CA2860142C - Alpha-amino boronic acid derivatives, selective immunoproteasome inhibitors - Google Patents

Alpha-amino boronic acid derivatives, selective immunoproteasome inhibitors Download PDF

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Publication number
CA2860142C
CA2860142C CA2860142A CA2860142A CA2860142C CA 2860142 C CA2860142 C CA 2860142C CA 2860142 A CA2860142 A CA 2860142A CA 2860142 A CA2860142 A CA 2860142A CA 2860142 C CA2860142 C CA 2860142C
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hal
phenyl
hplc
denotes
alkyl
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French (fr)
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CA2860142A1 (en
Inventor
Dominique Swinnen
Federica MORANDI
Stefano Crosignani
Jeyaprakashnarayanan SEENISAMY
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Ares Trading SA
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Ares Trading SA
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/025—Boronic and borinic acid compounds
    • 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
    • A61K31/69—Boron compounds
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • 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
    • 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
    • A61P37/02—Immunomodulators
    • 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
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Immunology (AREA)
  • Epidemiology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pulmonology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Rheumatology (AREA)
  • Neurology (AREA)
  • Dermatology (AREA)
  • Urology & Nephrology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Vascular Medicine (AREA)
  • Pain & Pain Management (AREA)
  • Transplantation (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Oncology (AREA)
  • Hematology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CA2860142A 2011-12-22 2012-12-21 Alpha-amino boronic acid derivatives, selective immunoproteasome inhibitors Active CA2860142C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201161579076P 2011-12-22 2011-12-22
US61/579,076 2011-12-22
EP11195107 2011-12-22
EP11195107.5 2011-12-22
PCT/EP2012/076595 WO2013092979A1 (en) 2011-12-22 2012-12-21 Alpha-amino boronic acid derivatives, selective immunoproteasome inhibitors

Publications (2)

Publication Number Publication Date
CA2860142A1 CA2860142A1 (en) 2013-06-27
CA2860142C true CA2860142C (en) 2020-10-27

Family

ID=48667763

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2860142A Active CA2860142C (en) 2011-12-22 2012-12-21 Alpha-amino boronic acid derivatives, selective immunoproteasome inhibitors

Country Status (15)

Country Link
US (1) US9688702B2 (enExample)
EP (1) EP2793900B1 (enExample)
JP (1) JP6129203B2 (enExample)
KR (1) KR20140114391A (enExample)
CN (1) CN104321060B (enExample)
AU (1) AU2012356890B2 (enExample)
BR (1) BR112014015363A8 (enExample)
CA (1) CA2860142C (enExample)
EA (1) EA201400735A1 (enExample)
ES (1) ES2699267T3 (enExample)
HK (1) HK1206261A1 (enExample)
IL (1) IL233200A (enExample)
MX (1) MX352652B (enExample)
SG (2) SG10201605152SA (enExample)
WO (1) WO2013092979A1 (enExample)

Families Citing this family (53)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL3412676T3 (pl) 2010-08-10 2021-04-06 Melinta Therapeutics, Inc. Cykliczne pochodne estrowe kwasu boronowego, sposób otrzymywania oraz ich zastosowania terapeutyczne
WO2013033461A1 (en) 2011-08-31 2013-03-07 Rempex Pharmaceuticals, Inc. Heterocyclic boronic acid ester derivatives and therapeutic uses thereof
US9156858B2 (en) 2012-05-23 2015-10-13 Rempex Pharmaceuticals, Inc. Boronic acid derivatives and therapeutic uses thereof
US10561675B2 (en) 2012-06-06 2020-02-18 Rempex Pharmaceuticals, Inc. Cyclic boronic acid ester derivatives and therapeutic uses thereof
BR112015012909A2 (pt) * 2012-12-03 2017-07-11 Hoffmann La Roche compostos de ácido borônico de triazol substituído
PL2928898T3 (pl) 2012-12-07 2021-10-25 VenatoRx Pharmaceuticals, Inc. Inhibitory beta-laktamaz
US9101638B2 (en) 2013-01-04 2015-08-11 Rempex Pharmaceuticals, Inc. Boronic acid derivatives and therapeutic uses thereof
EP2941246A4 (en) 2013-01-04 2016-12-21 Rempex Pharmaceuticals Inc BORONIC ACID DERIVATIVES AND THEIR THERAPEUTIC USES
KR20150103270A (ko) * 2013-01-04 2015-09-09 렘펙스 파머수티클스 인코퍼레이티드 보론산 유도체 및 그의 치료적 용도
US9241947B2 (en) 2013-01-04 2016-01-26 Rempex Pharmaceuticals, Inc. Boronic acid derivatives and therapeutic uses thereof
ES2730013T3 (es) 2013-01-10 2019-11-07 Venatorx Pharmaceuticals Inc Inhibidores de betalactamasa
US9944658B2 (en) 2013-03-14 2018-04-17 VenatoRx Pharmaceuticals, Inc. Beta-lactamase inhibitors
WO2015106200A2 (en) 2014-01-10 2015-07-16 Cornell University Dipeptides as inhibitors of human immunoproteasomes
US9687497B1 (en) 2014-05-05 2017-06-27 Rempex Pharmaceuticals, Inc. Salts and polymorphs of cyclic boronic acid ester derivatives and therapeutic uses thereof
EP3140310B1 (en) 2014-05-05 2019-08-07 Rempex Pharmaceuticals, Inc. Synthesis of boronate salts and uses thereof
AU2015264418A1 (en) 2014-05-19 2016-11-10 Rempex Pharmaceuticals, Inc. Boronic acid derivatives and therapeutic uses thereof
ES2874579T3 (es) 2014-06-11 2021-11-05 Venatorx Pharmaceuticals Inc Inhibidores de betalactamasa
US10206937B2 (en) 2014-07-01 2019-02-19 Qpex Biopharma, Inc. Boronic acid derivatives and therapeutic uses thereof
US11202817B2 (en) 2014-08-18 2021-12-21 Cornell University Dipeptidomimetics as inhibitors of human immunoproteasomes
ES2761774T3 (es) 2014-10-01 2020-05-21 Merck Patent Gmbh Derivados del ácido borónico
MX2017004037A (es) * 2014-10-01 2017-07-04 Merck Patent Gmbh Derivados de acido boronico.
SG11201702623TA (en) * 2014-10-01 2017-04-27 Merck Patent Gmbh Boronic acid derivatives
WO2016050356A1 (en) * 2014-10-01 2016-04-07 Merck Patent Gmbh Boronic acid derivatives
WO2016081297A1 (en) 2014-11-18 2016-05-26 Rempex Pharmaceuticals, Inc. Cyclic boronic acid ester derivatives and therapeutic uses thereof
US20180051041A1 (en) 2015-03-17 2018-02-22 Rempex Pharmaceuticals, Inc. Boronic acid derivatives and therapeutic uses thereof
CN108472284A (zh) 2015-09-11 2018-08-31 维纳拓尔斯制药公司 β-内酰胺酶抑制剂
EP3362754B1 (en) 2015-10-15 2021-12-22 Cornell University Proteasome inhibitors and uses thereof
WO2017100537A1 (en) 2015-12-10 2017-06-15 VenatoRx Pharmaceuticals, Inc. Beta-lactamase inhibitors
CN107151255A (zh) * 2016-03-06 2017-09-12 复旦大学 硼酸类化合物及其制备方法和用途
MY196909A (en) 2016-06-30 2023-05-09 Qpex Biopharma Inc Boronic acid derivatives and therapeutic uses thereof
EP3630782A4 (en) 2017-05-26 2021-03-03 Venatorx Pharmaceuticals, Inc. Penicillin-binding protein inhibitors
US11267826B2 (en) 2017-05-26 2022-03-08 VenatoRx Pharmaceuticals, Inc. Penicillin-binding protein inhibitors
CA3073611A1 (en) 2017-08-24 2019-02-28 Merck Patent Gmbh Boronic acid derivatives
EP3694864B1 (en) 2017-10-11 2025-03-05 Qpex Biopharma, Inc. Boronic acid derivatives and synthesis thereof
US11203613B2 (en) 2017-10-11 2021-12-21 Cornell University Peptidomimetic proteasome inhibitors
CN107556336A (zh) * 2017-10-16 2018-01-09 康化（上海）新药研发有限公司 一种呋喃‑2‑甲烷基硼酸频哪醇酯的合成方法
CN111491938B (zh) 2017-11-16 2024-05-24 普林斯匹亚生物制药公司 免疫蛋白酶体抑制剂
PL3710457T3 (pl) 2017-11-16 2023-02-20 Principia Biopharma Inc. Inhibitory immunoproteasomu
CN108130370B (zh) * 2018-01-05 2020-11-17 武汉惠康达科技有限公司 Psmb8及其抑制剂在制备治疗脂肪肝及其相关疾病药物中的应用
AU2019256351B2 (en) 2018-04-20 2024-02-29 Qpex Biopharma, Inc. Boronic acid derivatives and therapeutic uses thereof
EP3802551A4 (en) 2018-05-25 2022-03-02 Venatorx Pharmaceuticals, Inc. Penicillin-binding protein inhibitors
IL280376B2 (en) 2018-07-26 2024-08-01 Merck Patent Gmbh Boronic acid derivatives, their preparation and pharmaceutical compositions containing them
EP3886798B1 (en) 2018-11-29 2026-01-28 Venatorx Pharmaceuticals, Inc. Combination compositions comprising a beta-lactamase inhibitor and uses thereof
CN113135944A (zh) * 2020-01-19 2021-07-20 首药控股(北京)有限公司 硼酸衍生物
US12552815B2 (en) 2020-05-05 2026-02-17 Qpex Biopharma, Inc. Boronic acid derivatives and synthesis, polymorphic forms, and therapeutic uses thereof
CN114075227B (zh) * 2020-08-19 2023-07-04 北京嵩润医药科技有限责任公司 吡唑硼酸类化合物、包含其的药物组合物及它们的用途
WO2022187362A1 (en) * 2021-03-02 2022-09-09 Case Western Reserve University Β-lactamase inhibitors and uses thereof
JP7758028B2 (ja) * 2021-03-05 2025-10-22 Ａｇｃ株式会社 化合物、化合物の製造方法及び表面処理剤の製造方法
WO2023006863A1 (en) 2021-07-29 2023-02-02 Merck Patent Gmbh Novel crystalline forms of [(1r)-2-(1-benzofuran-3-yl)-1-{[(1s,2r,4r)-7- oxabicyclo[2.2.1]heptan-2-yl]formamido}ethyl]boronic acid, adducts thereof, and processes to obtain
KR20240090392A (ko) * 2021-10-14 2024-06-21 쇼우야오 홀딩스 (베이징) 코., 엘티디. 보론산 유도체
CN117003776A (zh) * 2022-04-29 2023-11-07 科辉智药生物科技(深圳)有限公司 一种硼酸类蛋白酶体抑制剂及其用途
WO2023232830A1 (en) 2022-06-02 2023-12-07 Merck Patent Gmbh Boronic acid adducts
TW202529745A (zh) 2023-11-21 2025-08-01 美商維納拓爾斯製藥公司 經口遞送之β-內醯胺酶抑制劑之檸檬酸鹽配位錯合物及其用途

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL111175A0 (en) 1993-10-07 1994-12-29 Du Pont Merck Pharma Electrophilic peptide analogs as inhibitors of trypsin-like serine proteases and pharmaceutical compositions containing them
US7271186B1 (en) * 2002-12-09 2007-09-18 Northwestern University Nanomolar β-lactamase inhibitors
US7332343B2 (en) 2004-01-16 2008-02-19 Board Of Regents, The University Of Texas System Determining enantiomeric excess using indicator-displacement assays
RS53259B (sr) 2004-03-30 2014-08-29 Millennium Pharmaceuticals Inc. Sinteza bortezomiba
US7855206B2 (en) 2006-11-14 2010-12-21 Merck Sharp & Dohme Corp. Tricyclic heteroaromatic compounds as dipeptidyl peptidase-IV inhibitors for the treatment or prevention of diabetes
EP2178888B1 (en) * 2007-08-06 2012-07-04 Millennium Pharmaceuticals, Inc. Proteasome inhibitors
JP5600595B2 (ja) * 2007-10-16 2014-10-01 ミレニアム ファーマシューティカルズ， インコーポレイテッド プロテアソーム阻害剤
CN101983203A (zh) * 2007-11-13 2011-03-02 诺瓦提斯国际药物有限公司 β-内酰胺酶抑制剂
AR075090A1 (es) * 2008-09-29 2011-03-09 Millennium Pharm Inc Derivados de acido 1-amino-2-ciclobutiletilboronico inhibidores de proteosoma,utiles como agentes anticancerigenos, y composiciones farmaceuticas que los comprenden.
JP5933523B2 (ja) * 2010-03-31 2016-06-08 ミレニアム ファーマシューティカルズ， インコーポレイテッドＭｉｌｌｅｎｎｉｕｍ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ， Ｉｎｃ． １−アミノ−２−シクロプロピルエチルボロン酸の誘導体
US8507494B2 (en) 2010-04-30 2013-08-13 Merck Sharp & Dohme Corp. Heterocyclic quinolizine derived M1 receptor positive allosteric modulators

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IL233200A0 (en) 2014-07-31
EP2793900B1 (en) 2018-08-22
BR112014015363A2 (pt) 2017-06-13
EP2793900A1 (en) 2014-10-29
AU2012356890B2 (en) 2017-06-08
AU2012356890A1 (en) 2014-08-07
KR20140114391A (ko) 2014-09-26
MX352652B (es) 2017-12-04
EA201400735A1 (ru) 2015-04-30
US9688702B2 (en) 2017-06-27
SG10201605152SA (en) 2016-08-30
HK1206261A1 (en) 2016-01-08
CN104321060B (zh) 2018-08-07
BR112014015363A8 (pt) 2017-06-13
SG11201403254QA (en) 2014-07-30
CA2860142A1 (en) 2013-06-27
ES2699267T3 (es) 2019-02-08
CN104321060A (zh) 2015-01-28
US20140364396A1 (en) 2014-12-11
JP6129203B2 (ja) 2017-05-17
IL233200A (en) 2017-08-31
MX2014007362A (es) 2014-08-01
WO2013092979A1 (en) 2013-06-27
JP2015502387A (ja) 2015-01-22

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