GB1309651A - Process for the preparation of 3-oxo-19 nor-delta 4- steroids via nitrogenous 4,5-secosteroids - Google Patents

Process for the preparation of 3-oxo-19 nor-delta 4- steroids via nitrogenous 4,5-secosteroids

Info

Publication number
GB1309651A
GB1309651A GB1563270A GB1563270A GB1309651A GB 1309651 A GB1309651 A GB 1309651A GB 1563270 A GB1563270 A GB 1563270A GB 1563270 A GB1563270 A GB 1563270A GB 1309651 A GB1309651 A GB 1309651A
Authority
GB
United Kingdom
Prior art keywords
acid
alkyl
compounds
reaction
formula
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
GB1563270A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche 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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB1309651A publication Critical patent/GB1309651A/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
    • 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
    • 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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1309651 Steroid synthesis; 4,5-secosteroids F HOFFMANN-LA ROCHE & CO AG 2 April 1970 [4 April 1969] 15632/70 Headings C2C and C2U The invention comprises compounds of Formulµ VI and VII and a process for preparing compounds of Formula I from compounds of Formula II by reaction sequence ABCDE or ABCDFG in the reaction scheme in which all compounds are d, l or dl, M is the remainder of the D ring of the steroid; R is OH, C 1-7 alkoxy or -NXY where X and Y are each C 1-7 alkyl; R<SP>1</SP> is primary C 1-5 alkyl, R<SP>2</SP>, R<SP>3</SP> and R<SP>5</SP> are each H or C 1-7 alkyl; and R<SP>6</SP> is H, monocyclic aryl- C 1-7 -alkyl, acyl or -CR<SP>7</SP>R<SP>8</SP>R<SP>9</SP> where R<SP>7</SP>, R<SP>8</SP> and R<SP>9</SP> are each C 1-7 alkyl. Reaction sequence A<SP>1</SP>B<SP>1</SP> is alternative to AB but does not form part of the invention and is not exemplified. The reaction steps are effected as follows: (A) heat and/or acid; (A<SP>1</SP>) and (B) hydrogenation with a noble metal catalyst in the presence of a base; (B<SP>1</SP>) heat and acid; (C) reaction with R-NH 2 or a salt thereof; (D) selective oxidation, e.g. with CrO 3 /acetone, metal alkoxide, silver carbonate, or CrO 3 /H 2 SO 4 /N,N-dialkylalkanamide; (E) aqueous acid in an inert watermiscible organic solvent; (F) reaction with a reactive carbonyl compound; e.g. acetone, pyruvic acid or levulinic acid; (G) cyclization which may be acid- or base-catalysed. A 17 oxo group (steroid numbering) in a compound of Formula III may be converted to an =NR group during step (C) and regenerated during step (E) or (G). Alternatively said 17- oxo group may be reduced to a 17#-hydroxy group or converted to a 17α-alkynyl-17#- hydroxy group immediately prior to step C. A 17-hydroxy group in a compound of Formula VI may be converted to an oxo group during step (D). Compounds of Formulµ III and IV comprise the subject-matter of Specification 1,309,652. Reference has been directed by the Comptroller to Specification 1,207,048.
GB1563270A 1969-04-04 1970-04-02 Process for the preparation of 3-oxo-19 nor-delta 4- steroids via nitrogenous 4,5-secosteroids Expired GB1309651A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US81369369A 1969-04-04 1969-04-04

Publications (1)

Publication Number Publication Date
GB1309651A true GB1309651A (en) 1973-03-14

Family

ID=25213104

Family Applications (2)

Application Number Title Priority Date Filing Date
GB2952172A Expired GB1309652A (en) 1969-04-04 1970-04-02 3-alkyl-4-oxa-steroids process for their preparation and hydro genation
GB1563270A Expired GB1309651A (en) 1969-04-04 1970-04-02 Process for the preparation of 3-oxo-19 nor-delta 4- steroids via nitrogenous 4,5-secosteroids

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB2952172A Expired GB1309652A (en) 1969-04-04 1970-04-02 3-alkyl-4-oxa-steroids process for their preparation and hydro genation

Country Status (13)

Country Link
JP (2) JPS5028952B1 (en)
BE (1) BE748356A (en)
CH (1) CH568336A5 (en)
DE (1) DE2015800C3 (en)
FR (1) FR2068452B1 (en)
GB (2) GB1309652A (en)
HU (1) HU163408B (en)
IE (1) IE34082B1 (en)
IL (1) IL34184A (en)
NL (1) NL7004801A (en)
PL (1) PL80640B1 (en)
SE (1) SE362421B (en)
SU (1) SU439089A3 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS53146139U (en) * 1977-04-22 1978-11-17
GB2514589B (en) 2013-05-30 2020-01-29 Nat Oilwell Varco Lp Centrifuge for separating solids from solids laden drilling fluid

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH503050A (en) * 1967-11-02 1971-02-15 Hoffmann La Roche Process for the preparation of polycyclic compounds

Also Published As

Publication number Publication date
PL80640B1 (en) 1975-08-30
IL34184A (en) 1973-08-29
FR2068452A1 (en) 1971-08-27
SE362421B (en) 1973-12-10
JPS5028952B1 (en) 1975-09-19
FR2068452B1 (en) 1973-07-13
NL7004801A (en) 1970-10-06
BE748356A (en) 1970-10-02
DE2015800A1 (en) 1970-10-22
IE34082L (en) 1970-10-04
IE34082B1 (en) 1975-01-22
GB1309652A (en) 1973-03-14
CH568336A5 (en) 1975-10-31
HU163408B (en) 1973-08-28
JPS4935626B1 (en) 1974-09-25
DE2015800C3 (en) 1979-06-13
IL34184A0 (en) 1970-05-21
DE2015800B2 (en) 1978-10-19
SU439089A3 (en) 1974-08-05

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee