Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1996-12-13
1998-10-06
Grumbling, Matthew V.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
546123, 544279, 514249, A61K 3147, C07D40114
Patent
active
058176691
DESCRIPTION:
BRIEF SUMMARY
This application claims priority under 35 U.S.C. .sctn. 371 from PCT/JP95/01110, filed Jun. 6, 1995.
TECHNICAL FIELD
This invention relates to novel pyridone-carboxylic acid derivatives, anti-tumor agents containing the same as effective ingredients, and processes for the preparation of the novel pyridone-carboxylic acid derivatives, etc.
BACKGROUND ART
There have been known both various pyridone-carboxylic acid derivatives per se which have 2-thiazolyl groups and the fact that these pyridone-carboxylic acid derivatives show anti-bacterial activity. For example, the following Compound A is disclosed in Example 24 of Japanese Patent Application Laid-Open (Kokai) No. 152682/1986 (hereinafter referred to as Ref. 1): ##STR3##
In Example 5 of said Ref. 1, the following Compound B is exhibited: ##STR4##
Further, in Example 12 of Ref. 1, the following Compound C is disclosed: ##STR5##
The above compounds B and C are also disclosed in Table 1 of Japanese Patent Application Laid-Open (Kokai) No. 33176/1987 (hereinafter referred to as Ref. 2).
Moreover, the following Compound D is mentioned in Example 24-4 of Japanese Patent Application Laid-Open (Kokai) No. 56959/1985 (corresponding to European Patent Application Laid-Open No. 131839 and U.S. Pat. No. 4,730,000; hereinafter referred to as Ref. 3 together) and in Example 15 of Japanese Patent Application Laid-Open (Kokai) No. 251667/1986 (hereinafter referred to as Ref. 4). ##STR6##
The following Compound E is mentioned in Example 28-16 of Japanese Patent Application Laid-Open (Kokai) No. 163866/1985 (corresponding to European Patent Application Laid-Open No. 154780 and U.S. Pat. No. 4,774,246; hereinafter referred to as Ref. 5 together). ##STR7##
Further, the following Compound F is shown in Example 8 of Japanese Patent Application Laid-Open (Kokai) No. 85255/1990 (hereinafter referred to as Ref. 6). ##STR8##
However, the chemical structure of these compounds is different from the structure of Compound (I) of this invention in the following points (1) and (2). fluorine atom. a substituted 1-pyrrolidinyl group.
In addition, Refs. 1 to 6 only mention that these Compounds A to F exhibit antibacterial activity, and teach nothing on their anti-tumor activity or anti-cancer activity.
It is known that certain kinds of pyridone-carboxylic acid derivatives show anti-tumor activity or anti-cancer activity. For example, Cancer Research 52, 2818 (1992) reports that the following Compound G has anti-tumor activity: ##STR9##
It is reported in this treatise that 90 kinds of pyridone-carboxylic acid derivatives were investigated for anti-tumor activity, and that most of said derivatives showed no anti-tumor activity with the exception of only several types of the derivatives. It is further taught that the cyclopropyl group which is substituted at the 1-position and the two halogen atoms which are each substituted at the 6- and 8-positions play an important role for the expression of anti-tumor activity, and that a pyridone-carboxylic acid derivative which is free from such substituents shows no anti-tumor activity.
BRIEF DESCRIPTION OF DRAWINGS
FIGS. 1 to 9 show the change of tumor growth inhibition rate (IR) with the lapse of days in the case where a compound of this invention was administered to nude mice into which various human cancer cells had been transplanted.
FIGS. 10 to 14 show the change of tumor weight with the lapse of days in the above experiment. Rate IR % on the last day of observation!.
FIGS. 15 to 19 show reaction formulae of the reactions which are mentioned be mentioned later.
DISCLOSURE OF INVENTION
Seeking intensively for compounds having anti-tumor activity, the present inventors have resultantly found that novel pyridone-carboxylic acid derivatives having such 2-thiazolyl groups as may be substituted show remarkable anti-tumor activity.
This invention relates to pyridone-carboxylic acid derivatives which have 2-thiazolyl groups and which have the following general formula (I). and to salts thereof: ##STR10## wherein R.sub.1 is a hydrogen atom, a
REFERENCES:
patent: 4730000 (1988-03-01), Chu
patent: 5059597 (1991-10-01), Petersen et al.
Yamashita et al., Cancer Research, vol. 32, pp. 2818-2822, May 15, 1992.
Chiba Katsumi
Kashimoto Shigeki
Shibamori Koh-ichiro
Tomita Kyoji
Tsuzuki Yasunori
Dainippon Pharmaceutical Co., Ltd.
Grumbling Matthew V.
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