GB1332784A - Nitrates of steroid 11 beta-ols - Google Patents

Nitrates of steroid 11 beta-ols

Info

Publication number
GB1332784A
GB1332784A GB1332784DA GB1332784A GB 1332784 A GB1332784 A GB 1332784A GB 1332784D A GB1332784D A GB 1332784DA GB 1332784 A GB1332784 A GB 1332784A
Authority
GB
United Kingdom
Prior art keywords
acetoxy
trien
prepared
ols
norpregna
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
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.)
Glaxo Laboratories Ltd
Original Assignee
Glaxo Laboratories Ltd
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 Glaxo Laboratories Ltd filed Critical Glaxo Laboratories Ltd
Publication of GB1332784A publication Critical patent/GB1332784A/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
    • C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond

Landscapes

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

Abstract

1332784 Steroid 11-nitrates GLAXO LABORATORIES Ltd 20 Nov 1970 [21 Nov 1969 27 Oct 1970] 57084/69 and 51028/70 Heading C2U Novel 9 - hydroxy - 11# - nitro - oxy - ring A aromatic steroids are prepared by oxidizing 9, 11-unsubstituted-ring A aromatic steroids or the corresponding 9-ols or #<SP>9(11)</SP>-steroids with ceric ions in the presence of nitrate ions. The starting materials must not contain in ring A an ether group together with an oxidizable CH 3 group. A preferred reagent is ceric ammonium nitrate. Some 9#-ol is formed along with the predominant 9α-ol and it may be separated from the epimer chromatographically. The products may subsequently be converted to the free 11#- ols and these oxidized to the 11-ones. 3 - Acetoxy - 9# - estra - 1,3,5(10) - trien - 17- one is prepared by acetylation of the 3-ol. The following are also prepared by acylation: 3, 20# - diacetoxy - 19 - norpregna - 1,3,5(10)- triene; 3 - tosyloxy - estra - 1,3,5(10) - trien - 17- one and the corresponding 3-phenylacetate and 3- propionate; 3 - acetoxy - 19 - norcholesta - 1,3, 5(10) - triene; 3 - acetoxy - 17# - benzoyloxyestra- 1,3,5(10)-triene (from the 17#-ol) and the corresponding 17# - mesylate; and 3 - acetoxy - 19- norpregna - 1,3,5(10) - trien - 20 - one. 3,17α- Diacetoxy - 19 - norpregna - 1,3,5(10) - trien - 20- one and the corresponding 9#-H compound are prepared by catalytic hydrogenation of the corsesponding 1,3,5(10),9(11)-tetraene. 3-Acetoxy - estra - 1,3,5(10),9(11) - tetraen - 17 - one is a by-product in the reaction of the corresponding 9α-ol with ceric ammonium nitrate.
GB1332784D 1969-11-21 1969-11-21 Nitrates of steroid 11 beta-ols Expired GB1332784A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB5708469 1969-11-21

Publications (1)

Publication Number Publication Date
GB1332784A true GB1332784A (en) 1973-10-03

Family

ID=10478326

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1332784D Expired GB1332784A (en) 1969-11-21 1969-11-21 Nitrates of steroid 11 beta-ols

Country Status (1)

Country Link
GB (1) GB1332784A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5554603A (en) * 1993-09-17 1996-09-10 The United States Of America As Represented By The Department Of Health And Human Services Orally active derivatives of 1,3,5(10)-estratriene

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5554603A (en) * 1993-09-17 1996-09-10 The United States Of America As Represented By The Department Of Health And Human Services Orally active derivatives of 1,3,5(10)-estratriene

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees