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AR072900A1 - Agentes terapeuticos derivados de pirazolo[3,4-d]pirimidina - Google Patents

Agentes terapeuticos derivados de pirazolo[3,4-d]pirimidina

Info

Publication number
AR072900A1
AR072900A1 ARP090102973A ARP090102973A AR072900A1 AR 072900 A1 AR072900 A1 AR 072900A1 AR P090102973 A ARP090102973 A AR P090102973A AR P090102973 A ARP090102973 A AR P090102973A AR 072900 A1 AR072900 A1 AR 072900A1
Authority
AR
Argentina
Prior art keywords
alkyl
pyridyl
ring
pyrazolo
pyrimidin
Prior art date
Application number
ARP090102973A
Other languages
English (en)
Original Assignee
Astrazeneca Ab
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 Astrazeneca Ab filed Critical Astrazeneca Ab
Publication of AR072900A1 publication Critical patent/AR072900A1/es

Links

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
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • 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

Landscapes

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

Abstract

Agentes terapéuticos derivados de pirazolo[3,4-d]pirimidina util en el tratamiento o prevencion de una enfermedad o afeccion médica mediada por glucoquinasa (GLK o GK), que conduce a una reduccion del umbral de glucosa para la secrecion de insulina, diabetes tipo 2 y obesidad. Reivindicacion 1: Un compuesto de formula (1) o una sal farmacéuticamente aceptable del mismo en donde A y B son cada uno N o CR6, siempre que al menos uno de A y B sea CR6; X es C o N; Y es CH o N; Z es C o N; en donde X, Y y Z se seleccionan de forma tal que al menos dos de X, Y y Z son N, el anillo que los contiene es aromático y ningun átomo de N del anillo está cuaternizado; R1 es alquilo C1-6, arilo, arilalquilo C1-6, o HET-1, en donde el arilo, arilalquilo C1-6 y HET-1 están opcionalmente sustituidos por uno, dos, o tres grupos que se seleccionan independientemente de halo, alquilo C1-4, alcoxi C1-4, trifluorometilo, alquil C1-6tio, alquil C1-6sulfinilo, alquil C1-6sulfonilo, ciano, carboxi, alcoxi C1-6carbonilo, carbamoilo, N-alquil C1-4carbamoilo, N,N-dialquil C1-4carbamoilo, aminosulfonilo, alquil C1-6aminosulfonilo, dialquil C1-6aminosulfonilo, alcanoil C1-4amino, hidroxialquilo C1-4, alcoxi C1-4-alquilo C1-4, alquil C1-4S(O)p-alquilo C1-4, aminoalquilo C1-4, alquil C1-4-aminoalquilo C1-4, dialquil C1-4-aminoalquilo C1-4, alcoxi C1-6-carbonilalquilo C1-4, alquil C1-6-sulfoniloxi, cicloalquil C3-6-sulfonilo, alquil C1-6-sulfonilamino, azetidinilcarbonilo, pirrolidinilcarbonilo y HET-3A; en donde HET-1 es un anillo heteroarilo unido a C de 5 o 6 miembros, o un sistema de anillos bicíclico fusionado de formula -D-E, en donde el anillo D está unido a Z y es un anillo arilo o heteroarilo de 6 miembros y un anillo E es un anillo heteroarilo, heterociclilo o cicloalquilo de 5 o 6 miembros que está fusionado al anillo D en cualquier posicion disponible; R2 es alquilo C1-6 opcionalmente sustituido por uno o dos hidroxi o por uno de los siguientes: carboxi, carbamoilo, N,N-dialquil C1-4carbamoilo, alcoxi C1-6carbonilo, un grupo -N(R7)COR8 o un grupo NR9R10; o R2 es un grupo -(CHR4)n-P-Q en donde n es 1, 2, 3 o 4; P es un enlazante que se selecciona de O, SO2, CONH y NHCO; Q se selecciona de alquilo C1-6, cicloalquilo C3-6 y un heterociclilo de 4, 5 o 6 miembros (en donde dicho anillo heterociclilo contiene 1, 2 o 3 heteroátomos que se seleccionan independientemente de O, N y S, siempre que no haya enlaces O-O, S-S ni O-S en donde un átomo de C disponible en el anillo puede oxidarse para convertirse en un grupo carbonilo, un átomo de S disponible en el anillo puede oxidarse para convertirse en un grupo SO o SO2 y en donde opcionalmente hay un enlace doble en el anillo) y Q está opcionalmente sustituido en un átomo de C disponible por hidroxi o alcoxi C1-4; R3 es HET-2 en donde HET-2 es un anillo heteroarilo monocíclico unido a C de 5 o 6 miembros, que contiene un átomo de N en la posicion 2 y opcionalmente 1 o 2 heteroátomos del anillo adicionales que se seleccionan independientemente de O, N y S; o HET-2 es un anillo heteroarilo bicíclico unido a C de 8, 9 o 10 miembros que contiene un átomo de N en la posicion 2 con hasta cinco heteroátomos del anillo adicionales que se seleccionan independientemente de O, N y S; en donde HET-2 está opcionalmente sustituido en un átomo de C disponible, o en un átomo de N del anillo siempre que no quede de este modo cuaternizado, con 1 o 2 sustituyentes que se seleccionan independientemente de R11; cada R4 se selecciona independientemente de H, hidroxi, metilo y etilo; siempre que cuando n es > 1, entonces no más de dos grupos R4 son hidroxi; R5 es H, alcoxi C1-4 o alquilo C1-4; R6 es H, alcoxi C1-4 o alquilo C1-4; R7 es H, o alquilo C1-4; R8 es alquilo C1-4; R9 es H o alquilo C1-4 opcionalmente sustituido por hidroxi o metoxi; R10 es H o alquilo C1-4; o -NR9R10 forma una azetidina opcionalmente sustituida por hidroxi; R11 se selecciona independientemente de halo, alquilo C1-4, alcoxi C1-4, trifluorometilo, alquil C1-6tio, alquil C1-6sulfinilo, alquil C1-6sulfonilo, ciano, carboxi, alcoxi C1-6carbonilo, carbamoilo, N-alquil C1-4carbamoilo, N,N-dialquil C1-4carbamoilo, aminosulfonilo, alquil C1-6aminosulfonilo, dialquil C1-6aminosulfonilo, alcanoil C1-4amino, hidroxialquilo C1-4, alcoxi C1-4-alquilo C1-4, alquil C1-4S(O)p-alquilo C1-4 (en donde p es 0, 1 o 2), aminoalquilo C1-4, alquil C1-4-aminoalquilo C1-4, dialquil C1-4-aminoalquilo C1-4, alcoxi C1-6-carbonilalquilo C1-4, alquil C1-6-sulfoniloxi, cicloalquil C3-6-sulfonilo, alquil C1-6-sulfonilamino, azetidinilcarbonilo, pirrolidinilcarbonilo y HET-3; HET-3 y HET-3A son cada uno independientemente un anillo heteroarilo insustituido unido a C o N de 5 o 6 miembros que contiene 1, 2 o 3 heteroátomos del anillo que se seleccionan independientemente de O, N y S, o un anillo heterociclilo saturado insustituido unido a C o N de 4, 5 o 6 miembros que contiene un heteroátomo del anillo que se selecciona de O, N y S; L es S, O o NR12; y R12 es H o alquilo C1-4; pero excluyendo N-(5-cloro-2-piridinil)-2-[(1-fenil-1H-pirazolo[3,4-d]pirimidin-4-il)tio]propanamida; N-[1-(1-metiletil)-1H-pirazol-5-il]-2-[(1-fenil-1H-pirazolo[3,4-d]pirimidin-4-il)tio]propanamida; N-(5-(metil)isoxazol-3-il)-2-[[1-(4-fluorofenil)-1H-pirazolo[3,4-d]pirimidin-4-il]tio]butanamida; N-(5-(metil)isoxazol-3-il)-2-[[1-(4-fluorofenil)-1H-pirazolo[3,4-d]pirimidin-4-il]tio]propanamida; (2R)-2-[1-(3-cloro-2-piridil)pirazolo[4,5-e]pirimidin-4-il]oxi-5-hidroxi-N-(5-metil-2-piridil)pentanamida; (2R)-N-(5-cloro-2-piridil)-2-[1-(3-cloro-2-piridil)pirazolo[4,5-e]pirimidin-4-il]oxi-5-hidroxi-pentanamida; (2S)-2-[1-(3-cloro-2-piridil)pirazolo[4,5-e]pirimidin-4-il]oxi-N-(5-ciano-2-piridil)-3-[(1S)-2-hidroxi-1-metil-etoxi]propanamida; (2R)-2-[1-(2-clorofenil)pirazolo[4,5-e]pirimidin-4-il]oxi-N-(5-ciano-2-piridil)-3-(2-hidroxietoxi)propanamida; (2S)-N-(5-ciano-2-piridil)-2-[1-(2,5-dimetilfenil)pirazolo[4,5-e]pirimidin-4-il]oxi-3-(2-hidroxietoxi)-propanamida; (2S)-3-(2-hidroxietoxi)-N-(5-metil-2-piridil)-2-(9-fenilpurin-6-il)oxi-propanamida; (2R)-2-[1-(2-clorofenil)pirazolo[4,5-e]pirimidin-4-il]oxi-N-(5-fluoro-2-piridil)-3-(2-hidroxietoxi)propanamida; (2S)-N-(5-cloro-2-piridil)-2-[1-(3-cloro-2-piridil)pirazolo[4,5-e]pirimidin-4-il]oxi-3-[(2R)-2-hidroxipropoxi]propanamida; (2R)-N-(5-cloro-2-piridil)-2-[1-(3-cloro-2-piridil)pirazolo[4,5-e]pirimidin-4-il]oxi-3-[(2R)-2-hidroxipropoxi]propanamida; (2S)-2-[1-(3-cloro-2-piridil)-pirazolo[4,5-e]pirimidin-4-il]oxi-N-(5-ciano-2-piridil)-3-(3-hidroxiciclobutoxi)propanamida; y (2S)-N-(5-cloro-2-piridil)-2-[1-(3-cloro-2-piridil)pirazolo[4,5-e]pirimidin-4-il]oxi-3-(3-hidroxiciclobutoxi)propanamida.
ARP090102973A 2008-08-04 2009-08-03 Agentes terapeuticos derivados de pirazolo[3,4-d]pirimidina AR072900A1 (es)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US8591908P 2008-08-04 2008-08-04
US16804809P 2009-04-09 2009-04-09

Publications (1)

Publication Number Publication Date
AR072900A1 true AR072900A1 (es) 2010-09-29

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Country Status (23)

Country Link
US (1) US8143263B2 (es)
EP (1) EP2324028A2 (es)
JP (1) JP2011529955A (es)
KR (1) KR20110052676A (es)
CN (1) CN102171213A (es)
AR (1) AR072900A1 (es)
AU (1) AU2009278929B2 (es)
BR (1) BRPI0917589A2 (es)
CA (1) CA2732165A1 (es)
CL (1) CL2011000249A1 (es)
CO (1) CO6351730A2 (es)
CR (1) CR20110065A (es)
DO (1) DOP2011000047A (es)
EA (1) EA201100097A1 (es)
EC (1) ECSP11010809A (es)
IL (1) IL210778A0 (es)
MX (1) MX2011001333A (es)
PE (1) PE20110568A1 (es)
SV (1) SV2011003829A (es)
TW (1) TW201011026A (es)
UY (1) UY32032A (es)
WO (1) WO2010015849A2 (es)
ZA (1) ZA201101663B (es)

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US8143263B2 (en) 2012-03-27
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CR20110065A (es) 2011-05-10
AU2009278929A1 (en) 2010-02-11
IL210778A0 (en) 2011-03-31
CA2732165A1 (en) 2010-02-11
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BRPI0917589A2 (pt) 2015-11-17
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UY32032A (es) 2010-03-26
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CN102171213A (zh) 2011-08-31
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SV2011003829A (es) 2011-07-01
CO6351730A2 (es) 2011-12-20
AU2009278929B2 (en) 2012-07-05
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