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Ethylamine Derivatives and Their Use As Antihypertensive Agents

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Ethylamine Derivatives and Their Use As Antihypertensive Agents Europaisches Patentamt European Patent Office (fl) Publication number: 0 294 183 Office europeen des brevets A1 ® EUROPEAN PATENT APPLICATION @ Application number: 88305012.2 ® int. a*: C 07 D 211/32 C 07 D 211/22, @ Date of filing: 01.06.88 C 07 D 211/18, C 07 D 285/24, C 07 D 401/06, A 61 K 31/445, A 61 K 31/54 (So) Priority: 02.06.87 JP 138405/87 Toyota, Kozo No. 1-1 Suzuki-cho Kawasaki-ku @ Date of publication of application : Kawasaki-shi Kanagawa-ken (JP) 07.12.88 Bulletin 88/49 Yoshimoto, Ryota No. 1-1 Suzuki-cho Kawasaki-ku @ Designated Contracting States: Kawasaki-shi Kanagawa-ken (JP) CH DE FR GB IT LI Koyama, Yosikatsu @ Applicant: AJINOMOTO CO., INC. No. 1-1 Suzuki-cho Kawasaki-ku 5-8, Kyobashi 1-chome, Chuo-ku Kawasaki-shi Kanagawa-ken (JP) Tokyo 104 (JP) Domoto, Hideki No. 1-1 Suzuki-cho Kawasaki-ku @ Inventor: Syoji, Masataka Kawasaki-shi Kanagawa-ken (JP) No. 1-1 Suzuki-cho Kawasaki-ku Kawasaki-shi Kanagawa-ken (JP) Kamimura, Akira No. 1-1 Suzuki-cho Kawasaki-ku Eguchi, Chikahiko Kawasaki-shi Kahagawa-ken (JP) No. 1-1 Suzuki-cho Kawasaki-ku Kawasaki-shi Kanagawa-ken (JP) Representative: Armitage, Ian Michael et al MEWBURN ELLIS & CO. 2/3 Cursitor Street London EC4A1BQ (GB) (54) Ethylamine derivatives and their use as antihypertensive agents. @ Novel ethylamine derivatives of the formula (I) and salts thereof are useful as antihypertensive agents. Q-X N CH2CH2-A-B (I) \ / CH^ CO 00 wherein A is a linking group wherein the linkage is formed by a carbon or nitrogen atom; B is an aryl-containing group; C is O) hydrogen or optionally substituted alkyl, aralkyl or aryl, or C may CM be bonded to A to form an optionally substituted alkylene bridge; Q is an aryl- or heterocyclic aryl-containing group; X is a linking group wherein the linkage is formed by optionally CL substituted alkylene having from 2 to 20 carbon atoms and/or HI one or more hetero atoms selected from nitrogen and sulfur. Bundesdruckerei Berlin 0 294183 Description ETHYLAMINE DERIVATIVES AND THEIR USE AS ANTIHYPERTENSIVE AGENTS The present invention relates to new ethylamine derivatives and their use as an antihypertensive drug. Hypertension is a common complaint, whose frequency increases with age. In addition, hypertension is an 5 important factor in cerebral apoplexy and cardiopathy which are also frequent causes of death. Accordingly, an antihypertensive drug is considered to be one of the most important medicines for geriatric diseases. In 90% or more of hypertensive patients the cause of the hypertension is not clear, and patients are required to take an antihypertensive drug ali their lives, and therefore the antihypertensive drug has to have high safety and reliable pharmaceutical activity against hypertension, as well as being long-acting. 10 Recently, serotonin-antagonistic antihypertensives have been reported, which, however, are not always satisfactory in view of their antihypertensive mode of action and their short activity. Such medicines have been reported to be effective also against various diseases caused by serotonin, for example, thrombosis, ulcer and the like, but the effect against such diseases is not clearly established. On the other hand, many of such antihypertensives and their synthetic intermediates are rather insoluble in organic solvents or are produced by 15 complicated and troublesome procedures. The present invention provides ethylamine derivatives represented by the following formula. Such compounds in general exhibit antihypertensive activity and can be prepared simply and industrially advantageously. 20 c Q - X N - CHpCHp-A-B y 25 x CH2CH2 (I) In the above formula (I): 30 A is a linking group wherein the linkage is formed by a carbon or nitrogen atom; B is an aryl-containing group; C is hydrogen or optionally substituted alkyl, aralkyl or aryl, or C may be bonded to A to form an optionally substituted alkylene bridge; Q is an aryl- or heterocyclic aryl-containing group; X is a linking group wherein the linkage is formed by optionally substituted alkylene having from 2 to 20 carbon atoms and/or one or more hetero atoms selected from nitrogen and sulfur. 35 For example the structure represented by Q in the formula includes any one of the following: z' z' H z> . 7* Z* (5) (P) (II) (J.) 50 55 CSL) (H) wherein E is a nitrogen atom, -NH or substituted -NH, an oxygen atom or a sulfur atom; Y, Z1, Z2, Z3 and Z4 are 60 independently selected from hydrogen, optionally substituted alkyl, aralkyl or aryl ; Y may optionally be bonded to X to provide a linking group in which the linkage is formed by an optionally substituted alkylene bridge and/or at least one oxygen, sulfur or nitrogen atom; and Z1 and Z2, Z2 and Z3, or Z3 and Z4 may optionally be bonded to each other to provide a linking group in which the linkage is formed by an optionally substituted 2 0 294183 alkylene bridge and/or at least one oxygen, sulfur or nitrogen atom. Specific examples of the substituent Q are given in the appended claims. In the formula (I), for example: B may represent an optionally substituted aralkyl or aryl group having from 6 to 16 carbon atoms; and C may represent hydrogen or an optionally substituted alkyl group having from 1 to 6 carbon atoms,' or C 5 may be bonded to A to form an optionally substituted alkylene bridge having from 1 to 6 carbon atoms. Further preferable structure represented by C is hydrogen, methyl, ethyl, propyl, butyl, pentyl or hexyl, or when bonded to A, methylene, ethylene or propylene. The structure as represented by >A-B in the formula includes, for example, the following: 10 15 20 25 30 ?5 10 '5 0 5 0 0 294 183 0 294 183 7 N-CH CH-O R ,0 KJ 75 V 20 25 30 in the above formulae it will be seen for example that A is typically > CH-, > C = , or > N-, or even > C(CN)-, in which one of the bonds shown may be linked to the group C in Formula I, or may carry hydrogen or a 35 substituent. B, on the other hand, can be regarded as optionally substituted aryl or aralkyl, which can be linked to A through a substituent such as sulfonyl or carbonyl. Examples of the linking group X are selected from the following (Vlll-X): 40 S(CH2)n- - C(CH2)n- is 45 (VIII) (IX) (X) 50 wherein, n represents an integer from 0 to 9; Z4 and Z5 are independently hydrogen, or alkyl or aralkyl optionally substituted by one or more hetero atoms and/or by one or more substituents optionally containing one or more hetero atoms. Further examples of the group X are selected from the following (XI-XIII): 55 <0 5 ) 294 183 z5 i _ -S02N- -SCH2- -C-(CH2)n- k ' z6 (XI) (XII) (XIII) w wherein n respresents an integer from 0 to 9; Z5 is an alkyl group of from 1 to 20 carbon atoms, optionally substituted by one or more hetero atoms and/or by one or more substituents optionally containing one or more hetero atoms; and Z6 is hydrogen, cyano, amino, nitro, carboxyl, ester or aminocarbonyl. The ester of Z6 15 may for example be alkoxycarbonyl or alkoxysulfonyl. it will be apparent, therefore, that X can consist merely of an optionally substituted alkylene group (formulae X and XIII), or form a linkage solely through a nitrogen and/or sulfur atom (formulae VIII or XI), or a combination of these (formulae IX and XII). The ethylamine derivative of the present invention may be in the form of a salt thereof. 20 Of course, when the salt of the said derivative is incorporated into an antihypertensive medicament of the present invention, it should be in the form of a pharmaceutical^ acceptable salt. The ethylamine derivative of the present invention is advantageous as an antihypertensive for treating hypertensive mammals including humans. This can be administered perorally in the form of a tablet, capsule or elixir, or parenterally in the form of a sterile solution or suspension, for the purpose of reducing blood 25 pressure. The ethylamine derivative of the present invention can be administered to patients or animals which are to be treated generally several times each in a unit dosage of from 0.2 to 500 mg/patient or animal, and accordingly, the total dosage of the derivative may be from 1 to 2000 mg/patient or animal/day. Of course, the amount of the dosage may be varied in accordance with the condition of the disease, the weight of the patient or animal and other factors which are considered appropriate by one skilled in the art. 30 The ethylamine derivative of the present invention can also be used together with another antihypertensive agent. As examples of such agents which can be used together with the derivative of the invention, there may be mentioned ai -antagonists such as prazosin, a calcium-antagonist such as nifedipine, nicardipine, diltiagen and verapamil, or a convertase inhibitor such as captoril or enalapril. The above-mentioned typical combinations may be formulated as a pharmaceutical composition in 35 conventional manner. From about 0.2 to about 500 mg of the derivative of the present invention or a physiologically acceptable salt thereof or a mixture thereof is blended together with a physiologically acceptable vehicle, carrier, extender, binder, antiseptic, stabilizer, flavour and the like, in amounts as required for conventional pharmaceutical preparations. Examples of pharmaceutical additives to be used for preparation of tablets, capsules and the like are: 40 binders such as tragacanth, gum arabic, corn starch or gelatin; vehicles such as fine crystalline cellulose; extenders such as corn starch, pre-gelatinised starch or alginic acid; sweeteners such as sucrose, lactose or saccharin; flavours such as peppermint, an oil from Gaulthenia adenothrix Maxim or cherry.
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