KR100939598B1 - 붕소산 에스테르와 산 화합물의 합성 - Google Patents

붕소산 에스테르와 산 화합물의 합성 Download PDF

Info

Publication number
KR100939598B1
KR100939598B1 KR1020067022780A KR20067022780A KR100939598B1 KR 100939598 B1 KR100939598 B1 KR 100939598B1 KR 1020067022780 A KR1020067022780 A KR 1020067022780A KR 20067022780 A KR20067022780 A KR 20067022780A KR 100939598 B1 KR100939598 B1 KR 100939598B1
Authority
KR
South Korea
Prior art keywords
group
formula
aliphatic
compound
water
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.)
Expired - Lifetime
Application number
KR1020067022780A
Other languages
English (en)
Korean (ko)
Other versions
KR20070007873A (ko
Inventor
아이. 프레져 픽커스길
존 비샵
크리스토프 코엘너
진-마르크 코메즈
아침 게이저
로버트 헤트
빈스 암모스카도
스테픈 뭉크
영 로
팡-팅 츄이
비탈란단드 알. 컬카르노
Original Assignee
밀레니엄 파머슈티컬스 인코퍼레이티드
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=34968044&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=KR100939598(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by 밀레니엄 파머슈티컬스 인코퍼레이티드 filed Critical 밀레니엄 파머슈티컬스 인코퍼레이티드
Publication of KR20070007873A publication Critical patent/KR20070007873A/ko
Application granted granted Critical
Publication of KR100939598B1 publication Critical patent/KR100939598B1/ko
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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
    • 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
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • A61P31/14Antivirals for RNA viruses
    • A61P31/18Antivirals for RNA viruses for HIV
    • 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
    • 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
    • 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
    • C07F5/04Esters of boric acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06Dipeptides
    • C07K5/06191Dipeptides containing heteroatoms different from O, S, or N
    • 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
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/55Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Immunology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Virology (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Transplantation (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • AIDS & HIV (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
KR1020067022780A 2004-03-30 2005-03-24 붕소산 에스테르와 산 화합물의 합성 Expired - Lifetime KR100939598B1 (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US55753504P 2004-03-30 2004-03-30
US60/557,535 2004-03-30

Publications (2)

Publication Number Publication Date
KR20070007873A KR20070007873A (ko) 2007-01-16
KR100939598B1 true KR100939598B1 (ko) 2010-02-01

Family

ID=34968044

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020067022780A Expired - Lifetime KR100939598B1 (ko) 2004-03-30 2005-03-24 붕소산 에스테르와 산 화합물의 합성

Country Status (41)

Country Link
US (14) US7714159B2 (https=)
EP (5) EP1756121B1 (https=)
JP (4) JP4558039B2 (https=)
KR (1) KR100939598B1 (https=)
CN (5) CN1960996B (https=)
AR (3) AR049374A1 (https=)
AT (1) ATE521612T1 (https=)
AU (1) AU2005230930B2 (https=)
BR (1) BRPI0509587A (https=)
CA (4) CA2859119A1 (https=)
CL (2) CL2010000350A1 (https=)
CR (1) CR8653A (https=)
CY (3) CY1112053T1 (https=)
DK (4) DK4008721T3 (https=)
DO (1) DOP2011000293A (https=)
EA (1) EA012927B1 (https=)
EC (1) ECSP066960A (https=)
ES (4) ES2899606T3 (https=)
FI (1) FI4008721T3 (https=)
HK (1) HK1246300A1 (https=)
HR (4) HRP20240307T3 (https=)
HU (2) HUE065769T2 (https=)
IL (3) IL178250A (https=)
LT (2) LT3385267T (https=)
ME (1) ME01975B (https=)
MX (1) MX367324B (https=)
MY (1) MY145427A (https=)
NL (3) NL1028639C2 (https=)
NO (4) NO338905B1 (https=)
NZ (3) NZ586824A (https=)
PE (3) PE20142402A1 (https=)
PL (4) PL1756121T3 (https=)
PT (4) PT2377869E (https=)
RS (4) RS51983B (https=)
SG (5) SG10201800972PA (https=)
SI (4) SI4008721T1 (https=)
TW (1) TWI386212B (https=)
UA (1) UA90108C2 (https=)
UY (3) UY28830A1 (https=)
WO (1) WO2005097809A2 (https=)
ZA (1) ZA200608689B (https=)

Families Citing this family (72)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6083903A (en) * 1994-10-28 2000-07-04 Leukosite, Inc. Boronic ester and acid compounds, synthesis and uses
ME01975B (me) 2004-03-30 2015-05-20 Millennium Pharm Inc Sinteza jedinjenja estra organoborne kiseline i organoborne kiseline
WO2008075376A1 (en) * 2006-12-18 2008-06-26 Natco Pharma Limited Polymorphic forms of bortezomib and process for their preparation
WO2009004350A1 (en) * 2007-07-03 2009-01-08 Pliva Hrvatska D.O.O. Methods for preparing bortezomib and intermediates used in its manufacture
PL2178888T3 (pl) 2007-08-06 2012-11-30 Millennium Pharm Inc Inhibitory proteasomów
EA034601B1 (ru) * 2007-08-06 2020-02-25 Милленниум Фармасьютикалз, Инк. Способ получения бороновых кислот
US7442830B1 (en) 2007-08-06 2008-10-28 Millenium Pharmaceuticals, Inc. Proteasome inhibitors
AU2016253697A1 (en) * 2007-08-06 2016-11-24 Millennium Pharmaceuticals, Inc. Proteasome inhibitors
US20110118274A1 (en) * 2007-08-23 2011-05-19 Cornell Research Foundation, Inc. Proteasome inhibitors and their use in treating pathogen infection and cancer
JP2010539183A (ja) * 2007-09-12 2010-12-16 ドクター・レディーズ・ラボラトリーズ・リミテッド ボルテゾミブおよびその生成のためのプロセス
US7838673B2 (en) 2007-10-16 2010-11-23 Millennium Pharmaceuticals, Inc. Proteasome inhibitors
EP2730579A1 (en) * 2008-06-17 2014-05-14 Millennium Pharmaceuticals, Inc. Boronate ester compounds and pharmaceutical compositions thereof
AU2013204874B2 (en) * 2008-09-29 2016-11-10 Millennium Pharmaceuticals, Inc. Derivatives of 1-amino-2-cyclobutylethylboronic acid
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.
EP2238973A1 (en) 2009-04-07 2010-10-13 Cephalon France Lyophilized preparations of proteasome inhibitors
CN101899062B (zh) * 2009-05-26 2015-04-15 上海威智医药科技有限公司 α-手性硼酸及硼酸酯的合成工艺
EP2280016A1 (en) 2009-07-27 2011-02-02 LEK Pharmaceuticals d.d. New synthetic route for the preparation of alpha-amino boronic esters via substituted alk-1-ynes
EP2443128B1 (en) 2009-06-19 2017-12-20 LEK Pharmaceuticals d.d. New synthetic route for the preparation of alpha-amino boronic esters
EP2270019A1 (en) 2009-06-19 2011-01-05 LEK Pharmaceuticals d.d. New synthetic route for the preparation of alpha-amino boronic esters
AU2010341530B2 (en) 2009-12-22 2016-03-10 Cephalon, Inc. Proteasome inhibitors and processes for their preparation, purification and use
US20110178287A1 (en) 2010-01-19 2011-07-21 Cerulean Pharma Inc. Cyclodextrin-based polymers for therapeutic delivery
EP2534159A1 (en) 2010-02-09 2012-12-19 Ranbaxy Laboratories Limited Process for the preparation of bortezomib
CN101781326B (zh) * 2010-02-11 2013-08-21 福建南方制药股份有限公司 一种制备手性氨基硼酸的中间体及其制备方法
WO2011107912A1 (en) 2010-03-04 2011-09-09 Ranbaxy Laboratories Limited Polymorphic forms of bortezomib
US8263578B2 (en) 2010-03-18 2012-09-11 Innopharma, Inc. Stable bortezomib formulations
AU2011227083B2 (en) * 2010-03-18 2013-07-18 Innopharma, Inc. Stable bortezomib formulations
MX2012011298A (es) 2010-03-31 2012-11-06 Millennium Pharm Inc Derivados del acido 1-amino-2-ciclopropiletilboronico.
CN101812026B (zh) * 2010-04-12 2013-08-28 亚邦医药股份有限公司 一种硼替佐米的合成方法
US20110300150A1 (en) 2010-05-18 2011-12-08 Scott Eliasof Compositions and methods for treatment of autoimmune and other disease
US8884009B2 (en) 2010-10-14 2014-11-11 Synthon Bv Process for making bortezomib and intermediates for the process
TW201309303A (zh) 2011-03-03 2013-03-01 Cephalon Inc 用於治療狼瘡的蛋白酶體抑制劑
CN102206188B (zh) * 2011-04-08 2013-02-27 苏州二叶制药有限公司 N-(吡嗪-2-基羰基)-l-苯丙氨酸的制备方法
US8497374B2 (en) 2011-05-12 2013-07-30 Scinopharm Taiwan, Ltd. Process for preparing and purifying bortezomib
CN102268029B (zh) * 2011-05-19 2013-10-09 苏州二叶制药有限公司 化合物(1s,2s,3r,5s)-蒎烷二醇-l-苯丙氨酸-l-亮氨酸硼酸酯的制备
WO2012177835A1 (en) 2011-06-22 2012-12-27 Cephalon, Inc. Proteasome inhibitors and processes for their preparation, purification and use
CN102351890B (zh) * 2011-09-30 2014-07-02 重庆泰濠制药有限公司 一种硼替佐米的合成方法
CN102492021B (zh) * 2011-12-13 2013-10-23 重庆泰濠制药有限公司 硼替佐米的制备工艺
SG11201403254QA (en) * 2011-12-22 2014-07-30 Ares Trading Sa Alpha-amino boronic acid derivatives, selective immunoproteasome inhibitors
CN103374026A (zh) * 2012-04-27 2013-10-30 重庆医药工业研究院有限责任公司 一种硼替佐米中间体的制备方法
CN103450331B (zh) * 2012-06-05 2016-05-25 山东新时代药业有限公司 一种硼替佐米的精制方法
CN104822688A (zh) * 2012-09-11 2015-08-05 西普拉有限公司 制备硼替佐米的方法
WO2014072985A1 (en) 2012-11-06 2014-05-15 Natco Pharma Limited Novel boronic acid derivatives as anti cancer agents
CA2891822A1 (en) 2012-11-16 2014-05-22 Shilpa Medicare Limited Crystalline bortezomib process
CN105026407B (zh) 2012-12-07 2017-09-08 维纳拓尔斯制药公司 β‑内酰胺酶抑制剂
CN103897027A (zh) * 2012-12-29 2014-07-02 曹亚英 关键中间体晶型,制备方法及其在硼替佐米合成中的运用
CN103897026A (zh) * 2012-12-29 2014-07-02 朱继东 硼替佐米关键中间体的晶型,制备方法及其运用
EP2943204B1 (en) 2013-01-10 2019-03-13 Venatorx Pharmaceuticals Inc Beta-lactamase inhibitors
CA2909519A1 (en) 2013-04-16 2014-10-23 Cipla Limited Process for the preparation of bortezomib mannitol ester
CN104211758B (zh) * 2013-05-29 2020-06-12 深圳翰宇药业股份有限公司 一种硼替佐米的制备方法
CN103497233B (zh) * 2013-09-30 2015-04-08 哈药集团技术中心 一种硼替佐米的制备方法
CN103554219A (zh) * 2013-10-01 2014-02-05 昆明贵研药业有限公司 一种制备硼替佐米的方法
KR101691353B1 (ko) * 2013-12-09 2016-12-30 주식회사 경보제약 보르테조밉의 제조방법 및 그의 신규 중간체
CN111116622A (zh) 2014-02-03 2020-05-08 俄亥俄州创新基金会 硼酸酯和其药物制剂
MA39964A (fr) 2014-05-20 2015-11-26 Millennium Pharm Inc Inhibiteurs du protéasome contenant du bore destinés à être utilisés après une thérapie contre le cancer primaire
PT3154989T (pt) 2014-06-11 2021-05-18 Venatorx Pharmaceuticals Inc Inibidores de beta-lactamase
JP6420629B2 (ja) * 2014-10-30 2018-11-07 ボーグワーナー インコーポレーテッド チェーンガイドおよびチェーンテンショナアーム
DE102015204151B4 (de) * 2015-03-09 2025-12-24 Adidas Ag Ball, insbesondere Fußball, und Verfahren zur Herstellung eines Balls
JP6223508B2 (ja) * 2016-06-27 2017-11-01 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Millennium Pharmaceuticals, Inc. プロテアソーム阻害剤
EP3494121B1 (en) 2016-08-04 2021-10-06 Venatorx Pharmaceuticals, Inc. Boron-containing compounds
CN110312727A (zh) * 2017-02-17 2019-10-08 费森尤斯卡比肿瘤学有限公司 一种改进的制备硼酸酯的方法
MA47743A (fr) 2017-03-06 2020-01-15 Venatorx Pharmaceuticals Inc Formes solides et compositions de combinaison comprenant un inhibiteur de bêta-lactamase et leurs utilisations
US11332485B2 (en) 2017-05-26 2022-05-17 VenatoRx Pharmaceuticals, Inc. Penicillin-binding protein inhibitors
EP3630783A4 (en) 2017-05-26 2021-03-03 Venatorx Pharmaceuticals, Inc. PENICILLIN-BINDING PROTEIN INHIBITORS
US11414437B2 (en) 2017-07-28 2022-08-16 Chengdu Origin Biotechnology Limited Company Borate compound, and synthesis method therefor and uses thereof
CN111065641A (zh) * 2017-09-02 2020-04-24 太阳制药工业有限公司 柠檬酸伊沙佐米的制备方法
EP3802551A4 (en) 2018-05-25 2022-03-02 Venatorx Pharmaceuticals, Inc. Penicillin-binding protein inhibitors
CN111187336B (zh) * 2018-11-14 2022-05-20 正大天晴药业集团股份有限公司 硼替佐米的精制方法
CN113382713A (zh) 2018-11-29 2021-09-10 维纳拓尔斯制药公司 包含β-内酰胺酶抑制剂的组合式组合物及其用途
US11964993B2 (en) 2021-07-03 2024-04-23 Shilpa Pharma Lifesciences Limited Crystalline bortezomib process
WO2025034812A2 (en) 2023-08-07 2025-02-13 Tae Life Sciences Llc Trifluoroborate (bf3) compositions for use in boron neutron capture therapy and methods thereof
WO2025080942A1 (en) * 2023-10-13 2025-04-17 The Brigham And Women’S Hospital, Inc. Proteasome inhibitors and methods of use thereof
CN120248757A (zh) * 2025-05-28 2025-07-04 滁州瑞达新能源材料有限公司 一种自清洁耐候的铝合金光伏组件边框及其制备方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4525309A (en) * 1983-03-15 1985-06-25 Washington State University Research Foundation, Inc. Lewis acid catalysis of the homologation of boronic esters with haloalkylmetal reagents
US6699835B2 (en) * 2001-01-25 2004-03-02 The United States Of America As Represented By The Department Of Health And Human Services Formulation of boronic acid compounds

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL31992A (en) * 1968-05-08 1973-07-30 American Cyanamid Co Synthetic thyrocalcitonins and method of making them
ZA794723B (en) * 1978-09-11 1980-08-27 Univ Miami Anti-hypertensive agents
US4499082A (en) * 1983-12-05 1985-02-12 E. I. Du Pont De Nemours And Company α-Aminoboronic acid peptides
US4537773A (en) 1983-12-05 1985-08-27 E. I. Du Pont De Nemours And Company α-Aminoboronic acid derivatives
ES8603405A1 (es) * 1985-04-22 1985-12-16 Inke Sa "procedimiento para la obtencion del ester benzilico de 1-(n-(1--etoxicarbonil-3-oxo-fenilpropil)-l-alanil)-l-prolina".
SE8506094D0 (sv) * 1985-12-20 1985-12-20 Astra Laekemedel Ab New antibacterial agents and intermediates therefor
US4701545A (en) * 1986-02-12 1987-10-20 Washington State University Research Foundation, Inc. Preparation of α,α-dihaloalkyl boronic esters
US5187157A (en) 1987-06-05 1993-02-16 Du Pont Merck Pharmaceutical Company Peptide boronic acid inhibitors of trypsin-like proteases
US5250720A (en) 1987-06-05 1993-10-05 The Dupont Merck Pharmaceutical Company Intermediates for preparing peptide boronic acid inhibitors of trypsin-like proteases
US5242904A (en) 1987-06-05 1993-09-07 The Dupont Merck Pharmaceutical Company Peptide boronic acid inhibitors of trypsin-like proteases
EP0315574A3 (de) 1987-11-05 1990-08-22 Hoechst Aktiengesellschaft Renin-Inhibitoren
US5106948A (en) * 1988-05-27 1992-04-21 Mao Foundation For Medical Education And Research Cytotoxic boronic acid peptide analogs
US6083903A (en) 1994-10-28 2000-07-04 Leukosite, Inc. Boronic ester and acid compounds, synthesis and uses
JPWO2003033507A1 (ja) 2001-10-12 2005-02-03 杏林製薬株式会社 ベンジルマロン酸誘導体およびそれを含有するプロテアソーム阻害薬
WO2003033506A1 (en) * 2001-10-12 2003-04-24 Kyorin Pharmaceutical Co., Ltd. Aminoborane acid derivative and proteasome inhibitory drug containing the same
ME01975B (me) 2004-03-30 2015-05-20 Millennium Pharm Inc Sinteza jedinjenja estra organoborne kiseline i organoborne kiseline
WO2009004350A1 (en) * 2007-07-03 2009-01-08 Pliva Hrvatska D.O.O. Methods for preparing bortezomib and intermediates used in its manufacture
US7838673B2 (en) * 2007-10-16 2010-11-23 Millennium Pharmaceuticals, Inc. Proteasome inhibitors
EP2443128B1 (en) * 2009-06-19 2017-12-20 LEK Pharmaceuticals d.d. New synthetic route for the preparation of alpha-amino boronic esters

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4525309A (en) * 1983-03-15 1985-06-25 Washington State University Research Foundation, Inc. Lewis acid catalysis of the homologation of boronic esters with haloalkylmetal reagents
US6699835B2 (en) * 2001-01-25 2004-03-02 The United States Of America As Represented By The Department Of Health And Human Services Formulation of boronic acid compounds

Also Published As

Publication number Publication date
CR8653A (es) 2007-10-23
IL178250A (en) 2012-06-28
ME01975B (me) 2015-05-20
ECSP066960A (es) 2006-12-20
CN108329337A (zh) 2018-07-27
NO344610B1 (no) 2020-02-10
SG10201800972PA (en) 2018-03-28
US20190112334A1 (en) 2019-04-18
CY1112053T1 (el) 2015-11-04
AR049374A1 (es) 2006-07-26
NO20161350A1 (no) 2006-12-22
MX367324B (es) 2019-08-15
HK1100004A1 (en) 2007-08-31
CA2560886A1 (en) 2005-10-20
WO2005097809A3 (en) 2006-02-16
EP1756121B1 (en) 2011-08-24
CL2010000350A1 (es) 2011-01-28
EP4008721A1 (en) 2022-06-08
HRP20140339T1 (hr) 2014-05-09
SG182999A1 (en) 2012-08-30
US20200369722A1 (en) 2020-11-26
UA90108C2 (uk) 2010-04-12
NZ586824A (en) 2012-03-30
JP5894952B2 (ja) 2016-03-30
SI2377869T1 (sl) 2014-05-30
US20200157143A1 (en) 2020-05-21
NZ550522A (en) 2010-08-27
US20160362449A1 (en) 2016-12-15
NL1033190C2 (nl) 2007-11-27
US20180265546A1 (en) 2018-09-20
US20210395301A1 (en) 2021-12-23
TW200616646A (en) 2006-06-01
US8283467B2 (en) 2012-10-09
FI4008721T3 (fi) 2024-03-19
CA2560886C (en) 2014-08-12
IL178250A0 (en) 2006-12-31
KR20070007873A (ko) 2007-01-16
CY1124753T1 (el) 2022-07-22
PT3385267T (pt) 2021-11-23
JP2007530687A (ja) 2007-11-01
PE20060162A1 (es) 2006-04-07
US20150038706A1 (en) 2015-02-05
RS65253B1 (sr) 2024-03-29
CA2738706A1 (en) 2005-10-20
UY28830A1 (es) 2005-09-30
DK1756121T3 (da) 2012-01-09
BRPI0509587A (pt) 2007-09-25
EP1756121A2 (en) 2007-02-28
ES2457593T3 (es) 2014-04-28
SI4008721T1 (sl) 2024-05-31
US20180044377A1 (en) 2018-02-15
JP2010241816A (ja) 2010-10-28
UY35578A (es) 2016-01-08
JP6193960B2 (ja) 2017-09-06
DOP2011000293A (es) 2011-12-15
EP2377869A1 (en) 2011-10-19
IL219856A (en) 2015-05-31
HK1257298A1 (zh) 2019-10-18
SG151322A1 (en) 2009-04-30
HRP20110846T1 (hr) 2011-12-31
EP2377869B1 (en) 2014-01-29
CA2738706C (en) 2014-10-14
ZA200608689B (en) 2007-09-26
WO2005097809A2 (en) 2005-10-20
CN107474062A (zh) 2017-12-15
HK1246300A1 (zh) 2018-09-07
US9862745B2 (en) 2018-01-09
JP2016056180A (ja) 2016-04-21
NL1033189A1 (nl) 2007-10-22
PT4008721T (pt) 2024-03-21
RS62738B1 (sr) 2022-01-31
ATE521612T1 (de) 2011-09-15
CN108329337B (zh) 2021-06-25
IL219853A0 (en) 2012-06-28
AU2005230930A1 (en) 2005-10-20
RS53259B (sr) 2014-08-29
CN1960996A (zh) 2007-05-09
US20100174072A1 (en) 2010-07-08
US20210171574A1 (en) 2021-06-10
US20190330270A1 (en) 2019-10-31
NZ598172A (en) 2013-08-30
SG182998A1 (en) 2012-08-30
CA2859119A1 (en) 2005-10-20
CN103396427B (zh) 2018-04-13
NO20191065A1 (no) 2006-12-22
MY145427A (en) 2012-02-15
HUE056859T2 (hu) 2022-03-28
NL1033190A1 (nl) 2007-04-23
US10000529B2 (en) 2018-06-19
JP5414625B2 (ja) 2014-02-12
NL1028639C2 (nl) 2007-01-17
RS51983B (sr) 2012-02-29
US20130005968A1 (en) 2013-01-03
ES2371652T3 (es) 2012-01-05
IL219856A0 (en) 2012-06-28
AU2005230930B2 (en) 2011-09-29
AR097310A2 (es) 2016-03-02
DK3385267T3 (da) 2021-11-01
CY1115336T1 (el) 2017-01-04
TWI386212B (zh) 2013-02-21
CN111925385B (zh) 2023-11-21
DK4008721T3 (da) 2024-03-25
NO343966B1 (no) 2019-07-29
JP4558039B2 (ja) 2010-10-06
PL1756121T3 (pl) 2012-02-29
NL1033189C2 (nl) 2008-08-14
SI1756121T1 (sl) 2012-03-30
DK2377869T3 (da) 2014-04-14
EP3385267A1 (en) 2018-10-10
JP2013100378A (ja) 2013-05-23
CN1960996B (zh) 2016-04-20
PL3385267T3 (pl) 2022-02-14
AR097309A2 (es) 2016-03-02
US20050240047A1 (en) 2005-10-27
LT3385267T (lt) 2021-11-10
PE20142402A1 (es) 2015-02-04
SG10201600029PA (en) 2016-02-26
PL2377869T3 (pl) 2014-07-31
PT1756121E (pt) 2011-11-30
NL1028639A1 (nl) 2005-10-20
HRP20212002T1 (hr) 2022-04-01
ES2974758T3 (es) 2024-07-01
IL219853A (en) 2015-05-31
CL2014002252A1 (es) 2014-12-05
US20220204558A1 (en) 2022-06-30
EA012927B1 (ru) 2010-02-26
NO338905B1 (no) 2016-10-31
NO20171939A1 (no) 2006-12-22
CA2853272A1 (en) 2005-10-20
CN103396427A (zh) 2013-11-20
LT4008721T (lt) 2024-03-25
PT2377869E (pt) 2014-04-15
HUE065769T2 (hu) 2024-06-28
HK1164320A1 (en) 2012-10-19
EP2377868A1 (en) 2011-10-19
EA200601795A1 (ru) 2007-04-27
PL4008721T3 (pl) 2024-05-13
UY34969A (es) 2015-02-27
EP4008721B1 (en) 2024-01-03
EP3385267B1 (en) 2021-09-29
CN111925385A (zh) 2020-11-13
US7714159B2 (en) 2010-05-11
NO20064893L (no) 2006-12-22
SI3385267T1 (sl) 2022-04-29
ES2899606T3 (es) 2022-03-14
HRP20240307T3 (hr) 2024-05-10
PE20110075A1 (es) 2011-02-17

Similar Documents

Publication Publication Date Title
KR100939598B1 (ko) 붕소산 에스테르와 산 화합물의 합성
AU2019222807A1 (en) Synthesis of boronic ester and acid compounds
HK40066099A (en) Synthesis of boronic ester and acid compounds
HK40066099B (en) Synthesis of boronic ester and acid compounds
AU2011265442B2 (en) Synthesis of boronic ester and acid compounds
HK40040733A (en) Synthesis of boronic ester and acid compounds
HK40040733B (zh) 硼的酯和酸化合物的合成
HK1257298B (en) Synthesis of boronic ester and acid compounds
HK1163106A (en) Synthesis of bortezomib
HK1100004B (en) Synthesis of boronic ester and acid compounds
AU2013202996A1 (en) Synthesis of boronic ester and acid compounds
MXPA06011276A (en) Synthesis of boronic ester and acid compounds

Legal Events

Date Code Title Description
PA0105 International application

St.27 status event code: A-0-1-A10-A15-nap-PA0105

PG1501 Laying open of application

St.27 status event code: A-1-1-Q10-Q12-nap-PG1501

P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

A201 Request for examination
P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

PA0201 Request for examination

St.27 status event code: A-1-2-D10-D11-exm-PA0201

E902 Notification of reason for refusal
PE0902 Notice of grounds for rejection

St.27 status event code: A-1-2-D10-D21-exm-PE0902

T11-X000 Administrative time limit extension requested

St.27 status event code: U-3-3-T10-T11-oth-X000

E13-X000 Pre-grant limitation requested

St.27 status event code: A-2-3-E10-E13-lim-X000

P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

E902 Notification of reason for refusal
PE0902 Notice of grounds for rejection

St.27 status event code: A-1-2-D10-D21-exm-PE0902

T11-X000 Administrative time limit extension requested

St.27 status event code: U-3-3-T10-T11-oth-X000

P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

E701 Decision to grant or registration of patent right
PE0701 Decision of registration

St.27 status event code: A-1-2-D10-D22-exm-PE0701

GRNT Written decision to grant
PR0701 Registration of establishment

St.27 status event code: A-2-4-F10-F11-exm-PR0701

PR1002 Payment of registration fee

St.27 status event code: A-2-2-U10-U12-oth-PR1002

Fee payment year number: 1

PG1601 Publication of registration

St.27 status event code: A-4-4-Q10-Q13-nap-PG1601

FPAY Annual fee payment

Payment date: 20130109

Year of fee payment: 4

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 4

FPAY Annual fee payment

Payment date: 20140108

Year of fee payment: 5

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 5

FPAY Annual fee payment

Payment date: 20150107

Year of fee payment: 6

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 6

FPAY Annual fee payment

Payment date: 20160111

Year of fee payment: 7

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 7

FPAY Annual fee payment

Payment date: 20170116

Year of fee payment: 8

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 8

R18-X000 Changes to party contact information recorded

St.27 status event code: A-5-5-R10-R18-oth-X000

FPAY Annual fee payment

Payment date: 20180109

Year of fee payment: 9

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 9

FPAY Annual fee payment

Payment date: 20190109

Year of fee payment: 10

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 10

FPAY Annual fee payment

Payment date: 20200110

Year of fee payment: 11

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 11

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 12

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 13

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 14

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 15

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 16

PC1801 Expiration of term

St.27 status event code: N-4-6-H10-H14-oth-PC1801

Not in force date: 20250325

Ip right cessation event data comment text: Termination Category : EXPIRATION_OF_DURATION