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United States Patent Office 3,836,671 Patented Sept. 17, 1974 United States Patent Office 2 A suitable value for R1 is, for example, alkyl or hy 3,836,671 droxyalkyl each of 3, 4 or 5 carbon atoms, which prefer ALKANOLAMINE DERVATIVES FOR PRODUC ING g-ADRENERGIC BLOCKADE ably is branched at the cy-carbon atom, for example iso Arthur Michael Barrett, Leeds, and John Carter, Roy propyl, S-butyl, t-butyl, 2-hydroxy-1,1-dimethylethyl or Hull, David James Le Count, and Christopher John 5 2-hydroxy-1-methylethyl. Particularly preferred values for Squire, Macclesfield, England, assignors to imperial Rare isopropyl and t-butyl. Chemical Industries Limited, London, England A suitable value for R is for example, acetyl, propi No Drawing. Continuation-in-part of application Ser. No. onyl, methoxycarbonyl, ethoxycarbonyl, cyano, carbam 9,451, Feb. 6, 1970, now Patent No. 3,663,607, which Oyl, carbazoyl, methylcarbamoyl, isopropylcarbamoyl, n is a continuation-in-part of abandoned application Ser. butylcarbamoyl or allylcarbamoyl. No. 199,011, Nov. 5, 1971. This application Mar. 10, A suitable value for A is, for example, methylene, 1972, Ser. No. 233,781 ethylene, ethylidene Claims priority, application Great Britain, Nov. 19, 1970, 55,028/70; Nov. 18, 1971, 53,544/71; Sept. 24, 1969, GH, 47,048/69; Feb. 21, 1969, 9,445/69 -C- int. C. A6k 27/00 trimethylene or vinylene. U.S. C. 424-324 5 Claims A suitable value for R3 is, for example, hydrogen, fluorine, chlorine, bromine, iodine, nitro, hydroxy, cy ABSTRACT OF THE DISCLOSURE ano, phenyl, phenoxy, benzyl, o-phenylethyl, benzyloxy, 1-(electronegatively - substituted - alkyl- or alkenyl 20 cyclopropyl, cyclobutyl, cyclopentyl, methyl, n-propyl, s phenoxy)-3-alkylamino-2-propanol derivatives, for exam butyl, allyl, acetyl, propionyl, methoxycarbonyl, ethoxy ple 1-p-carbamoylmethylphenoxy-3-isopropylamino-2-pro carbonyl, methylthio, methoxy, isopropoxy, allyloxy, hy panol and pharmaceutical compositions containing them droxymethyl, methoxymethyl or trifluoromethyl. possess (3-adrenergic blocking activity and are useful in Suitable non-toxic, pharmaceutically-acceptable acid the treatment of heart diseases and other complaints in 25 addition salts of the alkanolamine derivatives of the invention are, for example, salts derived from inorganic al acids, for example hydrochlorides, hydrobromides, phos This application is a continuation-in-part of Applica phates or Sulphates, or salts derived from organic acids, tions Ser. No. 9,451 (now Pat. No. 3,663,607) and for example oxalates, lactates, tartrates, acetates, salic Ser. No. 199,011, now abandoned. 30 ylates, citrates, benzoates, 3-naphthoates, adipates or 1,1- This invention relates to new alkanolamine derivatives methylene - bis-(2 - hydroxy - 3 - naphthoates), or salts which possess (3-adrenergic blocking activity. derived from acidic synthetic resins, for example sulpho According to the invention there is provided a new nated polystyrene resins, for example "Zeo-Karb' 225 alkanolamine derivative selected from compounds of (Zeo-Karb' is a trademark). 35 One preferred alkanolamine derivative of the inven the formula: tion is selected from compounds of the formula: R2-A. -OCH. CHOH.CHNHRi v-O- CH-CHOH.CHNHR1 40 (R3)n wherein R, R2, A and R3 have the meanings stated wherein above, and the non-toxic, pharmaceutically-acceptable R1 is alkyl or hydroxyalkyl each of up to 6 carbon atoms; acid-addition saits thereof. A particularly preferred de wherein either: rivative is selected from compounds of the latter formula A is alkylene of 1 to 5 carbon atoms and R is given above wherein R is isopropyl or t-butyl and where alkanoyl of up to 6 carbon atoms, carbamoyl or in either carbazoyl, or alkylcarbamoyl or alkenylcarbamoyl (a) R' is carbamoyl or alkylcarbamoyl of up to each of up to 7 carbon atoms; or 4 carbon atoms, A is methylene and R3 is hydrogen, A is alkenylene of 2 to 5 carbon atoms and R is halogen or alkyl, alkenyl or alkoxy each of up to 4 alkanoyl or alkoxycarbonyl each of up to 6 car carbon atoms; or bon atoms, cyano, carbamoyl or carbazoyl, or al (b) R is acetyl or carbamoyl, A is ethylene or vinylene kylcarbamoyl or alkenylcarbamoyl each of up to and R is alkoxy of up to 4 carbon atoms; or 7 carbon atoms; (c) R' is cyano, A is vinylene and R3 is alkoxy of up wherein n is the integer 1 or 2; and wherein R, the to 4 carbon atoms; values of which may be the same or different when in 55 is 2, is selected from hydrogen, halogen, nitro, hy and the non-toxic, pharmaceutically-acceptable acid-addi droxy, cyano, phenyl, phenoxy, benzyl, o-phenylethyl, tion salts thereof. benzyloxy, cycloalkyl of up to 8 carbon atoms, alkyl, A second preferred alkanolamine derivative of the alkenyl, alkanoyl and alkoxycarbonyl each of up to 6 invention is selected from compounds of the formula: carbon atoms, alkylthio, alkoxy and alkenyloxy each 60 of up to 5 carbon atoms, and alkyl of up to 5 carbon atoms which is substituted by hydroxy, alkoxy of up { X-0 CH.CHOH.CHNHR1 to 4 carbon atoms or halogen; A-R and the non-toxic, pharmaceutically-acceptable acid-addi wherein R and R2 have the meanings stated above and tion salts thereof. 65 wherein A is alkenylene of 2 to 5 carbon atoms, and the It is to be understood that the above definition of non-toxic pharmaceutically-acceptable acid-addition salts alkanolamine derivatives encompasses all possible stereo thereof. A particularly preferred derivative is selected from isomers thereof, and mixtures thereof, which possess (3- compounds of the last-mentioned formula given above adrenergic blocking activity, and in particular it encom wherein R is isopropyl or t-butyl, R is cyano or carbam passes racemic mixtures and any optical isomer which oyl and A is vinylene, and the non-toxic pharmaceuti possesses (3-adrenergic blocking activity. cally-acceptable acid-addition salts thereof. 3,836,671 3 4. Specific alkanolamine derivatives of the invention are, wherein R2, A, R3 and in have the meanings stated above, for example, those hereinafter described in the Examples. and wherein X stands for the group Of these, particularly active compounds are 1-p-carbamoylmethylphenoxy-3-isopropylamino-2-pro / o, panol; -CI-CI 1-p-(N-isopropylcarbamoylmethyl)phenoxy-3-isopropyl amino-2-propanol; or the group -CHOH.CHY, wherein Y stands for a 1-(2-bromo-4-carbamoylmethylphenoxy)-3-isopropyl halogen atom, or of mixtures of such compounds wherein amino-2-propanol; X has both meanings stated above, with an amine of the 1-p-carbamoylmethylphenoxy-3-t-butylamino-2-propanol; O formula NH2R, wherein R has the meaning stated above. 1-m-carbamoylmethylphenoxy-3-isopropylamino-2-pro A suitable value for Y is, for example, the chlorine or panol; bromine atom. The reaction may be carried out at ambient 1-(2-allyl-4-carbamoylmethylphenoxy)-3-isopropylamino temperature or it may be accelerated or completed by the 2-propanol; application of heat, for example by heating to a tempera 1-(4-carbamoylmethyl-2-methoxyphenoxy)-3-isopropyl ture of 90-110° C.; it may be carried out at atmospheric amino-2-propanol; or at an elevated pressure, for example by heating in a 1-p-(N-methylcarbamoylmethyl)phenoxy-3-isopropyl sealed vessel; and it may be carried out in an inert diluent amino-2-propanol; or solvent, for example methanol or ethanol, or an excess 1-(4-carbamoylmethyl-2-iodophenoxy)-3-isopropylamino of the amine of the formula NH2R, wherein R has the 2-propanol; meaning stated above, may be used as diluent or solvent. 1-(2-chloro-4-carbamoylmethylphenoxy)-3-isopropyl The starting material used in the above process may be amino-2-propanol; obtained by the reaction of the corresponding phenol with 1-(2-chloro-4-carbamoylmethylphenoxy)-3-t-butylamino an epihalohydrin, for example epichlorohydrin. The said 2-propanol; starting material may be isolated or it may be prepared 1-(2-fluoro-4-carbamoylmethylphenoxy)-3-isopropyl 25 and used in situ without isolation. amino-2-propanol; The alkanolamine derivatives of the invention in free 1-(2-fluoro-4-carbamoylmethylphenoxy)-3-t-butylamino base form may be converted into non-toxic, pharmaceuti 2-propanol; cally-acceptable acid-addition salts thereof by reaction 1-(4-carbamoylmethyl-2-methylphenoxy)-3-isopropyl with a suitable acid by conventional means. amino-2-propanol; 30 As stated above, the alkanolamine derivatives of the 1-(4-carbamoylmethyl-2-n-propylphenoxy)-3-isopropyl invention and the non-toxic, pharmaceutically-acceptable amino-2-propanol; acid-addition salts thereof possess 6-adrenergic blocking 1-(4-carbamoylmethyl-2-s-butylphenoxy)-3-isopropyl activity. Furthermore, many of these compounds possess amino-2-propanol; selective 6-adrenergic blocking activity. Compounds ex 1-(4-carbamoylmethyl-2-methoxyphenoxy)-3-t-butyl hibiting this selective action show a greater degree of amino-2-propanol; specificity in blocking the cardiac 3-receptors than the 6 1-(4-N-methylcarbamoylmethyl-2-n-propylphenoxy)-3- receptors in peripheral blood vessels and bronchial muscle. isopropylamino-2-propanol; Thus, a dose may be selected for such a compound at 1-(2-allyl-4-N-methylcarbamoylmethylphenoxy)-3-iso which the compound blocks the cardiac inotropic and propylamino-2-propanol; 40 chronotropic actions of a catecholamine for example iso 1-(2-allyl-4-N-methylcarbamoylmethylphenoxy)-3-t- prenaline, that is, 1-(3,4-dihydroxyphenyl)-2-isopropyl butylamino-2-propanol; aminoethanol but does not block the relaxation of tra 1-(4-carbamoylmethyl-2,5-dimethylphenoxy)-3-isopro cheal smooth muscle produced by isoprenaline or the pe pylamino-2-propanol; ripheral
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