FR2404014A1 - Nouveaux steroides et leur procede de preparation - Google Patents

Nouveaux steroides et leur procede de preparation

Info

Publication number
FR2404014A1
FR2404014A1 FR7817206A FR7817206A FR2404014A1 FR 2404014 A1 FR2404014 A1 FR 2404014A1 FR 7817206 A FR7817206 A FR 7817206A FR 7817206 A FR7817206 A FR 7817206A FR 2404014 A1 FR2404014 A1 FR 2404014A1
Authority
FR
France
Prior art keywords
hydroxy
cholecalciferol
cholesterol
intermediates
preparing
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.)
Withdrawn
Application number
FR7817206A
Other languages
English (en)
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of FR2404014A1 publication Critical patent/FR2404014A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
    • C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
    • 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
    • C07J41/0094—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing nitrile radicals, including thiocyanide radicals
    • 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
    • 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
    • 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)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Steroid Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Pour synthétiser l'hydroxy-25 cholestérol et l'hydroxy-25 cholécalciférol à partir de matières premières dérivant de la bile des animaux, on transforme l'acide hyodésoxycholique ou un de ses esters en un ester alkylique d'acide hydroxy-3 beta DELTA 5-cholénique que l'on transforme en hydroxy-3 beta cyano-25 DELTA 5-cholène selon une série de stades où l'on stabilise le noyau stérol par mise en place d'un groupe protecteur en position 3, puis on allonge la chaîne carbonée en position 4 par un radical cyanure en position 25; on soumet le composé ainsi formé à une série de réactions le transformant en hydroxy-25 déhydro-7 cholestérol, que l'on peut ensuite irradier par la lumière ultraviolette pour obtenir l'hydroxy-25 cholécalciférol; l'invention décrit de nouveaux procédés améliorés pour préparer ces produits finals et de nouveaux composés formés comme intermédiaires ainsi que des procédés pour préparer ces intermédiaires. L'invention s'applique en particulier à une synthèse industrielle utilisant des appareillages courants et des matières premières peu coûteuses pour préparer, avec des rendements élevés, de l'hydroxy-25 cholestérol ou de l'hydroxy-25 cholécalciférol.
FR7817206A 1977-07-18 1978-06-08 Nouveaux steroides et leur procede de preparation Withdrawn FR2404014A1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US05/816,478 US4183852A (en) 1977-07-18 1977-07-18 Process for preparing 25-hydroxycholesterol

Publications (1)

Publication Number Publication Date
FR2404014A1 true FR2404014A1 (fr) 1979-04-20

Family

ID=25220729

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7817206A Withdrawn FR2404014A1 (fr) 1977-07-18 1978-06-08 Nouveaux steroides et leur procede de preparation

Country Status (7)

Country Link
US (1) US4183852A (fr)
JP (1) JPS5422359A (fr)
CA (1) CA1150238A (fr)
DE (1) DE2830019A1 (fr)
FR (1) FR2404014A1 (fr)
GB (1) GB1582678A (fr)
IT (1) IT1097264B (fr)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL60270A0 (en) * 1979-06-14 1980-09-16 Diamond Shamrock Corp Preparation of 25-ydroxycholesterol
US4336193A (en) * 1980-08-04 1982-06-22 Wisconsin Alumni Research Foundation Process for preparing vitamin D-lactones
US4351767A (en) * 1981-06-29 1982-09-28 Kaiser Emil T Synthesis of 24,25-dihydroxycholesterol
US4411833A (en) * 1982-05-26 1983-10-25 Wisconsin Alumni Research Foundation Method for preparing 26,26,26,27,27,27-hexafluoro-1α,25-dihydroxycholesterol
CA1312637C (fr) * 1987-09-17 1993-01-12 Ronald C. Banko Dispositif de rangement d'objets en piles
JPH036144U (fr) * 1989-06-08 1991-01-22
JPH07504563A (ja) * 1992-02-28 1995-05-25 ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア 副産物としてコレステロールを同時に製造しつつ卵黄を脱コレステロールする方法
WO1997042215A1 (fr) * 1996-05-06 1997-11-13 Bionumerik Pharmaceuticals, Inc. Procede de preparation de 27-hydroxy cholesterol et de derives apparentes
JP2006503819A (ja) * 2002-08-29 2006-02-02 ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア 骨形成を増進するための作用剤および方法
JP4438308B2 (ja) * 2003-04-07 2010-03-24 三菱化学株式会社 ステロイド化合物の製造方法
US9532994B2 (en) * 2003-08-29 2017-01-03 The Regents Of The University Of California Agents and methods for enhancing bone formation by oxysterols in combination with bone morphogenic proteins
ATE422028T1 (de) * 2005-04-23 2009-02-15 Ixetic Mac Gmbh Axialkolbenmaschine
AU2006284650A1 (en) * 2005-09-02 2007-03-08 The Regents Of The University Of California Osteogenic and anti-adipogenic oxysterols
AU2007217366A1 (en) * 2006-02-27 2007-08-30 The Regents Of The University Of California Oxysterol compounds and the hedgehog pathway
WO2008011071A2 (fr) * 2006-07-19 2008-01-24 The Regents Of The University Of California Interactions des voies de signaux hedgehog et du récepteur x hépatique
AU2007339325A1 (en) 2006-12-19 2008-07-10 The Regents Of The University Of California Inhibition of PPAR gamma expression by specific osteogenic oxysterols
WO2008115469A2 (fr) * 2007-03-16 2008-09-25 The Regents Of The University Of California Rôle de la signalisation par hérisson dans l'athérosclérose et les maladies cardiovasculaires
US9526737B2 (en) * 2007-12-03 2016-12-27 The Regents Of The University Of California Oxysterols for activation of hedgehog signaling, osteoinduction, antiadipogenesis, and Wnt signaling
WO2013169399A1 (fr) 2012-05-07 2013-11-14 The Regents Of The University Of California Oxy133, un analogue de l'oxystérol, induisant l'ostéo-genèse et la signalisation hedgehog et inhibant l'adipogenèse
ES2886506T3 (es) * 2013-03-13 2021-12-20 Sage Therapeutics Inc Esteroides neuroactivos
US9683009B2 (en) 2013-05-02 2017-06-20 The Regents Of The University Of California Bone-selective osteogenic oxysterol-bone targeting agents
JP6882996B2 (ja) * 2015-07-06 2021-06-02 セージ セラピューティクス， インコーポレイテッド オキシステロールおよびそれらの使用の方法
HUE055199T2 (hu) 2015-07-06 2021-11-29 Sage Therapeutics Inc Oxiszterolok és alkalmazási eljárásaik
WO2017193046A1 (fr) 2016-05-06 2017-11-09 Sage Therapeutics, Inc. Oxystérols et méthodes d'utilisation associées
MA45598B1 (fr) 2016-07-07 2021-09-30 Sage Therapeutics Inc Stéroles 24-hydroxylés substitués en position 11 pour le traitement des maladies liées au récepteur nmda
CA3038900A1 (fr) 2016-09-30 2018-04-05 Sage Therapeutics, Inc. Oxysterols substitues en c7 et procedes en tant que modulateurs nmda
WO2020225830A1 (fr) 2019-05-09 2020-11-12 Fermenta Biotech Limited Nouveau procédé de synthèse de 25-oh cholestérol/calcifédiol à partir de phytostérol
CN112897512B (zh) * 2021-02-03 2022-11-04 中国科学院物理研究所 碳纳米管分散体和选择性分离碳纳米管的方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3257384A (en) * 1963-01-04 1966-06-21 Upjohn Co Derivatives of 25-azacholesterol and 22-oxa-25-azacholesterol
US3833622A (en) * 1969-03-17 1974-09-03 Upjohn Co Crystalline 25-hydroxycholecalciferol hydrate and structurally related compounds

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
EXBK/73 *

Also Published As

Publication number Publication date
CA1150238A (fr) 1983-07-19
JPS5751840B2 (fr) 1982-11-04
JPS5422359A (en) 1979-02-20
DE2830019A1 (de) 1979-01-25
GB1582678A (en) 1981-01-14
IT1097264B (it) 1985-08-31
IT7824940A0 (it) 1978-06-23
US4183852A (en) 1980-01-15

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