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AR092742A1 - Piridinonas antifibroticas - Google Patents

Piridinonas antifibroticas

Info

Publication number
AR092742A1
AR092742A1 ARP130103530A ARP130103530A AR092742A1 AR 092742 A1 AR092742 A1 AR 092742A1 AR P130103530 A ARP130103530 A AR P130103530A AR P130103530 A ARP130103530 A AR P130103530A AR 092742 A1 AR092742 A1 AR 092742A1
Authority
AR
Argentina
Prior art keywords
optionally substituted
group
alkyl
aryl
alkynyl
Prior art date
Application number
ARP130103530A
Other languages
English (en)
Inventor
Buckman Brad
b nicholas John
Y Ramphal Johnnie
Emayan Kumaraswamy
D Seiwert Scott
Original Assignee
Intermune Inc
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=50435378&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=AR092742(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Intermune Inc filed Critical Intermune Inc
Publication of AR092742A1 publication Critical patent/AR092742A1/es

Links

Classifications

    • 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
    • A61K31/4412—Non condensed pyridines; Hydrogenated derivatives thereof having oxo groups directly attached to the heterocyclic ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/4035—Isoindoles, e.g. phthalimide
    • A—HUMAN NECESSITIES
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    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
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    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
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    • C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings 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 ring carbon atoms
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    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
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    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
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  • Urology & Nephrology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Biomedical Technology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Indole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

Abstract

Reivindicación 1: Un compuesto caracterizado porque tiene la estructura de fórmula (1) o una de sus sales farmacéuticamente aceptables, en el cual: R¹ se selecciona entre el grupo que comprende halógeno, -CN, -C(O)R⁸, -SO₂R¹⁶, alquilo C₁₋₆ opcionalmente sustituido por uno o más R⁴, alquenilo C₂₋₆ opcionalmente sustituido por uno o más R⁴, alquinilo C₂₋₆ opcionalmente sustituido por uno o más R⁴, arilo C₆₋₁₀ opcionalmente sustituido por uno o más R⁴, un heteroarilo de 5 - 10 miembros opcionalmente sustituido por uno o más R⁴, carbociclilo C₃₋₁₀ opcionalmente sustituido por uno o más R⁴, y heterociclilo de 3 - 10 miembros opcionalmente sustituido por uno o más R⁴; R² se selecciona entre el grupo que comprende halógeno, -CN, -OR⁵, -SR⁵, -NR⁶R⁷, y -C(O)R⁸; R³ se selecciona entre el grupo que comprende hidrógeno, -(CH₂)ₙ-(arilo C₆₋₁₀), -(CH₂)ₙ-(heteroarilo de 5 - 10 miembros), -(CH₂)ₙ-(carbociclilo C₃₋₁₀), y -(CH₂)ₙ-(heterociclilo de 3 - 10 miembros), cada uno opcionalmente sustituido por uno o más R⁹; cada R⁴ se selecciona independientemente entre el grupo que comprende halógeno, -CN, -OH, -C(O)R⁸, -SO₂R¹⁶, alquilo C₁₋₆ opcionalmente sustituido, alquenilo C₂₋₆ opcionalmente sustituido, alquinilo C₂₋₆ opcionalmente sustituido, alcoxi C₁₋₆ opcionalmente sustituido, arilo C₆₋₁₀ opcionalmente sustituido por uno o más R¹¹, aralquilo C₇₋₁₄ opcionalmente sustituido por uno o más R¹¹, heteroarilo de 5 - 10 miembros opcionalmente sustituido por uno o más R¹¹, o independientemente dos R⁴ geminales juntos son oxo; cada R⁵ se selecciona independientemente entre el grupo que comprende hidrógeno, alquilo C₁₋₆ opcionalmente sustituido, alquenilo C₂₋₆ opcionalmente sustituido, alquinilo C₂₋₆ opcionalmente sustituido, alcoxialquilo C₂₋₈ opcionalmente sustituido, arilo C₆₋₁₀ opcionalmente sustituido por uno o más R¹¹, aralquilo C₇₋₁₄ opcionalmente sustituido por uno o más R¹¹, y -(CH₂)ₙ-(heterociclilo de 3 - 10 miembros) opcionalmente sustituido por uno o más R¹⁰; R⁶ se selecciona entre el grupo que comprende hidrógeno, alquilo C₁₋₆ opcionalmente sustituido, alquenilo C₂₋₆ opcionalmente sustituido, alquinilo C₂₋₆ opcionalmente sustituido, arilo C₆₋₁₀ opcionalmente sustituido por uno o más R¹¹, aralquilo C₇₋₁₄ opcionalmente sustituido por uno o más R¹¹, y alquilo(heteroarilo de 5 - 10 miembros) opcionalmente sustituido por uno o más R¹¹, -C(O)R⁸, y -C(O)OR⁵; R⁷ se selecciona entre el grupo que comprende hidrógeno, alquilo C₁₋₆ opcionalmente sustituido, alquenilo C₂₋₆ opcionalmente sustituido, alquinilo C₂₋₆ opcionalmente sustituido, arilo C₆₋₁₀ opcionalmente sustituido por uno o más R¹¹, aralquilo C₇₋₁₄ opcionalmente sustituido por uno o más R¹¹, y alquilo-(heteroarilo de 5 - 10 miembros) opcionalmente sustituido por uno o más R¹¹, -C(O)R⁸, y -C(O)OR⁵; o R⁶ y R⁷ junto con el nitrógeno al que están unidos forman un heterociclilo de 3 - 10 miembros opcionalmente sustituido por uno o más R¹⁰; cada R⁸ se selecciona independientemente entre el grupo que comprende hidrógeno, alquilo C₁₋₆ opcionalmente sustituido, alquenilo C₂₋₆ opcionalmente sustituido, alquinilo C₂₋₆ opcionalmente sustituido, arilo C₆₋₁₀ opcionalmente sustituido por uno o más R¹¹, aralquilo C₇₋₁₄ opcionalmente sustituido por uno o más R¹¹, -NR¹²R¹³, y -OR⁵; cada R⁹ se selecciona independientemente entre el grupo que comprende hidroxi, halógeno, alquilo C₁₋₆ opcionalmente sustituido, alquenilo C₂₋₆ opcionalmente sustituido, alquinilo C₂₋₆ opcionalmente sustituido, alquiltio-C₁₋₆ opcionalmente sustituido, alcoxialquilo C₂₋₈ opcionalmente sustituido, carbociclilo C₃₋₁₀ opcionalmente sustituido, arilo C₆₋₁₀ opcionalmente sustituido, -OR⁵, -NR¹⁴R¹⁵, -C(O)R⁸, -SO₂R¹⁶, -CN, y -NO₂; cada R¹⁰ se selecciona independientemente entre el grupo que comprende alquilo C₁₋₆ opcionalmente sustituido, alquenilo C₂₋₆ opcionalmente sustituido, y alquinilo C₂₋₆ opcionalmente sustituido, o independientemente dos R¹⁰ geminales juntos son oxo; cada R¹¹ se selecciona independientemente entre el grupo que comprende halógeno, -CN, alquilo C₁₋₆ opcionalmente sustituido, alquenilo C₂₋₆ opcionalmente sustituido, alquinilo C₂₋₆ opcionalmente sustituido, -O-(CH₂)ₙ-alcoxi C₁₋₈, -C(O)R⁸, y alcoxi C₁₋₆ opcionalmente sustituido; cada R¹² se selecciona independientemente entre el grupo que comprende hidrógeno, alquilo C₁₋₆ opcionalmente sustituido, alquenilo C₂₋₆ opcionalmente sustituido, alquinilo C₂₋₆ opcionalmente sustituido, arilo C₆₋₁₀ opcionalmente sustituido por uno o más R¹¹, aralquilo C₇₋₁₄ opcionalmente sustituido por uno o más R¹¹; cada R¹³ se selecciona independientemente entre el grupo que comprende hidrógeno, alquilo C₁₋₆ opcionalmente sustituido, alquenilo C₂₋₆ opcionalmente sustituido, alquinilo C₂₋₆ opcionalmente sustituido, arilo C₆₋₁₀ opcionalmente sustituido por uno o más R¹¹, aralquilo C₇₋₁₄ opcionalmente sustituido por uno o más R¹¹; R¹⁴ se selecciona entre el grupo que comprende hidrógeno, alquilo C₁₋₆ opcionalmente sustituido, arilo C₆₋₁₀ opcionalmente sustituido, y -C(O)R⁸; R¹⁵ se selecciona entre el grupo que comprende hidrógeno, alquilo C₁₋₆ opcionalmente sustituido, arilo C₆₋₁₀ opcionalmente sustituido, y -C(O)R⁸; cada R¹⁶ se selecciona independientemente entre el grupo que comprende alquilo C₁₋₆ opcionalmente sustituido, alquenilo C₂₋₆ opcionalmente sustituido, alquinilo C₂₋₆ opcionalmente sustituido, arilo C₆₋₁₀ opcionalmente sustituido por uno o más R¹¹, aralquilo C₇₋₁₄ opcionalmente sustituido por uno o más R¹¹, -NR¹²R¹³, y -OR⁵; Z se selecciona entre oxígeno y azufre; cada n es, independientemente, un entero que oscila entre 0 y 4; y los enlaces representados por una línea continua y de guiones se seleccionan independientemente entre el grupo que comprende un enlace simple y un enlace doble, siempre que cuando R³ es H, entonces R¹ se selecciona entre arilo C₆₋₁₀ opcionalmente sustituido por uno o más R⁴, o heteroarilo de 5 - 10 miembros opcionalmente sustituido por uno o más R⁴; cuando R² es -NH-(2-fluoro-4-bromo-fenil) y R¹ es C(O)OH, entonces R³ no es fenilo-CH₂; cuando R² es metoxi, R¹ es 4-metoxifenilo, y Z es O, entonces R³ no es 2-fluoro-4-cloro-fenilo-(CH₂); cuando R³ es un fenilo; R² es OR⁵ o NR⁶R⁷; entonces R¹ no es triazolilo; cuando R³ es 4-metil fenilo, R² es morfolinilo, y Z es O; entonces R¹ no es metilo; y cuando R³ es 4-metil fenilo, R² es -N(CH₃)₂, Z es O; entonces R¹ no es metilo.
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