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AR059643A1 - BICYCLE HETEROARYL DERIVATIVES AS CANABINOID RECEIVER MODULATORS - Google Patents

BICYCLE HETEROARYL DERIVATIVES AS CANABINOID RECEIVER MODULATORS

Info

Publication number
AR059643A1
AR059643A1 ARP070100803A ARP070100803A AR059643A1 AR 059643 A1 AR059643 A1 AR 059643A1 AR P070100803 A ARP070100803 A AR P070100803A AR P070100803 A ARP070100803 A AR P070100803A AR 059643 A1 AR059643 A1 AR 059643A1
Authority
AR
Argentina
Prior art keywords
substituted
unsubstituted
alkyl
cycloalkenyl
heteroaryl
Prior art date
Application number
ARP070100803A
Other languages
Spanish (es)
Inventor
Kundu Mrinalkanti
V Karnik Pellavi
M Nadkarni Suhas
Khairatkar-Joshi Neelima
Madhavrao Pensare Rameswar
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 AR059643A1 publication Critical patent/AR059643A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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
    • 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

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Diabetes (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

La presente está relacionada con derivados bicíclicos novedosos como moduladores del receptor canabinoide, en particular moduladores del receptor canabinoide 1 (CB1) o canabinoide 2 (CB2). Estos compuestos se suelen usar, para tratar dolor, trastornos neurodegenerativos, trastornos del comer, control o pérdida de peso, obesidad y para dejar de fumar, dependencia del alcohol, depresion, y trastorno de hiperactividad por déficit de atencion. También se proporcionan composiciones farmacéuticas que contienen los compuestos descritos, que pueden utilizarse para el tratamiento de enfermedades, condicion y/o trastornos mediados por el receptor canabinoide (tales como CB1 o CB2). Reivindicacion 1: Se reivindica un compuesto de formula (1) y análogos, N-oxidos, tautomeros, regioisomeros, estereoisomeros, prodrogas, polimorfos y sales, solvatos e hidratos farmacéuticamente aceptables de éste en donde: (i) X1 es CR y X2 es N, o (ii) X1 es N y X2 es CR; R, R1a, R1b, R2a, R2b, R2c, R2d, R2e, R3a, R3b, R3c, R3d y R3e son independientemente, H, ciano, formilo, acetilo, tio, nitro, halogeno, -OR4, -SR4, 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, grupo heterocíclico sustituido o no sustituido, heterociclilalquilo sustituido o no sustituido, -NR4R5, -C(=B)-R4, -C(O)O-R4, -C(O)NR4R5, -NR4C(O)-R5, - S(O)m-R4 o -S(O)m-NR4R5; cada presencia de R4 y R5 es independientemente H, nitro, halo, ciano, -ORa, -SRa, 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, grupo heterocíclico sustituido o no sustituido, heterociclilalquilo sustituido o no sustituido, -C(=B)-Ra, -C(O)O-Ra, -C(O)NRaRb, -S(O)m-Ra, -S(O)m-NRaRb, -NRaRb o un grupo de proteccion o R4 y R5 pueden estar unidos junto con el átomo de N al cual están unidos para formar un anillo cíclico insaturado o saturado de 3 a 7 miembros opcionalmente sustituidos, que opcionalmente pueden incluir al menos dos heteroátomos seleccionados de O, NRa o S; cada presencia de B es O, S o NRa; cada presencia de Ra y Rb es independientemente H, halogeno, nitro, ciano, formilo, acetilo, oxo, tio, -C(O)-Rc, -C(O)O-Rc, -C(O)NRcRd, -S(O)m-Rc, -S(O)m-NRcRd, NRcRd, -ORc, -SRd, un grupo de proteccion, 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, grupo heterocíclico sustituido o no sustituido, heterociclilalquilo sustituido o no sustituido o un heteroarilalquilo sustituido o no sustituido; o Ra y Rb pueden estar unidos junto con el átomo de N al cual están unidos para formar un anillo cíclico insaturado o saturado de 3 a 7 miembros opcionalmente sustituidos, que opcionalmente pueden incluir los heteroátomos seleccionados de O, NRa o S; cada presencia de Rc y Rd es independientemente H, halogeno, nitro, ciano, formilo, acetilo, oxo, tío, un grupo de proteccion, 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, grupo heterocíclico sustituido o no sustituido o heterociclilalquilo sustituido o no sustituido, y cada presencia de m es 0, 1 o 2.This is related to novel bicyclic derivatives as modulators of the cannabinoid receptor, in particular modulators of the cannabinoid receptor 1 (CB1) or cannabinoid 2 (CB2). These compounds are often used to treat pain, neurodegenerative disorders, eating disorders, weight control or loss, obesity and to quit smoking, alcohol dependence, depression, and attention deficit hyperactivity disorder. Pharmaceutical compositions containing the described compounds are also provided, which can be used for the treatment of diseases, conditions and / or disorders mediated by the cannabinoid receptor (such as CB1 or CB2). Claim 1: A compound of formula (1) and analogues, N-oxides, tautomers, regioisomers, stereoisomers, prodrugs, polymorphs and pharmaceutically acceptable salts, solvates and hydrates thereof is claimed wherein: (i) X1 is CR and X2 is N, or (ii) X1 is N and X2 is CR; R, R1a, R1b, R2a, R2b, R2c, R2d, R2e, R3a, R3b, R3c, R3d and R3e are independently, H, cyano, formyl, acetyl, thio, nitro, halogen, -OR4, -SR4, substituted alkyl or unsubstituted, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkylalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted cycloalkenyl alkyl, substituted or unsubstituted aryl, substituted or unsubstituted aryl substituted, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroarylalkyl, substituted or unsubstituted heterocyclic group, substituted or unsubstituted heterocyclyl alkyl, -NR4R5, -C (= B) -R4, -C (O) O-R4, -C (O) NR4R5, -NR4C (O) -R5, - S (O) m-R4 or -S (O) m-NR4R5; each presence of R4 and R5 is independently H, nitro, halo, cyano, -ORa, -SRa, substituted or unsubstituted alkyl ,, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkyl, substituted cycloalkylalkyl or unsubstituted, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted cycloalkenyl alkyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclic group, substituted heterocyclyl or alkyl substituted, -C (= B) -Ra, -C (O) O-Ra, -C (O) NRaRb, -S (O) m-Ra, -S (O) m-NRaRb, -NRaRb or a group or R4 and R5 may be attached together with the N atom to which they are attached to form an optionally substituted unsaturated or saturated cyclic ring of 3 to 7 members, which may optionally include at least two heteroatoms selected from O, NRa or S ; each presence of B is O, S or NRa; Each presence of Ra and Rb is independently H, halogen, nitro, cyano, formyl, acetyl, oxo, thio, -C (O) -Rc, -C (O) O-Rc, -C (O) NRcRd, -S (O) m-Rc, -S (O) m-NRcRd, NRcRd, -ORc, -SRd, a protection group, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted cycloalkyl or unsubstituted, substituted or unsubstituted cycloalkylalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted cycloalkenyl alkyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclic group, substituted heterocyclyl or alkyl substituted or a substituted or unsubstituted heteroarylalkyl; or Ra and Rb may be linked together with the N atom to which they are attached to form an optionally substituted unsaturated or saturated 3- to 7-membered cyclic ring, which may optionally include heteroatoms selected from O, NRa or S; each presence of Rc and Rd is independently H, halogen, nitro, cyano, formyl, acetyl, oxo, uncle, a protecting group, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted cycloalkyl or unsubstituted, substituted or unsubstituted cycloalkylalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted cycloalkenylalkyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryl, unsubstituted or heterocyclic group substituted or substituted or unsubstituted heterocyclylalkyl, and each presence of m is 0, 1 or 2.

ARP070100803A 2006-02-27 2007-02-27 BICYCLE HETEROARYL DERIVATIVES AS CANABINOID RECEIVER MODULATORS AR059643A1 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
IN275MU2006 2006-02-27
US78105506P 2006-03-10 2006-03-10
IN1146MU2006 2006-07-18
US82147506P 2006-08-04 2006-08-04
IN2088MU2006 2006-12-20

Publications (1)

Publication Number Publication Date
AR059643A1 true AR059643A1 (en) 2008-04-16

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Family Applications (1)

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ARP070100803A AR059643A1 (en) 2006-02-27 2007-02-27 BICYCLE HETEROARYL DERIVATIVES AS CANABINOID RECEIVER MODULATORS

Country Status (4)

Country Link
AR (1) AR059643A1 (en)
PE (1) PE20080114A1 (en)
TW (1) TW200745126A (en)
WO (1) WO2007096764A2 (en)

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