UA90108C2 - Способи одержання сполук боронового естеру та кислоти - Google Patents

Способи одержання сполук боронового естеру та кислоти

Info

Publication number
UA90108C2
UA90108C2 UAA200611339A UAA200611339A UA90108C2 UA 90108 C2 UA90108 C2 UA 90108C2 UA A200611339 A UAA200611339 A UA A200611339A UA A200611339 A UAA200611339 A UA A200611339A UA 90108 C2 UA90108 C2 UA 90108C2
Authority
UA
Ukraine
Prior art keywords
acid compounds
synthesis
boronic ester
boronic
acid
Prior art date
Application number
UAA200611339A
Other languages
English (en)
Russian (ru)
Inventor
І. Фрейзер Пікерсджилл
Джон Бішоп
Крістоф Келльнер
Жан-Марк Гомес
Ахім Гайзер
Роберт Хетт
Вінс Еммоскейто
Стефен Манк
Янг Ло
Фан-Тін Чуй
Вітхалананд Р. Кулкарні
Original Assignee
Мілленніум Фармасьютікалз, Інк.
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=UA90108(C2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Мілленніум Фармасьютікалз, Інк. filed Critical Мілленніум Фармасьютікалз, Інк.
Publication of UA90108C2 publication Critical patent/UA90108C2/uk

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
    • 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
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • 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
    • 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
    • C07F5/04—Esters of boric acids
    • Y—GENERAL 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design 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)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Cпособи одержання сполуки боронового естеру формули (І), аміноборонового естеру (VІІ) і бортезомібу інгібітора протеасоми (ХІV), в якій R1 являє собою необов'язково заміщену С1-8аліфатичну, С6-10арильну або (С6-10арил)(С1-6аліфатичну) групу; R2 являє собою водень або хлор; R3 являє собою хлор; і кожен з R4 і R5, незалежно, являє собою необов'язково заміщену С1-12аліфатичну, С6-14ароматичну або 5-14-членну гетероароматичну групу, або R4 і R5, взяті разом з проміжними атомами кисню і бору, утворюють необов'язково заміщений 5-10-членний цикл, що містить 0-2 додаткових циклічних гетероатоми, які вибирають з N, О або S; де вказаний спосіб включає: (a) забезпечення бор "ат" комплексу формули (II): в якій Y являє собою нуклеофужну групу; М+ являє собою катіон; і кожен з R1-R5 є таким, як визначено вище; і (b) контактування бор "ат" комплексу формули (II) з кислотою Льюїса в умовах, за яких одержують сполуку боронового естеру формули (І), де вказану стадію контактування проводять в реакційній суміші, яка містить: (і) координуючий естерний розчинник, який має низьку міру змішуваності з водою; або (іі) естерний розчинник, який має низьку міру змішуваності з водою, і координуючий співрозчинник; де розчинність води у кожному естерному розчиннику, що має низьку міру змішуваності з водою, становить менш, ніж 5 мас. %; (c) промивання реакційної суміші водним розчином; і (d) концентрування промитої реакційної суміші шляхом видалення розчинників з одержанням залишку, який містить сполуку боронового естеру формули (І) EMBED ISISServer , (І) EMBED ISISServer , (VІІ) EMBED ISISServer , (ХІV) EMBED ISISServer (II).
UAA200611339A 2004-03-30 2005-03-24 Способи одержання сполук боронового естеру та кислоти UA90108C2 (uk)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US55753504P 2004-03-30 2004-03-30
PCT/US2005/009774 WO2005097809A2 (en) 2004-03-30 2005-03-24 Synthesis of boronic ester and acid compounds

Publications (1)

Publication Number Publication Date
UA90108C2 true UA90108C2 (uk) 2010-04-12

Family

ID=34968044

Family Applications (1)

Application Number Title Priority Date Filing Date
UAA200611339A UA90108C2 (uk) 2004-03-30 2005-03-24 Способи одержання сполук боронового естеру та кислоти

Country Status (41)

Country Link
US (14) US7714159B2 (uk)
EP (5) EP2377868A1 (uk)
JP (4) JP4558039B2 (uk)
KR (1) KR100939598B1 (uk)
CN (5) CN107474062A (uk)
AR (3) AR049374A1 (uk)
AT (1) ATE521612T1 (uk)
AU (1) AU2005230930B2 (uk)
BR (1) BRPI0509587A (uk)
CA (4) CA2560886C (uk)
CL (2) CL2010000350A1 (uk)
CR (1) CR8653A (uk)
CY (3) CY1112053T1 (uk)
DK (4) DK4008721T3 (uk)
DO (1) DOP2011000293A (uk)
EA (1) EA012927B1 (uk)
EC (1) ECSP066960A (uk)
ES (4) ES2371652T3 (uk)
FI (1) FI4008721T3 (uk)
HK (4) HK1100004A1 (uk)
HR (4) HRP20240307T3 (uk)
HU (1) HUE056859T2 (uk)
IL (3) IL178250A (uk)
LT (2) LT3385267T (uk)
ME (1) ME01975B (uk)
MX (1) MX367324B (uk)
MY (1) MY145427A (uk)
NL (3) NL1028639C2 (uk)
NO (4) NO338905B1 (uk)
NZ (3) NZ586824A (uk)
PE (3) PE20060162A1 (uk)
PL (4) PL1756121T3 (uk)
PT (4) PT1756121E (uk)
RS (4) RS62738B1 (uk)
SG (5) SG182998A1 (uk)
SI (4) SI2377869T1 (uk)
TW (1) TWI386212B (uk)
UA (1) UA90108C2 (uk)
UY (3) UY28830A1 (uk)
WO (1) WO2005097809A2 (uk)
ZA (1) ZA200608689B (uk)

Families Citing this family (67)

* 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
EP2377868A1 (en) 2004-03-30 2011-10-19 Millennium Pharmaceuticals, Inc. Synthesis of Bortezomib
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
AU2016253697A1 (en) * 2007-08-06 2016-11-24 Millennium Pharmaceuticals, Inc. Proteasome inhibitors
US7442830B1 (en) 2007-08-06 2008-10-28 Millenium Pharmaceuticals, Inc. Proteasome inhibitors
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
WO2009026579A1 (en) * 2007-08-23 2009-02-26 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
GEP201706703B (en) 2008-06-17 2017-07-25 Millennium Pharmaceuticals Inc (A Delaware Corporation) Boronate ester compounds and pharmaceutical compositions thereof
AU2013204896A1 (en) * 2008-09-29 2013-05-16 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
US9315525B2 (en) 2009-06-19 2016-04-19 Lek Pharmaceuticals D.D. Synthetic route for the preparation of α-amino boronic acid derivatives via substituted alk-1-ynes
EP2270019A1 (en) 2009-06-19 2011-01-05 LEK Pharmaceuticals d.d. New synthetic route for the preparation of alpha-amino boronic esters
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
CN102725300B (zh) 2009-12-22 2015-03-11 赛福伦公司 蛋白酶体抑制剂及其制备、纯化、和应用的方法
US20110178287A1 (en) 2010-01-19 2011-07-21 Cerulean Pharma Inc. Cyclodextrin-based polymers for therapeutic delivery
US20130085277A1 (en) 2010-02-09 2013-04-04 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
US9061037B2 (en) * 2010-03-18 2015-06-23 Innopharma, Inc. Stable bortezomib formulations
US8263578B2 (en) 2010-03-18 2012-09-11 Innopharma, Inc. Stable bortezomib formulations
US8513218B2 (en) 2010-03-31 2013-08-20 Millennium Pharmaceuticals, Inc. Derivatives of 1-amino-2-cyclopropylethylboronic acid
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
CA2799202C (en) 2010-05-18 2016-07-05 Cerulean Pharma Inc. Compositions and methods for treatment of autoimmune and other diseases
EP2627636B1 (en) 2010-10-14 2015-09-02 Synthon BV Process for making bortezomib and the 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
KR20150067175A (ko) * 2012-09-11 2015-06-17 시플라 리미티드 보르테조밉을 제조하기 위한 방법
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
EP2928898B1 (en) 2012-12-07 2021-04-14 Venatorx Pharmaceuticals, Inc. Beta-lactamase inhibitors
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
WO2014110442A1 (en) 2013-01-10 2014-07-17 VenatoRx Pharmaceuticals, Inc. Beta-lactamase inhibitors
IN2013MU01431A (uk) 2013-04-16 2015-06-26 Cipla Ltd
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
US10167311B2 (en) 2014-02-03 2019-01-01 Ohio State Innovation Foundation Boronic acid esters and pharmaceutical formulations thereof
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
RU2686740C2 (ru) 2014-06-11 2019-04-30 Венаторкс Фармасьютикалс, Инк. Ингибиторы бета-лактамазы
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
DE102015204151A1 (de) * 2015-03-09 2016-09-15 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
WO2018027062A1 (en) 2016-08-04 2018-02-08 VenatoRx Pharmaceuticals, Inc. Boron-containing compounds
AU2018221670B2 (en) 2017-02-17 2021-02-04 Fresenius Kabi Oncology Ltd. An improved process for the preparation of boronic acid esters
CN110678186A (zh) 2017-03-06 2020-01-10 维纳拓尔斯制药公司 包含β-内酰胺酶抑制剂的固体形式和组合式组合物及其用途
US11332485B2 (en) 2017-05-26 2022-05-17 VenatoRx Pharmaceuticals, Inc. Penicillin-binding protein inhibitors
WO2018218154A1 (en) 2017-05-26 2018-11-29 VenatoRx Pharmaceuticals, Inc. Penicillin-binding protein inhibitors
CN109305980B (zh) 2017-07-28 2022-10-11 成都奥璟生物科技有限公司 一种硼酸酯化合物、其合成方法及其用途
EP3676272A4 (en) * 2017-09-02 2021-04-21 Sun Pharmaceutical Industries Limited IXAZOMIB CITRATE PREPARATION PROCESS
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
US11964993B2 (en) 2021-07-03 2024-04-23 Shilpa Pharma Lifesciences Limited Crystalline bortezomib process

Family Cites Families (17)

* 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
US4537773A (en) 1983-12-05 1985-08-27 E. I. Du Pont De Nemours And Company α-Aminoboronic acid derivatives
US4499082A (en) 1983-12-05 1985-02-12 E. I. Du Pont De Nemours And Company α-Aminoboronic acid peptides
US4701545A (en) 1986-02-12 1987-10-20 Washington State University Research Foundation, Inc. Preparation of α,α-dihaloalkyl boronic esters
US5250720A (en) 1987-06-05 1993-10-05 The Dupont Merck Pharmaceutical Company Intermediates for preparing peptide boronic acid inhibitors of trypsin-like proteases
US5187157A (en) 1987-06-05 1993-02-16 Du Pont Merck Pharmaceutical Company 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
EP1355910B1 (en) 2001-01-25 2011-03-09 The United States of America, represented by the Secretary, Department of Health and Human Services Formulation of boronic acid compounds
WO2003033507A1 (fr) 2001-10-12 2003-04-24 Kyorin Pharmaceutical Co., Ltd. Derives d'acide benzylmalonique et inhibiteurs de proteasomes les contenant
JPWO2003033506A1 (ja) * 2001-10-12 2005-02-03 杏林製薬株式会社 アミノボラ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
EP2377868A1 (en) 2004-03-30 2011-10-19 Millennium Pharmaceuticals, Inc. Synthesis of Bortezomib
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
US9315525B2 (en) * 2009-06-19 2016-04-19 Lek Pharmaceuticals D.D. Synthetic route for the preparation of α-amino boronic acid derivatives via substituted alk-1-ynes

Also Published As

Publication number Publication date
EP2377869A1 (en) 2011-10-19
NO20191065A1 (no) 2006-12-22
US20200157143A1 (en) 2020-05-21
US20220204558A1 (en) 2022-06-30
MY145427A (en) 2012-02-15
EP2377869B1 (en) 2014-01-29
HRP20240307T3 (hr) 2024-05-10
PT4008721T (pt) 2024-03-21
PT1756121E (pt) 2011-11-30
SI3385267T1 (sl) 2022-04-29
ES2371652T3 (es) 2012-01-05
LT3385267T (lt) 2021-11-10
NZ598172A (en) 2013-08-30
CN107474062A (zh) 2017-12-15
NL1028639C2 (nl) 2007-01-17
RS51983B (en) 2012-02-29
US20130005968A1 (en) 2013-01-03
US20210395301A1 (en) 2021-12-23
IL178250A0 (en) 2006-12-31
US20050240047A1 (en) 2005-10-27
WO2005097809A3 (en) 2006-02-16
NZ550522A (en) 2010-08-27
ATE521612T1 (de) 2011-09-15
CA2738706C (en) 2014-10-14
CN108329337B (zh) 2021-06-25
NO338905B1 (no) 2016-10-31
JP4558039B2 (ja) 2010-10-06
KR100939598B1 (ko) 2010-02-01
HK1100004A1 (en) 2007-08-31
ES2974758T3 (es) 2024-07-01
US20190112334A1 (en) 2019-04-18
HK1257298A1 (zh) 2019-10-18
EP4008721A1 (en) 2022-06-08
US10000529B2 (en) 2018-06-19
ZA200608689B (en) 2007-09-26
AU2005230930A1 (en) 2005-10-20
JP5894952B2 (ja) 2016-03-30
AR049374A1 (es) 2006-07-26
IL219856A0 (en) 2012-06-28
JP2010241816A (ja) 2010-10-28
CN1960996B (zh) 2016-04-20
HRP20140339T1 (hr) 2014-05-09
US20210171574A1 (en) 2021-06-10
PL4008721T3 (pl) 2024-05-13
ES2457593T3 (es) 2014-04-28
PL2377869T3 (pl) 2014-07-31
EP4008721B1 (en) 2024-01-03
BRPI0509587A (pt) 2007-09-25
DOP2011000293A (es) 2011-12-15
EP1756121B1 (en) 2011-08-24
IL219856A (en) 2015-05-31
NZ586824A (en) 2012-03-30
JP2016056180A (ja) 2016-04-21
NO20064893L (no) 2006-12-22
TW200616646A (en) 2006-06-01
EP3385267B1 (en) 2021-09-29
US7714159B2 (en) 2010-05-11
PT3385267T (pt) 2021-11-23
HRP20110846T1 (hr) 2011-12-31
FI4008721T3 (fi) 2024-03-19
DK4008721T3 (da) 2024-03-25
RS65253B1 (sr) 2024-03-29
ME01975B (me) 2015-05-20
AU2005230930B2 (en) 2011-09-29
NO20171939A1 (no) 2006-12-22
IL219853A0 (en) 2012-06-28
NO20161350A1 (no) 2006-12-22
RS62738B1 (sr) 2022-01-31
PT2377869E (pt) 2014-04-15
CL2014002252A1 (es) 2014-12-05
UY35578A (es) 2016-01-08
US20150038706A1 (en) 2015-02-05
US20200369722A1 (en) 2020-11-26
ES2899606T3 (es) 2022-03-14
CA2560886A1 (en) 2005-10-20
CY1115336T1 (el) 2017-01-04
US8283467B2 (en) 2012-10-09
US20160362449A1 (en) 2016-12-15
EP3385267A1 (en) 2018-10-10
AR097309A2 (es) 2016-03-02
EA200601795A1 (ru) 2007-04-27
EP2377868A1 (en) 2011-10-19
EP1756121A2 (en) 2007-02-28
US9862745B2 (en) 2018-01-09
NL1033189A1 (nl) 2007-10-22
SG10201600029PA (en) 2016-02-26
KR20070007873A (ko) 2007-01-16
CY1112053T1 (el) 2015-11-04
PE20110075A1 (es) 2011-02-17
SI1756121T1 (sl) 2012-03-30
UY34969A (es) 2015-02-27
JP6193960B2 (ja) 2017-09-06
SI4008721T1 (sl) 2024-05-31
EA012927B1 (ru) 2010-02-26
SG10201800972PA (en) 2018-03-28
ECSP066960A (es) 2006-12-20
US20180265546A1 (en) 2018-09-20
PE20142402A1 (es) 2015-02-04
WO2005097809A2 (en) 2005-10-20
MX367324B (es) 2019-08-15
RS53259B (en) 2014-08-29
TWI386212B (zh) 2013-02-21
CA2738706A1 (en) 2005-10-20
DK1756121T3 (da) 2012-01-09
CN111925385B (zh) 2023-11-21
JP5414625B2 (ja) 2014-02-12
CN111925385A (zh) 2020-11-13
CA2859119A1 (en) 2005-10-20
HK1246300A1 (zh) 2018-09-07
IL178250A (en) 2012-06-28
IL219853A (en) 2015-05-31
HUE056859T2 (hu) 2022-03-28
CN103396427B (zh) 2018-04-13
DK2377869T3 (da) 2014-04-14
NL1028639A1 (nl) 2005-10-20
CR8653A (es) 2007-10-23
CY1124753T1 (el) 2022-07-22
SG182998A1 (en) 2012-08-30
DK3385267T3 (da) 2021-11-01
CL2010000350A1 (es) 2011-01-28
HK1164320A1 (en) 2012-10-19
US20190330270A1 (en) 2019-10-31
PE20060162A1 (es) 2006-04-07
NO344610B1 (no) 2020-02-10
SG182999A1 (en) 2012-08-30
CA2853272A1 (en) 2005-10-20
CN103396427A (zh) 2013-11-20
CA2560886C (en) 2014-08-12
CN1960996A (zh) 2007-05-09
AR097310A2 (es) 2016-03-02
NL1033190A1 (nl) 2007-04-23
JP2007530687A (ja) 2007-11-01
NL1033190C2 (nl) 2007-11-27
NO343966B1 (no) 2019-07-29
CN108329337A (zh) 2018-07-27
LT4008721T (lt) 2024-03-25
SI2377869T1 (sl) 2014-05-30
HRP20212002T1 (hr) 2022-04-01
UY28830A1 (es) 2005-09-30
SG151322A1 (en) 2009-04-30
PL1756121T3 (pl) 2012-02-29
NL1033189C2 (nl) 2008-08-14
US20100174072A1 (en) 2010-07-08
US20180044377A1 (en) 2018-02-15
PL3385267T3 (pl) 2022-02-14
JP2013100378A (ja) 2013-05-23

Similar Documents

Publication Publication Date Title
MY145427A (en) Synthesis of boronic ester and acid compounds
PL1758852T3 (pl) Podstawione związki cyklopentenu
MX2007003108A (es) Compuestos imidazo-3-il-amina sustituidos y biciclicos.
MX2007004426A (es) Procesos para preparar telmisartan.
PL1891004T3 (pl) Pentafluorosulfanylo-podstawiony związek i jego zastosowanie do wytwarzania środków leczniczych
MX340573B (es) Proceso para la fabricacion de compuestos farmaceuticamente activos.
UA102817C2 (uk) Спосіб синтезу агомелатину
MX2007003118A (es) Procedimiento de intermediarios para preparar inhibidores de cisteina proteasa.
TW200728310A (en) Process for the preparation of ferri-succinylcasein
MX2010010660A (es) Nuevos complejos de rutenio como catalizadores para reacciones de metatesis.
UA102220C2 (uk) Спосіб синтезу агомелатину
IL180354A0 (en) Process for the preparation of atomoxetine hydrochloride
IN2012DN01968A (uk)
MX2012007341A (es) Inhibidores de proteasoma y procesos para su preparacion, purificacion y uso.
UA94837C2 (uk) Спосіб синтезу (7-метокси-1-нафтил)ацетонітрилу і застосування у синтезі агомелатину
MX2012003488A (es) Proceso para la elaboracion de n-acil-bifenil-alanina.
RS20060297A (en) Rearranged pentanols, a method for the production thereof, and their use as antiphlogistics
TW200738650A (en) Process for synthesis of aryloxy diaminopyrimidines
TW200806304A (en) Maitake mushroom extract and composition containing the same for enhance production of sebum
SG158860A1 (en) Processes for the preparation of aminoethoxybenzyl alcohols
MX2007013872A (es) Procedimiento para la produccion de 4-bifenililazetidina-2-onas.
MX2009007598A (es) Hexahidrato de enrofloxacino.
TW200728267A (en) Processes and intermediates for the preparation of prostaglandins
SG155231A1 (en) Process for synthesis of dialkoxyorganoboranes
IL184519A0 (en) Protease inhibitor precursor synthesis