AR124154A1 - CDK INHIBITORS - Google Patents

CDK INHIBITORS

Info

Publication number
AR124154A1
AR124154A1 ARP210103269A ARP210103269A AR124154A1 AR 124154 A1 AR124154 A1 AR 124154A1 AR P210103269 A ARP210103269 A AR P210103269A AR P210103269 A ARP210103269 A AR P210103269A AR 124154 A1 AR124154 A1 AR 124154A1
Authority
AR
Argentina
Prior art keywords
substituted
unsubstituted
nrzrz
orz
alkyl
Prior art date
Application number
ARP210103269A
Other languages
Spanish (es)
Inventor
Debnath Bhuniya
Srikant Viswanadha
Swaroop Kumar Venkata Satya Vakkalanka
Original Assignee
Rhizen Pharmaceuticals Ag
Incozen Therapeutics Pvt Ltd
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 Rhizen Pharmaceuticals Ag, Incozen Therapeutics Pvt Ltd filed Critical Rhizen Pharmaceuticals Ag
Publication of AR124154A1 publication Critical patent/AR124154A1/en

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
    • 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
    • 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

Abstract

La presente invención se refiere a compuestos de formula (1) y sales farmacéuticamente aceptables de los mismos como inhibidores de cinasa dependientes de ciclina (una o más de CDK1, CDK2, CDK4, y CDK6), métodos para prepararlos, y composiciones farmacéuticas que los contienen. Los compuestos de La presente invención son útiles en el tratamiento, prevención y/o mejora de enfermedades o trastornos asociados con una o más de CDK1, CDK2, CDK4, y CDK6. Reivindicación 1: Un compuesto de fórmula (1) o un tautómero del mismo, profármaco del mismo, N-óxido del mismo, estereoisómero del mismo, éster farmacéuticamente aceptable del mismo o sal farmacéuticamente aceptable del mismo, caracterizado porque Y¹ se selecciona a partir de CRᵃ o N; Y² se selecciona a partir de CRᵇ o N; con la condición de que al menos uno de Y¹ e Y² sea N; cada aparición de Rᵃ, Rᵇ, Rᶜ, Rᵈ, Rᵉ, Rᶠ y Rᵍ se selecciona independientemente a partir de hidrógeno, halógeno, hidroxi, alquilo sustituido o no sustituido, alquenilo sustituido o no sustituido, haloalquilo sustituido o no sustituido, alcoxi sustituido o no sustituido, aminoalquilo sustituido o no sustituido, hidroxialquilo sustituido o no sustituido, cicloalquilo sustituido o no sustituido, cicloalquilalquilo sustituido o no sustituido, heterociclilo sustituido o no sustituido, o heterociclilalquilo sustituido o no sustituido; Y se selecciona a partir de CRʰ o N; Z se selecciona a partir de CRⁱ o N; con la condición de que al menos uno de Y y Z sea N; cada aparición de Rʰ y Rⁱ se selecciona independientemente a partir de hidrógeno, halógeno, alquilo C₍₁₋₃₎ sustituido o no sustituido, o haloalquilo C₍₁₋₃₎ sustituido o no sustituido; X¹ es CR¹ o N; X² es CR² o N; X³ es CR³ o N; X⁴ es CR⁴ o N; cada aparición de R¹, R², R³, R⁴, R⁵ y R⁶ se selecciona independientemente a partir de hidrógeno, halógeno, hidroxi, alquilo sustituido o no sustituido, o haloalquilo sustituido o no sustituido, alcoxi sustituido o no sustituido, cicloalquilo sustituido o no sustituido, cicloalquilalquilo sustituido o no sustituido, heterociclilo sustituido o no sustituido, o heterociclilalquilo sustituido o no sustituido; L está ausente, NH, O, S-, -SO-, -SO₂-, -C(=O)-, o alquilo sustituido o no sustituido; el Anillo A es anillo de heterociclilo sustituido o no sustituido; cada aparición de R⁷ se selecciona independientemente a partir de hidrógeno, hidroxi, halógeno, alquilo sustituido o no sustituido, alcoxi sustituido o no sustituido, alquenilo sustituido o no sustituido, alquinilo sustituido o no sustituido, cicloalquilo sustituido o no sustituido, cicloalquenilo sustituido o no sustituido, cicloalquilalquilo sustituido o no sustituido, cicloalquenilalquilo sustituido o no sustituido, heterociclilo sustituido o no sustituido, heterociclilalquilo sustituido o no sustituido, arilo sustituido o no sustituido, arilalquilo sustituido o no sustituido, heteroarilo sustituido o no sustituido, heteroarilalquilo sustituido o no sustituido, oxo (=O), -C(=O)ORᶻ, -C(=O)Rᶻ, -C(=S)Rᶻ, -C(=O)NRᶻRᶻ, -C(=O)ONRᶻRᶻ, -NRᶻRᶻ, -NRᶻC(=O)NRᶻRᶻ, -NRᶻS(=O)Rᶻ, -NRᶻS(=O)₂Rᶻ, -N=NRᶻ, -NRᶻC(=O)ORᶻ, -NRᶻC(=O)Rᶻ, -NRˣC(=S)Rʸ, -NRᶻC(=S)NRᶻRᶻ, -SONRᶻRᶻ, -SO₂NRᶻRᶻ, -ORᶻ, -OC(=O)NRᶻRᶻ, -OC(=O)ORᶻ, -OC(=O)Rᶻ, -OC(=O)NRᶻRᶻ, -CRˣRʸ-NRᶻC(=O)Rᶻ, -CRˣRʸ-ORᶻ, -CRˣRʸ-C(=O)ORᶻ, -CRˣRʸ-C(=O)NRᶻRᶻ, -CRˣRʸ-OC(=O)Rᶻ, SRᶻ, -SORᶻ, -SO₂Rᶻ, -CRˣRʸC(=O)Rᶻ, o -CRˣRʸC(=S)Rᶻ; Rᶻ se selecciona a partir de hidrógeno, alquilo sustituido o no sustituido, alcoxi sustituido o no sustituido, alquenilo sustituido o no sustituido, alquinilo sustituido o no sustituido, arilo sustituido o no sustituido, arilalquilo sustituido o no sustituido, heteroarilo sustituido o no sustituido, heteroarilalquilo sustituido o no sustituido, cicloalquilo sustituido o no sustituido, cicloalquilalquilo sustituido o no sustituido, cicloalquenilo sustituido o no sustituido, heterociclilo sustituido o no sustituido, heterociclilalquilo sustituido o no sustituido, o amino sustituido o no sustituido, o cualesquiera dos de Rᶻ cuando se unen a un átomo común se pueden unir para formar (i) un anillo de 3 - 14 miembros saturado o insaturado, sustituido o no sustituido, que opcionalmente puede incluir uno o más heteroátomos que pueden ser los mismos o diferentes y se seleccionan a partir de O, NRᶻᵃ y S, o (ii) un grupo oxo (=O), tio (=S) o imino (=NRᶻᵃ); en donde Rᶻᵃ, Rˣ, y Rʸ en cada aparición se seleccionan independientemente a partir de hidrógeno, halo, hidroxi, amino, alcoxi, alquilo C₁₋₅, cicloalquilo C₃₋₇, arilo C₅₋₇, heteroarilo C₅₋₇, o heterocicloalquilo C₃₋₇; y n es un número entero seleccionado a partir de 0, 1, 2, 3 y 4. Reivindicación 20: Una composición farmacéutica, caracterizada porque comprende un compuesto de conformidad con cualquiera de las reivindicaciones 1 - 19 y un portador farmacéuticamente aceptable. Reivindicación 23: Un método para inhibir una actividad catalítica de una enzima CDK seleccionada de CDK1, CDK2, CDK4, CDK6, y cualquier combinación de cualquiera de las anteriores presente en una célula, caracterizado porque comprende poner en contacto la célula en una cantidad efectiva de un compuesto de conformidad con cualquiera de las reivindicaciones 1 - 19.The present invention relates to compounds of formula (1) and pharmaceutically acceptable salts thereof as inhibitors of cyclin-dependent kinase (one or more of CDK1, CDK2, CDK4, and CDK6), methods for preparing them, and pharmaceutical compositions containing them. they contain. The compounds of the present invention are useful in the treatment, prevention and/or amelioration of diseases or disorders associated with one or more of CDK1, CDK2, CDK4, and CDK6. Claim 1: A compound of formula (1) or a tautomer thereof, prodrug thereof, N-oxide thereof, stereoisomer thereof, pharmaceutically acceptable ester thereof or pharmaceutically acceptable salt thereof, characterized in that Y¹ is selected from CRᵃ or N; Y² is selected from CRᵇ or N; provided that at least one of Y¹ and Y² is N; each occurrence of Rᵃ, Rᵇ, Rᶜ, Rᵈ, Rᵉ, Rᶠ, and Rᵍ is independently selected from hydrogen, halogen, hydroxy, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted haloalkyl, substituted or unsubstituted alkoxy substituted, substituted or unsubstituted aminoalkyl, substituted or unsubstituted hydroxyalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkylalkyl, substituted or unsubstituted heterocyclyl, or substituted or unsubstituted heterocyclylalkyl; Y is selected from CRʰ or N; Z is selected from CRⁱ or N; provided that at least one of Y and Z is N; each occurrence of Rʰ and Rⁱ is independently selected from hydrogen, halogen, substituted or unsubstituted C₍₁₋₃₎ alkyl, or substituted or unsubstituted C₍₁₋₃₎ haloalkyl; X¹ is CR¹ or N; X² is CR² or N; X³ is CR³ or N; X⁴ is CR⁴ or N; each occurrence of R¹, R², R³, R⁴, R⁵ and R⁶ is independently selected from hydrogen, halogen, hydroxy, substituted or unsubstituted alkyl, or substituted or unsubstituted haloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted cycloalkyl , substituted or unsubstituted cycloalkylalkyl, substituted or unsubstituted heterocyclyl, or substituted or unsubstituted heterocyclylalkyl; L is absent, NH, O, S-, -SO-, -SO₂-, -C(=O)-, or substituted or unsubstituted alkyl; Ring A is substituted or unsubstituted heterocyclyl ring; each occurrence of R⁷ is independently selected from hydrogen, hydroxy, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl substituted, substituted or unsubstituted cycloalkylalkyl, substituted or unsubstituted cycloalkenylalkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heterocyclylalkyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroarylalkyl, oxo (=O), -C(=O)ORᶻ, -C(=O)Rᶻ, -C(=S)Rᶻ, -C(=O)NRᶻRᶻ, -C(=O)ONRᶻRᶻ, -NRᶻRᶻ, - NRᶻC(=O)NRᶻRᶻ, -NRᶻS(=O)Rᶻ, -NRᶻS(=O)₂Rᶻ, -N=NRᶻ, -NRᶻC(=O)ORᶻ, -NRᶻC(=O)Rᶻ, -NRˣC(=S) Rʸ, -NRᶻC(=S)NRᶻRᶻ, -SONRᶻRᶻ, -SO₂NRᶻRᶻ, -ORᶻ, -OC(=O)NRᶻRᶻ, -OC(=O)ORᶻ, -OC(=O)Rᶻ, -OC(=O)NRᶻRᶻ , -CRˣRʸ-NRᶻC(=O)Rᶻ, -CRˣRʸ-ORᶻ, -CRˣRʸ-C(=O)ORᶻ, -CRˣRʸ-C(=O)NRᶻRᶻ, -CRˣRʸ-OC(=O)Rᶻ, SRᶻ, -SORᶻ , -SO₂Rᶻ, -CRˣRʸC(=O)Rᶻ, or -CRˣRʸC(=S)Rᶻ; Rᶻ is selected from hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroarylalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkylalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heterocyclylalkyl, or substituted or unsubstituted amino, or any two of Rᶻ when bind to a common atom may join to form (i) a saturated or unsaturated, substituted or unsubstituted 3-14 membered ring, which may optionally include one or more heteroatoms which may be the same or different and are selected from O, NRᶻᵃ and S, or (ii) an oxo (=O), thio (=S) or imino (=NRᶻᵃ) group; wherein Rᶻᵃ, Rˣ, and Rʸ at each occurrence are independently selected from hydrogen, halo, hydroxy, amino, alkoxy, C₁₋₅ alkyl, C₃₋₇ cycloalkyl, C₅₋₇ aryl, C₅₋₇ heteroaryl, or C₃ heterocycloalkyl ₋₇; and n is an integer selected from 0, 1, 2, 3 and 4. Claim 20: A pharmaceutical composition, characterized in that it comprises a compound according to any of claims 1-19 and a pharmaceutically acceptable carrier. Claim 23: A method of inhibiting a catalytic activity of a CDK enzyme selected from CDK1, CDK2, CDK4, CDK6, and any combination of any of the above present in a cell, characterized in that it comprises contacting the cell in an effective amount of a compound according to any of claims 1-19.

ARP210103269A 2020-11-27 2021-11-26 CDK INHIBITORS AR124154A1 (en)

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IN202041051646 2020-11-27

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TW (1) TW202237585A (en)
WO (1) WO2022113003A1 (en)

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