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Process for preparing 3-heteroaryl-3-hydroxypropanoic acid derivatives

a technology of enantiomer and heteroaryl, which is applied in the field of preparing enantiomerenriched 3heteroaryl3hydroxypropanoic acid derivatives and 3heteroaryl1aminopropan3ols, can solve the problems of inability to exhibit undesirable side effects, inactive or less active enantiomers, and the total yield is economically unacceptabl

Inactive Publication Date: 2006-11-23
BERENDES FRANK +5
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0120] The process according to the invention enjoys the advantage that it is possible to use readily available starting compounds to synthesize enantiomer-enriched 3-heteroaryl-3-hydroxypropanoic acid derivatives and 3-heteroaryl-1-aminopropan-3-ols, and their secondary products, on an industrial scale in high overall yields, high enantiomer excesses and high purities.

Problems solved by technology

In the case of some of these inhibitors, it has been shown that certain enantiomers are not only inactive, or less active, but are even able to exhibit undesirable side-effects (U.S. Pat. No. 5,104,899).
This method suffers from the disadvantage that, in principle, only 50% of the desired enantiomer can be obtained when racemates are resolved enzymically and the total yield is therefore economically unacceptable.

Method used

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  • Process for preparing 3-heteroaryl-3-hydroxypropanoic acid derivatives
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  • Process for preparing 3-heteroaryl-3-hydroxypropanoic acid derivatives

Examples

Experimental program
Comparison scheme
Effect test

examples 1 and 2

Reduction of methyl 3-oxo-(2-thiophenyl)propanoate Using Different Strains of the Baker's Yeast Saccharomyces cereviseae

[0121] The yeast strains (Saccharomyces cereviseae NG 247, Uniferm GmbH & Co KG, Monheim; Saccharomyces cereviseae Y278, Deutsche Hefe Werke [German Yeast Works] GmbH & Co oHG, Hamburg) were grown overnight, at 28° C. and with shaking (200 rpm), in 100 ml Erlenmeyer flasks containing 25 ml of YM medium (yeast extract, 3.0 g / l; malt extract, 3.0 g / l; peptone, 5.0 g / l; glucose, 10.0 g / l).

[0122] Each of the two yeast strains was incubated, at 28° C. and while shaking (200 rpm), in three 1-litre Erlenmeyer flasks which contained 200 ml of YM medium which had previously been inoculated with 12 ml of preliminary culture. Growth was monitored by measuring the optical density at 600 nm (OD600). After 6-7 h, the cultures reached an OD600 of 3 and were harvested by centrifugation (15 min, 8 000×g) and stored overnight at 4° C. in a refrigerator. For the reaction, 250 μl of...

example 3

Reduction of 3-(2-thiophenyl)-3-oxopropano-1-nitrile Using Saccharomyces cereviseae Y278

[0123] The yeast cells were grown, and the reaction was carried out, as described in Examples 1 and 2. The result is recorded in Table 2.

TABLE 2StartingReactionYield ofExampleYeast straincompound conc.time [h]Productproductee (S)3Y27820 mM922%85%

examples 4 and 5

Reduction of methyl 3-(2-thiophenyl)-3-oxopropanoate Using Geotrichum candidum

[0124] 200 ml of YM medium were inoculated, in a 1-litre Erlenmeyer flask and as the 1st preliminary culture, with the strain Geotrichum candidum ATCC34614 and the flasks were incubated at 28° C. for 18 h while being shaken. As the 2nd preliminary culture, two 1-litre Erlenmeyer flasks, in each case containing 200 ml of GC medium (KH2PO4, 11.18 g / l; K2HPO4, 3.12 g / l; glycerol, 30.0 g / l; yeast extract, 10.0 g / l; polypeptone, 5.0 g / l), were in each case inoculated with 10 ml of the 1st preliminary culture and likewise shaken at 28° C. for 18 h.

[0125] As the main culture, a 10 litre fermenter was loaded with 4.6 litres of GC medium and inoculated with 400 ml of the 2nd preliminary culture. The culture was grown at 28° C. using an aeration rate of 10 l / min and a stirring rate of 800 rpm. After 10 h, the fermenter was harvested. The cells were sedimented by being centrifuged for 15 min at 6000×g and were then...

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Abstract

The invention relates to a process for preparing enantiomer-enriched 3-heteroaryl-3-hydroxypropanoic acid derivatives and 3-heteroaryl-1-aminopropan-3-ols, and to their use.

Description

[0001] This application is a divisional of U.S. Ser. No. 10 / 669,424, which is pending and claims foreign priority benefit under 35 U.S.C. §119 of the German Patent Application No. 102 44 811.6 filed Sep. 26, 2002.BACKGROUND OF THE INVENTION [0002] 1. Field of the Invention [0003] The invention relates to a process for preparing enantiomer-enriched 3-heteroaryl-3-hydroxypropanoic acid derivatives and 3-heteroaryl-1-aminopropan-3-ols, and to their use. [0004] 2. Description of Related Art [0005] 3-Heteroaryl-3-hydroxypropanoic acid derivatives and 3-heteroaryl-1-aminopropan-3-ols have gained industrial significance, in particular, as intermediates for producing medicaments. Thus, some 3-heteroaryl-3-hydroxypropanoic acid derivatives and 3-heteroaryl-1-aminopropan-3-ols are used, for example, as precursor substances for preparing inhibitors of the uptake of serotonin or noradrenaline. In the case of some of these inhibitors, it has been shown that certain enantiomers are not only inact...

Claims

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Application Information

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IPC IPC(8): C07D333/22C07D213/55C07D307/02C07D307/54C07D333/24C12P17/00C12P17/04C12P17/12C12R1/645
CPCC07D213/55C07D307/54C12P17/12C12P17/00C12P17/04C07D333/24
Inventor BERENDES, FRANKECKERT, MARKUSBRINKMANN, NILSDREISBACH, CLAUSMEISSNER, RUTHKOCH, RAINHARD
Owner BERENDES FRANK
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