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GB1452179A - 3-oximes of steroids - Google Patents

3-oximes of steroids

Info

Publication number
GB1452179A
GB1452179A GB916974A GB916974A GB1452179A GB 1452179 A GB1452179 A GB 1452179A GB 916974 A GB916974 A GB 916974A GB 916974 A GB916974 A GB 916974A GB 1452179 A GB1452179 A GB 1452179A
Authority
GB
United Kingdom
Prior art keywords
alkyl
ethisterone
cycloalkyl
reaction
oximes
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
Application number
GB916974A
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.)
Ortho Pharmaceutical Corp
Original Assignee
Ortho Pharmaceutical Corp
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 Ortho Pharmaceutical Corp filed Critical Ortho Pharmaceutical Corp
Publication of GB1452179A publication Critical patent/GB1452179A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07J1/0033—Androstane derivatives substituted in position 17 alfa and 17 beta
    • C07J1/004—Androstane derivatives substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being an unsaturated hydrocarbon group
    • C07J1/0048—Alkynyl derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton
    • C07J41/0016—Oximes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Steroid Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1452179 Steroid 3-oximes ORTHO PHARMACEUTICAL CORP 28 Feb 1974 [1 March 1973] 9169/74 Heading C2U The invention comprises compounds of formulae wherein R 1 is H or COR 2 ; R 2 is C 1-8 alkyl, phenyl, C 3-6 cycloalkyl, adamantyl or C 1-5 trihaloalkyl; R 3 is C 2-5 alkynyl, C 3-5 alkadienyl or C 3-6 cycloalkyl; R 4 is H, C 1-5 alkyl, N-(C 1-5 alkyl) carbamoyl or C 3-5 cycloalkyl; and R 5 is C 1-5 alkyl; with the proiiso that (i) in compounds I when R 1 is H or acetyl then R 4 is not H, and (ii) in compounds II when R 3 is alkynyl or alkadienyl then R 2 is not alkyl. Preparation is from the corresponding 3-ones by reaction with an appropriate hydroxylamine salt in the presence of a base, optionally followed by 17- esterification, or separation of syn and anti isomers by fractional crystallization or column chromatography. Also, ethisterone acetate oxime is converted to its o-(N-methylcarbamoyl) derivative by reaction with methyl isocyanate. The oximes of ethisterone and ethisterone acetate are separated into their syn and anti isomers by column chromatography on silica gel (Ex. III). Ethisterone is converted to its benzoate and cyclopropane-, cyclobutane-, and cyclopentanecarboxylates by reaction with the appropriate carboxylic acids in the presence of trifluoroacetic anhydride (Ex. IV). The cyclopropanecarboxylate is also prepared using cyclopropanecarbonyl chloride in refluxing benzene (Ex. 1). Oral antilittering compositions comprise a compound I and a carrier.
GB916974A 1973-03-01 1974-02-28 3-oximes of steroids Expired GB1452179A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US33723673A 1973-03-01 1973-03-01

Publications (1)

Publication Number Publication Date
GB1452179A true GB1452179A (en) 1976-10-13

Family

ID=23319690

Family Applications (1)

Application Number Title Priority Date Filing Date
GB916974A Expired GB1452179A (en) 1973-03-01 1974-02-28 3-oximes of steroids

Country Status (7)

Country Link
JP (1) JPS5926640B2 (en)
AT (1) AT343292B (en)
CA (1) CA1034942A (en)
CH (1) CH606108A5 (en)
DE (1) DE2409648A1 (en)
FR (1) FR2219783B1 (en)
GB (1) GB1452179A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005000867A1 (en) * 2003-06-30 2005-01-06 Richter Gedeon Vegyészeti Gyár Rt. PURE D-(17α)-13-ETHYL-17-HYDROXY-18,19-DINORPREGN-4-ENE-20-YNE-3-ONE-3E- AND -3Z-OXIME ISOMERS, AS WELL AS PROCESS FOR THE SYNTHESIS OF THE MIXTURE OF ISOMERS AND THE PURE ISOMERS
US7576226B2 (en) 2003-06-30 2009-08-18 Richter Gedeon Vegyeszeti Gyar Rt. Process of making isomers of norelgestromin and methods using the same

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2664895B1 (en) * 1990-07-20 1992-10-30 Theramex Laboratoire NEW DERIVATIVES OF 6-METHYL 19-NOR PROGESTERONE, SUBSTITUTED IN 3 AND THEIR PROCESS FOR OBTAINING.
WO1993013122A1 (en) * 1991-12-22 1993-07-08 Schering Aktiengesellschaft 3-methylsulphonylhydrazono and 3-oxyimino steroids, a method of preparing them, pharmaceutical preparations containing them and their use in the preparation of drugs
JPH0568898U (en) * 1992-02-19 1993-09-17 株式会社明和スクリーン Pull top opener

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3299107A (en) * 1965-02-12 1967-01-17 Searle & Co 17-(unsaturated hydrocarbon-substituted)-3-hydroxyimino-5alpha-androstan-17beta-ols,alkyl and acyl derivatives thereof
US3686237A (en) * 1969-12-04 1972-08-22 Ortho Pharma Corp O-(nitroaryl)oximes of 3-keto steroids

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005000867A1 (en) * 2003-06-30 2005-01-06 Richter Gedeon Vegyészeti Gyár Rt. PURE D-(17α)-13-ETHYL-17-HYDROXY-18,19-DINORPREGN-4-ENE-20-YNE-3-ONE-3E- AND -3Z-OXIME ISOMERS, AS WELL AS PROCESS FOR THE SYNTHESIS OF THE MIXTURE OF ISOMERS AND THE PURE ISOMERS
EA008174B1 (en) * 2003-06-30 2007-04-27 Рихтер Гедеон Ведьесети Дьяр Рт. PURE D-(17α)-13-ETHYL-17-HYDROXY-18,19-DINORPREGN-4-ENE-20-YNE-3-ONE-3E- AND -3Z-OXIME ISOMERS, AS WELL AS PROCESS FOR THE SYNTHESIS OF THE MIXTURE OF ISOMERS AND THE PURE ISOMERS
US7576226B2 (en) 2003-06-30 2009-08-18 Richter Gedeon Vegyeszeti Gyar Rt. Process of making isomers of norelgestromin and methods using the same
US7816546B2 (en) 2003-06-30 2010-10-19 Richter Gedeon Vegyeszeti Gyar Rt. Process for the synthesis of high purity d-(17α)-13-ethyl-17-hydroxy-18,19-dinorpregn-4-ene-20-yn-3-one-oxime

Also Published As

Publication number Publication date
AT343292B (en) 1978-05-26
ATA165374A (en) 1977-09-15
FR2219783A1 (en) 1974-09-27
JPS5926640B2 (en) 1984-06-29
JPS5029550A (en) 1975-03-25
CH606108A5 (en) 1978-10-13
CA1034942A (en) 1978-07-18
DE2409648A1 (en) 1974-09-12
FR2219783B1 (en) 1977-06-03

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Legal Events

Date Code Title Description
PS Patent sealed
704A Declaration that licence is not available as of right for an excepted use (par. 4a/1977)
PCNP Patent ceased through non-payment of renewal fee