IP Library › Granted Patent US 8,598,229
Granted Patent B2
US 8,598,229 · App. 12/158,461 · Granted Dec 3, 2013

Tiglien-3-one derivatives

Inventors: Paul Warren Reddell (Yungaburra, AU); Victoria Anne Gordon (Yungaburra, AU)
Assignee: QBiotics Limited
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Quick Facts
Patent No.
US 8,598,229
App. No.
12/158,461
Granted
Dec 3, 2013
Kind
B2
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.

Claims (87)

1. A compound of formula (II):

wherein:

X is —O—;

R 1 and R 2 are each independently hydrogen, —OH, —OC 1 -C 10 alkyl, —OC 2 -C 10 alkenyl, —OC 2 -C 10 alkynyl, —Ocycloalkyl, —OC(O)C 1 -C 10 alkyl, —OC(O)C 2 -C 10 alkenyl, —OC(O)C 2 -C 10 alkynyl, —OC(O)cycloalkyl, —OC(O)NHC 1 -C 10 alkyl, —OC(O)NHC 2 -C 10 alkenyl, —OC(O)NHC 2 -C 10 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(S)NHC 1 -C 10 alkyl, —OC(S)NHC 2 -C 10 alkenyl, —OC(S)NHC 2 -C 10 alkynyl, —OC(S)NHcycloalkyl, or —OC(S)NHaryl, or R 1 and R 2 taken together are ═O, ═S, ═NH or ═N(C 1 -C 6 alkyl);

R 3 is hydrogen, —C 1 -C 10 alkyl, —C 2 -C 10 alkenyl or —C 2 -C 10 alkynyl;

R 4 and R 5 are each independently hydrogen, —C 1 -C 10 alkyl, —C 2 -C 10 alkenyl, —C 2 -C 10 alkynyl, —OH, —OC 1 -C 10 alkyl, —OC 2 -C 10 alkenyl, —OC 2 -C 10 alkynyl, —Ocycloalkyl, —OC(O)C 1 -C 10 alkyl, —OC(O)C 2 -C 10 alkenyl, —OC(O)C 2 -C 10 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)NHC 1 -C 10 alkyl, —OC(O)NHC 2 -C 10 alkenyl, —OC(O)NHC 2 -C 10 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(S)NHC 1 -C 10 alkyl, —OC(S)NHC 2 -C 10 alkenyl, —OC(S)NHC 2 -C 10 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, F, Cl, Br, I, —CN, —NO 2 or N(R 25 ) 2 , or R 4 and R 5 taken together form a double bond or are —O—, —S—, —NR 25 — or —CR 26 R 27 —;

R 6 is hydrogen, —C 1 -C 10 alkyl, —C 2 -C 10 alkenyl or —C 2 -C 10 alkynyl;

R 8 is hydrogen, —C 1 -C 10 alkyl, —C 2 -C 10 alkenyl or —C 2 -C 10 alkynyl;

R 10 is hydrogen, —C 1 -C 10 alkyl, —C 2 -C 10 alkenyl or —C 2 -C 10 alkynyl;

R 11 is —OH, —OC 1 -C 20 alkyl, —OC 2 -C 20 alkenyl, —OC 2 -C 20 alkynyl, —Ocycloalkyl, —OC(O)C 2 -C 20 alkyl, —OC(O)C 2 -C 20 alkenyl, —OC(O)C 2 -C 20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)NHC 1 -C 20 alkyl, —OC(O)NHC 2 -C 20 alkenyl, —OC(O)NHC 2 -C 20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(S)NHC 1 -C 20 alkyl, —OC(S)NHC 2 -C 20 alkenyl, —OC(S)NHC 2 -C 20 alkynyl, —OC(S)NHcycloalkyl, or —OC(S)NHaryl, or R 10 and R 11 taken together form a carbonyl group (═O);

R 12 is —OH, —OC 1 -C 20 alkyl, —OC 2 -C 20 alkenyl, —OC 2 -C 20 alkynyl, —Ocycloalkyl, —OC(O)C 1 -C 20 alkyl, —OC(O)C 2 -C 20 alkenyl, —OC(O)C 2 -C 20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)NHC 1 -C 20 alkyl, —OC(O)NHC 2 -C 20 alkenyl, —OC(O)NHC 2 -C 20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(S)NHC 1 -C 20 alkyl, —OC(S)NHC 2 -C 20 alkenyl, —OC(S)NHC 2 -C 20 alkynyl, —OC(S)NHcycloalkyl, or —OC(S)NHaryl;

R 13 and R 14 are each independently hydrogen or —C 1 -C 10 alkyl;

R 18 is C 1 -C 20 alkyl, —C 2 -C 20 alkenyl, —C 2 -C 20 alkynyl, —OH, —OC 1 -C 20 alkyl, —OC 2 -C 20 alkenyl, —OC 2 -C 20 alkynyl, —Ocycloalkyl, —OC(O)C 1 -C 20 alkyl, —OC(O)C 2 -C 20 alkenyl, —OC(O)C 2 -C 20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —NHC 1 -C 20 alkyl, —NHC 2 -C 20 alkenyl, —NHC 2 -C 20 alkynyl, —NHcycloalkyl, —NHaryl, —OC(O)NHC 1 -C 20 alkyl, —OC(O)NHC 2 -C 20 alkenyl, —OC(O)NHC 2 -C 20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(S)NHC 1 -C 20 alkyl, —OC(S)NHC 2 -C 20 alkenyl, —OC(S)NHC 2 -C 20 alkynyl, —OC(S)NHcycloalkyl, or —OC(S)NHaryl;

R 19 and R 20 are each independently hydrogen, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 20 alkynyl, —OH, —OC 1 -C 6 alkyl, —OC 2 -C 6 alkenyl, —OC 2 -C 6 alkynyl, —Ocycloalkyl, —OC(O)C 1 -C 6 alkyl, —OC(O)C 2 -C 6 alkenyl, —OC(O)C 2 -C 6 alkynyl, —OC(O)cycloalkyl, or —OC(O)aryl, or R 19 and R 20 taken together form a carbonyl or thiocarbonyl group;

R 21 is hydrogen, —C 1 -C 10 alkyl, —C 2 -C 10 alkenyl or —C 2 -C 10 alkynyl;

R 22 is —OH, —OC 1 -C 20 alkyl, —OC 2 -C 20 alkenyl, —OC 2 -C 20 alkynyl, —Ocycloalkyl, —OC(O)C 1 -C 20 alkyl, —OC(O)C 2 -C 20 alkenyl, —OC(O)C 2 -C 20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)NHC 1 -C 20 alkyl, —OC(O)NHC 2 -C 20 alkenyl, —OC(O)NHC 2 -C 20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(S)NHC 1 -C 20 alkyl, —OC(S)NHC 2 -C 20 alkenyl, —OC(S)NHC 2 -C 20 alkynyl, —OC(S)NHcycloalkyl, or —OC(S)NHaryl, or R 21 and R 22 taken together form a carbonyl group;

R 23 is hydrogen, —OH, —OC 1 -C 20 alkyl, —OC 2 -C 20 alkenyl, —OC 2 -C 20 alkynyl, —Ocycloalkyl, —OC(O)C 1 -C 20 alkyl, —OC(O)C 2 -C 20 alkenyl, —OC(O)C 2 -C 20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)NHC 1 -C 20 alkyl, —OC(O)NHC 2 -C 20 alkenyl, —OC(O)NHC 2 -C 20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(S)NHC 1 -C 20 alkyl, —OC(S)NHC 2 -C 20 alkenyl, —OC(S)NHC 2 -C 20 alkynyl, —OC(S)NHcycloalkyl, or —OC(S)NHaryl;

R 24 is hydrogen, —OH, —OC 1 -C 20 alkyl, —OC 2 -C 20 alkenyl, —OC 2 -C 20 alkynyl, —Ocycloalkyl, —OC(O)C 1 -C 20 alkyl, —OC(O)C 2 -C 20 alkenyl, —OC(O)C 2 -C 20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)NHC 1 -C 20 alkyl, —OC(O)NHC 2 -C 20 alkenyl, —OC(O)NHC 2 -C 20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(S)NHC 1 -C 20 alkyl, —OC(S)NHC 2 -C 20 alkenyl, —OC(S)NHC 2 -C 20 alkynyl, —OC(S)NHcycloalkyl, or —OC(S)NHaryl;

R 25 is hydrogen or —C 1 -C 10 alkyl;

R 26 and R 27 are each independently hydrogen, —C 1 -C 10 alkyl, —OH, or —OC 1 -C 10 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, —CF 3 , —CO 2 R 28 , —COR 28 , —OR 28 , —SR 28 , —N(R 28 ) 2 , —NO 2 , —NR 28 OR 28 , —ON(R28)2, —SOR 28 , —SO 2 R 28 , —SO 3 R 28 , —SON(R 28 ) 2 , —SON(R 28 ) 2 , —SO 3 N(R 28 ) 2 , —P(R 28 ) 3 , —P(═O)(R 28 ) 3 , —OSi(R 28 ) 3 or —OB(R 28 ) 2 , and wherein R 28 is hydrogen, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 8 cycloalkyl, —C 6 -C 14 aryl, arylalkyl, —C 1 -C 6 haloalkyl, —C 1 -C 6 dihaloalkyl or —C 1 -C 6 trihaloalkyl;

and geometric isomers or stereoisomers thereof, or pharmaceutically, agriculturally or pesticidally acceptable salts thereof.

2. A compound according to claim 1 , wherein the compound is a compound of formula (III):

wherein:

R 3 is hydrogen, —C 1 -C 6 alkyl or —C 2 -C 6 alkenyl;

R 4 and R 5 are each independently hydrogen, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —OH, —OC 1 -C 6 alkyl, —OC 2 -C 6 alkenyl, —OC(O)C 1 -C 6 alkyl, —OC(O)C 2 -C 6 alkenyl, —OC(O)aryl, F, Cl, Br or I, or R 4 and R 5 taken together form a double bond or are —O—;

R 6 is hydrogen, —C 1 -C 6 alkyl or —C 2 -C 6 alkenyl;

R 8 is hydrogen, —C 1 -C 6 alkyl or —C 2 -C 6 alkenyl;

R 13 and R 14 are each independently hydrogen or —C 1 -C 6 alkyl;

R a is hydrogen, —C 1 -C 20 alkyl, —C 2 -C 20 alkenyl, —C 2 -C 20 alkynyl, —C(O)C 2 -C 20 alkyl, —C(O)C 2 -C 20 alkenyl, —OC(O)C 2 -C 20 alkynyl, —C(O)cycloalkyl, —C(O)aryl, —C(O)NHC 1 -C 20 alkyl, —C(O)NHC 2 -C 20 alkenyl, —C(O)NHC 2 -C 20 alkynyl, —C(O)NHcycloalkyl, —C(O)NHaryl, —C(S)NHC 1 -C 20 alkyl, —C(S)NHC 2 -C 20 alkenyl, —C(S)NHC 2 -C 20 alkynyl, —C(S)NHcycloalkyl, or —C(S)NHaryl;

R b , R C , R d , R e and R f are each independently hydrogen, —C 1 -C 20 alkyl, —C 2 -C 20 alkenyl, —C 2 -C 20 alkynyl, —C(O)C 1 -C 20 alkyl, —C(O)C 2 -C 20 alkenyl, —OC(O)C 2 -C 20 alkynyl, —C(O)cycloalkyl, —C(O)aryl, —C(O)NHC 1 -C 20 alkyl, —C(O)NHC 2 -C 20 alkenyl, —C(O)NHC 2 -C 20 alkynyl, —C(O)NHcycloalkyl, —C(O)NHaryl, —C(S)NHC 1 -C 20 alkyl, —C(S)NHC 2 -C 20 alkenyl, —C(S)NHC 2 -C 20 alkynyl, —C(S)NHcycloalkyl, or —C(S)NHaryl;

wherein each alkyl, alkenyl and aryl group is optionally substituted with one or more optional substituents, wherein each optional substituent is as defined in claim 1 ;

or geometric isomers or stereoisomers, or pharmaceutically, agriculturally or pesticidally acceptable salts thereof.

3. A compound according to claim 1 , wherein the compound is a compound of formula (IV):

wherein:

R 3 is hydrogen, —C 1 -C 6 alkyl or —C 2 -C 6 alkenyl;

R 4 and R 5 are each independently hydrogen, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —OH, —OC 1 -C 6 alkyl, —OC 2 -C 6 alkenyl, —OC(O)C 1 -C 6 alkyl, —OC(O)C 2 -C 6 alkenyl, —OC(O)aryl, —OC(O)heterocyclyl, —OC(O)heteroaryl, F, Cl, Br or I, or R 4 and R 5 taken together form a double bond or are —O—;

R 6 is hydrogen, —C 1 -C 6 alkyl or —C 2 -C 6 alkenyl;

R 8 is hydrogen, —C 1 -C 6 alkyl or —C 2 -C 6 alkenyl;

R 10 is hydrogen;

R 11 is hydroxy, —OC 1 -C 20 alkyl, —OC 2 -C 20 alkenyl, —OC(O)C 2 -C 20 alkyl, —OC(O)C 2 -C 20 alkenyl or —OC(O)aryl, or R 10 and R 11 taken together form a carbonyl group;

R 12′ is hydrogen, —C 1 -C 20 alkyl, —C 2 -C 20 alkenyl, —C(O)C 1 -C 20 alkyl, —C(O)C 2 -C 20 alkenyl or —C(O)aryl;

R 13 and R 14 are each independently hydrogen or —C 1 -C 6 alkyl;

R 18′ is hydrogen, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C(O)C 1 -C 6 alkyl, —C(O)C 2 -C 6 alkenyl or —C(O)aryl;

R 19 and R 20 are each independently hydrogen, —OH, —OC 1 -C 6 alkyl, or —OC 2 -C 6 alkenyl, or R 19 and R 20 taken together form a carbonyl group;

R 21 is hydrogen;

R 22 is hydroxy, —OC 1 -C 6 alkyl, —OC 2 -C 6 alkenyl, —OC(O)C 1 -C 6 alkyl, —OC(O)C 2 -C 6 alkenyl, or —OC(O)aryl, or R 21 and R 22 taken together form a carbonyl group;

wherein each alkyl, alkenyl and aryl is optionally substituted with one or more optional substituents, wherein each optional substituent is as defined in claim 1 ;

and geometric isomers or stereoisomers thereof, or pharmaceutically, agriculturally or pesticidally acceptable salts thereof.

4. A compound according to claim 1 wherein R 1 and R 2 are each independently hydrogen, hydroxy, —OC 1 -C 6 alkyl, —OC 2 -C 6 alkenyl, —OC(O)C 1 -C 6 alkyl or —OC(O)C 2 -C 6 alkenyl, or R 1 and R 2 taken together form a carbonyl group.

5. A compound according to claim 1 wherein R 4 and R 5 form a double bond or R 4 and R 5 are hydrogen or together are —O—.

6. A compound according to claim 1 wherein R 8 is hydrogen or —C 1 -C 3 alkyl.

7. A compound according to claim 1 wherein R 11 is hydroxy, —C 1 -C 20 alkyloxy, —C 2 -C 20 alkenyloxy, —OC(O)C 2 -C 20 alkyl or —OC(O)C 2 -C 20 alkenyl, and R 12 is hydroxy, —C 1 -C 20 alkyloxy, —C 2 -C 20 alkenyloxy, —OC(O)C 1 -C 20 alkyl or —OC(O)C 2 -C 20 alkenyl.

8. A compound according to claim 1 wherein R 13 and R 14 are each independently hydrogen or —C 1 -C 3 alkyl.

9. A compound according to claim 1 wherein R 19 and R 20 are each independently hydrogen, hydroxy, —OC 1 -C 3 alkyl, or —OC 2 -C 3 alkenyl, or R 19 and R 20 taken together form a carbonyl group and R 18 is hydroxy, —OC 1 -C 6 alkyl, —OC 2 -C 6 alkenyl, —OC(O)C 1 -C 6 alkyl or —OC(O)C 2 -C 6 alkenyl.

10. A compound according to claim 1 wherein R 22 is hydroxy, —OC 1 -C 6 alkyl, —OC 2 -C 6 alkenyl, —OC(O)C 1 -C 6 alkyl or —OC(O)C 2 -C 6 alkenyl.

11. A compound according to claim 1 wherein R 23 and R 24 are each hydroxy.

12. A compound according to claim 1 which is:

(12-tigloyl-13-(2-methylbutanoyl)-6,7-epoxy-4,5,9,12,13,20-hexahydroxy-1-tigliaen-3-one);

(12,13-di-(2-methylbutanoyl)-6,7-epoxy-4,5,9,12,13,20-hexahydroxy-tigliaen-3-one);

12-(dodeca-2,4,6-trienoyl)-13-(2-methylbutanoyl)-6,7-epoxy-4,5,9,12,13,20-hexahydroxy-1-tigliaen-3-one;

12-(deca-2,4-dienoyl)-6,7-epoxy-4,5,9,12,13,20-hexahydroxy-1-tigliaen-3-one;

12,13-di-(2-methylbutanoyl)-1,2-2H-1,2,6,7-diepoxy-6-carboxy-4,5,9,12,13-pentahydroxy-tigliaen-3-one; and

12,13-di-(2-methylbutanoyl)-5,20-di-acetoyl-4,5,9,12,13,20-hexahydroxy-tigliaen-3-one.

13. A pharmaceutical or pesticidal composition comprising a compound of formula (II):

wherein:

X is —O—;

R 1 and R 2 are each independently hydrogen, —OH, —OC 1 -C 10 alkyl, —OC 2 -C 10 alkenyl, —OC 2 -C 10 alkynyl, —Ocycloalkyl, —OC(O)C 1 -C 10 alkyl, —OC(O)C 2 -C 10 alkenyl, —OC(O)C 2 -C 10 alkynyl, —OC(O)cycloalkyl, —OC(O)NHC 1 -C 10 alkyl, —OC(O)NHC 2 -C 10 alkenyl, —OC(O)NHC 2 -C 10 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(S)NHC 1 -C 10 alkyl, —OC(S)NHC 2 -C 10 alkenyl, —OC(S)NHC 2 -C 10 alkynyl, —OC(S)NHcycloalkyl or —OC(S)NHaryl, or R 1 and R 2 taken together are ═O, ═S, ═NH or ═N(C 1 -C 6 alkyl);

R 3 is hydrogen, —C 1 -C 10 alkyl, —C 2 -C 10 alkenyl or —C 2 -C 10 alkynyl;

R 4 and R 5 are each independently hydrogen, —C 1 -C 10 alkyl, —C 2 -C 10 alkenyl, —C 2 -C 10 alkynyl, —OH, —OC 1 -C 10 alkyl, —OC 2 -C 10 alkenyl, —OC 2 -C 10 alkynyl, —Ocycloalkyl, —OC(O)C 1 -C 10 alkyl, —OC(O)C 2 -C 10 alkenyl, —OC(O)C 2 -C 10 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)NHC 1 -C 10 alkyl, —OC(O)NHC 2 -C 10 alkenyl, —OC(O)NHC 2 -C 10 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(S)NHC 1 -C 10 alkyl, —OC(S)NHC 2 -C 10 alkenyl, —OC(S)NHC 2 -C 10 alkynyl, —OC(S)NHcycloalkyl, —OC(S)NHaryl, F, Cl, Br, I, —CN, —NO 2 or N(R 25 ) 2 , or R 4 and R 5 taken together form a double bond or are —O—, —S—, —NR 25 — or —CR 26 R 27 —;

R 6 is hydrogen, —C 1 -C 10 alkyl, —C 2 -C 10 alkenyl or —C 2 -C 10 alkynyl;

R 8 is hydrogen, —C 1 -C 10 alkyl, —C 2 -C 10 alkenyl or —C 2 -C 10 alkynyl;

R 10 is hydrogen, —C 1 -C 10 alkyl, —C 2 -C 10 alkenyl or —C 2 -C 10 alkynyl;

R 11 is —OH, —OC 1 -C 20 alkyl, —OC 2 -C 20 alkenyl, —OC 2 -C 20 alkynyl, —Ocycloalkyl, —OC(O)C 1 -C 20 alkyl, —OC(O)C 2 -C 20 alkenyl, —OC(O)C 2 -C 20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)NHC 1 -C 20 alkyl, —OC(O)NHC 2 -C 20 alkenyl, —OC(O)NHC 2 -C 20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(S)NHC 1 -C 20 alkyl, —OC(S)NHC 2 -C 20 alkenyl, —OC(S)NHC 2 -C 20 alkynyl, —OC(S)NHcycloalkyl or —OC(S)NHaryl, or R 10 and R 11 taken together form a carbonyl group (═O);

R 12 is —OH, —OC 1 -C 20 alkyl, —OC 2 -C 20 alkenyl, —OC 2 -C 20 alkynyl, —Ocycloalkyl, —OC(O)C 1 -C 20 alkyl, —OC(O)C 2 -C 20 alkenyl, —OC(O)C 2 -C 20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)NHC 1 -C 20 alkyl, —OC(O)NHC 2 -C 20 alkenyl, —OC(O)NHC 2 -C 20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(S)NHC 1 -C 20 alkyl, —OC(S)NHC 2 -C 20 alkenyl, —OC(S)NHC 2 -C 20 alkynyl, —OC(S)NHcycloalkyl or —OC(S)NHaryl;

R 13 and R 14 are each independently hydrogen or —C 1 -C 10 alkyl;

R 18 is C 1 -C 20 alkyl, —C 2 -C 20 alkenyl, —C 2 -C 20 alkynyl, —OH, —OC 1 -C 20 alkyl, —OC 2 -C 20 alkenyl, —OC 2 -C 20 alkynyl, —Ocycloalkyl, —OC(O)C 1 -C 20 alkyl, —OC(O)C 2 -C 20 alkenyl, —OC(O)C 2 -C 20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —NHC 1 -C 20 alkyl, —NHC 2 -C 20 alkenyl, —NHC 2 -C 20 alkynyl, —NHcycloalkyl, —NHaryl, —OC(O)NHC 1 -C 20 alkyl, —OC(O)NHC 2 -C 20 alkenyl, —OC(O)NHC 2 -C 20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(S)NHC 1 -C 20 alkyl, —OC(S)NHC 2 -C 20 alkenyl, —OC(S)NHC 2 -C 20 alkynyl, —OC(S)NHcycloalkyl or —OC(S)NHaryl;

R 19 and R 20 are each independently hydrogen, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 20 alkynyl, —OH, —OC 1 -C 6 alkyl, —OC 2 -C 6 alkenyl, —OC 2 -C 6 alkynyl, —Ocycloalkyl, —OC(O)C 1 -C 6 alkyl, —OC(O)C 2 -C 6 alkenyl, —OC(O)C 2 -C 6 alkynyl, —OC(O)cycloalkyl or —OC(O)aryl, or R 19 and R 20 taken together form a carbonyl or thiocarbonyl group;

R 21 is hydrogen, —C 1 -C 10 alkyl, —C 2 -C 10 alkenyl or —C 2 -C 10 alkynyl;

R 22 is —OH, —OC 1 -C 20 alkyl, —OC 2 -C 20 alkenyl, —OC 2 -C 20 alkynyl, —Ocycloalkyl, —OC(O)C 1 -C 20 alkyl, —OC(O)C 2 -C 20 alkenyl, —OC(O)C 2 -C 20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)NHC 1 -C 20 alkyl, —OC(O)NHC 2 -C 20 alkenyl, —OC(O)NHC 2 -C 20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(S)NHC 1 -C 20 alkyl, —OC(S)NHC 2 -C 20 alkenyl, —OC(S)NHC 2 -C 20 alkynyl, —OC(S)NHcycloalkyl or —OC(S)NHaryl, or R 21 and R 22 taken together form a carbonyl group;

R 23 is hydrogen, —OH, —OC 1 -C 20 alkyl, —OC 2 -C 20 alkenyl, —OC 2 -C 20 alkynyl, —Ocycloalkyl, —OC(O)C 1 -C 20 alkyl, —OC(O)C 2 -C 20 alkenyl, —OC(O)C 2 -C 20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)NHC 1 -C 20 alkyl, —OC(O)NHC 2 -C 20 alkenyl, —OC(O)NHC 2 -C 20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(S)NHC 1 -C 20 alkyl, —OC(S)NHC 2 -C 20 alkenyl, —OC(S)NHC 2 -C 20 alkynyl, —OC(S)NHcycloalkyl or —OC(S)NHaryl;

R 24 is hydrogen, —OH, —OC 1 -C 20 alkyl, —OC 2 -C 20 alkenyl, —OC 2 -C 20 alkynyl, —Ocycloalkyl, —OC(O)C 1 -C 20 alkyl, —OC(O)C 2 -C 20 alkenyl, —OC(O)C 2 -C 20 alkynyl, —OC(O)cycloalkyl, —OC(O)aryl, —OC(O)NHC 1 -C 20 alkyl, —OC(O)NHC 2 -C 20 alkenyl, —OC(O)NHC 2 -C 20 alkynyl, —OC(O)NHcycloalkyl, —OC(O)NHaryl, —OC(S)NHC 1 -C 20 alkyl, —OC(S)NHC 2 -C 20 alkenyl, —OC(S)NHC 2 -C 20 alkynyl, —OC(S)NHcycloalkyl or —OC(S)NHaryl;

R 25 is hydrogen or —C 1 -C 10 alkyl;

R 26 and R 27 are each independently hydrogen, —C 1 -C 10 alkyl, —OH or —OC 1 -C 10 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, —CF 3 , —CO 2 R 28 , —COR 28 , —OR 28 , —SR 28 , —N(R 28 ) 2 , —NO 2 , —NR 28 OR 28 , —ON(R 28 ) 2 , —SOR 28 , —SO 2 R 28 , —SO 3 R 28 , —SON(R 28 ) 2 , —SON(R 28 ) 2 , —SO 3 N(R 28 ) 2 , —P(R 28 ) 3 , —P(═O)(R 28 ) 3 , —OSi(R 28 ) 3 or —OB(R 28 ) 2 , and wherein R 28 is hydrogen, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 8 cycloalkyl, —C 6 -C 14 aryl, arylalkyl, —C 1 -C 6 haloalkyl, —C 1 -C 6 dihaloalkyl or —C 1 -C 6 trihaloalkyl;

and geometric isomers or stereoisomers thereof, or pharmaceutically, agriculturally or pesticidally acceptable salts thereof;

and a pharmaceutically, agriculturally or pesticidally acceptable carrier.

Assignments (2)
CHANGE OF NAME Recorded Nov 11, 2019
From: QBIOTICS LIMITED
To: QBIOTICS PTY LTD
Reel/Frame 050987/0827 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 17, 2008
From: REDDELL, PAUL WARREN; GORDON, VICTORIA ANNE
To: QBIOTICS LIMITED
Reel/Frame 021844/0138 →
Priority Claims (1)
AU 2005907278 · Dec 23, 2005 · national
Continuity (1)
Related Publication 20090182042A1 · Jul 16, 2009