Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing heterocyclic carbon compound having only o – n – s,...
Patent
1996-11-29
1998-09-01
Walsh, Stephen
Chemistry: molecular biology and microbiology
Micro-organism, tissue cell culture or enzyme using process...
Preparing heterocyclic carbon compound having only o, n, s,...
435118, 435119, 435120, 435121, 435127, 435128, 435132, 435135, 435147, 435155, 435156, 435171, 514183, 5147288, 5142295, 5142305, 5147298, 514359, 514408, 514410, 514411, 514412, 514461, 514510, 544 1, 544 63, C12P 1700, C12P 1716, A61K 3133, A61K 31535
Patent
active
058010238
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to novel pyrrolobenzoxazine compounds, a process for their production and their use. More particularly, the present invention relates to a process for production of novel pyrrolobenzoxazine compounds by cultivating Aspergillus fischeri var. thermomutatis ATCC 18618. Further, the present invention relates to an antiparasitic agent which comprises a pyrrolobenzoxazine compound of this invention as an effective ingredient.
BACKGROUND ART
It is known that the pyrrolobenzoxazine UK-88,051 is a broad spectrum antiparasitic agent possessing anthelmintic, ectoparasiticidal, insecticidal activity with application in the areas of animal and human health, agriculture and horticulture (United Kingdom Patent No. 2240100). This compound is produced by fermentation of a fungal microorganism Chrysosporium sp. ATCC 20975. In this field, the investigation on novel compounds having excellent activity has been continuously carried out.
An objective of the present invention is to provide novel compounds with excellent activity against insect pests, acari, helminths (e.g., free living nematodes) and endo- and ecto-parasites afflicting animals. Also, another objective of the present invention is to provide a process for producing such compounds, and a pharmaceutical composition comprising the same.
BRIEF DESCRIPTION OF THE INVENTION
Accordingly, the present invention provides novel pyrrolobenzoxazine compounds of the following planar chemical formula or their pharmaceutically-acceptable salts: ##STR2## wherein R is hydrogen or chloro. It is believed that these compounds have the following absolute chemical formula: ##STR3## wherein R is hydrogen or chloro.
Also, the present invention provides a process for the production of the compound of formula I, which comprises fermenting a microorganism having the identifying characteristics of Aspergillus fischeri var. thermomutatus ATCC 18618, or a mutant, genetically-transformed or recombinant form thereof, having the ability to produce the compound of formula I, and then isolating the compound of formula I from the fermentation broth.
The pyrrolobenzoxazine compounds of formula I of this invention have broad antiparasitic activity, and thus are useful as antiparasitic agents, especially as ectoparaciticides. Accordingly, the present invention also provides a pharmaceutical composition for the treatment or prevention of parasitic infection in mammalian subject which comprises a therapeutically-effective amount of the compound of formula I together with a pharmaceutically-acceptable carrier; and a method for the treatment or prevention of a parasitic infection in non-human mammalian subject, which comprises administering to said subject a therapeutically-effective amount of the compound of formula I.
DETAILED DESCRIPTION OF THE INVENTION
The culture which produces the compounds of the present invention, Aspergillus fischeri var. thermomutatus ATCC 18618, was obtained from the American Type Culture Collection (ATCC located in 12301 Parklawn Drive, Rockville, Md. 20852, USA). The taxonomical properties of A. fischeri var. thermomutatus ATCC 18618 are reported in the literature (Mycopathol. Mycol. Appl., 36, 161-164, 1968). The culture has been deposited further at Agency of Industrial Science and Technology located in 1-3, Higashi 1-chome Tsukuba-shi, Ibaraki-ken, Japan on Dec. 15, 1993, under Accession No. FERM BP-4497.
In addition, mutant strains of Aspergillus fischeri var. thermomutatus ATCC 18618, can be used. Such mutant strains can be obtained spontaneously, or by the application of known techniques, such as exposure to ionising radiation, ultraviolet light, and/or chemical mutagens such as N-methyl-N-nitrosourethane, N-methyl-N'-nitro-N-nitrosoguanidine, ethyl methyl sulphate, etc. Genetically transformed and recombinant forms include mutants and genetic variants produced by genetic engineering techniques, including for example recombination, transformation, transduction, protoplast fusion, etc. The invention also extends to p
REFERENCES:
patent: 5073567 (1991-12-01), Kojima et al.
Paden, J.W. (1968) Mycopathol. Mycol. Appl. 36: 161-164, 1968.
Bishop Bernard F.
Kojima Nakao
Kojima Yasuhiro
Yamauchi Yuji
Benson Gregg C.
Goddard Carl J.
Pak Michael
Pfizer Inc.
Richardson Peter C.
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