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Phenylcarbinol kearny ester compounds

A compound, the technology of benzyloxycarbonyl, applied in the field of benzyl alcohol carnitide compound, can solve the problems of inconvenient research and development of preparations, difficult preparations and the like

Active Publication Date: 2010-12-08
SHANDONG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these carnitine derivatives have extremely strong hygroscopicity due to their special chemical structure, and they also have a strong tendency to hydrolyze in aqueous solution, which brings great inconvenience to the research and development of preparations. It is limited to a few dosage forms such as tablets, capsules, and freeze-dried powder injections, and the preparation is difficult

Method used

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  • Phenylcarbinol kearny ester compounds
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  • Phenylcarbinol kearny ester compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Preparation of cinnamoyl chloride

[0028] Take 29.6 g (0.2 mol) of cinnamic acid and add 100 ml (0.84 mol) of thionyl chloride, stir to dissolve, heat under reflux for 4 h, and evaporate the excess thionyl chloride to obtain a yellow solid, which is cinnamoyl chloride, which is directly used in the next reaction .

[0029] Preparation of Cinnamoyl-L-Carnitine Chloride Hydrochloride

[0030] Take 30.06g (0.125mol) of L-carnitine hydrochloride and add CF 3 100ml of COOH, stir and dissolve, add the cinnamoyl chloride obtained in the upper part at 0°C in stages, and heat up to 45-50°C after dropping, and keep the reaction for 20 hours. After the reaction is completed, take out and cool to room temperature, add 800 ml of acetone, stir for 2 hours, filter, add 1000 ml of diethyl ether to the filtrate, stir until a white precipitate is formed, put it in the refrigerator for 12 hours. After taking out, stir for 1 hour, filter, and dry to o...

Embodiment 2

[0040] According to the similar method of embodiment 1, replace cinnamoyl chloride with acetyl chloride, prepare R is CH 3 The compound of formula I.

[0041] 1 H NMR (300 Hz, D 2 O): 2.01 (3H, s, CH 3 COO-); 2.62-2.65 (2H, m, -CH 2 COO-); 3.12(9H, S, (CH 3 ) 3 N-); 3.58 (2H, d, d, -NCH 2 -); 4.56(2H, s, -CH2 C 6 H 5 ); 5.53 (1H, m, -NCH 2 CH -); 7.35-7.39 (5H, d, -CH2C 6 H 5 )

[0042] IR (KBr plate): 3013 (γ CH ), 1733 (γ C＝O )1478, 1411(δ CH2，CH3 ), 1215(v C-N ), 709, 726, 768, 934 (aromatic ring). ESI-MS (m / z): 294.4 [M+H] + .

Embodiment 3

[0044] According to the similar method of embodiment 1, replace cinnamoyl chloride with propionyl chloride, prepare R is CH 2 CH 3 The compound of formula I.

[0045] 1 H NMR (300 Hz, D 2 O): 1.00-1.05 (3H, t, CH 3 CH 2 COO-); 2.51-2.58 (2H, m, -CH 3 CH 2 COO-); 3.03-3.08 (2H, m, -CH 2 COO-); 3.19(9H, S, (CH 3 ) 3 N-); 3.58 (2H, d, d, -NCH 2 -); 4.49 (2H, s, -CH 2 C 6 H 5 ); 5.01(1H, m, -NCH2 CH -); 7.25-7.30 (5H, d, -CH 2 C 6 H 5 )

[0046] IR (KBr plate): 3061, 2926 (γ CH ), 1725 (γ C＝O ), 1479, 1403 (δ CH2，CH3 ), 1177(v C-N ), 727, 768, 876, 933 (aromatic ring). ESI-MS (m / z): 308.7 [M+H] + .

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Abstract

The invention discloses a group of benzyl alcohol Kearny ester compounds, which have low moisture and good stability and are the pro-drug of a carnitine with a completely new structure.

Description

technical field [0001] The present invention relates to the field of medicinal chemistry, more particularly, to a benzyl alcohol carnitide compound. Background technique [0002] The research on L-carnitine derivatives was carried out in the 1950s, mainly focusing on the biological activity of carnitine, imitating coenzyme A, and preparing various acylated carnitines. Since 1980, with the in-depth study of carnitine's mechanism of action in the human body, a series of carnitine transportases have been discovered, and the research on carnitine and its derivatives has been deepened, and its field of action has continued to expand. The medicinal value of derivatives is increasingly prominent, and the ones that have been used clinically include: acetyl carnitine, propionyl carnitine, citrate carnitine, etc. Among them, acetyl carnitine and propionyl carnitine have been used in Europe listed. Acetyl-L-carnitine is superior to L-carnitine in neuroprotective activity and is curre...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61P25/00A61K31/215A61P9/00C07C227/16C07C229/22
Inventor 徐文方贡肖巍冯波翟海民崔美兰王丽徐桂英张志华赵雪坤
Owner SHANDONG UNIV