AR117490A1 - Inhibidores de kif18a - Google Patents

Inhibidores de kif18a

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Publication number
AR117490A1
AR117490A1 ARP190103828A ARP190103828A AR117490A1 AR 117490 A1 AR117490 A1 AR 117490A1 AR P190103828 A ARP190103828 A AR P190103828A AR P190103828 A ARP190103828 A AR P190103828A AR 117490 A1 AR117490 A1 AR 117490A1
Authority
AR
Argentina
Prior art keywords
alc
nrara
group
halo
atoms
Prior art date
Application number
ARP190103828A
Other languages
English (en)
Inventor
Lei Jia
Matthew Paul Bourbeau
Ana Elena Minatti
Mary Walton
Liping H Pettus
Vu Van Ma
Jonathan D Low
Qingyian Liu
Kexue Li
Jian Jeffrey Chen
Michael J Frohn
James Brown
Abhisek Banerjee
Nuria A Tamayo
Original Assignee
Amgen Inc
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Publication date
Application filed by Amgen Inc filed Critical Amgen Inc
Publication of AR117490A1 publication Critical patent/AR117490A1/es

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    • 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
    • C07D401/02—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 two hetero rings
    • C07D401/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
    • 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
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • 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
    • 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
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D419/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms
    • C07D419/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems
    • C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring

Abstract

Compuestos de la fórmula (1), como se definen en el presente documento, e intermedios sintéticos de los mismos, que pueden modular la proteína KIF18A alterando de esta forma el proceso del ciclo celular y la proliferación celular para tratar el cáncer y enfermedades relacionadas con cáncer. La presente también incluye composiciones farmacéuticas, que incluyen los compuestos, y métodos para tratar patologías relacionadas con la actividad de KIF18A. Reivindicación 1: Un compuesto de fórmula (1), o cualquier sal farmacéuticamente aceptable del mismo, en el que: X¹ es N o -CR⁶; R¹ es -CN, o un grupo -Z-R¹² en el que Z es -alc C₀₋₄-, -NR¹¹-, -NR¹¹SO₂-, -SO₂NR¹¹-, -NR¹¹-S(=O)(=NH), -S(=O)(=NH)-, -S-, -S(=O)-, -SO₂-, -O-alc C₀₋₄, -(C=O)-, -(C=O)NR¹¹-, -C=N(OH)-, o -NR¹¹(C=O); o el grupo -Z-R¹² es -N=S(=O)-(R¹²)₂, en el que las dos parejas de R¹² se pueden combinar alternativamente con el átomo de azufre unido a cada uno de ellos para formar un anillo monocíclico saturado o parcialmente saturado de 3, 4, 5, ó 6 miembros que contiene 0, 1, 2 ó 3 átomos de N y 0, 1, ó 2 átomos seleccionados entre O y S; R² es halo o un grupo -Y-R¹³, en el que Y es -alc C₀₋₄-, -N(alc C₀₋₁)-alc C₀₋₄-, -C(=O)NRᵃRᵃ(alc C₁₋₄), -O-alc C₀₋₄-, S, S=O, S(=O)₂, -SO₂NR¹³, o -S(=O)(=NH)-; R³ es H, alc C₁₋₄, o haloalc C₁₋₄; R⁴ es H, halo, R⁴ᵃ o R⁴ᵇ; R⁵ es H, halo, alc C₁₋₈, o haloalc C₁₋₄; R⁶ es H, halo, alc C₁₋₈, haloalc C₁₋₄, -O-alc C₁₋₈, u -O-R⁶ᵃ; en el que R⁶ᵃ es un anillo monocíclico saturado o parcialmente saturado de 3, 4, 5 ó 6 miembros que contiene 0, 1, 2 ó 3 átomos de N y 0, 1, ó 2 átomos seleccionados entre O y S; R⁷ es H, halo, alc C₁₋₈, o haloalc C₁₋₄; R⁸ es H, halo, alc C₁₋₈, haloalc C₁₋₄, -OH, -O-R⁸ᵃ, o -OR⁸ᵇ; R⁹ es H, halo, alc C₁₋₈, o haloalc C₁₋₄; Rˣ se selecciona entre el grupo que consiste en los compuestos del grupo de fórmulas (2); cada uno de R¹⁰ᵃ, R¹⁰ᵇ, R¹⁰ᶜ, R¹⁰ᵈ, R¹⁰ᵉ, R¹⁰ᶠ, R¹⁰ᵍ, R¹⁰ʰ, R¹⁰ⁱ, y R¹⁰ʲ es H, halo, R¹⁰ᵏ, o R¹⁰ˡ; o alternativamente, cada uno de la pareja R¹⁰ᵃ y R¹⁰ᵇ, pareja R¹⁰ᶜ y R¹⁰ᵈ, pareja R¹⁰ᵉ y R¹⁰ᶠ, pareja R¹⁰ᵍ y R¹⁰ʰ, o pareja R¹⁰ⁱ y R¹⁰ʲ, independientemente, se pueden combinar con el átomo de carbono unido a cada uno de ellos para formar un anillo monocíclico saturado o parcialmente saturado de 3, 4, 5, 6 miembros formando un ciclo espiro con el anillo Rˣ; en el que dicho anillo monocíclico de 3, 4, 5, 6 miembros contiene 0, 1, 2 ó 3 átomos de N y 0, 1, ó 2 átomos seleccionados entre O y S, y además en el que dicho anillo monocíclico de 3, 4, 5, 6 miembros está sustituido por 0, 1, 2 ó 3 grupo(s) seleccionado(s) entre F, Cl, Br, alc C₁₋₆, haloalc C₁₋₄, -ORᵃ, -Ohaloalc C₁₋₄, CN, -NRᵃRᵃ, u oxo; R¹¹ es H, R¹¹ᵃ, o R¹¹ᵇ; R¹² es H, R¹²ᵃ, o R¹²ᵇ; R¹³ es R¹³ᵃ o R¹³ᵇ; R⁴ᵃ, R⁸ᵃ, R¹⁰ᵏ, R¹¹ᵃ, R¹²ᵃ, y R¹³ᵃ independientemente, en cada caso, se seleccionan entre el grupo que consiste en un anillo monocíclico de 3, 4, 5, 6 ó 7 miembros saturado, parcialmente saturado o insaturado o un anillo bicíclico de 4, 5, 6, 7, 8, 9, 10, 11 ó 12 miembros que contiene 0, 1, 2 ó 3 átomos de N y 0, 1, ó 2 átomos seleccionados entre O y S, que está sustituido por 0, 1, 2 ó 3 grupo(s) seleccionado(s) entre F, Cl, Br, alc C₁₋₆, haloalc C₁₋₄, -ORᵃ, -Ohaloalc C₁₋₄, CN, -C(=O)Rᵇ, -C(=O)ORᵃ, -C(=O)NRᵃRᵃ, -C(=NRᵃ)NRᵃRᵃ, -OC(=O)Rᵇ, -OC(=O)NRᵃRᵃ, -Oalc C₂₋₆NRᵃRᵃ, -Oalc C₂₋₆ORᵃ, -SRᵃ, -S(=O)Rᵇ, -S(=O)₂Rᵇ, -S(=O)₂NRᵃRᵃ, -NRᵃRᵃ, -N(Rᵃ)C(=O)Rᵇ, -N(Rᵃ)C(=O)ORᵇ, -N(Rᵃ)C(=O)NRᵃRᵃ, -N(Rᵃ)C(=NRᵃ)NRᵃRᵃ, -N(Rᵃ)S(=O)₂Rᵇ, -N(Rᵃ)S(=O)₂NRᵃRᵃ, -NRᵃalc C₂₋₆NRᵃRᵃ, -NRᵃalc C₂₋₆ORᵃ, -alc C₁₋₆NRᵃRᵃ, -alc C₁₋₆ORᵃ, -alc C₁₋₆N(Rᵃ)C(=O)Rᵇ, -alc C₁₋₆OC(=O)Rᵇ, -alc C₁₋₆C(=O)NRᵃRᵃ, -alc C₁₋₆C(=O)ORᵃ, R¹⁴, y oxo; R⁴ᵇ, R⁸ᵇ, R¹⁰ˡ, R¹¹ᵇ, R¹²ᵇ, y R¹³ᵇ se seleccionan independientemente, en cada caso, entre el grupo que consiste en alc C₁₋₆ sustituido por 0, 1, 2, 3, 4, ó 5 grupo(s) seleccionado(s) entre F, Cl, Br, -ORᵃ, -Ohaloalc C₁₋₄, o CN; R¹⁴ se selecciona independientemente, en cada caso, entre el grupo que consiste en un anillo monocíclico de 3, 4, 5, 6 ó 7 miembros saturado, parcialmente saturado o insaturado o un anillo bicíclico de 4, 5, 6, 7, 8, 9, 10, 11, ó 12 miembros que contiene 0, 1, 2 ó 3 átomos de N y 0 ó 1 átomos seleccionados entre O y S, que está sustituido por 0, 1, 2 ó 3 grupo(s) seleccionado(s) entre F, CI, Br, alc C₁₋₆, haloalc C₁₋₄, -ORᵃ, -Ohaloalc C₁₋₄, CN, -C(=O)Rᵇ, -C(=O)ORᵃ, -C(=O)NRᵃRᵃ, -C(=NRᵃ)NRᵃRᵃ, -OC(=O)Rᵇ, -OC(=O)NRᵃRᵃ, -Oalc C₂₋₆NRᵃRᵃ, -Oalc C₂₋₆ORᵃ, -SRᵃ, -S(=O)Rᵇ, -S(=O)₂Rᵇ, -S(=O)₂NRᵃRᵃ, -NRᵃRᵃ, -N(Rᵃ)C(=O)Rᵇ, -N(Rᵃ)C(=O)ORᵇ, -N(Rᵃ)C(=O)NRᵃRᵃ, -N(Rᵃ)C(=NRᵃ)NRᵃRᵃ, -N(Rᵃ)S(=O)₂Rᵇ, -N(Rᵃ)S(=O)₂NRᵃRᵃ, -NRᵃalc C₂₋₆NRᵃRᵃ, -NRᵃalc C₂₋₆ORᵃ, -alc C₁₋₆NRᵃRᵃ, -alc C₁₋₆ORᵃ, -alc C₁₋₆N(Rᵃ)C(=O)Rᵇ, -alc C₁₋₆OC(=O)Rᵇ, -alc C₁₋₆C(=O)NRᵃRᵃ, -alc C₁₋₆C(=O)ORᵃ, y oxo; Rᵃ es independientemente, en cada caso, H o Rᵇ; y Rᵇ es independientemente, en cada caso, alc C₁₋₆, fenilo o bencilo, en el que el alc C₁₋₆ está siendo sustituido por 0, 1, 2 ó 3 sustituyentes seleccionados entre halo, -OH, -Oalc C₁₋₄, -NH₂, -NHalc C₁₋₄, -OC(=O)alc C₁₋₄, o -N(alc C₁₋₄)alc C₁₋₄; y el fenilo o bencilo está siendo sustituido por 0, 1, 2 ó 3 sustituyentes seleccionados entre halo, alc C₁₋₄, haloalc C₁₋₃, -OH, -Oalc C₁₋₄, -NH₂, -NHalc C₁₋₄, -OC(=O)alc C₁₋₄, o -N(alc C₁₋₄)alc C₁₋₄.
ARP190103828A 2018-12-20 2019-12-20 Inhibidores de kif18a AR117490A1 (es)

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US (2) US11236069B2 (es)
EP (1) EP3897852A1 (es)
JP (1) JP7407196B2 (es)
KR (1) KR20210106474A (es)
CN (1) CN113226473A (es)
AR (1) AR117490A1 (es)
AU (1) AU2019403486A1 (es)
BR (1) BR112021011989A2 (es)
CA (1) CA3123871A1 (es)
CL (1) CL2021001634A1 (es)
CO (1) CO2021008224A2 (es)
CR (1) CR20210387A (es)
EA (1) EA202191730A1 (es)
IL (1) IL283639B1 (es)
JO (1) JOP20210154B1 (es)
MA (1) MA54543A (es)
MX (1) MX2021007156A (es)
PE (1) PE20211475A1 (es)
SG (1) SG11202106520VA (es)
TW (1) TW202034924A (es)
UY (1) UY38526A (es)
WO (1) WO2020132648A1 (es)

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WO2023088441A1 (zh) * 2021-11-19 2023-05-25 微境生物医药科技(上海)有限公司 Kif18a抑制剂
AR128353A1 (es) * 2022-01-26 2024-04-24 Amgen Inc Síntesis de un inhibidor de kif18a
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WO2023174175A1 (zh) * 2022-03-17 2023-09-21 微境生物医药科技(上海)有限公司 Kif18a抑制剂
WO2023198209A1 (zh) * 2022-04-15 2023-10-19 武汉人福创新药物研发中心有限公司 一种kif18a抑制剂及其用途
TW202400582A (zh) * 2022-05-13 2024-01-01 大陸商上海湃隆生物科技有限公司 驅動蛋白kif18a抑制劑及其應用
WO2024002328A1 (zh) * 2022-06-30 2024-01-04 勤浩医药（苏州）有限公司 一种含氮化合物及其应用
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WO2024035950A1 (en) * 2022-08-12 2024-02-15 Accent Therapeutics, Inc. Inhibitors of kif18a and uses thereof
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WO2024051812A1 (zh) * 2022-09-09 2024-03-14 先声再明医药有限公司 酰胺类化合物、其组合物及用途
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WO2024067675A1 (zh) * 2022-09-30 2024-04-04 长春金赛药业有限责任公司 稠环类kif18a抑制剂化合物、药物组合物及其制备方法和应用
CN115594664B (zh) * 2022-11-25 2023-02-24 英矽智能科技(上海)有限公司 一类螺环衍生物作为kif18a抑制剂
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