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Pyrimidinedione Derivative Compounds, Method of Producing

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Pyrimidinedione Derivative Compounds, Method of Producing Europa,schesP_ MM II M M MM II II II II III II I II J European Patent Office _ © Publication number: 0 369 627 B1 Office europeen* des.. brevets , © EUROPEAN PATENT SPECIFICATION © Date of publication of patent specification: 21.12.94 © Int. CI.5: C07D 239/54, C07D 401/12, A61K 31/505 © Application number: 89311135.1 @ Date of filing: 27.10.89 © Pyrlmldlnedlone derivative compounds, method of producing the same and antiarrythmic agents containing the same. © Priority: 29.10.88 JP 271992/88 © Proprietor: MITSUI TOATSU CHEMICALS, Inc. 06.12.88 JP 306840/88 2-5 Kasumigaseki 3-chome 06.12.88 JP 306841/88 Chiyoda-Ku 18.04.89 JP 96416/89 Tokyo 100 (JP) 18.04.89 JP 96417/89 18.04.89 JP 96418/89 @ Inventor: Katakami, Tsutomu 06.09.89 JP 229272/89 1651-17, Koshigoe 25.09.89 JP 246317/89 Kamakura-shi 25.09.89 JP 246318/89 Kanagawa-ken (JP) Inventor: Yokoyama, Tatsuro @ Date of publication of application: 3-5-10-404, Namiki 23.05.90 Bulletin 90/21 Kanazawa-ku Yokohama-shl © Publication of the grant of the patent: Kanagawa-ken (JP) 21.12.94 Bulletin 94/51 Inventor: Miyamoto, Mlchihiko 2882-3-31, lijimacho © Designated Contracting States: Sakae-ku AT BE CH DE ES FR GB IT LI NL SE Yokohama-shi Kanagawa-ken (JP) © References cited: Inventor: Mori, Haruki H-509, Nyuraifu DE-A- 2 819 629 Kanazawabunko 1200-6, Kamariyacho 00 CHEMICAL ABSTRACTS, vol. 112, 1990, page Kanazawa-ku IV 432, abstract no. 62669q, Columbus,Ohio, Yokohama-shi CM US; & JP-A-01 175 937 (MITSUI TOATSU Kanagawa-ken (JP) CO CHEMICALS, INC.) 12-07-1989 o> CO 00 Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid (Art. 99(1) European patent convention). Rank Xerox (UK) Business Services (3. 10/3.09/3.3.3) EP 0 369 627 B1 The Pharmacological Basis of Therapeutics, Inventor: Kawauchi, Nobuya Goodman and Gilman's eighth edition, 1990, 3-42-7-138, Hirado Pergamon Press, Chapter 35, pages 840-307. Totsuka-ku Yokohama-shi Drugs, vol. 35, pages 286-319, 1988. Kanagawa-ken (JP) Inventor: Nobori, Tadahlto Cardiovascular Pharmacology, Second edi- 502-1, Maedacho tlon, edited by Michael Antonaccio, Raven Totsuka-ku Press, 1984, pages 329-342. Yokohama-shi Kanagawa-ken (JP) Inventor: Sannohe, Kunio 2070, lijimacho Sakae-ku Yokohama-shi Kanagawa-ken (JP) Inventor: Kamlya, Joji 2141, Tougou Mobara-shi Chiba-ken (JP) Inventor: Ishli, Masaaki 2142, Tougou Mobara-shi Chiba-ken (JP) Inventor: Yoshihara, Kanjl 90-1, Machibo Mobara-shi Chiba-ken (JP) 0 Representative: Stuart, Ian Alexander et al MEWBURN ELLIS York House 23 Klngsway London WC2B 6HP (GB) 2 EP 0 369 627 B1 Description This invention relates to novel pyrimidinedione derivatives and acid addition salts thereof, to methods of producing the same and to pharmaceutical agents containing the same, which are effective for the 5 treatment of cardiac dysfunctions such as arrhythmia and cardiac insufficiency. The mechanism of the occurrence of arrhythmia is complicated. Abnormalities in stimulation production and disorders in the conducting system or combinations thereof are considered to be responsible. As to disorders in excitation conduction, the re-entry theory is representative. One of the conditions of occurrence of arrhythmia is irregularity in the refractory period in various parts io of the heart. In addition, one-directional block, shortened refractory period, delay in conduction, the presence of circus movement are complicatedly involved. Conventionally, varieties of antiarrhythmic agents have been used for the treatment of arrhythmia. The antiarrhythmic agents are classified into four groups according to their mode of action. Namely, E. M. Vaughan Williams (Vaughan Williams E. M.; "Advances in drug research, vol. 9"; ed. by 75 Harper N. J., Simmonds A. B., Academic Press, London, 1974; pages 69-101) classified the antiarrhythmic agents into the following four groups according to their action against the action potential of cardiac muscle or against the ionic current which generates the action potential. Class 1 : Sodium channel depressors 20 These agents are efficacious in repressing a sodium current. However, these agents have no or only minute effects on the retention time of the normal action potential and decrease the maximum rising velocity (Vmax) of the sodium current. The antiarrhythmic agents which belong to this class have a high antiarrhythmic activity but at the same time strongly repress cardiac functions. Careful consideration is 25 required in administering to patients with cardiac failure or hypotension. Class II: Beta-blocking agents The agents in this class, represented by propranolol, are efficacious in beta-blocking action and are 30 useful in treating patients with arrhythmia in which the sympathetic nerve is involved. However, care must be taken for use since these agents have side-effects caused by the beta-blocking action, such as depression of cardiac functions, induction of bronchial asthmatic attacks and hypoglycemic seizures. Class III: Pharmaceutical agents for prolonging the retention time of the action current. 35 These agents are efficacious in remarkably prolonging the retention time of the action current of the cardiac muscle and in prolonging an effective refractory period. Re-entry arrhythmia is considered to be suppressed by the action of the pharmaceutical agents of Class III. The medicaments of this Class III include amiodarone and bretylium. However, all the agents have severe side effects; therefore, careful 40 consideration is required for use. Class IV: Calcium antagonists These agents control a calcium channel and suppress arrhythmia due to automatic sthenia of sinoatrial 45 nodes and to ventricular tachycardia in which atrial nodes are contained in the re-entry cycle. Among these antiarrhythmic agents, pharmaceutical agents of the Class III type are considered to be particularly important and the most efficacious, and known to be effective on ventricular arrhythmia, the most fatal of all symptoms. Various medicinal agents have been developed and used as antiarrhythmic agents. 50 Search for ideal antiarrhythmic agents has been pursued for treatment of arrhythmia which has complicated generating mechanisms and requires administration of such agents for a long period of time. However, satisfactory results have not been achieved. The present invention has been accomplished in view of the present situation regarding antiarrhythmic agents. A preferred embodiment of one aspect of the present invention is a novel compound which is useful 55 as a Class III type antiarrhythmic agent; an embodiment of a second aspect may provide a process for producing the same. Embodiments of the present invention may provide a novel compound which is effective in improving cardiac dysfunction such as cardiac insufficiency and a process for the preparation of the same. 3 EP 0 369 627 B1 Embodiments of the present invention may provide a pharmaceutical agent, which contains the novel compound as an effective component, for the treatment of cardiac dysfunctions such as arrythmia and cardiac insufficiency. In the course of the intensive study to solve the above-mentioned problems, the present inventors 5 discovered compounds of the general formula (1) shown below and acid addition salts thereof, and then investigated the pharmacological properties of these compounds. As a result, the present inventors found that these compounds may have pharmacological characteristics to markedly prolong the retention time of the action potential of cardiomuscular cells and to markedly prolong the ventricular refractory period; and thus completed the present invention. io Furthermore, the present inventors found that preferred embodiments of the present invention have a positive inotropic action and are useful as therapeutic agents for cardiac insufficiency. Compounds according to the present invention are those of the general formula (1) shown below and acid addition salts thereof. More specifically, the compounds are described in Examples thereinafter as preferred embodiments. 15 N02 R 1 R*\3 0 20 OJ/hA-N-(CHz)n-N^ N-R" X2 R 3 0 25 In the formula, A represents -(CH2)m-, -B-(CH2)k-, -D-(CH2)r V y~ or -NHCH2CH-CH9- ; 30 OH B represents an oxygen or a sulfur atom, 35 RD 0 O ' II II -N-, -CNH- or -CO-; 40 D represents 0 OH 0 II I II 45 NHC-, -CH- or -C- ; R1 and R2 each independently represent a hydrogen atom, a lower alkyloxycarbonyl (Ci -5 alkyl) group, an unsaturated lower (C2 or C3) alkyl group or a lower (C1-5) alkyl group, any one of the hydrogen atoms of 50 said alkyl groups may be substituted by a group selected from the group consisting of a hydroxy group; a lower monoalkylamino (C1 or C2) group; a lower dialkylamino (C1 or C2) group; a lower alkyloxy group; a lower alkanoyloxy group; a benzoyloxy (C1-C5) group; a benzoyloxy group substituted by a halogen atom or a lower (C1-5) alkyloxy group; a phenyl group; a phenyl group substituted by a halogen atom or a lower (C1-5) alkyloxy group; and a lower alkyloxycarbonyl group (with C1-5 alkyl), or R1 and R2 may be so linked 55 as to form an ethylene or propylene chain and thus form a heterocyclic structure; R3 and R+ each independently represent a hydrogen atom or a lower (C1-5) alkyl group; X1 and X2 each independently represent a hydrogen atom, -CO-R6, a halogen atom, a lower (C1-5)
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