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Use of benzo-fused heterocycle sulfamide derivatives as neuroprotective agents

A technique for neuroprotection, uses, applied in the treatment of acute and/or chronic neurodegenerative disorders, a method for the treatment of acute or chronic neurodegenerative disorders characterized by neuronal destruction or death, benzo-fused heterocyclic sulfonamide derivatives as a neuroprotective agent

Inactive Publication Date: 2012-07-04
JANSSEN PHARMA NV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The difficulty with most treatments is that none of these treatments have an effect on the disease process caused by neuronal degeneration
Ultimately, a therapeutic point appears to be reached where pharmacology can no longer compensate for the loss of basal ganglia dopamine

Method used

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  • Use of benzo-fused heterocycle sulfamide derivatives as neuroprotective agents
  • Use of benzo-fused heterocycle sulfamide derivatives as neuroprotective agents
  • Use of benzo-fused heterocycle sulfamide derivatives as neuroprotective agents

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0152] ((3,4-Dihydro-2H-benzo[1,4]dioxepin-3-yl)methyl)sulfonamide (Compound #3)

[0153]

[0154] Catechol (5.09 g, 46.2 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.

[0155] MS (ESI): 163.2 (M+H + )

[0156] 1 H NMR (300MHz, CDCl 3 ), δ: 6.94 (m, 4H), 5.07 (s, 2H), 4.76 (s, 4H).

[0157] 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

[0163] N-(2,3-Dihydro-benzo[1,4]dioxin-2-ylmethyl)-sulfonamide (compound #1)

[0164]

[0165] 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.

[0166] mp: 97.5-98.5°C.

[0167] Elemental analysis:

[0168] Analytical theoretical values: C, 44.25; H, 4.95; N, 11.47; S, 13.13

[0169] Analytical found values: C, 44.28; H, 4.66; N, 11.21; S, 13.15

[0170] 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

[0172] ( Benzo[1,3]dioxol-2-ylmethyl)sulfonamide (Compound #2)

[0173]

[0174] 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. MS(ESI): 195.10(M+H + ).

[0175] 1 H NMR (300MHz, CDCl 3 ), δ: 6.89 (broad peak, 4H), 6.29 (s, 1H), 4.34 (q, J=7Hz, 2H), 1.33 (t, J=7Hz, 3H).

[0176] To methyl benzo[1,3]dioxol-2-carboxylate (7.21 g, 40.0 mmol) was added ammonium hydroxide (29...

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Abstract

The present invention is a methods for neuroprotection, for treating an acute neurodegenerative disorder, for treating a chronic neurodegenerative disorder and / or for preventing neuron death or damage following brain, head and / or spinal cord trauma or injury comprising administering to a subject in need thereof a therapeutically effective amount of one or more novel benzo-fused heterocycle sulfamide derivatives of formula (I) and formula (II) as herein defined.

Description

[0001] Cross Reference Related Applications [0002] This application claims the benefit of US Provisional Application 60 / 751,494, 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 as neuroprotective agents. The present invention further relates to the use of benzofused heterocyclic sulfonamide derivatives for the treatment of acute and / or chronic neurodegenerative disorders, more particularly, for the treatment of acute or chronic neurodegenerative disorders characterized by neuronal destruction or death. Background technique [0004] Neurodegenerative disorders afflict large numbers of individuals in the United States and abroad. For example, many individuals suffer from neurodegenerative diseases. These diseases include a number of severely debilitating conditions such as Parkinson's disease, amyotrophic...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/353A61P25/08A61K31/357A61P25/14A61P25/02A61P25/16
Inventor V·L·史密斯-斯温托斯基A·B·赖茨
Owner JANSSEN PHARMA NV
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