AR054724A1 - Derivados benzamida inhibidores de la enzima histona desacetilasa (hdac) - Google Patents

Derivados benzamida inhibidores de la enzima histona desacetilasa (hdac)

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Publication number
AR054724A1
AR054724A1 ARP060100215A ARP060100215A AR054724A1 AR 054724 A1 AR054724 A1 AR 054724A1 AR P060100215 A ARP060100215 A AR P060100215A AR P060100215 A ARP060100215 A AR P060100215A AR 054724 A1 AR054724 A1 AR 054724A1
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Argentina
Prior art keywords
alkyl
3alkyl
amino
alkoxy
cycloalkyl
Prior art date
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ARP060100215A
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English (en)
Inventor
Keith Gibson
Elaine Stokes
Mike Waring
David Andrews
Zbigniew Matusiak
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Astrazeneca Ab
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Filing date
Publication date
Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab
Publication of AR054724A1 publication Critical patent/AR054724A1/es

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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
    • C07D213/72—Nitrogen atoms
    • C07D213/73—Unsubstituted amino or imino radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/56—Amides
    • 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
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • 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
    • C07D213/82—Amides; Imides in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Procesos para su preparacion, composiciones farmacéuticas que los contienen y su uso en la fabricacion de un medicamento para su uso como agente antiproliferativo en la prevencion o el tratamiento de tumores u otros estados clínicos proliferativos sensibles a la inhibicion de histona deacetilasa (HDAC). Reivindicacion 1: Un compuesto caracterizado porque responde a la formula (1), donde: R1a se selecciona entre hidrogeno, amino, alquilo C1-3, N-alquilaminoC1-3, N,N-di-alquilaminoC1-3, o un grupo de subformula: R5R6N-X1-[CRaRb]q-, donde q es 1, 2 o 3; cada grupo Ra y Rb presente se selecciona en forma independiente entre hidrogeno, halo, hidroxi, o alquilo C1-4; X1 se selecciona entre un enlace directo o -C(O)-; y R5 y R6 se seleccionan en forma independiente entre sí, entre hidrogeno o alquilo C1-3; y donde si R1a es un grupo N-alquilaminoC1-3 o N,N- di-alquilaminoC1-3, la porcion alquilo C1-3 está opcionalmente sustituida con hidroxi o alcoxi C1-2; R1b se selecciona entre: i) hidrogeno, alquilo C1-6, halo-alquiloC1-6, hidroxi-alquiloC1-6, cicloalquilo C3-6, cicloalquilC3-6-alquiloC1-4, alcoxi C1-6, alcoxiC1-6-alquiloC1-6, N- alquilsulfamoiloC1-4; N,N-di(alquilC1-4)sulfamoilo; o ii) un grupo de subformula: R7R8N- [CRaRb]a-X2-, donde R7 y R8 se seleccionan en forma independiente entre hidrogeno, alquilo C1-6, cicloalquilo C3-6, cicloalquilC3-6-alquiloC1-6, alcoxiC1-6-alquiloC1-6, alquenilo C2-3, alquinilo C2-3, o un grupo de formula: R9R10N-[CRaRb]b-X3-, donde b es 1, 2, o 3; Ra y Rb tienen los valores que se han definido; X3 es un enlace directo o - C(O)-; R9 y R10 se seleccionan en forma independiente entre hidrogeno, alquilo C1-6, cicloalquilo C3-6, cicloalquilC3-6-alquiloC1-6, alcoxiC1-6- alquiloC1-6, o R9 y R10 están unidos de manera que, junto con el átomo de nitrogeno al cual están unidos, forman un anillo heterocíclico de 4, 5, 6 o 7 miembros, donde dicho anillo heterocíclico contiene opcionalmente, además del átomo de nitrogeno al cual R9 y R10 se unen, uno o más heteroátomos adicionales seleccionados entre N, O o S, y donde dicho anillo heterocíclico está opcionalmente sustituido con uno o más hidroxi, halo, alquilo C1-4, carbamoilo, oxo, -[CH2]e-NR11R12 (donde e es 0, 1 o 2, y R11 y R12 se seleccionan en forma independiente entre hidrogeno, alquilo C1-6, cicloalquilo C3-6 o cicloalquilC3-6-alquiloC1-6; o R7 y R8 están unidos de manera que, junto con el átomo de nitrogeno al cual están unidos, forman un anillo heterocíclico de 4, 5, 6 o 7 miembros, donde dicho anillo heterocíclico contiene opcionalmente, además del átomo de nitrogeno al cual R7 y R8 se unen, uno o más heteroátomos adicionales seleccionados entre N, O o S, y donde dicho anillo heterocíclico está opcionalmente sustituido con uno o más hidroxi, halo, alquilo C1-4, carbamoilo, oxo, alquenilo C2-4, alquinilo C2-4, alcoxi C1-4, alcoxiC1-4-alquiloC1-4, alquilC1-4-S(O)q- (donde q es 0, 1 o 2), un anillo heterocíclico de 5 o 6 miembros que comprende entre uno y tres heteroátomos seleccionados entre N, O o S o -[CH2]f-NR13R14 (donde f es 0, 1 o 2, y R13 y R14 se seleccionan en forma independiente entre hidrogeno, alquilo C1-6, cicloalquilo C3-6 o cicloalquilC3-6-alquiloC1- 6); X2 se selecciona entre un enlace directo, -O- o -C(O)-, con la condicion de que X2 solo puede ser -C(O)- si al menos uno de R7 o R8 es un grupo de formula: R9R10N-[CRaRb]b-X3-, como se ha definido; a es 0, 1, 2, 3 o 4; Ra y Rb tienen los valores que se han definido; o iii) un grupo de subformula: Q-Z-Y-, donde: Y es un enlace directo o -[CRaRb]x-, donde el entero x es entre 1 y 4 y Ra y Rb tienen los valores que se han definido; Z está ausente o se selecciona entre -O-, -S-, -SO-, SO2-, -NH- SO2-; -SO2-NH- o -C(O)-; y Q es un grupo heterociclilo unido mediante carbono o heterociclil-alquiloC1-6, donde dicho heterociclilo o heterociclil-alquiloC1-6 está opcionalmente sustituido sobre el anillo heterociclilo con uno o más grupos sustituyentes (por ejemplo 1, 2 o 3), que pueden ser iguales o diferentes, seleccionados entre halo, oxo, ciano, hidroxi, trifluorometilo, amino, carboxi, carbamoilo, mercapto, sulfamoilo, alquilo C1-3, alquenilo C2-3, alquinilo C2-3, alcoxi C1-3, alcanoilo C1-3, alcanoiloxi C1-3, alcoxiC1-3-alquiloC1-3, alcoxicarbonilo C1-3, halo- alquiloC1-3, N-(alquilC1-3)amino; N,N-di-(alquilC1-3)amino, N-(alcoxiC1-3-alquilC1-3)amino, N,N-di-(alcoxiC1-3-alquilC1-3)amino; N-(alcoxiC1-3-alquilC1-3)-N- (alquilC1-3)amino, N-alquilcarbamoiloC1-3, N,N-di-(alquilC1-3)carbamoilo, alquiltio C1-3, alquilsulfinilo C1-3, alquilsulfonilo C1-3, N-alquilsulfamoiloC1-3, N,N-di-(alquilC1-3)sulfamoilo; R1c se selecciona entre hidrogeno, halo, ciano, hidroxi, trifluorometilo, trifluorometoxi, amino, carboxi, carbamoilo, mercapto, sulfamoilo, alquilo C1-3, alquenilo C2-3, alquinilo C2-3, alcoxi C1-3, alcanoilo C1-3, alcanoiloxi C1-3, N-alquilaminoC1-3, N,N-di-(alquilC1-3)amino, alcanoilamino C1-3, N- alquilcarbamoiloC1-3, N,N-di- alquilcarbamoiloC1-3, alquiltio C1-3, alquilsulfinilo C1-3, alquilsulfonilo C1-3, alcoxicarbonilo C1-3, N-alquilsulfamoiloC1-3, y N,N-di- alquilsulfamoiloC1-3; el entero m es 0, 1, 2, 3 o 4; R2 es halo; el entero n es 0, 1, 2, 3, o 4; R3 se selecciona entre halo, ciano, hidroxi, trifluorometilo, trifluorometoxi, amino, carboxi, carbamoilo, mercapto, sulfamoilo, alquilo C1-3, alquenilo C2-3, alquinilo C2-3, alcoxi C1-3, alcanoilo C1-3, alcanoiloxi C1-3, N- alquilaminoC1-3, N,N-di-(alquilC1-3)amino, alcanoilamino C1-3, N-alquilcarbamoiloC1-3, N,N-di- alquilcarbamoiloC1-3, alquiltio C1-3, alquilsulfinilo C1-3, alquilsulfonilo C1-3, alcoxicarbonilo C1-3, N-alquilsulfamoiloC1-3, y N,N-di- alquilsulfamoiloC1- 3; R4 es amino o hidroxi; y W es metilo o etilo; o una sal aceptable para uso farmacéutico o prodroga del mismo.
ARP060100215A 2005-01-20 2006-01-20 Derivados benzamida inhibidores de la enzima histona desacetilasa (hdac) AR054724A1 (es)

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GBGB0501146.5A GB0501146D0 (en) 2005-01-20 2005-01-20 Novel benzamide derivatives

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AR054724A1 true AR054724A1 (es) 2007-07-11

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US (1) US20080119451A1 (es)
AR (1) AR054724A1 (es)
GB (1) GB0501146D0 (es)
TW (1) TW200637823A (es)
UY (1) UY29340A1 (es)
WO (1) WO2006077387A2 (es)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0521244D0 (en) 2005-10-19 2005-11-30 Astrazeneca Ab Benzamide compounds
GB0526351D0 (en) * 2005-12-23 2006-02-01 Astrazeneca Ab Novel benzamide derivatives
TW200740769A (en) 2006-03-16 2007-11-01 Astrazeneca Ab Novel process
SG163547A1 (en) 2006-05-29 2010-08-30 High Point Pharmaceuticals Llc 3- (1, 3-benz0di0x0l-5-yl) -6- (4-cyclopropylpiperazin-1-yl) -pyridazine, its salts and solvates and its use as histamine h3 receptor antagonist
EP2014656A3 (en) 2007-06-11 2011-08-24 High Point Pharmaceuticals, LLC New heteocyclic h3 antagonists
CN111909053B (zh) * 2020-08-06 2022-12-06 湖北省生物农药工程研究中心 基于二芳胺单元的酰胺类衍生物及其制备方法和应用

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CN101851173A (zh) * 2001-09-14 2010-10-06 梅特希尔基因公司 组蛋白脱乙酰化酶抑制剂
TWI319387B (en) * 2002-04-05 2010-01-11 Astrazeneca Ab Benzamide derivatives
WO2005034870A2 (en) * 2003-10-07 2005-04-21 Renovis, Inc. Amide compounds and ion channel ligands and uses thereof
AR050926A1 (es) * 2004-09-03 2006-12-06 Astrazeneca Ab Derivados de benzamida como inhibidores de la histonadesacetilasa(hdac)

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GB0501146D0 (en) 2005-02-23
US20080119451A1 (en) 2008-05-22
WO2006077387A3 (en) 2006-10-05
TW200637823A (en) 2006-11-01
UY29340A1 (es) 2006-08-31
WO2006077387A2 (en) 2006-07-27

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