AR095706A1 - Indazoles sustituidos con heteroarilo - Google Patents

Indazoles sustituidos con heteroarilo

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Publication number
AR095706A1
AR095706A1 ARP140101319A ARP140101319A AR095706A1 AR 095706 A1 AR095706 A1 AR 095706A1 AR P140101319 A ARP140101319 A AR P140101319A AR P140101319 A ARP140101319 A AR P140101319A AR 095706 A1 AR095706 A1 AR 095706A1
Authority
AR
Argentina
Prior art keywords
alkyl
haloalkyl
alkylene
haloalkoxy
cyano
Prior art date
Application number
ARP140101319A
Other languages
English (en)
Inventor
Dr Hitchcock Marion
Dr Mengel Anne
Dr Holton Simon
Dr Siemeister Gerhard
Dr Eis Knut
Dr Preusse Cornelia
Dr Ptter Vera
Dr Briem Hans
Ernesto Dr Fernndez-Montalvn Amaury
Dr Schrder Jens
Dr Bone Wilhelm
Original Assignee
Bayer Pharma Aktiengellschaft
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.)
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Publication date
Application filed by Bayer Pharma Aktiengellschaft filed Critical Bayer Pharma Aktiengellschaft
Publication of AR095706A1 publication Critical patent/AR095706A1/es

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    • 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
    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • 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
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic 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
    • A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • A61P35/00—Antineoplastic agents
    • A61P35/04—Antineoplastic agents specific for metastasis
    • 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
    • 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
    • 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
    • C07D403/04—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 directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

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

Abstract

Compuestos de la fórmula (1) que son inhibidores de Bub1 quinasa; procesos para su producción y su uso en fármacos para enfermedades hiperproliferativas (tumores hematológicos y tumores sólidos). Reivindicación 1: Un compuesto de la fórmula (1) en donde: T es CH, N; V es CH, N; Y es CR⁶, N; R¹ es hidrógeno, halógeno, alquilo C₁₋₃; R² / R³ son en forma independiente entre sí hidrógeno, halógeno, ciano, hidroxi, haloalquilo C₁₋₆, haloalcoxi C₁₋₆, alcoxi C₁₋₆; R⁴ es en forma independiente hidrógeno, hidroxi, halógeno, ciano, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, haloalquilo C₁₋₆, hidroxialquilo C₁₋₆, alcoxi C₁₋₆, -O-(alquilen C₂₋₄)-O-C(O)-(alquilo C₁₋₄), haloalcoxi C₁₋₆, -C(O)OR⁹, -C(O)-(alquilo C₁₋₆), -C(O)NR¹⁰R¹¹, cicloalquilo C₃₋₇, -S(O)₂NH-(cicloalquilo C₃₋₆), -S(O)₂NR¹⁰R¹¹, heteroarilo que está opcionalmente sustituido en forma independiente una o más veces con ciano, alquilo C₁₋₄, haloalquilo C₁₋₄, haloalcoxi C₁₋₄, donde dos de R², R³, (R⁴)ₙ, cuando están posicionados en posición orto entre sí, pueden formar junto con los dos átomos de carbono a los cuales están unidos, un anillo heterocíclico de 5, 6 ó 7 miembros que contiene 1 ó 2 heteroátomos seleccionados entre O ó N, y que opcionalmente contiene un enlace doble adicional y/o que está opcionalmente sustituido con un grupo oxo (=O) y/o un grupo alquilo C₁₋₄; n es 0, 1, 2 o 3; R⁶ es (a) hidrógeno; (b) hidroxi; (c) ciano; (d) alcoxi C₁₋₆ opcionalmente sustituido en forma independiente una o más veces con (d1) OH, (d2) -O-(alquilo C₁₋₆), (d3) -C(O)OR⁹, (d4) -C(O)NR¹⁰R¹¹, (d5) -NR¹²R¹³, (d6) -S-(alquilo C₁₋₆), (d7) -S(O)-(alquilo C₁₋₆), (d8) -S(O)₂-(alquilo C₁₋₆), (d9) -S(O)₂NR¹⁰R¹¹, (d10) heterociclilo, que está opcionalmente sustituido con -C(O)OR⁹ u oxo (=O), (d11) heteroarilo, que está opcionalmente sustituido en forma independiente una o más veces con ciano, alquilo C₁₋₄, haloalquilo C₁₋₄, haloalcoxi C₁₋₄, -C(O)OR⁹, -C(O)NR¹⁰R¹¹, -(alquilen C₁₋₄)-O-(alquilo C₁₋₄), (e) un resto de fórmula (2), donde el * es el punto de unión, (f) cicloalcoxi C₃₋₇, (g) haloalcoxi C₁₋₆, (h) -O-(alquilen C₂₋₆)-O-(alquilo C₁₋₆) que está opcionalmente sustituido con hidroxi, (i) -NR¹²R¹³, (j) -NHS(O)₂-(alquilo C₁₋₆), (k) -NHS(O)₂-(haloalquilo C₁₋₆); R⁷ es (a) hidrógeno, (b) alquilo C₁₋₄, que está opcionalmente sustituido con heteroarilo, (c) haloalquilo C₁₋₄, (d) hidroxialquilo C₂₋₄, (e) -CH₂-heteroarilo, donde el heteroarilo está opcionalmente sustituido en forma independiente una o más veces con hidroxi, halógeno, ciano, alquilo C₁₋₆ alquenilo C₂₋₆, alquinilo C₂₋₆, haloalquilo C₁₋₆, hidroxialquilo C₁₋₆, alcoxi C₁₋₆, haloalcoxi C₁₋₆, -(alquilen C₁₋₆)-O-(alquilo C₁₋₆), NR¹²R¹³, -C(O)OR⁹, -C(O)-(alquilo C₁₋₆), -C(O)NR¹⁰R¹¹, cicloalquilo C₃₋₇, -S(O)₂NH-(cicloalquilo C₃₋₆), -S(O)₂NR¹⁰R¹¹, (f) -bencilo, donde el anillo fenilo está opcionalmente sustituido en forma independiente una o más veces con halógeno, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄, haloalcoxi C₁₋₄, ciano, C(O)OR⁹, (g) -C(O)-(alquilo C₁₋₆), (h) -C(O)-(alquilen C₁₋₆)-O-(alquilo C₁₋₆), (i) -C(O)-(alquilen C₁₋₆)-O-(alquilen C₂₋₆)-O-(alquilo C₁₋₆), (j) -C(O)-heterociclilo, (k) un resto de fórmula (3), donde el * es el punto de unión; R⁸ es (a) heteroarilo de 5 miembros, (b) heteroarilo de 6 miembros seleccionado entre (b1) piridin-2-ilo, (b2) piridin-3-ilo, (b3) pirazin-2-ilo, (b4) piridazin-3-ilo, (b5) piridazin-4-ilo, (b6) pirimidin-2-ilo, (b7) pirimidin-4-ilo, (b8) pirimidin-5-ilo, (b9) 1,3,5-triazin-2-ilo, (b10) 1,2,4-triazin-3-ilo, (b11) 1,2,4-triazin-5-ilo, (b12) 1,2,4-triazin-6-ilo, (c) fenilo, donde dicho heteroarilo de 5 miembros o heteroarilo de 6 miembros o fenilo está opcionalmente sustituido en forma independiente una o más veces con halógeno, hidroxi, ciano, alquilo C₁₋₆, hidroxialquilo C₁₋₆, haloalquilo C₁₋₆, haloalcoxi C₁₋₆, -(CH₂)-O-(alquilo C₁₋₆), etoximetilo, -(alquilen C₂₋₆)-O-(alquilo C₁₋₆), -C(O)OR⁹, -C(O)NR¹⁰R¹¹, -NR¹²R¹³; R⁹ es (a) hidrógeno, (b) alquilo C₁₋₄ que está opcionalmente sustituido con hidroxi; R¹⁰, R¹¹ son en forma independiente entre sí hidrógeno, alquilo C₁₋₄, hidroxialquilo C₂₋₄, o junto con el átomo de nitrógeno al cual están unidos forman un anillo heterocíclico de 4 - 6 miembros que opcionalmente contiene un heteroátomo adicional seleccionado entre el grupo que consiste en O, S o N, y que está opcionalmente sustituido con 1 - 2 átomos de flúor o -C(O)OR⁹; R¹²,R¹³ son en forma independiente entre sí hidrógeno, alquilo C₁₋₄, hidroxialquilo C₂₋₄, -C(O)-(alquilo C₁₋₆), -C(O)-(alquilen C₁₋₆)-O-(alquilo C₁₋₆), -C(O)H, -C(O)OR⁹, o junto con el átomo de nitrógeno al cual están unidos forman un anillo heterocíclico de 4 - 6 miembros que opcionalmente contiene un heteroátomo adicional seleccionado entre el grupo que consiste en O, S o N, y que está opcionalmente sustituido con un grupo oxo (=O); o un N-óxido, una sal, un tautómero o un estereoisómero de dicho compuesto, o una sal de dicho N-óxido, tautómero o estereoisómero.
ARP140101319A 2013-03-21 2014-03-21 Indazoles sustituidos con heteroarilo AR095706A1 (es)

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US (1) US20160046610A1 (es)
EP (1) EP2976336A1 (es)
JP (1) JP2016514718A (es)
CN (1) CN105209455A (es)
AR (1) AR095706A1 (es)
CA (1) CA2907592A1 (es)
HK (1) HK1218750A1 (es)
TW (1) TW201514166A (es)
UY (1) UY35500A (es)
WO (1) WO2014147203A1 (es)

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CN105209455A (zh) 2015-12-30
US20160046610A1 (en) 2016-02-18
EP2976336A1 (en) 2016-01-27
JP2016514718A (ja) 2016-05-23
HK1218750A1 (zh) 2017-03-10
TW201514166A (zh) 2015-04-16
WO2014147203A1 (en) 2014-09-25
CA2907592A1 (en) 2014-09-25
UY35500A (es) 2014-10-31

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