NZ200659A

NZ200659A - Benzazepine derivatives and pharmaceutical compositions

Info

Publication number: NZ200659A
Application number: NZ200659A
Authority: NZ
Inventors: M Reiffen; J Heider; N Hauel; V Austel; W Eberlein; W Kobinger; C Lillie; K Knell; H Pieper; G Kruger; J Keck
Original assignee: Thomae Gmbh Dr K
Priority date: 1981-05-19
Filing date: 1982-05-18
Publication date: 1985-05-31
Also published as: KR890001544B1; JPH0136829B2; AU8379482A; UA8038A1; CS410291A3; NO159166C; ES517756A0; IL65814A0; IE53016B1; KR890001550B1; ES512285A0; JPS57193462A; ES517758A0; NO821645L; HU186584B; ZA823413B; AU551509B2; IL65814A; FI77856B; ES8308309A1

Description

<div class="application article clearfix" id="description"> New Zealand Paient Spedficaiion for Paient Number £00659 \ 2 006 5 9 Priority Date(s): P.7$!......... Complete Specification Ft Jed: Class: C°?&.f?.,.Ct7mK €m&5.. Aclk3f/55" * j MAV mm- Publication Date: ..... P. ). Ivy. IqqQ . P.O. Journal, Wo: . \^7P. Patents Form No.5 NEW ZEALAND PATENTS ACT 19 53 COMPLETE SPECIFICATION "CHEMICAL COMPOUNDS" -I-,WE DR. KARL THOMAE GESELLSCHAFT MIT BESCHRANKTER HAFTUNG, a Body corporate organised under the laws of the Federal Republic of Germany, of Biberach an der Riss, Federal Republic of Germany, hereby declare the invention, for which f/we pray that a patent may be granted to me/us, ,and the method by which it is to be performed, to be particularly described in and by the following statement:- -1- (followed by pa*® | A.) <* ft; 10, 15, 20. -1a - 200659 AK138-545 Chemical Compounds This invention relates to new benzazepine derivatives, to processes for their preparation and to pharmaceutical compositions containing them. Ntw Zealand Patent No. 1$S,081 , In/Dritioh P^feenfc 1,548,844,/ there is described, intier alia, the compound of formula OCH CH, , ^ CH-CH-CH-N-CH2-CH2 and pysiologically compatible acid addition salts thereof. These substances possess valuable pharmacological properties, i.e. not only a mild hypotensive effect, but more particularly a selective heart rate reducing effect. Surprisingly, we haye now found that compounds of general formula I E - W - G (I) wherein R^, Rj, R A, B, E and G are 3, ~6, as defined below, and physiologically compatible acid addition salts thereof have superior pharmacological properties, and in particular a more powerful heart rate reducing effect, with a longer duration of activity and reduced side-effects. Thus, according to one feature of the present C invention, there are provided compounds of general *' AN ,T* N - G (I) - 2 - n 0 S 5 9 [wherein A represents a group of formula -CH2-CH2~, h -CH=CH-, -NH-CO-, -CH2-CO- or -C=N- 5 5 5 (wherein represents an alkyl group containing 1 to 3 carbon atoms) and B represents a methylene or 5. carbonyl group, or A represents a -CO-CO- group and B represents a methylene group; E represents an ethylene, n-propylene or n-butylene group (optionally substituted by an alkyl group containing 1 to 3 carbon atoms), and n-propylene group substituted at the 2-position 10. by a hydroxy group or an n-butylene group substituted at the 2- or 3-position by a hydroxy group; G represents a methylene or ethylene group (optionally substitued by an alkyl group containing 1 to 3 carbon atoms); R^ and R2, which may be the same or different, each 15. represents a hydroxy group, an alkyl group containing 1 to 3 carbon atoms, or an alkoxy or phenylalkoxy group (in each of which the alkyl part may contain 1 to 3 carbon atoms) or one of the radicals R-^ or R2 represents a hydrogen atom or R^ and R2 together 20. represent an alkylenedioxy group containing 1 or 2 carbon atoms; R^ and R^ which may be the same or different, each represents a hydrogen or halogen atom, a hydroxy group, an alkyl or alkoxy group each of which may contain 1 to 4 carbon atoms, or a trifluoromethyl 25. or cyano group or one of the radicals R^ or R^ represents a nitro group or R^ and R^ together represent an alkylenedioxy group containing 1 or 2 carbon atoms; R^ represents a hydrogen atom, a hydroxy or amino group, an alkyl, alkoxy or alkylamino group containing 1 to 3 carbon 30. atoms, a dialkylamino, alkanoylamino, alkoxycarbonyl- amino or bis(alkoxycarbonyl)amino group, in each of which the alkyl part may contain from 1 to 3 carbon atoms, or a methylamino or ethylamino group substituted by a trifluoromethyl group; and Rg represents a hydrogen 35. atom, an alkyl group containing from 1 to 3 carbon atoms, or a phenylalkyl, alkanoyl or alkoxycarbonyl 2 HQS 59 - 3 - group, in each of which the alkyl part may contain from 1 to 3 carbon atoms, or an alkenyl group containing 3 to 5 carbon atoms] and acid addition salts thereof. It will be appreciated that, for pharmaceutical 5- use, the acid addition salts referred to above will be physiologically compatible acid addition salts, but other acid addition salts may find use, for example in the preparation of the compounds of general formula I and their physiologically compatible acid addition 10. salts. The term "acid addition salts" used herein includes salts formed with organic and inorganic acids. In the definition of the group A in general formula I above, the symbol '5' indicates the site of attachment to the phenyl nucleus. 15. Thus, in the compounds of formula I, R^ may, for example, represent a methyl, ethyl, propyl, isopropyl, hydroxy, methoxy, ethoxy, propoxy, isopropoxy, benzyloxy, 1-phenyl-ethoxy, 2-phenylethoxy or 3-phenylpropoxy group; R2 may, for example, represent a hydrogen atom 20. or a methyl, ethyl, propyl, isopropyl, hydroxy, methoxy, ethoxy, propoxy, isopropoxy, benzyloxy, 1-phenylethoxy, 2-phenylethoxy, 2-phenylpropoxy, or 3-phenylpropoxy group; R^ and R^, which may be the same or different, may, for example, each represent a hydrogen, fluorine, chlorine, bromine or iodine atom or a methyl, ethyl, propyl, isopropyl, n-butyl, hydroxy, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, trifluoromethyl or cyano group or one of the radicals R^ or R^ may represent a nitro group; R^ may, for example, represent a hydrogen 30. atom or a methyl, ethyl, propyl, isopropyl, hydroxy, methoxy, ethoxy, propoxy, isopropoxy, amino, methylamino, ethylamino, propylamino, isopropylamino, dimethylamino, diethylamino, dipropylamino, methyl — ethylamino, ethyl-propylamino, methyl-propylamino, formylamino, acetylamino, 35. propionylamino, methoxycarbonylamino, ethoxycarbonylamino, propoxycarbonylamino, isopropoxycarbonylamino, bis(ethoxy-carbonyl)-amino or 3»BrB-trifluoroethylamino group; Rg may, for example, represent a hydrogen atom or 25 ^ ^ ^ 5 - - 4 - a methyl, ethyl, propyl, isopropyl, benzyl, 1-phenylethyl 2-phenylethyl, 3-phenylpropyl, allyl, buten-2-yl, buten-3-yl, pentenyl, formyl, acetyl, propionyl, methoxy-carbonyl, ethoxycarbonyl, propoxycarbonyl or isopropoxy-carbonyl group; R^ and R2 together and/or R^ and R^ together may, for example, represent a methylenedioxy or ethylenedioxy group; E may, for example, represent an ethylene, n-propylene, n-butylene, 1-methyl-ethylene, 2-ethyl-ethylene, 1-propyl-ethylene, 1-methyl-n-propylene 2-methyl-n-propylene, 1-ethyl-n-propylene, 3-ethyl-n-propylene, 2-propyl-n-propylene, 2-methyl-n-butylene, 2-hydroxy-n-propylene, 2-hydroxy-n-butylene or 3-hydroxy-n-butylene group; and G may, for example, represent a methylene, ethylidene, propylidene, n-butylidene, 2-methyl-propylidene, ethylene, 1-methyl-ethylene, 2-ethyl-ethylene, 1-propyl-ethylene or 2-methyl-ethylene group. Preferred compounds of general formula I are those wherein A represents a group of formula -CH2-CH2-, -CH=CH-, ?H3 -NHCO-,-CH0-CO- or -C=N- 5 5 5 and B represents a methylene or carbonyl group or A represents a -CO-CO- group and B represents a methylen group, E represents an ethylene, n-propylene, n-butylene, 2-methyl-n-propylene or 2-hydroxy-n-propylene group, G represents a methylene, ethylene or 1-methyl-ethylene group, R^ represents a methyl, hydroxy or benxyloxy group or an alkoxy group containing 1 to 3 carbon atoms, R2 represents a hydrogen atom or a methyl, hydroxy or methoxy group, or R^ and R2 together represent a methylenedioxy group, R^ represents a hydrogen, fluorine, chlorine or bromine atom, a trifluoromethyl or nitro group or an alkyl or alkoxy group each containing 1 to 4 carbon atoms, - 5 - TL 0 0 5 9 R^represents a hydrogen, chlorine or bromine atom or a methyl, methoxy or cyano group or R^ and R^ together represent a methylenedioxy group, R^ represents a hydrogen atom or a hydroxy, methoxy, 5. amino, acetylamino, ethoxycarbonylamino, bis(ethoxy- carbonyl)-amino, dimethylamino or 3,$,3-trifluoroethyl-amino group and Rg represents a hydrogen atom, an alkyl group containing 1 to 3 carbon atoms or an allyl, benzyl, acetyl 10. or ethoxycarbonyl group. Particularly preferred compounds of general formula I are those wherein CH^ A represents a -CI^-CHj-, -CH=CH- or -C=N-group and 5 B represents carbonyl group, or A represents 15. a -CH=CH-, -NH-CO- or -CO-CO- 5 group and B represents a methylene group; E represents an n-propylene group; G represents an ethylene group; represents a methoxy or a hydroxy group; R2 represents a methoxy group; R^ represents a methoxy or trifluoromethyl 20. group, or a chlorine or bromine atom and R^ represents a methoxy group or a hydrogen, chlorine or bromine atom, or R^ and R^ together represent a methylenedioxy group; R^ represents a hydrogen atom or an amino or methoxy group; and R^ represents a hydrogen atom or 25. a methyl, ethyl, n-propyl or allyl group. Examples of particularly preferred compounds of general formula I include compounds of formula la R 2 2 2 ^ ^ ^ Rc ch-, I 3 wherein a represents a -cf^-c^-, -ch=ch- or —C=n-group and B represents a carbonyl group, or a represents 5. 10. 15. 20. ^& k - 6 - an -NH-CO- or -CO-CO- group and B represents a methylene 5 group; R-^ and R2 each represents a methoxy group; Rg represents a hydrogen atom or a methyl or allyl group; R3 represents a hydrogen atom or a methoxy group at the 3-position, and R^ represents a methoxy group at the 4-position, or R^ and R^ together represent a 3,4-methylenedioxy group; and R^ represents a hydrogen atom; or R^ at the 3-position represents a chlorine or bromine atom, R^ at the 5-position represents a chlorine or bromine atom, and R^ at the 4-position represents an amino group. The compounds of formula I may, for example, be prepared by the following processes, which processes constitute further features of the present invention: a) Reaction of a compound of general formula II R, A X (II) R ' 2 [wherein A and B are as hereinbefore defined and R^' and R2' each represent a hydroxy group protected by a protective radical (e.g. a trimethylsilyloxy, acetoxy, benzyloxy or tetrahydropyranyloxy group), or represent R^ and R2 as hereinbefore defined] with a compound of general formula III ^ , r6 3 Z-E-N-G_^ " (HI) V [wherein Rg, E and G are as hereinbefore defined R^', R^ and Rc>1 each represents a hydroxy group protected by a protective radical (e.g. a trimethylsilyloxy, acetoxy, benzyloxy or tetrahydropyranyloxy group) or represents R3, r4 and R5 as hereinbefore defined, and Z represents a nucleophilically exchangeable group such as a halogen atom or a sulfonyloxy group (e.g. a chlorine, bromine or iodine atom or a methanesulfonyloxy, p-toluenesulfonyloxy or ethoxysulfonyloxy group)], the corresponding internal quaternary salt of general formula Ilia (wherein E, G, Z, R^', **4'' Rs' an(^ are as hereinbefore defined) optionally being present in the reaction mixture, and optional subsequent cleavage of the protecting group. The reaction may optionally be carried out in a solvent or mixture of solvents, e.g. acetone, dimethyl-formamide, acetone/dimethylformamide, dimethylsulf-oxide or chlorobenzene, and depending on the reactivity of the radical Z, the reaction is conveniently carried out at temperatures between 0 and 150°C, preferably, however, at the boiling temperature of the solvent used. It is advantageous to carry out the reaction in the presence of an acid-binding agent, such as, for example, an alcoholate such as sodium methylate, an alkali metal hydroxide such as sodium hydroxide, an alkali metal carbonate such as potassium carbonate, an alkali metal amide such as sodamide, an alkali metal hydride such as sodium hydride or a tertiary organic base such as triethylamine or pyridine, or a reaction accelerator such as, for example, potassium iodide. The reaction may, hcwever, be carried out without a solvent. The cleavage of the protecting group, where present, is preferably carried out hydrolytically in an aqueous solvent, e.g. in water, isopropanol/water, 9 (Ilia) 4 r ' 5 - 8 - 006 5 9 tetrahydrofuran/water or dioxan/water, in the presence of an acid such as hydrochloric acid or sulfuric acid or in the presence of an alkali base such as sodium hydroxide or potassium hydroxide at temperatures between 5. 0 and 100°C, preferably at the boiling temperature of the reaction mixture. The cleavage of a benzyl radical, however, may be carried out hydrogenolytically, e.g. with hydrogen in the presence of a catalyst such as palladium/charcoal, in a solvent such as, for example, 10. methanol, ethanol, ethyl acetate or glacial acetic acid, optionally with addition of an acid such as hydrochloric acid at temperatures between 0 and 50°C (preferably room temperature) and a hydrogen pressure of 1 to 7 (preferably 3 to 5) bar. 15. b) For the preparation of compounds of general formula I wherein Rg represents a hydrogen atom, an alkenyl group containing 3 to 5 carbon atoms, an alkyl group containing 1 to 3 carbon atoms or a phenylalkyl group containing 1 to 3 carbon atoms in the alkyl part: 20. Reaction of a compound of general formula IV with a compound of general formula V C - V (V) wherein A, B, E and G are as hereinbefore defined 25. Rl'' R2'' R3'' R4* anc^ R5' eac^ represent a hydroxy group protected by a protective radical (e.g. a trimethyl-silyloxy, acetoxy, benzyloxy or tetrahydropyranyloxy - 9 - ^ I'Tt; - €*) group) or represent R^, R2, R-j, R^ and R5 as hereinbefore defined; one of the radicals U and V represents an Rg'-NH- group (wherein Rg' represents a hydrogen atom, an alkenyl group containing 3 to 5 carbon atoms, an 5. alkyl group containing 1 to 3 carbon atoms, or a phenylalkyl group containing 1 to 3 carbon atoms in the alkyl part), and the other of the radicals U and V represents a nucleophilically exhangeable group such as a halogen atom or a sulfonyloxy group, (e.g. a chlorine, bromine 10. or iodine atom or a methanesulfonyloxy, p-toluenesulfonyloxy or ethoxysulfonyloxy group); or the radical U together with a hydrogen atom at the 8-position of the radical E represents an oxygen atom and V represents an Rg,_ NH- group, wherein Rg' is as hereinbefore defined, 15. with optional subsequent cleavage of the protective radical, where present. The reaction is conveniently carried out in a solvent or mixture of solvents such as acetone, diethyl ether, methylformamide, dimethylformamide, 20 dimethylsulfoxide, benzene, chlorbenzene, tetrahydrofuran, benzene/tetrahydrofuran, dioxan or in an excess of the compounds of general formulae IV and/or V used, and optionally in the presence of an acid-binding agent (e.g. an alcoholate such as potassium tert.butylate, 3m an alkali metal hydroxide such as sodium or potassium hydroxide, an alkali metal carbonate such as potassium carbonate, an alkali metal amide such as sodamide, an alkali metal hydride such as sodium hydride, a tertiary organic base such as triethylamine or pyridine *0* whereby the last two may simultaneously serve as solvents) or a reaction accelerator such as potassium iodide, and, depending on the reactivity of the nucleophilically exchangeable group, the reaction may conveniently be carried out at temperatures from 0 to 150°C, preferably '5. 50 to 120°C, e.g. at the boiling temperature of the solvent used. However, the reaction may also be carried out without a solvent. It is, however, particularly advantageous to carry out the reaction in the presence - 10 - ? ^ n ^ 5 9 of a tertiary organic base or an excess of the amine of general formula V used. The optional subsequent cleavage of a used protective radical is preferably carried out hydrolytically in an aqueous solvent, e.g. in water, isopropanol/water, tetrahydrofuran/water or dioxan/water, in the presence of an acid such as hydrochloric acid or sulfuric acid or in the presence of an alkali base such as sodium hydroxide or potassium hydroxide at temperature between 0 and 100°C, preferably at the boiling temperature of the reaction mixture. The cleavage of a benzyl radical, however, may be carried out hydrogenolytically, e.g. with hydrogen in the presence of a catalyst such as palladium/charcoal, in a solvent such as methanol, ethanol, ethyl acetate or glacial acetic acid optionally with addition of an acid such as hydrochloric acid at temperatures between 0 and 50°C, preferably, however, at room temperature, and a hydrogen pressure of 1 to 7, preferably 3 to 5, bar. c) For the preparation of compounds of general formula 1 wherein Rg represents a hydrogen atom, an alkenyl group containing 3 to 5 carbon atoms, an alkyl group containing 1 to 3 carbon atoms or a phenylalkyl group containing 1 to 3 carbon atoms in the alkyl part: Reaction of a compound of general formula VI R a || ^ - E - H (VI) 2 (wherein A, B, E, R^ and R2 are as hereinbefore defined, expect that in the radical E two hydrogen atoms of a -CH2- or CH^- group are replaced by an oxygen atom) with an amine of general formula VII R. (VII) ^ ^ o ^ 5 ■ -11 - wherein G, R^, R^ and R^ are as hereinbefore defined and Rg' represents a hydrogen atom, an alkenyl group containing 3 to 5 carbon atoms, an alkyl group containing 1 to 3 carbon atoms or a phenylalkyl group containing 5. 1 to 3 carbon atoms in the alkyl part, in the presence of a reducing agent. The reaction is conveniently carried out in a solvent or mixture of solvents such as for example, methanol, ethanol, ethanol/ethyl acetate or dioxan 10. at temperatures between 0 and 100°C, preferably, however, at temperatures between 20 and 80°C. It is particularly advantageous to carry out the reductive animation in the presence of a complex metal hydride such as lithium or sodium cyanoborohydride 15. preferably at pH 6 - 7 and at room temperature, or, for the preparation of compounds of general formula I wherein Rg represents a hydrogen atom, in the presence of a hydrogenation catalyst, e.g. with hydrogen in the presence of palladium/charcoal at a hydrogen pressure 20. of 5 bar. By this means, optionally present benzyl groups may simultaneously be split off hydrogenolytically and/or double bonds may be hydrogenated. d) For the preparation of compounds of general formula I wherein Rg represents a hydrogen atom, an alkenyl 25. group containing 3 to 5 carbon atoms, an alkyl group containing 1 to 3 carbon atoms, or a phenylalkyl group containing 1 to 3 carbon atoms in the alkyl part: Reaction of a compound of general formula VIII ^ H (viii) II N - E - N N - E - N sS/ Jv / b R 2 30* (wherein A, B, E, R^ and R2 are as hereinbefore defined and Rg' represents a hydrogen atom, an alkenyl group containing 3 to 5 carbon atoms, an alkyl group containing 1 to 3 carbon atoms or a phenylalkyl group containing 1 to 3 carbon atoms in the alkyl part) with a compound '-~r - 12 - of general formula IX // H - G (IX) (wherein R^, R, R^ and G are as hereinbefore defined, 5. 10. 15. 20. 25. v3' 4' except that in the radical G two hydrogen atoms of a -CH2~ or CH^- group are replaced by an oxygen atom) in the presence of a reducing agent. The reaction is conveniently carried out in a solvent or mixture of solvents such as for example methanol, ethanol, ethanol/ethyl acetate or dioxan at temperatures between 0 and 100°C, preferably, however, at temperatures between 20 and 80°C. It is particularly advantageous to carry out the reductive amination in the presence of a complex metal hydride such as lithium or sodium cyanoborohydride preferably at pH 6 - 7 and at room temperature, or, for the preparation of compounds of general formula I wherein Rg represents a hydrogen atom, in the presence of a hydrogenation catalyst, e.g. with hydrogen in the presence of palladium/ charcoal at a hydrogen pressure of 5 bar. By this means, optionally present benzyl groups may simultaneously be split off hydrogenolytically and/or double bonds may be hydrogenated. e) For the preparation of compounds of general formula I wherein A represents a -NH-CO- group, E represents an ethylene, n-propylene or n-butylene group (optionally substituted by an alkyl group containing 1 to 3 carbon atoms) and Rg does not represent a hydrogen atom: Reaction of a compound of general formula X R, V I6 - N - G (X) - 13 - 7 0 06 5 9 (wherein B and G are as hereinbefore defined, E1 represents an ethylene, n-propylene or n-butylene group optionally substituted by an alkyl group containing 1 to 3 carbon atoms, 5. Ri'' R21' R3' anc^ R4' eac^ represents a hydroxy group protected by a protective radical (e.g. a trimethylsilyloxy, acetoxy, benzyloxy or tetrahydropyranyloxy group) or represent , Rj, R^ and R^ as hereinbefore defined, R^" represents a hydroxy, amino or alkylamino 10. group protected by a protective radical or has the meanings mentioned before for R^ with the exception of the amino or alkylamino group and Rg" has the meanings mentioned before for Rg with the exception of a hydrogen atom or represents a protective group for an amino 15. group) with a carbonic acid derivative of general formula XI W - CO - W (XI) [wherein W and W', which may be the same or different, each represent a nucleophilically exchangeable 20> group such as, for example, a chlorine or bromine atom, an alkoxy group containing 1 to 3 carbon atoms (optionally substitued by halogen atoms) or an imidazolyl-(2) group] with optional subsequent cleavage of a protective radical, where present. 25. The reaction is conveniently carried out in a solvent or mixture of solvents such as methylene chloride, carbon tetrachloride, benzene, tetrahydrofuran, benzene/tetrahydrofuran, dioxan or acetonitrile, conveniently at temperatures between 0 and 150°C, preferably, however, 30. at the boiling temperature of the solvent used (e.g. at temperatures between 40 and 100°C) and optionally in the presence of an acid-binding agent such as, for example, potassium carbonate, sodium hydroxide, potassium hydroxide, pyridine or triethylamine, whereby 35. the last two may simultaneously serve as solvents. However, the reaction may be carried out without a solvent. If in a used compound of general formula XI at least one of the radicals W and W' represents an alkoxy group containing 1 to 3 carbon atoms, the - 14 - reaction is preferably carried out in an excess of the ester as solvent. The optional subsequent cleavage of a protective radical is preferably carried out hydrolytically in 5. an aqueous solvent, e.g. water, isopropanol/water, tetrahydrofuran/water or dioxan/water, in the presence of an acid such as hydrochloric acid or sulfuric acid or sulfuric acid or in the presence of an alkali base such as sodium hydroxide or potassium hydroxide at 10. temperatures between 0 and 100°C, preferably at the boiling temperature of the reaction mixture. The cleavage of a benzyl radical, however, may be carried out hydrogenolytically, e.g. with hydrogen in the presence of a catalyst such as palladium/charcoal, 15. in a solvent such as, for example, methanol, ethanol, ethyl acetate or glacial acetic acid optionally with addition of an acid such as hydrochloric acid at temperatures between 0 and 50°C, preferably, however, at room temperature and a hydrogen pressure of 1 to 7, preferably 3 to 5, bar. 20 f) For the preparation of compounds of general formula I wherein A represents a -CH2~CH2- group, and R2 do not represent benzyloxy groups, R^ and R^ do not represent nitro groups and Rg does not represent a 25. benzyl group or an alkenyl group containing 3 to 5 carbon atoms: Hydrogenation of a compound of general formula XII R, (XII) wherein R^, R2, R3» R^, R^, B, E and G are as hereinbefore 30. defined, except that R^ or R^ may not represent a nitro group if R^ represents an amino group. 20. 25. 30. - 15 - /7 jyao The hydrogenation may be carried out in a solvent or mixture of solvents such as, for example methanol, ethanol, ethyl acetate or glacial acetic acid with catalytically activated hydrogen, e.g. with hydrogen in the presence of platinum or palladium/charcoal, at a hydrogen pressure of 1 to 7 , preferably 3 to 5, bar, and at temperatures between 0 and 75°C, preferably, however, at temperatures between 20 and 50°C. If in a compound of general formula XII Rg represents a benzyl group, this group may be replaced during the hydrogenation by a hydrogen atom, or if R1 and/or R2 represent a benzyloxy group, these radicals may each be replaced by a hydroxy group during the hydrogenation, g) Reaction of a compound of general formula XIII E—N (XIII) (wherein R^, R2, R^, R4» R5 to Rg, A, B, E and G are as hereinbefore defined, whereby, however, at least one of the radicals , R2, R^ and R^ must represent a hydroxy group or R^ represents a hydroxy group, an amino group or an alkylamino group containing 1 to 3 carbon atoms or Rg represents a hydrogen atom) with a compound of general formula XIV R8 - X (XIV) wherein Rg represents an alkyl group containing 1 to 3 carbon atoms or (if Rg represents a hydrogen atom) an alkenyl group containing 3 to 5 carbon atoms or (if R^ or R2 represent a hydroxy group and/or Rg represents a hydrogen atom) an alkyl group containing 1 to 3 carbon atoms substitued by a phenyl group, and X represents a nucleophilically exchangeable group such as a halogen atom or a sulfonyloxy group, e.g. a chlorine, bromine or iodine atom or a methanesulfonyloxy, p-toluenesulfonyloxy or methoxysulfonyloxy group; 7 0 0 5 9 ■I ( - 16 - or, if at least one of the radicals R^, Rj, R^, R4 and Rg represents a hydroxy group, X together with a hydrogen atom at the a-position of the radical Rg represents a diazo group, or also (if Rg represents a hydrogen atom or R^ represents an amino or alkylamino group) an oxygen atom. The reaction is conveniently carried out in a solvent or mixture of solvents such as diethyl ether, methanol, acetone, tetrahydrofuran, dioxan, acetonitrile, pyridine or dimethylformamide optionally in the presence of a base such as potassium carbonate, potassium hydroxide, potassium tert.butylate or sodium hydride at temperatures between 0 and 150°C, preferably, however, at temperatures between 20 and 120°C. If X represents a nucleophilically exchangeable group, the reaction is preferably carried out with an alkylating agent such as methyl iodide, dimethyl sulfate, ethyl iodide, diethyl sulfate, propyl bromide, allyl bromide, benzyl chloride, phenylethyl bromide or p-toluenesulfonic acid isopropyl ester in the presence of an acid-binding agent at temperatures between 20 and 80°C. The reaction may, however, be carried out without a solvent. If X together with the hydrogen atom at the a-position of the radical Rg represents a diazo group, the alkylation of a hydroxy group is preferably carried out with diazomethane or diazoethane at temperatures between 0 and 30°C, or if it represents an oxygen atom, the alkylation of a nitrogen atom may be carried out in the presence of a reducing agent at temperatures between 0 and 120°C, e.g. with formic acid at temperatures betwen 80° and 110°C or with sodium cyanoborohydride at room temperature and pH 6 - 7. h) For the preparation of compounds of general formula I wherein A does not represent a -CH=CH- group, R^ represents a chlorine or bromine atom and R^ represents an amino or alkylamino group: Halogenation of a compound of general formula XV "? a r< ^ * 25. (XV) wherein R^, R2, R^, Rg, B, E and G are as hereinbefore defined, A1 represents A as hereinbefore defined with the exception of a -CH=CH- group, and R^"" represents 5. an amino group or an alkylamino group containing 1 to 3 carbon atoms. The reaction is carried out with a halogenating agent, e.g. chlorine, bromine, tribromophenol/bromine or phenyl iodide dichloride, preferably in a solvent 10. or mixture of solvents, e.g. in 50 to 100% acetic acid or in tetrahydrofuran in the presence of a compound of a heavy metal such as mercuric oxide and conveniently at temperatures between 0 and 50°C. The compound of general formula XV may be used 15. either as a base or a salt (e.g. as its mono-, di-, or trihydrochloride). Conveniently 1 or 2 moles (or a slight excess) or halogenating agent per mole of compound of formula XV or its salt may be used. If a corresponding hydrogen halide salt is obtained 20. during the reaction, this may be directly isolated or, if desired, it may be further purified using a base. i) For the preparation of compounds of general formula I wherein A represents a -COCO- group, E represents an ethylene, n-propylene or n-butylene group (optionally substituted by an alkyl group containing 1 to 3 carbon atoms) and B represents a -CH2- group: Oxidation of a compound of general formula XVI (f*\ ^ /? r~- ^ -18- 10 20, 25. 30, R. wherein , R2, , (XVI) R. , Rr , R, and G are as hereinbefore 4' 5 6 defined, and E represents an ethylene, n-propylene or n-butylene group (optionally substituted by an alkyl group containing 1 to 3 carbon atoms). The oxidation is preferably carried out with an oxidizing agent such as potassium permanganate, selenium dioxide or sodium dichromate in a solvent or mixture of solvents such as, for example water, water/dioxan, glacial acetic acid, water/acetic acid or acetic anydride at temperatures between 0 and 100°C, preferably at temperatures between 20 and 80°C. If according to the invention a compound of general formula I is obtained wherein B represents a carbonyl group, this may, if desired, subsequently can be converted by reduction into a corresponding compound of general formula I wherein 3 represents a methylene group; and/or if a compound of general formula I is obtained wherein R7 A does not represent a -CH-CH- or -C=N- group and Rg represents a benzyl or 1-phenylethyl group, this may, if desired, subsequently be converted by catalytic hydrogenation into a corresponding compound of general formula I wherein Rg represents a hydrogen atom; and/or if a compound of general formula I is obtained wherein or R^ represents a nitro group, this may, if desired subsequently be converted by reduction into a corresponding .compound of general formula I wherein represents an amino group; and/or if a compound of general formula I wherein Rg represents a hydrogen atom and/or R^ represents an amino group is obtained, this may, if desired, subsequently be converted by acylation into a corresponding compound of general formula I wherein 7 'H 0 ^ - 19 - Rg represents an alkanoyl or alkoxycarbonyl group and/or Rg represents an alkanoylamino, alkoxycarbonylamino or bis(alkoxycarbonyl)amino group, wherein each alkyl part above may contain from 1 to 3 carbon atoms; and/or 5. if a compound of general formula I is obtained, wherein Rg represents an amino group, Rg does not represent a hydrogen atom, and neither R3 nor R4 represents a cyano group, this may, if desired, subsequently be converted via a corresponding diazonium salt into 10. a corresponding compound of general formula I wherein Rg represents a hydrogen atom, or a hydroxy or alkoxy group, or Rg represents a hydrogen atom and R^ represents a halogen atom or a cyano group. The subsequent reduction may preferably be carried 15. out with a metal hydride such as lithium aluminium hydride or diborane in a solvent such as, for example, diethyl ether, tetrahydrofuran or dioxan at temperatures between 0 and 100°C, preferably, however, at temperatures between 30 and 85°C. 20. The subsequent reduction or catalytic hydrogenation may be carried out in a solvent such as, for example, methanol, ethanol, ethyl acetate or glacial acetic acid with hydrogen in the presence of a catalyst such as platinum or palladium/charcoal at a hydrogen pressure 25. of 1 to 7, preferably 3 to 5, bar and at temperatures between 0 and 75°C, preferably 20 to 50°C. By this means, any nitro and cyano groups which are present may be simultaneously reduced. The subsequent acylation may be carried out 30. with, for example, acetyl chloride, acetic anhydride, propionic acid anhydride or a corresponding chloroformate, e.g. ethyl chlorformate, which simultaneously may serve as solvent, optionally in a solvent such as, for example, water/tetrahydrofuran, diethyl ether, 35. tetrahydrofuran or methylene chloride, optionally in the presence of a base such as triethylamine or pyridine, whereby a tertiary organic base simultaneously may serve as solvent, at temperatures between 0 and 100°C, preferably, however, at room temperature. - 20 - ^ -r-l q The reaction may, however, be carried out without a solvent. The subsequent reaction of a diazonium salt, e.g. of the fluoroborate, the hydrosulfate in sulfuric 5. acid, the hydrochloride or the hydroiodide, may be carried out, if desired, in the presence of copper or a corresponding copper (I) salt such as copper (I) chloride/hydrochloric acid, copper (I) bromide/hydro-bromic acid or trisodium copper (I) tetracyanide at 10. pH 7 at slightly elevated temperatures, e.g. at temperatures between 15 and 100°C; the subsequent reaction with hypophosphorous acid is preferably carried out at from -5 to 0°C. The diazonium salt necessary for this may be prepared in a solvent such as e.g. water-15. /hydrochloric aicd, methanol/hydrochloric acid, ethanol- /hydrochloric acid or dioxan/hydrochloric acid, by diazotization of a corresponding amino compound with a nitrite, e.g. sodium nitrite or an ester of nitrous acid, at lower temperatures, e.g. at temperatures 20. betweeen -10 and 5°C. Further, the compounds of formula I prepared as hereinbefore disclosed may optionally be converted with inorganic or organic acids into their physiologically compatible acid addition salts, for example by conventional 25. methods such as reacting the compounds as bases with a solution of the corresponding acids in a suitable solvent. /^\ ,/7 pro vl -21- Particularly preferred acids include, for example, hydrochloric, hydrobromic, sulfuric, phosphoric, acetic, lactic, citric, tartaric, succinic, maleic and fumaric acids. 5. The compounds of general formulae II to XVI used as starting materials are partly known from the literature, or may be obtained according to known processes. Thus, for example, compounds of general formulae 10. iv and VIII can be obtained, for example, by reaction of a corresponding benzazepine with a corresponding halogen compound and optional subsequent reaction with a corresponding amine. The benzazepine of general formula II necessary for this can be obtained, for 15. example, by cyclisation of an appropriate compound, e.g. by cyclisation of a compound of general formula XVII (XVIl) 5. 10. 15. 20. 25. 30. ^ 0 -22- or by ring closure of a corresponding o-amino compound and optional subsequent catalytic hydrogenation and/or reduction of the carbonyl group, for example with sodium borohydride/glacial acetic acid (see, for example, EP-A1 0.007.070) and/or oxidation, e.g. with selenium dioxide. Compounds of general formula VI can be obtained, for example, by reaction of a benzazepine with an appropriate halogen acetal and subsequent hydrolysis. Compounds of general formula X can be obtained, for example, by reduction of a corresponding nitro compound. Compounds of general formulae XII, XIII, XV or XVI can be obtained, for example by reaction of a halogen compound with an appropriate amine and optional subsequent cleavage of protective radicals, which are used for the protection of hydroxy groups. The compounds of general formula I and the physiologically compatible acid addition salts thereof with inorganic or organic acids possess valuable pharmacological properties, particularly a long-lasting heart rate-reducing effect, and a reduction in the Oj requirement of the heart, with only slight side-effects, e.g. only a slight antimuscarinic effect. For example the following compounds have been tested with regard to their biological properties: A = l-[7,8-Dimethoxy-l,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl]-3-[N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino]-propane dihydrochloride, B = l-[7,8-Dimethoxy-l,3-dihydro-2H-3-benzazepin-2-one-3-yl]-3-[N-methyl-N-(2-(3,4-dimethoxy-phenyl) -ethyl)-amino]-propane hydrochloride, C = l-[7,8-Dimethoxy-l,3,4,5-tetrahydro-2H-3-benzazepin-1,2-dion-3-yl]-3-[N-methyl-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino]-propane hydrochlor ide, 20. n n ft as ©) -23- D = 1—[7,8-Dimethoxy-l,3,4,5-tetrahydro-2H-l,3-benzo- diazepin-2-one-3-yl]-3-[N-methyl-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino]-propane, E = l-[7,8-Dimethoxy-l,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl]-3-[N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino]-propane hydrochloride, F = l-[7,8-Dimethoxy-l,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl]-3-[N-methyl-N-(2-(4-amino-3,5-dichloro-phenyl)-ethyl)-amino]-propane, G = l-[7,8-Dimethoxy-l,3-dihydro-2H-3-benzazepin- 2-one-3-yl]-3-[N-methyl-N-(2-(4-methoxy-phenyl)-ethyl)-amino]-propane hydrochloride, H = l-[7,8-Dimethoxy-l,3,4,5-tetrahydro-2H-3-benzazepin- 2-one-3-yl]-3-[N-methyl-N-(2-(4-methoxy-phenyl)-ethyl)-amino]-propane hydrochloride, I = 1-[7,8-Methylenedioxy-l,3,4,5-tetrahydro-2H- 3-benzazepin-2-one-3-yl]-3-[N-methyl-N-(2—(3,4— dimethoxy-phenyl)-ethyl-amino]-propane hydrochloride, J = l-[7,8-Dimethoxy-l,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl]-3-[N-allyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino]-propane hydrochloride and K = l-[7,8-Dimethoxy-l,3-dihydro-2H-3-benzazepin- 2-one-3-yl]-3-[N-methyl-N-(2-(3,4-methylenedioxy-phenyl)-ethyl)-amino]-propane hydrochloride, in comparison with L = l-[7,8-Dimethoxy-l,2,3,4-tetrahydro-5H-2-benzazepin-l-one-2-yl]-3-[N-methyl-N-(2-(3,4-dimethoxy-phenyl) -ethyl)-amino]-propane hydrochlor ide 1. Effect on heart rate in cats: r: @) -24- The effect of the test substances on the heart rate was investigated for each dose on 7 cats of both sexes, with an average weight of 2.5 to 3.5 kg. To do this, the cats were anaesthetised 5- with Nembutal (30 mg/kg i.p.) and chloralose urethane (40 mg/ml of chloralose + 200 mg/ml of urethane, as required). The substance to be tested was injected in aqueous solution into the vena saphena or into the duodenum. 10. The heart rate was recorded before and after the administration of the substance by means of a Grass tachograph from the electrocardiogram (taken from the chest wall) on a Grass polygraph. The results are shown in the following table: 15. 20. Substance Dose mg/kg Reduction in heart rate Half-life (minutes) A 1.0 i.v. - 55 % > 120 B 1.0 i.v. - 45 % > 120 C 1.0 i.v. - 44 % > 90 D 1.0 i.v. - 41 % 80 E 1.0 i.v. - 45 % > 90 F 1.0 i.v. - 51 % > 120 L 1.0 i.v. - 8.2 % 13 -25- 2 00^59 2. Effect on heart rate in guinea pig auricles: Isolated, spontaneously beating auricles from guinea pigs of both sexes, with a body weight of 300 to 400 g, were tested in tyrode solution in an organ bath. 5 The nutrient solution was supplied with Carbogen (95 % O2 + 5 % CO2) and kept at a constant temperature of 30°C. The contractions were recorded isometrically by means of a wire strain gauge on a Grass polygraph. The substances to be tested were added to the organ 10 baths in various concentrations. From the maximum effects, activity curves were prepared and from them the concentration which reduced the heart rate by 30% (= EC-603Q) was determined. 15 The results are shown in the following table: Substance EC-603q [pg/ml] A 0.030 C 0.097 D 0.058 E 0.066 F 0.014 G 0.014 H 0.0079 I 0.063 J 0.050 K 0.014 n o ^ ^ O ff - > C--'" / 3. Acute toxicity; The acute toxicity of the test substance was determined as a guide in mice (observation period: 14 days) after intravenous administration: Substance Toxicity (LD^q) 89 mg/kg i.v. 1,350 mg/kg p.o. The compounds of general formula I are suitable for the treatment of sinus tachycardia of various origins and for the prophylaxis and treatment of ischaemic cardiac diseases. According to a yet further feature of the present invention there are provided pharmaceutical compositions comprising, as active ingredient, at least one compound of general formula I as hereinbefore defined or a physiologically compatible acid addition salt thereof, in association with one or more pharmaceutical carriers or excipients. -27- 20VG59 For pharmaceutical administration the compounds of general formula I or their physiologically compatible acid addition salts may be incorporated into conventional preparations in either solid or liquid form, optionally in combination with other active ingredients. The compositions may, for example, be presented in a form suitable for oral, rectal or parenteral administration. Preferred forms include, for example, plain tablets, coated tablets, powders, suppositories, suspensions, drops, ampoules, capsules or syrups . The active ingredient may be incorporated in excipients customarily employed in pharmaceutical compositions such as, for example, corn starch, lactose, polyvinyl pyrrolidone, tartaric acid, magnesium stearate, cane sugar, citric acid, microcrystalline cellulose, aqueous or non-aqueous vehicles, fatty substances of animal or vegetable origin, paraffin derivatives, glycols, various wetting, dispersing or emulsifying agents and/or preservatives. Suitable dosages for adults are from 0.03 to 0.4 mg, preferably 0.07 to 0.25 mg, of active ingredient per kg of body weight, according to the invention. Such dosages may, for example, be administered 1 or 2 times daily. The total daily dosage may, however, be varied according to the compound used, the subject treated and the complaint concerned. ( 28 NOV 5984 ! \ - 28 - 200659 Advantageously the compositions may be formulated as dosage units, each dosage unit being adapted to supply a fixed dose of active ingredient. According to a still further feature of the 5. present invention there is provided a method of treating no*-human a^patient suffering from or susceptible to disorders of heart-rate, including sinus tachycardia and ischaemic cardiac diseases, which comprises administering to the said patient an effective amount of a compound 10. of formula I, as hereinbefore defined, or a physiolgically compatible acid addition salt thereof. The following non-limiting examples serve to illustrate the present invention. - 29 - 7. 0 0 5 Preparation of the starting compounds Example A 7,8-Dimethoxy-l,3-dihydro-2H-3-benzazepin-2-one a) 3,4-Dimethoxyphenylacetic acid chloride 5 600ml of thionyl chloride were added dropwise to a suspension of 549.4 g of 3,4-dimethoxyphenylacetic acid in 600ml of methylene chloride, with stirring, over a period of 2 hours. After the development of gas has ended (16 hours), the mixture was refluxed 10 for a further hour. After the volatile components have been eliminated, the residue was distilled in vacuo. Yield: 486 g (80.8 % of theory), Bp:13 4-136 °C/1.95 mbar 15 b) N- (2,2-dimethoxyethyl)-3,4-dimethoxyphenylacetamide Whilst cooling with ice, a solution of 485.2g of 3,4-dimethoxyphenylacetic acid chloride in 1.1 litres of methylene chloride at 15 to 20°C was added dropwise to a solution of 246.2 ml of aminoacetaldehyde dimethyl 20 acetal and 315 ml of triethylamine in 2.2 litres of methylene chloride and the mixture was stirred for one hour at 16 to 18°C. Then it was extracted with water several times, dried over magnesium sulphate and concentrated by evaporation. The oil obtained 25 slowly crystallised out. Yield: 608 g (95% of theory) Melting point: 66-69°C c) 7,8-Dimethoxy-l,3-dihydro-2H-3-benzazepin-2-one A solution of 600.6 g of N-(2,2-dimethoxyethyl)-3,4-30 dimethoxy-phenylacetamide in 3 litres of concentrated hydrochloric acid was mixed with 3 litres of glacial acetic acid. After standing for 17 hours at ambient temperature, the mixture was poured on to ice. The crystals precipitated were suction filtered, washed 35 with water until neutral and dried. Yield: 350 g (75.4% of theory) *700^ - 30 - * Melting point: 234-237°C Example B 7 ,8-Dimethoxy-lf3,4,5-tetrahydro-2H-3-benzazepin-2-one 5 A suspension of 21.9 g (0.1 mol) of 7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one and 1.5 g of 10% palladium/charcoal in 200 ml of glacial acetic acid was hydrogenated at 50°C and at a hydrogen pressure of 5 bar. After the catalyst had been filtered off, 10 the solvent was evaporated jLn vacuo and the residue was taken up in methylene chloride. After it has been extracted with sodium bicarbonate solution and washed with water, it was dried over magnesium sulphate, evaporated and purified over silica gel with methylene 15 chloride and then with increasing amounts of methanol (up to 10%). Yield: 12.6g (57% of theory) Melting point: 188-191°C Example C 20 7,8-Dimethoxy-2,3,4,5-tetrahydro-lH-3-benzazepine A solution of 1.8 g of glacial acetic acid in 10 ml of dioxan was added dropwise to a suspension of 1.3 g (6 mmol) of 7,8-dimethoxy-l,3,4,5-tetrahydro-2H-3-benzazepin-2-one and 1.1 g (3 mmol) of sodium 25 borohydride in 20 ml of dioxan, the mixture was refluxed for 3 hours, concentrated by evaporation and mixed with water. The mixture was extracted twice by shaking with methylene chloride, the extract was concentrated by evaporation and the residue taken up in ether. 30 After filtering, the ether was eliminated in vacuo. Yield: 1.1 g (92.7 % of theory) Melting point: 86-89°C. Example D N-[3-[N1-Methyl-N'-(2-(3,4-dimethoxy-phenyl)-ethyl)-35 amino]-propyl]-2-(2-amino-4,5-dimethoxy-phenyl)-acetamide 33.3g (0.07 mol) of N-[3-[N'-methyl-N'-(2-(3,4-dimethoxy- „ ^ ^ k Q, /'.-n - 31 - phenyl)-ethyl)-amino]-propyl]-2-(2-nitro-4,5-dimethoxy-phenyl)-acetamide, dissolved in 500 ml of methanol, were hydrogenated at 25°C and at a hydrogen pressure of 5 bar for 8 hours in the presence of 10% palladium/ 5 charcoal. After removal of the catalyst, the solvent was distilled off _in vacuo. Yield: 31.5g (100% of theory), viscous oil. Example E 6,9-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one 10 3 ml of polyphosphoric acid were poured on 2.0 g (0.007 mol) of N-(2,2-dimethoxyethyl)-2,5-dimethoxyphenyl acetamide and stirred for 60 minutes at 90°C. Subsequently the reaction mixture was mixed with ice water, the precipitated product was suction filtered and dried. 15 Yield: 0.98 g (64 % of theory), M.p.: 188 - 191°C. Example F 7.8-Dimethyl-1.3-dihvdro-2H-3-"benzazepin-2-one t Prepared analogously to Example E from N-(2,2-dimethoxy-20 ethyl)-3,4-dimethyl-phenylacetamide and polyphosphoric acid. Yield: 40.1 % of theory, M.p.: 220 - 224°C. " ? ^ ^ 5 9 _ 32 _ £ Example G 7,8-Dimethoxy-5-methyl-1,3-dihydro-314-benzodiazepin-2-one 19-5 g (0.082 mol) of 2-acetyl-4,5-dimethoxyphenylacetic acid were suspended in 200 ml of ethanol, mixed with 8.2 ml 5 of 98 % hydrazine hydrate and refluxed for 6 hours. The reaction mixture was evaporated in vacuo and purified over a silica gel column with methylene chloride and 1 % of ethanol as eluant. Yield: 9.6 g ( 50 % of theory), _ A 10 IR-spectrum (methylene chloride): 3300 cm" (NH) 2830 cm"1 (0CH3) 1650 cm"1 (CO) Example H 7.8-Dimethoxv-1,3.4,5-tetrahydro-2H-3-benzazepin-2.4-dione 15 a) 7.8-Dimethoxv-2-amino-4-bromo-1H-3-benzazepine-hydrobromide 3.7 g (0.017 mol) of 3,4-dimethoxy-o-phenylene-diaceto-nitrile were suspended in 10 ml of glacial acetic acid and mixed at 20°C with 12 ml of 30 ^ hydrobromic acid in glacial acetic acid. After stirring for 3 hours at room 15 temperature, the obtained precipitate was suction filtered, washed with glacial acetic acid and subsequently with acetone/ether and dried. Yield: 5.3 g (82.8 % of theory), M.p.: 210 - 211°C (decomp.). 20 b) 7,8-Dimethoxy-1,314,5-tetrahydro-2H-3-benzazepin-2,4-dione 5.3 g (0.014 mol) of 7,8-dimethoxy-2-amino-4-bromo-1H-3-benzazepine-hydrobromide were dissolved in 100 ml of water heated to 85°C, mixed with 1.3 g of anhydrous sodium acetate and heated for 1 hour up to 90°C. The reac-25 tion mixture was cooled, suction filtered, washed with cold water and dried. Yield: 2.9 g (88 % of theory), M.p.: 235°C (decomp.). 2 0 06 5 9 - 33 - Example I N-/3-(7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-vl)-propyl7methylamine hydrochloride Prepared analogously to Example B by catalytical hydrogenation of 1-/7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl7-3-(N-benzyl-methylamino)-propane. Yield: 87 % of theory, M.p.: 110°C (decomp.). Example J 1-Chioro-3-/N-methyl-N-(2-(3»4-dimethoxy-phenyl)-ethyl)-amino7propane a) 3-/N-Methyl-N-(2-(3,4-dimethoxy-phenyl)-ethylJ-amino/-propanol A mixture of 2.1 g (0.011 mol) of N-methyl-2-(3,4-di-methoxyphenyl)-ethyl-amine and 0.9 g (0.011 mol) of methyl acrylate was allowed to rest over night at room temperature. The addition product obtained hereby was dissolved in 40 ml of ether and added dropwise with stirring.within 15 minutes to a suspension of 0.3 g (0.008 mol) of lithium aluminium hydride in 20 ml of ether. After refluxing for 5 hours the reaction mixture was cooled and subsequently 30 ml of saturated aqueous sodium sulfate solution were dropped thereto. The precipitate obtained was suction filtered over kieselguhr and the filtrate was extracted with methylene chloride. The organic-phase was dried over sodium sulfate and evaporated to dryness. Yield: 3 g (89.7 % of theory), IR-spectrum (methylene chloride): 3600, 3230 cm 1 (OH) m/e = 253 (C14H23N03; 253.35). 2 0 f) Q b) 1-Chloro-3-/N-methyl-N-(2-(3»4-dimethoxy-phenyl)-ethyl)-amino7propane 2.75 g of benzenesulfonic acid chloride were added to 4 g of 3-/N-methyl-N-(2-(3,4-dimethoxyphenyl)-ethyl)-5 amino7propanol. After standing for 30 minutes the mixture was dissolved in methylene chloride, washed with 30 % sodium hydroxide solution and water, dried over sodium sulfate and evaporated in vacuo. After purifying over a silica gel column (eluant: methylene chloride/ 10 ethanol) a colourless oil was obtained. Yield: 1 g (17 % of theory), C14H22C1N02 (271.8) Calc.: C 61.86 H 8.15 N 5.15 Found: 62.00 8.00 4.63 15 Example K N-Methyl-N-/?-(3.4-dimethoxy-phenyl)-ethyl7acetidlnium-bromide 3 g (0.011 mol) of 3-/N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino7propanol were dissolved in 15 ml of methylene chloride and at 0 - 5°C a solution of 2 ml of phosphorus 20 tribromide in 5 ml of methylene chloride was dropped thereto. After heating to room temperature the reaction mixture was refluxed for 2 hours, evaporated to dryness, subsequently dissolved in methylene chloride, and washed with 2 n sodium hydroxide and water. The organic phase was dried over sodium 25 sulfate and evaporated to dryness. After purifying the crude product over a silica gel column (eluant: methylene chloride/ ethanol =100 : 5) the residue obtained was heated for 40 minutes up to 60 - 70°C. Yield: 1.8 g (48 % of theory), 30 M.p.: 175 - 180°C. 7 o * q Q • ' ---_f — ' J — ■ A boiling suspension of 0.8 g of lithium aluminium hydride in 100 ml of absolute dioxan was reacted with 2.2 g (0.01 mol) 5 of 7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one and subsequently refluxed for 3 hours. Ammonium chloride solution (10 90 was added whilst cooling with ice-water and the formed precipitate was suction filtered. The filtrate was evaporated in vacuo to a volume of approx. 20 ml, the obtained white preci-10 pitate was suction filtered and washed with little dioxan. Yield: 0.9 g (43.8 % of theory), M.p.: 162 - 163°C. ^ - 36 - Preparation of the end products Example 1 1~[7,8-Dimethoxy-l,3-dihydro-2H-3-benzazepin-2-on-3-yl]-3-[N-methyl-N-(2-(3, 4-dimethoxy-phenyl)-ethyl)-5 amino]-propane hydrochloride a) 1- (7,8-Dimethoxy-l,3-dihydro-2H-3-benzazepin- 2-on-3-yl)-3-chloropropane 131.5 g (0.6 mol) of 7,8-dimethoxy-l,3-dihydro-2H- 3-benzazepin-2-one were suspended in 900 ml of dimethyl-10 sulphoxide and mixed with 80.8 g (0.72 mol) of potassium tert.-butoxide, with stirring. After 10 minutes, the solution obtained was added dropwise, whilst being cooled with ice water, to 77 ml (0.72 mol) of l-bromo-3-chloropropane in 300 ml of dimethyl-15 sulphoxide. After one hour, the mixture was poured on to ice water. After a short time, the glutinous precipitate began to crystallize. The precipitate was suction filtered, dissolved in acetone, precipitated with water, then suction filtered and dried. 20 Yield: 155.5g (87.3% of theory) Melting point: 101-103°C b) 1—[7 r8-Dimethoxy-l,3-dihydro-2H-3-benzazepin-2-on-3-yl]-3-[N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino]-propane hydrochloride 25 5.9 g (0.02 mol) of 1-(7,8-dimethoxy-l,3-dihydro- 2H'-3-benzazepin-2-on-3-yl)-3-chloropropane and 11.7g (0.06 mol) of of N-methyl-2-(3,4-dimethoxy-phenyl)-ethylamine were heated to 100°C for 3 hours, then cooled and dissolved in ethyl acetate/water. The 30 organic phase was removed, washed three times with 1% acetic acid and extracted by shaking twice with 2N hydrochloric acid. The hydrochloric acid extract was made ammoniacal and extracted with methylene chloride. The solvent of the extract was removed 35 i_n vacuo, the residue was dissolved in acetone and the hydrochloride was precipitated out with ethereal hydrochloric acid. - 37 - 2 00659 Yield: 6.9 (70.3% of theory) Melting point: 190-191°C (decomp.) Example 2 1-[7,8-Dimethoxy-2,3,4,5-tetrahydro-lH-3,5-benzodiazepine-2,4-dion-3-yl]-3-[N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino]-propane hydrochlor ide 4.6 g (0.01 mol) of N-[3-[N'-methyl-N'-(2-(3,4-dimethoxy- phenyl) -ethyl)-amino]-propyl]-2-(2-amino-4,5-dimethoxy- phenyl ) -acetamide and 3.6 g (0.022 mol) of N,N'-carbonyl- diimidazole were boiled in 100 ml of acetonitrile for 33 hours. The solvent was removed i_n vacuo and the residue purified over alumina (Woelm N, Act. Ill) with methylene chloride and 15% acetone as eluant. The fractions were concentrated by evaporation in vacuo, the residue was dissolved in acetone and precipitated with ethereal hydrochloric acid. Yield: l.lg (21.7% of theory) Melting point: 125-130°C. Example 3 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(2-amino-3,5-dichloro-phenyl)-amino7-propane Prepared analogously to Example 1b by reaction of 1-(7,8-di-methoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl)-3-chloro-propane with N-/2-(2-amino-3,5-dichloro-phenyl)-ethyl7methylamine. Oil. UV-spectrum (ethanol): "X max 240 nm (0.34) 285 nm (0.14) 306 nm (0.10) IR-spectrum (dichloromethane): 2810cm"1 (N-alkyl) 2840 cm"1 (0-CH3) 1655 cm"1 (C=0) 1520 and 1620 cm"1 (C=C) - 38 - 200659 Example 4 1-[7,8-Dimethoxy-lf3,4,5-tetrahydro-2H-3-benzazepin- 2-one-3-yl]-3-[N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino] - propane dihydrochlor ide 5 5.8 g (0.0127 mol) of 1-[7 ,8-dimethoxy-l,3-dihydro-2H-3-benzazepin-2-one-3-yl ] -3- [N-methyl-N- (2- (3 , 4-d imethoxy-phenyl) -ethyl)-ami no] -propane , dissolved in 60 ml of glacial acetic acid, were hydrogenated for 5 hours at ambient temperature and at a hydrogen 10 pressure of 5 bar in the presence of 10% palladium/charcoal. The catalyst was filtered off, the filtrate was concentrated by evaporation _in vacuo and the residue taken up in methylene chloride/semisaturated potassium carbonate solution. The organic phase was treated with activated 15 charcoal/bleaching earth, filtered and evaporated in vacuo. Subsequently, the residue was dissolved in acetone and the dihydrochloride was precipitated with ethereal hydrochloric acid. Yield: 6.2 g (92 % of theory), 20 M.p.: 137°C (decomp.). When using an equimolar amount of ethanolic hydrochloric acid the hydrochloride was obtained having a melting point of 165 - 168°C. - 39 - ?. 0 0 6 5 Example 5 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(3»4-dimethoxy-phenyl)-ethyl)-amino7 propane dihydrochloride a) 1-(7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-vl)-3-chloro-propane Prepared analogously to Example 1a by reaction of 7,8-dimethoxy-l ,3,4,5-tetrahydro-2H-3-benzazepin-2-one with 1-bromo-3-chloropropane (yield: 50 % of theory) or analogously to Example 4 by catalytic hydrogenation of 1-(7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl)-3-chloro-propane (yield: 88 % of theory). M.p.: 84 - 85°C. b) 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(3»4-dimethoxy-phenyl)-ethyl)-amino7-propane dihydrochloride Prepared analogously to Example 1b by reaction of 1-(7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl)-3-chloro-propane with N-methyl-2-(3,4-dimethoxy-phenyl)-ethylamine. Yield: 75.2 % of theory, M.p.: 135 - 137°C (decomp.). > ■ -40- 2 0 0659 " ' Example 6 1—[7 , 8-Dimethoxy-2,3,4,5-tetrahydro-lH-3-benzazepin-3-yl]-3-[N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino]-propane dihydrochloride 5 2.7 g (6 mmol) of 1-[7,8-dimethoxy-l,3,A,5-tetrahydro-2H-3-benzazepin-2-one-3-yl]-3-[N-methyl-N- (2- (3, 4-dimethoxy-phenyl)-ethyl)-amino]-propane were dissolved in 100 ml of absolute ether and 100 ml of absolute tetrahydrofuran, then mixed with 0.25 g of lithium 10 aluminium hydride and refluxed for 3.5 hours. After cooling, a 10% ammonium chloride solution was added, whilst cooling was continued, then the mixture was suction filtered and the filtrate concentrated by evaporation. The residue was purified over a silica 15 gel column with methylene chloride. The fractions were concentrated by evaporation, the residue was dissolved in acetone and the dihydrochloride precipitated with methanolic hydrochloric acid. Yield: 1.5g (48.5% of theory), 20 Melting point: 270-271°C (decomp.). Example 7 1-/7>8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl7-3-/f?-methyl-N-(2-(4-methoxy-phenyl)-ethyl)-amino7propane hydrochloride 25 Prepared analogously to Example 1b by reaction of 1-(7,8-di-methox'y-l ,3-dihydro-2H-3-benzazepin-2-one-3-yl)-3-chloropropane with N-methyl-2-(4-methoxy-phenyl)-ethylamine. Yield: 76.2 % of theory, M.p.: 139 - 142°C. 7 o o ^ 5 9 - 41 - Example 8 1-/7,8-Dimethoxy-1, 3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(4-methoxy-phenyl)-ethyl)-amino7-propane hydrochloride Prepared analogously to Example 4 by catalytical hydrogenation of 1-/7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl.7- 3-/N-methyl-N-(2-(4-methoxy-phenyl)-ethyl)-amino7propane. Yield: 73.3 % of theory, M.p.: 175 - 177°C. Example 9 1-/7,8-Methylenedioxy-l,3-dihydro-2H-3-benzazepin-2-one-3-yl7- 3-/N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino7propane hydrochloride a) 1-(7,8-Methylenedioxy-l,3-dihydro-2H-benzazepin-2-one-3-yl)-3-chloro-propane Prepared analogously to Example 1a by reaction of 7,8-methylenedioxy-1,3-dihydro-2H-3-benzazepin-2-one (m.p.: 195°C (decomp.)) with 1-bromo-3-chloropropane. Yield: 72.1 % of theory, M.p.: 75 - 79°C. b) 1-/7,8-Methylenedioxy-l,3-dihydro-2H-3-benzazepin-2-one-3-yi7-3-/N-methyl-N-(2—(3,4-dimethoxy-phenyl)-ethyl)-amino7propane hydrochloride Prepared analogously to Example 1b by reaction of 1-(7,8-methylenedioxy-1,3-dihydro-2H-benzazepin-2-one-3-yl)-3-chloro-propane with N-methyl-2-(3,4-dimethoxy-phenyl)-ethylamine. Yield: 77.2 % of theory, M.p.: 185 - 187°C. Example 10 1-/7,8-Methylenedioxy-l,3,4,5-tetrahydro-2H-3-benzazepin- 2-one-3-yl7-3-/N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino7propane hydrochloride 5 Prepared analogously to Example 4 by catalytical hydrogenation of 1-/7,8-methylenedioxy-1,3-dihydro-2H-3-benzazepin- 2-one-3-yl7-3-/N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-aminojpropane. Yield: 77.3 % of theory, 10 M.p.: 210 - 212°C. Example 11 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one- 3-yl7-3-/N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino7-propane 15 0.05 ml of glacial acetic acid were added at room temperature to a mixture of 0.22 g (0.5 mmol) of 1-/7,8-dimethoxy-1,3,4,5- tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-(2-(3,4-dimethoxy- phenyl) -ethyl)-amino7propane, 0.5 ml of 37 % formalin solution, 2 ml of acetonitrile and 0.1 g of sodium cyanoborohydride. 20 After 2 hours, further 0.05 ml of glacial acetic acid were added and the mixture was stirred for 30 minutes. The further processing was carried out by evaporating, taking up in methylene chloride, washing in 2 n sodium hydroxide solution and water. The organic phase which was dried over sodium 25 sulfate was evaporated and purified over silica gel. Yield: 104 mg (45.5 % of theory), viscous oil, — 1 IR-spectrum (methylene chloride): 1645 cm (CO), 1510 cm 1 (aromatc C=C) M.p. of the dihydrochloride: 137°C (decomp.). Example 12 - 2 006 5 9 1-J7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino7-propane dihydrochloride 5 22 g (0.073 mol) of N-/3-(7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3~yl)-propyl7methylamine were heated with 7.2 g (0.036 mol) of 2-(3,4-dimethoxy-phenyl)-ethyl-chloride for 20 hours up to 140°C. After dissolving the reaction product in methylene chloride the solution was 10 washed twice with 2 n sodium hydroxide solution and twice with water, dried over sodium sulfate and evaporated. The residue was purified by chromatography on silica gel (corn size: 0.063 - 0.2 mm; eluant: methylene chloride/methanol = 10 : 1). The product thus obtained was dissolved in acetone 15 and the dihydrochloride was precipitated with ethereal hydrochloric acid. Yield: 8.0 g (45 % of theory), M.p.: 135 - 136°C (decomp.). Example 13 20 1-/7,8-Dimethoxy-1,3,4,5-tetrahyd^o-2H-3-benzazepin-2-one-3-yl7-3-/fr-methyl-N- (2-(4-acetylamino-3,5-dichloro-phenyl)-ethyl)-amino7propane 3 g (O.OO63 mol) of 1-/7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-,/N-methyl-N-(2-(4-amino-3,5-di-25 chloro-phenyl)-ethyl)-amino7propane in 50 ml of chloroform and 0.7 g (0.007 mol) of triethylamine were mixed «t boiling temperature in portions with altogether approx. 0.8 ml of acetyl chloride. After boiling for several hours, the reaction mixture was cooled to room temperature and washed 30 with water. The aqueous phase was made strongly alkaline by means of 2 n sodium hydroxide solution and extracted with methylene chloride. The separated organic phase was dried over sodium sulfate and evaporated. The crude product thus obtained was purified by chromatography on silica gel (corn 35 size: 0.063 - 0.2 mm, eluant: methylene chloride/ methanol = 8:1). M.p.: 144-146°c. - 44 - Example 14 2 006 1-/7»8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(4-amino-3,5-dibromo-phenyl)-ethyl)-amino7propane 5 0.8 g (0.005 mol) of bromine were dropped at room temperature with stirring to a solution of 1 g (0.0025 mol) of 1-/7,8-di-methoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(4-aminophenyl)-ethyl)-amino7propane in 20 ml of 95 % acetic acid. After approx. 60 minutes the solvent was 10 removed in a rotation evaporator and the residue was distributed between 2 n sodium hydroxide solution and methylene chloride. The methylene chloride phase was washed once with water, dried over sodium sulfate and evaporated in vacuo. The obtained oily residue crystallized at room temperature 15 and was recrystallized from absolute ethanol for further purification. M.p.: 105 - 110°C. Example 15 1-/?,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-20 3-yl7-3-/N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino7-propane 0.22 g (0.5 mmol) of 1-/7,8-dimethoxy-1,3,4,5-tetrahydro- 2H-3-benzazepin-2-one-3-yl7-3-\Z^-(2-(3,4-dimethoxy-phenyl)- ethyl)-amino7propane were heated with 0.2 ml of 37 ^ formalin 25 solution and 0.2 ml of 100 % formic acid for 20 minutes up to 90 - 100°C. The further processing was carried out analogously to Example 11. Viscous oil. — 1 IR-spectrum (methylene chloride): 1645 cm (CO), 1510 cm~1 (aromatic C=C) 30 M.p. of the dihydrochloride: 137°C (decomp.). Example 16 - 45 - 2 006 5 9 1-/7,8-Dimethoxy-1,3,4,5-tet^ahydro-2H-3-benzazepin-2-one-3-yl7~3-/N-methyl-N- (2-(3,4-dimethoxy-phenyl)-ethyl)-amino/-propane 5 1.26 g (20 mmol) of sodium cyanoborohydride were added to a solution of 3.29 g (10.0 mmol) of N-/3-(7,8-dimethoxy-1,3,4,5- tetrahydro-2H-3-benzazepin-2-one-3-yl)-propyl7methylamine- hydrochloride and 1.8 g (10.0 mmol) of 2-(3,4-dimethoxy-phenyl)- acetaldehyde in 40 ml of ethanol, whereby a pH-value of 6 - 7 10 was kept by the addition of 2 n hydrochloric acid, and stirring was continued for further 48 hours at room temperature. After evaporating the solution in vacuo, the residue was taken up in diluted hydrochloric acid and extracted twice with ether. Subsequently the aqueous phase was made alkaline, extrac- 15 ted thrice with methylene chloride, the organic phase was evaporated and purified over silica gel. Oil. — 1 IR-spectrum (methylene chloride): 1645 cm" (CO) _ A 1510 cm (aromatic C=C) M.p. of the dihydrochloride: 137°C (decomp.). 20 Example 17 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino7 -propane 1.26 g (20 mmol) of sodium cyanoborohydride were added to a 25 solution of 2.77 g (10 mmol) of 3-(7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl)-propionaldehyde and 1.95 g (10 mmol) of N-methyl-2-(3,4-dimethoxy-phenyl)-ethyl-amine in 40 ml of methanol, whereby a pH-value of 6 - 7 was adjusted by the addition of hydrochloric acid. At this pH-30 value the reaction mixture was stirred for 50 hours at room temperature. After evaporating the solution in vacuo, the - 46 - £ u y © ^ & residue was taken up in diluted hydrochloric acid and extracted thrice with ether. The aqueous phase was made alkaline, extracted thrice with methylene chloride, the organic phase was evaporated and purified over silica gel. Thereby a slight yellow, viscous oil was obtained. _ A IR-spectrum (methylene chloride): 1645 cm" (CO) _ A 1510 cm" (aromatic C=C) M.p. of the dihydrochloride: 137°C (decomp.). Example 18 1-/8-Methoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino/-propane dihydrochloride a) 1-(8-Methoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl)-3-chloro-propane Prepared analogously to Example 1a by reaction of 8-meth-oxy-1,3-dihydro-2H-3-benzazepin-2-one (m.p.: 189 - 190°C) with 1-bromo-3-chloropropane. Yield: 23 % of theory, IR-spectrum (methylene chloride): 1655 cm" (CO) b) 1-(8-Methoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-vl)-3-chloropropane Prepared analogously to Example 4 by catalytic hydrogenation of 1-(8-methoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl)-3-chloropropane. Yield: 67 % of theory, IR-spectrum (methylene chloride): 1645 cm (CO). c) 1-/^-Methoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino/-propane dihydrochloride Prepared analogously to Example 5b by reaction of 1 — (8— 200659 - 47 - methoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl)-3-chloropropane with N-methyl-2-(3,4-dimethoxy-phenyl)-ethylamine. Yield: 14 % of theory, 5 M.p.: 118 - 121°C. Example 19 1-Jj,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(4-amino-3-chloro-phenyl)-ethyl)-amino7-propane 10 Prepared analogously to Example 12 from N-/3-(7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl)-propyl7-methyl-amine and 2-(4-amino-3-chloro-phenyl)-ethylbromide. Oil. _ A IR-spectrum (methylene chloride): 3380, 3480 cm- (NH2) 1645 cm"1 (CO) 15 UV-spectrum (ethanol): max. 238 nm (0.16) 280 - 290 nm (0.05) Example 20 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-ethyl-N-(2-(4-amino-3»5-dichloro-phenyl)-ethyl)-20 amino7propane Prepared analogously to Example 12 from N-/3-(7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl)-propyl7-ethylamine and 2-(4-amino-3,5-dichloro-phenyl)-ethylchloride, Oil. _ A 25 IR-spectrum (methylene chloride): 3390, 3480 cm" (NH2) 1650 cm"2 (CO) UV-spectrum (ethanol): Ti max: 240 nm (0.13) 280 - 290 nm (0.05) Example 21 30 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(4-amino-3»5-dichloro-phenyl)-ethyl)-aminjp7propane 200 o - 48 - Prepared analogously to Example 12 from N-/3-(7,8-di-methoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl)-propyl7methylamine and 2-(4-amino-3,5-dichloro-phenyl)-ethylchloride. M.p.: 94 - 104°C. Example 22 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yi7-3-/N-methyl-N-(2-(4-amino-3,5-dibromo-phenyl)-ethyl)-amino7propane Prepared analogously to Example 12 from N-/3-(7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl)-propyl7methyl-amine and 2-(4-amino-3,5-dibromo-phenyl)-ethylchloride. M.p.: 108 - 112°C. Example 23 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yi7-3-/N-methyl-N-(2-(4-ethoxycarbonylamino-3,5-dichloro-phenyl)-ethyl)-amino7propane Prepared analogously to Example 13 from 1-/7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(4-amino-3,5-dichloro-phenyl)-ethyl)-amino7propane and ethyl chloroformate. Oil. IR-spe.ctrum (methylene chloride): 3410 cm (NH) 1650 cm"1 (CO-NC) 1735 cm"1 (C0-0-) 1800 cm"1 (C0-0-) UV-spectrum (ethanol): 'X max: 240 nm (shoulder, 0.08) 280 - 290 nm (0.03) - 49 - 2 0 06 5 Example 24 1-Jj,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl/-3-/N-methyl-N-(2-(4-bis-(ethoxycarbonyl)-amino-3,5-di-chlorophenyl)-ethyl)-amino7propane Prepared analogously to Example 13 from 1-/7,8-dimethoxy-1,3, 4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(4-amino-3,5-dichloro-phenyl)-ethyl)-amino/propane and ethyl chloroformate. Oil. _ A IR-spectrum (methylene chloride): 1650 cm" (CO-NC) 1730 cm"1 (C0-0-) 1760 cm"1 (C0-0-) 1800 cm"1 (C0-0-) UV-spectrum (ethanol): ^ max: 228 nm (shoulder, 0.15) 282 nm (0.03) Example 25 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl/-3-/N-methyl-N-(2-(4-ethoxycarbonylamino-3-cyano-5- fluoro-phenyl)-ethyl)-amino7propane Prepared analogously to Example 13 from 1 -D ,8-dimethoxy- 1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl/-3-/N-methyl- N-(2-(4-amino-3-cyano-5-fluoro-phenyl)-ethyl)-amino/-propane and ethyl chloroformate in the presence of triethylamine. — 1 IR-spectrum (methylene chloride): 3400 cm (NH) 2830 cm"1 (0CH3) 1730, 1650, 1510 cm"2 (CO) 9 0 0 - 50 - •' '' " 1 & Example 26 1-/7,8-Dimethoxy-1,3>4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N- (2- (4-dimethylamino-3,5-dichloro-phenyl)-ethyl)-amino7propane 5 Prepared analogously to Example 11 from 1-/7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(4-amino-3,5-dichloro-phenyl)-ethyl)-amino7propane, paraformaldehyde and sodium cyanoborohydride in methanol. Oil. — A 10 IR-spectrum (methylene chloride): 1650 cm" UV-spectrum (ethanol): ^ max: 227 nm (shoulder, 0.16) 280 nm (0.12) Example 27 1-/7,8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl.7-15 3-/N-methyl-N-(2-(4-amino-3,5-dichloro-phenyl)-ethyl)-amino7propane Prepared analogously to Example 1b from 1-(7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl)-3-chloro-propane and 2-(4-amino-3»5-dichloro-phenyl)-N-methyl-ethylamine. Oil, _ A 20 IR-spectrum (methylene chloride): 3390, 3480 cm" (NH2) 1655 cm"1 (CO) UV-spectrum (ethanol): ^ max: 238 nm (shoulder, 0.25) 280 nm (0.1) 303 nm (0.12) 25 Example 28 1-/7»8-Dimethoxy-l,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-vl7-3-/^-methyl-N-(2-(4-amino-3,5-dichloro-phenyl)-ethyl)-amino7propane 30 Prepared analogously to Example 4 from 1-/7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl,7-3-/N-methyl-N-(2-(4-amino-3,5-dichloro-phenyl)-ethyl)-amino7propane and - 51 - 200659 hydrogen in the presence of palladium/coal in glacial acetic acid. M.p.: 94 - 104°C. Example 29 5 1-/7, 8-Dimethoxy-1,3,4,5-tet^ahyd^o-2H-3-benzazepin-2-one-3-yl7-3-/N-ethyl-N- (2-(4-amino-3,5-dibromo-phenyl)-ethyl)-amino7propane Prepared analogously to Example 5b from 1-(7,8-dimethoxy-1 > 3»4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl)-3-chloro-10 propane and 2-(4-amino-3»5-dibromo-phenyl)-N-ethyl-ethyl-amine. Oil. IR-spectrum (methylene chloride): 3380, 3480 cm""1 (NH2) 1645 cm""1 (CO) UV-spectrum (ethanol): max: 240 nm (shoulder, 0.13) 15 280 - 290 nm (0.04) I Example 30 1-Jj,8-Dimethoxy-1,3»4,5-tetrahydro-2H-3-benzazepin-2-one-3-yi7-3-/N-methyl-N-(2-(4-amino-3»5-dichloro-phenyl)-ethyl)-aminoTpropane 20 Prepared analogously to Example 5b from 1-(7,8-dimethoxy-1,3 > 4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl)-3-chloropropane and 2-(4-amino-3,5-dichloro-phenyl)-N-methyl-ethyl-amine. M.p.: 94 - 104°C. 2 0 06 5 9 - 52 - Example 31 1-Jj,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-isopropyl-N-(2-(4-amino-3,5-dichloro-phenyl)-ethyl)-amino7propane Prepared analogously to Example 5b from 1-(7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl)-3-chloropropane and 2-(4-amino-3,5-dichloro-phenyl)-N-isopropyl-ethylamine. M.p. of the hydrochloride: 90°C (sintering from 70°C). — 1 IR-spectrum (methylene chloride): 3390, 3480 cm" (NH2) 1650 cm"1 (CO) UV-spectrum (ethanol): 'X max: 238 nm (0.13) 280 - 290 nm (0.05) Example 32 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yi7-3-/N-methyl-N-(1-methyl-2-(4-amino-3,5-dichloro-phenyl)-ethyl)-amino7propane hydrochloride Prepared analogously to Example 5b from 1-(7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl)-3-chloropropane and 2-(4-amino-3,5-dichloro-phenyl)-1-methyl-N-methyl-ethylamine. M.p.: 118 - 128°C (decomp.). Example 33 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-(2-(4-amino-3,5-dichloro-phenyl)-ethyl)-amino7-propane hydrochloride Prepared analogously to Example 5b from 1-(7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl)-3-chloro- - 53 - 2 00659 propane and 2-(4-amino-3,5-dichloro-phenyl)-ethylamine. M.p.: 236 - 241°C. Example 34 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin- 2-one-3-yl7-3-/N-methyl-N-(2-(4-amino-3-chloro-5-methyl-phenyl)-ethyl)-amino7propane Prepared analogously to Example 5b from 1-(7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl)-3-chloro-propane and 2-(4-amino-3-chloro-5-methyl-phenyl)-N-methyl-ethylamine. M.p.: 60°C (sintering, melting at 73°C). _ A IR-spectrum (methylene chloride): 3390, 3480 cm (N^) 1650 cm"1 (CO) UV-spectrum (ethanol): ^ max: 237 nm (0.14) 280-290 nm (0.05) Example 35 1-/7 ,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one- 3-y.l7-3-/N-methyl-N-(2-(3,5-dichloro-4-hydroxy-phenyl)-ethyl)-amino7propane hydrochloride Prepared analogously to Example 5b from 1-(7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl)-3-chloro-propane and 2-(3,5-dichloro-4-hydroxy-phenyl)-N-methyl-ethyl-amine. M.p.: 225°C. 20065 - 54 - Example 36 1-/7,8-Dimethoxy-l,3,4,5-tetrahyd^o-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N- (2- (3-chloro-5-fluoro-4-B,B, B -trifluoro-ethylaminophenyl)-ethyl)-amino7propane 5 Prepared analogously to Example 5b from 1-(7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl)-3-chloropropane and 2-(3-chloro-5-fluoro-4-B,B,B-trifluoroethyl-amino-phenyl)-N-methy1-ethylamine. m/e = 545/547 (C26H32C1FAN303; 546.03) 10 Example 37 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(4-amino-3-chloro-5-fluoro-phenyl)-ethyl)-amino7propane Prepared analogously to Example 5b from 1-(7,8-dimethoxy-15 1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl)-3-chloro-propane and 2-(4-amino-3-chloro-5-fluoro-phenyl)-N-methyl-ethylamine. m/e = 463/465 (C24H31C1FN303; 463.99) Example 38 20 1-/7,8-Dimethoxy-1,3,4,5-tetrahyd^o-2H-3-benzazepin-2-one-3-yl7-3-/N-Inethyl-N-(2-(4-amino-3-chlo^o-5-t^i^'luo^omethyl-phenyl)-ethyl)-amino7propane Prepared analogously to Example 5b from 1-(7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl)-3-chloro-25 propane and 2-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-N-methyl-ethylamine. Oil. - 55 - 2 0 06 5 9 _ A IR-spectrum (methylene chloride): 3410, 3510 cm" (NH2) 1650 cm"1 (CO) 1610, 1520 cm"1 (C=C) 2800 cm"1 (N-alkyl) 5 2830 cm"1 (0CH3) UV-spectrum (ethanol): A max: 241 nm (0.33) 285 nm (0.10) 310 nm (0.08) Example 39 10 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl,7-3-/N-methyl-N-(2-(4-amino-3-cyano-5-fluoro-phenyl)-ethyl)-amino7propane Prepared analogously to Example 5b from 1-(7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl)-3-chloro-15 propane and N-methyl-(2-(4-amino-3-cyano-5-fluoro-phenyl)-ethyl)-amine. — 1 IR-spectrum (methylene chloride): 3400, 3490 cm (NH2) 2830 cm"1 (0CH3) 2220 cm"1 (CN) 20 1650 cm"1 (CO) Example 40 1-/7,8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl7-3-/N-benzyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino/-propane hydrochloride . 25 Prepared analogously to Example 1b from 1-(7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl)-3-chloro-propane and 2-(3,4-dimethoxy-phenyl)-N-benzyl-ethylamine. Yield: 51 % of theory, M.p.: 102°C (decomp.). - 56 - Example 41 1-/7,8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(3,4-methylenedioxy-phenyl)-ethyl)-amino7- propane hydrochloride 5 Prepared analogously to Example 1b from 1-(7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl)-3-chloro-propane and 2-(3 ,4-methylenedioxy-phenyl)-N-methyl-ethylamine. Yield: 48 % of theory, M.p.: 160 - 162°C. 10 Example 42 1-/7,8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl7-3-(N-benzyl-methylamino)-propane hydrochloride Prepared analogously to Example 1b from 1-(7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl)-3-chloro-propane 15 and N-methyl-benzylamine. Yield: 92 % of theory, M.p.: 208 - 209°C. Example 43 1-/7,8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl7~ 20 4-/N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino7-butane hydrochloride Prepared analogously to Example 1b from 1-(7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-on-3-yl)-4-chloro-butane and N-methyl-2-(3,4-dimethoxy-phenyl)-ethylamine. 25 Yield: 85 % of theory, M.p.: 162 - 164°C. 200659 - 57 - Example 44 1-/5-Propoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl/- 2-/N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino/ -.ethane hydrochloride Prepared analogously to Example 1b from 1-(8-propoxy-1,3-di-hydro-2H-3-benzazepin-2-one-3-yl)-2-chloro-ethane and N-methyl-2-(3,4-dimethoxy-phenyl)-ethylamine. Yield: 31 % of theory, M.P.: 155 - 157°C. Example 45 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one- 3-yl/-4-/Ff-me thyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino/-butane hydrochloride Prepared analogously to Example 4 by catalytic hydrogenation of 1-/7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl7-4-/N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino/-butane. M.p.: 192 - 194°C. Example 46 1-/7 ,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yi/-3-/FT-methyl-N-(2-(3,4-methylenedioxy-phenyl)-ethyl)-amlno7-propane hydrochloride Prepared analogously to Example 4 by catalytic hydrogenation of 1-/7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(3,4-methylenedioxy-phenyl)-ethyl)-amino/-propane. Yield: 72 % of theory, M.p.: 191 - 193° C. - 58 - 2 0 06 5 9 Example 47 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-3-one-3-yl7-3-/N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino7propane hydrochloride Prepared analogously to Example 4 by catalytic hydrogenation of 1 -Z7.S -dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl7~3-/N-benzyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino/-propane. Yield: 81 % of theory, M.p.: 152 - 154°C. Example 48 1-Z7 ,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3- /N-allyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino7-propane hydrochloride 3.1 g (0.007 mol) of 1-/7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl/-3-/ft-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino/-propane were refluxed for 21 hours with 1.0 g (0.007 mol) of potassium carbonate and 0.6 ml (0.007 mol) of allyl bromide in 100 ml of chloroform. Subsequently the organic phase was extracted with water, dried, evaporated in vacuo and the residue obtained was purified over an aluminium oxide column (300 g, neutral, activity III) with methylene chloride containing 2 % of acetone as eluant. Subsequently the hydrochloride was precipitated. Yield: 40 % of theory, M.p.: 153 - 155°C. - 59 - 2 00659 Example 49 1-/7, 8-Dimeth.oxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-propyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino7-propane hydrochloride Prepared analogously to Example 48 from 1-/7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino7propane and 1-bromopropane. Yield: 53 % of theory, M.p.: 80°C (decomp.). Example 30 Mixture of isomers of 1 -D ,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl7-3-/n-methyl-N-(2-(2- and 4-nitro phenyl)-ethyl)-amino7propane Prepared analogously to Example 1b from 1-(7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl)-3-chloro-propane and N-methyl-2-(4- and 2-nitro-phenyl)-ethylamine. Yield: 70 % of theory, _ A IR-spectrum (methylene chloride): 1635 cm (CO) 1510 and 1345 cm"1 (N02) NMR-spectrum (CDCl^/DgO): Se 8.10 ppm, d(J=9Hz), 2H (aromat.), (4-nitro compound), S « 7.83 ppm, d(Je7Hz), 2H (aromat.), (2-nitro compound). 2 - 60 - Example 51 Mixture of isomers of 1 -ff, 8 -dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yi7-3-/N-methyl-N-(2-(2-amino-and 4-amino-phenyl)-ethyl)-amino7propane-hydrochloride 5 Prepared analogously to Example 4 by catalytic . reduction of a isomer mixture of 1-/7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(2- and 4-nitro-phenyl)-ethyl)-amino7propane. Yield: 34 % of theory, 10 M.p.: 100°C (decomp.) IR-spectrum (methylene chloride): 1660 cm*"1 (CO) C24H31N3°3 x HC1 (446.0) Calc.: C 64.34 H 7.65 N 9.38 CI 7.91 Found: 63.60 7.20 9.28 7.94 15 Example 52 1-/7,8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl7- 3-/fT-methyl-N- (2- (4-ac etylamino-phenyl) -ethyl) -amino7propane and 1-/7,8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl.7-20 3-/H-methyl-N-(2-(2-acetylamino-phenyl)-ethyl)-amino7propane 1.8 g (0.004 mol) of a isomer mixture of 1-/7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl7-3-/fi-methyl-N-(2-(2- and 4-amino-phenyl)-ethyl)-amino7propane were stirred at room temperature for 1 hour in a mixture of 10 ml of 25 glacial acetic acid and 10 ml of acetic anhydride. Subsequently water was added, the reaction mixture was neutralized with sodium bicarbonate and extracted with methylene chloride. The organic phase was dried and eraporated in vacuo and the residue was chromatographed over aluminium oxide (200 g, 30 neutral, activity IV) (eluant: methylene chloride + 1 % methanol) - 61 - ^ z7. (0s ^ </ ; " '. • ' / Yield in 2-acetylamino compound: 0.24 g (14 % of theory), M.p.: 62 - 66°C. Yield in 4-acetylamino compound: 0.5 g (28 % of theory), M.p. : 69 - 72°C. Example 55 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-1\3-benzodiazepin-2-one 3-yl/-3-/R-methyl-N- ( 2- (3,4-dimethoxy-phenyl)-ethyl) -amino/ ~ propane a) N-/5-/fi'-Methyl-N' - (2- (3,4-dimethoxy-phenyl)-ethyl)-amino/-propyl7-2-(2-amino-4.5-dimethoxy-phenyl)-ethylamine 4.5 g (0.01 mol) of -methyl-N'-(2-(3,4-dimethoxy- phenyl )-ethyl)-amino/-propyl/-2-(2-amino-4,5-dimethoxy-phenyl)-acetamide were dissolved in 100 ml of tetrahydro-furan and reacted under nitrogen atmosphere with 60 ml of a 1 Molar diborane solution in tetrahydrofuran. The clear solution was allowed to rest for 2 days at room temperature and then mixed with 20 ml of semi-conc. hydrochloric acid with cooling. The tetrahydrofuran was distilled off in vacuo and the remaining hydrochloric residue was made alkaline with conc. sodium hydroxide solution under cooling. The precipitated oil was taken up in methylene chloride, the organic solution was separated, dried and evaporated in vacuo. The oily residue was purified over silica gel with methylene chloride and 1 % of methanol. Yield: 2.9 g (67.2 % of theory), IR-spectrum (methylene chloride): 2830 cm" (OCH^) 2800 cm"1 (N-alkyl) - 62 - 2 b) 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-1,3-benzodiazepin-2-one-3-yl7-3-/N-methyl-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino7propane Prepared analogously to Example 2 by reaction of N-/3-5 & -methyl-N• -(2-(3,4-dimethoxy-phenyl)-ethyl)-amino7- propyl7-2-(2-amino-4,5-dimethoxy-phenyl)-ethylamine with N,N'-carbonyl diimidazole. Yield: 0.9 g (61.6 % of theory), M.p.: 116 - 117°C. 10 Example 54 1-/7,8-Dimethoxy-5-methyl-1,3-dihydro-2H-3,4-benzodiazepin- 2-one-3-yl7-3-^f-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-aminoTpropane dihydrochloride Prepared analogously to Example 1b by reaction of 1-(7,8-di-15 methoxy-5-methyl-1,3-dihydro-2H-3,4-benzodiazepin-2-one-3-yl) 3-chloro-propane with N-methyl-2-(3,4-dimethoxy-phenyl)-ethyl amine. Yield: 24.2 % of theory, M.p.: 106°C. 20 Example 55 1-/7»8-Dimethoxy-l,3-dihydro-2H-3-benzazepin-2-one-3-yl7- 2-hydroxy-3-/H-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-ftinlnri/prnpane a) 1-(7,8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl)-25 2.3-epoxv-propane Prepared analogously to Example 1a by reaction of 7,8-di- 7. O CM? - 63 - methoxy-1,3-dihydro-2H-3-benzazepin-2-one with epichloro-hydrin. Yield: 94.5 % of theory, A IR-spectrum (methylene chloride): 2830 cm (OCH^) 1660 cm"1 (CO) b) 1-/7,8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl7-2-hydroxy-3-/N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino7propane 8.25 g (0.03 mol) of 1-(7»8-dimethoxy-1,3-dihydro-2H-10 3-benzazepin-2-one-3-yl)-2,3-epoxy-propane were dissolved in 100 ml of methanol, reacted with 5.85 g (0.03 mol) of N-methyl-2-(3,4-dimethoxy-phenyl)-ethylamine and refluxed for 3 hours. The methanol was distilled off In vacuo and the residue was purified over a silica gel column 15 with methylene chloride + 1 % of ethanol. Yield: 7.8 g (55.2 % of theory), IR-spectrum (methylene chloride): 3600 cm"*1 (OH) 1650 cm"1 (CO) C26H34N2°6 WO. 6) 20 Calc.: C 66.36 H 7.28 N 5.95 Found: 66.16 7.26 5.80 Example 56 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-1,2-dion-3-yl7-3-/N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino7-25 propane hydrochloride To a mixture of 150 ml of dioxan and 6 ml of water 3.5 g of selenium dioxide were added at 70°C, stirred for 15 minutes and reacted with 3 g of kieselguhr and 14.8 g (0.03 mol) of 1-/7,8 -dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3 0 3-yl7-3-/fr-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino7-propane hydrochloride. The mixture was refluxed for 6 hours, cooled and filtered. The filtrate was evaporated in vacuo - 64 - 7 <o) /f^ ^ and the residue was purified over a silica gel column with methylene chloride + 1 % of ethanol. The fractions were evaporated in vacuo, the residue was dissolved in acetone and the hydrochloride was precipitated with ethereal hydrochloric acid. 5 Yield: 13.8 g (90.7 % of theory), M.p.: 196 - 197°C. Example 57 1-/7 ♦8-Dimethoxy-1,3, 4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-2-hydroxy-3-/N-methyl-N-(2-(3»4-dimethoxy-phenyl)-10 ethyl)-amino7propane Prepared analogously to Example 4 by catalytic hydrogenation of 1-/7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl7-2-hydroxy-3-/N-methyl-N-(2-(3»4-dimethoxy-phenyl)-ethyl)-amino7propane, however, in ethanol at 50 bar and 15 70°C with platinum oxide as catalyst. Yield: 37.5 96 of theory, IR-spectrum (methylene chloride): 3470 cm (OH) 1635 cm"1 (CO) C26H36N2°6 <472'6) 20 Calc.: C 66.08 H 7.68 N 5.93 Found: 66.22 7.57 5.85 Example 58 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(4-nitro-phenyl)-ethyl)-amino7propane 25 hydrochloride Prepared analogously to Example 5b by reaction of 1-/7,8-di methoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7- 2 0 3-chloro-propane with N-methyl-2-(4-nitro-phenyl)-ethylamine. Yield: 56.5 % of theory, M p.: 182°C. Example 59 5 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3- /N-methyl-N-(2-(3-nitro-4-acetylamino-phenyl)-ethyl)-amino7propane dihydrochloride 0.3 g (1.18 mmol) of N-/3-(7,8-dimethoxy-1,3,4,5-tetrahyd^o-2H-3-benzazepin-2-one-3-yl)-p^opyll7methylamine and 0.34 g 10 (1.3 mmol) of 2-(3-nitro-4-acetylamino-phenyl)-ethylbromide were refluxed for 1 hour in 5 ml of chlorobenzene and 0.1 ml of pyridine. The reaction mixture was cooled and the precipitated pyridine hydrobromide was suction filtered. The filtrate was evaporated In vacuo and the residue was puri-15 fied over aluminium oxide (neutral, activity II) with methylene chloride and 0.5 96 of ethanol as eluant. The oil thus obtained was dissolved in acetone and the dihydrochloride was precipitated with ethereal hydrochloric acid. Yield: 230 mg (57.7 % of theory), 20 M.p.: 170°C. Example 60 1-Z7 ,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/Fi-methyl-N-(2-(4-fluoro-phenyl)-ethyl)-amino/-propane dihydrochloride 25 Prepared analogously to Example 5b by reaction of 1-(7,8-di-methoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl)-3-chloro-propane with N-methyl-2-(4-fluoro-phenyl)-ethylamine. Yield: 68.7 % of theory, M.p.: 203°C. >0065 - 66 - Example 61 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-acetyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino7-propane 5 2 g (0.0045 mol) of 1-/7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino/propane were reacted with 15 ml of acetic anhydride and stirred for 30 minutes at room temperature. The mixture was poured on ice water, neutralized with sodium bicarbonate 10 and subsequently extracted with methylene chloride. The organic extract was dried over magnesium sulfate, filtered, and evaporated in vacuo. The residue was purified over aluminium oxide (neutral, activity II) with methylene chloride as eluant. Yield: 1.5 g (68.5 % of theory, 15 IR-spectrum (methylene chloride): 2830 cm" (OCH^) 1640 cm"1 (CO) C27H36N2°6 Calc.: C 66.92 H 7.49 N 5.78 Found: 66.75 7.44 5.80 20 Example 62 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl/-3-/R-ethoxycarbonyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amirtn/propane 2.5 g (0.00565 mol) of 1-/7,8-dimethoxy-1,3,4,5-tetrahydro-2 5 2H-3-benzaz epin-2-one-3-yl/-3-/fl-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino/propane and 2.45 g (0.024 mol) of triethylamine were dissolved in 20 ml of methylene chloride. After addition of 2.6 g (0.024 mol) of ethyl chloroformate stirring was continued for 30 minutes at room temperature, the solution 30 was washed twice with water, dried over magnesium sulfate and evaporated in vacuo. The residue was purified over / / • ' " - 67 - aluminium oxide (neutral, activity II) with methylene chloride as eluant. Yield: 1.5 g (51.6 % of theory), IR-spectrum (methylene chloride): 1690, 1650 cm (CO) C28H38N2°7 (514.6) Calc.: C 65.30 H 7.44 N 5.44 Found: 64.19 7.14 5.27 Example 63 1-/7,8 -Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yi7-3-/fr-methyl-N-(2-(2,6-dichloro-phenyl)-ethyl)-amino7-propane dihydrochloride Prepared analogously to Example 5b by reaction of 1-(7,8-di-methoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl)-3-chloro-propane with N-methyl-2-(2,6-dichloro-phenyl)-ethylamine. Yield: 70.5 % of theory, M.p.: 147°C. Example 64 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl/-3-/H-methyl-N-(2-(3,4-dichloro-phenyl)-ethyl)-amino/-propane dihydrochloride Prepared analogously to Example 5b by reaction of 1-(7,8-di-methoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl)-3-chloro-propane with N-methyl-2-(3»4-dichloro-phenyl)-ethyl-amine. Yield: 57.6 % of theory, M.p.: 161°C. - 68 - 2 006 5 9 Example 65 1-/7,8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl7_ 2-/N-methyl-N-(2-(3.4-dimethoxy-phenvl)-ethyl)-amino7ethane a) 1-(7,8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl)-2-chloro-ethane Prepared analogously to Example 1a by reaction of 7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one with 1-chloro-2-bromo-ethane. Yield: 20 % of theory, M.p.: 114°C. b) 1-^, 8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yi7-2-/fT-methyl-N- (2- (3,4-dimethoxy-phenyl)-ethyl )-amino7ethane Prepared analogously to Example 1b by reaction of 1 — (7 >8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl)- 2-chloro-ethane with N-methyl-2-(3,4-dimethoxy-phenyl)-ethylamine. Yield: 72 % of theory, IR-spectrum (methylene chloride): 2830 cm (OCH^) 2790 cm"1 (N-alkyl) 1655 cm"1 (CO) NMR-spectrum (CDCl^): / « 2.3 ppm, s, 3H (NCH^); 3.85 ppm, s, 12H (OCH^); 6.15 ppm, d(J=8Hz), 1H (olefin.); 6.35, d(J=8Hz), 1H (olefin.). * 69 " *7 ^ ^ ^ €| Example 66 ' ' - y ^ 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-2-/N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino/-ethane hydrochloride ; Prepared analogously to Example 4 by catalytical hydrogenation of 1-/7,8-dimethoxy-1,3-dihydro-2H-3-henzazepin-2-one-3-yl7-2-/N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino7-ethane. Yield; 59 % of theory, M.p.: 188 - 189°C. Example 67 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2,4-dione-3-yl7-3-/fJ-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino7-propane hydrochloride a) 1-(7,8-Dimethoxy-1,3»4,5-tetrahydro-2H-3-benzazepin-2,4-dion-3-vl)-3-chloro-propane Prepared analogously to Example 1a by reaction of 7,8-di-methoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2,4-dion (m.p.: 235°C (decomp.)) with 1-bromo-3-chloropropane. Yield: 26 % of theory, IR-spectrum (KBr): 1660 cm"1 (CO) b) 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2,4-dion-3-yl7-3-/^-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amin£7-propane hydrochloride Prepared analogously to Example 5b by reaction of 1-(7,8-di-methoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2,4-dion-3-yl)-3-chloro-propane with N-methyl-2-(3,4-dimethoxy-phenyl)- . ethylamine. Yield: 35 % of theory, M.p.: 163 - 164°C. ■ yj (r>\ ^ .'"V /o"1 - 70 - Example 68 1-/7-Benzyloxy-8-hydroxy-1, 3, A,5-tetrahydro-2H-3-benzazepin- 2-one-3-yl7-3-/N-methyl-N-(2-(3 >A-dimethoxy-phenyl)-ethyl)- a) 1-(7,8-Dihydroxy-1,3,A,5-tetrahydro-2H-3-benzazepin-2-one-3-vl)-3-chloro-propane 8.9 g (0.03 mol) of 1-(7,8-dimethoxy-1,3,A,5-tetrahydro-2H-3-benzazepin-2-one-3-yl)-3-chloro-propane were dissolved in 100 ml of methylene chloride and reacted at -60°C with 2.1 ml of boron tribromide. After removing the cooling bath the reaction temperature raised to 20°C and at this temperature stirring was continued for 10 hours. The resinous precipitate was made crystalline by addition of 100 ml of water and subsequent stirring for 1 hour. The precipitate was suction filtered and washed with water and methylene chloride. For purification the crystalline product was stirred with acetone and suction filtered. Yield: 7.3 g (90.2 % of theory), M.p.: 177 - 178°C. b) 1-(7-Hydroxy-8-benzyloxy-1,3,4,5-tetrahydro-2H-3-benzazepin- 2-one-3-vl)-3-chloro-propane and 1-(7-Benzyloxy-8-hydroxy-1,3,A,5-tetrahydro-2H-3-benzazepin- 2-one-3-vl)-3-chloro-propan e 19 g (0.07 mol) of 1-(7,8-dihydroxy-1,3,A,5-tetrahydro-2H- 3-benzazepin-2-one-3-yl)-3-chloro-propane and 10.6 g of potassium carbonate in 250 ml of dimethyl sulfoxide were reacted with 19.5 g (0.154 mol) of benzyl chloride. The mixture was stirred for 2 days at room temperature, then 2^0659 poured on ice water and extracted several times with ethyl acetate. The organic extracts were washed thrice with water, dried over magnesium sulfate and evaporated in vacuo. The isomer separation was carried out over silica gel with methylene chloride and 3 % of acetone as eluant. Yield in 7-hydroxy compound: 6 g (23.8 % of theory), M.p.: 163 - 165°C, Yield in 8-hydroxy compound: 4.5 g (17.9 % of theory), M.p.: 185 - 186°C. c) 1-/7-Benzyloxy-8-hydroxy-1,3»4,5-tet^ahydro-2H-3-benzazepin- 2-one-3-yl7-3-Zf'j-methyl-N- (2-(3,4-dimethoxy-phenyl)-ethyl)-amino7propane Prepared analogously to Example 5b by reaction of 1-(7-benz-yloxy-8-hydroxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one- 3-yl)-3-chloro-propane with N-methyl-2-(3,4-dimethoxy-phenyl )-ethylamine. Yield: 75.4 % of theory, M.p.: 128 - 129°C. Example 69 1- /7-Hydroxy-8-benzyloxy-1,3,4,5-tetrahydro-2H-3-benzazepin- 2-one-3-yl7-3-/N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino7propane Prepared analogously to Example 5b by reaction of 1-(7-hydroxy-8-benzyloxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl)- 3-chloro-propane with N-methyl-2-(3,4-dimethoxy-phenyl)-ethyl-amine. Yield: 47.2 % of theory, M.p.: 157 - 158°C. 5 9 - 72 - Example 70 1-/7»8-Dihyd.roxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl/-3-/N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino/-propane 5 0.52 g (0.001 mol) of 1-/7-hydroxy-8-benzyloxy-1,3,4,5-tetra-hydro-2H-3-benzazepin-2-one-3-yl/-3-/N-methyl-N-(2-(3,4-dimethoxy-phenyl )-ethyl)-amino/propane were hydrogenated for 5 hours at 20°C and 5 bar in 100 ml of methanol and 0.2 g of palladium/charcoal (10 %). The catalyst was suction filtered, 10 the filtrate was evaporated In vacuo and the residue was purified over silica gel with methylene chloride + 1 % of ethanol as eluant. Yield: 0.2 g (43-9 % of theory), IR-spectrum (methylene chloride): 3520 cm"1 (OH) 15 1640 cm"1 (CO) C24H32N2°5 x 1/2 H2° (*55.5) Calc.: C 63.28 H 7.74 N 6.15 Found: 63.44 7.77 6.13 Example 71 20 1-/7-Benzyloxy-8-methoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-* amino/propane dihydrochloride 0.52 g (0.001 mol) of 1-/7-benzyloxy-8-hydroxy-1,3,4,5-tet^a-hyd^o-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(3,4-di-25 methoxy-phenyl)-ethyl)-amino/-propane were dissolved in 30 ml of dimethyl formamide and reacted with 50 mg of 50 % sodium hydride dispersion (in oil). The mixture was warmed for 30 minutes up to 60°C, mixed with 0.1 ml of dimethyl sulfate and warmed for further 2 hours up to 60°C. The dimethyl formamide 30 was distilled off in vacuo, the residue was taken up in methylene chloride, the organic phase was washed with water, dried and evaporated in vacuo. The resinous residue was purified over aluminium oxide (neutral, activity II) with methylene chloride as eluant. The oil obtained was dissolved in acetone 2 0 0 6 5 9 - 73 - and the dihydrochloride was precipitated by reaction with ethereal hydrochloric acid. Yield: 250 mg (41 % of theory), M.p.: 117 - 120°C. Example 72 1-/7-Methoxy-8-benzyloxy-1,3,4,5-tetrahydro-2H-3-benzazepin- 2-one-3-yi7-3-/N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino7propane Prepared analogously to Example 71 by reaction of 1-/7-hydroxy-8-benzyloxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7- 3-/IT-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino/-propane with dimethyl sulfate. Yield: 70 % of theory, _ A IR-spectrum (methylene chloride): 1655 cm (CO) NMR-spectrum (CDCl^/D^): f «2.3 ppm, s, 3H (NCH^); 5,1 ppm, s, 2H (benzyl.); 6.5 - 6.8 ppm, m, 5H (aromat.); 7.4 ppm, s, 5H (aromat.). Example 73 1-/7-Hydroxy-8-methoxy-1,3,4,5-tetrahydro-2H-3-benzazepin- 2-one-3-yl7-3-/K-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino7propane hydrochloride Prepared analogously to Example 70 from 1-/7~benzyloxy-8-methoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino7propane hydrochloride by catalytic debenzylation. ?. 0 06 - 74 - Yield: 45.2 % of theory, -1 IR-spectrum (methylene chloride): 3530 cm" (OH) 3 2830 cm"1 (OCH,) 1650 cm"1 (CO)' 5 C25H34N2°5 x HC1 (479.0) Calc.: C 62.69 H 7.36 N 5.85 Found: 63.15 7.57 5.64 Example 74 1-/7-Methoxy-8-hydroxy-1,3*4,5-tetrahydro-2H-3-benzazepin-10 2-one-3-yl7-3-/N-methyl-N-(2-(3»4-dimethoxy-phenyl)-ethyl)-amino7propane Prepared analogously to Example 70 from 1-/7-methoxy-8-benzyl-oxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino/propane by catalytic 15 debenzylation. Yield: 29.4 % of theory, IR-spectrum (methylene chloride): 1640 cm"1 (CO) C25H34N2°5 (442.56) Calc.: C 67.85 H 7.74 N 6.33 20 Found: 67.50 7.97 6.18 Example 75 1-/7» 8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/fJ-methyl-N-(2-(3,4-dimethyl-phenyl)-ethyl)-amino7propane dihydrochloride 25 Prepared analogously to Example 5b by reaction of 1-(7,8-di- methoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl)-3-chloropropane with N-methyl-2-(3,4-dimethyl-phenyl)-ethylamine. Yield: 54.3 % of theory, M.p.: 170 - 172°C. - 75 - Example 76 2 A 0 S 5 9 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(4-tert.butyl-phenyl)-ethyl)-amino/-propane dihydrochloride Prepared analogously to Example 5b by reaction of 1-(7,8-di-methoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl)-3-chloropropane with N-methyl-2-(A-tert.butyl-phenyl)-ethylamine. Yield: 49.A % of theory, M.p.: 1A6 - 1A9°C. Example 77 1-/7,8-Dimethoxy-1,3,4,5-tet^ahyd^o-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N- (2- (4-n-butoxy-phenyl )-ethyl )-amino7propane Prepared analogously to Example 5b by reaction of 1-(7,8-di-methoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl)-3-chloropropane with N-methyl-2-(4-n-butoxy-phenyl)-ethylamine. Yield: 55.3 % of theory, M.p.: 67 - 69°C. Example 78 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7- 3-/N-methyl-N-(2-(2,4,6-trimethoxy-phenyl)-ethyl)-amino7propane Prepared analogously to Example 5b by reaction of 1-(7,8-di-methoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl)-3-chloropropane with N-methyl-2-(2,4,6-trimethoxy-phenyl)-ethylamine. Yield: 57.8 % of theory, © Example 79 1-fl,8-Dimethyl-1,3-dihydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino7propane hydrochloride a) 1-(7,8-Dimethyl-1,3-dihydro-2H-3-benzazepin-2-one-3-yl)-3-chloro-propane Prepared analogously to Example 1a by reaction of 7,8-di-methyl-1,3-dihydro-2H-3-benzazepin-2-one (m.p.: 220 - 224°C) with 1-bromo-3-chloropropane. Yield: 99 % of theory, M.p.: 62 - 64°C. b) 1-/7,8-Dimethyl-1,3-dihydro-2H-3-benzazepin-2-one-3-yl7- 3-^J-methyl-N-(2-(3»4-dimethoxy-phenyl)-ethyl)-amin£7propane hydrochloride Prepared analogously to Example 1b by reaction of 1-(7,8-dimethyl-1,3-dihydro-2H-3-benzazepin-2-one-3-yl)-3-chloro-propane with N-methyl-2-(3,4-dimethoxy-phenyl)-ethylamine. Yield: 70.9 % of theory, M.p.: 105 - 107°C. - 76 - 2 00 A IR-spectrum (methylene chloride): 1650 cm" (CO) A 1520 cm" (aromat. C=C) C27H38N2°6 x HC1 (523.2) Calc.: C 62.00 H 7.51 N 5.35 CI 6.77 Found: 61.75 7.52 .5.18 7.34 2 00659 - ii - Example 80 1-Z7 ,8-Dimethyl-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino/-propane dihydrochloride Prepared analogously to Example 4 by catalytical hydrogenation of 1-/7,8-dimethyl-1,3-dihydro-2H-3-benzazepin-2-one-3-yl/-3-/N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino/-propane. Yield: 83.8 % of theory, M.p.: 154 - 157°C. Example 81 1-/7,8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl/- 2-methyl-3-/N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino/-propane a) 1-(7,8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl)-2-methyl-3-chloro-propane Prepared analogously to Example 1a by reaction of 7,8-di-methoxy-1,3-dihydro-2H-3-benzazepin-2-one with 1-bromo-2-methyl-3-chloro-propane. Yield: 97.5 % of theory, M.p.: 45 - 47°C. b) 1-/7r8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl7-2-methyl-3-/N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino7propane Prepared analogously to Example 1b by reaction of 1-(7,8-di methoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl)-2-methyl-3-chloro-propane with N-methyl-2-(3,4-dimethoxy-phenyl)-ethylamine. Yield: 36 % of theory, M.p.: 30 - 32°C. , . 7 °> 0 ^ 5 - 78 - Example 82 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yi7-2-methyl-3-/N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino7propane hydrochloride 5 Prepared analogously to Example 4 by catalytic hydrogenation of 1-/7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin- 2-one-3-yl7-2-methyl-3-/ft-methyl-N- (2- (3,4-dimethoxy-phenyl )-ethyl)-amino7propane. Yield: 73.7 % of theory, 10 M.p.: 99 - 101°C. # Example 83 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-1,2-dion-3-yl/-3-/N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino7propane hydrochloride 15 3 g of sodium dichromate x 2 1^0 were given to 2.45 g (0.005 mol) of 1-/7,8-dimethoxy-1,3,4,5-tet^ahydro-2H- 3-benzazepin-2-one-3-yl7-3- /jT-methyl-N-(2-(3»4-dimethoxy-phenyl)-ethyl)-amino/propane hydrochloride in 50 ml of glacial acetic acid. The mixture was stirred for 2 hours 20 at room temperature, poured on ice water, neutralized with potassium carbonate and extracted several times with methylene chloride. The organic extracts were dried over magnesium .sulfate and evaporated in vacuo. The residue was purified over a silica gel column with methylene chloride + 1 % 25 of ethanol as eluant. The product thus obtained was dissolved and the hydrochloride was precipitated with ethereal hydrochloric acid. Yield: 1.3 g (51.3 % of theory), M.p.: 197 - 198°C. Example 84 - 79 - 2 0 06 5 9 1~Z7> 8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-1,2-dion-3-yl7-3-/ff-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino7propane hydrochloride 5 1.98 g (4.0 mmol) of 1-/7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-^-methyl-N-(2-(3,4-dimethoxy-phenyl) -ethyl )-amin£7propane hydrochloride were suspended in 50 ml of acetic anhydride, the suspension mixed with 2.5 g of potassium permanganate and stirred for 20 minu-10 tes at 20°C. The reaction mixture was poured on ice water and made ammoniacal with conc. ammonia. The precipitated manganese-dioxide was suction filtered and the filtrate was extracted several times with methylene chloride. The extract was dried over magnesium sulfate, evaporated in vacuo and 15 the residue was purified over a silica gel column with methylene chloride + 1 % of ethanol as eluant. The product thus obtained was dissolved in acetone and the hydrochloride was precipitated with ethereal hydrochloric acid. Yield: 0.7 g (34.5 % of theory), 20 M.p.: 196 - 197°C. Example 85 1-/5,9 -Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(3.4-dlmethoxy-phenyl)-ethyl)-amlno7propane a) 1-:(6,9-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl)-25 3-chloro-propane Prepared analogously to Example 1a by reaction of 6,9-di-methoxy-1,3-dihydro-2H-3-benzazepin-2-one (m.p.: 188 - 191°C) with 1-bromo-3-chloro-propane. Yield: 27 % of theory, 30 M.p.: 97 - 99°C. - so - 2 006 5 9 b) 1-/£,9-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl/-3-/N-methyl-N-(2-(3.4-dimethoxy-phenyl)-ethyl)-amino7propane Prepared analogously to Example 1b by reaction of 1 — (6,9— dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl)-3-chloro-propane with N-methyl-2-(3,4-dimethoxy-phenyl)-ethylamine. Yield: 90 % of theory, _ A IR-spectrum (methylene chloride): 1658 cm" (CO) NMR-spectrum (CDC13/D20): £ = 2.2 ppm, s, 3H (NCH^); 3.7 - 3.8 ppm, 4s, 12H (0CH3); 6.25 ppm, d (J = 9Hz), 1H (olefin.). Example 86 1-/£,9-Dimethoxy-1,3,4,5-tetrahydro-2H-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino7propane hydrochloride Prepared analogously to Example 4 by catalytic hydrogenation of 1-/?>,9-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl/-3-/ff-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino/propane. Yield: 85 % of theory, M.p.: 73 - 76°C. Example 87 1-/S,9-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl/-3-,/N-methyl-N- (2- (3,4-dimethoxy-phenyl)-ethyl)-amino/-propane hydrochloride a) 1-(8,9-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl)-3-chloro-propane Prepared analogously to Example 1a by reaction of 8,9-di-methoxy-1,3-dihydro-2H-3-benzazepin-2-one (m.p.: 165 -168°C) with 1-bromo-3-chloropropane. Yield: 45 % of theory, m.p.: 67 - 71°C. b) 1-/5,9-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino7-propane hydrochloride Prepared analogously to Example 1b by reaction of 1-(8,9-5 dixnethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl)-3-chloropropane with N-methyl-2-(3,4-dimethoxy-phenyl)-ethylamine . Yield: 64 96 of theory, M.p.: 64 - 68°C. Example 88 10 1-/3 ,9-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3- /N-methyl-N- (2- (3,4-dimethoxy-phenyl) -ethyl) -aminoJ -propane hydrochloride Prepared analogously to Example 4 by catalytic hydrogenation of 1-/5,9-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yl7- 15 3-/W-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amin£7propane. Yield: 75 % of theory, M.p.: 131 - 133°C. Example 89 1-/7»8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-20 3-yl7-3-/M-methyl-N-(2-(3,4,5-trimethoxy-phenyl)-ethyl)-amlno7propane dihydrochloride Prepared analogously to Example 5b by reaction of 1-(7,8-di methoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl)-3-chloro-propane with N-methyl-2-(3,4,5-trimethoxy-phenyl)-25 ethylamine. Yield: 44 % of theory, M.p.: 131°C (decomp.). Example 90 - 82 - 200659 Isomer mixture of 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl.7-3-/N-methyl-N-(2-(2- and 4-nitro-phenvl)-ethyl)-amino7propane Prepared analogously to Exsunple 1b from 1-/7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-chloro-propane and N-methyl-2-(2- and 4-nitro-phenyl)-ethylamine. Yield: 72 % of theory, IR-spectrum (methylene chloride): 1650 cm"" (CO) Example 91 Isomer mixture of 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/H-methyl-N-(2-(2- and 4-amino-phenyl)-ethyl)-amino7propane Prepared analogously to Example 4 by catalytic hydrogenation of a isomer mixture of 1-/7,8-dimethoxy-1,3,4,5-tetrahydro- 2H-3-benzazepin-2-one-3-yi7-3-/N-methyl-N-(2-(2- and 4-nitro- phenyl )-ethyl)-amino7propane. Yield: 81 % of theory, ^ IR-spectrum (methylene chloride): 1645 cm~ (CO). - 83 - Example 92 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7~3-/N-methyl-N-(2-(2-ac etylamino-phenyl)-ethyl)-amin£7-propane hydrochloride and 1"/J,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-niethyl-N-(2-(4-acetylamino-phenyl)-ethyl)-amin£7-propane hydrochloride Prepared analogously to Example 52 by reaction of a isomer mixture of 1-/7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benz-azepin-2-one-3-yl7-3-/N-methyl-N- (2-(2- and 4-amino-phenyl)-ethyl)-amin£7propane with glacial acetic acid and acetic anhydride. Yield in 2-acetylamino compound: 26 % of theory, M.p.: 102 - 105°C (decomp.) Yield in 4-acetylamino compound: 49 % of theory, M.p.: 89 - 93°C (decomp.). Example 93 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-vl7-3-/N-methyl-N-(2-(4-amino-phenyl)-ethyl)-amlno7propane 4.85 g (0.0107 mol) of 1-/7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl;7-3-/N-methyl-N-(2-(4-acetylamino-phenyl)-ethyl)-amin£7propane were stirred for 34 hours at 40°C with 80 ml of methanolic hydrochloric acid. After evaporating the solution, the residue was dissolved in methylene chloride, extracted with sodium bicarbonate solution and washed with water. The organic phase was dried, evaporated in vacuo and the oil obtained was subsequently dried at 50°C in vacuo. Yield: 88 % of theory, IR-spectrum (methylene chloride): 1645 cm" (CO) NMR-spectrum (CDCl^A^O): « 2.25 ppm, s, 3H (NCH^); 3.8 ppm, s, 12H (OCH^); 6.9 ppm, d (J«7Hz), 2H (aromat.). /p\ Z7 '7rj // ;i . v ^7 t - 84 - Example 94 1-Jj,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yi7-3-/N-methyl-N-(2-(4-chloro-phenyl)-ethyl)-amino7-propane dihydrochloride 5 1.01 g (0.00245 mol) of 1-/7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/ft-methyl-N-(2-(4-amino-phenyl)-ethyl)-amino7propane were dissolved in 5 ml of semi-conc. hydrochloric acid and diazotized with 0.17 g (0.00245 mol) of sodium nitrite. Subsequently the solution was stirred at 55°C 10 until no nitrogen escaped. The solution was made weakly alkaline and extracted with methylene chloride. After drying and evaporating in vacuo, the obtained oil was purified over aluminium oxide (200 g, neutral, activity II) (eluant: methylene chloride + 2 % of ethanol) and the di-15 hydrochloride was precipitated from acetone with ethereal hydrochloric acid. Yield: 21 % of theory, M.p.: 148 - 151°C. Example 95 20 1-/7,8 -Dimethoxy-2,3-dihydro-1H-3-benzazepin-3-yl7-3- /fT-methyl-N-(2-(3.4-dimethoxy-phenyl)-ethyl)-amlno7propane 2.3 g (0.005 mol) of 1-/7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one-3-yi7-3-/N-methyl-N-(2-(3,4-dimethoxy-phenyl) -ethyl )-amino7propane were dissolved in 150 ml of 25 absolute ether, mixed with 0.6 g of lithium aluminium hydride and stirred for 2 hours at room temperature. With ice cooling 10 % ammonium chloride-solution was added, the precipitate was suction filtered and the solvent was removed in vacuo. The oily residue was purified over aluminium oxide (neutral, 30 activity II) with methylene chloride as eluant. - 85 - Yield: 1.6 g (72.7 % of theory), 2^0 6 5 9 ^ <4 IR-spectrum (methylene chloride): 2830 cm (OCH^) 2790 cm"1 (N-alkyl) C26H36N2°4 (440.6) Calc.: C 70.88 H 8.24 N 6.36 5 Found: 70.50 8.80 6.22 Example 96 1-/7»8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(4-hydroxy-phenyl)-ethyl)-amino7-propane hydrochloride 10 1.1 g (2.67 mmol) of 1-/7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(4-amino-phenyl)-ethyl)-amino/propane were dissolved in 10 ml of semi-conc. sulfuric acid and diazotized at 0°C with 0.18 g (2.67 mmol) of sodium nitrite. The solution was heated on the steam bath 15 for 20 minutes, diluted with water, made weakly alkaline with sodium hydroxide solution and extracted with methylene chloride. After drying and evaporating in vacuo, the obtained oil was purified over 100 g of aluminium oxide (neutral, activity II) with methylene chloride + 2 % of ethanol as eluant, 20 The hydrochloride was precipitated from acetone/ethereal hydrochloric acid. Yield: 0.17 g (15 96 of theory), M.p.: 109 - 112°C (decomp.). Example 97 25 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one- 3-yl7-3-/N-methyl-N-(2-(4-dimethy1amino-phenyl)-ethyl)-amino/-propane dihydrochloride Prepared analogously to Example 11 by reaction of 1-/7,8-di-methoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-30 methyl-N-(2-(4-amino-phenyl)-ethyl)-amino7propane with - 86 - 2 00^ - 37 % formalin solution and sodium cyanoborohydride. Yield: 40 % of theory, M.p.: 193 - 196°C. Example 98 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-1,3-benzodiazepin- 2-one-3-yl7~3-/N-methyl-N-(2-(4-amino-3,5-dichloro-phenyl)-ethyl)-amino7propane a) N-/3-/N1-Methyl-N1 -(2-(4-amino-3,5-dichloro-phenyl)-ethyl)-amino7-propyl7-2-(2-amino-4,5-dimethoxy-phenyl)-ethylamine hydrochloride Prepared analogously to Example 53a from N-/5-/N'-methyl-N1-(2-(4-amino-3,5-dichloro-phenyl)-ethyl)-amino7-propyl/-2-(2-amino-4,5-dimethoxy-phenyl)-acetamide and lithium aluminium hydride. M.p.: 182 - 188°C (decomp.). b) 1-jj,8-Dimethoxy-1,3,4,5-tetrahydro-2H-1,3-benzodiazepin-2-one-3-yl.7-3-/N-methyl-N-(2-(4-amino-3,5-dichloro-phenyl)-ethyl)-amino7propane Prepared analogously to Example 53b from N-/3-/N'-methyl-N1-(2-(4-amino-3,5-dichloro-phenyl)-ethyl)-amino7-propyl7-2-(2-amino-4,5-dimethoxy-phenyl)-ethylamine hydrochloride and N,N'-carbonyl diimidazole. M.p.: 163 - 166°C. 2 0 0659 - 87 - Example 99 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-1,2-dion-3-yl7-3-/N-methyl-N-(2-(4-amino-3,5-dichloro-phenyl)-ethyl)-amino7propane Prepared analogously to Example 5b from 1-/7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl- N-(2-(4-amino-3,5-dichloro-phenyl)-ethyl)-amino/propane and selenium dioxide. M.p.: 118 - 130°C, m/e = 493/495 (C^H^Cl^O^; 494.43) Example 100 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yi7-3-/N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino7-propane dihydrochloride 1.1 g (5.0 mmol) of 7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one were suspended in 20 ml of dimethyl sulfoxide and mixed with stirring with 0.6 g (5.3 mmol) of potassium tert.butylate. After 10 minutes the solution was mixed with 2.0 g (7.4 mmol) of 1-chloro-3-/N-methyl-N-(2-(3,4-dimethoxy-phenyl) -ethyl)-amino7propane, subsequently stirred for 1 hour at 50°C, poured on water, extracted with ethyl acetate and the organic phase was evaporated in vacuo. The residue was purified over silica gel with methylene chloride + 10 % of methanol as eluant and the dihydrochloride was precipitated from acetone with ethereal hydrochloric acid. M.p.: 136 - 137°C. Example 101 - 88 - 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amin£7-propane dihydrochloride Prepared analogously to Example 100 from 7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one and N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-azetidinium bromide. M.p.: 137°C. Example 102 1-/7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl/-3-/N-methyl-N-(2-(3-amino-4-chloro-phenyl)-ethyl)-aminoTpropane Prepared analogously to Example 12 by reaction of N-/5-(7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl)-propyl7methylamine with 2-(3-amino-4-chloro-phenyl)-ethylchloride. Oil. UV-spectrum (ethanol): ^ max: 238 nm (0.26) 285 nm (0.19) 304 nm (0.06) IR-spectrum (dichloromethane): 3390 and 3480 cm (nh2) (co) (och3) 1650 cm-1 2830 cm"1 2795 cm"1 (ch3-nc (c-c) 1520 and 1620 cm"1 200659 - 89 - Example I Tablets containing 10 mg of 1-/7,8-dimethoxy-1,3,4,5-tetra-hydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(3,4-di-methoxv-phenyl)-ethyl)-amino7propane hydrochloride 5 Composition: 1 tablet contains: Active ingredient 10.0 mg Corn starch 57.0 mg Lactose 48.0 mg 10 Polyvinyl pyrrolidone 4.0 mg Magnesium stearate 1.0 mg 120.0 mg Method of preparation: The active ingredient, corn starch, lactose and polyvinyl 15 pyrrolidine were mixed together and moistened with water. The moist mixture was forced through a screen with a mesh size of 1.5 mm and then dried at about 45°C. The dry granulate was passed through a screen with a mesh size of 1.0 mm and then mixed with magnesium stearate. The finished mixture 20 was compressed in a tablet press with punches 7 mm in diameter and marked with a notch, to form tablets. Weight of tablet: 120 mg Example -II Coated tablets containing 5 mg of 1-/?,8-dimethoxy-1,3,4,5-25 tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/R-methyl-N-(2-(3.4-dimethoxv-phenvl)-ethyl)-amino7propane hydrochloride 1 Coated tablet core contains: Active ingredient 5.0 mg Corn starch 41.5 mg 30 Lactose 30.0 mg 2 0 0 6* Method of preparation: 5 The active ingredient, corn starch, lactose and polyvinyl pyrrolidone were thoroughly mixed and moistened with water. The moist mass was forced through a screen with a mesh size of 1 mm, then dried at about 45°C and the granulate was then passed through the same screen. After the addition of magne-10 sium stearate, convex tablet cores with a diameter of 6 mm were produced by compression in a tablet-making machine. The tablet cores thus produced were coated in known manner with a covering consisting essentially of sugar and talc. The finished coated tablets were polished with wax. 15 Weight of coated tablet: 130 mg. Example III Ampoules containing 5 mg of .1 -n ,8-dimethoxy-1,3,4,5-tetra-hydro-2H-3-benzazepin-2-one-3-yi7-3-/N-methyl-N-(2-(3,4-di-methoxy-phenyl)-ethyl)-amino7propane hydrochloride 20 1 Ampoule contains: Active ingredient 5.0 mg Sorbitol 50.0 mg Water for injection ad 2.0 ml Method of preparation: 25 In a suitable container, the active ingredient was dissolved in water for injection purposes and the solution was made isotonic with sorbitol. After being filtered through a membrane filter, the solution was decanted into clean, sterilized ampoules under an N2 atmosphere and autoclaved for 20 minutes 30 in a current of steam. Polyvinyl pyrrolidine 3.0 mg Magnesium stearate 0.5 mg 80.0 mg -si- 20065 Example IV Suppositories containing 15 mg of 1-/7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/N-methyl-N-(2-(3.4-dimethoxy-phenyl)-ethyl)amino7propane hydrochloride 5 1 Suppository contains: Active ingredient 0.015 g Hard fat (e.g. Witepsol H 19 and W 45) 1.685 g 1.700 g Method of preparation: 10 The hard fat was melted. At 38°C the ground active ingredient was homogeneously dispersed in the melt. It was cooled to 35°C and poured into slightly pre-cooled suppository moulds. Example V Drops solution containing 10 mg of 1 -Z7.e -dimethoxy-1,3,4,5-15 tetrahydro-2H-3-benzazepin-2-one-3-yl7-3-/Fi-methyl-N-(2-(3,4-dlmethoxy-phenyl)-ethyl)-amino7propane hydrochloride per 5 ml 100 ml of solution contain: 20 25 Active ingredient 0.2 g Hydroxy ethylcellulose 0.15 g Tartaric acid 0.1 g Sorbitol solution containing 70 % dry matter 30.0 g Glycerine 10.0 g Benzoic acid 0.15 g Distilled water ad 100.0 ml </div>

Claims

<div class="application article clearfix printTableText" id="claims"> - 92 - Distilled water was heated to 70°C. The hydroxy ethyl-cellulose, benzoic acid and tartaric acid were dissolved therein with stirring. The mixture was cooled to ambient temperature and the glycerine and sorbitol solution were added with stirring. At ambient temperature, the active ingredient was added and stirred until completely dissolved. Then the mixture was evacuated, with stirring, in order to eliminate air from the liquid. t -93- WHAT WE CLAIM IS; 1. Compounds of general formula I 200659 - e - n - g (I) [wherein A represents a group of formula i7 -CH=CH-, -NH-CO-, -CH2-C0- or -C=N-5 5 5 (wherein R^ represents an alkyl group containing 1 to 3 carbon atoms) and B represents a methylene or carbonyl group, or A represents a -CO-CO- group and B represents a methylene group; E represents an ethylene, n-propylene or n-butylene group (optionally substituted by an alkyl group containing 1 to 3 carbon atoms), an n-propylene group substituted at the 2-position by a hydroxy group or n-butylene group substituted at the 2- or 3-position by a hydroxy group; G represents a methylene or ethylene group (optionally substituted by an alkyl group containing 1 to 3 carbon atoms); and R2, which may be the same or different, each represents a hydroxy group, an alkyl group containing 1 to 3 carbon atoms, or an alkoxy or phenylalkoxy group (in each of which the alkyl part may contain 1 to 3 carbon atoms) or one of the radicals R^ and R2 represents a hydrogen atom or R^ together with R2 represents an alkylenedioxy group containing 1 or 2 carbon atoms; R^ and R^, which may be the same or different, each represents a hydrogen or halogen 200659 -94- atom, a hydroxy group, an alkyl or alkoxy group, each of which may contain 1 to 4 carbon atoms, or a trifluoro-methyl or cyano group or one of the radicals R^ or R4 represents a nitro group or together with R^ represents an alkylenedioxy group containing 1 or 2 carbon atoms; R^ represents a hydrogen atom, a hydroxy or amino group, an alkyl, alkoxy or alkylamino group containing 1 to 3 carbon atoms, or a dialkylamino, alkanoylamino, alkoxycarbonylamino or bis(alkoxycarbonyl)-amino group, in each of which the alkyl part may contain from 1 to 3 carbon atoms, or a methylamino or ethylamino group substituted by a trifluoromethyl group; and Rg represents a hydrogen atom, an alkyl group containing from 1 to 3 carbon atoms, or a phenylalkyl, alkanoyl or alkoxycarbonyl group, in each of which the alkyl part may contain from 1 to 3 carbon atoms, or an alkenyl group containing 3 to 5 carbon atoms] and acid addition salts thereof. 2. Physiologically compatible acid addition salts of compounds of formula I as defined in claim 1. 3. Salts as claimed in claim 2 formed with hydrochloric, hydrobromic, sulfuric, phosphoric, acetic, lactic, aa'4s. citric, tartaric, succinic, maleic or fumaric jb^id./ 4. Compounds as claimed in any one of the preceding claims, wherein A represents a -CI^-CI^-, -CH=CH-, CHo

1 3 -NH-CO-, -CH--CO- or -C=N- group and B represents 5 5 5 a methylene or carbonyl group, or A represents a -CO-CO-group and B represents a methylene group; E represents an ethylene, n-propylene, n-butylene, 2-methyl-n-propylene or 2-hydroxy-n-propylene group; G represents a methylene, ethylene, or 1-methyl-ethylene group? R^ represents a methyl, hydroxy, or benzyloxy group or an alkoxy group containing 1 to 3 carbon atoms and R2 represents a hydrogen atom or a methyl, hydroxy or methoxy group, or R^ and R2 together represent a methylenedioxy group; R3 represents a hydrogen, fluorine, chlorine or bromine atom, a trifluoromethyl or nitro group, or an alkyl or alkoxy -95- ^ f> 6 5 9 group containing 1 to 4 carbon atoms each and R^ represents a hydrogen, chlorine or bromine atom or a methyl, methoxy or cyano group or R^ and R^ together represent a methylenedioxy group; R^ represents a hydrogen atom or a hydroxy, methoxy, amino, acetylamino, ethoxycarbonylamino, bis(ethoxycarbonyl)-amino, dimethyl-amino or B,8,6,-trifluoroethylamino group; and Rg represents a hydrogen atom, an alkyl group containing 1 to 3 carbon atoms or an allyl, benzyl, acetyl or ethoxycarbonyl group. 5. Compounds as claimed in claim 4, wherein A represents CH0 I 3 a -CH2-CH2-, -CH=CH- or -C=N- group and B represents 5 a carbonyl group, or A represents a -CH=CH-, -NH-CO- 5 or -CO-CO- group and B represents a methylene group; E represents an n-propylene group; G represents an ethylene group; R^ represents a methoxy or hydroxy group and R2 represents a methoxy group, or R1 and R2 together represent a methylenedioxy group; R^ represents a methoxy or trifluoromethyl group or a chlorine or bromine atom and R^ represents a methoxy group or a hydrogen, chlorine or bromine atom, or R^ and R^ together represent a methylenedioxy group; R^ represents a hydrogen atom or an amino or methoxy group; and Rg represents a hydrogen atom or a methyl, ethyl, n-propyl or allyl group. 6. Compounds of general formula la, \ a r6 n-ch„-ch^-ch„-n-ch„-ch^-< (ia) ch2-b' CH-, I 3 wherein A represents a -CH--CH--, -CH=CH- or -C=N- t t 5 -96- 7 0 O1 ^ group and B represents a carbonyl group, or A represents an -NH-CO- or -COCO- group and B represents a methylene 5 group; and R2 each represents a methoxy group; Rg represents a hydrogen atom or a methyl or allyl group; R^ represents a hydrogen atom or a methoxy group at the 3-position and R^ represents a methoxy group at the 4-position or R^ and R^ together represent a 3,4-methylenedioxy group, and R^ represents a hydrogen atom; or R^ at the 3-position represents a chlorine or bromine atom, R^ at the 5-position represents a chlorine or bromine atom and R^ at the 4-position represents an amino group, and acid addition salts thereof with inorganic or organic acids. 7. 1-17,8-Dimethoxy-l,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl]-3-[N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino]-propane. 8. 1-[7,8-Dimethoxy-l,3,4,5-tetrahydro-2H-3-benzazepin-1,2-dion-3-yl] -3-[N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino]-propane. 9. 1-[7,8-Dimethoxy-l,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl]-3-[N-methyl-N-(2-(4-amino-3,5-dichloro-phenyl) -ethyl) -amino] -propane. 10. 1-[7,8-Dimethoxy-l,3,4,5-tetrahydro-2H-3-benzazepin-2-one-3-yl]-3-[N-methyl-N-(2-(4-methoxy-phenyl)-ethyl)-amino]-propane. 11. Physiologically compatible acid addition salts of compounds as claimed in any one of claims 6 to 10. 12. Hydrochloric, hydrobromic, sulfuric, phosphoric, acetic, lactic, citric, tartaric, succinic, maleic or fumaric acid addition salts of compounds as claimed in any one of claims 6 to 10. 13. Compounds as claimed in claim 1 wherein A represents a group of formula -CH2-CH2~, -CH=CH- or -NH-CO-; 5 B represents a methylene or carbonyl group; R^ represents an alkoxy group containing 1 to 3 carbon atoms, R2 -97- 2 0 06 5 9 represents a hydrogen atom or an alkoxy group containing 1 to 3 carbon atoms, or R^ and R2 together represent a methylenedioxy group; R^ and R^, which may be the same or different, each represents a hydrogen atom or an alkoxy group containing 1 to 3 carbon atoms, or R^ and R^ together represent a methylenedioxy group; R^ represents a hydrogen atom; Rg represents a hydrogen atom, an alkyl group containing 1 to 3 carbon atoms (optionally substituted by a phenyl group) or an allyl group; E represents an ethylene, n-propylene or n-butylene group; and G represents an ethylene group. 14. Compounds as claimed in claim 1 as herein described in any one of the Examples. 15. Compounds as claimed in claim 13 as herein described in any one of Examples 1, 2 and 4-10. 16. A process for the preparation of compounds as claimed in claim 1, which comprises reacting a compound of general formula II (wherein A and B are as defined in claim 1, R^' and R2* each represents a hydroxy group protected by a protective radical or represent R^ and R2 as defined in claim 1) with a compound of general formula III P ' R » (III) -98- «•} ^ ^ ^ Q (wherein Rg, E and G are as defined in claim 1, R^', R^' and R^' each represent a hydroxy group protected by a protective radical or represent R^, R4 and R^ as defined in claim 1, and Z represents a nucleophilically exchangeable group) or the corresponding internal' quaternary salt thereof, optionally present in the reaction mixture, of general formula Ilia (wherein E, G, Z, R^' R^', R^' and Rg are as hereinbefore defined) and optionally subsequently cleaving the protective radical or radicals. 17. A process as claimed in claim 16 wherein Z represents a chlorine, bromine or iodine atom, a methanesulfonyloxy, p-toluenesulfonyloxy or ethoxysulfonyloxy group. 18. A process as claimed in claim 16 or claim 17 wherein the reaction is carried out in a solvent. 19. A process as claimed in any one of claims 16 to 18 wherein the reaction is carried out at temperatures between 0 and 150°C. 20. A process as claimed in claim 18 wherein the reaction is carried out at the boiling point of the solvent. 21. A process as claimed in any one of claims 16 to 20 wherein the reaction is carried out in the presence of a base. 22. A process as claimed in any one of claims 16 to 21 wherein at least one protective radical is split off hydrolytically in the presence of an acid or base, or if the protective radical is a benzyl radical, R 1 4 (Ilia) R • 5 -99- 200659 is optionally alternatively split off hydrogenolytically. 23. A process for the preparation of compounds as claimed in claim 1 wherein Rg represents a hydrogen atom, an alkenyl group containing 3 to 5 carbon atoms, an alkyl group containing 1 to 3 carbon atoms, or a phenylalkyl group containing 1 to 3 carbon atoms in the alkyl part, which comprises reacting a compound of general formula IV X B N - E - U / (IV) with a compound of general formula V + G - V (V) [wherein A, B, E and G are as defined in claim 1, Rl'f R2'' *3'' **4' an(^ Rs' eacb represent a hydroxy group protected by a protective radical or represent Rl' R2r R3' R4 an(^ R5 as *n claim 1, one of the radicals U and V represents an Rg'-NH- group (wherein Rg' represents^ hydrogen atom, an alkenyl group containing 3 to 5 carbon atoms, an alkyl group containing 1 to 3 carbon atoms, or a phenylalkyl group containing 1 to 3 carbon atoms in the alkyl part), and the other -100- 200659 of the radicals U and V represents a nucleophilically exchangeable group, or the radical U together with a hydrogen atom at the B-position of the radical £ represents an oxygen atom and V represents an Rg'-NH- group (wherein Rg' is as defined above)]and optionally subsequently cleaving the protective radical or radicals. 24. A process as claimed in claim 23 wherein the reaction is carried out in a solvent. 25. A process as claimed in claim 23 or 24 wherein the reaction is carried out at temperatures between 0 and 150°C. 26. A process as claimed in claim 24 wherein the reaction is carried out at the boiling temperature of the solvent. 27. A process as claimed in any one of claims 23 to 26 wherein the reaction is carried out in the presence of a base. 28. A process as claimed in any one of claims 23 to 27 wherein at least one protective radical is split off hydrolytically in the presence of an acid or base, or, if the protective radical is a benzyl radical, is optionally alternatively split off hydrogenolytically. 29. A process for the preparation of compounds as claimed in claim 1 wherein Rg represents a hydrogen atom, an alkenyl group containing 3 to 5 carbon atoms, an alkyl group containing 1 to 3 carbon atoms or a phenylalkyl group containing 1 to 3 carbon atoms in the alkyl part, which comprises reacting a compound of general formula VI N - E - H (VI) -101- 7 006 5 9 t-1« (wherein A, B, E, R1 and R2 are as defined in claim 1, except that in the radical E two hydrogen atoms of -CH2~ or CH^- group are replaced by an oxygen atom) with an amine of general formula VII (wherein G, R^, R^ and R^ are as defined in claim 1 and Rg' represents a hydrogen atom, an alkenyl group containing 3 to 5 carbon atoms, an alkyl group containing 1 to 3 carbon atoms, or a phenylalkyl group containing 1 to 3 carbon atoms in the alkyl part) in the presence of a reducing agent. 30. A process as claimed in claim 29 wherein the reaction is carried out in a solvent. 31. A process as claimed in claim 29 or claim 30 wherein the reaction is carried out at temperatures between 0 and 100°C. 32. A process as claimed in any one of claims 29 to 31, wherein Rg represents a hydrogen atom and the reaction is carried out in the presence of hydrogen and a hydrogenation catalyst. 33. A process as claimed in any one of claims 29 to 31 wherein the reaction is carried out in the presence of a complex metal hydride at pH 6-7 at room temperature. 34. A process as claimed in claim 33 wherein the complex metal hydride comprises lithium cyanoborohydride or sodium cyanoborohydride. 35. A process for the preparation of compounds as claimed in claim 1 wherein Rg represents a hydrogen atom, an alkenyl group containing 3 to 5 carbon atoms, an alkyl group containing 1 to 3 carbon atoms or a R (VII) -102-

2 0P65 phenylalkyl group containing 1 to 3 carbon atoms in the alkyl part, which comprises reacting a compound of general formula VIII - e - n h V (viii) (wherein A,B,E,R^ and R2 are as defined in claim 1 and Rg' represents a hydrogen atom, an alkenyl group containing 3 to 5 carbon atoms, an alkyl group containing 1 to 3 carbon atoms, or a phenylalkyl group containing 1 to 3 carbon atoms in the alkyl part) with a compound of general formula IX h - g (ix) (wherein G, R^, R^ and R^ are as defined in claim 1, except that in the radical G two hydrogen atoms in a -CH2- or CH^- group are replaced by an oxygen atom) in the presence of a reducing agent. 36. A process as claimed in claim 35 wherein the reaction is carried out in a solvent. 37. A process as claimed in claim 35 or claim 36 wherein the reaction is carried out at temperatures between 0 and 100°C. 38. A process as claimed in any one of claims 35 to 37, wherein Rg represents a hydrogen atom and the reaction is carried out in the presence of hydrogen and a hydrogenation catalyst. 39. A process as claimed in any one of claims 35 to 37 wherein the reaction is carried out in the presence -103- 9 n 0 ^ 5 of a complex metal hydride at pH 6-7 at room temperature. 40. A process as claimed in claim 39 wherein the complex metal hydride comprises lithium cyanoborohydride or sodium cyanoborohydride. 41. A process for the preparation of compounds as claimed in claim 1 wherein A represents a -NH-CO-group, E represents an ethylene, n-propylene or n-butylene group (optionally substituted by an alkyl group containing 1 to 3 carbon atoms) and Rg does not represent a hydrogen atom, which comprises reacting a compound of general formula X v¥r ? ch2 - b - a (wherein B and G are as defined in claim 1, E' represents an ethylene, n-propylene or n-butylene group optionally substituted by an alkyl group containing 1 to 3 carbon atoms, R2'' R3' an(^ R4' each represent a hydroxy group protected by a protective radical or represent R^, R2, R-j and R^ as defined in claim 1, R^" represents a hydroxy, amino or alkylamino group protected by a protective radical or represents R^ as defined in claim 1 with the exception of an amino or alkylamino group, and Rg" represents Rg as defined in claim 1 with the exception of a hydrogen atom or represents a protective group for an amino group) with a carbonic acid derivative of general formula XI W - CO - W (XI) [wherein W and W, which may be the same or different, each represent a nucleophilically exchangeable group, an alkoxy group containing 1 to -104- 200659

3 carbon atoms (optionally substituted by halogen atoms) or an imidazolyl-(2) group] and optionally subsequently cleaving the protective radical or radicals. 42. A process as claimed in claim 41 wherein W and W* each represent a chlorine or bromine atom. 43. A process as claimed in claim 41 or claim 42 wherein the reaction is carried out in the presence of a base. 44. A process as claimed in any one of claims 41 to 43 wherein the reaction is carried out in a solvent at temperatures between 0 and 150°C. 45. A process as claimed in claim 44 wherein the reaction is carried out at the boiling temperature of the solvent. 46. A process as claimed in any one of claims 41 to 45 wherein at least one protective radical is split off hydrolytically in the presence of an acid or base, or if the protective radical is a benzyl radical, is optionally alternatively split off hydrogenolytically. 47. A process for the preparation of compounds as claimed in claim 1 wherein A represents a group, R^ and R2 do not represent benzyloxy groups, and do not represent nitro groups and R^ does not represent a benzyl group or an alkenyl group containing 3 to 5 carbon atoms, which comprises hydrogenating a compound of general formula XII R 1 R CH=CH B / \ N - E - N - G (XII) R R 2 5 wherein R^, R2, 1*3* R^* R^, B, E and G are as defined in claim 1 except that R3 or R4 may not represent a nitro group if represents an amino group. -105- 1 A ■ J .J! 48. A process as claimed in claim 47 wherein the reaction is carried out in a solvent. 49. A process as claimed in claim 47 or claim 48 wherein the hydrogenation is carried out at a hydrogen pressure of 1 to 7 bar. 50. A process as claimed in claim 49 wherein the hydrogen pressure is 3 to 5 bar. 51. A process as claimed in any one of claims 47 to 50 wherein the reaction is carried out at temperatures between 0 and 75°C. 52. A process as claimed in claim 51 wherein the temperatures are between 20 and 50°C. 53. A process for the preparation of compounds as claimed in claim 1 which comprises reacting a compound of general formula XIII \ N / B - E - N - G (XIII) (wherein R^, R2, R3, R^, R5, Rgr A, B, E and G are as defined in claim 1, whereby however, at least one of the radicals R^, R2, R3 and R^ represents a hydroxy group or R^ represents a hydroxy group, an amino group or an alkylamino group containing 1 to 3 carbon atoms or Rg represents a hydrogen atom) with a compound of general formula XIV R8 - X (XIV) wherein Rg represents an alkyl group containing 1 to 3 carbon atoms or (if Rg represents a hydrogen atom) an alkenyl group containing 3 to 5 carbon atoms, or (if R^ or represents a hydroxy group and/or Rg represents a hydrogen atom) an alkyl group containing -106- 7 0 0 6 5 ■3 * ^ 1 to 3 carbon atoms substituted by a phenyl group, and X represents a nucleophilically exchangeable group; or (if at least one of the radicals R^, R2, R3» R^ and R^ represents a hydroxy group) X together with the hydrogen atom at the a-position of the radical Rg may represent a diazo group or (if Rg represents a hydrogen atom or Rg represents an amino or alkylamino group) an oxygen atom. 54. A process as claimed in claim 53 wherein the nucleophilically exchangeable group X comprises a halogen atom or a sulfonyloxy group. 55. A process as claimed in claim 53 or claim 54 wherein the reaction is caried out in a solvent. 56. A process as claimed in any one of claims 53 to 55 wherein the reaction is carried out at temperatures between 0 and 150°C. 57. A process as claimed in any one of claims 53 to 56, wherein X represents a nucleophilically exchangeable group and the reaction is carried out in the presence of an acid-binding agent, at temperatures between 20 and 80°C. 58. A process as claimed in any of claims 53 to 57 wherein at least one of the radicals R^, R2, R3, R^ and Rg represents a hydroxy group and the reaction is carried out with a diazo compound of general formula XIV, at temperatures between 0 and 30°C. 59. A process as claimed in any one of claims 53 to 57, wherein Rg represents a hydrogen atom and/or Rg represents an amino or alkylamino group and the reaction is carried out with an aldehyde of general formula XIV in the presence of a reducing agent at temperatures between 0 and 120°C. 60. A process as claimed in claim 59 wherein the reaction is carried out in the presence of formic acid as the reducing agent at the boiling temperature of the reaction mixture. 61. A process as claimed in claim 59 wherein the reaction is carried out in the presence of sodium -107- 200659 cyanoborohydride as the reducing agent, at room temperature and at pH 6-7. 62. A process for the preparation of compounds as claimed in claim 1 wherein A does not represent a -CH=CH- group, represents a chlorine or bromine atom and R^ represents an amino or alkylamino group, which comprises halogenating a compound of general formula XV wherein R-^, R2, R^, Rg> B, E and G are as defined in claim 1, A' represents A as defined in claim 1 with the exception of a -CH=CH- group and Rg"" represents an amino group or an alkylamino group containing 1 to 3 carbon atoms. 63. A process as claimed in claim 62 wherein the compound of general formula XV is used in the form of an acid addition salt thereof. 64. A process as claimed in claim 62 or claim 63 wherein the reaction is carried out in a solvent. 65. A process as claimed in any one of claims 62 to 64 wherein the reaction is carried out at temperatures between 0 and 50"C. 66. A process as claimed in any one of claims 62 to 65 wherein the reaction is carried out in the presence mercuric oxic\e. of /a hoa^Vy motal compound./ 67. A process for the preparation of compounds as claimed in claim 1 wherein A represents a -COCO- group,- V -108- 200659 and E B represents a methylene group /E^and/ represents an ethylene, n-propylene or n-butylene group (optionally substituted by an alkyl group containing 1 to 3 carbon atoms), which comprises oxidising a compound of general formula XVI (XVI) ch2-ch2 wherein R1# R2, R3, R4, R5, Rg and G are as defined in claim 1, and E represents an ethylene, n-propylene or n-butylene group (optionally substituted by an alkyl group containing 1 to 3 carbon atoms). 68. A process as claimed in claim 67 wherein the reaction is carried out in a solvent. 69. A process as claimed in claim 67' or claim 68 wherein the oxidation is carried out using an oxidising agent. 70. A process as claimed in claim 69 wherein the oxidising agent comprises potassium permanganate, selenium dioxide or sodium dichromate. 71. A process as claimed in any one of claims 67 to 70 wherein the reaction is carried out at temperatures between 0 and 100°C. 72. A process as claimed in claim 71 wherein the temperature range is from 20 to 80°C. 73. A process as claimed in any one of claims 16 to 72 wherein a compound of general formula I wherein B represents a carbonyl group, initially obtained, is subsequently converted by reduction into a compound of general formula I wherein B represents a methylene group; and/or a compound of general formula I, wherein b A does not represent -CH=CH- or -ON- group and R, 6 does not represent a benzyl or 1-phenylethyl group, . x -ioy- 7 Q ff P-. ^ ^ initially obtained is subsequently converted by means of catalytic hydrogenation into a compound of general formula I wherein Rg represents a hydrogen atom; and/or a compound of general formula I wherein R^ or R^ represents a nitro group, initially obtained, is subsequently converted by reduction into a compound of general formula I wherein R^ represents an amino group; and/or a compound of general formula I wherein Rg represents a hydrogen atom and/or R^ represents an amino group initially obtained, is subsequently converted by acylation into a compound of general formula I wherein Rg represents an alkanoyl or alkoxycarbonyl group and/or R^ represents an alkanoylamino, alkoxycarbonylamino or bis(alkoxycarbonyl)-amino group, wherein the alkyl part may contain from 1 to 3 carbon atoms each; and/or a compound of general formula I wherein R5 represents an amino group, Rg does not represent a hydrogen atom and neither R^ nor R^ represents a cyano group, initially obtained, is subsequently converted via a diazonium salt into a compound of general formula I wherein R^ represents a hydrogen atom, a hydroxy or alkoxy group or R^ represents a hydrogen atom and R^ represents a halogen atom or a cyano group. 74. A process as claimed in any one of claims 16 to 73 wherein a compound of formula I initially obtained is subsequently converted into an acid addition salt thereof or an acid addition salt of a compound of formula I initially obtained is subsequently converted into a compound of formula I. 75. A process as claimed in any one of claims 16 to 74 for the preparation of compounds as claimed in claim 13. 76. A process for the preparation of compounds as claimed in claim 1 substantially as herein described in any one of the Examples. 77. A process for the preparation of compounds as claimed in claim 13 substantially as herein described in any one of Examples 1, 2 and

4-10. 1 200653 -110- 78. Compounds as claimed in claim 1 when prepared by a process as claimed in any one of claims 16 to 77. 79. Compounds as claimed in claim 13 when prepared by a process as claimed in claim 75 or 77. 80. Pharmaceutical compositions comprising as active ingredient at least one compound of formula I as defined in claim 1 or a physiologically compatible acid addition salt thereof, in association with one or more pharmaceutical carriers or excipients. 81. Compositions as claimed in claim 80 in a form suitable for oral, rectal or parenteral administration. 82. Compositions as claimed in claim 80 or claim 81 in the form of tablets, coated tablets, capsules, drops, suppositories, ampoules, suspensions, powders or syrups . 83. Compositions as claimed in any one of claims 80 to 82 in the form of dosage units. 84. Compositions as claimed in any one of claims 80 to 83 wherein the compounds of formula I are as defined in claim 13. 85. Pharmaceutical compositions as claimed in claim 80 substantially as herein described. 86. Pharmaceutical compositions substantially as herein described in any one of Examples I to V. 87. Compounds of general formula I as claimed in physt* loot Coity claim 1 and /phyftiolgically/ compatible acid addition salts thereof|for use in a method of treatment of patients suffering from disorders of heart-rate, including sinus tachycardia and ischaemic cardiac diseases. 88. A method of treating^patients suffering from, or susceptible to, disorders of heart-rate which comprises ad rvuiuifcnVq jfrdmiftotoring/ to the said patient an effective amount of~a compound of formula I as defined in claim 1 or a physiologically compatible acid addition salt thereof. 89 . Bach qnd every novel yethodj proccooy—compound -or oompocition herein dioofl-oocd. vol ioofloi BALDWIN, SON & CAREY ATTORNEYS FOR THE APPLiCANiS </div>