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Use of benzo-fused heterocycle sulfamide derivatives for preparing drugs of treatment of epilepsy

A use, technology for epilepsy, applied in the field of benzo-condensed heterocyclic sulfonamide derivatives, treatment or preventive treatment, prevention, prevention or inhibition of epilepsy and epilepsy, reversal, can solve the inability to produce, no anti-epileptic drugs, etc. question

Inactive Publication Date: 2013-11-27
JANSSEN PHARMA NV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0022] Currently, there is no known method of inhibiting the epileptogenic process to prevent epilepsy or other similar seizure-related disorders in asymptomatic patients who have or are at risk of developing the disease without knowing it. disease development
In addition, there is no known method to prevent the development of the epileptogenesis process or to reverse the epileptogenesis process, so that the collection of neurons in the epileptogenic zone that is the source of seizure activity, or prone to participate or able to participate in seizure activity, is not displayed. Abnormal, spontaneous, sudden, recurrent, or excessive discharges of neural tissue that are sensitive or incapable of producing such seizure activity
Furthermore, there are no approved or unapproved drugs recognized as having antiepileptic properties such that there are no true antiepileptic drugs (AEGDs) (see, Schmidt, D. and Rogawski, M.A., Epilepsy Research, 2002, 50; 71-78)

Method used

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  • Use of benzo-fused heterocycle sulfamide derivatives for preparing drugs of treatment of epilepsy
  • Use of benzo-fused heterocycle sulfamide derivatives for preparing drugs of treatment of epilepsy
  • Use of benzo-fused heterocycle sulfamide derivatives for preparing drugs of treatment of epilepsy

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0212] ((3,4-Dihydro-2H-benzo[1,4]dioxepin-3-yl)methyl)sulfonamide (Compound #3)

[0213]

[0214] Catechol (5.09 g, 46. mmol) and potassium carbonate were mixed in acetonitrile and heated to reflux for one hour. 2-Chloromethyl-3-chloro-1-propene (5.78 g, 46.2 mmol) was added and the reaction was continued at reflux for 24 hours. The solution was cooled to room temperature and filtered. The filtrate was evaporated and the residue was diluted with water and extracted with diethyl ether (3x). via MgSO 4 The combined organic solutions were dried and concentrated. Chromatography (2% diethyl ether in hexanes) gave 3-methylene-3,4-dihydro-2H-benzo[b][1,4]dioxepatriene as a colorless oil.

[0215] MS (ESI): 163.2 (M+H + )

[0216] 1 H NMR (300 MHz, CDCl 3 ), δ: 6.94 (m, 4H), 5.07 (s, 2H), 4.76 (s, 4H).

[0217] 3-Methylene-3,4-dihydro-2H-benzo[b][1,4]dioxepatriene (5.00 g, 30.8 mmol) was dissolved in anhydrous THF (100 ml). At 0 °C, borane-THF (1.0 M in THF, 10.3 ml) w...

Embodiment 2

[0223] N-(2,3-Dihydro-benzo[1,4]dioxin-2-ylmethyl)-sulfonamide (compound #1)

[0224]

[0225] Mix racemic 2,3-dihydro-1,4-benzodioxin-2-ylmethylamine (4.4 g, 26 mmol) and sulfonamide (5.1 g , 53mmol), and refluxed for 2 hours. The reaction was cooled to room temperature and a small amount of solid was filtered and discarded. The filtrate was evaporated in vacuo and purified using flash column chromatography (DCM:methanol-10:1) to give a white solid. This solid was recrystallized from DCM to give the title compound as a white solid.

[0226] mp: 97.5-98.5°C.

[0227] Elemental analysis:

[0228] Analytical theoretical values: C, 44.25; H, 4.95; N, 11.47; S, 13.13

[0229] Analytical found values: C, 44.28; H, 4.66; N, 11.21; S, 13.15

[0230] 1 H NMR (DMSO d6) δ6.85 (m, 4H), 6.68 (bd s, 3H, NH), 4.28 (m, 2H), 3.97 (dd, J=6.9, 11.4Hz, 1H), 3.20 (m, 1H), 3.10(m, 1H).

Embodiment 3

[0232] (Benzo[1,3]dioxol-2-ylmethyl)sulfonamide (Compound #2)

[0233]

[0234] Catechol (10.26 g, 93.2 mmol), sodium methoxide (25% by weight in methanol, 40.3 g, 186 mmol) and methyl dichloroacetate (13.3 g, 93.2 mmol) were mixed in dry methanol (100 mL). The solution was heated to reflux overnight. The reaction was cooled to room temperature, acidified by the addition of concentrated hydrochloric acid, then reduced in vacuo to about 50ml in volume. Water was added and the mixture was extracted with ether (3 x 100ml). with MgSO 4 The combined organic solution was dried, concentrated to a brown solid, and chromatographed (2% ethyl acetate in hexanes) to afford benzo[1,3]dioxole-2 as a colorless oil - methyl carboxylate.

[0235] MS(ESI): 195.10(M+H + ).

[0236] 1 H NMR (300 MHz, CDCl 3 ), δ: 6.89 (broad peak, 4H), 6.29 (s, 1H), 4.34 (q, J=7Hz, 2H), 1.33 (t, J=7Hz, 3H).

[0237] To methyl benzo[1,3]dioxol-2-carboxylate (7.21 g, 40.0 mmol) was added ammonium hydr...

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Abstract

The present invention is a method for treating, preventing, reversing, arresting or inhibiting the occurrence, development and maturation of seizures or seizure-related disorders. More specifically, the present invention is directed to uses of benzo-fused heterocycle sulfamide derivatives of formula (I) and formula (II) as described herein for the manufacture of a medicament to therapeutically or prophylactically treat, prevnet, reverse, arrest or inhibit epileptogenesis and epilepsy.

Description

[0001] Cross Reference Related Applications [0002] This application claims the benefit of US Provisional Application 60 / 751,496, filed December 19, 2005, the entire contents of which are incorporated herein by reference. technical field [0003] The present invention relates to the use of benzo-condensed heterocyclic sulfonamide derivatives for treating, preventing, reversing, arresting or inhibiting the occurrence, development and maturation of seizures or seizure-related diseases. More particularly, the present invention relates to methods of using benzofused heterocyclic sulfonamide derivatives for the therapeutic or prophylactic treatment, prevention, reversal, arrest or inhibition of epileptogenesis and epilepsy. Background technique [0004] Various injuries or traumas to the central nervous system (CNS) or peripheral nervous system (PNS) can produce profound and long-lasting neurological and psychiatric symptoms and disorders. A common mechanism for these effects ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/353A61K31/357A61P25/08
Inventor V·L·史密斯-斯温托斯基
Owner JANSSEN PHARMA NV
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