AR066155A1 - Compuestos de pirazol, simil tiroideo, composicion farmaceutica, proceso y uso en terapia - Google Patents

Compuestos de pirazol, simil tiroideo, composicion farmaceutica, proceso y uso en terapia

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Publication number
AR066155A1
AR066155A1 ARP080102438A ARP080102438A AR066155A1 AR 066155 A1 AR066155 A1 AR 066155A1 AR P080102438 A ARP080102438 A AR P080102438A AR P080102438 A ARP080102438 A AR P080102438A AR 066155 A1 AR066155 A1 AR 066155A1
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AR
Argentina
Prior art keywords
alkyl
aryl
nhc
conh
nhso2
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ARP080102438A
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English (en)
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Torrent Pharmaceuticals Ltd
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Publication of AR066155A1 publication Critical patent/AR066155A1/es

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    • 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
    • C07D403/06—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 carbon chain containing only aliphatic carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • 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
    • 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
    • A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
    • 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
    • A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
    • A61P5/16—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4 for decreasing, blocking or antagonising the activity of the thyroid hormones
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic 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
    • C07D231/12—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic 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
    • C07D231/14—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic 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
    • C07D231/14—Heterocyclic 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
    • C07D231/18—One oxygen or sulfur atom
    • 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
    • C07D403/10—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 carbon chain containing aromatic 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
    • C07D403/12—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
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D413/06—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 carbon chain containing only aliphatic carbon atoms

Abstract

Los compuestos de formula (1) poseen una afinidad de enlace significativamente baja con receptores tiroideos y por lo tanto carecen de manera considerable de efectos tirotoxicos. También se refiere al uso del compuesto de formula (1) para la preparacion de un medicamento para tratar diversas afecciones patologicas tales como obesidad, dislipidemia, síndrome metabolico y co-morbilidades asociadas con síndrome metabolico. Reivindicacion 1: Un compuesto de formula (1) donde, R1 y R3 son iguales o diferentes y son seleccionados de manera independiente de H, alquilo C1-6, cicloalquilo C3-7, halo, CN, CF3, -O-alquilo C1-6, -CO2-alquilo C1-6, -COOH, -CONH-alquilo C1-6, -CONH-arilo, -NH2, -CONH-R6, -CONR5, -alquil C1-3-arilo, -alquilo C1-3-R6, -NH-alquilo C1-6, -NH-arilo, -NH-SO2-alquilo C1-6, -CH2NH-alquilo C1-6, -CH2-O-alquilo C1-6, -alquil C1-3-NR5, R6, R7, donde alquilo C1-6 y cicloalquilo C3-7 están sustituidos en forma opcional con uno o mas sustituyentes seleccionados de alquilo C1-6, halo, ciano, -OH, oxo, -COOH, -O-alquilo C1-6, -O-bencilo, -COO-alquilo C1-6, -CONH-alquilo C1-6, -CONR5, -CONH-arilo, -CONH-heteroarilo o -CH2NR5; R2 se selecciona de alquilo C1-6, cicloalquilo C3-6, alquenilo C3-6, alquinilo C3-6, -C(O)-alquil C1-3-COOH, -alquil C1-3-COOH, -C(O)-alquil-C1-3-COO-alquilo, -C(O)-C(O)O-alquilo C1-6, -C(O)-alquil- C1-3-NH-alquilo C1-6, -C(O)-O-alquilo C1-6, -C(O)NR5, -C(O)NH-alquilo C1-6, -C(O)-alquilarilo C1-3, -C(O)-alquil C1-3-R6, R6, R7, donde dicho alquilo C1-6, cicloalquilo C3-6, alquenilo C3-6, alquinilo C3-6 están sustituidos en forma opcional con uno o más sustituyentes seleccionados de perhaloalquilo, oxo, -C(O)OH, -C(O)-O-alquilo C1-3, -C(O)-O-alquil C1-3-arilo, -C(O)-O-alquil C1-3-R6, -CONH2, -CONH-alquilo C1-3, -C(O)NH-arilo, -C(O)NH-R6, -CONR5, -CONHNH2, -C(=NH)NH-alquilo C1-6, -C(=NH)NH2, C(=NH)NHOH, -C(O)-R8, -C(O)NHSO2-alquilo C1-6, -C(O)NHSO2-arilo, -C(O)NHOH, -C(O)NHSO2-R6, -C(O)NHNH-alquilo C1-6, -C(O)NHNH-arilo, -CONH-alquil C1-2-arilo, -C(O)NH-alquil C1-2-R6, -CH2NR5, -NH2, -NH-alquilo C1-6, -NH-C(O)-O-alquilo C1-3, -NH-C(O)-alquilo C1-3, -NHC(O)-arilo, -NHC(O)-alquilarilo C1-3, -NHC(O)-R6, -NH-C(O)NR5, -NH-C(O)NH-arilo, -NHC(O)NH-alquilo C1-6, -NHSO2-alquilo C1-6, -NH-SO2-arilo, -NH-SO2-R6, halo, ciano, -OH, -O-alquilo C1-6, -O-arilo, -O-heteroarilo, -O-alquil-C1-2-arilo, -SO3H, -SO2NH-arilo, -SO2NH-R6 o -SO2NH-alquilo C1-6, R6 o R7; R5 junto con el átomo de nitrogeno al que está unido forman un anillo saturado o insaturado de C3-6 miembros, que puede contener además 1-2 heteroátomos seleccionados de O, N o S y puede estar sustituido opcionalmente con uno o más sustituyentes seleccionados de oxo, -COOH, halo, -OH, -O-alquilo C1-6, o -alquilo C1-6; R6 se selecciona de fenilo o heteroarilo de 5-8 miembros que contiene 1-4 heteroátomos seleccionados de O, N o S, donde dicho anillo heteroarilo o fenilo están sustituidos en forma opcional con uno o más sustituyentes seleccionados de halogeno, -OH, -O-alquilo C1-6, -perhaloalquilo, -alquilo C1-6, -cicloalquilo C3-6, -SO2-alquilo C1-6, ciano, -COOH, -C(O)O-alquilo C1-6, -C(O)O-CH2-arilo, -C(O)O-arilo, -CONH-alquilo C1-3, nitro, -NH2, -NH-alquilo C1-6, -NHC(O)-alquilo C1-6, -NHC(O)-arilo, -NHSO-alquilo C1-6, -CONH2, -SO2-alquilo C1-6, -NHSO2-alquilo C1-6 o -COR8; R7 es un anillo heterocíclico de 3-6 miembros que contiene 1-4 heteroátomos seleccionados de O, N o S, y el mencionado anillo heterocíclico está sustituido opcionalmente con uno o más sustituyentes seleccionado de oxo, halogeno, -O-alquilo C1-6, -OH, -CF3, alquilo C1-6, cicloalquilo C3-6, ciano, -COOH, -C(O)O-alquilo C1-6, -C(O)O-CH2-arilo, -C(O)O-arilo, -NH2, -NH-alquilo C1-6, -NHC(O)-alquilo C1-6, -NHC(O)-arilo, -CONH2, -SO2-arilalquilo C1-6, -SO2-alquilo C1-6, -NHSO2-alquilo C1-6 o -COR8; R8 es un aminoácido que está enlazado a través de su átomo de nitrogeno; Z = O, CH2 o NH; R4 se selecciona de las formulas P, Q o T; R9 se selecciona de -OH, -O-alquilo, -OSO3H, halogeno, -C(O)O-alquilo C1-6, -C(O)NHR8, -OC(O)-alquilo C1-6, -O-perhaloalquilo, -OC(O)O-alquilo C1-6, -CONR5 , -NHCO-alquilo C1-6, -NHC(O)-O-alquilo C1-6, -NHC(O)-O-arilo, -NHSO2-alquilo C1-6, -NHSO2-arilo, -NHCONR5 o de formula (2); R10 se selecciona de H, halogeno, alquilo C1-6, alcoxi, ariloxi, -NHCO-alquilo C1-6, -NHSO2-alquilo C1-6 o -NH-SO2-arilo; R11 es -CO-alquilo C1-6, -SO2-alquilo C1-6 o -SO2-arilo; G' se selecciona de H, halogeno o alquilo C1-6; G'' se selecciona de hidrogeno, alquilo C1-6, cicloalquilo C3-6, arilo, halogeno, perhaloalquilo, CN, CHO, -alquilarilo-C1-3, -alquil C1-6-O-alquilo C1-6, -CH2R9, -CH2-arilo, -CH2NR5, -COOH, -C(O)O-alquilo C1-6, -CONH-alquilo C1-6, -CONR5, -SO2NR5, -SO2NH-alquilo C1-6, -SO2NH-arilo; n puede ser uno o dos; incluyendo sus sales aceptables para uso farmacéutico y sus hidratos, solvatos, atropisomeros, regioisomeros, enantiomeros, diasteromeros, tautomeros, polimorfos y profármacos de los mismos, con la salvedad que: cuando R4 es Q entonces R2 es diferente de R6 y R7; incluyendo sus sales aceptables para uso farmacéutico y sus hidratos, solvatos, atropisomeros, regioisomeros, enantiomeros, diasteromeros, tautomeros, polimorfos y profármacos de los mismos.
ARP080102438A 2007-06-06 2008-06-06 Compuestos de pirazol, simil tiroideo, composicion farmaceutica, proceso y uso en terapia AR066155A1 (es)

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IN857KO2007 2007-06-06

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US (2) US8143424B2 (es)
EP (1) EP2061766B1 (es)
JP (1) JP5243537B2 (es)
KR (1) KR101152965B1 (es)
CN (1) CN101772487B (es)
AR (1) AR066155A1 (es)
AT (1) ATE478053T1 (es)
AU (1) AU2008259314B2 (es)
CA (1) CA2698704C (es)
CY (1) CY1110925T1 (es)
DE (1) DE602008002205D1 (es)
DK (1) DK2061766T3 (es)
EA (1) EA019084B1 (es)
ES (1) ES2351274T3 (es)
HK (1) HK1129221A1 (es)
HR (1) HRP20100611T1 (es)
IL (1) IL202515A (es)
MX (1) MX2009013070A (es)
NZ (1) NZ582273A (es)
PL (1) PL2061766T3 (es)
PT (1) PT2061766E (es)
RS (1) RS51501B (es)
SI (1) SI2061766T1 (es)
TW (1) TWI360541B (es)
UA (1) UA98962C2 (es)
WO (1) WO2008149379A2 (es)
ZA (1) ZA200908760B (es)

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