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Novel pyridyl cyanoguandine compounds
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A compound, pyridyl technology, applied in the field of pharmaceutical preparation
Inactive Publication Date: 2006-03-29
LEO PHARMA AS
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Replacement of the side chain of pinacidil with a longer side chain-containing aryl group resulted in the loss of antihypertensive activity, but on the other hand, in a rat model with Yoshida ascites tumor, oral administration of drug, the compound was found to exhibit antitumor activity
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[0115] This compound was prepared as described in Preparation 1, except that 2-hydroxyquinoline was substituted for 3-hydroxypyridine. The crude product was purified by silica gel chromatography using ethyl acetate as eluent to give the desired compound as a colorless oil.
[0119] 2-[6-(N-tert-butoxycarbonylamino)-1-hexyl-oxy]-quinoline (480 mg) was treated with excess hydrogen chloride in ether and stirred at room temperature for 1 hour. The crystals were separated by filtration, redissolved in water, made strongly basic with sodium hydroxide, and extracted twice with chloroform. Drying over potassium carbonate, filtration and evaporation of the organic phase gave the title compound as a colorless oil.
[0123] 3-[6-Amino-1-hexyl-oxy]-pyridine (150 mg), S-methyl-N-cyano-N'-4-pyridyl-isothiourea (123 mg), triethylamine ( A mixture of 0.18ml), 4-(N,N-dimethylamino)-pyridine (3.5mg) and pyridine (5ml) was stirred overnight at 60°C. After cooling to room temperature, pyridine was removed by evaporation twice with toluene in vacuo and the residue was partitioned between water and ethyl acetate. The organic phase is dried and evaporated and the crude product obtained is purified by chromatography on silica gel using ethyl acetate / methanol / ammonia (40:10:2.5) as eluent. The pure fractions were collected and evaporated to crystallize the title compound from ethyl acetate.
[0127] This compound was prepared as described in Example 1 except that 1-(6-amino-1-hexyl)-imidazole was substituted for 3-[6-amino-1-hexyl]-pyridine.
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Abstract
Compounds according to formula (I) wherein R1 represents hydrogen, halogen or one or more straight or branched, saturated or unsaturated C1-6 hydrocarbon radical, optionally substituted with halogen, hydroxy, cyano, nitro, carboxy, alkoxy, alkoxycarbonyl, alkylcarbonyl, formyl, amico, aminoalkyl, aminocarbonyl, alkylcarbonylamino, sulfo, aminosulfonyl, alkylsulfonylamino, hydroxysulfonyloxy, dihydroxyphosphinoyloxy or phosphono; X represents a straight or branched, saturated or unsaturated C1-12 hydrocarbon diradical, optionaly substituted with halogen, hydroxy, cyano, nitro, carboxy, alkoxy, alkoxycarbonyl, alkylcarbonyl, formyl, amino, aminoalkyl, aminocarbonyl, alkylcarbonylamino, sulfo, aminosulfonyl, alkylsulfonylamino, hydroxysulfonyloxy, dihydroxyphosphinoyloxy or phosphono; Y represents a bond, O, C(O), S, S(O), S(O)2, C(O)O, NH, C(O)NH, OC(O) or NHC(O); Z represents an aromatic or non-aromatic heterocyclic radical with 5-12 ring atoms, optionally substituted with halogen, hydroxy, cyano, nitro, alkoxy, alkoxycarbonyl, alkylcarbonyl, formyl, aminoalkyl or straight or branched, saturated or unsaturated C1-4 hydrocarbon radical, optionally substituted with halogen, hydroxy, cyano, nitro, alkoxy, alkoxycarbonyl, alkylcarbonyl, formyl or aminoalkyl; provided that R1 is not attached to the nitrogen-atom in the pyridyl ring, and pharmaceutically acceptable salts, solvates, hydrates, N-oxides and prodrugs thereof are disclosed. The compounds are useful in therapy.
Description
field of invention [0001] The present invention relates to new pyridyl cyanoguanidine medicine and its pharmaceutical composition, and their application in medicine preparation. Background of the invention [0002] Pyridylcyanoguanidine as pinacidil (N-1,2,2-trimethylpropyl-N'-cyano-N"-(4-pyridyl)guanidine), originally discovered for potassium The opening of the channel was subsequently developed as an antihypertensive agent. Replacement of the side chain of pinacidil with a longer aryl group containing a side chain resulted in the disappearance of the antihypertensive activity, but on the other hand, in patients with Yoshida In the rat model of ascites tumor, the compound was found to exhibit antitumor activity after oral administration to rats. [0003] Different classes of pyridylcyanoguanidines with antiproliferative activity have been disclosed, for example in EP 660823, WO 98 / 54141, WO 98 / 54143, WO 98 / 54144, WO 98 / 54145, WO00 / 61559 and WO 00 / 61561 . C. Schou et al. ...
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