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US 8,013,012 B2Granted
Spiroketals
AssigneeEcoBiotics Ltd
InventorsPaul Warren Reddell, Victoria Anne Gordon
Life of this patent
Estimating the term…
Abstract
The present invention relates to spiroketal compounds that are useful in methods of treating or preventing protozoal infections, parasitic infections, bacterial infections, cell proliferative disorders and anti inflammatory disorders. The spiroketal compounds are also useful as immunosuppressive agents, and also in methods of controlling pests.
Claims17
A compound of formula (II):
- wherein
- X, Y and Z are independently selected from —O—, —S—, —NH—, —N(C1-C6 alkyl)- and —CH2-;
- R50 is selected from —CH3, —C3-C8 cycloalkyl, aryl, heterocyclyl and heteroaryl;
- R51, R52, R57, R58, R61, R62, R67, R68, R69 and R70 are independently selected from hydrogen, —C1-C20 alkyl, —C2-C20 alkenyl, C2-C20 alkynyl, —C3-C8 cycloalkyl, —C6-C14 aryl, —C5-C14 heteroaryl, —C3-C14 heterocyclyl, arylalkyl, heteroarylalkyl, heterocyclylalkyl, alkoxyalkyl, halo, —CN, —NO2, —C1-C 10 haloalkyl, —C1-C10 dihaloalkyl, —C1-C10 trihaloalkyl, —COR, —CO2R, —OR, —SR, —N(R)2, —NROR, —ON(R)2, —SOR, —SO2R, —SO3R, —SON(R)2, —SO2N(R)2, —SO3N(R)2, —P(R)3, —P(O)(R)3, —OSi(R)3, —OB(R)2, —C(W)R and —WC(W)R;
- R53 to R56 are independently selected from hydrogen, —C1-C20 alkyl, —C2-C20 alkenyl, —C2-C20 alkynyl, —C3-C8 cycloalkyl, —C6-C14 aryl, —05-C14 heteroaryl, —C3-C14 heterocyclyl, arylalkyl, heteroarylalkyl, heterocyclylalkyl, alkoxyalkyl, halo, —CN, —NO2, —C1-C10 haloalkyl, —C1-C10 dihaloalkyl, —C1-C10 trihaloalkyl, —COR, —CO2R, —OR, —SR, —N(R)2, —NROR, —ON(R)2, —SOR, —SO2R, —SO3R, —SON(R)2, —SO2N(R)2, —SO3N(R)2, —P(R)3, —P(O)(R)3, —OSi(R)3, —OB(R)2, —C(W)R and —WC(W)R;
- or R54 and R55 taken together form a double bond or are —O—;
- or R53 and R54 or R55 and R56 taken together form a carbonyl group;
- R59 and R60 are independently selected from hydrogen, —C1-C20 alkyl, —C2-C20 alkenyl, —C2-C20 alkynyl, —C3-C8 cycloalkyl, —C6-C14 aryl, —C5-C14 heteroaryl, —C3-C14 heterocyclyl, arylalkyl, heteroarylalkyl, heterocyclylalkyl, alkoxyalkyl, halo, —CN, —NO2, —C1-C10 haloalkyl, —C1-C10 dihaloalkyl, —C1-C10 trihaloalkyl, —COR, —CO2R, —OR, —SR, —N(R)2, —NROR, —ON(R)2, —SOR, —SO2R, —SO3R, —SON(R)2, —SO2N(R)2, —SO3N(R)2, —P(R)3, —P(O)(R)3, —OSi(R)3, —OB(R)2, —C(W)R and —WC(W)R;
- or R59 and R60 taken together form a carbonyl group;
- R63 to R66 are independently selected from hydrogen, —C1-C20 alkyl, —C2-C20 alkenyl, —C2-C20 alkynyl, —C3-C8 cycloalkyl, —C6-C14 aryl, —C5-C14 heteroaryl, —C3-C14 heterocyclyl, arylalkyl, heteroarylalkyl, heterocyclylalkyl, alkoxyalkyl, halo, —CN, —NO2, —C1-C10 haloalkyl, —C1-C10 dihaloalkyl, —C1-C10 trihaloalkyl, —COR, —CO2R, —OR, —SR, —N(R)2, —NROR, —ON(R)2, —SOR, —SO2R, —SO3R, —SON(R)2, —SO2N(R)2, —SO3N(R)2, —P(R)3, —P(O)(R)3, —OSi(R)3, —OB(R)2, —C(W)R and —WC(W)R;
- or R64 and R65 taken together form a double bond or are —O—;
- or R63 and R64 or R65 and R66 taken together form a carbonyl group;
- R71 and R72 are independently selected from hydrogen, —C1-C20 alkyl, —C2-C20 alkenyl, —C2-C20 alkynyl, —C3-C8 cycloalkyl, —C6-C14 aryl, —C5-C14 heteroaryl, —C3-C14 heterocyclyl, arylalkyl, heteroarylalkyl, heterocyclylalkyl, alkoxyalkyl, halo, —CN, —NO2, —C1-C10 haloalkyl, —C1-C10 dihaloalkyl, —C1-C10 trihaloalkyl, —COR, —CO2R, —OR, —SR, —N(R)2, —NROR, —ON(R)2, —SOR, —SO2R, —SO3R, —SON(R)2, —SO2N(R)2, —SO3N(R)2, —P(R)3, —P(O)(R)3, —OSi(R)3, —OB(R)2, —C(W)R and —WC(W)R;
- or R71 and R72 taken together form a carbonyl group;
- R73 to R76 are independently selected from hydrogen, —C1-C20 alkyl, —C2-C20 alkenyl, —C2-C20 alkynyl, —C3-C8 cycloalkyl, —C6-C14 aryl, —C5-C14 heteroaryl, —C3-C14 heterocyclyl, arylalkyl, heteroarylalkyl, heterocyclylalkyl, alkoxyalkyl, halo, —CN, —NO2, —C1-C10 haloalkyl, —C1-C10 dihaloalkyl, —C1-C10 trihaloalkyl, —COR, —CO2R, —OR, —SR, —N(R)2, —NROR, —ON(R)2, —SOR, —SO2R, —SO3R, —SON(R)2, —SO2N(R)2, —SO3N(R)2, —P(R)3, —P(O)(R)3, —OSi(R)3, —OB(R)2, —C(W)R and —WC(W)R;
- or R74 and R75 taken together form a double bond or are —O—;
- or R73 and R74 or R75 and R76 taken together form a carbonyl group;
- R77 and R78 are independently selected from hydrogen, —C1-C10 alkyl, —C2-C10 alkenyl and —C2-C10 alkynyl;
- W is selected from —O—, —S—, —NH— and —N(C1-C6 alkyl)-;
- R is selected from hydrogen, —C1-C20 alkyl, —C2-C20 alkynyl, —C2-C20 alkynyl, —C3-C8 cycloalkyl, —C6-C14 aryl, —C5-C14 heteroaryl, —C3-C14 heterocyclyl, arylalkyl, heteroarylalkyl, heterocyclylalkyl, —C1-C10 haloalkyl, —C1-C10 dihaloalkyl and —C1-C10 trihaloalkyl;
- p and q are independently 0 or 1;
- and
- r is an integer from 1 to 8;
- wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocyclyl and heteroaryl is optionally substituted;
- or a pharmaceutically, agriculturally or pesticidally acceptable salt thereof.
22 more elements
Dependencies are inferred from the claim text.