AR115920A1 - Inhibidores tipo indol y azaindol de enzimas pad - Google Patents

Inhibidores tipo indol y azaindol de enzimas pad

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Publication number
AR115920A1
AR115920A1 ARP190102237A ARP190102237A AR115920A1 AR 115920 A1 AR115920 A1 AR 115920A1 AR P190102237 A ARP190102237 A AR P190102237A AR P190102237 A ARP190102237 A AR P190102237A AR 115920 A1 AR115920 A1 AR 115920A1
Authority
AR
Argentina
Prior art keywords
substituted
chrd
alkyl
occurrence
heterocyclyl
Prior art date
Application number
ARP190102237A
Other languages
English (en)
Inventor
Khehyong Ngu
Robert J Cherney
Anurag S Srivastava
Original Assignee
Bristol Myers Squibb Co
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Publication date
Application filed by Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co
Publication of AR115920A1 publication Critical patent/AR115920A1/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
    • C07D471/08—Bridged systems
    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
    • 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
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • 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
    • C07D401/14—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 three or more hetero rings
    • 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
    • C07D403/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Epidemiology (AREA)
  • Rheumatology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Hematology (AREA)
  • Oncology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Immunology (AREA)
  • Pain & Pain Management (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

Reivindicación 1: Un compuesto de la fórmula (1), o una sal farmacéuticamente aceptable del mismo, en donde: Q se selecciona a partir de N y CH; el anillo A es heterociclilo de 4 a 15 miembros sustituido por 1 - 4 R⁷; R¹ se selecciona de CH₃ y CD₃ y -CH₂-heterociclilo de 5 miembros que comprende átomos de carbono y de 1 a 3 heteroátomos seleccionados a partir de N, N-alquiloC₁₋₄, O, y S; R² se selecciona de H, alquilo C₁₋₃ sustituido por 0 - 5 Rᵉ, y -(CH₂)ʳ-cicloalquilo C₃₋₆ sustituido por 0 - 5 Rᵉ; R³ se selecciona de H, F, Cl, Br, -ORᵇ, y alquilo C₁₋₃ sustituido por 0 - 5 Rᵉ; L está ausente o se selecciona de NRᵈ-, -O-, -C(=O)NRᵈ-, y -S(O)ₚ-; R⁴ se selecciona de -(CH₂)ʳ-arilo sustituido por 1 - 7 R⁵, -(CH₂)ʳ-cicloalquilo C₃₋₁₂ sustituido por 1 - 7 R⁵, -(CH₂)ʳ-cicloalquiloC₃₋₁₂ (sustituido con 1 - 2 ORᵇ, C(=O)ORᵇ, -C(=O)NRᵃRᵃ, -NRᵃC(=O)Rᵇ), -(CH₂)ʳ-heterociclilo que comprende átomos de carbono y 1 - 3 heteroátomos seleccionados de N, NR⁶, O, y S y sustituido por 1 - 7 R⁵; R⁵, en cada aparición, se selecciona independientemente de H, F, Cl, Br, CN, =O, nitro, alquilo C₁₋₄ sustituido por 0 - 5 Rᵉ, alquenilo C₂₋₄ sustituido por 0 - 5 Rᵉ, alquinilo C₂₋₄ sustituido por 0 - 5 Rᵉ, -(CHRᵈ)ʳORᵇ, -(CHRᵈ)ʳS(O)ₚRᶜ, -(CHRᵈ)ʳS(O)ₚNRᵃRᵃ, -(CHRᵈ)ʳNRᵃS(O)ₚRᶜ, -(CHRᵈ)ʳNRᵃRᵃ, -(CHRᵈ)ʳNRᵃC(=O)Rᵇ, -(CHRᵈ)ʳNRᵃC(=O)ORᵇ, -(CHRᵈ)ʳNRᵃC(=O)NRᵃRᵃ, -(CHRᵈ)ʳC(=O)Rᵇ, -(CHRᵈ)ʳC(=O)ORᵇ, -(CHRᵈ)ʳC(=O)NRᵃRᵃ, -(CHRᵈ)ʳOC(=O)Rᵇ, -(CHRᵈ)ʳOC(=O)ORᵇ, -(CHRᵈ)ʳO(CH₂)ʳC(=O)NRᵃRᵃ, cicloalquilo C₃₋₆ sustituido por 0 - 4 Rᵉ, arilo sustituido por 0 - 4 Rᵉ, y heterociclilo sustituido por 0 - 4 Rᵉ; R⁶ se selecciona de H, alquilo C₁₋₃ sustituido por 0 - 4 Rᵉ, -S(O)ₚRᶜ, -(CH₂)ʳC(=O)Rᵇ, -(CH₂)ʳC(=O)ORᵇ, -(CH₂)ʳC(=O)(CH₂)ʳNRᵃRᵃ, -C(=O)(CH₂)ʳNRᵃC(=O)Rᵇ, -S(O)ₚNRᵃRᵃ, -(CH₂)ʳ-cicloalquilo C₃₋₆ sustituido por 0 - 4 Rᵉ, -(CH₂)ʳ-arilo sustituido por 0 - 4 Rᵉ, y -(CH₂)ʳ-heterociclilo sustituido por 0 - 4 Rᵉ; R⁷ se selecciona de H, F, Cl, CN, alquilo C₁₋₃, =N-ORᵇ, -(CH₂)ʳORᵇ, -(CH₂)ʳNRᵃRᵃ, -NRᵃC(=NH)alquilo C₁₋₃, -NRᵃC(=O)ORᵇ, carbociclilo, y heterociclilo; alternativamente, dos grupos R⁷ se toman juntos para formar carbociclilo o heterociclilo; R⁸, en cada aparición, se selecciona independientemente de H, F, Cl, Br, y alquilo C₁₋₄ sustituido por 0 - 5 Rᵉ; Rᵃ, en cada aparición, se selecciona independientemente de H, alquilo C₁₋₆ sustituido por 0 - 5 Rᵉ, alquenilo C₂₋₆ sustituido por 0 - 5 Rᵉ, alquinilo C₂₋₆ sustituido por 0 - 5 Rᵉ, -(CH₂)ʳ-carbociclo C₃₋₁₀ sustituido por 0 - 5 Rᵉ, y -(CH₂)ʳ-heterociclilo sustituido por 0 - 5 Rᵉ; o Rᵃ y Rᵃ junto con el átomo de nitrógeno al cual están unidos forman un anillo heterocíclico sustituido por 0 - 5 Rᵉ; Rᵇ, en cada aparición, se selecciona independientemente de H, alquilo C₁₋₆ sustituido por 0 - 5 Rᵉ, alquenilo C₂₋₆ sustituido por 0 - 5 Rᵉ, alquinilo C₂₋₆ sustituido por 0 - 5 Rᵉ, -(CH₂)ʳ-carbociclilo C₃₋₁₀ sustituido por 0 - 5 Rᵉ, y -(CH₂)ʳ-heterociclilo sustituido por 0 - 5 Rᵉ; Rᶜ, en cada aparición, se selecciona independientemente de alquilo C₁₋₆ sustituido por 0 - 5 Rᵉ, alquenilo C₂₋₆ sustituido por 0 - 5 Rᵉ, alquinilo C₂₋₆ sustituido por 0 - 5 Rᵉ, -(CH₂)ʳ-carbociclo C₃₋₆ sustituido por 0 - 5 Rᵉ, y -(CH₂)ʳ-heterociclilo sustituido por 0 - 5 Rᵉ; Rᵈ, en cada aparición, se selecciona independientemente de H, alquilo C₁₋₆ sustituido por 0 - 5 Rᵉ, y OH, Rᵉ, en cada aparición, se selecciona independientemente de alquilo C₁₋₆ sustituido por 0 - 5 Rᶠ, alquenilo C₂₋₆, alquinilo C₂₋₆, -(CH₂)ʳ-cicloalquilo C₃₋₆, -(CH₂)ʳ-arilo, -(CH₂)ʳ-heterociclilo, Si(alquilo C₁₋₄)₃, F, Cl, Br, CN, NO₂, =O, CO₂H, -(CH₂)ʳORᶠ, S(O)ₚRᶠ, C(=O)NRᶠRᶠ, S(O)ₚNRᶠRᶠ, y -(CH₂)ʳNRᶠRᶠ; Rᶠ, en cada aparición, se selecciona independientemente de H, F, Cl, Br, CN, OH, alquilo C₁₋₅ opcionalmente sustituido por OH, alquenilo C₂₋₅, alquinilo C₂₋₅, cicloalquilo C₃₋₆, y fenilo, o Rᶠ y Rᶠ junto con el átomo de nitrógeno al cual están unidos forman un anillo heterocíclico opcionalmente sustituido por alquilo C₁₋₄; p, en cada aparición, se selecciona independientemente de cero, 1, y 2; r, en cada aparición, se selecciona independientemente de cero, 1, 2, 3, y 4; siempre que: [1] cuando L está ausente, R⁴ no es un compuesto del grupo de fórmulas (2); [2] cuando L es -NRᵈ-, R⁴ no es un compuesto del grupo de fórmulas (3); y [3] cuando L es -O-, R⁴ no es cicloalquilo C₃₋₆.
ARP190102237A 2018-08-08 2019-08-07 Inhibidores tipo indol y azaindol de enzimas pad AR115920A1 (es)

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US201862715850P 2018-08-08 2018-08-08

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US (1) US11524959B1 (es)
EP (1) EP3833440A1 (es)
JP (1) JP2021534108A (es)
KR (1) KR20210042934A (es)
CN (1) CN112805067A (es)
AR (1) AR115920A1 (es)
AU (1) AU2019319835A1 (es)
BR (1) BR112021002091A2 (es)
CA (1) CA3108791A1 (es)
CL (1) CL2021000296A1 (es)
CO (1) CO2021001217A2 (es)
EA (1) EA202190462A1 (es)
IL (1) IL280650A (es)
MX (1) MX2021001565A (es)
PE (1) PE20211068A1 (es)
SG (1) SG11202101174RA (es)
TW (1) TW202019415A (es)
WO (1) WO2020033520A1 (es)

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Publication number Priority date Publication date Assignee Title
CN112566916B (zh) 2018-08-08 2023-10-20 百时美施贵宝公司 作为pad4抑制剂的经取代的噻吩并吡咯
JP2021534108A (ja) 2018-08-08 2021-12-09 ブリストル−マイヤーズ スクイブ カンパニーBristol−Myers Squibb Company Ｐａｄ酵素のインドールおよびアザインドール阻害剤
CR20220550A (es) * 2020-04-30 2022-12-15 Gilead Sciences Inc Inhibidores macrocíclicos de las peptidilarginina deiminasas
CN111943947B (zh) * 2020-07-24 2021-04-30 重庆文理学院 1H-吡咯[2,3-b]吡啶衍生物及其合成方法与应用
US11878965B2 (en) 2020-12-22 2024-01-23 Gilead Sciences, Inc. Inhibitors of peptidylarginine deiminases
US20220227787A1 (en) * 2020-12-22 2022-07-21 Gilead Sciences, Inc. Inhibitors of peptidylarginine deiminases

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CA2879341C (en) * 2012-07-26 2019-06-11 Glaxo Group Limited 2- (azaindol-2-yl) benzimidazoles as pad4 inhibitors
EP3298003B1 (en) * 2015-05-21 2023-04-19 GlaxoSmithKline Intellectual Property Development Limited Benzoimidazole derivatives as pad4 inhibitors
AR107030A1 (es) * 2015-12-09 2018-03-14 Padlock Therapeutics Inc Inhibidores aza-bencimidazol de pad4
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PT3697785T (pt) 2017-10-18 2023-04-03 Jubilant Epipad LLC Compostos de imidazopiridina como inibidores de pad
WO2020033514A1 (en) 2018-08-08 2020-02-13 Bristol-Myers Squibb Company Benzimidazole inhibitors of pad enzymes
JP2021534108A (ja) 2018-08-08 2021-12-09 ブリストル−マイヤーズ スクイブ カンパニーBristol−Myers Squibb Company Ｐａｄ酵素のインドールおよびアザインドール阻害剤
CN112566916B (zh) 2018-08-08 2023-10-20 百时美施贵宝公司 作为pad4抑制剂的经取代的噻吩并吡咯
KR20210042932A (ko) 2018-08-08 2021-04-20 브리스톨-마이어스 스큅 컴퍼니 Pad4 억제제로서의 치환된 벤즈이미다졸

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JP2021534108A (ja) 2021-12-09
SG11202101174RA (en) 2021-03-30
CL2021000296A1 (es) 2021-06-25
WO2020033520A1 (en) 2020-02-13
KR20210042934A (ko) 2021-04-20
BR112021002091A2 (pt) 2021-05-04
IL280650A (en) 2021-03-25
US11524959B1 (en) 2022-12-13
MX2021001565A (es) 2021-04-19
EA202190462A1 (ru) 2021-06-03
CO2021001217A2 (es) 2021-02-26
CA3108791A1 (en) 2020-02-13
CN112805067A (zh) 2021-05-14
TW202019415A (zh) 2020-06-01
PE20211068A1 (es) 2021-06-09
EP3833440A1 (en) 2021-06-16
AU2019319835A1 (en) 2021-03-25

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