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US 10,583,140 B2Granted
Ingenol analogs, pharmaceutical compositions and methods of use thereof
AssigneeGlaxoSmithKline Intellectual Property Development Limited
InventorsVincent Wing-Fai Tai, Jun Tang
Life of this patent
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Abstract
The invention relates to compounds of Formula (I), (II), (III) or (IV), salts thereof, pharmaceutical compositions thereof, as well as methods of treating, curing or preventing HIV in subjects.
Claims13
A compound according to formula (II):
- or a pharmaceutically acceptable salt thereof:
- X is selected from O or N, wherein when X is O, then R3 is absent;
- R1 is optionally present, and when present, the group:
- is represented as:
- and R1 is —C(O)R4;
- R2 and R3 are independently selected from the group consisting of —H, methyl, —C(O)R10, —C(O)N(R6)2, —S(O)2CH3, (C6)heteroaryl and (C9)heteroaryl, wherein when X is N, then R2 and R3 may be taken together to form a pyrrolidine group optionally substituted by one or more R12;
- R4 is —N(R6) R7;
- R6 is methyl;
- R7 is phenyl optionally substituted with one or more R13;
- R10 is selected from the group consisting of (C1-C4)alkyl, (C3-C9)cyclohexyl, (C5-C6)heterocycle, and phenyl, wherein the cyclohexyl, (C5-C6) heterocycle and phenyl are optionally substituted with one or more R11;
- and
- wherein R11,R12 and R13 are independently selected from the group consisting of methyl, methoxy, oxo, trifluoromethyl and chloro;
- with the proviso that when X is O and R2 is H, R1 is not present.
10 more elements
A compound selected from the group consisting of:
- ((1aR,2S,5R,5aS,6S,8aS,9R, 10aR)-6-(((4-chlorophenyl) (methyl)carbamoyl)oxy)- 5,5a-dihydroxy-1,1,7,9- tetramethyl-11-oxo- 1a,2,5,5a,6,9,10,10a- octahydro-1H-2,8a- methanocyclopenta[a] cyclopropa[e][10]annulen- 4-yl)methyl acetate
- ((1aR,2S,5R,5aS,6S,8aS, 9R,10aR)-6-(((4- chlorophenyl) (methyl)carbamoyl)oxy)- 5,5a-dihydroxy-1,1,7,9- tetramethyl-11-oxo- 1a,2,5,5a,6,9,10,10a- octahydro-1H-2,8a- methanocyclopenta [a]cyclopropa[e][10] annulen-4-yl)methyl benzoate
- (1aR,2S,5R,5aS,6S,8aS, 9R,10aR)-4-((1,3- dioxoisoindolin-2- yl)methyl)-5,5a-dihydroxy- 1,1,7,9-tetramethyl-11- oxo-1a,2,5,5a,6,9,10,10a- octahydro-1H-2,8a- methanocyclopenta[a] cyclopropa[e][10]annulen- 6-yl(4-chlorophenyl) (methyl)carbamate
- (1aR,2S,5R,5aS,8aS,9R, 10aR)-5,5a-dihydroxy-4- (hydroxymethyl)-1,1,7,9- tetramethyl- 1a,2,5,5a,10,10a- hexahydro-1H-2,8a- methanocyclopenta[a] cyclopropa[e][10]annulene- 6,11(9H)-dione
- ((1aR,2S,5R,5aR,6S,8aS, 9R,10aR)-5,5a,6- trihydroxy-1,1,7,9- tetramethyl-11-oxo- 1a,2,5,5a,6,9,10,10a- octahydro-1H-2,8a- methanocyclopenta[a] cyclopropa[e][10]annulen-4- yl)methyl (4- chlorophenyl)(methyl) Carbamate
- ((1aR,2S,5R,5aR,6S,8aS, 9R,10aR)-5,5a,6- trihydroxy-1,1,7,9- tetramethyl-11-oxo- 1a,2,5,5a,6,9,10,10a- octahydro-1H-2,8a- methanocyclopenta[a] cyclopropa[e][10]annulen-4- yl)methyl phenylcarbamate
- ((1aR,2S,5R,5aR,6S,8aS, 9R,10aR)-5,5a,6- trihydroxy-1,1,7,9- tetramethyl-11-oxo- 1a,2,5,5a,6,9,10,10a- octahydro-1H-2,8a- methanocyclopenta[a] cyclopropa[e][10]annulen-4- yl)methyl butylcarbamate
- ((1aR,2S,5R,5aR,6S,8aS, 9R,10aR)-5,5a,6- trihydroxy-1,1,7,9- tetramethy1-11-oxo- 1a,2,5,5a,6,9,10,10a- octahydro-1H-2,8a- methanocyclopenta[a] cyclopropa[e][10]annulen-4- yl)methyl benzylcarbamate
- ((1aR,2S,5R,5aR,6S,8aS, 9R,10aR)-5,5a,6- trihydroxy-1,1,7,9- tetramethyl-11-oxo- 1a,2,5,5a,6,9,10,10a- octahydro-1H-2,8a- methanocyclopenta[a] cyclopropa[e][10] annulen-4- yl)methyl cyclohexyl(methyl) Carbamate
- ((1aR,2S,5R,5aR,6S,8aS, 9R,10aR)-5,5a,6- trihydroxy-1,1,7,9- tetramethyl-11-oxo- 1a,2,5,5a,6,9,10,10a- octahydro-1H-2,8a- methanocyclopenta[a] cyclopropa[e][10]annulen-4- yl)methyl indoline-1- carboxylate
- (1aR,2S,5R,5aS,6S,8aS, 9R,10aR)-5,5a-dihydroxy-4- (((indoline-1- carbonyl)oxy)methyl)- 1,1,7,9-tetramethyl-11- oxo-1a,2,5,5a,6,9,10,10a- octahydro-1H-2,8a- methanocyclopenta[a] cyclopropa[e][10]annulen- 6-yl indoline-1-carboxylate
- (1aR,2S,5R,5aR,6S,8aS, 9R,10aR)-5,5a,6-trihydroxy- 1,1,7,9-tetramethyl-4-(((5- (trifluoromethyl)pyrimidin- 2-yl)oxy)methyl)- 1a,2,5,5a,6,9,10,10a- octahydro-1H-2,8a- methanocyclopenta[a] cyclopropa[e][10]annulen- 11-one
- and pharmaceutically acceptable salts thereof.
10 more elements
Dependencies are inferred from the claim text.