EA201301316A1 - Способ получения интермедиатов эстетрола - Google Patents

Способ получения интермедиатов эстетрола

Info

Publication number
EA201301316A1
EA201301316A1 EA201301316A EA201301316A EA201301316A1 EA 201301316 A1 EA201301316 A1 EA 201301316A1 EA 201301316 A EA201301316 A EA 201301316A EA 201301316 A EA201301316 A EA 201301316A EA 201301316 A1 EA201301316 A1 EA 201301316A1
Authority
EA
Eurasian Patent Office
Prior art keywords
compound
formula
group
alkyl
reacting
Prior art date
Application number
EA201301316A
Other languages
English (en)
Other versions
EA023991B1 (ru
Inventor
Жан-Клод Паскаль
Original Assignee
Эстетра С.А.
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 Эстетра С.А. filed Critical Эстетра С.А.
Publication of EA201301316A1 publication Critical patent/EA201301316A1/ru
Publication of EA023991B1 publication Critical patent/EA023991B1/ru

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00Drugs for disorders of the endocrine system
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J75/00Processes for the preparation of steroids in general
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J1/00Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C07J1/0051Estrane derivatives
    • C07J1/0066Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J1/00Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C07J1/0051Estrane derivatives
    • C07J1/0066Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa
    • C07J1/007Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/56Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/565Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00Drugs for disorders of the endocrine system
    • A61P5/24Drugs for disorders of the endocrine system of the sex hormones
    • A61P5/30Oestrogens
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J1/00Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C07J1/0051Estrane derivatives
    • C07J1/0059Estrane derivatives substituted in position 17 by a keto group
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J13/00Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
    • C07J13/005Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17 with double bond in position 16 (17)
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J51/00Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
    • 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)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Endocrinology (AREA)
  • Engineering & Computer Science (AREA)
  • Diabetes (AREA)
  • Epidemiology (AREA)
  • Steroid Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Изобретение относится к способу получения соединения формулы (I)включающему следующие стадии: а) взаимодействие соединения формулы (II) с ацилирующим или с силилирующим агентом с получением соединения формулы (III), где Ри Р, каждый независимо, представляет собой защитную группу, выбранную из R-Si-RRили RCO-, где Rпредставляет собой группу, выбранную из Cалкильной или С-циклоалкильной группы, каждая из которых может быть необязательно замещена одним или несколькими заместителями, независимо выбранными из фтора или Cалкильной группы; R, Rи Rкаждый независимо представляет собой группу, выбранную из Cалкильной или фенильной группы, каждая из которых может быть необязательно замещена одним или несколькими заместителями, независимо выбранными из фтора или Cалкильной группы;b) взаимодействие соединения формулы (III) в присутствии ацетата палладия или его производного с получением соединения формулы (IV); ис) взаимодействие соединения формулы (IV) с восстановителем с получением соединения формулы (I).
EA201301316A 2011-06-01 2012-06-01 Способ получения интермедиатов эстетрола EA023991B1 (ru)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201161492300P 2011-06-01 2011-06-01
EP11168561 2011-06-01
PCT/EP2012/060447 WO2012164096A1 (en) 2011-06-01 2012-06-01 Process for the production of estetrol intermediates

Publications (2)

Publication Number Publication Date
EA201301316A1 true EA201301316A1 (ru) 2014-04-30
EA023991B1 EA023991B1 (ru) 2016-08-31

Family

ID=45003353

Family Applications (1)

Application Number Title Priority Date Filing Date
EA201301316A EA023991B1 (ru) 2011-06-01 2012-06-01 Способ получения интермедиатов эстетрола

Country Status (24)

Country Link
US (1) US11053274B2 (ru)
EP (1) EP2714710B1 (ru)
JP (2) JP6425540B2 (ru)
KR (1) KR101994805B1 (ru)
CN (2) CN107266514A (ru)
AU (1) AU2012264602B2 (ru)
BR (1) BR112013030830B1 (ru)
CA (1) CA2835981C (ru)
CY (1) CY1118150T1 (ru)
DK (1) DK2714710T3 (ru)
EA (1) EA023991B1 (ru)
ES (1) ES2579175T3 (ru)
HR (1) HRP20160692T2 (ru)
HU (1) HUE029252T2 (ru)
ME (1) ME02454B (ru)
MX (1) MX341561B (ru)
PL (1) PL2714710T3 (ru)
PT (1) PT2714710T (ru)
RS (1) RS54880B1 (ru)
SG (1) SG195118A1 (ru)
SI (1) SI2714710T1 (ru)
SM (1) SMT201600206B (ru)
WO (1) WO2012164096A1 (ru)
ZA (1) ZA201308446B (ru)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RS54880B1 (sr) 2011-06-01 2016-10-31 Estetra Sprl Postupak proizvodnje intermedijarnih proizvoda estetrola
PT2714712T (pt) 2011-06-01 2016-11-08 Estetra Sprl Processo para a produção de intermediários de estetrol
EP2383279A1 (en) 2011-07-19 2011-11-02 Pantarhei Bioscience B.V. Process for the preparation of estetrol
PT2764008T (pt) 2011-10-07 2016-11-10 Estetra Sprl Processo para a produção de estetrol
MY195019A (en) 2015-06-18 2023-01-03 Estetra Sprl Orodispersible dosage unit containing an estetrol component
HUE054551T2 (hu) 2015-06-18 2021-09-28 Estetra Sprl Ösztetrolt tartalmazó, szájban diszpergálódó tabletta
UA123099C2 (uk) 2015-06-18 2021-02-17 Естетра Спрл Диспергована в порожнині рота одиниця дозування, яка містить естетрольний компонент
LT3310345T (lt) 2015-06-18 2021-06-25 Estetra Sprl Burnoje disperguojama tabletė, turinti estetrolio
CN105837424A (zh) * 2016-03-31 2016-08-10 常州大学 一种1-氯-3-甲基-3-丁烯-2-酮的合成方法
KR20220144885A (ko) 2016-08-05 2022-10-27 에스테트라, 소시에떼 아 레스폰서빌리떼 리미떼 월경통 및 생리통의 관리방법
JP6935766B2 (ja) 2018-02-15 2021-09-15 日本精工株式会社 スピンドル装置
TWI801561B (zh) 2018-04-19 2023-05-11 比利時商依思特拉私人有限責任公司 化合物及其用於緩解絕經相關症狀的用途
JOP20200260A1 (ar) 2018-04-19 2019-10-19 Estetra Sprl مركبات واستخداماتها للتخفيف من الأعراض المصاحبة لانقطاع الطمث
IT201900017414A1 (it) 2019-09-27 2021-03-27 Ind Chimica Srl Processo per la preparazione di (15α,16α,17β)-estra-1,3,5(10)-triene-3,15,16,17-tetrolo (Estetrolo) ed intermedi di detto processo
IT201900021879A1 (it) 2019-11-22 2021-05-22 Ind Chimica Srl PROCESSO PER LA PREPARAZIONE DI (15α,16α,17β)-ESTRA-1,3,5(10)-TRIENE-3,15,16,17-TETROLO (ESTETROLO) ED INTERMEDI DI DETTO PROCESSO
DE112020004564T5 (de) 2019-09-27 2022-06-15 Industriale Chimica S.R.L. VERFAHREN ZUM HERSTELLEN VON (15α,16α,17β)-ESTRA-1,3,5(10)-TRIEN-3,15,16,17-TETROL (ESTETROL) UND ZWISCHENSTUFEN DES VERFAHRENS
WO2023021026A1 (en) 2021-08-17 2023-02-23 Aspen Oss B.V. A synthetic pathway to estra-1,3,5(10)-triene-3,15a,16a,17b-tetrol
CA3232558A1 (en) 2021-10-01 2023-04-06 Roberto Lenna Process for preparing (15alpha,16alpha,17 eta)-estra-1,3,5(10)-triene-3,15,16,17-tetrol (estetrol) monohydrate

Family Cites Families (69)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE144266C (ru)
US3138588A (en) 1962-08-24 1964-06-23 American Home Prod 17-ketals of estrone and derivatives thereof
US3177206A (en) 1963-03-07 1965-04-06 American Home Prod Selective bromination of a-ring aromatic 17-ketalized steroids
US3433785A (en) 1966-07-11 1969-03-18 Sterling Drug Inc 15,16-disubstituted aromatic steroids,intermediates and processes
US3673180A (en) 1970-06-18 1972-06-27 Merck & Co Inc 19-nor-6,6-ethylene-20-spiroxenes
US4792620A (en) 1983-10-14 1988-12-20 Bp Chemicals Limited Carbonylation catalysts
US4739078A (en) 1984-02-17 1988-04-19 The Upjohn Company Use of borohydride-salt lanthanide salt reagents for stereo selective reduction of C-15-keto prostaglandin precursors
IE60780B1 (en) 1987-01-23 1994-08-10 Akzo Nv New 11-aryl steroid derivatives
DE3710728A1 (de) 1987-03-31 1988-10-13 Schering Ag Verfahren zur herstellung von 17(alpha)-ethinyl-17ss-hydroxy-18-methyl-4,15-estradien-3-on und die neuen zwischenprodukte fuer dieses verfahren
US5073374A (en) 1988-11-30 1991-12-17 Schering Corporation Fast dissolving buccal tablet
US5340586A (en) 1991-04-12 1994-08-23 University Of Southern California Methods and formulations for use in treating oophorectomized women
JPH07101977A (ja) 1993-10-05 1995-04-18 Kureha Chem Ind Co Ltd ホルモン作用を軽減した新規なエストラジオール誘導体及びその増殖因子阻害剤
WO1997004752A1 (en) 1995-07-26 1997-02-13 Duramed Pharmaceuticals, Inc. Pharmaceutical compositions of conjugated estrogens and methods for their use
US6117446A (en) 1999-01-26 2000-09-12 Place; Virgil A. Drug dosage unit for buccal administration of steroidal active agents
TW548277B (en) 1999-07-16 2003-08-21 Akzo Nobel Nv Orally active androgens
US20020132801A1 (en) 2001-01-11 2002-09-19 Schering Aktiengesellschaft Drospirenone for hormone replacement therapy
EP1260225A1 (en) 2001-05-18 2002-11-27 Pantarhei Bioscience B.V. A pharmaceutical composition for use in hormone replacement therapy
US8048869B2 (en) 2001-05-18 2011-11-01 Pantarhei Bioscience B.V. Pharmaceutical composition for use in hormone replacement therapy
ES2296943T3 (es) 2001-05-23 2008-05-01 Pantarhei Bioscience B.V. Sistema de administracion de un medicamento estrogeno tetrahidroxilado destinado a la contracepcion hormonal.
CA2448273C (en) 2001-05-23 2010-06-29 Christian Franz Holinka Drug delivery system comprising a tetrahydroxylated estrogen for use in hormonal contraception
WO2003018026A1 (en) 2001-08-31 2003-03-06 Pantarhei Bioscience B.V. Use of estrogenic compounds in combination with progestogenic compounds in hormone-replacement therapy
CA2467222C (en) 2001-11-15 2010-06-08 Herman Jan Tijmen Coelingh Bennink Use of estrogenic compounds in combination with progestogenic compounds in hormone-replacement therapy
US6723348B2 (en) 2001-11-16 2004-04-20 Ethypharm Orodispersible tablets containing fexofenadine
HU227198B1 (en) 2001-11-27 2010-10-28 Richter Gedeon Nyrt Pharmaceutical composition for emergency contraception containing levonorgestrel
BR0215613A (pt) 2002-02-21 2004-12-07 Schering Ag Composições farmacêuticas que compreendem um ou mais esteróides, um ou mais componentes tetrahidrofolato e vitamina b12
US20050147670A1 (en) 2002-05-29 2005-07-07 Impax Laboratories Inc. Oral disintegrating dosage forms
SI1511496T1 (sl) 2002-06-11 2007-04-30 Pantarhei Bioscience Bv Metoda zdravljenja ali prevencije imunsko mediiranih motenj in farmacevtska formulacija za njeno uporabo
US7943604B2 (en) 2002-06-11 2011-05-17 Pantarhei Bioscience B.V. Method of treating human skin and a skin care composition for use in such a method
ES2299730T3 (es) 2002-07-12 2008-06-01 Pantarhei Bioscience B.V. Composicion farmaceutica que comprende derivados de estetrol para el uso en la terapia del cancer.
SI1556058T1 (sl) 2002-10-23 2008-02-29 Pantarhei Bioscience Bv Farmacevtski sestavki, ki obsegajo estetrolne derivate, za uporabo pri zdravljenju raka
US20060211669A1 (en) * 2002-11-08 2006-09-21 Verhaar Mark T Synthesis of estetrol via estrone derived steroids
EP1624878B1 (en) 2003-05-22 2006-09-27 Pantarhei Bioscience B.V. Use of compositions comprising an estrogenic component for the treatment and prevention of musculoskeletal pain
ES2388297T3 (es) 2005-05-26 2012-10-11 Abbott Products Gmbh Inhibidores de 17-HSD1 y STS
DE502006007749D1 (de) 2005-07-25 2010-10-07 Riboxx Gmbh Verfahren und Kit zur Amplifikation von heteropolymerer oder poly(C)- RNA
US20070048369A1 (en) 2005-08-26 2007-03-01 National Starch And Chemical Investment Holding Corporation Mucosal delivery tablet
EP1971344B1 (en) 2006-01-09 2010-09-22 Pantarhei Bioscience B.V. A method of treating an acute vascular disorder
US20080113953A1 (en) 2006-06-08 2008-05-15 Warner Chilcott Company, Inc. Methods to administer solid dosage forms of ethinyl estradiol and prodrugs thereof with improved bioavailability
MX2008014941A (es) 2006-06-08 2008-12-10 Warner Chilcott Co Inc Metodos para administrar formas de dosificacion solida de etinil estradiol y profarmacos del mismo con biodisponibilidad mejorada.
US20070286819A1 (en) 2006-06-08 2007-12-13 Warner Chilcott Company, Inc. Methods to administer ethinyl estradiol and prodrugs thereof with improved bioavailability
GB0621926D0 (en) 2006-11-03 2006-12-13 Medlock Medical Ltd Multi directional stretch tubular bandages
MX2009005724A (es) 2006-11-29 2009-06-12 Wyeth Corp Comprimidos bicapa de estrogenos/serm y estrogenos/progestina.
RU2465907C2 (ru) 2006-12-20 2012-11-10 Тева Вимен'С Хелс, Инк. Распадающиеся в полости рта твердые дозированные формы, содержащие прогестин, и способы получения и применение указанных дозированных форм
WO2008085038A2 (en) 2007-01-08 2008-07-17 Pantarhei Bioscience B.V. Method of treating or preventing infertility in a female mammal and pharmaceutical kit for use in such method
CL2008000095A1 (es) 2007-01-12 2008-05-16 Wyeth Corp Composicion de tableta en tableta que comprende una tableta central con estrogenos, un rellenador/diluyente, un rellenador/aglomerante, un componente polimerico y una capa de tableta exterior comprimida con agentes terapeuticos, un rellenador/diluyen
ES2378117T3 (es) 2007-06-21 2012-04-09 Pantarhei Bioscience B.V. Tratamiento del Síndrome de aspiración de meconio con estrógenos
WO2009011576A1 (en) 2007-07-19 2009-01-22 Pantarhei Bioscience B.V. Treatment or prevention of hypertensive disorders of pregnancy or fetal growth retardation
US8394995B2 (en) 2007-08-31 2013-03-12 National University Corporation Nagoya University Process for preparation of carbonyl compound and pro-oxidant for preparation of carbonyl compound
EP2077272A1 (en) 2007-12-21 2009-07-08 Affibody AB Polypeptide libraries with a predetermined scaffold
EP2077273B1 (en) 2007-12-31 2011-09-14 Animal Technology Institute Taiwan Methods for separating casein from soluble proteins in a composition
US20110250274A1 (en) 2008-09-19 2011-10-13 Shaked Ze Ev Estriol formulations
DE102009007771B4 (de) 2009-02-05 2012-02-16 Bayer Schering Pharma Aktiengesellschaft Bukkales Applikationssystem, 17α-Estradiol enthaltend
CN102058604A (zh) 2009-11-17 2011-05-18 北京万全阳光医学技术有限公司 一种含有地诺孕素和戊酸雌二醇的药物组合物及其制备方法
US9603860B2 (en) 2010-07-28 2017-03-28 Laboratorios Leon Farma Sa Pharmaceutical compositions comprising active drugs, contraceptive kits comprising active drugs, and methods of administering the same
RS54880B1 (sr) 2011-06-01 2016-10-31 Estetra Sprl Postupak proizvodnje intermedijarnih proizvoda estetrola
PT2714712T (pt) 2011-06-01 2016-11-08 Estetra Sprl Processo para a produção de intermediários de estetrol
EP2383279A1 (en) 2011-07-19 2011-11-02 Pantarhei Bioscience B.V. Process for the preparation of estetrol
ES2545337T3 (es) 2011-07-19 2015-09-10 Pantarhei Bioscience B.V. Comprimido que contiene dehidroepiandrosterona (DHEA)
ES2631359T3 (es) 2011-08-11 2017-08-30 Estetra S.P.R.L. Uso del estetrol como anticonceptivo de emergencia
JP6174585B2 (ja) 2011-09-16 2017-08-02 フェリング ベスローテン フェンノートシャップ 速溶性医薬組成物
PT2764008T (pt) 2011-10-07 2016-11-10 Estetra Sprl Processo para a produção de estetrol
EP2653163A1 (en) 2012-04-19 2013-10-23 Université de Liège Estrogenic components for use in the treatment of neurological disorders
US9808470B2 (en) 2012-04-19 2017-11-07 Universite De Liege Estrogenic components for use in the treatment of neurological disorders
WO2014159377A1 (en) 2013-03-14 2014-10-02 Teva Women's Health, Inc. Compositions containing tanaproget and natural estrogens
CA2924255C (en) 2013-09-18 2022-11-22 Crystal Pharma, S.A.U. Process for the preparation of estetrol
AU2014363599B2 (en) 2013-12-12 2019-10-31 Estetra Srl Orally disintegrating solid dosage unit containing an estetrol component
HUE054551T2 (hu) 2015-06-18 2021-09-28 Estetra Sprl Ösztetrolt tartalmazó, szájban diszpergálódó tabletta
UA123099C2 (uk) 2015-06-18 2021-02-17 Естетра Спрл Диспергована в порожнині рота одиниця дозування, яка містить естетрольний компонент
MY195019A (en) 2015-06-18 2023-01-03 Estetra Sprl Orodispersible dosage unit containing an estetrol component
LT3310345T (lt) 2015-06-18 2021-06-25 Estetra Sprl Burnoje disperguojama tabletė, turinti estetrolio

Also Published As

Publication number Publication date
CA2835981A1 (en) 2012-12-06
HUE029252T2 (en) 2017-02-28
KR20140036205A (ko) 2014-03-25
CN107266514A (zh) 2017-10-20
MX2013014045A (es) 2014-08-22
MX341561B (es) 2016-08-25
NZ617613A (en) 2015-12-24
PL2714710T3 (pl) 2017-03-31
HRP20160692T2 (hr) 2016-09-23
AU2012264602B2 (en) 2017-03-09
HRP20160692T1 (hr) 2016-08-12
PT2714710T (pt) 2016-07-12
JP6425540B2 (ja) 2018-11-21
ZA201308446B (en) 2016-08-31
BR112013030830A2 (pt) 2016-08-30
DK2714710T3 (en) 2016-06-27
BR112013030830B1 (pt) 2019-12-03
SG195118A1 (en) 2013-12-30
US20140107358A1 (en) 2014-04-17
EP2714710B1 (en) 2016-04-06
KR101994805B1 (ko) 2019-07-01
CN103703014A (zh) 2014-04-02
US11053274B2 (en) 2021-07-06
ES2579175T3 (es) 2016-08-05
EA023991B1 (ru) 2016-08-31
CY1118150T1 (el) 2017-06-28
SI2714710T1 (sl) 2016-08-31
JP2014518199A (ja) 2014-07-28
RS54880B1 (sr) 2016-10-31
EP2714710A1 (en) 2014-04-09
JP6479912B2 (ja) 2019-03-06
WO2012164096A1 (en) 2012-12-06
CA2835981C (en) 2018-07-24
ME02454B (me) 2016-09-20
SMT201600206B (it) 2016-08-31
JP2018024673A (ja) 2018-02-15

Similar Documents

Publication Publication Date Title
EA201301316A1 (ru) Способ получения интермедиатов эстетрола
EA201391180A1 (ru) Способ получения оптически активных производных дигидробензофурана
EA201500173A1 (ru) Фунгицидные композиции
EA201591503A1 (ru) Производные нафтиридина, полезные в качестве антагонистов альфа-v-бета-6 интегрина
UA111626C2 (uk) Похідні дигідрохінолін-2-ону
EA201301315A1 (ru) Способ получения промежуточных соединений эстетрола
EA201390235A1 (ru) Способ получения карбонильных соединений
NZ707276A (en) Compounds useful in the synthesis of benzamide compounds
UA111333C2 (uk) Спосіб одержання l-аргінінової солі периндроприлу
IN2014DN00144A (ru)
CR20130597A (es) Isoxazolinas como agentes terapèuticos
EA201490998A1 (ru) Способ получения сложных эфиров (5-фтор-2-метил-3-хинолин-2-илметил-индол-1-ил)-уксусной кислоты
IN2014MN00850A (ru)
MX369470B (es) Medios y método para el tratamiento de tumores sólidos.
EA201291235A1 (ru) Новые способы
CY1111873T1 (el) Νεα μεθοδος παραλαβης της κρυσταλλικης μορφης v της αγομελατινης
EA201300792A1 (ru) Химические соединения
BR112013024361A2 (pt) novos compostos de azaspirodecanona como inibidores de hsl
CY1120784T1 (el) Νεα κρυσταλλικη μορφη
MX2015005592A (es) Método de preparación de los compuestos de ceramidas de alfa-galactosilo.
EA201300794A1 (ru) Новый способ синтеза агомелатина
EA201490019A1 (ru) Способ получения производных имидазола
EA201300650A1 (ru) Разделение энантиомеров производных триазина с использованием винной кислоты
MX2015001455A (es) Procedimiento multietapa para la preparacion de sales de metales alcalinos de esteres 4-hidroxi-2-oxo-2,5-dihidrofuran-3-carboxilicos especificos.
MX369283B (es) Preparacion de 2-amino-5-ciano-n, 3-dimetilbenzamida.

Legal Events

Date Code Title Description
PD1A Registration of transfer to a eurasian application by order of succession in title