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New process for the synthesis of moguisteine

A technology of methyl and dioxolane, applied in the new field of synthesizing mojisteine, can solve problems such as removal

Inactive Publication Date: 2013-03-27
DOMPE FARM SPA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, high molecular weight impurities are difficult to remove by usual purification methods and require distillation under high vacuum (114 °C, 0.5 mm Hg)

Method used

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  • New process for the synthesis of moguisteine
  • New process for the synthesis of moguisteine
  • New process for the synthesis of moguisteine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] Step a) Preparation of formula 2-[(2-methoxyphenoxy)methyl]-1,3-dioxolane in 1-methoxy-2-propanol Intermediate of ring (4) (4)

[0071] The raw materials were used in the amounts shown in Table 1 below.

[0072] Table 1: Substances and amounts of Example 1

[0073] Raw materials

Density

g

ml

Moore

The molar ratio of

Guaiacol

1.129

297.6

263.6

2.40

1.00

1-methoxy-2-propanol

0.920

607.2

660.0

*

*

Potassium carbonate powder

497.6

3.60

1.50

97% 2-bromomethyl-1,3-dioxide

Pentacyclic

1.628

475.2

291.9

2.76

1.15

50% KOH solution

1.516

84.2

55.5

0.75

0.31

Deionized water, first serving

1.00

660.0

660.0

*

*

Deionized water, second portion

1.00

1320.0

1320.0

*

*

Deionized water for washing

1.00

2x500

2x500

*

*

[0074] Under a nitrogen atmosphere, load potassium carbonate fine powder and 1-methoxy-2-propanol into a completely dry 6-liter flask and place the material under stirrin...

Embodiment 2

[0100] Step a) Preparation of formula 2-[(2-methoxyphenoxy)methyl]-1,3-dioxolane in N-methylpyrrolidone Intermediate of ring (4) (4)

[0101] The following raw materials were used in the amounts shown in Table 2.

[0102] Table 2: Substances and amounts used in Example 2

[0103] Raw materials

Density

g

ml

Moore

The molar ratio of

Guaiacol

1.129

99.2

87.9

0.80

1.00

N-methylpyrrolidone

1.028

514.0

500.0

*

*

Potassium carbonate powder

221.14

1.60

2.00

97% 2-bromomethyl-1,3-dioxide

Pentacyclic

1.628

158.4

97.3

0.92

1.15

Deionized water for quenching

1.00

1400.0

1400.0

Toluene for extraction

0.865

692.0

800.0

Deionized water, first wash

1.00

800.0

800.0

30% NaOH solution

1.335

50.0

37.5

Deionized water, second wash

1.00

800.0

800.0

30% NaOH solution

1.335

50.0

37.5

Deionized water, third wash

1.00

800.0

800.0

30% NaOH solution

1.335

50.0

37.5

Carbon

5.0

Tolue...

Embodiment 3-31

[0114] Step a) Intermediate (4) of formula 2-[(2-methoxyphenoxy)methyl]-1,3-dioxolane (4) preparation

[0115] By following the same procedure as shown in Example 1, but using the amount, reaction solvent, time, and temperature shown in Table 3, the yield and purity shown in Table 4 below were used to obtain Intermediate (4).

[0116] Table 3: Reaction conditions of Example 3-31

[0117]

[0118] Example

[0119] Table 4: Yield and purity of intermediate (4) obtained in Example 3-31

[0120]

[0121] Therefore, in all the examples, intermediate (4) was obtained in high yield and with a purity of greater than 99%. According to the present invention, the intermediates of Examples 1, 28, 29 and 31 have the best appearance and quality.

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Abstract

The invention relates to a process for the synthesis of moguisteine that is ethyl ester of (R,S)-3-[2-[(2-methoxyphenoxy)methyl]-1,3-thiazolidin-3-yl]-3-oxypropanoic acid which comprises the steps of forming a new cyclic intermediate of formula 2-[(2-methoxyphenoxy)methyl]-1,3-dioxolane (4), forming (R,S)-2-[(2-methoxyphenoxy)methyl]-1,3-thiazolidine (6) and reacting this latter with monoethylmalonic acid (7) or a salt thereof. The moguisteine of the invention is obtained in high yield and purity.

Description

Invention field [0001] The present invention relates to the synthesis of (R,S)-3-[2-[(2-methoxyphenoxy)methyl]-1,3-thiazolidine- of formula (1) commonly referred to as mogistein A new method for ethyl 3-yl]-3-oxopropionate. [0002] [0003] The present invention also relates to a new intermediate named 2-[(2-methoxyphenoxy)methyl]-1,3-dioxolane (4). Background technique [0004] Mojistan is a peripheral antitussive that has shown a potent effect on the treatment of dry cough without phlegm, which is usually associated with respiratory disorders of different severity. [0005] In EP 169581 B1, a compound with a 3-acyl-2-substituted-thiazolidine structure was first described as an antitussive agent. [0006] In EP 333080 B1, Mojistan was prepared for the first time and described as the selected compound within the 3-acyl-2-substituted-thiazolidine family. [0007] N-acyl-substituted thiazolidines were prepared according to the teachings given in the patent, wherein the acyl groups are ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/04C07D317/22
CPCC07D317/22C07D277/04A61P11/14
Inventor 恩里科·维加诺马西米利亚诺·阿瑞吉雷纳托·莫尔特尼西蒙娜·兰弗兰科尼欧内斯托·兰多尼奥
Owner DOMPE FARM SPA
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