Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Nitrogen containing other than solely as a nitrogen in an...
Patent
1997-02-24
1998-12-15
Kumar, Shailendra
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Nitrogen containing other than solely as a nitrogen in an...
514138, 514197, 514198, A61K 3116, C07C23102, C07C23305
Patent
active
058497978
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/JP95/01680, filed Aug. 24, 1995.
TECHNICAL FIELD
This invention relates to an (R)-3,6-diamino-N-(.omega.-aminoalkyl)hexanamide which is a novel compound active for inhibiting the growth of Gram-positive bacteria and Gram-negative bacteria, the infection of human T-cells with AIDS virus, namely HIV, and the growth of tumor cells and which is represented by the following general formula (I): ##STR2## wherein n stands for an integer of 2-5. This novel compound of the general formula (I) above is useful as a chemotherapeutic agent for various purposes. This invention also relates to a process for the preparation of the above-described novel compound.
BACKGROUND ART
The present inventors discovered that D-.beta.-lysyl-methanediamine which corresponds to such compound of the general formula (I) above where n stands for 1 and is hence represented by the formula (A): ##STR3## is produced and accumulated in a culture of an actino-mycetes strain ("J. Antibiotics", 39, 476(1986) and Japanese Patent Application Laid-Open Publication No. SHO 62-114947, published May 26, 1987). Development and researches are now made for utilization of D-.beta.-lysyl-methanediamine as a therapeutic agent for the treatment of AIDS (Japanese Patent Application No. HEI 3-346341 filed on Dec. 27, 1991; U.S. patent application Ser. No. 08/256,121; and European patent application publication No. 653207-A1).
AIDS is a disease caused by the infection with an AIDS virus (HIV). Several drugs which can inactivate HIV have been reported as therapeutics for AIDS, but any of them are not satisfactory. There is hence a continued demand for providing such a novel drug having low toxicity but high anti-HIV activities.
Through a study of the present inventors, the chemical structure of D-.beta.-lysylmethanediamine (which is generally called "Bellenamine") was determined to be unique since its total synthesis was somewhat difficult with starting from an amino-protected D-.beta.-lysylglycine via its acid D-.beta.-lysylmethanediamine, its total synthesis process is troublesome to be achieved.
D-.beta.-lysylmethanediamine, that is, Bellenamine, which was found in the culture of the microorganism of actino-mycetes and discovered by the present inventors and which has anti-HIV activities, has the linear aldoaminal structure that is discovered firstly to exist in the nature, so that Bellenamine is chemically instable.
DISCLOSURE OF THE INVENTION
The present inventors therefore have now conducted research on the synthesis of novel and useful Bellenamine-related substances. An object of the present invention is to provide an (R)-3,6-diamino-N-(.omega.-aminoalkyl)hexanamide as a novel compound which can be considered to be analogous to D-.beta.-lysylmethanediamine but is chemically more stable. Another objects of the present invention will be clear from the following descriptions.
The present inventors have now succeeded in synthesizing a series of (R)-3,6-diamino-N-(.omega.-aminoalkyl)hexanamides, which each is a novel compound having higher chemical stability than D-.beta.-lysylmethanediamine and having antibacterial activity and anti-HIV activities as well as antitumor activity and which is collectively represented by the general formula (I) as above. It has now been found that among the compounds of the general formula (I), (R)-3,6-diamino-N-(2-aminoethyl)hexanamide and (R)-3,6-diamino-N-(3-aminopropyl)hexanamide have antibacterial and anti-HIV activities comparable to or sometime superior to those of D-.beta.-lysylmethanediamine and also exhibit an antitumor activity superior to that of D-.beta.-lysylmethanediamine.
According to a first aspect of the present invention, therefore, there is provided an (R)-3,6-diamino-N-(.omega.-aminoalkyl)hexanamide represented by the general formula (I): ##STR4## wherein n stands for an integer of 2-5, or an acid addition salt thereof.
According to a second aspect of the present invention, there is provided a process for the preparation of an (R)-3,6-diamino-N-(.omega.-aminoalkyl)hexa
REFERENCES:
Ikeda et al, The Journal of Antibiotics, vol. 45, No. 10, 1677-1680, 1992.
Gomi Shuichi
Hoshino Hiroo
Ikeda Yoko
Kondo Shin-ichi
Shibahara Seiji
Kumar Shailendra
Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai
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