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Claims for Patent: 3,927,046

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Claims for Patent: 3,927,046

Title: Novel 11,11-alkylidene steroids
Abstract:The invention relates to novel 11,11-alkylidene steroids of the estrane and (19-nor-)pregnane series having a double bond starting from carbon atom 5, the alkylidene group in 11-position having the formula ##EQU1## wherein R.sub.1 and R.sub.2 are hydrogen or an alkyl group having 1-2 C-atoms, and to processes for their preparation. The novel compounds have very interesting biological activities, such as anabolic, androgenic, estrogenic, progestative, anti-androgenic, anti-oestrogenic, ovulation-inhibiting and gonad-inhibiting activities.
Inventor(s): van den Broek; Albertus Joannes (Oss, NL)
Assignee: Akzona Incorporated (Asheville, NC)
Application Number:05/420,823
Patent Claims: 1. An 11,11-alkylidene steroid of the formula: ##SPC4##

wherein R.sub.1 and R.sub.2 are selected from the group consisting of hydrogen and methyl; R.sub.3 is selected from the group consisting of methyl and ethyl; R.sub.5 is selected from the group consisting of oxygen, .alpha.H (.beta.R.sub.6) and .alpha. R.sub.7 (.beta.R.sub.6), wherein R.sub.6 is selected from the group consisting of hydroxy and acylated hydroxy, the acyl group of which is derived from a saturated or unsaturated organic carboxylic acid having 1-18 carbon atoms; R.sub.7 is saturated or unsaturated alkyl having 1-4 carbon atoms; X is selected from the group consisting of H.sub.2, oxygen and H(R.sub.8), where H.sub.8 is selected from the group consisting of hydroxy and acetoxy; and a double bond is present starting from carbon atom 5.

2. An 11,11-alkylidene steroid of the formula: ##SPC5##

wherein R.sub.1 and R.sub.2 are selected from the group consisting of hydrogen and methyl; R.sub.3 is methyl; R.sub.4 is selected from the group consisting of hydrogen and hydroxy; R.sub.5 is selected from the group consisting of oxygen, .alpha.H (.beta. OH) and .alpha.R.sub.7 (.beta. OH), wherein R.sub.7 is saturated or unsaturated alkyl having 1-4 carbon atoms; and R.sub.8 is selected from the group consisting of hydroxy and methoxy.

3. An 11,11-alkylidene steroid of the formula: ##SPC6##

wherein R.sub.1 and R.sub.2 are selected from the group consisting of hydrogen and methyl; R.sub.9 and R.sub.12 are selected from the group consisting of oxygen and H(R.sub.8a), wherein R.sub.8a is selected from the group consisting of hydroxy and acetoxy; R.sub.10 is selected from the group consisting of hydrogen and methyl, R.sub.11 is selected from the group consisting of hydrogen, fluoro, hydroxy and acylated hydroxy, the acyl group of which has been derived from a saturated or unsaturated organic carboxylic acid having 1-18 carbon atoms; R.sub.13 is selected from the group consisting of hydrogen, methyl hydroxy and acylated hydroxy, the acyl group of which has been derived from a saturated or unsaturated organic carboxylic acid having 1-18 carbon atoms with the proviso that when R.sub.13 is not hydrogen, R.sub.11 is hydrogen; R.sub.14 is selected from the group consisting of H.sub.2,H(alkyl), the alkyl group of which has 1-4 carbon atoms, and methylene; R.sub.15 is selected from the group consisting of hydrogen, methyl and chloro; R.sub. 16 and R.sub.17 are hydrogen or together form a methylene group with the proviso that when R.sub.16 and R.sub.17 are not hydrogen, R .sub.11, R .sub.13, R.sub.14 and R.sub.15 are hydrogen; and a double bond may be present between carbon atoms 6 and 7.
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