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Substituted benzimidazoles and their use for inducing apoptosis
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a technology of benzimidazoles and inducible apoptosis, which is applied in the direction of biocide, plant growth regulators, animal husbandry, etc., can solve the problems of loss of normal cell division regulation control and failure to undergo appropriate cell death
Inactive Publication Date: 2007-07-19
BASILEA PHARMACEUTICA AG
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These compounds demonstrate therapeutic efficacy by inducing apoptosis in various tumor cell lines and autoimmune disease models, offering a potential alternative with reduced side effects and improved treatment outcomes for malignancies and autoimmune disorders.
Problems solved by technology
Such cells may lose the normal regulatory control of cell division, and may also fail to undergo appropriate cell death.
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[0183] A suspension of 3-amino-2-(1H-benzimidazol-2-yl)-1,2,4-triazole (0.15 g, 0.75 mol), 3,4-dimethyl phenacylbromide (0.204 g, 0.9 mmol) and dry potassiumcarbonate (0.258 g, 1.87 mmol) is stirred at room temperature for 16 hours. The mixture is diluted with water and the product extracted with ethyl acetate. The product is purified by chromatography on silicagel. M.p. 190-193C, 1H-NMR (400 MHz, d6-DMSO): 7.84 (m, 1H); 7.77 (m, 3H); 7.65 (m, 2H); 7.50 (s, 1H); 7.33 (d, 1H); 6.22 (s, 2H); 2.30 (s, 6H).
[0184] To a solution of 2-hydrazino-1H-benzimidazole (5.0 g, 33.7 mmol) in ethanol (30 ml) is added sequentially triethylamine (5 ml, 33.7 mmol) and N-cyanoformimidic acid ethyl ester (3.3 g, 33.7 mmol) with cooling. After stirring for 2 hours at 0° C. the resulting precipitate is filtered with suction and dried to give 3-amino-2-(1H-benzimidazol-2-yl)-1,2,4-triazole. 1H-NMR (400 MHz, d6-DMSO): 13.0 (s,1H); 7.77 (s,1H); 7.70 (m, 2H); 7.50 (m, 2H); 7.20 (s, 2H).
[0185] To a mixture of 2-mercapto-1H-benzimidazole (15 g, 100 mmol), sodiumhydroxide (4.4 g, 110 mmol) and a catalytic amount of tungstic acid is added hydrogenperoxide (43 ml, 100 mmol of a 30% aqueous solution) within 2 hours keeping the temperature at 25° C. Additional hydrogenperoxide (3×1 ml) is added to complete the transformation. After the addition of hydrazine hydrate (15 g, 300 mmol) the mixture is heated at 80° C. for 5 hours. On cooling the 2-hydrazino-1H-benzimidazole starts crystallizing. Filtration with sucking, washing with ether and drying yields the pure product. 1H-NMR (400 MHz, d6-DMSO): 10.9 (s,1H); 7.78 (m,1H); 7.10 (m, 2H); 6.84 (m, 2H); 4.42 (s, 2H).
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Abstract
The invention relates to compounds of formula (I) wherein R represents aryl or heteroaryl, X is a bond, a carbonyl group, a derivative of a carbonyl group, an ethylene group or an ethylenecarbonyl group, R1 is optionally substituted amino or hydroxy, and the substituents R2 to R6 have the meanings given in the specification, to methods of synthesis of such compounds, to pharmaceutical compositions containing compounds of formula (I), to intermediates, to the use of a compounds of formula (I) as a medicament and for the preparation of a pharmaceutical composition for the treatment of neoplastic and autoimmune diseases, and to methods of treatment of neoplastic and autoimmune diseases using such compounds of formula (I) or of pharmaceutical compositions containing same.
Description
[0001] The invention relates to novel substituted benzimidazoles, processes for the preparation thereof, pharmaceutical compositions containing same, the use thereof optionally in combination with one or more other pharmaceutically active compounds for the therapy of neoplastic diseases and autoimmune diseases, and a method for the treatment of such a diseases. BACKGROUND OF THE INVENTION [0002] Cancer is one of the leading causes of death in humans. Although a variety of drugs against neoplastic diseases have been developed and techniques are available such as surgery and radiation therapy, there is still a need for alternative and improved methods of treatment of neoplastic diseases. [0003] Autoimmune diseases are associated with abnormal lymphoproliferation as a result of defects in the termination of lymphocyte activation and growth. Often, such diseases are associated with inflammation like rheumatoid arthritis, insulin dependent diabetes mellitus, multiple sclerosis, systemic ...
Claims
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Patent Type & Authority Applications(United States)
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