AU2021395816B2 - N-(imidazo[1,2-b]pyridazin-3-yl)-1-cyclohexyl-2h-indazole-5-carboxamide and n-(pyrazolo[1,5-a]pyrimidin-3-yl)-1-cyclohexyl-2h-indazole-5-carboxamide derivatives as irak4 inhibitors for the treatment of asthma - Google Patents

N-(imidazo[1,2-b]pyridazin-3-yl)-1-cyclohexyl-2h-indazole-5-carboxamide and n-(pyrazolo[1,5-a]pyrimidin-3-yl)-1-cyclohexyl-2h-indazole-5-carboxamide derivatives as irak4 inhibitors for the treatment of asthma Download PDF

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AU2021395816B2
AU2021395816B2 AU2021395816A AU2021395816A AU2021395816B2 AU 2021395816 B2 AU2021395816 B2 AU 2021395816B2 AU 2021395816 A AU2021395816 A AU 2021395816A AU 2021395816 A AU2021395816 A AU 2021395816A AU 2021395816 B2 AU2021395816 B2 AU 2021395816B2
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indazole
carboxamide
methoxy
cyclohexyl
mmol
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AU2021395816A1 (en
AU2021395816A9 (en
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Anna Ingrid Kristina Berggren
Hui-Fang Chang
Stefan Schiesser
Ina TERSTIEGE
Yafeng Xue
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AstraZeneca AB
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AstraZeneca AB
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04Ortho-condensed systems
    • 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
    • A61K31/495Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/50Pyridazines; Hydrogenated pyridazines
    • A61K31/5025Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
    • 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
    • A61K31/495Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • 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
    • 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
    • A61P35/00Antineoplastic agents
    • A61P35/02Antineoplastic agents specific for leukemia
    • 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
    • A61P37/06Immunosuppressants, e.g. drugs for graft rejection
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/08Antiallergic agents

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Immunology (AREA)
  • Pulmonology (AREA)
  • Dermatology (AREA)
  • Rheumatology (AREA)
  • Pain & Pain Management (AREA)
  • Transplantation (AREA)
  • Epidemiology (AREA)
  • Oncology (AREA)
  • Hematology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
AU2021395816A 2020-12-10 2021-12-09 N-(imidazo[1,2-b]pyridazin-3-yl)-1-cyclohexyl-2h-indazole-5-carboxamide and n-(pyrazolo[1,5-a]pyrimidin-3-yl)-1-cyclohexyl-2h-indazole-5-carboxamide derivatives as irak4 inhibitors for the treatment of asthma Active AU2021395816B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US202063199160P 2020-12-10 2020-12-10
US63/199,160 2020-12-10
PCT/EP2021/084916 WO2022122876A1 (en) 2020-12-10 2021-12-09 N-(imidazo[1,2-b]pyridazin-3-yl)-1-cyclohexyl-2h-indazole-5-carboxamide and n-(pyrazolo[1,5-a]pyrimidin-3-yl)-1-cyclohexyl-2h-indazole-5-carboxamide derivatives as irak4 inhibitors for the treatment of asthma

Publications (3)

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AU2021395816A1 AU2021395816A1 (en) 2023-07-13
AU2021395816B2 true AU2021395816B2 (en) 2024-04-04
AU2021395816A9 AU2021395816A9 (en) 2025-03-13

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US (3) US11866405B2 (enExample)
EP (1) EP4259632B1 (enExample)
JP (1) JP7749015B2 (enExample)
KR (1) KR20230118153A (enExample)
CN (1) CN116583285B (enExample)
AR (1) AR124303A1 (enExample)
AU (1) AU2021395816B2 (enExample)
CA (1) CA3203569A1 (enExample)
CL (1) CL2023001662A1 (enExample)
CO (1) CO2023007624A2 (enExample)
CR (1) CR20230264A (enExample)
DK (1) DK4259632T3 (enExample)
DO (1) DOP2023000119A (enExample)
EC (1) ECSP23050553A (enExample)
ES (1) ES2989489T3 (enExample)
FI (1) FI4259632T3 (enExample)
HR (1) HRP20241312T1 (enExample)
HU (1) HUE068584T2 (enExample)
IL (1) IL303356B1 (enExample)
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MA (1) MA62535B1 (enExample)
MX (1) MX2023006816A (enExample)
PE (1) PE20240684A1 (enExample)
PL (1) PL4259632T3 (enExample)
PT (1) PT4259632T (enExample)
RS (1) RS66095B1 (enExample)
SI (1) SI4259632T1 (enExample)
SM (1) SMT202400417T1 (enExample)
TW (1) TWI902994B (enExample)
UA (1) UA130417C2 (enExample)
UY (1) UY39561A (enExample)
WO (1) WO2022122876A1 (enExample)
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Families Citing this family (3)

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Publication number Priority date Publication date Assignee Title
JP7555519B2 (ja) * 2022-02-14 2024-09-24 アストラゼネカ・アクチエボラーグ Irak4阻害剤
US20250326757A1 (en) * 2022-05-26 2025-10-23 Astrazeneca Ab Solid forms of heterocyclylamides as irak4 inhibitors
TW202508568A (zh) 2023-04-07 2025-03-01 瑞典商阿斯特捷利康公司 Irak4蛋白水解靶向嵌合體

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110003219A (zh) 2010-07-13 2019-07-12 弗·哈夫曼-拉罗切有限公司 作为irak4调节剂的吡唑并[1,5a]嘧啶和噻吩并[3,2b]嘧啶衍生物
BR112013015460B1 (pt) 2010-12-20 2022-01-25 Merck Serono S.A. Derivados de indazolil triazol, kit, e composição farmacêutica
BG111378A (bg) * 2013-01-14 2015-01-30 Николай Цветков Субституирани индазолови производни като in-vitro mao-b инхибитори
DK2970139T3 (en) 2013-03-15 2018-08-13 Biomarin Pharm Inc HDAC inhibitors
EP3092226B1 (en) 2014-01-10 2019-03-13 Aurigene Discovery Technologies Limited Indazole compounds as irak4 inhibitors
DK3126330T3 (en) 2014-04-04 2019-04-23 Pfizer BICYCLE-FUSED HETEROARYL OR ARYL COMPOUNDS AND USE THEREOF AS IRAC4 INHIBITORS
JO3705B1 (ar) 2014-11-26 2021-01-31 Bayer Pharma AG إندازولات مستبدلة جديدة، عمليات لتحضيرها، مستحضرات دوائية تحتوي عليها واستخدامها في إنتاج أدوية
TW201701879A (zh) 2015-04-30 2017-01-16 拜耳製藥公司 Irak4抑制劑組合
CN108024971A (zh) 2015-07-15 2018-05-11 奥列基因发现技术有限公司 作为irak-4抑制剂的取代的氮杂化合物
JP2018524372A (ja) 2015-07-15 2018-08-30 アウリジーン ディスカバリー テクノロジーズ リミテッド Irak−4阻害剤としてのインダゾール及びアザインダゾール化合物
CN105503863A (zh) * 2015-12-11 2016-04-20 南京华威医药科技开发有限公司 新型抗肿瘤化合物
CN108473498B (zh) 2015-12-22 2021-11-02 豪夫迈·罗氏有限公司 作为IRAK4调节剂的吡唑并[1,5a]嘧啶衍生物
WO2017148902A1 (de) 2016-03-03 2017-09-08 Bayer Pharma Aktiengesellschaft Neue 2-substituierte indazole, verfahren zu ihrer herstellung, pharmazeutische präparate die diese enthalten, sowie deren verwendung zur herstellung von arzneimitteln
US10059708B2 (en) 2016-04-26 2018-08-28 Northwestern University Therapeutic targeting of the interleukin 1 receptor-associated kinase 4 (IRAK4) in leukemias characterized by rearrangements in the mixed lineage leukemia gene (MLL-r)
SG10202011653WA (en) 2016-06-01 2020-12-30 Bayer Pharma AG Use of 2-substituted indazoles for the treatment and prophylaxis of autoimmune diseases
EP3642201A1 (en) 2017-06-21 2020-04-29 H. Hoffnabb-La Roche Ag Isoindolinone derivatives as irak4 modulators
JP2020524692A (ja) 2017-06-21 2020-08-20 エフ.ホフマン−ラ ロシュ アーゲーF. Hoffmann−La Roche Aktiengesellschaft Irak4調節因子としてのベンゾフラン
US20230002361A1 (en) 2019-06-27 2023-01-05 Biogen Ma Inc. 2h-indazole derivatives and their use in the treatment of disease
JP7576581B2 (ja) 2019-06-27 2024-10-31 バイオジェン・エムエイ・インコーポレイテッド イミダゾ[1,2-a]ピリジニル誘導体及び疾患の処置におけるそれらの使用

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Zhai, W., et al, 2021. Discovery and optimization of a potent and selective indazolamine series of IRAK4 inhibitors. Bioorganic & Medicinal Chemistry Letters, 31, p.127686. *

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US20240182479A1 (en) 2024-06-06
ECSP23050553A (es) 2023-08-31
TWI902994B (zh) 2025-11-01
EP4259632A1 (en) 2023-10-18
CN116583285B (zh) 2026-03-24
PL4259632T3 (pl) 2024-12-16
PE20240684A1 (es) 2024-04-10
UA130417C2 (uk) 2026-02-11
US20260092069A1 (en) 2026-04-02
IL303356B1 (en) 2026-04-01
US20220185817A1 (en) 2022-06-16
MA62535B1 (fr) 2024-11-29
LT4259632T (lt) 2024-10-10
IL303356A (en) 2023-08-01
WO2022122876A1 (en) 2022-06-16
HUE068584T2 (hu) 2025-01-28
HRP20241312T1 (hr) 2024-12-20
AR124303A1 (es) 2023-03-15
US12448385B2 (en) 2025-10-21
UY39561A (es) 2022-06-30
CO2023007624A2 (es) 2023-06-30
DK4259632T3 (da) 2024-10-21
SMT202400417T1 (it) 2024-11-15
MX2023006816A (es) 2023-06-21
KR20230118153A (ko) 2023-08-10
EP4259632B1 (en) 2024-07-24
DOP2023000119A (es) 2023-07-09
CR20230264A (es) 2023-07-26
AU2021395816A1 (en) 2023-07-13
ZA202306848B (en) 2024-04-24
CA3203569A1 (en) 2022-06-16
FI4259632T3 (fi) 2024-10-24
JP7749015B2 (ja) 2025-10-03
RS66095B1 (sr) 2024-11-29
TW202237612A (zh) 2022-10-01
CN116583285A (zh) 2023-08-11
CL2023001662A1 (es) 2024-01-12
JP2023552838A (ja) 2023-12-19
US11866405B2 (en) 2024-01-09
SI4259632T1 (sl) 2024-12-31
PT4259632T (pt) 2024-10-24
AU2021395816A9 (en) 2025-03-13
ES2989489T3 (es) 2024-11-26

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