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Process for synthesizing Tuoteluodin L-tartrate

A synthesis method and tartaric acid technology are applied in chemical instruments and methods, preparation of organic compounds, preparation of aminohydroxy compounds, etc., and can solve the problems of anti-muscarinic side effects, difficulty in eye adjustment, serious side reactions, etc., and reduce side effects, The effect of rapid absorption and short response time

Inactive Publication Date: 2002-11-13
SHANGHAI INST OF PHARMA IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The muscarinic receptor antagonist oxybutynin has been used clinically as a drug for the treatment of unstable bladder, but it has antimuscarinic side effects, including dry mouth, difficulty in eye adjustment and rapid heart rate, often caused by severe side effects treatment interruption

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Preparation of 6-methyl-4-phenyl-3,4-dihydrocoumarin [I]

[0013] Cinnamic acid (74g, 0.5mol), p-methylphenol (54g, 0.5mol), and concentrated sulfuric acid (20ml) were mixed, heated to 120-125°C, stirred for 1 hour, TLC (petroleum ether: ethyl acetate=4:1 ) after showing that the raw material has reacted completely, it is cooled to room temperature, and the reactant is extracted with ethyl acetate (250ml×2), the organic layer is washed with water, and anhydrous Na 2 SO 4 After drying, the ethyl acetate was evaporated to give [I] 108g, the yield was 90.8%. mp: 83-86°C, directly put into the next reaction without purification.

Embodiment 2

[0015] Preparation of 3-(2-methoxy-5-methylphenyl)-3-phenylpropanoic acid [II] [I] (71.4 g, 0.3 mol) was dissolved in 10% NaOH solution (480 ml) at room temperature Add dropwise (CH 3 ) 2 SO 4 (94.5g, 0.75mol), and vigorously stirred, and after the solution became clear, heated at 80°C for 0.5 hours, TLC (same as above), cooled, acidified with hydrochloric acid, and dried to give milky white solid [II] 68.5g (85% yield Rate), mp = 133 ~ 135 ° C, no need to purify directly into the next step reaction.

Embodiment 3

[0017] Preparation of N,N-diisopropyl-3-(2-methoxy-5-methylphenyl)-3-phenylpropanamide [III].

[0018] [II] (1 3.5g, 0.05mol) and SOCl 2 (50ml) mixed, heated to reflux and stirred for 3 hours, evaporated excess SOCl 2 , to obtain brown acid chloride, the resulting acid chloride was dissolved in dichloromethane (50ml), and added dropwise to diisopropylamine (20.2g, 0.20mol) in 100ml of dichloromethane solution at 0°C, stirred for 2-4 hours, TLC (same as above ), after distilling off the solvent, put it into ice water, filter out the solid, wash with water and dry to obtain 14 g of light yellow solid [III] with a yield of 79%.

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PUM

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Abstract

A process for synthesizing Tuoteluodin L-tartrate is disclosed, and features cheap raw materials, gentle reaction condition, short reaction period, and stable quality of product.

Description

technical field [0001] The present invention relates to the technical field of pharmaceutical synthesis, in particular to (R)-N,N-diisopropyl-3-(2-hydroxyl-5-methylphenyl)-3-phenylpropylamine.L-bitartrate hydrogen salt resolve resolution. Background technique [0002] Overactive bladder is a common and distressing problem that affects the normal life of people of different ages - a common disease that occurs in both men and women, especially women and the elderly. Currently, the incidence of this disease is very high. According to the survey in Beijing, my country, the incidence of urinary incontinence in men over 50 years old is 16.4%, and the total incidence of mixed urinary incontinence and urge incontinence in women over 18 years old is as high as 40.4%. As my country enters the ranks of aging countries, it is related to An increase in overactive bladder will significantly affect the quality of life of older adults. [0003] The muscarinic receptor antagonist oxybutynin ...

Claims

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Application Information

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IPC IPC(8): C07C213/02C07C215/54
Inventor 袁哲东俞雄王强张秀平
Owner SHANGHAI INST OF PHARMA IND