Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
  • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
  • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D233/91—Nitro radicals
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P33/00—Antiparasitic agents
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P33/00—Antiparasitic agents
  • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis

Definitions

• the molecule A / -benzyl-2- (2-nitro-1 H -amidazol-1-yl) acetamide is an antiparasitic, anti-protozoan derivative of 2-nitro-1 H-imidazole with activity against Trypanosoma cross], prepared and presented in 1966 by Hoffmann-La Roche & CO, patent granted in 1969 (Lon. Pat. L138,529).
• Patent US 6,870,057 B1 presents the synthesis of the antifungal Bifenilimidazoyl- (l) -phenylmethane, one of the steps of synthesis consists in the solid phase reaction of biphenylfincarbinol with excess of midazole, under microwave irradiation conditions (850-700W), 30 minutes, level 4 of the oven. Description of the invention.
• the present invention relates to the synthesis of an imidazole derivative with trypanocidal activity.
• the synthesis procedure is carried out in a dry environment, it is a simple, economical and friendly procedure with the environment.
• the synthesis consists of the manufacture of / V-benzyl-2- (2-nitro-1 H -amidazol-1-yl) acetamide.
• the method makes it possible to obtain / V-benzyl-2- (2-nitro-1 H-imidazol-1-yl) acetamide using as starting materials N-benzyl-2-hydroxyacetamide and 2-nitroimidazole, adding each of the materials of Start in equimolar relation.
• the procedure is clean, it is carried out by mixing both start and subsequent activation materials by microwave irradiation to form the / V-benzyl-2- (2-nitro-1 H -amidazol-1-yl) acetamide.
• the synthesis is quick and easy to execute.
• the reaction mixture is purified by passing it through a chromatography column, using alumina as the stationary phase and ethyl acetate as the mobile phase. The method does not require acidic or basic catalysts in the synthesis process.
• the process presented in this invention can be used to obtain other imidazole derivatives such as A / -benzyl-2- (1 H-imidazol-1-yl) acetamide using as starting materials 1 H-imidazole and N-benzyl 2-hydroxyacetamide or 1 H-imidazole and N-benzyl-2-chloroacetamide
• N-benzyl-2-hydroxyacetamide is mixed with 2-nitroimidazole in equimolar ratio.
• the starting materials are mixed in the solid state, in the absence of organic or inorganic solvent, placed in a transparent container to the microwave, in a silica bath and irradiated with microwave (700W), level 4 to 7 of the oven, during approximately 10 minutes.
• the reaction mixture is purified by passing it through a chromatography column, using alumina as the stationary phase and ethyl acetate as the mobile phase.
• the product obtained was analyzed by TLC, infrared spectroscopy, mass spectrometry.
• IR 1 156 and 1 145 cm “1 (NC, tertiary amine), 1539.3 and 1367cm “ 1 (CN, nitro group), 1660.3 cm -1 (CO-NH amide), 3275.3 crrf 1 (NH-amide).

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• Organic Chemistry (AREA)
• Chemical & Material Sciences (AREA)
• Health & Medical Sciences (AREA)
• Veterinary Medicine (AREA)
• Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Medicinal Chemistry (AREA)
• Tropical Medicine & Parasitology (AREA)
• Pharmacology & Pharmacy (AREA)
• Life Sciences & Earth Sciences (AREA)
• Animal Behavior & Ethology (AREA)
• General Health & Medical Sciences (AREA)
• Public Health (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
• Nitrogen Condensed Heterocyclic Rings (AREA)
• Plural Heterocyclic Compounds (AREA)

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Cited By (2)

Citations (2)

• 2013
  • 2013-11-19 SV SV2013004584A patent/SV2013004584A/es active IP Right Grant
• 2014
  • 2014-11-19 WO PCT/SV2014/000001 patent/WO2015076760A1/es not_active Ceased
  • 2014-11-19 US US15/033,238 patent/US9765036B2/en active Active - Reinstated
  • 2014-11-19 BR BR112016011160-5A patent/BR112016011160B1/pt active IP Right Grant
  • 2014-11-19 JP JP2016554169A patent/JP6425734B2/ja active Active

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