WO2013091062A3 - Aldimine-derived compounds, pharmaceutical compositions and use - Google Patents

Aldimine-derived compounds, pharmaceutical compositions and use Download PDF

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Publication number
WO2013091062A3
WO2013091062A3 PCT/BR2012/000562 BR2012000562W WO2013091062A3 WO 2013091062 A3 WO2013091062 A3 WO 2013091062A3 BR 2012000562 W BR2012000562 W BR 2012000562W WO 2013091062 A3 WO2013091062 A3 WO 2013091062A3
Authority
WO
WIPO (PCT)
Prior art keywords
aldimine
drugs
pharmaceutical compositions
derived compounds
medicinal
Prior art date
Application number
PCT/BR2012/000562
Other languages
French (fr)
Portuguese (pt)
Other versions
WO2013091062A2 (en
Inventor
Angelo DE FÁTIMA
Stoianoff DE RESENDE
Daniel DE ASSIS SANTOS
Adão APARECIDO SABINO
Rosemeire BRONDI ALVEZ
Cleiton MOREIRA DA SILVA
Cleide VIVIANE BUZANELLO MARTINS
Thais FURTADO FERREIRA MAGALHÃES
Danielle LETÍCIA DA SILVA
Alan KIILL GASPAROTO
Original Assignee
Universidade Federal De Minas Gerais - Ufmg
Fundação De Amparo A Pesquisa De Minas Gerais - Fapemig
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from BRPI1106432 external-priority patent/BRPI1106432A2/en
Priority claimed from BR102012023898-5A external-priority patent/BR102012023898B1/en
Application filed by Universidade Federal De Minas Gerais - Ufmg, Fundação De Amparo A Pesquisa De Minas Gerais - Fapemig filed Critical Universidade Federal De Minas Gerais - Ufmg
Publication of WO2013091062A2 publication Critical patent/WO2013091062A2/en
Publication of WO2013091062A3 publication Critical patent/WO2013091062A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
    • C07C251/04—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C251/10—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
    • C07C251/16—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
    • C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/61—Carboxylic acid nitriles containing cyano groups and nitrogen atoms being part of imino groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/33—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring
    • C07C323/35—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring the thio group being a sulfide group
    • C07C323/36—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring the thio group being a sulfide group the sulfur atom of the sulfide group being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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
    • C07D307/70—Nitro radicals
    • C07D307/71—Nitro radicals attached in position 5
    • C07D307/72—Nitro radicals attached in position 5 with hydrocarbon radicals, substituted by nitrogen-containing radicals, attached in position 2
    • C07D307/73—Nitro radicals attached in position 5 with hydrocarbon radicals, substituted by nitrogen-containing radicals, attached in position 2 by amino or imino, or substituted amino or imino radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/58—Radicals substituted by nitrogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

The present invention comprises aldimine-derived compounds, pharmaceutical compositions containing such compounds and pharmaceutically acceptable excipients, beside the use thereof for treating fungal infections of medicinal and/or veterinary importance. Aldimines and derivatives thereof have been shown to exhibit antifungal activity equivalent to or better than that of commercially available medicinal drugs, such as fluconazole. Since these drugs are new, pathogen resistance to these drugs is quite low. Aldimine synthesis is carried out in a single-step process in which the reaction is completed in two minutes, with yields of 70-98%, making large-scale production possible, since it is a fast and low-cost process, when compared to the production process of other pharmaceuticals available.
PCT/BR2012/000562 2011-09-23 2012-09-24 Aldimine-derived compounds, pharmaceutical compositions and use WO2013091062A2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
BRPI1106432-3 2011-09-23
BRPI1106432 BRPI1106432A2 (en) 2011-09-23 2011-09-23 aldimine-derived compounds, pharmaceutical compositions and use
BR102012023898-5A BR102012023898B1 (en) 2012-09-21 2012-09-21 Compounds derived from aldimines, pharmaceutical compositions and use
BRBR1020120238985 2012-09-21

Publications (2)

Publication Number Publication Date
WO2013091062A2 WO2013091062A2 (en) 2013-06-27
WO2013091062A3 true WO2013091062A3 (en) 2013-10-10

Family

ID=48669624

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/BR2012/000562 WO2013091062A2 (en) 2011-09-23 2012-09-24 Aldimine-derived compounds, pharmaceutical compositions and use

Country Status (1)

Country Link
WO (1) WO2013091062A2 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106397233A (en) * 2016-08-26 2017-02-15 南通奥凯生物技术开发有限公司 Preparation method of pharmaceutical grade disodium ethylene diamine tetraacetate

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4198349A (en) * 1977-10-06 1980-04-15 William H. Rorer, Inc. Benzylideneaniline derivatives
US20090298905A1 (en) * 2005-04-15 2009-12-03 Fernando Pedro Cossio Nitrogenatd trans-stilbene analogs, method for the obtention and medical applications thereof

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4198349A (en) * 1977-10-06 1980-04-15 William H. Rorer, Inc. Benzylideneaniline derivatives
US20090298905A1 (en) * 2005-04-15 2009-12-03 Fernando Pedro Cossio Nitrogenatd trans-stilbene analogs, method for the obtention and medical applications thereof

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
CLEITON M. DA SILVA ET AL.: "Schiff bases: A short review of their antimicrobial activities", JOURNAL OF ADVANCED RESEARCH, vol. 2, 2011, pages 1 - 8 *
K. MOUNIKA ET AL.: "Synthesis, Characterization and Biological Activity of a Schiff Base Derived from 3-Ethoxy Salicylaldehyde and 2-Amino Benzoic acid and its Transition Metal Complexes", J. SCI. RES., vol. 2, no. 3, 2010, pages 513 - 524 *
MOHAMED N IBRAHIM ET AL.: "Synthesis, Characterization and Study of the Biological activity of Some Aldimines Derivatives", E-JOURNAL OF CHEMISTRY, vol. 3, no. 4, October 2006 (2006-10-01), pages 257 - 261 *
S.ARULMURUGAN ET AL.: "Biological Activities of Schiff Base and Its Complexes: a Review", RASAYAN J. CHEM., vol. 3, no. 3, 2010, pages 385 - 410 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106397233A (en) * 2016-08-26 2017-02-15 南通奥凯生物技术开发有限公司 Preparation method of pharmaceutical grade disodium ethylene diamine tetraacetate

Also Published As

Publication number Publication date
WO2013091062A2 (en) 2013-06-27

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