AR114417A1 - Compuestos y métodos de uso - Google Patents

Compuestos y métodos de uso

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AR114417A1
AR114417A1 ARP190100499A ARP190100499A AR114417A1 AR 114417 A1 AR114417 A1 AR 114417A1 AR P190100499 A ARP190100499 A AR P190100499A AR P190100499 A ARP190100499 A AR P190100499A AR 114417 A1 AR114417 A1 AR 114417A1
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Argentina
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alkyl
alkenyl
cycloalkyl
heterocyclyl
heteroaryl
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ARP190100499A
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Athisayamani Jeyaraj Duraiswamy
Biswajit Kalita
Anjali Pandey
Ruihong Chen
Chun Jiang
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Ferro Therapeutics Inc
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Publication of AR114417A1 publication Critical patent/AR114417A1/es

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    • 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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    • 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
    • A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K31/00—Medicinal preparations containing organic active ingredients
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    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
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    • 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
    • A61K31/535—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
    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • A61K47/40—Cyclodextrins; Derivatives thereof
    • 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
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
    • C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
    • C07D217/06—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with the ring nitrogen atom acylated by carboxylic or carbonic acids, or with sulfur or nitrogen analogues thereof, e.g. carbamates
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    • C07D—HETEROCYCLIC COMPOUNDS
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    • C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
    • C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
    • C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
    • C07D217/16—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals substituted by oxygen atoms
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
    • C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems

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  • Inorganic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

Esta presente divulgación se refiere a compuestos con actividad inductora de ferroptosis, un método para tratar a un sujeto con cáncer con los compuestos, y tratamientos de combinación con un segundo agente terapéutico. Reivindicación 1: Un compuesto de fórmula (1), o un tautómero, estereoisómero, mezcla de estereoisómeros, análogo isotópicamente enriquecido, o sal farmacéuticamente aceptable del mismo, en donde: anillo A es cicloalquilo C₄₋₁₀, heterociclilo, arilo, o heteroarilo; X es NR⁵, O ó S; p es 0, 1, 2 ó 3; q es 0, 1, 2 ó 3; R¹ es alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, haloalquilo C₁₋₆, cicloalquilo C₃₋₁₀, -CN, -OH, -C(O)OR⁶, -C(O)N(R⁷)₂, -OC(O)R⁶, -S(O)₂R⁸,-S(O)₂N(R⁷)₂, -S(O)N(R⁷)₂, -S(O)R⁸, -NH₂, -NHR⁸, -N(R⁸)₂, -NO₂, -OR⁸, alquilo -C₁₋₆-OH, alquilo -C₁₋₆-OR⁸, o -Si(R¹⁵)₃; R² es -C(O)R⁹; cada R³ es independientemente halo, -CN, -OH, -OR⁸, -NH₂, -NHR⁸, -N(R⁸)₂, -S(O)₂R⁸, -S(O)R⁸, -S(O)₂N(R⁷)₂, -S(O)N(R⁷)₂, -NO₂, -Si(R¹²)₃, -SF₅, -C(O)OR⁶, -C(O)N(R⁷)₂, -NR¹²C(O)R⁸, -NR¹²C(O)OR⁸, -OC(O)R⁸, -C(O)R⁶, -OC(O)CHR⁸N(R¹²)₂, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₁₀, heterociclilo, arilo, heteroarilo, alquilo C₁₋₆-cicloalquilo C₃₋₁₀, alquenilo C₂₋₆-cicloalquilo C₃₋₁₀, alquilo C₁₋₆-heterociclilo, alquenilo C₂₋₆-heterociclilo, alquilo C₁₋₆-arilo, alquenilo C₂₋₆-arilo, alquilo C₁₋₆-heteroarilo, o alquenilo C₂₋₆-heteroarilo; en donde cada alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₁₀, heterociclilo, arilo, heteroarilo, alquilo C₁₋₆-cicloalquilo C₃₋₁₀, -alquenilo C₂₋₆-cicloalquilo C₃₋₁₀, alquilo C₁₋₆-heterociclilo, alquenilo C₂₋₆-heterociclilo, alquilo C₁₋₆-arilo, alquenilo C₂₋₆-arilo, alquilo C₁₋₆-heteroarilo, o alquenilo C₂₋₆-heteroarilo de R³ está opcionalmente independientemente sustituido con uno a tres R¹⁰; cada R⁴ es independientemente halo, -CN, -OH, -OR⁸, -NH₂, -NHR⁸, -N(R⁸)₂, -S(O)₂R⁸, -S(O)R⁸, -S(O)₂N(R⁷)₂, -S(O)N(R⁷)₂, -NO₂, -Si(R¹⁵)₃, -C(O)OR⁶, -C(O)N(R⁷)₂, -NR¹²C(O)R⁸, -OC(O)R⁸, -C(O)R⁶, -OC(O)CHR⁸N(R¹²)₂, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₁₀, heterociclilo, arilo, heteroarilo, alquilo C₁₋₆-cicloalquilo C₃₋₁₀, alquenilo C₂₋₆-cicloalquilo C₃₋₁₀, alquilo C₁₋₆-heterociclilo, alquenilo C₂₋₆-heterociclilo, alquilo C₁₋₆-arilo, alquenilo C₂₋₆-arilo, alquilo C₁₋₆-heteroarilo, o alquenilo C₂₋₆-heteroarilo; en donde cada alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₁₀, heterociclilo, arilo, heteroarilo, alquilo C₁₋₆-cicloalquilo C₃₋₁₀, alquenilo C₂₋₆-cicloalquilo C₃₋₁₀, alquilo C₁₋₆-heterociclilo, alquenilo C₂₋₆-heterociclilo, alquilo C₁₋₆-arilo, alquenilo C₂₋₆-arilo, alquilo C₁₋₆-heteroarilo, o alquenilo C₂₋₆-heteroarilo de R⁴ está opcionalmente independientemente opcionalmente sustituido con uno a tres R¹⁰; R⁵ es hidrógeno o alquilo C₁₋₆; cada R⁶ es independientemente hidrógeno, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₁₀, heterociclilo, arilo, heteroarilo, alquilo C₁₋₆-cicloalquilo C₃₋₁₀, alquenilo C₂₋₆-cicloalquilo C₃₋₁₀, alquilo C₁₋₆-heterociclilo, alquenilo C₂₋₆-heterociclilo, alquilo C₁₋₆-arilo, alquenilo C₂₋₆-arilo, alquilo C₁₋₆-heteroarilo, o -alquenilo C₂₋₆-heteroarilo; en donde cada R⁶ está además sustituido independientemente con uno a tres R¹¹; cada R⁷ es independientemente hidrógeno, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₁₀, heterociclilo, arilo, heteroarilo, alquilo C₁₋₆-cicloalquilo C₃₋₆, alquenilo C₂₋₆-cicloalquilo C₃₋₆, alquilo C₁₋₆-heterociclilo, alquenilo C₂₋₆-heterociclilo, alquilo C₁₋₆-arilo, alquenilo C₂₋₆-arilo, alquilo C₁₋₆-heteroarilo, -alquenilo C₂₋₆-heteroarilo, o dos R⁷ junto con el nitrógeno al que están unidos, forman un heterociclilo de 4 a 7 miembros; en donde cada R⁷ o anillo formado con los mismos está además sustituido independientemente con uno a tres R¹¹; cada R⁸ es independientemente alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₁₀, heterociclilo, arilo, heteroarilo, alquilo C₁₋₆-cicloalquilo C₃₋₁₀, alquenilo C₂₋₆-cicloalquilo C₃₋₁₀, alquilo C₁₋₆-heterociclilo, alquenilo C₂₋₆-heterociclilo, alquilo C₁₋₆-arilo, alquenilo C₂₋₆-arilo, alquilo C₁₋₆-heteroarilo, o alquenilo C₂₋₆-heteroarilo; en donde cada R⁸ está además sustituido independientemente con uno a tres R¹¹; R⁹ es haloalquilo C₁₋₂, -alquenilo C₂₋₃, -haloalquenilo C₂₋₃, alquinilo C₂, o -CH₂OS(O)₂-fenilo, en donde el haloalquilo C₁₋₂ y -haloalquenilo C₂₋₃ están opcionalmente sustituidos con uno o dos -CH₃, y el alquinilo C₂ y fenilo están opcionalmente sustituido con un -CH₃; cada R¹⁰ es independientemente halo, -CN, -OR¹², -NO₂, -N(R¹²)₂, -S(O)R¹³, -S(O)₂R¹³, -S(O)N(R¹²)₂, -S(O)₂N(R¹²)₂, -Si(R¹²)₃, -C(O)R¹², -C(O)OR¹², -C(O)N(R¹²)₂, -NR¹²C(O)R¹², -OC(O)R¹², -OC(O)OR¹², -OC(O)N(R¹²)₂, -NR¹²C(O)OR¹², -OC(O)CHR¹²N(R¹²)₂, alquilo C₁₋₆, haloalquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₁₀, heterociclilo, arilo, o heteroarilo, en donde cada alquilo C₁₋₆, haloalquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₁₀, heterociclilo, arilo, o heteroarilo de R¹⁰ está opcionalmente independientemente sustituido con uno a tres R¹¹; cada R¹¹ es independientemente halo, -CN, -OR¹², -NO₂, -N(R¹²)₂, -S(O)R¹³, -S(O)₂R¹³, -S(O)N(R¹²)₂, -S(O)₂N(R¹²)₂, -Si(R¹²)₃, -C(O)R¹², -C(O)OR¹², -C(O)N(R¹²)₂, -NR¹²C(O)R¹², -OC(O)R¹², -OC(O)OR¹², -OC(O)N(R¹²)₂, -NR¹²C(O)OR¹², -OC(O)CHR¹²N(R¹²)₂, alquilo C₁₋₆, haloalquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₁₀, heterociclilo, arilo, o heteroarilo; cada R¹² es independientemente hidrógeno, alquilo C₁₋₆ o cicloalquilo C₃₋₁₀; y cada R¹³ es independientemente alquilo C₁₋₆ o cicloalquilo C₃₋₁₀; con la condición de que: (a) cuando X es NH, R¹ es -C(O)OR⁶, R² es -C(O)CH₂Cl o C(O)CH₂F, q es 1, p es 0, y anillo A con el R³ es de fórmula (2); entonces (i) R³ y R⁶ no son simultáneamente -NO₂ y -CH₃, respectivamente, y (ii) cuando R⁶ es -CH₃, entonces R³ es otro que H, halo, y -NO₂; y (b) cuando X es NH, R¹ es -C(O)OR⁶, R² es -C(O)CH₂Cl o C(O)CH₂F, q es 1, p es 0, anillo A con el R³ es de fórmula (2), y R³ es -C(O)OR⁶; entonces ambos R⁶ no son simultáneamente (i) -CH₃; (ii) -CH₃ y alquinilo C₂₋₆, respectivamente; o (iii) -CH₂CH₃ y -CH₃, respectivamente; y (c) cuando X es NH, R¹ es -C(O)OCH₃, R² es -C(O)CH₂Cl o -C(O)CH₂F, q es 1, p es 0, y R³ es H; entonces anillo A es otro que fenilo; y (d) cuando X es NH, R¹ es -C(O)N(R⁷)₂, en donde R⁷ son H, R² es -C(O)CH₂Cl o -C(O)CH₂F, q es 1, p es 0, y anillo A es fenilo; entonces R³ es otro que H o halo; y (e) el compuesto no es seleccionado del grupo de fórmulas (3).
ARP190100499A 2018-02-28 2019-02-28 Compuestos y métodos de uso AR114417A1 (es)

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EP3931183A1 (en) * 2019-02-27 2022-01-05 Ferro Therapeutics, Inc. Compounds with ferroptosis inducing activity and methods of their use
US11040964B2 (en) 2019-02-27 2021-06-22 Ferro Therapeutics, Inc. Compounds and methods of use
CN110511253B (zh) * 2019-09-04 2023-10-13 上海药明康德新药开发有限公司 DNA编码化合物库构建中On-DNA四氢-β-咔啉类化合物的合成方法
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