Tiglien-3-one derivatives

A pharmaceutical composition comprising a compound of formula (II):

• wherein:
• X is —O—;
• R1 and R2 are each independently hydrogen, —OH, —OC1-C10 alkyl, —OC2-C10 alkenyl, —OC2-C10 alkynyl, —Ocycloalkyl, —OC(O)C1-C10 alkyl, —OC(O)C2-C10 alkenyl, —OC(O)C2-C10 alkynyl, —OC(O)cycloalkyl, —OC(O)NHC1-C10 alkyl or —OC(O)NHC2-C10 alkenyl, —OC(O)NHC2-C10 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(S)NHC1-C10 alkyl, —OC(S)NHC2-C10 alkenyl, (S)NHC2-C10 alkynyl, —OC(S)NHcycloalkyl or —OC(S)NHaryl, or R1 and R2 taken together are ═O, ═S, ═NH or ═N(C1-C6 alkyl);
• R3 is hydrogen, —C1-C10 alkyl, —C2-C10 alkenyl or —C2-C10 alkynyl;
• R4 and R5 are each independently hydrogen, —C1-C10 alkyl, —C2-C10 alkenyl, —C2-C10 alkynyl, —OH, —OC1-C10 alkyl, —OC2-C10 alkenyl, —OC2-C10 alkynyl, —Ocycloalkyl, —OC(O)C1-C10 alkyl, —OC(O)C2-C10 alkenyl, —OC(O)C2-C10 alkynyl, —OC(O)cycl ° alkyl, —OC(O)aryl, —OC(O)NHC1-C10 alkyl, —OC(O)NHC2-C10 alkenyl, —OC(O)NHC2-C10 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(S)NHC1-C10 alkyl, —OC(S)NHC2-C10 alkenyl, —OC(S)NHC2-C10 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, F, Cl, Br, I, —CN, —NO2 or N(R25)2, or R4 and R5 taken together form a double bond or are —O—, —S—, —NR25— or —CR26R27—;
• R6 is selected from the group consisting of hydrogen, —C1-C10 alkyl, —C2-C10 alkenyl and —C2-C10 alkynyl;
• R8 is selected from the group consisting of hydrogen, —C1-C10 alkyl, —C2-C10 alkenyl and —C2-C10 alkynyl;
• R10 is selected from the group consisting of hydrogen, —C1-C10 alkyl, —C2-C10 alkenyl and —C2-C10 alkynyl;
• R11 is —OH, —OC1-C20 alkyl, —OC2-C20 alkenyl, —OC2-C20 alkynyl, —Ocycloalkyl, —OC(O)C2-C20 alkyl, —OC(O)C2-C20 alkenyl, —OC(O)C2-C20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl or —OC(S)NHaryl, or R10 and R11 taken together form a carbonyl group (═O);
• R12 is —OH, —OC1-C20 alkyl, —OC2-C20 alkenyl, —OC2-C20 alkynyl, —Ocycloalkyl, —OC(O)C1-C20 alkyl, —OC(O)C2-C20 alkenyl, —OC(O)C2-C20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl or —OC(S)NHaryl;
• R13 and R14 are each independently hydrogen or —C1-C10 alkyl;
• R18 is C1-C20 alkyl, —C2-C20 alkenyl, —C2-C20 alkynyl, —OH, —OC1-C20 alkyl, —OC2-C20 alkenyl, —OC2-C20 alkynyl, —Ocycloalkyl, —OC(O)C1-C20 alkyl, —OC(O)C2-C20 alkenyl, —OC(O)C2-C20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —NHC1-C20 alkyl, —NHC2-C20 alkenyl, —NHC2-C20 alkynyl, —NHcycloalkyl, —NHaryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl or —OC(S)NHaryl;
• R19 and R20 are each independently hydrogen, —C1-C6 alkyl, —C2-C6 alkenyl, —C2-C20 alkynyl, —OH, —OC1-C6 alkyl, —OC2-C6 alkenyl, —OC2-C6 alkynyl, —Ocycloalkyl, —OC(O)C1-C6 alkyl, —OC(O)C2-C6 alkenyl, —OC(O)C2-C6 alkynyl, —OC(O)cycloalkyl or —OC(O)aryl, or R19 and R20 taken together form a carbonyl or thiocarbonyl group;
• R21 is hydrogen, —C1-C10 alkyl, —C2-C10 alkenyl or —C2-C10 alkynyl;
• R22 is —OH, —OC1-C20 alkyl, —OC2-C20 alkenyl, —OC2-C20 alkynyl, —Ocycloalkyl, —OC(O)C1-C20 alkyl, —OC(O)C2-C20 alkenyl, —OC(O)C2-C20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)NH C1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl and —OC(S)NHaryl, or R21 and R22 taken together form a carbonyl group;
• R23 is hydrogen, —OH, —OC1-C20 alkyl, —OC2-C20 alkenyl, —OC2-C20 alkynyl, —Ocycloalkyl, —OC(O)C1-C20 alkyl, —OC(O)C2-C20 alkenyl, —OC(O)C2-C20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl or —OC(S)NHaryl;
• R24 is hydrogen, —OH, —OC1-C20 alkyl, —OC2-C20 alkenyl, —OC2-C20 alkynyl, —Ocycloalkyl, —OC(O)C1-C20 alkyl, —OC(O)C2-C20 alkenyl, —OC(O)C2-C20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl or —OC(S)NHaryl;
• R25 is hydrogen or —C1-C10 alkyl;
• R26 and R27 are each independently hydrogen, —C1-C10 alkyl, —OH or —OC1-C10 alkyl;
• wherein each alkyl, alkenyl, alkynyl, cycloalkyl and aryl is optionally substituted with one or more optional substituents, wherein each optional substituent is independently —F, —Cl, —Br, —I, —CN, —CF3, —CO2R28, —COR28, —SR28, —N(R28)2, —NO2, —NR28OR28, —ON(R28)2, —SOR28, —SO2R28, —SO3R28, —SON(R28)2, —SO3N(R28)2, —P(R28)3, —P(═O)(R28)3, —OSi(R28)3, —OB(R28)2 and wherein R28 is hydrogen, —C1-C6 alkyl, —C2-C6 alkenyl, —C2-C6 alkynyl, —C3-C8 cycloalkyl, —C6-C14 aryl, arylalkyl, —C1-C6 haloalkyl, —C1-C6 dihaloalkyl or —C1-C6 trihaloalkyl;
• and geometric isomers or stereoisomers thereof and pharmaceutically, agriculturally or pesticidally acceptable salts thereof;
• and
• a pharmaceutically, agriculturally or pesticidally acceptable carrier comprising at least one of cellulose derivatives, malt, gelatine, talc, calcium sulphate, vegetable oils, synthetic oils, alginic acid, phosphate buffered solutions, emulsifiers, isotonic saline, magnesium carbonate, magnesium stearate, lactose, pectin, tragacanth, cocoa butter, low melting wax, propylene glycol, polyethylene glycol, acetone, ethanol, acacia, sucrose, glycerin, cyclodextrin, benzyl alcohol, cremaphor and a propellant.