Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1998-09-03
2000-07-11
Richter, Johann
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
435156, 4352561, 4352543, 435913, 514721, C07C 4323, C12P 722, A61K 31075
Patent
active
060875402
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a compound which is useful as a pharmaceutical ingredient, a process for producing the same and use of the same. Specifically, a novel terphenyl compound which has an immunosuppressive, antiinflammatory and antitumor activity, a process for producing the same and an immunosuppressive, antiinflammatory and antitumor agent which comprises the same are provided.
BACKGROUND ART
A transplantation of a tissue or an organ which is frequently performed in recent years is attracting attention as a method for recovering a dysfunctional organ or tissue. However, a rejection symptom for excluding a transplanted part after an operation is a serious problem and it is not going too far to say that a success of the transplantation depends on prevention of the rejection symptom.
In these situations, an immunosuppressive agent is being used for prevention and a treatment of a rejection symptom against a transplantation of an organ or a tissue or a graft-versus-host reaction which is caused by a bone marrow transplantation and is an important pharmaceutical agent. The immunosuppressive agent is often used for treating not only a rejection symptom caused by a transplantation but also autoimmune diseases such as chronic rheumatoid arthritis, allergic diseases and the like. Recently, various immunosuppressive agents such as azathioprine, corticoid, cyclosporin A, tacrolimus and the like are developed and clinically used but they are not so satisfactory in view of their effect and side effect.
Many antitumor agents are also clinically used, but most of them have both a potent antitumor activity and toxicity as a side effect, which limits the dosage.
In these situations, a development of an immunosuppressive or antitumor agent which has a potent activity and can safely be used has been desired.
The compounds which belong to the same type as the compounds of the present invention are described in Chemical Pharmaceutics Bulletin, 24 (4). 613-620 (1976), The Journal of Antibiotics, 32 (6), 559-564 (1979), Agricultural Biological Chemistry, 49 (3), 867-868 (1985) and the like. In these literature, these compounds are indicated to have a toxicity against sea urchin embryo cells and Hela cells but their immunosuppressive and antiinflammatory activity are not mentioned at all.
DISCLOSURE OF INVENTION
An object of the present invention is to provide a novel compound which has an immunosuppressive, antiinflammatory or antitumor activity, a process for producing the same and an immunosuppressive, antiinflammatory or antitumor agent comprising the same.
The present inventors found a compound which has a potent immunosuppressive, antiinflammatory and antiproliferative activity on tumor cells in a culture broth of Aspergillus candidus RF-5762, a kind of filamentous fungus, isolated and purified the active compound and accomplished the present invention.
The present invention provides a compound of the formula (I): ##STR2## wherein R.sup.1 is hydrogen or hydroxy and R.sup.2 is hydroxy or methoxy, pharmaceutically acceptable salts or hydrates thereof. The present invention provides a process for producing the compound (I) which comprises cultivating a microorganism which belongs to the genus Aspergillus and can produce the compound (I) and collecting the compound (I) from the obtained culture.
Furthermore, the present invention provides the process for producing the compound (I) which comprises a compound of the formula (II), a precursor of the compound (I): ##STR3## wherein R.sup.1 and R.sup.2 are the same as defined above is subjected to a reaction of 3-methyl-2-butenylation.
In an other embodiment, the present invention provides a pharmaceutical composition, specifically, an immunosuppressive, antiinflammatory or antitumor agent comprising the compound (I). Furthermore, the present invention provides a method for suppressing an immune reaction, treating or preventing inflammation or treating tumor which comprises administering the compound (I). Another object of this invention is to pro
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Kamigauchi Toshiyuki
Suzuki Ryuji
Keys Rosalynd
Richter Johann
Shionogi & Co. Ltd.
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