CA2986199C - Benzoimidazole derivatives as pad4 inhibitors - Google Patents

Benzoimidazole derivatives as pad4 inhibitors Download PDF

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Publication number
CA2986199C
CA2986199C CA2986199A CA2986199A CA2986199C CA 2986199 C CA2986199 C CA 2986199C CA 2986199 A CA2986199 A CA 2986199A CA 2986199 A CA2986199 A CA 2986199A CA 2986199 C CA2986199 C CA 2986199C
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Prior art keywords
methyl
mmol
indo1
compound
ethyl
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CA2986199A
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English (en)
French (fr)
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CA2986199A1 (en
Inventor
Dominique AMANS
Stephen John Atkinson
Michael David Barker
Matthew Campbell
Hawa Diallo
Clement Douault
Neil Stuart Garton
John Liddle
Jessica Fanny Renaux
Robert John Sheppard
Ann Louise Walker
Christopher Roland Wellaway
David Matthew Wilson
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GlaxoSmithKline Intellectual Property Development Ltd
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GlaxoSmithKline Intellectual Property Development Ltd
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Priority to CA3199601A priority Critical patent/CA3199601A1/en
Publication of CA2986199A1 publication Critical patent/CA2986199A1/en
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41Heterocyclic 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
    • A61K31/41641,3-Diazoles
    • A61K31/41841,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/14Heterocyclic 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic 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
    • A61K31/44Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445Non condensed piperidines, e.g. piperocaine
    • A61K31/4523Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/454Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • A61P11/06Antiasthmatics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/06Antipsoriatics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • A61P19/02Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/02Immunomodulators
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D498/00Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02Heterocyclic 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
    • C07D498/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D498/00Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02Heterocyclic 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
    • C07D498/06Peri-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Immunology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Rheumatology (AREA)
  • Pulmonology (AREA)
  • Epidemiology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Dermatology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pain & Pain Management (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Materials For Medical Uses (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
CA2986199A 2015-05-21 2016-05-19 Benzoimidazole derivatives as pad4 inhibitors Active CA2986199C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA3199601A CA3199601A1 (en) 2015-05-21 2016-05-19 Benzoimidazole derivatives as pad4 inhibitors

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201562164906P 2015-05-21 2015-05-21
US62/164,906 2015-05-21
PCT/IB2016/000761 WO2016185279A1 (en) 2015-05-21 2016-05-19 Benzoimidazole derivatives as pad4 inhibitors

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CA3199601A Division CA3199601A1 (en) 2015-05-21 2016-05-19 Benzoimidazole derivatives as pad4 inhibitors

Publications (2)

Publication Number Publication Date
CA2986199A1 CA2986199A1 (en) 2016-11-24
CA2986199C true CA2986199C (en) 2023-07-18

Family

ID=56235853

Family Applications (2)

Application Number Title Priority Date Filing Date
CA2986199A Active CA2986199C (en) 2015-05-21 2016-05-19 Benzoimidazole derivatives as pad4 inhibitors
CA3199601A Pending CA3199601A1 (en) 2015-05-21 2016-05-19 Benzoimidazole derivatives as pad4 inhibitors

Family Applications After (1)

Application Number Title Priority Date Filing Date
CA3199601A Pending CA3199601A1 (en) 2015-05-21 2016-05-19 Benzoimidazole derivatives as pad4 inhibitors

Country Status (15)

Country Link
US (2) US10407407B2 (enExample)
EP (1) EP3298003B1 (enExample)
JP (1) JP6703553B2 (enExample)
KR (1) KR20180005250A (enExample)
CN (1) CN107849015B (enExample)
AR (1) AR106863A1 (enExample)
AU (1) AU2016264958B2 (enExample)
BR (1) BR112017024678A2 (enExample)
CA (2) CA2986199C (enExample)
EA (1) EA033680B1 (enExample)
ES (1) ES2945314T3 (enExample)
IL (2) IL255666A (enExample)
MX (1) MX387321B (enExample)
TW (1) TW201706263A (enExample)
WO (1) WO2016185279A1 (enExample)

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AR107032A1 (es) 2015-12-09 2018-03-14 Padlock Therapeutics Inc Inhibidores bicíclicos de pad4
CA3015482A1 (en) * 2016-02-23 2017-08-31 Padlock Therapeutics, Inc. Heteroaryl inhibitors of pad4
WO2018022897A1 (en) * 2016-07-27 2018-02-01 Padlock Therapeutics, Inc. Covalent inhibitors of pad4
US11026937B2 (en) 2016-09-12 2021-06-08 Padlock Therapeutics, Inc. Heteroaryl inhibitors of PAD4
RU2764243C2 (ru) * 2017-09-22 2022-01-14 ДЖУБИЛАНТ ЭПИПЭД ЭлЭлСи Гетероциклические соединения в качестве ингибиторов PAD
AU2018352142B2 (en) * 2017-10-18 2022-08-25 Jubilant Epipad LLC Imidazo-pyridine compounds as PAD inhibitors
US11629135B2 (en) 2017-11-06 2023-04-18 Jubilant Prodell Llc Pyrimidine derivatives as inhibitors of PD1/PD-L1 activation
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MX2020009517A (es) 2018-03-13 2021-01-20 Jubilant Prodel LLC Compuestos biciclicos como inhibidores de la interaccion/activacio n de pdl/pd-l1.
ES2942319T3 (es) 2018-03-22 2023-05-31 Hoffmann La Roche Inhibidores de oxacina monoacilglicerol lipasa (MAGL)
MX2021001565A (es) * 2018-08-08 2021-04-19 Bristol Myers Squibb Co Inhibidores tipo indol y azaindol de enzimas peptidil arginina deiminasas (pad).
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MX2021001471A (es) * 2018-08-08 2021-04-28 Bristol Myers Squibb Co Benzimidazoles sustituidos como inhibidores de peptidil arginina deiminasa 4 (pad4).
JP7447080B2 (ja) 2018-08-08 2024-03-11 ブリストル-マイヤーズ スクイブ カンパニー Pad4阻害剤としての置換チエノピロール
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AU2019322161A1 (en) 2018-08-13 2020-11-12 F. Hoffmann-La Roche Ag New heterocyclic compounds as monoacylglycerol lipase inhibitors
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US20210094971A1 (en) 2019-09-09 2021-04-01 Hoffmann-La Roche Inc. Heterocyclic compounds
CN114269755A (zh) 2019-09-12 2022-04-01 豪夫迈·罗氏有限公司 作为magl抑制剂的4,4a,5,7,8,8a-六吡啶并[4,3-b][1,4]噁嗪-3-酮化合物
WO2021058443A1 (en) 2019-09-24 2021-04-01 F. Hoffmann-La Roche Ag Fluorescent probes for monoacylglycerol lipase (magl)
CR20220117A (es) 2019-09-24 2022-04-20 F Horrmann La Roche Ag Compuestos heterocíclicos
WO2021058445A1 (en) 2019-09-24 2021-04-01 F. Hoffmann-La Roche Ag New heterocyclic monoacylglycerol lipase (magl) inhibitors
TW202115083A (zh) * 2019-09-27 2021-04-16 大陸商南京藥捷安康生物科技有限公司 肽醯精胺酸脫亞胺酶抑制劑及其用途
WO2021158840A1 (en) * 2020-02-06 2021-08-12 Bristol-Myers Squibb Company Macrocyclic pad4 inhibitors useful as immunosuppressant
TW202140477A (zh) 2020-02-12 2021-11-01 美商必治妥美雅史谷比公司 雜環pad4抑制劑
WO2021174024A1 (en) 2020-02-28 2021-09-02 First Wave Bio, Inc. Methods of treating iatrogenic autoimmune colitis
WO2021222353A1 (en) * 2020-04-30 2021-11-04 Gilead Sciences, Inc. Macrocyclic inhibitors of peptidylarginine deiminases
US20220047569A1 (en) * 2020-08-12 2022-02-17 Jubilant Epipad LLC Method and compound for use, in treating and/or preventing netosis
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TW202233174A (zh) 2020-12-22 2022-09-01 美商基利科學股份有限公司 肽基精胺酸去亞胺酶之抑制劑
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Also Published As

Publication number Publication date
BR112017024678A2 (pt) 2018-07-31
MX2017014714A (es) 2018-01-25
MX387321B (es) 2025-03-11
EP3298003A1 (en) 2018-03-28
CA2986199A1 (en) 2016-11-24
EA033680B1 (ru) 2019-11-15
ES2945314T3 (es) 2023-06-30
IL255666A (en) 2018-01-31
IL278916A (en) 2021-01-31
EA201792517A1 (ru) 2018-04-30
JP6703553B2 (ja) 2020-06-03
WO2016185279A1 (en) 2016-11-24
US20200095227A1 (en) 2020-03-26
JP2018520105A (ja) 2018-07-26
AR106863A1 (es) 2018-02-28
AU2016264958A1 (en) 2017-12-07
TW201706263A (zh) 2017-02-16
US20180297983A1 (en) 2018-10-18
CN107849015B (zh) 2021-03-19
KR20180005250A (ko) 2018-01-15
US10815218B2 (en) 2020-10-27
CN107849015A (zh) 2018-03-27
EP3298003B1 (en) 2023-04-19
AU2016264958B2 (en) 2020-10-29
US10407407B2 (en) 2019-09-10
CA3199601A1 (en) 2016-11-24

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