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Method for synthe sizing (3aS)-5, 5-dioxo-2, 3, 3a, 4-tetrahydric-1H-pyrrolo [2,1-c] [1,2,4] benzodiazine

A technology of benzothiadiazine and dioxo, applied in the synthesis of (3aS)-5,5-dioxo-2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c A new field of ][1,2,4]benzothiadiazines, which can solve problems such as low enantioselectivity and laborious enrichment

Inactive Publication Date: 2002-11-27
LES LAB SERVIER SA
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  • Abstract
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  • Application Information

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Problems solved by technology

[0007] However, the low enantioselectivity of the reduction requires laborious enrichment to obtain compounds of formula (I) in optically pure form

Method used

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  • Method for synthe sizing (3aS)-5, 5-dioxo-2, 3, 3a, 4-tetrahydric-1H-pyrrolo [2,1-c] [1,2,4] benzodiazine

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Embodiment Construction

[0010] The following examples illustrate the invention but do not limit it in any way.

[0011] The chemical purity of the compound of formula (I) was determined by HPLC chromatography, using a HYPERSIL BDS C18 column, and a mixture of water / acetonitrile=25 / 75 as the eluent. (Detector: 210 nm; oven temperature (oven): 30° C.; flow rate 1 ml / min.)

[0012] The enantiomeric purity of the compound of formula (I) was determined by HPLC chromatography using a CHIRALPACKAS (Daicel) column with a mixture of ethanol / heptane = 70 / 30 as eluent. (Detector: 212nm; Furnace temperature: 25°C; Flow rate 1ml / min.) Abbreviation: BINAP: 2,2'-(bis(diphenylphosphino))-1,1'-binaphthyl DPEN: diphenyl Ethylenediamine Example: (3aS)-5,5-dioxo-2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,2,4]benzothio diazine

[0013] The reaction was carried out in an autoclave.

[0014] Dissolve 40 g of 5,5-dioxo-2,3-dihydro-1H-pyrrolo[2,1-c][1,2,4]benzothiadiazine in 450 ml of toluene previously degassed with nitrog...

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Abstract

The present invention relates to the industrial enantioselective catalytic hydrogenation of 5,5-dioxo-2,3-dihydro-1H-pyrrolo[2,1-c][1,2,4]benzothiadiazine Synthesis of formula (I)(3aS)-5,5-dioxo-2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,2,4]benzothiadi method of oxazine.

Description

technical field [0001] The present invention relates to the industrial synthesis of formula (I) (3aS)-5,5-dioxo-2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,2,4] Novel process for the formation of benzothiadiazines and their addition salts with pharmaceutically acceptable acids. [0002] Formula (I) compound and salt thereof have strong activity, contribute to the activation that glutamic acid causes at AMPA receptor level, make it can be used for the treatment and prevention and glutamatergic (glutamatergic) neurotransmission dysfunction relevant Pathological conditions such as memory impairment and cognitive impairment associated with aging and with anxiety and depressive syndromes, memory deficits in progressive neurodegenerative diseases, and sequelae of acute neurodegenerative diseases. Background technique [0003] EP 0 692 484 patent specification describes compounds of formula (I), their use in therapy and processes for their preparation. [0004] Considering the phar...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/06A61K31/549A61P25/00A61P25/22A61P25/24A61P25/28C07B61/00C07D513/04
CPCC07D513/04A61P25/00A61P25/22A61P25/24A61P25/28C07D513/06
Inventor E·福切尔G·托米诺特J-P·勒库夫J·A·兰斯登C·J·考布里
Owner LES LAB SERVIER SA
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