AR055622A1 - Metodos de preparacion de benzimidazoles sustituidos y compuestos derivados de los mismos. - Google Patents

Metodos de preparacion de benzimidazoles sustituidos y compuestos derivados de los mismos.

Info

Publication number
AR055622A1
AR055622A1 ARP060103802A ARP060103802A AR055622A1 AR 055622 A1 AR055622 A1 AR 055622A1 AR P060103802 A ARP060103802 A AR P060103802A AR P060103802 A ARP060103802 A AR P060103802A AR 055622 A1 AR055622 A1 AR 055622A1
Authority
AR
Argentina
Prior art keywords
compound
formula
alkyl
halo
tautomer
Prior art date
Application number
ARP060103802A
Other languages
English (en)
Inventor
Martin Dimitroff
Bridget R Miller
Brady S Stillwell
David A Siesel
Tyson Swiftney
Brian Diaz
Danlin Gu
Dyck Jonathan P Van
David Ryckman
Original Assignee
Novartis Ag
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 Novartis Ag filed Critical Novartis Ag
Publication of AR055622A1 publication Critical patent/AR055622A1/es

Links

Classifications

    • 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
    • C07D401/14—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 three or more hetero rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • 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
    • 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
    • C07D403/14—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 three or more hetero rings
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oncology (AREA)
  • Hematology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Reivindicacion 1: Un método para preparar un compuesto de formula (1) o un tautomero, estereoisomero, éster, metabolito, prodroga, o sal aceptable para uso farmacéutico del mismo en donde cada R1 se selecciona en forma independiente entre hidroxi, halo, alquilo C1-6, alcoxi C1-6, (alquil C1-6)sulfanilo, (alquil C1-6)sulfonilo, cicloalquilo, heterocicloalquilo, fenilo, y heteroarilo; R2 es C1-6 alquilo o halo(alquilo C1-6); cada R3 se selecciona en forma independiente entre halo, alquilo C1-6, y alcoxi C1-6, cada R4 se selecciona en forma independiente entre hidroxi, alquilo C1-6, alcoxi C1-6, halo, heterocicloalquilcarbonilo, carboxilo, alcoxi C1-6)carbonilo, aminocarbonilo, alquilaminocarbonilo C1-6, carbonitrilo, cicloalquilo, heterocicloalquilo, fenilo, y heteroarilo; en donde R1, R2, R3, y R4 pueden estar opcionalmente sustituidos con uno o más sustituyentes seleccionados en forma independiente entre hidroxi, halo, alquilo C1-6, halo(alquil C1-6), alcoxi C1-6, y halo(alcoxi C1-6); a es 1, 2, 3, 4 o 5; b es 0, 1, 2, o 3; c es 1 o 2; caracterizado porque comprende: (a) hacer reaccionar un compuesto de formula (2) con un compuesto de formula (3) para obtener un compuesto de formula (4) en donde Q es NH2 o NO2; uno de L1 o L2 es halo y el otro de L1 o L2 es OH o un anion del mismo Z es cano, COOR5, CH2OR5, CHO, o imidazol-2-ilo sustituido con uno o dos Grupos R4 y en donde R5 es H o un grupo protector de hidroxi; (b) cuando en el compuesto de formula (4) Z es ciano, COOR5 o CH2OR5, convertir dicho compuesto en un compuesto de formula (4) en donde Z es CHO; (c) cuando en el compuesto de formula (4) Z es ciano, convertir la funcionalidad ciano en una funcionalidad amidino y hacer reaccionar dicha funcionalidad amidino con un compuesto de formula (5a) bajo condiciones de formacion del anillo imidazol; o cuando en el compuesto de formula (49 Z es CHO, hacer reaccionar dicho compuesto con un compuesto de formula (5b) para obtener un compuesto de formula (6) en donde Xa en la formula (5a) es un grupo saliente y R4p y R4q en la formula (5b) son en forma independiente H o R4; con la salvedad de que al menos uno de R4p y R4q es R4 y Xb es =O o =NHOH y con la salvedad de que c es 1 cuando un compuesto de formula (6) se prepara a partir de un compuesto de formula (5a); (d) cuando en el compuesto de formula (6) Q es NO2, convertir dicho compuesto en un compuesto de formula (6) en donde Q es NH2; (e) hacer reaccionar el compuesto de formula (6) en donde Q es NH2 con un compuesto de formula (7) para obtener un compuesto de formula (8) o un tautomero del mismo, (f) hacer reaccionar el compuesto de formula (8) o un tautomero del mismo con un agente desulfurizante para obtener un compuesto de formula (1); (g) opcionalmente hacer reaccionar el compuesto de formula (1) o un tautomero del mismo con un ácido para dar una primera sal aceptable para uso farmacéutico; (h) opcionalmente convertir la primera sal aceptable para uso farmacéutico de un compuesto de formula (1) o un tautomero del mismo en una segunda sal aceptable para uso farmacéutico, y (i) opcionalmente convertir un compuesto de formula (1) o un tautomero o sal aceptable para uso farmacéutico del mismo en un éster, metabolito, o prodroga de formula (1).
ARP060103802A 2005-08-30 2006-08-30 Metodos de preparacion de benzimidazoles sustituidos y compuestos derivados de los mismos. AR055622A1 (es)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US71253905P 2005-08-30 2005-08-30
US71310805P 2005-08-30 2005-08-30
US73159105P 2005-10-27 2005-10-27
US77468406P 2006-02-17 2006-02-17

Publications (1)

Publication Number Publication Date
AR055622A1 true AR055622A1 (es) 2007-08-29

Family

ID=37434025

Family Applications (2)

Application Number Title Priority Date Filing Date
ARP060103801A AR057109A1 (es) 2005-08-30 2006-08-30 Benzimidazoles sustituidos y metodos para usarlos como inhibidores de las quinasas asociadas con la tumorigenesis
ARP060103802A AR055622A1 (es) 2005-08-30 2006-08-30 Metodos de preparacion de benzimidazoles sustituidos y compuestos derivados de los mismos.

Family Applications Before (1)

Application Number Title Priority Date Filing Date
ARP060103801A AR057109A1 (es) 2005-08-30 2006-08-30 Benzimidazoles sustituidos y metodos para usarlos como inhibidores de las quinasas asociadas con la tumorigenesis

Country Status (37)

Country Link
US (6) US20070049622A1 (es)
EP (2) EP1924577B1 (es)
JP (4) JP5210866B2 (es)
KR (2) KR20080039965A (es)
AR (2) AR057109A1 (es)
AT (2) ATE526325T1 (es)
AU (2) AU2006287688B2 (es)
BR (2) BRPI0615314A2 (es)
CA (2) CA2620472C (es)
CR (1) CR9716A (es)
CU (1) CU23784B7 (es)
CY (2) CY1111871T1 (es)
DE (1) DE602006021036D1 (es)
DK (2) DK1924577T3 (es)
EA (1) EA014230B1 (es)
EC (2) ECSP088210A (es)
ES (1) ES2374451T3 (es)
GE (1) GEP20105004B (es)
GT (1) GT200600394A (es)
HK (2) HK1117519A1 (es)
HN (1) HN2008000317A (es)
HR (2) HRP20110312T1 (es)
IL (2) IL189080A (es)
MA (2) MA29772B1 (es)
MY (2) MY163886A (es)
NI (1) NI200800060A (es)
NO (1) NO20081476L (es)
NZ (2) NZ565450A (es)
PE (2) PE20070427A1 (es)
PL (2) PL1926722T3 (es)
PT (2) PT1924577E (es)
RS (1) RS52099B (es)
SI (2) SI1924577T1 (es)
SM (1) SMAP200800022A (es)
TN (2) TNSN08088A1 (es)
TW (2) TW200804345A (es)
WO (2) WO2007030377A1 (es)

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