EA201290334A1 - Способы синтеза и очистки дезоксихолевой кислоты - Google Patents

Способы синтеза и очистки дезоксихолевой кислоты

Info

Publication number
EA201290334A1
EA201290334A1 EA201290334A EA201290334A EA201290334A1 EA 201290334 A1 EA201290334 A1 EA 201290334A1 EA 201290334 A EA201290334 A EA 201290334A EA 201290334 A EA201290334 A EA 201290334A EA 201290334 A1 EA201290334 A1 EA 201290334A1
Authority
EA
Eurasian Patent Office
Prior art keywords
methods
synthesis
acid
dezoxyleic
cleaning
Prior art date
Application number
EA201290334A
Other languages
English (en)
Other versions
EA031768B1 (ru
Inventor
Роберт М. Мориарти
Джон Грегори Рейд
Рой А. Сваринген Мл.
Original Assignee
Китера Биофармасьютикалз, Инк.
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 Китера Биофармасьютикалз, Инк. filed Critical Китера Биофармасьютикалз, Инк.
Publication of EA201290334A1 publication Critical patent/EA201290334A1/ru
Publication of EA031768B1 publication Critical patent/EA031768B1/ru

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
    • C07J9/005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane containing a carboxylic function directly attached or attached by a chain containing only carbon atoms to the cyclopenta[a]hydrophenanthrene skeleton
    • 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
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • 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
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C07J1/0003—Androstane derivatives
    • C07J1/0011—Androstane derivatives substituted in position 17 by a keto group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
    • C07J13/007—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17 with double bond in position 17 (20)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J21/005—Ketals
    • C07J21/008—Ketals at position 17
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
    • C07J5/0046—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa
    • C07J5/0053—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa not substituted in position 16
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/0055—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
    • C07J41/0061—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives one of the carbon atoms being part of an amide group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
    • 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)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Diabetes (AREA)
  • Engineering & Computer Science (AREA)
  • Child & Adolescent Psychology (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Steroid Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

В настоящем изобретении предложены способы синтеза для получения дезоксихолевой кислоты и промежуточных соединений, синтетическая дезоксихолевая кислота высокой чистоты, композиции и способы применения. Также предложены способы синтеза 12-кето или 12-α-гидроксистероидов из Δ-9,11-ен, 11-кето или 11-гидрокси-β-стероидов. Настоящее изобретение также относится к новым соединениям, полученным в ходе синтеза. Настоящее изобретение также относится к синтезу дезоксихолевой кислоты, начиная с гидрокортизона.
EA201290334A 2009-12-18 2010-12-17 Способы синтеза промежуточных соединений для применения в синтезе дезоксихолевой кислоты EA031768B1 (ru)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US28813209P 2009-12-18 2009-12-18
US30200710P 2010-02-05 2010-02-05
US30381610P 2010-02-12 2010-02-12
GB1008726A GB2480632A (en) 2010-05-25 2010-05-25 Preparation of 12-keto and 12-alpha-hydroxy steroids
US34868610P 2010-05-26 2010-05-26
PCT/US2010/061150 WO2011075701A2 (en) 2009-12-18 2010-12-17 Methods for the purification of deoxycholic acid

Publications (2)

Publication Number Publication Date
EA201290334A1 true EA201290334A1 (ru) 2013-06-28
EA031768B1 EA031768B1 (ru) 2019-02-28

Family

ID=42341289

Family Applications (2)

Application Number Title Priority Date Filing Date
EA201290334A EA031768B1 (ru) 2009-12-18 2010-12-17 Способы синтеза промежуточных соединений для применения в синтезе дезоксихолевой кислоты
EA201791511A EA035380B1 (ru) 2009-12-18 2010-12-17 Способ и композиция для уменьшения подкожных жировых отложений

Family Applications After (1)

Application Number Title Priority Date Filing Date
EA201791511A EA035380B1 (ru) 2009-12-18 2010-12-17 Способ и композиция для уменьшения подкожных жировых отложений

Country Status (16)

Country Link
US (5) US20130137884A1 (ru)
EP (2) EP3040342A1 (ru)
JP (2) JP6393023B2 (ru)
KR (3) KR101862599B1 (ru)
CN (3) CN107011401A (ru)
AU (1) AU2010330760B2 (ru)
CA (1) CA2782478A1 (ru)
EA (2) EA031768B1 (ru)
ES (1) ES2575559T3 (ru)
GB (1) GB2480632A (ru)
IL (2) IL220225A0 (ru)
MY (1) MY167891A (ru)
NZ (1) NZ700195A (ru)
SG (3) SG181768A1 (ru)
WO (1) WO2011075701A2 (ru)
ZA (1) ZA201204388B (ru)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060127468A1 (en) 2004-05-19 2006-06-15 Kolodney Michael S Methods and related compositions for reduction of fat and skin tightening
US8101593B2 (en) 2009-03-03 2012-01-24 Kythera Biopharmaceuticals, Inc. Formulations of deoxycholic acid and salts thereof
GB2480632A (en) 2010-05-25 2011-11-30 Kythera Biopharmaceuticals Inc Preparation of 12-keto and 12-alpha-hydroxy steroids
US20120237492A1 (en) 2011-02-18 2012-09-20 Kythera Biopharmaceuticals, Inc. Treatment of submental fat
US8653058B2 (en) 2011-04-05 2014-02-18 Kythera Biopharmaceuticals, Inc. Compositions comprising deoxycholic acid and salts thereof suitable for use in treating fat deposits
TWI572616B (zh) * 2011-06-16 2017-03-01 凱瑟拉生物製藥有限公司 去氧膽酸之組成物及用途及其相關方法
WO2013044119A1 (en) * 2011-09-22 2013-03-28 Kythera Biopharmaceuticals, Inc. Compositions and methods related to deoxycholic acid and its polymorphs
US20130102580A1 (en) * 2011-09-22 2013-04-25 Kythera Biopharmaceuticals, Inc. Compositions and methods related to deoxycholic acid and its polymorphs
CN104447929B (zh) * 2014-10-28 2016-06-29 湖南科瑞生物制药股份有限公司 一种合成3-羰基-4-雄烯-17β羧酸的方法
CN106146593B (zh) * 2015-04-14 2021-06-01 南京迈诺威医药科技有限公司 一种制备去氧胆酸的方法
CN106046093A (zh) * 2016-05-30 2016-10-26 华东师范大学 一种石胆酸的合成方法
US11117925B2 (en) 2016-06-06 2021-09-14 Bionice, S.L.U. Methods for the preparation of deoxycholic acid, and intermediates useful in the preparation of deoxycholic acid
JP2019509333A (ja) * 2016-08-11 2019-04-04 サムスン ライフ パブリック ウェルフェア ファウンデーションＳａｍｓｕｎｇ Ｌｉｆｅ Ｐｕｂｌｉｃ Ｗｅｌｆａｒｅ Ｆｏｕｎｄａｔｉｏｎ デオキシコール酸を有効成分に含む脱毛の予防、改善、または治療用組成物
JP6937893B2 (ja) 2017-08-03 2021-09-22 メディトックス インク． 胆汁酸類を製造するための方法
JP6899529B2 (ja) 2017-08-10 2021-07-07 パナソニックＩｐマネジメント株式会社 冷凍サイクル用作動媒体および冷凍サイクルシステム
CN114478676B (zh) * 2022-02-18 2024-05-10 国药集团化学试剂有限公司 一种脱氧胆酸钠的制备方法
CN116444597A (zh) * 2023-03-30 2023-07-18 南京迈诺威医药科技有限公司 一种制备去氧胆酸中间体和去氧胆酸的方法

Family Cites Families (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US53446A (en) 1866-03-27 Improvement in cultivators
US2321598A (en) 1940-10-07 1943-06-15 George A Breon & Company Inc Preparation of desoxycholic acid
US2509248A (en) * 1947-09-05 1950-05-30 Merck & Co Inc Process for producing delta9, 11-3(alpha)-hydroxy-17-ketoetiocholene
GB695504A (en) 1950-10-18 1953-08-12 Drug Res Inc Method of isolating and purifying cholic and desoxycholic acids
GB716670A (en) 1951-06-19 1954-10-13 Armour & Co Improved process for purifying desoxycholic acid from contaminating cholic acid
US2651643A (en) * 1951-06-19 1953-09-08 Armour & Co Purification of desoxycholic acid
US2891972A (en) 1952-08-19 1959-06-23 Drug Res Inc Process of separating desoxycholic acid from mixed crude bile acids or salts thereof
US3533908A (en) 1967-05-19 1970-10-13 Brown Co Porous paperboard sheet having plastic microspheres therein
IT1202370B (it) 1976-07-12 1989-02-09 Hoffmann La Roche Soluzioni inietabili in cui l'atti vita' emolitica degli agenti di formazione di micelle naturali e' evitata mediante l'aggiunta di lipoidi e relativi prodotti
FR2446293A1 (fr) 1978-12-11 1980-08-08 Roussel Uclaf Procede de purification de l'acide chenodesoxycholique
IT8167097A0 (it) 1981-01-26 1981-01-26 Unilever Nv Composizione cosmetica per il trattamento della pelle o dei capelli
AU618350B2 (en) 1988-04-08 1991-12-19 Aventis Pharma S.A. 9-alpha-hydroxy-17-methylene steroids, process for their preparation and their use in the preparation of corticosteroids
US5085864A (en) 1989-10-30 1992-02-04 Abbott Laboratories Injectable formulation for lipophilic drugs
CA2033725C (en) 1990-01-24 2001-05-29 Folker Pittrof Pharmaceutical and cosmetic compositions containing a salt of cholanic acid
MX9701430A (es) 1994-07-25 1997-12-31 Nda Int Inc Un metodo de tratamiento de dependencia quimica en mamiferos y una composicion para el mismo.
US20020107291A1 (en) 1997-05-26 2002-08-08 Vincenzo De Tommaso Clear, injectable formulation of an anesthetic compound
IL123998A (en) 1998-04-08 2004-09-27 Galmed Int Ltd Conjugates of bile salts and pharmaceutical preparations containing them
US6417179B1 (en) 1998-10-13 2002-07-09 Craig G. Burkhart Ear wax solution
AU2879300A (en) * 1999-02-12 2000-08-29 Cellpath, Inc. Methods for anti-tumor therapy
JP2004500378A (ja) 2000-02-04 2004-01-08 ヨー、セオ、ホン 胆汁酸を含有する清浄水溶液製型の製造
AU2002257453B2 (en) * 2001-05-22 2008-04-10 Inflazyme Pharmaceuticals Limited Process for the production of 6, 7 - dihydroxy steroid compounds by allylic oxidation of steroid - 5 - ene compounds to steroid - 5 - ene - 7 - one compounds followed by hydroboration and oxidation and intermediates of this process
EP3424508B1 (en) 2004-05-19 2021-05-05 Lundquist Institute for Biomedical Innovation at Harbor-UCLA Medical Center Use of sodium deoxycholate for the removal of localized fat accumulation
US20060127468A1 (en) 2004-05-19 2006-06-15 Kolodney Michael S Methods and related compositions for reduction of fat and skin tightening
US7754230B2 (en) 2004-05-19 2010-07-13 The Regents Of The University Of California Methods and related compositions for reduction of fat
US20060222695A1 (en) 2005-04-01 2006-10-05 Filiberto Zadini Deoxycholic acid liposome-based dermatological topical preparation
CN101148468A (zh) 2006-09-19 2008-03-26 天津科技大学 以动物胆汁为原料高效提取胆红素和胆汁酸技术
EA017714B1 (ru) * 2007-01-19 2013-02-28 Интерсепт Фармасьютикалз, Инк. Модуляторы tgr5 и способы их применения
JOP20180077A1 (ar) 2007-06-19 2019-01-30 Kythera Biopharmaceuticals Inc تركيبات وطرق لحمض صفراوي تخليقي
US20080318870A1 (en) 2007-06-19 2008-12-25 Kythera Biopharmaceuticals, Inc. Synthetic bile acid compositions and methods
WO2008157635A2 (en) 2007-06-19 2008-12-24 Kythera Biopharmaceuticals, Inc. Synthetic bile acid composition, method, and preparation
GB0716670D0 (en) 2007-08-28 2007-10-03 Owen Peter Electrical back box installation aid and installation method
PL2300489T3 (pl) * 2008-06-06 2016-11-30 Sposoby wytwarzania 17-alkinylo-7-hydroksysteroidów i związków pokrewnych
GB2480632A (en) 2010-05-25 2011-11-30 Kythera Biopharmaceuticals Inc Preparation of 12-keto and 12-alpha-hydroxy steroids
TWI572616B (zh) 2011-06-16 2017-03-01 凱瑟拉生物製藥有限公司 去氧膽酸之組成物及用途及其相關方法
US20130102580A1 (en) 2011-09-22 2013-04-25 Kythera Biopharmaceuticals, Inc. Compositions and methods related to deoxycholic acid and its polymorphs

Also Published As

Publication number Publication date
US20190135855A1 (en) 2019-05-09
SG10201509046TA (en) 2015-12-30
KR20180059568A (ko) 2018-06-04
US20200095274A1 (en) 2020-03-26
CN107011401A (zh) 2017-08-04
ES2575559T3 (es) 2016-06-29
EA031768B1 (ru) 2019-02-28
GB2480632A (en) 2011-11-30
US20170320905A1 (en) 2017-11-09
EP2513132A2 (en) 2012-10-24
JP2016193948A (ja) 2016-11-17
EA201791511A1 (ru) 2018-03-30
US9683007B2 (en) 2017-06-20
JP2013515006A (ja) 2013-05-02
KR20170049635A (ko) 2017-05-10
EP2513132B1 (en) 2016-03-09
JP6568025B2 (ja) 2019-08-28
EP3040342A1 (en) 2016-07-06
MY167891A (en) 2018-09-26
SG181768A1 (en) 2012-07-30
ZA201204388B (en) 2013-07-31
CN102812035A (zh) 2012-12-05
CA2782478A1 (en) 2011-06-23
CN106955287A (zh) 2017-07-18
IL220225A0 (en) 2012-07-31
US20150141679A1 (en) 2015-05-21
AU2010330760B2 (en) 2015-01-22
WO2011075701A4 (en) 2012-09-13
KR102058420B1 (ko) 2019-12-24
KR20120107982A (ko) 2012-10-04
GB201008726D0 (en) 2010-07-07
KR101862599B1 (ko) 2018-05-31
AU2010330760A1 (en) 2012-06-21
US10472384B2 (en) 2019-11-12
WO2011075701A3 (en) 2012-07-26
NZ700195A (en) 2016-03-31
US20130137884A1 (en) 2013-05-30
US10005813B2 (en) 2018-06-26
US10981946B2 (en) 2021-04-20
WO2011075701A2 (en) 2011-06-23
EA035380B1 (ru) 2020-06-04
EP2513132B9 (en) 2017-12-27
SG10201803507YA (en) 2018-05-30
JP6393023B2 (ja) 2018-09-19
IL261526A (en) 2018-10-31
KR101787719B1 (ko) 2017-10-18

Similar Documents

Publication Publication Date Title
EA201290334A1 (ru) Способы синтеза и очистки дезоксихолевой кислоты
EA201070429A1 (ru) Кристаллические пептидные кето-эпоксидные ингибиторы протеаз и синтез кето-эпоксидов аминокислот
EA201270575A1 (ru) Соединения
NZ612647A (en) Anti-bcma antibodies
MX353461B (es) PROCESOS PARA PREPARAR COMPUESTOS ÚTILES COMO INHIBIDORES DE CINASA ATAXIA TELANGIECTASIA MUTADA Y Rad3 RELACIONADOS (ATR).
EA200971078A1 (ru) Противовирусные соединения
MX2018009945A (es) Composiciones y metodos novedosos para el tratamiento de las enfermedades relacionadas con la inmunidad.
CR11313A (es) Composiciones y metodos de uso para anticuerpos contra la esclerostina
EA201390579A1 (ru) Производные хиназолин-4(3h)-она, используемые как ингибиторы pi3-киназы
CL2009000503A1 (es) Proceso de preparacion de compuestos derivados de acido 2-amino-5-cianobenzoico-3-sustituidos o 1h-pirazol-5-carboxamida.
MX2015000479A (es) Metodos para sintetizar bloque de construccion de amatoxina y amatoxinas.
MX350211B (es) Proceso para la preparacion del etil-ester del acido n- (4-ciclohexil-3-trifluoro-metil-benciloxi) -acetimidico.
MY162312A (en) Synthesis of 18f-radiolabeled styrylpyridines from tosylate precersors and stable pharmaceutical compositions thereof
SG178920A1 (en) Novel polymorphs of rebaudioside c and methods for making and using the same
TW201206878A (en) A method of producing ingenol-3-angelate
MX2018014164A (es) Intermedios para la sintesis de derivados de acido biliar, en particular, de acido obeticolico.
IN2012DN05209A (ru)
MX2010004546A (es) Nuevos intermedios de pregabalina y procedimiento para prepararlos y para preparar pregabalina.
IN2014CN03854A (ru)
EA201200820A1 (ru) Способ синтеза промежуточных продуктов, применимых для получения замещенных индазолов и азаиндазолов
EA201001870A1 (ru) Новые кристаллические формы рабепразола натрия
EA200602049A1 (ru) Пролекарства стероидов с андрогенным действием
ATE518828T1 (de) Ein-topf-verfahren zur herstellung von 3-(2,2,2- trimethylhydrazinium)propionat-dihydrat
EA201690467A1 (ru) Промышленный способ синтеза улипристала ацетата и его 4'-ацетильного аналога
EA201291235A1 (ru) Новые способы

Legal Events

Date Code Title Description
MM4A Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s)

Designated state(s): AM AZ BY KZ KG MD TJ TM