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ES2086201T3 - Nuevo procedimiento de preparacion de esteroides 16-alfa-metilados. - Google Patents

Nuevo procedimiento de preparacion de esteroides 16-alfa-metilados.

Info

Publication number
ES2086201T3
ES2086201T3 ES93401482T ES93401482T ES2086201T3 ES 2086201 T3 ES2086201 T3 ES 2086201T3 ES 93401482 T ES93401482 T ES 93401482T ES 93401482 T ES93401482 T ES 93401482T ES 2086201 T3 ES2086201 T3 ES 2086201T3
Authority
ES
Spain
Prior art keywords
alpha
hydrogen
beta
delta
hydroxy
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
ES93401482T
Other languages
English (en)
Inventor
Jean Buendia
Patrick Roussel
Michel Vivat
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.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf SA
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 Roussel Uclaf SA filed Critical Roussel Uclaf SA
Application granted granted Critical
Publication of ES2086201T3 publication Critical patent/ES2086201T3/es
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0005—Oxygen-containing hetero ring
    • C07J71/001—Oxiranes
    • C07J71/0015—Oxiranes at position 9(11)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • C07J5/0061—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 substituted in position 16
    • C07J5/0069—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 substituted in position 16 by a saturated or unsaturated hydrocarbon group
    • C07J5/0076—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 substituted in position 16 by a saturated or unsaturated hydrocarbon group by an alkyl group

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pain & Pain Management (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Rheumatology (AREA)
  • Veterinary Medicine (AREA)
  • Steroid Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Breeding Of Plants And Reproduction By Means Of Culturing (AREA)

Abstract

LA INVENCION CONCIERNE A UN NUEVO PROCESO PARA PREPARAR LOS COMPUESTOS DE FORMULA (I), EN LA CUAL LOS CICLOS A Y B REPRESENTAN UN RESTO 3-CETO 4 6-R3, EVENTUALMENTE BAJO FORMA PROTEGIDA EN 3, O 3-CETO 1,4 6-R3, R ES METILO O -CH2OR'' DONDE R'' ES HIDROGENO O UN RESTO ETER O ESTER, R1 Y R2 FORMAN UN EPOXIDO EN , UN SEGUNDO ENLACE, O R1 ES HIDROGENO, CETONA O HIDROXI EN O , EVENTUALMENTE BAJO FORMA ETERIFICADA O ESTERIFICADA, Y R2 ES HIDROGENO, O R1 ES HIDROGENO Y R2 ES -HIDROXI, O R1 ES -HIDROXI EVENTUALMENTE ETERIFICADO O ESTERIFICADO Y R2 ES UN FLUOR O UN BROMO EN , R3 ES HIDROGENO, FLUOR O METILO EN O , SEGUN EL CUAL SE TRATA UN DERIVADO 16(17) POR UN AGENTE DE METILACION, DESPUES POR HIDROLISIS INTERMEDIARIA Y OXIDO ENOL ASI OBTENIDO POR EL OXIGENO MOLECULAR EN PRESENCIA DE UN REDUCTOR APROPIADO. LOS COMPUESTOS (I) SON ANTIINFLAMATORIOS CONOCIDOS O PRECURSORES POSIBLES.
ES93401482T 1992-06-11 1993-06-10 Nuevo procedimiento de preparacion de esteroides 16-alfa-metilados. Expired - Lifetime ES2086201T3 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR929207048A FR2692266B1 (fr) 1992-06-11 1992-06-11 Nouveau procede de preparation de sterouides 16 alpha-methyles.

Publications (1)

Publication Number Publication Date
ES2086201T3 true ES2086201T3 (es) 1996-06-16

Family

ID=9430628

Family Applications (1)

Application Number Title Priority Date Filing Date
ES93401482T Expired - Lifetime ES2086201T3 (es) 1992-06-11 1993-06-10 Nuevo procedimiento de preparacion de esteroides 16-alfa-metilados.

Country Status (18)

Country Link
US (2) US6194565B1 (es)
EP (1) EP0574318B1 (es)
JP (1) JP3349554B2 (es)
KR (1) KR100274368B1 (es)
CN (1) CN1052489C (es)
AT (1) ATE136902T1 (es)
AU (1) AU666945B2 (es)
CA (1) CA2098148C (es)
DE (1) DE69302220T2 (es)
DK (1) DK0574318T3 (es)
ES (1) ES2086201T3 (es)
FR (1) FR2692266B1 (es)
GR (1) GR3019664T3 (es)
HU (1) HU213683B (es)
MX (1) MX9303420A (es)
RU (1) RU2125575C1 (es)
TW (1) TWI222976B (es)
ZA (1) ZA934144B (es)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2700548B1 (fr) * 1993-01-20 1995-03-03 Roussel Uclaf Nouveau procédé de préparation de stéroïdes 16 alpha-méthylés.
US6040468A (en) * 1996-10-25 2000-03-21 Alcon Laboratories, Inc. Method of preparing 16α, 17α-dialkylated steroids
CN100387611C (zh) * 2006-02-23 2008-05-14 中国科学院上海有机化学研究所 一类16α-溴代甾体化合物及其合成方法
CN101168555B (zh) * 2006-10-27 2011-05-04 天津药业研究院有限公司 一种药物及其衍生物的制备
WO2009155056A2 (en) 2008-05-28 2009-12-23 Validus Genetics Non-hormonal steroid modulators of nf-kb for treatment of disease
US20120178124A1 (en) 2009-01-07 2012-07-12 Mitsubishi Chemical Corporation Sterol side chain-cleaving enzyme protein and use thereof
US9198921B2 (en) 2010-04-05 2015-12-01 Reveragen Biopharma, Inc. Non-hormonal steroid modulators of NF-κB for treatment of disease
CN103936809B (zh) * 2014-04-03 2017-01-04 上海新华联制药有限公司 一种改进的地塞米松磷酸钠中间体制备方法
US10799514B2 (en) 2015-06-29 2020-10-13 Reveragen Biopharma, Inc. Non-hormonal steroid modulators of NF-kappa beta for treatment of disease
CN105693802B (zh) * 2016-04-12 2017-08-25 湖南新合新生物医药有限公司 16β‑甲基甾族化合物的制备方法
RU2663484C1 (ru) * 2017-05-18 2018-08-06 Федеральное государственное бюджетное образовательное учреждение высшего образования "Московский государственный университет имени М.В. Ломоносова" (МГУ) СПОСОБ ПОЛУЧЕНИЯ 6α-МЕТИЛГИДРОКОРТИЗОНА ИЛИ ЕГО ЭФИРОВ ИЗ 21-АЦЕТАТА ГИДРОКОРТИЗОНА
US11382922B2 (en) 2019-03-07 2022-07-12 Reveragen Biopharma, Inc. Aqueous oral pharmaceutical suspension compositions
CN115322242B (zh) * 2022-09-14 2023-09-12 山东赛托生物科技股份有限公司 一种高品质甾体药物中间体的制备方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3876633A (en) * 1973-02-21 1975-04-08 Omni Research Processes and intermediates for 16-substituted corticoid synthesis
GB2001990B (en) * 1977-07-16 1982-01-13 Lark Spa Process for the preparation of prednisolone derivatives
US4530795A (en) * 1984-02-27 1985-07-23 The Upjohn Company Process for preparation of 16 α-methyl corticoids from Δ16 -steroids
JPH085910B2 (ja) * 1986-06-04 1996-01-24 ジ・アップジョン・カンパニー １６α―メチル化方法
FR2678275B1 (fr) * 1991-06-25 1995-06-23 Roussel Uclaf Nouveaux sterouides 16-methyl substitue derives de la pregna 1,4-diene 3,20-dione leur preparation, leur application a la preparation de sterouides 16-methylene et nouveaux intermediaires.

Also Published As

Publication number Publication date
HUT64771A (en) 1994-02-28
CN1052489C (zh) 2000-05-17
ATE136902T1 (de) 1996-05-15
MX9303420A (es) 1994-01-31
CA2098148A1 (fr) 1993-12-12
GR3019664T3 (en) 1996-07-31
FR2692266A1 (fr) 1993-12-17
DE69302220D1 (de) 1996-05-23
AU4120293A (en) 1993-12-23
ZA934144B (en) 1994-06-13
CN1083487A (zh) 1994-03-09
DK0574318T3 (da) 1996-07-29
EP0574318B1 (fr) 1996-04-17
DE69302220T2 (de) 1996-10-24
EP0574318A1 (fr) 1993-12-15
FR2692266B1 (fr) 1994-08-05
KR100274368B1 (ko) 2001-02-01
CA2098148C (fr) 2004-05-04
AU666945B2 (en) 1996-02-29
HU9301693D0 (en) 1993-09-28
RU2125575C1 (ru) 1999-01-27
HU213683B (en) 1997-09-29
JPH0656879A (ja) 1994-03-01
TWI222976B (en) 2004-11-01
US6194565B1 (en) 2001-02-27
US5731447A (en) 1998-03-24
JP3349554B2 (ja) 2002-11-25

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