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(S)-nifuratel, preparation method and application thereof

A nifuratel, reaction technology, applied in the direction of pharmaceutical formula, medical preparations containing active ingredients, organic active ingredients, etc.

Active Publication Date: 2007-09-19
SUNSTONE TANGSHAN PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The present inventors tried to obtain two isomers by the method of enantiomer resolution, but failed

Method used

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  • (S)-nifuratel, preparation method and application thereof
  • (S)-nifuratel, preparation method and application thereof
  • (S)-nifuratel, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0049] Preparation of Example 1 Intermediate 4

[0050] Intermediate 4 was prepared according to the following reaction:

[0051]

[0052] In a 2000mL reaction flask equipped with a high-efficiency reflux condenser and a dropping funnel, add 250g (3.125mol) of thiourea and 110mL of water, stir to partially dissolve the thiourea, stir for 10min under ice water cooling, remove the ice water, and add dropwise Dimethyl sulfate 15mL, the reaction spontaneously started under stirring, and exothermic, very violent at the beginning, after the reaction was stable, then slowly add the remaining dimethyl sulfate 155mL in the reaction bottle (about 1.5h), always Maintain a slightly boiling state, after the addition, continue to reflux for 1 hour, let stand overnight, add 260 mL of 95% ethanol, stir for a while, cool, filter, wash twice with 95% ethanol, and dry to obtain 4364 g of the product, with a yield of 84%, mp. 236°C (dec).

preparation Embodiment 2

[0053] Preparation Example 2. Preparation of Intermediate 5

[0054]

[0055] Ingredients:

[0056]

Reagent name

molecular weight

weight

(g)

moles

(mole)

level

Manufacturer

Remark

4

139

139g

1.0

self made

(S)-Epichlorohydrin

92.5

78.5mL

1.0

A.R.

Aldrich

Catalyst tetra-n-butyl

ammonium bromide

6.4g

TBAB

benzene

500ml

A.R.

beijing chemical reagent factory

30%NaOH

500mL

A.R.

beijing chemical reagent factory

self-provided

[0057] operate:

[0058] Add 4139g (1.0mol), (S)-epichlorohydrin 78.5mL (92.6g, 1.0mol), benzene 500mL, 30% sodium hydroxide 500mL and catalyst tetra-n-butylammonium bromide 6.4g in 2000mL reaction flask , reacted at room temperature for 6 hours under high-efficiency stirring, separated the ...

preparation Embodiment 3

[0061] Preparation Example 3. Preparation of Intermediate 6

[0062]

[0063]

Reagent name

molecular weight

weight

(g)

moles

(mole)

level

Manufacturer

5

104

88.5g

0.85

self made

Hydrazine hydrate

200mL

85％

Beijing Chemical Plant

[0064] operate:

[0065] Add 200mL of hydrazine hydrate into the reaction flask, heat to 90°C, add 588.5g (0.85mol) dropwise with stirring, and control the internal temperature at about 90°C, complete the addition in about 0.5h, and continue the reaction at 90°C for 1h. Excess hydrazine and water were removed by rotary evaporation to obtain a viscous colorless liquid. It can be directly used in the next reaction without purification, and the yield is quantitative.

[0066] If the obtained crude product is purified by vacuum distillation, a colorless transparent viscous pure product 6 is obtained, with a...

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Abstract

The invention discloses a nifuratel with a optical activity. Specifically, the invention provides a (S)-nifuratel, i.e. (S)-5-[(methylthio)methyl]-3-[(5-nitryl-2-furan)methylene]amido]-2-oxazolidone, the producing method and the combination including the optical activity compound. Compared to the racemic nifuratel, (S)-nifuratel has a better anti-inflammatory and anti-fungi activity. The invention also discloses the producing method for (S)-nifuratel which has the (S)-chloroepoxy propane as initial material, adopts the 3-dimension and selective synthesis method and produce a high optical purity (S)-nifuratel with a high yield.

Description

technical field [0001] The present invention relates to an optically active nifuratel, (S)-nifuratel, namely (S)-5-[(methylthio)methyl]-3-[[(5-nitro-2 -furyl)methylene]amino]-2-oxazolidinone, its preparation method and application. Background technique [0002] Nifuratel (Nifuratel), its chemical name: 5-[(methylthio)methyl]-3-[[(5-nitro-2-furan)methylene]amino]-2-oxazolidine Ketone, the English chemical name is: 5-[(Methylthio)methyl]-3-[[(5-nitro-2-furanyl)methylene]amino]-2-oxazolidinone, which is a nitrofuran antibiotic, has a significant therapeutic effect on vaginal Therapeutic effect of mixed infections. Its trichomonad killing activity is equivalent to metronidazole; at the same time, it has antibacterial (G+, G+) effect, and can effectively kill Chlamydia trachomatis and mycoplasma, and has certain activity against Candida; nifuratel is administered orally and vaginally It shows that it is well tolerated and has no drug resistance. The cure rate for bacterial vag...

Claims

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Application Information

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IPC IPC(8): C07D413/12A61K31/422A61P29/00A61P31/10
Inventor 韩志强
Owner SUNSTONE TANGSHAN PHARM CO LTD
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