AR098003A1 - KRAS G12C INHIBITORS - Google Patents

KRAS G12C INHIBITORS

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Publication number
AR098003A1
AR098003A1 ARP140103797A ARP140103797A AR098003A1 AR 098003 A1 AR098003 A1 AR 098003A1 AR P140103797 A ARP140103797 A AR P140103797A AR P140103797 A ARP140103797 A AR P140103797A AR 098003 A1 AR098003 A1 AR 098003A1
Authority
AR
Argentina
Prior art keywords
alkyl
separately
aminylcarbonyl
cyanoalkyl
carbocyclic
Prior art date
Application number
ARP140103797A
Other languages
Spanish (es)
Inventor
Wu Tao
Ren Pingda
Liu Yi
Liu Yuan
Oliver Long Yun
Li Liangsheng
Feng Jun
Original Assignee
Araxes Pharma Llc
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 Araxes Pharma Llc filed Critical Araxes Pharma Llc
Publication of AR098003A1 publication Critical patent/AR098003A1/en

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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

Se proporcionan compuestos que tienen actividad como inhibidores de la proteína KRAS mutante G12C. Se proporcionan también métodos de preparación y el uso para el tratamiento de trastornos, como por ejemplo, el cáncer. Reivindicación 1: Un compuesto que tiene la estructura de fórmula (1) o una sal aceptable farmacéuticamente, tautómero, profármaco o estereoisómero del mismo, en donde: A es CR¹, CR²ᵇ, NR⁷ ó S; B es una unión, CR¹ ó CR²ᶜ; G¹ y G² son cada uno por separado N ó CH; W, X e Y son cada uno por separado N, NR⁵ ó CR⁶; Z es una unión, N ó CR⁶ᵃ ó Z es NH cuando Y es C=O; L¹ es una unión ó NR⁷; L² es una unión o alquileno; R¹ es heterociclilo, heteroarilo o arilo; R²ᵃ, R²ᵇ y R²ᶜ son cada uno por separado H, halo, hidroxilo, C₁₋₆ alquilo, C₁₋₆ haloalquilo, C₁₋₆ alcoxi, C₃₋₈ cicloalquilo, heteroarilo o arilo; R³ᵃ y R³ᵇ son, en cada caso, por separado H, -OH, -NH₂, -CO₂H, halo, ciano, C₁₋₆ alquilo, C₁₋₆ alquinilo, hidroxilalquilo, aminiloalquilo, alquiloaminiloalquilo, cianoalquilo, carboxialquilo, aminilocarbonilalquilo o aminilocarbonilo; o R³ᵃ y R³ᵇ se unen para formar un anillo carbocíclico o heterocíclico; o R³ᵃ es H, -OH, -NH₂, -CO₂H, halo, ciano, C₁₋₆ alquilo, C₁₋₆ alquinilo, hidroxilalquilo, aminiloalquilo, alquiloaminiloalquilo, cianoalquilo, carboxialquilo, aminilocarbonilalquilo o aminilocarbonilo y R³ᵇ se une con R⁴ᵇ para formar un anillo carbocíclico o heterocíclico; R⁴ᵃ y R⁴ᵇ son, en cada caso, por separado H, -OH, -NH₂, -CO₂H, halo, ciano, C₁₋₆ alquilo, C₁₋₆ alquinilo, hidroxilalquilo, aminiloalquilo, alquiloaminiloalquilo, cianoalquilo, carboxialquilo, aminilocarbonilalquilo o aminilocarbonilo; o R⁴ᵃ y R⁴ᵇ se unen para formar un anillo carbocíclico o heterocíclico; o R⁴ᵃ es H, -OH, -NH₂, -CO₂H, halo, ciano, C₁₋₆ alquilo, C₁₋₆ alquinilo, hidroxilalquilo, aminiloalquilo, alquiloaminiloalquilo, cianoalquilo, carboxialquilo, aminilocarbonilalquilo o aminilocarbonilo y R⁴ᵇ se une con R³ᵇ para formar un anillo carbocíclico o heterocíclico; R⁵ es, en cada caso, por separado H, C₁₋₆ alquilo o una unión a L¹; R⁶ es, en cada caso, por separado H, oxo, ciano, cianoalquilo, amino, aminiloalquilo, aminiloalquiloaminilo, aminilocarbonilo, aminilsulfonilo, -CO₂NRᵃRᵇ, en donde Rᵃ y Rᵇ, son cada uno por separado H ó C₁₋₆ alquilo o Rᵃ y Rᵇ se unen para formar un anillo carbocíclico o heterocíclico alquiloaminilo, haloalquiloaminilo, hidroxilalquiaminilo, amindiniloalquilo, amidiniloalcoxi, amindiniloalquiloaminilo, guanidiniloalquilo, guanidiniloalcoxi, guanidiniloalquiloaminilo, C₁₋₆ alcoxi, aminiloalcoxi, alquiloaminiloalcoxi, alquilocarbonilaminiloalcoxi, C₁₋₆ alquilo, heterociclilo, heterocicliloxi, heterociclilalquilooxi, heterociclilaminilo, heterociclilalquiloaminilo, heteroarilo, heteroarilooxi, heteroariloalquilooxi, heteroariloaminilo, heteroariloalquiloaminilo, arilo, arilooxi, ariloaminilo, ariloalquiloaminilo, ariloalquilooxi o una unión a L¹; R⁶ᵃ es H, alquilo o una unión a L¹; R⁷ es H o C₁₋₆ alquilo; m₁ y m₂ son cada uno por separado 1, 2 ó 3; ⁻ ⁻ ⁻ ⁻ ⁻ indica un enlace sencillo o doble de modo que todas las valencias se cumplen; y E es una fracción electrofílica capaz de formar una unión covalente con el residuo de cisteína en la posición 12 de una proteína KRAS, HRAS o NRAS mutante G12C, en donde como mínimo uno de W, X y o Z es CR⁶ donde R⁶ es una unión a L¹ o como mínimo uno de W, X o Y es NR⁵, en donde R⁵ es una unión a L¹ y en el entendido de que como mínimo uno de R²ᵃ, R²ᵇ o R²ᶜ no es H cuando R¹ es piridilo.Compounds that have activity as inhibitors of the G12C mutant KRAS protein are provided. Methods of preparation and use for the treatment of disorders, such as cancer, are also provided. Claim 1: A compound having the structure of formula (1) or a pharmaceutically acceptable salt, tautomer, prodrug or stereoisomer thereof, wherein: A is CR¹, CR²ᵇ, NR⁷ or S; B is a union, CR¹ or CR²ᶜ; G¹ and G² are each separately N or CH; W, X and Y are each separately N, NR⁵ or CR⁶; Z is a union, N or CR⁶ᵃ or Z is NH when Y is C = O; L¹ is a union or NR⁷; L² is a bond or alkylene; R¹ is heterocyclyl, heteroaryl or aryl; R²ᵃ, R²ᵇ and R²ᶜ are each separately H, halo, hydroxyl, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₃₋₈ cycloalkyl, heteroaryl or aryl; R³ᵃ and R³ᵇ are, in each case, separately H, -OH, -NH₂, -CO₂H, halo, cyano, C₁₋₆ alkyl, C₁₋₆ alkynyl, hydroxylalkyl, aminylalkyl, alkylaminoalkyl, cyanoalkyl, carboxyalkyl, aminylcarbonylalkyl or aminylcarbonyl; or R³ᵃ and R³ᵇ join to form a carbocyclic or heterocyclic ring; or R³ᵃ is H, -OH, -NH₂, -CO₂H, halo, cyano, C₁₋₆ alkyl, C₁₋₆ alkynyl, hydroxylalkyl, aminylalkyl, alkylaminoamylalkyl, cyanoalkyl, carboxyalkyl, aminylcarbonylalkyl or aminylcarbonyl and R³ᵇ binds with R⁴ᵇ to form a carbocyclic or heterocyclic ring; R⁴ᵃ and R⁴ᵇ are, in each case, separately H, -OH, -NH₂, -CO₂H, halo, cyano, C₁₋₆ alkyl, C₁₋₆ alkynyl, hydroxylalkyl, aminylalkyl, alkylaminoalkyl, cyanoalkyl, carboxyalkyl, aminylcarbonylalkyl or aminylcarbonyl; or R⁴ᵃ and R⁴ᵇ join to form a carbocyclic or heterocyclic ring; or R⁴ᵃ is H, -OH, -NH₂, -CO₂H, halo, cyano, C₁₋₆ alkyl, C₁₋₆ alkynyl, hydroxylalkyl, aminylalkyl, alkylaminoamylalkyl, cyanoalkyl, carboxyalkyl, aminylcarbonylalkyl or aminylcarbonyl and R⁴ᵇ binds with R³ᵇ to form a carbocyclic or heterocyclic ring; R⁵ is, in each case, separately H, C₁₋₆ alkyl or a binding to L¹; R⁶ is, in each case, separately H, oxo, cyano, cyanoalkyl, amino, aminyloalkyl, aminyloalkyloaminyl, aminylcarbonyl, aminylsulfonyl, -CO₂NRᵃRᵇ, where Rᵃ and Rᵇ are each separately H or C₁₋₆ alkyl or Rᵃ and Rᵇ join to form a carbocyclic or heterocyclic alquiloaminilo, haloalquiloaminilo, hidroxilalquiaminilo, amindiniloalquilo, amidiniloalcoxi, amindiniloalquiloaminilo, guanidiniloalquilo, guanidiniloalcoxi, guanidiniloalquiloaminilo, C₁₋₆ alkoxy, aminiloalcoxi, alquiloaminiloalcoxi, alquilocarbonilaminiloalcoxi, C₁₋₆ alkyl, heterocyclyl, heterocyclyloxy, heterociclilalquilooxi, heterocyclylaminyl, heterocyclylalkyl amino, heteroaryl, heteroaryloxy, heteroaryloalkyloxy, heteroaryloaminyl, heteroaryloalkyloaminyl, aryl, aryloxy, arylaminoyl, arylalkyloaminyl, arylalkyloxy or an L¹ bond; R⁶ᵃ is H, alkyl or a bond to L¹; R⁷ is H or C₁₋₆ alkyl; m₁ and m₂ are each separately 1, 2 or 3; ⁻ ⁻ ⁻ ⁻ ⁻ Indicates a single or double bond so that all valences are met; and E is an electrophilic fraction capable of forming a covalent bond with the cysteine residue at position 12 of a G12C mutant KRAS, HRAS or NRAS protein, where at least one of W, X, and Z is CR⁶ where R⁶ is a junction to L¹ or at least one of W, X or Y is NR⁵, where R⁵ is a union to L¹ and with the understanding that at least one of R²ᵃ, R²ᵇ or R²ᶜ is not H when R¹ is pyridyl.

ARP140103797A 2013-10-10 2014-10-10 KRAS G12C INHIBITORS AR098003A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US201361889460P 2013-10-10 2013-10-10

Publications (1)

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AR098003A1 true AR098003A1 (en) 2016-04-27

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ARP140103797A AR098003A1 (en) 2013-10-10 2014-10-10 KRAS G12C INHIBITORS

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AR (1) AR098003A1 (en)

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