CA2824599C - Arginase inhibitors and methods of use thereof - Google Patents

Arginase inhibitors and methods of use thereof Download PDF

Info

Publication number
CA2824599C
CA2824599C CA2824599A CA2824599A CA2824599C CA 2824599 C CA2824599 C CA 2824599C CA 2824599 A CA2824599 A CA 2824599A CA 2824599 A CA2824599 A CA 2824599A CA 2824599 C CA2824599 C CA 2824599C
Authority
CA
Canada
Prior art keywords
alkyl
amino
compound
aryl
borono
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.)
Active
Application number
CA2824599A
Other languages
English (en)
French (fr)
Other versions
CA2824599A1 (en
Inventor
Bruce Edward Tomczuk
Gary Lee Olson
Richard Scott Pottorf
Jane Wang
Bhaskara Rao Nallaganchu
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.)
AstraZeneca UK Ltd
Original Assignee
AstraZeneca UK Ltd
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 AstraZeneca UK Ltd filed Critical AstraZeneca UK Ltd
Publication of CA2824599A1 publication Critical patent/CA2824599A1/en
Application granted granted Critical
Publication of CA2824599C publication Critical patent/CA2824599C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02Boron compounds
    • C07F5/025Boronic and borinic acid compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/185Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19Carboxylic acids, e.g. valproic acid
    • A61K31/195Carboxylic acids, e.g. valproic acid having an amino group
    • 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/69Boron compounds
    • 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
    • A61P13/00Drugs for disorders of the urinary system
    • A61P13/12Drugs for disorders of the urinary system of the kidneys
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00Drugs for genital or sexual disorders; Contraceptives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00Drugs for genital or sexual disorders; Contraceptives
    • A61P15/06Antiabortive agents; Labour repressants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00Drugs for genital or sexual disorders; Contraceptives
    • A61P15/10Drugs for genital or sexual disorders; Contraceptives for impotence
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/02Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • 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
    • 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
    • A61P19/00Drugs for skeletal disorders
    • A61P19/04Drugs for skeletal disorders for non-specific disorders of the connective tissue
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00Drugs for disorders of the muscular or neuromuscular system
    • A61P21/02Muscle relaxants, e.g. for tetanus or cramps
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/02Drugs for disorders of the nervous system for peripheral neuropathies
    • 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
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04Antibacterial agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10Antimycotics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00Antiparasitic agents
    • 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
    • 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
    • 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
    • A61P7/00Drugs for disorders of the blood or the extracellular fluid
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00Drugs for disorders of the blood or the extracellular fluid
    • A61P7/08Plasma substitutes; Perfusion solutions; Dialytics or haemodialytics; Drugs for electrolytic or acid-base disorders, e.g. hypovolemic shock
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/08Vasodilators for multiple indications
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/12Antihypertensives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/14Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02Boron compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J43/00Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J43/003Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00Preparations for testing in vivo
    • A61K49/0004Screening or testing of compounds for diagnosis of disorders, assessment of conditions, e.g. renal clearance, gastric emptying, testing for diabetes, allergy, rheuma, pancreas functions
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/02Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
    • A61K51/04Organic compounds
    • A61K51/041Heterocyclic compounds
    • A61K51/044Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02ATECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Immunology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Epidemiology (AREA)
  • Hematology (AREA)
  • Pulmonology (AREA)
  • Diabetes (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Reproductive Health (AREA)
  • Endocrinology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Neurosurgery (AREA)
  • Dermatology (AREA)
  • Gynecology & Obstetrics (AREA)
  • Rheumatology (AREA)
  • Pain & Pain Management (AREA)
  • Pregnancy & Childbirth (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Transplantation (AREA)
CA2824599A 2010-12-31 2011-07-26 Arginase inhibitors and methods of use thereof Active CA2824599C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201061428894P 2010-12-31 2010-12-31
US61/428,894 2010-12-31
US201161450804P 2011-03-09 2011-03-09
US61/450,804 2011-03-09
PCT/US2011/045373 WO2012091757A1 (en) 2010-12-31 2011-07-26 Arginase inhibitors and methods of use thereof

Publications (2)

Publication Number Publication Date
CA2824599A1 CA2824599A1 (en) 2012-07-05
CA2824599C true CA2824599C (en) 2020-03-10

Family

ID=46380935

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2824599A Active CA2824599C (en) 2010-12-31 2011-07-26 Arginase inhibitors and methods of use thereof

Country Status (7)

Country Link
US (2) US8894970B2 (enExample)
EP (1) EP2658580A4 (enExample)
JP (4) JP2014506253A (enExample)
CN (3) CN104857005B (enExample)
CA (1) CA2824599C (enExample)
RU (2) RU2695650C2 (enExample)
WO (1) WO2012091757A1 (enExample)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2011242794B2 (en) 2010-04-22 2016-11-24 Mars, Incorporated Inhibitors of arginase and their therapeutic applications
ES2568680T3 (es) 2010-10-26 2016-05-03 Mars, Incorporated Boratos como inhibidores de arginasa
US9266908B2 (en) * 2011-10-19 2016-02-23 Mars, Incorporated Inhibitors of arginase and their therapeutic applications
CA2944903A1 (en) 2014-04-24 2015-10-29 Dana-Farber Cancer Institute, Inc. Tumor suppressor and oncogene biomarkers predictive of anti-immune checkpoint inhibitor response
PL410665A1 (pl) * 2014-12-29 2016-07-04 Oncoarendi Therapeutics Spółka Z Ograniczoną Odpowiedzialnością Inhibitory arginazy oraz ich zastosowania terapeutyczne
MX385315B (es) 2015-06-23 2025-03-14 Calithera Biosciences Inc Composiciones y metodos para inhibir actividad de arginasa.
CN108601767A (zh) * 2015-10-05 2018-09-28 卡利泰拉生物科技公司 用谷氨酰胺酶抑制剂和免疫肿瘤学药剂的组合疗法
CA3001964A1 (en) 2015-10-16 2017-04-20 Takeda Pharmaceutical Company Limited Method for producing heterocyclic compound
TWI710565B (zh) 2015-10-30 2020-11-21 美商卡利泰拉生物科技公司 用於抑制精胺酸酶活性之組合物及方法
PL417066A1 (pl) 2016-05-04 2017-11-06 Oncoarendi Therapeutics Spółka Z Ograniczoną Odpowiedzialnością Inhibitory arginazy oraz ich zastosowania terapeutyczne
CA3042878A1 (en) 2016-11-08 2018-05-17 Calithera Biosciences, Inc. Arginase inhibitor combination therapies
MX378460B (es) * 2016-12-22 2025-03-10 Calithera Biosciences Inc Composiciones y métodos para inhibir la actividad de la arginasa.
BR112019023582A2 (pt) 2017-05-12 2020-06-02 Calithera Biosciences Inc. Método de preparar (3r,4s)-3-acetamido-4-alil-n-(terc-butil)pirrolidina-3-carboxamida
CA3091365A1 (en) 2018-02-17 2019-08-22 Astrazeneca Ab Arginase inhibitors and methods of use thereof
EA202092086A1 (ru) 2018-03-05 2021-02-09 Аркус Байосайенсиз, Инк. Ингибиторы аргиназы
WO2019177873A1 (en) * 2018-03-13 2019-09-19 Merck Sharp & Dohme Corp. Arginase inhibitors and methods of use
PL3774843T3 (pl) 2018-03-29 2022-11-14 Molecure Sa Dipeptydowe pochodne piperydyny
CN111770756B (zh) * 2018-04-27 2023-03-31 四川科伦博泰生物医药股份有限公司 非天然氨基酸类衍生物、包含其的药物组合物及其制备方法和用途
US11274111B2 (en) 2018-06-20 2022-03-15 Merck Sharp & Dohme Corp. Arginase inhibitors and methods of use
AU2019379808C1 (en) 2018-11-16 2024-01-25 Arcus Biosciences, Inc. Inhibitors of ARG1 and/or ARG2
WO2020131598A1 (en) 2018-12-18 2020-06-25 Merck Sharp & Dohme Corp. Arginase inhibitors and methods of use
JP7579324B2 (ja) * 2019-07-23 2024-11-07 アストラゼネカ・アクチエボラーグ アルギナーゼ阻害剤及びその使用方法
US20230149521A1 (en) * 2020-04-17 2023-05-18 Bio-Cancer Treatment International Limited Methods of treating viral infections using arginase
TW202228720A (zh) 2020-12-22 2022-08-01 波蘭商昂科艾倫迪治療法股份公司 精胺酸酶抑制劑及其使用方法
US20240298987A1 (en) * 2021-06-23 2024-09-12 Yale University Compounds For Molecular Imaging of Collagen Turnover and Methods Using Same

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4477391A (en) 1981-08-14 1984-10-16 Collins James F Amino acid isomers, their production and their medicinal use
US5792769A (en) * 1995-09-29 1998-08-11 3-Dimensional Pharmaceuticals, Inc. Guanidino protease inhibitors
JP2000503010A (ja) * 1995-12-29 2000-03-14 スリー―ダイメンショナル・ファーマスーティカルス・インコーポレーテッド アミジノプロテアーゼ阻害剤
ES2273365T3 (es) * 1996-03-29 2007-05-01 Ortho-Mcneil Pharmaceutical, Inc. Amidinohidrazonas utiles como inhibidores de proteasa.
TW499412B (en) * 1996-11-26 2002-08-21 Dimensional Pharm Inc Aminoguanidines and alkoxyguanidines as protease inhibitors
EP1049660A1 (en) * 1997-10-10 2000-11-08 The Trustees Of The University Of Pennsylvania Compositions and methods for inhibiting arginase activity
ATE344246T1 (de) * 1997-11-26 2006-11-15 Ortho Mcneil Pharm Inc Heteroaryl aminoguanidin- und alkoxyguanidinderivate und ihre verwendung als proteasehemmer
US6344486B1 (en) * 1998-04-03 2002-02-05 3-Dimensional Pharmaceuticals, Inc. Benzamide and sulfonamide substituted aminoguanidines and alkoxyguanidines as protease inhibitors
IL139162A0 (en) * 1998-04-24 2001-11-25 Dimensional Pharm Inc Amidinohydrazone, alkoxyguanidine and aminoguanidine derivatives, processes for the preparation thereof and pharmaceutical compositions containing the same
EP1086122B1 (en) * 1998-06-11 2005-08-24 Johnson & Johnson Pharmaceutical Research & Development, L.L.C. Pyrazinone protease inhibitors
US6344484B1 (en) * 1999-02-12 2002-02-05 3-Dimensional Pharmaceuticals, Inc. Tyrosine alkoxyguanidines as integrin inhibitors
JP2003501352A (ja) * 1999-05-27 2003-01-14 3−ディメンショナル ファーマシューティカルズ, インコーポレイテッド プロテアーゼ阻害剤としてのオキサザ複素環
EP1303510A2 (en) * 2000-07-17 2003-04-23 3-Dimensional Pharmaceuticals, Inc. Cyclic oxyguanidine pyrazinones as protease inhibitors
US6635637B2 (en) * 2000-08-04 2003-10-21 Dimensional Pharmaceuticals, Inc. Cyclic oxyguanidine protease inhibitors
UA75093C2 (en) * 2000-10-06 2006-03-15 Dimensional Pharm Inc Aminopyridinyl-,aminoguanidinyl-, and alkoxyguanidinesubstituted phenylsubstituted phenylacetamides as protease inhibitors
US20040057926A1 (en) * 2002-03-12 2004-03-25 Lsu Medical Center Modulation of the immune response through the manipulation of arginine levels
US20050176651A1 (en) * 2002-09-09 2005-08-11 Trigen Limited Peptide boronic acids useful in making salts thereof
GB0405267D0 (en) * 2004-03-09 2004-04-21 Trigen Ltd Compounds
EP1863431A1 (en) * 2005-03-18 2007-12-12 L'Oréal Hair and/or eyelash care composition containing aminexil in combination with an agent for promoting the no production and uses thereof
CN101932599A (zh) * 2005-11-10 2010-12-29 阿波罗生命科学有限公司 分子及其嵌合分子
HUE046932T2 (hu) 2009-01-26 2020-04-28 Univ Pennsylvania Argináz inhibitorok és felhasználási eljárások
AU2011242794B2 (en) 2010-04-22 2016-11-24 Mars, Incorporated Inhibitors of arginase and their therapeutic applications

Also Published As

Publication number Publication date
US20120171116A1 (en) 2012-07-05
RU2695650C2 (ru) 2019-07-25
CN110123820B (zh) 2022-05-31
RU2019121905A (ru) 2019-09-03
JP6442629B2 (ja) 2018-12-19
CN104857005B (zh) 2019-04-26
EP2658580A1 (en) 2013-11-06
JP2018083833A (ja) 2018-05-31
US8894970B2 (en) 2014-11-25
CN110123820A (zh) 2019-08-16
WO2012091757A1 (en) 2012-07-05
JP2019052161A (ja) 2019-04-04
CA2824599A1 (en) 2012-07-05
CN103402549A (zh) 2013-11-20
US20160039847A1 (en) 2016-02-11
JP2016117735A (ja) 2016-06-30
EP2658580A4 (en) 2014-07-23
RU2013145548A (ru) 2015-04-20
JP2014506253A (ja) 2014-03-13
JP6724115B2 (ja) 2020-07-15
US9447122B2 (en) 2016-09-20
CN104857005A (zh) 2015-08-26
HK1213769A1 (zh) 2016-07-15

Similar Documents

Publication Publication Date Title
CA2824599C (en) Arginase inhibitors and methods of use thereof
JP6177832B2 (ja) アルギナーゼ阻害剤および使用方法
AU2013296627C1 (en) Deuterated ibrutinib
CA3041942A1 (en) Amino pyrazolopyrimidine compound used as neurotrophic factor tyrosine kinase receptor inhibitor
WO2019218904A1 (zh) 非天然氨基酸类衍生物、其制备方法及用途
AU2010206535B2 (en) Arginase inhibitors and methods of use
HK40012747B (en) Arginase inhibitors and methods of use thereof
HK40012747A (en) Arginase inhibitors and methods of use thereof
HK1213769B (zh) 精氨酸酶抑制剂及其使用方法
HK1164831B (en) Arginase inhibitors and methods of use
HK1164831A (en) Arginase inhibitors and methods of use
JP2018002669A (ja) グルタチオンs−トランスフェラーゼ阻害剤

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20160719