GB934574A - Steroids - Google Patents

Steroids

Info

Publication number
GB934574A
GB934574A GB209661A GB209661A GB934574A GB 934574 A GB934574 A GB 934574A GB 209661 A GB209661 A GB 209661A GB 209661 A GB209661 A GB 209661A GB 934574 A GB934574 A GB 934574A
Authority
GB
United Kingdom
Prior art keywords
formula
ring
aryl
steroido
triazoles
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
GB209661A
Inventor
Giangiacomo Nathansohn
Emilio Testa
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.)
Gruppo Lepetit SpA
Original Assignee
Lepetit SpA
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 to NL273722D priority Critical patent/NL273722A/xx
Application filed by Lepetit SpA filed Critical Lepetit SpA
Priority to GB209661A priority patent/GB934574A/en
Priority to DEL40751A priority patent/DE1170943B/en
Priority to CH1509361A priority patent/CH453372A/en
Priority to FR884863A priority patent/FR1310385A/en
Publication of GB934574A publication Critical patent/GB934574A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C07D249/18—Benzotriazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0036—Nitrogen-containing hetero ring
    • C07J71/0042—Nitrogen only
    • C07J71/0047—Nitrogen only at position 2(3)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general

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)

Abstract

The invention comprises steroido-[2,3-d]-triazoles having at ring A the formula <FORM:0934574/IV(a)/1> having an alpha or beta configuration at C5 and wherein R represents a hydrogen atom or an aryl radical, and acid addition salts thereof, and having at ring A the formula <FORM:0934574/IV(a)/2> wherein Y represents an alkyl, aryl or aralkyl radical and NR12 represents a dialkylamine or morpholine residue, and the preparation of steroido-[2,3-d]-triazoles of the first general formula above wherein R represents an aryl radical by reacting 3-ketosteroids having at ring A the formula <FORM:0934574/IV(a)/3> with a dialkylamine or morpholine in an inert organic solvent in the presence of a catalytic amount of a proton donor such as p-toluene sulphonic acid, and reacting the resulting steroid enamines having at ring A the formula <FORM:0934574/IV(a)/4> wherein NR12 has the above significance, with an aryl azide in an inert organic solvent, and the preparation of steroido-[2,3-d]-triazoles of the first general formula above wherein R represents a hydrogen atom by reacting the steroid enamines of the fourth general formula above with an azide of the formula YOCON3, wherein Y represents an alkyl, aryl or aralkyl radical, such as benzyl azidoformate, in an inert organic solvent, and subjecting the resulting steroido-[2,3-d]-triazoles having at ring A the second formula above wherein Y and NR12 have the above significance to reduction, for example, by means of lithium aluminium hydride or hydrogen in the presence of a hydrogenation catalyst, or to hydrolysis, for example, by means of a solution of an alkali metal hydroxide. In the above compounds and processes, the steroids may be of the 5a - and 5b -pregnane, androstane and cholestane series. Benzyl azidoformate is prepared by reacting benzyl chloroformate and sodium azide.
GB209661A 1961-01-18 1961-01-18 Steroids Expired GB934574A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
NL273722D NL273722A (en) 1961-01-18
GB209661A GB934574A (en) 1961-01-18 1961-01-18 Steroids
DEL40751A DE1170943B (en) 1961-01-18 1961-12-20 Process for the preparation of [2, 3-d] -triazolo-steroids of the 5ª ‡ -Pregnan-, -Androstan- and -Cholestanreihe
CH1509361A CH453372A (en) 1961-01-18 1961-12-28 Process for the production of therapeutically effective steroids
FR884863A FR1310385A (en) 1961-01-18 1962-01-15 Process for the preparation of nitrogenous steroids, intermediate useful for this preparation and new compounds obtained by carrying out said process

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB209661A GB934574A (en) 1961-01-18 1961-01-18 Steroids

Publications (1)

Publication Number Publication Date
GB934574A true GB934574A (en) 1963-08-21

Family

ID=9733520

Family Applications (1)

Application Number Title Priority Date Filing Date
GB209661A Expired GB934574A (en) 1961-01-18 1961-01-18 Steroids

Country Status (5)

Country Link
CH (1) CH453372A (en)
DE (1) DE1170943B (en)
FR (1) FR1310385A (en)
GB (1) GB934574A (en)
NL (1) NL273722A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005523254A (en) * 2002-01-22 2005-08-04 ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア Non-steroidal ligands for glucocorticoid receptors, compositions thereof and uses

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005523254A (en) * 2002-01-22 2005-08-04 ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア Non-steroidal ligands for glucocorticoid receptors, compositions thereof and uses
US7947726B2 (en) 2002-01-22 2011-05-24 The Regents Of The University Of California Non-steroidal ligands for the glucocorticoid receptor, and compositions thereof

Also Published As

Publication number Publication date
CH453372A (en) 1968-06-14
NL273722A (en)
FR1310385A (en) 1962-11-23
DE1170943B (en) 1964-05-27

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