Novel benzo-fused heteroaryl sulfamide derivatives useful as anticonvulsant agents

A compound and a pharmaceutical technology, applied in the field of benzo-fused heteroaryl aminosulfonamide derivatives, can solve the problems of adverse side effects, weight loss, paresthesia and the like

Inactive Publication Date: 2007-12-19
JANSSEN PHARMA NV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, systemic antiglaucoma drugs such as acetazolamide have potentially adverse side effects, including paresthesias, nephrolithiasis, and weight loss

Method used

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  • Novel benzo-fused heteroaryl sulfamide derivatives useful as anticonvulsant agents
  • Novel benzo-fused heteroaryl sulfamide derivatives useful as anticonvulsant agents
  • Novel benzo-fused heteroaryl sulfamide derivatives useful as anticonvulsant agents

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preparation example Construction

[0167] Where the preparation of the compounds of the invention results in mixtures of stereoisomers, these isomers may be separated by conventional techniques such as preparative chromatography. Compounds may be prepared in racemic form, or by enantiospecific synthesis or resolution as individual enantiomers. The compounds can be resolved into their individual enantiomers by standard techniques, such as first reacting with an optically active acid such as (-)-di-p-toluoyl-D-tartaric acid and / or (+)-di-p-toluoyl -L-tartaric acid) to form a diastereomer pair as a salt, followed by fractional crystallization and regeneration as the free base. Compounds can also be resolved by first forming the diastereoisomeric esters or amides, followed by chromatographic separation and removal of the chiral prosthetic group. Alternatively, the compounds can be resolved using a chiral HPLC column.

[0168] During any of the preparations of the compounds of the invention, it may be necessary to...

Embodiment 1

[0185] N-(Benzo[b]thiophen-3-ylmethyl)-sulfamic acid amide (compound #1)

[0186]

[0187] Thianthene-3-carbaldehyde (1.62 g, 10.0 mmol) was dissolved in absolute ethanol (50 ml). Sulfuramide (4.0 g, 42 mmol) was added and the mixture was heated to reflux for 16 hours. Cool the mixture to room temperature. Sodium borohydride (0.416 g, 11.0 mmol) was added, and the mixture was stirred at room temperature for 3 hours. The reaction was diluted with water (50ml) and extracted with chloroform (3 x 75ml). The extracts were concentrated and chromatographed (5% methanol / DCM) to afford the title compound (white solid).

[0188] 1 H NMR (DMSO-d 5 ): δ7.98 (1H, dd, J = 6.5, 2.3Hz), 7.92 (1H, dd, J = 6.6, 2.4Hz), 7.62 (1H, s), 7.36-7.45 (2H, m), 7.08 ( 1H, t, J=6.3Hz), 6.72(2H, s), 4.31(2H, d, J=6.3Hz).

Embodiment 2

[0190] N-[(5-Chlorobenzo[b]thiophen-3-yl)methyl]-sulfamic acid amide (compound #3)

[0191]

[0192] (5-Chloro-1-benzothiophen-3-yl)methanamine (0.820g, 4.15mmol) and sulfuramide (2.5g, 26mmol) were mixed in anhydrous dioxane (50ml), and the mixture was heated to Reflux for 4 hours. The reaction was cooled and diluted with water (50ml). The solution was extracted with chloroform (3 x 75ml). The extracts were concentrated and chromatographed (5% methanol / DCM) to afford the title compound (white solid).

[0193] 1 H NMR (DMSO-d 6 ): δ8.05(2H, m), 7.74(1H, s), 7.40(1H, d, J=6.5Hz), 7.07(1H, t, J=6.3Hz), 6.72(2H, s), 4.26 (2H, d, J=6.4Hz).

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Abstract

The present invention relates to novel benzo-fused heteroaryl aminosulfonamide derivatives, pharmaceutical compositions containing them and their use in the treatment of epilepsy and related diseases.

Description

[0001] Cross References to Related Applications [0002] This application claims priority to US Provisional Application 60 / 604,134, filed August 24, 2004, which is hereby incorporated by reference in its entirety. field of invention [0003] The present invention relates to novel benzo-fused heteroaryl aminosulfonamide derivatives, pharmaceutical compositions containing them and their use in the treatment of epilepsy and related diseases. Background of the invention [0004] Epilepsy is a disorder in which patients experience recurrent seizures due to a chronic, underlying course. Because epilepsy has many forms and causes, epilepsy is a clinical phenomenon rather than a single disease. If epilepsy is defined by more than two unprovoked seizures, it is estimated that the incidence of epilepsy is about 0.3-0.5%, and the prevalence of epilepsy is about 5-10‰ in different populations around the world. [0005] A necessary step in the evaluation and treatment of patients with...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/58C07D307/81C07D209/14A61K31/381A61K31/343A61K31/404A61P25/08
CPCC07D333/20C07C307/06C07D307/81C07D409/12C07D209/14C07D333/58A61P25/08C07D333/60A61K31/381A61K31/343
Inventor 迈克尔·H·帕克A·B·赖茨B·E·玛丽亚诺夫
Owner JANSSEN PHARMA NV
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