AR122928A1 - 1,6-SUBSTITUTED NAPHTHYRIDINES INHIBITOR OF CDK5 - Google Patents

1,6-SUBSTITUTED NAPHTHYRIDINES INHIBITOR OF CDK5

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Publication number
AR122928A1
AR122928A1 ARP210101930A ARP210101930A AR122928A1 AR 122928 A1 AR122928 A1 AR 122928A1 AR P210101930 A ARP210101930 A AR P210101930A AR P210101930 A ARP210101930 A AR P210101930A AR 122928 A1 AR122928 A1 AR 122928A1
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Argentina
Prior art keywords
alkyl
ring
optionally substituted
c4alkylene
hydroxyalkyl
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ARP210101930A
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Spanish (es)
Inventor
Goran Malojcic
Matthew H Daniels
Brett W Williams
Maolin Yu
Mark W Ledeboer
Jean Harmange
P - Wang Jenna Lijie Christophe
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Goldfinch Bio Inc
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Publication of AR122928A1 publication Critical patent/AR122928A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • 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

Compuestos que tienen la fórmula estructural (1), y sales y composiciones farmacéuticas relacionadas. También se describen métodos terapéuticos, por ejemplo, para tratar enfermedades y condiciones tales como enfermedad renal, insuficiencia renal, cálculos renales, o enfermedad de riñón poliquístico, usando los compuestos de fórmula (1), y sales y composiciones farmacéuticas relacionadas. Reivindicación 1: Un compuesto caracterizado porque tiene la fórmula estructural (1), o una sal farmacéuticamente aceptable del mismo, donde: el anillo A es un cicloalquilo monocíclico o bicíclico o un heterociclilo saturado monocíclico o bicíclico; el anillo B es arilo monocíclico o bicíclico, heteroarilo monocíclico o bicíclico, o heterociclilo monocíclico o bicíclico; R¹ es -N(R⁵)-, -C(O)-, -S-, -S(O)-, -S(O)₂-, -[C(R⁴)₂]₁₋₂-, -[C(R⁴)₂]₀₋₁-CH=, -N(R⁵)-S(O)₂-, -S(O)₂-N(R⁵), -C(R⁴)₂-N(R⁵)-, -N(R⁵)-C(R⁴)₂-, -C(R⁴)₂-S(O)₂-, -C(=N-OH)-, -C(=N-O-C₁-C₄ alquilo)-, o -S(O)₂-C(R⁴)₂-; cada R² es en forma independiente halo, -OH, -C₁-C₆ alquilo, -C₁-C₆ haloalquilo, -C₁-C₆ hidroxialquilo, -(C₀-C₄ alquilen)-C(O)-OH, -(C₀-C₄ alquilen)-C(O)-O-C₁-C₄ alquilo, -(C₀-C₄ alquilen)-O-C₁-C₄ alquilo, -(C₀-C₄ alquilen)-O-C₁-C₄ hidroxialquilo, -(C₀-C₄ alquilen)-C(O)-N(R⁶)₂, -(C₀-C₄ alquilen)-N(R⁶)₂, o -(C₀-C₄ alquilen)-heterociclilo saturado, donde el heterociclilo saturado está opcionalmente sustituido con halo, -OH, o -CH₃; cada R³ es en forma independiente halo; -CN; -OH; -N(R⁶)₂; -C₁-C₄ alquilo; -O-C₁-C₄ alquilo; -O-C₁-C₄ alquilen-C(O)-N(R⁶)₂; -C(O)-O-C₁-C₄ alquilo; -C(O)-N(R⁶)₂; -S(O)₂-N(R⁶)₂; -S(O)₂-C₁-C₄ alquilo; C₂-C₄ alquinilo opcionalmente sustituido con uno o más -OH; 1,2,4-triazol-1-ilmetilo; morfolinilmetilo; ciclopropilo; =O; -CH₂CH₂-C(O)-O-CH₃; -N(R⁶)-S(O)₂-CH₃; un arilo opcionalmente sustituido; un heteroarilo opcionalmente sustituido; o un heterociclo opcionalmente sustituido, donde cualquier porción alquilo de R³ está opcionalmente sustituida con uno o más de halo, -CN, o -N(R⁶)₂, o -OH; cada R⁴ es en forma independiente hidrógeno, halo, -OH, -CN, -N(R⁶)₂, -C₁-C₄ alquilo opcionalmente sustituido con uno o más de -OH, halo, -CN, o -N(R⁶)₂; o O-C₁-C₄ alquilo opcionalmente sustituido con uno o más de -OH, halo, -CN, o -N(R⁶)₂; o un R⁴ se toma junto con un átomo de carbono del anillo A para formar un anillo cicloalquilo o heterociclilo que está espirofusionado, fusionado o forma un puente con el anillo A; o dos R⁴ unidos al mismo átomo de carbono se toman juntos para formar =CH₂-(C₀-C₃ alquilo), un C₃-C₆ cicloalquilo, o un C₄-C₇ heterociclilo; R⁵ es hidrógeno; C₁-C₄ alquilo opcionalmente sustituido con uno o más de -CN, -OH, -COOH, C(O)-O-C₁-C₄ alquilo, o pirazolilo; -S(O)₂-C₁-C₄ alquilo; -C(O)C(O)OH; -COOH; o -C(O)-O-C₁-C₄ alquilo; o R⁵ se toma junto con un átomo de carbono del anillo A para formar un anillo heterociclilo que está espirofusionado, fusionado o forma un puente con el anillo A; cada R⁶ es en forma independiente hidrógeno o -C₁-C₄ alquilo; m es 0, 1, 2, 3, 4, 5, ó 6; n es 0, 1, 2, 3, 4, 5, ó 6; y “----” representa una unión simple o una unión doble, donde: se cumplen una o más de las siguientes condiciones: a. el anillo B es piperidin-4-ilo, oxetan-3-ilo, azetidin-3-ilo, 2-oxaespiro[3.5]nonan7-ilo, indazolilo, o 1,3-dihidro-2H-benzo[d]imidazolilo; b. un R³ es -CH₂CF₃, -CH(OH)CHF₂, -CH(CH₃)CF₃, -OCH(CH₃)₂, -CH(CH₃)CH₂OH, -OCH(CH₃)CH₂OH, -S(O)₂CH(CH₃)₂, -OCH₂CH(CH₃)₂, -OCH₂CH(CH₃)₂, -CF₃, -OCF₃, -CHF₂, o -OCHF₂; c. un R³ es arilo, heteroarilo, o heterociclilo, donde el R³ está sustituido con hasta tres sustituyentes seleccionados en forma independiente entre -C(O)-C₁-C₄ alquilo, -C₁-C₄ alquilen-COOH, -S(O)₂-C₁-C₄ alquilo, -C(O)-N(R⁶)-C₁-C₄ hidroxialquilo, -C₁-C₄ alquilen-C(O)-N(R⁶)₂, -C(O)N(R⁶)-heterociclilo saturado, -C(O)-heterociclilo saturado, -C(O)-C₃-C₇ cicloalquilo, y -O-C₁-C₄ hidroxialquilo, donde al menos un sustituyente es -C(O)-C₁-C₄ alquilo, -C₁-C₄ alquilen-COOH, -S(O)₂-C₁-C₄ alquilo, -C(O)-N(R⁶)-C₁-C₄ hidroxialquilo, -C₁-C₄ alquilen-C(O)-N(R⁶)₂, -C(O)N(R⁶)-heterociclilo saturado, -C(O)-heterociclilo saturado, -C(O)-C₃-C₇ cicloalquilo, o -O-C₁-C₄ hidroxialquilo; d. un R³ es oxetan-3-ilo, azetidin-1-ilo, 1,4-oxazepan-4-ilo, piridazin-4-ilo, 1,2-dihidropirazin-2-ilo, 1,6-dihidropirimdin-5-ilo, 1,6-dihidropiridazin-4-ilo, piperidin-3-ilo, piperidin-4-ilo, pirimidin-2-ilo, 3,6-dihidro-2H-piran-4-ilo, 2-oxa-5-azabiciclo[2.2.1]heptan-5-ilo, 2-oxa-6-azaespiro[3.3]heptan-6-ilo, hexahidropirimidin-1-ilo, 2,5-dioxa-8-azaespiro[3.5]nonan-8-ilo, 8-oxa-3-azabiciclo[3.2.1]octan-3-ilo, 2,6-diazaespiro[3.3]heptan-2-ilo, o 2-oxa-6-azaespiro[3.5]nonan-6-ilo donde el R³ está opcionalmente sustituido en forma independiente con hasta 3 sustituyentes seleccionados en forma independiente entre halo, =O, -OH, CN, C₁-C₄ alquilo, C₁-C₄ hidroxialquilo, C₁-C₄ haloalquilo, -COOH, -C(O)-N(R⁶)₂, -(C₀-C₄ alquilen)-C(O)-O-C₁-C₄ alquilo, -OC₁-C₄ alquilo, -C(O)-C₁-C₄ alquilo, -C₁-C₄ alquilen-COOH, -S(O)₂-C₁-C₄ alquilo, -C(O)-N(R⁶)-C₁-C₄ hidroxialquilo, -C₁-C₄ alquilen-C(O)-N(R⁶)₂, -C(O)N(R⁶)-heterociclilo saturado, -C(O)-heterociclilo saturado, -C(O)-C₃-C₇ cicloalquilo, y -O-C₁-C₄ hidroxialquilo; e. un R² es -C(O)NH₂, -CH₂CN, -CH₂CHF₂, -CH₂COOH, -CH₂CH₂F, CH₂C(O)NHCH₃, CH₂C(O)N(CH₃)₂, -CH₂CH(OH)CH₃, -CH(CH₃)CH₂OH, -CH₂CH₂OCH₃, azetidin-3-ilo, azetidin-3-ilmetilo, u oxazol-2-ilmetilo; f. R¹ es -C(OH)(CHF₂)-, -C(NH₂)(CF₃)-, oxiran-2,2-diilo, o 1,3-dioxolan-2,2-diilo; y/o g. R¹ está fusionado al anillo A para formar 2-oxo-octahidro-2H-imidazo[4,5-c]piridin-1-ilo, 1-oxa-6-azaespiro[2.5]octan-2-ilo, octahidro-1H-pirrolo[3,2-c]piridin-1-ilo, 2-oxo-hexahidrooxazolo[5,4-c]piridin-1-ilo, o 2,2-dioxo-octahidro-[1,2,5]tiadiazolo[3,4-c]piridin-1-ilo.Compounds having the structural formula (1), and salts and related pharmaceutical compositions. Therapeutic methods are also described, for example, for treating diseases and conditions such as kidney disease, kidney failure, kidney stones, or polycystic kidney disease, using the compounds of formula (1), and salts and related pharmaceutical compositions. Claim 1: A compound characterized in that it has the structural formula (1), or a pharmaceutically acceptable salt thereof, where: ring A is a monocyclic or bicyclic cycloalkyl or a monocyclic or bicyclic saturated heterocyclyl; ring B is monocyclic or bicyclic aryl, monocyclic or bicyclic heteroaryl, or monocyclic or bicyclic heterocyclyl; R¹ is -N(R⁵)-, -C(O)-, -S-, -S(O)-, -S(O)₂-, -[C(R⁴)₂]₁₋₂-, -[ C(R⁴)₂]₀₋₁-CH=, -N(R⁵)-S(O)₂-, -S(O)₂-N(R⁵), -C(R⁴)₂-N(R⁵)- , -N(R⁵)-C(R⁴)₂-, -C(R⁴)₂-S(O)₂-, -C(=N-OH)-, -C(=N-O-C₁-C₄ alkyl)- , or -S(O)₂-C(R⁴)₂-; each R² is independently halo, -OH, -C₁-C₆ alkyl, -C₁-C₆ haloalkyl, -C₁-C₆ hydroxyalkyl, -(C₀-C₄ alkylene)-C(O)-OH, -(C₀-C₄ alkylene )-C(O)-O-C₁-C₄alkyl, -(C₀-C₄alkylene)-O-C₁-C₄alkyl, -(C₀-C₄alkylene)-O-C₁-C₄hydroxyalkyl, -(C₀-C₄alkylene )-C(O)-N(R⁶)₂, -(C₀-C₄alkylene)-N(R⁶)₂, or -(C₀-C₄alkylene)-saturated heterocyclyl, where the saturated heterocyclyl is optionally substituted with halo, - OH, or -CH₃; each R³ is independently halo; -CN; -OH; -N(R⁶)₂; -C₁-C₄ alkyl; -O-C₁-C₄ alkyl; -O-C₁-C₄ alkylene-C(O)-N(R⁶)₂; -C(O)-O-C₁-C₄ alkyl; -C(O)-N(R⁶)₂; -S(O)₂-N(R⁶)₂; -S(O)₂-C₁-C₄ alkyl; C₂-C₄ alkynyl optionally substituted with one or more -OH; 1,2,4-triazol-1-ylmethyl; morpholinylmethyl; cyclopropyl; =O; -CH₂CH₂-C(O)-O-CH₃; -N(R⁶)-S(O)₂-CH₃; an optionally substituted aryl; an optionally substituted heteroaryl; or an optionally substituted heterocycle, where any alkyl portion of R³ is optionally substituted with one or more of halo, -CN, or -N(R⁶)₂, or -OH; each R⁴ is independently hydrogen, halo, -OH, -CN, -N(R⁶)₂, -C₁-C₄ alkyl optionally substituted with one or more of -OH, halo, -CN, or -N(R⁶)₂ ; or O-C₁-C₄ alkyl optionally substituted with one or more of -OH, halo, -CN, or -N(R⁶)₂; or an R⁴ is taken together with a carbon atom from ring A to form a cycloalkyl or heterocyclyl ring that is spirofused, fused to, or bridged with ring A; or two R⁴ attached to the same carbon atom are taken together to form =CH₂-(C₀-C₃ alkyl), a C₃-C₆ cycloalkyl, or a C₄-C₇ heterocyclyl; R⁵ is hydrogen; C₁-C₄ alkyl optionally substituted with one or more of -CN, -OH, -COOH, C(O)-O-C₁-C₄ alkyl, or pyrazolyl; -S(O)₂-C₁-C₄ alkyl; -C(O)C(O)OH; -COOH; or -C(O)-O-C₁-C₄ alkyl; or R⁵ is taken together with a carbon atom from ring A to form a heterocyclyl ring that is spirofused, fused to, or bridged with ring A; each R⁶ is independently hydrogen or -C₁-C₄ alkyl; m is 0, 1, 2, 3, 4, 5, or 6; n is 0, 1, 2, 3, 4, 5, or 6; and ---- represents a single union or a double union, where: one or more of the following conditions are met: a. ring B is piperidin-4-yl, oxetan-3-yl, azetidin-3-yl, 2-oxaspiro[3.5]nonan7-yl, indazolyl, or 1,3-dihydro-2H-benzo[d]imidazolyl; b. an R³ is -CH₂CF₃, -CH(OH)CHF₂, -CH(CH₃)CF₃, -OCH(CH₃)₂, -CH(CH₃)CH₂OH, -OCH(CH₃)CH₂OH, -S(O)₂CH(CH₃) ₂, -OCH₂CH(CH₃)₂, -OCH₂CH(CH₃)₂, -CF₃, -OCF₃, -CHF₂, or -OCHF₂; c. an R³ is aryl, heteroaryl, or heterocyclyl, where R³ is substituted with up to three substituents independently selected from -C(O)-C₁-C₄alkyl, -C₁-C₄alkylene-COOH, -S(O)₂- C₁-C₄ alkyl, -C(O)-N(R⁶)-C₁-C₄ hydroxyalkyl, -C₁-C₄ alkylene-C(O)-N(R⁶)₂, -C(O)N(R⁶)-saturated heterocyclyl , -C(O)-saturated heterocyclyl, -C(O)-C₃-C₇ cycloalkyl, and -O-C₁-C₄ hydroxyalkyl, where at least one substituent is -C(O)-C₁-C₄ alkyl, -C₁- C₄ alkylene-COOH, -S(O)₂-C₁-C₄ alkyl, -C(O)-N(R⁶)-C₁-C₄ hydroxyalkyl, -C₁-C₄ alkylene-C(O)-N(R⁶)₂, -C(O)N(R⁶)-saturated heterocyclyl, -C(O)-saturated heterocyclyl, -C(O)-C₃-C₇ cycloalkyl, or -O-C₁-C₄ hydroxyalkyl; d. an R³ is oxetan-3-yl, azetidin-1-yl, 1,4-oxazepan-4-yl, pyridazin-4-yl, 1,2-dihydropyrazin-2-yl, 1,6-dihydropyrimdin-5-yl , 1,6-dihydropyridazin-4-yl, piperidin-3-yl, piperidin-4-yl, pyrimidin-2-yl, 3,6-dihydro-2H-pyran-4-yl, 2-oxa-5-azabicyclo [2.2.1]heptan-5-yl, 2-oxa-6-azaspiro[3.3]heptan-6-yl, hexahydropyrimidin-1-yl, 2,5-dioxa-8-azaspiro[3.5]nonan-8-yl , 8-oxa-3-azabicyclo[3.2.1]octan-3-yl, 2,6-diazaspiro[3.3]heptan-2-yl, or 2-oxa-6-azaspiro[3.5]nonan-6-yl R³ is optionally independently substituted with up to 3 substituents independently selected from halo, =O, -OH, CN, C₁-C₄ alkyl, C₁-C₄ hydroxyalkyl, C₁-C₄ haloalkyl, -COOH, -C(O) -N(R⁶)₂, -(C₀-C₄alkylene)-C(O)-O-C₁-C₄alkyl, -OC₁-C₄alkyl, -C(O)-C₁-C₄alkyl, -C₁-C₄alkylene- COOH, -S(O)₂-C₁-C₄ alkyl, -C(O)-N(R⁶)-C₁-C₄ hydroxyalkyl, -C₁-C₄ alkylene-C(O)-N(R⁶)₂, -C( O)N(R⁶)-saturated heterocyclyl, -C(O)-saturated heterocyclyl, -C(O)-C₃-C₇ cycloalkyl, and -O-C₁-C₄ hydroxyalkyl; and. an R² is -C(O)NH₂, -CH₂CN, -CH₂CHF₂, -CH₂COOH, -CH₂CH₂F, CH₂C(O)NHCH₃, CH₂C(O)N(CH₃)₂, -CH₂CH(OH)CH₃, -CH(CH₃) CH₂OH, -CH₂CH₂OCH₃, azetidin-3-yl, azetidin-3-ylmethyl, or oxazol-2-ylmethyl; F. R¹ is -C(OH)(CHF₂)-, -C(NH₂)(CF₃)-, oxiran-2,2-diyl, or 1,3-dioxolan-2,2-diyl; I g. R¹ is fused to ring A to form 2-oxo-octahydro-2H-imidazo[4,5-c]pyridin-1-yl, 1-oxa-6-azaspiro[2.5]octan-2-yl, octahydro-1H- pyrrolo[3,2-c]pyridin-1-yl, 2-oxo-hexahydrooxazolo[5,4-c]pyridin-1-yl, or 2,2-dioxo-octahydro-[1,2,5]thiadiazolo[ 3,4-c]pyridin-1-yl.

ARP210101930A 2020-07-10 2021-07-08 1,6-SUBSTITUTED NAPHTHYRIDINES INHIBITOR OF CDK5 AR122928A1 (en)

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