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WO2007118717A3 - METHOD FOR PREPARING 4-[17β-METHOXY-17α-METHOXYMETHYL-3-OXOESTRA-4,9-DIEN-11β-YL]BENZALDEHYDE (E)-OXIME (ASOPRISNIL) - Google Patents

METHOD FOR PREPARING 4-[17β-METHOXY-17α-METHOXYMETHYL-3-OXOESTRA-4,9-DIEN-11β-YL]BENZALDEHYDE (E)-OXIME (ASOPRISNIL) Download PDF

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Publication number
WO2007118717A3
WO2007118717A3 PCT/EP2007/003723 EP2007003723W WO2007118717A3 WO 2007118717 A3 WO2007118717 A3 WO 2007118717A3 EP 2007003723 W EP2007003723 W EP 2007003723W WO 2007118717 A3 WO2007118717 A3 WO 2007118717A3
Authority
WO
WIPO (PCT)
Prior art keywords
asoprisnil
oxoestra
dien
benzaldehyde
methoxymethyl
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.)
Ceased
Application number
PCT/EP2007/003723
Other languages
French (fr)
Other versions
WO2007118717A2 (en
Inventor
Detlef Grawe
Sabine Gliesing
Hagen Gerecke
Peter Hoesel
Uwe Mueller
Thomas Michel
Robert Eilers
Uwe Knabe
Bernd Erhart
Michael Mosebach
David Voigtlaender
Ulf Tilstam
Juergen Jacke
Klaus Bahl
Ulf Bohlmann
Dieter Wehmeier
Michael Sander
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.)
Bayer Pharma AG
Original Assignee
Bayer Schering Pharma AG
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 Bayer Schering Pharma AG filed Critical Bayer Schering Pharma AG
Priority to AU2007237457A priority Critical patent/AU2007237457A1/en
Priority to BRPI0710517-7A priority patent/BRPI0710517A2/en
Priority to MX2008013336A priority patent/MX2008013336A/en
Priority to JP2009505800A priority patent/JP2009534345A/en
Priority to EP07724653A priority patent/EP2010555A2/en
Priority to CA2648537A priority patent/CA2648537C/en
Publication of WO2007118717A2 publication Critical patent/WO2007118717A2/en
Publication of WO2007118717A3 publication Critical patent/WO2007118717A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • 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
    • C07J41/0077—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom
    • C07J41/0083—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom substituted in position 11-beta by an optionally substituted phenyl group not further condensed with other rings
    • 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
    • A61K31/565—Compounds 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
    • A61P5/36—Antigestagens
    • 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
    • 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
    • C07J1/0051—Estrane derivatives
    • C07J1/0059—Estrane derivatives substituted in position 17 by a keto group
    • 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
    • C07J1/0051—Estrane derivatives
    • C07J1/0081—Substituted in position 17 alfa and 17 beta
    • 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
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Endocrinology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Diabetes (AREA)
  • Reproductive Health (AREA)
  • Epidemiology (AREA)
  • Steroid Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The present invention relates to a method for the reliable and reproducible preparation of 4-[17β-methoxy-17α-methoxymethyl-3-oxoestra-4,9-dien-llβ- yl]benzaldehyde (E)-oxime (asoprisnil) on the pilot and manufacturing scale. Asoprisnil, which is prepared by this method, is distinguished by a very good physical stability and is therefore particularly suitable for the manufacture of solid pharmaceutical forms (tablets, coated tablets, etc.).
PCT/EP2007/003723 2006-04-18 2007-04-17 METHOD FOR PREPARING 4-[17β-METHOXY-17α-METHOXYMETHYL-3-OXOESTRA-4,9-DIEN-11β-YL]BENZALDEHYDE (E)-OXIME (ASOPRISNIL) Ceased WO2007118717A2 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
AU2007237457A AU2007237457A1 (en) 2006-04-18 2007-04-17 Method for preparing 4-[17beta-methoxy-17alpha-methoxymethyl-3-oxoestra-4,9-dien-11beta-yl]benzaldehyde (E)-oxime (asoprisnil)
BRPI0710517-7A BRPI0710517A2 (en) 2006-04-18 2007-04-17 method for preparing 4- [17 beta-methoxy-17alpha-methoxymethyl-3-oxoestra-4,9-diean-11beta-yl] benzaldehyde (e) -oxime (asoprisnyl)
MX2008013336A MX2008013336A (en) 2006-04-18 2007-04-17 Method for preparing 4-[17î²-methoxy-17î±-methoxymethyl-3-oxoestr a-4,9-dien-11î²-yl]benzaldehyde (e)-oxime (asoprisnil).
JP2009505800A JP2009534345A (en) 2006-04-18 2007-04-17 Process for the preparation of 4- [17β-methoxy-17α-methoxymethyl-3-oxoestradi-4,9-dien-11β-yl] benzaldehyde (E) -oxime (assoprisnil)
EP07724653A EP2010555A2 (en) 2006-04-18 2007-04-17 Method for preparing 4-[17beta -methoxy-17 -alpha methoxymethyl-3-oxoestra-4,9-dien-11beta -yl]benzaldehyde (e)-oxime (asoprisnil)
CA2648537A CA2648537C (en) 2006-04-18 2007-04-17 Method for preparing 4-[17.beta.-methoxy-17.alpha.-methoxymethyl-3-oxoestra-4,9-dien-11.beta.-yl]benzaldehyde (e)-oxime (asoprisnil)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102006018888.8 2006-04-18
DE102006018888A DE102006018888A1 (en) 2006-04-18 2006-04-18 Process for the preparation of 4- [17beta-methoxy-17alpha-methoxymethyl-3-oxoestra-4,9-diene-11beta-yl] benzaldehyde (E) -oxime (asoprisnil)

Publications (2)

Publication Number Publication Date
WO2007118717A2 WO2007118717A2 (en) 2007-10-25
WO2007118717A3 true WO2007118717A3 (en) 2008-04-24

Family

ID=38536818

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2007/003723 Ceased WO2007118717A2 (en) 2006-04-18 2007-04-17 METHOD FOR PREPARING 4-[17β-METHOXY-17α-METHOXYMETHYL-3-OXOESTRA-4,9-DIEN-11β-YL]BENZALDEHYDE (E)-OXIME (ASOPRISNIL)

Country Status (12)

Country Link
EP (1) EP2010555A2 (en)
JP (1) JP2009534345A (en)
KR (1) KR20080110629A (en)
CN (1) CN101466724A (en)
AU (1) AU2007237457A1 (en)
BR (1) BRPI0710517A2 (en)
CA (2) CA2839228A1 (en)
DE (1) DE102006018888A1 (en)
MX (2) MX2007000450A (en)
RU (1) RU2008145098A (en)
WO (1) WO2007118717A2 (en)
ZA (1) ZA200809787B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108003210A (en) * 2018-01-24 2018-05-08 四川理工学院 A kind of preparation method of female steroid -4,9- diene -3,17- diketone

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR5183M (en) * 1966-03-04 1967-06-19
DD296931A5 (en) * 1987-08-28 1991-12-19 Jenapharm Gmbh Jena,De PROCESS FOR THE PREPARATION OF 13 BETA-ALKYL-5 (10), 9 (11) -GONADIEN DERIVATIVES
WO2001090137A2 (en) * 2000-05-23 2001-11-29 Schering Ag NOVEL SOLID BODY FORMS OF MESOPROGESTIN 11β-[4E-(HYDROXYIMINOMETHYL)-PHENYL]-17α-METHOXYMETHYL-17β-METHOXY-ESTRA-4,9-DIEN-3-ONE
DE10056675A1 (en) * 2000-11-10 2002-05-16 Jenapharm Gmbh Preparation of estradienyl-benzaldoxime derivative preparation in high yield, for use e.g. in treating endometriosis, from estradienone by multi-stage process including selective Grignard reaction
DE10311092A1 (en) * 2003-03-07 2004-10-07 Schering Ag Use of trifluoroacetic acid and cyclohexanone to prepare steroidal 17-ketones by Oppenauer oxidation
DE102004021060A1 (en) * 2004-04-29 2005-11-24 Schering Ag Pharmaceutical substance steroid production installation cross contamination reduction procedure uses special investigation techniques

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ZA8231B (en) * 1981-01-09 1982-11-24 Roussel Uclaf New 11 -substituted steroid derivatives, their preparation, their use as medicaments, the compositions containing them and the new intermediates thus obtained
US4910191A (en) * 1988-06-28 1990-03-20 Merrell Dow Pharmaceuticals Inc. 19-substituted progesterone derivatives useful as 19-hydroxylase inhibitors
DE4332283A1 (en) * 1993-09-20 1995-04-13 Jenapharm Gmbh Novel 11-benzaldoximestradiene derivatives, processes for their preparation and medicaments containing these compounds
DE10056676A1 (en) * 2000-11-10 2002-05-16 Jenapharm Gmbh Preparation of estradienyl-benzaldoxime derivative preparation in high yield, for use e.g. in treating endometriosis, from epoxy-estrenone by multi-stage process including selective Grignard reaction
JP4197890B2 (en) * 2001-05-24 2008-12-17 興和創薬株式会社 Method for oxidizing primary allyl alcohols

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR5183M (en) * 1966-03-04 1967-06-19
DD296931A5 (en) * 1987-08-28 1991-12-19 Jenapharm Gmbh Jena,De PROCESS FOR THE PREPARATION OF 13 BETA-ALKYL-5 (10), 9 (11) -GONADIEN DERIVATIVES
WO2001090137A2 (en) * 2000-05-23 2001-11-29 Schering Ag NOVEL SOLID BODY FORMS OF MESOPROGESTIN 11β-[4E-(HYDROXYIMINOMETHYL)-PHENYL]-17α-METHOXYMETHYL-17β-METHOXY-ESTRA-4,9-DIEN-3-ONE
DE10056675A1 (en) * 2000-11-10 2002-05-16 Jenapharm Gmbh Preparation of estradienyl-benzaldoxime derivative preparation in high yield, for use e.g. in treating endometriosis, from estradienone by multi-stage process including selective Grignard reaction
DE10311092A1 (en) * 2003-03-07 2004-10-07 Schering Ag Use of trifluoroacetic acid and cyclohexanone to prepare steroidal 17-ketones by Oppenauer oxidation
DE102004021060A1 (en) * 2004-04-29 2005-11-24 Schering Ag Pharmaceutical substance steroid production installation cross contamination reduction procedure uses special investigation techniques

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
GEBHARD R ET AL: "11,21-Bisphenyl-19-norpregnane derivatives are selective antiglucocorticoids", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, OXFORD, GB, vol. 7, no. 17, 9 September 1997 (1997-09-09), pages 2229 - 2234, XP004136418, ISSN: 0960-894X *
J. J. BROWN ET AL: "A novel isomerization of steroidal delta-4,9(10)-3-ketones", STEROIDS., vol. 1, 1963, USELSEVIER SCIENCE PUBLISHERS, NEW YORK, NY., pages 113 - 116, XP002454066 *
J. J. BROWN ET AL: "The preparation of steroidal delta-5(10),9(11)-3-ketones", STEROIDS., vol. 8, no. 1, 1966, USELSEVIER SCIENCE PUBLISHERS, NEW YORK, NY., pages 87 - 107, XP002454067 *
LIU A ET AL: "SYNTHESIS OF HIGH AFFINITY FLUORINE-SUBSTITUTED LIGANDS FOR THE ANDROGEN RECEPTOR. POTENTIAL AGENTS FOR IMAGING PROSTATIC CANCER BY POSITRON EMISSION TOMOGRAPHY", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY. WASHINGTON, US, vol. 35, no. 11, 29 May 1992 (1992-05-29), pages 2113 - 2129, XP002454065, ISSN: 0022-2623 *
MENZENBACH, B. ET AL: "Synthesis of potential metabolities of STS 557 (dienogest). 3. 17.alpha.-Hydroxymethyl-17.beta.-hydroxyestra-4,9-dien-3-one", PHARMAZIE , 39(7), 496-7 CODEN: PHARAT; ISSN: 0031-7144, 1984, XP002009736 *

Also Published As

Publication number Publication date
DE102006018888A1 (en) 2007-10-25
MX2007000450A (en) 2009-02-11
EP2010555A2 (en) 2009-01-07
WO2007118717A2 (en) 2007-10-25
ZA200809787B (en) 2010-01-27
CA2839228A1 (en) 2007-10-25
JP2009534345A (en) 2009-09-24
CA2648537C (en) 2014-09-23
CN101466724A (en) 2009-06-24
AU2007237457A1 (en) 2007-10-25
CA2648537A1 (en) 2007-10-25
MX2008013336A (en) 2008-10-31
BRPI0710517A2 (en) 2011-08-16
RU2008145098A (en) 2010-05-27
KR20080110629A (en) 2008-12-18

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