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US 8,940,892 B2Granted
Triazine derivatives for use in the treatment of malaria
AssigneeCsir
InventorsAmanda Louise Rousseau, David Gravestock, Anna Catharina Uys Lourens
Life of this patent
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Abstract
The invention provides compounds of formula (I), in which R1 and R2 are independently selected from H, alkyl, aryl and heteroaryl, or R1 and R2 together form a C5-C7 ring, R3-R7 are independently selected from H, halogen, alkyl and alkoxy, X is (CH2)n in which n is 0-5, Y is selected from CH2, NR8, O or S in which R8 is H or alkyl, salts thereof and stereoisomers thereof, for the prophylaxis or treatment of malaria.
Claims9
A method of treating malaria in a subject comprising administering to said subject a compound of formula I,
- in which
- R1 and R2 are independently selected from the group consisting of H, alkyl, aryl and heteroaryl, or R1 and R2 together form a C5-C7 ring,
- R3-R7 are independently selected from the group consisting of H, halogen, alkyl and alkoxy,
- X is (CH2)n in which n is 0-5,
- Y is selected from the group consisting of CH2, NR8, O or S in which R8 is H or alkyl,
- a salt thereof and a stereoisomer thereof,
- in which
- “alkyl” means a group selected from the group consisting of:
- C1-C7 straight chain alkyl groups, optionally substituted with one or more F, Cl, Br, O, S or N, and
- C1-C7 branched alkyl groups optionally substituted with one or more F, Cl, Br, O, S or N,
- “aryl” means a group selected from the group consisting of:
- phenyl, and
- phenyl substituted with one or more F, Cl, Br, S, N, C1-C7 alkoxy, nitrile, trifluoromethyl, C1-C7 straight chain alkyl groups and C1-C7 branched alkyl groups, the alkyl groups being optionally substituted with one or more F, Cl, Br, O, S or N,
- “heteroaryl” means a group selected from the group consisting of thiophenyl, furyl, pyridinyl, isoxazolinyl, pyrrolinyl, oxazolinyl, thiazolinyl, imidazolyl which is optionally substituted with one or more F, Cl, Br, S, N, C1-C7 alkoxy, nitrile, trifluoromethyl, C1-C7 straight chain alkyl groups and C1-C7 branched alkyl groups, the alkyl groups being optionally substituted with one or more F, Cl, Br, O, S or N,
- “halogen” means F, Cl or Br, and
- “alkoxy” means a C1-C7 alkoxy group
- provided that:
- (1) when R1 and R2 are both methyl, X is (CH2)n, n is 2-5 and Y is O, then R3-R7 are not all H,
- (2) when R1 and R2 are independently selected from the group consisting of H, methyl, isopropyl, propyl, cyclohexyl, phenyl, 4-fluorophenyl, 4-chlorophenyl, 3,4-methylenedioxyphenyl, 4-acetamidophenyl, 4-methylthiophenyl or R1 and R2 together form —(CH2)2CH(CH3)-(CH2)2—, X is (CH2)n, n is 0-3 and Y is CH2, then R3-R7 are not all H;
- (3) when R1 and R2 are both methyl, X is CH2, NR8 is NH, and R3, R4, R6 and R7 are H, then R5 may not be Cl, F or H;
- (4) when R1 and R2 are both methyl, X is CH2, NR8 is NH and R3, R6 and R7 are H, then R4 and R5 may not both be Cl;
- and
- (5) when R1 and R2 are both methyl, X is CH2 and NR8 is NMe, not all of R3, R4, R5, R6, R7 may be H.
20 more elements
A compound of formula I,
- in which
- R1 and R2 are independently selected from the group consisting of H, alkyl, aryl and heteroaryl, or R1 and R2 together form a C5-C7 ring,
- R3-R7 are independently selected from the group consisting of H, halogen, alkyl and alkoxy,
- X is (CH2)n in which n is 0-5,
- Y is selected from the group consisting of CH2, NR8, O or S in which R8 is H or alkyl,
- a salt thereof and a stereoisomer thereof,
- in which
- “alkyl” means a group selected from the group consisting of:
- C1-C7 straight chain alkyl groups, optionally substituted with one or more F, Cl, Br, O, S or N, and
- C1-C7 branched alkyl groups optionally substituted with one or more F, Cl, Br, O, S or N,
- “aryl” means a group selected from the group consisting of:
- phenyl, and
- phenyl substituted with one or more F, Cl, Br, S, N, C1-C7 alkoxy, nitrile, trifluoromethyl, C1-C7 straight chain alkyl groups and C1-C7 branched alkyl groups, the alkyl groups being optionally substituted with one or more F, Cl, Br, O, S or N,
- “heteroaryl” means a group selected from the group consisting of thiophenyl, furyl, pyridinyl, isoxazolinyl, pyrrolinyl, oxazolinyl, thiazolinyl, imidazolyl which is optionally substituted with one or more F, Cl, Br, S, N, C1-C7 alkoxy, nitrile, trifluoromethyl, C1-C7 straight chain alkyl groups and C1-C7 branched alkyl groups, the alkyl groups being optionally substituted with one or more F, Cl, Br, O, S or N,
- “halogen” means F, Cl or Br, and
- “alkoxy” means a C1-C7 alkoxy group provided that:
- (1) when R1 and R2 are both methyl, X is (CH2)n, n is 2-5 and Y is O, then R3-R7 are not all H,
- (2) when R1 and R2 are independently selected from the group consisting of H, methyl, isopropyl, propyl, cyclohexyl, phenyl, 4-fluorophenyl, 4-chlorophenyl, 3,4-methylenedioxyphenyl, 4-acetamidophenyl, 4-methylthiophenyl or R1 and R2 together form —(CH2)2CH(CH3)—(CH2)2—, X is (CH2)1, n is 0-3 and Y is CH2, then R3-R7 are not all H,
- (3) when R1 is selected from the group consisting of H, trifluoromethyl, undecyl, tert-butyl or phenyl and R2 is H or methyl, Y is CH2 for X═(CH2)n and n=0 and R5 is H or chlorine, then R3, R4, R6 and R7 are not all H and when R4 and R5 are methoxy then not all of R3, R6 and R7 are H, and
- (4) when R1 and R2 are both methyl, X is (CH2)n, n is 0-3 and Y is CH2, then neither R3 nor R7 is H;
- (5) when R1 and R2 are both methyl, X is CH2, NR8 is NH, and R3, R4, R6 and R7 are H, then R5 may not be Cl, F or H;
- (6) when R1 and R2 are both methyl, X is CH2, NR8 is NH and R3, R6 and R7 are H, then R4 and R5 may not both be Cl;
- and
- (7) when R1 and R2 are both methyl, X is CH2 and NR8 is NMe, not all of R3, R4, R5, R6, R7 may be H.
21 more elements
Dependencies are inferred from the claim text.