-Azido-4,6-pregnadieno(3,2-c)pyrazoles, processes for their prep

Details -Azido-4,6-pregnadieno(3,2-c)pyrazoles, processes for their prep -Azido-4,6-pregnadieno(3,2-c)pyrazoles, processes for their prep

1974-04-22

1976-01-13

Roberts, Elbert L.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260349, 26039745, 26023955D, 424241, C07J 100

Patent

active

039323889

ABSTRACT:
Steroidal 6-azido-4,6-pregnadieno[3,2-c]pyrazoles having glucocorticoid activity are prepared by treating a 6-unsubstituted-4,6-pregnadieno[3,2-c]pyrazole with a halogen azide followed by treatment of the thereby formed 6-azido-7-halogeno-6,7-dihydro-4-pregnene[3,2-c]pyrazole with a dehydrohalogenating agent. Other methods of preparing these compounds are described, including the process of treating a 6-azido-17.alpha.,20; 20,21-bismethylenedioxy-4,6-pregnadiene-3-one with an alkyl formate in the presence of base followed by treatment of the resulting 2-hydroxymethylene derivative with a hydrazine or, alternatively, by converting said 2-hydroxymethylene to a 2-alkoxymethylene derivative followed by treatment thereof with a hydrazine.
Preferred compounds include 6-azido-11.beta.,17.alpha.,21-trihydroxy-20-keto-4,6-pregnadieno[3,2-c]pyr azoles, particularly 2'-phenyl-9.alpha.-fluoro(and 9.alpha.-chloro)-16-methyl-derivatives thereof which possess potent anti-inflammatory activity. Of interest is 2'-phenyl-6-azido-9.alpha.-fluoro-11.beta.,17.alpha.,21-trihydroxy-16.alph a.-methyl-20-keto-4,6-pregnadieno[3,2-c]pyrazole.

REFERENCES:
patent: 3376292 (1968-04-01), Beard et al.
patent: 3475417 (1969-10-01), Nelson
patent: 3475418 (1969-10-01), Hirschmann et al.
patent: 3784603 (1974-01-01), Shapiro et al.

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