Hepodxilin analog enantiomers
AssigneeCecil Pace-Asciak
InventorsCecil Pace-Asciak, Alexandra SantAna Sorensen, Jean-Philippe Meyer, Peter Denim
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Abstract
The present invention relates to enantiomeric forms of hepoxilin analogs of Formula I-VIII, pharmaceutical compositions thereof, a method for the separation of said enantiomeric forms of hepoxilin analogs comprising applying said hepoxilin to a chiral phase HPLC column and eluting said hepoxilin with an alkane and alcohol solvent mixture. Said enantiomeric forms of hepoxilin analogs of Formula I-VIII were found to be useful in controlling the biological effects of PPAR mediated transcriptional control for the treatment of diseases such as cancer, thromboxane-mediated diseases and for modulating intracellular calcium concentration.
Claims19
A compound of formula:
- wherein,
- X is CH2;
- R1 is lower alkyl, alkenyl or alkynyl;
- lower alcohol, saturated or unsaturated;
- aryl;
- substituted aryl;
- —(CH2)n-phenyl where n is 1 to 9;
- or Z-R5, wherein Z is a single bond or a C1-C10 carbon chain optionally substituted with —OH and/or halogen and/or optionally containing up to three double or triple bonds or a mixture of double and triple bonds up to a maximum of three;
- and R5 is C1-C10 alkyl OH, C1-C10 alkyl-halide, C1-C10 alkyl N3, C1-C10 alkyl-NH2 or COOR6 or CONHR6, wherein R6 is H, C5 or C6 cycloalkyl, C5-C6 aryl, a sugar moiety or C1-C10 alkyl or alkenyl optionally substituted with COOH, C5-C6 aryl, heterocycle or a sugar moiety;
- R2 OH, halogen, NH2, SH, OPO3H, lower alkyl, alkenyl or alkynyl, lower alcohol, O-lower alkyl or alkenyl, S-lower alkyl or alkenyl, NH-lower alkyl or alkenyl, or N his-lower alkyl or alkenyl;
- and
- R3 is a C4-C15 carbon chain optionally substituted with —OR7, wherein R7 is H, lower alkyl, alkenyl or alkynyl;
- wherein R3 optionally contains up to three double or triple bonds or a mixture of double and triple bonds up to a maximum of three;
- or a pharmaceutical salt, methyl ester, sugar amide, or sugar ester thereof.
A compound of formula:
- wherein X is CH2;
- R2 is H, OH, halogen, NH2, SH, OPO3H, lower alkyl, alkenyl or alkynyl, lower alcohol, O-lower alkyl or alkenyl, S-lower alkyl or alkenyl, NH-lower alkyl or alkenyl, or N bis-lower alkyl or alkenyl;
- R3 is a C4-C15 carbon chain optionally substituted with —OR7, wherein R7 is —H, lower alkyl, alkenyl or alkynyl;
- and wherein R3 optionally contains up to throe double or triple bonds or a mixture of double and triple bonds up to a maximum of three;
- and
- R4 is lower alkyl, alkenyl or alkynyl;
- lower alcohol, saturated or unsaturated;
- aryl;
- substituted aryl;
- —(CH2)n-phenyl where n is 1 to 9;
- or Z—R5 , wherein Z is a single bond or a C1-C10carbon chain optionally substituted with —OH and/or halogen and/or optionally containing up to three double or triple bonds or a mixture of double and triple bonds up to a maximum of three;
- and R5 is C1-C10alkyl OH, C1-C10 alkyl-halide, C1-C10 alkyl N3, C1-C10 alkyl —NH2 or COOR6 or CONHR6, wherein R6 is H, C5 or C6 cycloalkyl, C5-C6 aryl, a sugar moiety or C1-C10 alkyl or alkenyl optionally substituted with COOH, C5-C6 aryl, heterocycle or a sugar moiety;
- or a pharmaceutical salt, methyl ester, sugar amide, or sugar ester thereof.
Dependencies are inferred from the claim text.