N-(5-membered aromatic ring)-amido anti-viral compounds

Technology of a compound, heteroaryl, applied in the field of medicinal chemistry

Inactive Publication Date: 2008-12-24
SMITHKLINE BECKMAN CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0021] However, none of the compounds described above has progressed past clinical trials

Method used

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  • N-(5-membered aromatic ring)-amido anti-viral compounds
  • N-(5-membered aromatic ring)-amido anti-viral compounds
  • N-(5-membered aromatic ring)-amido anti-viral compounds

Examples

Experimental program
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example

[0296] In the following examples and throughout the application, the following abbreviations have the following meanings. If not defined, terms have their generally accepted meanings.

[0297] atm = atmospheric pressure

[0298] cm = centimeter

[0299] DIEA = Diisopropylethylamine

[0300] DMF = dimethylformamide

[0301] DMSO = dimethyl sulfoxide

[0302] eq. = equivalent

[0303] F.W. = formula weight

[0304] g = gram

[0305] HATU = N-[(dimethylamino)-1H-1,2,3-triazolo[4,5-b]pyridin-1-ylmethylene]-N-methylmethanoammonium N-hexafluorophosphate -Oxide

[0306] HPLC = High Pressure Liquid Chromatography

[0307] KOAc = potassium acetate

[0308] L = liter

[0309] MeCN = acetonitrile

[0310] mg = milligram

[0311] mL = milliliter

[0312] mmol = millimole

[0313] MS = mass spectrum

[0314] TEA = Triethylamine

[0315] TFA = trifluoroacetic acid

[0316] THF = Tetrahydrofuran

[0317] TLC = Thin Layer Chromatography

[0318] v / v = volume / volume

[031...

example 1

[0369] 2-[4-(3-Amino-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester (compound 5001)

[0370] Thiourea (0.31 g, 4.1 mmol) and sodium acetate (0.44 g, 5.3 mmol) were combined in 30 mL of absolute ethanol. To this suspension was added 2-bromo-1-(3-nitro-phenyl)-ethanone (1.0 g, 4.1 mmol). The reaction mixture was stirred overnight at room temperature. The reaction mixture was evaporated to dryness to yield 4-(3-nitro-phenyl)-thiazol-2-ylamine which was used in the next step without any further purification. MS: 222.0 (M+H + ).

[0371] Z-Pro-OH (1.5 g, 6.15 mmol) and HATU (2.3 g, 6.15 mmol) were combined in 30 mL of anhydrous DMF. To this solution was added DIEA (1.5 mL, 8.8 mmol). This solution was stirred at room temperature for 1 hour. To this solution was added 4-(3-nitro-phenyl)-thiazol-2-ylamine (0.9, 4.1 mmol). The reaction mixture was stirred overnight at room temperature. The crude material was purified using reverse phase HPLC to yield...

example 2

[0374] 2-(4-Benzoyl-5-yl-thiazol-2-ylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester (compound 5002)

[0375] From 10 mg of 4-benzo[1,2]dioxol-5-yl-thiazol-2-ylamine in 1 mL solution using general procedure G. MS: 452.0 (M+H + ).

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Abstract

Disclosed are compounds having Formula (I) and the compositions and methods thereof for treating or preventing a viral infection mediated at least in part by a virus in the Flaviviridae family of viruses, wherein A, R<2>, m, R, V, W, T, Z, R<1>, Y and p are disclosed herein.

Description

[0001] This application claims the benefit of co-pending US Provisional Patent Application No. 60 / 749,855, filed December 12, 2005, under 35 U.S.C. 119(e), which is incorporated herein by reference in its entirety. technical field [0002] The present invention relates to the field of medicinal chemistry, and in particular to compounds, formulations, compositions and methods for treating viral infections in patients at least partially mediated by viruses of the Flaviviridae family. [0003] references [0004] The following publications are referenced in this application with superscript numbers: [0005] 1. Szabo et al., Pathol. Oncol. Res. 2003, 9: 215-221. [0006] 2. Hoofnagle JH, Hepatology 1997, 26:15S-20S. [0007] 3. Thomson BJ and Finch RG, Clin Microbial Infect. 2005, 11:86-94. [0008] 4. Moriishi K and Matsuura Y, Antiviral Chemistry and Chemotherapy (Antivir. Chem. Chemother.) 2003, 14: 285-297. [0009] 5. Fried et al., N. Engl. J Med 2002, 347: 975-982. [...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/12C07D413/12C07D417/12C07D417/14C07D495/04C07D513/04A61K31/427A61K31/4155A61K31/4436
CPCC07D403/12C07D413/12C07D417/12C07D417/14C07D495/04C07D513/04A61P31/12A61P31/14A61K31/4155
Inventor 弗朗兹·乌尔里希·施米茨克里斯托弗·唐·罗伯茨阿里·德加尼·穆罕默德·阿巴迪罗纳德·康拉德·格里菲斯马丁·罗伯特·利弗斯伊琳娜·斯洛博多夫鲁帕·拉伊
Owner SMITHKLINE BECKMAN CORP
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