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US 8,598,229 B2Granted
Tiglien-3-one derivatives
AssigneeQBiotics Limited
InventorsPaul Warren Reddell, Victoria Anne Gordon
Life of this patent
Estimating the term…
Abstract
The present invention relates to tiglien-3-one compounds and their use in methods of treating or preventing protozoal infections, bacterial infections, parasitic infections and cell proliferative disorders. The tiglien-3-one compounds are also used in methods of controlling pests in humans, animals, plants and the environment.
Claims13
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, —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, 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)cycloalkyl, —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 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)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)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 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, —OR28, —SR28, —N(R28)2, —NO2, —NR28OR28, —ON(R28)2, —SOR28, —SO2R28, —SO3R28, —SON(R28)2, —SON(R28)2, —SO3N(R28)2, —P(R28)3, —P(═O)(R28)3, —OSi(R28)3 or —OB(R28)2, and wherein R28 is hydrogen, —C1-C6alkyl, —C2-C6alkenyl, —C2-C6alkynyl, —C3-C8cycloalkyl, —C6-C14aryl, arylalkyl, —C1-C6haloalkyl, —C1-C6dihaloalkyl or —C1-C6trihaloalkyl;
- and geometric isomers or stereoisomers thereof, or pharmaceutically, agriculturally or pesticidally acceptable salts thereof.
18 more elements
A pharmaceutical or pesticidal 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, —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 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)cycloalkyl, —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 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)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)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 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, —OR28, —SR28, —N(R28)2, —NO2, —NR28OR28, —ON(R28)2, —SOR28, —SO2R28, —SO3R28, —SON(R28)2, —SON(R28)2, —SO3N(R28)2, —P(R28)3, —P(═O)(R28)3, —OSi(R28)3 or —OB(R28)2, and wherein R28 is hydrogen, —C1-C6alkyl, —C2-C6alkenyl, —C2-C6alkynyl, —C3-C8cycloalkyl, —C6-C14aryl, arylalkyl, —C1-C6haloalkyl, —C1-C6dihaloalkyl or —C1-C6trihaloalkyl;
- and geometric isomers or stereoisomers thereof, or pharmaceutically, agriculturally or pesticidally acceptable salts thereof;
- and a pharmaceutically, agriculturally or pesticidally acceptable carrier.
19 more elements
Dependencies are inferred from the claim text.