GB966072A - Improvements in or relating to oxapregn-4-ene-3,20-diones and compounds related thereto - Google Patents

Improvements in or relating to oxapregn-4-ene-3,20-diones and compounds related thereto

Info

Publication number
GB966072A
GB966072A GB41955/62A GB4195562A GB966072A GB 966072 A GB966072 A GB 966072A GB 41955/62 A GB41955/62 A GB 41955/62A GB 4195562 A GB4195562 A GB 4195562A GB 966072 A GB966072 A GB 966072A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
compounds
alkanoyloxy
pregn
diones
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
GB41955/62A
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.)
GD Searle LLC
Original Assignee
GD Searle LLC
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
Priority claimed from US173800A external-priority patent/US3080381A/en
Application filed by GD Searle LLC filed Critical GD Searle LLC
Publication of GB966072A publication Critical patent/GB966072A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07D311/78—Ring systems having three or more relevant rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
    • C07C59/46—Unsaturated compounds containing hydroxy or O-metal groups containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/76—Unsaturated compounds containing keto groups
    • C07C59/92—Unsaturated compounds containing keto groups containing —CHO groups
    • 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
    • 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
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/16—Benz[e]indenes; Hydrogenated benz[e]indenes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)

Abstract

The invention comprises compounds of the formula: <FORM:0966072/C1/1> (wherein A is methylene or ethylene, R is hydrogen or alkanoyloxy of 1 to 6 carbon atoms and R1 is hydrogen or methyl) and the 4,5-dehydro, 4a ,5-dehydro and 4,5:6,7-bisdehydro derivatives thereof, and the corresponding hydroxy-acids and salts thereof; and their preparation by reduction of compounds of the formulae: <FORM:0966072/C1/2> and <FORM:0966072/C1/3> (wherein M is hydrogen or an ammonium or alkali metal cation, the dotted lines are optional 4(5), 4a(5) and 4(5), 6(7) double bonds, and R11 is a b -hydrogen atom or, when there is no 6(7) double bond, a hydroxy radical) by use of a metallic reagent capable of reducing a formyl group to a carbinol group followed by, when R11 is OH, dehydration, and when the 20-oxo group has been reduced to a hydroxy group, oxidation of this group. Double bonds may also be reduced in this process or they may be subsequently reduced or introduced. In a modification, 6-acyloxy compounds are used in the reduction process and subsequently hydrolysed. Dehydration may result in a 5,6-dehydro-lactone which is then isomerized to the corresponding 4,5-dehydro-lactone. The lactones of the invention are stated to be in equilibrium with the corresponding hydroxy-acids in solution. Examples are given. Compounds of formula III wherein R11 is hydrogen are prepared by hydroxylating appropriate pregna-1, 4-diene-3, 20-diones to the corresponding 1,2-diols and cleaving these to give 1,2-seco-A-norpregn-3-en-2-oic acids which may be hydrogenated to the corresponding 1,2-seco-A-norpregnan-2-oic acids. Compounds of formula III wherein R11 is hydroxy and R is alkanoyloxy are prepared by epoxidising a 17a -alkanoyloxy-3b -hydroxy-pregn-5-en-20-one, reacting the 5,6-epoxide so formed with acetone in aqueous chromic acid to give the corresponding 17a -alkanoyloxy-5a , 6b -dihydroxy-pregnane-3, 20-dione or with chromium trioxide in pyridine (used on the a -epoxide) to give the corresponding 17a - alkanoyloxy -6a - hydroxy-pregn -4- ene -3, 20-dione, reacting either of these products with dichlorodicyano benzoquinone to yield the corresponding 17a -alkanoyloxy-6a or b -hydroxy-pregn-1, 4-diene-3, 20-diones and then hydroxylating these and cleaving the 1,2-glycols so formed. The products may then be hydrogenated to give the 4,5-saturated compounds or dehydrated to give the 6(7)-unsaturated compounds. Compounds of formula IV are prepared by converting pregn-4-ene-3, 20-diones to the corresponding 2a -hydroxy-pregn-4-ene-3, 20-diones (either via the 6-bromo- and then the 2a -acetoxy-compounds or directly via the latter), and reacting these with periodic acid in aqueous pyridine.
GB41955/62A 1961-11-07 1962-11-06 Improvements in or relating to oxapregn-4-ene-3,20-diones and compounds related thereto Expired GB966072A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US15066261A 1961-11-07 1961-11-07
US173800A US3080381A (en) 1962-02-16 1962-02-16 Optionally 6-methylated and optionally 17-alkanoyloxygenated 2-oxapregnane-3, 20-diones, a-homo compounds corresponding, and 4, 5-dehydro and 4, 5; 6, 7-bisdehydro derivatives thereof

Publications (1)

Publication Number Publication Date
GB966072A true GB966072A (en) 1964-08-06

Family

ID=26847909

Family Applications (1)

Application Number Title Priority Date Filing Date
GB41955/62A Expired GB966072A (en) 1961-11-07 1962-11-06 Improvements in or relating to oxapregn-4-ene-3,20-diones and compounds related thereto

Country Status (5)

Country Link
BE (1) BE624512A (en)
CH (1) CH411868A (en)
DE (1) DE1195765B (en)
FR (2) FR1345183A (en)
GB (1) GB966072A (en)

Also Published As

Publication number Publication date
BE624512A (en) 1963-05-07
FR2724M (en) 1964-08-17
DE1195765B (en) 1965-07-01
CH411868A (en) 1966-04-30
FR1345183A (en) 1963-12-06

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