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US 5,703,066 AGranted
Progestationally active 19,11-bridged 4-estrenes
AssigneeSchering Corporation
InventorsEckhard Ottow, Wolfgang Schwede, Wolfgang Halfbrodt, Karl-Heinrich Fritzemeier, Rolf Krattenmacher
Life of this patent
Estimating the term…
Abstract
In this invention, the new etheno- and ethano-19,11-bridged 4-estrenes of general formula I ##STR1## are described, in which W, R.sup.1, R.sup.2, R.sup.6a, R.sup.6b, R.sup.7, R.sup.14, R.sup.15, R.sup.16, R.sup.11, R.sup.11' and R.sup.19 have the meaning indicated in the description, as well as a process for their production. The new compounds have strong progestational activity and are suitable for the production of pharmaceutical agents.
Claims13
A 19,11-Bridged 4-estrene of general formula I ##STR16## in which W is the hydroxyimino group, /N.about.OH, or two hydrogen atoms;
- R.sup.1 and R.sup.2 are each a hydrogen atom or together form an additional bond or form a methylene bridge in .alpha.-position;
- R.sup.6a and R.sup.6b are each a hydrogen atom or together form a methylene group or together form a three-membered ring with carbon atom 6, R.sup.7 is a hydrogen atom, a straight-chain or branched-chain, saturated alkyl radical in the .alpha.- or .beta.-position with up to 4 carbon atoms or a thio group --SR.sup.20, in which R.sup.20 is a hydrogen atom or an alkanoyl group with 1 to 4 carbon atoms;
- R.sup.6a is a hydrogen atom or a fluorine, chlorine, bromine or iodine atom or a straight-chain or branched-chain, saturated alkyl radical in the .alpha.- or .beta.-position with up to 4 carbon atoms, and R.sup.6b and R.sup.7 are each a hydrogen atom or together form an additional bond;
- or
- R.sup.6b and R.sup.7 together are a methylene bridge in the .alpha.- or .beta.-position, and R.sup.6a is a hydrogen atom;
- R.sup.14, R.sup.15 and R.sup.16 are each a hydrogen atom;
- or
- R.sup.14 is a hydrogen atom in the .alpha.-position and R.sup.15 and R.sup.16 together form an additional bond or form a methylene bridge in the .alpha.- or .beta.-position;
- or
- R.sup.14 and R.sup.15 are each a hydrogen atom and R.sup.16 is a C.sub.1-4 -alkyl group in the .alpha.- or .beta.-position or together with R.sup.17.alpha. forms a methylene bridge in the .alpha.-position and R.sup.17.beta. is a group ##STR17## R.sup.16 is a hydrogen atom and R.sup.14 and R.sup.15 together form an additional bond;
- R.sup.11, R.sup.11' and R.sup.19 are each a hydrogen atom;
- or
- R.sup.11 is a hydrogen atom in the .alpha.-position, and R.sup.11' and R.sup.19 together form an additional bond;
- or
- R.sup.19 is a hydrogen atom and R.sup.11 and R.sup.11' together form an additional bond,
- R.sup.17.beta. /R.sup.17.alpha. are the following combinations:
- --OR.sup.21 /--(CH.sub.2).sub.n --A,
- --OR.sup.21 /--(CH.sub.2).sub.m --C.tbd.C--B,
- --OR.sup.21 /--(CH.sub.2).sub.p --CH.dbd.CH--(CH.sub.2).sub.k --D,
- --OR.sup.21 /--HC.dbd.C.dbd.CEG,
- --OR.sup.21 /--CF.sub.3, ##STR18## or R.sup.17.beta. /R.sup.17.alpha. together form ##STR19## wherein x=1 or 2, ##STR20## and when, R.sup.17.beta. /R.sup.17.alpha. forms a ring, W is additionally an oxygen atom
- R.sup.21 and R.sup.23 are each a hydrogen atom, a C.sub.1-4 -alkyl or a C.sub.1-4 -alkanoyl group;
- R.sup.22 is a C.sub.1-3 -alkyl group;
- A is a hydrogen atom, a cyano group, --COOR.sup.24 or --OR.sup.25 in which R.sup.24 is C.sub.1-4 -alkyl and R.sup.25 is hydrogen, C.sub.1-4 -alkyl or C.sub.1-4 -alkanoyl;
- B is a hydrogen atom;
- a C.sub.1-4 -alkyl group;
- a C.sub.2 - or C.sub.3 -alkinyl group;
- a fluorine, chlorine, bromine or iodine atom;
- a hydroxyalkyl, alkoxyalkyl or alkanoyloxyalkyl group with 1 to 4 carbon atoms each in the alkyl, alkoxy or alkanoyloxy part;
- D is a hydrogen atom, a hydroxy, C.sub.1-4 -alkoxy or C.sub.1-4 -alkanoyloxy group;
- E and G are each hydrogen or C.sub.1-3 -alkyl;
- n is 0, 1, 2, 3 or 4;
- m is 0, 1 or 2;
- p is 0 or 1;
- k is 0, 1, 2 or 3;
- and
- R.sup.18 is a hydrogen atom or a methyl group.
34 more elements
Dependencies are inferred from the claim text.