AR073677A1 - Derivados ciclicos de benzimidazol activadores de proteinquinasas de amp, composiciones farmaceuticas que los contienen y uso de los mismos en el tratamiento de diabetes tipo ii, obesidad y otras enfermedades. - Google Patents

Derivados ciclicos de benzimidazol activadores de proteinquinasas de amp, composiciones farmaceuticas que los contienen y uso de los mismos en el tratamiento de diabetes tipo ii, obesidad y otras enfermedades.

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Publication number
AR073677A1
AR073677A1 ARP090103683A ARP090103683A AR073677A1 AR 073677 A1 AR073677 A1 AR 073677A1 AR P090103683 A ARP090103683 A AR P090103683A AR P090103683 A ARP090103683 A AR P090103683A AR 073677 A1 AR073677 A1 AR 073677A1
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alkyl
heteroaryl
cycloalkyl
aryl
unsubstituted
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Merck Sharp & Dohme
Metabasis Therapeutics Inc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
    • C07D235/26—Oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
    • C07D235/28—Sulfur 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
    • 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
    • C07D403/12—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 linked by a chain containing hetero atoms as chain links
    • 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
    • C07D405/02—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 two hetero rings
    • C07D405/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms 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)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Diabetes (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

Reivindicacion 1: Un compuesto de formula estructural 1: o una sal farmacéuticamente aceptable del mismo, en el que: X está ausente o se selecciona entre; (24) -CH2-, (25) -CHF-, (26) -CF2-, (27) -S-, (28) -O-, (29) -O-CH2-, (30) -NH-, (31) -C(O)-, (32) -NHC(O)-, (33) -C(O)NH-, (34) -NHSO2-, (35) -SO2NH-, y (36) -CO2-, donde cada CH2 está sin sustituir o sustituido por 1 o 2 sustituyentes seleccionados entre: hidroxi, halogeno, NH2, alquilo C1-6, CO2H, CO2alquilo C1-6, COalquilo C1-6, fenilo y -CH2fenilo, y donde cada NH está sin sustituir o sustituido por 1 sustituyente seleccionado entre: alquilo C1-6, CO2H, CO2alquilo C1-6, COalquilo C1-6, fenilo y -CH2fenilo; Y se selecciona entre: (6) cicloalquilo C3 10, (7) cicloalquenilo C3-10, (8) cicloheteroalquilo C2-10, (9) cicloheteroalquenilo C2-10, (10) arilo, y (11) heteroarilo, donde el cicloalquilo, cicloalquenilo, cicloheteroalquilo, cicloheteroalquenilo, arilo y heteroarilo están sin sustituir o sustituidos por 1, 2, 3 o 4 sustituyentes seleccionados entre Rb se selecciona entre: (35) oxo, (36) -CN, (37) -(CH2)nCO2H, (38) -(CH2)nCO2Ri, (39) -(CH2)nOH, (40) -(CH2)nC(O)NHRg, (41) -(CH2)nNHC(O)alquilo C1-6, (42) -(CH2)nNHSO2Ri, (43) -(CH2)nSO2NHRg, (44) (CH2)nSO2NHC(O)Ri, (45) -(CH2)nSO2NHCO2Ri, (46) -(CH2)nSO2NHCON(Rg)2, (47) -(CH2)nC(O)NHSO2Ri, (48) -(CH2)nNHC(O)N(Rg)2, (49) -(CH2)ncicloalquil C3-10-CO2Re, (50) heteroarilo, (51) -cicloheteroalquenilo C2-10, y (52) -cicloheteroalquilo C2-10, donde cada CH2 está sin sustituir o sustituido por 1 o 2 sustituyentes seleccionados entre alquilo C1-6, -OH y -NH2, donde cada NH está sin sustituir o sustituido por 1 sustituyente seleccionado entre Rc, y donde cada alquilo, cicloalquilo, cicloheteroalquilo, cicloheteroalquenilo, arilo y heteroarilo está sin sustituir o sustituido por 1, 2, 3 o 4 sustituyentes seleccionados entre Rc; cada R1 y R2 se selecciona independientemente entre: (1) hidrogeno, (2) halogeno, (3) -CH, (4) -CF3, (5) -alquilo C1-6, (6) -alquenilo C2-6, (7) alquinilo C2-6, (8) -(CH2)pcicloalquilo C3-10, (9) (CH2)pcicIoaIquil C3-7-arilo, (10) -(CH2)pcicloalquil C3-7-heteroarilo, (11) -(CH2)pcicloalquenilo C4-10, (12) -(CH2)pcicloaIquenil C4-7-arilo, (13) -(CH2)pcicloalquenil C4-7-heteroarilo, (14) -(CH2)pcicloheteroalquilo C2-10, (15) -(CH2)pcicIoheteroaqueniIo C2-10, (16) -(CH2)parilo, (17) bifenilo, (18) -(CH2)pheteroarilo, (19) -alquenil C2-6-alquilo, (20) -alquenil C2-6-arilo, (21) -alquenil C2-6-heteroarilo, (22) -alquenil C2-6-cicloalquiIo C3-7, (23) -alquenil C2 6-cicloalquenilo C3-7, (24) -alquenil C2-6-cicloheteroalquilo C2-7, (25) -alquenil C2-6-cicloheteroalquenilo C2-7, (26) -alquinil C2-6-(CH2)1-3-O-arilo, (27) -alquinil C2-6-alquilo, (28) -alquinil C2-6-arilo, (29) -alquinil C2-6-heteroarilo, (30) -alquinil C2-6-cicloalquilo C3-7, (31) -alquinil C2-6-cicloalquenilo C3-7, (32) -alquinil C2-6 -cicloheteroalquilo C3-7, (33) -alquinil C2-6-cicloheteroalquenilo C2-7, y (34) -C(O)NH-(CH2)0-3fenilo, donde cada CH2 está sin sustituir o sustituido por 1 o 2 sustituyentes seleccionados entre: halogeno, CF3, -OH, -NH2, -alquilo C 1-6, -Oalquilo C1-6, -NHalquilo C1-6 y -N(alquilo C1-6)2, donde cada alquilo, alquenilo y alquinilo está sin sustituir o sustituido por 1, 2 o 3 sustituyentes seleccionados entre: halogeno, CF3, -OH, -NH2, -alquilo C1-6, -Oalquilo C1-6, -NHalquilo C1-6 y -N(alquilo y donde cada cicloalquilo, cicloalquenilo, cicloheteroalquilo, cicloheteroalquenilo, fenilo, arilo y heteroarilo está sin sustituir o sustituido por 1, 2, 3 o 4 sustituyentes seleccionados independientemente entre Ra, con la condicion de que al menos uno de solo uno de R1 y R2 se seleccione entre el grupo que consiste en: hidrogeno, halogeno, -CN, -CF3, -alquilo C1-6, -alquenilo C2-6 y -alquinilo C2-6, y con la condicion de que si R1 o R2 es hidrogeno, entonces al menos uno de R3 y R4 no sea hidrogeno; R3 y R4 cada uno de se selecciona independientemente entre: (5) hidrogeno, (6) halogeno, (7) -alquilo C1-6, (8) -alquenilo C2-6, (9) -alquinilo C2-6, (10) -cicloalquilo C3-10, (11) -cicloalquenilo C3-10, (12) arilo, (13) heteroarilo, (14) -CN, (15) -CF3, (16) -OH, (17) -Oalquilo C1-6, (18) -NH2, (19) -NHalquilo C1-6, (20) -N(alquilo C1-6)2, (21) -Salquilo C1-6, (22) -SOalquilo C1-6, (23) -SO2alquilo C1-6, (24) -NHSO2alquilo C1-6, (25) -NHC(O)alquilo C1-6, (26) -SO2NHalquilo C1-6, y (27) -C(O)NHalquilo C1-6; R5 se selecciona entre: (7) hidrogeno, (8) -alquilo C1-6, (9) -CH2CO2H, y (10) -CH2CO2alquilo C1-6; cada Ra se selecciona independientemente entre el grupo que consiste en: (1) halogeno, (2) oxo, (3) -(CH2)mOH, (4) (CH2)mN(Rj)2, (5) (CH2)mNO2, (6) (CH2)mCN, (7) -alquilo C1-6, (8) -(CH2)mCF3, (9) -(CH2)mOCF3, (10) -OCH2OaIquilo C1-6, (11) -OCH2-arilo, (12) -(CH2)mC(=N-OH)N(Rj)2, (13) -(CH2)mOalquilo C1-6, (14) -(CH2)mO-arilo, (15) -OCH2fenilo, (16) (CH2)mSalquilo C1-6, (17) (CH2)mS(O)alquilo C1-6, (18) -(CH2)mS(O)2alquilo C1-6, (19) -(CH2)mNHS(O)2alquilo C1-6, (20) -(CH2)mC(O)Rf, (21) (CH2)mC(O)N(Rj)2, (22) -(CH2)mN(Rj)C(O)Rf, (23) -(CH2)mN(Rj)C(O)N(Rj)2, (24) -(CH2)mCO2H, (25) -(CH2)mOC(O)H, (26) (CH2)mCO2Rf, (27) -(CH2)mOC(O)Rf, (28) -(CH2)mcicloalquilo C3-7, (29) -(CH2)mcicloalquenilo C3-7, (30) -(CH2),mcicloheteroaIquiIo C2-6, (31) -(CH2)mcicloheteroaIquenilo C2-6, (32) -(CH2)rnarilo, y (33) -(CH2)mheteroarilo, donde cada CH2 está sin sustituir o sustituido por 1 o 2 sustituyentes seleccionados entre: oxo, -(CH2)0-3OH, -CN, -NH2, -NH(alquilo C1-6), -N(alquilo C1-6)2, -alquilo C1-6, -Oalquilo C1-6, halogeno, -CH2F, -CHF2, -CF3, -CO2H, -CO2alquilo C1-6, -cicloalquilo C3-7, fenilo, CH2fenilo, heteroarilo y CH2heteroarilo, y donde el alquilo, cicloalquilo, cicloheteroalquilo, fenilo, arilo y heteroarilo están sin sustituir o sustituidos por 1, 2, 3 o 4 sustituyentes seleccionados entre: oxo, -(CH2)0-3OH, -CN, -NH2, -NH(alquilo C1-6), -N(alquilo C1-6)2, -alquilo C1-6, -Oalquilo C1-6, halogeno, -CH2F, -CHF2, -CF3, -CO2H, -CO2alquilo C1-6, -cicloalquilo C3-7, fenilo, CH2fenilo, heteroarilo y CH2heteroarilo; cada Rb se selecciona independientemente entre: (14) hidrogeno, (15) -alquilo C1-6, (16) -cicloalquilo C3-6, (17) -cicloalquenilo C3-6, (18) -cicloheteroalquilo C3-6, (19) arilo, (20) heteroarilo, (21) halogeno, (22) -OH, (23) -NO2, (24) -NH2, (25) -NH(alquilo C1-6), (26) -N(alquilo C1-6)2, (27) -Oalquilo C1-6, (28) -(CH2)qCO2H, (29) -(CH2)qCO2alquilo C1-6, (30) -CF3, (31) -CN (32) -SO2alquilo C1-6, y (33) -(CH2)qCON(Re)2, donde cada CH2 está sin sustituir o sustituido por 1 o 2 halogenos, y donde cada alquilo, cicloalquilo, cicloalquenilo, cicloheteroalquilo, arilo y heteroarilo están sin sustituir o sustituidos por 1, 2 o 3 halogenos; cada Rc se selecciona independientemente entre: (21) halogeno, (22) oxo, (23) -(CH2)rOH, (24) -(CH2)rN(Re)2, (25) -(CH2)rCN, (26) -alquilo C1-6, (27) -CF3, (28) -alquil C1-6-OH, (29) -OCH2Oalquilo C1-6, (30) -(CH2)rOalquilo C1-6, (31) -OCH2arilo, (32) -(CH2)rSalquilo C1-6, (33) -(CH2)rC(O)Rf, (34) -(CH2)rC(O)N(Re)2, (35) -(CH2)rCO2H, (36) -(CH2)rCO2Rf, (37) -(CH2)rcicloalquilo C3-7, (38) -(CH2)rcicloheteroalquilo C2-6, (39) -(CH2)rarilo, y (40) -(CH2)rheteroarilo, donde cada CH2 está sin sustituir o sustituido por 1 o 2 sustituyentes seleccionados entre: oxo, -OH, -CN, -N(Rh)2, -alquilo C1-6, -Oalquilo C1-6, halogeno, -CHF2, -CHF2, -CF3, -CO2H, -CO2alquilo C1-6, -cicloalquilo C3-7 y heteroarilo, y donde el alquilo, cicloalquilo, cicloheteroalquilo, arilo y heteroarilo están sin sustituir o sustituidos por 1, 2, 3 o 4 sustituyentes seleccionados entre: oxo, -OH, -CN, -N(Rh)2, -alquilo C1-6, -Oalquilo C1-6, halogeno, -CHF2, -CHF2, -CF3, -CO2H, -CO2alquilo C1-6, -cicloalquilo C3-7 y heteroarilo; cada Re, Rg y Rh se selecciona independientemente entre: (1) hidrogeno, y (2) alquilo donde el alquilo está sin sustituir o sustituido por 1, 2, 3 o 4 sustituyentes seleccionados entre: -OH, oxo, halogeno, alquilo -Oalquilo C1-6, -NH2, -NH(alquilo C1-6) y -N(alquilo C1-6)2; cada Rj se selecciona independientemente entre: (1) hidrogeno, (2) alquilo C1-6, (3) cicloalquilo C3-6, (4) -C(O)Ri, y (5) -SO2Ri, donde el alquilo y el cicloalquilo están sin sustituir o sustituidos por 1, 2, 3 o 4 sustituyentes seleccionados entre: -OH, oxo, halogeno, alquilo C1-6, -Oalquilo C1-6, -NH2, -NH(alquilo C1-6) y -N(alquilo C1-6)2; cada Rf y Ri se selecciona independientemente entre: (19) alquilo C1-6, (20) cicloalquilo C4-7, (21) cicloalquenilo C4-7, (22) cicloheteroalquilo C3-7, (23) cicloheteroalquenilo C3-7, (24) arilo, y (25) heteroarilo, donde el alquilo, cicloalquilo, cicloalquenilo, cicloheteroalquilo, cicloheteroalquenilo, arilo y heteroarilo están sin sustituir o sustituidos por 1, 2, 3 o 4 sustituyentes seleccionados entre: oxo, -OH, -CN, -NH2, -alquilo C1-6, -Oalquilo C1-6, halogeno, -CH2F, -CHF2, -CF3, -CO2H, -CO2alquilo C1-6, -cicloalquilo C3-7 y heteroarilo; n es 0, 1, 2, 3 o 4; m es 0, 1, 2, 3 o 4; p es 0, 1, 2 o 3; q es 0, 1, 2, 3 o 4; y r es 0, 1 o 2.
ARP090103683A 2008-09-26 2009-09-24 Derivados ciclicos de benzimidazol activadores de proteinquinasas de amp, composiciones farmaceuticas que los contienen y uso de los mismos en el tratamiento de diabetes tipo ii, obesidad y otras enfermedades. AR073677A1 (es)

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