Non-estrogenic estradiol derivative compounds with anti-oxidative activity
AssigneeJenapharm GmbH & Co. KG
InventorsPeter Droescher, Bernd Menzenbach, Wolfgang Roemer, Birgitt Schneider, Walter Elger, Guenter Kaufmann
Life of this patent
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Abstract
New non-estrogenic derivative compounds of estradiol, which have no estrogenic activity and comparatively high anti-oxidative activity, are disclosed. These new non-estrogenic derivative compounds are potentially useful as non-estrogenic antioxidants, especially for administration in post-menopausal women and in men. The compounds of the invention can also inhibit aromatase and sulfatase.
Claims5
A non-estrogenic estradiol compound with antioxidative activity of the formula I:
- wherein R1 is H or OH,
- R2 and R3 are the same or different and are each, independently of each other, H or CH3,
- R4 and R5 are the same or different and are each, independently of each other, —OH, —O(CO)R6, —OR6 or —OSO2NR7R8, wherein R6 represents an alkyl group having 1 to 4 carbon atoms, and the R7 and R8 groups are each, independently of each other, H or an alkyl group having one to four carbon atoms, or R7 and R8 together with the N atom represent a polymethylenimino group with 4 to 6 carbon atoms or a morpholino group,
- each of the dashed lines represent either an additional bond or not in the ring positions indicated by the respective dashed lines so that either a double bond or a single bond is present at said ring positions;
- and
- wherein R5 is a 17α group.
A non-estrogenic estradiol compound with antioxidative activity of the formula II:
- wherein R1 is H or OH,
- R2 and R3 are the same or different and are each, independently of each other, H or CH3,
- Z is an unsubstituted group represented by —(CH2)nAPh, wherein Ph represents an unsubstituted phenyl group or a substituted phenyl group and A represents a bond for n=0 or a bond, O, S or Se for n=1, said substituted phenyl group having from 1 to 2 hydroxy group substituents and 0 to 2 methyl group substituents or a dimethylaminophenyl group and 0 to 2 methyl group substituents;
- R4 and R5 are the same or different and are each, independently of each other, —OH, —O(CO)R6, —OR6 or —OSO2NR7R8, wherein R6 represents an aryl group or an alkyl group having 1 to 4 carbon atoms, and the R7 and R8 groups are each, independently of each other, H or an alkyl group having one to four carbon atoms, or R7 and R8 together with the N atom represent a polymethylenimino group with 4 to 6 carbon atoms or a morpholino group, and each of the dashed lines represent either an additional bond or not in the ring positions indicated by the respective dashed lines so that either a double bond or a single bond is present at said ring positions.
A non-estrogenic estradiol compound selected from the group consisting of 4-methylestra-1,3,5(10)-trien-1,17α-diol 4-methylestra-1,3,5(10),6-tetraen-1,17α-diol.
4-methylestra-1,3,5(10 )-trien-1,17α-diol.
A non-estrogenic estradiol compound selected from the group consisting of 4-methylestra-1,3,5(10),6-tetraen-1,17β-diol, 4-methylestra-1,3,5(10),6,8-pentaen-1,17β-diol, 17α-4′-hydroxyphenylmethyl-4-methylestra-1,3,5(10)-trien-1,17β-diol, 17α-4′-hydroxyphenoxymethyl-4-methylestra-1,3,5(10)-trien-1,17β-diol, 17α-4′-hydroxythiophenoxymethyl-4-methylestra-1,3,5(10)-trien-1,17β-diol, 17α-4′-dimethylaminophenylmethyl-4-methylestra-1,3,5(10)-trien-1,17β-diol, 17α-3′,5′-dimethyl-4′-hydroxy-phenylmethyl-4-methylestra-1,3,5(10 )-trien-1,17β-diol, 17α-3′,5′-dimethyl-4′-hydroxy-phenylmethyl-4-methylestra-1,3,5(10), 6-tetraen-1,17β-diol and 17α-4′-hydroxy-phenoxymethyl-4-methylestra-1,3,5(10),6-tetraen-1,17β-diol.
Dependencies are inferred from the claim text.