Chemistry of hydrocarbon compounds – Aromatic compound synthesis – Having alkenyl moiety – e.g. – styrene – etc.
Patent
1994-10-14
1996-11-26
Pal, Asok
Chemistry of hydrocarbon compounds
Aromatic compound synthesis
Having alkenyl moiety, e.g., styrene, etc.
C07C 1518
Patent
active
055787428
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
The present invention concerns new chemical compounds from the group of bis-phenyl-hex-3-enes, a process for their production and their use as therapeutic agents.
Numerous diseases in humans are due to an uncontrolled growth of body cells. This disturbance in proliferation can lead to a benign degeneration e.g. psoriasis vulgaris in the case of keratinocytes or .beta.-thalassaemia in the case of erythrocytes or it can also lead to a malignant degeneration such as in all forms of cancer.
The aim of a cancer therapy is to completely destroy or at least to significantly inhibit the growth of the tumour cells. In addition to surgical measures and radiation therapy, chemotherapeutic agents such as 5-fluorouracil, cytosine-arabinoside etc. are also available nowadays for the treatment of cancer patients. A disadvantage in the use of these chematherapeutic agents is, however, that in addition to the tumour cells they also can damage healthy regions of the organism. Therefore a search has been going on for several years for less aggressive methods of treatment. Thus the use of tamoxifen for mammacarcinomas brought the first very promising results (Jordan, Antiestrogens in Cancer Treatment, in: Stoll, B. A., Endocrine Management of Cancer, Karger, Basel (1988), 57-65). However, numerous cancer diseases (e.g. colonic and pancreatic carcinoma) cannot yet be treated to an adequate extent by drugs (Cohen et al., Colorectal Cancer, and Brennan et al., Cancer of the Pancreas in: DeVita, V. T., Helman, S. and Rosenberg, St. A., Cancer, Lippincott Co., 3rd Edition (1989)).
One of the main causes for carcinogenesis is considered to be mistakes in the expression of so-called oncogenes such as myc or ras (Tabin et al., Nature, 300 (1982), 143-149). An important regulation mechanism of gene expression--also in oncogenes--is the degree of methylation of DNA (Doerfler, J. gen. Virol., 57 (1981) 1-20). Thus using ras and myc oncogenes as an example it was possible to detect a hypomethylation in the expressed cancerogenic status (Feinberg et al., Biophys. Res. Comm., 111 (1983) 47-54; Cheah et al., J. Nat. Cancer Inst., 73, (1984), 1057-1061)). Furthermore it is known that the growth as well as the correct somatic function of degenerate cells can be regulated by a targetted control of DNA methylation. This was shown by Ley et al. (DNA methylation and globin gene expression in patients treated with 4-azacytidine, in: Globin Gene Expression and Hematopoietic Differentiation, Alan P. Liss, N.Y. (1983), 457-474). A further direct correlation between the methylation of DNA and disturbances in the central nervous system were found in HIV-positive patients (Keating et al., Lancet, 337 (1991) 935-939).
Moreover it was possible in in vitro cell culture experiments to establish a direct correlation between malignant transformation and DNA hypomethylation on the one hand and between concentration-dependent growth inhibition of tumour cells (from humans and animals) and DNA hypermethylation on the other hand (Pechan, (1987), Dissertation, University Wurzburg).
SUMMARY OF THE INVENTION
An object of the present invention was to provide new compounds which exhibit a pharmaceutical efficacy in the treatment of diseases that are associated with degenerate cell growth i.e. disturbances of cell proliferation.
The object according to the invention is achieved by a 3,4-bis(4-X-phenyl)-3-hexene in which the groups X in each case represent alkyl, alkenyl or alkinyl residues with 1 to 10 carbon atoms which are substituted if desired, or aralkyl residues with 1 to 10 non-aromatic carbon atoms which are substituted if desired.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The groups X are preferably alkyl, alkenyl or alkinyl residues each with 1 to 5 carbon atoms which are substituted if desired.
The groups X in the compounds according to the invention are particularly preferably alkyl residues with 2 to 4 carbon atoms, the groups X are most preferably ethyl, n-propyl, isopropyl, sec.-butyl or tert. butyl residues.
The term "a
REFERENCES:
Chemical Abstract CA 77:14579 (1972).
Chemical Abstract CA 99:70314 (published 1983).
Chemical Abstracts, vol. 77, No. 3, 17 Jul. 1972, Abstract No. 14579x.
Owen et al., "Papillomatous Growths 'on Internal Genitalia of Bitches Administered the Synthetic Estrogen Tran-4,4'-Dimethyl-.alpha.,.alpha..sup.1 -Diethylstilbene", Technology and Applied Pharmacology, 21, 582-585 (1972).
Metzler Manfred
Pechan Reinhard
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