AR123089A2 - Compuesto de piridinona - Google Patents

Compuesto de piridinona

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Publication number
AR123089A2
AR123089A2 ARP210102120A ARP210102120A AR123089A2 AR 123089 A2 AR123089 A2 AR 123089A2 AR P210102120 A ARP210102120 A AR P210102120A AR P210102120 A ARP210102120 A AR P210102120A AR 123089 A2 AR123089 A2 AR 123089A2
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Argentina
Prior art keywords
optionally substituted
group
alkyl
aryl
alkynyl
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ARP210102120A
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English (en)
Inventor
Brad Buckman
John B Nicholas
Johnnie Y Ramphal
Kumaraswamy Emayan
Scott D Seiwert
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Intermune Inc
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Publication of AR123089A2 publication Critical patent/AR123089A2/es

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—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
    • 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/04—Drugs for skeletal disorders for non-specific disorders of the connective tissue
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—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
    • 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/69—Two or more 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
    • C07D217/24—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/16—Ring systems of three rings containing carbocyclic rings other than six-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/18—Ring systems of four or more rings
    • 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
    • C07D401/04—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
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  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • Biomedical Technology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Dermatology (AREA)
  • Pulmonology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Un compuesto de piridinona que presenta la estructura de fórmula (1) o una de sus sales farmacéuticamente aceptables, en la 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, alqueniloC₂₋₆ 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, -CN, -SO₂R¹⁶, 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-fenilo) y R¹ es C(O)OH, entonces R³ no puede ser 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. Se proveen entonces el compuesto de piridinona descrito, un método para preparar este compuesto y métodos para tratar trastornos fibróticos.
ARP210102120A 2012-10-02 2021-07-26 Compuesto de piridinona AR123089A2 (es)

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AR092742A1 (es) 2012-10-02 2015-04-29 Intermune Inc Piridinonas antifibroticas
US9770443B2 (en) 2014-01-10 2017-09-26 Genoa Pharmaceuticals, Inc. Aerosol pirfenidone and pyridone analog compounds and uses thereof
KR102373700B1 (ko) 2014-04-02 2022-03-11 인터뮨, 인크. 항섬유성 피리디논
CN104031044A (zh) * 2014-06-06 2014-09-10 江西科技师范大学 电子受体吡啶并杂环化合物的制备方法
MA40940A (fr) * 2014-11-10 2017-09-19 Constellation Pharmaceuticals Inc Pyrrolopyridines substituées utilisées en tant qu'inhibiteurs de bromodomaines
MA40943A (fr) * 2014-11-10 2017-09-19 Constellation Pharmaceuticals Inc Pyrrolopyridines substituées utilisées en tant qu'inhibiteurs de bromodomaines
JP6639497B2 (ja) 2014-11-10 2020-02-05 ジェネンテック， インコーポレイテッド ブロモドメインインヒビターおよびその使用
JP6709792B2 (ja) 2015-01-29 2020-06-17 ジェネンテック， インコーポレイテッド 治療用化合物およびその使用
KR20180039117A (ko) 2015-08-11 2018-04-17 네오메드 인스티튜트 아릴-치환된 디히드로퀴놀리논, 그의 제조법 및 제약으로서의 그의 용도
US10836742B2 (en) 2015-08-11 2020-11-17 Neomed Institute N-substituted bicyclic lactams, their preparation and their use as pharmaceuticals
EP3334719B1 (en) 2015-08-12 2021-09-15 Neomed Institute Substituted benzimidazoles, their preparation and their use as pharmaceuticals
WO2017066876A1 (en) 2015-10-21 2017-04-27 Neomed Institute Substituted imidazopyridines, their preparation and their use as pharmaceuticals
WO2017127930A1 (en) 2016-01-28 2017-08-03 Neomed Institute Substituted [1,2,4]triazolo[4,3-a]pyridines, their preparation and their use as pharmaceuticals
CA3020779A1 (en) * 2016-04-14 2017-10-19 Shijiazhuang Sagacity New Drug Development Co., Ltd. Pyridone derivative and its use for treating fibrosis and inflammatory diseases
MA44674B1 (fr) 2016-04-15 2020-06-30 Abbvie Inc Inhibiteurs de bromodomaine
EP3661506A4 (en) * 2017-07-31 2021-04-21 Washington University PIRFENIDONE DERIVATIVES FOR MODULATION OF B LYMPHOCYTE ACTIVITY AND ORGAN PROTECTION
GB201801128D0 (en) 2018-01-24 2018-03-07 Univ Oxford Innovation Ltd Compounds

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JP5627574B2 (ja) * 2008-06-03 2014-11-19 インターミューン， インコーポレイテッド 炎症性および線維性疾患を治療するための化合物および方法

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