14-aminosteroid derivatives, application in therapy and process of preparation
AssigneeEtablissements Nativelle S.A.
InventorsFrancois-Xavier Jarreau, Jean-Jacques Koenig
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Abstract
The present invention relates to new 14-aminosteroids and their application in therapy and also to a process for their preparation.
Claims9
A method for the treatment of cardiac insufficiencies which comprises administering to an afflicted subject a therapeutically effective amount of 14-amino steroid represented by the general formula (I):
- ##STR4## in which R represents a hydrogen atom or a lower alkyl group containing 1 to 4 carbon atoms and R.sub.1 represents a hydrogen atom or a hydroxyl group, or a pharmaceutically acceptable salt thereof.
A 14-aminosteroid which is represented by the general formula (I) ##STR5## in which R is a hydrogen atom or a lower alkyl group containing 1 to 4 carbon atoms and R.sub.1 is a hydrogen atom or a hydroxyl group, R and R.sub.1 not geing a hydrogen atom simultaneously, it being understood that when R.sub.1 is a hydrogen atom, the --OH group in the 20-position has the .beta. configuration when the --OH group in the 3-position has the .beta. configuration and when the hydrogen atom in the 17-position possesses the .alpha. configuration.
A process for the preparation of a 14-aminosteroid of the general formula (I):
- ##STR6## in which R is a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms and R.sub.1 represents a hydrogen atom or hydroxyl group, which comprises reducing and then acetylating a 3,14-hihydroxysteroid of the formula (II):
- ##STR7## in which R has the dame definition as above, to form an 0-acetylated 3,14,20-trihyrdoxysteroid of the formula (III):
- ##STR8## in which R has the same meaning as above, R.sub.1 in a hydrogen atom or an acetyl group and Ac is an acetyl group, reacting a hydrozoic acid/boron trifluoride complex with the compound of the formula (III) to form the corresponding 14-azido derivative, and the reducing this with a metal hydride or by catalytic hydrogenation.
A pharmaceutical composition for the treatment of cardiac insufficiencies which contains a therapeutically effective amount of a 14-aminosteroid represented by the general formula (I):
- ##STR9## in which R represents a hydrogen atom or a lower alkyl group containing 1 to 4 carbon atoms and R.sub.1 represents a hydrogen atom or a hydroxyl group, R and R.sub.1 not being a hydrogen atom simultaneously, it being understood that when R.sub.1 is a hydrogen atom, the --OH group in the 20-position has the .beta. configuration when the --OH group in the 3-position has the .beta. configuration and when the hydrogen atom in the 17-position possesses the .alpha. configuration or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.
Dependencies are inferred from the claim text.