AR118205A1 - Compuestos que tienen actividad inductora de ferroptosis - Google Patents

Compuestos que tienen actividad inductora de ferroptosis

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Publication number
AR118205A1
AR118205A1 ARP200100540A ARP200100540A AR118205A1 AR 118205 A1 AR118205 A1 AR 118205A1 AR P200100540 A ARP200100540 A AR P200100540A AR P200100540 A ARP200100540 A AR P200100540A AR 118205 A1 AR118205 A1 AR 118205A1
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Argentina
Prior art keywords
alkyl
alkenyl
6aryl
cycloalkyl
alkynyl
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ARP200100540A
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English (en)
Inventor
Athisayamani Jeyaraj Duraiswamy
Biswajit Kalita
Ruihong Chen
Chun Jiang
Anjali Pandey
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Ferro Therapeutics Inc
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Application filed by Ferro Therapeutics Inc filed Critical Ferro Therapeutics Inc
Publication of AR118205A1 publication Critical patent/AR118205A1/es

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • 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
    • A61K31/4353—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
    • 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
    • A61K31/535—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
    • C—CHEMISTRY; METALLURGY
    • 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
    • C—CHEMISTRY; METALLURGY
    • 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
    • C—CHEMISTRY; METALLURGY
    • 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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

Reivindicación 1: Un compuesto de fórmula (1) o un tautómero, estereoisómero, mezcla de estereoisómeros, análogo enriquecido isotópicamente, o una sal farmacéuticamente aceptable del mismo, en donde: el anillo A es cicloalquilo-C₄₋₁₀, heterociclilo, arilo o heteroarilo; X es -O-, -S-, -NR⁹-, -CR⁵=CR⁵-, o -CR⁵=N-; p es 0, 1 ó 2; 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, -OR⁷, -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, -N(R⁷)₂, -NO₂, alquilo-C₁₋₆-OR⁷, o -Si(R¹⁵)₃; R² 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 sustituidos con un -CH₃; 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)N(R⁷)₂, -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, alquil-C₁₋₆cicloalquilo-C₃₋₁₀, alquenil-C₂₋₆cicloalquilo-C₃₋₁₀, alquil-C₁₋₆heterociclilo, alquenil-C₂₋₆heterociclilo, alquil-C₁₋₆arilo, alquenil-C₂₋₆arilo, alquilo-C₁₋₆heteroarilo, o alquenil-C₂₋₆heteroarilo; en donde cada alquilo-C₁₋₆, alquenilo-C₂₋₆, alquinilo-C₂₋₆, cicloalquilo-C₃₋₁₀, heterociclilo, arilo, heteroarilo, alquil-C₁₋₆cicloalquilo-C₃₋₁₀, alquenil-C₂₋₆cicloalquilo-C₃₋₁₀, alquil-C₁₋₆heterociclilo, alquenil-C₂₋₆heterociclilo, alquil-C₁₋₆arilo, alquenil-C₂₋₆arilo, alquilo-C₁₋₆heteroarilo, o alquenil-C₂₋₆heteroarilo de R³ es independientemente opcionalmente 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, -NR¹²C(O)OR⁸, -OC(O)N(R⁷)₂, -OC(O)CHR⁸N(R¹²)₂, alquilo-C₁₋₆, alquenilo-C₂₋₆, alquinilo-C₂₋₆, cicloalquilo-C₃₋₁₀, heterociclilo, arilo, heteroarilo, alquil-C₁₋₆cicloalquilo-C₃₋₁₀, alquenil-C₂₋₆cicloalquilo-C₃₋₁₀, alquil-C₁₋₆heterociclilo, alquenil-C₂₋₆heterociclilo, alquil-C₁₋₆arilo, alquenil-C₂₋₆arilo, alquilo-C₁₋₆heteroarilo, o alquenil-C₂₋₆heteroarilo; en donde cada alquilo-C₁₋₆, alquenilo-C₂₋₆, alquinilo-C₂₋₆, cicloalquilo-C₃₋₁₀, heterociclilo, arilo, heteroarilo, alquil-C₁₋₆cicloalquilo-C₃₋₁₀, alquenil-C₂₋₆cicloalquilo-C₃₋₁₀, alquil-C₁₋₆heterociclilo, alquenil-C₂₋₆heterociclilo, alquil-C₁₋₆arilo, alquenil-C₂₋₆arilo, alquilo-C₁₋₆heteroarilo, o alquenil-C₂₋₆heteroarilo de R⁴ está opcionalmente independientemente opcionalmente sustituido con uno a tres R¹⁰; cada R⁵ es independientemente hidrógeno, 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, -NR¹²C(O)OR⁸ ,-OC(O)N(R⁷)₂,-OC(O)CHR⁸N(R¹²)₂, alquilo-C₁₋₆, alquenilo-C₂₋₆, alquinilo-C₂₋₆, cicloalquilo-C₃₋₁₀, heterociclilo, arilo, heteroarilo, alquil-C₁₋₆cicloalquilo-C₃₋₁₀, alquenil-C₂₋₆cicloalquilo-C₃₋₁₀, alquil-C₁₋₆heterociclilo, alquenil-C₂₋₆heterociclilo, alquil-C₁₋₆arilo, alquenil-C₂₋₆arilo, alquilo-C₁₋₆heteroarilo, o alquenil-C₂₋₆heteroarilo; en donde cada alquilo-C₁₋₆, alquenilo-C₂₋₆, alquinilo-C₂₋₆, cicloalquilo-C₃₋₁₀, heterociclilo, arilo, heteroarilo, alquil-C₁₋₆cicloalquilo-C₃₋₁₀, alquenil-C₂₋₆cicloalquilo-C₃₋₁₀, alquil-C₁₋₆heterociclilo, alquenil-C₂₋₆heterociclilo, alquil-C₁₋₆arilo, alquenil-C₂₋₆arilo, alquilo-C₁₋₆heteroarilo, o alquenil-C₂₋₆heteroarilo de R⁵ está opcionalmente independientemente opcionalmente sustituido con uno a tres R¹⁰; cada R⁶ es independientemente hidrógeno, alquilo-C₁₋₆, alquenilo-C₂₋₆, alquinilo-C₂₋₆, cicloalquilo-C₃₋₁₀, heterociclilo, arilo, heteroarilo, alquil-C₁₋₆cicloalquilo-C₃₋₁₀, alquenil-C₂₋₆cicloalquilo-C₃₋₁₀, alquil-C₁₋₆heterociclilo, alquenil-C₂₋₆heterociclilo, alquil-C₁₋₆arilo, alquenil-C₂₋₆arilo, alquilo-C₁₋₆heteroarilo, o alquenil-C₂₋₆heteroarilo; en donde cada R⁶ está independientemente sustituido adicionalmente 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, alquil-C₁₋₆cicloalquilo-C₃₋₆, alquenil-C₂₋₆cicloalquilo-C₃₋₆, alquil-C₁₋₆heterociclilo, alquenil-C₂₋₆heterociclilo, alquil-C₁₋₆arilo, alquenil-C₂₋₆arilo, alquil-C₁₋₆heteroarilo, alquenil-C₂₋₆heteroarilo, o dos R⁷ junto con el átomo de nitrógeno al que están unidos, forman un heterociclilo de 4 a 7 miembros; en donde cada R⁷ o anillo formado de ese modo está independientemente sustituido adicionalmente con uno a tres R¹¹; cada R⁸ es independientemente alquilo-C₁₋₆, alquenilo-C₂₋₆, alquinilo-C₂₋₆, cicloalquilo-C₃₋₁₀, heterociclilo, arilo, heteroarilo, alquil-C₁₋₆cicloalquilo-C₃₋₁₀, alquenil-C₂₋₆cicloalquilo-C₃₋₁₀, alquil-C₁₋₆heterociclilo, alquenil-C₂₋₆heterociclilo, alquil-C₁₋₆arilo, alquenil-C₂₋₆arilo, alquil-C₁₋₆heteroarilo, o alquenil-C₂₋₆heteroarilo; en donde cada R⁸ está independientemente sustituido adicionalmente con uno a tres R¹¹; R⁹ es hidrógeno o alquilo-C₁₋₆; 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; cada R¹³ es independientemente alquilo-C₁₋₆ o cicloalquilo-C₃₋₁₀; y cada R¹⁵ es independientemente alquilo-C₁₋₆, alquenilo-C₂₋₆, arilo, heteroarilo, alquil-C₁₋₆arilo, alquenil-C₂₋₆arilo, alquil-C₁₋₆heteroarilo, y alquenil-C₂₋₆heteroarilo.
ARP200100540A 2018-02-28 2020-02-27 Compuestos que tienen actividad inductora de ferroptosis AR118205A1 (es)

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