DK2802558T3 - Forbindelser med antibakteriel aktivitet, fremgangsmåde til deres fremstilling og farmaceutiske præparater, der omfatter dem - Google Patents

Forbindelser med antibakteriel aktivitet, fremgangsmåde til deres fremstilling og farmaceutiske præparater, der omfatter dem Download PDF

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Publication number
DK2802558T3
DK2802558T3 DK13709265.6T DK13709265T DK2802558T3 DK 2802558 T3 DK2802558 T3 DK 2802558T3 DK 13709265 T DK13709265 T DK 13709265T DK 2802558 T3 DK2802558 T3 DK 2802558T3
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Denmark
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compound
group
pharmaceutically acceptable
mmol
alkyl group
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DK13709265.6T
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English (en)
Inventor
Gerardo Burton
Mario Martinez
Elvira Zini
Fernando Durã�N
Muã`Oz Veronica Mora
Lucila Bertoncello
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Consejo Nac De Investig Científicas Y Técnicas (Conicet)
Laboratorios Richmond Soc Anónima Com Ind Y Financiera
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/86—Hydrazides; Thio or imino analogues thereof
    • 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
    • A61P31/04—Antibacterial agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C235/38—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
    • C07C259/08—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/58—Preparation of carboxylic acid halides
    • C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • 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

Claims (15)

1. Forbindelse med følgende strukturformel:
kendetegnet ved, at Ri er valgt blandt H, en lineær eller forgrenet (Cl-C5)-alkylgruppe og en COR4-gmppe, R2 er valgt blandt H, en lineær eller forgrenet (Cl-C5)-alkylgruppe og en COR5-gruppe, R3 er valgt blandt H, en lineær eller forgrenet (Cl-C5)-alkylgruppe, en lineær eller forgrenet (Cl-C5)-0-alkylgruppe, en cycloalkyl af (C5-C6)-carbonatomer, en arylgruppe og en aryl-(Cl-C5)-alkylgruppe, hvor arylgruppen kan være en usubstitueret aryl eller en aryl substitueret med en eller flere R6-grupper og en NHCOR5-gruppe, eller R2- og R3-grupperne sammen med N kan danne en substitueret eller usubstitueret piperidin-, morpholin- eller piperazingruppe, R4 er valgt blandt H og en (Cl-C5)-alkylgruppe, R5 er valgt blandt en usubstitueret arylgruppe eller en arylgruppe substitueret med en eller flere Re-grupper, lineære eller forgrenede (Cl-C5)-alkyl- eller pyridyngrupper og en pyridingruppe, R6 er valgt blandt (Cl-C5)-alkylgrupper, halogen og nitro, forudsat at Ri, R2 og R3 ikke samtidig er H-atomer, et farmaceutisk acceptabelt salt deraf, en stereoisomer deraf eller en blanding af stereoisomerer deraf.
2. Forbindelse ifølge krav 1, et farmaceutisk acceptabelt salt deraf, kendetegnet ved, at det er valgt blandt følgende forbindelser:
3. Farmaceutisk præparat, kendetegnet ved at omfatte mindst én forbindelse ifølge krav 1 og farmaceutisk acceptable excipienser.
4. Farmaceutisk præparat, kendetegnet ved at omfatte mindst én forbindelse eller et farmaceutisk acceptabelt salt deraf ifølge krav 2, og farmaceutisk acceptable excipienser.
5. Forbindelse ifølge krav 1 eller 2 til anvendelse som et medikament.
6. Farmaceutisk præparat, kendetegnet ved at omfatte mindst én forbindelse eller et farmaceutisk acceptabelt salt, en stereoisomer eller en blanding af stereoisomerer deraf ifølge krav 1, hvilket præparat yderligere omfatter mindst ét andet terapeutisk aktivt stof, som adskiller sig fra den første forbindelse.
7. Forbindelse ifølge krav 1 eller 2 til anvendelse i behandlingen af infektioner, kendetegnet ved at omfatte administration af en forbindelse eller et farmaceutisk acceptabelt salt deraf ifølge krav 1.
8. Fremgangsmåde til fremstilling af forbindelser ifølge formel I, kendetegnet ved at omfatte følgende trin: a) kobling af 2-methoxy-5-iodbenzaldehyd eller 2-acetyloxy-5-iodbenzaldehyd med acrylsyre eller kobling af 2-methoxy-5-iodbenzaldehyd med en ester af acrylsyre, efterfulgt af hydrolyse, b) behandling af det fra trin a) resulterende kanelsyrederivat med en fluorering sreagens, c) omsætning af det i trin b) opnåede acylfluorid med en amin eller et derivat deraf i nærværelse af en base.
9. Fremgangsmåde ifølge det foregående krav, kendetegnet ved, at acrylsyreesteren er methylacrylat.
10. Fremgangsmåde ifølge krav 8, kendetegnet ved, at fluoreringsreagensen er bis-[(2-methoxyethyl)amino] svovltrifluorid (DeoxoFluor®).
11. Fremgangsmåde ifølge krav 8, kendetegnet ved yderligere at omfatte mindst ét trin med nedsivning af den fra fluoreringsreaktionen resulterende blanding gennem et silicagellag for at opnå en acylfluoridopløsning uden biprodukter fra fluorering sreaktionen.
12. Fremgangsmåde ifølge det foregående krav, kendetegnet ved, at acylfluoridopløsningen uden biprodukter fra fluoreringsreaktionen behandles direkte med en amin i nærværelse af en base for således at opnå det tilsvarende amid.
13. Fremgangsmåde ifølge krav 11, kendetegnet ved, at acylfluoridopløsningen uden biprodukter fra fluoreringsreaktionen behandles direkte med et aminsalt og en base for således at opnå det tilsvarende amid.
14. Fremgangsmåde ifølge krav 11, kendetegnet ved, at acylfluoridopløsningen uden biprodukter fra fluoreringsreaktionen behandles direkte med et hydrazinderivat og en base for således at opnå det tilsvarende hydrazid.
15. Fremgangsmåde ifølge krav 12, 13 og 14, kendetegnet ved, at basen er en tertiær amin valgt blandt triethylamin, l,4-diazabicyclo-(2,2,2)-octan eller diazabicycloundecan (DBU).
DK13709265.6T 2012-01-11 2013-01-10 Forbindelser med antibakteriel aktivitet, fremgangsmåde til deres fremstilling og farmaceutiske præparater, der omfatter dem DK2802558T3 (da)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ARP120100090A AR085073A1 (es) 2012-01-11 2012-01-11 Compuestos con actividad antibacteriana, un procedimiento para su obtencion y composiciones farmaceuticas que los comprenden
PCT/IB2013/050235 WO2013105053A1 (en) 2012-01-11 2013-01-10 Compounds having antibacterial activity, process for their preparation and pharmaceutical compositions comprising them

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DK2802558T3 true DK2802558T3 (da) 2016-09-12

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US (1) US9255071B2 (da)
EP (1) EP2802558B1 (da)
AR (1) AR085073A1 (da)
BR (1) BR112014017190B1 (da)
CA (1) CA2863221C (da)
DK (1) DK2802558T3 (da)
ES (1) ES2588597T3 (da)
MX (1) MX355456B (da)
PT (1) PT2802558T (da)
WO (1) WO2013105053A1 (da)

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CN104926721A (zh) * 2014-03-21 2015-09-23 兰州大学 异烟肼咖啡酸酰胺化衍生物及在抗结核杆菌药物中的应用

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IL77905A (en) * 1985-02-18 1989-10-31 Wellcome Found Dieneamides,their preparation and their use as insecticides and acaricides
IT1255467B (it) * 1992-07-29 1995-11-02 Dompe Farmaceutici Spa Ammidi acriliche farmacologicamente attive
DE4421536A1 (de) * 1994-06-20 1995-12-21 Hoechst Ag Perfluoralkylgruppen tragende phenylsubstituierte Alkenylcarbonsäure-guanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
CN1046730C (zh) * 1994-06-21 1999-11-24 株式会社大塚制药工场 吡唑并[1,5-a]嘧啶衍生物
DE19610784A1 (de) * 1996-03-19 1997-09-25 Hoechst Ag Fluoralkyl- und Fluoralkoxysubstituierte heterocyclische Bradykinin-Antagonisten, Verfahren zu ihrer Herstellung und ihre Verwendung
US6046239A (en) * 1997-08-05 2000-04-04 American Home Products Corporation Anthranilic acid analogs
US6239077B1 (en) * 1998-05-01 2001-05-29 Nihon Nohyaku Co., Ltd. Aminoacetonitrile derivative agricultural and horticultural insecticide containing the same and use thereof
WO2004052371A2 (en) * 2002-12-11 2004-06-24 7Tm Pharma A/S Cyclic quinoline compounds for use in mch receptor related disorders

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US9255071B2 (en) 2016-02-09
CA2863221A1 (en) 2013-07-18
BR112014017190A2 (pt) 2017-06-27
BR112014017190B1 (pt) 2020-12-29
ES2588597T3 (es) 2016-11-03
AR085073A1 (es) 2013-09-11
PT2802558T (pt) 2016-09-02
WO2013105053A1 (en) 2013-07-18
CA2863221C (en) 2020-09-08
EP2802558A1 (en) 2014-11-19
MX355456B (es) 2018-04-19
US20140357678A1 (en) 2014-12-04
MX2014008437A (es) 2015-02-24
EP2802558B1 (en) 2016-06-01

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