AR042131A1 - Compuestos de piperidina fenil sustituidas y su uso como activadores de ppar - Google Patents

Compuestos de piperidina fenil sustituidas y su uso como activadores de ppar

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AR042131A1
AR042131A1 ARP030104332A ARP030104332A AR042131A1 AR 042131 A1 AR042131 A1 AR 042131A1 AR P030104332 A ARP030104332 A AR P030104332A AR P030104332 A ARP030104332 A AR P030104332A AR 042131 A1 AR042131 A1 AR 042131A1
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Argentina
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alkyl
optionally
ring
mono
amino
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ARP030104332A
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Pfizer Prod Inc
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
    • A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • 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
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • 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
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • 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
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen 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
    • C07D401/06—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
    • 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
    • C07D405/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D417/02—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 two hetero rings
    • C07D417/06—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 two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Diabetes (AREA)
  • Cardiology (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Rheumatology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Endocrinology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Urology & Nephrology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Pain & Pain Management (AREA)
  • Vascular Medicine (AREA)
  • Emergency Medicine (AREA)
  • Hospice & Palliative Care (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

Su uso como activadores de PPAR alfa, las composiciones farmacéuticas que contienen dichos compuestos y el uso de dichos compuestos para elevar ciertos niveles de lípido en plasma, incluyendo colesterol de lipoproteína de alta densidad y para disminuir otros ciertos niveles de lípido en plasma, como por ejemplo colesterol LDL y triglicéridos y, según esto, tratar enfermedades que empeoran con niveles bajos de colesterol HDL y/o niveles altos de colesterol LDL y triglicéridos, como por aterosclerosis y enfermedades cardiovasculares, en mamíferos, incluyendo seres humanos. Reivindicación 1: Un compuesto caracterizado porque es de fórmula (1), un isómero del mismo, un profármaco de dicho compuesto o isómero, o una sal farmacéuticamente aceptables de dicho compuestos, isómero o profármaco; en el que m y n son, cada uno independientemente, uno o dos; V e Y son, cada uno independientemente, a) metileno, o b) carbonilo; F y G son, cada uno independientemente, a) hidrógeno, b) halo, c) alquilo C1-4 sustituido opcionalmente con de uno a nueve átomos de flúor, d) cicloalquilo C3-6¸ e) hidroxi, f) alcoxi C1-4 o g) alquiltio C1-4; X es a) -Z o b) -B-C(R1R2)-Z; B es a) oxi, b) tio, c) sulfinilo, d) sulfonilo, e) metileno, o f) -N(H)-; Z es a) -C(O)OH, b) -C(O)O-alquilo C1-4, c) -C(O)O-(alquil C0-4)arilo, d) -C(O)-NH2, e) hidroxiaminocarbonilo, f) tetrazolilo, g) tetrazolilaminocarbonilo, h) 4,5-dihidro-5-oxo-1,2,4-oxadiazol-3-ilo, i) 3-oxoisoxazolidin-4-il-aminocarbonilo, j) -C(O)N(H)SO2R4, o k) -NHSO2R4; en el que R4 es a) alquilo C1-6, b) amino o c) mono-N o di-N,N-(alquil C1-6)amino, estando los sustituyentes alquilo C1-6 en R4 opcionalmente e independientemente sustituidos con de uno a nueve átomos de flúor; R1 es a) H, b) alquilo C1-4 o c) cicloalquilo C3-6; R2 es a) H, b) cicloalquilo C3-6 o c) una cadena de carbono de uno a cuatro miembros, lineal o ramificado, total o parcialmente saturado o totalmente insaturada; en la que el(los) carbono(s) de la cadena de carbono pueden reemplazarse con uno o dos heteroátomos seleccionados independientemente entre oxígeno y azufre; y en la que el azufre está opcionalmente mono o disustituido con oxo; en la que el(los) carbono(s) de la cadena de carbono de R2 están opcionalmente sustituidos independientemente como sigue: a) el(los) carbono(s) están opcionalmente mono, di o trisustituidos independientemente con halo, b) el(los) carbono(s) están opcionalmente monosustituidos con hidroxi o alcoxi C1-4, y c) el(los) carbono(s) están opcionalmente monosustituidos cono oxo; y en la que el(los) carbono(s) de la cadena de carbono de R2 están opcionalmente monosustituidos con Q; en la que Q es un anillo de tres a ocho miembros, parcial o totalmente saturado o totalmente insaturado, que tiene, opcionalmente, de uno a cuatro heteroátomos seleccionados independientemente entre oxígeno, azufre y nitrógeno, o es un anillo bicíclico que consiste en dos anillos condensados de tres a seis miembros parcial o totalmente insaturados, considerados independientemente; en la que el anillo bicíclico tiene, opcionalmente, de uno a cuatro heteroátomos seleccionados independientemente entre oxígeno, azufre y nitrógeno; en la que el anillo Q está opcionalmente mono, di, o trisustituido independientemente con a) halo, b) alquenilo C2-6, c) alquilo C1-6, d) hidroxi, e) alcoxi C1-6, f) (alquil C1-4)tio, g) amino, h) nitro, i) ciano, j) oxo, k) carboxi, l) (alquil C1-6)oxicarbonilo, o m) mono-N o di-N,N-(alquil C1-6)amino; en la que los sustituyentes alquilo C1-6 y alcoxi C1-6 en el anillo Q están opcionalmente mono, di trisustituidos independientemente con a) halo, b) hidroxi, c) alcoxi C1-6, d) (alquil C1-4)tio, e) amino, f) nitro, g) ciano, h) oxo, i) carboxi, j) (alquil C1-6)oxicarbonilo, o k) mono-N o di-N,N-(alquil C1-6)amino; en los cuales el sustituyentes alquilo C1-6 que está en el anillo Q está también opcionalmente sustituido con de uno a nueve átomos de flúor; o en la que R1 y R2 se unen conjuntamente para formar un anillo carbocíclico de tres a seis miembros completamente saturado, que tiene, opcionalmente, un heteroátomo seleccionado entre oxígeno, azufre o nitrógeno para formar un anillo heterocíclico; E es a) carbonilo, b) sulfonilo o c) metileno; W es a) un enlace, b) carbonilo, c) -N(H)-, d) -N(alquil C1-4)-, e) alquenilo C2-6, f) oxo, g) -(alquilC1-4)-O-, h) -NH-(alquil C1-4)-, o i) -alquil (C1-6; en la cual los grupos alquilo C1-6 y alquenilo C2-6 de W pueden estar, opcionalmente, mono o disustituidos independientemente con a) oxo, b) halo, c) (alcoxi C1-6)carbonilo, d) alquilo C1-6, e), alquenilo C2-6, f) cicloalquilo C3-7, g) hidroxi, h) alcoxi C1-6, i) (alquil C1-4)tio, j) amino, k) ciano, l) nitro, m) mono-N- o di-N,N-alquilamino C1-6, o n) -NH-alquilamino C1-4; o en la que W es CR7R8, en la que R7 y R8 están unidos conjuntamente para formar un anillo carbocíclico de tres a seis miembros totalmente saturado; A es a) mono-N o di-N,N-(alquil C1-6)amino, b) (alcanoil C2-6)amino, c) alcoxi C1-6, d) un anillo de tres a ocho miembros parcialmente o totalmente saturado o totalmente insaturado que tenga opcionalmente de uno a cuatro heteroátomos seleccionados independientemente entre oxígeno, azufre y nitrógeno, o e) un anillo bicíclico que consiste en dos anillos de tres a seis miembros condensados, parcialmente o totalmente saturados o totalmente insaturados, considerados independientemente; en la que el anillo bicíclico opcionalmente tiene de uno a cuatro heteroátomos seleccionados independientemente entre oxígeno, azufre y nitrógeno; y en la que el anillo A está opcionalmente mono, di o trisustituido independientemente con a) oxo, b) carboxi, c) halógeno, d) alcoxicarbonilo C1-6, e) alquilo C1-6, f) alquenilo C2-6, g) cicloalquilo C3-7, h) (cicloalquil C3-7)alquilo C1-6, i) hidroxi), j) alcoxi C1-6, k) (alquil C1-4)tio; l) (alquil C1-4)sulfonilo; m) amino, n) ciano, o) nitro, o p) mono-N- o di-N,N-alquilamino C1-6); en el que los sustituyentes alquilo C1-6 y alcoxi C1-6 del anillo A están también opcionalmente mono, di o trisustituidos, independientemente, con a) halo, b) hidroxi, c) alquilo C1-4 opcionalmente sustituido con de uno a nueve átomos de flúor, d) cicloalquilo C1-6, e) alcoxi C1-6, f) amino, g) mono-N- o di-N,N-alquilamino C1-6; o en la que el anillo A está opcionalmente monosustituido con un anillo de tres a ocho miembros parcial o totalmente saturado o totalmente insaturado, que tiene opcionalmente de uno a cuatro heteroátomos seleccionados independientemente entre oxígeno, azufre y nitrógeno; también en la que este anillo de tres a ocho miembros está opcionalmente mono, di o trisustituido independientemente con a) halo, b) hidroxi, c) alquilo C1-4 opcionalmente sustituido con de uno a nueve átomos de flúor, d) cicloalquilo C3-6, e) alcoxi C1-6, f) amino, g) mono-N- o di-N,N-(alquil C1-6)amino, o h) alquil C1-4, con tal que: a) cuando V e Y son cada uno metileno y m y n están cada uno formando un anillo de piperidinilo de seis miembros; este anillo está sustituido por el anillo de fenilo (denominado como J) en una posición distinta de la 4; b) cuando E es carbonilo, W es un enlace y X es -B-C(R1R2)-Z en la que R1 y R2 son, cada uno, hidrógeno, B es -O- o -N(H)-, Z es -C(O)OH o -C(O)O-alquilo C1-4, entonces uno de F o G debe ser: a) -alquilo C1-4, b) cicloalquilo C3-6, c) alcoxi C1-4 o d) (alquil C1-4)tio.
ARP030104332A 2002-11-26 2003-11-24 Compuestos de piperidina fenil sustituidas y su uso como activadores de ppar AR042131A1 (es)

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KR (2) KR100875318B1 (es)
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AT (1) ATE425966T1 (es)
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