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New process for the synthesis of moguisteine

A technology of methyl and methoxyphenoxy, which is applied in the new field of synthesizing mogisteine, which can solve the problems of removal

Inactive Publication Date: 2010-11-10
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 material

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

*

*

[0074] raw material

density

g

ml

Moore

The molar ratio of

Deionized water for washing

1.00

2x500

2x500

*

*

[0075] Under a nitrogen atmosphere, load potassium carbonate fine powder and 1-methoxy-2-propanol into a completely dry 6-liter flask a...

Embodiment 2

[0101] Step a) Preparation of formula 2-[(2-methoxyphenoxy)methyl]-1,3-dioxolane in N-methylpyrrolidone Intermediate of ring (4) (4)

[0102] The following raw materials were used in the amounts shown in Table 2.

[0103] Table 2: Substances and amounts used in Example 2

[0104] raw material

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

[0105] raw material

density

g

ml

Moore

Th...

Embodiment 3-31

[0116] Step a) Intermediate (4) of formula 2-[(2-methoxyphenoxy)methyl]-1,3-dioxolane (4) preparation

[0117] By following the same procedure as shown in Example 1, but using the amount, reaction solvent, time, and temperature shown in Table 3, intermediate (4) was obtained in the yield and purity shown in Table 4 below.

[0118] Table 3: Reaction conditions of Example 3-31

[0119]

[0120]

[0121]

[0122]

[0123]

[0124] Table 4: Yield and purity of intermediate (4) obtained in Example 3-31

[0125]

[0126]

[0127] Therefore, in all the examples, intermediate (4) was obtained in high yield and with a purity 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 mogistan 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 said patent, wherein said acyl groups are...

Claims

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Application Information

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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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