WO2016037072A3 - Analogues d'enopeptine s et leurs procédés d'utilisation - Google Patents

Analogues d'enopeptine s et leurs procédés d'utilisation Download PDF

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Publication number
WO2016037072A3
WO2016037072A3 PCT/US2015/048568 US2015048568W WO2016037072A3 WO 2016037072 A3 WO2016037072 A3 WO 2016037072A3 US 2015048568 W US2015048568 W US 2015048568W WO 2016037072 A3 WO2016037072 A3 WO 2016037072A3
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WIPO (PCT)
Prior art keywords
enopeptin
analogs
methods
compounds
bacterial
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PCT/US2015/048568
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English (en)
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WO2016037072A2 (fr
WO2016037072A8 (fr
Inventor
Jason K SELLO
Daniel William CARNEY
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Brown University
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Publication of WO2016037072A2 publication Critical patent/WO2016037072A2/fr
Publication of WO2016037072A8 publication Critical patent/WO2016037072A8/fr
Publication of WO2016037072A3 publication Critical patent/WO2016037072A3/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/48—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a saturated carbon skeleton containing rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/49—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/50—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of an unsaturated carbon skeleton containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne des analogues d'enopeptine répondant à la Formule (I) ou (II) : et des sels pharmaceutiquement acceptables de ceux-ci, et des compositions pharmaceutiques de ceux-ci, dans laquelle R1, R2, R3, R4, R5, R6, m, X, RXa et Y sont tels que définis aux présentes. Ces composés ont montré une activité antibactérienne, interfèrent de façon concurrentielle avec la pompe à efflux bactérien, et/ou potentialisent les activités d'autres agents antibactériens, tel qu'un ADEP4, contre des bactéries qui ne sont pas sensibles du fait des pompes d'efflux. L'invention concerne en outre des méthodes de traitement et des procédés d'utilisation de tels composés.
PCT/US2015/048568 2014-09-04 2015-09-04 Analogues d'enopeptine s et leurs procédés d'utilisation WO2016037072A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201462046092P 2014-09-04 2014-09-04
US62/046,092 2014-09-04

Publications (3)

Publication Number Publication Date
WO2016037072A2 WO2016037072A2 (fr) 2016-03-10
WO2016037072A8 WO2016037072A8 (fr) 2016-06-23
WO2016037072A3 true WO2016037072A3 (fr) 2016-08-18

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PCT/US2015/048568 WO2016037072A2 (fr) 2014-09-04 2015-09-04 Analogues d'enopeptine s et leurs procédés d'utilisation

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Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9193767B2 (en) 2011-03-30 2015-11-24 Brown University Enopeptins, uses thereof, and methods of synthesis thereto

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997006162A1 (fr) * 1995-08-07 1997-02-20 Zeneca Limited Synthese en un seul creuset de derives de 2-oxazolidinone
WO2001055106A2 (fr) * 2000-01-28 2001-08-02 Melacure Therapeutics Ab Nouveaux agonistes et antagonistes de recepteurs des melanocortines
US20050026973A1 (en) * 2003-07-28 2005-02-03 Veronique Leclerc New heterocyclic oxime compounds
WO2012135615A2 (fr) * 2011-03-30 2012-10-04 Brown University Enopeptines, utilisations de celles-ci, et procédés de synthèse de celles-ci
CN102838523A (zh) * 2011-06-23 2012-12-26 南开大学 抗肠病毒71(ev71)戊内酰胺类化合物及其制备方法和用途
CN103130710A (zh) * 2011-11-29 2013-06-05 南开大学 抗肠病毒71(ev71)己内酰胺醛类化合物及其制备方法和用途
CN103145608A (zh) * 2011-12-07 2013-06-12 南开大学 抗肠病毒71(ev71)己内酰胺类化合物及其制备方法和用途

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997006162A1 (fr) * 1995-08-07 1997-02-20 Zeneca Limited Synthese en un seul creuset de derives de 2-oxazolidinone
WO2001055106A2 (fr) * 2000-01-28 2001-08-02 Melacure Therapeutics Ab Nouveaux agonistes et antagonistes de recepteurs des melanocortines
US20050026973A1 (en) * 2003-07-28 2005-02-03 Veronique Leclerc New heterocyclic oxime compounds
WO2012135615A2 (fr) * 2011-03-30 2012-10-04 Brown University Enopeptines, utilisations de celles-ci, et procédés de synthèse de celles-ci
CN102838523A (zh) * 2011-06-23 2012-12-26 南开大学 抗肠病毒71(ev71)戊内酰胺类化合物及其制备方法和用途
CN103130710A (zh) * 2011-11-29 2013-06-05 南开大学 抗肠病毒71(ev71)己内酰胺醛类化合物及其制备方法和用途
CN103145608A (zh) * 2011-12-07 2013-06-12 南开大学 抗肠病毒71(ev71)己内酰胺类化合物及其制备方法和用途

Non-Patent Citations (9)

* Cited by examiner, † Cited by third party
Title
13 June 2011 (2011-06-13), retrieved from STN Database accession no. 1308980-53-1 *
15 August 2012 (2012-08-15), retrieved from STN Database accession no. 1391543-99-9 *
7 March 2014 (2014-03-07), retrieved from STN Database accession no. 1563579-82-7 *
CARIELLO, N. F. ET AL.: "Comparison of the computer programs DEREK and TOPK AT to predict bacterial mutagenicity", MUTAGENESIS, vol. 17, no. 4, 2002, pages 321 - 329, XP009001387, DOI: doi:10.1093/mutage/17.4.321 *
CARNEY, D. W. ET AL.: "A simple fragment of the cyclic acyldepsipeptides is necessary and sufficient for ClpP activation and antibacterial activity", C HEMBIOCHEM, vol. 15, no. 15, October 2014 (2014-10-01), pages 2216 - 2220 *
COMPTON, C. L. ET AL.: "Fragment-Based Strategy for Investigating and Suppr essing the Efflux of Bioactive Small Molecules", ACS INFECTIOUS DISEASES, vol. 1, no. 1, pages 53 - 58 *
GEORGIEV, L. ET AL.: "Anti-tyrosinase, antioxidant and antimicrobial activi ties of hydroxycinnamoylamides", MEDICINAL CHEMISTRY RESEARCH, vol. 22, no. 9, 2013, pages 4173 - 4182 *
RACHID, S. ET AL.: "Characterization of a Novel Type of Oxidative Decarboxy lase Involved in the Biosynthesis of the Styryl Moiety of Chondrochloren fro m an Acylated Tyrosine", JOURNAL OF BIOLOGICAL CHEMISTRY, vol. 285, no. 17, 2010, pages 12482 - 12489 *
WEI, Q. Y. ET AL.: "Antimicrobial activities of the cinnamoyl amide of amin o acid derivatives", ASIAN JOURNAL OF CHEMISTRY, vol. 24, no. 6, 2012, pages 2383 - 2388 *

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WO2016037072A8 (fr) 2016-06-23

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