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US 5,344,834 AGranted
Functionalized vinyl azoles and methods of use
AssigneeSchering Corporation
InventorsPeter Strehlke, Rolf Bohlmann, Martin Schneider, Yukishige Nishino, Hans-Peter Muhn-Seipoldy
Life of this patent
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Abstract
Pharmaceutical preparations comprising functionalized vinyl azoles of formula I ##STR1## wherein the substituents are as defined herein, including novel compounds, as well as methods of use and methods of their preparation, are provided.
Claims30
A pharmaceutical preparation comprising an effective amount of a vinyl azole of formula I ##STR17## wherein X is N or CH,
- Y is S or CH.dbd.CH,
- Z is cyano, and one of R.sup.1 or R.sup.2 is carboxyl unsterified or esterified with C.sub.1-10 straightchain, branched-chain or cyclic O-alkyl;
- or with O-aryl, wherein aryl is phenyl or naphthyl, unsubstituted or substituted by 1-3 C.sub.1-4 -alkyl or halogen;
- or with an O-aralkyl, wherein aryl and alkyl have the indicated meanings, carboxylic acid amide, wherein the carboxyl has the above-indicated meaning;
- unsubstituted or substituted with 1-2 same or different C.sub.1-10 straight-chain or branched-chain alkyl;
- or C.sub.6-10 aryl, unsubstituted or substituted by 1-3 C1-4 alkyl or halogen;
- and the amide N can also be part of a 5-8membered heterocyclic ring, containing no additional heteroatom or an additional ring heteroatom N, O or S, and the additional N is unsubstituted or substituted by R.sup.6, wherein R.sup.6 is H or C.sub.1-6 straight-chain or branched-chain alkyl, aldehyde, alkylketone --CO--R.sup.7, wherein R.sup.7 iS a straight-chain or branched-chain C.sub.1-10 alkyl or C.sub.3-12 cycloalkyl, arylketone --CO--R.sup.8, wherein R.sup.8 is phenyl, naphthyl or heteroaryl, unsubstituted or substituted 1-3 times by C.sub.1-4 alkyl, halogen, hydroxy or C.sub.1-4 alkoxy, sulfonamide, unsubstituted or substituted by R.sup.6, or cyano;
- and the respective other R.sup.1 or R.sup.2 is hydrogen, C.sub.1-4 lower-alkyl or cycloalkyl, unsubstituted or substituted aryl, aralkyl, unesterified or esterified carboxyl, unsubstituted or substituted carboxylic acid amide, aldehyde, alkylketone or arylketone or cyano, each as defined above;
- R.sup.1 and R.sup.2 together with the carbon atom on which they are bound form a 5-, 6- or 7-membered ring, which further contains a ketone, ester, lactone, lactam or imide, wherein at least one carbonyl is conjugated with a vinyl double bond;
- and
- R.sup.3 is hydrogen;
- or
- R.sup.3 together with R.sup.2 are
- --O--C.dbd.O or --N--C.dbd.O, unsubstituted or substituted on the N,
- wherein
- the carbonyl is conjugated with a vinyl double bond, and a pharmaceutically acceptable excipient, wherein the preparation is in a unit dosage form for oral administration, is sterile for parenteral administration, or is a cream or ointment for topical administration.
13 more elements
A vinyl azole of formula 1a ##STR20## wherein X is N or CH,
- Y is S or CH.dbd.CH,
- Z.sup.a is cyano and
- R.sup.1a or R.sup.2a is carboxyl unesterified or esterified with C straightchain or branched-chain or cyclic 0-alkyl;
- or with O-aryl, wherein aryl is phenyl or naphthyl, unsubstituted or substituted 1-3 times by C.sub.1-4 -alkyl or halogen;
- or with O-aralkyl, wherein aryl and alkyl have the indicated meanings, carboxylic acid amide, wherein the carboxyl has the above-indicated meaning unsubstituted or substituted 1-2 times by same or different C.sub.1-10 straight-chain or branched-chain alkyl;
- or C.sub.6-10 aryl unsubstituted or substituted 1-3 times by C.sub.1-4 alkyl or halogen, and the amide N is optionally can be part of a 5-8membered heterocyclic ring, containing no additional heteroatom or an additional ring heteroatom N, O or S, and the additional N is unsubstituted or substituted by R.sup.6, wherein R.sup.6 is H or C.sub.1-6 straight-chain or branched-chain alkyl, aidehyde, arylketone -CO-R.sup.8, wherein R.sup.a is phenyl, naphthyl or heteroaryl, unsubstituted or substituted 1-3 times by C.sub.1-4 alkyl, halogen, hydroxy or C.sub.1-4 alkoxy, sulfonamide, unsubstituted or substituted by R.sup.6, or cyano and the respective other R.sup.TM or R.sup.2a is hydrogen, lower-alkyl or cycloalkyl, unsubstituted or substituted aryl, aralkyl, unesterified or esterified carboxyl, unsubstituted or substituted carboxylic acid amide, aldehyde, arylketone or cyano, each as defined above,
- with the proviso that R.sup.TM and R.sup.2a are not simultaneously hydrogen and arylketone,
- R.sup.2a and R.sup.2a together with the carbon on which they are bound form a 5-, 6- or 7-membered ring, which further contains a ketone, ester, lactone, lactam or imide, wherein at least one carbonyl is conjugated with a vinyl double bond;
- and
- R.sup.3 [means]is hydrogen;
- or
- R.sup.3 together with R.sup.2a are --OC --O--N--C .dbd.or unsubstituted or substituted on the N, wherein the carbonyl group is conjugated with a vinyl double bond.
9 more elements
Dependencies are inferred from the claim text.