AR053894A1 - Derivados de los acidos cinamico y fenilpropiolico utiles como agentes antiumorales - Google Patents

Derivados de los acidos cinamico y fenilpropiolico utiles como agentes antiumorales

Info

Publication number
AR053894A1
AR053894A1 ARP060102416A ARP060102416A AR053894A1 AR 053894 A1 AR053894 A1 AR 053894A1 AR P060102416 A ARP060102416 A AR P060102416A AR P060102416 A ARP060102416 A AR P060102416A AR 053894 A1 AR053894 A1 AR 053894A1
Authority
AR
Argentina
Prior art keywords
aryl
group
substituted
heterocycle
alkyl
Prior art date
Application number
ARP060102416A
Other languages
English (en)
Inventor
Mauro Marzi
Gianfranco Battistuzzi
Marzo Maria Di
Giuseppe Giannini
Claudio Pisano
Loredana Vesci
Franco Zunino
Ricardo Pezzi
Original Assignee
Sigma Tau Ind Farmaceuti
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
Application filed by Sigma Tau Ind Farmaceuti filed Critical Sigma Tau Ind Farmaceuti
Publication of AR053894A1 publication Critical patent/AR053894A1/es

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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
    • C07C251/32—Oximes
    • C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
    • C07C251/52—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by halogen atoms or by nitro or nitroso groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • 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
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/04—Antineoplastic agents specific for metastasis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C251/36—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atoms of the oxyimino groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C251/36—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atoms of the oxyimino groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C251/40—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atoms of the oxyimino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
    • C07C251/60—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/72—Hydrazones
    • C07C251/86—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C313/08—Sulfenic acids; Derivatives thereof
    • C07C313/18—Sulfenamides
    • C07C313/26—Compounds containing any of the groups, X being a hetero atom, Y being any atom
    • C07C313/28—Y being a hydrogen or a carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • 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
    • C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Oncology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Hematology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Indole Compounds (AREA)

Abstract

La presente se refiere a que tienen actividad antitumoral y quimiosensibilizante. También se describen composiciones farmacéuticas que contienen los compuestos mencionados para el tratamiento de los tumores. Reivindicacion 1: Un compuesto que tiene la siguiente formula (1), caracterizado porque: n es o bien 0 o 1; cuando n es 0, A es un grupo monovalente y es seleccionado entre el grupo que consiste en: OH, NH-OG, el grupo de formula (2), en donde G y G' son iguales o diferentes y son H, glicosidos o acetilo; cuando n es 1, A es un grupo divalente seleccionado entre el grupo que consiste en: NH-S-S-NH y CH2-S-CH2; Y es un grupo seleccionado HC=CH, FC=CF, FC=CH, CH=F, CH2-CH2 y C:::C; R es el grupo de formula (2), en donde X es o bien O, NH; R es el grupo de formulas (3) y (4); Z es seleccionado entre el grupo que consiste en: H; arilo C6-11 o arilo C6-11 sustituido con nitro, halogeno, alcoxicarbonilo C1-4, hidroxilo o amino; alquilo C1-4, alquenilo C2-4, alquinilo C2-4; ariloC6-11(CH2)n', en donde arilo está sustituido con nitro, halogeno, alcoxicarbonilo C1-4, hidroxilo o amino; en donde n' = 0-3; ariloC6-11-CO, en donde arilo está sustituido con nitro halogeno, alcoxicarbonilo C1-4, hidroxi, amino; heterocicloC2- 4-alquiloC1-3 en donde por lo menos uno de los CH2 del heterociclo está sustituido por O, S, NH; R1 es seleccionado entre el grupo que consiste en: H; NH2; alquilo C1-4, alquenilo C2-4, alquinilo C2-4; NH-alquiniloC1-3; NO2; alquinilo C1-3; halogeno; arilo C6-12; ariloC6-12-alquiniloC1-3; heterocicloC2-4-alquiniloC1-3 en donde por lo menos uno de los CH2 del heterociclo está sustituido por O, S, NH; o R y R1 tomados junto con el grupo aromático, forman un grupo policíclico que tiene la formula (5); R2 es seleccionado entre el grupo que consiste en: H; arilo C6-11 o arilo C6-11 sustituido con nitro, halogeno, alcoxicarbonilo C1-4, hidroxilo o amino; alquilo C1-4, alquenilo C2-4, alquinilo C2-4; ariloC6-11(H2)n'', en donde arilo está sustituido con nitro, halogeno, alcoxicarbonilo C1-4, hidroxilo o amino; en donde n'' = 0-3; ariloC6-11-CO, en donde arilo está sustituido con nitro halogeno, alcoxicarbonilo C1-4, hidroxi, amino; heterocicloC2-4-alquiloC1-3 en donde por lo menos uno de los CH2 del heterociclo está sustituido por O, S, NH; R3 es seleccionado entre el grupo que consiste en: H; alquiloC1-4, alquenilo C1-4; alquiloC1-4-NH; alquiloC1-4-heterocicloC3-6 en donde por lo menos uno de los CH2 del heterociclo está sustituido por O, S, NH; arilo C6-11; heteroarilo C3-6 en donde por lo menos uno de los CH del heterociclo está sustituido por O, S, NH; R4 es seleccionado entre el grupo que consiste en: H; alquilo C1-4; arilo C6-11; ariloC6-11-alquiniloC1-4; alcanoilo C2-4; CO-ariloC6-11; R5 es seleccionado entre el grupo que consiste en: H; alquilo C1-6 lineal o ramificado; alquenilo C2-6 lineal o ramificado; OR6, en donde R6 es H, alquilo C1-4, mesilo; tosilo, alcanoilo C1-4.
ARP060102416A 2005-06-10 2006-06-09 Derivados de los acidos cinamico y fenilpropiolico utiles como agentes antiumorales AR053894A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP05012561 2005-06-10

Publications (1)

Publication Number Publication Date
AR053894A1 true AR053894A1 (es) 2007-05-23

Family

ID=35004351

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP060102416A AR053894A1 (es) 2005-06-10 2006-06-09 Derivados de los acidos cinamico y fenilpropiolico utiles como agentes antiumorales

Country Status (13)

Country Link
US (1) US7816386B2 (es)
EP (1) EP1893561A1 (es)
JP (1) JP2008545772A (es)
KR (1) KR20080040665A (es)
CN (1) CN101193854A (es)
AR (1) AR053894A1 (es)
AU (1) AU2006256769A1 (es)
BR (1) BRPI0611730A2 (es)
CA (1) CA2607184A1 (es)
EA (1) EA013845B1 (es)
MX (1) MX2007015293A (es)
TW (1) TW200718691A (es)
WO (1) WO2006131482A1 (es)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI429628B (zh) 2010-03-29 2014-03-11 Univ Taipei Medical 吲哚基或吲哚啉基羥肟酸化合物

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3763213A (en) * 1971-11-10 1973-10-02 R Heck Introduction of organic groups into ethylenically unsaturated carboxylic nitriles using a group viii metal salt
US6248752B1 (en) 1998-02-27 2001-06-19 Charles Duane Smith Azabicyclooctane compositions and methods for enhancing chemotherapy
TWI311133B (en) * 2001-04-20 2009-06-21 Eisai R&D Man Co Ltd Carboxylic acid derivativeand the salt thereof
US6800618B2 (en) * 2001-05-07 2004-10-05 The United States Of America As Represented By The Secretary Of The Army Chemosensitizing agents against chloroquine resistant plasmodium falciparum and methods of making and using thereof
DE10225635C1 (de) 2002-06-07 2003-12-24 Aventis Pharma Gmbh N-Benzoylureido-Zimtsäurederivate, Verfahren zu deren Herstellung und deren Verwendung

Also Published As

Publication number Publication date
WO2006131482A1 (en) 2006-12-14
US20080194659A1 (en) 2008-08-14
EA013845B1 (ru) 2010-08-30
BRPI0611730A2 (pt) 2010-09-28
AU2006256769A1 (en) 2006-12-14
MX2007015293A (es) 2008-02-22
KR20080040665A (ko) 2008-05-08
EP1893561A1 (en) 2008-03-05
CN101193854A (zh) 2008-06-04
US7816386B2 (en) 2010-10-19
CA2607184A1 (en) 2006-12-14
EA200702668A1 (ru) 2008-04-28
TW200718691A (en) 2007-05-16
JP2008545772A (ja) 2008-12-18

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