DE2523565A1 - Araliphatic amines and derivs. - with antiphlogistic, hypolipaemic, analgesic, antipyretic, antithrombotic, etc., activity - Google Patents

Abstract

Araliphatic N cpds. of formula (I) and their salts are new: R-A-Z (I): (where R is a 4-biphenylyl or 4-phenoxyp phenyl gp. opt. mono- or polysubstd. by F, Br and/or Cl; A is -CH(Me)-CH2-(CH2)n-, -C(Me)=CH-(CH2)n or -C(OH)(Me)-CH2-(CH2)n-; Z is N R1 R2, imidazol-1-yl, phthalimide or 3,4-dihydro-4-oxo-phthalazin-1-ylamino; R1 and R2 are H, 1-6C alkyl, 1-6C azaalkyl or 1-6C acyl, or together form 4-7C alkylene, 3-oxapentamethylene or 3-R3-3-azapentamethylene; R3 is H, 1-6C alkyl or 1-6C hydroxyalkyl; n=0, 1 or 2). Cpds. (I) have antiphlogistic, anti-arteriosclerotic, hypolipaemic, analgesic-antipyretic enzyme-inducing, fibrinolytic and thrombocyte aggregation inhibiting activity, and are also useful as intermediates for other medicaments.

Description

Araliphatic nitrogen compounds

and processes for their preparation. The invention relates to novel araliphatic ones Nitrogen compounds of the general formula I R-A-Z 1 in which R is an unsubstituted one or a mono- or polysubstituted by F, Cl and / or Br 4-biphenylyl- or 4-phenoxyphenyl residue, A -CH (CH3) -CH2- (CH2) n 2 -C (CH3) = CH- (CH2) n or -c (OH) (CH3) ~ CII2 (CII2) n, Z -NR¹R², imidazol-1-yl, phthalimido or 3,4-dihydro-4-oxo-phthalazin-1-yl-amino, R1 and R2 (identical or different) each have H, alkyl, azaalkyl or acyl with each 1 - 6 carbon atoms or together alkyl with 4-7 carbon atoms, 3-oxapentamethylene or 3-R3-3-azapentamethylene, R3 denotes H, alkyl or hydroxyalkyl each with up to 6 carbon atoms and n denotes O, 1 or 2, -as well as their physiologically harmless acid addition salts.

The invention was based on the object of finding new compounds that can be used to manufacture drugs. This task was solved by providing the compounds of formula I.

It has been found that the compounds of the formula I are well tolerated have valuable pharmacological properties. In particular, anti-inflammatory occur Effects on, for example, in the adjuvant arthritis test using the Newbould (Brit. J. Pharmacol. 21.

(1963) pages 127-136) on rats.

Furthermore, anti-arteriosclerotic, cholesterol-lowering effects are found (detectable in the serum of rats according to the method of Levine et al., Automation in Analytical Chemistry, Technicon Symposium 1967, Mediad, New York, pages 25 - 28) and triglyceride level-lowering effects (verifiable using the Noble method and Campbell, Clin. Chem. 16 (1970), pp. 166-170).

Furthermore, analgesic, antipyretic, enzyme-inducing, fibrinolytic and uronibocyte-aggregation-inhibiting effects according to common Methods are observed.

The compounds of the formula I and their pnarsiologically harmless Acid addition salts can therefore be used as drugs and also as intermediates used in the manufacture of other drugs. For example, the primary amines of the formula I (Z = NH2) by reaction with nitrous acid into the corresponding alcohols and through their oxidation into the corresponding carboxylic acids be transferred, which in turn have valuable anti-inflammatory properties.

The invention relates to compounds of the formula I and their physiologically harmless salts.

In the compounds of the formula I, the radical R is preferably an unsubstituted or, in particular, one which is simply substituted as indicated 4-biphenylyl or 4-phenoxyphenyl radical.

Among the substituents of the biphenylyl radical is primarily F, in the second place Cl is preferred. The substituents are preferably in the 4 'position (e.g. 4'-fluoro-4-biphenylyl, 4'-chloro-4-biphenylyl, 4'-bromo-4-biphenylyl).

There is also a substitution of the biphenylyl radical in the 2 'position preferred (e.g. 2 1-fluoro-4-biphenylyl, 2'-chloro-4-biphenylyl, 2'-bromo-4-biphenylyl). The biphenylyl radical can, however, also be substituted in the 2-, 3- and / or 3'-position be. Among the multiply substituted biphenylyl residues are the doubly substituted, in particular those disubstituted in the 2 ', 4' position, preferred; however it is too 3-, 4-, 5-, 6-, 7-, 8- or 9-fold substitution of the biphenylyl radical is possible. Preferred among the polysubstituted biphenylyl radicals are those which carry the same substituents, e.g. difluoro-4-biphenylyl such as 2 ', 4'-difluoro-4-biphenylyl, Dichloro-4-biphenylyl such as 2 ', 4'-dichloro-4-biphenylyl, dibromo-4-biphenylyl such as 2', 4'-dibromo-4-biphenylyl.

Among the biphenylyl radicals that contain various substituents, those which carry at least one fluorine atom are preferred, e.g. 2'-fluoro-4'-chloro-4-biphenylyl, 2'-fluoro-4'-bromo-4-biphenylyl, 2'-chloro-4'-fluoro-4-biphenylyl, 2'-bromo-4'-fluoro-4-biphenylyl. Also among the multiply substituted biphenylyl radicals are the fluorine-substituted ones preferred, e.g., nonafluoro-4-bphenyly.

Cl is preferred among the substituents on the 4-phenoxyphenyl radical. The substituents of the 4-phenoxyphenyl radical are preferably in the phenoxy group, especially in the p-, but also in the o-position. Preferred substituted 4-phenoxyphenyl radicals are e.g. 4-p-chlorophenoxyphenyl, 4-o-chlorophenoxyphenyl, -p-fluorophenoxyphenyl and 4-p-bromophenoxyphenyl. The phenoxy group can, however, also be substituted in the m-position be. The phenyl radical (substituted in the 4-position by the phenoxy group) can also be used be substituted in the 2-, 3-, 5- and / or 6-position by F, Cl and / or Br. Under the multiply substituted 4-phenoxyphenyl radicals are twofold, in particular those substituted in the 2- and 4-positions of the phenoxy group are preferred; it however, it is also a 3-, 4-, 5-, 6-, 7-, 8- or 9-fold substitution of the 4-phenoxyphenylresi: es possible. Among the polysubstituted 4-phenoxyphenyl radicals are those preferred to have the same substituents, e.g. 4- (2,4-difluorophenoxy) -phenyl, 4- (2,4-dichlorophenoxy) phenyl, 4 (2,4-dibromophenoxy) phenyl or 4- (pentafluorophenoxy) phenyl.

The parameter n is preferably 1, so that the remainder A is preferably Has 4 carbon atoms. The radical A preferably means -CH (CH3) -CH2- (CH2) n- or -C (OH) (CH3) -CH2 (CH2) n in particular -CH (CH3) -CH2-CH2- or -C (OH) (CH3) -CH2-CH2-, furthermore e.g.

-C (CH3) = CH-CH2-, -CH (CH3) -CH2-, -C (OH) (CH3) -CH2-, -CH (CH3) - (CH2) 3-, -C (OH) (CH3) - or -C (CH3) = CH (CH2) 2-.

In the definition of the radicals R1 and R2, alkyl preferably denotes Methyl, ethyl, n-propyl or isopropyl, further e.g.

n-butyl, isobutyl, sec-butyl, tert-butyl, 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-1-butyl, 2-methyl-2-butyl, 3-methyl-1-butyl (isoamyl), 3-methyl-2butyl, 2,2-dimethyl-1-propyl (neopentyl), 1-hexyl- or 4-methyl-1-pentyl. If R¹ is alkyl means sit R2 preferably H or the same alkyl group. Azaalkyl is preferably branched and preferably represents dimethylaminoethyl such as 2-dimethylaminoethyl, Diethylaminoethyl such as 2-diethylaminoethyl, dimethylaminopropyl such as 2- or 3-dimethylaminopropyl. Acyl is preferably alkanoyl, especially acetyl, also e.g. formyl, propionyl, Butyryl, isobutyryl, valeryl, isovaleryl, trimethylacetyl, methylethylacetyl, capronyl, Isocapronyl, tert-butylacetyl, diethylacetyl, nicotinoyl.

if R¹ is acyl, R² is preferably H. Alkylene is preferably for tetramethylene, 1- or 2-methyltetramethylene, pentamethylene, 1-, 2- or 3-methylpentarnetby1.en, 1,5-dimethylpentamethylene or hexamethylene, also e.g. for 1- or 2-ethyltetramethylene, 1- or 2-n-propyltetramethylene, 1- or 2-isopropyltetramethylene, 1,2-, 1,3-, 1,4- or 2,3-dimethyltetramethylene, 1,2-, 1,3-, 1,4-, 2,3- or 2,4-dimethylpentamethylene, 1-, 2- or 3-ethylpentamethylene, 1-, 2-, 3- or 4-methylhexamethylene. R3 is preferably H, methyl, ethyl or 2-hydroxyethyl.

12 Accordingly, R preferably denotes amino, methylamino, ethylamino, n-propylamino, isopropylamino, dimethylamino, diethylamino, di-n-propylamino, diisopropylamino, 2-dimethylaminoethylamino, 2-diethylaminoethylamino, 2- or 3-dimethylaminopropylamino, Acetamido, pyrrolidine, piparidino, 2-, 3- or 4-methylpiperidino, 2,6-dimethylpiperidino, Homopiperidino, morpholino, piperazino, 4-methylpiperazino, 4-ethylpiperazino or 4- (2-hydroxyethyl) piperazino.

Accordingly, the invention particularly relates to those Compounds of the formula I in which at least one of the radicals R, A and Z is one of the has preferred meanings given above. Some preferred groups of Compounds can be expressed by the following sub-formulas Ia to It, which correspond to formula I and in which the unspecified Radicals have the meaning given for the formula I, but in which R in Ia unsubstituted or monosubstituted or polysubstituted by F, Cl and / or Br 4-biphenylyl radical; in Ib R one unsubstituted or one or more than one is 4-phenoxyphenyl radical substituted by F, Cl and / or Br; in Ic R 4-biphenylyl, Fluoro-4-biphenylyl, chloro-4-biphenylyl, bromo-4-biphenylyl, difluoro-4-biphenylyl, is p-phenoxyphenyl, 4- (chlorophenoxy) phenyl or 4- (bromophenoxy) phenyl; in Id R p-biphenylyl, 2'-fluoro-4-biphenylyl, 4'-fluoro-4-biphenylyl, 4'-chloro-4-biphenylyl, 4'-bromo-4-biphenylyl, 2 ', 4'-difluoro-4-biphenylyl, 4-p-chlorophenoxyphenyl or 4-p-bromophenoxyphenyl means; in Ie R p-biphenylyl, 4'-fluoro-4-biphenylyl, 4'-chloro-4-biphenylyl or Is 4-p-chlorophenoxyphenyl; in If A -CH (CH3) -CH2CH2-, -C (OH) (CH3) -CH2- (CH2) n ~ or -C (CH3) = CH-CH, -; in Ig A is -c (OH) (CH3) -CH2- (CH2) n; in you A is -CH (CH3) -CH2CH2- or -C (OH) (CH3) -CH2CH2-; in Ii A -C (OH) (CH3) -CH2CH2- means; in Ij Z amino, diethylamino, 2-diethylaminoethylamino, acetamido, piperidino, 4-methylpiperidino, morpholino, 4- (2-hydroxyethyl) piperazino, imidazol-1 -yl, Phthalimido or 3,4-dihydro-4-oxo-phthaiazin-1-yl-amino means; in Ik Z amino, diethylamino, acetamido, piperidino, morpholino, imidazol-1-yl or Means phthalimido; in II Z is amino; in Im Z is morpholino; in In Z is phthalimido; in Io R one unsubstituted or one single or multiple 4-biphenylyl radical substituted by F, Cl and / or Br, A -CH (CH3) - (CH2) 2-, -C (CH3) = CHCH2- or -C (OH) (CH3) - (CH2) 2- and Z are amino; in Ip R p-biphenyl, 2'-fluoro-4-biphenyl, 4'-fluoro-4-biphenyl, 4'-chloro-4-biphenyl, 4'-bromo-4-biphenyl, 2 ', 4'-difluoro-4-biphenyl, 4-p-chlorophenoxyphenyl or 4-p-bromophenoxyphenyl, A -CH (CH3) - (CH2) 2-, -C (OH) (CH3) -CH2- (CH2) n or -C (CH3) = CH-CH2- and Z amino, diethylamino, 2-diethylaminoethylamino, Acetamido, piperidino, 4-methylpiperidino, morpholino, 4- (2-hydroxyethyl) piperazino, Imidazol-1-yl, phthalimido or 3,4-dihydro-4-oxo-phthalazin-1-yl-amino; in Iq R p-biphenylyl, 2'-fluoro-4-biphenylyl, 4'-fluoro-4-biphenyl, 4'-chloro-4-biphenyl, 4'-Bromo-4-biphenylyl or 2 ', 4'-Difluoro-4-biphenylyl, A -CH (CH3) - (CH2) 2-, -C (OH) (CH3) -CH2- (CH2) n or -C (CH3) = CH-CH2- and Z amino, diethylamino, 2-diethylaminoethylamino, Acetamido, piperidino, 4-methylpiperidino, morpholino, 4- (2-hydroxyethyl) piperazino, Imidazol-1-yl, phthalimido or 3,4-dihydro-4-oxo-phthalazin-1-yl-amino; in Ir R 4-p-Ciilorphenoxyphenyl or 4-p-Bromophenoxyphenyl, A -C11 (CH3) - (CH2) 2 or -C (OH) (CH3) - (CH2) 2- and Z amino, piperidino, 4-methylpiperidino, morpholino or Mean phthalimido; in Is R p-biphenylyl, 4'-fluoro-4-biphenylyl, 4'-chloro-4-biphenylyl or 4-p-chlorophenoxyphenyl, A -CH (C113) - (CH2) 2- or -C (OH) (CH3) - (CH2) 2- and Z Amino, diethylamino, acetamido, piperidino, morpholino, imidazol-1-yl or phthalimido mean; in It R p-biphenylyl, 4'-fluoro-4-biphenylyl, 4'-chloro-4-biphenylyl or 4-p-Chlorophenoxyphenyl, A -CH (CH3) - (CH2) 2- or -C (OH) (CH3) - (CH2) 2- and Z amino mean.

The invention also relates to a method for production the compounds of the formula I and their physiologically acceptable acid addition salts, characterized in that a compound of the general formula II R-Q II wherein Q is a radical reducible to the group -A-Z and R, A and Z are as above meaning given have treated with a reducing agent or that a compound which corresponds to the general formula I, but in which the Amino and / or the hydroxyl group is present in functionally modified form, with treated with a solvolyzing agent or that one can combine the general Formula III R-E III wherein E is -C (CH3) (OH) - (CH2) m-CH = CH2, -CH (CH3) - (CH2) m -CH = CH2 or -A-X, m O or 1, X Cl, Br, J, OH or reactively functionally modified OH and R and A have the meanings given above with a compound of the general formula H-Z or a reactive derivative of such a compound or that an amine of the general formula IV R-A-N (CH2CH2oH) -CH2CH2 IV wherein R, A and X have the meanings given above with an HX-splitting off Agent treated or that an amine of the general formula V R-A-N (CH2CH2X) 2 V wherein R, A and X have the meanings given above with one Reacts compound of the general formula H2NR³ or that a compound of general formula VI R4 -A-Z VI wherein R4 is one or more times by NH2 and optionally additionally substituted one or more times by F, Cl and / or Br 4-biphenylyl or 4-phenoxyphenyl radical and A and Z denote those given above Have meanings diazotized and the diazonium salt obtained then with a Halogenating agent treated Or that you can use a compound of the general formula VII Q¹-R5-A-Z VII or a salt of such a compound with a compound of general formula VIII R6-Q2 VIII or a salt of such a compound in which one of the groups Q 1 or Q 2 OH, the other of these groups R5 is an unsubstituted one or a p-phenylene radical which is monosubstituted or polysubstituted by F, Cl and / or Br and R6 has one unsubstituted or one or more times F, Cl and / or Br are substituted phenyl radicals and A, Z and X are those given above Have meanings, and that one optionally obtained a hydroxy compound of the formula I / A = -C (OH) (CH3) -CH2 '(CH2) n- / with a dehydrating agent and / or a compound of the formula I / A = -C (OH) (CH3) -CH2- (CH2) n- or CtCH3, = CH- (CH2) n-7 treated with a reducing agent and / or in a obtained Compound of formula I by treatment with chlorinating or brominating agents introduces one or more chlorine or bromine atoms and / or in a compound obtained of the formula I the radical Z by treatment with alkylating, acylating, solvolyzing and / or reducing agents converts into another radical Z and / or obtained one Base of the formula I by treatment with an acid in one of its physiologically harmless ones Converts acid addition salts.

The compounds of the formula I are also prepared according to methods known per se, as they are in the literature (e.g. in the standard works such as Houben-Weyl, methods of organic chemistry, Georg-Thieme-Verlag, Stuttgart) are described, namely among those known for the reactions mentioned and suitable reaction conditions. You can also use something known per se, here make use of variants not mentioned in more detail In all before and The following general formulas R, A and Z have the meaning given for formula I, unless expressly stated otherwise.

The starting materials for the preparation of the compounds of formula I. are partly known. They can be produced by processes known per se will. If desired, the starting materials can also be formed in situ, arart that they are not isolated from the reaction mixture, but immediately further to the compounds of formula I.

The compounds of formula I are, for example, by reduction of the compounds of the formula II available.

In particular, the primary amines of the formula I (Z = NH2) with Advantage can be produced in this way.

In the compounds of the formula II, the radical Q is preferably the group -A¹-Y, in which A¹ -CH (CH3) - (CH2) n-, -C (CH3) = CH- (CH2) m- or -C (OH) (CH3) - (CH2) n-, m 0 or 1 and Y CN, CONR¹R², CH2NO2, CH2N3, CH2NR¹-W (where W and Y are CN, R, CH2N02, CH2N3, CH2NR1-W (where W is a benzyl group or another which can be split off by hydrogenolysis Radical), CH2N (W) 2, CH = NOH, CHOH-NR R, 7 7 CH = NR ', CH2NR (where R is an alkylidene or azaalkylidene group each with 1 -6 carbon atoms, an oxoalkylene group with 4 - 7 carbon atoms, an oxo-3-oxapentamethylene group or an oxo-3-R³-3-azapentamethylene group means) or another radical which can be reducible to the CH2-NR¹R² group. The group Q can also mean, for example: -C (= CH2) - (CH2) n + 1-Z, -C (= CH2) - (CH2) n-Y, -CH (CH3) -CH = CH-Z, -CH (CH3) -CH = CH-Y, -C (OH) (CH3) -CH = CH-Z, -C (OH) (CH3) -CH = CH-Y, -C (= CH2) -CH = CH-Z, -C (= CH2) -CH = CH-Y.

The starting materials of the formula II are generally new; you can however, they can be produced in analogy to known processes. So are the acid amides of the formula R-C (OH) (CH3) - (CH2) p-CONR¹R² (p = 1 or 2), for example by Friedel-Crafts acetylation of the biphenyls or diphenyl ethers of the formula R-H to the ketones of the formula R-COCH3, Reformatskij reaction to hydroxyesters of the formula R-C (OH) (CH3) - (CH2) p-COOC2H5 and reaction with a compound of the formula HNR R. Elimination of water leads to the unsaturated amides of the formula R-C (CH3) = CH- (CH2) m-CONR R, reduction to the saturated amides of the formula R-CH (CH3) - (CH2) p-CONR¹R². reduction the mentioned hydroxyester with HJ leads to the acids with simultaneous saponification of the formula R-CH (CH3) - (CH2) p-COOH, which with LiAlH4 in the corresponding alcohols of the formula R-CH (CH3) - (CH2) p CH2OH. Alcohols of the formula R-C (OH) (CH3) - (CH2) pCH 2OH are by reduction of the above mentioned hydroxyesters obtainable with LiAlH4, alcohols of the formula R-C (CH3) = CH- (CH2) p-OH by dehydration and subsequent reduction of the hydroxy esters. By implementing the ketones of the formula R-CO-CH3 with KCN gives the cyanohydrins of the formula R-C (OH) (CH3) -CN, which lead to the amides of the formula R-C (OH) (CH3) -CONH2 or the hydroxy acids of the formula R-C (OH) (CH3) -COOH can be hydrolyzed. Reduction of hydroxy acids according to different Methods provides the acids of the formula R-CH (CH3) -COOH, the glycols of the formula R-C (OH) (CH3) -CH2OH and the alcohols of the formula R-CH (CH3) -CH2OH. From the alcohols mentioned the corresponding halides can be prepared in the usual way, e.g. with SOCl2 or PBr3 Manufacture that with alkali metal nitrites in the corresponding nitro compounds of the formula R-A1 -CH2NO2, with alkali metal azides into the azides of the formula R-A1-CH2N3, with amines of the formula W-NH2 (e.g. benzylamine) or (W) 2NH into the amines of the formula R-A1 -CH2-NH-W or R-A1 -CH2N (W) 2 can be converted.

Oxidation of the alcohols leads to the corresponding aldehydes of the formula R-A -CHO, which with hydroxylamine in the corresponding oximes of the formula R-A1-CH = NOH and with compounds of the formula HNR 1R2 into the corresponding aldehyde ammonia of the formula R-A1-CHOH-NR R2 or imines of the formula R-A1-CH = NR1 can. Unsaturated nitriles of the formula R-C (CH3) = CH-CN are, for example, from the mentioned ketones of the formula R-COCH3 and cyanoacetic acid can be prepared.

Among the starting materials of the formula II are the amides of the formula R-A -CONR1R and the nitriles of the formula R-A1-CN are preferred.

The starting materials of the formula II can, for example, by catalytic Hydrogenation, with nasal hydrogen, with complex metal hydrides or with Converted into the compounds of formula I using other chemical reducing agents will. The most suitable reduction methods for the individual starting materials are generally dependent on the nature of the functional group Y and the person skilled in the art according to the information in the literature. E.g.

Nitriles, amines of the formulas R-A-NH-W or R-A-N (W) 2, oximes and aldehyde ammonia particularly advantageous kata'yt sch are hydrogenated. A reduction in acid amides takes place particularly advantageously with complex metal hydrides or with diborane.

For example, noble metal, Nickel or cobalt catalysts, as well as mixed catalysts such as copper chromium oxide. As noble metals are primarily platinum and palladium into consideration Carriers (e.g. on carbon, calcium carbonate or strontium carbonate), as oxides (e.g. Platinum oxide) or in can be in finely divided form. Nickel- and cobalt catalysts are expediently used as Raney metals. One can expediently at pressures between about 1 and 200 at and at temperatures between about -80 and +1500, preferably between 20 and 1000 hydrogenate. The hydrogenation takes place in the presence of an inert solvent, e.g. an alcohol such as methanol, Ethanol or isopropanol, a carboxylic acid such as acetic acid, an ester such as ethyl acetate, an ether such as tetrahydrofuran (THF) or dioxane. Mixtures of solvents can also be used use, e.g. also mixtures containing water. It can also be beneficial be a base such as sodium or potassium hydroxide or ammonia in the hydrogenation to be added, e.g. in the hydrogenation of nitriles.

Furthermore, complex metal hydrides such as LiAlH4, NaBH4 or NaA1 (OC, CHOCH3), H, as well as diborane can be used, if desired under Addition of catalysts such as BF3, AlCl3 or LiBr. Suitable solvents are for this purpose in particular ethers such as diethyl ether, THF, dioxane, 1,2-dimethoxyethane or Diglyme as well as hydrocarbons such as benzene. For a reduction with NaBH4, in primarily alcohols such as methanol or ethanol are suitable as solvents. To this Methcde is preferably reduced at temperatures between about -80 and +1500, especially between around 20 and 1200.

A further reduction method is the reaction with nascent Suitable for hydrogen. This can be done, for example, by treating metals with Acids or bases are generated. For example, the systems zinc / acid, zinc / alkali, Iron / acid or tin / acid can be used. Hydrochloric acid, for example, are suitable as acids or acetic acid. Also an alkali metal like sodium in an alcohol how Ethanol, isopropanol, n-butanol, amyl alcohol, isoamyl alcohol or in phenol can can be used as a reducing agent, as well as an aluminum-nickel alloy, for example in alkaline-aqueous or alkaline-aqueous alcoholic solution, as well as sodium or aluminum amalgam in aqueous-alcoholic or aqueous solution.

In these methods, the reaction temperatures are between about 0 and about 150 °, preferably between about 20 and 120 °.

The starting compounds of the formula II can also be cathodic Reduction can be converted into compounds of formula I, expediently in aqueous-alcoholic or aqueous acetic acid medium. Further suitable reducing agents are, for example Matrium dithionite in aqueous-alcoholic or alkaline solution, also iron (III) hydroxide, Tin (11) chloride, hydrogen sulfide, hydrogen sulfides, sulfides, polysulfides, hydrazine, all according to the conditions given in the literature for such reductions come into use.

Appropriate choice of reagents and reaction conditions succeed also selective reductions. So can Schiff bases that have a C-C double bond in the remainder A1 are reduced with LiAlH4 to the corresponding unsaturated amines.

The compounds of formula I are also preferred by solvolysis Hydrolysis, obtainable from starting materials which correspond to the formula I, but in which the amino and / or the hydroxyl group is present in a functionally modified form.

The starting materials for solvolysis are usually new, they can however, they can be prepared in analogy to methods known per se. With these The starting materials are, for example, acyl derivatives of the amines of Formula I, in particular the amides of the formula R-A-NR1-Ac (where Ac is any but means an acyl radical different from R2, the nature of which is not critical, since it is split off during solvolysis, but preferably 7-10 carbon atoms possesses, e.g. aroyl with up to 10 carbon atoms like benzoyl). The amides mentioned are e.g.

by Friedel-Crafts alkylation of the biphenyls of the formula R-H with Halogen amides of the formula Cl-A-NR1-Ac or Br-A-NR1-Ac are available. Furthermore are to be mentioned as starting materials, the isocyanates of the formula R-A-NCO, as not isolated intermediate products in the Hofmann degradation of corresponding acid amides of the formula R-A-CONH2, in Curtius degradation, corresponding azides of the formula R-A-CON3, in Lossen degradation corresponding hydroxamic acids of the formula R-A-CO-NHOH or corresponding in the case of Schmidt degradation Carboxylic acids of the formula R-A-COOH are formed. The starting materials for these degradation reactions underlying carboxylic acids of the formula R-A-COOH are, for example, by Friedel-Crafts acylation the biphenyls or diphenyl ethers of the formula R-H with succinic anhydride to the Keto acids of the formula R-COCH2CH2COOH and subsequent reaction with methyl magnesium iodide to hydroxy acids of the formula R-C (OH) (CH3) -CH2CH2COOH and, if desired, subsequent Dehydration and / or reduction available.

Starting materials for solvolysis in which the OH group is functional modified are e.g. the corresponding alcoholates, especially the magnesium or lithium alcoholates, such as those used as reaction products in Grignard reactions or arise from reactions with organolithium compounds, the esters (e.g. the carboxylic acid esters, with the carboxylic acid radical preferably having up to 7 carbon atoms has, e.g., acetyl or benzoyl, the alkyl or aryl sulfonic acid esters in which the Alkyl radical preferably 1 - 6, the aryl radical preferably contains 6 - 10 carbon atoms) and the ethers (e.g. the alkyl ethers in which the alkyl group is preferably up to 6 Contains carbon atoms, the aryl ethers, in which the aryl group is preferably 6-10 carbon atoms contains, and the aralkyl ethers, in which the aralkyl group preferably contains 7-11 carbon atoms owns). Furthermore, e.g.

the boric acid ester into consideration, the intermediate in the oxidative Hydrcborierung arise. Furthermore, instead of the hydroxyl group, a chlorine or Iodine atom, there are then the corresponding hydrohalic acid esters.

The magnesium alcoholates mentioned are, for example, due to the conversion of ketones of the formula R-CO- (CH2) n + 1-z with methyl magnesium iodide or by reacting aryl magnesium halides of the formula R-MgCl or R-MgBr with ketones of the formula CH3CO- (CH2) n + 1-Z available. Halides of the formula R-CBr (CH3) - (CH2) n + 1 -Z or R-CCl (CH3) - (CH2) n + 1 -Z can e.g. are prepared by halogenation of acid amides of the formula R-A-COZ and subsequent reduction with LiAlH4.

From the halides, the corresponding esters are of the formula R-C (OAc) (CH3) - (CH2) n + 1-Z can be produced by reaction with potassium acylates, e.g. potassium acetate.

The solvolysis of these compounds is expediently achieved by action a solvent such as water (hydrolysis) or an alcohol with preferably 1 - 4 carbon atoms (alcoholysis) in the presence of an acidic or basic catalyst, e.g. a mineral acid such as sulfuric acid or hydrochloric acid, a metal hydroxide such as sodium, potassium, calcium, barium, lead or silver hydroxide, or one Metal- or ammonium salt such as sodium or potassium carbonate or ammonium chloride. As alcohols are preferably methanol, ethanol or isopropanol, you can also use mixtures of Use water with one of these alcohols. The solvolysis is expediently carried out at Temperatures between about 0 and about 1200.

In detail, the amides mentioned are expediently by several hours Cooking with aqueous, aqueous-alcoholic or alcoholic hydrochloric acid, sulfuric acid, Sodium hydroxide or potassium hydroxide hydrolyzed The mentioned Magneslumalkoholate are expediently not in isolation, but after their formation in the Grignard reaction in situ with dilute acids, e.g. sulfuric acid or hydrochloric acid or with aqueous Ammonium chloride solution hydrolyzed. The halides and esters mentioned are preferred saponified in aqueous or aqueous alcoholic solution or suspension, whereby, if desired, a solubilizer can be present, e.g. an alcohol, glycol or glycol ether. Alkalis are preferably used as the saponification agent like NaOH or KOH.

The compounds of the formula I can also be obtained by reaction a compound of the formula R-E (III) with a compound of the formula H-Z or a reactive derivative of such a compound, e.g. a metal derivative (such as PhthalimidkaliuX. The starting materials of the formula III are new.

For example, they can be produced by the Grignard reaction of ketones of the formula R-CO- (CH2) n + 1-X with CH3MgJ to carbinols of the formula R-C (OH) (CH3) (CH2) n + 1X and, if desired, subsequent dehydration and / or HX cleavage and / or Reduction. The starting materials of the formula H-Z are usually known.

The reaction of compounds of the formula III with compounds of the Formula H-Z is expediently carried out at temperatures between approximately 0 and 250 °, preferably between about 50 and 120 °, and at pressures between about 1 and about 50 at. One can in the presence of an inert Solvent work, e.g. one Alcohol such as methanol, ethanol, isopropanol, n-butanol, an ether such as diethyl ether, Diisopropyl ether, THF, dioxane, a hydrocarbon such as benzene, toluene, xylene, an amide such as dimethylformamide (DMF), a sulfoxide such as dimethyl sulfoxide if desired, a catalyst may be present, e.g., sodium amide, which is also made from sodium and liquid ammonia can be generated in situ, as well as bases such as sodium carbonate, Potassium carbonate, sodium bicarbonate, or potassium bicarbonate.

It is also possible to use an excess of the compound of the formula H-Z to use as a solvent, expediently at the boiling point. If in the formula III the radical E represents the group -A-X, X is preferably Cl, Br or J. If X is a reactive, functionally modified OH group, then stands it is preferably an alkyl or arylsulfonyloxy group with in particular up to to 10 carbon atoms ~ n. Secondary amines of the formula R-A-NflAlkyl can also be obtained by heating of alcohols of the formula R-A-OH with alkylamines in the presence of Raney nickel will.

Morpholine derivatives of the formula I (Z = morpholino) can also by HX elimination can be obtained from amines of the formula IV. The amines of formula IV are new; they can be obtained, for example, by reacting halogen compounds of the formula R-A-Cl or R-A-Br with amines of the formula HN (CH2CH20H) -CH2CH2X, e.g. diethanolamine. In the compounds of the formula IV, X preferably denotes an OH group. Dehydration Such diols are made possible, for example, by the action of an acidic catalyst such as sulfuric acid or a sulfonic acid such as p-toluenesulfonic acid in an inert solvent, e.g.

a hydrocarbon such as benzene, toluene or xylene at temperatures between about 0 and about 1500. If the radical X in the compounds of the formula IV denotes a halogen atom or a reactive, functionally modified OH group, In contrast, the HX cleavage is preferably carried out under the action of a base such as NaOH or KOH, preferably in an alcoholic or aqueous-alcoholic medium at temperatures between about 0 and about 100 degrees.

Piperazine derivatives of the formula I (Z = one unsubstituted in the 4-position or piperazino group substituted by alkyl or hydroxyalkyl with up to 6 carbon atoms each) can also be obtained by reacting an amine of the formula V with a Compound of the formula H2NR³ (e.g.

Ammonia, methylamine, 2-hydroxyethylamine). The compounds of the formula V (which include the compounds of the formula IV) are new; they can out Halogen compounds of the formulas R-A-Cl or R-A-Br with amines of the formula HN (CH2CH2X) 2 (e.g. diethanolamine) can be obtained, then, if desired, existing Convert OH groups into other X groups by reaction with e.g. SOCl2 or PBr3 can. The reaction of the amines of the formula V with the compounds of the formula H2NR³ usually takes place in the presence of an inert solvent such as benzene or toluene or xylene at temperatures between about 0 and about 1580, using a catalyst, e.g. add a strong acid such as sulfuric acid or an organic sulfonic acid can.

Furthermore, you can halogen-containing compounds of the formula I from the corresponding amino compounds of the formula VI obtained by first diazotized, e.g. with a salt or an ester of nitrous Acid (such as NaN02 or n-butyl nitrite) in aqueous hydrochloric acid at temperatures between converts about -20 ° and +100, and the resulting diazonium salt then into the desired halogen compound of formula I converts. This is how you get the appropriate Fluorine compounds preferably by reaction of the diazonium salt with HBF4 to form the diazonium tetrafluoroborate and subsequent thermal decomposition at about 100 to 200 ° in the absence of or Presence of an inert solvent such as toluene, xylene or dioxane. A decomposition at room temperature in an aqueous medium in the presence of copper powder is also possible. If one diazotizes with NaNO2 in anhydrous hydrofluoric acid, then one obtains by following Heat the desired fluorine compound directly.

An exchange of the diazonium group for chlorine or bromine is preferred in hot aqueous solution in the presence of Cu2Cl2 or Cu2Br2. The starting materials of the formula VI can be obtained, for example, by reducing the corresponding nitro compounds, this in turn by nitration of corresponding unsubstituted compounds of Formula 1.

Diphenyl ether derivatives of the formula I (R = unsubstituted or like specified substituted 4-phenoxyphenyl radical) can also be produced, by adding a compound of formula VII or a salt of such a compound with a compound of the formula VIII or a salt of such a compound. The starting materials of the formula VII can, for example, by reacting halogen compounds of the formulas Q1-R5-A-Cl or Q1-R5-A-Br with compounds of the formula HZ will. The starting materials of the formula VIII are generally known. You can either a phenol of the formula VII (Q1 = OH) with a compound of the formula VIII (Q2 = X) or a compound of the formula VII = = X) with a phenol of the formula VIII (Q2 = OH).

In this reaction, the phenols are preferably in the form of the corresponding ones Phenolates, especially the corresponding sodium or potassium phenates. the The reaction is expediently carried out in the presence of an inert solvent such as DMF or Phosphoric acid hexamethyltriamide (HMPT) in the presence of catalysts such as copper powder at temperatures between about 50 and about 200, preferably between 80 and 1300.

If desired, an obtained hydroxy compound of the formula R-C (OH) (CH3) -CH2- (CH2) n-Z to the corresponding unsaturated compound of the formula R-C (CH3) = CH- (CH2) nZ are dehydrated, expediently by the action of a acidic catalyst such as sulfuric acid or a sulfonic acid such as p-toluenesulfonic acid in an inert solvent, e.g. a hydrocarbon such as benzene or toluene, at temperatures between about 0 and about 1500, preferably between 80 and 1100.

Furthermore, if desired, the above-mentioned hydroxy compounds can be used of the formula R-C (OH) (CH3) -CH2- (CH2) nZ and unsaturated compounds of the formula R-C (CH3) = CH- (CH2) n ~ Z to the saturated compounds of the formula R-CH (CH3) -CH- (CH2) n ~ Z. the Reduction of the hydroxy compounds is achieved, for example, with hydriodic acid, preferably in acetic acid at temperatures between 200 and (preferably) boiling temperature. The unsaturated compounds can be preferably catalytically among the above hydrogenate specified conditions, for example on a noble metal catalyst such as palladium on charcoal at room temperature and normal pressure.

Furthermore, you can in a compound of formula I obtained according to Methods described in the literature by halogenating one or more chlorine or introduce bromine atoms. This is possible, for example, through direct implementation with elementary Chlorine or bromine in an inert solvent such as ether, carbon tetrachloride or Acetic acid, with catalysts such as iron filings, iodine or AlCl3 being present, preferably at temperatures between about -30 and 100 a compound of formula I obtained, the radical Z by alkylation, acylation, Convert solvolysis and / or reduction into another radical Z.

For example, a obtained primary (I, Z = NH2) or secondary Amine (I, Z = NTAlkyl) by treatment with alkylating agents in a secondary or tertiary amine of the formula I can be converted. Suitable as alkylating agents according to the invention, for example, compounds of the formulas R1-X, R2-X or optionally X-R1R2-X, e.g. methyl chloride, methyl bromide, methyl iodide, dimethyl sulfate, p-toluenesulfonic acid methyl ester, Ethyl chloride, ethyl bromide, ethyl iodide, diethyl sulfate, n-propyl chloride, bromide or -iodide etc., but also 1,4-dichlorobutane, 1,4-dibromobutane, 1,4-diiodobutane, 1,5-dichloro, , 1,5-dibromo or 1,5-diiodopentane, 2,2'-dichloro, 2,2'-dibromo or 2,2'-diiodo diethyl ether.

You can also with aldehydes or ketones to form aldehyde-ammonia compounds or condense Schiff's bases and then either as stated above hydrogenate or treat with an alkylating agent and the quaternary obtained Then hydrolyze the salt. For example, you can use a primary amine Convert condensation with benzaldehyde into the N-benzylidene compound and this convert with an alkyl halide into one of their quaternary salts, the following e.g. by treatment with aqueous alcohol with elimination of Benzaldehyde can be converted into the secondary amine.

You can also use aldehydes or ketones under reducing conditions alkylate, the corresponding aldehyde ammonia being formed as intermediate products. For example, you can have one or two methyl groups with formaldehyde in the presence of formic acid. You can also use an alcohol with 1 - 6 carbon atoms possesses, alkylate in the presence of Raney nickel. The alkylation is expedient in the presence or absence of one of the inert solvents mentioned at temperatures between about 0 and about 120 °, preferably between 40 and 100 °, made, wherein a catalyst can also be present, preferably a base such as potassium tert-butoxide.

As an acylating agent for the acylation of obtained primary or Secondary amines of the formula I are suitably the halides (e.g. chlorides or bromides) or anhydrides of carboxylic acids with 1 - 6 carbon atoms, e.g. acetic anhydride, Propionyl chloride, isobutyryl bromide, formic acid-acetic anhydride or phthalic anhydride. The addition of a base such as pyridine or triethylamine in the acylation is possible, but not necessary. The acylation is conveniently carried out in the presence or absence one of the inert solvents mentioned, e.g. benzene, at temperatures between about 0 and about 1600, preferably between about 20 and 1200.

Furthermore, in a compound of the formula I (Z = phthalimido or NR-acyl) the radical Z by solvolysis into another radical Z (in particular Z = NHR1 or 3,4-dihydro-4-oxo-phthalazin-1-yl-amino). So they can mentioned imides and amides of the formula I are hydrolyzed under the conditions given above be, expediently with aqueous, aqueous-alcoholic or alcoholic hydrochloric acid, Sulfuric acid, caustic soda or potassium hydroxide at temperatures between about 0 and about 1200, preferably at boiling temperature.

A particular embodiment of solvolysis is hydrazinolysis of the phthalimido compounds of formula I with hydrazine, preferably in the form of hydrazine hydrate in alcoholic or aqueous-alcoholic solution at temperatures between about 20 and 80 ° are converted into the mentioned dihydrophthalazin-4-ones can. These dihydrophthalazin-4-ones can be used under milder conditions than the corresponding phthalimides are hydrolyzed to the amines of the formula I (Z = NH2) e.g.

by brief treatment with aqueous-alcoholic mineral acids, preferably with aqueous-ethanolic hydrochloric acid at temperatures between 50 and 800.

It is also possible to add an acyl group in the radical Z after one of the Above given methods to reduce the corresponding alkyl group, preferably with a complex metal hydride such as LiAlH4.

A base of the formula I obtained can with an acid in the usual way Way to be transferred into the associated acid addition salt. For this purpose traces that provide physiologically harmless salts are suitable. So can inorganic Acids such as sulfuric acid, hydrohalic acids such as hydrochloric acid or hydrobromic acid, phosphoric acids such as orthophosphoric acid, nitric acid, Sulfamic acid, also organic acids, in particular aliphatic, alicyclic, araliphatic, aromatic or heterocyclic mono- or polybasic carbon or Sulfonic acids, such as formic acid, acetic acid, propionic acid, pivalic acid, diethyl acetic acid, Malonic acid, Succinic acid, pimelic acid, fumaric acid, maleic acid, lactic acid, tartaric acid, malic acid, Benzoic acid, salicylic acid, 3-phenylpropionic acid, citric acid, gluconic acid, ascorbic acid, Nicotinic acid, isonicotinic acid, methane and ethanesulphonic acid, ethane disulphonic acid, 2-hydroxyethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, naphthalene mono- and disulfonic acids.

The free bases of the formula I can, if desired, from their salts by treatment with strong bases like sodium or potassium hydroxide, or sodium Potassium carbonate can be set free.

The compounds of the formula I can have one or more centers of asymmetry contain. In this case, they are usually in a racemic form. Received Racemates can be converted mechanically or chemically into their optical antipodes are separated.

Preferably from the racemic mixture by reaction with an optically active separating agent formed diastereomers. Suitable as a release agent e.g. optically active acids, such as the D- and L-forms of tartaric acid, diacetyltartaric acid, Dibenzoyltartaric acid, mandelic acid, malic acid, lactic acid or the various optically active ones Camphorsulfonic acids such as ß-camphorsulfonic acid.

Of course, it is also possible to use optically active compounds of the formula I can be obtained by the methods described above by using starting materials, which are already optically active.

The new compounds of the formula I and their physiologically harmless ones Acid addition salts can be mixed with solid, liquid and / or semi-liquid Excipients as medicinal products in human and veterinary medicine be used. Organic or inorganic substances are used as carrier substances in question, which are suitable for enteral, parenteral or topical application and do not react with the new compounds, for example water, vegetable Oils, benzyl alcohols, polyethylene glycols, gelatine, lactose, starch, magnesium stearate, Talc, petroleum jelly, cholesterol. Tablets in particular are used for enteral administration, Dragees, capsules, syrups, juices, drops or suppositories, for parenteral application Solutions, preferably oily or aqueous solutions, as well as suspensions and emulsions or implants, for topical application ointments, creams or powders. The new Compounds can also be lyophilized and the lyophilizates obtained e.g.

be used for the production of injection preparations.

These preparations can be sterilized and / or auxiliary substances such as lubricants, preservatives, stabilizers and / or wetting agents, emulsifiers, salts to influence the osmotic pressure, buffer substances, color, taste and / or contain flavorings. You can also use one or more, if desired contain other active ingredients, e.g. one or more vitamins.

The new compounds are usually made in analogy to known, commercially available anti-inflammatory drugs applied, preferably in doses between about 10 and 1000 mg, in particular between 30 and 300 mg per dosage unit. The daily dosage is preferably between about 0.2 and 20 mg / kg of body weight. However, the specific dose for each patient depends on a variety of factors from, e.g. on the effectiveness of the special compound used, on the age, Body weight, general health, Gender, the diet, the time and route of administration, the rate of elimination, Drug combination and severity of the respective illness. Oral application is preferred.

Each of the compounds of the formula mentioned in the following examples I is particularly suitable for the production of pharmaceutical preparations.

In the examples below, customary work-up means: man gives water if necessary or, if the product is a base, diluted Add sodium hydroxide solution, extracted with an organic solvent, mixed with water is not miscible (e.g. benzene, chloroform or dichloromethane), separates off, dries the organic phase over sodium sulfate, filtered, evaporated and purified thoroughly Chromatography and / or crystallization. If the product is basic, it can can also be purified by crystallizing one of its acid addition salts.

Example 1 To a suspension of 7.6 g of LiAlH4 in 250 ml of absolute A solution of 23.9 g of 3-p-biphenylyl-butyramide [F. 156 - 158 °; obtainable by Friede1Crafts acetylation from biphenyl to 4-acetylbiphenyl (F. 118 - 1200)> Reaction with ethyl bromoacetate / zinc to form 3-p-biphenylyl-3-hydroxy-butyric acid ethyl.

ester (F. 55 - 56 °), treatment with HJ / acetic acid, conversion of the obtained 3-p-Biphenylyl-butyric acid (F. 118-1200) with SOC12 to chlorine and reaction with Ammonia] in 500 ml of THF, boiled for 16 hours, mixed with methyl acetate while cooling, then with 32% sodium hydroxide solution, works up as usual and receives 3-p-biphenylyl-butylamine, Hydrochloride, m.p. 226-228 °.

The following can be obtained analogously from the corresponding amides: 2-p-biphenylyl-propylamine 2- (4'-fluoro-4-biphenylyl) -propylamine, dl-malate, m.p. 2157-159 ° 2- (4'-chloro-4-biphenylyl) -propylamine 2- (4'-p-Chlorophenoxyphenyl) propylamine 3- (2-fluoro-4-biphenylyl) -butylamine 3 (3-fluoro-4-biphenylyl) -butylamine 3- (2'-Fluoro-4-biphenylyl) -butylamine, dl-malate, m.p. 150 ° 3- (3'-Fluoro-4-biphenylyl) -butylamine 3- (4'-Fluoro-4-biphenylyl) -butylamine, hydrochloride, m.p. 222-224 ° 3- (2-Chloro-4-biphenylyl) -butylamine 3- (3-chloro-4-biphenylyl) -butylamine 3- (2'-chloro-4-biphenylyl) -butylamine 3- (3'-chloro-4-biphenylyl) -butylamine 3- (4'-chloro-4-biphenylyl) butylamine, tartrate, mp 200-202 °; Hydrochloride, m. 256 - 2590 3- (2-Bromo-4-biphenylyl) -butylamine 3- (3-Bromo-4-biphenylyl) -butylamine 3- (2'-Bromo-4-biphenylyl) -butylamine 3- (2'-Bromo-4-biphenylyl) -butylamine 3- (4'-Bromo-4-biphenylyl) -butylamine 3- (2 ', 4'-difluoro-4-biphenylyl) -butylamine, dl-Maalt, m.p. 152-154 ° 3- (2', 4'-dichloro-4-biphenylyl) -butylamine, dl-Malate, m.p. 179-180 ° 3- (2 ', 4'-Dibromo-4-biphenylyl) -butylamine 3- (2'-fluoro-4'-chloro-4-biphenylyl) -butylamine 3- (2'-Fluoro-4'-bromo-4-biphenylyl) -butylamine 3- (2'-Chloro-4'-fluoro-4-biphenylyl) -butylamine -Bromo-4 "-fluoro-4-biphenylyl) -butylamine 3- p-phenoxypheny 1-buty lamin 3- (4-o-fluorophenoxyphenyl) -butylamine 3- (4-p-fluorophenoxyphenyl) -butylamine 3- (4-o-chlorophenoxyphenyl) -butylamine 3- (4-p-chlorophenoxyphenyl) -butylamine, Hydrochloride, mp 125-127 ° 3- (4-o-bromophenoxyphenyl) -butylamine 3- (4-p-bromophenoxyphenyl) -butylamine 3- [4- (2,4-Difluorophenoxy) phenyl] butylamine 3- [4- (2,4-dichlorophenoxy) phenyl] butylamine dl-Malate, m.p. 115-1170 (decomposition) 3 - [- 4- (2,4-Dibromophenoxy) phenyl] butylamine 4-p-biphenylyl-pentylamine 4- (4'-fluoro-4-biphenylyl) -petylamine, dl-malate, m.p. 159-161 ° 4- (4'-Chloro-4-biphenylyl) -pentylamine 4- (4'-p-Chlorophenoxyphenyl) -pentylamine, Example 2 Analogously to Example 1, 3-p-biphenylyl-3-hydroxybutyramide (can be prepared from the corresponding ethyl ester (mp 55-56 °) with NH3) with LiAlH4 the 3-p-biphenylyl-3-hydroxy-butylamine.

Hydrochloride, m.p. 272-275 °.

The following can be obtained analogously from the corresponding hydroxyamides: 2-p-biphenylyl-2-hydroxypropylamine 2- (4'-fluoro-4-biphenylyl) -2-hydroxypropylamine 2- (4'-chloro-4-biphenylyl) 2-hydroxypropylamine 2- (4-p-Chlorophenoxyphenyl) -2-hydroxy-propylamine 3- (2-fluoro-4-biphenylyl) -3-hydroxy-butylamine 3- (3-fluoro-4-biphenylyl) -3-hydroxy-butylamine 3- (2-fluoro-4-biphenylyl) -3-hydroxy-butylamine, Hydrochloride, F. 200 - 2020 3- (3'-Fluoro-4-biphenylyl) -3-hydroxy-butylamine 3- (4'-Fluoro-4-biphenylyl) -3-hydroxy-butylamine, M.p. 144-146 ° 3- (2-chloro-4-biphenylyl) -3-hydroxy-butylamine 3- (3-chloro-4-biphenylyl) -3-hydroxy-butylamine 3- (2'-chloro-4-biphenylyl) -3-hydroxy-butylamine 3- (3'-chloro-4-biphenylyl) -3-hydroxy-butylamine 3- (4'-chloro-4-biphenylyl) -3-hydroxy-butylamine, hydrochloride, m.p. 290-2930; Tartrate, M.p. 191-194 ° (decomposition) 3- (2-bromo-4-biphenylyl) -3-hydroxy-butylamine 3- (3-bromo-4-biphenylyl) -3-hydroxy-butylamine 3- (2'-Bromo-4-biphenylyl) -3-hydroxy-butyl 3- (3'-Bromo-4-biphenylyl) -3-hydroxy-butylamine 3- (4'-Bromo-4-biphenylyl) -3-hydroxy-butylamine 3- (2 ', 4'-difluoro-4-biphenylyl) -3-hydroxy-butylamine 3- (2 ', 4'-dichloro-4-biphenylyl) -3-hydroxy-butylamine, 4'-dibromo-4-biphenylyl) -3-hydroxy-butylamine 3- (2'-Fluoro-4'-chloro-4-biphenylyl) -3-hydroxy-butylamine 3- (2'-fluoro-4'-bromo-4-biphenylyl) -3-hydroxy-butylamine 3- (2'-chloro-4'-fluoro-4-biphenylyl) "3-hydroxy-butylamine 3- (2'-bromo-4'-fluoro-4-biphenylyl) -3-hydroxy-butylamine 3-p-phenoxyphenyl-3-hydroxy-butylamine 3- (4-o-fluorophenoxyphenyl) -3-hydroxy-butylamine 3- (4-p-fluorophenoxyphenyl) -3-hydroxy-butylamine 3- (4-o-chlorophenoxyphenyl) -3-hydroxy-butylamine 3- (4-p-chlorophenoxyphenyl) -3-hydroxy-butylamine, F.96-980 3- (4-o-bromophenoxyphenyl) -3-hydroxy-butylamine 3- (4-p-bromophenoxyphenyl) -3-hydroxy-butylamine 3- [4- (2,4-Difluorophenoxy) phenyl] -3-hydroxy-butylamine 3- [4- (2,4-dichlorophenoxy) -phenyl] -3-hydroxy-butylamine 3- [4- (2,4-dibromophenoxy) -phenyl] -3-hydroxy-butylamine, Malat, F. 880 (decomposition) 4-p-biphenylyl-4-hydroxypentylamine 4- (4'-fluoro-4-biphenylyl) -4-hydroxypentylamine 4- (4'-chloro-4-biphenylyl) -4-hydroxypentylamine 4- (4-p-chlorophenoxyphenyl) -4-hydroxypentylamine.

Example 3 A solution of 2.37 g of 3-p-biphenylyl-2-butenoamide (Can be prepared from the corresponding 3-hydroxy-butyramide and p-toluenesulfonic acid in toluene) in 30 ml of benzene is stirred to a suspension of 5 g of sodium aluminiurabis- (2-methoxyethoxy) dihydride added dropwise in 30 ml of benzene.

You boil overnight, cool, carefully decompose with water, work as usual and receives 3-p-Diphenylyi 2-butenyl-1-amine.

The following is obtained analogously from the corresponding butenic acid amides: 3- (2-fluoro-4-biphenylyl) -2-butenyl-1-amine 3- (3-fluoro-4-biphenylyl) -2-butenyl-1-amine 3- (2'-fluoro-4-biphenylyl) -2-butenyl-1-amine 3- (3'-Fluoro-4-biphenylyl) -2-butenyl-1-amine 3- (4'-Fluoro-4-biphenylyl) -2-butenyl-1-amine 3- (2-chloro-4-biphenylyl) -2-butenyl-1-amine 3- (3-chloro-4-biphenylyl) -2-butenyl-1-amine 3- (2'-chloro-4-biphenylyl) -2-butenyl-1-amine 3- (3'-chloro-4-biphenylyl) -2-butenyl-1-amine 3- (4'-chloro-4-biphenylyl) -2-butenyl-1-amine 3- (2-bromo-4-biphenylyl) -2-butenyl-1-amine 3- (3-Bromo-4-biphenylyl) -2-butenyl-1-amine 3- (2'-Bromo-4-biphenylyl) -2-butenyl-1-amine 3- (3'-Bromo-4-biphenylyl) -2-butenyl-1-amine 3- (4'-Bromo-4-biphenylyl) -2-butenyl-1-amine 3- (2 ', 4'-difluoro-4-biphenylyl) -2-butenyl-1-amine 3- (2 ', 4'-dichloro-3-biphenylyl) -2-butenyl-1-amine 3- (2', 4'-dibromo-4-biphenylyl) -2-butenyl-1-amine 3- (2'-Fluoro-4'-chloro-4-biphenylyl) -2-butenyl-1-amine 3- (2'-Fluoro-4'-bromo-4-biphenylyl) -2-butenyl-1-amine 3- (2'-Chloro-4'-fluoro-4-biphenylyl) -2-butenyl-1-amine 3- (2'-Bromo-4'-fluoro-4-biphenylyl) -2-butenyl-1-amine 3-p-phenoxyphenyl-2-butenyl-1-amine 3- (4-o-fluorophenoxyphenyl) -2-butenyl-1-amine 3- (4-p-Fluorophenoxyphenyl) -2-butenyl-1-amine 3- (4-o-Chlorophenoxyphenyl) -2-butenyl-1-amine 3- (4-p-Chlorophenoxyphenyl) -2-butenyl-1-amine 3- (4-o-Bromophenoxyphenyl) -2-butenyl-1-amine 3- (4-p-Bromophenoxyphenyl) -2-butenyl-1-amine 3- [4- (2,4-Difluorophenoxy) -phenyl] -2-butenyl-1-amine 3- [4- (2,4-dichlorophenoxy) -phenyl] -2-butenyl-1-amine 3- [4- (2,4-dibromophenoxy) -phenyl] -2-butenyl-1-amine, Example 4 A solution of 27.5 g of 3- (4'-chloro-4-biphenylyl) butyramide is added dropwise with stirring [F. 185-187 °; obtainable from p-chlorobiphenyl via 4-acetyl-4'-chlorobiphenyl (F. 100-103 °), 3- (4'-chloro-4-biphenylyl) -3-hydroxybutyric acid ethyl ester (m.p. 71-74 °) and 3- (4'-chloro-4-biphenylyl) butyric acid (m.p. 154-156) 7 in 300 ml of THF to one Solution of 4.6 g of diborane in 50 ml of THF, boiled for two hours, cooled and then added with 25% hydrochloric acid. Then you pour into water, work with sodium hydroxide solution and ethyl acetate and receives 3- (4 '-chloro-4-biphenylyl) -hutylamine. Hydrochloride, F.256-2590, example 5 A solution of 23.9 g of 3- (4'-fluoro-4-biphenylyl) butyronitrile (available from the amide with p-tolucl sulfonyl chloride / pyridine) - in 250 ml of methanol with addition of 8 g of KOH and 12 g of Raney nickel at about 80 at and 800 for 3 hours, filtered, evaporated and works with water and dichloromethane. After drying and evaporation the organic phase gives 3- (4'-fluoro-4-biphenylyl) butylamine.

Hydrochloride, F. 222-2240, Example 6 A solution of 27.3 g of 1-nitro-3- (4'-fluoro-4-biphenylyl) -butane Obtainable by reducing 3- (4'-fluoro-4-biphenylyl) -butyric acid with LiAlH4 to alcohol, reaction with PBr3 to 1-bromo-3- (4'-fluoro-4-biphenylyl) -butane and conversion with NaN027 in 500 ml of hot ethanol is mixed with a solution of 80 g of Na2S204 in 350 ml of water are added.

The mixture is boiled for one hour, filtered, the solution concentrated, works with aqueous sodium hydroxide solution and chloroform and receives 3- (4'-fluoro-4-biphenylyl) -butylamine.

Hydrochloride, m.p. 222-2240.

Example 7 A mixture of 24.2 g of 3- (4'-fluoro-4-biphenylyl) -butanal / obtainable by oxidation of 3- (4'-fluoro-4-biphenylyl) -butanol with CrOJI 40 g liquid ammonia and 400 ml of methanol is heated to 1000 for 12 hours. This creates as Intermediates presumably 1-hydroxy-3- (4'-fluoro-4-biphenylyl) -butylamine and 3- (4'-fluoro-4-biphenylyl) -butylidene-imine, that are not isolated. Then 30 g of Raney nickel are added, approximately hydrogenated 20 hours at 100 at and 100 °, filtered, evaporated and obtained 3- (4'-fluoro-4-biphenylyl) butylamine. Hydrochloride, mp 222-224 ° Example 8 25.7 g of 3- (4'-fluoro-4-biphenylyl) -butanaldoxime are dissolved (obtainable from the aldehyde and hydroxylamine) in 500 ml of ethanol, hydrogenated on 3 g PtO2 at 200 and normal pressure up to the standstill, filtered, evaporated and preserved 3- (4'-fluoro-4-biphenylyl) butylamine. Hydrochloride, mp 222-224 ° Example 9 Dissolve 23.7 g of 3- (4'-fluorobiphenylyl) -2-butenoic acid nitrile (obtainable from 4-acetyl-4'-fluorobiphenyl and cyanoacetic acid) in 150 ml of isopropanol, gives 15 g of liquid NH3 and 3 g of isopropanol moist Raney Ni added and hydrogenated at 80 ° and 80 at 4 hours. After filtering and Evaporation gives 3 - (4 '-fluoro-4-biphenylyl) -butylamine. Hydrochloride, F.222-2240.

Example 10 A solution of 33.3 g of N-benzyl-3- (4'-fluoro-4-biphenylyl) -1-butylamine [obtainable by reaction of 3- (4'-fluoro-4-biphenylyl) -butanol with SOCl2 to give 1-chloro-3- (4'-fluoro-4-biphenylyl) -butane and reaction with benzylamine7 in 500 ml of methanol is added to 8 g of 5% Pd-charcoal 200 and normal pressure hydrogenated. After filtration and evaporation, 3- (4'-fluoro-4-biphenylyl) -butylamine is obtained. Hydrochloride, m.p. 222-224 °.

The same product is analogous from N-benzylidene-3- (4'-fluoro-4-biphenylyl) -1-butylamine or from N, N-dibenzyl-3- (4'-fluoro-4-biphenylyl) -l-butylamine.

Example 11 A solution of 2.79 g of 1-isobutylideneamino-3-p-biphenylylbutane (obtainable by 5-hour weeks of 3-p-biphenylylbutylamine with isobutyraldehyde in benzene) in 75 ml of methanol after adding 0.3 g of PtO2 at 200 and normal pressure hydrogenated until the end of hydrogen uptake. It is filtered} works as usual and receives 1-isobutylamino-3-p-biphenylyl-butane.

Example 12 A solution of 2.65 g of 1-isopropylimino-3-p-biphenylylbutane (obtainable from 3-p-biphenylyl-butanal and isopropylamine) in 25 ml of dioxane is an 0> 2 g of platinum hydrogenated at 20 ° and normal pressure until the hydrogen uptake has ended. It is filtered, evaporated and 1-isopropylamino-3-p-biphenylyl-butane, example 13 A solution of 2.22 g of 3p-biphenylyl-2-buten-1-al (obtainable from Reaction of 4-acetylbiphenyl with 2,2-diethoxyethylmagnesium bromide and subsequent Treating with p-toluenesulfonic acid) and 0.6 g of isopropylamine in 25 ml of methanol im Tube to 2000 for 5 hours. After cooling, 0.5 g of Raney nickel moist with methanol is added and hydrogenated the Schiff base obtained at 100 at and 800 an hour.

It is cooled, filtered and l-isopropylamino-pbiphenylyl-butane is obtained.

Example 14 A solution of 2.63 g of 1-isopropylimino-3-p-bipnenylyl-2-butene (obtainable from 3-p-biphenylyl-2-butenal and isopropylanine) in 20 ml of absolute ether is added dropwise to a solution of 0.6 g of LiAlH4 in 20 ml of absolute ether. Afterward the mixture is boiled for 5 hours, water is carefully added, and the process is carried out as usual and receives 1-isopropylamino-3-p-biphenylyl-2-butene, Example 15 A solution of 2.77 g of 1-pyrrolidino-3-p-biphenylyl-1-butene (obtainable from 3-p-biphenylyl-butanal and pyrrolidine) in 35 ml of ethanol is applied to 0.5 g of Raney nickel at 6 at and 60 ° 3 Hydrogenated for hours. The catalyst is filtered off, evaporated and l-pyrrolidino-3-p-biphenylyl-butane is obtained.

Example 16 A solution of 2.39 g of 3-p-biphenylyl-butanaldoxime in 25 ml of acetic acid are mixed with 1.5 g of zinc dust while stirring. One stirs more 4 hours, filtered, diluted with water, made alkaline with ammonia and extracted with chloroform. Customary work-up gives 3-p-biphenylyl-butylamine. Hydrochloride, m.p. 226-228 °.

Example 17 Analogously to Example 1, the corresponding Di is obtained ethylamides, morpholides or piperidides with LiAlH4: 1-diethylamino-3- (4'-chloro-4-biphenylyl) butane, M.p. 42-44 ° 1-piperidino-3-p-biphenylyl-butan-3-ol, M.p. 102-104 ° 1-piperidino-3- (4'-fluoro-4-biphenylyl) -butan-3-ol, M.p. 107-109 ° 1-piperidino-3- (4'-bromo-4-biphenylyl) -butan-3-ol, M.p. 89-91 ° 1-piperidino-3- (4-p-chlorophenoxyphenyl) -butan-3-ol, M.p. 73-75 ° 1-piperidino-3- (4-p-bromophenoxyphenyl) -butan-3-ol, M.p. 73-75 ° 1-morpholino-3-p-biphenylyl-butan-3-ol , M.p. 116-118 ° 1-morpholino-3- (4'-fluoro-4-biphenylyl) -butan-3-ol, m.p. 152-154 ° 1-morpholino-3- (4'-chloro-4-biphenylyl ) -butan-3-ol, M.p. 106-108 ° 1-morpholino-3- (4'-bromo-4-biphenylyl) -butan-3-ol, M.p. 97-99 ° 1-morpholino-3- (4-p-chlorophenoxyphenyl) -butan-3-ol, F.66-67 ° Example 18 @@@@@@ Example 1 is obtained from 1 - (@ - @@ - Oxo-piperidino) -3-pbiphenylyl-butan-3-ol, obtainable from 3-p-biphenylyl-3-hydroxybutylamine and 5-bromovalerybromide @@ @@ A1F4 the 1-piperidino-3-p-biphenylyl-butan-3-ol F. 1 @@ - @@@ °.

Example 19 A mixture of 3.29 g of 1- (4-oxopiperidino) -3-p-biphenylylbutan-3-ol (obtainable from 1-chloro-5-p-biphenylyl-butan-3-ol and 4-piperidone) - 1.5 g KOH 2,3 ml of 85% hydrazine and 25 ml of diethylene glycol is heated to 100 ° for 1 hour. Man slowly increases the temperature until the hydrazone decomposes, cooks for another 4 hours, cools down, works up as usual and receives 1-piperidino-3-p-biphenylyl-butan-3-ol, 102-104 °.

Example 20 4.05 g of 1-dibenyzlamino-3-p-biphenylyl-butane (available by reaction of 1-chloro-3-p-biphenylyl-butan-3-ol with dibenzylamine to 1-dibenzylamino-3-p-biphenylyl-butan-3-ol and subsequent reduction with HJ) in 50 ml of ethyl acetate and hydrogenated on 0.5 g of 10% Pd-C at 200 and 1 at up to Standstill. It is filtered and evaporated, and 3-p-biphenylyl-butylamine is obtained. Hydrochloride, F. 226-2280.

Example 21 A solution of 27.1 g of 4- (4'-fluoro-4-biphenylyl) pentanoic acid amide / Obtainable by reaction of 4-fluorobiphenyl with succinic anhydride / A1C13 to 4- (4'-fluoro-4-biphenilyl) -4-oxobutanoic acid, reaction with CH3MgJ to form 4- (4'-fluoro-4-biphenylyl) -4-hydroxypentanoic acid, de-hydroxylation with HJ / acetic acid to 4- (4'-fluoro-4-biphenylyl) pentanoic acid, Conversion into the chloride with SOCl2 and reaction with NH3 7 in 150 ml of dioxane is at Oo was added dropwise to a solution of 24 g of bromine in 120 ml of 20% strength potassium hydroxide solution. Man stirs for another 1 hour, takes up in ether, separates, dries over sodium sulfate and evaporates. The crude product obtained is with 60 g of KOH, 250 ml of methanol and 65 ml of water boiled for 20 hours, resulting in 3- (4'-fluoro-4-biphenylyl) -butyl-isocyanate, that is not isolated. After cooling down, work up with water and ether and receives 3- (4'-fluoro-4-biphenylyl) -butylamine; Hydrochloride, F. 222-224 Example 22 A solution of 24.4 g of 1-amino-3- (4 -'-fluoro-4-biphenylyl) propan-3-one [available by reaction of 1-chloro-3- (4'-fluoro-4-biphenylyl) -propan-3-one with phthalimide potassium and subsequent hydrolysis] in 200 ml of THF is carried out with stirring at 200 to a Grignard solution prepared from 30 g of cH3J and 5 g of magnesium in 1000 ml of ether was added dropwise. The mixture is stirred for a further 4 hours and the alcoholate obtained is decomposed with water and dilute sulfuric acid, works up as usual and receives 3- (4'-fluoro-4-biphenylyl) -3-hydroxybutylamine, F. 144-1460.

The hydrolysis of 1-morpholino-3- (4'-chloro-4-biphenvlvl! Propan-3-one is obtained analogously (available from 4-p-chlorophenylacetophenone, morpholine and formaldehyde) and CII3MgJ produced alcoholate the 1-morpholino-3- (4'-chloro-4-biphenylyl) -butan-3-ol, 106-108 °.

Example 23 A Grignard solution of 25.1 g of 4'-fluoro-4-bromobiphenyl is added (obtainable by bromination of 4-fluorobiphenyl) and 2.43 g of magnesium in 1000 ml Ether dropwise with 4.35 g of 1-aminobutan-3-one in 400 ml of ether with stirring 20 °, stir for another two hours, decompose the alcoholate obtained with dilute sulfuric acid, works up as usual and receives 3- (4'-fluoro-4-biphenylyl) -3-hydroxybutylamine, F. 144 - 146 °.

Example 24 3.59 g of 3-bromo-3- (4'-fluoro-4-biphenylyl) butylamine are dissolved hydrochloride [obtainable by reacting 3-hydroxy-3- (4'-fluoro-4-biphenylyl) butyramide with PBr3 to 3-bromo-3- (4'-fluoro-4-biphenylyl) -butyramide and reduction with LiAlil ] in a 4 mixture of 15 ml of acetone and 15 ml of water, add 1 drop of sulfuric acid added, heated to 450 for 4 hours, works up as usual and receives 3- (4'-fluoro-4-biphenylyl) -3-hydroxybutylamine, F. 144 - 1460. As a by-product there is some 3- (4'-fluoro-4-biphenylyl) -2-butenylamine, which can be separated chromatographically (on SiO2).

Example 25 30.1 g of 3-acetoxy-3- (4 '-fluoro-4-biphenylyl) are boiled -1-butylamine / obtainable from 3-bromo-3- (4'-fluoro-4-biphenylyl) -1-butylamine and potassium acetate7 with 20 g of KOH in 500 ml of methanol for 2 hours, works up with water and chloroform and receives 3- (4'-fluoro-4-biphenylyl) -3-hydroxybutylamine, mp 144-146 °.

Example 26 24.2 g of 3- (4'-fluoro-4-biphenylyl) -1-buten-3-ol are heated available from 4-acetyl-4 '~ fluorobiphenyl and vinyl magnesium bromide) together with 8 g ammonia and 0.25 g sodium 8 hours to 180 - 2000, cools down, works with Water and chloroform to give 3- (4'-fluoro-4-biphenylyl) -3-hydroxy-butylamine F. 144-1460.

3- (4'-Fluoro-4-biphenylyl) -1-butene is obtained analogously from 3- (4'-Fluoro-4-biphenylyl) -butylamine; Hydrochloride, m.p. 222-2240.

Example 27 A solution of 26.25 g of 1-chloro-3- (4'-fluoro-4-biphenylyl) -butane [obtainable by Friedel-Crafts reaction of 4-fluorobiphenyl with 3-chloropropionyl chloride to 4'-fluoro-4- (3-chloropropionyl) -biphenyl (F. 96-970), reaction with CH3MgJ to 1-Chloro-3- (4'-fluoro-4-biphenylyl) -butan-3-ol (M.p. 78-790) and reduction with HJ7 in 150 ml of absolute ethanol at 00 becomes a solution of 10 g of NH3 in 150 ml of absolute Dripped ethanol. The mixture is stirred for a further 2 hours at 20 °, the solution is concentrated and the process is carried out with aqueous sodium hydroxide solution and ether to obtain 3- (4'-fluoro-4-biphenylyl) butylamine; Hydrochloride, m.p. 222-2240.

Example 28 A solution of 2.6 g of 1-chloro-3-p-biphenylyl-butan-3-ol [F. 68-700; obtainable by Friedel-Crafts reaction of biphenyl with 3-chloropropionyl chloride to 4- (3-chloropropionyl) biphenyl and reaction with CH3MgJ; or 3.05 g of 1-bromo-3-pbiphenylyl-butan-3-ol or 3.96 g of 1-p-toluenesulfonyloxy-3-pbiphenylyl-butan-3-ol] and 30 g of methylamine in 100 ml of methanol is heated to 120 ° in the autoclave for 2 hours. After cooling down and customary work-up gives l-methylamino-3-p-biphenylylbutan-3-ol.

Analogously, one obtains from the corresponding chlorine or bromine compounds: 1-methylamino-3- (4'-fluoro-4-biphenylyl) -butan-3-ol 1-methylamino-3- (4'-chloro-4-biphenylyl) -butan-3-ol 1-methylamino-3- (4-p-chlorophenoxyphenyl) -butan-3-ol 1-ethylamino-3-p-biphenylyl-butan-3-ol 1-ethylamino-3- (4'-fluoro-4-biphenylyl) -butan-3-ol 1-ethylamino-3- (4'-chloro-4-biphenylyl) -butan-3-ol 1-ethylamino-3- (4-p-chlorophenoxyphenyl) -butan-3-ol 1-n-propylamino-3-p-biphenylyl-butan-3-ol 1-n-Propylamino-3- (4 1-fluoro-4-biphenylyl) -butan-3-ol 1-n-Propylamino-3- (4'-chloro-4-biphenylyl) -butan-3-ol 1-n-Propylamino-3- (4-p-chlorophenoxyphenyl) -butan-3-ol 1-I-propylamino-3-p-biphenyl-butan-3-ol 1-Isopropylamino-3- (4'-fluoro-4-biphenylyl) -butan-3-ol 1-Isopropylamino-3- (4'-chloro-4-biphenylyl) -butan-3-ol 1- isopropylamino-3- (4-p-chlorophenoxyphenyl) -butan-3-ol 1-n-Butylamino-3-p-biphenylyl-butan-3-ol 1-n-Butylamino-3- (4'-fluoro-4-biphenylyl) -butan-3-ol 1-n-Butylamino-3- (4'-chloro-4-biphenylyl) -butan-3-ol t-n-Butylamino-3- (4-p-chlorophenoxyphenyl) -butall-3-ol 1-isobutylamino-3-p-biphenylyl-butan-3-ol 1-Isobutylamino-3- (4'-fluoro-4-biphenylyl) -butan-3-ol 1-Isobutylamino-3- (4'-chloro-4-biphenylyl) -butan-3-ol 1-Isobutylamino-3- (4-p-chlorophenoxyphenyl) -butar.-3-ol 1-sec.-Butylamino-3-p-biphenylyl-butan-3-ol l-sec, -butylanino-3- (4'-fluoro-4-biphenylyl) -butan-3-ol l-sec-butylamino-3- (4'-chloro-4-biphenylyl-butan-3-ol 1-sec-Butylamino-3- (4-p-chlorophenoxyphenyl) -butan-3-ol 1-tert-Butylamino-3-p-biphenylyl-butan-3-ol l-tert-butylamino-3M (4'-fluoro "4-bipllenylyl) -butane-3Mol l tert.-butylamino-3- (4'-chloro-4-biphenylyl) butan-3-ol 1-tert-butylamino-3- (4-p-chlorophenoxyphenyl) -butan-3-ol 1-n-pentylamino-3-p-biphenylyl-butan-3-ol 1-n-Hexylamino-3-p-biphenylyl-butan-3-ol, Example 29 2.6 g of 1-chloro-3-p-bipheny are boiled lyl-butan 3-ol with 30 nil morpholine for 1.5 hours, cools down, works up as usual and receives 1-morpholino-3-p-biphenylyl-butan-3-ol, mp 116-118 °.

Analogously, one obtains from the corresponding chlorine or bromine compounds: 1-Morpholino-2-p-biphenylyl-propan-2-ol 1-Morpholino-2- (4'-fluoro-4-biphenylyl) -propan-2-ol 1-Morpholino-2- (4'-chloro-4-biphenylyl) -propan-2-ol 1-Morpholino-2- (4'-bromo-4-biphenylyl) -propan-2-ol 1-morpholino-2- (4-p-chlorophenoxyphenyl) propan-2-ol l-Morpholino-3- (2'-fluoro-4-biphenylyl) -butan-3-ol 1-morpholino-3- (4'-fluoro-4-biphenyl) -butan-3-ol, m.p. 152-154 ° 1-morpholino-3- (2'-chloro-4-biphenyl) -butane-3- oil 1-Morpholino-3- (4'-chloro-4-biphenylyl) -butan-3-ol, m.p. 106-1080 1-Morpholino-3- (2'-bromo-4-biphenyl) -butan-3-ol 1-Morpholino-3- (4'-bromo-4-biphenyl) -butan-3-ol, m.p. 97-99 ° 1-Morpholino-3- (2 ', 4'-dlfluoro-4 biphenylyl) "cutan-3-ol l-morpholino-3- (2 ', 4'-dichloro-4-biphenylyl) -butene-3Sol 1-morpholino-3- (2', 4'-dibromo-4-biphenylyl) -butane-3-ol l - ',' orpholino-3-p-phenoxyphen; q-butar. "3» ol 1-morpholino-3- (4-o-fluorophenoxyphenyl) -butan-3-ol 1-morpholino-3- (4-p-fluorophenoxyphenyl) -butan-3-ol 1-morpholino-3- (4-o-chlorophenoxyphenyl) -butan-3-ol 1-morpholino-3- (4-p-chlorophenoxyphenyl) -butan-3-ol, m.p. 66 b70 1-morpholino-3- (4-o-bromophenoxyphenyl) -butan-3-ol 1-Morpholino-3- (4-p-bromophenoxyphenyl) -butan-3-ol 1-Morpholino-3- [4- (2,4-difluorophenoxy) -phenyl] -butan-3-ol l-Morpholino-3- [4- (2,4-di ¢ chlorophenoxy) -phenyl-3-butan-3-ol 1-morpholino-3- [4- (2,4-dibromophenoxy) -phenyl] -butane-3- oil 1-Morpholino-3-p-biphenylyl-pentan-4-ol 1-Morpholino-4- (4'-fluoro-4-biphenylyl) -pentan-4-ol 1-Morpholino-4- (4'-chloro-4-biphenylyl) -pentan-4-ol 1-Morpholino-4- (4'-bromo-4-biphenylyl) -pentan-4-ol 1-morpholino-4- (4-p-chlorophenoxyphenyl) -pentan-4-ol.

Example 30 Analogously to Example 29, one obtains from the corresponding chlorine or bromine compounds with pyrrolidine, piperidine, 4-methylpiperidine, homopiperidine or piperazine: 1-pyrrolidino-3-p-biphenylyl-butan-3-ol 1-pyrrolidino-3- (2'-fluoro-biphenylyl) -butan-3-ol 1-pyrrolidino-3- (4'-fluoro-biphenylyl) -butan-3-ol fumarate, m. 195-1970 l-pyrrolidino -3- (2'-chloro-4-biphenylyl) -butan-3-ol 1-pyrrolidino -3- (4'-chloro-4-biphenylyl) -butan-3-ol 1-pyrrolidino-3- (2'-bromo-4-biphenylyl) -butan-3-ol 1-pyrrolidino-3- (4'-bromo-4-biphellylyl) -butan-3-ol l-pyrrolidino-3- (2 ', 4s-difluoro-4-biphenylyl) -butan-3-ol l-pyrrolidino-3- (2s, 4'-dichloro-4-biphenylyl) -butan-3-ol 1-pyrrolidino-3- (2 ', 4'-dibromo-4-biphenylyl) -butan-3-ol 1-pyrrolidino-3-p-phenoxyphenyl-butan-3-ol 1-pyrrolidino-3- (4-o-fluorophenoxyphenyl) -butane "3-ol 1-pyrrolidino-3- (4-p-fluorophenoxyphenyl) -butan-3-ol 1-pyrrolidino-3- (4-o-chlorophenoxyphenyl) -butan-3-ol 1-pyrrolidino 3- (4-p-chlorophenoxyphenyl) -butan-3-ol 1-pyrrolidino-3- (4-o-bromophenoxyphenyl) -butan-3-ol 1-pyrrolidino-3- (4-p-bromophenoxyphenyl) -butan-3-ol l-pyrrolidino-3- [4- (2,4-difluorophenoxy) -phenyl] -butan-3-ol 1-pyrrolidino-3- [4- (2,4-dichlorophenoxy) -phenyl] -butane-3- oil l ~ pyrrolidino-3- [2,4-dibromophenoxy) phenyl] butan-3-ol 1-piperidino-2-p-biphenylyl-propan-2-ol 1-piperidino-2- (4'-fluoro-4-biphenylyl) propan-2-ol, hydrochloride, m.p. 232-2330 1-piperidino-2- (4'-chloro-4-biphenylyl) propan-2-ol l-piperidino-2- (4 4-biphenylyl) propan-2-ol, Hydrochloride, m.p. 245-2470 l-piperidino-2- (4-p-chlorophenoxyphenyl) propan-2-ol 1-piperidino-3-p-biphenylyl-butan-3-ol, m.p. 102-104 ° 1-piperidino-3- (2'-fluoro-4-biphenylyl) -butan-3-ol l-piperidino-3- (4'-fluoro-4-biphenylyl) -butan-3-ol, F, 107-1090; Hydrochloride, F. 238 - 2420 I-piperidino-3- (2'-chloro-4-kiphenylyl) -b 1-piperidino-3- (4'-chloro-4-biphenylyl) -butan-3-ol, F. 90-910 1-piperidino-3- (2'-bromo-4-biphenylyl) -butan-3-ol 1-piperidino-3- (4'-bromo-4-biphenylyl) -butan-3-ol, F. 89-91 ° 1-piperidino-3- (2 ', 4'-difluoro-4-biphenylyl) -butan-3-ol 1-piperidino-3- (2', 4'-dichloro-4-biphenylyl) -butane-3-ol 1-piperidino-3- (2 ', 4'-dibromo-4-biphenylyl) -butan-3-ol 1-piperidino-3-p-phenoxy-butan-3-ol 1-piperidino-3- (4-o-fluorophenoxyphenyl) -butan-3-ol 1-piperidino-3- (4-p-fluorophenoxyphenyl) -butan-3-ol, 50-51 ° 1-piperidino-3- (4-o-chlorophenoxyphenyl) -butan-3-ol 1-piperidino-3- (4-p-chlorophenoxyphenyl) -butan-3-ol 1-piperidino-3- (4-o-bromophenoxyphenyl) -butan-3-ol 1-piperidino-3- (4-p-bromophenoxyphenyl) -butan-3-ol 1-piperidino-3- [4- (2,4-difluorophenoxy) -phenyl] -butan-3-ol 1-piperidino-3- [4- (2,4-dichlorophenoxy) -phenyl] -butan-3-ol 1-piperidino-3- [4- (2,4-dibromophenoxy) -phenyl] -butan-3-ol 1-piperidino-4-p-biphenylyl-pentan-4-ol 1-piperidino-4- (4'-fluoro-4-biphenylyl) -pentan-4-ol 1-piperidino-4- (4'-chloro-4-biphenylyl) -pentan-4-ol 1-piperidino-4- (4'-bromo-4-biphenylyl) -pentan-4-ol hydrochloride, m.p. 282 - 283 ° 1-piperidino-4- (4-p-chlorophenoxyphenyl) -pentane-4- oil 1- (4-methylpiperidino) -3-p-biphenylyl-butan-3-ol 1- (4-methylpiperidino) -3- (2'-fluoro-4-biphenylyl) -butan-3-ol 1- (4-Methylpiperidino) -3- (4'-fluoro-4-biphenylyl) -butan-3-ol hydrochloride, m.p. 222 ° 1- (4-methylpiperidino) -3- (2'-chloro-4-biphenylyl) -butan-3-ol 1- (4-methylpiperidino) -3- (4'-chloro-4-biphenylyl) -butane-3 -oil 1- (4-methylpiperidino) -3- (2'-bromo-4-biphenylyl) -butan-3-ol 1- (4-methylpiperidino) -3- (4'-bromo-4-biphenylyl) -butane-3 -oil 1- (4-methylpiperidino) -3- (2 ', 4'-difluoro-4-biphenylyl) -butan-3-ol 1- (4-methylpiperidino) -3- (2', 4'-dichloro-4- biphenylyl) butan-3-ol 1- (4-Methylpiperidino) -3- (2 ', 4'-dibromo-4-biphenylyl) -butan-3-ol 1- (4-methylpiperidino) -3-p-phenoxy-butan-3-ol 1- (4-methylpiperidino) -3- (4-o-fluorophenoxyphenyl) -butan-3-ol 1- (4-methylpiperidino) -3- (4-p-fluorophenoxyphenyl) -butan-3-ol 1- (4-methylpiperidino) -3- (4-o-chlorophenoxyphenyl) -butan-3-ol 1- (4-methylpiperidino) -3- (4-p-chlorophenoxyphenyl) -butan-3-ol, F. 81-82 ° 1- (4-methylpiperidino) -3- (4-o-bromophenoxyphenyl) ~ butan 3-ol 1- / 4-methylpiperidino) -3- (4-p-bromophenoxyphenyl) - butan-3-ol, F. 78-79.5 ° 1- / 4-methylpiperidino) -3- [4- (2,4-difluorophenoxy) phenyl] butan-3-ol 1- (4-methylpiperidino) 3- [4- (2,4-dichlorophenoxy) -phenyl] -butan-3-ol 1- / 4-methylpiperidino) -3- [4- (2,4-dibromophenoxy) -phenyl] -butan-3-ol 1-homopiperidino-3-p-biphenylyl-butan-3-ol, m.p. 66-67 ° 1-homopiperidino-3- (2'-fluoro-4-biphenylyl) -butan-3-ol Hydrochloride, m.p. 160-161 ° 1-homopiperidino-3- (4'-fluoro-4-biphenylyl) -butan-3-ol l-IIomopiperidino-3 (2-chloro-4-biphenylyl) -butan-3-ol l-IIomopiperidino-3- (4'-chloro-4-biphenylyl) -butan-3-ol 1-homopiperidino-3- (2'-bromo-4-biphenylyl) -butan-3-ol 1-homopiperidino-3- (4'-bromo-4-biphenylyl) -butan-3-ol 1-homopiperidino-3- (2 ', 4'-difluoro-4-biphenylyl) -butan-3-ol 1-iomopiperidino-3- (2' , 4'-dichloro-4-biphenylyl) -butan-3-ol 1-xomopiperidino-3- (2 ', 4'-dibromo "4-biphenylyl) -butan-3-ol 1-homopiperidino-3-p-phenoxyphenyl-butan-3-ol 1-homopiperidino-3- (4-o-fluorophenoxyphenyl) -butan-3-ol 1-Homopiperidino-3- (4-p-fluorophenoxyphenyl) -butan-3-ol 1-Itomopiperidino-3- (4-o-chlorophenoxyphenyl) -butan-3-ol l-Uomopiperidino-3- (4-p-chlorophenoxyphenyl) -butan-3-ol hydrochloride, F. 180-1810 l-IIomopiperidino »3" (4-o-bromophenoxyphenyl) -butan-3-ol 1-Homopiperidino-3- (4-p-bromophenoxy-phenyl) -butane-3-ol. 1-Homopiperidino-3- [4- (2,4-difluorophenoxy) -phenyl] -butan-3-ol l-Homopiperidino «3- [4- (2,4-dichlorophenoxy) -phenyl}}) utan-3-ol 1-Homopiperidino-3- [4- (2,4-dibromophenoxy) -phenyl] -butane-3- oil 1-piperazino-3-p-biphenylyl-butan-3-ol 1-piperazino-3- (2'-fluoro-4-biphenylyl) -butan-3-ol l-piperasino-3 »(4'-fluoro-4-biphenylyl) -butan-3-ol, M.p. 168-1 (390 1-piperazino-3- (2'-chloro-4-biphenylyl) -butane-3 -oil 1-piperazino-3- (4'-chloro-4-biphenylyl) -butan-3-ol 1-piperazino-3- (2'-bromo-4-biphenylyl) -butan-3-ol 1-piperazino-3- (4'-bromo-4-biphenylyl) -butan-3-ol 1-piperazino-3- (2 ', 4'-difluoro-4-bipheilylyl) -butan-3-ol 1-piperazino-3- (2 ', 4'-dichloro-4-biphenylyl) -butan-3-ol 1-piperazino-3- (2', 4'-dibromo-4-biphenylyl) -butan-3-ol 1-piperazino-3-p-phenoxyphenyl-butan-3-ol 1-piperazino-3- (4-o-fluorophenoxyphenyl) -butan-3-ol 1-piperazino-3 (4-p-fluorophenoxyphenyl) -but an-3-ol 1-piperazino-3- (4-o-chlorophenoxyphenyl) -butan-3-ol 1-piperazino-3- (4-p-chlorophenoxyphenyl) -butan-3-ol 1-piperazino-3- (4-p-bromophenoxyphenyl) -butan-3-ol 1-piperazino-3- (4-p-bromophenoxyphenyl) -butan-3-ol 1-piperazino-3- [4- (2,4-difluorophenoxy) -phenyl] -butall-3-ol 1-Piperazino-3- [4- (2,4-dichlorophenoxy) -phenyl] -butan-3-ol 1-Piperazino-3- [4- (2,4-dibromophenoxy) -phenyl] -butan-3-ol Example 31 Example 29 is obtained from the corresponding chlorine or bromine compounds with di-n-propylamine, diisopropylamine, di-n-butylamine, diisobutylamine, di-n-pentylamine, Di-n-hexylamine, 2-dimethylamino-ethylamine, 2-diethylamino-ethylamine, 3-dimethylamino-propylamine, 2-methylpiperidine, 3-methylpiperidine, 2,6-dimethylpiperidine, 1-methylpiperazine, 1-ethylpiperazine, 1-n-hexylpiperazine or 1- (2-hydroxyethyl) piperazine: 1-di-n-propylamino-3-p-biphenylyl-butan-3-ol 1-di-n-propylamino-3- (4'-fluoro-4-biphenylyl) -butan-3-ol 1-di-n-propylamino-3- (4'-chloro-4-biphenylyl) -butane-3 -oil 1-di-n-propylamino-3- (4-p-chlorophenoxyphenyl) -butan-3-ol 1-diisopropylamino-3-p-biphenylyl-butan-3-ol 1-Diisopropylamino-3- (4'-fluoro-4-biphenylyl) -butan-3-ol 1-Diisopropylamino-3- (4'-chloro-4-biphenylyl) -butan-3-ol 1-diisopropylamino-3- (4-p-chlorophenoxyphenyl) -butan-3-ol 1-di-n-butylamino-3-p-biphenylyl-butan-3-ol 1-di-n-butylamino-3- (4'-fluoro-4-biphenylyl) -butan-3-ol l-di-n-butylamino-3- (4'-chloro-4-biphenylyl) ~ butane-3 -oil 1-di-n-butylamino-3- (4-p-chlorophenoxy-phenyl) -butan-3-ol 1-diisobutylamino-3-p-biphenylyl-butan-3-ol 1-diisobutylamino-3- (4'-fluoro-4-biphenylyl) -butan-3-ol 1-diisobutylamino-3- (4'-chloro-4-biphenylyl) -butan-3-ol 1-diisobutylamino-3- (4-p-chlorophenoxyphenyl) -butan-3-ol 1-di-n -pentylamino-3-p-biphenylyl-butan-3-ol 1-Di-n -pentylamino-3- (4'-fluoro-4-biphenylyl) -butanH3-ol 1-Di-n-pentylamino-3- (4'-chloro-4-biphenylyl) -bucan-3-ol 1-Di-n-pen-tylamino-3- (4-p.-chlorophenoxyphenyl) -butan-3-ol 1-di-n-hexylamino-3-p-biphenylyl-butan-3-ol 1-Di ~ n-hexylamino-3- (4'-fluoro-4-biphenylyl) -butan-3-ol 1-di-n-hexylamino-3- (4'-chloro-4-biphenylyl) -butane-3 -oil 1-Di-n-hexylamino-3- (4p-chlorophenoxy-pheny1) -butan-3-ol 1- (2-dimethylamino-ethylamino) -3-p-biphenylyl-butan-3-ol 1- (2-Dimethylamino-ethylamino) -3- (4 -fluoro-4-biphenylyl) -butan-3-ol 1- (2-Dimethylamino-ethylamino) -3- (4'-chloro-4-biphenylyl) - butan-3-ol 1- (2Diniethy1amino-ethylamino) -3- (4p-chlorophenoxy-pheny1) -butan-3-ol 1- (2-diethylamino-ethylamino) -3-p-biphenylyl-butan-3-ol 1- (2-diethylamino-ethylamino) -3- (4'-fluoro-4-biphenylyl) -butan-3-ol, mp 74 °; Dihydrochloride, M.p. 198 ° 1- (2-diethylamino-ethylamino) -3- (4'-chloro-4-biphenylyl) -butan-3-ol 1- (2-diethylamino-ethylamino) -3- (4-p-chlorophenoxy -phenyl) -butan-3-ol 1- (3-Dimethylamino-propylamino) -3-p-biphenylyl-butan-3-ol 1- (3-Dimethylamino-propylamino) -3- (4'-fluoro-4-biphenyly) -butan-3-ol l- (3-Dimethylamino-propylamino> 3- (4'-chloro-4-biphenylyl) -butan-3-ol 1- (3-dimethylamino-propylamino) -3- (4-p-chlorophenoxyphenyl) E) utawl-3-ol 1- (2-methylpiperidino) -3-p-biphenylyl-3-ol 1- (2-methylpiperidino) -3- (4'-fluoro-4-biphenylyl) -butan-3-ol l- (2-methylpiperidino) -3- (4'-chloro-4-b, phenylyl) -butan-3-ol 1- (2-methylpiperidino) -3- (4-p-chlorophenoxyphenyl) -butane 3-ol 1- (3-methylpiperidino) -3-p-biphenylyl-butan-3-ol 1- (3-methylpiperidino) -3- (4'-fluoro-4-biphenylyl) -butan-3-ol 1- (3-methylpiperidino) -3- (4'-chloro-4-biphenylyl) -butan-3-ol 1- (3-methylpiperidino) -3- (4-p-chlorophenoxyphenyl) -butane-3- oil 1- (2,5-Dimethylpiperidino) -3-p-biphenynyl-butan-3-ol 1- (2,5-Dimethylpiperidino) -3- (4'-fluoro-4-biphenylyl) -butan-3-ol 1- (2,5-Dimethylpiperidino) -3- (4'-chloro-4-biphenylyl) -butan-3-ol 1- (2,5-Dimethylpiperidino) -3- (4-p-chlorophenoxyphenyl) - butan-3-ol 1- (4-Methyl-piperazino) -3-p-biphenylyl-butan-3-ol 1- (4-Methyl-piperazino) -3- (4'-fluoro-4-biphenylyl) -butan-3-ol 1- (4-methyl-piperazino) -3- (4'-chloro-4-biphenylyl) -butan-3-ol 1- (4-methyl-piperazino) -3- (4-p-chlorophenoxyphenyl) - butan-3-ol 1- (4-ethyl-piperazino) -3-p-biphenylyl-butan-3-ol 1- (4-ethyl-piperazino) -3- (4'-fluoro-4-biphenylyl) -butan-3-ol 1- (4-ethyl-piperazino) -3- (4'-chloro-4-biphenylyl) -butane-3-ol 1- (4-Ethyl-piperazino) -3- (4-p-chlorophenoxyphenyl) -butan-3-ol 1- (4-hexyl-piperazino) -3-p-biphenylyl-butan-3-ol 1- (4-hexyl-piperazino) -3- (4'-fluoro-4-biphenylyl) -butan-3-ol 1- (4-hexyl-piperazino) -3- (4'-chloro-4-biphenylyl) -butane-3-ol 1- (4-Hexyl-piperazino) -3- (4-p-chlorophenoxyphenyl) -butan-3-ol 1- [4- (2-Hydroxyethyl) -piperazino] -3-p-biphenylyl-butane-3 -oil 1- [4- (2-Hydroxyethyl) piperazino] -3- (4'-fluoro-4-biphenylyl) -butan-3-ol, m.p. 76 - 78; Dihydrochloride, m.p. 246-247 ° 1- [4- (2-Hydroxyethyl) -piperazino] -3- (4'-chloro-4-biphenylyl) -butan-3-ol 1- [4- (2-Hydroxyethyl) piperazino] -3- (4-p-chlorophenoxyphenyl) butan-3-ol.

Example 32 2.6 g of 1-chloro-3-p-biphenylyl-butan-3-ol are heated with 30 ml of diethylamine in the autoclave at 150 ° for 15 hours, cools down, works as usual and receives t 1-diethylamino-3-p-biphenylyl butan-3-ol.

Analogously, one obtains from the corresponding chlorine or bromine compounds: 1-diethylamino-3- (2'-fluoro-4-biphenylyl) -butan-3-ol 1-diethylamino-3- (4'-fluoro-4-biphenylyl) -butan-3-ol, F. 67-68 1-Diethylamino-3- (2'-chloro-4-biphenylyl) -butan-3-ol 1-Diethylamino-3- (4'-chloro-4-biphenylyl) -butan-3-ol F. 61-630 1-Diethylamino-3- (2'-bromo-4-biphenylyl) -butan-3-ol 1-Diethylamino-3- (4'-bromo-4-biphenylyl) -butan-3-ol 1-diethylamino-3- (2 ', 4'-difluoro-4-biphenylyl) -butan-3-ol 1-diethylamino-3- (2', 4'-dichloro-4-biphenylyl) -butan-3-ol 1-Diethylamino-3- (2 ', 4'-dibromo-4-biphenylyl) -butan-3-ol 1-Diethylamino-3-p-phenoxyphenyl-butan-3-ol 1-diethylamino-3- (4-o-fluorophenoxy-phenyl) -butan-3-ol l-diethylamino-3 (4-p-fluorophenoxy-phenyl) -butan-3-ol l-diethylamino-3- (4-o-chlorophenoxy-phenyl) -butall-3-ol l-diethyl.ami.no-3- (4-p-chlorophenoxy-pllellyl) -butane ~ 3 ~ ol 1-diethylamino-3- (4-o-bromophenoxyphenyl) -butan-3-ol 1-diethylamino-3 (4-p-bromophenoxyphenyl ) -butan-3-ol 1-diethylamino-3- [4- (2,4-difluorophenoxy) phenyl] butan-3-ol 1-diethylamino-3- [4- (2,4-dichlorophenoxy) phenyl ] -butan-3-ol 1-Diethylamino-3- [4- (2,4-dibromophenoxy) -phenyl] -butan-3-ol Example 33 A mixture from 2.6 g of 1-chloro-3-p-biphenylyl-butan-3-ol, 2.04 g of phthalimide potassium and 40 ml of DMF is heated to 1100 for 1.5 hours. After cooling, it is worked up as usual and receives 1-phthalimido-3-p-biphenylyl-butan-3-ol, melting point 153-155 °.

Analogously, one obtains from the corresponding chlorine or bromine compounds: 1-Phthalimido-3- (2'-fluoro-4-biphenylyl) -butan-3-ol, F, 125-127 ° 1-phthalimido-3- (41-fluoro-4-biphenylyl) -butan-3-ol , M.p. 150-152 ° 1-phthalimido-3- (2'-chloro-4-biphellylyl) -butan-3-ol 1-phthalimido-3- (4'-chloro-4-biphenylyl) -butan-3-ol , M.p. 177-179 ° 1-Phthalimido-3- (2'-bromo-4-biphenylyl) -butan-3-ol 1-Phthalimido-3- (4'-bromo-4-biphenylyl) -butan-3-ol l-Phthalimi.do-3- (2 ', 4'-difluoro-4-biphenylyl) -butane-3-oN mp 128-130 ° 1-phthalimido-3- (2 ', 4'-dichloro-4-biphenylyl) -butan-3-ol 1-phthalimido-3- (2 ', 4'-dibromo-4-biphenylyl) -butan-3-ol 1-phthalimido-3-p-phenoxyphenyl-butan-3-ol l-Phthalimiclo-3 ~ (4-o-fluoxphenoxyphenyl) -butan-3-ol 1-Phthalimido-3- (4-p-fluorophenoxyphenyl) -butan-3-ol 1-phthalimido-3- (4-o-chlorophenoxyphenyl) -butan-3-ol 1-phthalimido-3- (4-p-chlorophenoxyphen.yl) -butan-3-ol , F. 135-137 ° l-phthalimido- 3- (4-o-bromophenoxy-phenyl) -butan-3- ol l-phthalimido-3- (4-p-bromobenoxy-phenyl) -butan-3-ol 1-phthalimido-3- [4- (2,4-difluorophenoxy) phenyl] butan-3-ol 1-Phthalimido-3- [4- (2,4-dichlorophenoxy) -phenyl] -butan-3-ol 1-Phthalimido-3 ~ [4- (2,4-dibromophenoxy) -phenyl-3-huta 3-ol.

Example 34 A mixture of 2.6 g of 1-chloro-3-p-biphenylyl-butan-3-ol and 1.36 g of imidazole is heated to 1400 for 3 hours. After cooling down and more usual Working up gives 1- (1-imidazolyl) -3-p-biphenylyl-butan-3-ol.

Analogously, one obtains from the corresponding chlorine or bromine compounds: 1- (1-Imidazolyl) -3- (2'-fluoro-4-biphenylyl) -butan-3-ol 1- (1-imidazolyl) -3- (4'-fluoro-4-biphenylyl) -butane-3 -oil F. 205-207 ° 1- (1-imidazolyl) -3- (2'-chloro-4-biphenylyl) -butan-3-ol 1- (1-imidazolyl) -3- (4'-chloro-4- biphenylyl) butan-3-ol F. 201-2030 1- (1-Imidazolyl) -3- (2'-bromo-4-biphenylyl) -butan-3-ol 1- (1-imidazolyl) -3- (4'-bromo-4-biphenylyl ) -butan-3-ol 1- (l-imidazolyl) -3- (2 ', 4'-difluoro-4-biphenylyl) -butan-3-ol 1- (1-imidazolyl) -3- (2', 4'-dichloro-4- biphenylyl) butan-3-ol 1- (1-imidazolyl) -3- (2 ', 4'-dibromo-4-biphenylyl) -butan-3-ol 1- (1-imidazoyl) -3-p-phenoxyphenyl-butan-3-ol midazolyl) -3- (4-o-fluo.rpllenoxy-phenyl) -butan-3-ol 1- (1-imidazoyl) -3- (4-p-fluorophenoxyphenyl) -butan-3-ol 1- (1-imidazoyl) -3- (4-o-chlorophenoxyphenyl) -butan-3-ol 1- (1-imidazoyl) -3- (4-p-chlorophenoxyphenyl) -butan-3-ol F. 125 - 1270 l- (l ~ imidazolyl) ~ 3- (4-o-bromophenoxyphenyl) - butan-3-ol 1- (1-imidazoyl) -3- (4-p-bromophenoxyphenyl) -butane-3-ol 1- (1-imidazoyl) -3- [4- (2,4-difluorophenoxy) -phenyl] -butan-3-ol 1- (1-imidazoyl) -3- [4- (2,4-dichlorophenoxy) - phenyl] butan-3-ol , 20 1,5972 1- (1-imidazoyl) -3- [4- (2,4-dibromophenoxy) phenyl] butan-3-ol Example 35 Dissolve 2.26 g of 3-p-biphenylylbutan-i-ol in 10 ml of isopropylamine and shake the solution after adding 0.5 g of Raney nickel for 15 hours at 1600 in the tube. To cooling, filtering off the catalyst and evaporation gives l-isopropylamino-3-p-biphenylyl-butane.

Example 36 3.48 g of 1-bis- (2-hydroxyethyl) -3- (4'-chloro-4-biphenylyl) butane are dissolved [available from 1-chloro-3- (4-chloro-4-biphenylyl) butane and diethanolamine] in 100 ml of xylene, mixed with 2 drops of H2SO4 and boiled for one hour. After cooling down and customary work-up gives 1-morpholino-3- (4'-chloro-4-biphenylyl) butane, F. 77-790.

Example 37 A solution of 3.48 g of 1-bis (2-hydroxyethyl) -3- (4'-chloro-4 biphenylyl) butane and 0.61 g of 2-aminoethanol in 100 ml of toluene is mixed with 0.1 g of p-toluenesulfonic acid added, boiled for 2.5 hours and cooled. Customary work-up gives 1- [4- (2-Hydroxyethyl) piperazino] -3- (4'-chloro-4-biphenylyl) butane.

Example 38 To 3.26 g of 1-morpholino-3- (4'-amino-4-biphenylyl) -butan-3-ol [obtainable by nitration of l-morpholino-3- (4-biphenylyl) -butan-3-ol and Reduction of the 1-morpholino-3- (4'-nitro-4-biphenylyl) -butan-3-ol] obtained] one at 0 ° 3 ml of concentrated hydrochloric acid, then with stirring at 0 ° a solution of 1.4 g NaNO2 in 6 ml water. After adding a solution of 0.7 g of boric acid in 1.5 g 60% hydrofluoric acid is stirred for 40 minutes, filtered, washed with water, Methanol and ether and dried. The diazonium salt obtained is until the end of the Decomposition heated to around 1500. L-Morpholino-3- (4'-fluoro-4-hipheylyl) -btan-3-ol is obtained, Example 39 3.26 g of 1-morpholino-3- (4'-amino-4-biphenylyl) -butan-3-ol are dissolved in 30 ml of 10% hydrochloric acid, mixed at 0 to 0 with 0.7 g of STaN02 in 2 ml of water, are added dropwise the diazonium salt solution obtained slowly to a hot Cu2Cl2 solution (obtained by reducing 2.1 g of copper sulfate with SO2 in 13 ml of water in the presence of 2.6 g NaCl) added, heated for a further 30 minutes to 90 to 95 °, cools down, works as usual and receives 1-morpholino-3- (4'-chloro-4-biphenylyl) -butan-3-ol, F. 106 - 108 ° Example 40 Analogously to Example 39, with Cu2Br2 (instead of Cu2Cl2) l-Morpholino-3- (4'-bltom-4 ~ biphenylyl) -butane »3 ~ ol, F. 97-990.

Example 41 A mixture of 2.22 g of p = iodofluorobenzene and 2.71 g of the sodium salt of 1-piperidino-3-p-hydroxyphenyl-butan-3-ol (obtainable by reaction of p-hydroxyacetophenone with ethyl bromoacetate and zinc, reduction of the 3-p-llydroxyphenyl obtained 3-hydroxybutyric acid ethyl ester with LiAlH4 to 3-p-hydroxyphenyl-butane-1,3-diol, Reaction with SOCl2 to 1-chloro-3-p-hydroxyphenyl-butan-3-ol and reaction with piperidine) is heated to 900 for 8 hours in the presence of 1 g of copper powder in 10 ml of HNST and then worked up as usual. 1-piperidino-3- (4-fluorophenoxyphenyl) -butan-3-ol is obtained, Example 42 A solution of 3.59 g of 1-piperidino-3-p-iodophenyl-butan-3-ol (available by reaction of 1-chloro-3-p-iodophenylbut-an-3-ol and piperidine) and 1.51 g of sodium p-chlorophenolate in 20 ml of DMF is heated to 1300 for 8 hours. Customary work-up gives 1-piperidino-3- (4-p-chlorophenoxyphenyl) -butan-3-ol, mp 73-75 °.

Example 43 25.9 g of 3- (4'-fluoro-4-biphenylyl) -3-hydroxy-butyl are boiled amine p-toluenesulfonate with 1 g of p-toluenesulfonic acid in 500 ml of toluene for 2 hours with Water separator, cools down, works up with sodium hydroxide solution and receives 3- (4'-fluoro-4-biphenylyl) -2-buten-1-yl-amine Analogue obtained by dehydrating the corresponding hydroxyamines with p-toluenesulfonic acid: 1-methylamino-3-p-biphenylyl-2-butene 1-methylamino-3- (4'-fluoro-4-biphenylyl) -2-butene l-methylamino-3- (4'-chloro-4-biphanylyl) -2-butene l-methylamino-3- (4-p-chlorophenoxyphenyl) -2-butene 1-ethylamino-3-p-biphenylyl-2-butene 1-ethylamino-3- (4'-fluoro-4-biphenylyl) -2-butene 1-ethylamino-3- (4'-chloro-4-biphenylyl) -2-butene i-.sethylamino-3- (4-p-chlorophenoxyphenyl) butene 1-n-propylamino-3-p-biphenylyl-2-butene 1-n-propylamino-3- (4'-fluoro-4-biphenylyl) -2-butene 1-n-Propylamino-3- (4'-chloro-4-biphenylyl) -2-butene l-n-Propylamino-3- (4-p-chlorophenoxyphenyl) ~ 2-buGen 1- isopropylamino-3-p-biphenylyl-2-butene 1-isopropylamino-3- (4'-fluoro-4-biphenylyl) -2-butene 1-Isopropylamino-3- (4'-chloro-4-biphenylyl) -2-butene 1-isopropylamino-3- (4-p-chlorophenoxyphenyl) -2-butene 1-n-Butylamino-3-p-biphenylyl-2-butene 1-n-Butylamino-3- (4'-fluoro-4-biphenylyl) -2-butene 1-n-Butylamino-3- (4'-chloro-4-biphenylyl) -2-butene 1-n-Butylamino-3- (4-p-chlorophenoxyphenyl) -2-butene 1-Isobutylamino-3-p-biphenylyl-2-butene 1-Isobutylamino-3- (4'-fluoro-4-biphenylyl) -2-butene 1-Isobutylamino-3- (4'-chloro-4-biphenylyl) -2-butene 1-Isobutylamino-3- (4-p-chlorophenoxyphenyl) -2-butene l-sec-Butylamino-3-p-biphenylyl-2-butene l-sec-butylamino-3- (4'-fluoro-4- biphenylyl) -2-butene l-sec-Butylamino-3- (4'-chloro-4-biphenylyl) -2-butene l-sec, -butylamino-3- (4-p-chlorophenoxyphenyl) -2-butene 1-tert-Butylamino-3-p-biphenylyl-2-butene 1-tert-Butylamino-3- (4'-fluoro-4-biphenylyl) -2-butene l-tert-butylamino "3- (4'-chloro-4-kiphenylyl) -2-butene l-tert-butylamino-3- (4-p-chlorophenoxyphenyl) -2-butene.

Example 44 A mixture of 3.1 g of 1-morpholino-3-p-biphenylyl-butan-3-ol, 0.1 g of benzenesulfonic acid and 80 ml of benzene are boiled with a water separator for 24 hours. Customary work-up gives 1-morpholino-3-biphenylyl-2-butene.

Analogously, by dehydrating the corresponding hydroxy amines, one obtains: 1-morpholino-3- (2'-fluoro-4-biphenylyl) -2-butene 1-morpholino-3- (4'-fluoro-4-biphenylyl) -2-butene 1-morpholino-3- (2'-chloro-4-biphenylyl) -2-butene 1-morpholino-3- (4'-chloro-4-biphenylyl) -2-butene, F. 109-1110 1-Morpholino-3- (2'-bromo-4-biphenylyl) -2-butene 1-morpholino-3- (4'-bromo-4-biphenylyl) -2-butene l-Morpholino-3- (2 ', 4'-difluoro-4-biphenylyl) -2-butene l-Morpholino-3- (2', 4 '"diclllor ~ 4-biphenylyl) -2 ~ butene 1-Morpholino-3- (2 ', 4'-dibromo-4-biphenylyl) -2-butene 1-Morpholino-3-p-phenoxyphenyl2 butene 1-morpholino-3- (4-o-fluorophenoxyphenyl) -2-butene 1-morpholino-3- (4-p-fluorophenoxyphenyl) -2-butene l-morpholino-3- (4-o-chlorophenoxy-pbenyl) -2-butene 1-morpholino-3- (4-p-chlorophenoxyphenyl) -2-butene, F. 95-970 1-Morpholino-3- (4-o-bromophenoxyphenyl) -2-butene 1-morpholino-3- (4-p-bromophenoxyphenyl) -2-butene 1-Morpholino-3 "[4 ~ (2,4-difluorophenoxy) -phenyl] -2-butene 1-morpholino-3- [4- (2,4-dichlorophenoxy) ~ phenyl] ~ 2 ~ butene l-Morpholino-3- [4- (2,4-dibromophenoxy) -phenyl] -2-butene-l-orpholino-4-p-biphenylyl-3-pentene 1-morpholino- (4'-fluoro-4-biphenylyl) -3-pentene 1-morpholino- (4'-chloro-4-biphenylyl) -3-pentene 1-morpholino- (4'-bromo-4-biphenylyl) -3-pentene, 1-morpholino- (4-p-chlorophenoxyphenyl) -3-pentene 1-pyrrolidino-3-p-biphenylyl-2-butene 1-pyrrolidino-3- (2'-fluoro-4-biphenylyl) -2-butene 1-pyrrolidino-3- (4'-fluoro-4-biphenylyl) -2-butene 1-pyrrolidino-3- (2'-chloro-4-biphenylyl) -2-butene 1-pyrrolidino-3- (4'-chloro-4-biphenylyl) -2-butene 1-pyrrolidino-3- (2'-bromo-4-biphenylyl) -2-butene 1-pyrrolidino-3- (4'-bromo-4-biphenylyl) -2-butene 1-pyrrolidino-3- (2 ', 4'-difluoro-4-biphenylyl) -2-butene 1-pyrrolidino-3- (2', 4'-dichloro-4-biphenylyl) -2-butene 1-pyrrolidino-3- (2 ', 4'-dibromo-4-biphenylyl) -2-butene 1-pyrrolidino-3-p-phenoxyphenyl-2-butene 1-pyrrolidino-3- (4-o-fluorophenoxyphenyl) -2-butene 1-pyrrolidino-3- (4-p-fluorophenoxyphenyl) -2-butene 1-pyrrolidino-3- (4-o-chlorophenoxyphenyl) -2-butene 1-pyrrolidino-3- (4-p-chlorophenoxyphenyl) -2-butene 1-pyrrolidino-3- (4-o-bromophenoxyphenyl) -2-butene 1-pyrrolidino-3- (4-p-bromophenoxyphenyl) -2-butene 1-pyrrolidino-3- [4- (2,4-difluorophenoxy) phenyl] -2-butene 1-pyrrolidino-3- [4- (2,4-dichlorophenoxy) phenyl] -2-butene 1-pyrrolidino-3- [4- (2,4-dibromophenoxy) phenyl] -2-butene 1-pyrrolidino-3-p-biphenylyl-2-butene 1-pyrrolidino-3- (2'-fluoro-4-biphenylyl) -2-butene 1-pyrrolidino-3- (4'-fluoro-4-biphenylyl) -2-butene 1-pyrrolidino-3- (2'-chloro-4-biphenylyl) -2-butene 1-pyrrolidino-3- (4'-chloro-4-biphenylyl) -2-butene 1-pyrrolidino-3- (2'-bromo-4-biphenylyl) -2-butene 1-pyrrolidino-3- (4'-bromo-4-biphenylyl) -2-butene M.p. 130-132 ° 1-pyrrolidino-3- (2 ', 4'-difluoro-4-biphenylyl) -2-butene 1-pyrrolidino-3- (2', 4'-dichloro-4-biphenylyl) -2 -but 1-pyrrolidino-3- (2 ', 4'-dibromo-4-biphenylyl) -2-butene 1-pyrrolidino-3-p-phenoxyphenyl-2-butene 1-pyrrolidino-3- (4-o-fluorophenoxyphenyl) -2-butene 1-pyrrolidino-3- (4-p-fluorophenoxyphenyl) -2-butene 1-pyrrolidino-3- (4-o-chlorophenoxyphenyl) -2-butene 1-pyrrolidino-3- (4-p-chlorophenoxyphenyl) -2-butene l-piperidino-3- (4-o-bromophenoxyphenyl) -2-butene l-piperidino-3- (4-p-bromophenoxyphenyl) -2-butene l-piperidino-3- [4- (2} 4-difluorophenoxy) phenyl3-2-butene l-piperidino-3- [4- (2,4-dichlorophenoxy) phenyl3-2-butene l-piperidino-3- [4- (2,4-dibromophenoxy) phenyl3-2-butene 1-piperidino-4-p-biphenylyl-3-pentene 1-piperidino-4- (4'-fluoro-4-biphenylyl) -3-pentene 1-piperidino-4- (4'-chloro-4-biphenylyl) -3-pentene 1-piperidino-4- (4'-bromo-4-biphenylyl) -3-pentene 1-piperidino-4- (4-p -chlorophenoxyphenyl) -3-pentene 1- (4-methylpiperidino) -3-p-biphenylyl-2-butene 1- (4-methylpiperidino) ~ 3- (2'-fluoro-4-biphenylyl) -2-butene 1- (4-methylpiperidino) -3- (4'-fluoro-4-biphenylyl) -2-butene 1- (4-methylpiperidino) -3- (2'-chloro-4-biphenylyl) -2-butene 1- (4-methylpiperidino) -3- (4'-chloro-4-biphenylyl) -2-butene 1- (4-Methylpiperidino) -3- (2'-bromo-4-biphenylyl) -2-butene 1- (4-methylpiperidino) -3- (4'-bromo-4-biphenylyl) -2-butene 1- (4-methylpiperidino) -3- (2 ', 4'-difluoro-4-biphenylyl) -2-butene 1- (4-methylpiperidino) -3- (2', 4'-dichloro-4-biphenylyl) -2-butene 1- (4-methylpiperidino) -3- (2 ', 4'-dibromo-4-biphenylyl) -2-butene 1- (4-methylpiperidino) -3-p-phenoxyphenyl-2-butene 1- (4-methylpiperidino) -3- (4-o-fluorophenoxyphenyl) -2-butene 1- (4-methylpiperidino) -3- (4-p-fluorophenoxyphenyl) -2-butene 1- (4-methylpiperidino) -3- (4-o -chlorophenoxyphenyl) -2-butene 1- (4-methylpiperidino) -3- (4-p -chlorophenoxyphenyl) -2-butene 1- (4-methylpiperidino) -3- (4-o-bromophenoxyphenyl) -2-butene 1- (4-methylpiperidino) -3- (4-p-bromophenoxyphenyl) -2-butene 1- (4-Methylpiperidino) -3- [4- (2,4-difluorophenoxy) -phenyl] -2-butene 1- (4-WIethylpiperidino) -3- [4- (2,4-dichlorophenoxy) -phenyl] -2-butene 1- (4-Methylpiperidino) -3- [4- (2X4-dibromophenoxy) phenyl] -2-butene 1-homopiperidino-3-p-biphenylyl-3-butene 1-homopiperidino-3- (2'-fluoro-4-biphenylyl) -2-butene 1-homopiperidino-3- (4'-fluoro-4-biphenylyl) -2-butene 1-homopiperidino-3- (2'-chloro-4-biphenylyl) -2-butene 1-homopiperidino-3- (4'-chloro-4-biphenylyl) -2-butene 1-homopiperidino-3- (2'-bromo-4-biphenylyl) -2-butene 1-homopiperidino-3- (4'-bromo-4-biphenylyl) -2-butene 1-homopiperidino-3- (2 ', 4'-difluoro-4-biphenylyl) -2-butene 1-homopiperidino-3- (2', 4'-dichloro-4-biphenylyl) -2-butene 1-homopiperidino-3- (2 ', 4'-dibromo-4-biphenylyl) -2-butene 1-homopiperidino-3-p-phenoxyphenyl-2-butene 1-homopiperidino-3- (4-o-fluorophenoxyphenyl) -2-butene 1-homopiperidino-3- (4-p-fluorophenoxyphenyl) -2-butene 1-homopiperidino-3- (4-o-chlorophenoxyphenyl) -2-butene 1-homopiperidino-3- (4-p-chlorophenoxyphenyl) -2-butene 1-homopiperidino-3- (4-o-bromophenoxyphenyl) -2-butene 1-homopiperidino-3- (4-p-bromophenoxyphenyl) -2-butene 1-homopiperidino-3- [4- (2,4-difluorophenoxy) phenyl] -2-butene 1-homopiperidino-3- [4- (2,4-dichlorophenoxy) phenyl] -2-butene 1-homopiperidino-3- [4- (2,4-dibromophenoxy) phenyl] -2-butene 1-piperazino-3-p-biphenylyl-2-butene 1-piperazino-3- (2'-fluoro-4-biphenylyl) -2-butene 1-piperazino-3- (4'-fluoro-4-biphenylyl) -2-butene 1-piperazino-3- (2'-chloro-4-biphenylyl) -2-butene 1-piperazino-3- (4'-chloro-4-biphenylyl) -2-butene 1-piperazino-3- (2'-bromo-4-biphenylyl) -2-butene 1-piperazino-3- (4'-bromo-4-biphenylyl) -2-butene 1-piperazino-3- (2 ', 4'-difluoro-4-biphenylyl) -2-butene 1-piperazino-3- (2', 4'-dichloro-4-biphenylyl) -2-butene 1-piperazino-3- (2 ', 4'-dibromo-4-biphenylyl) -2-butene 1-piperazino-3-p-phenonxy-phenyl-2-butene 1-piperazino-3- (4-o-fluorophenoxyphenyl) -2-butene 1-piperazino-3- (4-p-fluorophenoxyphenyl) -2-butene 1-piperazino-3- (4-o-chlorophenoxyphenyl) -2-butene 1-piperazino-3- (4-p-chlorophenoxyphenyl) -2-butene 2-piperazino-3- (4-o-bromophenoxyphenyl) -2-butene 2-piperazino-3- (4-p-bromophenoxyphenyl) -2-butene 2-piperazino-3- [4- (2,4-difluorophenoxy) phenyl] -2-butene 2-piperazino-3- [4- (2,4-dichlorophenoxy) phenyl] -2-butene 2-piperazino-3- [4- (2,4-dibromophenoxy) phenyl] -2-butene 1-Dietylamino-3-p-biphenylyl-2-butene 1-Dietylamino-3- (2'-fluoro-4-biphenylyl) -2-butene 1-diethylamino-3- (4'-fluoro-4-biphenylyl) -2-butene 1-dietylamino-3- (2'-chloro-4-biphenylyl) -2-butene 1-diethylamino-3- (4'-chloro-4-biphenylyl) -2-butene 1-dietylamino-3- (2'-bromo-4-biphenylyl) -2-butene 1-dietylamino-3- (4'-bromo-4-biphenylyl) -2-butene 1-dietylamino-3- (2 ', 4'-difluoro-4-biphenylyl) -2-butene 1-dietylamino-3- (2 ', 4'-dichloro-4-biphenylyl) -2-butene 1-dietylamino-3- (2', 4'-dibromo-4-biphenylyl) -2-butene 1-diethylamino-3-p-phenoxyphenyl-2-butene 1-diethylamino-3- (4-o-fluorophenoxy) phenyl] -2-butene 1-diethylamino-3- (4-p-fluorophenoxy) phenyl] -2-butene 1-diethylamino-3- (4-o-chlorophenoxy) phenyl] -2-butene 1-diethylamino-3- (4-p-chlorophenoxy) phenyl] -2-butene 1-diethylamino-3- (4-o-bromophenoxy) phenyl] -2-butene 1-diethylamino-3- (4-p-bromophenoxy) phenyl] -2-butene 1-diethylamino-3- [4- (2,4-difluorophenoxy) phenyl] -2-butene 1-diethylamino-3- [4- (2,4-dichlorophenoxy) phenyl] -2-butene 1-diethylamino-3- [4- (2,4-dibromophenoxy) phenyl] -2-butene 1-phthalimido-3-p-biphenylyl-2-butene 1-phthalimido-3- (2'-fluoro-4-biphenylyl) -2-butene 1-phthalimido-3- (4'-fluoro-4-biphenylyl) -2-butene 1-phthalimido-3- (2'-chloro-4-biphenylyl) -2-butene 1-phthalimido-3- (4'-chloro-4-biphenylyl) -2-butene 1-phthalimido-3- (2'-bromo-4-biphenylyl) -2-butene 1-phthalimido-3- (4'-bromo-4-biphenylyl) -2-butene 1-phthalimido-3- (2 ', 4'-difluoro-4-biphenylyl) -2-butene 1-phthalimido-3- (2 ', 4'-dichloro-4-biphenylyl) -2-butene 1-phthalimido-3- (2 ', 4'-dibromo-4-biphenylyl) -2-butene 1-phthalimido-3-p-phenoxyphenyl-2-butene 1-phthalimido-3- (4-o-fluorophenoxyphenyl) -2-butene 1-phthalimido-3- (4-p-fluorophenoxyphenyl) -2-butene 1-phthalimido-3- (4-o-chlorophenoxyphenyl) -2-butene 1-phthalimido-3- (4-p-chlorophenoxyphenyl) -2-butene 1-phthalimido-3- (4-o-bromophenoxyphenyl) -2-butene 1-phthalimido-3- (4-p-bromophenoxy-phenyl) -2-butene 1-phthalimido-3- [4- (2,4-difluorophenoxy) phenyl) -2-butene 1-phthalimido-3- [4- (2,4-dichlorophenoxy) phenyl) -2-butene 1-phthalimido-3- [4- (2,4-dibromophenoxy) phenyl) -2-butene 1- (1-imidazolyl) -3-p-biphenylyl-2-butene 1- (1-imidazolyl) -3- (2'-fluoro-4-biphenylyl) -2-butene 1- (1-imidazolyl) -3- (4'-fluoro-4-biphenylyl) -2-butene 1- (1-imidazolyl) -3- (2'-chloro-4-biphenylyl) -2-butene 1- (1-imidazolyl) -3- (4'-chloro-4-biphenylyl) -2-butene 1- (1-imidazolyl) -3- (2'-bromo-4-biphenylyl) -2-butene 1- (1-imidazolyl) -3- (4'-bromo-4-biphenylyl) -2-butene 1- (1-imidazolyl) -3- (2 ', 4'-difluoro-4-biphenylyl) -2- buten 1- (1-imidazolyl) -3- (2 ', 4'-dichloro-4-biphenylyl) -2-butene 1- (1-imidazolyl) -3- (2', 4'-dibromo-4-biphenylyl) -2-butene 1- (1-imidazolyl) -3-p-phenoxyphenyl-2-butene 1- (1-imidazolyl) -3- (4-o-fluorophenoxyphenyl) -2-butene 1- (1-imidazolyl) -3- (4-p-fluorophenoxyphenyl) -2-butene 1- (1-imidazolyl) -3- (4-o-chlorophenoxyphenyl) -2-butene 1- (1-Imidazolyl) -3- (4-p-chlorophenoxyphenyl) -2-butene m.p. 79-81 ° 1- (1-Imidazolyl) -3- (4-o-bromophenoxyphenyl) -2 -but 1- (1-Imidazolyl) -3- (4-p-bromophenoxy-phenyl) -2-butene 1- (1-imidazolyl) -3- [4- (2,4-difluorophenoxy) -phenyl] -2-butene 1- (1-Imidazolyl) -3- [4- (2,4-dichlorophenoxy) phenyl] -2-butene nD20 1,5671 1- (1-imidazolyl) -3- [4- (2,4-dibromophenoxy ) -phenyl] -2-butene. fital Example 45 Analogously to Example 44, dehydration is used of the corresponding hydroxyamines: 1-di-n-propylamino-3-p-biphenylyl-2-butene l-di-n-propylamino-3- (4'-fluoro-4-biphenylyl) -2-butene 1-di-n-propylamino-3- (4'-chloro-4-biphenylyl) -2-butene l-di-n-propylamino-3- (4-p-chlorophenoxyphenyl) -2-butene 1-diisopropylamino-3-p-biphenylyl-2-butene 1-diisopropylamino-3- (4'-fluoro-4-biphenylyl) -2-butene 1-diisopropylamino-3- (4'-chloro-4-biphenylyl) -2-butene 1-diisopropylamino-3- (4-p-chlorophenoxyphenyl) -2-butene 1-di-n-butylamino-3-p-biphenylyl-2-butene 1-di-n-butylamino-3- (4'-fluoro-4-biphenylyl) -2-butene l-di-n-butylamino-3- (4'-chloro-4-biphenylyl) -2-butene l-di-n-butylamino-3- (4-p-chlorophenoxyphenyl) -2-butene 1-diisobutylamino-3-p-biphenylyl-2-butene 1-diisobutylamino-3- (4'-fluoro-4-biphenylyl) -2-butene 1-diisobutylamino-3- (4'-chloro-4-biphenylyl) -2-butene 1-diisobutylamino-3- (4-p-chlorophenoxyphenyl) -2-butene l-di-n -pentylamino-3-p-biphenylyl-2-butene l-di-n-pentylamino-3- (4 '~ fluoro-4-biphenylyl) -2-butene l-di-n -pentylamino-3- (4'-chloro-4-biphenylyl) -2-butene l-di-n -pentylamino-3- (4-p-chlorophenoxyphenyl) -2-butene 1-di-n-hexylamino-3-p-biphenylyl-2-butene 1-di-n-hexylamino-3- (4'-fluoro-4-biphenylyl) -2-butene l-di-n-hexylamino-3- (4'-chloro-4-biphenylyl) -2-butene l-di-n-hexylamino-3- (4-p-chlorophenoxyphenyl) -2-butene 1- (2-Dimethylamino-ethylamino) -3-p-biphenylylA2-butene 1- (2-Dimethylamino-ethylamino) -3- (4'-fluoro-4-biphenylyl) -2-butene 1- (2-dimethylamino-ethylamino) -3- (4'-chloro-4-biphenylyl) -2-butene 1- (2-dimethylamino-ethylamino) -3- (4-p-chlorophenoxyphenyl) 2-butene 1- (2-diethylamino-ethylamino) -3-p-biphenylyl-2-butene 1- (2-diethylamino-ethylamino) -3- (4'-fluoro-4-biphenylyl) -2-butene 1- (2-diethylamine-p-ethylamino) -3- (4'-chloro-4-biphenylyl) -2-butene 1- (2-diethylamino-ethylamino) -3- (4-p-chlorophenoxyphenyl) -2-butene 1- (3-dimethylamino-propylamino) -3-p-biphenylyl-2-butene 1- (3-Dimethylamino-propylamino) -3- (4'-fluoro-4-biphenylyl) -2-butene 1- (3-dimethylamino-propylamino) -3- (4'-chloro-4-biphenylyl) -2 -but 1- (3-Dimethylainino-propylamino) -3- (4-p -chlorophenoxy-phenyl) -2-butene 1- (2-methylpiperidino) -3-p-biphenylyl-2-butene 1- (2-methylpiperidino) -3- (4'-fluoro-4-biphenylyl) -2-butene 1- (2-methylpiperidino) -3- (4 -chlor-4-biphenylyl) -2-butene 1- (2-methylpiperidino) -3- (4-p-chlorophenoxyphenyl) -2-butene 1- (3-methylpiperidino) -3-p-biphenylyl-2-butene 1- (3-methylpiperidino) -3- (4'-fluoro-4-biphenylyl) -2-butene 1- (3-methylpiperidino) -3- (41-chloro-4-biphenylyl) -2-butene 1- (3-methylpiperidino) -3- (4-p -chlorophenoxyphenyl) -2-butene 1- (2,6-Dimethylpiperidino) -3-p-biphenylyl-2-butene 1- (2,6-Dimethylpiperidino) -3- (4th -fluoro-4-biphenylyl) -2-butene 1- (2,6-dimethylpiperidino) -3- (4'-chloro-4-biphenylyl) -2-butene 1- (2,6-Dimethylpiperidino) -3- (4-p -chlorophenoxyphenyl) -2-butene 1- (4-methyl-piperazino) -3-p-biphenyl-2-butene 1- (4-methyl-piperazino) -3- (4-fluoro-4-biphenylyl) -2-butene 1- (4-methyl-piperazino) -3- (4'-chloro-4-biphenylyl) -2- buten 1- (4-methyl-piperazino) -3- (4-p-chlorophenoxyphenyl) -2-butene 1- (4-ethyl-piperazino) -3-p-biphenylyl-2-butene 1- (4-ethyl-piperazino) -3- (4'-fluoro-4-biphenylyl) -2-butene 1- (4-ethyl-piperazino) -3- (4'-chloro-4-biphenylyl) -2 -but 1- (4-ethyl-piperazino) -3- (4-p-chlorophenoxyphenyl) -2-butene 1- (4-n-hexyl-piperazino) -3-p-biphenylyl-2-butene 1- (4-n-Hexyl-piperazino) -3- (4'-fluoro-4-biphenylyl) -2-butene 1- (4-n-HeXyl-piperazino) -3- (4'-chloro-4- biphenylyl) -2-butene 1- (4-n-Hexyl-piperazino) -3- (4-p-chlorophenoxyphenyl) -2-butene 1- [4- (2-hydroxyethyl) piperazino] -3-p-biphenylyl-2-butene 1- [4- (2-Hydroxyffithyl) piperazino] -3- (4'-fluoro-4-biphenylyl) -2-butene 1- [4- (2-hydroxyethyl) piperazino] -3- (F4'- chloro-4-biphenylyl) -2- butene 1- L4- (2-Bydroxyäthyl) -piperazino3-3- (4-p-chlorophenoxyphenyl) -2-butene, example 46 A mixture of 1 g of 3- (4'-chloro-4-biphenylyl) -3-hydroxybutylamine, 2.5 ml of a 67 win solution of HJ in acetic acid and 5 ml of acetic acid is boiled for 90 minutes, evaporated and worked up with water and chloroform, one obtains 3- (4'-chloro-4-biphenylyl-butylamine-hydroiodide, which is converted into the free base with sodium hydroxide solution. Tartrate, F. 200 - 202 °.

Analogously, one obtains from the corresponding hydroxyamines with EIF / acetic acid: 1-methylanino-3-p-biphenylyl-butane 1-methylamino-3- (4'-fluoro-4-biphenylyl) -butane 1-methylamino-3- (4'-chloro-4-biphenylyl) butane 1-methylamino-3- (4-p-chlorophenoxyphenyl) butane l-ethylamino-3-p-biphenylyl-butane l-ethylamino-3- (4'-fluoro-4-biphenylyl) -butane 1-ethylamino-3- (4'-chloro-4-biphenylyl) -butane 1-ethylamino-3- (4-p-chlorophenoxyphenyl) -butane 1- n-Propylamino-3-p-biphenylyl-butane 1-n-Propylamino-3- (4'-fluoro-4-biphenylyl) -butane l-n-Propylamino-3- (4'-chloro-4-biphenylyl) -butane l-n-propylamino-3- (4-p-chlorophelloxyphenyl) -butane 1-Isopropylamino-3-p-biphenylyl-butane 1-Isopropylamino-3- (4'-fluoro-4-biphenylyl) -butane 1-Isopropylamino-3- (4'-chloro-4-biphenylyl) -butane 1-Isopropylamino-3- (4-p-chlorophenoxyphenyl) -butane 1-n-Butylamino-3-p-biphenylyl-butane 1-n-Butylamino-3- (4'-fluoro-4-biphenylyl) -butane 1-n-Butylamino-3- (4'-chloro-4-biphenylyl) -butane 1-n-Butylamino-3- (4-p-chlorophenoxyphenyl) -butane 1-Isobutylamino-3-p-biphenylyl-butane 1-Isobutylamino-3- (4'-fluoro-4-biphenylyl) -butane 1-isobutylamino-3- (4'-chloro-4-biphenylyl) -butane 1-1 sobutylamino-3- (4-p-chlorophenoxyphenyl) - butane 1-sec-butylamino-3-p-biphenylyl-butane 1-sec-butylamino-3- (4'-fluoro-4-biphenylyl) -butane 1-sec-Butylamino-3- (4'-chloro-4-biphenylyl) -butane 1-sec-Butylamino-3- (4-p-chlorophenoxyphenyl) -butane 1-tert-Butylamino-3-p-biphenylyl-butane 1-tert-Butylamino-3- (4'-fluoro-4-biphenylyl) -butane 1-tert-butylamino-3- (4'-chloro-biphenylyl) -lutane 1-tert-butylamino-3- (4-p-chlorophenoxyphenyl) -butane.

Example 47 A mixture of 3.1 g of 1-morpholino-3-p-biphenylyl-butan-3-ol, 10 ml of 67% hydroiodic acid and 18 ml of acetic acid are brought to 1500 for 1.5 hours heated. After cooling and the usual work-up, 1-morpholino-3-p-biphenylyl-butane is obtained.

Analogously, by reducing the corresponding hydroxyamines, one obtains: 1-morpholino-2-p-biphenylyl propane 1-morpholino-2- (4'-fluoro-4-biphenylyl) propane 1-morpholino-2- (4'-chloro-4-biphenylyl) propane 1-morpholino-2- (4'-bromo-4-biphenylyl) propane 1-morpholino-2- (4-p-chlorophenoxyphenyl) propane 1-morpholino-2- (2'-fluoro-4-biphenylyl) -butane 1-morpholino-3- (4'-fluoro-4-biphenylyl) -butane, F. 54-560 1-morpholino-3- (2'-chloro-4-biphenylyl) -butane 1-morpholino-3- (4'-chloro-4-biphenylyl) -butane, F. 77-790 l - Morpholino-3- (2'-bromo -4-biphenylyl) -butane 1-morpholino-3- (4'-bromo-4-biphenylyl) -butane 1-Morpholino-3- (2 ', 4'-difluoro-4-biphenylyl) -butane hydrochloride, mp 198-200 ° 1-Morpholino-3- (2', 4'-dichloro-4-biphenylyl) -butane 1-Morpholino-3- (2 ', 4'-dibromo-4-biphenylyl) -butane 1-Morpholino-3-p-phenoxyphenyl-butane 1-Morpholino-3- (4-o-fluorophenoxyphenyl) -butane 1-Morpholino-3- (4-p-fluorophenoxyphenyl) -butane l-morpholino-3- (4-o-chlorophenoxyphenyl) -butane 1-morpholino-3- (4-p-chlorophenoxyphenyl) -butane, Hydrochloride, F. 172 - 1740 1-Morpholino-3- (4-o-bromophenoxyphenyl) -butane l-Morpholino-3- (4-p-Bromophenoxy-phenyl) -butane 1-Morpholino-3- [4- (2,4-difluorophenoxy) -phenyl] -butane 1-morpholino-3- [4- (2,4-dichlorophenoxy) phenyl] butane 1-morpholino-3- [4- (2,4-dibromophenoxy) phenyl] butane 1-Morpholino-4-p-biphenylyl-pentane 1-Morpholino-4- (4'-fluoro-4-biphenyly) -pentane 1-Morpholino-4- (4'-chloro-4-biphenylyl) -p 1-Morpholino-4- (4'-bromo-4-biphenylyl) pentane 1-morpholino-4- (4-p-chlorophenoxyphenyl) -pentane 1-pyrrolidino-3-p-biphenylyl-butane 1-pyrrolidino-3- (2'-fluoro-4-biphenylyl) -butane 1-pyrrolidino-3- (4'-fluoro-4-biphenylyl) -butane Fumarate, F. 150-1520 1-pyrrolidino-3- (2'-chloro-4-biphenylyl) butane 1-pyrrolidino-3- (4'-chloro-4-biphenylyl) -butane 1-pyrrolidino-3- (2'-bromo-4-biphenylyl) -butane 1-pyrrolidino-3- (4'-bromo-4-biphenylyl) -butane 1-pyrrolidino-3- (2 ', 4'-difluoro-4-biphenylyl) -butane 1-pyrrolidino-3- (2 ', 4'-dichloro-4-biphenylyl) -butane 1-pyrrolidino-3- (2', 4'-dibromo-4-biphenylyl) -butane 1-pyrrolidino-3-p-phenoxyphenyl-butane 1-pyrrolidino-3- (4-o-fluorophenoxyphenyl) butane 1-pyrrolidino-3- (4-p-fluorophenoxyphenyl) -butane 1-pyrrolidino-3- (4-o-chlorophenoxyphenyl) -butane 1-pyrrolidino-3- (4-p-chlorophenoxyphenyl) -butane 1-pyrrolidino-3- (4-o-bromophenoxyphenyl) -butane 1-pyrrolidino-3- (4-p-bromophenoxy-phenyl) -butane 1-pyrrolidino-3- [4- (2,4-difluorophenoxy) -phenyl] -butane 1-pyrrolidino-3- [4- (2,4-dichlorophenoxy) phenyl] butane 1-pyrrolidino-3- [4- (2,4-dibromophenoxy) phenyl] butane 1-piperidino-2-p-biphenylyl-propane 1-piperidino-2- (4'-fluoro-4-biphenylyl) -propane, Hydrochloride, m.p. 226-227 ° 1-piperidino-2- (4'-chloro-4-biphenylyl) propane 1-piperidino-2- (4'-bromo-4-biphenylyl) propane, Hydrochloride, m.p. 260-261 1-piperidino-2- (4-p -chlorophenoxyphenyl) propane 1-piperidino-3-p-biphenylyl-butane 1-piperidino-3- (2'-fluoro-4-biphenylyl) -butane 1-piperidino-3- (4'-fluoro-4-biphenylyl) -butane, Hydrochloride, m.p. 207-209 ° 1-piperidino-3- (2'-chloro-4-biphenylyl) -butane 1-piperidino-3- (4'-chloro-4-biphenylyl) -butane, Hydrochloride, m.p. 215 ° 1-piperidino-3- (2'-bromo-4-biphenylyl) -butane 1-piperidino-3- (4'-bromo-4-biphenylyl) -butane 1-piperidino-3- (2 ', 4'-difluoro-4-biphenylyl) -butane 1-piperidino-3- (2', 4'-dichloro-4-biphenylyl) -butane 1-piperidino-3- (2 ', 4'-dibromo-4-biphenylyl) butane 1-piperidino-3-p-phenoxyphenyl-butane 1-piperidino-3- (4-o-fluorophenoxyphenyl) -butane 1-piperidino-3- (4-p-fluorophenoxyphenyl) -butane 1-piperidino-3- (4-o-chlorophenoxyphenyl) butane 1-piperidino-3- (4-p-chlorophenoxyphenyl) butane 1-piperidino-3- (4-o-bromophenoxyphenyl) -butane 1-piperidino-3- (4-p-bromophenoxyphenyl) -butane 1-piperidino-3- [4- (2,4-difluorophenoxy) phenyl] butane 1-piperidino-3- [4- (2,4-dichlorophenoxy) phenyl] butane 1-piperidino-3- [4- (2,4-dibromophenoxy) phenyl] butane 1-piperidino-4-p-biphenylyl pentane 1-piperidino-4- (4'-fluoro-4-biphenyly) -pentane 1-piperidino-4- (4'-chloro-4-biphenyly) -pentane 1-piperidino-4- (4'-bromo-4-biphenylyl) pentane hydrochloride, mp 235 °; Hydroiodide, M.p. 212-214 ° 1-piperidino-4- (4-p-chlorophenoxyphenyl) -pentane 1- (4-methylpiperidino) -3-p-biphenylyl-butane 1- (4-methylpiperidino) -3- (2'-fluoro-4-biphenylyl) -butane 1- (4-methylpiperidino) -3- (4'-fluoro-4-biphenylyl) -butane 1- (4-methylpiperidino) -3- (2'-chloro-4-biphenylyl) -butane 1- (4-methylpiperidino) -3- (4'-chloro-4-biphenylyl) -butane 1- (4-methylpiperidino) -3- (2'-bromo-4-biphenylyl) -butane 1- (4-methylpiperidino) -3- (4'-bromo-4-biphenylyl) -butane 1- (4-methylpiperidino) -3- (2 ', 4'-difluoro-4-biphenylyl) -butane 1- (4-methylpiperidino) -3- (2', 4'-dichloro-4-biphenylyl) -butane 1- (4-methylpiperidino) -3- (2 ', 4'-dibromo-4-biphenylyl) -butane 1- (4-methylpiperidino) -3-p-phenoxyphenyl-butane 1- (4-methylpiperidino) -3- (4-o-fluorophenoxyphenyl) -butane 1- (4-methylpiperidino) -3- (4-p-fluorophenoxyphenyl) -butane 1- (4-methylpiperidino) -3- (4-o-chlorophenoxyphenyl) -butane 1- (4-methylpiperidino) -3- (4-p -chlorophenoxyphenyl) -butane 1- (4-methylpiperidino) -3- (4-o-bromo-phenoxyphenyl) -butane 1- (4-methylpiperidino) -3- (4-p-bromo-phenoxyphenyl) -butane 1- (4-methylpiperidino) -3- [4- (2,4-difluorophenoxy) phenyl] butane 1- (4-methylpiperidino) -3- [4- (2,4-dichlorophenoxy) phenyl] butane 1- (4-methylpiperidino) -3- [4- (2,4-dibromophenoxy) phenyl] butane 1-homopiperidino-3-p-biphenylyl-butane 1-homopiperidino-3- (2'-fluoro-4-biphenylyl) -butane 1-homopiperidino-3- (4'-fluoro-4-biphenylyl) -butane 1-homopiperidino-3- (2'-chloro-4-biphenylyl) -butane 1-homopiperidino-3- (4'-chloro-4-biphenylyl) -butane 1-homopiperidino-3- (2'-bromo-4-biphenylyl) -butane 1-homopiperidino-3- (4'-bromo-4-biphenylyl) -butane 1-homopiperidino-3- (2 ', 4'-difluoro-4-biphenylyl) -butane 1-homopiperidino-3- (2 ', 4'-dichloro-4-biphenylyl) -butane 1-homopiperidino-3- (2', 4'-dibromo-4-biphenylyl) -butane 1-homopiperidino-3-p-phenoxyphenyl-butane 1-homopiperidino-3- (4-o-fluorophenoxyphenyl) butane 1-homopiperidino-3- (4-p-fluorophenoxyphenyl) -butane 1-homopiperidino-3- (4-o-chlorophenoxyphenyl) -butane 1-homopiperidino-3- (4-p-chlorophenoxyphenyl) -butane 1-homopiperidino-3- (4-o-bromophenoxyphenyl) -butane 1-homopiperidino-3- (4-p-bromophenoxy-phenyl) -butane 1-homopiperidino-3- [4- (2,4-difluorophenoxy) -phenyl] -butane 1-homopiperidino-3- [4- (2,4-dichlorophenoxy) phenyl] butane 1-homopiperidino-3- [4- (2,4-dibromophenoxy) phenyl] butane 1-piperazino-3-p-biphenylyl-butane 1-piperazino-3- (2'-fluoro-4-biphenylyl) -butane 1-piperazino-3- (4'-fluoro-4-biphenylyl) -butane, 67-69 ° 1-piperazino-3- (2'-fluoro-4-biphenylyl) -butane 1-piperazino-3- (4'-fluoro-4-biphenylyl) -butane 1-piperazino-3- (2'-fluoro-4-biphenylyl) -butane 1-piperazino-3- (4'-fluoro-4-biphenylyl) -butane 1-piperazino-3- (2 ' , 4'-difluoro-4-biphenylyl) butane 1-piperazino-3- (2 ', 4'-dichloro-4-biphenylyl) butane l-piperazino-3- (2 1, 4'-dibromo-4-biphenylyl) -butane l-piperazino-3-p-phenoxyphenyl-butane l-piperazino-3- (4-o-fluorophenoxyphenyl) butane l-piperazino-3- (4-p-fluorophenoxyphenyl) butane l-piperazino-3- (4-o-chlorophenoxyphenyl) butane l-piperazino-3- (4-p-chlorophenoxyphenyl) butane 1-piperazino-3- (4-o-bromophenoxyphenyl) -butane 1-piperazino-3- (4-p-bromophenoxyphenyl) -butane 1-piperazino-3- [4- (2,4-difluorophenoxy) phenyl] butane 1-piperazino-3- [4- (2,4-dichlorophenoxy) phenyl] butane l-piperazino-3- [4- (2,4-dibromophenoxy) phenyl] butane l-diethyamino-3-p-biphenylyl butane 1-diethylamino-3- (2'-fluoro-4-biphenylyl) -butane 1-diethylamino-3- (4'-fluoro-4-biphenylyl) -butane, Bp 145 ° / C. 1 mm 1-diethylamino-3- (2'-chloro-4-biphenylyl) -butane 1-diethylamino-3- (4'-chloro-4-biphenylyl) -butane, M.p. 42-44 °, b.p. 175-180 ° / 0.1 mm 1-diethylamino-3- (2'-bromo-4-biphenylyl) -butane 1-Diethylamino-3- (4'-bromo-4-biphenylyl) -butane 1-Diethylamino-3- (2 ', 4'-difluoro-4-biphenylyl) -butane 1-Diethylamino-3- (2 ', 4'-dichloro-4-biphenylyl) -butane 1-Diethylamino-3- (2', 4'-dibromo-4-biphenylyl) -butane l-diethylamino-3-p-phenoxyphenyl-butane l-diethylamino-3- (4-o-fluorophenoxyphenyl) butane 1-Diethylamino-3- (4-p-fluorophenoxyphenyl) -butane 1-Diethylamino-3- (4-o-chlorophenoxyphenyl) -butane 1-diethylamino-3- (4-p-chlorophenoxyphenyl) -butane 1-diethylamino-3- (4-o-bromophenoxyphenyl) -butane 1-Diethylamino-3- (4-p-bromophenoxy-phenyl) -butane 1-Diethylamino-3- [4- (2,4-difluorophenoxy) -phenyl] -butane 1-DiSthylamino-3- [4- (2,4-dichlorophenoxy) -phenyla-buta 1-diethylamino-3- [4- (2,4-dibromophenoxy) -phenyl] -butane l-phthalimido-3-p-biphenylyl-butane, 120-1230 1-Phthalimido-3- (2'-fluoro-4-biphenylyl) -butane, 75-79 ° 1-Phthalimido-3- (4'-fluoro-4-biphenylyl) -butane, F. 142-144 ° l-phthalimido-3- (2'-chloro-4-biphenylyl) -butane 1-phthalimido-3- (4'-chloro-4-biphenylyl) -butane, 174-176 ° 1-Phthalimido-3- (2'-bromo-4-biphenylyl) -butane 1-Phthalimido-3- (4'-bromo-4-biphenylyl) -butane , Mp 180; 182 ° 1-phthalimido-3- (2 ', 4'-difluoro-4-biphenylyl) butane, mp 95-96 ° 1-phthalimido-3- (2', 4'-dichloro- 4-biphenylyl) butane, F. 108-1090 1-Phthalimido-3- (2 ', 4'-dibromo-4-biphenylyl) -butane 1-Phthalimido-3-p-phenoxyphenyl-butane 1-phthalimido-3- (4-o-fluorophenoxyphenyl) butane 1-phthalimido-3- (4-p-fluorophenoxyphenyl) butane 1-phthalimido-3- (4-p-chlorophenoxyphenyl) -butane 1-phthalimido-3- (4-p-chlorophenoxyphenyl) -butane, F. 60-62 ° 1-phthalimido-3- (4-p-bromophenoxyphenyl) -butane 1-phthalimido-3- (4-p-bromophenoxyphenyl) -butane 1-Phthalimido-3-E 4- (2,4-difluorophenoxy) phenyl] butane 1-phthalimido-3- [4- (2,4-dichlorophenoxy) phenyl] butane l-phthalimido-3- [4- (2,4-dibromophenoxy) phenyl3-butane l- (l-imidazolyl) -2- (4-p-chlorophenoxyphenyl) propane, Fumarate, F, 135-1370 1- (1-rmidazolyl) -3-p-biphenylyle-butane 1- (1-imidazolyl) -3- (2'-fluoro-4-biphenylyl) -butane 1- (1-imidazolyl) -3- (4'-fluoro-4-biphenylyl) -butane, m.p. 101-103 ° 1- (1-imidazolyl) -3- (2'-chloro-4-biphenylyl) - butane 1- (1-Imidazolyl) -3- (4'-chloro-4-biphenylyl) -butane m.p. 129-131 ° 1- (1-Imidazolyl) -3- (2'-bromo-4-biphenylyl) -butane 1- (1-Imidazolyl) -3- (4'-bromo-4-biphenylyl) -butane, hydrochloride, m.p. 230-2320 1- (1-imidazolyl) -3- (2 ', 4'-difluoro-4 -biphenylyl) -butane Hydrochloride, F, 81-830 l- (l-imidazolyl) -3- (2 ', 4' ~ dichloro ^ 4 ~ biphenylyl) -butane 1- (1-imidazolyl) -3- (2 ', 4'-dibromo-4-biphenylyl) -butane 1- (1-imidazolyl) -3-p-phenoxyphenyl-butane 1- (1-imidazolyl) -3- (4-o-fluorophenoxyphenyl) -butane 1- (1-imidazolyl) -3- (4-p-fluorophenoxyphenyl) -butane 1- (1-Imidazolyl) -3- (4-o-chlorophenoxyphenyl) -butane 1- (1-imidazolyl) -3- (4-p-chlorophenoxyphenyl) -butane JF.66-7oQ 1- (1-imidazolyl) -3- (4-o-bromophenoxyphenyl) butane 1- (1-imidazolyl) -3- (4-p-bromophenoxyphenyl) -butane 1- (1-Imidazolyl) -3- [4- (2,4-difluorophenoxy) phenyl] butane 1- (1-imidazolyl) -3- [4- (2,4-dichlorophenoxy) phenyl] butane 1- (1-Imidazolyl) -3- [4- (2,4-dibromophenoxy) phenyl] butane, Example 48 Analogous to the example 47 is obtained by reducing the corresponding hydroxyamines with HJ: 1-di- n-propylamino- 3-p- biphenylyl-butane 1-di-n-propylamino-3- (4'-fluoro-4-biphenylyl) -butane 1-di-n-propylamino-3- (4'-chloro-4-biphenylyl) - butane 1-di-n-propylamino-3- (4-4-chlorophenoxy-phenyl) -butane 1-diisopropylamino-3-p-biphenylyl-butane 1-Diisopropylamino-3- (4'-fluoro-4-biphenylyl) -butane 1-Diisopropylamino-3- (4'-chloro-4-biphenylyl) -butane 1-Di-isopropylamino-3- (4-p-chlorophenoxy-plieny 1) - butane 1-di-n-butylamino-3-p-biphenylyl-butane 1-di-n-butylamino-3 (4'-fluoro-4-bipenyly 1-di-n-butylamino-3- (4'-chloro-4-biphenylyl) butane 1-di-n-butylamino-3- (4-p-chlorophenoxy-phenyl) -butane l-diisobutylamino-3-p-biphenylyl-butane-1-diisobutylamino-3- (4'-fluoro-4-biphenylyl) - butane 1-diisobutylamino-3- (4'-chloro-4-biphenylyl) -butane l-diisobutylamino-3- (4-p-chlorophelloxyphenyl) ~ butane 1-di-n -pentylamino-3-p-biphenylyl-butane l-di-n -pentylamino-3- (4'-fluoro-4-biphenylyl) -butane 1-Di-n -pentylamino-3- (4'-chloro-4-biphenylyl) -butane 1-Di-n -pentylamino-3- (4-p-chlorophenoxyphenyl) -butane 1-di-n-hexylamino-3-p-biphenylyl-butane 1-di-n-hexylamino-3- (4'-fluoro-4-biphenylyl) -butane 1-di-n-hexylamino-3- (4'-chloro-4-biphenylyl) -butane l-di-n-hexylamino-3- (4-p-chlorophenoxyphenyl) -butane 1- (2-Dimethylanino-ethylamine) -3-p-biphe l-t2-dimethylamino-ethylamino) -3- (4'-fluoro-4-biphenylyl) -butane l- (2-Dimethylamino-ethylamino) -3- (4'-chloro-4-biphenylyl) -butane 1- (2-dimethylamino-ethylamino) -3- (4-p-chlorophenoxyphenyl) butane 1- (2-diethylamino-ethylamino) -3-p-biphenylyl-butane 1- (2-diethylamino-ethylamino) -3- (4'-fluoro-4-biphenylyl) ~ butane 1- (2-diethylamino-ethylamino) -3- (4'-chloro-4-biphenylyl) butane.

1- (2-diethylamino-ethylamino) -3- (4-p-chlorophenoxyphenyl) -butane 1- (3-dimethylar, ino-propylamino) -3-p biphenylyl ~ butane 1- (3-dimethylamino-propylamino) -3- (4'-fluoro-4-biphenyl) -butane 1- (3-dimethylamino-propylamino> 3- (4'-chloro-4-biphenylyl) -butane 1- (3-Dimethylamino-propylamino) -3- (4p-chlorophenoxy-pheny1) -butane 1- (2-methylpiperidino) -3-p-biphenylyl-butane 1- (2-methylpiperidino) -3- (4'-fluoro-4-biphenylyl) -butane 1- (2-methylpiperidino) -3- (4'-chloro-4-biphenylyl) -butane 1- (2-methylpiperidino) -3- (4-p -chlorophenoxyphenyl) -butane 1- (3-methylpiperidino) -3-p -biphenylyl-butane 1- (3-Methylpiperidino) -3- (4-fluoro-4-biphenylyl) -butane 1- (3-Methylpiperidino) -3- (4'-chloro-4- biphenylyl) -butane 1- (3-methylpiperidino) -3- (4-p -chlorophenoxyphenyl) -butane 1- (2,6-dimethylpiperidino) -3-p -biphenylyl-butane 1- (2,6-Dimethylpiperidino) -3- (4'-chloro-4-biphenylyl) -butane 1- (2,6-Dimethylpiperidino) -3- (4'-chloro-4-biphenylyl) -butane 1- (2,6-Dimethylpiperidino) -3- (4-p -chlorophenoxyphenyl) -butane 1- (4-Methyl-piperazino) -3-p -biphenylyl-butane 1- (4-Methyl-piperazino) -3- (4'-fluoro-4-biphenylyl) -butane 1- (4-Methyl-piperazino) -3- (42-chloro-4-biphenylyl) -butane 1- (4-methyl-piperaSino) -3- (4-p-chlorophenoxyphenyl) butane 1- (4-ethyl-piperazino) -3-p-biphenylyl) -butane 1- (4-ethyl-piperazino) -3- (4'-fluoro-4-biphenylyl) -butane 1- (4-ethyl-piperazino) -3- (4'-chloro-4-biphenylyl) -butarS t 4-ethyl-piperazino) -3- (4-p-chlorophenoxyphenyl) -butane 1- (4-n-hexyl-piperazino) -3-p-biphenylyl-butane 1- (4-n-Hexyl-piperazino) -3 ~ (4 '~ fluoro-4-biphenylyl) -butane 1- (4-n-Hexyl-piperazino) -3- (4'-chloro-4-biphenylyl) -butane 1- (4-n-Hexyl-piperazino) -3- (4-p-chlorophenoxyphenyl) -butane 1- [4- (2-Hydroxyethyl) -piperazino] -3-p-biphenylyl-butane 1-4- (2-hydroxyethyl) piperazino] -3- (4'-fluoro-4-biphenylpl) -butane 1- [4- (2-hydroxyethyl) -piperazino] -3- (4'-chloro-4 -biphenylyl) butane 1- [4- (2-hydroxyethyl) piperazino] -3- (4-p-chlorophenoxyphenyl) butane.

Example 49 A solution of 24.1 g of 3- (4'-fluoro-4-biphenylyl) -2-buten-1-ylamine in 500 ml of ethyl acetate is 10 g of 5% Pd-C at 200 and normal pressure up to Hydrogenated at the end of the hydrogen uptake.

It is filtered and evaporated to give 3- (4'-fluoro-4-biphenylyl) butylamine, Hydrochloride, m.p. 222-224 °.

Example 50 3.71 g of 1-phthalimido-3-p-biphenylyl-butan-3-ol are dissolved in 20 ml of acetic acid, added dropwise with stirring at 200 with a solution of 0.8 g of chlorine in 20 ml of acetic acid, stir for another hour and evaporate. To Customary work-up gives l-phthalimido-3- (4'-chloro-4-biphenylyl) -butan-3-ol, 177-179 °, Example 51 Analogously to Example 50, 1-piperidino-3-p-biphenylylbutan-3-ol is obtained l-piperidino-3- (4'-bromo-4-biphenylyl) -butan-3-ol with the equivalent amount of bromine in acetic acid, F. 89-91o Example 52 A solution of 2.25 g of 3-p-biphenylyi-butylamine and 1.5 g Benzaldehyde in 25 ml of benzene is boiled on a water separator for 2 hours. The solution of the l-benzylidene-amino-3-pbiphenylylbutane obtained is mixed with 5 g of methyl iodide 12 Heated to 1500 hours in the tube and then evaporated. The Quaternary received Salt is boiled in 90% ethanol for 10 minutes.

It is evaporated again, taken up in dilute hydrochloric acid and extracted the split off benzaldehyde with ether.

The acidic aqueous solution is made alkaline with sodium hydroxide solution and worked up as usual. 1-methylamino-3-p-biphenylyl-butane is obtained.

Example 53 Rin mixture of 2.62 g of 3-p-Bipheny1ylutyRamin-hydroehlorld, 5 ml of formic acid, 0.7 g of sodium formate and 4 ml of 40% formaldehyde solution is used Heated to 60 ° for 3 hours and then to 100 ° for 12 hours. After the usual work-up l-dimethylamino-3-p-biphenylyl-butane is obtained, analogously from the corresponding primary amines: l-Dimethylamino-3- (2'-fluoro-4-biphenylyl) -butane 1-Dimethylamino-3- (4'-fluoro-4-biphenylyl) -butane 1-Dimethylamino-3- (2'-chloro-4-biphenylyl) -butane 1-Dimethylamino-3- (4'-bromo-4-biphenylyl) -butane 1-Dimethylamino-3- (2'-bromo-4-biphenylyl) -butane 1-Dimethylamino-3- (4'-bromo-4-biphenylyl) -butane 1-Dimethylamino-3- (2 ', 4'-difluoro-4-biphenylyl) -butane l-Dimethylamino-3- (2 ', 4t ~ dichloro ~ 4-biphenylyl) ~ butane l-Dimethylamino-3- (2', 4'-dibromo-4-biphellylyl) butane 1-Dimethylamino-3-p-phenoxyphenyl-butane 1-Dimethylamino-3- (4-o-fluorophenoxyphenyl) butane 1-Dimethylamino-3- (4-p-fluorophenoxyphenyl) -butane 1-Dimethylamino-3- (4-o-chlorophenoxyphenyl) -butane 1-Dimethylamino-3- (4-p-chlorophenoxy-pllenyl) -butane 1-Dimethylamino-3- (4-o-bromophenoxyphenyl) -butane 1-Dimethylamino-3- (4-p-bromophenoxyphenyl) -butane 1-Dimethylamino-3- [4- (2S4-difluorophenoxyFphenylI-butall 1-Dimethylamino-3- [4- (2,4-dichlorophenoxy) -phenyl] -butane 1-Dimethylamino-3- [4- (2,4-dibromophenoxy! -phenyl-1-butane.

Example 54 A mixture of 2.67 g l isopropylamino-3-p-biphenylylbutane, 12 ml of formic acid and 2 g of 40% formaldehyde solution is then set to 600 for 3 hours Heated to 1000 for 12 hours and then evaporated. After the usual work-up 1- (N-methyl-N-isopropylamino) -3-p-biphenylyl-butane is obtained.

Example 55 A mixture of 2.25 g of 3-p-biphenylyl-butylamine, 1.38 g of potassium carbonate, -2.53 g of 1,5-dibromopentane and 15 ml of n-butanol are added with stirring Cooked for 24 hours. It is filtered off with suction, the filtrate is evaporated and worked up as usual and receives l-piperidino-3-p-biphenylylbutane.

Example 56 A mixture of 2.25 g of 3-p-biphenylyl-butylamine is stirred, 20 ml of benzene, 1 ml of pyridine and 1 ml of acetic anhydride 3 hours at 250. According to the usual Working up gives l-acetamido-3-p-biphenylyl-butane.

Analogously, acetylation gives the corresponding primary or secondary amines: 1-acetamido-3- (2 1-fluoro-4-biphenylyl) -butane 1-acetamido-3- (4'-fluoro-4-biphenylyl) -butane l-acetamido-3- (2'-chloro-4-biphenylyl) -butane 1-acetamido-3- (4'-chloro-4-biphenylyl) -butane, F. 118-1200 1-Acetamido-3- (2'-bromo-4-biphenylyl) -butane 1-acetamido-3- (4'-bromo-4-biphenylyl) -butane 1-acetamido-3- (2 ', 4'-difluoro-4-biphenylyl) -butane 1-acetamido-3- (2', 4'-dichloro-4-biphenylyl) -butane 1-Acetamido-3- (2 ', 4'-dibromo-4-biphenylyl) -butane 1-Acetamido-3-p-phenoxyphenyl-butane 1-acetamido-3- (4-o-fluorophenoxyphenyl) butane 1-acetamido-3- (4-p-fluorophenoxyphenoxy) butane 1-acetamido-3- (4-o-chlorophenox-phenyl) -butane 1-acetamido-3- (4-p-chlorophenoxyphenyl) -butane l-acetamido-3- (4-o-bromophenoxyphenyl) -butane l-acetamido-3- (4-p-bromophenoxyphenyl) -butane 1-Acetamido-3- [4- (2,4-difluorophenoxy) phenyl] butane 1-acetamido-3- [4- (2,4-dichlorophenoxy) phenyl] butane 1-Acetamido-3- [4- (2S4-dibromophenoxy) -phenyl] -butane 1-acetamido-3-p-biphenylyl-3-butanol 1-acetamido-3- (2'-fluoro-4-biphenylyl) -3-butanol 1-acetamido-3- (4'-fluoro-4-biphenylyl) -3-butanol 1-acetamido-3- (2'-chloro-4-biphenylyl) -3-butanol 1-acetamido-3- (4'-chloro-4-biphenylyl) -3-butanol 1-acetamido-3- (2'-bromo-4-biphenylyl) -3-butanol 1-acetamido-3- (4'-bromo-4-biphenylyl) -3-butanol 1-acetamido-3- (2 ', 4'-difluoro-4-biphenylyl) -3-butanol 1-acetamido-3- (2 ', 4'-dichloro-4-biphenylyl) -3-butanol 1-acetamido-3- (2', 4'-dibromo-4-biphenylyl) -3-butanol 1-acetamido-3-p-phenoxyphenyl-3-butanol 1-acetamido-3- (4-o-fluorophenoxyphenyl) -3-butanol 1-Acetamido-3- (4-p-fluorophenoxy-phenyl) -3-butanol 1-acetamido-3- (4-o-chlorophenyl .. y-phenyl) -3-butanol 1-acetamido-3- (4-p-chlorophenoxyphenyl) -3-butanol 1-acetamido-3- (4-o-bromophenoxyphenyl) -3-butanol 1-acetamido-3- (4-p-bromophenoxyphenyl) -3-butanol 1-acetamido-3- [4- (2,4-difluorophenoxy) phenyl] -3-butanol 1-Acetamido-3- [4- (2,4-dichlorophenoxy) -phenyl1-3-butanol 1-acetamido-3- [4- (2,4-dibromophenoxy) -phenyl] -3-butanol 1- (N-methyl-acetamido) -3-p-biphenylyl-butan-3-ol.

Example 57 A mixture of 2.6 g of 3- (4'-chloro-4-biphenylyl) butylamine, 12 ml of pyridine and 1 ml of acetyl chloride stand for 2 hours, decomposed with water, works as usual and receives 1-acetamido-3- (4'-chloro-4-biphenylyl) -butane, F. 118120O.

Analogously, acylation of the corresponding primary or secondary amines: l-propionamido-3-p-biphenylyl-butane 1-propionamido-3- (4'-fluoro-4-biphenylyl) -butane 1-propionamido-3- (4'-chloro-4-biphenylyl) -butane 1-propionamido-3- (4-p-chlorophenoxyphenyl) -butane 1-butyramido-3-p-biphenylyl-butane 1-butyramido-3- (4'-fluoro-4-biphenylyl) -b 1-butyramido-3- (4'-chloro-4-biphenylyl) butane 1-butyramido-3- (4-p-chlorophenoxyphenyl) butane 1-isobutyramido-3-p-biphenylyl-butane 1-Isobutyramido-3- (4'-fluoro-4-biphenylyl) -butane 1-Isobutyramido-3- (4'-chloro-4-biphenylyl) -butane 1-Isobutylamido-3- (4-p-chlorophenoxy-phenyl) -butane 1-propionamido-3-p-biphenylyl-butan-3-ol 1-propionamido-3- (4'-fluoro-4-biphenylyl) -butan-3-ol 1-propionamido-3- (4'-chloro-4-biphenylyl) -butan-3-ol 1-propionamido-3- (4-p-chlorophenoxyphenyl) -butan-3-ol 1-butyramido-3-p-biphenylyl-butan-3-ol 1-Butyramido-3- (4'-fluoro-4-biphenylyl) -butan-3-ol 1-Butyramido-3- (4'-chloro-4-biphenylyl) -butan-3-ol 1-butyramido-3- (4-p-chlorophenoxy-phenyl) -butan-3-ol 1-isobutyramido-3-p-biphenylyl-butan-3-ol 1-Isobutyramido-3- (d'-flucr-4-biphenylyl) -butan-3-ol 1-Isobutyramido-3- (4'-chloro-4-biphenylyl) -butan-3-ol l-Isobutyramido-3- (4-p-chlorophenoxy-phenyl) -butan-3-ol 1- (N-methyl-propionamido) - 3-p-biphenylyl-butan-3-o1 l-raleramido-3-p-biphenylyl-butan-3-ol.

1-capronamido-3-p-biphenylyl-butan-3-ol.

Example 58 2.25 g of 3-p-biphenylyl-butylamine and 5 g of phthalic acid hydride are heated 9 minutes to 1200, cools down, works as usual on un receives 1-phthalimido-3-o-biphenylyl-butane, F. 120 - 123 °.

Example 59 A solution of 28.5 g of 1-acetamido-3- (4'-fluoro-4-biphenylyl) -butane in 800 ml of 10% methanolic KOH solution is boiled for 48 hours. One concentrates the solution works up with water and ether and receives 3- (4'-fluoro-4-biphenylyl) -butylamine; Hydrochloride, m.p. 222-2240.

Example 60 37.3 g of 1-phthalimido-3- (4'-fluoro-4-biphenylyl) -butane are boiled with 400 ml of 20% aqueous hydrochloric acid for 6 hours, evaporated, works with sodium hydroxide solution and ether and receives 3- (4'-fluoro-4-biphenylyl) -butylamine, hydrochloride, F. 222-2240.

Example 6i A solution of 3.55 g of 1-phthalimido-3-p-biphenylyl-butane and 1.25 ml of 80% hydrazine hydrate in 40 ml of methanol is boiled for 4 hours. By Addition of water becomes 1- (3,4-DI-hydro-4-oxo-1-phthalazinyl-amino) -3-p-biphenylyl-butane failed.

Similarly, ester corresponding phthalimides are obtained by hydrazinolysis: 1- (3,4-Dihydro-4-oxo-1-phthalazinyl-amino) -3- (2'-fluoro-4-biphenylyl) -butane 1- (3,4-Dihydro-4-cxc-1-phthalazinyl -amino) "3" luorb 4-biphenylyl) butane, m.p. 150-1680 1- (3,4-dihydro-4-oxo-1-phthalazinyl-amino) -3- (2'-chloro-4-biphenylyl) butane 1- (3,4-Dihydro-4-oxo-1-phthalazinyl-amino) -3- (4'-chloro-4-biphenylyl) -butane, F. 1950 l- (3,4-dihydro-4-oxo-l-phthalazinyl-amino) -3- (s'-bromo-4-biphenylyl) -butane 1- (3,4-dihydro-4-oxo-1-phthalazinyl-amino) -3- (4'-bromo ~ 4-biphenylyl) -butane 1- (3,4-Dihydro-4-oxo-1-phthalazinlyl-amino) -3- (2 ', 4'-difluoro-4-biphenylyl) butane 1- (3,4-Dihydro-4-oxo-1-phthalazinyl-amino) -3- (2 ', 4'-dichloro-4-biphenylyl) butane 1- (3,4-Dihydro-4-oxo-1-phthalazinlyl-amino) -3- (2 ', 4'-dibromo-4-biphenyly 1) - butane l- (3,4-Dihydro-4-oxo l-phthalazinyl-amino) -3-p-phenoxyS phenyl-butane l- (3,4-Dihydro-4-oxo-l-phthalazinyl-amino) -3- ( 4-o-fluorophenoxy-phcnyl) -butane 1- (3, 4-dihydro-4-oxo-1-phthalazinyl-amino) -3- (4-p-fluorophenoxyphenyl) -butane l- (3,4-dihydro-4-oxo-l-phthalazinyl-amino) -3- (4-o-chlorophenoxyphenyl) -butane l- (3,4-dihydro-4-oxo-l-phthalazinyl- amino) -3- (4-p-chlorophenoxyphenyl) -butane l- (3,4-dihydro-4-oxo-l-phthalazinyl-amino) -3- (4-o-bromo ~ phenoxyphenyl) -butane l- (3,4-dihydro-4-oxo-l- phthalazinyl-amino) -3- (4-p-bromophenoxyphenyl) -butane 1- (3,4-Dihydro-4-oxo-1-phthalazinyl-amino) -3- [4- (2,4-difluorophenoxy) phenyl] butane 1- (3,4-Dihydro-4-oxo-1-phthalazinyl-amino) -3- [4- (2,4-dichlorophenoxy) phenyl] butane 1- (3,4-Dihydro-4-oxo-1-phthalazinyl-amino) -3-E4- (2,4-dibromophenoxy) phenyl] butane.

Example 62 38.95 g of 1-phthalimido-3- (4'-chloro-4-biphenylyl) butane are boiled with 12.2 ml of 8Q 4% hydrazine hydrate in 400 ml of ethanol 2 hours with stirring, water is added, the mixture is cooled and the 1- (3,4-dihydro-4-oxo-1-phthalazinyl-amino) -3 obtained is filtered (4'-chloro-4-biphenylyl) -butane (F. 1950), dissolve it in 450 ml of ethanol and 450 ml 37% hydrochloric acid and boil for 30 minutes while stirring. One concentrates the solution, works with sodium hydroxide solution and ethyl acetate and receives 3- (4'-chloro-4-biphenylyl) butylamine. Hydrochloride, m.p. 256-2590.

Example 63 a) Analogously to Example 1, 1-acetamido-3- (4'-chloro-4-biphenylylj-butane is obtained and LiAlH4 l-ethylamio-3- (4'-chloro-4-biphenylyl) -butane.

b) As in Example 26, 1-ethylamino-3- (4'-chloro-4-biphenylyl) butane is acetylated to l- (N-ethyl-acatamido) -3- (4'-chloro-4-biphenylyl) butane, c) as in Example 1 the 1- (N-ethylcacetamido) -3- (4'-chloro-4-biphenylyl) butane is reduced with LiAlH4 to 1-diethylamino 3- (4'-chloro-4-biphenylyl) butane, mp 42-44 °.

Example 64 A mixture of 2.82 g of l-acetamido-3-p-biphenylyl-butan-3-ol, 0.1 g of p-toluenesulfonic acid and 70 ml of toluene are boiled with a water separator for 2 hours. Customary work-up gives 1-acetamido-3-p-biphenylyl-2-butene.

Analogously, by dehydrating the corresponding alcohols, one obtains: 1-acetamido-3- (2'-fluoro-4-biphenylyl) -2-butene 1-Acetamido-3- (4'-fluoro-4-biphenylyl) -2-butene, m.p. 174-176 ° 1-Acetamido-3- (2'-chloro-4-biphenylyl) -2-butene 1-acetamido-3- (4'-chloro-4-biphenylyl) -2-butene 1-acetamido-3- (2'-bromo-4-biphenylyl) -2-butene 1-Acetamido-3- (4'-bromo-4-biphenylyl) -2-butene 1-acetamido-3- (2 ', 4'-difluoro-4-biphenylylj-2-butene 1-acetamido-3- (2 ', 4'-dichloro-4-biphenylyl) -2-butene 1-acetamido-3- (2', 4'-dibromo-4-biphenylyl) -2-butene 1-acetamido-3-p-phenoxypenyl-2-butene 1-acetamido-3- (4-o-fluorophenoxyphenyl) -2-butene 1-acetamido-3- (4-p-fluorophenoxyphenyl) -2-butene 1-acetamido-3- (4-o-chlorophenoxyphenyl) -2-butene 1-acetamido-3- (4-p-chlorophenoxyphenyl) -2-butene 1-acetamido-3- (4-o-bromophenoxyphenyl) -2-butene 1-acetamido-3- (4-p-bromophenoxyphenyl) -2-butene 1-acetamido-3- [4- (2,4-difluorophenoxy) phenyl3-2-butene 1-acetamido-3- [4- (2,4-dichlorophenoxy) phenyl] -2-butene 1-acetamido-3- [4- (2,4-dibromophenoxy) phenyl] -2-butene.

Example 65 2.25 g of 3-p-biphenylyl-butylamine are dissolved in 30 ml of formic acid, added dropwise at 600 with 10 ml of acetic anhydride with stirring, left overnight stand, works up as usual and receives l-formamido-3-p-biphenylyl-butane.

The following examples relate to pharmaceutical preparations, the amines of the formula I or their acid addition salts contain: Example A: Tablets A mixture of 1 kg of 3- (4'-chloro-4-biphenylyl) butylamine tartrate, 4 kg of lactose, 1,2 kg of potato starch, 0.2 kg of talc and>, 1 kg of magnesium stearate is more common Compressed into tablets in such a way that each tablet contains 100 mg of active ingredient.

Example B: Dragees Analogously to Example A, tablets are pressed which then in the usual way with a coating of sucrose, potato starch, Talc, tragacanth and dye are coated.

Example C: Capsules 5 kg of 3- (4'-fluoro-4-biphenylyl) butylamine hydrochloride are filled in hard gelatin capsules in the usual manner, so that each capsule 250 mg of the active ingredient.

Similarly, tablets, coated tablets and capsules are available that have one or several of the other active ingredients of the formula I and / or their physiologically harmless Contain acid addition salts.

Claims (5)

Claims: 1. Araliphatic nitrogen compounds of the general Formula I R-A-Z 1 wherein R is one unsubstituted or one or more than one F, Cl and / or Br substituted 4-biphenylyl or 4-phenoxyphenyl radical, A -CH (CH3) -CH2- (CH2) n-, -C (CH3) = (CH2) n- or -C (OH) (CH3) -CH2- (CGH2) n-, Z -NR¹R², imindazol-1-yl, phthalimido or 3,4-dihydro-4-oxo-phthalazin-1-yl-amino, R¹ and R² (same or different) in each case H, alkyl, azaalkyl or acyl each having 1 - 6 carbon atoms or together alkylene with 4 - 7 carbon atoms, 3-oxapentamethylene or 3-R³-3-azapentamethylene, R3 H, alkyl or hydroxyalkyl each having up to 6 carbon atoms and n denotes O, 1 or 2, and their physiologically harmless acid addition salts. 2. a) 3-p-Biphenylyl-butylamine. b) 3-p-biphenylyl-3-hydroxy-butylamine. c) 3-p-biphenylyl-2-butenyl-1-amine. d) 2- (4'-fluoro-4-biphenylyl) propylamine. e) 3- (2'-fluoro-4-biphenylyl) butylamine. f) 3- (2'-fluoro-4-biphenylyl) -3-hydroxy-butylamine. g) 3- (4'-fluoro-4-biphenylyl) -butylamine. h) 3- (4'-fluoro-4-biphenylyl) -3-hydroxy-butylamine. i) 3- (4'-Fluoro-4-biphenylyl) -2-butenyl-1-amine. j) 4- (4'-fluoro-4-biphenylyl) pentylamine. k) 3- (4'-chloro-4-biphenylyl) butylamine. l) 3- (4'-chloro-4-biphenylyl) -3-hydroxy-butylamine. m) 3- (4'-chloro-4-biphenylyl) -2-butenyl-1-amine. n) 3- (2 ', 4'-Difluoro-4-biphenylyl-butylamine. o) 3- (2 ', 4'-difluoro-4-biphenylyl) -3-hydroxy-butylamine. pj 3-qZ ', 4 | -Difluoro-4-biphenyly l) -2-butenyl-1-amine. q) 3- (4-p-chlorophenoxyphenyl) butylamine. r) 3- (4-p-Chlorophenoxyphenyl) -3-hydroxy-butylamine. s) 1-Diethylamino-3- (4'-chloro-4-biphenylyl) -butane. t) 1- (2-diethylamine-ethylamino) -3 (4 '-fluoro-4-biphenylyl) -butan-3-ol. u) 1-Acetamido-3- (4'-chloro-4-biphenylyl) -butane. v) 1-acetamido-3- (4'-fluoro-4-biphenylyl) -2-butene. w) 1-piperidino-3-p-biphenylyl-butan-3-ol. x) 1-piperidino-3- (4'-fluoro-4-biphenylyl) -butane. y) 1-piperidino-3- (4'-fluoro-4-biphenylyl) -butan-3-ol. z) 1-Piperidino-3- (4'-bromo-4-biphenylyl) -butan-3-ol. za) I-piperidino-3- (4-p-chlorophenoxyphenyl) -butan-3-ol. e.g. 1-piperidino-3- (4-p-bromophenoxyphenyl) -butan-3-ol. zc) 1- (4-methylpiperidino) -3- (4-p-bromophenoxyphenyl) -butan-3-ol. zd) 1-Morpholino-3-p-biphenylyl-butan-3-ol. ze) 1-Morpholino-3-p- (4'-fluoro-4-biphenylyl) -butane. zf) 1-Morpholino-3-p- (4'-fluoro-4-biphenylyl) -butan-3-ol. zg) 1-Morpholino-3-p- (4'-chloro-4-biphenylyl-butane. zh) 1-Morpholino-3- (4'-chloro-4-biphenylyl) -butan-3-ol. zi) 1-Morpholino-3- (4'-bromo-4-biphenylyl) -butan-3-ol. zj) 1-Morpholino-3- (4-p-chlorophenoxyphenyl) -butane. zk) 1-morpholino-3- (4-p-chlorophenoxyphenyl) -butan-3-ol. zl) 1- [4- (2-hydroxyethyl) piperazino] -3- (4'-fluoro-4-biphenylyl) -butan-3-ol. zm) 1- (1-imidazolyl) -3- (4'-fluoro-4-biphenylyl) -butan-3-ol. zn) 1-phthalimido-3-p-biphenylyl-butane. zo) 1-Phthalimido-3-p-biphenylyl-butan-3-ol. zp) 1-phthalimido-3- (2'-fluoro-4-biphenylyl) -butane. zq) 1-Phthalimido-3- (2'-fluoro-4-biphenylyl) -butan-3-ol. zr) 1-phthalimido-3- (4'-fluoro-4-kiphenylyl) -butane. zs) 1-Phthalimido-3- (4'-fluoro-4-biphenylyl) -butan-3-ol. zt) 1-phthalimido-3- (4'-chloro-4-biphenylyl) -butane. to) 1-phthalimido-3- (4'-chloro-4-biphenylyl) -butan-3-ol. zv) 1-phthalimido-3- (4'-chloro-4-biphenylyl) -2-butene. zw) 1-phthalimido-3- (2 ', 4'-difluoro-4-biphenylyl) -butan-3-ol. zx) 1-Phthalimido-3- (4-p-chlorophenoxyphenyl) -butane. zy) 1-Phthalimido-3- (4-p-chlorophenoxyphenyl) -butan-3-ol. zz) 1- (3,4-Dihydro-4-oxo-phthalazin-1-yl-amino) -3- (4 1-fluoro-4-bipehnylyl) -butane. zza) 1- (3,4-Dihydro-4-oxo-phthalazin-1-yl-amino) -3- (4'-chloro-4-biphenylyl) -butane. 3. Process for the production of araliphatic nitrogen compounds of the general formula I R-A-Z 1 wherein R is an unsubstituted or a single or 4-biphenylyl or 4-phenoxyphenyl radical substituted several times by F, Cl and / or Br, A -CH (CH3) -CH32- (CH2) n-, -C (CH3) = CH-CH2) n- or -C (OH) (CH3) -CH2- (CH2) n-, Z -NR12, Imidazol-1-yl, phthalimido or 3,4-dihydro-4-oxo-phthalazin-1-yl-amino, R¹ and R² (identical or different) in each case H, alkyl, azaalkyl or acyl, each with 1 - 6 carbon atoms or together alkylene with 4 - 7 carbon atoms, 3-oxapentamethylene or 3-R³-3-azapentamethyl R3 denotes H, alkyl or hydroxyalkyl each with up to 6 carbon atoms and n denotes O, 1 or 2, as well as their physiologically harmless acid addition salts, characterized in that that a compound of the general formula II R-Q wherein Q is one of the group -A-Z Reducible radical means and R, A and Z have the meanings given above with treated with a reducing agent or that one has a compound that is general Formula I corresponds, in which, however, the amino and / or the hydroxyl group is functional modified form is present, treated with a solvolyzing agent or that a compound of the general formula III R - E III in which E -C (CH3) (OH) - (CH2) m-CH-CH2, -CH (CH3) - (CH2) m CH = CN or -A-X, m 0 or 1, X Cl, Br, J, OH or reactive Functionally modified OH is and R and A are as defined above have with a compound of the general formula H-Z or a reactive one Reacts derivative of such a compound or that an amine of the general formula IV R-A-N (CH2CH2OH) -CH2CH2X IV in which R, A and X have the meanings given above have treated with an HX-releasing agent or that one has an amine of the general Formula V R-A-N (CH2CH2X) 2 V in which R, A and X have the meanings given above with a compound of the general formula H2NR3 or that a compound of the general formula VI R4-A-Z VI where R4 is one or more times through NH2 are optionally additionally one or more times through F, C1 and / or Br is substituted 4-biphenylyl or 4-phenoxyphenyl radical and A and Z denote The meanings given above have diazotized and then the diazonium salt obtained treated with a halogenating agent or that a compound of the general Formula VII -A-Z VII or a salt of such a compound with a compound of the general formula VTIT R6-Q² VIII or a salt of such a compound wherein one of the groups Q1 or Q2 is OH, the other of these groups R5 is an unsubstituted one or a p-phenylene radical which is monosubstituted or polysubstituted by F, Cl and / or Br and R6 is one unsubstituted or one or more than one by F, Cl and / or Br are substituted phenyl radicals and A, Z and X have the meanings given above have implemented and that optionally a hydroxy compound obtained of the formula I / A = -C (OH) (CH3) -CH2- (CH2) -7 with a dehydrating agent and / or a compound of the formula I obtained ZA = -C (OH) (CH3) -CH2- (CH2) n- or -C (CH3) = CH- (CH2) n-7 treated with a reducing agent and / or into a compound obtained Formula I by treating one or more with chlorinating or brominating agents Introduces chlorine oaer bromine atoms and / or in a compound of the formula obtained 1. the radical Z by treatment with alkylating, acylating, solvolyzing and / or reducing agent converts into another radical Z and / or a obtained one Base of the formula I by treatment with an acid in one of its physiologically harmless ones Converts acid addition salts. 4. Process for the production of pharmaceutical preparations, characterized in that that a compound of the formula I and / or one of its physiologically harmless Acid addition salts together with at least one solid, liquid or semi-liquid Auxiliary or carrier and optionally together with a further active ingredient into a suitable dosage form. 5. Pharmaceutical preparation containing a compound of the general Formula I and / or one of its physiologically acceptable acid addition salts.