Fluorinated 2-amino-4-(benzylamino)phenylcarbamate derivatives

A technology of compounds and compositions, applied in the direction of palladium organic compounds, platinum group organic compounds, active ingredients of heterocyclic compounds, etc.

Inactive Publication Date: 2015-03-25
SCIFLUOR LIFE SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004]Despite the fact that there are approved medications for epilepsy, many patients are not adequately treated with currently available options
It is estimated that nearly one-third of patients with epilepsy have refractory or uncontrollable seizures, or have significant adverse side effects secondary to medications that limit their ability to adequately control their epilepsy with medication

Method used

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  • Fluorinated 2-amino-4-(benzylamino)phenylcarbamate derivatives
  • Fluorinated 2-amino-4-(benzylamino)phenylcarbamate derivatives
  • Fluorinated 2-amino-4-(benzylamino)phenylcarbamate derivatives

Examples

Experimental program
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preparation example Construction

[0114] Begin with Compound A or E in the preparation outlined in Schemes 1A and 2A. Both are commercially available from chemical suppliers.

[0115] In Step 1 of Scheme 1A, the fluorine atom adjacent to the nitro group of compound A is converted to an amino group to form compound B. For example, compound A can be treated with methanolic ammonia to form compound B. In step 2, the remaining fluorine atom is coupled to the benzylamino compound to form compound C. For example, the fluorine atom of compound B can use Et 3 N, I 2 Coupling with 4-fluorobenzylamine with DMSO forms compound C. In step 3, the nitro group of compound C is reduced and carbamate is formed to provide compounds of formula I. For example, the nitro group of compound C can be reduced using zinc powder and ammonium chloride in methanol. Carbamate formation can be carried out using ethyl chloroformate. In some cases, Compound B is commercially available, in which case the synthetic scheme starts at Step ...

Embodiment 1

[0298] Example 1. Experimental Procedures and Characterization of Compounds

Embodiment 1A

[0299] Example 1A: Synthesis of ethyl (2-amino-3-fluoro-4-((4-fluorobenzyl)amino)phenyl)carbamate (Compound 1A in Table 1)

[0300]

[0301] 2,3-Difluoro-6-nitroaniline (2)

[0302] A solution of 1,2,3-trifluoro-4-nitrobenzene (1) (1.00 g, 5.64 mmol, 1.00 equiv) in methanolic ammonia (1.5 mL) was placed in a microwave vial and heated under microwave to 70°C for 90 minutes. The solvent was evaporated in vacuo to give a crude product which was purified by silica gel column chromatography (EtOAc / Hexane 1:49) to give compound 2 (0.350 g, 35.6%) as a yellow solid. TLC: 10% EtOAc / hexane (R f : 0.10); 1 H NMR (500 MHz, DMSO- d 6 ): δ 7.94-7.91 (m, 1H), 7.51 (s, 2H), 6.75-6.70 (m, 1H); LC-MS: m / z= 173 (M + -1) 3.15 (99.8% purity) at room temperature.

[0303] 2-Fluoro-N1-(4-fluorobenzyl)-4-nitrobenzene-1,3-diamine (3)

[0304] To a stirred suspension of compound 2 (0.100 g, 0.570 mmol, 1.00 equiv) in dry DMSO (4.6 mL) was added 4-fluorobenzylamine (0.210 g, 1.72 mmol, ...

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Abstract

The invention relates to fluorinated compounds and their use as anti-epileptic, muscle- relaxing, fever-reducing and peripherally analgesically acting medications and as imaging agents. Novel fluorinated 2-amino-4-(benzylamino)phenyl carbamate derivatives of ezogabine and pharmaceutically acceptable salts or solvates thereof and their use are described.

Description

[0001] related application [0002] This application claims priority under 35 U.S.C. § 119(e) of U.S. Provisional Application Nos. 61 / 640157 and 61 / 697690, filed April 30, 2012, and September 6, 2012, respectively, which are incorporated by reference to this article. [0003] background [0004] Epilepsy is one of the most common chronic neurological disorders. It is usually diagnosed after two or more unprovoked episodes at least 1 day apart, and it affects approximately 50 million people worldwide. Epilepsy is a serious and potentially life-threatening condition, and patients with epilepsy have significantly increased morbidity, including closed head injuries, fractures, burns, dental injuries, and soft tissue injuries. In patients with epilepsy, decline or deterioration of memory, cognition, depression and sexual function and other lifestyle restrictions often occur. Patients with epilepsy are also at increased risk of mortality compared with the general population. [0...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C271/28C07D213/75A61K31/27A61K31/44A61P25/08A61B8/13
CPCA61K51/0406A61P1/00A61P21/02A61P25/00A61P25/02A61P25/06A61P25/08A61P25/18A61P25/22A61P25/30A61P27/02A61P27/16A61P29/00C07B59/001C07C271/28C07D213/75C07F5/025C07F15/006A61K31/27A61K51/0455C07B59/002C07B2200/05
Inventor M. E. 杜根T. 富鲁亚S. D. 爱德华兹A. 普罗希特
Owner SCIFLUOR LIFE SCI
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