Charterhouse Therapeutics Ltd.

Crawford Healthcare Holdings Limited

Stanley Michael Roberts

Maria Gabriella Santoro

Alan Michael Happe

Paul Evans

Vasudev Jadhav

Gabriella Santoro

Mazhar Iqbal

Jérôme Dauvergne

Nicolette Christa Ross

Timothy James Snape

The present invention relates to compounds of formula I or II:&#x2014;wherein R is an alkyl, alkenyl, alkynyl, aryl, aralkyl, aralkenyl, or aralkynyl group, that may be substituted or unsubstituted, and that optionally includes at least one heteroatom in its carbon skeleton; Ris hydrogen, or an alkyl, substituted alkyl, alkenyl, alkynyl, aryl, substituted aryl, or aralkyl group; and Ris an alkyl, alkenyl, alkynyl, aryl, aralkyl, aralkenyl, or aralkynyl group containing 4-12 carbon atoms, that may be substituted or unsubstituted, and that optionally includes at least one heteroatom in its carbon skeleton; provided that in a compound of formula I, when Ris an iso-propyl or phenyl group, Ris not an acetyl or tert-butyldimethylsilyl group; and their use in therapeutic, diagnostic and research methods. 

Pharmaceutical compositions

A compound comprising a cyclopentanone, cyclopentenone, cyclohexanone or cyclohexenone group, wherein a first ring carbon atom carries an &#x2014;SR substituent, R is a substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, aralkyl, aralkenyl, or aralkynyl group that, optionally, includes at least one heteroatom in its carbon skeleton, the remaining available ring carbon atoms are optionally substituted, and said compound either: &#x2014;(a) is more soluble in water at a temperature of 20-40&#xb0; C.; (b) is less lipophilic; and/or, (c) has a greater therapeutic index; or; (d) is less soluble in water at a temperature of 20-40&#xb0; C.; (e) is more lipophilic; and/or, (f) has a greater therapeutic index; than an equivalent cyclohex-2-en-1-one or cyclopent-2-en-1-one derivative in which a hydrogen atom replaces said &#x2014;SR group. 

A method of preparing prostanoid cross-conjugated dienones, via a tandem conjugate addition-Peterson olefination reaction route is described. Such compounds may be useful in medicine and other fields.

Synthetic method and novel chemical compounds

A compound of formula (I) or (II): wherein A is hydrogen or CRR; Y and Z are each, independently, hydrogen or a halogen; X is &#x2014;NRR, or R; Ris hydrogen, or a substituted or unsubstituted alkyl or alkenyl group containing 1&#x2013;4 carbon atoms; when X is &#x2014;NRR, Ris a substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, aralkyl aralkenyl, or aralkynyl group, that optionally includes at least one heteroatom in its carbon skeleton and contains 1&#x2013;12 carbon atoms; when X is R, Ris an unsubstituted alkyl, alkenyl or alkynyl group, or a substituted or unsubstituted aryl, aralkyl aralkenyl, or aralkynyl group, that optionally includes at least one heteroatom in its carbon skeleton and contains 1&#x2013;12 carbon atoms; Ris a substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, aralkyl aralkenyl, or aralkynyl group, that optionally includes at least one heteroatom in its carbon skeleton and contains 1&#x2013;12 carbon atoms; Ris hydrogen, a substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, aralkyl aralkenyl, or aralkynyl group, that optionally includes at least one heteroatom in its carbon skeleton and contains 1&#x2013;12 carbon atoms, &#x2014;COOR, or &#x2014;COR; Ris hydrogen, or a substituted or unsubstituted alkyl or alkenyl group containing 1&#x2013;5 carbon atoms; Ris an unsubstituted alkyl, alkenyl, or alkynyl group, that contains 1&#x2013;4 carbon atoms; and, Ris an unsubstituted or halo-substituted alkyl, aryl, or aralkyl group, that contains 1&#x2013;12 carbon atoms 

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Kersbrook, United Kingdom

Stanley Michael Roberts