Phenanthridine derivatives, methods of producing them and medica

Details Phenanthridine derivatives, methods of producing them and medica Phenanthridine derivatives, methods of producing them and medica

1998-04-13

2000-02-29

Kight, John

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

546 61, A61K 3144, C07D22118

Patent

active

060309814

DESCRIPTION:

BRIEF SUMMARY
BACKGROUND OF THE INVENTION

The invention relates to new phenanthridine derivatives, which have an amino-group in position 6, a method for their production and for producing medicines containing phenanthridine derivatives.
Presently known syntheses of benzo(c)phenanthridine, its 11,12 dihydro-derivatives and similar compounds are very complex. The methods of Robinson et al. concerning the Bischler-Napieralski cyclisation and also of Ninomiya et al. using photocyclisation by Enamiden or by Shamma et al. and Cushman et al. concerning the Dickman-Thorpe-cyclisation should be mentioned here, said methods all extending over a great number of reaction steps (see I. Ninomya and T. Naito: Synthesis of the benzo(c)phenanthridine alkaloids. Recent. Dev. Nat. Carbon compd. 10, 11-90 (1984) and the literature mentioned there). p Furthermore, benzo(c)phenanthridine derivatives and their anti-tumour effect are known from Pharmacy 44 pp. 593-597 (1989). Further phenanthridine derivatives are described in Tetrahedron 49 pp. 10305-10316 (1993) and in J. Chem. Soc. Perkin Trans. I, pp. 1137-1140 (1983) and in J. Me. Chem. 36, pp. 3686-3692 (1993). In the publications in J. Med. Chem. and Tetrahedron, derivatives with an amino-group in position 6 were also indeed described, said amino-group being substituted however in every case. Other derivatives have up till now not become known. This can be attributed mainly to the fact that the presently known derivatives are based on synthesis methods which are costly and complex. Therefore production of other phenanthridine derivatives was up till now not possible.


OBJECT OF THE INVENTION

This assumed, it is the object of the present invention to make known new phenanthridine derivatives, a method for their production and their application.
The object is achieved, with respect to the phenanthridine derivatives, by the characterising features of claim 1 and, with respect to the production method, by the features of claim 5. The application according to the invention of these phenanthridine derivatives is mentioned in claim 10. The subclaims demonstrate advantageous further developments.
According to claim 1, the new phenanthridine derivatives are defined by the general formulae I and II, ##STR2## in which R.sub.1 means a hydrogen atom, an aromatic or heterocyclic residue, and R.sub.2 and R.sub.3, which can be the same or different, mean hydrogen atoms an alkyl-oxy residue, an alkylene-oxy residue, a halogen atom or a nitro group.
By an aromatic carbocyclic residue R.sub.1 can be understood particularly such residues as are derived from benzene, naphthalene, anthracine, phenanthrene and pyrene. By an aromatic heterocyclic residue R.sub.1 can be understood particularly residues, which are derived from furane, thiophene, pyridine, 1,2,4-oxdiazole, 1,2,3-triazole, benzofurane, benzoxazole, benzimidazole, benzthiazole, also the corresponding naphtho-analogues of the type named benzo-five ring heterocyclenes and from indole, quinolene and isoquinolene. The aromatic carbocyclic or heterocyclic residues can be substituted once or several times.
For this purpose, as substitutes under the reaction conditions, inert groups and/or atoms may be considered such as mono-amino groups, alkyl amino groups, dialkyl amino groups, alkyl groups, alkoxyl groups, alkylene oxy groups and halogens.
On the basis of the found pharmacological characteristics, the derivatives which are of particular importance are those in which R.sub.2 and R.sub.3 hydrogen, and R.sub.1 hydrogen are an unsubstituted phenyl residue, a phenyl residue with one or several methoxyl groups or a N,N-dimethyl amino function. For this purpose, those derivatives in which R.sub.1 is a substituted or unsubstituted phenyl residue, in particular 2,4-dimethoxyphenyl or 3,4-dimethoxyphenyl, may be emphasized. The 2,4-dimethoxyphenyl derivative is particularly preferred here. The phenanthridine derivatives according to the invention readily form physiologically acceptable salts. Such salts are e.g. salts with inorganic and organic acids, e.g. d

REFERENCES:
patent: 5747502 (1998-05-01), Hanaoka et al.

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