AR052244A1 - Inhibidores de hmg co-a reductasa derivados de pirazol para el tratamiento de enfermedades relacionadas, un metodo para su preparacion y composiciones farmaceuticas que los contienen - Google Patents

Inhibidores de hmg co-a reductasa derivados de pirazol para el tratamiento de enfermedades relacionadas, un metodo para su preparacion y composiciones farmaceuticas que los contienen

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AR052244A1
AR052244A1 ARP050104871A ARP050104871A AR052244A1 AR 052244 A1 AR052244 A1 AR 052244A1 AR P050104871 A ARP050104871 A AR P050104871A AR P050104871 A ARP050104871 A AR P050104871A AR 052244 A1 AR052244 A1 AR 052244A1
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Argentina
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aralkyl
aryl
alkyl
heteroaralkyl
heteroaryl
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Warner Lambert Co
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D231/00Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4151,2-Diazoles
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    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00Drugs for disorders of the urinary system
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    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • A61P19/08Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
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    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/06Antihyperlipidemics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/08Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D231/00Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/02Heterocyclic 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
    • C07D401/06Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/02Heterocyclic 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
    • C07D401/12Heterocyclic 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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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic 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
    • C07D405/02Heterocyclic 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
    • C07D405/06Heterocyclic 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

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  • Chemical & Material Sciences (AREA)
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  • Health & Medical Sciences (AREA)
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  • Hematology (AREA)
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  • Urology & Nephrology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Orthopedic Medicine & Surgery (AREA)
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  • Emergency Medicine (AREA)
  • Psychiatry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Steroid Compounds (AREA)

Abstract

Compuestos y composiciones farmacéuticas utiles como agentes hipocolesterolémicos e hipolipidémicos. Más específicamente, se describen potentes inhibidores de la enzima 3-hidroxi-3-metilglutaril-coenzima A reductasa (ôHMG CoA reductasaö). Se describen también procedimientos de preparacion de tales compuestos y composiciones para tratar sujetos, incluyendo seres humanos, que sufren hiperlipidemia, hipercolesterolemia, hipertrigliceridemia, aterosclerosis, enfermedad de Alzheimer, hipertrofia prostática benigna (HPB), diabetes y osteoporosis. Reivindicacion 1: Un compuesto de formula (1), o una de sus sales, ésteres, amidas, hidratos, estereoisomeros o profármacos farmacéuticamente aceptables, o una sal farmacéuticamente aceptable del profármaco, en la que: R1 es hidrogeno, halogeno, alquilo C1-7, cicloalquilo C3-8, arilo, aralquilo, heteroarilo o heteroaralquilo; estando el alquilo, cicloalquilo, arilo, aralquilo, heteroarilo o heteroaralquilo de R1 opcionalmente sustituido; R2 es hidrogeno, halogeno, alquilo C1-7, cicloalquilo C3-8, arilo, aralquilo, heteroarilo, heteroaralquilo, NC-, R2bR2aNCO(CH2)n-, R2bR2aNS(O)n-, R2cS(O)n-, R2bR2aN(CH2)n-, R2b-J-C(O)NR2a(CH2)n-, R2b-J-SO2NR2a(CH2) n-, R2b-J-SONR2a(CH2)n, R7OOC(CH2)n-, o R7CO(CH2)n-; estando el alquilo, cicloalquilo, arilo, aralquilo, heteroarilo o heteroaralquilo de R2 opcionalmente sustituido; J es un enlace directo, O o N; cada uno de R2a y R2b es independientemente hidrogeno, alquilo C1-10, cicloalquilo C3-8, arilo, aralquilo, heteroarilo o heteroaralquilo; estando el alquilo, cicloalquilo, arilo, aralquilo, heteroarilo o heteroaralquilo de R2a y R2b opcionalmente sustituido; o R2a y R2b tomados junto con el nitrogeno al que están unidos forman un anillo de 4-11 miembros que opcionalmente contiene al menos un heteroátomo adicional seleccionado de O, N y S, estando dicho anillo opcionalmente sustituido con al menos uno de arilo, aralquilo, heteroarilo, heteroaralquilo, alquilo C1-10, haloalquilo C1-10, cicloalquilo C3-8, halogeno, R7O-, R7OOC(CH2)n-, R7R8NCO(CH2)n-, R7O2S(CH2)n-, R8R7NSO2- o NC-; R2c es arilo, aralquilo, alquilo, heteroarilo o heteroaralquilo; estando el arilo, aralquilo, alquilo, heteroarilo o heteroaralquilo de R2c opcionalmente sustituido; cada uno de R7 y R8 es independientemente hidrogeno, alquilo C1-12, arilo o aralquilo; estando el alquilo, arilo o aralquilo de R7 y R8 opcionalmente sustituido; n es 0, 1 o 2; R3 es hidrogeno, alquilo C1-6, cicloalquilo C3-8, arilo, aralquilo, heteroarilo o heteroaralquilo; estando el alquilo, cicloalquilo, arilo, aralquilo, heteroarilo o heteroaralquilo de R3 opcionalmente sustituido; y ôla línea de puntoö es un enlace o está ausente. Reivindicacion 12: Un compuesto de formula (2), o una de sus sales, ésteres, amidas, hidratos, estereoisomeros o profármacos farmacéuticamente aceptables, o una de las sales farmacéuticamente aceptables del profármaco, en la que: R1 es hidrogeno, halogeno, alquilo C1-7, cicloalquilo C3-8, arilo, aralquilo, heteroarilo o heteroaralquilo; estando el alquilo, cicloalquilo, arilo, aralquilo, heteroarilo o heteroaralquilo de R1 opcionalmente sustituido; R2 es hidrogeno, halogeno, alquilo C1-7, cicloalquilo C3-8, arilo, aralquilo, heteroarilo, heteroaralquilo, NC-, R2bR2aNCO(CH2)n-, R2bR2aNS(O)n-, R2cS(O)n-, R2bR2aN(CH2)n-, R2b-J-C(O)NR2a(CH2)n-, R2b-J-SO2NR2a(CH2) n-, R2b-J-SONR2a(CH2)n, R7OOC(CH2)n-, o R7CO(CH2)n-; estando el alquilo, cicloalquilo, arilo, aralquilo, heteroarilo o heteroaralquilo de R2 opcionalmente sustituido; J es un enlace directo, O o N; cada uno de R2a y R2b es independientemente hidrogeno, alquilo C1-10, cicloalquilo C3-8, arilo, aralquilo, heteroarilo o heteroaralquilo; estando el alquilo, cicloalquilo, arilo, aralquilo, heteroarilo o heteroaralquilo de R2a y R2b opcionalmente sustituido; o R2a y R2b tomados junto con el nitrogeno al que están unidos forman un anillo de 4-11 miembros que opcionalmente contiene al menos un heteroátomo adicional seleccionado de O, N y S, estando dicho anillo opcionalmente sustituido con al menos uno de arilo, aralquilo, heteroarilo, heteroaralquilo, alquilo C1-10, cicloalquilo C3-8, halogeno, R7O- , R7OOC(CH2)n-, R7R8NCO(CH2)n-, R7O2S(CH2)n-, R8R7NSO2- o NC-; R2c es arilo, aralquilo, alquilo, heteroarilo o heteroaralquilo; estando el arilo, aralquilo, alquilo, heteroarilo o heteroaralquilo de R2c opcionalmente sustituido; cada uno de R7 y R8 es independientemente hidrogeno, alquilo C1-12, arilo o aralquilo; estando el alquilo, arilo o aralquilo de R7 y R8 opcionalmente sustituido; n es 0, 1 o 2; R3 es hidrogeno, alquilo C1-6, cicloalquilo C3-8, arilo, aralquilo, heteroarilo o heteroaralquilo; estando el alquilo, cicloalquilo, arilo, aralquilo, heteroarilo o heteroaralquilo de R3 opcionalmente sustituido; y ôla línea de puntoö es un enlace o está ausente. Reivindicacion 14: Un compuesto de formula (3), o una de sus sales, ésteres, amidas, hidratos, estereoisomeros o profármacos farmacéuticamente aceptables, o una de las sales farmacéuticamente aceptables del profármaco, en la que: R1 es hidrogeno, halogeno, alquilo C1-7, cicloalquilo C3-8, arilo, aralquilo, heteroarilo o heteroaralquilo; estando el alquilo, cicloalquilo, arilo, aralquilo, heteroarilo o heteroaralquilo de R1 opcionalmente sustituido; R2 es hidrogeno, halogeno, alquilo C1-7, cicloalquilo C3-8, arilo, aralquilo, heteroarilo, heteroaralquilo, NC-, R2bR2aNCO(CH2)n-, R2bR2aNS(O)n-, R2cS(O)n-, R2bR2aN(CH2)n-, R2b-J-C(O)NR2a(CH2)n-, R2b-J-SO2NR2a(CH2) n-, R2b-J-SONR2a(CH2)n, R7OOC(CH2)n-, o R7CO(CH2)n-; estando el alquilo, cicloalquilo, arilo, aralquilo, heteroarilo o heteroaralquilo de R2 opcionalmente sustituido; J es un enlace directo, O o N; cada uno de R2a y R2b es independientemente hidrogeno, alquilo C1-10, cicloalquilo C3-8, arilo, aralquilo, heteroarilo o heteroaralquilo; estando el alquilo, cicloalquilo, arilo, aralquilo, heteroarilo o heteroaralquilo de R2a y R2b opcionalmente sustituido; o R2a y R2b tomados junto con el nitrogeno al que están unidos forman un anillo de 4-11 miembros que opcionalmente contiene al menos un heteroátomo adicional seleccionado de O, N y S, estando dicho anillo opcionalmente sustituido con al menos uno de arilo, aralquilo, heteroarilo, heteroaralquilo, alquilo C1-10, cicloalquilo C3-8, halogeno, R7O-, R7OOC(CH2)n-, R7R8NCO(CH2)n-, R7O2S(CH2)n-, R8R7NSO2- o NC-; R2c es arilo, aralquilo, alquilo, heteroarilo o heteroaralquilo; estando el arilo, aralquilo, alquilo, heteroarilo o heteroaralquilo de R2c opcionalmente sustituido; cada uno de R7 y R8 es independientemente hidrogeno, alquilo C1- 12, arilo o aralquilo; estando el alquilo, arilo o aralquilo de R7 y R8 opcionalmente sustituido; n es 0, 1 o 2; R3 es hidrogeno, alquilo C1-6, cicloalquilo C3-8, arilo, aralquilo, heteroarilo o heteroaralquilo; estando el alquilo, cicloalquilo, arilo, aralquilo, heteroarilo o heteroaralquilo de R3 opcionalmente sustituido; y ôla línea de puntoö es un enlace o está ausente. Reivindicacion 20: Un compuesto de formula (4), en la que: R1 es hidrogeno, halogeno, alquilo C1-7, cicloalquilo C3- 8, arilo, aralquilo, heteroarilo o heteroaralquilo; estando el alquilo, cicloalquilo, arilo, aralquilo, heteroarilo o heteroaralquilo de R1 opcionalmente sustituido; cada uno de R2a y R2b es independientemente hidrogeno, alquilo C1-10, cicloalquilo C3-8, arilo, aralquilo, heteroarilo o heteroaralquilo; estando el alquilo, cicloalquilo, arilo, aralquilo, heteroarilo o heteroaralquilo de R2a y R2b opcionalmente sustituido; o R2a y R2b tomados junto con el nitrogeno al que están unidos forman un anillo de 4-11 miembros que opcionalmente contiene al menos un heteroátomo adicional seleccionado de O, N y S, estando dicho anillo opcionalmente sustituido con al menos uno de arilo, aralquilo, heteroarilo, heteroaralquilo, alquilo C1-10, cicloalquilo C3-8, halogeno, R7O-, R7OOC(CH2)n-, R7R8NCO(CH2)n-, R7O2S(CH2)n-, R8R7NSO2- o NC-; cada uno de R7 y R8 es independientemente hidrogeno, alquilo C1-12, arilo o aralquilo; estando el alquilo, arilo o aralquilo de R7 y R8 opcionalmente sustituido; n es 0, 1 o 2; R3 es hidrogeno, alquilo C1-6, cicloalquilo C3-8, arilo, aralquilo, heteroarilo o heteroaralquilo; estando el alquilo, cicloalquilo, arilo, aralquilo, heteroarilo o heteroaralquilo de R3 opcionalmente sustituido. Reivindicacion 21: Un compuesto de formula (5), en la que: R1 es hidrogeno, halogeno, alquilo C1-7, cicloalquilo C3-8, arilo, aralquilo, heteroarilo o heteroaralquilo; estando el alquilo, cicloalquilo, arilo, aralquilo, heteroarilo o heteroaralquilo de R1 opcionalmente sustituido; cada uno de R2a y R2b es independientemente hidrogeno, alquilo C1-10, cicloalquilo C3-8, arilo, aralquilo, heteroarilo o heteroaralquilo; estando el alquilo, cicloalquilo, arilo, aralquilo, heteroarilo o heteroaralquilo de R2a y R2b opcionalmente sustituido; o R2a y R2b tomados junto con el nitrogeno al que están unidos forman un anillo de 4-11 miembros que opcionalmente contiene al menos un heteroátomo adicional seleccionado de O, N y S, estando dicho anillo opcionalmente sustituido con al menos uno de arilo, aralquilo, heteroarilo, heteroaralquilo, alquilo C1-10, cicloalquilo C3-8, halogeno, R7O-, R7OOC(CH2)n-, R7R8NCO(CH2)n-, R7O2S(CH2)n-, R8R7NSO2- o NC-; cada uno de R7 y R8 es independientemente hidrogeno, alquilo C1-12, arilo o aralquilo; estando el alquilo, arilo o aralquilo de R7 y R8 opcionalmente sustituido; n es 0, 1 o 2; R3 es hidrogeno, alquilo C1-6, cicloalquilo C3-8, arilo, aralquilo, heteroarilo o heteroaralquilo; estando el alquilo, cicloalquilo, arilo, aralquilo, heteroarilo o heteroaralquilo de R3 opcionalmente sustituido; y X es anion F, Cl, Br o I. Reivindicacion 26: Un procedimiento que comprende las etapas de: a) hacer reaccionar un compuesto hidroxilado de formula (6), en condiciones suficientes par formar un compuesto de formula (7); b) hacer reaccionar un compuesto de formula (7), en condiciones suficientes para formar un compuesto de formula (8); c
ARP050104871A 2004-11-23 2005-11-21 Inhibidores de hmg co-a reductasa derivados de pirazol para el tratamiento de enfermedades relacionadas, un metodo para su preparacion y composiciones farmaceuticas que los contienen AR052244A1 (es)

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