Cyclic peptide nuclei and derivatives thereof

Details Cyclic peptide nuclei and derivatives thereof Cyclic peptide nuclei and derivatives thereof

1997-09-29

1999-09-14

Davenport, Avis M.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Peptide containing doai

514 11, 530317, A61K 3800, A61K 3812, C07K 500, C07K 700

Patent

active

059522992

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

This invention relates to new peptide compounds and pharmaceutically acceptable salts thereof which are useful as a medicament.


BACKGROUND ART

Some peptide compounds have been known as described, for example, in WO 92/19648.


DISCLOSURE OF INVENTION

This invention relates to new peptide compounds.
One object of this invention is to provide the new and useful peptide compounds and pharmaceutically acceptable salts thereof which possess a high antimicrobial activity (especially, antifungal activity) and a strong inhibitory activity on .beta.-1,3-glucan synthase.
Another object of this invention is to provide process for preparation of the peptide compounds and salts thereof.
A further object of this invention is to provide a pharmaceutical composition comprising, as an active ingredient, said peptide compounds or a pharmaceutically acceptable salt thereof.
Still further object of this invention is to provide a use of said peptide compounds or a pharmaceutically acceptable salt thereof as a medicament for prophylactic and therapeutic treatment of infectious diseases including Pneumocystis carinii infection (e.g., Pneumocystis carinii pneumonia, etc.) caused by a variety of pathogenic microorganisms in human being and animals.
The object peptide compounds of the present invention are novel and can be represented by the following general formula (I) (SEQ ID NO:1): ##STR2## wherein R.sup.1 is alkyl or aralkyl, --O-- or --NH--), and
The object compound (I) of the present invention can be prepared by the processes as illustrated in the following. ##STR3## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and --Z-- are each as defined above,
The starting compounds (II) and (IV) of the present invention can be prepared by the processes as illustrated in the following. ##STR4## wherein R.sup.1 and R.sup.2 are each as defined above.
Suitable pharmaceutically acceptable salts of the object compound (I) are conventional non-toxic salts and may include a salt with a base or an acid addition salt such as a salt with an inorganic base, for example, an alkali metal salt (e.g., sodium salt, potassium 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, pyridine 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, fumarate, methanesulfonate, benzenesulfonate, toluenesulfonate, etc.); a salt with a basic or acidic amino acid (e.g., arginine, aspartic acid, glutamic acid, etc.).
In the above and subsequent descriptions of the present specification, suitable examples and illustration of the various definitions which the present invention intends to include within the scope thereof are explained in detail as follows.
The term "lower" is used to intend a group having 1 to 6, preferably 1 to 4, carbon atom(s), unless otherwise provided.
The term "higher" is used to intend a group having 7 to 20 carbon atoms, unless otherwise provided.
Suitable "lower alkyl" and "lower alkyl moiety" in the terms "amino(lower)alkyl", "acylamino(lower)alkyl" and "protected amino(lower)alkyl" may include straight or branched one having 1 to 6 carbon atom(s), such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, tert-pentyl, hexyl, and the like.
Suitable "alkyl" and "alkyl moiety" in the term "aralkyl" may include straight or branched one having 1 to 20 carbon atom(s), such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, tert-pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, and the like.
Suitable "aryl moiety" in the term "aralkyl" may include phenyl, naphthyl and the like.
Suitable "

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