Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing heterocyclic carbon compound having only o – n – s,...
Patent
1998-05-19
1999-07-27
Richter, Johann
Chemistry: molecular biology and microbiology
Micro-organism, tissue cell culture or enzyme using process...
Preparing heterocyclic carbon compound having only o, n, s,...
435127, 435170, 514453, 549276, A61K 3135, C07D31178, C12P 1500, C12P 1706
Patent
active
059289104
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention is useful in the pharmaceutical field. More specifically, the present invention relates to novel compounds which provide antifungal effects, a process for their production and applications thereof, and a microorganism which produces such compounds.
BACKGROUND ART
In the field of chemotherapy against microbism, many compounds have already been practically used as pharmaceutical products. However, existing chemotherapic agents are not necessarily adequate in their effects against mycosis due to infection of so-called eumycetes such as fungi or yeast, and emergence of resistant strains has become a serious clinical problem.
DISCLOSURE OF THE INVENTION
It is an object of the present invention to find out a novel antifungal agent having stronger antifungal activities against fungi.
The present inventors have conducted screening of secondary metabolites of microorganisms widely with respect to the substances having antifungal activities to accomplish the object, and as a result, have found that the compound represented by the after-mentioned general formula (I) has excellent antifungal activities, and the present invention has been accomplished.
Namely, the present invention provides a novel compound represented by the general formula (I): ##STR3## wherein R.sub.1 is a hydrogen atom, or ##STR4## and R.sub.2 is a hydrogen atom or a lower alkanoyl group; a process for its production and its application, and a microorganism belonging to genus Paecilomyces, which is capable of producing a compound represented by the general formula (II): ##STR5## wherein R.sub.20 is a hydrogen atom, and R.sub.1 is as defined above.
Among the compounds of the general formula (I) of the present invention, a compound wherein R.sub.1 is a group represented by ##STR6## and R.sub.2 is a hydrogen atom, will be referred to as BE-49385A, a compound wherein R.sub.1 is a group represented by ##STR7## and R.sub.2 is a hydrogen atom, will be referred to as BE-49385B, a compound wherein R.sub.1 is a group represented by ##STR8## and R.sub.2 is a hydrogen atom, will be referred to as BE-49385C, a compound wherein R.sub.1 is a group represented by ##STR9## and R.sub.2 is a hydrogen atom, will be referred to as BE-49385D, a compound wherein R.sub.1 is a group represented by ##STR10## and R.sub.2 is a hydrogen atom, will be referred to as BE-49385E, a compound wherein each of R.sub.1 and R.sub.2 is a hydrogen atom, will be referred to as BE-49385F, a compound wherein R.sub.1 is a group represented by ##STR11## and R.sub.2 is a hydrogen atom, will be referred to as BE-49385G, a compound wherein R.sub.1 is a group represented by ##STR12## and R.sub.2 is a hydrogen atom, will be referred to as BE-49385H, and a compound wherein R.sub.1 is a group represented by ##STR13## and R.sub.2 is an acetyl group, will be referred to as BE-49385A-Ac.
The term "lower" used in the present specification means that the carbon number of the group having this term affixed, is at most 6, preferably at most 4. The "lower alkanoyl group" means a C.sub.1-6 linear or branched alkanoyl group, such as, a formyl group, an acetyl group, a propionyl group, an isopropionyl group, an isobutyryl group, a sec-butyryl group, a tert-butyryl group, a pentanoyl group, an isopentanoyl group, a neopentanoyl group or a hexanoyl group.
Now, the physicochemical characteristics of the antifungal substances BE-49385 of the present invention will be shown. The abbreviations in the NMR measurements have the following meanings.
s: singlet
d: doublet
t: triplet
q: quartet
m: multiplet
br: broad
J: coupling constant
Hz: hertz
Nature: White amorphous solid or crystals
Molecular formula: C.sub.34 H.sub.54 O.sub.7 CHCl.sub.3)
Ultraviolet absorption spectrum: Terminal absorption is shown.
Infrared absorption spectrum: (KBr, cm.sup.-1):
.sup.1 H-NMR spectrum (500MHz, CDCl.sub.3) .delta. ppm:
5.30(1H, dt, J=7.3, 4.0 Hz), 5.14(1H, s), 5. 04(1H, brt, J=9.0 Hz), 4.71(1H, s), 4.38(1H, dq, J=10.0, 6.4H z), 4.22(1H, d, J=4.0 Hz), 3.58(1H, s), 3.12(2H, m), 3.07 (1H, d,
REFERENCES:
patent: 5233062 (1993-08-01), Horn et al.
Sutterlin et al. EMBO, vol. 16 211, pp. 6374-6383, 1997.
Kawamura Kenji
Kojiri Katsuhisa
Kushida Hiroshi
Nagashima Masao
Nakajima Shigeru
Banyu Pharmaceutical Co. Ltd.
Richter Johann
Solola Taofiq A.
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