US 4,330,539 A · Novel 17-amino-16-hydroxy steroids of the androstane and oestrane series and derivatives thereof

Abstract

New and pharmacologically useful 17-amino-16-hydroxy-steroids of the androstane and oestrane series are disclosed having the formula I: ##STR1## and pharmaceutically acceptable non-toxic acid addition salts thereof, wherein: R.sub.1 =H or hydrocarbyl of one to six carbon atoms (preferably lower alkyl, such as methyl); R.sub.2 =H or hydrocarbyl of one to six carbon atoms (preferably lower alkyl, such as methyl); R.sub.3 =a free, esterified or etherified hydroxyl group; ring A inclusive carbon atoms 6 and 9 has one of the following configurations: ##STR2## in which R.sub.4 =a free, esterified or etherified hydroxyl group; R.sub.5 =O or H(R.sub.7), wherein R.sub.7 is a free, esterified or etherified hydroxyl group; R.sub.6 =H or methyl; and the dotted lines represent an optional double bond in 4,5- or 5,6-position; as well as the enantiomers and racemates of these steroids. The novel compounds have antiarrhythmic properties.

Claims9

Dependent claims

Steroids of the androstane and oestrane series selected from the group consisting of compounds having the formula I:

##STR7## and pharmaceutically acceptable non-toxic acid additional salts thereof, wherein:
R.sub.1 =H or hydrocarbyl of one to six carbon atoms;
R.sub.2 =H or hydrocarbyl of one to six carbon atoms;
R.sub.3 =a free, esterified or etherified hydroxyl group;
ring A, inclusive of carbon atoms 6 and 9, has one of the following configurations:
##STR8## in which R.sub.4 =a free, esterified or etherified hydroxyl group;
R.sub.5 =O or H(R.sub.7), wherein R.sub.7 is a free, esterified or etherified hydroxyl group;
R.sub.6 =H or methyl and
the dotted lines represent an optional double bond in the 4,5-position when R.sub.5 is O or H(R.sub.7), or in the 5,6-position when R.sub.5 is H(R.sub.7), and the enatiomers and racemates of these steroids.

6 more elements

A compound selected from the group consisting of 16.alpha.-hydroxy-17.beta.-methylamino-5.alpha.-androstane-3-one maleate, 17.beta.-methylamino-5.alpha.-androstane-3.beta.,16.alpha.-diol maleate, 17.beta.-amino-5.alpha.-androstane-3.beta.,16.alpha.-diol maleate, 17.beta.-methylamino-5.alpha.-androstane-3.beta.,16.alpha.-diol 3-acetate hydrocloride, 17.beta.-methylamino-androst-5-ene-3.beta.,16.alpha.-diol maleate, 16.alpha.-hydroxy-17.beta.-methylamino-androst-4-en-3-one maleate, 16.alpha.-hydroxy-17.beta.-methylene-androsta-1,4-dien-3-one maleate, 16.beta.-hydroxy-17.beta.-methylamino-5.alpha.-androstan-3-one maleate, 17.beta.-methylamino-5.alpha.-androstane-3.alpha.,16.beta.-diol maleate, 16.beta.-hydroxy-17.alpha.-methylamino-5.alpha.-androstan-3-one maleate, 17.beta.-methylamino-oestra-1,3,5(10)-triene-3,16.beta.-diol hydrochloride, 17.beta.-methylamino-oestra-1,3,5(10)-triene-3,16.beta.-diol hydronitrate, 17.beta.-methylamino-oestra-1,3,5(10)-triene-3,16.beta.-diol 3-methylether hydrochloride, 17.beta.-methylamino-oestra-1,3,5(10)-triene-3,16.alpha.-diol hydrochloride, 17.beta.-methylamino-oestra-1,3,5(10)-triene-3,16.alpha.-diol 3-methylether hydrochloride, 17.beta.-methylamino-oestra-1,3,5(10)-triene-3,16.alpha.-diol maleate, 17.beta.-dimethylamino-oestra-1,3,5(10)-triene-3,16.alpha.-diol maleate, 1-methyl-17.beta.-methylamino-oestra-1,3,5(10)-triene-3,16.alpha.-diol hydrochloride, 17.beta.-ethylamino-oestra-1,3,5(10)-triene-3,16.alpha.-diol maleate, 17.beta.-amino-oestra-1,3,5(10)-triene-3,16.alpha.-diol citrate, 17.beta.-methylamino-oestra-1,3,5(10)-triene-3,16.alpha.-diol methane-sulfonate, 17.beta.-isopropylamino-oestra-1,3,5(10)-triene-3,16.alpha.-diol citrate, 17.beta.-dimethylamino-oestra-1,3,5(10)-triene-3,16.alpha.-diol 3-acetate maleate, dl-17.beta.-methylamino-oestra-1,3,5(10)-triene-3,16.alpha.-diol 3-methylether hydrochloride, dl-17.beta.-methylamino-oestra-1,3,5(10)-triene-3,16.alpha.-diol hydrochloride, ent-17.beta.-methylamino-oestra-1,3,5(10)-triene-3,16.alpha.-diol 3-methylether hydrochloride, ent-17.beta.-methylamino-oestra-1,3,5(10)-triene-3,16.alpha.-diol hydrochloride, 17.beta. -methylamino-oestra-1,3,5(10)-triene-3,16.alpha.-diol 3-ethylether methanesulfonate, 17.beta.-methylamino-oestra-1,3,5(10)-triene-3,16.alpha.-diol 3-propylether methane-sulfonate, 17.beta.-methylamino-oestra-1,3,5(10)-triene-3,16.alpha.-diol 3-acetate maleate, 17.beta.-methylamino-oestra-1,3,5(10)-triene-3,16.alpha.-diol 3-propionate maleate, 17.beta.-methylamino-oestra-1,3,5(10)-triene-3,16.alpha.-diol 3-pivalate maleate, 17.alpha.-methylamino-oestra-1,3,5(10)-triene-3,16.beta.-diol 3-methylether hydrochloride, and 17.beta.-amino-oestra-1,3,5(10)-triene-3,16.beta.-diol 3-methylether hydrochloride.

Dependencies are inferred from the claim text.

Novel 17-amino-16-hydroxy steroids of the androstane and oestrane series and derivatives thereof

Life of this patent

Novel 17-amino-16-hydroxy steroids of the androstane and oestrane series and derivatives thereof

Life of this patent

Abstract

Claims9