~4.10 (1H, t, J=3.9Hz), 3.88-3.93 (2H, m), 3.79 (3H, s) Absorption peak s of methoxyl proton: singlet , d: doublet, t: triplet, m: multiplet)

[0082] 13C NMR (CD3OD): δ52.69, 55.10, 59.67, 168.37 carbonyl absorption peaks

[0083] (2) Synthesis...

Embodiment 2

[0091] [Example 2] Synthesis of N-stearyl-o-phosphatidylcholine-L-serine hydroxymethyl (CHJ-0013)

[0092] (1) Synthesis of L-serine methyl ester hydrochloride

[0093] 47.7mmol of L-serine was dissolved in 476ml of methanol, saturated with hydrochloric acid and reacted at room temperature for 2 hours. After recovering the solvent, recrystallize with methanol and ether to obtain the target compound L-serine methyl ester hydrochloride (yield: 98%, melting point: 161-162°C, [α]25D=+3.4 (c 0.2, MeOH)). The structures of the synthesized compounds were confirmed by FTIR, 1H-NMR and 13C-NMR.

[0094] FTIR (KBr, cm-1): 3349 O-H absorption peak, 2943 sp3 C-H absorption peak, 1749 ester carbonyl absorption peak

[0095] 1H NMR (CD3OD): δ4.07~4.10 (1H, t, J=3.9Hz), 3.88~3.93 (2H, m), 3.79 (3H, s) the absorption peak of the methoxy proton (s: singlet , d: doublet, t: triplet, m: multiplet)

[0096] 13C NMR (CD3OD): δ2.69, 55.10, 59.67, 168.37 carbonyl absorption peaks

[0097] (2) S...

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Abstract

The present invention relates to a pharmaceutical composition for preventing and / or treating metabolic bone disease. The pharmaceutical composition comprises an effective dose of an N-acyl lysophosphatidylcholine compound (chemical formula 1) and a carrier thereof that can be used in pharmaceutical preparations . Furthermore, the present invention relates to a preparation method for preparing the N-acyl lysophosphatidylcholine compound of Chemical Formula 1 from serine.

Description

field of invention [0001] The present invention relates to a pharmaceutical composition for preventing and / or treating metabolic bone disease, the pharmaceutical composition comprising an effective dose of N-acyl lysophosphatidylcholine compound (chemical formula 1) and its carrier which can be used for pharmaceutical preparations . Background technique [0002] Bone is composed of bone cells such as osteocytes, osteoclasts, and osteoblasts, hydroxyapatite crystals, collagenous fibers, mucopolysaccharides, and other bone matrix, as well as spaces such as bone marrow cavity, blood vessels, tubules, and small bone cavities (Stavros C.M., Endocrine Reviews, 21(2), 115-137(2000)). The main function of bone is to mechanically support the limbs, protect major organs, provide the microenvironment necessary for hematopoiesis, and store calcium and various minerals. [0003] Bone is constantly repeating the process of growth, development and maintenance. Old bone is continuously r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/661A61K31/14A61K31/16A61K31/6615C07F9/09C07F9/10
CPCA61K31/14A61K31/16A61K31/6615C07F9/091C07F9/10A01M29/30A01M2200/012
Inventor 钱吉子韩素叶李章熙金洪姬李银姬金英娥郭韩福
Owner EWHA UNIV IND COLLABORATION FOUND
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