DD284678A5 - PROCESS FOR THE PREPARATION OF NEW CYCLIC AMINE DERIVATIVES - Google Patents

Abstract

Cyclic amine derivatives of the formula <IMAGE> in which A, B, E, G, R, R1, R2, m and n are as defined in Claim 1, their enantiomers, their diastereomers, their N-oxides and their acid addition salts have useful pharmacological properties, in particular a bradycardic action. The novel compounds can be prepared by processes known per se.

Description

Process for the preparation of novel cyclic amine derivatives Field of application of the invention

The erfindungsgemäeri. Compounds are used in the pharmaceutical industry. They are suitable for the manufacture of medicaments which have a hypotensive, a long-lasting heart rate lowering effect and a lowering effect on the oxygen demand of the heart.

Characteristic of the known technical solutions

In British Patent 1,543,344 u. a. the connection of the Jormel

CCH

and their physiologically tolerated acid addition salts, which have valuable plaque pharmacological properties, in addition to a mild hypotensive action, in particular a selective heart rate lowering effect.

Object of the invention

The invention provides novel cyclic i-siiinderivate whose john-

rneren whose diastereoisomers, their IT oxides and their acid addition salts, in particular their physiologically acceptable Süureadditionssalze nit inorganic or organic acids ready, have the valuable pharraakologische properties.

Loan of "the invention of the invention

The invention has for its object to provide new cyclic Jüninderivate nit valuable Pharraakologisehen properties.

The present invention relates to processes for the preparation of the novel cyclic ikaine derivatives of Fornel I,

Π - E - CH IT-G-R, (I)

their enantiomers, their Diaatereoneren, their ΙΓ-Gjcide, Suureadditionssalze, in particular for the pharmaceutical use of their physiologically contractual SL'.ureadditioncsalzc nit inorganic or organic acids co v / i e method for preparing these compounds containing drugs.

In the above general formula I, A is a -CII ₂ , -CH ₂ -CII ₂ or -ClbCII group, 3 is a -CH ₂ -, -CII ₂ -CIi ₂ -, -CO- or -CHgCO group .

wherein the Rait χ marked carbon atom with the phenyl nucleus is linked,

E is a straight-chain alkylene group having 1 to 3 carbon atoms optionally substituted by an alkyl group having 1 to 3 carbon atoms,

G is a straight-chain alkylene group having 1 to Kohlenstoffatomen carbon atoms optionally substituted by an alkyl group having 1 to 3 carbon atoms, wherein the ethylenic group connected to an aromatic or heteroaromatic group R is a straight-chain alkylene group having 3 to Kohlenstoffatomen carbon atoms optionally substituted by an alkyl group having 1 to 3 carbon atoms through an oxygen or

Sulfur atom, a sulfinyl, sulfonyl or optionally substituted by an alkyl group having 1 to 3 carbon atoms imino group may be replaced,

R _{1 represents} a hydrogen or halogen atom, a trifluoromethyl, nitro, amino, alkylamino, dialkylamino, alkyl, hydroxy, alkoxy or phenylalkoxy group, each alkyl moiety each containing from 1 to 3 carbon atoms,

1 * 2 represents a hydrogen atom or halogen atom, a hydroxy, alkoxy, phenylalkoxy or alkyl group, each alkyl moiety each containing 1 to 3 carbon atoms, or

R ₁ and R ₂ together represent an alkylenedioxy group having 1 or 2 carbon atoms,

m is the number 1, 2, 3, 4, 5 or 6 and

η is the number 0, 1, 2 or 3, but where η + m is 3, 4, 5 or 6, and

R is a 5- or 6-membered heteroaromatic ring bonded via a carbon or nitrogen atom and containing an oxygen, sulfur or nitrogen atom, two nitrogen atoms or a nitrogen atom and one oxygen or sulfur atom, and to which a phenyl ring may additionally be fused in which case the bond can also be via the phenyl nucleus and in which the carbon skeleton of the abovementioned mono- and bicyclic rings is replaced by a halogen atom, an alkyl, hydroxy, alkoxy, phenylalkoxy, phenyl, dimethoxyphenyl, Nitro, amino, acetylamino, carbamoylamino, N-alkylcarbamoylamino, hydroxymethyl, mercapto, alkylmercapto, alkylsulfinyl, alkylsulfonyl, alkylsulfonyloxy, alkylsulfonylamino, alkoxycarbonylmethoxy, carboxymethoxy or alkoxymethyl

* 0 group mono- or disubstituted or by a methylene

or an ethylenedioxy group may be substituted and at the same time an optionally present imino group in the above-mentioned heteroaromatic rings may be substituted by an alkyl, phenylalkyl or phenyl group, an indolyl group mentioned above additionally being substituted by a methylamino, dimethylamine, methoxy, acetoxy, Trifluoromethyl, trichloromethyl, carboxy, methoxycarbonyl, ethoxycarbonyl, cyano, cyclohexyl, trimethoxyphenyl, trifluorophenyl, trichlorophenyl, tribromophenyl, dihaloaraino-phenyl, benzyl, benzyloxy or benzylamino groups and in which case the abovementioned benzyl, benzyloxy or benzylamino substituents of the indolyl group in the benzyl nucleus can be mono-, di- or tri-substituted by methoxy or methyl groups, where the substituents can be identical or different, optionally by an alkylenedioxy group having 1 or 2 carbon atoms substituted naphthyl group or a d by halogen atoms, alkyl, hydroxy, alkoxy, alkylsulfonyloxy, nitro, amino or alkanoyiaminogruppen mono- or disubstituted naphthyl group, wherein the substituents may be identical or different, a benzyloxy or 4,5,6,7-tetrahydro benzo [b] thienyl group, or even when B represents a -CH ₂ - or -OO- group, a phenyl optionally substituted by an alkylenedioxy group having 1 or 2 carbon atoms, one represented by a halogen atom, an alkyl, hydroxy, alkoxy , Phenylalkoxy, nitro, amino, alkanoylamino, alkylsulfonylamino, bis (alkylsulfonyl) amino, alkylsulfonyloxy, trifluoromethyl, trifluoromethoxy or trifluoromethylsulfonyloxy group-substituted phenyl group, phenyl group disubstituted by halogen atoms, alkyl or alkoxy groups, wherein the substituents may be the same or different, a trialkoxyphenyl, tetraalkylphenyl or dihalo-aminophenyl group, which, unless otherwise stated, in the Definitio n of the radical R mentioned above alkyl, alkoxy or alkanoyl may each contain 1 to 3 carbon atoms.

For the meanings mentioned in the definition of the radicals at the outset, for example

R 1 represents hydrogen, fluorine, chlorine or bromine, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, hydroxy, methoxy, ethoxy, n-propoxy, isopropoxy, Nitro, amino, methylamino, ethylamino, n-propylamino, isopropylamino, dimethylamino, diethylamino, di-n-propylamino, diisopropylamino, N-methyl-ethylamino, N-methyl-n-propylamino , N-methyl-isopropylamino, N-ethyln-propylamino, benzyloxy, 1-phenylethoxy, 1-phenylpropoxy, 2-phenylethoxy or 3-phenylpropoxy group,

for R 1, the hydrogen, chlorine or bromine atom, the methyl, ethyl, n-propyl, isopropyl, hydroxy, methoxy, ethoxy, n-propoxy, isopropoxy, benzyloxy, 1 Phenylethoxy, oxy, 2-phenylethoxy, 2-phenylpropoxy or 3-phenylpropoxy group or together with R, the methylenedioxy or ethylenedioxy group,

for E, the methylene, ethylene, n-propylene, ethylidene, n-propylidene, n-butylidene, 2-methyl-n-propylidene, 1-methyl-ethylene, 1-ethyl-ethylene , 2-methyl-ethylene, 2-ethylethylene, 1-n-propyl-ethylene, 1-methyl-n-propylene, 2-methyln-propylene, 3-methyl-n-propylene, 1-ethyl n-propylene, 2-n-propyl-n-propylene or 3-ethyl-n-propylene group,

for G, the methylene, ethylidene, n-propylidene, n-butylidene, 2-methyl-propylidene, ethylene, 1-methyl-ethylene, 1-ethyl-ethylene, 1-propyl-ethylene , 2-methyl-ethylene, 2-ethyl-ethylene, n-propylene, n-butylene, n-pentylene, n-hexylene, 1-methyl-n-propylene, 1-methyl-n- butylene, 1-methyl-n-pentylene, 1-ethyl-n-propylene, 2-ethyl-n-propylene, l-ethyl-n-butylene, ethyleneoxy, n-propyleneoxy, n-butyleneoxy , Ethylene thio, n-propylene thio, n-butyl thio, ethylene sulfinyl, ethylene sulfonyl, n-propylene sulfinyl, n-propyl

pylenesulfonyl, n-butylenesulfinyl, ethyleneamino, n-propyleneamino, n-butyleneamino, N-methylethyleneamino, N-methyl-n-propyleneamino, N-ethyl-n-propyleneamino, N-isopropyl n-propyleneamino or N-methyl-n-butyleneamino group and

for R, the pyrrolyl-2-, pyrrolyl-3, N-methylpyrrolyl-2-, N -methyl-pyrrolyl-3-, 1'-dimethyl-pyrrolyl, -, г ^ -БітеиЬуі-руггоіуі-З- , Furyl-2-, furyl-3-, 5-methyl-furyl-2-, 2-methyl-furyl-3, 5-nitro-furyl-2-, 5-methoxymethyl-furyl-2-, benzo [b ] furyl-2, benzo [b] furyl-3, 7-methylbenzo [b] furyl-3, 2-methoxy-benzo [b] furyl-3, 3-methoxybenzo [b] furyl-2, 4-methoxy-benzo [b] furyl-3, 5-methoxybenzo [b] furyl-3, 6-methoxy-benzo [b] furyl-3, 7-methoxybenzo [b] furyl-3, 5 Methoxy-3-phenyl-benzo [b] furyl-2, 3-methyl-5-methoxy-benzo [b] furyl-2, thienyl-2, thienyl-3,

¹ ^ S-methyl-thienyl-2-, г-Меііпуі-Ъпіепуі-З-, 3-methyl-thienyl-2-, 2,5-dimethyl-thienyl-3, 4,5,6,7-tetrahydro- benzo [b] thienyl-3, 4,5,6,7-tetrahydrobenzo [b] thienyl-2-, S-chlorothienyl-2-, 5-bromo-thienyl-2-, S-phenyl -thienyl-2-, 2-phenyl-thienyl-3, benzo [b] thienyl-2-, benzo [b] thienyl-3, 2,5-dimethyl-benzo [b] thienyl-3, 5 Methyl benzo [b] thienyl-3, 6-methylbenzo [b] thienyl-3, 5-chloro-benzo [b] thienyl-2-, 5-bromo-benzo [b] thienyl-3, 6-Hydroxybenzo [b] thienyl-3, 7-hydroxybenzo [b] thienyl-3, 5-hydroxybenzo [b] thienyl-2-, 6-hydroxybenzo [b] thienyl- 2-, 7-Hydroxy-benzo [b] thienyl-2-, 6-methanesulfonyloxy-benzo [b] thienyl-3, 3-methoxy-benzo [b] thienyl-2-, 4-methoxy-benzo [b ] thienyl-2-, 5-methoxy-benzo [b] thienyl-2- _r 6-methoxy-benzo [b] thienyl-2-, 7-methoxy-benzo [b] thienyl-2,2-methoxy-benzo [b] thienyl-3, benzo [b] thienyl-4, benzo [b] thienyl-5, benzo [b] thienyl-6,

Benzo [b] thienyl-7-, 4-methoxybenzo [b] thienyl-3, 5-methoxybenzo [b] thienyl-3, 6-methoxybenzo [b] thienyl-3-, 7- Methoxy-benzo [b] thienyl-3, 5,6-dimethoxy-benzo [b] thienyl-3, 5,6-methylenedioxy-benzo [b] thienyl-3, 6-ethoxybenzo [b] thienyl-3-, 6-propoxy-benzo [b] thienyl-3-, 6-isopropoxy

benzo [b] thienyl-3-, 6-mercapto-benzo [b] thienyl-3-, 6-methyl-

mercapto-benzo [b] thienyl-3- / 6-methylsulfinyl-benzo [b] thienyl-3, 6-methylsulfonyl-benzo [b] thienyl-3, 6-methylsulfonyloxy-benzo [b] thienyl-3, 6-Methoxycarbonylmethoxybenzo [b] thienyl-3-, 6-ethoxycarbonylmethoxybenzo [b] thienyl-3, 6-carboxymethoxybenzo [b] thienyl-3- / 6-aminobenzo [b] thienyl- 3-, 6-Methylamino-benzo [b] thienyl-3, 6-dimethylaminobenzo [b] thienyl-3, б-diethylaraino-benzo [b] thienyl-3, ib-acetaminobenzo [b] thienyl- 3-, 6-Methylsulfonylamino-benzo [b] thienyl-3, pyrazolyl-1, pyrazolyl-3, 3,5-dimethyl-pyrazolyl-1-,!, S-dimethyl-pyrazolyl-S-, imidazolyl -1-, imidazolyl-2, imidazolyl-4 (5) -, 1-methylimidazolyl-4-, 1-benzyl-imidazolyl-4-, 5-nitro-2-methyl-imidazolyl-l, 2- (3,4-dimethoxy-phenyl) -imidazolyl-4 (5) -, benzo [d] imidazolyl-1, 2-benzyl-benzo [d] imidazolyl-1, benzo [d] imidazolyl-2, imidazo [1,2-a] pyridyl-3, oxazolyl-4, oxazolyl-5, isoxazolyl-3, 3-methylisoxazolyl-S, S-methyl-isoxazolyl-3, 3,5-dimethyl -isoxazolyl-4-, 4-methyl-thiazolyl-5, benzo [d] -oxazolyl-2, Benzo [d] isoxazolyl-3-, benzo [d] thiazolyl-2-, 5-ethoxy-benzo [d] thiazolyl-2-, benzo [d] isothiazolyl-3-, benzo [d] pyrazolyl-l, benzo [d] pyrazolyl-3, pyridyl-2, pyridyl-3, pyridyl-4, pyridyl-3-N-oxide, 6-methyl-pyridyl-2-, 4-nitro-pyridyl-2, 4-Amino-pyridyl-2-, 4-acetylamino-pyridyl-2-, 4-carbamoylamidopyridyl-2-, 4-N-methylcarbamoylamino-pyridyl-2-, г-СЬІог-ругіауі-З-, 2-chloro -pyridyl-4, б-СЬІог-ругіауі-г-, 6-hydroxymethyl-pyridyl-2, quinolyl-2, isoquinolyl-1, 2-methyl-quinolyl-4-, 7-methyl-quinolyl-2 , 4-chloro-quinolyl-2-, 6,7-dimethoxy-quinolyl-4-, 6,7-dimethoxy-isoquinolyl-4-, 6,7-dimethoxy-isoquinolyl-4-N-oxide, indolyl- 2-, indolyl-3, 5,7-dibromo-6-cyano-indolyl-3, 5,7-dichloro-b-ami-pocarbo-ipol-i-dipolyl-3, 4,6-dibromo-5-aminocarbonyl-indolyl- 3-, 5,7-Dibromo-6-methoxy-indolyl-3, 5,6-dihydroxy-indolyl-3,4-dimethylaminoindolyl-3,4-methoxy-6-dimethyl-1-ipodolyl-3,4 Methyl 6-dimethylethyl indolyl-3, S-acetoxy-6-dimethylamino-indolyl-3, S-acetamido ^ dimethylamino-indolyl-S,

S-dimethylaminocarbonyl-indolyl-S-, б-СагЬоху-паоіуі-З-, 5-acetamido-indolyl-3-, 4-nitro-5-acetamido-indolyl-3-, S-acetamido-δ-nitro-indolyl- S-, S-nitro-6-acetamido-indolyl-3-, ö-acetamido -nitro-indolyl-1-chloro-S-acetamidoindolyl-3-, S-acetamido-6-chloro-indolyl-S-, 5-Chloro-6-acetamido-indolyl-3, ö-acetamido-1-chloro-indolyl-S, 5-dimethylamino-indolyl-3, 6-dimethylamino-indolyl-S, 7-dimethylamino-indolyl-3 , S-dimethylamino-6-chloro-indolyl-S, S-chloro-e-diraethyl-ara-n-indolyl-S, T-benzyl-indolyl-S-, 4- (3,4,5-trimethoxy-benzyl) -indolyl-3-, 5- (3,4,5-trimethoxy-benzyl) -indolyl-3-, 6- (3,4,5-trimethoxy-benzyl) -indolyl-3-, 7- (3,4 , 5-trimethoxybenzyl) indolyl-3,4-trifluoromethyl-indolyl-3,4-trichloromethyl-indolyl-3,4,5-methylenedioxy-indolyl-3,4,5-dimethoxy-indolyl- 3-, 4,5-dimethyl-indolyl-3-, S-methyl-6-methoxy-indolyl-3,4-methyl-5-methoxy-indolyl-3,5-trifluoromethyl-indolyl-3-, S -Methoxy-7-bromo-indolyl-3, 5-Bact-7-methoxy-indolyl-3, 5-bromo-indolyl -3-, б-Спіог-іпаоіуі-З-, 5- (3,4,5-trimethoxybenzyloxy) indolyl-3-, 6- (3,4,5-trimethoxy-benzyloxy) -indolyi-3-, 5 - (3,4,5-trimethoxybenzylamino) -indolyl-3-, 6- (3,4,5-trimethoxy-benzylamino) -indolyl-3-, 5- (3,5-dichloro-4-amino- benzyloxy) -indolyl-3-, 6- (3, S-dibromo -aminobenzyloxy) -indolyl-3, 5- (3, S-dichloro-amino-benzylamino) indolyl-3-, 6- (3, S-dibromoM-aminobenzylamino) -indolyl-3, S-benzyl-indolyl-S, 4-benzyl-indolyl-3-, 6-benzyl-indolyl-3, 5,6,7-trimethoxy-indolyl -3-, 5,6,7-trimethyl-indolyl-3-, S-nitro-indolyl-3, 4, б-Оіспіог-б-атіпо-іпаоіуі-З-, 4,6-dichloro-5-nitro indolyl-3, 5,7-dibromo-6-amino-indolyl-3, S-dibromo-o-quitro-indolyl-S, 4, 6-dichloro-S-methoxy-indolyl-3, 5,6-dimethoxy-indolyl-3-, 5,7-dimethoxy-indolyl-3-, 6,7-dimethoxy-indolyl-3,4,7-dimethoxy-indolyl-3, 5,6-methylenedioxy- indolyl-3-, 6,7-methylenedioxy-indolyl-3, S, -dimethyl-indolyl-S, 5,7-dimethyl-i-dipolyl-3, 6,7-dimethylindolyl-3, 4, 7-dimethyl-i-dipolyl-3-, 6-methoxy y-7-methyl-i-dipolyl-3, 4, б-ОіЬгот-б-сагЬоху-паоіуі-З-, 5,7-dichloro---carboxy-i-dipolyl-3, 5-ethoxycarbonyl-indole

yl-3, δ-ethoxycarbonyl-indolyl-S, 4, δ-dibromo-S-ethoxycarbonyl-indolyl-3-, 5,7-dichloro-6-ethoxycarbonyl-1-indoly-1,3-, Б-уапо-іпаоіуі- З-, б-Суапо-Паоіуі-З-, 4-Суапо-апаоіуі-З-, 4-HyOrOXy-IIiDOIyI-S-, 7-hydroxy-indolyl-3, 5-phenyl-indolyl-3, б- Рпепуі-Паоіуі-З-, 5- (3,4,5-tribromo-phenyl) -indolyl-3-, 6- (3,4,5-trimethoxyphenyl) -indolyl-3-, 5- (4- Trifluoro-ethyl-phenyl) -indolyl-3-, 6- (3,5-difluoro-4-amino-phenyl) -indolyl-3, 4-phenyl-indolyl-3, 5-cyclohexyl-indolyl-3, 5 - (2-methoxybenzyl) -indolyl-3-, 6- (2-methoxy-phenyl) -indolyl-3-, 6- (2,4-dimethyl-benzyl) -indolyl-3, 5- (2 , 4-Dimethoxy-benzyl) -indolyl-3-, 7- (2-methoxy-benzyloxy) -indolyl-3-, 4- (2,4-di-methyl-benzyloxy) -indolyl-3-, 5- (2, 4-Dimethoxy-benzyloxy-indolyl-3-, 6- (2-methoxybenzylamino) -indolyl-3-, 5- (2-methoxy-4-methyl-benzylamino) -indolyl-3-, 4- (2, 4-dimethoxy-benzylamino) -indolyl-3, 5,7-di-ω-γ-ω-уупо-іпаоіуі-г, 5,7-dichloro-б-ami-pocarbo-ipol-i-dipolyl 2-, 4,6-dibromo-5-aminocarbonyl-indolyl-2-, 5,7-dibromo-6-methoxy-indolyl-2-, 5,6-dihydroxy-indolyl-2-, 4-dimethylaraino-indolyl- 2-, 4-Methoxy-β-dimethylamino-i-dipolyl-2-, 4-methyl-β-dimethylamino-i-dipolyl-2-, S-acetoxy-6-dimethylamino-indolyl-2-, 5-acetamido-7-dimethylamino iпdolyl-2,

апаоіуі-г, 5-carboxy-indolyl-2, -г-, 4-nitro-5-acetamido-i-dipolyl-2-, S-acetamido-δ-nitro-indolyl-2-, 5-nitro-6-one acetamido-indolyi-2, б-acetamido-7-pitro-i-dipolyl-2-, 4-chloro-5-acetamidoindolyl-2-, S-acetamido-6-chloro-indolyl-1 -, S-chloro-6-acetamido -indolyl-2-, б-acetamido-7-chloro-i-dipolyl-2-, 5-dimethylamino-indolyl-2-, 6-dimethylamino-indolyl-2-, 7-dimethyl-amino-indolyl-2-, S-dimethylamino ö-chloro-indolyl ^ -,

™ 5-chloro-β-dimethylamino-i-dipolyl-2-, 7-benzyl-indolyl-2-, 4- (3,4,5-trimethoxy-benzyl) -indolyl-2-, 5- (3,4,5 Trimethoxy-benzyl) -indolyl-2-, 6- (3,4,5-trimethoxy-benzyl) -indolyl-2-, 7- (3,4,5-trimethoxy-benzyl) -indolyl-2-, 4 Trifluoromethyl-indolyl-2-, 4-trichloromethyl-indolyl-2-, 4,5-methylenedioxy-indolyl-2-, 4,5-dimethoxy-indolyl-2-, 4,5-dimethyl-indolyl-2, 5-methyl-6-methoxy-indolyl-2-, 4-methyl-5-

methoxy-indolyl-2-, 5-trifluoromethyl-indolyl-2-, 5-methoxy-7-bromo-indolyl-2-, S-bromo-1-methoxy-indolyl-2-, 5-bromoindolyl-2, б- СЫог-іпаоіуі-г-, 5- (3,4,5-trimethoxy-benzyloxy) -indolyl-2-, 6- (3,4,5-trimethoxy-benzyloxy) -indolyl-2-, 5- (3, 4,5-trimethoxybenzylamino) indolyl-2-, 6- (3,4,5-trimethoxybenzylamino) indolyl-2-, 5- (3,5-dichloro-4-aminobenzyloxy) -indolyl-2 -, 6- (3,5-dibromo-4-amino-benzyloxy) -indolyl-2-, 5- (3,5-dichloro-4-amino-benzylamino) -indolyl-2-, 6- (3,5 Dibromo-4-amino-benzylamino) -indolyl-2-, 5-benzyl-indolyl-2-, 4-benzyl-indolyl-2-, 6-benzyl-indolyl-2-, 5,6,7-trimethoxy indolyl-2-, 5,6,7-trimethyl-indolyl-2-, 5-nitroindolyl-2-, 4, 6-dichloro-S-amino-indolyl-, 4,6-dichloro-S-nitro -indolyl ^ -, 5, Т-ОіЬгот-б-атіпо-паоіуі-г-, 5,7-dibrо-б-η-indol-indolyl-2-, 4-δ-dichloro-S-methoxy-indolyl-2-, 5,6-dimethoxy-indolyl-2-, 5,7-dimethoxy-indolyl-2-, 6,7-dimethoxy-indolyl-2-, 4,7-dimethoxy-indolyl-2-, 5,6-methylenedioxy- indolyl-2-, 6,7-methylenedioxy-indo lyl-2-, S, -dimethyl-indolyl-, 5,7-dimethyl-indolyl-2-, 6,7-dimethyl-indolyl-2-, 4,7-dimethyl-indolyl-2-, 6-methoxy -7-methyl-indolyl-2-, 4, ö-dibromo-S-carboxy-indolyl-2-, 5,7-di-

6-ethoxycarbonyl-indolyl-2-, 4, 6-dibromo-S-ethoxycarbonyl-indolyl-2-, 5,7-dichloro-6-ethoxycarbonyl-indolyl-2-, 5-cyanoindolyl-2-, 6-cyano- indolyl-2-, 4-cyano-indolyl-2-, 4-hydroxy-indolyl-2-, 7-hydroxy-indolyl-2-, 5-phenyl-indolyl-2-, 6-phenyl-indolyl-2-, 5- (3,4,5-tribromo-phenyl) -indolyl-2-, 6- (3,4,5-trimethoxyphenyl) -indolyl-2-, 5- (4-trifluoromethyl-phenyl) -indolyl- 2-, 6- (3,5-Difluoro-4-amino-phenyl) -indolyl-2-, 4-phenyl-indolyl-2-, 5-cyclohexyl-indolyl-2-, 5- (2-methoxy-benzyl ) -indolyl-2-, 6- (2-methoxy-phenyl) -indolyl-2-, 6- (2,4-dimethyl-benzyl) -indolyl-2-, 5- (2,4-dimethoxy-benzyl) -indolyl-2-, 7- (2-methoxy-benzyloxy) -indolyl-2-, 4- (2,4-dimethyl-benzyloxy) -indolyl-2-, 5- (2,4-dimethoxybenzyloxy-indolyl-2 , 6- (2-methoxybenzylamino) -indolyl-2-, 5- (2-methoxy-4-methylbenzylamino) -indolyl-2-, 4- (2,4-dimethoxybenzylamino) indolyl- 2-, phenyl, 4-methylphenyl,

3-methyl-phenyl, 2-methyl-phenyl, 4-ethyl-phenyl, 4-isopropyl-phenyl, 4-cyano-phenyl, 4-trifluoromethyl-phenyl, 2-methoxy-phenyl, 3 -Methoxy-phenyl, 4-methoxy-phenyl, 2-ethoxy-phenyl, 4-nitro-phenyl, 2-nitro-phenyl, 4-methyl-amino-phenyl, 4-ethyl-amino-phenyl, 4- n-propylaminophenyl, 4-dimethylamino-phenyl, 4-diethylamino-phenyl, 4-di-n-propylamino-phenyl, 4-N-ethyl-methyl-amino-phenyl, 4-formyl-ara-n-phenyl, 4- Acetamido-phenyl, 4-propionylamino-phenyl, 3,4-methylenedioxy-phenyl, 3,4-ethylenedioxy-phenyl, 3,4-dimethoxy-phenyl, 3,5-dimethoxy-phenyl, 2, 6-dimethoxy-phenyl, 2,4-dimethoxy-phenyl, 3,4-diethoxyphenyl, 3,4-dimethyl-phenyl, 3,5-dimethyl-phenyl, 2,6-dimethyl-phenyl, 2,4-dimethyl-phenyl, 3,4-diethyl-phenyl, 2,4-dichloro-phenyl, 2,4-dibromo-phenyl, 3-methyl-4-methoxy-phenyl, S-methoxy ^ -methyl-phenyl, 3-chloro-4-methylphenyl, 3-bromo-4-methyl-phenyl, 3-chloro-4-mcthoxy-phenyl, З-ω-4-methoxy-phenyl, 3 -Methyl-4-chloro-phenyl, 3-methyl-4-bromo-pheny 1-, 3-methoxy-4-chlorophenyl, 3-methoxy-4-bromo-phenyl, benzyloxy, naphthyl-1, naphthyl-2, 2-methyl-naphthyl-1-, 6-methoxy -naphthyl-2-, 7-methoxynaphthyl-2-, 5-methyl-6-methoxynaphthyl-2-, 5,6-dimethoxy-naphthyl-2-, 5,6-dichloro-naphthyl-2-, 5,6-Dimethoxy-naphthyl-l, 5,6-dichloro-naphthyl-1, ib-methoxy-naphthyl-l, 5-methyl-6-methoxynaphthyl-1, 6-nitro-naphthyl- 1-, 6-nitro-naphthyl-2-, 6-methoxy-S-nitro-naphthyl-1-, 6-methoxy-5-nitronaphthyl-2-, 6-amino-naphthyl-2-, 4-methoxynaphthyl -l, 5, ö-diethoxy-naphthyl ^, 5, б-di-п-propoxy-2-paphthyl-2-, 6-chloro-naphthyl-l, ö-chloro-naphthyl-2, ö-Chloc -T-nitronaphthyl-2-, 6-chloro-7-amiopo-naphthyl-2-, 6-chloro-T-acetamido-naphthyl-2-, 5,6-methylepdioxy-p-p-butyl-2-, 5-chloro-6 methoxy-naphthyl-2-, 6-ethyl-naphthyl-2-, 6-methylmercapto-naphthyl-2- and 6-isopropyl-naphthyl-2-group.

For example, mention may be made of the following compounds which fall within the scope of the present invention, but are not described explicitly in the examples:

2- [(N- (2- (naphthyl-2) -ethyl) -hexahydro-azepinyl-3) -methyl] -6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline,

2 - [(N- (2- (2-naphthyl) ethyl) -azacyclooctyl-3) -methyl] -6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline,

2 - [(N- (2- (l-naphthyl) ethyl) hexahydro-azepinyl-3) -methyl] -6,7-dimethoxy-l-oxo-l, 2,3,4-tetrahydro-isoquinoline,

2 - [(N- (2- (1-naphthyl) ethyl) -azacyclooctyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline,

2 - [(N- (2-methyl-l-naphthyl) -methyl) -pyrrolidyl-3) -methyl] -6,7-dimethoxy-l-oxo-1,2,3,4-tetrahydro-isoquinoline,

2- [3- (N- (2-methyl-l-naphthyl) methyl) -piperidyl-3) -propyl] -6,7-dimethoxy-l-oxo-l, 2,3,4-tetrahydro-isoquinoline .

2 - [(N- (2- (5-methyl-6-methoxynaphthyl-2) -ethyl) -pyrrolidyl-3) -methyl] -6,7-dimethoxy-1,2,3,4-tetrahydro- isoquinoline,

2 - [(N- (2- (5-methyl-6-methoxynaphthyl-2) -ethyl) -azacyclooctyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3, 4-tetrahydro-isoquinoline,

2 - [(N- (2- (6-Methoxy-naphthyl-2) -ethyl) -hexahydro-azepinyl-3) methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro isoquinoline,

2- [(N- (2- (6-Methoxy-naphthyl-2) -ethyl) -azacyclooctyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro- isoquinoline,

2- [3- (N- (2- (6-methoxy-naphthyl-2) -ethyl) pyridyl-3) -propyl] -6,7-dimethoxy-l-oxo-l, 2,3,4- tetrahydro-isoquinoline,

2 - [(N- (4- (naphthyl-2-oxy) butyl) -azacyclooctyl-3) -methyl] -6,7-dimethoxy-l, 2,3,4-tetrahydro-isoquinoline,

2- [2- (N- (4- (naphthyl-2-oxy) butyl) -piperidyl-2) -ethyl] -6,7-dimethoxy-l-oxo-1,2 / 3,4-tetrahydro- isoquinoline,

(N- (3- (naphthyl-2-oxy) -propyl) -azacyclooctyl-3) 2-t -methyl] -6,7-dimethoxy-l-oxo-l, 2,3,4-tetrahydro-isoquinoline,

(N- (3- (2-naphthyl) -propyl) -piperidyl-3) 2-t -methyl] -6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline,

2 - [(N- (3- (2-naphthyl) -propyl) -azacyclooctyl-3) -methyl] -6,7-dimethoxy-l-oxo-1,2,3,4-tetrahydro-isoquinoline,

2 - [(N- (2- (2-naphthyl) ethyl) -piperidyl-3) -methyl] -6,7-methylenedioxy-1,2,3,4-tetrahydro-isoquinoline,

2 - [(N- (2- (2-naphthyl) ethyl) -azacyclooctyl-3) -methyl] -6,7-methylenedioxy-1,2,3,4-tetrahydro-isoquinoline,

2-t (N- (2-methyl-l-naphthyl) -methyl) -pyrrolidyl-3) -methyl] -6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline,

(N- (2-methyl-l-naphthyl) methyl) 2-t-3 -piperidyl) methyl] -6,7-methylenedioxy-1,2,3,4-tetrahydro-isoquinoline,

2 - [(N- (2-methyl-naphthyl-1-methyl) -azacyclooctyl-3) -methyl] 6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline,

2 - [(N- (2- (5-methyl-6-methoxy-naphthyl-2) -ethyl) -azacycloocty1-3) methyl] -6,7-methylenedioxy-l-oxo-l, 2,3, 4-tetrahydroisoquinoline,

2- [2- (N- (2- (5-Methyl-6-methoxynaphthyl-2) -ethyl) -piperidyl-3) -methyl] -6,7-methylenedioxy-1-oxo-1, 2, 3,4-tetrahydroisoquinoline,

2- [(N- (2- (6-Methoxy-naphthyl-2) -ethyl) -piperidyl-3) -methyl] -6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydro- isoquinoline,

2- [(N- (4- (Naphthyl-2-oxy) -butyl) -pyrrolidyl-3) -methyl] -6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline,

2 - [(N- (4- (naphthyl-2-oxy) butyl) -piperidyl-3) -methyl] -6,7-methylenedioxy-l-oxo-1,2,3,4-tetrahydro-isoquinoline,

2 - [(N- (4- (naphthyl-2-oxy) -butyl) -hexahydro-azepinyl-3) -methyl] -6,7-methylenedioxy-1,2,3,4-tetrahydro-isoquinoline,

2 - [(N- (2- (2-naphthyl) ethyl) -pyrrolidyl-3) -methyl] -6,7-dimethyl-l-oxo-1,2,3,4-tetrahydro-isoquinoline,

2 - [(N- (2- (2-naphthyl) ethyl) -piperidyl-3) -methyl] -6,7-dimethy1-1,2,3,4-tetrahydro-isoquinoline,

2 - [(N- (2- (naphthyl-2) -ethyl) -azacyclooctyl-3) -methyl] -6, 7-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline,

2 - [(N- (2- (2-naphthyl) ethyl) -azacyclooctyl-3) -methyl] -6,7-dimethy1-1,2,3,4-tetrahydro-isoquinoline,

2 - [(N- (2- (1-naphthyl) ethyl) -pyrrolidyl-3) -methyl] -6,7-dimethyl-1,2,3,4-tetrahydro-isoquinoline,

2 - [(N- (2- (1-naphthyl) ethyl) hexahydro-azepinyl-3) -methyl] -6,7-dimethyl-l, 2,3,4-tetrahydro-isoquinoline,

2- [3- (N- (2- (naphthyl-1) -ethyl) -piperidyl-3) -propyl] -6,7-dimethy1-1-oxo-1,2,3,4-tetrahydro-isoquinoline,

2 - [(N- (2-methyl-naphthyl-1) -methyl) -piperidyl-3) -methyl] -6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline,

2 - [(N- (2-methyl-l-naphthyl) methyl) -piperidyl-3) -methyl] -6,7-dimethyl-1,2,3,4-tetrahydro-isoquinoline,

2 - [(N- (2-methyl-l-naphthyl) -methyl) -azacyclooctyl-3) -methyl] -6,7-dimethy1-1-oxo-1,2,3,4-tetrahydro-isoquinoline,

2- [2- (N- (2-methyl-l-naphthyl) methyl) -piperidyl-2) ethyl] -6,7-dimethy1-1-oxo-1,2,3,4-tetrahydro-isoquinoline .

2 - [(N- (2- (5-methyl-6-methoxy-naphthyl-2) -ethyl) -piperidyl-3) -methyl] -6,7-dimethy1-1-oxo-1,2,3, 4-tetrahydro-isoquinoline,

2 - [(N- (2- (5-methyl-6-methoxy-naphthyl-2) -ethyl) -hexahydroazepinyl-3) -methyl] -6,7-dimethy1-1-oxo-1,2,3, 4-tetrahydroisoquinoline,

2 - [(N- (2- (5-methyl-6-methoxynaphthyl-2) -ethyl) -azacyclooctyl-3) -methyl] -6,7-dimethyl-1-oxo-l, 2,3, 4-tetrahydro-isoquinoline,

2 - [(N- (2- (5-Methyl-6-methoxynaphthyl-2) -ethyl) -azacyclooctyl-3) -methyl] -6,7-dimethyl-1,2,2,4,4-tetrahydro- isoquinoline,

2 - [(N- (2- (6-methoxy-naphthyl-2) -ethyl) -pyrrolidyl-3) -methyl] -6,7-dimethy1-1,2,3,4-tetrahydro-isoquinoline,

2 - [(N- (2- (6-methoxy-naphthyl-2) -ethyl) -piperidyl-3) -methyl] -6,7-dimethyl-l, 2,3,4-tetrahydro-isoquinoline,

2 - [(N- (2- (o-methoxy-naphthyl-2) -ethyl) -hexahydro-azepinyl-3) -methyl] -1,2,3,4-tetrahydro-isoquinoline,

2- [2- (N- (2- (6-methoxy-naphthyl-2) -ethyl) -piperidyl-2) ethyl] -6,7-dimethy1-1-oxo-l, 2,3,4- tetrahydro-isoquinoline,

2- [(N- (4- (Naphthyl-2-oxy) -butyl) -piperidyl-3) -methyl] -6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline,

2 - [(N- (4- (Naphthyl-2-oxy) -butyl) -hexahydro-azepinyl-3) -methyl] -6, 7-dimethyl-1-oxo-1,2,3,4-tetrahydro- isoquinoline,

2 - [(N- (4- (naphthyl-2-oxy) -butyl) -azacyclooctyl-3) -methyl] -6,7-dimethyl-1,2,2,4,4-tetrahydro-isoquinoline,

2 - [(N- (3- (6-methoxynaphthyl-2-oxy) -propyl) -hexahydro-azepinyl-3) -methyl] -6,7-dimethyl-1-oxo-l, 2,3, 4-tetrahydro-isoquinoline,

2 - [(N- (3- (6-methoxynaphthyl-2-oxy) -propyl) -azacyclooctyl-3) -methyl] -O-dimethyl-1-oxo-1,3,1,4-tetrahydro- isoquinoline,

2 - [(N- (3- (5,6-dimethoxy-naphthyl-2-oxy) -propyl) -azacyclooctyl-3) -methyl] -6,7-dimethyl-l-oxo-l, 2,3, 4-tetrahydro-isoquinoline,

2- [(N- (3- (naphth-2-yl) -propyl) -azacyclooctyl-3) -methyl] -6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline,

3 - [(N- (3- (3-pyridyl) propyl) -pyrrolidyl-3) -methyl] -7,8-methylenedioxy-2-oxo-l, 3,4,5-tetrahydro-2H-3- benzazepine,

3 - [(N- (1- (pyridyl-3) -methyl) -pyrrolidyl-3) -methyl] -7,8-methylenedioxy-1,3,4,5-tetrahydro-2H-3-benzazepine,

3 - [(N- (3- (4-pyridyl) propyl) -pyrrolidyl-3) -methyl] -7,8-dimethyl-1,3,4,5-tetrahydro-2H-3-benzazepine,

2-t (N- (1- (pyridyl-3) -methyl) -pyrrolidyl-3) -methyl] -6,7-dimethyl-1-oxo-1,2,4,4-tetrahydro-isoquinoline,

2 - [(N- (3- (3-pyridyl) propyl) -pyrrolidyl-3) -methyl] -5,6-methylenedioxy-l-oxo-1,3-dihydro-isoindole,

2 - [(N- (3- (4-pyridyl) propyl) -pyrrolidyl-3) -methyl] -5,6-methylenedioxy-1,3-dihydro-isoindole,

2 - [(N- (2- (6-Methyl-pyridyl-2) -ethyl) -pyrrolidyl-3) -methyl] -5,6-methylenedioxy-l-oxo-l, 3-dihydro-isoindole,

2 - [(N- (2- (6-Methyl-pyridyl-2) -ethyl) -pyrrolidyl-3) -methyl] -5,6-methylenedioxy-l, 3-dihydro-isoindole,

2 - [(N- (1- (3-pyridyl) methyl) -pyrrolidyl-3) -methyl] -5,6-dimethy1-1,3-dihydro-isoindole,

3 - [(N- (3- (3-pyridyl) propyl) -pyrrolidyl-3) -methyl] -7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepine,

2 - [(N- (3- (4-pyridyl) propyl) -pyrrolidyl-3) -methyl] -5,6-dimethoxy-1,3-dihydro-isoindole,

2 - [(N- (I- (3-pyridyl) methyl) -pyrrolidyl-3) -methyl] -5,6-dimethoxy-1 ,. 3-dihydro-isoindole,

2 - [(N- (I- (3-pyridyl) methyl) -pyrrolidyl-3) -methyl] -5,6-dimethoxy-l-oxo-1,3-dihydro-isoindole,

2 - [(N- (2- (6-Methyl-pyridyl-2) -ethyl) -pyrrolidyl-3) -methyl] -6,7-dimethoxy-l, 2,3,4-tetrahydro-isoquinoline,

2 - [(N- (2- (6-Methyl-pyridyl-2) -ethyl) -pyrrolidyl-3) -methyl] -5,6-dimethoxy-l, 3-dihydro-isoindole,

2 - [(N- (2- (6-Methyl-pyridyl-2) -ethyl) -pyrrolidyl-3) -methyl] -6,7-dimethoxy-l-oxo-l, 2,3,4-tetrahydro- isoquinoline,

2 - [(N- (2- (6-Methyl-pyridyl-2) -ethyl) -pyrrolidyl-3) -methyl] -5,6-dimethoxy-l-oxo-l, 3-dihydro-isoindole,

2- [2- (N- (3- (pyridyl-4) -propyl) -piperidyl-2) -ethyl] -6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline,

2- [2- (N- (3- (pyridyl-4) -propyl) -piperidyl-2) -ethyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline,

3 - [(N- (2- (6,7-Dimethoxy-isoquinolyl-4) -ethyl) -piperidyl-2) -methyl] -7,8-dimethyl-2-oxo-1, 3,4,5 tetrahydro-2H-3-benzazepine,

2 - [(N- (I- (4-pyridyl) methyl) -piperidyl-3) -methyl] -6,7-dimethyl-1,2,3,4-tetrahydro-isoquinoline,

2 - [(N- (2- (6,7-dimethoxy-4-isoquinolyl) ethyl) -piperidyl-3) -methyl] -5,6-methylenedioxy-l-oxo-l, 3-dihydro-isoindole,

2- [2- (N- (3- (pyridyl-4) -propyl) -piperidyl-2) -ethyl] -5,6-methylenedioxy-1,3-dihydroisoindole,

2 - [(N- (3- (3-pyridyl) propyl) hexahydro-azepinyl-3) -methyl] -6,7-dimethy1-1-oxo-1,2,3,4-tetrahydro-isoquinoline,

2 - [(N- (3- (3-pyridyl) propyl) hexahydro-azepinyl-3) -methyl] -6,7-dimethy1-1,2,3,4-tetrahydro-isoquinoline,

2 - [(N- (2- (6-Methyl-pyridyl-2) ethyl) hexahydro-azepinyl-3) -methyl] -5,6-dimethoxy-l, 3-dihydro-isoindole,

2 - [(N- (2- (6-Methyl-pyridyl-2) ethyl) hexahydro-azepinyl-3) -methyl] -5,6-dimethoxy-l-oxo-l, 3-dihydro-isoindole,

3 - [(N- (3- (5-hydroxy-indolyl-3) -propyl) -pyrrolidyl-3) -methyl] -7,8-dimethyl-2-oxo-l, 3,4,5-tetrahydro- 2H-3-benzazepine,

2- [(N- (3- (5-Hydroxy-indolyl-3) -propyl) -pyrrolidyl-3) -methyl] -6,7-methylenedioxy-1,2,3,4-tetrahydro-isoquinoline,

3 - [(N- (3- (5-methoxy-indolyl-3) -propyl) -pyrrolidyl-3) -methyl] -7,8-dimethyl-l, 3,4,5-tetrahydro-2H-3- benzazepine _f

2 - [(N- (3- (5-methoxy-indolyl-3) -propyl) -pyrrolidyl-3) -methyl] -5,6-methylene-dioxy-l, 3-dihydro-isoindole,

2 - [(N- (3- (S-Benzyloxy-indolyl-3) -propyl) -pyrrolidyl-3) -methyl] -6, V -methylenedioxy-1-oxo-1-yl / Sf't-tetrahydro-isoquinoline .

2 - [(N- (3- (S-benzyloxy-indolyl-3) -propyl) -pyrrolidyl-3) -methyl] -5,6-methylenedioxy-1-oxo-1,3-dihydro-isoindole,

3 - [(N- (3- (N-methyl-indolyl-3) -propyl) -pyrrolidyl-3) -methyl] -7,8-methylenedioxy-1,3,4,5-tetrahydro-2H-3- benzazepine,

2 - [(N- (3- (N-methyl-indolyl-3) -propyl) -pyrrolidyl-3) -methyl] -o ^ -dimethyl-l ^^^ - tetrahydro-isoquinoline,

2 - [(N- (3- (3-indolyl) propyl) -pyrrolidyl-3) -methyl] -5,6-dimethyl-1,3-dihydro-isoindole,

3 - [(N- (3- (3-indolyl) propyl) -pyrrolidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro-2H-3- benzazepine,

2 - [(N- (3- (5-hydroxy-indolyl-3) -propyl) -pyrrolidyl-3) -methyl] -5,6-dimethyl-l-oxo-l, 3-dihydro-isoindole,

2 - [(N- (3- (5-hydroxy-indolyl-3) -propyl) -pyrrolidyl-3) -methyl] -6,7-dimethoxy-l-oxo-l, 2,3,4-tetrahydro- isoquinoline,

3- [(N- (3- (5-Methoxy-indolyl-3) -propyl) -pyrrolidyl-3) -methyl] -7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3 benzazepine,

2 - [(N- (3- (5-methoxy-indolyl-3) -propyl) -pyrrolidyl-3) -methyl] -5, б-dimethoxy-l-oxo-l, 3-dihydro-isoindole,

2 - [(N- (3- (S-benzyloxy-indolyl-3) -propyl) -pyrrolidyl-3) -methyl] -6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline,

2 - [(N- (3- (S-Benzyloxy-indolyl-3) -propyl) -pyrrolidyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro- isoquinoline,

2 - [(N- (3- (N-methyl-indolyl-3) -propyl) -pyrrolidyl-3) -methyl] -5, б-dimethyl-l-oxo-l, 3-dihydro-isoindole,

2 - [(N- (3- (N-methyl-indolyl-3) -propyl) -pyrrolidyl-3) -methyl] -5,6-dimethoxy-l, 3-dihydro-isoindole,

2- [(N- (2- (3,4-Dimethoxy-phenyl) -ethyl) -hexahydro-azepinyl-3) -methyl] -6,7-methylenedioxy-1-oxo-1,2,3,4- tetrahydro-isoquinoline,

2 - [(N- (3- (3,4-methylenedioxy-phenoxy) -propyl) -hexahydro-azepinyl-3) -methyl] -6, V -methylenedioxy-1-oxo-1,1,3,4-tetrahydro isoquinoline,

2 - [(N- (2- (4-trifluoromethoxy-phenyl) -ethyl) -piperidyl-3) -methyl] -5,6-dimethoxy-1-oxo-1,3-dihydro-isoindole,

2 - [(N- (2- (4-trifluoromethyl-1-phenyl) -ethyl) -piperidyl-3) -methyl] -5,6-dimethoxy-1-oxo-1,3-dihydroisoindole,

2- [(N- (2- (3,4-dichloro-phenyl) -ethyl) -piperidyl-3) -methyl] - S ₁ 6-dimethoxy-l-oxo-l, 3-dihydro-isoindole,

2- [(N- (2- (3,4,5-trimethoxy-phenyl) -ethyl) -piperidyl-3) -methyl] -5, б-dimethoxy-1-oxo-1,3-dihydroisoindole,

2 - [(N- (2- (4-methoxy-phenyl) -ethyl) -piperidyl-3) -methyl] -5,6-dimethoxy-1-oxo-1,3-dihydro-isoindole,

2 - [(N- (2- (3-methyl-phenyl) -ethyl) -piperidyl-3) -methyl] -5,6-dimethoxy-1-oxo-1,3-dihydro-isoindole,

2 - [(N- (2- (3,4-Dimethyl-phenyl) -ethyl) -piperidyl-3) -methyl] -5,6-dimethoxy-l-oxo-l, 3-dihydro-isoindole,

2 - [(N- (2- (2,3,4,5-tetramethyl-phenyl) -ethyl) -piperidyl-3) -methyl] -5,6-dimethoxy-1-oxo-1,3-dihydro- isoindole,

2- [ (N- (2- (4-Benzyloxy-phenyl) -ethyl) -piperidyl-3) -methyl] -5,6-dimethoxy-1-oxo-1,3-dihydro-isoindole,

2 - [(N- (2- (4-hydroxy-phenyl) -ethyl) -piperidyl-3) -methyl] -5,6-dimethoxy-l-oxo-1,3-dihydro-isoindole,

2 - [(N- (2- (4-Methanesulfonyloxy-phenyl) -ethyl) -piperidyl-3) -methyl] -5,6-dimethoxy-1-oxo-1,3-dihydroisoindole,

2 - [(N- (2- (4-trifluoro-ethanesulfonyloxy-phenyl) -ethyl) -piperidyl-3) -methyl] -5,6-dimethoxy-1-oxo-1,3-dihydroisoindole,

2 - [{N- (2- (4-methanesulfonylamino-phenyl) -ethyl) -piperidyl-3) -methyl] -5,6-dimethoxy-l-oxo-l, 3-dihydro-isoindole,

2 - [(N- (2- (4-Dimethanesulfonylamino-phenyl) -ethyl) -piperidyl-3) -methyl] -5,6-dimethoxy-1-oxo-1,3-dihydroisoindole,

2 - [(N- (3- (4-bromo-phenyl) -propyl) -piperidyl-3) -methyl] -5,6-dimethoxy-l-oxo-1,3-dihydro-isoindole,

2 - [(N- (3- (4-methoxy-phenyl) -propyl) -piperidyl-3) -methyl] -5, δα-imethoxy-1-oxo-1,3-dihydroisoindole,

2 - [(N- (3- (3-methoxy-phenyl) -propyl) -piperidyl-3) -methyl] -5,6-dimethoxy-l-oxo-1,3-dihydro-isoindole,

2 - [(N- (3- (3,4-dimethoxy-phenyl) -propyl) -piperidyl-3) -methyl] -5, б-dimethoxy-l-oxo-l, 3-dihydro-isoindole,

2- [(N- (4- (4-methoxy-phenyl) -butyl) -piperidyl-3) -methyl] -5,6-dimethoxy-1-oxo-1,3-dihydroisoindole,

2 - [(N- (3- (4-amino-3,5-dibromo-phenoxy) -propyl) -piperidyl-3) -methyl] -5,6-dimethoxy-l-oxo-l, 3-dihydro- isoindole,

3- [(N- (2- (2,5-dimethyl-thienyl-3) -ethyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4,5- tetrahydro-2H-3-benzazepine,

3 - [(N- (2- (5-methoxy-benzo [b] thienyl-3) ethyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4, 5-tetrahydro-2H-3-benzazepine,

3- [(N- (2- (b-Methoxy-benzo [b] thienyl-3) -ethyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4, 5-tetrahydro-2H-3-benzazepine,

3 - [(N- (2- (6-Bromo-benzo [b] thienyl-3) -ethyl) -piperidyl-3) -methyl] ^, e-dimethoxy ^ -oxo-1 H / S-tetrahydro ^ HS-benzazepine,

3- [(N- (2- (Benzo [b] thienyl-2) -ethyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro- 2H-3-benzazepine,

3- [(N- (2- (Benzo [b] furyl-3) -ethyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro- 2H-3-benzazepine,

3-t (N- (2- (2,5-dimethyl-3-thienyl) ethyl) -piperidyl-3) -methyl] -7,8-dimethyl-2-oxo-l, 3,4,5- tetrahydro-2H-3-benzazepine,

3- [(N- (2- (5-Methoxy-benzo [b] thienyl-3) -ethyl) -piperidyl-3) -methyl] -7,8-dimethyl-2-oxo-l, 3,4, 5-tetrahydro-2H-3-benzazepine,

3 - [(N- (2- (6-methoxy-benzo [b] thienyl-3) ethyl) -piperidyl-3) -methyl] -7,8-dimethyl-2-oxo-l, 3,4, 5-tetrahydro-2H-3-benzazepine _f

3 - [(N- (2- (6-Bromo-benzo [b] thienyl-3) -ethyl) -piperidyl-3) -methyl] -7,8-dimethyl-2-0X0-1,3,4, 5-tetrahydro-2H-3-benzazepine,

3 - [(N- (2- (benzo [b] thienyl-2) -ethyl) -piperidyl-3) -methyl] -7,8-dimethyl-2-oxo-l, 3,4,5-tetrahydro- 2H-3-benzazepine,

3 - [(N- (2- (benzo [b] furyl-3) ethyl) -piperidyl-3) -methyl] -7,8-dimethyl-2-oxo-l, 3,4,5-tetrahydro- 2H-3-benzazepine,

3 - [(N- (2- (2,5-dimethyl-3-thienyl) ethyl) -piperidyl-3) -methyl] -7, e-methylenedioxy-2-oxo-l, 3,4,5- tetrahydro-2H-3-benzazepine,

3 - [(N- (2- (5-methoxy-benzo [b] thienyl-3) ethyl) -piperidyl-3) -methyl] -7, S-methylenedioxy-2-oxo-l, 3,4, 5-tetrahydro-2H-3-benz-azepine,

3 - [(N- (2- (6-Methoxy-benzo [b] thienyl-3) -ethyl) -piperidyl-3) -methyl] -7, e -methylenedioxy ^ -oxo-1, 3, 4, 5 tetrahydro-2H-3-benzazepine,

3 - [(N- (2- (6-Bromo-benzo [b] thienyl-3) -ethyl) -piperidyl-3) -methyl] -7,8-methylenedioxy-2-oxo-l, 3,4, 5-tetrahydro-2H-3-benzazepine,

3- [(N- (2- (Benzo [b] thienyl-2) -ethyl) -piperidyl-3) -methyl] -7,8-methylenedioxy-2-oxo-1,3,4,5-tetrahydro- 2H-3-benzazepine,

3- [(N- (2- (Benzo [b] fury1-3) -ethyl) -piperidyl-3) -methyl] -7,8-methylenedioxy-2-oxo-l, 3,4,5-tetrahydro- 2H-3-benzazepine,

3 - [(N- (3- (2,5-dimethyl-thienyl-3) -propyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4,5- tetrahydro-2H-3-benzazepine,

3 - [(N- (3- (5-Methoxy-benzo [b] thienyl-3) -propyl) -piperidyl-3) -methyl] -7, e -dimethoxy ^ -oxo-l, 3,4, S tetrahydro ^ HS-benzazepine,

3 - [(N- (3- (6-methoxy-benzo [b] thienyl-3) -propyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4, 5-tetrahydro-2H-3-benzazepine,

3 - [(N- (3- (6-Bromo-benzo [b] thienyl-3) -propyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4, 5-tetrahydro-2H-3-benzazepine,

3- [(N- (3- (Benzo [b] thienyl-2) -propyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro- 2H-3-benzazepine,

3 - [(N- (3- (benzo [b] furyl-3) -propyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro- 2H-3-benzazepine,

3 - [(N- (3- (2,5-dimethyl-thienyl-3) -propyl) -piperidyl-3) -methyl] -7,8-dimethyl-2-oxo-l, 3,4,5- tetrahydro-2H-3-benzazepine,

3 - [(N- (3- (6-methoxy-benzo [b] thienyl-3) -propyl) -piperidyl-3) -methyl] -7,8-dimethyl-2-oxo-l, 3,4, 5-tetrahydro-2H-3-benzazepine,

3 - [(N- (3- (benzo [b] thienyl-2) -propyl) -piperidyl-3) -methyl] -7,8-dimethyl-2-oxo-1,3,4,5-tetrahydro- 2H-3-benzazepine,

2.0 3- [(N- (3- (Benzo [b] furyl-3) -propyl) -piperidyl-3) -methyl] -7, 8-dimethyl-2-oxo-1, 3,4,5-tetrahydro -2H-3-benzazepine,

3 - [(N- (3- (2,5-dimethyl-thienyl-3) -propyl) -piperidyl-3) -methyl] -7,8-methylenedioxy-2-oxo-1,3,4,5- tetrahydro-2H-3-benzazepine,

3- [(N- (3- (6-Methoxy-benzo [b] thienyl-3) -propyl) -piperidyl-3) -methyl] -7,8-methylenedioxy-2-oxo-l, 3,4, 5-tetrahydro-2H-3-benzazepine,

3 - [(N- (3- (Benzo [b] thienyl-2) -propyl) -piperidyl-3) -methyl] -7, e -methylenedioxy ^ -oxo-1,3,4,5-tetrahydro-2H -3-benzazepine,

3 - [(N- (3- (Benzo [b] furyl-3) -propyl) -piperidyl-3) -methyl] -7, e -methylenedioxy ^ -oxo-l, 3,4, 5-tetrahydro-2H -3-benzazepine,

3 - [(N - (2- (Thienyl-2) -ethyl) -piperidyl-3) -methyl] -7,8-dimethyl 2-oxo-1,3,4,5-tetrahydro-2H-3-benzazepine .

3 - [(N- (2- (benzo [b] thienyl-3) ethyl) -piperidyl-3) -methyl] -7,8-dimethyl-2-oxo-l, 3,4,5-tetrahydro- 2H-3-benzazepine,

3 - [(N- (2- (Benzo [b] furyl-2) -ethyl) -piperidyl-3) -methyl] -7,8- "^ O-dimethyl-2-oxo-1,3,4,5 tetrahydro-2H-3-benzazepine,

3 - [(N- (2- (2-thienyl) ethyl) -piperidyl-3) -methyl] -7,8-methylenedioxy-2-oxo-l, 3,4,5-tetrahydro-2H-3- benzazepine,

3 - [(N- (2- (benzo [b] thienyl-3) ethyl) -piperidyl-3) -methyl] -7,8-methylenedioxy-2-oxo-l, 3,4,5-tetrahydro- 2H-3-benzazepine,

3 - [(N- (2- (benzo [b] furyl-2) -ethyl) -piperidyl-3) -methyl] -7,8-methylenedioxy-2-oxo-l, 3,4,5-tetrahydro- 2H-3-benzazepine,

3 - [(N- (2- (Thienyl-2) -ethyl) -hexahydro-azepinyl-3) -methyl] -7,8-dimethyl-2-oxo-l, 3,4,5-tetrahydro-2H- 3-benzazepine,

3 - [(N- (2- (benzo [b] thienyl-3) ethyl) hexahydro-azepinyl-3) -methyl] -7,8-dimethyl-2-oxo-l, 3,4,5- tetrahydro-2H-3-benzazepine,

3 - [(N- (2- (Benzo [b] furyl-2) -ethyl) -hexahydro-azepinyl-3) -methyl] -7,8-dimethyl-2-oxo-l, 3,4,5- tetrahydro-2H-3-benzazepine,

3 - [(N- (2- (2-thienyl) ethyl) hexahydro-azepinyl-3) -methyl] -7,8-methylenedioxy-2-oxo-l, 3,4,5-tetrahydro-2H- 3-benzazepine,

3 - [(N- (2- (Benzo [b] thienyl-3) -ethyl) -hexahydro-azepinyl-3) -methyl] -7, e -methylenedioxy ^ -oxo-l, 3,4, S-tetrahydro ^ HS-benzazepine,

3 - [(N- (2- (Benzo [b] furyl-2) -ethyl) -hexahydro-azepinyl-3) -methyl] -7, e -methylenedioxy ^ -oxo-1, 3,4, 5-tetrahydro -2H-3-benzazepine,

3 - [(N- (2- (2-thienyl) ethyl) -pyrrolidyl-3) -methyl] -7,8-dimethyl-2-oxo-l, 3,4,5-tetrahydro-2H-3- benzazepine,

3 - [(N- (2- (benzo [b] thienyl-3) ethyl) -pyrrolidyl-3) -methyl] -7,8-dimethyl-2-oxo-l, 3,4,5-tetrahydro- 2H-3-benzazepine,

3 - [(N- (2- (benzo [b] furyl-2) -ethyl) -pyrrolidyl-3) -methyl] -7,8-dimethyl-2-oxo-l, 3,4,5-tetrahydro- 2H-3-benzazepine,

3 - [(N- (2- (2-thienyl) ethyl) -pyrrolidyl-3) -methyl] -7,8-methylenedioxy-2-oxo-l, 3,4,5-tetrahydro-2H-3- benzazepine,

3 - [(N- (2- (benzo [b] thienyl-3) ethyl) -pyrrolidyl-3) -methyl] -7,8-methylenedioxy-2-oxo-l, 3,4,5-tetrahydro- 2H-3-benzazepine,

3- [(N- (2- (Benzo [b] furyl-2) -ethyl) -pyrrolidyl-3) -methyl] -7,8-methylenedioxy-2-oxo-l, 3,4,5-tetrahydro- 2H-3-benzazepine,

3 - [(N- (2- (2-thienyl) ethyl) -pyrrolidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro-2H-3- benzazepine,

3 - [(N- (2- (Benzo [b] thienyl-3) -ethyl) -pyrrolidyl-3) -methyl] -7,8 · dimethoxy-2-oxo-1,3,4,5-tetrahydro 2H-3-benzazepine,

3 - [(N- (2- (benzo [b] furyl-2) -ethyl) -pyrrolidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro- 2H-3-benzazepine,

3 - [(N- (2- (2-thienyl) ethyl) hexahydro-azepinyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro-2H- 3-benzazepine,

3 - [(N- (2- (Benzo [b] thienyl-3) -ethyl) -hexahydro-azepinyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4,5- tetrahydro-2H-3-benzazepine,

3 - [(N- (2- (Benzo [b] furyl-2) -ethyl) -hexahydco-azepinyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4,5- tetrahydro-2H-3-benzazepine,

3 - [(N- (4- (thienyl-2) -butyl) -piperidyl-3) -methyl] -7, 8-dimethyl-2-oxo-1,3,4-s-tetrahydro-H-S-benzazepine,

3 - [(N- (4- (benzo [b] thienyl-3) -butyl) -piperidyl-3) -methyl] -7,8-dimethyl-2-oxo-l, 3,4,5-tetrahydro- 2H-3-benzazepine,

3 - [(N- (4- (benzo [b] furyl-2) -butyl) -piperidyl-3) -methyl] -7, 8-dimethyl-2-one-Ι, 3,4, 5-tetrahydro- 2H-3-benzazepine,

3 - [(N- (5- (2-thienyl) pentyl) -piperidyl-3) -methyl] -7,8-dimethyl-2-oxo-l, 3,4,5-tetrahydro-2H-3- benzazepine,

3 - [(N- (5- (benzo [b] thienyl-3) -pentyl) -piperidyl-3) -methyl] -7,8-dimethyl-2-oxo-l, 3,4,5-tetrahydro- 2H-3-benzazepine,

3 - [(N- (5- (benzo [b] furyl-2) -pentyl) -piperidyl-3) -methyl] -7,8-dimethyl-2-oxo-l, 3,4,5-tetrahydro- 2H-3-benzazepine,

3 - [(N- (4- (2-thienyl) butyl) -piperidyl-3) -methyl] -7,8-methylenedioxy-2-oxo-l, 3,4,5-tetrahydro-2H-3- benzazepine,

3 - [(N- (4- (benzo [b] thienyl-3) -butyl) -piperidyl-3) -methyl] -7,8-methylenedioxy-2-oxo-l, 3,4,5-tetrahydro- 2H-3-benzazepine,

3 - [(N- (4- (benzo [b] fury1-2) butyl) -piperidyl-3) -methyl] -7,8-methylenedioxy-2-oxo-l, 3,4,5-tetrahydro- 2H-3-benzazepine,

3 - [(N- (5- (2-thienyl) pentyl) -piperidyl-3) -methyl] -7,8-methylenedioxy-2-oxo-l, 3,4,5-tetrahydro-2H-3- benzazepine,

3 - [(N- (5- (benzo [b] thienyl-3) -pentyl) -piperidyl-3) -methyl] -7,8-methylenedioxy ^ -oxo-l ^^ S-tetrahydro ^ H-S-benzazepine,

3 - [(N- (5- (benzo [b] furyl-2) -pentyl) -piperidyl-3) -methyl] -7,8-methylenedioxy-2-oxo-l, 3,4,5-tetrahydro- 2H-3-benzazepine,

3 - [(N- (4- (benzo [b] thienyl-3) -butyl) -piperidyl-3) -methyl] -7, S- dimethoxy-2-oxo-l, 3,4,5-tetrahydro 2H-3-benzazepine,

3 - [(N- (4- (Benzo [b] furyl-2) -butyl) -piperidyl-3) -methyl] -7, 8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro 2H-3-benzazepine,

3 - [(N- (5- (benzo [b] thienyl-3) -pentyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydro 2H-3-benzazepine and

3 - [(N- (5- (benzo [b] furyl-2) -pentyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro- 2H-3-benzazepine as well

their enantiomers, their diastereomers, their N-oxides and their acid addition salts, in particular for the pharmaceutical use of their physiologically acceptable acid addition salts.

Preferred compounds of the above general formula I are those in which

A, B, m and η are as defined above,

E is a straight-chain alkylene group having 1 to 3 carbon atoms,

G is a straight-chain alkylene group having 1 to 6 carbon atoms, one having an aromatic or heteroaromatic

may be replaced by an oxygen atom, a methylimino or ethylimino group, the radical R connected methylene group of a straight-chain alkylene group having 3 to 6 carbon atoms,

Rjl is a methyl or methoxy group,

R _{2 is} a methyl or methoxy group or R ^ and R ₂ together form a methylenedioxy group and

R is a furyl, thienyl, pyridyl, benzo [b] furyl or benzo [b] thienyl group optionally substituted by a methyl group, a benzo [b] thienyl group substituted by a halogen atom, a methoxy or methanesulfonyloxy group, optionally substituted by a hydroxy, methoxy or benzyloxy substituted indolyl or N-methylindolyl group, a dimethylthienyl or dimethoxyisoquinolyl group, a naphthyl group optionally mono- or disubstituted by methyl or methoxy groups, where the substituents may be the same or different, or also when B represents a -CH ₂ - or СO-group, a phenyl group optionally substituted by a methylenedioxy group, a phenyl group mono- or disubstituted by chlorine or bromine atom, methyl or methoxy groups, wherein the substituents may be the same or different, a through a hydroxy, benzyloxy, methanesulfonyloxy, trifluoromethanesulfonyloxy, trifluoromethyl, trifluoromethoxy , Nitro, amino, acetamido, methanesulfonylamino or bis (methanesulfonyl) amino group substituted phenyl group, a trimethoxyphenyl, tetramethylphenyl or Dihalogenaminophenylgruppe mean, but especially the compounds of the general formula

L U N-E-CH N-G-R, (Ia)

'η

in the

R ^, R2, Rf A, B, E, G, m and η are defined as mentioned above, and their enantiomers, their diastereomers, their N-oxides and their acid addition salts, in particular for the pharmaceutical application of their physiologically acceptable acid addition salts.

Very particularly preferred compounds of the above general formula Ia are those in which

A a -

B is a -CH ₂ -, -CH ₂ -CH ₂ -, -CO- or -CH ₂ CO radical, where

x at the carbon atom marked with χ with the phenyl

core is linked,

E is a methylene or ethylene group,

G is a straight-chain alkylene group having 2 to 4 carbon atoms, wherein the methylene group of a straight-chain alkylene group having 3 or 4 carbon atoms connected to an aromatic or heteroaromatic radical R may be replaced by an oxygen,

R ^ is a methoxy group,

R _{2 is} a methoxy group or R 1 and R ₂ together form a methylenedioxy group,

m is the number 2, 3 or 4, η is the number 1 and

R is a naphthyl-2-, 6-methoxynaphthyl-2-, 5-methyl-6-methoxynaphthyl-2-, thienyl-2-, benzo [b] furyl-2 or benzo [b] thienyl 3-group or even if B is the -CI ^ - or -CO-

Represent group, a 4-methoxyphenyl or 3,4-dimethoxyphenyl, their enantiomers, their diastereomers and their physiologically acceptable acid addition salts.

The following are mentioned as particularly preferred compounds:

3 - [(N- (2- (2-naphthyl) ethyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro-2H-3- benzazepine,

3 - [(N- (2- (5-Methyl-6-methoxynaphthyl-2) -ethyl) -piperidyl-3) methyl] -7,8-dimethoxy-2-oxo-1, 3,4,5 tetrahydro-2H-3-benzaze pin,

3- [2- (N- (2- (6-Methoxy-naphthyl-2) -ethyl) -piperidyl-2) -ethyl] 7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydro -2H-3-benzazepine,

2 - [(N- (2- (6-methoxy-naphthyl-2) -ethyl) -hexahydro-azepinyl-3) -methyl] -6,7-methylenedioxy-l-oxo-l, 2,3,4- tetrahydro-isoquinoline,

2 - [(N- (2- (2-naphthyl) ethyl) hexahydro-azepinyl-3) -methyl] -6,7-methylenedioxy-l-oxo-l, 2,3,4-tetrahydro-isoquinoline,

2 - [(N- (2- (3,4-dimethoxy-phenyl) -ethyl) -piperidyl-3) -methyl] -6,7-dimethy1-1,2,3,4-tetrahydro-isoquinoline,

2 - [(N- (2- (3,4-dimethoxy-phenyl) -ethyl) -piperidyl-3) -methyl] -6,7-dimethyl-l-oxo-l, 2,3,4-tetrahydro- isoquinoline,

2 - [(N- (3- (4-methoxy-phenoxy) -propyl) -piperidyl-3) -methyl] -6,7-dimethyl-l-oxo-l, 2,3,4-tetrahydro-isoquinoline,

3 - [(N- (4- (2-thienyl) butyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro-2H-3- benzazepine,

3- [(N- (2- (Benzo [B] furyl-2) -ethyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydro-2H -3-benzazepine,

3 - [(N- (2- (benzo [b] thienyl-3) ethyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro- 2H-3-benzazepine,

2 - [(N- (3- (6-methoxy-naphthyl-2-oxy) -propyl) -pyrrolidyl-3) -methyl] -6,7-dimethoxy-l-oxo-1,2,3,4 tetrahydro-isoquinoline,

2 - [(N- (2- (6-methoxy-naphthyl-2) -ethyl) -hexahydro-azepinyl-3) -methyl] -6,7-methylenedioxy-l-oxo-l, 2,3,4- tetrahydro-isoquinoline,

3 - [(N- (2- (4-methoxy-phenyl) -ethyl) -hexahydro-azepinyl-3) -methyl] -7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydro- 2H-3-benzazepine and

3 - [(N- (2- (3,4-Dimethoxy-phenyl) -ethyl) -hexahydro-azepinyl-3) -methyl] ^, e -methylenedioxy ^ -oxo-l, 3,4, 5-tetrahydro- 2H-3-benzazepine,

but in particular the following compounds:

3- [(N- (2- (Naphthyl-2) -ethyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydro-2H-3- benzazepine,

2- [(N- (3- (4-methoxy-phenoxy) -propyl) -piperidyl-3) -methyl] -b, 7-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline,

3- [(N- (4- (Thienyl-2) -butyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydro-2H-3- benzazepine,

2 - [(N- (3- (6-methoxynaphthyl-2-oxy) -propyl) -pyrrolidyl-3) -methyl] -6, 7-di-n-ethoxy-1-oxo-l, 2,3, 4-tetrahydro-isoquinoline,

2 - [(N- (2- (6-Methoxy-naphthyl-2) -ethyl) -hexahydro-azepinyl-3) methyl] -6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydro isoquinoline,

3 - [(N- (2- (4-methoxy-phenyl) -ethyl) -hexahydro-azepinyl-3) -methyl] -7,8-diraethoxy-2-oxo-l, 3,4,5-tetrahydro- 2H-3-benzazepine and

3 - [(N- (2- (3,4-Dimethoxy-phenyl) -ethyl) -hexahydro-azepinyl-3) methyl] -7, в-теЫіуіепаіоху-г-охо-і, 3,4,5-tetrahydro -2H-3-benzazepine,

their enantiomers, their diastereomers and their acid addition salts.

According to the invention, the novel compounds of general formula I are obtained by the following processes:

a) reaction of a compound of the general formula

в.-J-II N-E-CH N-H, (II)

in the

Rt, R2, A, B, E, m and η are as defined above, with a compound of the general formula

Z ₁ -GR, (III)

in the

R and G are as defined above and

Z represents a nucleophilic leaving group such as a halogen atom or a sulphonyloxy group, for example a chlorine, bromine or iodine atom, the methanesulphonyloxy, p-toluenesulphonyloxy or ethoxysulphonyloxy group, or a hydroxy group or Z ₁ together with a hydrogen atom of the adjacent methylene group represents an oxygen atom.

If Z _{1 is} a nucleophilic leaving group, the reaction is expediently carried out in a solvent or solvent mixture such as acetone, diethyl ether, methylformamide, dimethylformamide, dimethyl sulfoxide, benzene, chlorobenzene, tetrahydrofuran, benzene / tetrahydrofuran, dioxane or in an excess of the compounds of the general formulas II and / or III and optionally in the presence of an acid-binding agent, for example an alcoholate such as potassium tert-butylate, an alkali metal hydroxide such as sodium or potassium hydroxide, an alkali metal carbonate such as potassium carbonate, an alkali metal amide such as sodium amide, an alkali metal hydride such as sodium hydride, a tertiary organic base such as Triethylamine or pyridine, the latter can also serve as a solvent, or a reaction accelerator such as potassium iodide depending on the reactivity of the nucleophilically exchangeable radical expediently at temperatures between 0 and 150 ⁰ C, preferably at T emperatures between 50 and 12O ⁰ C, for example, in the boiling temperature of the solvent used, carried out. However, the reaction can also be carried out without a solvent. However, the reaction is carried out particularly advantageously in the presence of a tertiary organic base or an excess of the amine of general formula II used.

If Z ₁ denotes a hydroxyl group, the reaction is preferably carried out in a suitable solvent such as methanol, ethanol, tetrahydrofuran, dioxane, ethyl acetate or glacial acetic acid with hydrogen in the presence of a hydrogenation catalyst.

lysators such as platinum, palladium / carbon or Raney nickel at a hydrogen pressure of 2 to 10 bar, preferably at 5 bar, and at temperatures between 20 and 12O ⁰ C, preferably at temperatures between 50 and 100 ⁰ C performed.

When Z, together with a hydrogen atom of the adjacent methylene group, means an acid atom, the reaction is preferably carried out in a suitable solvent such as methanol, ethanol, tetrahydrofuran, dioxane, ethyl acetate or glacial acetic acid with hydrogen in the presence of a hydrogenation catalyst such as platinum, palladium / carbon or Raney nickel at a hydrogen pressure of 2 to 10 bar, preferably at 5 bar, and at temperatures between 20 and 12O ⁰ C, preferably at temperatures between 50 and 100 ⁰ C, or in the presence of a suitable complex metal hydride such as sodium cyanoborohydride in a suitable solvent such as methanol, Ethanol, tetrahydrofuran, dioxane or acetonitrile at temperatures between 0 and 50 ⁰ C, but preferably at room temperature, carried out.

b) reaction of a compound of the general formula

.... _{t ч}

(IV)

in the

R ₁ , R ₂ , A and B are as defined above, with a compound of the general formula

Z-E-CH N-G-R, (V)

⁴ CCH ₂ ) /

in the

R, E, G, m and η are as defined above and Z _{2 represents} a nucleophilic leaving group such as a halogen atom or a sulfonyloxy group, for example a chlorine, bromine or iodine atom, the methanesulfonyloxy, p-toluenesulfonyloxy or ethoxysulfonyloxy group.

The reaction is conveniently carried out in a solvent or solvent mixture such as methylformamide, dimethylformamide, dimethylsulfoxide, benzene, chlorobenzene, tetrahydrofuran, benzene / tetrahydrofuran or dioxane in the presence of an acid binding agent, e.g. an alcoholate such as potassium tert-butylate, an alkali hydroxide such as sodium or potassium hydroxide, an alkali carbonate such as potassium carbonate, an alkali metal amide such as sodium amide or an alkali hydride

^ ** as sodium hydride expediently at temperatures between 0 and 150 ⁰ C, preferably at temperatures between and 50 ⁰ C, carried out.

c) For the preparation of compounds of general formula I in which B represents a -CH ₂ - or -CH ₂ CH ₂ group:

Reduction of a compound of general formula R ₁

R ₂ L Π NE-CH NGR, (VI)

in the

R, R ₁ , R ₂ , A, E, G, m and η are as defined above

Bi is a -CO- or -C ^ CO group, with the χ

χ characterized carbon atom is linked to the phenyl nucleus.

The reduction is preferably with a metal hydride such as lithium aluminum hydride or diborane or with a complex of borane and a thioether, for example with borane-dimethyl sulfide complex, in a suitable solvent such as diethyl ether or tetrahydrofuran at temperatures between 0 and 80 ⁰ C, but preferably at temperatures between 10 and 45 ⁰ C, performed.

d) For the preparation of compounds of general formula I in which A represents a -CH ₂ group and B represents a -CO- or -CH ₂ CO- group:

Reduction of a compound of the general formula

ч ѵ ^со \ -E- ^ CH ₂ V Cn » N - G - R R-L N CH К '

(VII)

in the

R, R- ^, R ₂ , E, G, m and η are as defined above and B2 represents a -CO- or -CH 2 CO group, wherein the with

χ marked carbon atom is linked to the phenyl nucleus, with nascent hydrogen.

The reduction is in a suitable solvent such as glacial acetic acid, glacial acetic acid / water or glacial acetic acid / ethanol with nascent hydrogen, for example in the presence of zinc / glacial acetic acid, tin / hydrochloric acid or tin dichloride / hydrochloric acid at temperatures between 20 and 150 ⁰ C, but preferably at the boiling point of the reaction mixture, for example at temperatures between 80 and 100 ⁰ C, carried out.

e) For the preparation of compounds of the general formula I in which G, with the exception of those containing a sulfur atom, a SuIf inyl- or sulfonyl group, has the meanings mentioned for G and A is the -CH ₂ -CH ₂ group and B is the methylene or carbonyl group represents:

Hydrogenation of a compound of the general formula

N-E

^CH 2>

2> m

CH N (CH ₂ ) /

- R

, (VIII)

in the

R, R

1'

B, E, m and η are as defined above,

Gi with the exception of those containing a sulfur atom, a sulfinyl or sulfonyl group which has the meanings mentioned for G and BJ represents a -CH ₂ - or -СО group.

The hydrogenation is carried out in a solvent or solvent mixture such as methanol, ethanol, ethyl acetate or glacial acetic acid with catalytically excited hydrogen, for example with hydrogen in the presence of platinum or palladium / carbon, at a hydrogen pressure of 1 to 7 bar, but preferably from 3 to 5 bar and at temperatures between 0 and 75 ° C, but preferably at temperatures between 20 and 50 ⁰ C performed.

In the reaction described above, optionally present reactive groups such as hydroxyl, amino, alkylamino or imino groups can be protected during the reaction by übliehe protecting groups, which are cleaved again after the reaction.

For example, comes as a protective group for a hydroxy group, the trimethylsilyl, acetyl, benzoyl, benzyl or tetrahydropyranyl and as a protective group for an amino, alkylamino or imino group, the acetyl, benzoyl, ethoxycarbonyl or benzyl group into consideration.

The optional subsequent cleavage of a protective moiety used is preferably carried out hydrolytically in an aqueous solvent, for example in water, isopropanol / water, tetrahydrofuran / water or dioxane / water, in the presence of an acid such as hydrochloric acid or sulfuric acid or in the presence of an alkali metal base such as sodium hydroxide or potassium hydroxide at temperatures between 0 and 100 ^° C., preferably at the boiling point of the reaction mixture. However, if the cleavage of a benzyl group preferably by hydrogenolysis, for example 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 the addition of an acid such as hydrochloric acid at temperatures between 0 and 5O ⁰ C, but preferably Room temperature, and a hydrogen pressure of 1 to 7 bar, but preferably from 3 to 5 bar.

If, according to the invention, a compound of the general formula I in which R contains a nitro group, this can be converted into a corresponding amino compound of the general formula I by reduction or

a compound of the general formula I in which R contains an amino group, it can be converted by acylation into a corresponding alkanoylamino compound of the general formula I.

The subsequent reduction of the nitro compound is preferably carried out in a solvent such as water, water / ethanol, methanol, glacial acetic acid, ethyl acetate or dimethylformamide.

amide suitably with hydrogen in the presence of a hydrogenation catalyst such as Raney nickel, platinum or palladium / carbon, with metals such as iron, tin or zinc in the presence of an acid, with salts such as iron (II) sulfate, stannous chloride or sodium dithionite or with hydrazine in the presence of Raney nickel at temperatures between 0 and 50 ⁰ C, but preferably at room temperature, carried out.

The subsequent acylation is conveniently carried out in a solvent such as methylene chloride, chloroform, carbon tetrachloride, ether, tetrahydrofuran, dioxane, benzene, toluene, acetonitrile or dimethylformamide preferably with a reactive derivative of the acid, for example with acetyl chloride, acetic anhydride or propionic anhydride, and optionally in the presence of an inorganic Base such as sodium carbonate or a tertiary organic base such as triethylamine or pyridine, which may also serve as a solvent, at temperatures between -25 ° C and 100 ⁰ C, but preferably at temperatures between -10 ⁰ C and the boiling temperature of the solvent used, carried out.

2-® The compounds of the general formula I obtained, since they have at least one chiral center, can be resolved by conventional methods into their diastereomers, for example by column chromatography, and into their enantiomers, for example by column chromatography on a chiral phase or by crystallization with optical active acids, for example with D- or L-monomethyltartaric, D- or L-diacetyltartaric, D- or L-tartaric acid, D- or L-lactic acid or D- or L-camphoric acid.

The resulting compounds of general formula I can be further converted into their acid addition salts, in particular for their pharmaceutical use in their physiologically acceptable acid addition salts with inorganic or organic acids. As acids hereby come in

hydrochloric, hydrobromic, sulfuric, phosphoric, acetic, lactic, citric, tartaric, succinic, maleic or fumaric acid.

The compounds of the general formulas II to VIII used as starting materials are known from the literature in some cases or are obtained by processes known per se.

Thus, for example, a starting compound of the general formula II is obtained by alkylating a corresponding imino compound of the general formula IV with a N-atom protected by a customary protecting group cyclic amine which is substituted in the carbon skeleton by an alkyl radical, which in turn terminally substituted by a nucleophilic leaving group is, and subsequent cleavage of the protective moiety used. The cyclic amine required for this purpose is obtained by converting a corresponding substituted by a hydroxyalkyl radical cyclic amine in its suitable halogen or sulfonic acid ester and the requisite imino compound of the general formula IV by cyclization of a corresponding compound, e.g. by cyclization of a compound of the general formula

, (IX)

or the general formula

^R 1

P Ι]

NH - COCH Cl

optionally subsequent catalytic hydrogenation and / or reduction of the carbonyl group, for example with sodium borohydride / glacial acetic acid (see EP-Al 0.007.070, EP-Al 0.065.229 and EP-Al 0.109.639).

A compound of the general formula V used as starting material is obtained by N-alkylation of a corresponding in the carbon skeleton by a hydroxyalkyl substituted cyclic amine with a corresponding compound or with a corresponding l, t * -Dihalogenalkan and subsequent reaction with a corresponding HO, SH or HN compound and, if necessary, subsequent oxidation, in which case a hydroxyalkyl compound thus obtained is converted into its reactive halogen or sulfonic acid ester.

A compound of the general formulas VI, VII and VIII used as starting material is preferably obtained by reacting a corresponding halogen compound with a corresponding amine and, if appropriate, subsequent removal of protective radicals which are used to protect amino groups.

As already mentioned, the new compounds of the general formula I and their physiologically acceptable acid addition salts with inorganic or organic acids have valuable pharmacological properties, in particular with low central side effects a hypotensive and a particularly long-lasting heart rate lowering effect and a reduction of the 0 ^ requirement of the heart.

- 43 For example, the compounds were

A = 3 - [(N- (2- (Naphthyl-2) -ethyl) -piperidyl-3) -methyl] -7,8-di-methoxy-2-oxo-1, 3,4 »S-tetrahydro ^ HS-benzazepine hydrochloride,

5B = 3- [(N- (2- (5-methyl-6-methoxynaphthyl-2) -ethyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-1, 3, 4,5-tetrahydro-2H-3-benzazepine hydrochloride,

C = 3- [2- (N- (2- (6-methoxynaphthyl-2) -ethyl) -piperidyl-2) -ethyl] -7,8-dimethoxy-2-oxo-l, 3,4, 5-tetrahydro-2H-3-benzazepine hydrochloride,

D = 2 - [(N- (2- (6-methoxynaphthyl-2) -ethyl) -hexahydro-azepinyl-3) -methyl] -6,7-methylenedioxy-1-oxo-l, 2,3, 4-tetrahydro-isoquinoline hydrochloride,

E = 2 - [(N- (2- (naphthyl-2) -ethyl) -hexahydro-azepinyl-3) -methyl] -6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydro- isoquinoline hydrobromide,

F = 2 - [(N- (2- (3,4-Dimethoxy-phenyl) -ethyl) -piperidyl-3) -methyl] -6,7-dimethyl-1,2,3,4-tetrahydro-isoquinoline dihydrochloride,

2Og = 2 - [(N- (2- (3,4-Dimethoxy-phenyl) -ethyl) -piperidyl-3) -methyl] -6,7-dimethyl-1-oxo-1,2,3,4- tetrahydro-isoquinoline,

H = 2- [(N- (3- (4-methoxy-phenoxy) -propyl) -piperidyl-3) -methyl] -6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro- isoquinoline,

I = 3- [(N- (4- (thienyl-2) -butyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-1,3,4-s-tetrahydro-HS- benzazepine hydrochloride,

K = 3 - [(N- (2- (benzo [b] furyl-2) -ethyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4,5- tetrahydro-2H-3-benzazepine hydrochloride and

L = 3 - [(N- (2- (benzo [b] thienyl-3) -ethyl) -piperidyl-3) -methyl] .7,8-dimethoxy-2-oxo-l, 3,4,5- tetrahydro-2H-3-benzazepine hydrochloride

investigated for their biological properties as follows: effect on heart rate in rats:

The effect of the substances to be tested on the heart rate was investigated per dose in 2 rats with an average weight of 250-300 g. The rats were anesthetized with pentobarbital (50 mg / kg i.p. and 20 mg / kg s.c.). The substances to be investigated were injected in aqueous solution into the jugular vein (0.1 ml / 100

Blood pressure was measured by cannula attached to the carotid artery and the heart rate was recorded from an ECG (II or III lead) derived from needle electrodes. The heart rate of the animals in the control period was between 350 and 400 beats / minute (bpm).

The following table contains the found values:

substance dose Heart rate reduction , to Lowering blood pressure to in bpm 20 min. in mmHg 20 min. [Mg / kq] 5 min. - 259 5 min. - 32 A 5.0 - 218 - 218 - 46 - 15 В 5.0 - 188 - 194 - 22 - 31 С 5.0 - 236 - 123 - 40 - 16 D 5.0 - 173 - 150 - 21 - 16 e 5.0 - 169 - 120 - 30 - 27 F 5.0 - 150 - 101 - 49 - 8th G 5.0 - 207 - 180 - 57 - 33 H 5.0 - 190 - 253 - 57 - 32 I 5.0 - 320 - 156 - 65 К 2.5 - 138 - 163 - 36 - 24 L 2.5 - 110 - 40

The compounds according to the invention have no toxic side effects at therapeutic doses. Thus, for example, with an intravenous administration of the substance A and L, even in a high dose of 20 mg / kg of mice, no toxic side effects could be observed except a slight sedation.

On account of their pharmacological properties, the compounds prepared according to the invention are suitable for the treatment of sinus tachycardia of various origins and for the prophylaxis and therapy of ischemic heart diseases.

The dosage required to achieve a corresponding effect is advantageously 0.01 to 0.2 mg / kg body weight, preferably 0.03 to 0.15 mg / kg body weight, once to twice daily. For this purpose, the compounds of the general formula according to the invention can be

I and their physiologically tolerated acid addition salts with inorganic or organic acids, optionally in combination with other active substances, together with one or more inert conventional carriers and / or diluents, e.g. with corn starch, lactose, cane sugar, microcrystalline cellulose, magnesium stearate, polyvinyl pyrrolidone, citric acid, tartaric acid, water, water / ethanol, water / glycerine, water / sorbitol, water / polyethylene glycol, propylene glycol, carboxymethyl cellulose or fatty substances such as hard fat or their suitable mixtures, in conventional galenic preparations such as tablets, dragees, capsules, powders, suspensions, drops, ampoules, juices or suppositories incorporate.

The following examples are intended to explain the invention in more detail:

Exemplary embodiments A

2- / - (piperidyl-3) -me-thyl-6-7-dimethoxy-1-oxo-1,2,3,4 -tetrahydro-isoquinoline

a) IT "-Benzyl-3- (hydroxymethyl) -piperidine

A mixture of 40.3 g (0.35 here) of 3- (hydroxyethyl) piperidine, 97.4 mL (0.70 mole) of triethylamine, and 40.3 mL (0.35 Hole) of benzyl chloride is added within 30 minutes heated to 95 ⁰ G and left for 2 hours at this temperature. The cooled reaction mixture is dissolved in a mixture of 2 molar sodium hydroxide solution and ethyl acetate. The organic phase is washed with water, separated, dried over IIagnes ium sulfate and evaporated in vacuo.

Yield: 57.2 g (79.6 ^c / y of theory),

R f value: 0.45 (aluminum oxide neutral, eluent: У / о ethanol in methylene chloride).

b) II-Benzyl-3- (benzenesulfonyloxymeth.vl) -piperidine

A mixture of 6.8 g (0.033 mole) of 1-benzyl-3- (hydroxymethyl) piperidine, 6.7 ml (0.052 mole) of benzenesulfuric acid chloride, 50 ml of 20% aqueous sodium hydroxide, 100 ml of toluene and 1 Spatula tip Tetrabutylammonium bromide is stirred for 3 hours at room temperature, then the organic phase is diluted with 10 ml of ethyl acetate and water, the organic phase is separated off, dried over magnesium sulfate and evaporated to dryness in vacuo of the residue is over 200 g of silica gel (0.063 - 0.2 mm) with llethylenchlorid and then increasing proportions of ethanol (to 5 ^c .o) · Yield: 9.4 g (92 °, Ό of theory), Rf - '/ ert 0.5 (silica gel, eluent: 5% ethanol in methylene chloride),

с) 2-C (N-Benzyl-piperidyl-3) -methyl] -6,7-dimethoxy-1-oxo- 1,2,3,4-tetrahydro-isoquinoline

5.2 g (0.025 mol) of 6,7-dimethoxy-l-oxo-l, 2,3,4-tetrahydro-isoquinoline are dissolved in 70 ml of dimethyl sulfoxide and tert with stirring with 3.1 g (0.025 mol) of potassium tert added butylate. After half an hour, 9.3 g (0.0275 mol) of N-benzyl-3- (benzenesulfonyloxy-methyl) -piperidine in 20 ml of dimethyl sulfide are added to the potassium salt suspension obtained and the mixture is stirred at 40 ^° C. for 2 hours. It is poured onto ice-water and extra-

Ю hiert 3 χ with 120 ml ethyl acetate. The combined organic phases are washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue obtained is chromatographed over 200 g of silica gel (0.063-0.2 mm) with methylene chloride and then increasing amounts of ethane.

¹ ^ nol (to 2%).

Yield: 7.7 g (78.5% of theory),

Rf value: 0.5 (silica gel, eluent: 5% ethanol in methylene chloride and 1 drop of ammonia).

d) 2 - [(piperidyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4- tetrahydro-isoquinoline

9.4 g (0.0238 mol) of 2 - [(N-benzyl-piperidyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline are dissolved in 200 ml of methanol in the presence of 2 g of 20% palladium hydroxide / carbon hydrogenated for 3 hours at room temperature and 5 bar of hydrogen. The catalyst is then filtered off with suction and the filtrate is evaporated to dryness in vacuo. Yield: 7.2 g (99% of theory),

Rf value: 0.15 (silica gel, eluent: 10% ethanol in methylene chloride and 1 drop of ammonia).

- 49 Example В

3-Chloromethyl-N-C3- (naphthyl-2-oxy) -propyl- 3 -piperidine a) 3- (Hvdroxymethyl) -N-C3- (naphthyl-2-oxy) -propyl-3-piperidine

A mixture of 11.5 g (0.2 mol) of 3-hydroxy-methyl-piperidine and 11 g of 2- (3-chloropropoxy) -naphthalene is heated for 1 hour at 120 ° C. The residue is passed through silica gel (0.063 0, 2 mm) with ethyl acetate / ethanol / ammonia = 90: 10: 1. Yield: 11.5 g (76.6% of theory), melting point: 99-101 ° C.

b) 3-Chloromethyl-N-C3- (naphthyl-2-oxy) -propyl] -piperidine

A solution of 1.5 g (5 mmol) of 3- (hydroxymethyl) -N- [3- (naphthyl-2-oxy) -propyl] -piperidine in 25 ml of chloroform is treated with 1.5 ml of thionyl chloride and 1 l / Boiled for 2 hours at reflux. It is evaporated to dryness in vacuo. The residue is taken up in methylene chloride, washed with water, molar sodium hydroxide solution and again with water. After drying the methylene chloride phase over magnesium sulfate is evaporated in vacuo

 Yield: 1.4 g (87.5% of theory), R f value: 0.8 (silica gel, eluent: ethyl acetate / ethanol /

Ammonia = 90: 40: 2).

Example C

2 - [(Hexahydro-azepinyl-3) -methyl] -6,7-methylenedioxy-1-oxo- 1,2,3,4-tetrahydro-isoquinoline

a) N-benzyl-caprolactam

33.9 g (0.3 mol) of caprolactam are dissolved in 250 ml of dimethyl sulfoxide and 37 g (0.33 mol) of potassium tert.

butoxide added. In this case, the reaction temperature rises to 60 ⁸ C. The mixture is stirred for 1/2 hour at 60 ^° C. and then 35 ml (0.3 mol) of benzyl bromide are added dropwise. After a further 2 1/2 hours at 60 ° C is poured onto 1 1 of ice water and extracted 3 times with ethyl acetate. The organic phases are combined, washed with water, dried over magnesium sulfate and evaporated in vacuo. Yield: 60.3 g (99% of theory), Rf value: 0.6 (silica gel, eluent: 5% ethanol in methylene chloride).

b) 1-Benzyl-caprolactam-S-carboxylic acid

To 33.9 g = 47.1 ml (0.33 mol) of diisopropylamine in 450 ml of absolute ether are added with stirring and nitrogen at -60 ° C 180 ml of 2.6 molar butyl lithium solution in η-hexane.

Then, with further cooling, 48.8 g (0.24 mol) of N-benzyl-caprolactam, dissolved in 150 ml of absolute ether, are added dropwise. After stirring for 10 minutes, the cold bath is removed and carbon dioxide is introduced for 15 minutes. The reaction mixture is poured onto ice, the ethereal phase separated and shaken twice with 2 molar sodium hydroxide solution. The aqueous-alcoholic phases are combined, extracted with ether, acidified with concentrated hydrochloric acid and extracted by shaking twice with methylene chloride. The combined methylene chloride phases are dried over magnesium sulfate and the solvent is distilled off in vacuo. Yield: 15.7 g (26.5% of theory), IR spectrum (methylene chloride): 1735 and 1600 cm (CO).

c) 1-Benzyl-3-hydroxymethyl-hexahydro-azepine

To 6.84 g (0.28 mol) of lithium aluminum hydride in 300 ml of absolute tetrahydrofuran are added dropwise 14.8 g (0.06 mol) of 1-benzyl-caprolactam-3-carboxylic acid dissolved in 300 ml of absolute tetrahydrofuran. Thereafter, it is refluxed for 6 hours.

heated, then with ice water citrification with 6.8 ml of water, 6.8 ml of 2-molar sodium hydroxide solution and 21 ml of water. The precipitate is filtered off, washed with tetrahydrofuran and the filtrate concentrated in vacuo. The residue is purified by column chromatography on alumina N (activity II, eluent: methylene chloride). Yield: 8.4 g (63.8% of theory), IR spectrum (methylene chloride): 3620 cm ^-1 (OH).

d) 1-Benzyl-3- (4-toluenesulfonyloxymethyl) -hexahydro-azepine

15 g (0.0684 mol) of 1-benzyl-3-hydroxymethyl-hexahydro-azepine are dissolved in 150 ml of pyridine and 14.3 g (0.075 mol) of p-toluenesulfonyl chloride are added with stirring and stirred for 1 hour at room temperature. It is evaporated in vacuo, taken up in methylene chloride, washed with 2 molar sodium hydroxide solution and water. After drying over magnesium sulfate, the organic phase is evaporated in vacuo. Yield: 23.3 g (91.3% of theory),

Rf value: 0.45 (silica gel, eluent: 5% ethanol in methylene chloride).

e) 2 - [(N-Benzyl-hexahydro-azepinyl-3) -methyl] -6,7-methylenedioxy -1-oxo-1,2,3,4-tetrahydro-isoquinoline

7.4 g (0.0387 mol) of 6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline are dissolved in 100 ml of dimethyl sulphoxide, with 4.5 g (0.04 mol) of potassium tert-butylate and stirred for 1/2 hour at room temperature. Subsequently, 16.8 g (0.044 mol) of 1-benzyl-3- (4-toluenesulfonyloxymethyl) hexahydro-azepine are added and stirred for 3 hours at room temperature. The reaction mixture is dissolved in ethyl acetate and extracted by shaking twice with water. The organic phase is dried over magnesium sulfate and concentrated in vacuo. The residue is purified over alumina N (activity II, eluent: methylene chloride, methylene chloride + 2% ethanol).

Yield: 3.0 g (19.6% of theory),

Rf value: 0.6 (silica gel, eluent: 5% ethanol in methylene chloride).

f) 2 - [(Hexahydro-azepinyl-3) -methyl] -6,7-methylenedioxy-1-oxo- 1,2,3,4-tetrahydro-isoquinoline

6.7 g (0.017 mol) of 2 - [(N-benzyl-hexahydro-azepinyl-3) -methyl] -6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline are dissolved in 250.degree ml of methanol in the presence of 2 g of 20% palladium hydroxide / carbon hydrogenated for 4 hours at room temperature and 5 bar hydrogen. The catalyst is then filtered off with suction and the filtrate is evaporated to dryness in vacuo. The residue crystallizes from acetone. Yield: 4.9 g (95% of theory), m.p .: 267-269 ^e C.

Example D

3-Chloromethyl-N- [3- (naphthyl-2-oxy) -propy1] hexahydro-azepine

a) 3-hydroxymethyl-hexahydro-azepine

16.6 g (0.0757 mol) of 1-benzyl-3-hydroxymethyl-hexahydro-azepine are hydrogenated in 500 ml of methanol in the presence of 16.2 g of 20% palladium hydroxide / carbon for 2 hours at room temperature and 5 bar of hydrogen. The catalyst is then filtered off with suction and the filtrate is evaporated in vacuo. Yield: 8 g (81.8% of theory), Rf value: 0.5 (silica gel, eluent: methylene chloride / ethanol / ammonia = 5: 4: 1).

b) 3-Hydroxymethyl-N- [3- (naphthyl-2-oxy) -propyl13-hexahydro- azepine hydrochloride

A mixture of 7.8 g (0.06 mol) of 3-hydroxymethyl-hexahydroxy

Azepine and 6.7 g (0.03 mol) of 2- (3-chloropropoxy) naphthalene are heated to 120 ⁰ C for 1 hour. The reaction mixture is purified over silica gel (0.063-0.2 mm) with ethyl acetate / ethanol / ammonia = 90: 10: 1

Yield: 2.3 g (24.3% of theory), Melting point: 127-129 ⁰ C.

с) 3-Chloromethyl-NC 3- (naphthyl-2-oxy) -propyl] -hexahydro- azepine

2.4 g (6.86 mmol) of 3-hydroxymethyl-N- [3- (naphthyl-2-oxy) -propyl] -hexahydro-azepine hydrochloride dissolved in 30 ml of chloroform are treated with 5 ml of thionyl chloride and 1 Cooked at reflux. It is evaporated to dryness in vacuo. The residue is dissolved in methylene chloride, shaken with water, 2 molar sodium hydroxide solution and again with water. The methylene chloride phase is dried over magnesium sulfate and evaporated in vacuo. Yield: 1.1 g (48.5% of theory),

Rf value: 0.55 (silica gel, eluent: 5% ethanol in methylene chloride).

Example E

2-C (pyrrolidyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetra -hydroxysilanol η

a) N-benzyl-2-pyrrolidone

To 25.5 g (0.3 mol) of 2-pyrrolidone in 300 ml of absolute dimethyl sulfoxide are added in portions 14.4 g (0.33 mol) of 50% sodium hydride dispersion in oil. Then for 5 hours at 40 to 50 "C is stirred and added dropwise at 25-30 ⁰ C 56.4 g = 39.2 ml (0.33 mol) of benzyl bromide. After stirring for 10 hours at room temperature, the reaction rate is

dissolved in 500 ml of ethyl acetate and extracted several times with water. The organic phase is separated, dried over magnesium sulfate and the solvent removed in vacuo. The residue obtained is purified over 900 g of aluminum oxide (neutral, activity II) with methylene chloride and 0.1% ethanol.

Yield: 35.6 g (67.7% of theory),

Rf value: 0.77 (alumina, neutral, eluent: 5% ethanol in methylene chloride).

b) N-Benzyl-2-pyrrolidone-3-carboxylic acid

To 28.3 g = 39.3 ml (0.28 mol) of diisopropylamine in 400 ml of absolute ether are added under stirring and under nitrogen at -60 "C 150 ml of 1.6 molar butyllithium solution in η-hexane to 35.1 g (0.2 mol) of N-benzyl-2-pyrrolidone, dissolved in 150 ml of absolute ether at -60 C. the ^e Kä'ltebad is removed and forwards 15 minutes, a dry carbon dioxide. After 10 minutes Stirring is carried out on ice, the organic phase is separated off and extracted by shaking twice with 2 molar sodium hydroxide solution, the combined aqueous phases are shaken out once with ether and then acidified with concentrated hydrochloric acid while cooling The aqueous phase is extracted by shaking twice with methylene chloride and after drying the organic phase concentrated over magnesium sulfate in vacuo

 Yield: 35 g (79.8% of theory),

Rf value: 0.42 (silica gel, eluent: 5% ethanol in methylene chloride).

c) N-Benzyl-3-hydroxymethyl-pyrrolidine

To 12.2 g (0.32 mol) of lithium aluminum hydride in 350 ml of absolute tetrahydrofuran is added dropwise with stirring 35 g (0.16 mol) of N-benzyl ^ -pyrrolidone-S-carboxylic acid, dissolved in 250 ml of absolute tetrahydrofuran. After heating for 6 hours under reflux,

River is added under ice-water cooling with 18.2 ml of water, 12.2 ml of 15% aqueous sodium hydroxide solution and 36.6 ml of water. The resulting precipitate is filtered off with suction and washed with tetrahydrofuran. The combined filtrates are concentrated in vacuo and the residue obtained is purified over 900 g of aluminum oxide (neutral, activity II) with methylene chloride and then with increasing proportions of ethanol (up to 2%).

Yield: 16 g (52.3% of theory),

Rf value: 0.42 (alumina, neutral, eluent: 5% ethanol in methylene chloride).

d) 3- (benzenesulfonyloxymethyl) -1-benzyl-pyrrolidine

To a mixture of 3.8 g (20 mmol) of N-benzyl-3-hydroxymethyl-pyrrolidine and 3.7 ml (24 mmol) of benzenesulfonyl chloride are added dropwise 40 ml of 20% sodium hydroxide solution for one hour. It is mixed with 150 ml of toluene, the organic phase is washed with water, dried over magnesium sulfate and evaporated to dryness in vacuo

 Yield: 5.9 g (89.4% of theory), Rf value: 0.4 (silica gel, eluent: 5% ethanol in methylene chloride).

e) 2- [N- (Benzyl-pyrrolidyl-3) -methyl] -6,7-dimethoxy-1-oxo- 1,2,3,4-tetrahydro-isoquinoline

3.3 g (15.9 mmol) of 6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydroisoquinoline are dissolved in 50 ml of dimethyl sulfoxide and stirred at room temperature with 2 g (17.5 mmol) of potassium tert added butylate. After 1/2 hour, 5.8 g (17.5 mmol) of 3- (benzenesulfonyloxymethyl) -1-benzylpyrrolidine in 10 ml of dimethyl sulfoxide is added to the resulting potassium salt suspension and stirred at 60 ^° C. for 3 hours. It is poured onto ice-water and extracted with ethyl acetate. The combined organic phases are washed with water and dried over magnesium

dried umsulfat. The organic phase is concentrated in vacuo and the residue obtained is purified over 350 g of alumina N (activity II) with methylene chloride and then increasing proportions of ethanol (to 1%). Yield: 3.3 g (54.4% of theory), Rf value: 0.74 (alumina N, eluent: 5% ethanol in methylene chloride).

f) 2- [(Pyrrolid-3-yl) -methyl] -6,7-dimethoxy-1-oxo -1,2,3,4-tetrahydro-isoquinoline

3.2 g (8.4 mmol) of 2 - [(N-benzyl-pyrrolid-3-yl) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline are added in 250 ml ml of methanol and hydrogenated in the presence of 1 g of 20% palladium hydroxide / carbon for 3 hours at room temperature and 5 bar of hydrogen. The catalyst is then filtered off with suction and the filtrate is evaporated to dryness in vacuo. The residue is purified over 150 g of silica gel (0.063-0.2 mm) with methylene chloride / ethanol / ammonia = 6: 1: 0.5. Yield: 0.9 g (37.5% of theory), Rf value: 0.6 (silica gel, eluent: methylene chloride / ethanol / ammonia = 5: 4: 1).

Example F

3- (p-Toluenesulfonyloxymethyl) -N- [2- (6- methoxynaphthyl -2) -ethyl] -pyrrolidine

a) 3-hydroxymethylpyrrolidine

14 g (0.073 mol) of N-benzyl-3-hydroxymethylpyrrolidine are hydrogenated for 7 hours at 50 ^° C. and 5 bar in 300 ml of methanol and in the presence of 1.5 g of 20% palladium hydroxide / activated carbon. The catalyst is then filtered off with suction and the filtrate is concentrated in vacuo.

Yield: 7.3 g (99% of theory), mass spectrum: Molpeak 101.

b) 3-hydroxymethyl-N- [2- (6-methoxy-naphthyl-2) -ethyl] -pyrrolidine

A mixture of 3.6 g (29.4 mmol) of 3-hydroxymethyl-pyrrolidine and 4.7 g (14.7 mmol) of 2- (2-bromoethyl) -6-methoxy-naphthalene is heated 2 hours at 120 ⁰ C. , The reaction mixture is purified over 200 g of silica gel (0.063-0.2 mm) with methylene chloride and then increasing proportions of ethanol (to 5%).

Yield: 3.48 g (82.5% of theory), m.p .: 121-123 ° C.

c) 3- (p- Toluene-sulfonyloxymethyl ) -N- [2- (6-methoxy-naphtha- lin-2) -ethyl] -pyrrolidine

0.8 g (2.8 mmol) of 3-hydroxymethyl-N- [2- (6-methoxynaphth-2-yl) -ethyl] -pyrrolidine are dissolved in 10 ml of pyridine and 1.2 g (6 , 3 mmol) of p-toluenesulfonyl chloride was added. After 2 hours at room temperature, it is evaporated to dryness in vacuo. The residue is dissolved in methylene chloride, washed with 2 molar sodium hydroxide solution and water. The organic phase is then dried over magnesium sulfate and concentrated in vacuo. The residue is purified over 150 g of silica gel (0.063-0.2 mm) with ethyl acetate and then increasing proportions of ethanol. Yield: 0.6 g (48.8% of theory), Rf value: 0.45 (silica gel, mobile phase: 5% ethanol in methyl

lenchlorid).

- 58 Example G

2- [(azacyclooctyl-B) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4- tetrahydro-isoquinoline

a) 1-Benzyl-2-oxo-azacyclooctane

25 g (0.196 mol) of 2-Azacyclooctanon are dissolved in 150 ml of dimethyl sulfoxide and treated with stirring with 24.2 g (0.216 mol) of potassium tert.butylat and stirred for 1/2 hour at 40 ⁰ C. Subsequently, 24 ml (0.2 mol) of benzyl bromide are added dropwise over 1/4 hour, during which the temperature rises to 8O ⁰ C. It is stirred for 2 hours, with the reaction temperature drops back to room temperature. The reaction mixture is poured into 1 liter of ice-water and shaken out 4 times with 150 ml of ethyl acetate each time. The combined organic phase is washed with water, dried over magnesium sulfate and evaporated in vacuo.

Yield: 42.7 g (100% of theory),

Rf value: 0.55 (silica gel, eluent: 5% ethanol in methylene chloride).

b) 1-Benzyl-azacyclooctane-2-oxo-3-carboxylic acid

To 26.7 g = 38.4 ml (0.26 mol) of diisopropylamine in 250 ml of absolute ether are added dropwise with stirring and nitrogen at -60 ⁰ C 147 ml of 1.6 molar butyllithium solution in η-hexane. Then added dropwise at -60 ⁰ C 42.7 g (0.196 mol) of 1-benzyl-2-oxo-azacyclooctane in 100 ml of absolute ether, to. After 10 minutes, dry carbon dioxide is introduced for 20 minutes. The reaction mixture is poured onto ice, the ethereal phase separated and shaken twice with 2 molar sodium hydroxide solution. The combined aqueous phases are extracted by shaking 1 time with ether and then acidified with concentrated hydrochloric acid while cooling. It is shaken out 3 times with methylene chloride, the methylene chloride phase is dried over magnesium sulfate and concentrated in vacuo.

Yield: 25.9 g (50.6% of theory),

Rf value: 0.15 (aluminum oxide, eluent: 5% ethanol in methylene chloride).

c) 1-Benzyl-S-hydroxymethyl-azacyclooctane

To 22.7 g (0.6 mol) of lithium aluminum hydride in 800 ml of absolute ether is added dropwise with stirring 53.6 g (0.205 mol) of 1-benzyl-2-oxo-azacyclooctan-3-carboxylic acid, dissolved in 100 ml of absolute tetrahydrofuran. After heating for 1/2 h under reflux, 28.4 ml of water, 19 ml of 15% sodium hydroxide solution and 57 ml of water are added with ice-water cooling. The resulting precipitate is filtered off with suction and washed with tetrahydrofuran. The combined filtrates are concentrated in vacuo and the residue obtained is purified over 700 g of aluminum oxide (neutral, activity II) with 1% ethanol in methylene chloride.

Yield: 9.3 g (19.6% of theory),

Rf value: 0.5 (silica gel, eluent: 5% ethanol in methylene chloride).

d) 1-Benzyl-3-chloromethyl-azacyclooctane

9.3 g (39.8 mmol) of l-benzyl-S-hydroxymethyl-azacyclooctane are mixed in 30 ml of pyridine with 10 ml (79.6 mmol) of benzenesulfonyl chloride and stirred for 2 1/2 hours at room temperature. The reaction mixture is evaporated in vacuo. The remaining residue is dissolved in 150 ml of methylene chloride, washed with 2N sodium hydroxide solution and water. The organic phase is dried over magnesium sulfate, evaporated to dryness and purified over 150 g of silica gel (0.063-0.2 mm) with methylene chloride

 Yield: 3.5 g (35% of theory)

Rf value: 0.75 (silica gel, eluent: 5% ethanol in methylene chloride).

e) 2 - [(N-Benzyl-azacyclooctyl-3) -methyl] -6,7-dimethoxy-1-oxo- 1,2,3,4-tetrahydro-isoquinoline

2.3 g (11/1 mmol) of 6, 7-dimethoxy-l-oxo-l, 2, 3, 4-tetrahydro-isoquinoline are dissolved in 40 ml of dimethyl sulfoxide and with stirring with 1.33 g (12.2 mmol ) Potassium tert-butylate added. After 1/2 hour, 3.5 g (9.4 mmol) for 2 hours at 120 ^e C to the obtained potassium salt suspension added l-benzyl-3-chloromethyl-azacyclooctane in 40 ml of dimethylsulfoxide and 2 l / stirred. Pour on ice water and extract 3 times with each

Ю 50 ml of ethyl acetate. The combined organic phases are washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue obtained is purified over 150 g of silica gel (0.063-0.2 mm) with 1% ethanol in methylene chloride.

Yield: 1 g (25.1% of theory),

Rf value: 0.5 (silica gel, eluent: 2% ethanol in methylene chloride)

f) 2 - [(Azacyclooctyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4- tetrahydro-isoquinoline

0.85 g (2 mmol) of 2 - [(N-benzyl-azacyclooctyl-S) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline are dissolved in 50 ml of methanol hydrogenated in the presence of 0.85 g of 20% palladium hydroxide / carbon for 4 1/2 hours at room temperature and 5 bar hydrogen. The catalyst is then filtered off with suction and the filtrate is evaporated to dryness. Yield: 0.5 (74.6% of theory),

Rf value: 0.45 (silica gel, eluent: 25% ethanol in methylene chloride and 1 drop of ammonia)

Example 61 L-Chloro-3- [N- (4-methoxy-phenyl) -methyl-amino-propane

10 g (0.073 mol) of N-methyl-4-methoxy-aniline are dissolved in 50 ml of dimethyl sulfoxide and added with stirring 9 g (0.08 mol) of potassium tert-butylate. After 1/2 hour, 10 ml of 1-bromo-3-chloropropane are added and the mixture is stirred at room temperature for 3 hours. It is poured onto ice water, extracted with ethyl acetate, the organic phase is washed with water, dried over sodium sulfate and concentrated to dryness. The residue is purified over silica gel (0.063-0.2 mm) with methylene chloride.

Yield: 9.1 g (58.3% of theory), Rf value: 0.55 (silica gel, eluent: methyl ethyl ketone / xylene = 1: 6)

Calc .: C 61.82 H 7.55 N 6.55 Cl 16.59 F .: 61.71 7.88 6.69 16.24.

Example I

2- [(N- (3- (Pyridyl-3) -propyl) -piperidyl-3) -methyl] -5,6- methylenedioxy-phthalimide

2.1 g (0.011 mol) of 5,6-methylenedioxy-phthalimide are dissolved in 100 ml of dimethyl sulfoxide and added with stirring 1.25 g (0.012 mol) of potassium tert-butylate. The potassium salt precipitates. The mixture is stirred for 1/2 hour at room temperature, a solution of 2.5 g (0.01 mol) of 3-chloromethyl-N- (3- (pyridyl-3) propyl) -piperidine in 20 ml of dimethyl sulfoxide was added and 8 hours heated to 120 ⁰ C. It is poured into ice-water, shaken out 3 times with 150 ml of ethyl acetate and the organic phase is concentrated after drying over magnesium sulfate in vacuo. The residue is purified over 200 g of silica gel (0.063-0.2 mm) with ethyl acetate / ethanol / ammonia = 80: 10: 0.5.

Yield: 3 g (74% of theory),

Ber. (2 χ HCl): C, 55.42, H, 5.86, N, 8.43, Cl, 14.22

Gef .: 55.28 6.06 8.26 14.64

Example K

2 - [(N-3-Chloropropyl) -piperidyl-3-methyl-6,7-dimethoxy-1- oxo-1,2,3,4-tetrahydro-isoquinoline

3 g (0.01 mol) of 2 - [(piperidyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline are dissolved in 50 ml of dimethyl sulfoxide and stirred 1.3 g (0.011 mol) of potassium tert-butoxide added. After 1/2 hour, 3 ml of 1-bromo-3-chloro-propane are added and stirred for one hour at room temperature. It is poured into ice water, extracted with ethyl acetate, the organic phase is washed with water, dried over sodium sulfate and concentrated to dryness in vacuo.

Yield: 2.7 g (71% of theory),

Rf value: 0.65 (silica gel, eluent: ethyl acetate / ethanol / ammonia = 50: 45: 5).

- 63 Example 1

2 - [(N- (3- (Naphthyl-2) -propyl) -piperidyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline hydrochloride

A mixture of Ig (3.2 mmol) 2- (piperidyl-3-methyl) -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline, 5 ml dimethylsulfoxide, 0.5 g (0.36 mmol) of potassium carbonate and 0.75 g (3.66 mmol) of 2- (3-chloropropyl) naphthalene is heated at 120 ⁰ C for 3 hours. The reaction mixture is poured into ice-water and shaken out 3 times with 50 ml of ethyl acetate each time. The combined organic phases are washed with 2 molar sodium hydroxide solution and water, dried over magnesium sulfate, concentrated in vacuo and the residue obtained is purified on silica gel (0.063-0.2 mm) with 1% ethanol in methylene chloride. From a solution in acetone, the hydrochloride is precipitated with ethereal hydrochloric acid and crystallized from acetone.

Yield: 0.74 g (44% of theory), melting point: 179-181 ° C calc .: C 70.77 H 7.37 N 5.50 Cl 6.96 F .: 70.47 7.40 5, 47 7.06.

Example 2

2 - [(N- (3- (naphthyl-2-oxy) -propyl) -piperidyl-3) -methyl] -6,7-dimethyl-l-oxo-1,2,3,4-tetrahydro-isoquinoline hydrochloride hydrate

1.58 g (9 mmol) of 6,7-diethyl-1-oxo-l, 2,3,4-tetrahydro-isoquinoline are dissolved in 30 ml of dimethyl sulfoxide and while stirring with 1.1 g (9.9 mmol) of potassium added tert-butylate. After one hour, a solution of 2.9 g (9.1 mmol) of 3-chloro-1-N- [3- (naphthyl-2-oxy) -propyl] -piperidine in

Added 10 ml of dimethyl sulfoxide and the reaction mixture for 16 hours at 8O ⁰ C stirred. It is then poured into ice-water, shaken 3 times with 50 ml of ethyl acetate, the organic phase is washed with water, dried over magnesium sulfate and after evaporation on silica gel (0.63 0.2 mm) with ethyl acetate / ethanol / ammonia - 95: 5: 0.5. From a solution in acetone is obtained with ethereal hydrochloric acid, the hydrochloride as a hydrate

Yield: 2 g (45.1% of theory), Melting point: 152-154 ⁰ C.

Calc .: C 70.50 H 7.69 N 5.49 Cl 6.93 F .: 70.31 7.52 5.49 7.10

Example 3

2 - [(N- (3- (2-naphthyl) -propyl) -piperidyl-3) -methyl] -6,7-dimethyl-1,2,3,4-tetrahydro-isoquinoline dihydrochloride

0.8 g (18 mmol) of 2 - [(N- (3- (naphthyl-2) -propyl) -piperidyl-3) -methyl] -6,7-dimethyl-1-oxo-l, 2,3, Dissolve 4-tetrahydro-isoquinoline in 10 ml of absolute tetrahydrofuran and 20 ml of absolute ether, add 70 mg (18 mmol) of lithium aluminum hydride and reflux for 1 hour. The reaction mixture is decomposed by addition of 5 ml of saturated aqueous sodium sulfate solution, filtered from the precipitated sodium sulfate and washed with tetrahydrofuran. The filtrate is dried over magnesium sulfate and purified after concentration over 150 g of silica gel (0.063-0.2 mm) with ethyl acetate / ethanol / ammonia = 90: 10: 0.05. From a solution in acetone, the hydrochloride is precipitated with ethereal hydrochloric acid.

Yield: 0.49 g (54.4% of theory), m.p .: 148-15O ⁰ C

Calc .: C 69.61 H 8,18 N 5,41 Cl 13,70 Found: 69,46 8,32 5,26 14,17

- 65 Example 4

2 - [(N- (3- (3-pyridyl) propyl) -piperidyl-3) -methyl] -5,6-methylenedioxy-l-oxo-1,3-dihydro-isoindole dihydrochloride

2.4 g (5.9 mmol) of 2 - [(N- (3- (pyridyl-3) -propyl) -piperidyl-3) -methyl] -5,6-methylenedioxy-phthalimide are dissolved in 50 ml of glacial acetic acid and Cooked for 5 hours at reflux. At intervals of one hour each, 1 g of zinc dust is added. After completion of the reaction time is filtered off with suction, evaporated with ethanol. The residue is dissolved in methylene chloride, shaken out with concentrated ammonia, dried over magnesium sulfate and, after concentration in vacuo, purified over 150 g of silica gel (0.063-0.2 mm) ethyl acetate / ethanol / ammonia = 90: 10: 0.2. From a solution in acetone, the hydrochloride is precipitated.

Yield: 2.05 g (75% of theory),

Melting point: 165-167 ⁰ C

Ber. : C 59.22 H 6.27 N 9.00 Cl 15.20 Gef.: 59.03 6.45 8.85 15.06

Example 5

3 - [(N- (3- (3-pyridyl) propyl) -pyrrolidyl-3) -methyl 1-7, 8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro-2H-3- benzoazepine dihydrochloride

1.1 g (2.6 mmol) of 3 - [(N- (3- (pyridyl-3) -propyl) -pyrrolidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3 Dihydro-2H-3-benzoazepine, dissolved in 50 ml of ethanol, is hydrogenated in the presence of 1 g of 10% palladium on activated charcoal at 80 ° C. and 5 bar of hydrogen for 2 hours, after which the catalyst is filtered off with suction and the filtrate after concentration in vacuum over

100 g of silica gel (0.063-0.2 mm) with ethyl acetate / ethanol / ammonia = 80: 40: 1 purified. From a solution in acetone, the hydrochloride is precipitated.

Yield: 0.37 g (33% of theory), mp: 96-98 ° C

Calc .: C 60.42 H 7.11 N 8.46 Cl 14.28 V: 60.35 7.46 8.43 14.58

Example 6

2- [(N- (3- (N-ethyl-3,4-dimethylanilino) -propyl) -piperidyl-3) -methyl] -6,7-dimethoxy-1-oxo-l, 2,3, 4-tetrahydro-isoquinoline dihydrochloride

A mixture of 1.3 g (0.0034 mol) of 2 - [(N- (З-СЬІогцгоруі) -piper-idyl-3) -methyl] -6,7-dimethoxy-1-oxo-l, 2,3, 4-tetrahydroisoquinoline, 15 ml of dimethyl sulfoxide, 1.4 g (0.1 MoI) potassium carbonate and 1 g (0.0066 mol) of N-ethyl-3,4-dimethyl-aniline are heated at 120 ⁰ C for 6 hours. The reaction mixture is poured onto ice-water, shaken out with ethyl acetate, the organic phase is washed with water, dried over sodium sulfate and evaporated in vacuo. The residue obtained is purified over silica gel (0.032-0.063 mm) with 5% ethanol in methylene chloride. From a solution in acetone, the dihydrochloride was precipitated with ethereal hydrochloric acid. Yield: 633 mg (37.7% of theory), Melting point: 97-100 ⁰ C.

Calcd .: C, 61.63, H, 8.10, N, 7.1, Cl, 12, 12, Found: 61.52, 8.15 -6.92, 11.82

Example 7

2 - [(N- (2- (4-Amino-phenyl) -ethyl) -piper-idyl-3) -methyl] -5,6-dimethoxy-1-oxo-1,3-dihydro-isoindole-dihydrochloride id

2.1 g (4.78 mmol) of 2 - [(N- (2- (4-nitro-phenyl) -ethyl) -piperidyl-3) -methyl] -5,6-dimethoxy-1-oxo-1, 3-dihydro-isoindole are dissolved in 50 ml of glacial acetic acid and, while stirring, 0.4 ml (8.22 mmol) of hydrazine hydrate and 1 spatula tip of Raney nickel are added. The addition of 0.2 ml of hydrazine hydrate and 1 spatula tip Raney nickel is repeated at intervals of one hour times. It is filtered off with suction from the catalyst, washed with methanol, the filtrate is dried with magnesium sulfate, concentrated in vacuo and the residue obtained is purified over alumina (neutral, activity II) with methylene chloride and then increasing proportions of ethanol.

Yield: 1.8 g (91.8% of theory), 1 g is dissolved in acetone and the dihydrochloride is precipitated with ethereal hydrochloric acid.

Yield: 1.02 g (86.4% of theory based on base), m.p .: 232-235 ° C

Calc .: C 59.72 H 6.89 N 8.71 Cl 14.69 F .: 59.54 7.08 8.56 14.45

Example 8

2 - [(N- (2- (4-Acetamino-phenyl) -ethyl) -piperidyl-3) -methyl] -5,6-dimethoxy-1-oxo-1,3-dihydro-isoindole

819 mg (2 mmol) of 2 - [(N- (2- (4-amino-phenyl) -ethyl) -piperidyl-3) -methyl] -5,6-dimethoxy-1-oxo-1,3-dihydro -isoindole are added dropwise in 10 ml of methylene chloride and after the addition of 0.3 ml (2.2 mmol) of triethylamine with 0.16 ml (2.2 mmol)

Acetyl chloride added. In this case, the reaction temperature rises to 3O ⁰ C. The mixture is stirred for 1/2 hour at room temperature, shaken twice with water, the organic phase is dried over magnesium sulfate and concentrated in vacuo. The residue is crystallized from acetone

Yield: 660 mg (73.2% of theory), Melting point: 195-196 ⁰ C.

Calc .: C 69.16 H 7,37 N 9,31 F .: 69,33 7,11 9,16

Example 9

3 - [(N- (3- (2-furyl) propyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro-2H-3- benzazepine hydrochloride

3.2 g (0.010 mol) of 3 - [(piperidyl-3) methyl] -7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydro-2H-3-benzazepine are dissolved in 100 ml of absolute Ethanol in the presence of 1.3 g (0.010 mol) of 3- (furyl-2) -propanal and 1 g Raney nickel at 8O ⁰ C for 2 days at 5 bar hydrogenated. It is suctioned off from the catalyst, concentrated and purified on a silica gel column with methylene chloride / methanol as eluent. The hydrochloride is precipitated with ethereal hydrochloric acid and crystallized from acetone

Yield: 0.50 g (11% of theory), Melting point: 204-206 ⁰ C.

Calc .: C 64.85 H 7.62 N 6.05 Cl 7.66 F .: 64.88 7.76 5.93 7.55

Rf value: 0.69 (silica gel, methylene chloride / methanol = 10: 1, ammonia / atmosphere)

- 69 Example 10

2 - [(N- (3- (3-Methylphenoxy) -propyl) -piperidyl-3) -methyl] -6,7-dimethoxy-1,2,3-tetrahydro-isoquinoline dihydrochloride

Prepared from 2 - [(N- (3- (3-methylphenoxy) -propyl) -piperidyl-3) -methyl] -b, 7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline and Lithium aluminum hydride in diethyl ether and tetrahydrofuran analogously to Example 3. Yield: 92.9% of theory, melting point: 100-103 ^e C

Calc .: C 61.23 H 7.99 N 5.29 Cl 13.39 Vessel: 61.21 8.13 5.10 13.15

Example 11

2 - [(N- (3- (naphthyl-2-oxy) -propyl) -pyrrolidyl-3) -methyl] -6,7-dimethoxy-l-oxo-1,2,3,4-tetrahydro-isoquinoline hydrochloride

Prepared from 6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 3-chloromethyl-N- [3- (naphthyl-2-oxy) -propyl] -pyrrolidine analogously to Example 2

 Yield: 22% of theory, melting point: 78-80 ° C

Ber. (XH ₂ O): C 65.83 H 7.04 N 5.29 Cl 6.70 V: 65.79 7.00 5.03 6.99

Example 12

2 - [(N- (3- (naphthyl-2-oxy) -propyl) -pyrrolidyl-3) -methyl] -6,7-methylenedioxy-l-oxo-1,2,3,4-tetrahydro-isoquinoline hydrochloride

Prepared from 6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydroisoquinoline and 3-chloromethyl-N- [3- (naphthyl-2-oxy) -propyl] -pyrrolidine analogously to Example 2.

Yield: 53% of theory,

Melting point: 78-80 ⁰ C Ber. (x H ₂ O): C 65.56 H 6.48 N 5.46 Cl 6.91

F .: 65.44 6.32 5.38 7.13

Example 13

2- [(N- (2- (Naphthyl-2) -ethyl) -pyrrolidyl-3) -methyl] -6, 7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline hydrochloride

Prepared from 2 - [(N- (2- (naphthyl-2) -ethyl) -pyrrolidyl-3) -methyl] -6,7-direthoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline; Lithium aluminum hydride in tetrahydrofuran and ether analogously to Example 3.

Yield: 66.2% of theory, melting point: 239-241 ° C

Ber. (x H ₂ O): C, 64.48, H, 7.44, N, 5.37, Cl, 13.91, Found: 64.30, 7.34, 5.52, 13.69

Example 14

2 - [(N - ((2-methyl-naphthyl-1) -methyl) -hexahydro-azepinyl-3) methyl] -6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline-hydro-chloride

Prepared from 2 - [(N - ((2-methyl-naphthyl-1) -methyl) -hexahydro-azepinyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4- tetrahydro-isoquinoline and lithium aluminum hydride in tetrahydrofuran and ether analogously to Example 3

 Yield: 73.8% of theory, melting point: 182-184 ° C

Ber. (x H ₂ O): C 65.56 H 7,70 N 5,09 Cl 12,90 Found: 65,52 7,57 5,32 12,72

- 72 Example 15

2- [(N- (4- (Naphthyl-2-oxy) -butyl) -pyrrolidyl-3) -methyl] -6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline hydrochloride

Prepared from 2- (pyrrolidyl-3-methyl) -6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 2- (4-bromo-butyloxy) -naphthalene analogously to Example 1

 Yield: 30% of theory, melting point: 133-136 ° C

Calc .: C 67.02 H 6.92 N 5.21 Cl 14.86 Found: 67.26 7.03 5.36 14.89

Example 16

2 - [(N- (2-methyl-l-naphthyl) -methyl) -pyrrolidyl-3) -methyl] -6,7-dimethyl-l-oxo-l, 2,3,4-tetrahydro-isoquinoline hydrochloride

Prepared from 2- (pyrrolidyl-3-methyl) -6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 1-chloromethyl-2-methylnaphthalene analogously to Example 1.

Yield: 32.5% of theory,

Melting point: 142-144 ° C

Calc .: C 69.34 H 7.69 N 5.77 Cl 7.37 F .: 69.59 7.63 5.72 7.89

- 73 Example 17

2 - [(N- (2- (5-methyl-6-methoxy-naphthyl-2) -ethyl) -pyrrolidyl-3) -methyl] -6,7-dimethyl-l-oxo-l, 2,3, 4-tetrahydro-isoquinoline hydrobromide

Prepared from 2- [N- (pyrrolidyl-3-methyl)] - 6, 7-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 2- (2-bromoethyl) -5-methyl-6- Methoxy-naphthalene analogously to Example 1. Yield: 19% of theory, melting point: 230-232 ^e C

Calc .: C 67.02 H 6.93 N 5.21 Br 14.86 Found: 67.10, 7.12, 5.33, 15.01

Example 18

2 - [(N- (2- (2-naphthyl) ethyl) -pyrrolidyl-3) -methyl] -6,7-dimethoxy-l-oxo-1,2,3,4-tetrahydro-isoquinoline hydrochloride

Prepared from 2- (pyrrolidyl-3-methyl) -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 2- (2-bromoethyl) -naphthalene analogously to Example 1

 Yield: 7.8% of theory, melting point: 219-22 ° C

Ber. (xH ₂ O): C 67.39 H 7.07 N 5.61 Cl 7.10 Found: 67.21 7.23 5.57 7.63

- 74 Example 19

2- [(N- (2- (6-Methoxy-naphthyl-2) -ethyl) -pyrrolidyl-3) -methyl] 6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline hydrochloride

Prepared from 2 - ((pyrrolidyl-3) -methyl) -6,7-dimethoxy-loxo-1,2,3,4-tetrahydro-isoquinoline and 2- (2-bromoethyl) -6-methoxynaphthalene analogously to Example 1 Yield: 39.2% of theory, m.p .: 224-226 ° C

Ber. (x H ₂ O): C 65.84 H 7.05 N 5.29 Cl 7.05 Found: 66.08 7.13 5.39 6.77

Example 20

2- [(N- (3- (Naphthyl-2) -propyl) -piperidyl-3) -methyl] -6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline hydrochloride

Prepared from 6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 3-chloromethyl-N- [3- (naphthyl-2) -propyl] -piperidine analogously to Example 2

 Yield: 40.4% of theory, melting point: 185-187 ° C

Calc .: C 75.52 H 7.82 N 5.87 Cl 7.43 V .: 75.39 7.85 5.82 7.52

Example 21

2- [2- (N- (3- (Naphthyl-2-oxy) -propyl) -piperidyl-2) -ethyl] -6,7 · methylenedioxy-1-oxo-1,2,3,4-tetrahydro isoquinoline hydrochloride

Prepared from 2 - ((piperidyl-2) -ethyl) -6,7-methylenedioxy-loxo-1,2,3,4-tetrahydro-isoquinoline and 2- (3-chloropropoxy) -naphthalene analogously to Example 1

 Yield: 21.2% of theory, melting point: 85-87 ° C

Ber. (x H ₂ O): C 66.59 H 6.89 N 5.17 Cl 6.53 V .: 66.77 6.98 4.95 6.74

Example 22

2- [ (N- (3- (Naphthyl-2-oxy) -propyl) -piperidyl-3) -methyl] -6,7-dimethyl-1,2,3,4-tetrahydro-isoquinoline-dihydrochloride

Prepared from 2 - [(N- (3- (naphthyl-2-oxy) -propyl) -piperidyl-3) -methyl] -6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro- isoquinoline and lithium aluminum hydride in tetrahydrofuran / ether analogously to Example 3

 Yield: 53% of theory,

20 Melting point: 133-135 ⁰ C Ber. (x H ₂ O): C 68.30 H Gef .: 68.05

6 87 N 5, 31 Cl 13 44 6 85 5, 23 13 03

- 76 Example 23

2-C (N- (3- (naphthyl-2-oxy) -propyl) -piperidyl-3) -methyl] -6,7-methylenedioxy-1,2,3,4-tetrahydro-isoquinolin ~ dihydrochloride

Prepared from 2 - [(N- (3- (naphthyl-2-oxy) -propyl) -piperidyl-3) -methyl] -6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydro-1-one isoquinoline and lithium aluminum hydride in tetrahydrofuran / ether analogously to Example 3

Yield: 44.7% of theory, Melting point: 130-132 C ^e

Ber. (XH ₂ O): C 63.62 H 6,62 N 5,11 Cl 12,95 Found: 63,49 6,86 4,97 12,64

Example 24

2-C (N - ((2-methyl-naphthyl-1) -methyl) -piper-idyl-3) -methyl] -6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline-dihydrochloride

Prepared from 2-ί (N - ((2-methyl-naphthyl-1) -methyl) -piperidyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro- isoquinoline and lithium aluminum hydride in tetrahydrofuran / ether analogously to Example 3

 Yield: 80.5% of theory,

Melting point: 210-212 ^e C

Ber. (xH ₂ 0): C 65.05 H 7.53 N 5.23 F .: 65.23 7.78 5.03

Example 25

2- [2- (N- (2- (6-Methoxy-naphthyl-2) -ethyl) -piperidyl-2) -ethyl] 6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydro -isoquinoline hydrochloride

Prepared from 2- [2- (piperidyl-2) -ethyl) -6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 2- (2-bromoethyl) -6-methoxy naphthalene as in example 1. yield: 27.6% of theory, melting point: 112-117 ⁰ C.

Ber. (x 1/2 H ₂ O): C 67.74 H 6.82 N 5.26 Cl 6.65 Fe.i 67.54 6.73 5.47 6.86

Example 26

2 - [(N- (2- (l-naphthyl) ethyl) -piperidyl-3) -methyl] -6,7-dimethoxy-l-oxo-1,2,3,4-tetrahydro-isoquinoline hydrochloride

Prepared from 2 - [(piperidyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline and benzenesulfonic acid 2-ethyl (naphthyl-1) -ester analog Example 1.

Yield: 26.9% of theory,

Melting point: 220-225 ⁰ C Calc .: C 67.89 H 7.27 N 5.46 Cl 6.91 Found .: 67.75 6.92 5.56 7.00

Example 27

2 - [(N- (2- (2-naphthyl) ethyl) -piperidyl-3) -methyl] -6,7-methylenedioxy-l-oxo-1,2,3,4-tetrahydro-isoquinoline hydrochloride

Prepared from 2 - [(piperidyl-3) -methyl3-6, 7-methylenedioxy-1-oxo-l, 2,3,4-tetrahydro-isoquinoline and benzenesulfonic acid 2-ethyl (naphthyl-2) ester analogously to Example 1. Yield: 27.9% of theory, m.p .: 128-130 ° C

Ber. (xH ₂ 0): C 67.66 H 6.69 N 5.63 Cl 7.13 Found: 67.64 6.70 5.76 7.35

Example 28

2-C (N- (2- (5-Methyl-6-methoxynaphthyl-2) -ethyl) -piperidyl-3) methyl] -6,7-methylenedioxy-1-oxo-1,2,3,4 tetrahydro-isoquinoline hydrochloride

Prepared from 2 - [(piperidyl-3) -methyl] -6,7-methylenedioxy-oxo-1,2,3,4-tetrahydro-isoquinoline and 2- (2-bromoethyl) -5-methyl-6-methoxy naphthalene analogously to Example 1. Yield: 51.2% of theory, melting point: 128-131 ° C

Calc .: C 68.88 H 6, 74 N 5.34 Cl 6.77 V .: 68.90 6.61 5.30 7.05

Example 29

2-C (N - ((2-methyl-naphthyl-1-methyl) -piperidyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline hydrochloride

Prepared from 2 - [(piperidyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 1-chloromethyl-2-methylnaphthalene analogously to Example 1

Yield: 57.9% of theory, m.p .: 212-214 ⁸ C

Ber. (x 2 H ₂ O): C, 67.63, H, 7.63, N, 5.44, Cl, 6.88, Found: 67.46, 7.56, 5.54, 6.67

Example 30

2 - [(N- (4- (Naphthyl-2-oxy) -butyl) -piperidyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline hydrochloride

Prepared from 2 - [(piperidyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 2- (4-bromo-butoxy) -naphthalene analogously to Example 1

 Yield: 46.3% of theory, m.p .: 80-84 "C

Ber. (XH ₂ O): C 66.83 H 7.41 N 5.03 Cl 6.36 V .: 66.79 7.22 4.90 6.64

- 80 Example 31

2 - [(N- (2- (6-methoxy-naphthyl-2) -ethyl) -piperidyl-3) -methyl] -б, 7-dimethoxy-l-oxo-l, 2,3,4-tetrahydro- isoquinoline hydrochloride

Prepared from 2 - [(piperidyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 2- (2-bromo-ethyl) -6-methoxy naphthalene analogously to Example 1

Yield: 22.8% of theory, m.p. 80-85 ⁰ C

Calc .: (x H ₂ O χHCl χCH ₃ COCH ₃ ): С 64.01 H 7.65 N 4.52 Cl 5.72 V: 64.26 7.70 4.62 5.49

Example 32

2- [3- (N- (2- (6-methoxy-naphthyl-2) -ethyl) -piperidyl-3) -propyl] -6,7-methylenedioxy-l-oxo-l, 2,3,4- tetrahydro-isoquinoline

Prepared from 2- [3- (piperidyl-3) -propyl] -6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 2- (2-bromoethyl) -6-methoxy- naphthalene analogously to Example 1. Yield: 36.8% of theory, melting point: 118-121 ° C.

Calc .: C 74.37 H 7.25 N 5.60 F .: 74.60 7.43 5.65

Example 33

2- [3- (N- (2- (Naphthyl-1) -ethyl) -piperidyl-3) -propyl] -6,7-methylenedioxy-1-oxo-1,2,3- _r 4-tetrahydro-isoquinoline hydrochloride

Prepared from 2- [3- (piperidyl-3) -propyl] -6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline and benzenesulfonic acid 2-ethyl- (naphthyl-1) - ester analogously to Example 1. Yield: 20.8% of theory, melting point: 195-197 ° C

Calc .: C, 71.07, H, 6.95, N, 5.53, Cl, 6.99, Found: 71.30, 6.95, 5.65, 6.80

Example 34

2- [2- (N- (2- (5-Methyl-6-methoxynaphthyl-2) -ethyl) -piperidyl-2) -ethyl] -6,7-dimethoxy-1-oxo-1, 2, 3,4-tetrahydroisoquinoline hydrochloride id

Prepared from 2- [2- (piperidyl-2) -ethyl] -6,7-dimethoxy-loxo-1,2,3,4-tetrahydro-isoquinoline and 2- (2-bromo-ethyl) -5-methyl- 6-methoxynaphthalene analogously to Example 1.

Yield: 33.6% of theory,

Melting point: 95-100 ⁰ C Ber. (x 1/2 H ₂ O): C 68.38 H 7.52 N 4.98 Cl 6.30

Gef .: 68.14 7.43 4.92 6.77

Example 35

2 - [(N- (3- (naphthyl-2-oxy) -propyl) -piperidyl-3) -methyl] -6,7-methylenedioxy-l-oxo-1,2,3,4-tetrahydro-isoquinoline hydrochloride

Prepared from 6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydroisoquinoline and 3-chloromethyl-N- [3- (naphthyl-2-oxy) -propyl] -piperidine analogously to Example 2

Yield: 27.3% of theory, Melting point: 104-106 ⁰ C.

Ber. (x H ₂ O): C 66.09 H 6.69 N 5.31 Cl 6.72 V .: 66.19 6.34 5.24 7.22

Example 36

2 - [(N- (3- (naphthyl-2-oxy) -propyl) -piperidyl-3) -methyl] -6,7-dimethoxy-l-oxo-1,2,3,4-tetrahydro-isoquinoline hydrochloride

Prepared from 6,7-dimethoxy-l-oxo-l, 2,3,4-tetrahydro-isoquinoline and 3-chloromethyl-N- [3- (naphthyl-2-oxy) -propyl] -piperidine analogously to Example 2.

Yield: 28.6% of theory,

Melting point: 191-193 ⁰ C Ber. (x H ₂ O): C 66.34 H 7.23 N 5.15 Cl 6.53

Gef .: 66.59 7.19 5.03 6.65

Example 37

2- I (N- (3- (Naphthyl-2-oxy) -propyl) -hexahydro-azepinyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro- isoquinoline

Prepared from 2 - [(hexahydro-azepinyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 2- (3-chloropropoxy) -naphthalene analogously to Example 1

 Yield: 16.1% of theory, melting point: 86-88 ° C

Ber. (x H ₂ O): C 66.83 H 7.42 N 5.03 Cl 6.36 V: 66.90 7.40 5.26 6.87

Example 38

2- [(N- (3- (Naphthyl-2-oxy) -propyl) -hexahydro-azepinyl-3) -methyl] -6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro- isoquinoline

Prepared from 6,7-dimethyl-1-oxo-l, 2,3,4-tetrahydro-isoquinoline and 3-chloromethyl-N- [3- (naphthyl-2-oxy) -propyl] -hexahydro-azepine analogously to Example 2 Yield: 22.5% of theory, m.p .: 191-193 ° C

Calc .: C 73.42 H 7.75 N 5.52 Cl 6.99 F .: 73.37 7.67 5.52 7.12

Example 39

2 - [(N- (2- (5-methyl-6-methoxy-naphthyl-2) -ethyl) -hexahydroazepinyl-3) -methyl] -6,7-dimethoxy-l, 2,3,4-tetrahydro- isoquinoline dihydrochloride

Prepared from 2- [(N- (2- (S-methyl-6-methoxy-naphthyl) ethyl) -hexahydro-azepinyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2, 3,4-tetrahydro-isoquinoline and lithium aluminum hydride in tetrahydrofuran analogously to Example 3. Yield: 77.6% of theory, melting point: 170-172 ⁰ C.

Ber. (x H ₂ O): C 64.96 H 7.49 N 4.73 Cl 11.98 F .: 65.11 7.62 4.95 11.84

Example 40

(N- (2- (5-methyl-6-methoxy-naphthyl-2) -ethyl) -hexahydroazepinyl-3) 2-t -methyl] -6,7-dimethoxy-l-oxo-l, 2,3, 4-tetrahydroisoquinoline

Prepared from 2 - [(hexahydro-azepinyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 2- (2-bromoethyl) -S-methyl- δ-Methoxynaphthalene analogously to Example 1. Yield: 43.5% of theory, melting point: 125-127 ° C. Calc .: C 74.39 H 7.80 N 5.42 V .: 74.31 7.82 5 35

- 85 Example 41

2 - [(N- (2-Methyl-naphthyl-1) -methyl) -hexahydro-azepinyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline hydrochloride

Prepared from 2 - [(hexahydro-azepinyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 1-chloromethyl-2-methylnaphthalene analogously to Example 1 Yield: 67.5% of theory, melting point: 128-13O ⁰ C

Ber. (x 2 H ₂ O): C 66.10 H 7.58 N 5.13 Cl 6.50 V .: 66.24 7.44 5.23 6.85

Example 42

2-C (N- (4- (naphthyl-2-oxy) butyl) hexahydro-azepinyl-3) -methyl] -6,7-dimethoxy-l-oxo-l, 2,3,4-tetrahydro- isoquinoline

Prepared from 2 - [(hexahydro-azepinyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 2- (4-bromo-butyloxy) -naphthalene analog example 1

Yield: 26% of theory, Melting point: 192-194 C ^e

Calcd .: C, 69.22, H, 7.80, N, 5.04, Cl, 6.38, Found: 70.01, 7.70, 5.15, 6.48

Example 43

2 - [(N- (2- (Naphthyl-1) -ethyl) -hexahydro-azepinyl-3) -methylΙό, 7-methylenedioxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline-hydro-chloride

Prepared from 2 - [(hexahydro-azepinyl-3) -methyl] -6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 2- (2-benzenesulfonyloxy-ethyl) -naphthalene analog example 1. yield: 15.4% of theory, melting point: 236-238 ⁰ C.

Ber. (x 1/2 H ₂ O): C 69.40 H 6.82 N 5.58 Cl 7.06 Found .: 69.07 6.74 6.13 7.29

Example 44

2-C (N- (2- (2-naphthyl) ethyl) hexahydro-azepinyl-3) -methyl] -6,7-methylenedioxy-l-oxo-l, 2,3,4-tetrahydro-isoquinoline hydrobromide

Prepared from 2 - [(hexahydro-azepinyl-3) -methyl] -6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 2- (2-bromoethyl] -naphthalene analogously to Example 1

Melting point: 100-102 ^e C Yield: 31.6% of theory,

Calc .: C 64.80 H 6.18 N 5.21 Br 14.86 F .: 65.02 6.07 5.39 14.78

Example 45

2- [(N- (2- (6-Methoxy-naphthyl-2) -ethyl) -hexahydro-azepinyl-3) methyl] -6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydro -isoquinoline hydrochloride

Prepared from 2 - [(hexahydro-azepinyl-3) -methyl] -6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydroisoquinoline and 2- (2-bromoethyl] -6-methoxy naphthalene analogously to Example 1. Yield: 34.1% of theory, melting point: 147-149 ° C.

Ber. (x H ₂ O): C 68.62 H 7.10 N 5.33 Cl 6.75 V .: 68.88 6.98 5.41 6.78

Example 46

2- [(N- (2- (5-Methyl-6-methoxy-naphthyl-2) -ethyl) -hexahydroazepinyl-3) -methyl] -6,7-methylenedioxy-1-oxo-l, 2,3, 4-tetrahydro-isoquinoline hydrochloride

Prepared from 2 - [(hexahydro-azepinyl-3) -methyl] -6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 2- (2-bromoethyl] -S-methyl- e-methoxy-naphthalene analogously to Example 1. Yield: 36.1% of theory, melting point: 112-114 ° C

Ber. (x H ₂ O): C 67.07 H 7.08 N 5.04 Cl 6.38 V: 67.13 7.15 4.97 6.56

- Example 47

2 - [(N- (3- (4-Methoxy-phenoxy) -propyl) -piperidyl-3) -methyl] -6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline-dihydrochloride

Prepared from 2 - [(N- (3- (4-methoxy-phenoxy) -propyl) -piperidyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro- isoquinoline and lithium aluminum hydride in tetrahydrofuran analogously to Example 3.

Yield: 88.5% of theory, melting point: 189-191 ^e C

Calcd .: C 59.44 H 7, 76 N 5.13 Cl 12.99 Found: 59.55 7.99 5.12 12.61

Example 48

2 - [(N- (2- (3,4-Dimethoxy-phenyl) -ethyl) -piperidyl-3) -methyl] -6,7-dimethoxy-1,2,4-tetrahydro-isoquinoline-dihydrochloride

Prepared from 2 - [(N- (2- (3,4-dimethoxy-phenyl) -ethyl) -piperidyl-3) -methyl] -6, 7-dimethoxy-1-oxo-1, 2, 3,4- tetrahydro-isoquinoline and lithium aluminum hydride in tetrahydrofuran analogously to Example 3

 Yield: 92.8% of theory,

Melting point: 175-176 ° C

Calc .: C 60.66 H 7, 35 N 5.33 Cl 13.49 Found: 60.58 7.56 5.32 13.22

- 89 Example 49

2 - [(N- (3- (3-Methoxy-phenoxy) -propyl) -piperidyl-3) methyl] -6,7-methylenedioxy-1,2-sulfo-isoquinoline dihydrochloride

Prepared from 2 - [(N- (3- (3-methoxy-phenoxy) -propyl) -piperidyl-3) -methylJ-6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydroisoquinoline and lithium aluminum hydride in tetrahydrofuran analogously to Example 3

 Yield: 96.6% of theory, m.p .: 178-181 ° C

Calc .: C 59.08 H 7.62 N 5.30 Cl 14.31 F .: 58.90 7.50 5.40 14.15

Example 50

2-1 (N- (3- (3-Methoxy-phenoxy) -propyl) -piperidyl-3) -methylJ-6,7-methylenedioxy-1,2,3,4-tetrahydro-isoquinoline-dihydrochloride

Prepared from 2 - [(N- (3- (3-methoxy-phenoxy) -propyl) -piperidyl-3) -methyl] -6: 7-methylenedioxy-1-oxo-1,2,3,4-tetrahydroisoquinoline; Lithium aluminum hydride in tetrahydrofuran analogously to Example 3.

Yield: 94.5% of theory,

Melting point: 169-171 "C

Calc .: C 57.03 H 7.36 N 5.11 Cl 13.86

Gef .: 56.91 7.26 5.15 13.68

- 90 Example 51

2 - [(N- (2- (3,4-Dimethoxyphenyl) ethyl) piperidyl-3) methyl] 6,7-dimethyl-1,2,3,4-tetrahydroisoquinoline dihydrochloride

Prepared from 2 - [(N- (2- (3,4-Dimethoxy-phenyl) -ethyl) -piperidyl-3) -methyl] -6,7-dimethyl-1-oxo-1, 2, 3, 4 tetrahydro-isoquinoline and lithium aluminum hydride in tetrahydrofuran analogously to Example 3

Yield: 91.3% of theory, melting point: 140-142 ⁰ C.

Calc .: C 62.00 H 8, 34 N 5.27 Cl 13.44 F .: 61.85 8.27 5.31 13.33

Example 52

2-C (N- (3- (4-Methoxy-phenoxy) -propyl) -piperidyl-3) -methyl] -6,7-dimethyl-1,2,3,4-tetrahydro-isoquinoline-dihydrochloride

Prepared from 2 - [(N- (3- (4-methoxy-phenoxy) -propyl) -piperidyl-3) -methyl] -6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro- isoquinoline and lithium aluminum hydride in tetrahydrofuran analogously to Example 3

 Yield: 88.3% of theory,

Melting point: 170-172 ⁰ C

Calc .: C 63.14 H 8.24 N 5.65 Cl 14.31 V .: 63.09 8.33 5.82 14.02

- 91 Example 53

2 - [(N- (2- (3,4-Dimethoxy-phenyl) -ethyl) -piper-idyl-3) -methyl] -6,7-methylenedioxy-1,2,3,4-tetrahydro-isoquinoline-dihydrochloro -

Prepared from 2- [ (N- (3- (3,4-Dimethoxy-phenyl) -ethyl) -piperidyl-3) -methyl] -6,7-methylenedioxy-1-oxo-1,2,3,4- tetrahydroisoquinoline and lithium aluminum hydride in tetrahydrofuran analogously to Example 3

Yield: 93.3% of theory, Melting point: 150-154 ⁰ C.

Calc .: C 60.01 H 7.34 N 5.39 Cl 13.64 F .: 59.96 7.41 5.25 13.43

Example 54

2 - [(N- (3- (4-methoxy-phenoxy) -propyl) -piperidyl-3) -methyl] -6,7-dimethoxy-l, 2,3,4-tetrahydro-isoquinoline dihydrochloride

Prepared from 2 - [(N- (3- (4-methoxy-phenoxy) -propyl) -piperidyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro- isoquinoline and lithium aluminum hydride in tetrahydrofuran analogously to Example 3

 Yield: 95.3% of theory, melting point: 182-185 ° C

Calc .: C 61.05 H 7.09 N 5.48 Cl 13.86 F .: 61.10 6.95 5.68 13.55

- 92 Example 55

2- [2- (N- (3- (3,4-methylenedioxy-phenoxy) -propyl) -piperidyl-3) -ethyl] -6, 7-dimethoxy-1-oxo-1, 2, 3,4- tetrahydro-isoquinoline hydrochloride

Prepared from 2- [(piperidyl-3) -ethyl] -6,7-diethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 1-chloro-3- (3,4-methylenedioxy-phenoxy ) propane as in example 1. yield: 35.5% of theory, melting point: 97-100 ⁰ C.

Calcd .: C 59.09 H 7.28 N 4.62 Cl 6.65 F .: 58.97 7.36 4.66 6.52

Example 56

2- [2- (N- (2- (3,4-Dimethoxy-phenyl) -ethyl) -piperidyl-3) -ethyl] 6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro -isoquinoline hydrochloride

Prepared from 2 - [(piperidyl-3) -ethyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 1-bromo-2- (3,4-dimethoxyphenyl) - ethane analogously to Example 1

Yield: 35.9% of theory, Melting point: 103-105 ⁰ C.

Calc .: C 62.60 H 7.79 N 5.21 Cl 6.83 F .: 62.41 7.82 5.09 7.19

- 91 Example 57

2-С 3- (N- (2- (3,4-Dimethoxy-phenyl) -ethyl) -piperidyl-3) -propyl] -6,7-dimethoxy-1-oxo-1,2,3,4- tetrahydro-isoquinoline hydrochloride

Prepared from 2- [3- (piperidyl-3) -propyl] -6,7-dimethoxy-loxo-l, 2,3,4-tetrahydro-isoquinoline and 1-bromo-2- (3,4-dimethoxy-phenyl ) -ethane analogously to Example 1

Yield; 32.6% of theory, melting point: 102-106 ⁰ C.

Ber. : C 63.20 H 7.86 N 5.08 Cl 6.43 F .: 63.39 7.90 4.86 6.13

Example 58

2- [3- (N- (3- (3,4-methylenedioxy-phenoxy) -propyl) -piperidyl-3) -propyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro -isochinolinhydrochlorid

Prepared from 2- [3- (piperidyl-3) -propyl] -6,7-dimethoxy-loxo-l, 2, 3,4-tetrahydro-isoquinoline and 1-chloro-3- (3,4-methyl-1-dioxy) phenoxy) propane as in example 1. yield: 29.7% of theory, melting point: 97-100 C ^e

Calc .: C 61.63 H 7.31 N 4.96 Cl 6.47 V .: 61.94 7.46 5.16 6.48

- 94 Example 59

2 - [(N- (3,4-Dimethoxy-benzyl) -piperidyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline hydrochloride

Prepared from 2- (piperidyl-3-methyl) -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 3,4-dimethoxybenzylbromide analogously to Example 1

Yield: 53.3% of theory, Melting point: 127-132 ⁰ C.

Calc .: C 63.58 H 7,18 N 5,70 Cl 7,22 Vessel: 63,30 7,22 5,52 7,14

Example 60

2-E (N- (3- (4-methoxy-phenyl) -propyl) -piperidyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline hydrochloride

Prepared from 2- (piperidyl-3-methyl) -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 1-bromo-3- (4-methoxyphenyl) -propane analogously to Example 1 ,

Yield: 42% of theory,

Melting point: 229-231 "C

Calcd .: 66.37 7.67 Cl 7.25 Found: 66.27 7.64 5.65 7.33

- 95 Example 61

2- [2- (N- (3- (3-methyl-phenoxy) -propyl) -piperidyl-2) -ethyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro- isoquinoline hydrochloride

Prepared from 2- [2- (piperidyl-2) -ethyl] -6,7-dimethoxy-loxo-l, 2,3,4-tetrahydro-isoquinoline and 1-chloro-3- (3-methylphenoxy) -propane analog example 1. yield: 52.4% of theory, melting point: 142-144 ⁰ C.

Calc .: C, 66.85, H, 7.81, N, 5.57; Cl, 7.05; Vents: 66.73, 7.68, 5.53, 6.94

Example 62

2-C 2- (N- (2- (3, 4-Dimethoxy-phenyl) -ethyl) -piper-idyl-2) -ethyl] 6,7-dimethoxy-1-oxo-1,2,3,4 tetrahydro-isoquinoline hydrochloride

Prepared from 2- [2- (piperidyl-2) -ethyl] -6,7-dimethoxy-loxo-l, 2,3,4-tetrahydro-isoquinoline and 1-bromo-2- (3,4-dimethoxy-phenyl ) -ethane analogously to Example 1. Yield: 47.3% of theory, melting point: 150-155 ° C

Calc .: 64.74 7.83 5.67 6.90

Example 63

2- [2- (N- (3-Benzyloxy-propyl) -piperidyl-2) -ethyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline hydrochloride

Prepared from 2- [2- (piperidyl-2) ethyl] -6,7-dimethoxy-1-5 oxo-1,2,3,4-tetrahydro-isoquinoline and 1-chloro-3-benzyloxypropane analogously to Example 1

Yield: 56.3% of theory, melting point: 116-12O ⁰ C.

Ber. : C 66.85 H 7,81 N 5,57 Cl 7,05 Vessel: 66,60 7,75 5,25 7,25

Example 64

2- C 2- (N- (4- (4-Methoxy-phenyl) -butyl) -piper-2-ethyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro -isoquinoline hydrochloride

Prepared from 2- [2- (piperidyl-2) -ethyl] -6,7-dimethoxy-loxo-1,2,3,4-tetrahydro-isoquinoline and 1-bromo-4- (4-methoxyphenyl) -butane analog Example 1.

Yield: 42.8% of theory, Melting point: 107-112 ⁰ C.

Calcd .: C, 67.36, H, 7.99, N, 5.42, Cl, 6.86, Found: 67.16, 8.05, 5.35, 7.34

- 97 Example 65

2- [2- (N- (3- (3,5-dimethoxy-phenoxy) -propyl) -pipe r idy1-2) -ethyl] -6,7-dimethoxy-1-oxo-1,2,3 4-tetrahydro-isoquinoline hydrochloride

Prepared from 2- [2- (piperidyl-2) -ethyl] -6,7-dimethoxy-loxo-1,2,3,4-tetrahydro-isoquinoline and 1-chloro-3- (3,5-dimethoxy-phenoxy ) -propane analogously to Example 1. Yield: 56.3% of theory, melting point: 127-132 ° C

Ber. : C 61.41 H 7.64 N 5.10 Cl 6.46 Vessel: 61.56 7.65 5.28 6.89

Example 66

2- [2- (N- (3- (3,4-methylenedioxy-phenoxy) -propyl) -piperidyl-2) -ethyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro -isochinolinhydrochlorid

Prepared from 2- [2- (piperidyl-2) -ethyl] -6,7-dimethoxy-loxo-l, 2,3,4-tetrahydro-isoquinoline and 1-chloro-3- (3,4-methyl-1-dioxy) phenoxy) propane as in example 1. yield: 49% of theory, melting point: 118-120 ⁰ C.

Calc .: C 63.09 H 7.00 N 5.26 Cl 6.65 V: 62.90 7.04 5.46 6.79

- 98 Example 67

2-C (N- (3- (3,5-dimethoxy-phenoxy) -propyl) -piperidyl-3) -methyl] -6,7-dimethoxy-l-oxo-l, 2,3,4-tetrahydro- isoquinoline

Prepared from 2 - [(piperidyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 1-chloro-3- (3,5-dimethoxyphenoxy) - Propane analogously to Example 1. Yield: 37.5% of theory, melting point: 98-102 ^e C

Ber. : C, 62.85, H, 7.35, N, 5.24, Cl, 6.63, Gef.: 62.81, 7.41, 5.10, 6.75

Example 68

2 - [(N- (3- (3,4-methylenedioxy-phenoxy) -proru1) -piperidyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro isoquinoline

Prepared from 2 - [(piperidyl-2) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 1-chloro-3- (3,4-methylenedioxyphenyl) - Propane analogous to Example 1. Yield: 50% of theory, melting point: 236-238 "C

Calc .: C, 64.46; H, 7.01; N, 5.57, Cl, 7.04, Found: 64.30, 6.97, 5.59, 7.08

- 99 Example 69

2 - [(N- (3- (3,4-methylenedioxy-phenoxy) -prору1) -piperidyl-3) -methyl] -6,7-dimethoxy-l-oxo-l, 2,3,4-tetrahydro- isoquinoline

Prepared from 2 - [(piperidyl-2) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 1-chloro-3- (3,4-methylenedioxy-phenoxy ) -propane analogously to Example 1. Yield: 46.2% of theory, melting point: 149-153 ⁰ C.

Ber. C 60.38 H 6.94 N 5.21 Cl 6.60 V: 60.30 6.93 5.29 6.37

Example 70

2 - [(N- (3- (2,6-dimethyl-phenoxy) -propyl) -piperidyl-3) -methyl] -6,7-dimethoxy-l-oxo-l, 2,3,4-tetrahydro- isoquinoline hydrochloride

Prepared from 2 - [(piperidyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 1-chloro-3- (2,6-dimethylphenoxy) - Propane analogously to Example 1

Yield: 53.3% of theory, Melting point: 131-135 ⁰ C.

Calc .: C, 66.85, H, 7.81, N, 5.57, Cl, 7.05. Fet .: 66.88, 7.95, 5.59, 6.85

- 100 Example 71

2 - [(N- (4- (2,4-dichloro-phenoxy) -butyl) -piperidyl-3) -methyl] o, 7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline hydrochloride

Prepared from 2 - [(piperidyl-3) -methyl] -6,7-dimethoxy-1-oxo

1,2,3,4-tetrahydro-isoquinoline and 1-chloro-4- (2,4-dichloro)

phenoxy) -butane analogously to Example 1

 Yield: 54.1% of theory, m.p .: 125-128 ° C

Ber. : C, 58.12 H, 6.32, N, 5.02, Cl, 19.06, Found: 58.21, 6.38, 5.0, 18.85

Example 72

2-C (N- (2- (3,4-dimethoxy-phenyl) -ethyl) -piperidyl-3) -methyl] -6,7-dimethoxy-l-oxo-l, 2,3,4-tetrahydro- isoquinoline-hydrochlo _rid

Prepared from 2 - [(piperidyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 1-bromo-2- (3,4-dimethoxyphenyl) - ethane analogously to Example 1

Yield: 57.5% of theory, m.p .: 118-121 ^e C

Calc .: C 64.21 H 7, 38 N 5.55 F .: 64.18 7.36 5.19

- 101 Example 73

2-С (N- (3- (3,4-Dimethoxy-phenoxy) -propyl) -piperidyl-3) -methyl] -6, 7-dimethoxy-1-oxo-1,2,3,4-tetrahydro -isochinolinhydrochlorid

Prepared from 2 - [(3-piperidyl) methyl] -6, 7-dimethoxy-l-oxo-1, 2, 3,4-tetrahydro-isoquinoline and l-chloro-3- (3,4-dimethoxyphenoxy) - Propane analogously to Example 1

Yield: 62.5% of theory, Melting point: 112-115 ⁰ C.

Calc .: C 60.80 H 7.47 N 5.24 V: 60.65 7.69 5.27

Example 74

2 - [(N- (3- (3,4-dimethoxy-phenoxy) -propyl) -piperidyl-3) -methyl] -6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydro- isoquinoline hydrochloride

Prepared from 2 - [(piperidyl-3) -methyl] -6,7-methylenedioxy-oxo-1,2,3,4-tetrahydro-isoquinoline and 1-chloro-3- (3,4-dimethoxy-phenoxy) - propane analogously to example 1. yield: 60% of theory, melting point: 97-100 ⁰ C.

Calc .: C 60.38 H 6.94 N 5.40 Cl 6.60 V .: 60.20 6.97 5.21 6.83

- 102 Example 75

2 - [(N- (2- (4-methoxy-phenyl) -ethyl) -piperidyl-3) -methy1] -б, 7-methylenedioxy-l-oxo-1 / 2,3,4-tetrahydro-isoquinoline hydrochloride

Prepared from 2 - [(piperidyl-3) -methyl] -6,7-methylenedioxy-loxo-1,2,3,4-tetrahydro-isoquinoline and 1-chloro-2- (4-methoxyphenyl) -ethane analogously to Example 1

Yield: 71.4% of theory, Melting point: 195-197 ⁰ C.

Ber. C, 62.94, H, 6.97, N, 5.87, C, 7.73, V: 62.90, 6.98, 5.68, 8.04

Example 76

2-C (N- (2- (3,4-Dimethoxy-phenyl) -ethyl) -piperidyl-3) -methyl] .6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro- isoquinoline hydrochloride

Prepared from 2 - [(piperidyl-3) -methyl] -6, 7-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 1-bromo-2- (3,4-dimethoxyphenyl) - ethane analogously to Example 1

 Yield: 41.9% of theory, m.p .: 132-134 ° C

Calc .: C 63.57 H 8.10 N 5.49 Cl 6.95 F .: 63.70 8.26 5.45 7.13

- 103 Example 77

2-C (N- (3- (4-methoxy-phenoxy) -propyl) -piperidyl-3) -methyl] -b, 7-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline hydrochloride

Prepared from 2 - [(piperidyl-3) -methyl] -6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 1-chloro-3- (4-methoxyphenoxy) -propane analog example 1. yield: 57.8% of theory, melting point: 144-146 ⁰ C.

Ber. : C 68.55 H 7.88 N 5.92 Cl 7.49 F .: 68.45 7.80 6.11 7.33

Example 78

2 - [(N- (3- (3-methoxy-phenoxy) -propyl) -piperidyl-3) -methyl] -6,7-methylenedioxy-l-oxo-l, 2,3,4-tetrahydro-isoquinoline hydrochloride

Prepared from 2-Е (piperidyl-3) -methyl] -6,7-methylenedioxy-oxo-l, 2,3,4-tetrahydro-isoquinoline and 1-chloro-3- (3-methoxy-phenoxy) -propane analog Example 1. Yield: 32.5% of theory, m.p .: 142-145 "C

Calc .: C 60.58 H 6.95 N 5.52 Cl 6.99 Found: 60.42 6.92 5.50 7.18

- 104 Example 79

2 - [(N- (3- (З-Methy1-phenoxy) -propyl) -piper-idyl-3) -methyl] -6,7-methylenedioxy-1-oxo-1 / 2,3,4-tetrahydro-isoquinoline hydrochloride

Prepared from 2 - [(piperidyl-3) -methyl] -6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 3- (3-methyl-phenoxy) -! Chloro-propane analogously to Example 1. Yield: 31.6% of theory, melting point: 178-180 ^e C

Ber. : C 63.59 H 6.97 N 5.70 Cl 7.22 Vessel: 63.59 6.92 5.86 7.50

Example 80

2-C (N- (3- (4-methoxy-N-methyl-phenylamino) -propyl) -piper-idyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4 tetrahydro-isoquinoline dihydrochloride

Prepared from 2 - [(piperidyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 1-chloro-3- <4-methoxy-N-methyl phenylamino) propane as in example 1. yield: 52.5% of theory, Melting point: 180-183 ⁰ C.

Calc .: C 60.64 H 7.45 N 7.58 Cl 12.79 V: 60.50 7.35 7.56 12.87

- 105 Example 81

2-С (N- (3- (4-methoxy-phenoxy) -propyl) -pyrrolidy1-3) methyl] -б, 7-dimethoxy-l-oxo-l, 2,3,4-tetrahydro-isoquinoline hydrochloride

Prepared from 6,7-dimethoxy-l-oxo-l, 2,3,4-tetrahydro-iso-quinoline and N- (3- (4-methoxy-phenoxy) -propyl) -3-benzenesulfonyloxymethyl-pyrrolidine analogously to Example 2 Yield: 84.4% of theory, melting point: 142-144 ⁹ C

Ber. : C 63.60 H 7,18 N 5,71 Cl 7,22 V .: 63,75 7,12 5,64 7,32

Example 82

2 - [(N- (3- (6-Methoxynaphthyl-2-oxy) -propyl) -pyrrolidyl-3) 6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline

¹ ^ Prepared from 6,7-dimethoxy-l-oxo-l, 2,3,4-tetrahydro-isoquinoline and 3- (p-toluenesulfonyloxymethyl) -N- (6-methoxynaphthyl-2-oxy) -pyrrolidine analogously to Example 2 . yield: 47% of theory, melting point: 142-144 ⁰ C.

Calc .: C 71.41 H 7.19 N 5.55 F .: 71.14 7.16 5.53

- 106 Example 83

2-C (N- (3- (4-Methoxy-phenoxy) -propyl) -pyrrolidyl-3) -methyl] -b, 7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline dihydrochloride

Prepared from 2 - [(N- (3- (4-methoxy-phenoxy) -propyl-pyrrolidyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-iso - Quinoline and lithium aluminum hydride in tetrahydrofuran analogously to Example 3

Yield: 90.9% of theory, melting point: 248-250 ^e C

Calcd .: C, 60.81, H, 7.46, N, 5.46, Cl, 13.81, Gef.: 60.79, 7.61, 5.48, 13.84

Example 84

2 - [(N- (3- (4-methoxy-phenoxy) -proru1) -pyrrolidyl-3) -methylΙό, 7-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline-hydrochlo-

Prepared from 6,7-dimethyl-l-oxo-l, 2, 3,4-tetrahydro-isoquinoline and N- [3- (4-methoxy-phenoxy) -propyl] -3-benzenesulfonyloxymethyl-pyrrolidine analogously to Example 2

Yield: 60.6% of theory, Melting point: 118-121 ⁰ C.

Calc .: C, 68.03, H, 7.69, N, 6.10, C, 7.72, F: 67.90, 7.71, 6.04, 7.90

Example 85

2-С (N- (2- (3,4-Dimethoxy-phenyl) -ethyl) -pyrrolidyl-3) -methyl] .6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro- isoquinoline hydrochloride

Prepared from 6,7-dimethoxy-l-oxo-l, 2,3,4-tetrahydro-isoquinoline and N-C2- (3,4-dimethoxy-phenoxy) -ethyl] -3-benzenesulphonyloxymethylpyrrolidine analogously to Example 2. Yield: 56.7% of theory, m.p .: 116-118 ° C

Ber. : C 63.60 H 7,19 N 5,71 Cl 7,22 Vessel: 63,82 7,32 5,60 7,66

Example 86

2-C (N- (3- (4-Methoxy-phenoxy) -propyl) -pyrrolidyl-3) -methyl3-6,7-dimethyl-1,2,3,4-tetrahydro-isoquinoline-dihydrochloride

Prepared from 2- [N- (3- (4-methoxy-phenoxy) -propyl) -pyrrolidyl-3) -methyl] -6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline and lithium aluminum hydride in tetrahydrofuran analogously to Example 3

 Yield: 90.9% of theory,

Melting point: 243-246 ⁰ C

Calc .: C 64.85 H 7.95 N 5.82 Cl 14.73 V .: 64.88 7.92 5.63 14.80

- 108 Example 87

2-C (N- (2- (3,4-Dimethoxy-phenyl) -ethyl) -pyrrolidyl-3) -methyl] 6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline-dihydrochloride

Prepared from 2 - [(N- (2- (3,4-Dimethoxy-phenyl) -ethyl) -pyrrolidyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4- tetrahydro-isoquinoline and lithium aluminum hydride in tetrahydrofuran analogously to Example 3

Yield: 92.9% of theory, melting point: 240-242 ^e C

Calc .: C 60.81 H 7.46 N 5.46 Cl 13.81 F .: 60.64 7.61 5.31 13.50

Example 88

2-C (N- (3-pyridyl-4) -propyl) -pyrrolidyl-3) -methyl] -5,6-dimethyl-1-oxo-1,3-dihydroisoindole dihydrochloride semihydrate

Prepared from 2 - [(N- (3-pyridyl-4) -propyl) -pyrrolidyl-3) -methyl] -5,6-dimethyl-phthalimide and zinc / glacial acetic acid analogously to Example 4.

Yield: 65% of theory, m.p .: 119-122 ° C

Calc .: C 62.02 H 7.24 N 9.43 Cl 15.92 F .: 62.25 7.47 9.39 15.90

- 109 Example 89

2-C 3- (N- (3- (Pyridyl-3-propyl) -piperidyl-3) -propyl] -5,6-dimethoxy-1-oxo-1,3-dihydroisoindole dihydrochloride monohydrate

Prepared from 2- [3- (N- (3-pyridyl-3) -propyl) -piperidyl-3) -propyl] -5, б-dimethoxy-phthalimide and zinc / glacial acetic acid analogously to Example 4.

Yield: 72% of theory, m.p .: 118-121 ^e C

Calc .: C 59.08 H 7.43 N 7.95 Cl 13.41 Mixture: 59.02 7.23 7.12 13.27

Example 90

2-C (N- (3- (3-pyridyl) propyl) -piperidyl-3) -methyl] -5,6-diraethoxy-l-oxo-1,3-dihydro-isoindole dihydrochloride monohydrate

Prepared from 2 - [(N- (3-pyridyl-3) -propyl) -piperidyl-3) -methyl] -5,6-dimethoxy-phthalimide and zinc / glacial acetic acid analogously to Example 4.

Yield: 42% of theory, m.p .: 91-96 "C

Calc .: C 59.08 H 7.43 N 7.95 Cl 13.41 Found: 59.02 7.23 7.12 13.27

Example 91

2-C (N- (2- (6,7-Dimethoxy-isoquinolyl-4) -ethyl) -piperidyl-3) methyl-3 -5, ib-dimethoxy-1-oxo-1,3-dihydro-isoindole

Prepared from 2 - [(N- (2- (6,7-dimethoxy-isoquinolyl-4) -ethyl) -piperidyl-3) -methyl] -5,6-dimethoxy-phthalimide and zinc / glacial acetic acid analogously to Example 4

Yield: 64% of theory, m.p .: 85-88 ^e C

Calc .: C 65.39 H 7,19 N 7,88 Found: 65,16 7,27 7,53

Example 92

2-C 2- (N- (3- (pyridyl-4) -propyl) -piperidyl-2) -ethyl] -5,6-dimethyl-1-oxo-1,3-dihydro-isoindole

Prepared from 2- [2- (N- (3- (pyridyl-4) -propyl) -piperidyl-2) -ethyl] -5,6-dimethyl-phthalimide and zinc / glacial acetic acid analogously to Example 4.

Yield: 73% of theory, melting point: 103-104 ^e C calc .: C 76.68 H 8.49 N 10.73 Gef.: 76.57 8.54 10.60

Example 93

2-C (N- (3- (4-pyridyl) -propy1) -pyrrolidyl-3) -methyl3-5,6-dimethyl-1,3-dihydro-isoindol-trihydrochloride semihydrate

Prepared from 2-C (N- (3- (pyridyl-4) -propyl) -pyrrolidyl-3) -

- Ill -

methyl] -5,6-dimethyl-1-oxo-1,3-dihydro-isoindole and lithium aluminum hydride in tetrahydrofuran / ether as in Example 3. Yield: 68% of theory, melting range: 118-127 ° C. (amorphous)

Calc .: C, 59.03, H, 7.54, N, 8.98, Cl, 22.73, Found: 58.93, 7.48, 8.84, 22.92

Example 94

2- [2- (N- (3- (4-pyridyl) propyl) -piperidyl-2) ethyl] -5,6-dimethyl-1,3-dihydro-isoindol

Prepared from 2- [2- (N- (3- (pyridyl-4) -propyl) -piperidyl-2) -ethyl 3-5, б-dimethyl-1-oxo-1,3-dihydro-isoindole and lithium aluminum hydride in Tetrahydrofuran / ether analogously to Example 3. Yield: 70% of theory, melting range: 135-148 ^e C (amorphous)

Calc .: C 54.59 H 8, 24 N 7.63 Cl 19.33 F .: 54.48 8.26 7.51 19.60

Example 95

2- £ (N- (l- (4-pyridyl) methyl) -piperidyl-3) -methyl] -5,6-dimethoxy-1,3-dihydro-isoindol-trihydrochloride trihydrate

Prepared from 2 - [(N- (1- (pyridyl-4) -methyl) -piperidyl-3) -methyl] -5,6-dimethoxy-phthalimide and lithium aluminum hydride in ether analogously to Example 3.

Yield: 68% of theory,

Melting range: 176-189 ° C (amorphous) Calc .: C 49.76 H 7,21 N 7,91 Cl 20,03 Found: 49,93 7,12 8,00 20,44

Example 96

2-C (N- (2- (6,7-Dimethoxy-isoquinolyl-4) -ethyl) -piperidyl-3) methyl] -5, ib-dimethyl-1,3-dihydro-isoindole-dihydrochloride-hemihydrate

Prepared from 2 - [(N- (2- (6,7-dimethoxy-isoquinolyl-4) -ethyl) -piperidyl-3) -methyl] -5, γ-dimethyl-1-oxo-1,3-dihydroisoindole and Lithium aluminum hydride in tetrahydrofuran / ether analogously to Example 3

Yield: 22.7% of theory, melting range: 222-236 ^e C (amorphous)

Calc .: C 62.22 H 7.20 N 7.50 Cl 15.83 Vessel: 62.01 7.64 7.08 15.79

Example 97

2 - [(N- (I- (Pyridy1-4) methyl) -piperidyl-3) -methyl] -5,6-methylenedioxy-1,3-dihydro-isoindol-trihydrochloride semihydrate

Prepared from 2 - [(N- (1- (pyridyl-4) -methyl) -piperidyl-3) -methyl] -5,6-methylenedioxy-phthalimide and lithium aluminum hydride in tetrahydrofuran / ether as in Example 3. Yield: 55% of Theory, Melting Range: 215-225 ^e C (amorphous)

Calc .: C 53.68 H 6.22 N 8.94 Cl 22.63 F .: 53.60 6.45 8.65 22.28

Example 98

2 - [(N- (3- (4-pyridyl) propyl) -pyrrolidyl-3) -methyl] -6,7-dimethyl-1,2,3,4-tetrahydro-isoquinoline trihydrochloride monohydrate

Prepared from 2 - [(N- (3- (pyridyl-4) -propyl) -pyrrolidyl-3) -methyl] -6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline; Lithium aluminum hydride in tetrahydrofuran / ether analogously to Example 3.

Yield: 63% of theory, m.p .: 254-256 ^e C

Calc .: C, 58.71, H, 7.80, N, 8.56, Cl, 21.66, Gef., 58.53, 7.72, 8.25, 21.53

Example 99

2 - [(N- (l- (Pyridy1-4) methyl) -piperidy1-3) methyl] -6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline trihydrochloride dihydrate

Prepared from 2 - [(N- (1- (pyridyl-4) -methyl) -piperidyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3-4-tetrahydro-isoquinoleaA and Lithium aluminum hydride in tetrahydrofuran / ether analogously to Example 3

 Yield: 63% of theory,

Melting range: 158-169 ^e C (amorphous)

Calc .: C 52.42 H 7.27 N 7.97 Cl 20.18

Gef .: 52.55 7.49 7.57 20.25

- 114 Example 100

2- [2- (N- (3- (4-pyridyl) propyl) -piperidyl-2) -ethyl] -6,7-methylenedioxy-1,2,3,4-tetrahydro-isoquinoline trihydrochloride trihydrate

Prepared from 2- [2- (N- (3- (pyridyl-4) -propyl) -piperidyl-2) -ethyl] -6,7-methylenedioxy-1-oxo-1,2,3-4-tetrahydro- Isoquinoline and lithium aluminum hydride in tetrahydrofuran / ether analog

Example 3.

Yield: 90% of theory, Melting range: 108-119 ^e C (amorphous) Calc .: C 52.58 H 7.41 N 7.36 Cl 18.62 F .: 52.56 7.25 7.38 19, 49

Example 101

2 - [(N- (3- (Pyridyl-3) -propyl) -piperidyl-3) -methyl] -6,7-methylenedioxy-1,2,3,4-tetrahydro-isoquinoline dihydrochloride monohydrate

Prepared from 2 - [(N- (3- (pyridyl-3) -propyl) -piperidyl-3) -methyl] -6,7-methylenedioxy-1-oxo-1,2,4-tetrahydro-isoquinoline; Lithium aluminum hydride in tetrahydrofuran / ether analogously to Example 3.

Yield: 72% of theory,

Melting range: 126-138 ° C (amorphous) Calc .: C 59.50 H 7.28 N 8.67 Cl 14.64 Found: 59.57 7.29 8.49 14.51

Example 102

2 - [(N- (3- (Pyridyl-3) -propyl) -piperidyl-3) -methyl] -6 _/ 7-dimethyl-1,2,3,4-tetrahydro-isoquinoline-trihydrochloride

Prepared from 2 - [(N- (3- (pyridyl-3) -propyl) -piperidyl-3) -methyl] -6,7-dimethyl-1-oxo-1,2,3,3-tetrahydro-isoquinoline; Lithium aluminum hydride in tetrahydrofuran / ether analogously to Example 3.

Yield: 59% of theory, Melting range: 138-154 ^е С (amorphous)

Calc .: C 61.66 H 7.86 N 8.62 Cl 21.84 Vessel: 61.53 8.00 8.64 21.35

Example 103

2-C (N- (3- (Pyridyl-4-propyl) -pyrrolidyl) -3) -methyl] -6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline dihydrochloride monohydrate

Prepared from 6,7-dimethyl-1-oxo-l, 2,3-4-tetrahydro-isoquinoline and 3-chloromethyl-N- [3- (pyridyl-4) -propyl] -pyrrolidine analogously to Example 2

Yield: 39% of theory, Melting range: 74-86 ^e C (amorphous)

Calc .: C 61.53 H 7.53 N 8.97 Cl 15.13 F .: 61.42 7.62 8.83 15.05

- 116 Example 104

2- [(N- (3- (Pyridyl-3) -propyl) -piperidyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline dihydrochloride monohydrate

Prepared from 6,7-dimethoxy-l-oxo-l, 2,3-4-tetrahydro-isoquinoline and 3-benzenesulfuric acid N- [3- (pyridyl-3) -propyl) -piperidyl-3] -methyl ester in dimethyl sulfoxide with potassium tert-butylate analogously to Example 2

Yield: 45% of theory, Melting range: 140-148 ⁰ C (amorphous) Ber. (x 2 HCl χH ₂ O): C, 58.36 H Gef. 58.35

Example 105

2- [3- (N- (3- (4-pyridyl) propyl) -piperidyl-3) -propyl] -6,7-dimethoxy-l-oxo-1,2,3,4-tetrahydro-isoquinoline dihydrochloride dihydrate

Prepared from 2- [3- (piperidyl-3) -propyl] -6,7-dimethoxy-loxo-l, 2,3-4-tetrahydro-isoquinoline and 4- (3-chloropropyl) -pyridine analogously to Example 1

 Yield: 48% of theory,

Melting range: 85-96 ° C (amorphous)

Calcd .: C 57.84 H 7.73 N 7.49 Cl 12.65

Gef .: 57.71 7.91 7.35 13.04

7, 25 N 8th, 16 Cl 13 78 7, 32 8th, 04 13 65

Example 106

2- [3- (N- (2- (6,7-Dimethoxy-isoquinolyl-4) -ethyl) -piperidyl-3) -propyl] -6,7-dimethoxy-1-oxo-1,2,3,4 tetrahydro-isochinolindihydrochlorid-monohyrat

Prepared from 2- [3- (pyridyl-3) -propyl] -6,7-dimethoxy-1-oxo-1,2, 3-4-tetrahydro-isoquinoline and 4- (2-chloroethyl) -6,7- dimethoxy-isoquinoline analogous to Example 1. Yield: 34% of theory, melting range: 162-171 ^е С (amorphous)

Ювег .: С 60,17 H 7,10 N 6,57 Cl 11,10 Found: 59,85 7,00 6,86 11,04

Example 107

2-C (N- (3- (3-pyridyl) propyl) -piperidyl-3) -methyl] -6,7-methylenedioxy-l-oxo-1,2,3,4-tetrahydro-isoquinoline hydrochloride

Prepared from 6,7-methylenedioxy-1-oxo-l, 2,3-4-tetrahydroisoquinoline and 3-chloromethyl-N- [3- (pyridyl-3) -propyl] -piperidine analogously to Example 2

Yield: 60% of theory, Melting range: 194-196 'C (amorphous)

20s .: C 64.92 H 6.81 N 9.46 Cl 7.98 F .: 64.91 6.95 9.67 7.80

- 118 Example 108

2 - [(N- (I- (4-pyridyl) methyl) -piperidyl-3) -methyl] -6,7-dimethoxy-l-oxo-1,2,3,4-tetrahydro-isoquinoline-dihydrochloride monohydrate

Prepared from 6,7-dimethoxy-l-oxo-l, 2,3-4-tetrahydro-isoquinoline in dimethylsulfoxide with potassium tert -butylate and 3-chloromethyl-N-Cl- (pyridyl-4) -methyl] -piperidine analogously to Example 2.

Yield: 41% of theory, melting range: 142-158 ^e C (amorphous)

Calc .: C 56.78 H 6.83 N 8.63 Cl 14.58 V: 56.45, 6.59, 8.66, 14.62

Example 109

2-C (N- (2- (6,7-Dimethoxy-isoquinolyl-4) -ethyl) -piperidyl-3) methyl] -6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro -isoquinoline ihydrochloro id

Prepared from 6,7-dimethyl-l-oxo-l, 2,3-4-tetrahydro-isoquinoline in dimethylsulfoxide with potassium tert -butylate and 3-chloromethyl-N- [2- (6,7-dimethoxy-isoquinolyl- 4) -ethyl] -piperidine analogously to Example 2.

Yield: 62% of theory,

Melting range: 148-162 ° C (amorphous)

Calc .: C 64.27 H 7.01 N 7.49 Cl 12.65 F .: 64.11 7.20 7.59 12.89

Example 110

2-C2- (N- (3- (pyridyl-4) -propyl) -piperidyl-2) -ethyl-3-6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline dihydrochloride dihydrate

Prepared from 6,7-methylenedioxy-1-oxo-l, 2,3-4-tetrahydroisoquinoline and 2- (2-chloroethyl) -N- [3- (pyridyl-4) -propyl] -piperidine analogously to Example 2

 Melting range: 115-128 "C (amorphous) Calc .: C 56.59 H 7.03 N 7.92 Cl 13.37 V .: 56.61 6.90 7.84 13.41

Example 111

2-C (N- (3- (3-pyridyl) propyl) -piperidyl-3) -methyl] -6,7-dimethyl-l-oxo-1,2,3,4-tetrahydro-isoquinoline dihydrochloride dihydrate

Prepared from 6,7-dimethyl-1-oxo-l, 2,3-4-tetrahydro-isoquinoline in dimethylsulfoxide with potassium tert -butylate and 3-chloromethyl) -N-C3- (pyridyl-3) -propyl] - piperidine analogously to Example 2

 Yield: 62% of theory,

Melting range: 118-127 ° C (amorphous) Calc .: C 60.00 H 7.85 N 8.39 Cl 14.16 V: 60.24 8.07 8.36 14.62

- 120 Example 112

2 - [(N- (3- (Pyridyl-3) -propyl) -pyrrolidyl-3) -methyl] -6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline-dihydrochloride

Prepared from 6,7-methylenedioxy-1-oxo-l, 2,3-4-tetrahydroisoquinoline and 3-chloroethyl-N- [3- (pyridyl-3) -propyl] -pyrrolidine analogously to Example 2

Yield: 26% of theory, Melting range: 102-113 ⁰ C (amorphous) Calc .: C 59.22 H 6.27 N 9.01 Cl 15.20 Found .: 59.27 6.49 8.92 14 48

Example 113

2 - [(N- (3- (Pyridyl-4) -propyl) -pyrrolidyl-3) -methyl] -7,8-methylenedioxy-2-oxo-1,3-dihydro-2H-3-benzazepine dihydrochloride

Prepared from 7,8-methylenedioxy-2-oxo-1,3-dihydro-2H-3-benzazepine and 3-chloromethyl-N- [3- (pyridyl-4) -propyl] -pyrrolidine analogously to Example 2

 Yield: 58% of theory, Melting range: 132-141 ° C (amorphous) Calc .: C 60.25 H 6.11 N 8.78 Cl 14.82 Found: 60.00 6.40 8.52 14, 56

Example 114

2- [(N- (3- (pyridyl-3) -propyl) -piperid-3-yl) -methyl] -7,8-dimethoxy-2-oxo-1,3-dihydro-2H-3-benzazepine dihydrochloride dihydrate

Prepared from 7,8-dimethoxy-2-oxo-1,3-dihydro-2H-3-benz-

azepine and 3-chloromethyl-N- [3- (pyridyl-3) -propyl] -piperidine analogously to Example 2

 Yield: 67% of theory, Melting range: 128-134 ° C (amorphous) Calc .: C 57.34 H 7,21 N 7,71 Cl 13,02 Found: 57,80 7,37 7,92 13, 06

Example 115

3 - [(N- (3- (3-pyridyl) propyl) -piperidyl-3) -methyl] -7,8-dimethy1-2-oxo-1,3-dihydro-2H-3-benzazepine dihydrochloride dihydrate

Prepared from 7,8-dimethyl-2-oxo-1,3-dihydro-2H-3-benzazepine and 3-chloromethyl-N- [3- (pyridyl-3) -propyl] -piperidine analogously to Example 2

 Yield: 94% of theory, Melting range: 77-86 ° C (amorphous) Calc .: C 60.92 H 7.67 N 8.19 Cl 13.83 Found: 60.75 7.60 8.37 13, 72

Example 116

3- [2- (N- (3- (Pyridyl-4) -propyl) -piperidyl-2) -ethyl] -7,8-dimethyl-2-oxo-1,3-dihydro-2H-3-benzazepine dihydrochloride

Prepared from 7,8-dimethyl-2-oxo-1,3-dihydro-2H-3-benzazepine and 2- (2-chloroethyl) -N- [3- (pyridyl-4) -propyl] -piperidine analogously to Example 2 ,

Yield: 94% of theory,

Melting range: 118-130 ⁰ C (amorphous) Calc .: C 66.11 H 7.60 N 8.56 Cl 14.45 Found .: 65.92 7.86 8.33 14.09

- 122 Example 117

3 - [(N- (2- (6,7-Dimethoxy-i-quinolyl-4) -ethyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-1,3-dihydro-2H- 3-benzazepinmonohydrat

Prepared from 7,8-dimethoxy-2-oxo-1,3-dihydro-2H-3-benzazepine and 3-chloromethyl-N- [2- (6,7-dimethoxy-isoquinolyl-4) -ethyl] -piperidine analog Example 2. Yield: 69% of theory, Melting range: 85-96 ^e C (amorphous) Calc .: C 67.73 H 7,15 N 7,64 F .: 67,96 7,19 7,75

Example 118

3-C3- (N- (3- (3-pyridyl) propyl) -piperidyl-3) -propyl] -7,8-dimethoxy-2-oxo-l, 3-dihydro-2H-3-benzazepine dihydrochloride monohydrate

Prepared from 7,8-dimethoxy-2-oxo-1,3-dihydro-2H-3-benzazepine and S-iS-chloropropyl-N-CS-ipyridyl-S, -propylD analogous to Example 2

Yield: 72% of theory, Melting range: 94-106 ⁰ C (amorphous)

Calc .: C 60.64 H 7.45 N 7.57 Cl 12.78 F .: 60.80 7.44 7.46 12.59

Example 119

3- [2- (N- (3- (Pyridyl-4) -propyl) -piperidyl-2) -ethyl] -7,8-methyl-1-endioxy-2-oxo-1, S-dihydro-1H-benzazepine dihydrochloride dihydrate

Prepared from 7,8-methylenedioxy-2-oxo-1,3-dihydro-2H-3-benzazepine and 2- (2-chloroethyl) -N- [3- (pyridyl-4) -propyl] -piperidine in dimethylsulfoxide and Potassium tert-butylate analogously to Example 2

 Yield: 67% of theory,

O Melting range: 148-161 "C (amorphous) Calc .: C 57.56 H 6.87 N 7.74 Cl 13.07

Gef .: 57.72 7.03 7.61 13.62

Example 120

3-C (N- (1- (pyridyl-4) -methyl) -piperidyl-3) -methyl] -7,8-dimethyl-2-oxo-1, S-dihydro-1 H-S-benzazepine dihydrochloride monohydrate

Prepared from 7,8-dimethoxy-2-oxo-1,3-dihydro-2H-3-benzazepine and S-chloromethyl-N-Cl-fpyridyl-1-methyl-1-piperidine in dimethyl sulfoxide and potassium tert-butylate analogously to Example 2 ,

Yield: 75 % of theory,

Melting range: 113-127 ^e C (amorphous) Calc .: C, 61.79, H, 7.13, N, 9.01, Cl, 15.20

F .: 61.55 7.32 9.04 15.11

- 124 Example 121

3-C (N- (3- (pyridyl-4) -propyl) -pyrrolidyl-3) -methyl] -7,8-methyl-1-dioxy-2-oxo-1,3,3,4,5-tetrahydro-2H- 3-benzazepine dihydrochloride monohydrate

Prepared from 3 - [(N- (3- (pyridyl-4) -propyl) -pyrrolidyl-3) -methyl] -7,8-methylenedioxy-2-oxo-1,3-dihydro-2H-3H-benzazepine; 10% palladium / carbon and a hydrogen pressure of 5 bar at room temperature analogously to example 5. yield: 71% of theory, melting range: 95-106 ⁰ C (amorphous)

Calc .: C 57.83 H 6.67 N 8.43 Cl 14.22 Vessel: 57.67 6.82 8.27 14.05

Example 122

3- [2- (N- (3- (Pyridyl-4) -propyl) -piperidyl-2) -ethyl 3-7,8-dimethyl-2-oxo-l, 3,4, S-tetrahydro ^ HS- benzazepin-dihydrochloridsemihydrat

Prepared from 3- [2- (N- (3- (pyridyl-4) -propyl) -piperidyl-2) -ethyl] -7,8-dimethyl-2-oxo-1,3-dihydro-2H-3- Benzazepine and 10% palladium / carbon and a hydrogen pressure of 5 bar at 80 ^e C analogously to Example 5

Yield: 73% of theory, m.p .: 236-238 ^e C

Calc .: C, 64.65, H, 8.04, N, 8.37, Cl, 14.14, F, 64.91, 8.02, 8.25, 13.92

- 125 Example 123

3- [3- (N- (2- (2-methyl-6-pyridyl) ethyl) -piperidyl-3) -propyl] -7,8-dimethoxy-2-oxo-l, 3,4,5- tetrahydro-2H-3-ben2azepin dihydrochloride monohydrate

Prepared from 3- [3- (piperidyl-3) -propyl) -7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydro-2H-3-benzazepine and 2-benzenesulfonic acid (6 Methyl-pyridyl-2) -ethyl ester in dimethyl sulfoxide with potassium carbonate at 120 ^e C analogously to Example 1. Yield: 29% of theory, melting range: 105-113 "C (amorphous) Calc .: C 60.42 H 7.78 N 7.55 vessels: 60.68 7.50 7.42

Example 124

3 - [(N- (3- (Pyridy1-3) propyl) -piperidy1-3) methyl] -7,8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro-2H-3- benzazepine dihydrochloride

Prepared from 3 - [(N- (3-pyridyl-3) -propyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-1,3-dihydro-2H-3-benzazepine by hydrogenation at 5 bar hydrogen pressure in ethanol with 10% palladium / carbon at 70 ^e C as in Example 5. Yield: 52% of theory,

Melting range: 113-122 ° C (amorphous) Calc .: C 61.17 H 7.30 N 8.23 F .: 61.31 7.50 8.28

- 126 Example 125

3-C (N- (2- (6,7-dimethoxy-4-isoquinolyl) ethyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4,5- tetrahydro-2H-3-benzazepine χ 1/2 H ₂ O.

Prepared from 3 - [(N- (2- (6,7-dimethoxy-isoquinolyl-4) -ethyl) -piperidyl-3) -methyl] -7, 8-dimethoxy-2-oxo-1,3-dihydroxy- 2H-3-benzazepine by hydrogenation at 5 bar hydrogen pressure with 10% palladium / carbon in ethanol at 70 ^e C analogously to Example 5

 Yield: 50% of theory,

Melting range: 82-86 "C (amorphous) Calc .: C 66.40 H 7.55 N 7.48 Vessel: 66.26 7.50 7.59

Example 126

3- [3- (N- (3- (3-pyridyl) propyl) -piperidyl-3) -propyl] -7,8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro-2H- 3-benzazepine dihydrochloride dihydrate

Prepared from 3- [3- (N- (3- (pyridyl-3) -propyl) -piperidyl-3) -propyl] -7,8-dimethoxy-2-oxo-1,3-dihydro-2H-3- benzazepine by hydrogenation at 5 bar hydrogen pressure with 10% palladium / carbon in ethanol at 70 ⁰ C analogously to Example 5. Yield: 64% of theory, melting range: 106-115 ^e C (amorphous) calc .: C 58.53 H 7 , 89 N 7.31 Cl 12.34 Found: 58.46 7.61 7.14 12.57

- 127 Example 127

3 - [(N- (3- (3-pyridyl) propyl) -piperidyl-3) -methyl] -7,8-methylenedioxy-2-oxo-l, 3,4,5-tetrahydro-2H ~ 3- benzazepine dihydrochloride monohydrate

Prepared from 3 - [(N- (3- (pyridyl-3) -propyl) -piperidyl-3) -methyl] -7, e -methylenedioxy-oxo-1,3-dihydro-2H-3-benzazepine at 5 bar hydrogen pressure with 10% palladium / carbon in ethanol at 80 ^e C analogously to Example 5. Yield: 81% of theory, melting range: 126-138 ^e C (amorphous) calc .: C 58.58 H 6.88 N 8, 19 Cl 13.83 Gef.: 58.43 7.00 7.85 13.71

Example 128

3- [2- (N- (3- (Pyridyl-4) -propyl) -piperidyl-2) -ethyl] -7,8-ethylenedioxy-2-oxo-l, 3,4, S-tetrahydro ^ HS- benzazepine dihydrochloride monohydrate

Prepared from 3- [2- (N- (3- (pyridyl-4) -propyl) -piperidyl-2) -ethyl] -7,8-methylenedioxy-2-oxo-1,3-dihydro-2H-3- Benzazepine at 5 bar hydrogen pressure with 10% palladium / carbon in ethanol at 80 ° C as in Example 5. Yield: 74% of theory, melting range: 132-146 ° C (amorphous) Calc .: C 59.31 H 7.08 N 7,98 Cl 13,46 F .: 59,18 7,41 7,80 13,25

- 128 Example 129

3- [(N- (3- (Pyridyl-3) -propyl) -piperidyl-3) -methyl] -7,8-dimethyl-2-oxo-1,3,4,5-tetrahydro-2H-3- benzazepine dihydrochloride

Prepared from 3 - [(N- (3- (pyridyl-3) -propyl) -piperidyl-3) -methyl] -7,8-dimethyl-2-oxo-1,3-dihydro-2H-3-benzazepine; 5 bar hydrogen pressure with 10% palladium / carbon in ethanol at 80 ⁰ C analogously to Example 5

Yield: 54% of theory, Melting range: 92-105 ⁰ C (amorphous)

Calc .: C 62.90 H 7.92 N 8.46 Cl 14.28 F .: 63.19 7.90 8.45 14.30

Example 130

3 - [(N- (3- (Pyridyl-4) -propyl) -pyrrolidyl-3) -methyl] -7,8-methylene-dioxy-1,3,4-S-tetrahydro-H-S-benzazepine trihydrochloride monohydrate

Prepared from 3 - [(N- (3- (pyridyl-4) -propyl) -pyrrolidyl-3) -methyl] -7,8-methylenedioxy-2-oxo-l, 3,4,5-tetrahydro-2H- 3-Benzazepine and lithium aluminum hydride in tetrahydrofuran / ether analogously to Example 3

 Yield: 73% of theory,

Melting range: 96-108 ⁰ C (amorphous)

Calc .: C 55.33 H 6.97 N 8.06 Cl 20.42

Gef .: 55.06 7,28 7,77 20,07

Example 131

3-C (N- (3- (pyridyl-3-propyl) -piperidyl-3) -methyl3-7,8-dimethoxy-1,3,5,4-tetrahydro-2H-3-benzazepine dihydrochloride

Prepared from 3 - [(N- (3- (pyridyl-3) -propyl) -piperidyl-3) -methyl] -7, S-dimethoxy ^ -oxo-l, 3, 4, 5-tetrahydro-2H-3 benzazepine and lithium aluminum hydride in tetrahydrofuran / ether analogously to Example 3

Yield: 71% of theory, melting point ι 208-210 ^e C

Calc .: C, 62.89, H, 7.91, N, 8.46, Cl, 14.28, Gef.: 62.70, 7.53, 8.22, 14.50

Example 132

3-C2- (N- (3- (4-pyridyl) propyl) -piperidyl-2) -ethyl] -7,8-methylenedioxy-1,3,4,5-tetrahydro-2H-3-benzazepin-trihydrochloride

Prepared from 3-Е2- (N- (3- (pyridyl-4) -propyl) -piperidyl-2) -ethyl] -7,8-methylenedioxy-2-oxo-1,3,4,5-tetrahydro-2H -3-benzazepine and lithium aluminum hydride in tetrahydrofuran / ether analogously to Example 3

 Yield: 63% of theory,

Melting range: 123-136 ⁰ C (amorphous) Calc .: C 58.81 H 7.21 N 7.91 Cl 20.00 Found .: 58.51 7.41 7.92 19.86

- 130 Example 133

- ?, 8-methylated

lendioxy-1,3,4, S-tetrahydro ^ H-S-benzazepin-trihydrochloridsemihydrat

Prepared from 3-C- (N- (3- (pyridyl-3) -propyl) -piperidyl-3) -methyl] -7, 8-ethylenedioxy-2-oxo-l / 3, 4, S-tetrahydro ^ HS azepine and lithium aluminum hydride in tetrahydrofuran / ether analogously to Example 3

Yield: 75% of theory, Melting range: 126-138 ^e C (amorphous) Ber. $ C 57.09 H 7.10 N 7.99 Cl 20.22 Vessel: 57.05 7.32 8.05 20.37

Example 134

3- [ 2- (N- (3- (pyridyl-4) -propyl) -piperidyl-2) -ethyl] -7,8-dimethyl-1,3,4,5-tetrahydro-2H-3-benzazepine trihydrochloride

Prepared from 3-E2- (N- (3- (pyridyl-4) -propyl) -piperidyl-2) ethyl] -7,8-dimethyl-2-oxo-1,3,4,5-tetrahydro-2H -3-benzazepine and lithium aluminum hydride in tetrahydrofuran / ether analogously to Example 3

Yield: 92% of theory, Melting point: 180-182 ⁰ C.

Calc .: C 62.96 H 8.22 N 8.16 Cl 20.65 F .: 63.00 8.29 8.16 20.34

- 131 Example 135

3-C (N- (3- (3-pyridyl) propyl) -piperidyl-3) -methyl] -7,8-diinethyl-1,3,4,5-tetrahydro-2H-3-benzazepin-trihydrochloride

Prepared from 3-ε (N- (3- (pyridyl-3) -propyl) -piperidyl-3) -methyl] -7,8-dimethyl-2-oxo-l, 3,4, S-tetrahydro ^ HS- benzazepine and lithium aluminum hydride in tetrahydrofuran / ether analogously to Example 3

Yield: 81% of theory, melting range: 184-196 ^e C (amorphous)

Ber. : C 60.17 H 8.16 N 8.10 Cl 20.49 F .: 60.28 8.25 8.00 20.39

Example 136

3-C2- (N- (2- (6-methoxy-naphthyl-2-ethyl) -piperidyl-2) -ethyl] -7, 8-dimethoxy-2-oxo-1, 3,4, S-tetrahydro ^ HS-benzazepine hydrochloride

Prepared from 3- [2- (piperidyl-2) -ethyl] -7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydro-2H-3-benzazepine and 2- (6-methoxynaphthyl -2) -ethyl bromide analogously to Example 1. Yield: 20% of theory, melting point: 158-160 ° C.

Ber. C, 69.48; H, 7.47; N, 5.06; C, 6.41; F: 69.40, 7.56, 5.67, 6.62

- 132 Example 137

3-C 2- (N- (2- (5-methyl-6-methoxynaphthyl-2) -ethyl) -piperidyl-2) -ethyl] -7, 8-dimethoxy-2-oxo-1, 3, 4, S-tetrahydro-HS-benzazepine hydrochloride

Prepared from 3- [2- (piperidyl-2) -ethyl] -7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydro-2H-3-benzazepine and 2- (5-methyl-6 -methoxy-naphthyl-2) -ethylbromide analogous to Example Yield j 28% of theory, melting point: 140-143 ^e C

Ber. C 69.88 H 7.64 N 4.94 Cl 6.25 V: 69.06 7.57 4.84 6.44

Example 138

3- [2- (N- (2- (Naphthyl-1-oxy) -ethyl) -piperidyl-2) -ethyl] -7, θα i -hoxy-2-oxo-1,3,4-s-tetrahydro ^ HS-benzazepine hydrochloride

Prepared from 3- [2- (piperidyl-2) -ethyl] -7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydro-2H-3-benzazepine and 2- (naphthyl-loxy) - ethylbromide analogously to example 1. yield: 27% of theory, melting point: 146-148 ⁰ C.

Calc .: C 69.06 H 7.29 N 5.20 Cl 6.58 F .: 69.00 7.07 5.31 6.68

Example 139

3- [2- (N- (2- (l-naphthyl) ethyl) -piperidyl-2) -ethyl] -7,8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro-2H- 3-benza2epin hydrochloride

Prepared from 3- [2- (piperidyl-2) -ethyl] -7,8-dimethoxy-2-5 oxo-1,3,4,5-tetrahydro-2H-3-benzazepine and 2- (naphthyl-1) ethyl bromide analogously to Example 1.

Yield: 24% of theory,

Melting point: 148-150 ^e C

Ber. : C, 71.18, H, 7.51, N, 5.36, Cl, 6.78, O, V, 70.92, 7.44, 5.57, 7.06

Example 140

3- [2- (N- (4- (naphthyl-2-oxy) butyl) -piperidyl-2) -ethyl] -7,8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro- 2H-benzazepine hydrochloride

Prepared from 3- [2- (piperidyl-2) -ethyl] -7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydro-2H-3-benzazepine and 4- (naphthyl-2-oxy ) -butyl bromide analogously to Example 1.

Yield: 39% of theory,

Melting point: 112-114 ⁰ C

Calc .: C, 69.88, H, 7.64, N, 4.64, Cl, 6.25, F, 69.69, 7.58, 4.82, 6.52

Example 141

3- [2- (N- (2- (2-naphthyl) ethyl) -piperidyl-2) ~ ethyl] -7,8-diroethoxy-2-oxo-l, 3,4,5-tetrahydro-2H- 3-benzazepine hydrochloride

Prepared from 3- [2- (piperidyl-2) -ethyl] -7,8-dimethoxy-2-

oxo-1,3,4,5-tetrahydro-2H-3-benzazepine and 2- (naphthyl-2) ethylbromide analogously to Example 1. Yield: 41% of theory, melting point: 120-122 ^e C

Calcd .: C, 71.18, H, 7.51, N, -36, Cl, 6.78, F, 71.10, 7.31, 5.40, 7.05

Example 142

3-C2 (N - ((2-methy1-naphthy1-1) methyl) -piperidyl-2) -ethyl] -7,8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro-2H -3-benzazepine hydrochloride

Prepared from 3- [2- (piperidyl-2) -ethyl] -7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydro-2H-3-benzazepine and 1-chloromethyl-2-methyl- naphthalene analogously to example 1. yield: 24% of theory, melting point: 144-146 ⁰ C.

Calc .: C, 71.18, H, 7.51, N, 5.36, Cl, 6.78, F, 70.93, 7.38, 5.48, 6.89

Example 143

3-C (N- (2- (Naphthyl-2) -ethyl) -hexahydroazepin-3-yl) -methyl] -7, 8-dimethoxy-2-oxo-l, 3, 4, S-tetrahydro ^ HS- benzazepine hydrochloride

Prepared from 3-C (hexahydro-azepin-3-yl) -methyl] -7, 8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro-2H-3-benzazepine and 2- (naphthyl- 2) -ethylbromide analogously to example 1. yield: 58% of theory, melting point: 204-205 ⁰ C.

Ber. : С 71 , 18 H 7, 52 N 5, 36 Cl б, 78 Gef .: 71 , 41 7, 51 5, 35 б, 50 example 144

3 - [(N- (2- (Naphthyl-2) -ethyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-1,3,4-tetrahydro-HS benzazepine hydrochloride

Prepared from 3 - [(piperidyl-3) -methyl] -7, 8-dimethoxy-2-oxo-1,3,4,5-tetrahydro-2H-3-benzazepine and 2- (naphthyl-2) -ethylbromide analog example 1

Yield: 35% of theory, m.p .: 239-240 ^e C

Calc .: 70.70 7.10 5.46 7.16

Example 145

3 - [(N - ((Naphthyl-2) -methyl) -piperidyl-3) -methyl] -7, 8-dimethoxy-2-oxo-1, 3,4,5-tetrahydro-2H-3-benzazepine

Prepared from 3 - [(piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydro-2H-3-benzazepine and 2-bromomethylnaphthalene analogously to Example 1

 Yield: 27% of theory, m.p .: 176-177 "C

Calc .: C 75.95 H 7,47 N 6,11 F .: 76,11 7,28 6,10

- 136 Example 146

3-C (N- (4- (naphthyl-2-oxy) butyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro-2H- 3-benzazepine hydrochloride

Prepared from 3 - [(piperidyl-3) -methyl] -7, 8-dimethoxy-2-5 oxo-1,3,4,5-tetrahydro-2H-3-benzazepine and 4- (naphthyl-2-oxy) butyl bromide analogously to Example 1.

Yield: 24% of theory,

Melting point: 196-197 * C

Ber. : C, 69.48, H, 7.47, N, 5.06, Cl, 6.41, O, V: 69.30, 7.36, 4.99, 6.56

Example 147

3-C (N- (4- (l-naphthyl) ethyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro-2H-3- benzazepine hydrochloride

Prepared from 3 - [(piperidyl-3) -methyl] -7, 8-dimethoxy-2-oxo-1,3,4,5-tetrahydro-2H-3-benzazepine and 2- (naphthyl-1) -ethylbromide analog Example 1.

Yield: 18% of theory, Melting point: 230-231 ⁰ C.

Calc .: C, 70.78, H, 7.33, N, 5.50, Cl, 6.96, Found: 70.71, 7.07, 5.67, 6.99

Example 148

3 - [(N- (2- (Naphthyl-1-oxy) -ethyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydro-2H- 3-benzazepine hydrochloride

Prepared from 3-C (piperidyl-3) -methyl] -7,8-dimethoxy-2-

oxo-1,3,4,5-tetrahydro-2H-3-benzazepine and 2- (naphthyl-loxy) -ethylbromide analogously to Example 1. Yield: 40% of theory, melting point: 214-215 ^e C

Ber. : C, 68.62, H, 7.10, N, 5.34, Cl, 6.75, Gef.: 68.40, 7.10, 5.21, 6.77

Example 149

3 - [(N - ((2-methyl-naphthyl-1) -methyl) -piperidyl-3) -methyl] -7, 8-dimethoxy-2-oxo-l, 3,4, S-tetrahydro ^ HS- benzazepine-hydro-chloride

Prepared from 3 - [(piperidyl-3) -methyl] -7, 8-dimethoxy-2-oxo-1,3,4,5-tetrahydro-2H-3-benzazepine and 1-chloromethyl-2-methyl-naphthalene analog Example 1. Yield: 67% of theory, m.p .: 242-243 "C

Calc .: C 70.78 H 7,33 N 5,50 Cl 6,96 F .: 70,50 7,22 5,34 6,89

Example 150

3 - [(N- (2- (6-methoxy-naphthy1-2) ethyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro- 2H-3-benzazepine hydrochloride

Prepared from 3 - [(piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydro-2H-3-benzazepine and 2- (6-methoxynaphthyl-2 ) -ethyl bromide analogously to Example 1. Yield: 50% of theory, melting point: 156-157 "C

Ber. : С 74, 07 H 7, 62 N 5, 57 Gef .: 73 90 7, 55 5, 64 example 151

3 - [(N- (2- (S-methyl-ö-methoxy-naphth ^ -yl) ethyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4 , 5-tetrahydro-2H-3-benzazepine hydrochloride

Prepared from 3 - [(piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydro-2H-3-benzazepine and 2- (5-methyl-6-methoxy naphth-2-yl) -ethylbromide analogously to example 1. yield: 53% of theory, melting point: 240-241 ⁰ C.

Calc .: C, 69.48, H, 7.47, N, 5.06, Cl, 6.41, F: 69.58, 7.48, 5.00, 6.54

Example 152

2- [N- (2- (3,4-Dimethoxy-phenyl) -ethyl) -piperidyl-3) -methyl] 5,6-dimethoxy-1-oxo-1,3-dihydroisoindole hydrochloride

Prepared from 2 - [(piperidyl-3) -methyl] -5,6-dimethoxy-1,3-dihydro-isoindole and 2- (3,4-dimethoxyphenyl) -ethylbromide analogously to Example 1

Yield: 68% of theory, Melting point: 225-226 ⁰ C.

Ber. : C 63 60 H 7, 18 N 5, 20 Cl 7, 22 Gef .: 63 61 7, 30 5, 70 7, 44

- 139 Example 153

2 - [(N- (2- (6-methoxy-naphthyl-2) -ethyl) -piperidyl-3) -methyl] -5,6-dimethoxy-l-oxo-l, 3-dihydro-isoindole hydrochloride

Prepared from 2 - [(piperidyl-3) -methyl] -5,6-dimethoxy-1-5-oxo-1,3-dihydro-isoindole and 2- (6-methoxynaphthyl-2) -ethylbromide analogously to Example 1

Yield: 75% of theory, m.p .: 234-236 ^e C

Ber. : C 68, 16 H 6 90 N 5, 48 Cl 6 94 Gef .: 68 10 7, 10 5, 39 7, 10 example 154

2-C (N- (2- (Naphthyl-1-oxy) -ethyl) -piperidyl-3) -methyl] -5,6-dimethoxy-1-oxo-1,3-dihydro-isoindole hydrochloride

Prepared from 2 - [(piperidyl-3) -methyl] -5,6-dimethoxy-loxo-1,3-dihydro-isoindole and 2- (naphthyl-1-oxy) -ethylbromide analogously to Example 1.

Yield: 60% of theory,

Melting point: 150-152 ^e C

Calc .: C, 67.66, H, 6.69, N, 5.63, Cl, 7.13, Found: 67.50, 6.76, 5.74, 7.54

Example 155

2-C (N- (2- (4-methyl-phenyl) -ethyl) -piperidyl-3) -methyl] -5,6-dimethoxy-l-oxo-1,3-dihydro-isoindol

Prepared from 2 - [(piperidyl-3) -methyl] -5,6-dimethoxy-l-

oxo-isoindole and 2- (4-methyl-phenyl) -ethylbromide analogously to Example 1.

Yield: 57% of theory, m.p .: 134-136 ° C Calc .: C 73.50 H 7, 90 N 6.86 V: 73.40 8.04 7.06

Example 156

2-C (N- (2- (3-methoxy-phenyl) -ethyl) -piperidy1-3) methyl] -5,6-dimethoxy-l-oxo-1,3-dihydro-isoindole hydrochloride

Prepared from 2-Е (piperidyl-3) -methyl] -5,6-dimethoxy-1-oxo-isoindole and 2- (3-methoxy-phenyl) -ethylbromide analogously to Example 1.

Yield: 54% of theory, m.p .: 226-228 "C

Calc .: C 65.28 H 7.01 N 6.09 Cl 7.71 V .: 65.30 7.37 5.91 7.61

Example 157

2 _ [(N- (2- (5-methyl-6-methoxy-naphthyl-2-ethyl) -piper-idyl-3) -methyl] -5,6-dimethoxy-1-oxo-1,3-dihydroxy- isoindole hydrochloride

Prepared from 2 - [(piperidyl-3) -methyl] -5,6-dimethoxy-loxo-1,3-dihydro-isoindole and 2- (5-methyl-6-methoxy-naphthyl-2) -ethylbromide analogously to Example 1 Yield: 38% of theory, m.p .: 214-216 ° C

Calcd .: C, 68.62, H, 7.10, N, 5.33, Cl, 6.75, F, 68.94, 7.23, 4.98, 6.61

- 141 Example 153

2-C (N- (2- (4-Nitrо-phenyl) -ethyl) -piperidyl-3) -methyl] -5,6-dimethoxy-l-oxo-1,3-dihydro-isoindole hydrochloride

Prepared from 2 - [(piperidyl-3) -methyl] -5,6-dimethoxy-1-5-oxo-1,3-dihydro-isoindole and 2- (4-nitrophenyl) -ethylbromide analogously to Example 1

Yield: 79% of theory, Melting point: 215-218 'C

Ber. : C 60.56 H 6.35 N 8.83 Cl 7.45 Gef.: 60.41 6.26 8.84 7.62

Example 159

3 - [(N- (2- (2-thienyl) ethyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro-2H-3- benzazepine hydrochloride

Prepared from 3 - [(piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydro-2H-3-benzazepine and 2- (2-bromo-ethyl) -thiophene analogously to Example 1.

Yield: 43% of theory,

Melting point: 232-236 ⁰ C

Cl 7.62 S 6.89 F .: 61.90 7.06 5.78 7.96 6.84

Ber , : C 61, 99 H 7, 15 N 6 02 Found , : 61, 90 7, 06 5, 78 at Game 160

3-C (N- (2- (3-thienyl) ethyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4, 5-tetrahydro-2H-3- benzazepine hydrochloride id

Prepared from 3 - [(piperidyl-3) -methyl] -7,8-dimethoxy-2-

oxo-1,3,4,5-tetrahydro-2H-3-benzazepine and 3- (2-bromo-ethyl) thiophene analogously to Example 1

 Yield: 36% of theory,

Melting point: sinters at 75-80 °, melts at 225-230 "C calc .: C 61.99 H 7,15 N 6,02 Cl 7,62 S 6,89 V .: 62,00 7,08 5, 98 8.43 6.62

Example 161

3-C (N- (4- (Thienyl-2-butyl) -piperidyl-3) -methyl] -7, 8-dimethoxy-2-oxo-1, 3,4,5-tetrahydro-2H-3- benzazepine hydrochloride

Prepared from 3-Е (piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydro-2H-3-benzazepine and 2- (4-bromo-butyl) thiophene analogously to Example 1.

Yield: 68% of theory,

Melting range: 190-196 ^e C calc .: C 63.33 H 7.56 N 5.68 Cl 7.19 S 6.50 V .: 63.18 7.72 5.72 7.29 6.59

Example 162

3-C (N- (2- (BenzoCb) furyl-2) -ethyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4, S-tetrahydro ^ HS- benzazepine hydrochloride

Prepared from 3-Е (piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydro-2H-3-benzazepine and 2- (2-bromo-ethyl) - benzoEb] furan analogously to Example 1

Yield: 22% of theory, Melting point: above 216 ⁰ C (decomp.) Calc .: C 67.39 H 7.07 N 5.61 Found .: 67.14 7.36 5.53

- 143 Example 163

3-C (N- (2- (benzo [b] thienyl-3) ethyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4, S-tetrahydro ^ HS-benzazepine hydrochloride

Prepared from 3 - [(piperidyl-3) methyl] -7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydro-2H-3-benzazepine and 3- (2-bromo-ethyl) - benzo [b] thiophene analogously to Example 1. Yield: 73% of theory, melting range: 70-75 ^e C (dec.) calc .: C 65.29 H 6.85 N 5.44 g .: 65.10 6, 87 5.73

Example 164

3 - [(N- (2- (4-Methoxy-benzo [b] thienyl-3) -ethyl) -piperidyl-3) .methyl] -7 _/ 8-dimethoxy-2-oxo-l _/ 3,4, 5-tetrahydro-2H-3-benzazepine hydrochloride

Prepared from 3- [(piperidyl-3) -methyl] -7, S-dimethoxy-1-oxo-1,3,4,5-tetrahydro-2H-3-benzazepine and 3- (2-chloroethyl) -4- methoxy-benzo [b] thiophene analogously to Example 1. Yield: 25% of theory, melting range: 85-105 (dec.)

Calc .: C 63.96 H 6.84 N 5.14 Cl 6.50 S 5.88 F .: 63.95 6.85 4.99 6.53 5.75

Example 165

4, 60 Cl 5, 82 S 10 53 4, 50 5, 97 10 36

3-C (N- (2- (6-Methylsulfonylo3cy-benzo [b] thienyl-3) ethyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4, 5-tetrahydro-2H-3-benzazepine hydrochloride

Prepared from 3 - [(piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydro-2H-3-benzazepine and 3- [2- (methylsulfonyloxy) -ethyl ] -6-methylsulfonyloxy-benzo [b] thiophene analogously to Example 1.

Yield: 55% of theory, melting point: 90 ^e C (dec.)

Calc .: C 57.18 H 6, 12 N Gef .: 57.25 6.14

Example 166

3-C (N- (5- (2-thienyl) pentyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro-2H-3- benzazepine hydrochloride

Prepared from 3 - [(piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydro-2H-3-benzazepine and 2- (5-methylsulfonyloxy-pentyl) - thiophene analogous to Example 1. Yield: 39% of theory, melting point: 177 ^° C.

Calc .: 633.70 7.92 5.40 7.24 6.62. Found: C 63-95 H 7.75 N 5.52 Cl 6.99 S 6.32

- 145 Example 167

3-C (N- (2- (2-furyl) ethyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro-2H-3- benzazepine hydrochloride

Prepared from 3 - [(piperidyl-3) -raethyl] -7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydro-2H-3-benzazepine and 2- (2-methylsulfonyloxy-ethyl) - furan analogously to Example 1

Yield: 44% of theory, Melting range: 205-215 ⁰ C.

Calc .: C 64 20 H 7,41 N 6,24 Cl 7,90 Found: 64,00 7,45 6,00 7,80

Example 168

3-C (N- (3- (2-furyl) propyl) -piperidyl-3) -methyl3-7,8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro-2H-3-benzazepin hydrochloride

Prepared from 3 - [(piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-1, 3,4,5-tetrahydro-2H-3-benzazepine and 3- (puryl-2) -propionaldehyde analog Example 9

Yield: 11% of theory, Melting point: 201-206 ⁰ C.

N 6.05 Cl 7.66 5.93 7.55

Ber. : C64 85 H 7, 62 20 Gef .: 64 88 7, 76 example 169

3-ЙN- (6- ( ^1- TMenyl-2) -hexyl) -piperidyl-3) -methyl] -7, 8-dimethoxy-2-oxo-1, 3,4,5-tetrahydro-2H-3-benzazepine hydrochloride

Prepared from 3 - [(piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo

1,3,4,5-tetrahydro-2H-3-benzazepine and 2- (6-methylsulfonyloxy-hexyl) -thiophene analogously to Example 1.

Yield: 27% of theory,

Melting point: 160 "C

Calc .: C 64.39 H 8.10 N 5.40 Cl 6.79 Vessel: 64.55 7.90 5.23 7.00

Example 170

3 - [(N- (3- (3-indolyl) propyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro-2H-3- benzazepine hydrochloride

Prepared from 3 - [(piperidyl-3) -methyl3-7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydro-2H-3-benzazepine and 3- (3-methylsulfonyloxy-propyl) -indole analogously to Example 1.

Yield: 19% of theory,

Melting point:> 80 ^e C (decomp.) Calc .: C 60.42 H 6 30 N 6.45 Gef .: 60.32 6.57 6.67

Example 171

3-C (N- (2- (3-indolyl) ethyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro-2H-3- benzazepine hydrochloride

Prepared from 3 - [(piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydro-2H-3-benzazepine and 3- (2-methylsulfonyloxy-ethyl) - indole analogously to Example 1.

Yield: 23% of theory,

Melting point:> 80 ° C (dec.) Calc .: C 65.53 H 6.42 N 7.69 F .: 65.33 6.55 7.80

- 147 Example 172

2 - [(N- (3- (Naphthyl-2-oxy) -propyl) -hexahydro-azepinyl-3) -methyl] -6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydro- isoquinoline

Prepared from 6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydroisoquinoline and 3-chloromethyl- [N- (3-naphthyl-2-oxy) -propyl] -hexahydro-azepine analogously to Example 2

Yield: 21% of theory, Melting point: 74-76 ⁰ C

Ber. (x 2 H ₂ O): C 64.45 H 7.02 N 5.01 Cl 6.34 V: 64.32 7.20 5.28 6.44

Example 173

2 - [(N- (3- (2-naphthyl) -propyl) -pyrrolidyl-3) -methyl] -6,7-dimethyl-l-oxo-1,2,3,4-tetrahydro-isoquinoline

Prepared from 6,7-dimethyl-l-oxo-l, 2,3,4-tetrahydro-isoquinoline and 3- (p-toluenesulfonyloxymethyl) -N- [3- (naphthyl-2) -propyl] -pyrrolidine analogously to Example 2 ,

Yield: 20% of theory,

Melting point: 72-76 ⁰ C

Ber. (x H ₂ O): C, 72.41, H, 7.75, N, 5.82, Cl, 7.36, Found: 72.27, 7.85, 5.70, 7.96

- 148 Example 174

2-C (N- (3- (5,6-dimethoxy-naphthy1-2-oxy) -propyl) -pyrrolidyl-3) -methyl] -6,7-dimethoxy-l-oxo-l, 2,3, 4-tetrahydro-isoquinoline hydrochloride

Prepared from 6,7-dimethoxy-l-oxo-l, 3,4,5-tetrahydro-isoquinoline and 3- (p-toluenesulfonyloxymethyl) -N- [S- (S, 6-dimethoxy-naphthyl-2-oxy) - propyl] -pyrrolidine analogously to Example 2, yield: 9.5% of theory, melting point: 60-63 ^e C

Ber. (x H ₂ O): C 63.20 H 7.01 N 4.75 Cl 6.02 Found: 63.40 7.04 4.49 6.38

Example 175

2-C (N- (3- (5,6-dimethoxy-naphthyl-2-oxy) -propyl) -hexahydroazepinyl-3) -methyl] -6,7-dimethoxy-1-oxo-l, 2,3, 4-tetrahydroisoquinoline hydrochloride

Prepared from 6,7-dimethoxy-l-oxo-l, 2,3,4-tetrahydro-isoquinoline and 3- (p-toluenesulfonyloxymethyl) -N- [3- (5,6-dimethoxy-naphthyl-2-oxy) -propyl] -hexahydro-azepiη analogous to Example 2.

Yield: 63.2% of theory, m.p .: 199-201 "C

Calc .: C 66.15 H 7.23 N 4.67 Cl 5.92 F .: 65.99 7.00 4.44 6.02

Example 176

2- [(N- (3- (5, 6-Dimethoxy-naphthyl) -oxy) -propyl) -hexahydroazepinyl-3) -methyl] -6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline dihydrochloride

Prepared from 2-ε (N- (3- (5,6-dimethoxy-naphthyl-2-oxy) -propyl) -hexahydro-azepinyl-3) -methyl] -6,7-dimethoxy-1-oxo-1, 2,3,4-tetrahydro-isoquinoline and lithium aluminum hydride in tetrahydrofuran / ether as in Example 3. Yield: 86.3% of theory, melting point: 114-116 ^e C

Calcd .: C, 61.97, H, 7.56, N, 4.38, Cl, 11.08, Found: 62.05, 7.65, 4.06, 10.84

Example 177

2 - [(N- (2- (4-methoxy-phenyl) -ethyl) -pyrrolidyl-3) -methyl] -6,7-methylenedioxy-1,2,3,4-tetrahydro-isoquinoline dihydrochloride

Prepared from 2 - [(N- (2- (4-methoxy-phenyl) -ethyl) -pyrrolidyl-3) -methyl] -6,7-methylenedioxy-1-oxo-1,2,4,4-tetrahydroisoquinoline; Lithium aluminum hydride / tetrahydrofuran analogously to Example 3.

Yield: 86.7% of theory, melting point: 213-215 ° C

Calcd .: C, 60.49, H, 6.98, N, 5.87, Cl, 14.88, Found: 60.59, 6.96, 5.84, 14.98

- 150 Example 178

2-ε (N- (3- (3,4-Dimethoxy-phenoxy) -propyl) -pyrrolidyl-3) -methyl] -6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydro- isoquinoline

Prepared from 1-oxo-l, 2,3,4-tetrahydro-6, V-methylenedioxyisoquinoline and N-C3- (3,4-dimethoxy-phenoxy) -propylJ-3-benzosulphonyloxymethyl-pyrrolidine analogously to Example 2. Yield: 57 , 4% of theory, melting point: 108-110 ^e C

Ber. : C 59.76 H 6, 74 N 5.35 Cl 7.02 Found: 60.07 6.87 5.23 7.61

Example 179

2-C (N- (2- (4-Methoxy-phenyl) -ethyl) -pyrrolidyl-3) -methyl] -6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline hydrochloride

Prepared from 1-oxo-l, 2,3,4-tetrahydro-6, 7-methylenedioxyisoquinoline and N- [2- (4-methoxyphenyl) ethyl] -3-benzenesulfonyloxy-ethylpyrrolidine analogously to Example 2. Yield: 54.7 % of theory, melting point: 105-108 ⁰ C.

Calc .: C 62.26 H 6.74 N 6.05 Cl 7.97 F .: 62.34 6.74 5.88 8.05

- 151 Example 180

3- [(N- (3- (4-methoxy-N-methyl-phenylamino) -propyl] -piperid-3-yl) -methyl] -7, S -methylenedioxy-2-oxo-l, 3,4, 5-tetrahydro-2H-3-benzazepine dihydrochloride

Prepared from 3- (piperidyl-3-methyl) -7,8-methylenedioxy-2-oxo-1,3,4,5-tetrahydro-2H-3-benzazepine and 1-chloro-3- (4-methoxy-N -methyl-phenylamino) propane as in example 1. yield: 24.2% of theory, melting point: 219-221 ⁰ C.

Calc .: C 58.94 H 7.25 N 7.61 F .: 59.08 7.45 7.75

Example 181

3 - [(N- (2- (6-Methyl-pyridyl-2) -ethyl) -pyrrolidyl-3) -methyl] 7,8-dimethyl-1,3,4,5-tetrahydro-2H-3-benzazepine χ 2.5 HCl χ H ₂ O

Prepared from 3 - [(N- (2- (6-methyl-pyridyl-2) -ethyl) -pyrrolidyl-3) -methyl] -7,8-dimethyl-2-oxo-l, 3,4,5- tetrahydro-2H-3-benzazepine and lithium aluminum hydride in diethyl ether and tetrahydrofuran analogously to Example 3

Yield: 50% of theory, melting point: 80-91 ⁰ C amorphous

Calc .: C 61.68 H 8,18 N 8,63 Cl 18,21 F .: 61,55 8,36 8,44 18,10

Example 182

3 - [(N- (2- (6-Methylpyr-idyl-2) -ethyl) -pyrrolidyl-3) -methyl] -7,8-dimethyl-2-oxo-1,3,4,5-tetrahydro 2H-3-benzazepine dihydrochloride semihydrate

Prepared from 3 - [(N- (2- (6-methyl-pyridyl-2) -ethyl) -pyrrolidyl-3) -methyl] -7,8-dimethyl-2-oxo-1,3-dihydro-2H- 3-benzazepine with 10% palladium / carbon at 5 bar hydrogen and at 80 ° C in ethanol as in Example 5. Yield: 92% of theory, melting point: 86-94 ^e C amorphous

Calc .: C 63.41 H 7.66 N 8.87 Cl 14.97 F .: 63.52 7.14 8.81 14.94

Example 183

2 - [(N- (3- (6-methoxynaphthyl-2-oxy) -propyl) -pyrrolidyl-3) -methyl] -6,7-dimethyl-1-oxo-1, 2, 3,4- tetrahydro-isoquinoline

Prepared from 6,7-dimethoxy-l-oxo-l, 2,3,4-tetrahydro-isoquinoline and S-ip-toluenesulfonyloxymethyl-N-CS-i-methoxynaphthyl-2-oxy) -propyl] -pyrrolidine analog example 2. yield: 44.7% of theory, melting point: 102-104 ⁰ C.

Calc .: C 76.24 H 7.68 N 5.93 F .: 75.90 7.62 5.94

- 153 Example 184

2-C ( Ы- (3- (6- methoxynaphthyl -2-oxy) -propyl) -pyrrolidyl-3) methyl] -6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline

Prepared from 2- [N- (3- (6-methoxynaphthyl-2-oxy) -propyl) -pyrrolidyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4 -tetrahydro-isoquinoline and lithium aluminum hydride in tetrahydrofuran and ether analogously to Example 3. Yield: 68% of theory, melting point: 106-108 "C Ber .: C 73.44 H 7.82 N 5.71 Gef .: 73.26 7 , 72 5.81

Example 185

3 - [(N- (3- (3-indolyl) propyl) -pyrrolidyl-3) -methyl] -7,8-methylenedioxy-2-oxo-l, 3,4,5-tetrahydro-2H-3- benzazepine monohydrate

Prepared from 3- [N- (3- (indolyl-3) -propyl) -pyrrolidyl-3) -methyl] -7,8-methylenedioxy-2-oxo-1,3-dihydro-2H-3-benzazepine with 20 % palladium / carbon at 5 bar hydrogen in ethanol at 80 ^e C analogously to example 5. yield: 40% of theory, melting range: 67-74 ⁰ C Calc .: C 69.95 H 7, 17 N 9.06 Found. : 70.00 7.03 8.97

- 154 Example 186

3 - [(N- (2- (6-Methyl-pyridyl-2) ethyl) -pyrrolid-3-yl) methyl] -7,8-dimethyl-2-oxo-l, 3-dihydro-2H- 3-benzazepine dihydrochloride semihydrate

Prepared from 7,8-dimethyl-2-oxo-1,3-dihydro-2H-3-benzazepine and 3-chloromethyl-N- [2- (6-methyl-pyridyl-2) -ethyl] -pyrrolidine analogously to Example 2

 Yield: 81% of theory, melting point: 86-98 ° C amorphous

10 Ber. : C 63 68 H 7, 27 N 8th, 91 Cl 15 04 Gef .: 63 39 7, 43 8th, 87 14 93 example 187

2- [(N- (3- (3-Methylphenoxy) propyl) piperidyl] -3) methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydroisoquinoline hydrochloride

Prepared from 6,7-dimethoxy-l-oxo-l, 2,3,4-tetrahydro-isoquinoline and N- [3- (3-methylphenoxy) propyl] -3-benzenesulfonyloxymethyl-piperidine analogously to Example 2.

Yield: 75.6% of theory,

Melting point: 106-109 ⁰ C amorphous Calc .: C 63.95 H 7.75 N 5.52 Cl 7.25 Found .: 64.66 7.91 5.48 7.28

- Example 188

2 - [(N- (2- (5-Methyl-6-methoxynaphth-2-yl) -pyrrolidyl-3) -methyl] -6,7-methylenedioxy-1-oxo-1,2,3,4 tetrahydro-isoquinoline

Prepared from 6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydroisoquinoline and 3- (p-toluenesulfonyloxymethyl) -N- [2- (5-methyl-6-methoxynaphth-2-yl) -ethyl] -pyrrolidine analogously to Example 2.

Yield: 27.1% of theory, Melting point: 249-251 ⁰ C.

Calc .: C 68.43 H 6,53 N 5,50 Cl 6,96 F .: 68,47 6,66 5,30 7,16

Example 189

2 - [(N- (3- (2-naphthyl) -propyl) -pyrrolidyl-3) -methyl] -6,7-dimethoxy-1-oxo-isoquinoline hydrochloride

Prepared from 6,7-dimethoxy-l-oxo-l, 2,3,4-tetrahydroisoquinoline and 3- (p-toluenesulfonyloxymethyl) -N- [3- (naphthyl-2) -propyl] -pyrrolidine analogously to Example 2. Yield : 20.2% of theory, m.p .: 84-86 ° C

Calc .: C, 67.88, H, 7.26, N, 5.46, Cl, 6.91, Found: 67.86, 7.40, 5.40, 7.17

- 156 Example 190

2-C (N- (3- (3,4-Dimethoxyphenoxy) propyl) -pyrrolidyl-3) -methyl] -6,7-dimethoxy-l, 2,3,4-tetrahydro-isoquinoline dihydrochloride

Prepared from 2 - [(N-C3- (3,4-dimethoxyphenoxy) -propyl) -pyrrolidyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydroisoquinoline and lithium aluminum hydride in diethyl ether and tetrahydrofuran analogously to Example 3

 Yield: 92.3% of theory,

Melting point: 220-221 "C

Calc. C 59.20 H 6.88 N 5.31 Cl 13.44 F .: 59.28 6.97 5.20 13.44

Example 191

2-C (N- (2- (3,4-Dimethoxyphenyl) -ethyl) -pyrrolidyl-3) -methyl] 6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline

Prepared from 6,7-dimethyl-l-oxo-l, 2,3,4-tetrahydro-isoquinoline and N- [2- (3,4-dimethoxyphenyl) ethyl] -3-benzosulfonyloxymethylpyrrolidine analogously to Example 2. Yield : 70% of theory, melting point: 168-170 ⁰ C.

Calc .: C 73.90 H 8.11 N 6.63 F .: 73.96 8.11 6.55

- 157 Example 192

2-C (N- (3- (4-methoxyphenoxy) propyl) piperidyl-3) methyl] 6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline hydrochloride

Prepared from б, 7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline and N- [3- (4-methoxyphenoxy) -propyl] -3-benzosulfonyloxymethyl-piperidine analogously to Example 2. Yield: 78 , 7% of theory, melting point: 98-102 ⁰ C.

Ber. : C 63.08 H 7.51 N 5.35 Cl 7.02 Gef.: 62.87 7.69 5.16 7.28

Example 193

2-E (N- (3- (3-methoxy-phenoxy) -propyl) -piperidyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline-hydro- chloride

Prepared from 6,7-dimethoxy-l-oxo-l, 2, 3,4-tetrahydro-isoquinoline and N- [3- (3-methoxyphenoxy) propyl] -3-benzosulfonyloxymethyl-piperidine analogously to Example 2. Yield: 87 % of theory, melting point: 103-105 ⁰ C.

Calc .: C, 64.21, H, 7.38, N, 5.55, Cl, 7.02, F: 64.00, 7.55, 5.37, 7.12

Example 194

2 - [(N- (3- (3-Methoxy-phenoxy) -propyl) -piperidyl-3) -methyl], 7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline dihydrochloride

Prepared from 2 - [(N- (3- (3-methoxy-phenoxy) -propyl) -piperidyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,4,4-tetrahydro-isoquinoline; Lithium aluminum hydride in diethyl ether and tetrahydrofuran analogously to Example 3

Yield: 95.4% of theory, melting point: 170-173 ^e C

Re: C 60.43 H 7.70 N 5.22 Cl 13.21 Vessel: 60.50 7.71 4.91 12.97

Example 195

2-C (N- (2- (3,4-Dimethoxyphenyl) ethyl) pyrrolidyl-3) -methyl] -6,7-dimethyl-1,2,3,4-tetrahydro-isoquinoline dihydrochloride

Prepared from 2 - [(N- (2- (3,4-Dimethoxyphenyl) -ethyl) -pyrrolidyl-3) -methyl] -6,7-dimethyl-1-oxo-1,2,3,4-tetrahydroisoquinoline; Lithium aluminum hydride in diethyl ether and tetrahydrofuran analogously to Example 3

 Yield: 94.1% of theory,

Melting point: 260-262 ^e C

Calc .: C 64.85 H 7.96 N 5.82 Cl 14.73 V .: 64.60 8.11 5.91 14.67

Example 196

2 - [(N- (3- (6-methoxynaphthyl-2-oxy) -propyl) azacyclooctyl-S) methyl] -6,7-dimethoxy-1-oxo-1,2,4,4-tetrahydro -isochinolinhydrochlorid

Prepared from 2 - [(azacyclooctyl-i) -methyl) -6,7-dimethoxyl-oxo-1,2,3,4-tetrahydro-isoquinoline and 2- (3-chloropropoxy) -6-methoxynaphthalene analogously to Example 1 Yield: 24.4% of theory, m.p .: 176-178 ° C

Calc .: C, 67.96; H, 7.43; N, 4.80; Cl, 6.08; 67.74 7.29 4.71 6.23

Example 197

3 - [(N- (3- (3-indolyl) propyl) -pyrrolidyl-3) -methyl] -7,8-dimethyl-2-oxo-l, 3,4,5-tetrahydro-2H-3- benzazepine hydrochloride

Prepared from 3 - [(pyrrolidyl-3) -methyl] -7,8-dimethyl-2-oxo> 1,2,3,4-tetrahydro-2H-3-benzazepine and 3- (3-benzenesulfonyloxy-propyl) - indole analogously to Example 1.

Yield: 62% of theory,

Melting point: 106-108 ⁰ C Calc .: C 69.47 H 7.91 N 8.68 Cl 7.32 Found .: 69.57 7.80 8.67 8.51

- 160 Example 198

3- [(N- (3- (6-Methoxy-naphthyl-2-oxy) -propyl) -hexahydro-azepinyl-3) -methyl] -7,8-dimethoxy-1,2,3,4-tetrahydro- 2H-3-benzazepin

Prepared from 3 - [(N- (3- (6-methoxynaphthyl-2-oxy) -propyl) -hexahydro-azepinyl-3) -methyl] -7,8-dimethoxy-l, 2,3,4- tetrahy- dro-2-oxo-2H-3-benzazepine and lithium aluminum hydride in tetrahydrofuran / ether analogously to example 3. yield: 26.8% of theory, melting point: 98-100 ⁰ C.

Ber. (x H ₂ O): C, 71.97 H, 8.42, N, 5.09, Found: 72.07, 8.23, 5.10

Example 199

3 - [(N- (3- (6-methoxynaphthyl-2-oxy) -propyl) -hexahydro-azepinyl-3) -methyl] -1,2,3,4-tetrahydro-2-oxo-2H- 3-benzazepine

Prepared from 3 - [(hexahydro-azepinyl-3) -methyl] -1,2,3,4-tetrahydro-2-oxo-2H-3-benzazepine and 2- (3-chloropropoxy) -6-methoxy-naphthalene analog Example 1.

Yield: 45% of theory,

Melting point: 109-111 ⁰ C Calc .: C 72.50 H 7.74 N 5.12 Found .: 72.35 7.68 4.93

Example 200

2- [(N- (3- (6-Methoxy-naphthyl-2-oxy) -propyl) -hexahydro-azepinyl-3) -methyl] -1,3-dihydro-5,6-dimethoxyisoindole

Prepared from 2 - [(N- (3- (6-methoxynaphthyl-2-oxy) -propyl) -

hexahydro-azepinyl-3) methyl] -5,6-dimethoxy-phthalimide and lithium aluminum hydride in tetrahydrofuran / ether analog

Example 3.

Yield: 49.2% of theory,

Melting point: 104 to 146 ⁰ C

Calc .: C 73.78 H 7.99 N 5.55 F .: 73.63 7.99 5.39

Example 201

3- [(N- (3- (Indolyl-3) -propyl) -pyrrolidyl-3) -methyl] -7,8-dimethyl-1, S, 5'-tetrahydro ^ H-S-benzazepine dihydrochloride monohydrate

Prepared from 3 - [(N- (3- (indolyl-3) -propyl) -pyrrolidyl-3) -methyl] -7,8-dimethyl-2-oxo-l, 3,4,5-tetrahydro-2H- 3-Benzazepine and lithium aluminum hydride in tetrahydrofuran / ether analogously to Example 3.

Yield: 65% of theory,

Melting point: 168-170 ⁰ C

Calc .: C 66.39 H 8.16 N 8.29 Cl 13.99 F .: 66.29 8.44 8.08 14.08

Example 202

3- [(N- (3- (6-Methoxy-naphthyl-2-oxy) -propyl) -hexahydro-azepinyl-1-methyl-1,3,3,5,5-tetrahydro-7,8-methylenedioxy 2H-3-benzazepin

Prepared from 3 - [(N- (3- (6-methoxynaphthyl-2-oxy) -propyl) -hexahydro-azepinyl-3) -methyl] -1,3,4,5-tetrahydro-7,8- methylene · dioxy-2-oxo-2H-3-benzazepine and lithium aluminum hydride / tetrahydrofuran / ether analogously to Example 3.

Yield: 25% of theory, Melting point: 109-111 ⁰ C Ber. : C 74.39 H 7.80 N 5.42 F .: 74.27 7.94 5.43

Example 203

3- [(N- (3- (6-Methoxynaphthyl-2-oxy) -propyl) -hexahydro-azepinyl-3) -methyl] -1, 3, 4, 5-tetrahydro-7, e -methylenedioxy ^ oxo ^ H-3-benzazepine hydrochloride

Prepared from 3 - [(hexahydro-azepinyl-3) -methyl] -I, 3,4,5-tetrahydro-7,8-methylenedioxy-2-oxo-2H-3-benzazepine and 2- (3-chloropropoxy) - 6-methoxynaphthalene analogously to Example 1.

Yield: 68.1% of theory,

Melting range: 104-108 ⁰ C

Ber. (x 2 H ₂ O): C 65.46 H 7.38 N 4.79 Cl 6.06 Found: 65.60 7.25 5.01 6.43

Example 204

2- [(N- (3- (6-methoxynaphthyl-2-oxy) -propyl) -hexahydro-azepinyl-3) -methyl] -6,7-methylenedioxy-1-oxo-l, 2,3, 4-tetrahydro-isoquinoline hydrochloride

Prepared from 2 - [(hexahydro-azepinyl-3) -methyl] -6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 2- (3-chloropropoxy) -6-methoxy naphthalene analogously to Example 1

 Yield: 18.2% of theory, m.p .: 65-67 ° C

Ber. (x H ₂ O): C 65.19 H 6.88 N 4.90 Cl 6.20 V .: 65.20 6.75 4.82 6.54

- 163 Example 205

2 - [(N- (3- (6-methoxy-naphthyl-2-oxy) -propyl) -piperidyl-3) -methyl] -6,7-methylenedioxy-l-oxo-l, 2,3,4- tetrahydro-isoquinoline

Prepared from 6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydroisoquinoline and 3- (benzenesulfonyloxymethyl) -N- [3- (6-methoxynaphthyl-2-oxy) -propyl] -piperidine analogously to Example 2 . yield: 5.3% of theory, melting point: 144-146 ⁰ C Calc .: C 71.69 H 6.82 N 5.57 Found .: 71.52 6.62 5.46

Example 206

2- [(N- (3- (6-Methoxy-naphthyl-2-oxy) -propyl) -hexahydro-azepinyl-3) -methyl] -5,6-dimethyl-1,3-dihydro-1-oxo isoindole

Prepared from 2 - [(N- (3- (6-methoxynaphthyl-2-oxy) -propyl) -hexahydro-azepinyl-3) -methyl] -5,6-dimethyl-phthalimide and zinc / glacial acetic acid analogously to Example 4 ,

Yield: 18.2% of theory,

Melting point: 232-234 ° C

Ber. (x acetone): C, 74.97, H, 8.14, N, 5.14, Found: 74.96, 7.30, 5.30

Example 207

2 - [(N- (3- (6-methoxy-naphthyl-2-oxy) propyl) hexahydro-azepinyl-3) -methyl] -6,7-dimethyl-l-oxo-l, 2,3, 4-tetrahydro-isoquinoline-hypochlorohydride

Prepared from 2 - [(hexahydro-azepinyl-3) -methyl] -6,7-dime

ethyl-1-oxo-1-yl-tetrahydro-isoquinoline and 2- (3-chloropropoxy) -b-methoxynaphthalene analogously to Example 1. Yield: 17.3% of theory, melting range: 68-73 ° C

Ber. (x 2 H ₂ O): C, 67.06, H, 7.93, N, 4.46, Cl, 6.66, Fn: 67.05, 7.73, 4.88, 6.18

Example 208

2 - [(N- (3- (6-methoxynaphthyl-2-oxy) -propyl) -piperidyl-3) -methyl] -O -dimethoxy-1-oxo-1,3,4-tetrahydro isoquinoline

Prepared from 6,7-dimethoxy-l-oxo-l, 2,3,4-tetrahydro-isoquinoline and 3- (benzenesulfonyloxymethyl) -N- [3- (6-methoxynaphthyl-2-oxy) -propyl] -piperidine analog Example 2. Yield: 12.9% of theory, m.p .: 124-126 ° C

Calc .: C, 71.79, H, 7.38, N, 5.40, F, 71.83, 7.33, 5.21

Example 209

3- [(N- (3- (5, 0-Dimethoxy-naphthyl) -oxy) -propyl) -hexahydroazepinyl-3) -methyl] -1,3,4,5-tetrahydro-7,8-dimethoxy-2H -3-benzazepine

Prepared from 3 - [(N- (3- (5,6-dimethoxy-naphthyl-2-oxy) -propyl) -hexahydro-azepinyl-3) -methyl] -1,3,4,5-tetrahydro-7, 8-dimethoxy-2-oxo-2H-3-benzazepine and lithium aluminum hydride / tetrahydrofuran / ether analogously to Example 3. Yield: 29.1% of theory, melting point: 94-96 ° C calc .: C 72.57 H 8.24 N 4,98 Found: 72,56 8,35 4,94

- 165 Example 210

2 - [(N- (3- (6-methoxy-naphthyl-2-oxy) propyl) hexahydro-azepinyl-3) -methyl] -1, 3-dihydro-5, 6-dimethoxy-l-oxo- isoindole

Prepared from 2 - [(N- (3- (6-methoxynaphthyl-2-oxy) -propyl) -hexahydro-azepinyl-3) -methyl] -5,6-dimethoxy-phthalimide and zinc / glacial acetic acid analogously to Example 4

 Yield: 20.5% of theory, melting point: 265-267 ° C

Ber. (x 2 H ₂ O): C 67.13 H 7.63 N 5.05 Found: 67.11 7.64 5.07

Example 211

3 - [(N- (3- (5,6-Dimethoxy-naphthyl-2-oxy) -propyl) -hexahydro-azepinyl-3) -methyl] -1,3,4,5-tetrahydro-7,8- dimethoxy-2-oxo-2H-3-benzazepin

Prepared from 3 - [(hexahydro-azepinyl-3) -methyl] -1,3,4,5-tetrahydro-7,8-dimethoxy-2-oxo-2H-3-benzazepine and 2- (3-chloropropoxy) - 5,6-dimethoxy-naphthalene in analogy to example 1. yield: 52.4% of theory, melting point: 129-131 ⁰ C.

Calc .: C 70.81 H 7.69 N 4.86 F .: 70.66 7.84 4.63

- 166 Example 212

2-t (N- (3- (5, 0-dimethoxy-naphthyl-oxy) -propyl) -hexahydro-aze-pinyl-3) -methyl] -5,6-dimethoxy-1,3-dihydroxy isoindole dihydrochloride

Prepared from 2- [(N- (3- (5, 6-dimethoxy-naphthyl) -oxy) -propyl) -hexahydro-azepinyl-3) -methyl] -5,6-dimethoxy-phthalimide and lithium aluminum hydride in tetrahydrofuran / ether analogously to Example 3.

Yield: 48.2% of theory, Melting range: 172-177 ⁰ C.

Ber. (x H ₂ O): C 61.43 H 7.41 N 4.47 Cl 11.33 F .: 61.50 7.71 4.59 11.45

Example 213

2 - [(N- (3- (5,6-Dimethoxy-naphthyl-2-oxy) -propyl) -hexahydro-aze -pinyl-3) -methyl] -5,6-dimethoxy-1,3-dihydroxy- l-oxo-isoindole hydrochloride

Prepared from 2 - [(N- (3- (5,6-dimethoxy-naphthyl-2-oxy) -propyl) -hexahydro-azepinyl-3) -methyl] -5,6-dimethoxy-phthalimide and zinc / glacial acetic acid analogously Example 4

 Yield: 36.4% of theory, melting range: 215-223 ° C

Ber. (x H ₂ O): C 61.87 H 7.30 N 4.50 Cl 5.70 V .: 62.08 7.15 4.55 5.80

Example 214

2- [(N- (3- (Indolyl-3) -propyl) -pyrrolidyl-3) -methyl] -5,6-dimethoxy-1-dihydroisoindole dihydrochloride monohydrate

Prepared from 2- ( (Ы- (3- (indolyl-3-propyl-руггоіігіуі-З] -methyl] -5,6-dimethoxy-phthaliride and lithium aluminum hydride in tetrahydrofuran analogously to Example 3. Yield: 87% of theory, m.p .: 262-264 ⁰ C

Calc .: C 61.17 H 7.30 N 8.23 Cl 13.89 F .: 61.34 7.26 7.92 13.90

Example 215

3 - [(N- (3- (5,6-dimethoxy-naphthyl-2-oxy) propyl) hexahydro-azepinyl-3) -methyl] -1,3,4,5-tetrahydro-7,8 dimethyl-2H-3-benzazepine dihydrochloride

Prepared from 3 - [(N- (3- (5,6-dimethoxy-naphthyl-2-oxy) -propyl) -hexahydro-azepinyl-3) -methyl] -1,3,4,5-tetrahydro-7, 8-dimethyl-2-oxo-2H-3-benzazepine and lithium aluminum hydride / tetrahydrofuran / ether as in Example 3. Yield: 76.9% of theory,

Melting range: 138-144 ⁰ C

Calc .: C, 67.64, H, 8.01, N, 4.64, Cl, 11.74, Found: 67.73, 8.26, 4.47, 11.50

- 168 Example 216

3 - [(N- (3- (5,6-dimethoxy-naphthyl-2-oxy) -propyl) -hexahydroazepinyl-3) -methyl] -1,3,4,5-tetrahydro-7,8-dimethyl- 2-oxo-2H-3-benzazepine hydrochloride

Prepared from 3- [(hexahydro-azepinyl-3) -methyl] -I, 3,4,5-tetrahydro-7,8-dimethyl-2-oxo-2H-3-benzazepine and 2- (3-chloro-propoxy ) -5,6-dimethoxy-naphthalene in analogy to example 1. yield: 47.5% of theory, melting range: 90-96 ⁰ C

Ber. (x H ₂ O): C 68.15 H 7.90 N 4.67 Cl 5.91 F .: 67.93 7.94 5.05 6.09

Example 217

2- [(N- (3- (5,6-dimethoxy-naphthyl-2-oxy) -propyl) -piperidyl-3) methyl] -6,7-methylenedioxy-1-oxo-1,2,3,4 tetrahydro-isoquinoline hydrochloride

Prepared from 2 - [(piperidyl-3) -methyl] -6,7-methylenedioxy-loxo-1,2,3,4-tetrahydro-isoquinoline and 2- (3-chloro-propoxy) -5,6-dimethoxy-naphthalene analog Example 1. Yield: 22.5% of theory, melting range: 93-98 ° C

Ber. (x H ₂ O): C 63.42 H 6.69 N 4.77 Cl 6.03 Found: 63.59 6.80 4.70 6.28

- 169 Example 218

2 - [(N- (3- (5,6-Dimethoxy-naphthyl-2-oxy) -propyl) -pyrrolidyl-3) methyl] -O-methylenedioxy-1-oxo-1,3,1,4-tetrahydro -isoquinoline hydrochloride

Prepared from 2 - [(pyrrolidyl-3) -methyl] -6,7-methylenedioxy-oxo-1,2,3,4-tetrahydro-isoquinoline and 2- (3-chloro-propoxy) -5,6-dimethoxy-naphthalene analog example 1. yield: 22.5% of theory, melting point: 87-9O ⁰ C

Ber. (x H ₂ O): C 62.87 H 6.50 N 4.88 Cl 6.18 V: 62.72 6.38 4.93 6.30

Example 219

2- [(N- (3- (5,6-dimethoxy-naphthyl-2-oxy) -propyl) -piperidyl-3) methyl] -O-dimethyl-1-oxo-1: 3,4-tetrahydro -isochinolinhydrochlorid

Prepared from 2 - [(piperidyl-3) -methyl] -6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 2- (3-chloropropoxy) -5,6-dimethoxy naphthalene analogously to Example 1. Yield: 21.3% of theory, melting range: 72-78 ° C.

Ber. (x H ₂ O): C 67.30 H 7.59 N 4.90 Cl 6.21 V: 67.44 7.74 5.06 6.53

- 170 Example 220

2 - [(N- (3- (5,6-dimethoxy-naphthyl-2-oxy) propyl) hexahydro-azepinyl-3) -methyl] -6,7-dimethyl-l-oxo-l, 2, 3,4-tetrahydro-isoquinoline hydrochloride

Prepared from 2 - [(hexahydro-azepinyl-3) -methyl] -6,7-dimethyl-1-oxo-1-methyl-tetrahydro-isoquinoline and 2- (3-chloro-propoxy) -5,6-dimethoxy-naphthalene analogously to example yield: 12% of theory, melting range: 84-90 ⁰ C

Ber. (x H ₂ O): C 67.73 H 7.73 N 4.78 Cl 6.06 Found: 67.64 7.81 4.94 6.20

Example 221

2- [(N- (2- (4-methoxy-phenyl) -ethyl) -hexahydro-azepinyl-3) -methyl] -O-methyl-dioxy-1-oxo-1,3,1,4-tetrahydro-isoquinoline hydrochloride

Prepared from 6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydroisoquinoline and N- [2- (4-methoxyphenyl) ethyl] -3-chloromethylhexahydro-azepine analogously to Example Yield: 46.7 % of theory, melting point: 101-105 ⁰ C Calc .: C 62.44 H 7.26 N 5.60 Cl 7.50 Found .: 62.62 7.27 5.48 7.66

- 171 Example 222

2- [ (N- (3- (4-methoxy-phenoxy) -propyl) -hexahydro-azepinyl-3) -methyl] -6, 7-methylenedioxy-1-oxo-1,2,3,4-tetrahydro- isoquinoline

Prepared from 6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydroisoquinoline and N- [3- (4-methoxy-phenoxy) -propyl] -3-chloromethyl-hexahydro-azepine analogous to Example Yield: 43 , 8% of theory, melting point: 123-126 ⁰ C calc .: C 62.23 H 7,16 N 5,37 Cl 7,05 Gef .: 62,42 7,34 5,30 6,94

Example 223

2 - [(N- (3- (4-Methoxy-phenoxy) -propyl) -hexahydro-azepinyl-3) methyl] -6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline hydrochloride

Prepared from 6,7-dimethyl-l-oxo-l, 2,3,4-tetrahydro-isoquinoline and N- [3- (4-methoxy-phenoxy) -propyl] -3-chloromethylhexahydro-azepine analogous to Example Yield: 42 % of theory, melting point: 172-173 ⁰ C Calc .: C 69.04 H 8.07 N 5.75 Cl 7.28 Found .: 69.06 8.25 5.57 7.39

Example 224

2- ((N- (3- (4-Methoxy-phenoxy) -propyl) -hexahydro-azepinyl-3) methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline hydrochloride

Prepared from 6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline and N- [3- (4-methoxy-phenoxy) -propyl] -3-chloromethyl-hexahydro-azepine analogously to Example 2

Yield: 63.3% of theory, Melting range: 115-120 ⁰ C.

Calc .: C 62.58 H 7.67 N 5.21 Cl 6.83 F .: 62.44 7.68 4.91 6.81

Example 225

2 - [(N- (2- (4-methoxyphenyl) -fochyl) -hexahydro-azepinyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro- isoquinoline hydrochloride

Prepared from 6,7-dimethoxy-l-oxo-l, 2,3,4-tetrahydro-isoquinoline and N- [2- (4-methoxyphenyl) ethyl] -3-chloromethylhexahydro-azepine analogously to Example 2

Yield: 51.6% of theory, Melting point: 110-113 ⁰ C.

Calc .: C, 61.75, H, 7.87, N, 5.28, Cl, 7.25, F, 61.84, 8.02, 5.16, 7.22

- 173 Example 226

2- [ (N- (2- (3,4-Dimethoxyphenyl) ethyl) hexahydro-azepinyl-3) methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro -isochinolinhydrochlorid

Prepared from 6,7-dimethoxy-l-oxo-l, 2,3,4-tetrahydro-isoquinoline and N- [2- (3,4-dimethoxy-phenyl) -ethyl] -3-chloromethyl-hexahydro-azepine analog example yield: 45.5% of theory, melting point: 107-111 ⁰ C Calc .: C 62.61 H 7.69 N 5.21 Cl 6.60 Found .: 62.78 8.00 5.00 6, 43

Example 227

2- [(N- (2- (3,4-Dimethoxy-phenyl) -ethyl) -hexahydro-azepinyl-3) methyl] -O-dimethyl-1-oxo-1,1,3,4-tetrahydro-isoquinoline hydrochloride

Prepared from 6,7-dimethyl-l-oxo-l, 2,3,4-tetrahydro-isoquinoline and N- [2- (3,4-dimethoxy-phenyl) -ethyl] -3-chloromethyl-hexahydro-azepine analog Example yield: 44.8% of theory, melting point: 162-163 ° C calc .: C 66.57 H 8,18 N 5,54 Cl 7,02 Gef .: 66,67 8,47 5,35 7, 11

- 174 Example 228

3 - [(N- (2- (3,4-Dimethoxyphenyl) ethyl) hexahydro-azepinyl-3) methyl] -7,8-dimethoxy-2-oxo-l, 3,4, S- tetrahydro ^ H ^ benzazepine hydrochloride

Prepared from 7, S-dimethoxy-2-oxo-l, 3,4,5-tetrahydro-2H-3-benzazepine and N- [2- (3,4-dimethoxyphenyl) ethyl] -3-chloromethyl- hexahydro-azepine analogously to example 2. yield: 41.7% of theory, melting point: 102-105 ⁰ C.

Calc .: C 63.19 H 7.36 N 5.08 Cl 6.65 V .: 63.09 7.52 4.94 6.72

Example 229

3- [(N- (2- (3,4-Dimethoxyphenyl) ethyl) hexahydro-azepinyl-3) methyl] -7,8-raethylenedioxy-2-oxo-l, 3,4,5- tetrahydro-2H-3-benz · azepine hydrochloride

Prepared from 7,8-methylenedioxy-2-oxo-l, 3,4,5-tetrahydro-2H-3-benzazepine and N- [2- (3,4-dimethoxyphenyl) ethyl] -3-chloromethyl- hexahydro-azepine analogously to example 2. yield: 38.7% of theory, melting point: 98-102 ⁰ C.

Calc .: C 61.01 H 7.69 N 5.08 Cl 6.43 V .: 60.86 7.43 4.87 6.25

- 175 Example 230

3-t (N- (2- (4-methoxy-phenyl) -ethyl) -hexahydro-azepinyl-3) -methyl] -7, 8-dimethoxy-2-oxo-1,3,4-S-tetrahydro ^ HS-benzazepine

Prepared from 7,8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro-2H-3-benzazepine and N- [2- (4-methoxy-phenyl) -ethyl] -3-chloromethylhexahydro-azepine analog Example 2

Yield: 51.2% of theory, Melting point: 110-113 ⁰ C.

Calc .: C, 63.43, H, 7.98, N, 5.28, Cl, 7.02, F, 63.31, 7.99, 4.93, 7.05

Example 231

3 - [(N- (3- (3,4-methylenedioxy-phenoxy) -propyl) -hexahydro-azepinyl-3) -methyl] -7,8-methylenedioxy-2-oxo-l, 3,4,5- tetrahydro-2H-3-benzazepine hydrochloride

Prepared from 7,8-methylenedioxy-2-oxo-l, 3,4,5-tetrahydro-2H-3-benzazepine and N- [3- (3,4-methylenedioxy-phenoxy) -propyl] -3-chloromethyl- hexahydro-azepine analogously to example 2. yield: 30.6% of theory, melting point: 106-109 ⁰ C.

Calc .: C 62.27 H 6.71 N 5.18 Cl 6.68 F .: 62.36 6.70 5.00 6.46

- 176 Example 232

3- [(N- (3- (3-methyl-phenoxy) -propyl) -hexahydro-azepinyl-3) -methyl] -7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydro 2H-3-benzazepine hydrochloride

Prepared from 7,8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro-2H-3-benzazepine and N- [3- (3-methylphenoxy) propyl] -3-chloroethylhexahydro-azepine analog Example 2

Yield: 44.4% of theory, Melting point: 112-115 ⁰ C.

Calc .: C 66.20 H 8.04 N 5.32 Cl 6.86 F .: 65.98 7.96 5.36 6.90

Example 233

3 - [(N- (3- (4-methoxy-phenoxy) propyl) hexahydro-azepinyl-3) -methyl] -6,7-methylenedioxy-2-oxo-l, 3,4,5-tetrahydro- 2H-3-benz · azepine hydrochloride

Prepared from 6,7-methylenedioxy-2-oxo-l, 3,4,5-tetrahydro-2H-3-benzazepine and N- [3- (4-methoxy-phenoxy) -propyl] -3-chloro-methyl- hexahydro-azepine analogously to Example 2. Yield: 38.7% of theory, melting point: 121-126 ° C

Calcd .: C, 62.84, H, 7.34, N, 5.23, Cl, 6.86, Found: 63.05, 7.33, 5.28, 7.04

- 177 Example 234

2 - [(N- (3- (3-methyl-phenoxy) -propyl) -hexahydro-azepinyl-3) -methyl] -6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydro- isoquinoline hydrochloride

Prepared from 6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydroisoquinoline and N- [3- (3-methyl-phenoxy) -propyl] -3-chloromethyl-hexahydro-azepine analogously to Example 2. Yield : 46.8% of theory, melting point: 159-161 ⁰ C.

Calc .: C, 65.37, H, 7.31, N, 5.64, Cl, 7.28, V: 65.44, 7.40, 5.39, 7.23

Example 235

2 - [(N- (3- (3-methyl-phenoxy) -propyl) -hexahydro-azepinyl-3) -methyl] -6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro- isoquinoline hydrochloride

Prepared from 6,7-dimethoxy-l-oxo-l, 2,3,4-tetrahydro-isoquinoline and N- [3- (3-methoxy-phenoxy) -propyl] -3-chloromethylhexahydro-azepine analogously to Example 2

Yield: 55.2% of theory, Melting point: 107-111 ⁰ C.

Calc .: C 65.67 H 7.87 N 5.47 Cl 7.05 Found: 65.47 8.00 5.50 6.97

Example 236

2 - [(N- (3- (3,4-methylenedioxy-phenoxy) -propyl) -hexahydro-azepine-yl-3) -methyl] -6,7-dimethyl-1-oxo-l, 2,3, 4-tetrahydro-isoquinoline hydrochloride

Prepared from 6,7-Dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline and N- [3- (3,4-methylenedioxy-phenoxy) -propyl] -3-chloromethyl-hexahydro-azepine analog example 2. yield: 40.6% of theory, melting point: 123-126 ⁰ C.

Calc .: C, 64.78; H, 7.57; N, 5.39; Cl, 6.83; F, 64.88, 7.59, 5.29, 7.18

Example 237

2 - [(N- (3- (3,4-dimethoxy-phenoxy) -propyl) -hexahydro-azepine-yl-3) -methyl] -6,7-di-methoxy-1-oxo-1,2 3,4-tetrahydroisoquinoline hydrochloride

Prepared from 6,7-dimethoxy-l-oxo-l, 2,3,4-tetrahydro-isoquinoline and N- [3- (3,4-dimethoxy-phenoxy) -propyl] -3-chloromethyl-hexahydro-azepine analog example 2. yield: 30.6% of theory, melting point: 101-105 ⁰ C.

Calc .: C, 62.61, H, 7.59, N, 5.01, Cl, 6.4, V, 62.56, 7.76, 4.94, 6.39

Example 238

2- [(N- (2- (3,4-Dimethoxy-phenyl) -ethyl) -hexahydro-azepinyl-3) -methyl] -5, б-dimethoxy-1-oxo-1,3-dihydro-isoindole hydrochloride

Prepared from 2 - [(N- (2- (3,4-dimethoxy-phenyl) -ethyl) -hexahydro-azepinyl-3) -methyl] -5,6-dimethoxy-phthalimide and zinc / glacial acetic acid analogously to Example 4

Yield: 41.8% of theory, Melting point: 150-151 ⁰ C.

Ber. : C 61, 99 H 7, 57 N 5, 35 Cl 6 57 10 Gef .: 61, 89 7, 48 5, 17 6 52 example 239

2- [(N- (3- (3-methyl-phenoxy) -propyl) -hexahydro-azepinyl-3) -methyl] -5, ib-dimethoxy-1-oxo-1,3-dihydroisoindole hydrochloride

Prepared from 2 - [(N- (3- (3-methyl-phenoxy) -propyl) -hexahydro-azepinyl-3) -methyl] -5,6-dimethoxy-phthalimide and zinc / glacial acetic acid analogously to Example 4

Yield: 88.9% of theory, Melting point: 95-100 ⁰ C.

Ber. : C 63 95 H 7th 75 N 5, 52 Cl 7, 25 20 Gef .: 64 09 7, 64 5, 35 7, 37 example 240

2 - [(N- (3- (4-methoxy-phenoxy) propyl) hexahydro-azepinyl-3) -methyl] -5,6-dimethoxy-l-oxo-l, 3-dihydro-isoindole hydrochloride

Prepared from 2 - [(N- (3- (4-methoxy-phenoxy) -propyl) -hexahyne

dro-azepinyl-3) -methyl] -5,6-dimethoxy-phthalimide and zinc / glacial acetic acid analogously to Example 4.

Yield: 87.1% of theory,

Melting point: 107-112 ⁰ C

Calcd .: C, 61.99, H, 7.51, N, 5.35, Cl, 7.02, Found: 62.07, 7.37, 5.28, 7.31

Example 241

2 - [(N- (3- (3,4-methylenedioxy-phenoxy) -propyl) -hexahydro-azepine-yl-3) -methyl] -5,6-dimethoxy-1-oxo-1,3-dihydro- isoindole-hydro-chloride

Prepared from 2 - [(N- (3- (3,4-methylenedioxy-phenoxy) -propyl) -hexahydro-azepinyl-3) -methyl] -5,6-dimethoxy-phthalimide and zinc / glacial acetic acid analogously to Example 4

Yield: 59% of theory, Melting point: 104-107 ⁰ C.

Calc .: C 60.38 H 6.94 N 5.20 Cl 7.31 Found: 60.40 7.15 4.95 7.25

Example 242

2 - [(N- (3- (3,4-methylenedioxy-phenoxy) propyl) hexahydro-azepinyl-3) -methyl] -5,6-dimethoxy-l-oxo-l, 3-dihydro-isoindol hydrochloride

Prepared from 2 - [(N- (3- (3,4-methylenedioxy-phenoxy) -propyl) -hexahydro-azepinyl-3) -methyl] -5,6-dimethoxy-phthalimide and zinc / glacial acetic acid analogously to Example 4

 Yield: 79.4% of theory, melting point: 112-116 ° C

Ber .: C 62 , 23 H 7, 15 N 5, 37 Cl 7, 05 Gef . : 62 16 7, 25 4, 96 7, 03 example 243

3 - [(N- (3- (pyridyl-3) -propyl) -hexahydro-azepinyl-3) -methyl] -7, S-dimethoxy-2-oxo-1, S-dihydro ^ H ^ benzazepine dihydrochloride dihydrate

Prepared from 7,8-dimethoxy-2-oxo-1,3-dihydro-2H-3-benzazepine and N- [3- (pyridyl-3) -propyl] -3-chloromethyl-hexahydro-azepine in dimethylsulfoxide with potassium tert.butylate analogously to Example 2.

Yield: 86% of theory,

Melting point: 106-108 ⁰ C

Calc .: C, 58.05, H, 7.40, N, 7.52, Cl, 12.69, Found: 57.94, 7.55, 7.75, 12.42

Example 244

3 - [(N- (3- (3-pyridyl) propyl) hexahydro-azepinyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro-2H- 3-Benzazepine dihydrochloride dihydrate

Prepared from 3 - [(N- (3- (pyridyl-3) -propyl) -hexahydro-azepinyl-3) -methyl] -7,8-dimethoxy-2-oxo-1,3-dihydro-2H-3- Benzaze- pin and 5 bar of hydrogen in the presence of 10% palladium on carbon in dimethylformamide at 8O ⁰ C analogously to Example 5.

Yield: 43% of theory,

Melting point: 119-121 ° C Calc .: C 57.85 H 7.73 N 7.49 Cl 12.65 V .: 57.74 7.79 7.23 12.50

- 182 Example 245

3- [(N- (3- (Pyridyl-3) -propyl) -hexahydro-azepinyl-3) -methyl] 7, 8-dimethoxy-l, 3,4, S-tetrahydro ^ H-S-benzazepine trihydrochloride monohydrate

Prepared from 3 - [(N- (3- (pyridyl-3) -propyl) -hexahydroazepinyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro-2H- 3-Benzazepine and lithium aluminum hydride in tetrahydrofuran and diethyl ether analogously to Example 3. Yield: 82% of theory, melting point: 139-141 ° C.

Calc .: C 57.39 H 7.85 N 7.43 Cl 18.82 V: 57.42 8.15 7.56 19.04

Example 246

2 - [(N- (I- (3-pyridyl) methyl) -pyrrolidy1-3) methyl] -6,7-methylenedioxy-l-oxo-1,2,3,4-tetrahydro-isoquinoline-dihydrochloride dihydrate

Prepared from 6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydroisoquinoline and 3-chloromethyl-N - [(pyridyl-3) -methyl] -pyrrolidine in dimethyl sulfoxide with potassium tert-butylate analogously to Example 2 ,

Yield: 46% of theory,

Melting point: 91-93 ° C

Calc .: C 53.17 H 6.16 N 8.85 Cl 14.95

Gef .: 53.31 5.93 8.71 15.01

Example 247

2 - [(N- (1- (Pyridyl-3) -methyl) -pyrrolidyl-3) -methyl] -6,7-methylenedioxy-1,2,3,4-tetrahydro-isoquinoline-trihydrochloride - 1.5 χ hydrate

Prepared from 2 - [(N- (1- (pyridyl-3) -methyl) -pyrrolidyl-3) -methyl] -6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline; lithium aluminum hydride in tetrahydrofuran and diethyl ether analogously to example yield: 67% of theory, melting point: 178-181 ⁰ C Calc .: C 51.70 H 6.41 N 8.61 Cl 21.80 Found .: 51.63 6.62 8 , 45 21.07

Example 248

3 - [(N- (2- (6-Methyl-pyridyl-2) -ethyl) -hexahydro-azepinyl-3) methyl] ^, S-dimethoxy ^ dihydrochloride dihydrate

Prepared from 7,8-dimethoxy-2-oxo-l, 3-dihydro-2H-3-benzazepine and N- [2- (6-methyl-pyridyl-2) -ethyl] -3-chloromethylhexahydro-azepine in dimethyl sulfoxide with Potassium tert-butylate analogously to Example 2.

Yield: 63% of theory, Melting point: 134-136 ⁰ C Calc .: C 58.05 H 7.40 N 7.52 Cl 12.69 Found .: 58.15 7.60 7.45 12.45 "

- 184 Example 249

3- [(N- (2- (6-Methyl-pyridyl-2) -ethyl) -pyrrolidyl-3) -methyl] -7, e -dimethoxy ^ -oxo-1, S-dihydro ^ H ^ -benzazepine dihydrochloride χ 1.5 hydrate

Prepared from 7,8-dimethoxy-2-oxo-l, 3-dihydro-2H-3-benzazepine and 3-chloromethyl-N- [2- (6-methyl-pyridyl-2) -ethyl] -pyrrolidine in dimethylsulfoxide with Potassium tert-butylate analogously to Example 2

Yield: 61% of theory, Melting point: 78-80 ⁰ C

Calc .: C 57,58 H 6,96 N 8,06 Cl 13,60 Found: 57,40 7,18 8,24 13,39

Example 250

3- [(N- (2- (6-Methyl-pyridyl-2) -ethyl) -hexahydro-azepinyl-3-methyl] -7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydro -2H-3-benzazepine dihydrochloride χ 2.5 hydrate

Prepared from 3 - [(N- (2- (6-methyl-pyridyl-2) -ethyl) -hexahydro-azepinyl-3) -methyl] -7,8-dimethoxy-2-oxo-1,3-dihydroxy- 2H-3-benzazepine and 5 bar of hydrogen in the presence of palladium / carbon and dimethylformamide analogously to Example 5. Yield: 34% of theory, melting point: 112-114 ° C

Calc .: C 56.93 H 7.78 N 7.38 Cl 12.45 F .: 56.83 8.04 7.43 12.26

- 185 Example 251

3 - [(N- (2- (6-Methyl-pyridyl-2) -ethyl) -hexahydro-azepinyl-3) methyl] -7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3 -benzazepintrihydrochlorid dihydrate

Prepared from 3 - [(N- (2- (6-methyl-pyridyl-2) -ethyl) -hexahydro-azepinyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4, 5-tetrahydro-2H-3-benzazepine and lithium aluminum hydride in tetrahydrofuran and diethyl ether analogously to example 3. yield: 74% of theory, melting point: 148-150 ⁰ C.

Calc .: C 55.61 H 7.95 N 7.20 Cl 18.24 V: 55.72 8.10 7.03 18.00

Example 252

3-t (N- (2- (6-methyl-pyridyl-2) -ethyl) -pyrrolidyl-3) -methyl] -7, S-dimethoxy-2-oxo-1,3,3,5-tetrahydro 2H-3-benzazepine dihydrochloride dihydrate

Prepared from 3 - [(N- (2- (6-methyl-pyridyl-2) -ethyl) -pyrrolidyl-3) -methyl] -7, e-dimethoxy ^ -oxo-l, З ^ хЬуаго-ЗН-З -Ьепгаге-ргп and palladium / carbon in dimethylformamide at 50 ⁰ C and 6 bar hydrogen pressure as in Example 5. Yield: 28% of theory, melting point: 87-90 ⁰ C.

Calcd .: C, 56.38, H, 7.38, N, 7.89, Cl, 13.31, Found: 56.33, 7.53, 8.09, 13.43

- 186 Example 253

3- [(N- (2- (6-Methyl-pyridyl-2) -ethyl) -pyrrolidyl-3) -methyl] -7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepine -trihydrochlorid dihydrate

Prepared from 7,8-dimethoxy-l, 3,4,5-tetrahydro-2H-3-benzazepine and N- [2- (6-methyl-pyridyl-2) -ethyl] -3- (benzenesulfonyloxy-methyl) - pyrrolidine in dimethylformamide and triethylamine analogously to Example 2

 Yield: 42% of theory, melting point: 225-227 ° C

Calc .: C 54.10 H 7.62 N 7.57 Cl 19.16 F .: 54.18 7.55 7.51 19.30

Example 254

2 - [(N- (3- (Indolyl-3) -propyl) -piperidyl-3) -methyl] -5,6-dimethoxy-1-oxo-1,3-dihydro-isoindole χ 1,5-benzenesulfonate trihydrate

Prepared from 2 - [(piperidyl-3) -methyl] -5,6-dimethoxy-1-oxo-1,3-dihydro-isoindole and 3- (3-benzenesulfonyloxy-propyl) -indole in dimethylformamide and triethylamine analogously to Example 1 Yield: 45% of theory, m.p .: 87-89 ° C

Calcd .: C 58.51 H 6.54 N 5.68 F .: 58.66, 6.43, 5.34

Example 255

2 - [(N- (3- (3-indolyl) propyl) -piperidyl-3) -methyl] -6,7-dimethyl-l-oxo-1,2,3,4-tetrahydro-isoquinoline-benzenesulfonate dihydrate

Prepared from 2 - [(piperidyl-3) -methyl] -6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 3- (3-benzenesulfonyloxypropyl) -indole in dimethylformamide and triethylamine analogously Example 1.

Yield: 94% of theory, Melting point: 117-119 ⁰ C.

Calc .: C 65.46 H 7.27 N 6.73 V .: 65.51 6.91 6.72

Example 256

3 - [(N- (3- (indolyl-3) -propyl) -pyrrolidyl-3) -methyl] -7,8-dimethoxy-2-oxo-1,3,4-s-tetrahydro-1H-benzazepine hydrochloride monohydrate

Prepared from 3 - [(N- (3- (indolyl-3) -propyl) -pyrrolidyl-3) -methyl] -7,8-dimethoxy-2-oxo-1,3-dihydro-2H-3-benzazepine; 5 bar hydrogen in the presence of palladium / carbon in dimethylformamide at 8O ⁰ C analogously to Example 5. Yield: 58% of theory, melting point: 128-13O ⁰ C.

Calc .: C 65.16 H 7.42 N 8.14 Cl 6.87 Found: 65.12 7.55 8.11 7.06

- Example 257

3 - [(N- (3- (3-indolyl) propyl) hexahydro-azepinyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4,5 ~ tetrahydro-2H- 3-benzazepine monohydrate

Prepared from 3 - [(hexahydro-azepinyl-3) -methyl] -7,8-dimethoxy-2-oxo-1, 3,4,5-tetrahydro-2H-3-benzazepine and 3- (3-benzenesulfonyloxy-propyl ) Indole in dimethylformamide and triethylamine analogously to Example 1

 Yield: 49% of theory, melting point: 56-58 ° C

Calc .: C 70.98 H 8,14 N 8,27 F .: 71,08 8,10 8,16

Example 258

3 - [(N- (3- (3-indolyl) propyl) hexahydro-azepinyl-3) -methyl] -7,8-methylenedioxy-l, 3,4,5-tetrahydro-2H-3-benzazepin Dihydrochloride monohydrate

Prepared from 3 - [(N- (3- (indolyl-3) -propyl) -hexahydro-azepinyl-3) -methyl] -7,8-methylenedioxy-2-oxo-l, 3,4,5-tetrahydro- 2H-3-benzazepine and lithium aluminum hydride in diethyl ether and tetrahydrofuran analogously to Example 3. Yield: 56% of theory, melting point: 155-158 ° C.

Calc .: C 62.26 H 7.50 N 7.63 Cl 12.88 F .: 62.31 7.82 7.40 12.89

- 189 Example 259

3 - [(N- (3- (3-indolyl) propyl) -pyrrolidyl-3) -methyl] -7,8-dimethoxy-1,3,4, S-tetrahydro ^ H-S-benzazepine dihydrochloride monohydrate

Prepared from 3 - [(N- (3- (indolyl-3) -propyl) -pyrrolidyl-3) -methyl] -7, 8-dimethoxy-2-oxo-l, 3, 4, S-tetrahydro ^ HS- benzazepine and lithium aluminum hydride in diethyl ether and tetrahydrofuran analogously to Example 3

 Yield: 60% of theory, melting point: 125-128 ° C

Calc .: C, 62.44, H, 7.67, N, 7.80, Cl, 13, 16 Found: 62.35, 7.87, 7.59, 13.67

Example 260

2 - [(N- (3- (Indolyl-3) -propyl) -piperidyl-3) -methyl] -6,7-dimethyl-1,2, S, -tetrahydro-isoquinoline dihydrochloride monohydrate

Prepared from 2 - [(N- (3- (indolyl-3) -propyl) -piperidyl-3) -methyl] -6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline; Lithium aluminum hydride in diethyl ether and tetrahydrofuran analogously to Example 3.

Yield: 90% of theory, Melting point: 198-201 ⁰ C.

Ber. : C 66 , 38 H 8th 16 N 8th, 29 Cl 14 00 Gef .: 66 , 29 8th , 21 8th, 46 13 , 82

- 190 Example 261

3 - [(N- (3- (indolyl-3) -propyl) -hexahydro-azepinyl-3) -methyl] 7, e -methylenedioxy ^ -oxo-l, 3, 4,5-tetrahydro-2H-3- benzazepinmonohydrat

Prepared from 3 - [(hexahydro-azepinyl-3) -methyl] -7,8-methylenedioxy-2-oxo-1, 3,4,5-tetrahydro-2H-3-benzazepine and 3- (3-benzenesulfonyloxy-propyl ) -indole analogously to Example 1. Yield: 61.5% of theory, melting point: 62-64 ° C.

Calc .: C, 70.84, H, 7.59, N, 8.55, Found: 70.73, 7.59, 8.42

Example 262

2 - [(N- (3- (3-indolyl) propyl) -pyrrolidyl-3) -methyl] -6,7-dimethyl-1,2,3,4-tetrahydro-isoquinoline dihydrochloride semihydrate

Prepared from 2 - [(N- (3- (indolyl-3) -propyl) -pyrrolidyl-3) -methyl] -6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline and lithium aluminum hydride in ether as in Example 3. Yield: 86% of theory,

Melting point: 143-145 ° C

Calc .: C 67.06 H 7.92 N 8.69 Cl 14.66 F .: 66.92 8.07 8.48 14.87

- 191 Example 263

2 - [(N- (3- (Indolyl-3) -propyl) -pyrrolidyl-3) -methyl] -6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline hydrochloride χ 1.5 hydrate

Prepared from 2 - [(pyrrolidyl-3) -methyl] -6,7-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinoline and 3- (3-benzenesulfonyloxypropyl) -indole analogously to Example 1

Yield: 67% of theory, Melting point: 117-120 ⁰ C.

Calc .: C 67.69 H 7.78 N 8.77 Cl 7.40 F .: 67.62 7.80 8.72 7.93

Example 264

3 - [(N- (3- (indolyl-3) -propyl) -pyrrolidyl-3) -methyl] -7,8-methyl-lendioxy-1,3,4-s-tetrahydro-HS-benzazepine-dihydrochloride 1.5 χ hydrate

Prepared from 7,8-methylenedioxy-l, 3,4,5-tetrahydro-2H-3-benzazepine and 3- (benzenesulfonyloxy-methyl) -N- [3- (indolyl-3) propyl] -pyrrolidine analogously to Example 2. Yield: 75% of theory, m.p .: 191-193 ° C

Calc .: C 61.01 H 7.21 N 7.90 Cl 13.34 V: 60.90 7.27 7.85 13.70

- 192 Example 265

3 - [(N- (3- (indolyl-3) -propyl) -hexahydro-azepinyl-3) -methyl] 7, 8-dimethoxy-1,3,4-s-tetrahydro ^ H ^ benzazepine dihydrochloride monohydrate

Prepared from 3 - [(N- (3- (indolyl-3) -propyl) -hexahydro-azepinyl-3) -methyl] -7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydro- 2H-3-benzazepine and lithium aluminum hydride in tetrahydrofuran and diethyl ether analogously to Example 3

Yield: 53% of theory, melting point: 158-16O ⁰ C.

Calc .: C 63.58 H 8.00 N 7.41 Cl 12.51 F .: 63.41 8.18 7.36 12.23

Example 266

3 - [(N- (3- (Indolyl-3) -propyl) -pyrrolidyl-3) -methyl] -7,8-dimethyl-1,3,4-S-tetrahydro-H-S-benzazepine dihydrochloride monohydrate

Prepared from 3 - [(N- (3- (indolyl-3) -propyl) -pyrrolidyl-3) -methyl] ^, e-dimethyl ^ -oxo-l, 3, 4, 5-tetrahydro-2H-3- benzazepine and lithium aluminum hydride in tetrahydrofuran / ether analogously to Example 3.

Yield: 65% of theory, melting point: 168-170 ⁰ C.

Ber. : C 66 39 H 8th, 16 N 8th , 29 Cl 13 99 Gef .: 66 29 8th, 44 8th , 08 14 08

- 193 Example I

Tablets containing 7.5 mg of 3 - [(N- (2- (naphthyl-2) -ethyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-1, 3,4, 5- tetrahydro-2H-3-benzazepine hydrochloride

Composition: 7.5 mg 1 tablet contains: 59.5 mg active substance 48.0 mg corn starch 4.0 mg lactose 1.0 mg polyvinylpyrrolidone Magnesiusistearat

Magnesiusistearat

120.0 mg

production method

The active ingredient, corn starch, lactose and polyvinylpyrrolidone are mixed and moistened with water. The wet mixture is printed through a 1.5 mm mesh screen and dried at about 45 ^° C. The dry granules are beaten through a 1.0 mm mesh screen and mixed with magnesium stearate. The finished mixture is compressed on a tablet press with punches of 7 mm diameter, which are provided with a partial notch, into tablets. Tablet weight: 120 mg

Example II

Dragees to 5 mg of 3 - [(N- (2- (naphthyl-2) -ethyl) -piperidyl-3) -methyl] -7,8-dimethoxy-2-oxo-l, 3,4,5-tetrahydro- 2H-3-benzaze · pin hydrochloride

1 drag core contains:

Active substance 5.0 mg

Corn starch 41.5 mg

Lactose 30.0 mg

Polyvinylpyrrolidone 3.0 mg

Magnesium stearate 0.5 mg

80.0 mg

production method

The active ingredient, corn starch, lactose and polyvinylpyrrolidone are mixed well and moistened with water. The

Press the moist mass through a sieve with a 1 mm mesh size, dry at about 45 ^° C. and then beat the granules through the same sieve. After admixing magnesium stearate, curved tablet cores with a diameter of б mm are pressed on a tableting machine. The Drageekerne thus prepared are in a known manner with a

Coated layer consisting essentially of sugar and talc. The finished dragees are polished with wax. Dragee weight: 130 mg

- 195 Example III

Ampoules of 5 mg of 3 - [(N- (2- (naphthyl-2) -ethyl) -piperidyl-3) -methyl] -TS-dimethoxy-oxo-1,3,4,5-tetrahydro-2H-3 benzazepine hydrochloride

1 ampoule contains:

Active substance 5.0 mg

Sorbitol 50.0 mg

Water for injections ad 2.0 ml

production method

In a suitable mixing vessel, the active ingredient is dissolved in water for injection and the solution is made isotonic with sorbitol.

After filtration through a membrane filter, the solution is filled under N ₂ gassing into purified and sterilized ampoules and autoclaved for 20 minutes in flowing steam.

Example IV

Suppositories to 10 mg of 3 - [(N- (2- (naphthyl-2) -ethyl) -piperidyl-3) -methyl] -7, .8-dimethoxy-2-oxo-1,3,4,5-tetrahydro 2H-3-benzazepine hydrochloride

1 suppository contains:

Active substance 0,010 g

Hard grease (eg Witepsol H 19 and W 45) 1.690 g

1,700 g

- 196 manufacturing process;

The hard fat is melted. At 38 ^e C, the ground active substance is homogeneously dispersed in the melt. It is cooled to 35 ^e C and poured into slightly pre-cooled suppository molds.

Example V

10 mg of 3 - [(N- (2- (naphthyl-2) -ethyl) -piperidyl-3) -methyl] -7,8-diraethoxy-2-oxo-1,3,4,5-tetrahydro- 2H-3-benzazepine hydrochloride

100 ml solutions contain:

Active ingredient 0.2 g

Hydroxyethyl cellulose 0.15 g

Tartaric acid 0.1 g

Sorbitol solution 70% dry substance 30.0 g

Glycerol 10.0 g

Benzoic acid 0.15 g

Dest.Wasser ad 100 ml

Production method;

Dest. Water is heated to 70 ⁰ C. Herein, hydroxyethyl cellulose, benzoic acid and tartaric acid are dissolved with stirring. It is cooled to room temperature and in this case the glycerol and the sorbitol solution are added with stirring. At room temperature, the active ingredient is added and stirred until complete dissolution. The mixture is then evacuated with stirring to vent the juice.

Claims (17)

claims 1) 3-Z ~ (H- (2- (BHnzo _/> "" b_7thienyl-3) -etliyl) -piperidyl-3) -netayl _i 7-7, C-dimethoxy-2-oxo-1>3> 4 , 5-tetrahydro-2H-3-benzazepine, ra) 2- / ~ (LI- (3- (6-i-thethoxy-naphthyl-2-oxy) -propyl) -pyrrolidyl-3) -Lithyl7-6,7-diynethoxy-1-oxo -1,2,3 »4-tet raliydro-i so chiolin, n) 2- / ~ (L ^r - (2- (6-ethoxy-naphthyl-2) -tet'ayl) -liexahydro-azepinyl-3) -methyl-6,7-net-hydroxy-dioxy-1-oxo 1,2,3 »4th te rahydro-i so chino о) 3 - /, "((IT- (2- (4-ethyl) -phenyl) -3-ethyl-7,3-diniethioxy-2-oxo-1,3 , 4, 5-tetrahydro-2H-3-ben3a2epine and -208- p) 3 - / _ "" (Ii- (2- (3,4-diraethoxyphenyl) -etb.yl) -he3cah. hydro-aaepinyl-3) -nethy] 7-7,8-methylenedioxy-2- oxo-1,3,4,5-tetrahydro-2K-3-benzazepine their Snantioneren, their diastereoranes and their acid addition salts are prepared. 1. A process for the preparation of novel cyclic amine derivatives of the general formula H-E CH CCH ₂ ) Ή-G-R, (I) in the A a - - or -CHsCH group, B is a -CH ₂ -, -CH ₂ CH ₂ -, -CO- or -CHgCO group, wherein the carbon atom indicated by x. is linked to the phenyl nucleus, 2. The method according to claim 1, characterized in that cyclic amine derivatives of the general formula I are prepared, in which A, B, m and η are as defined in claim 1, E is a straight-chain alkylene group having 1 to 3 carbon atoms, G is a straight-chain alkylene group having 1 to 6 carbon atoms, one with an aromatic or heteroaromatic radical -204- R bonded methylene group of a straight-chain alkylene group having 3 to б carbon atoms may be replaced by an oxygen atom, a LIethylimino- or Sthyliminogruppe R _{1 is} a LIethyl or Liethoxygruppe, R _{2 is} a LIethyl- or Liethoxygruppe or R ₁ and R "together a LIethylendioxygruppe and R is an optionally substituted by a methyl group, puryl, thienyl, pyridyl, benzo / ~ b7furyl or benzo / b / -thienyl, substituted by a halogen atom, a LIethoxy- or Llethansulfonyloxygruppe Benzo / ~ b_7thienylgruppe, optionally substituted by a hydroxy, lethoxy or benzyl oxy group substituted indolyl or H-LIethyl-indolyl, a Dirnethyl-thienyl or dimethoxy-isoquinolyl, optionally mono- or disubstituted by LIethyl- or Liethoxygruppen ilaphthyl group, wherein the substituents may be the same or different or also when B represents a -CIL.sup.- or .sup.SO group, a phenyl group optionally substituted by an ethylenedioxy group, a phenyl group which is mono- or disubstituted by chlorine or bromine atom, ethyl or diethoxy groups, where the substituents may be identical or different , one by a hydroxy, benzyloxy, LIes thansulfonyloxy, Trifluormethansulfonyloxy-, Trifluorraethy A substituted phenyl group, a Tribiethoxyphenyl-, Tetramethylphenyl- or Oihalogenaninophcnylgruppe, their enantiomersη, their diate isomers, their ll-oxides and their sour dressing salts. -205- 3 · Process according to Claims 1 and 2, characterized in that cyclic amine derivatives of the general formula (Ia) in the R ₁ , Rp, A, B, E, G, η and η v / ie are defined in claim 2, whose enantiomers, their diastereomers, their IT oxides and their acid addition salts prepared r / earth. 3 - CH IT-G-R, (VII) Jx о in the R, R _1, Rp, E, G, га and η are as defined above and Bp represents a -CO- or -CHpCO group, it being understood that χ characterized carbon atom is vorknüp with the phenyl nucleus, is reduced with nascent hydrogen or e) for the preparation of compounds of the general formula I in which G, with the exception of the radicals containing one sulfur atom, one sulfinyl or sulfonyl group, has the meanings mentioned above for G and A is the -CHp-CHp group and B is the ethylene or carbonyl group, a compound of the general formula - CII ⁴ EC ₁ -S, (VIII) 3 represents a straight-chain alkylene group having 1 to 3 carbon atoms optionally substituted by an alkyl group having 1 to 3 carbon atoms, G is a straight-chain alkylene group having 1 to 6 carbon atoms optionally substituted by an alkyl group having 1 to 3 carbon atoms, wherein the Ⓒ group bonded to an aromatic or heteroaronic radical R is a straight-chain alkylene group having 3 to G optionally substituted by an alkyl group having 1 to 3 carbon atoms Carbon atoms by a Gauerotoff- or Sulfur atom, a sulfinyl, sulfonyl or optionally substituted by an alkyl group having 1 to 3 carbon atoms imino group may be replaced, R _{1 is} a hydrogen or halogen atom, a trifluoromethyl, ITitro, amino, alkylamino, di alkyl amino, alkyl, hydroxy, alkoxy or phenylalkoxy group, each alkyl part may contain in each case 1 to 3 carbon atoms, R _{2 is} a hydrogen atom or halogen atom, a hydroxy, alkoxy, phenylalkoxy or alkyl group, wherein each alkyl portion may each contain from 1 to 3 carbon atoms, or R ₁ and R p together represent an alkylenedioxy group having 1 or 2 carbon atoms, m is the number 1, 2, 3, 4, 5 or б and η is the number 0, 1, 2 or 3, but where η + m must represent the number 3, 4, 5 or б, and R is a 5- or 6-membered heteroaromatic ring bonded via a carbon or nitrogen atom and containing an oxygen, sulfur or nitrogen atom, two nitrogen atoms or one nitrogen atom and one oxygen or sulfur atom, and to which a phenyl ring may additionally be fused in which the pail can also be attached via the phenyl nucleus, and in which the carbon skeleton of the abovementioned mono- and bicyclic rings is replaced by an ilohalogen atom, an alkyl, hydroxy, alkoxy, phenylalkoxy, phenyl, dimethoxyphenyl, Nitro, amino, acetylamino, carbamoylamino, ІГ-ЛГ.іуі-сагЬапоуіапіпо, hydroxymethyl, IIercapto, alkylnercapto, alkyl sulfinyl, alkyl sulfonj * !, alkyl sulfonyloxy, alkylsulfonylamino, alkoxy carbonylmet hoxy, carboxyniethoxy or alkoxymettryl mono- or disubstituted or may be substituted by a LIethylen- or ethylenedioxy and equilateral gegebanenfalls an existing imino group in the above-mentioned heteroaromatic rings by an alkyl, phenylalkyl or phenyl group may be substituted with one above-mentioned indolyl group amino- additionally by a methyl, Dimethylamine-, LIethoxy-, Acetox3 ^r -, trifluoromethyl, trichloromethyl, carboxyl, Llethoxycarbonyl-, ethoxycarbonyl, cyano, cyclohexyl, trimethoxyphenyl, rrifluorophenyl, trichlorophenyl, tribromophenyl, Dihalogenaminophenyl-, benzyl, benzyloxy or benzylamino group may be substituted and here the above-mentioned benzyl, benzyloxy or Benzylaminosubstituenten the indolyl in the benzyl nucleus by Uethoxy- or IJethyl groups mono-, di- or may be trisubstituted, the substituents may be the same or different, an optionally substituted by an alkylenedioxy having 1 or 2 carbon atoms, ilaphthyl group or by halogen atoms, alkyl, hydroxy, alkoxy, alkylsulfonyloxy, nitro, amino or alkanoylamino mono- or disubstituted naphthyl group, wherein the Substituents may be the same or different, a benzyloxy or 4 _} 5,6,7-Tetrahyäro-benzo / "~ b7-thienyl group, and, when B represents a -CH ₂ - or -CO- # group, also an optionally an alkylenedioxy group having 1 or 2 carbon atoms substituted phenyl group, one represented by a halogen atom, an alkyl, hydroxy, alkoxy, phenylalkoxy, nitro, amino, alkanoylamino, alkylsulfonylamino, bis (alkylsulfonyl) amino, alkylsulfonyloxy -, trifluoromethyl, trifluoromethoxy or trifluoromethylsulfonyloxy group substituted phenyl group, a thyl group disubstituted by halogen atoms, alkyl or alkoxy groups, wherein the substituents are the same or variously , a trialkoxyphenyl, tetraalkylphenyl or dihaloaminophenyl group, unless otherwise indicated, the in the definition of the radical R mentioned above, alkyl, alkoxy or alkanoyl moieties may each contain 1 to 3 carbon atoms, their enantiomers, their diastereomers, their N-oxides and their acid addition salts and optionally a medicament, suitable for the treatment of and ischemic heart disease, characterized in that a) a compound of the general formula - E - ОН N-H, (II) (CH ₂ ) _n in the R 1, R ₂ , A, B, Ξ, m and η are as defined above, with a Compound of the general formula Z ₁ -GR in the R and G are as defined above and , (III) a nucleophilic leaving group, a hydroxy group or together with a hydrogen atom of the adjacent methylene groups represents an oxygen atom, is reacted or -200a- b) a compound of the general formula Л - H (IV) -201- in the R ₁ , Rp, A and B are as defined above, with a compound of the general formula Z ₂ -S-CII JI-GR, (V) ^X (CH ₂ ) _n in the R, Б, G, m and η are as defined above and Zp represents a nucleophilic leaving group c) for the preparation of compounds of the general formula I in which B represents a -CHp- or -CHpCHp group, a compound of the general formula H-S-CHH-G-D, (VI) / \ / B ₁ ^CII 2 η in the R, R ₁ , Rp, A, U, G, m and η are as defined above and B _{1 represents} a -CC- or -ÖKpCO-group, said with: c characterized carbon atom is linked to the phenyl nucleus, is reduced or d) for the preparation of compounds of the general formula I in which A is a -CIIp group and B is a -CO- or -CII ₀ CO-GrUpPe, a compound of the general formula -202- 4. The method according to claim 1 to 3, characterized in that cyclic amine derivatives of the general formula Ia according to claim 3, in which A is a -CHpCHp group, B is a -CII ₂ , -CII ₂ -GH ₂ , -GO or -CI ^ CO group, wherein the nitro χ is carbon linked to the phenyllene, D is an ethylene or ethylene group, G is a straight-chain alkylene group having 2 to 4 carbon atoms, wherein the IJethylengruppe connected to an aromatic or heteroaromatic radical R is a straight-chain -206- Alkylengruppe nit 3 or 4 carbon atoms may be replaced by an oxygen, R _{1 is} a liethoxy group, Ep is a methoxy group or R ₁ and R ₂ together represent a Llethylendioxygruppe, m is the number 2, 3 or 4,
η is the number 1 and R is a naphthyl-2-, 6-lethoxy-naphthyl-2-, 5-methyl-6-methoxynaphthyl-2, thienyl-2, benzo / β-furyl-2 or 3enzo / ~ b7 -thienyl-3-group or also, when B represents the -Clip- or -CO-group, a 4-Kethoxyphenyl- or 3,4-dimethoxyphenyl group, their enantiomers, their diastereomers and their acid addition salts are prepared. ⁴ (CH) / in the R, R ₁ , R _? , 3, E, η and η are as defined above, G ₁ except the group containing a sulfur atom, a Sulfinj ^ i- or sulfonyl group having the meanings mentioned for G in claims 1 to 7 and B_ is a -CII ₀ - or Represents -СО group, is hydrogenated and -203- if desired, subsequently a protecting residue used during the reactions a) to e) to protect reactive groups such as hydroxyl, amino, alkylamino or imino groups is split off, if desired subsequently a compound of general formula I in which R contains a nitro group, is converted by reduction into a corresponding amino compound of general formula I and / or a compound of general formula I in which R contains an amino group is converted by means of acylation into a corresponding alkanoylamino compound of general formula I and / or a compound of the general formula I thus obtained, which contains at least one chiral center, is resolved into its diastereomers or into their enantiomers, and / or a compound of the general formula I thus obtained is converted into its acid addition salts, in particular into its physiologically tolerated acid addition salts with inorganic or organic acids and, if appropriate, by non-chemical means a compound of general formula I or its physiologically acceptable acid addition salt in one or more inert carriers and / or diluents is incorporated. 5. Process according to claims 1 to 4, characterized s that as cyclic Arainderivate the general Poпае1 Ia ge according to claim 3 a) 3- / ~ (n- (2- (1-naphthyl-2) -ethyl) -piperidyl-3) -metbyl7-7, S-dimethoxy-2-oxo-1,3,4-> 5-tetrahydro-2H- 3-benzazepine, b) 3 - / "(1T- (2- (5-lethyl-6-methoxynaphthyl-2) -ethyl) -piperi dyl-3) -methyl_7-7,8-diniethoxy-2-ozo-1,3,4T5-tctrah7dro-2H-3-benzazepine, c) 3-2Γ "2- (ΐ :-( 2- (6 et _'L iyl7-7, o-dmetho; cy-2-o; o-1, 3i ^i' -, 5-tetra'a - dro-2II-3-benzazcpiu, -207- d) 2- (2- (6-Iethoxy-naphthyl-2) -ethyl) -hex; ahydro-aaepinyl-3) -methyl7-6,7-ethylenedioxy-i-oxo-i, 2,3,4-tetrahydroisoc'ainoline, e) 2- / ~ (1-T- (2- (1-jlbyl-2) -ethyl) -hexahydro-azepinyl-3) -methyl7-6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydro- isoquinoline, f) 2-7 "(1I- (2- (3,4-Dimethy-phenyl) -ethyl) -piperidyl-3) -methyl7-6,7-dimethyl-1,3,3,4-tetrahydro-isocliinoline . g) 2- / ~ (II- (2- (3,4-Dimethoxy-phenyl) -ethyl) -piperidyl-3) -meth3'-l7-6,7-dinethyl-1-oxo-1,2,3 , 4-tetrahydro-isoquinoline, h) 2- _/> "" (II- (3- (4-nethoxy-phenoxy) -propyl) -piperidyl-3) -methyl7-6,7-diinethyl-1-oxo-1,2,3> 4- tetrahydro-isoquinoline, i) 3- (II- (4- (thienyl-2) -butyl) -piperidyl-3) -niethyl-7-7, o -dimethoxy-2-0X0-1,3,4,5-tetrahydro-2H- 3-Ьenza2epin, k) 3-Z ~ (LT- (2- (benzo / ~ D__7furyl-2) -etli3a) -piperidyl-3) -neäiy _i l7-7,3-dinethoxy-2-oxo-1,3,4,5 tetrahydro-2H-3-beпzazepiп, 6. Process according to claims 1 to 5, characterized in that cyclic Jiminderivate of the general formula Ia according to claim 3 netho; cy-2-o: ro-1,3,4 »5-tetrahydro-2H-3-benzazepine, b) 2 - / "(1T- (3- (4-Hethoxy-phenoxy) -propyl) -piperidyl-3) -ethyl-6,7-dimethyl-1-0X0-1,2,3,4-tetrahydro- isoquinoline, c) 3- / ~ (H- (4-thienyl-2) -butyl) -piperidyl-3) -ethyl-7-7, u-dimetho: cy-2-o: o-1,3,4, tetrahydro ^ H ^ benzazepine, d) 2 - / "" (ΙΪ 3- (6-lethoxy-naphthyl-2-oxy) -propyl) -pyrrolidyl-3) -methyl7-6,7-dimetho2: y-1-oxo-1,2, 3,4-tetrahydro-isoquinoline, e) 2 - /, "" (II- (2- (6-lethethoxnaphthyl-2) -ethyl) -liexahydro-azopinyl-3) -ethyl7-6,7-methylenedioxy-1-0X0-1,2, 3,4-tetrahydro-isoquinoline, f) 3 - / _ '' '(I \ - (2- (4-IIethoxy-phenyl) -ethyl) -hexahydro-azepinyl-3) -r.iethyl7-7,3-dinetho2: y-2-oxo-1 , 3,4,5-tetrahydro-2II-3-benzazepine and s) 3-Z "" (1- (2- (3,4-Dinethoxy-phenyl) -ethyl) -hexahydro-azepinyl-3) -ethyl-7,0-ethylenedioxy-2-o: o-1 , 3,4,5-tetrahydro-2 II-3 bensaGepin -209- their enantiomers, their diastereomers and their acid addition salts are prepared. 7. Process according to claims 1 to 6, characterized in that 3-ZT "(N- (2- (naphthyl-2) -ethyl) -piperidyl-3) -methyl7-7,8-dimethoxy-2-oxo 1,3,4,5-tetrahydro-2H-3-benzazepine, its enantiomers, its diastereomers and acid addition salts thereof are prepared. 8. Process according to claims 1 to 7, characterized in that physiologically acceptable acid addition salts of the compounds according to claims 1 to 7 are prepared with inorganic or organic acids. 9. Process according to claims 1 to 8, characterized in that the reactions are carried out in a solvent. 10. The method according to claims 1a, 1b and 9, characterized in that the reaction is carried out in the presence of an acid-binding LIittels. 11. The method according to claims 1a, 1b and 9 »characterized in that the reaction, if Z .. or Zp represents a nucleophilic leaving group is carried out at temperatures between 0 and 150 ⁰ C. 12. The method according to claims 1a and 9, characterized in that the reaction, if Z-. a hydroxy group or together with a hydrogen atom of the adjacent methylene group represents an oxygen atom, with hydrogen in opposite -210- wart of a hydrogenation catalyst at temperatures zvri see 20 and 120 ⁰ C, preferably at temperatures between 50 and 100 ⁰ C, performed. 13. The method according to claims 1a and 9, characterized in that the reaction, if Z-. together with a hydrogen atom of the adjacent methylene group represents an oxygen atom, in the presence of a suitable complex metal hydride at temperatures between 0 and 50 ⁰ G, but preferably at room temperature, is performed. 14. The method according to claims 1c and 9, characterized in that the reduction with a metal hydride, with diborane or with a complex of borane and a thioether at temperatures between 0 and 80 ⁰ C, but preferably ta. Temperatures between 10 and 45 ⁰ C, is performed. 15 »Process according to claims 1d and 9, characterized in that the reduction with nascent hydrogen at temperatures between 20 and 150 ⁰ C, but preferably at the boiling temperature of the reaction mixture, for. B. at temperatures between 80 and 100 ⁰ C, is performed. 16. The method according to claims 1c and 9, characterized in that the reduction with catalytically excited hydrogen at temperatures between 0 and 70 C, but preferably at temperatures between 20 and 50 ⁰ C, is performed. 17. The method according to claims 1 to 8, characterized in that the elimination of the protective groups used is carried out hydrolytically or hydrogenolytically.