Chemistry: natural resins or derivatives; peptides or proteins; – Peptides of 3 to 100 amino acid residues – Cyclic peptides
Patent
1996-03-06
1997-07-08
Schain, Howard E.
Chemistry: natural resins or derivatives; peptides or proteins;
Peptides of 3 to 100 amino acid residues
Cyclic peptides
930 30, C07K 1102, A61K 1395
Patent
active
056462441
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to new depsipeptide derivatives having antiparasitic activity.
BACKGROUND ART
Japanese Kokai Tokkyo Koho 3-35796 and 5-170749 disclose depsipeptide derivatives prepared by culturing microorganisms.
As depsipeptide substances having parasiticidal activity, substance PF1022 (Japanese Kokai Tokkyo Koho 3-35,796) and substance PF1022B, substance PF1022C, substance PF1022D (Japanese Kokai Tokkyo Koho 5-170,749) are known, and among these compounds the effectiveness of substance PF1022 on gastrointestinal parasites (whipworms, haemonchus, hairworms and roundworms living in the stomach and intestine) has been confirmed. This time, the object was to find a drug having a stronger effect on gastrointestinal parasites and also effective on tissue parasites (for example filariid worms living in blood vessels, lungworms living in the lungs, liver flukes living in the liver).
DISCLOSURE OF INVENTION
The object compound of the present invention, depsipeptide derivatives (I) can be represented by the following general formula: ##STR2## wherein A is benzyl group which has suitable substituent (s), A.sup.a, B and D are each lower alkyl, and
According to the present invention, the object compound, the depsipeptide derivatives (I) can be prepared by the following processes.
It should be indicated that any of D-configured compound, L-configured compound and/or DL-configured compound are included in the scope of the present invention; however, for the convenience, only D-configured compounds and L-configured compounds are explained in the process for preparation as follows. ##STR3## wherein A, A.sup.a, B, C and D are each as defined above, R is hydrogen or amino protective group, and lower alkoxy,
A.sup.3 is benzyl group which has amino, or benzyl group which has amino and lower alkoxy, group which has mono- or di- lower alkylamino and lower alkoxy, cyclic amino and lower alkoxy, hydroxy and lower alkoxy,
Throughout the present specification, the amino acids, peptides, protective groups, condensing agents, etc. are indicated by the abbreviations according to the IUPAC-IUB (Commission on Biological Nomenclature) which are in common use in the field of art.
Moreover, unless otherwise indicated, the amino acids and their residues when shown by such abbreviations are meant to be L-configured compounds and residues, and when shown by D-abbreviations, they are meant to be D-configured compounds and residues.
In the present invention, there are employed the following abbreviations. [.beta.-(p-dimethylaminophenyl)lactic acid] [.beta.-(p-morpholinophenyl)lactic acid] [.beta.-(p-methoxyphenyl)lactic acid] [.beta.-(p-nitrophenyl)lactic acid] [.beta.-(p-aminophenyl)lactic acid] [.beta.-(p-methoxycarbonylaminophenyl)lactic acid]
Suitable salts of the compound (I) are conventional non- toxic salt and may include a salt with a base or an acid addition salt such as a salt with an inorganic base, for example, an alkaline metal salt [e.g. sodium salt, potassium salt, cesium salt, etc.], an alkaline earth metal salt [e.g. calcium salt, magnesium salt, etc.], an ammonium salt; a salt with an organic base, for example, an organic amine salt [e.g. triethylamine salt, pyridinium salt, picoline salt, ethanolamine salt, triethanolamine salt, dicyclohexylamine salt, N,N'-dibenzylethylenediamine salt, etc.]; an inorganic acid addition salt [e.g. hydrochloride, hydrobromide, sulfate, phosphate,etc.]; an organic carboxylic or sulfonic acid addition salt [e.g. formate, acetate, trifluoroacetate, maleate, tartrate, methanesulfonate, benzenesulfonate, p-toluenesulfonate, etc.]; a salt with a basic or acidic amino acid [e.g. arginine salt, aspartic acid salt, glutamic acid salt, etc.]; and the like.
In the above and subsequent descriptions of the present specification, suitable examples and illustrations of the various definitions to be included within the scope of the invention are explained in detail as follows.
The term "lower" is intended to mean 1 to 6 carbon atom (s), preferably 1 to 4 carbon atom (s),
REFERENCES:
patent: 5514773 (1996-05-01), Nishiyama et al.
Hara Toshihiko
Nishiyama Hitoshi
Ohgaki Masaru
Yamanishi Ryo
Fujisawa Pharmaceutical Co. Ltd.
Schain Howard E.
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