Antiparasitic artemisinin derivatives (endoperoxides)
AssigneeThe Hong Kong University of Science and Technology
InventorsRichard K. Haynes, William Wai-Lun 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 substituted 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.
Claims3
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 R1 represents a hydrogen atom or a C1-6 alkyl group and R2 represents a C1-6 alkyl, C3-8 cycloalkyl, C6-10 aryl or C7-16 aralkyl group, or R1 and R2 together with the interjacent nitrogen atom represent a 5- to 10-membered heterocyclic group or an amino group derived from a C1-6 alkyl ester of an amino acid, each group being optionally substituted by one or more substituents selected from the group consisting of halogen atoms, C1-4 alkyl, C1-4 haloalkyl, C1-6 alkoxycarbonyl, phenyl, halophenyl, C1-4 alkylphenyl, C1-4 haloalkylphenyl, C1-4 alkoxyphenyl, benzyl, pyridyl and pyrimidinyl groups.
A method for treating or preventing a disease caused by infection with a parasite of the genus Plasmodium which comprises administering to a host in need of such treatment a therapeutically effective amount of a compound of the general formula I
- wherein R1 represents a hydrogen atom or a C1-6 alkyl group and R2 represents a C1-6 alkyl, C3-8 cycloalkyl, C6-10 aryl or C7-16 aralkyl group, or R1 and R2 together with the interjacent nitrogen atom represent a 5- to 10-membered heterocyclic group or an amino group derived from a C1-6 alkyl ester of an amino acid, each group being optionally substituted by one or more substituents selected from the group consisting of halogen atoms, C1-4 alkyl, C1-4 haloalkyl, C1-6 alkoxycarbonyl, phenyl, halophenyl, C1-4 alkylphenyl, C1-4 haloalkylphenyl, C1-4 alkoxyphenyl, benzyl, pyridyl and pyrimidinyl groups.
A process for preparing a compound of general formula I
- wherein R1 represents a hydrogen atom or a C1-6 alkyl group and R2 represents a C1-6 alkyl, C3-8 cycloalkyl, C6-10 aryl or C7-16 aralkyl group, or R1 and R2 together with the interjacent nitrogen atom represent a 5- to 10-membered heterocyclic group or an amino group derived from a C1-6 alkyl ester of an amino acid, each group being optionally substituted by one or more substituents selected from the group consisting of halogen atoms, C1-4 alkyl, C1-4 haloalkyl, C1-6 alkoxycarbonyl, phenyl, halophenyl, C1-4 alkylphenyl, C1-4 haloalkylphenyl, C1-4 alkoxyphenyl, benzyl, pyridyl and pyrimidinyl groups comprising the steps of:
- i) reacting the compound of general formula II
- in which Q represents a hydrogen atom or trimethylsilyl group, with a suitable halogenating agent to form a compound of the general formula III
- in which Y2 represents a halogen atom;
- and
- ii) reacting the compound of the general formula III thus formed with an amine of the general formula HNR1R2 to form a compound of general formula I.
Dependencies are inferred from the claim text.