Antiparasitic artemisinin derivatives (endoperoxides)
AssigneeBayer Aktiengesellschaft
InventorsRichard Haynes, William Lam, Ho-Wai Chan, Hing-Wo Tsang, Man-Ki Cheung, Gisela Greif, Gabriele Schmuck, Arnd Voerste
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Abstract
This invention relates to the use of certain C-10 substituted derivatives of artemisinin of general formula (I) in the treatment and/or prophylaxis of diseases caused by infection with a parasite, certain novel C-10 substitued derivatives of artemisinin, processes for their preparation and pharmaceutical compositions containing such C-10 substituted derivatives. The compounds are particularly effective in the treatment of malaria, neosporosis and coccidiosis.
Claims28
A method of treating or preventing a disease caused by infection with a parasite other than an organism of the genus Plasmodium, comprising administering to a host in need thereof an effective amount of a compound of the general formula I
- or a salt thereof,
- in which
- Y represents a halogen atom, an optionally substituted cycloalkyl, aryl, C-linked heteroaryl or heterocyclylalkyl group or a group —NR1R2;
- where
- R1 represents a hydrogen atom or an optionally substituted alkyl, alkenyl or alkynyl group;
- R2 represents an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl or aralkyl group;
- or
- R1 and R2 together with the interjacent nitrogen atom represent an optionally substituted heterocyclic group or an amino group derived from an optionally substituted amino acid ester.
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A compound of the general formula I
- or a salt thereof,
- in which
- Y represents a halogen atom an optionally substituted cycloalkyl, aryl, C-linked heteroaryl or heterocyclylalkyl group or a group —NR1R2;
- where
- R1 represents a hydrogen atom or an optionally substituted alkyl, alkenyl or alkynyl group;
- R2 represents an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl or aralkyl group;
- or
- R1 and R2 together with the interjacent nitrogen atom represent an optionally substituted aromatic heterocyclic group or an amino group derived from an optionally substituted amino acid ester
- with the proviso that, when Y is a group —NR1R2 and R2 represents a phenyl, 3-chlorophenyl, 4-chlorophenyl, 3-bromophenyl, 4-bromophenyl, 4-iodophenyl, 4-methylphenyl, 4-methoxyphenyl, 3-carboxylphenyl or 4-carboxylphenyl group, then R1 is an optionally substituted alkyl group.
A process for the preparation of a compound of the general formula I according to claim 28 in which Y represents an optionally substituted cycloalkyl, aryl, C-linked heteroaryl or heterocyclylalkyl group which comprises reacting 9,10-anhydroartemisinin with a compound of the general formula Y—H, where Y is as defined above in claim 16, in the presence of a suitable Lewis acid.
A process for the preparation of a compound of the general formula I according to claim 28 in which Y represents an optionally substituted aryl or C-linked heteroaryl group which comprises reacting 10-trichloroacetimidoyl-10-deoxoartemisinin with a compound of the general formula Y—H, where Y is as defined above in claim 16, in the presence of a suitable Lewis acid.
A process for the preparation of a compound of the general formula I according to claim 28 in which Y represents an optionally substituted aryl or C-linked heteroaryl group which comprises reacting a 10-acyloxyartemisinin compound in which the acyloxy group is of formula A-(C═O)—O—, where A represents an optionally substituted alkyl, cycloalkyl, aryl, aralkyl, heterocyclic or polycyclic group, with a compound of the general formula Y—H, where Y is as defined above in claim 16, in the presence of a Lewis acid.
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Dependencies are inferred from the claim text.