AR068742A1 - Cis-imidazolinas quirales, composicion farmaceutica, proceso y uso para cancer - Google Patents

Cis-imidazolinas quirales, composicion farmaceutica, proceso y uso para cancer

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Publication number
AR068742A1
AR068742A1 ARP080104381A ARP080104381A AR068742A1 AR 068742 A1 AR068742 A1 AR 068742A1 AR P080104381 A ARP080104381 A AR P080104381A AR P080104381 A ARP080104381 A AR P080104381A AR 068742 A1 AR068742 A1 AR 068742A1
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AR
Argentina
Prior art keywords
substituted
piperidinyl
ch2oh
thienyl
heteroaryl
Prior art date
Application number
ARP080104381A
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English (en)
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Hoffmann La Roche
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Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of AR068742A1 publication Critical patent/AR068742A1/es

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    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • C07D401/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/10—Spiro-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Reivindicacion 1: Un compuesto de la formula (1) en la que X, Y y Z son carbono o nitrogeno, con la condicion de que por lo menos uno de X, Y y Z sea nitrogeno; v1 y v2 se eligen entre el grupo formado por halogeno, acetileno, ciano, trifluorometilo y nitro; R1 y R2 son -H o -CH3, con la condicion de que R1 y R2 no sean ambos -H; R3 es -H o -C(=O)-R6; R4 es -OCH3, -OCH2CH3, -OCH2CH2F, -OCH2CH2OCH3 o -OCH(CH3)2; R5 se elige entre el grupo formado por i) -H, ii) -halogeno, iii) -CH3, iv) -CF3, v) -OCH3 o -COCH2CH3, vi) -C(CH3)2, vii) -ciano, viii) -C(CH3)3, ix) -C(CH3)2-OR (en el que R es -H, -CH3 o -CH2CH3), x) -C(CH3)2CH-OR (en el que R es -H, -CH3, -CH2CH2OH o -CH2CH2OCH3), xi) -C(CH3)2CN, xii) -C(CH3)2COR (en el que R es -CH3), xiii) -C(CH3)2COOR (en el que R es -H, -CH3 o -CH2CH3), xiv) -C(CH3)2CONRaRb (en el que Ra es -H o -CH3 y Rb es -H o -CH3), xv) -SCH3 o -SO2CH3, xvi) -NRaRb (en el que Ra es -H o -CH3 y Rb es -H o -CH3) y xvii) 4-morfolinilo; y R6 se elige entre el grupo formado por i) -alquilo inferior, ii) -ciclopropilo o ciclobutilo, iii) -fenilo o fenilo sustituido por cloro, -OCH3 o ciano, iv) 4-morfolinilo, 1-(3-oxopiperazinilo), 1-piperidinilo, 4-tiomorfolinilo, 4-tiomortolinilo-1,1-dioxido o 1-(1,4-diazepinil-5-oxo), v) -NRc2 (en el que Rc es hidrogeno, -CH3, -CH2CH3, -CH2H2OH, -CH2CH2OCH3 o -CH2CH(OH)CH2OH), vi) una piperazina sustituida de la formula (2), en la que R se elige entre el grupo formado por a) hidrogeno, b) alquilo inferior, c) -CH2CH(OH)CH2OH, -CH2CH2CH(OH)CH2OH o 4-tetrahidro-2H-tiopiranilo-1,1-dioxido, d) -CH2CH2Rd (en el que Rd es -OH, -OCH3, -OCH2CH2OH, -OCH2CH2OCH3, -CN, -CF3, -SO2CH3, -SO2NH2, -SO2N(CH3)2, -CONH2, -CON(CH3)2, -NH2, -NHCOCH3, -NHSO2CH3, -N(CH3)2, 1-pirrolidinilo, 1-piperidinilo o 4-morfolinilo), e) -CH2CH2CH2Re (en el que Re es -OH, -OCH3, -SO2CH3, -SO2CH2CH3, -SO2N(CH3)2, -CN, -N(CH3)2, 1-pirrolidinilo, 1-piperidinilo, 4-rnorfolinilo, -COOCH3, -COOCH2CH3, -COOC(CH3)3, -CON(CH3)2, -CO-Rf (en el que Rf es -CH3, -CH2CH3, ciclopropilo, fenilo, 2-tienilo, 3-tienilo, 2-furanilo o 3-furanilo), -COCH2-Rg (en el que Rg es -H, -NHCH2CH2OH, -NHCH2CH2OCH3, -NHCH2CH2N(CH3)2, 1-piperidinilo, 1-(piperidinil-4-metanol), 4-morfolinilo o -N(CH3)-(3-(1-metil- pirrolidinilo))), f) -CH2-CO-Rh (en el que Rh es alquilo inferior sustituido o sin sustituir, -OH, -OCH3, -OCH2CH3, -NH2, heteroarilo sustituido por -(CH2) o sin sustituir, en el que n es el numero 0 o 1, -NH-cicloalquilo, -N-(alquilo inferior) en el que n es el numero 1 o 2; -NHCH2C(OH)CH2OH, -NHCH2CF3, -NHCH2CH2CH2OH, -N(CH2CH2OH)2, -N(CH2CH2OCH3)2, -N(CH3)CH2CH2OH, -NH(CH2OH)(CH3)CH2CH2OH, -NH(CH2OH)(CH3)CH3, -CH2CH2CH2SO2NH2, -N(CH2CH3)-heteroarilo, -N(CH3)CH2CH2OCH3, -NHCH2CH2OCH3, heteroarilo mono- o di-sustituido por -NH(CH2)n en el que n es el numero 0 o 1, heteroarilo sustituido por -NHCH2CH2 o sin sustituir, arilo mono- o di-sustituido por -NH, -NH(CH2)n-heterociclo, en el que n es el numero 0 o 1, -NH(CH2)n-OH en el que n es el numero 2 o 3, heterociclo sustituido por -(CH2)n o sin sustituir, en el que n es el numero 1 o 2 o heteroarilo mono- o di-sustituido por -N(CH2CH3)), g) -SO2Ri (en el que Ri es -CH3, -CH2CH3, -CH(CH3)2, fenilo, 4-metilfenilo, 4-propilfenilo, -CF3, 2-tienilo, 3-tienilo, -NH2, -NHCH3, -N(CH3)2, -NHCH2CH2OCH3, -N(CH2CH2OCH3)2, 1-pirrolidinilo, 1-piperidinilo, 4-morfolinilo, 1-piperazil-4-etanol, 1-(4-acetilpiperazinilo) o 1-(3-oxopiperazinilo)) y h) -CORj (en el que Rj es alquilo inferior que está sustituido o sin sustituir, cicloalquilo, 2-tetrahidrofuranilo, 2-tienilo, 3-tienilo, -NH2, -NHCH3, -N(CH3)2, 1-pirrolidinilo, 1-piperidinilo, 4-morfolinilo, 1-piperazinil-4-etanol, 1-(4-acetilpiperazinilo) o 1-(3-oxopiperazinilo)) y i) heteroarilo o heterociclo sustituido o sin sustituir; vii) una piperidina sustituida de la formula (3), en la que R es hidrogeno, alquilo inferior, -CH2CH(OH)CH2OH, -CH2CH2CH(OH)CH2OH o 4-tetrahidro-2H-tiopiranilo-1,1-dioxido, -CH2CH2Rd (en el que Rd es -OH, -OCH3, -OCH2CH2OH, -OCH2CH2OCH3, -CN, -CF3, -SO2CH3, -SO2NH2, -SO2N(CH3)2, -CONH2, -CON(CH3)2, -NH2, -NHCOCH3, -NHSO2CH3, -N(CH3)2, 1-pirrolidinilo, 1-piperidinilo o 4-morfolinilo), -CH2CH2CH2Re (en el que Re es -OH, -OCH3, -SO2CH3, -SO2CH2CH3, -SO2N(CH3)2, -CN, -N(CH3)2, 1-pirrolidinilo, 1-piperidinilo, 4-morfolinilo, -COOCH3, -COOCH2CH3, -COOC(CH3)3, -CON(CH3)2, -CO-Rf (en el que Rf es -CH3, -CH2CH3, ciclopropilo, fenilo, 2-tienilo, 3-tienilo, 2-furanilo o 3-furanilo), -COCH2-Rg (en el que Rg es H, -NHCH2CH2OH, -NHCH2CH2OCH3, -NHCH2CH2N(CH3)2, 1-piperidinilo, 1-(piperidinil-4-metanol), 4-morfolinilo o -N(CH3)-(3-(1-metilpirrolidinilo)), -CH2-CO-Rh (en el que Rh es alquilo inferior sustituido o sin sustituir, -OH, -OCR3, -OCH2CH3, -NH2, -(CH2)n-heteroarilo, en el que n es el numero 0 o 1; -NH-alquilo inferior, -NH-cicloalquilo, -N-(alquilo inferior)n en el que n es el numero 1 o 2, -NHCH2C(OH)CH2OH, -NHCH2CF3, -NHCH2CH2CH2OH, -N (CH2CH2OH)2, -N(CR2CH2OCH3)2, -N(CH3)CH2CH2OH, -NH(CH2OH)(CH3)CH2CH2OH, -NH(CH2OH)(CH3)CH3, -CH2CH2CH2SO2NH2, -N(CH2CH3)heteroarilo, -N(CH3)CH2CH2OCH3, -NHCH2CH2OCH3, heteroarilo mono- o di- sustituido por -NH(CH2)n, en el que n es el numero 0 o 1, heteroarilo sustituido por -NHCH2CH2 o sin sustituir, arilo mono- o di-sustituido por -NH, -NH(CH2)n-heterociclo, en el que n es el numero 0 o 1, heterociclo sustituido por -NH(CH2)n-OH en el que n es el numero 2 o 3, o sin sustituir; o heteroarilo mono- o di-sustituido por -N(CH2CH3); -SO2Ri (en el que Ri es -CH3, -CH2CH3, -CH(CH3)2, fenilo, 4-metilfenilo, 4-propilfenilo, -CF3, 2-tienilo, 3-tienilo, -NHCH3, -N(CH3)2, -NHCH2CH2OCH3, -N(CH2CH2OCH3)2, 1-pirrolidinilo, 1-piperidinilo, 4-morfolinilo, 1-piperazil-4-etanol, 1-(4-acetilpiperazinilo) o 1-(3-oxopiperazinilo); -CORj (en el que Rj es alquilo inferior, cicloalquilo, 2-tetrahidrofuranilo, 2-tienilo, 3-tienilo, -NH2, -NHCH3, -N(CH3)2, 1-pirrolidinilo, 1-piperidinilo, 4-morfolinilo, 1-piperazinil-4-etanol, 1-(4-acetilpiperazinilo) o 1-(3-oxopiperazinilo)), heteroarilo o heterociclo sustituido o sin sustituir, -NH2, -NHCOCH3, -NHCOCH2NH2, -NHCOCH2NHCH3, -NHCOCH2N(CH3)2, -NHCOCH2N(CH2CH2OH)2, -NHCOCH2N(CH2CH2OCH3)2, -NHCOCH2NHCH2CH2OH, -NHCOCH2-(1-(4-acetilpiperazinilo)), -NHCOCH2-(1-(3-oxopiperazinilo)), -NHCOCH2-NHCONHCH3, -NHCOO-alquilo inferior, -NHCHCH3, -NHCO-alquilo inferior, -NH(CH2)n-SO2-CH3 en el que n es un numero 0-2, -NH(CH3)SO2CH3, (1-piperidinacarboxamida), -NHCOCH2-(N,Ndietil-1-piperidinilcarboxamida), -NHCOCH2-(1-(3-hidroxi-piperidinilo)), -NHCOCH2-(1-(piperidinil-4-metanol)), -NHCON(CH3)2, -NHCSNHCH3, -NHCSNHPh, -NHCH2CONH2 o -NHCH2CH2SO2CH3 y viii) una piperidina sustituida de la formula (4), en la que R es -OH, -CH2OH, -CH2CH2OH o -C(O)NH2; y sus sales y ésteres farmacéuticamente aceptables.
ARP080104381A 2007-10-09 2008-10-07 Cis-imidazolinas quirales, composicion farmaceutica, proceso y uso para cancer AR068742A1 (es)

Applications Claiming Priority (2)

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US97850607P 2007-10-09 2007-10-09
US9275908P 2008-08-29 2008-08-29

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US (1) US8513239B2 (es)
EP (2) EP2203437B1 (es)
JP (1) JP5324586B2 (es)
KR (1) KR101203020B1 (es)
CN (2) CN101821251A (es)
AR (1) AR068742A1 (es)
AU (1) AU2008309759A1 (es)
BR (1) BRPI0817850A2 (es)
CA (1) CA2701932C (es)
CL (1) CL2008002982A1 (es)
CO (1) CO6280486A2 (es)
CR (1) CR11333A (es)
ES (1) ES2395210T3 (es)
IL (1) IL204653A0 (es)
MA (1) MA31754B1 (es)
MX (1) MX2010003868A (es)
PE (1) PE20090814A1 (es)
RU (1) RU2487127C2 (es)
TW (1) TW200916446A (es)
WO (1) WO2009047161A1 (es)

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KR20100051742A (ko) 2010-05-17
BRPI0817850A2 (pt) 2015-04-07
PE20090814A1 (es) 2009-06-27
MX2010003868A (es) 2010-04-27
CN104710408A (zh) 2015-06-17
MA31754B1 (fr) 2010-10-01
EP2203437B1 (en) 2012-11-07
JP5324586B2 (ja) 2013-10-23
EP2325180A1 (en) 2011-05-25
CL2008002982A1 (es) 2009-10-16
AU2008309759A1 (en) 2009-04-16
ES2395210T3 (es) 2013-02-11
CA2701932C (en) 2015-10-20
US20090111789A1 (en) 2009-04-30
CR11333A (es) 2010-06-21
US8513239B2 (en) 2013-08-20
IL204653A0 (en) 2010-11-30
CO6280486A2 (es) 2011-05-20
KR101203020B1 (ko) 2012-11-20
WO2009047161A1 (en) 2009-04-16
TW200916446A (en) 2009-04-16
EP2203437A1 (en) 2010-07-07
CN101821251A (zh) 2010-09-01
RU2010118018A (ru) 2011-11-20
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CA2701932A1 (en) 2009-04-16
JP2010540675A (ja) 2010-12-24

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