CA3236104A1 - Piperidinyl indole derivatives, preparation methods and medicinal uses thereof - Google Patents

Piperidinyl indole derivatives, preparation methods and medicinal uses thereof Download PDF

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Publication number
CA3236104A1
CA3236104A1 CA3236104A CA3236104A CA3236104A1 CA 3236104 A1 CA3236104 A1 CA 3236104A1 CA 3236104 A CA3236104 A CA 3236104A CA 3236104 A CA3236104 A CA 3236104A CA 3236104 A1 CA3236104 A1 CA 3236104A1
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CA
Canada
Prior art keywords
alkyl
alkoxy
halogen
haloalkyl
hydrogen
Prior art date
Legal status (The legal status 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 status listed.)
Pending
Application number
CA3236104A
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English (en)
French (fr)
Inventor
Hugh Y. Zhu
Avinash KHANNA
Matthew KIER
Lisa A. De Meese
Wei Zhou
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Jiangsu Hansoh Pharmaceutical Group Co Ltd
Shanghai Hansoh Biomedical Co Ltd
Hansoh Bio LLC
Original Assignee
Jiangsu Hansoh Pharmaceutical Group Co Ltd
Shanghai Hansoh Biomedical Co Ltd
Hansoh Bio LLC
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
Application filed by Jiangsu Hansoh Pharmaceutical Group Co Ltd, Shanghai Hansoh Biomedical Co Ltd, Hansoh Bio LLC filed Critical Jiangsu Hansoh Pharmaceutical Group Co Ltd
Publication of CA3236104A1 publication Critical patent/CA3236104A1/en
Pending legal-status Critical Current

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    • 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
    • C07D403/10—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 linked by a carbon chain containing aromatic 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
    • C07D403/02—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
    • C07D403/06—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 linked by a carbon chain containing only aliphatic carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • 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
    • A61K31/40—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
    • A61K31/404—Indoles, e.g. pindolol
    • 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
    • A61K31/40—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
    • A61K31/404—Indoles, e.g. pindolol
    • A61K31/4045—Indole-alkylamines; Amides thereof, e.g. serotonin, melatonin
    • 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
    • A61K31/438—The ring being spiro-condensed with carbocyclic or heterocyclic ring 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
    • A61K31/4439—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
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/32—Oxygen atoms
    • 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
    • C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D401/10—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 linked by a carbon chain containing aromatic 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
    • C07D401/14—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
    • 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
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic 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
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic 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
    • C07D487/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems
    • C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/05—Isotopically modified compounds, e.g. labelled

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (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)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Immunology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicinal Preparation (AREA)
CA3236104A 2021-10-27 2022-10-27 Piperidinyl indole derivatives, preparation methods and medicinal uses thereof Pending CA3236104A1 (en)

Applications Claiming Priority (11)

Application Number Priority Date Filing Date Title
US202163263108P 2021-10-27 2021-10-27
US63/263,108 2021-10-27
US202263268655P 2022-02-28 2022-02-28
US63/268,655 2022-02-28
US202263362916P 2022-04-13 2022-04-13
US63/362,916 2022-04-13
US202263365029P 2022-05-20 2022-05-20
US63/365,029 2022-05-20
US202263366101P 2022-06-09 2022-06-09
US63/366,101 2022-06-09
PCT/CN2022/127975 WO2023072197A1 (en) 2021-10-27 2022-10-27 Piperidinyl indole derivatives, preparation methods and medicinal uses thereof

Publications (1)

Publication Number Publication Date
CA3236104A1 true CA3236104A1 (en) 2023-05-04

Family

ID=86160494

Family Applications (1)

Application Number Title Priority Date Filing Date
CA3236104A Pending CA3236104A1 (en) 2021-10-27 2022-10-27 Piperidinyl indole derivatives, preparation methods and medicinal uses thereof

Country Status (9)

Country Link
US (1) US20250243186A1 (https=)
EP (1) EP4423076A4 (https=)
JP (1) JP2024541929A (https=)
KR (1) KR20240090506A (https=)
AU (1) AU2022376760A1 (https=)
CA (1) CA3236104A1 (https=)
MX (1) MX2024004921A (https=)
TW (1) TW202334121A (https=)
WO (1) WO2023072197A1 (https=)

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CN120081822A (zh) * 2021-06-03 2025-06-03 诺瓦提斯药物公司 经取代的吲哚化合物及其使用方法
EP4389742A4 (en) * 2021-08-18 2026-01-14 Xizang Haisco Pharmaceutical Co Ltd HETEROAROMATIC CYCLE DERIVATIVE CONTAINING BENZO NITROGEN AND ITS USE IN MEDICINE
CA3247772A1 (en) * 2022-01-24 2023-07-27 Novartis Ag Spirocyclic piperidinyl derivatives as complement factor B inhibitors and their uses
CN119301114A (zh) * 2022-06-07 2025-01-10 正大天晴药业集团股份有限公司 双环取代的芳香羧酸类氘代化合物
WO2023246677A1 (zh) * 2022-06-20 2023-12-28 深圳信立泰药业股份有限公司 一种吲哚-苯基哌啶化合物及其制备方法与应用
TW202423426A (zh) * 2022-08-31 2024-06-16 美商奇努克醫療股份有限公司 經取代之吲哚化合物及其使用方法
IL320661A (en) * 2022-11-14 2025-07-01 Novartis Pharma Ag Solid forms of complement factor B inhibitors
TW202506657A (zh) * 2023-04-27 2025-02-16 大陸商上海翰森生物醫藥科技有限公司 一種哌啶基吲哚化合物的鹽及其製備方法
CN121889385A (zh) 2023-07-04 2026-04-17 希塔拉生物有限公司 作为因子b抑制剂的2-(1h-吲哚-4-基)甲基)2h-吲唑衍生物
IL325760A (en) 2023-07-04 2026-03-01 Sitala Bio Ltd History of 2-(1H-indol-4-yl)methyl)-isoindoline as factor B inhibitors
WO2025008517A1 (en) 2023-07-06 2025-01-09 Sitala Bio Ltd Indole derivatives with factor b inhibitory activity
WO2025008516A2 (en) 2023-07-06 2025-01-09 Sitala Bio Ltd Novel compounds
CN119371402A (zh) * 2023-07-26 2025-01-28 上海美悦生物科技发展有限公司 螺环烯基类或氮杂烯基类化合物及其药物组合物、制备方法和用途
TW202542111A (zh) * 2023-12-27 2025-11-01 大陸商海思科醫藥集團股份有限公司 一種苯基呱啶衍生物的製備方法
WO2025148628A1 (zh) * 2024-01-10 2025-07-17 河北以岭医药研究院有限公司 哌啶基吲哚衍生物及其制备方法和应用
WO2025172535A1 (en) 2024-02-15 2025-08-21 Sitala Bio Ltd Indole and benzimidazole compounds as factor b inhibitors
TW202543599A (zh) * 2024-03-08 2025-11-16 大陸商江蘇豪森藥業集團有限公司 一種多元螺環化合物的晶型、其製備方法和醫藥用途
WO2025185734A1 (zh) * 2024-03-08 2025-09-12 江苏豪森药业集团有限公司 一种多元螺环化合物的盐及其晶型、其制备方法和医药用途
WO2025252133A1 (zh) * 2024-06-07 2025-12-11 润尔眼科药物（广州）有限公司 一种含吲哚基团的化合物及其用途
WO2025256600A1 (zh) * 2024-06-12 2025-12-18 润尔眼科药物（广州）有限公司 一种杂环化合物及其用途

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JO3425B1 (ar) * 2013-07-15 2019-10-20 Novartis Ag مشتقات البابيريدينيل-اندول واستخدامها كعامل متمم لمثبطات b
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WO2022028507A1 (zh) * 2020-08-07 2022-02-10 上海美悦生物科技发展有限公司 一种杂环类化合物、其制备方法及用途
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EP4389742A4 (en) * 2021-08-18 2026-01-14 Xizang Haisco Pharmaceutical Co Ltd HETEROAROMATIC CYCLE DERIVATIVE CONTAINING BENZO NITROGEN AND ITS USE IN MEDICINE
CA3247772A1 (en) * 2022-01-24 2023-07-27 Novartis Ag Spirocyclic piperidinyl derivatives as complement factor B inhibitors and their uses

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KR20240090506A (ko) 2024-06-21
EP4423076A4 (en) 2026-01-07
US20250243186A1 (en) 2025-07-31
JP2024541929A (ja) 2024-11-13
MX2024004921A (es) 2024-06-19
EP4423076A1 (en) 2024-09-04
AU2022376760A1 (en) 2024-05-02
WO2023072197A1 (en) 2023-05-04
TW202334121A (zh) 2023-09-01

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