GB1069847A - 6-oxasteroid and d-homo-6-oxasteroid 3-ketones and their enol ethers - Google Patents

6-oxasteroid and d-homo-6-oxasteroid 3-ketones and their enol ethers

Info

Publication number
GB1069847A
GB1069847A GB962764A GB962764A GB1069847A GB 1069847 A GB1069847 A GB 1069847A GB 962764 A GB962764 A GB 962764A GB 962764 A GB962764 A GB 962764A GB 1069847 A GB1069847 A GB 1069847A
Authority
GB
United Kingdom
Prior art keywords
group
carbonyl
oxasteroid
compound
trans
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
GB962764A
Inventor
Gordon Alan Hughes
Herchel Smith
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
Priority to GB962264A priority Critical patent/GB1069842A/en
Priority to NL6402297A priority patent/NL6402297A/xx
Priority to GB962764A priority patent/GB1069847A/en
Priority to GB962364A priority patent/GB1069843A/en
Priority to NL6402300A priority patent/NL6402300A/xx
Priority to NL6402399A priority patent/NL6402399A/xx
Priority to SE302764A priority patent/SE324562B/xx
Priority to BE645390A priority patent/BE645390A/xx
Priority to CH345264A priority patent/CH472400A/en
Priority to CH345464A priority patent/CH461525A/en
Priority to BE645391A priority patent/BE645391A/xx
Priority to FR968703A priority patent/FR1397508A/en
Priority to FR968701A priority patent/FR1397506A/en
Priority to CH41565A priority patent/CH471112A/en
Priority to BE658257D priority patent/BE658257A/xx
Priority to FR1838A priority patent/FR1431733A/en
Priority to DE19651518297 priority patent/DE1518297B1/en
Priority to NL6500434A priority patent/NL6500434A/xx
Priority to ES0308112A priority patent/ES308112A1/en
Publication of GB1069847A publication Critical patent/GB1069847A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J73/00—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms
    • C07J73/001—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms by one hetero atom
    • C07J73/003—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms by one hetero atom by oxygen as hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4

Landscapes

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

Abstract

The invention comprises compounds of formulae <FORM:1069847/C2/1> <FORM:1069847/C2/2> wherein the 3-ketones have an ethylenic bond terminating at the 5-position, R1 is an alkyl group, Q is a methylene or ethylene group, Y is a carbonyl or hydroxymethylene group or a group -CR2OH- wherein R2 is an alkyl, alkenyl, alkynyl or chloroethynyl group trans to the group R1, RO is an etherified hydroxy group, the hydrogen atoms at the 14, 8 and 9 positions have the trans-anti-trans configuration with respect to the group R1, and the hydrogen atom at the 10-position, when present, is anti to that at the 9-position, and their preparation by subjection of a 3-etherified hydroxy-1,3,5(10)-triene or 1,3,5(10), 9(11)-tetraene to a Birch reduction to obtain a D 2'5(10) compound of the invention, followed, if desired, by one or more of (a) hydrolysis to form a 3-keto-D 4 or 3-keto-D 5(10) compound, (b) acid isomerization of a D 5(10) product to a D 4 product, (c) oxidation of a hydroxymethylene group Y to a carbonyl group, (d) reduction of a carbonyl group Y to a hydroxymethylene group, or (e) reaction of a carbonyl group Y with a Grignard reagent or an alkali metal alkyl or alkynyl compound. The compounds of the invention have progestational activity and may be used in pharmaceutical compositions in combination with a carrier, for example in forms suitable for oral, parenteral or rectal administration.
GB962764A 1964-01-15 1964-03-06 6-oxasteroid and d-homo-6-oxasteroid 3-ketones and their enol ethers Expired GB1069847A (en)

Priority Applications (19)

Application Number Priority Date Filing Date Title
GB962264A GB1069842A (en) 1964-01-15 1964-03-06 Chromane derivatives
NL6402297A NL6402297A (en) 1964-01-15 1964-03-06
GB962764A GB1069847A (en) 1964-01-15 1964-03-06 6-oxasteroid and d-homo-6-oxasteroid 3-ketones and their enol ethers
GB962364A GB1069843A (en) 1964-01-15 1964-03-06 Ethylidene chromanes
NL6402300A NL6402300A (en) 1964-01-15 1964-03-06
NL6402399A NL6402399A (en) 1964-01-15 1964-03-09
SE302764A SE324562B (en) 1964-01-15 1964-03-11
BE645390A BE645390A (en) 1964-01-15 1964-03-18
CH345264A CH472400A (en) 1964-01-15 1964-03-18 Process for making tetracyclic compounds
CH345464A CH461525A (en) 1964-01-15 1964-03-18 Process for making 6-oxa steroids
BE645391A BE645391A (en) 1964-01-15 1964-03-18
FR968703A FR1397508A (en) 1964-01-15 1964-03-25 Process for the preparation of new 6 oxa-steroids
FR968701A FR1397506A (en) 1964-01-15 1964-03-25 Process for the preparation of new tetracyclic compounds
CH41565A CH471112A (en) 1964-01-15 1965-01-12 Process for the preparation of 4-vinylchroman-4-ols
BE658257D BE658257A (en) 1964-01-15 1965-01-13
FR1838A FR1431733A (en) 1964-01-15 1965-01-13 New heterocyclic steroids and their preparation process
DE19651518297 DE1518297B1 (en) 1964-01-15 1965-01-14 Process for the preparation of substituted 4-AEthylidenechromanen
NL6500434A NL6500434A (en) 1964-01-15 1965-01-14
ES0308112A ES308112A1 (en) 1964-01-15 1965-01-14 A procedure for preparing a heterociclic steroid compound. (Machine-translation by Google Translate, not legally binding)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US33786464A 1964-01-15 1964-01-15
GB962764A GB1069847A (en) 1964-01-15 1964-03-06 6-oxasteroid and d-homo-6-oxasteroid 3-ketones and their enol ethers
BE645390A BE645390A (en) 1964-01-15 1964-03-18
BE645391A BE645391A (en) 1964-01-15 1964-03-18

Publications (1)

Publication Number Publication Date
GB1069847A true GB1069847A (en) 1967-05-24

Family

ID=27424754

Family Applications (3)

Application Number Title Priority Date Filing Date
GB962364A Expired GB1069843A (en) 1964-01-15 1964-03-06 Ethylidene chromanes
GB962764A Expired GB1069847A (en) 1964-01-15 1964-03-06 6-oxasteroid and d-homo-6-oxasteroid 3-ketones and their enol ethers
GB962264A Expired GB1069842A (en) 1964-01-15 1964-03-06 Chromane derivatives

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB962364A Expired GB1069843A (en) 1964-01-15 1964-03-06 Ethylidene chromanes

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB962264A Expired GB1069842A (en) 1964-01-15 1964-03-06 Chromane derivatives

Country Status (7)

Country Link
BE (3) BE645391A (en)
CH (3) CH472400A (en)
DE (1) DE1518297B1 (en)
FR (2) FR1397506A (en)
GB (3) GB1069843A (en)
NL (3) NL6402297A (en)
SE (1) SE324562B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3407214A (en) * 1966-04-08 1968-10-22 American Home Prod 5-hydroxy-6-oxagonan-3-ones
EP0381138A3 (en) * 1989-01-30 1991-11-06 Banyu Pharmaceutical Co., Ltd. Antitumor substance be-12406

Also Published As

Publication number Publication date
GB1069843A (en) 1967-05-24
BE645390A (en) 1964-07-16
CH471112A (en) 1969-04-15
SE324562B (en) 1970-06-08
DE1518297B1 (en) 1972-04-27
BE658257A (en) 1965-07-13
CH472400A (en) 1969-05-15
NL6500434A (en) 1965-07-16
FR1431733A (en) 1966-03-18
BE645391A (en) 1964-09-18
NL6402300A (en) 1965-07-16
CH461525A (en) 1968-08-31
FR1397506A (en) 1965-04-30
GB1069842A (en) 1967-05-24
NL6402297A (en) 1965-07-16

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