WO2023006019A1 - Inhibiteur de pd-l1 benzène polysubstitué, composition et utilisation associées - Google Patents

Inhibiteur de pd-l1 benzène polysubstitué, composition et utilisation associées Download PDF

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Publication number
WO2023006019A1
WO2023006019A1 PCT/CN2022/108538 CN2022108538W WO2023006019A1 WO 2023006019 A1 WO2023006019 A1 WO 2023006019A1 CN 2022108538 W CN2022108538 W CN 2022108538W WO 2023006019 A1 WO2023006019 A1 WO 2023006019A1
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Prior art keywords
methyl
compound
amino
benzo
difluoromethyl
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PCT/CN2022/108538
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English (en)
Chinese (zh)
Inventor
吴一哲
周星露
刘兴国
胡苗
朱建荣
Original Assignee
杭州和正医药有限公司
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Publication of WO2023006019A1 publication Critical patent/WO2023006019A1/fr

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    • 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
    • A61K31/41—Heterocyclic 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
    • A61K31/42—Oxazoles
    • A61K31/423—Oxazoles condensed with carbocyclic rings
    • 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
    • A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/4375—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
    • 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
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
    • 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
    • A61K31/495—Heterocyclic 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
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with 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
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    • 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
    • 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

Definitions

  • the object of the present invention is to provide a novel multi-substituted benzene compound or its stereoisomer or its stereoisomer mixture or a pharmaceutically acceptable salt thereof.
  • alkoxy refers to -O-alkyl, wherein alkyl is as defined above.
  • alkoxy include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy and tert-butoxy.
  • Alkoxy also includes substituted alkoxy, whose substituents can be halogen, amino, hydroxy, C 1 -C 6 alkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 alkoxy, C 1 -C 6 cycloalkyl, 3- to 10-membered heterocyclic group, C 6 -C 12 aryl, C 5 -C 14 heteroaryl.
  • salts of the compounds described in the present invention can be prepared by methods well known to those skilled in the art.
  • Described salt can be organic acid salt, inorganic acid salt etc., and described organic acid salt comprises citrate, fumarate, oxalate, malate, lactate, camphorsulfonate, p- Tosylate, methanesulfonate, etc.; the inorganic acid salts include hydrohalides, sulfates, phosphates, nitrates, etc.
  • a preparation comprising one or more of the compounds described in any of the above schemes.
  • the carrier includes conventional diluents, excipients, fillers, binders, wetting agents, disintegrants, absorption accelerators, surfactants, adsorption carriers, lubricants, etc. in the pharmaceutical field, and fragrances can also be added if necessary agents, sweeteners, etc.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Virology (AREA)
  • Immunology (AREA)
  • Oncology (AREA)
  • Pulmonology (AREA)
  • Epidemiology (AREA)
  • Communicable Diseases (AREA)
  • Molecular Biology (AREA)
  • Neurosurgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Hematology (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Dermatology (AREA)
  • Rheumatology (AREA)
  • Diabetes (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Biotechnology (AREA)
  • Transplantation (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

La présente invention concerne un inhibiteur de PD-L1 benzène polysubstitué, une composition et une utilisation associées. Le composé a une structure telle que représentée par la formule générale (I). L'inventeur de la présente invention a confirmé au moyen d'une expérience que le composé selon la présente invention a une forte activité de blocage PD-1/PD-L1 et une activité d'occupation PD-L1 significative, et peut inverser une fonction de cellule T inhibée par PD-L1. De plus, le composé selon la présente invention peut être absorbé par voie orale, a une bonne propriété pharmacocinétique, et a une bonne activité inhibitrice contre les tumeurs in vivo. Par conséquent, le composé selon la présente invention peut être utilisé, seul ou en combinaison avec d'autres médicaments dans le traitement de maladies, de troubles ou d'états pathologiques qui peuvent bénéficier de l'inhibition de l'activité de PD1 ou de PD-L1, comprenant des maladies infectieuses, des maladies immunitaires, des maladies inflammatoires et des cancers.
PCT/CN2022/108538 2021-07-28 2022-07-28 Inhibiteur de pd-l1 benzène polysubstitué, composition et utilisation associées WO2023006019A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN202110859819 2021-07-28
CN202110859819.3 2021-07-28

Publications (1)

Publication Number Publication Date
WO2023006019A1 true WO2023006019A1 (fr) 2023-02-02

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Application Number Title Priority Date Filing Date
PCT/CN2022/108538 WO2023006019A1 (fr) 2021-07-28 2022-07-28 Inhibiteur de pd-l1 benzène polysubstitué, composition et utilisation associées

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WO (1) WO2023006019A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110267953A (zh) * 2016-12-22 2019-09-20 因赛特公司 四氢咪唑并[4,5-c]吡啶衍生物作为pd-l1内在化诱导剂
CN110582493A (zh) * 2016-12-22 2019-12-17 因赛特公司 作为免疫调节剂的苯并噁唑衍生物
WO2020156323A1 (fr) * 2019-01-31 2020-08-06 Betta Pharmaceuticals Co., Ltd Immunomodulateurs, compositions et procédés associés
CN112135824A (zh) * 2018-03-30 2020-12-25 因赛特公司 作为免疫调节剂的杂环化合物

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110267953A (zh) * 2016-12-22 2019-09-20 因赛特公司 四氢咪唑并[4,5-c]吡啶衍生物作为pd-l1内在化诱导剂
CN110582493A (zh) * 2016-12-22 2019-12-17 因赛特公司 作为免疫调节剂的苯并噁唑衍生物
CN112135824A (zh) * 2018-03-30 2020-12-25 因赛特公司 作为免疫调节剂的杂环化合物
WO2020156323A1 (fr) * 2019-01-31 2020-08-06 Betta Pharmaceuticals Co., Ltd Immunomodulateurs, compositions et procédés associés

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