Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2003-05-02
2004-06-08
Aulakh, Charanjit S. (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C546S061000
Reexamination Certificate
active
06747038
ABSTRACT:
The invention relates to new phenanthridine derivatives as well as pharmaceuticals for a antitumoural therapy and prophylaxis which contain these phenanthridine derivatives. As state of the art WO 97/14683 should be mentioned where phenanthridine derivatives and methods of their preparation are described.
While the synthesis of phenanthridine derivatives is well known for a long time from the technical state and many different synthetic routes exist, the pharmalogical activity has been detected just recently. Thus WO 97/14683 describes for the first time the antitumoral activity of these compounds. However, the antitumoral activity of the described derivatives is limited for a medical application. Starting from this, the objective of this invention is to present new phenanthridine derivatives, similar to the ones described in WO 97/14683, which show a higher antitumoral activity, in comparison to the state of the art.
The objective is achieved with respect to the phenanthridine derivatives by characterising features of claim
1
, and with respect to pharmaceuticals by the features of claim
7
.
The subclaims demonstrate advantageous further developments. The application of the phenanthridines is mentioned in claims
12
to
16
.
In accordance with the invention new phenanthridine derivatives with excellent antitumoural and cytotoxic properties could be delivered. They are defined by the general formular I
The residues R
1
to R
4
are selected in a way that three of them are methoxy groups and one is a hydrogen.
Surprisingly it could be demonstrated that phenanthridine derivatives substituted in this way have—from the state of the art—unknown and unexpected antitumour properties. This refers to the subcutaneous as well as to the intraperitoneal application. The known derivatives from WO 97/14683 show less activity in terms of subcutaneous and intraperitoneal usage.
The phenanthridine derivatives presented here show excellent anti-tumour, anti-microbial, anti-fungicidal, anti-viral and anti-inflammatory properties. For the studies of the pharmacological properties, the derivatives have been tested in a “in-vivo-antitumor-Screening” of the National Cancer Institute (NCI) Bethesda, Md., USA.
The derivatives have been tested against a standard panel of twelve human pathogenic tumor cell lines of six different cancer types (non-small cell lung cancer, melanoma, breast cancer, ovarian cancer, colon cancer, CNS cancer).
In the prefered way, the derivatives are present in an ionic from, especially prefered as salts. In accordance with the invention the phenanthridine derivatives exist in acceptable physiologicals salts. Such salts are e.g. salts of inorganic an organic acids, for example hydrochlorides, hydrobromides and sulfates. Especially well suited salts from organic acids are formed with aliphatic mono- and dicarboxylic acids. Examples are acetates, maleates and fumarates.
The following derivatives are prefered according to the highest anti-tumour activity:
A) 6-Amino-11-(3′,4′,5′-trimethoxyphenyl)benzo[c]phenanthridine perchlorate with the structure presented by formula III,
B) 6-Amino-11,12-dihydro- 11-(2′,3′,4′-trimethoxyphenyl)benzo[c ]phenanthridine hydrochloride with the structure presented by formula IV
C) 6-Amino- 11,12-dihydro- 11-(3′,4′,5′-trimethoxyphenyl)benzo[c ]phenanthridine hydrochloride with the structure represented by formula V
The invention also relates therefor to medicines containing phenanthridine derivatives which are described here. The medicine contains, for this purpose, at least one phenanthridine derivative, in the manner described here, together with at least one inert pharmaceutically acceptable carrier or dilution medium. A derivative of the general formula III, IV and/or V is preferred as a phenanthridine derivative. The compound, according to the invention, can be administered orally, topically or parenterally, or in the form of suppositories. The preferred mode of administration is oral administration. This can be administered in the form of the base or as a physiologically acceptable salt. It is generally mixed with a pharmaceutically acceptable carrier or dilution medium, in order to create a medicine. For oral administration the medicine can be made available most usefully in the form of capsules or tablets or possibly even slow-release tablets. They can also be available in the form of dragees or in syrup form. Suitable topic preparations are e.g. salts, lotions, creams, powders and sprays.
In the same way the invention concerns the usage of at least one of the above named phenanthridine derivatives for the preparation of a medicine for an anti-tumour therapy and prophylaxis.
The further examples and figures describe in greater detail the properties of the compounds presented in this invention.
REFERENCES:
patent: 6030981 (2000-02-01), Clement et al.
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