AR063872A1 - Derivados de acetileno como inhibidores de estearoil coa desaturasa - Google Patents

Derivados de acetileno como inhibidores de estearoil coa desaturasa

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Publication number
AR063872A1
AR063872A1 ARP070105150A ARP070105150A AR063872A1 AR 063872 A1 AR063872 A1 AR 063872A1 AR P070105150 A ARP070105150 A AR P070105150A AR P070105150 A ARP070105150 A AR P070105150A AR 063872 A1 AR063872 A1 AR 063872A1
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AR
Argentina
Prior art keywords
substituted
unsubstituted
alkyl
case
cycloalkenyl
Prior art date
Application number
ARP070105150A
Other languages
English (en)
Inventor
Rakesh Datta
Neelima Khairatkar-Joshi
Shantaram Kashinath Phatangare
Dattaguru Anandrao More
Deepak Vitthal Ukride
Prasada Rao V S Lingam
Daisy Manis Shah
Original Assignee
Glenmark Pharmaceuticals Sa
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Glenmark Pharmaceuticals Sa filed Critical Glenmark Pharmaceuticals Sa
Publication of AR063872A1 publication Critical patent/AR063872A1/es

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having 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
    • C07D237/20—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D277/18—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
    • C07D401/10—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 aromatic rings
    • 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
    • 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
    • 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
    • C07D405/10—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 aromatic rings

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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)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Pyridine Compounds (AREA)

Abstract

La presente proporciona inhibidores de estearoil CoA desaturasa (SCD). En particular, los compuestos descriptos en la presente son útiles en el tratamiento o la prevención de enfermedades, condiciones y/o trastornos modulados por inhibidores de estearoil CoA desaturasa 1 (SCD1). También se proporcionan en la presente, procesos para preparar los compuestos descriptos en ella, los compuestos intermedios y su síntesis, composiciones farmacéuticas de éstas, y métodos para el tratamiento o prevención de enfermedades, condiciones y/o trastornos modulados por inhibidores de estearoil CoA desaturasa, como obesidad, trastorno del apetito, glucosa, insulina, lípidos, síndrome metabólico, enfermedad hígado adiposo. Reivindicación 1: Un compuesto de fórmula (1) A-U-B'-s-Q o una sal de ésta, un solvato de ésta, un profármaco de ésta, un estereoisómero de ésta o un N-óxido de ésta farmacéuticamente aceptables; donde: A es R'W-; R' se selecciona de alquilo sustituido o no sustituido, alquenilo sustituido o no sustituido, alquinilo sustituido o no sustituido, cicloalquilo sustituido o no sustituido, cicloalquilalquilo sustituido o no sustituido, cicloalquenilo sustituido o no sustituido, cicloalquenilalquilo sustituido o no sustituido, arilo sustituido o no sustituido, arilalquilo sustituido o no sustituido, heteroarilo sustituido o no sustituido, heteroarilalquilo sustituido o no sustituido, heterocíclico sustituido o no sustituido y heterociclilalquilo sustituido o no sustituido; W se selecciona de (CR1R2)p, C(=Y) , C(=Y)O, OC(=Y), O, CONR1, S(O)r, S(O)rNR1, NR1(CH2)nO, NR1 o NR1C(=Y)NR2; Q se selecciona de hidrógeno, hidroxilo, alquilo sustituido o no sustituido, alquenilo sustituido o no sustituido, alquinilo sustituido o no sustituido, cicloalquilo sustituido o no sustituido, cicloalquilalquilo sustituido o no sustituido, cicloalquenilo sustituido o no sustituido, cicloalquenilalquilo sustituido o no sustituido, arilo sustituido o no sustituido, arilalquilo sustituido o no sustituido, heteroarilo sustituido o no sustituido, heteroarilalquilo sustituido o no sustituido, heterocíclico sustituido o no sustituido y heterociclilalquilo sustituido o no sustituido; (CR1R2)nOR5, COR1, COOR1, CONR1R2, S(O)rNR1R2, NR1R2, (CH2)nNR1R2, (CH2)nCHR1R2, (CR1R2)NR5R6, (CR1R2)NR5CONR6R7, (CH)nNHCOR1 y (CH2)nNHSO2R1; U se selecciona de un enlace y el grupo de fórmula (2), donde V es CR y N y B es CR o N, o B junto con un átomo de carbono con anillo adyacente y A forman un anillo seleccionado de fórmulas (3), B' se selecciona de fórmulas (4); U y V son independientemente CR o N; en cada caso, R se selecciona independientemente de hidrógeno, hidroxilo, alquilo sustituido o no sustituido, alquenilo sustituido o no sustituido, alquinilo sustituido o no sustituido, cicloalquilo sustituido o no sustituido, cicloalquilalquilo sustituido o no sustituido, cicloalquenilo sustituido o no sustituido, cicloalquenilalquilo sustituido o no sustituido, arilo sustituido o no sustituido, arilalquilo sustituido o no sustituido, heteroarilo sustituido o no sustituido, heterociclilo sustituido o no sustituido, heterociclialquilo sustituido o no sustituido, heteroarilalquilo sustituido o no sustituido; en cada caso, m es independientemente un entero 0-4; en cada caso, n, n' y r son independientemente 0, 1 o 2; p es 0, 1, 2, 3, o 4; en cada caso, R1, R2, R5, R6 y R7 pueden ser idénticos o diferentes y se seleccionan independientemente de hidrógeno, halógeno, alquilo sustituido o no sustituido, alquenilo sustituido o no sustituido, alquinilo sustituido o no sustituido, cicloalquilo sustituido o no sustituido, cicloalquilalquilo sustituido o no sustituido, cicloalquenilo sustituido o no sustituido, cicloalquenilalquilo sustituido o no sustituido, arilo sustituido o no sustituido, arilalquilo sustituido o no sustituido, heteroarilo sustituido o no sustituido, heterocíclico sustituido o no sustituido, heterociclialquilo sustituido o no sustituido, heteroarilalquilo sustituido o no sustituido; o, cuando R1 y R2 están unidos a un átomo común, forman con el átomo común un heterociclilo de 3-7 miembros; en cada caso X1 a X4 son independientemente N o CR; en cada caso, X y X5 a X7 son independientemente CHR4, CO, CS, O, S(O)r, N, o NR4; en cada caso, R4 se selecciona independientemente de hidrógeno, hidroxilo, alquilo sustituido o no sustituido, cicloalquilo sustituido o no sustituido, arilo sustituido o no sustituido, heteroarilo sustituido o no sustituido, y heterociclilo sustituido o no sustituido; en cada caso, R3 se selecciona de hidrógeno, nitro, ciano, halógeno, COR1, alquilo sustituido o no sustituido, arilo sustituido o no sustituido, heteroarilo sustituido o no sustituido, alcoxi sustituido o no sustituido, COOR1, CONR1R2, S(O)rR1, S(O)rNR1R2 y NR1R2, y en cada caso, Y es O o S.
ARP070105150A 2006-11-20 2007-11-20 Derivados de acetileno como inhibidores de estearoil coa desaturasa AR063872A1 (es)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
IN1917MU2006 2006-11-20
IN2175MU2006 2006-12-29
IN1375MU2007 2007-07-17
US95410807P 2007-08-06 2007-08-06

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AR063872A1 true AR063872A1 (es) 2009-02-25

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US (1) US20080182851A1 (es)
EP (1) EP2099755A2 (es)
JP (1) JP2010510201A (es)
KR (1) KR20090083477A (es)
AR (1) AR063872A1 (es)
AU (1) AU2007323193A1 (es)
TW (1) TW200831482A (es)
WO (1) WO2008062276A2 (es)

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PT1942106E (pt) * 2003-08-01 2011-12-22 Euro Celtique Sa Agentes terapêuticos úteis para o tratamento da dor
WO2009048101A1 (ja) * 2007-10-10 2009-04-16 Takeda Pharmaceutical Company Limited アミド化合物
US20100234383A1 (en) * 2009-03-13 2010-09-16 Gilles Klopman Treating, preventing or ameliorating a hyperproliferative disease/disorder

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AU2007323193A1 (en) 2008-05-29
WO2008062276A3 (en) 2009-03-05
KR20090083477A (ko) 2009-08-03
TW200831482A (en) 2008-08-01
EP2099755A2 (en) 2009-09-16

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