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Compounds for the treatment of arenavirus infection

A technology of arenaviruses and compounds, applied in antiviral agents, organic chemistry, medical preparations containing active ingredients, etc.

Pending Publication Date: 2021-08-31
阿里桑治疗药物公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In some cases, however, hydrogen-deuterium exchange may lead to redirected metabolic sites ("metabolic switching") [Horning, M.G. et al. Metabolic switching of drug pathways as d consequence of drug substitution. Proceedings of the Second International Conference on Stable Isotopes( Klein. E.R. and Klein. P.D. eds.) (1976) 41-54; Miwa, G.T.; Lu, A.Y.H. Kinetic isotope effects and 'metabolic switching' incytochrome P450-catalyzed reactions. Bioessays (1987) 7: 215-219]

Method used

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  • Compounds for the treatment of arenavirus infection
  • Compounds for the treatment of arenavirus infection
  • Compounds for the treatment of arenavirus infection

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0254] Preparation of intermediates used in Examples A1 to A3.

[0255] 5-Bromo-N 1 -(4-isopropoxyphenyl)-4-methylbenzene-1,2-diamine

[0256]

[0257]To a solution of 1-bromo-5-fluoro-2-methyl-4-nitrobenzene (200 mg, 0.85 mmol) in isopropanol (2 mL) was added 4-isopropoxyaniline (129 mg, 0.85 mmol). The resulting mixture was stirred at 120 °C for 30 min under microwave irradiation. After cooling to room temperature, the reactant was concentrated under reduced pressure, and the residue was dissolved in ethanol (0.6 mL), dioxane (0.6 mL) and water (0.3 mL). Add iron (476mg, 8.5mmol) and NH to the solution 4 Cl (457 mg, 8-5 mmol). The reaction was stirred at 80 °C for 2 hours. After cooling to room temperature, the reaction was filtered through a pad of celite. The filtrate was concentrated under reduced pressure, and the residue was poured into water and extracted with ethyl acetate. The organic phase was subjected to Na 2 SO 4 Dry, filter and concentrate in vacuo...

Embodiment A1

[0267] Example A1: 2-(4-(1-(4-(tert-butoxy)phenyl)-5-methyl-1H-benzo[d]imidazol-6-yl)phenyl)propan-2- alcohol

[0268]

[0269] To 6-bromo-1-(4-(tert-butoxy)phenyl)-5-methyl-1H-benzo[d]imidazole (1g, 2.79mmol) in 1,4-dioxane (15mL) (4-(2-hydroxyprop-2-yl)phenyl)boronic acid (0.502g, 2.79mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II ) dichloride (230mg, 0.279mmol), potassium carbonate (1.15g, 8.4mmol) and water (5mL). The resulting reaction mixture was degassed with nitrogen for 10 min, then heated to 100 °C overnight. The reaction mixture was then diluted with ethyl acetate and washed with water. The organic phase was subjected to Na 2 SO 4 Dry, filter and concentrate in vacuo. Pass the residue through SiO 2 Purification by column chromatography (7:3 to 1:4 hexanes / EtOAc) afforded 826 mg of the product as a colorless oil. 1 H NMR (500MHz, DMSO-d6) δ8.48(s, 1H), 7.67(s, 1H), 7.58(d, 2H), 7.52(d, 2H), 7.31(s, 1H), 7.29(d, 2H), 7.17 (d, 2H), 5.01 (s, 1H), ...

preparation Embodiment C10 to C18

[0340]

[0341]

[0342]

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Abstract

Compounds as exemplified by compound A are useful in the treatment of arenavirus infections and viral infections mediated by arenavirus glycoproteins.

Description

[0001] Cross References to Related Applications [0002] This patent application is a continuation-in-part of and claims the benefit of priority of U.S. Provisional Patent Application Serial No. 62 / 776,390 filed December 6, 2018, which is hereby incorporated by reference in its entirety for all purposes. [0003] Statement of Rights Concerning Inventions Made Under Federally Sponsored Research and Development [0004] This invention was made with government support under R44 AI112097 awarded by the National Institutes of Health. The US Government has certain rights in this invention. [0005] ACCESSORIES TO SEQUENCE LISTINGS, TABLES OR COMPUTER PROGRAM LISTINGS FILLED ON COMPACT DISK [0006] Not applicable technical field [0007] The present invention relates to the use of heterocyclic compounds to inhibit arenavirus infection in humans, other mammals, or in cell culture, and to treat arenavirus infections such as Lassa (Lassa) hemorrhagic fever, Bolivian (Bolivian) hemor...

Claims

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Application Information

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IPC IPC(8): A61K31/4184C07D249/16
CPCA61K31/4184C07D471/04C07D249/18C07D235/06C07D487/04A61K31/437A61K31/4192A61K31/519A61P31/14C07D235/04
Inventor E.布朗V.R.甘特拉N.索科洛娃M.B.普勒韦G.亨克尔K.麦克科马克
Owner 阿里桑治疗药物公司
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