Tiglien-3-one derivatives

A method of treating a bacterial or nematode infection comprising administering to a subject in need thereof a compound of formula (II):

• wherein:
• X is —O—, —S— or —NR25—;
• 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)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C10 alkyl, —OC(O)NHC2-C10 alkenyl, —OC(O)NHC2-C10 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C10 alkyl, —OC(S)NHC2-C10 alkenyl, —OC(S)NHC2-C10 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, —OC(S)NHheteroaryl 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)cycloalkyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C10 alkyl, —OC(O)NHC2-C10 alkenyl, —OC(O)NHC2-C10 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C10 alkyl, —OC(S)NHC2-C10 alkenyl, —OC(S)NHC2-C10 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, —OC(S)NHheteroaryl, 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 hydrogen, —C1-C10 alkyl, —C2-C10 alkenyl or —C2-C10 alkynyl;
• R8 is hydrogen, —C1-C10 alkyl, —C2-C10 alkenyl or —C2-C10 alkynyl;
• R10 is hydrogen, —C1-C10 alkyl, —C2-C10 alkenyl or —C2-C10 alkynyl;
• R11 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)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, or —OC(S)NHheteroaryl;
• 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)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, or —OC(S)NHheteroaryl;
• 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, —OC(O)heterocyclyl, —OC(O)heteroaryl, —NHC1-C20 alkyl, —NHC2-C20 alkenyl, —NHC2-C20 alkynyl, —NHcycloalkyl, —NHaryl, —NHheterocyclyl, —NHheteroaryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, or —OC(S)NHheteroaryl;
• 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, —OC(O)aryl, —OC(O)heterocyclyl, or —OC(O)heteroaryl;
• 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)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, or —OC(S)NHheteroaryl;
• 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)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, or —OC(S)NHheteroaryl;
• 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)heterocyclyl, —OC(O)heteroaryl, —OC(O)NHC1-C20 alkyl, —OC(O)NHC2-C20 alkenyl, —OC(O)NHC2-C20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(O)NHheterocyclyl, —OC(O)NHheteroaryl, —OC(S)NHC1-C20 alkyl, —OC(S)NHC2-C20 alkenyl, —OC(S)NHC2-C20 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, —OC(S)NHheterocyclyl, or —OC(S)NHheteroaryl;
• 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, aryl, heterocyclyl and heteroaryl is optionally substituted;
• or a geometric isomer or stereoisomer thereof or a pharmaceutically acceptable salt thereof.