Tetrahydrocarbazole derivatives of the general formula I ##STR1## in which Thc is a 1,2,3,4-tetrahydro-3-carbazolyl radical which can be substituted once or twice by alkyl, O-alkyl, S-alkyl, SO-alkyl, SO.sub.2 -alkyl, OH, F, Cl, Br, CF.sub.3 and/or CN or by a methylenedioxy group, the two radicals Y are each H or together are a C--C bond, one radical Z is Ar and the other radical Z is H, A is --CH.sub.2 -- or --CH.sub.2 CH.sub.2 -- and Ar is a phenyl group which is unsubstituted or substituted once or twice by alkyl, O-alkyl, S-alkyl, SO-alkyl, SO.sub.2 -alkyl, OH, F, Cl, Br, CF.sub.3 and/or CN or by a methylenedioxy group, or is a 2- or 3-thienyl radical, and in which the alkyl groups each have 1-4 C atoms, and their physiologically acceptable acid addition salts have effects on the central nervous system.

The invention relates to new tetrahydrocarbazole derivatives. 
SUMMARY OF THE INVENTION 
It is an object of this invention to provide new compounds which can be 
used for producing valuable medicaments. 
Upon further study of the specification and appended claims, further 
objects and advantages of this invention will become apparent to those 
skilled in the art. 
These objects have been achieved by providing compounds of formula I 
##STR2## 
in which Thc is a 1,2,3,4-tetrahydro-3-carbazolyl radical which can be 
substituted once or twice by alkyl, O-alkyl, S-alkyl, SO-alkyl, SO.sub.2 
-alkyl, OH, F, Cl, Br, CF.sub.3 and/or CN or by a methylenedioxy group, 
the two radicals Y are each H or together are a C--C bond, one radical Z 
is Ar and the other radical Z is H, A is --CH.sub.2 -- or --CH.sub.2 
CH.sub.2 -- and Ar is a phenyl group which is unsubstituted or is 
substituted once or twice by alkyl, O-alkyl, S-alkyl, SO-alkyl, SO.sub.2 
-alkyl, OH, F, Cl, Br, CF.sub.3 and/or CN or by a methylenedioxy group, or 
is a 2- or 3-thienyl radical, and in which the alkyl groups each have 1-4 
C atoms, and their physiologically acceptable acid addition salts. 
It has been found that the compounds of the formula I and their 
physiologically acceptable acid addition salts have valuable 
pharmacological properties. Thus, in particular, they have effects on the 
central nervous system, especially dopamine-stimulating (antiparkinsonism) 
effects. Specifically, the compounds of the formula I induce contralateral 
turning behaviour in rats with hemiparkinsonism (which may be demonstrated 
by the method of Ungerstedt et al., Brain Res. 24, (1970), 485-493) and 
they inhibit the binding of tritiated dopamine agonists and antagonists to 
striatal receptors (which may be demonstrated by the method of Schwarcz et 
al., J. Neurochemistry, 34, (1980), 772-778 and Creese et al., European J. 
Pharmacol., 46, (1977), 377-381). In addition, the compounds inhibit the 
linguomandibular reflex in the anaesthetised rat (which may be 
demonstrated by methods derived from Barnett et al., European J. 
Pharmacol. 21, (1973), 178-182, and from Ilhan et al., European J. 
Pharmacol. 33, (1975) 61-64). Moreover, analgesic and hypotensive effects 
occur; thus after intragastric administration of the compounds, the 
directly measured arterial blood pressure of catheterized, conscious 
spontaneously hypertensive rats (strain SHR/NIH-MO/CHB-EMD; for method, 
see Weeks and Jones, Proc. Soc. Exptl. Biol. Med. 104, (1960), 646-648) is 
decreased. 
Thus, compounds of the formula I and their physiologically acceptable acid 
addition salts can be used as active compounds in medicaments and also as 
intermediate products for the preparation of other active compounds in 
medicaments. 
The invention relates to the tetrahydrocarbazole derivatives of the formula 
I and their physiologically acceptable acid addition salts. 
DETAILED DISCUSSION 
In the radicals Thc and Ar, alkyl is preferably methyl, but is also ethyl, 
n-propyl, isopropyl, n-butyl, isobutyl, sec.-butyl or tert.-butyl. O-Alkyl 
is preferably methoxy, but is also ethoxy, n-propoxy, isopropoxy, 
n-butoxy, isobutoxy, sec.-butoxy or tert.-butoxy, S-alkyl is preferably 
methylthio, but is also ethylthio, n-propylthio, isopropylthio, 
n-butylthio, isobutylthio, sec.-butylthio or tert.-butylthio. SO-Alkyl is 
preferably methylsulfinyl, but is also ethylsulfinyl, n-propylsulfinyl, 
isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, sec.-butylsulfinyl 
or tert.-butylsulfinyl. SO.sub.2 -Alkyl is preferably methylsulfonyl, but 
is also ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, 
n-butylsulfonyl, isobutylsulfonyl, sec.-butylsulfonyl or 
tert.-butylsulfonyl. 
The radical Thc is, in particular, an unsubstituted 
1,2,3,4-tetrahydro-3-carbazolyl radical. However, if Thc is a substituted 
1,2,3,4-tetrahydro-3-carbazolyl radical, then it is preferably substituted 
once, in particular in the 6- or 7-position. Substitution is also possible 
at the 1-, 2-, 3-, 4-, 5-, 8- or 9-position. Preferred disubstituted 
1,2,3,4-tetrahydro-3-carbazolyl radicals are substituted in the 
6,7-positions; disubstitution is also possible in the 1,1-, 1,2-, 1,3-, 
1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 1,9-, 2,2-, 2,3-, 2,4-, 2,5-, 2,6-, 2,7-, 
2,8-, 2,9-, 3,4-, 3,5-, 3,6-, 3,7-, 3,8-, 3,9-, 4,4-, 4,5-, 4,6-, 4,7-, 
4,8-, 4,9-, 5,6-, 5,7-, 5,8-, 5,9-, 6,8-, 6,9-, 7,8-, 7,9- or 
8,9-positions. In all these cases, the substituents can be identical or 
different. 
Specifically, the preferred substituents in the benzene ring in the radical 
Thc are methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, OH, F, Cl, 
Br, CF.sub.3 and CN. Accordingly, some preferred meanings of the radical 
Thc are 1,2,3,4-tetrahydro-3-carbazolyl, also 1-, 2-, 3-, 4-, 5-, 6-, 7-, 
8- or 9-methyl-1,2,3,4-tetrahydro-3-carbazolyl, 1-, 2-, 3-, 4-, 5-, 6-, 
7-, 8- or 9-ethyl-1,2,3,4-tetrahydro-3-carbazolyl, 5-, 6-, 7- or 
8-methoxy-1,2,3,4-tetrahydro-3-carbazolyl, 5-, 6-, 7- or 
8-ethoxy-1,2,3,4-tetrahydro-3-carbazolyl, 5-, 6-, 7- or 
8-methylthio-1,2,3,4-tetrahydro-3-carbazolyl, 5-, 6-, 7- or 
8-ethylthio-1,2,3,4-tetrahydro-3-carbazolyl, 5-, 6-, 7- or 
8-methylsulfinyl-1,2,3,4-tetrahydro-3-carbazolyl, 5-, 6-, 7- or 
8-methylsulfonyl-1,2,3,4-tetrahydro-3-carbazolyl, 5-, 6-, 7- or 
8-hydroxy-1,2,3,4-tetrahydro-3-carbazolyl, 5-, 6-, 7- or 
8-fluoro-1,2,3,4-tetrahydro-3-carbazolyl, 5-, 6-, 7- or 
8-chloro-1,2,3,4-tetrahydro-3-carbazolyl, 5-, 6-, 7- or 
8-bromo-1,2,3,4-tetrahydro-3-carbazolyl, 5-, 6-, 7- or 
8-trifluoromethyl-1,2,3,4-tetrahydro-3-carbazolyl, 5-, 6-, 7- or 
8-cyano-1,2,3,4-tetrahydro-3-carbazolyl, 1,2-, 1,4-, 1,5-, 1,6-, 1,7-, 
1,8-, 1,9-, 2,4-, 2,5-, 2,6-, 2,7-, 2,8-, 2,9-, 4,5-, 4,6-, 4,7-, 4,8-, 
4,9-, 5,6-, 5,7-, 5,8-, 5,9-, 6,7-, 6,8-, 6,9-, 7,8-, 7,9- or 
8,9-dimethyl-1,2,3,4-tetrahydro-3 -carbazolyl, 5-, 6-, 7- or 
8-methoxy-9-methyl-1,2,3,4-tetrahydro-3-carbazolyl, 5-, 6-, 7- or 
8-methylthio-9-methyl-1,2,3,4-tetrahydro-3-carbazolyl, 5-, 6-, 7- or 
8-fluoro-9-methyl-1,2,3,4-tetrahydro-3-carbazolyl, 5-, 6-, 7- or 
8-chloro-9-methyl-1,2,3,4-tetrahydro-3-carbazolyl, 5-, 6-, 7- or 
8-bromo-9-methyl-1,2,3,4-tetrahydro-3-carbazolyl, 5-, 6-, 7- or 
8-trifluoromethyl-9-methyl-1,2,3,4-tetrahydro-3-carbazolyl, 5-, 6-, 7- or 
8-cyano-9-methyl-1,2,3,4-tetrahydro-3-carbazolyl, 1- or 2-methyl-5-, -6-, 
-7- or -8-methoxy-1,2,3,4-tetrahydro-3-carbazolyl, 1- or 2-methyl-5-, -6-, 
-7- or -8-methylthio-1,2,3,4-tetrahydro-3-carbazolyl, 1- or 2-methyl-5-, 
-6-, -7- or -8-fluoro-1,2,3,4-tetrahydro-3-carbazolyl, 1- or 2-methyl-5-, 
-6-, -7- or -8-chloro-1,2,3,4-tetrahydro-3-carbazolyl, 1- or 2-methyl-5-, 
-6-, -7- or -8-bromo-1,2,3,4-tetrahydro-3-carbazolyl, 1- or 2-methyl-5-, 
-6-, -7- or -8-trifluoromethyl-1,2,3,4-tetrahydro-3-carbazolyl, 1- or 
2-methyl-5-, -6-, -7- or -8-cyano-1,2,3,4-tetrahydro-3-carbazolyl, 
6-methyl-7-fluoro-1,2,3,4-tetrahydro-3-carbazolyl, 6-fluoro-7- or 
-9-methyl-1,2,3,4-tetrahydro-3-carbazolyl, 
6-methyl-7-chloro-1,2,3,4-tetrahydro-3-carbazolyl, 
6-chloro-7-methyl-1,2,3,4-tetrahydro-3-carbazolyl, 5-chloro-6- or 
-7-methyl-1,2,3,4-tetrahydro-3-carbazolyl, 5,6-, 5,7-, 5,8-, 6,7-, 6,8- or 
7,8-dimethoxy-1,2,3,4-tetrahydro-3-carbazolyl, 5,6-, 5,7-, 5,8-, 6,7-, 
6,8- or 7,8-dichloro-1,2,3,4-tetrahydro-3-carbazolyl, 
5-trifluoromethyl-6-, -7- or -8-chloro-1,2,3,4-tetrahydro-3-carbazolyl, 
5,6-, 6,7- or 7,8-methylenedioxy-1,2,3,4-tetrahydro-3-carbazolyl. 
The radical A is preferably --CH.sub.2 --. 
The radical Ar is preferably unsubstituted phenyl. When Ar is a substituted 
phenyl group, then it is preferably substituted once. However, it can also 
be substituted twice, it being possible for the substituents to be 
identical or different. Preferred substituents on the phenyl group are 
methyl, F, Cl, Br and trifluoromethyl. Specifically, Ar is preferably 
phenyl, o-, m- or p-fluorophenyl, o-, m- or p-chlorophenyl, o-, m- or 
p-bromophenyl, o-, m- or p-tolyl, o-, m- or p-methoxyphenyl, o-, m- or 
p-trifluoromethylphenyl, also, for example, o-, m- or p-ethylphenyl, o-, 
m- or p-n-propylphenyl, o-, m- or p-isopropylphenyl, o-, m- or 
p-n-butylphenyl, o-, m- or p-isobutylphenyl, also dihalogenophenyl, such 
as 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-difluorophenyl, 2,3-, 2,4-, 2,5-, 
2,6-, 3,4- or 3,5-dichlorophenyl, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 
3,5-dibromophenyl, 2-fluoro-4-chlorophenyl, 2-bromo-4-chlorophenyl; 
dimethylphenyl, such as 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 
3,5-dimethylphenyl; methylchlorophenyl, such as 2-methyl-4-chlorophenyl; 
dimethoxyphenyl, such as 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 
3,5-dimethoxyphenyl; 2,3- or 3,4-methylenedioxyphenyl. 
Accordingly, the invention particularly relates to those compounds of the 
formula I in which at least one of the radicals mentioned has one of the 
meanings indicated above, especially one of the preferred meanings 
indicated above. Some preferred groups of compounds can be expressed by 
the following formulae Ia to Ig which correspond to the formula I and 
wherein the radicals which are not specified have the meaning indicated 
for formula I, but wherein 
in Ia, Thc is 1,2,3,4-tetrahydro-3-carbazolyl, 
methyl-1,2,3,4-tetrahydro-3-carbazolyl, 
methoxy-1,2,3,4-tetrahydro-3-carbazolyl, 
dimethoxy-1,2,3,4-tetrahydro-3-carbazolyl, 
hydroxy-1,2,3,4-tetrahydro-3-carbazolyl, 
dihydroxy-1,2,3,4-tetrahydro-3-carbazolyl, 
fluoro-1,2,3,4-tetrahydro-3-carbazolyl, 
chloro-1,2,3,4-tetrahydro-3-carbazolyl, 
dichloro-1,2,3,4-tetrahydro-3-carbazolyl, 
bromo-1,2,3,4-tetrahydro-3-carbazolyl, 
cyano-1,2,3,4-tetrahydro-3-carbazolyl or 
methylenedioxy-1,2,3,4-tetrahydro-3-carbazolyl, the substituents 
preferably being in the 6- and/or 7-position; 
in Ib, Thc is 1,2,3,4-tetrahydro-3-carbazolyl, 6- or 
7-methyl-1,2,3,4-tetrahydro-3-carbazolyl, 
6,7-dimethyl-1,2,3,4-tetrahydro-3-carbazolyl, 6- or 
7-methoxy-1,2,3,4-tetrahydro-3-carbazolyl, 
6,7-dimethoxy-1,2,3,4-tetrahydro-3-carbazolyl, 6- or 
7-chloro-1,2,3,4-tetrahydro-3-carbazolyl, 6- or 
7-hydroxy-1,2,3,4-tetrahydro-3-carbazolyl, 
6,7-dihydroxy-1,2,3,4-tetrahydro-3-carbazolyl or 
6,7-methylenedioxy-1,2,3,4-tetrahydro-3-carbazolyl; 
in Ic, A is --CH.sub.2 --; 
in Id, Ar is phenyl, tolyl, methoxyphenyl, fluorophenyl, chlorophenyl, 
trifluoromethylphenyl or chlorotrifluoromethylphenyl; 
in Ie, Ar is phenyl, 
in If, Thc is 1,2,3,4-tetrahydro-3-carbazolyl, 6- or 
7-methoxy-1,2,3,4-tetrahydro-3-carbazolyl, 6- or 
7-hydroxy-1,2,3,4-tetrahydro-3-carbazolyl, 
6,7-dimethoxy-1,2,3,4-tetrahydro-3-carbazolyl, 6- or 
7-chloro-1,2,3,4-tetrahydro-3-carbazolyl or 
6,7-dihydroxy-1,2,3,4-tetrahydro-3-carbazolyl and Ar is phenyl; 
in Ig, Thc is 1,2,3,4-tetrahydro-3-carbazolyl, 6- or 
7-hydroxy-1,2,3,4-tetrahydro-3-carbazolyl, A is --CH.sub.2 -- and Ar is 
phenyl. 
The compounds of the formula I have an asymmetric carbon atom in the 
3-position of the tetrahydrocarbazole ring. They can also have other 
asymmetric carbon atoms. Thus, they can exist as racemates and, if several 
asymmetric carbon atoms are present, they can also exist as mixtures of 
several racemates and in various optically active forms. 
The invention also relates to a process for the preparation of the 
compounds of the formula I and of their physiologically acceptable acid 
addition salts, which is characterised in that a compound of the general 
formula II 
EQU Thc--A--X.sup.1 II 
in which X.sup.1 is X or NH.sub.2 and X is Cl, Br, I, OH or a reactive 
derivative of an OH group, and Thc and A have the meanings indicated, is 
reacted with a compound of the general formula III 
##STR3## 
in which X.sup.2 and X.sup.3 can be identical or different and, when 
X.sup.1 is NH.sub.2, are both X, but otherwise are together NH, and Y and 
Z have the meaning indicated, or in that a compound which corresponds to 
the formula I, apart from containing one or more reducible group(s) and/or 
one or more additional C--C and/or C--N bond(s) in place of one or more 
hydrogen atoms, is treated with a reducing agent, or in that a compound 
corresponding to the formula I, apart from containing one or more group(s) 
which can be eliminated by solvolysis in place of one or more hydrogen 
atoms, is treated with a solvolysing agent, or in that, to prepare 
compounds of the formula I in which the two radicals Y are together a C--C 
bond, a compound of the formula IV 
##STR4## 
in which one radical E is X, CN or NH.sub.2, and the other radical E is H, 
and Thc, A, X and Z have the meanings indicated, is treated with an agent 
which eliminates HE, and/or in that, where appropriate in a compound of 
the formula I, a thioether group is oxidized to a SO group or SO.sub.2 
group, or a SO group is oxidized to a SO.sub.2 group, and/or an alkoxy 
group is cleaved with formation of an OH group, and/or a C--C double bond 
is hydrogenated, and/or in that a resulting base of the formula I is 
converted into one of its physiologically acceptable acid addition salts 
by treatment with an acid. 
The preparation of the compounds of the formula I is otherwise carried out 
by methods known per se, as are described in the literature (for example 
in the standard works, such as Houben-Weyl, Methoden der Organischen 
Chemie (Methods of Organic Chemistry), Georg-Thieme-Verlag, Stuttgart; 
Organic Reaclions, John Wiley & Sons, Inc., New York), namely under react 
on conditions as are known and suitable for the reactions mentioned. Use 
can also be made in these preparations of variants known per se which are 
not mentioned in more detail here. 
The starting materials can, if desired, also be formed in situ in such a 
manner that they are not isolated from the reaction mixture but are 
immediately reacted further to give the compounds of the formula I. 
In the tetrahydrocarbazole derivatives of the formula II, X.sup.1 is 
preferably X; accordingly, in the compounds of the formula III, X.sup.2 
and X.sup.3 together are preferably NH. The radical X is preferably Cl or 
Br; however, it can also be I, OH or a reactive derivative of an OH group, 
in particular alkylsulfonyloxy having 1-6 (for example 
methanesulfonyloxy), or arylsulfonyloxy having 6-10 C atoms (for example 
benzenesulfonyloxy, p-toluenesulfonyloxy, 1- or 2-naphthalenesulfonyloxy). 
Accordingly, the tetrahydrocarbazole derivatives of the formula I can be 
obtained, in particular, by reaction of the compounds of the formula 
Thc--A--Cl or Thc--A--Br with piperidine derivatives of the formula III, 
in which X.sup.2 and X.sup.3 together are a NH group (denoted by IIIa in 
the following text). 
Some of the compounds of the formulae II and, in particular, III are known; 
the unknown compounds of the formulae II and III can be easily prepared in 
analogy to the known compounds from known or readily prepared starting 
materials. 
Thus, the compounds of the formula II (A=--CH.sub.2 --) can be obtained, 
for example, by reducing the carboxylic acids of the formula Thc--COOH, 
which are generally known and can be prepared from the corresponding 
phenylhydrazines and the corresponding cyclohexanone-4-carboxylic esters 
by means of the Fischer indole synthesis, to give the corresponding 
carbinols of the formula Thc--CH.sub.2 OH, and converting the latter, for 
example with SOCl.sub.2, into the corresponding chlorides of the formula 
Thc--CH.sub.2 Cl or, for example with PBr.sub.3, into the corresponding 
bromides of the formula Thc--CH.sub.2 Br. Reaction of the last-mentioned 
chlorides or bromides with KCN leads to the acetonitriles of the formula 
Thc--CH.sub.2 CN, which can be hydrolyzed to give the acetic acids of the 
formula Thc--CH.sub.2 COOH. Reduction and further analogous reactions 
provide compounds of the formulae Thc--CH.sub.2 CH.sub.2 OH, Thc--CH.sub.2 
CH.sub.2 Cl and Thc--CH.sub.2 CH.sub.2 Br. 
The iodine compounds of the formula Thc--A--I, for example 
3-iodomethyl-1,2,3,4-tetrahydrocarbazole can be obtained, for example, by 
the action of potassium iodide on the relevant p-toluenesulfonic esters. 
The amines of the formula Thc--A--NH.sub.2 are accessible, for example, 
from the halides using potassium phthalimide or by reduction of the 
corresponding nitriles. 
Most of the piperidine derivatives IIIa are known (compare German 
Offenlegungsschrift No. 2,060,816) and can be obtained, for example, by 
reaction of 3- or 4-piperidone with organometallic compounds of the 
formula M-Ar (in which M is a Li atom or MgHal) and subsequent hydrolysis 
to give the corresponding 3-Ar-3- or 4-Ar-4-hydroxypiperidines, followed 
if desired, by dehydration to give 3-Ar- or 4-Ar-3,4- dehydropiperidines 
and, if desired, by hydrogenation to give 3-Ar- or 4-Ar-piperidines. 
Compounds of the formula III (X.sup.2 and X.sup.3 each being X) can be 
prepared, for example, by reduction of 2- or 3-Ar-glutaric esters, and of 
2- or 3-Ar-2-pentene-1,5-dioic esters, to 2- or 3-Ar-1,5-pentanediols, and 
2- or 3-Ar-2-pentene-1,5-diols respectively, and, where appropriate, 
subsequent reaction with SOCl.sub.2 or PBr.sub.3. 
The reaction of the compounds II and III takes place by methods as are 
known from the literature for the alkylation of amines. It is possible to 
fuse the components together in the absence of a solvent, if appropriate 
in a closed tube or in an autoclave. However, it is also possible to react 
the compounds in the presence of an inert solvent. Examples of suitable 
solvents are hydrocarbons, such as benzene, toluene or xylene; ketones, 
such as acetone or butanone; alcohols, such as methanol, ethanol, 
isopropanol or n-butanol; ethers, such as tetrahydrofuran (THF) or 
dioxane; amides, such as dimethylformamide (DMF) or N-methylpyrrolidone; 
nitriles, such as acetonitrile, and, if appropriate, mixtures with water. 
The addition of an acid-binding agent, for example an alkali metal or 
alkaline earth metal hydroxide, carbonate or bicarbonate or another salt 
of the alkali metals or alkaline earth metals, preferably of potassium, 
sodium or calcium, with a weak acid, or the addition of an organic base, 
such as triethylamine, dimethylaniline, pyridine or quinoline or an excess 
of the amine component Thc--A--NH.sub.2 or of the piperidine derivative of 
the formula IIIa can be advantageous. Depending on the conditions used, 
the reaction time is between a few minutes and 14 days, and the reaction 
temperature is between about 0.degree. and 150.degree., normally between 
20.degree. and 130.degree.. 
Furthermore, it is possible to obtain a compound of the formula I by 
treating a precursor, which has one or more reducible group(s) and/or one 
or more additional C--C and/or C--N bond(s) in place of hydrogen atoms, 
with reducing agents, preferably at temperatures between -80.degree. and 
+250.degree. in the presence of at least one inert solvent. 
Reducible groups (which can be replaced by hydrogen) are, in particular, 
oxygen in a carbonyl group, hydroxyl, arylsulfonyloxy (for example 
p-toluenesulfonyloxy), N-benzenesulfonyl, N-benzyl or O-benzyl. 
It is possible in principle to convert compounds which contain only one of 
the abovementioned groups or additional bonds or those compounds which 
contain together two or more of the abovementioned groups or additional 
bonds into a compound of the formula I by reduction. Nascent hydrogen or 
complex metal hydrides, but also reduction by the method of Wolff-Kishner, 
is preferably used for this purpose. 
Preferred starting materials for the reduction correspond to the formula V 
EQU Thc'--L--Q--Ar' V 
in which Thc' is a 1,2,3,4-tetrahydro-3-carbazolyl radical which can be 
substituted once or twice by alkyl, O-alkyl, S-alkyl, SO-alkyl, SO.sub.2 
-alkyl, OH, F, Cl, Br, CF.sub.3, CN and/or O-benzyl or by a methylenedioxy 
group and/or by an arylsulfonyl group or a benzyl group in the 9-position, 
L is --CH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CO--, --CH.sub.2 CO--, 
--COCH.sub.2 -- or --COCO--, Q is 
##STR5## 
An.sup..crclbar. is an anion of a strong acid and Ar' is a phenyl group 
which is unsubstituted or substituted once or twice by alkyl, O-alkyl, 
S-alkyl, SO-alkyl, SO.sub.2 -alkyl, OH, F, Cl, Br, CF.sub.3, CN and/or 
O-benzyl or by a methylenedioxy group, or is a 2- or 3-thienyl radical, 
but wherein it is not possible at the same time for Thc' to be Thc, L to 
be A, Q to be 
##STR6## 
and Ar' to be Ar. L in the compounds of the formula V is preferably --CO-- 
or --CH.sub.2 --CO--. 
Compounds of the formula V can be prepared, for example, by reaction of a 
3- or 4-Ar'-piperidine, -1,2,3,6-tetrahydropyridine or -pyridine with a 
compound of the formula VI 
EQU Thc'--L--X.sup.1 VI 
in which Ar', Thc', L and X.sup.1 have the meanings indicated above, under 
the conditions which are indicated above for the reaction of II with III. 
It is possible to prepare amides of the formulae V (L=--CO-- or --CH.sub.2 
CO--, 
##STR7## 
for example, from the free carboxylic acids o the formulae Thc--COOH or 
Thc--CH.sub.2 --COOH and piperidines of the formula IIIa in the presence 
of a dehydrating agent, for example carbonyldiimidazole or 
dicyclohexylcarbodiimide in one of the inert solvents indicated, 
preferably THF. 
If nascent hydrogen is used as the reducing agent, this can be produced by, 
for example, treatment of metals with weak acids or with bases. Thus, for 
example, a mixture of zinc with alkali metal hydroxide solution or of iron 
with acetic acid can be used. It is also suitable to use sodium or another 
alkali metal in an alcohol, such as ethanol, isopropanol, butanol, amyl or 
isoamyl alcohol or phenol. It is also possible to use an aluminum/nickel 
alloy in an aqueous alkaline solution, optionally with the addition of 
ethanol. Sodium amalgam or aluminum amalgam in aqueous alcoholic or 
aqueous solution are also suitable to produce nascent hydrogen. The 
reaction can also be carried out in heterogeneous phases, it being 
preferable to use an aqueous and a benzene or toluene phase. 
Moreover, it is possible to use with particular advantage complex metal 
hydrides, such as LiAlH.sub.4, NaBH.sub.4, diisobutylaluminum hydride or 
NaAl(OCH.sub.2 CH.sub.2 OCH.sub.3).sub.2 H.sub.2 and diborane, as the 
reducing agent, if desired with the addition of catalysts, such as 
BF.sub.3, AlCl.sub.3 or LiBr. Solvents which are particularly suitable for 
this purpose are ethers, such as diethyl ether, di-n-butyl ether, THF, 
dioxane, diglyme or 1,2-dimethoxyethane, and hydrocarbons, such as 
benzene. For reduction with NaBH.sub.4, alcohols, such as methanol or 
ethanol, but also water and aqueous alcohols, are primarily suitable as 
the solvent. Reduction by these methods is preferably carried out at 
temperatures between -80.degree. and +150.degree., in particular between 
about 0.degree. and about 100.degree.. 
It is possible particularly advantageously to reduce --CO-- groups in 
amides with LiAlH.sub.4 in THF at temperatures between about 0.degree. and 
66.degree. to give CH.sub.2 groups. During this, arylsulfonyl protective 
groups located in the 9-position of the 1,2,3,4-tetrahydrocarbazole ring 
can simultaneously be reductively split off. 
It is possible to reduce the pyridinium salts of the formula V (in which Q 
is 
##STR8## 
and An.sup..crclbar. is preferably Cl or Br, to give compounds of the 
formula I, for example using NaBH.sub.4 in water, methanol or ethanol or 
in mixtures of these solvents, with the addition, if desired, of a base, 
such as NaOH, at temperatures between about 0.degree. and 80.degree.. 
N-Benzyl groups can be reductively split off using sodium in liquid 
ammonia. 
Moreover, it is possible to reduce one or more carbonyl groups to CH.sub.2 
groups by the method of Wolff-Kishner, for example by treatment with 
anhydrous hydrazine in absolute ethanol under pressure at temperatures 
between about 150.degree. and 250.degree.. Sodium alcoholate is 
advantageously used as a catalyst. The reduction can also be modified by 
the method of Huang-Minlon by carrying out the reaction with hydrazine 
hydrate in a high-boiling solvent which is miscible with water, such as 
diethylene glycol or triethylene glycol, in the presence of alkali, such 
as sodium hydroxide. As a rule, the reaction mixture is boiled for about 
3-4 hours. The water is then distilled off and the hydrazone formed is 
decomposed at temperatures up to about 200.degree.. The Wolff-Kishner 
reduction can also be carried out with hydrazine in dimethyl sulfoxide at 
room temperature. 
Compounds which otherwise correspond to formula I but, in place of one or 
more H atoms, contain one or more group(s) which can be split off by 
solvolysis can be solvolyzed, in particular hydrolyzed, to give compounds 
of the formula I. The starting materials for the solvolysis can be 
obtained, for example, by reaction of IIIa with compounds which correspond 
to the formula II (X.sup.1 =X) but which contain, in place of one or more 
H atoms, one or more group(s) which can be split off by solvolysis. Thus, 
1-acyl-1,2,3,4-tetrahydrocarbazole derivatives (corresponding to the 
formula I but containing an acyl group, preferably an alkanoyl, 
alkylsulfonyl or arylsulfonyl group, each having up to 10 C atoms, such as 
methane-, benzene- or p-toluene-sulfonyl, in the 9-position of the Thc 
radical) can be hydrolyzed to give the corresponding 
1,2,3,4-tetrahydrocarbazole derivatives which are unsubstituted in the 
1-position of the 1,2,3,4-tetrahydrocarbazole ring, for example in acid, 
but better in neutral or alkaline medium at temperatures between 0.degree. 
and 200.degree.. Sodium, potassium or calcium hydroxide, sodium or 
potassium carbonate or ammonia are preferably used as the basic catalysts. 
The solvents which are preferably chosen are water, lower alcohols, such 
as methanol or ethanol, ethers, such as THF or dioxane, sulfones, such as 
tetramethylenesulfone, or their mixtures. Hydrolysis can even take place 
just on treatment with water alone, in particular at the boiling point. 
Moreover, the compounds of the formula I in which the two radicals Y are 
together a C--C bond are also accessible by eliminating HE from compounds 
of the formula IV with the formation of a double bond. Depending on the 
definition of E, this can be, for example, elimination of hydrogen halide, 
water (dehydration), a carboxylic acid or another acid, of ammonia or of 
HCN. The starting materials of the formula IV can be obtained, for 
example, by reaction of II (X.sup.1 =X) with a compound of the formula IX 
##STR9## 
in which E and Z have the meanings indicated. 
If one of the radicals E is Hal, this substituent can easily be eliminated 
under basic reaction conditions. The following can be used as bases: 
alkali metal hydroxides, alkali metal carbonates, alcoholates, such as, 
for example, potassium tert.-butylate, amines, such as, for example, 
dimethylaniline, pyridine, collidine or quinoline; the solvent used is, 
for example, benzene, toluene, cyclohexane, methanol, dioxane, THF or 
tert.-butanol. The amines used as bases can also be employed in excess as 
the solvent. If one of the radicals E is an OH group, then acids, such as 
acetic acid, hydrochloric acid or mixtures of the two, are preferably used 
as the agent to eliminate water. The addition of a solvent (for example 
water or ethanol) can be advantageous. The elimination of acyl, 
alkylsulfonyl and alkoxysulfonyloxy or amino radicals can be carried out 
under similar conditions. An elimination of sulfonic acid radicals, for 
example mesylates or tosylates, takes place under mild conditions by 
boiling in DMF or dimethyl sulfoxide with alkali metal carbonates, for 
example Li.sub.2 CO.sub.3, or with potassium acetate. Ammonia can be 
eliminated by just heating the salts of the corresponding amino compounds 
(especially the 4-amino derivatives). In a similar manner, HCN can be 
eliminated from compounds of the formula IV (one group E=CN) by heating. 
The elimination of HE from IV generally takes place at temperatures 
between about 0.degree. and about 250.degree., preferably between 
50.degree. and 200.degree.. 
Furthermore, the thioether group in a thioether of the formula I can be 
oxidized to a SO group or to a SO.sub.2 group, or the SO group in a 
sulfoxide of the formula I can be oxidized to a SO.sub.2 group. The 
thioether or sulfoxide groups to be oxidized can be present as 
substituents in the radical Thc and/or in the radical Ar. If the intention 
is to obtain the sulfoxides, then the oxidation is carried out with, for 
example, hydrogen peroxide, peracids, such as m-chloroperbenzoic acid, 
Cr(VI) compounds, such as chromic acid, KMnO.sub.4, 1-chlorobenzotriazole, 
Ce(IV) compounds, such as (NH.sub.4).sub.2 Ce(NO.sub.3).sub.6, negative 
substituted aromatic diazonium salts, such as o- or p-nitrophenyldiazonium 
chloride, or electrolytically under relatively mild conditions and at 
relatively low temperatures (about -80.degree. to +100.degree.). If, on 
the other hand, the intention is to obtain the sulfones (from the 
thioethers or the sulfoxides), then the same oxidizing agents are used 
under more forcing conditions and/or in excess and, as a rule, at higher 
temperatures. It is possible in these reactions for the customary inert 
solvents to be present or absent. Examples of suitable inert solvents are 
water, aqueous mineral acids, aqueous alkali metal hydroxide solutions, 
lower alcohols, such as methanol or ethanol, esters, such as ethyl 
acetate, ketones, such as acetone, lower carboxylic acids, such as acetic 
acid, nitriles, such as acetonitrile, hydrocarbons, such as benzene, 
chlorinated hydrocarbons, such as chloroform or CCl.sub.4. A preferred 
oxidizing agent is 30% aqueous hydrogen peroxide. On using the calculated 
amount in solvents such as acetic acid, acetone, methanol, ethanol or 
aqueous sodium hydroxide solution at temperatures between -20.degree. and 
100.degree., this leads to the sulfoxides, while in excess at higher 
temperatures, preferably in acetic acid or in a mixture of acetic acid and 
acetic anhydride, this leads to the sulfones. 
Ethers of the formula I in which the radicals Thc and/or Ar are substituted 
once or twice by O-alkyl can be cleaved by methods known from the 
literature, the corresponding hydroxy derivatives being produced. For 
example, the ethers can be cleaved by treatment with HBr or HI in aqueous 
or acetic acid solution, by heating with Lewis acids, such as AlCl.sub.3 
or boron trihalides, or by fusing with pyridine or aniline hydrohalides, 
preferably pyridine hydrochloride, at about 150.degree.-250.degree.. 
Reductive cleavage using diisobutylaluminium hydride (for method, compare 
Synthesis 1975, 617) is particularly mild. 
If desired, unsaturated compounds of the formula I in which the two 
radicals Y are together a C--C bond can be hydrogenated to give the 
corresponding saturated compounds of the formula I in which the two 
radicals Y are each H, preferably in the presence of a heavy metal 
catalyst, such as platinum, palladium or Raney nickel, in an inert 
solvent, for example an alcohol such as methanol or ethanol, at 
temperatures between about 0.degree. and 150.degree., and under pressures 
between about 1 and 200 bar. 
A base of the formula I which has been obtained can be converted into the 
relevant acid addition salt using an acid. Acids which provide 
physiologically acceptable salts are suitable for this reaction. Thus, 
inorganic acids can be used, for example sulfuric acid, hydrohalic acids, 
such as hydrochloric acid or hydrobromic acid, phosphoric acids, such as 
orthophosphoric acid, nitric acid or sulfamic acid, but also organic 
acids, specifically aliphatic, alicyclic, araliphatic, aromatic or 
heterocyclic monobasic or polybasic carboxylic, sulfonic or sulfuric 
acids, such as formic acid, acetic acid, propionic acid, pivalic acid, 
diethylacetic acid, malonic acid, succinic acid, pimelic acid, fumaric 
acid, maleic acid, lactic acid, tartaric acid, malic acid, benzoic acid, 
salicylic acid, 2-phenylpropionic acid, citric acid, gluconic acid, 
ascorbic acid, nicotinic acid, isonicotinic acid, methane- or 
ethanesulfonic acid, ethanedisulfonic acid, 2-hydroxyethanesulfonic acid, 
benzenesulfonic acid, p-toluenesulfonic acid, naphthalenemonosulfonic and 
naphthalenedisulfonic acids, and laurylsulfuric acid. 
It is possible, if desired, to liberate the free bases of the formula I 
from their salts by treatment with strong bases, such as sodium or 
potassium hydroxide or sodium or potassium carbonate. 
The invention also relates to the use of the compounds of the formula I and 
their physiologically acceptable salts for the preparation of 
pharmaceutical formulations, in particular by non-chemical means. For this 
purpose, it is possible to convert them into a suitable form for 
administration together with at least one vehicle or auxiliary and, where 
appropriate, combined with one or more other active compound(s). 
The invention also relates to agents, especially pharmaceutical 
formulations, containing at least one compound of the formula I and/or one 
of its physiologically acceptable salts. These formulations can be 
employed as medicaments in human or veterinary medicine. Suitable vehicles 
are organic or inorganic substances which are suitable for enteral (for 
example oral), parenteral or topical administration and which do not react 
with the new compounds, for example water, vegetable oils, benzyl 
alcohols, polyethylene glycols, gelatine, carbohydrates, such as lactose 
or starch, magnesium stearate, talc and vaseline. In particular, tablets, 
coated tablets, capsules, syrups, liquids, drops or suppositories are used 
for enteral administration, solutions, preferably oily or aqueous 
solutions, but also suspensions, emulsions or implants are used for 
parenteral administration, and ointments, creams or powders are used for 
topical application. It is also possible to freeze-dry the new compounds 
and use the lyophilizates obtained, for example for the preparation of 
products for injection. 
The indicated formulations can be sterilized and/or contain auxiliaries, 
such as lubricants, preservatives, stabilizers and/or wetting agents, 
emulsifiers, salts to modify the osmotic pressure, buffer substances, 
colorants, flavorings and/or aromatic substances. If desired, they can 
also contain one or more other active compounds, for example one or more 
vitamins. 
The invention also relates to the use of the compounds of the formula I and 
their physiologically acceptable salts for the therapeutic treatment of 
the human or animal body and for the control of illnesses, especially of 
parkinsonism, of extrapyramidal disturbances associated with neuroleptic 
therapy, of depression and/or psychosis and of side effects of treatment 
for hypertension (for example with .alpha.-methyldopa). The compounds can 
also be used in endocrinology and gynaecology, for example for the therapy 
of acromegaly, hypogonadism, secondary amenorrhoea, premenstrual syndrome, 
undesired puerperal lactation and generally as prolactin inhibitors, also 
for the therapy of cerebral disturbances (for example migraine) and 
especially in geriatrics, similarly to certain ergot alkaloids. 
For these purposes, as a rule the substances according to the invention are 
administered in analogy to known and commercially available products (for 
example bromocriptine and dihydroergocornine), preferably in doses between 
about 0.2 and 500 mg, in particular between 0.2 and 50 mg per dosage unit. 
The daily dose is preferably between about 0.001 and 10 mg/kg of body 
weight. In this context, the low doses (about 0.2 to 1 mg per dosage unit; 
about 0.001 to 0.005 mg/kg of body weight) are particularly suitable for 
use as agents for migraine; doses between 10 and 50 mg per dosage unit are 
preferred for the other indications. Preferred dose ranges for specific 
indications are as follows: parkinsonism 1 to 200, preferably 40 to 100; 
dyskinesia 40 to 100; psychosis, for example schizophrenia, 2 to 20; 
acromegaly 2 to 50 mg per dosage unit. However, the specific dose for each 
particular patient depends on a wide variety of factors, for example on 
the efficacy of the specific compound employed, on the age, body weight, 
general state of health, sex, on the diet, on the timing and mode of 
administration, on the rate of excretion, and on medicaments used in 
combination and the severity of the particular disorder to which the 
therapy is applied. Oral administration is preferred. 
The chemical reactions described above are generally disclosed in terms of 
their broadest application to the preparation of the compounds of this 
invention. Occasionally, the reactions may not be applicable as described 
to each compound included within the disclosed scope. The compounds for 
which this occurs will be readily recognized by those skilled in the art. 
In all such cases, either the reactions can be successfully performed by 
conventional modifications known to those skilled in the art, e.g., by 
appropriate protection of interfering groups, by changing to alternative 
conventional reagents, by routine modification of reaction conditions, 
etc., or other reactions disclosed herein or otherwise conventional, will 
be applicable to the preparation of the corresponding compounds of this 
invention. In all preparative methods, all starting materials are known or 
readily preparable from known starting materials. 
Without further elaboration, it is believed that one skilled in the art 
can, using the preceding description, utilize the present invention to its 
fullest extent. The following preferred specific embodiments are, 
therefore, to be construed as merley illustrative, and not limitative of 
the remainder of the disclosure in any way whatsoever. In the following 
examples, all temperatures are set forth uncorrected in degrees Celsius; 
unless otherwise indicated, all parts and percentages are by weight. 
In the examples below, "usual work-up" denotes: 
Water is added if necessary, the mixture is extracted with an orqanic 
solvent, such as toluene, chloroform dichloromethane, the phases are 
separated, the organic phase is dried over sodium sulfate, filtered and 
evaporated and the product is purified by chromatography and/or 
crystallization. Temperatures are reported in degrees centigrade. Rf 
values on silica gel (CH.sub.2 Cl.sub.2 /methanol 95:5 unless otherwise 
indicated).

EXAMPLE 1 
A solution of 2.19 g of 3-chloromethyl-1,2,3,4-tetrahydrocarbazole (or 2.63 
g of 3-bromomethyl-1,2,3,4-tetrahydrocarbazole) (obtainable by reduction 
of 1,2,3,4-tetrahydrocarbazole-3-carboxylic acid with LiAlH.sub.4 to give 
3-hydroxymethyl-1,2,3,4-tetrahydrocarbazole, followed by reaction with 
SOCl.sub.2 or PBr.sub.3) and 1.6 g of 4-phenyl-1,2,3,6-tetrahydropyridine 
in 10 ml of acetonitrile is stirred at 20.degree. for 12 hours, worked up 
as usual and 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-1,2,3,4-tetrahydrocarbazol 
e ("P") is obtained. M.p. 163.degree.-165.degree.. 
In analogy, from the appropriate 3-chloroalkyl- or 
3-bromoalkyl-1,2,3,4-tetrahydrocarbazoles, for example 
3-chloromethyl-6-methoxy-1,2,3,4-tetrahydrocarbazole, 
3-chloromethyl-7-methoxy-1,2,3,4-tetrahydrocarbazole, 
3-chloromethyl-6-hydroxy-1,2,3,4-tetrahydrocarbazole, 
3-chloromethyl-7-hydroxy-1,2,3,4-tetrahydrocarbazole, 
3-chloromethyl-6,7-dimethoxy-1,2,3,4-tetrahydrocarbazole, 
3-(2-chloroethyl)-1,2,3,4-tetrahydrocarbazole, 
3-(2-chloroethyl)-6-methoxy-1,2,3,4-tetrahydrocarbazole, 
3-(2-chloroethyl)-7-methoxy-1,2,3,4-tetrahydrocarbazole, 
3-(2-chloroethyl)-6-hydroxy-1,2,3,4-tetrahydrocarbazole, 
3-(2-chloroethyl)-7-hydroxy-1,2,3,4-tetrahydrocarbazole, 
3-(2-chloroethyl)-7-chloro-1,2,3,4-tetrahydrocarbazole or 
3-(2-chloroethyl)-6,7-dimethoxy-1,2,3,4-tetrahydrocarbazole, 
with the appropriate 4-aryl-1,2,3,6-tetrahydropyridines, the following are 
obtained: 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-6-methyl-1,2,3,4-tetrahydro 
carbazole, 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-7-methyl-1,2,3,4-tetrahydro 
carbazole, 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-9-methyl-1,2,3,4-tetrahydro 
carbazole, 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-6-methoxy-1,2,3,4-tetrahydr 
ocarbazole, m.p. 161.degree.-163.degree., 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-7-methoxy-1,2,3,4-tetrahydr 
ocarbazole, m.p. 164.degree.-166.degree. 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-8-methoxy-1,2,3,4-tetrahydr 
ocarbazole, 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-6-ethoxy-1,2,3,4-tetrahydro 
carbazole, 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-6-methylthio-1,2,3,4-tetrah 
ydrocarbazole, 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-7-methylthio-1,2,3,4-tetrah 
ydrocarbazole, 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-6-methylsulfinyl-1,2,3,4-te 
trahydrocarbazole, 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-7-methylsulfinyl-1,2,3,4-te 
trahydrocarbazole, 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-6-methylsulfonyl-1,2,3,4-te 
trahydrocarbazole, 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-7-methylsulfonyl-1,2,3,4-te 
trahydrocarbazole, 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-5-hydroxy-1,2,3,4-tetrahydr 
ocarbazole, 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-6-hydroxy-1,2,3,4-tetrahydr 
ocarbazole, Rf 0.2 (toluene/triethylamine 9:1), 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-7-hydroxy-1,2,3,4-tetrahydr 
ocarbazole, Rf 0.28 (CH.sub.2 Cl.sub.2 /methanol 9:1) 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-8-hydroxy-1,2,3,4-tetrahydr 
ocarbazole, 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-6-fluoro-1,2,3,4-tetrahydro 
carbazole, 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-7-fluoro-1,2,3,4-tetrahydro 
carbazole, 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-6-chloro-1,2,3,4-tetrahydro 
carbazole, 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-7-chloro-1,2,3,4-tetrahydro 
carbazole, 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-6-bromo-1,2,3,4-tetrahydroc 
arbazole, 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-7-bromo-1,2,3,4-tetrahydroc 
arbazole, 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-6-trifluoromethyl-1,2,3,4-t 
etrahydrocarbazole, 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-7-trifluoromethyl-1,2,3,4-t 
etrahydrocarbazole, 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-6-cyano-1,2,3,4-tetrahydroc 
arbazole, 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-7-cyano-1,2,3,4-tetrahydroc 
arbazole, 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-8-cyano-1,2,3,4-tetrahydroc 
arbazole, 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-6,7-dimethoxy-1,2,3,4-tetra 
hydrocarbazole, m.p. 178.degree.-180.degree., 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-6,7-methylenedioxy-1,2,3,4- 
tetrahydrocarbazole, 
3-(4-o-tolyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-1,2,3,4-tetrahydrocarbazol 
e, 
3-(4-m-tolyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-1,2,3,4-tetrahydrocarbazol 
e, 
3-(4-p-tolyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-1,2,3,4-tetrahydrocarbazol 
e, 
3-(4-o-methoxyphenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-1,2,3,4-tetrahydro 
carbazole, 
3-(4-m-methoxyphenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-1,2,3,4-tetrahydro 
carbazole, 
3-(4-p-methoxyphenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-1,2,3,4-tetrahydro 
carbazole, 
3-(4-o-hydroxyphenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-1,2,3,4-tetrahydro 
carbazole, 
3-(4-m-hydroxyphenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-1,2,3,4-tetrahydro 
carbazole, 
3-(4-p-hydroxyphenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-1,2,3,4-tetrahydro 
carbazole, 
3-(4-o-fluorophenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-1,2,3,4-tetrahydroc 
arbazole, 
3-(4-m-fluorophenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-1,2,3,4-tetrahydroc 
arbazole, 
3-(4-p-fluorophenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-1,2,3,4-tetrahydroc 
arbazole, 
3-(4-o-chlorophenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-1,2,3,4-tetrahydroc 
arbazole, 
3-(4-m-chlorophenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-1,2,3,4-tetrahydroc 
arbazole, 
3-(4-p-chlorophenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-1,2,3,4-tetrahydroc 
arbazole, 
3-(4-p-bromophenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-1,2,3,4-tetrahydroca 
rbazole, 
3-(4-m-trifluoromethylphenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-1,2,3,4-te 
trahydrocarbazole, 
3-(4-p-cyanophenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-1,2,3,4-tetrahydroca 
rbazole, 
3-[4-(3,4-dimethoxyphenyl)-1,2,3,6-tetrahydro-1-pyridylmethyl]-1,2,3,4-tetr 
ahydrocarbazole, 
3-[4-(3,4-methylenedioxyphenyl)-1,2,3,6-tetrahydro-1-pyridylmethyl]-1,2,3,4 
-tetrahydrocarbazole, 
3-[4-(4-chloro-3-trifluoromethylphenyl)-1,2,3,6-tetrahydro-1-pyridylmethyl] 
-1,2,3,4-tetrahydrocarbazole, 
3-[2-(4-phenyl-1,2,3,6-tetrahydropyridyl)ethyl]-1,2,3,4-tetrahydrocarbazole 
, hydrochloride, m.p. 263.degree.-265.degree., 
3-[2-(4-phenyl-1,2,3,6-tetrahydropyridyl)ethyl]-6-methyl-1,2,3,4-tetrahydro 
carbazole, 
3-[2-(4-phenyl-1,2,3,6-tetrahydropyridyl)ethyl]-6-methoxy-1,2,3,4-tetrahydr 
ocarbazole, hydrochloride, m.p. 214.degree.-216.degree., 
3-[2-(4-phenyl-1,2,3,6-tetrahydropyridyl)ethyl]-7-methoxy-1,2,3,4-tetrahydr 
ocarbazole, hydrochloride, m.p. 2I58.degree.-260.degree., 
3-[2-(4-phenyl-1,2,3,6-tetrahydropyridyl)ethyl]-6-methylthio-1,2,3,4-tetrah 
ydrocarbazole, 
3-[2-(4-phenyl-1,2,3,6-tetrahydropyridyl)ethyl]-7-methylthio-1,2,3,4-tetrah 
ydrocarbazole, 
3-[2-(4-phenyl-1,2,3,6-tetrahydropyridyl)ethyl]-5-hydroxy-1,2,3,4-tetrahydr 
ocarbazole, 
3-[2-(4-phenyl-1,2,3,6-tetrahydropyridyl)ethyl]-6-hydroxy-1,2,3,4-tetrahydr 
ocarbazole, hydrochloride, m.p. 290.degree.-292.degree., 
3-[2-(4-phenyl-1,2,3,6-tetrahydropyridyl)ethyl]-7-hydroxy-1,2,3,4-tetrahydr 
ocarbazole, m.p. 206.degree.-208.degree. 
3-[2-(4-phenyl-1,2,3,6-tetrahydropyridyl)ethyl]-8-hydroxy-1,2,3,4-tetrahydr 
ocarbazole, 
3-[2-(4-phenyl-1,2,3,6-tetrahydropyridyl)ethyl]-6-fluoro-1,2,3,4-tetrahydro 
carbazole, 
3-[2-(4-phenyl-1,2,3,6-tetrahydropyridyl)ethyl]-7-fluoro-1,2,3,4-tetrahydro 
carbazole, 
3-[2-(4-phenyl-1,2,3,6-tetrahydropyridyl)ethyl]-6-chloro-1,2,3,4-tetrahydro 
carbazole, 
3-[2-(4-phenyl-1,2,3,6-tetrahydropyridyl)ethyl]-7-chloro-1,2,3,4-tetrahydro 
carbazole, m.p. 182.degree.-184.degree., 
3-[2-(4-phenyl-1,2,3,6-tetrahydropyridyl)ethyl]-6-bromo-1,2,3,4-tetrahydroc 
arbazole, 
3-[2-(4-phenyl-1,2,3,6-tetrahydropyridyl)ethyl]-7-bromo-1,2,3,4-tetrahydroc 
arbazole, 
3-[2-(4-phenyl-1,2,3,6-tetrahydropyridyl)ethyl]-6-trifluoromethyl-1,2,3,4-t 
etrahydrocarbazole, 
3-[2-(4-phenyl-1,2,3,6-tetrahydropyridyl)ethyl]-7-trifluoromethyl-1,2,3,4-t 
etrahydrocarbazole, 
3-[2-(4-phenyl-1,2,3,6-tetrahydropyridyl)ethyl]-6-cyano-1,2,3,4-tetrahydroc 
arbazole, 
3-[2-(4-phenyl-1,2,3,6-tetrahydropyridyl)ethyl]-7-cyano-1,2,3,4-tetrahydroc 
arbazole, 
3-[2-(4-phenyl-1,2,3,6-tetrahydropyridyl)ethyl]-8-cyano-1,2,3,4-tetrahydroc 
arbazole, 
3-[2-(4-phenyl-1,2,3,6-tetrahydropyridyl)ethyl]-6,7-dimethoxy-1,2,3,4-tetra 
hydrocarbazole, hydrochloride, m.p. 172.degree.-174.degree., or 
3-[2-(4-phenyl-1,2,3,6-tetrahydropyridyl)ethyl]-6,7-methylenedioxy-1,2,3,4- 
tetrahydrocarbazole. 
EXAMPLE 2 
A mixture of 4.54 g of 
3-p-toluenesulfonyloxymethyl-1,2,3,4-tetrahydrocarbazole and 3.18 g of 
4-phenyl-1,2,3,6-tetrahydropyridine is heated at 130.degree.. After the 
exothermic reaction has subsided and the mixture has cooled, it is worked 
up as usual and "P" of m.p. 163.degree.-165.degree. is obtained. 
In analogy, the following are obtained from the appropriate tosylates: 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-1-methyl-1,2,3,4-tetrahydro 
carbazole, 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-2-methyl-1,2,3,4-tetrahydro 
carbazole, 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-3-methyl-1,2,3,4-tetrahydro 
carbazole, 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-4-methyl-1,2,3,4-tetrahydro 
carbazole, 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-6-butyl-1,2,3,4-tetrahydroc 
arbazole, 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-6-butoxy-1,2,3,4-tetrahydro 
carbazole and 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-6-butylthio-1,2,3,4-tetrahy 
drocarbazole. 
EXAMPLE 3 
3.1 g of 3-iodomethyl-1,2,3,4-tetrahydrocarbazole, 1.59 g of 
4-phenyl-1,2,3,6-tetrahydropyridine and 1.5 g of anhydrous potassium 
carbonate in 25 ml of n-butanol are boiled with stirring for 2 hours, 
allowed to cool, worked up as usual and "P" of m.p. 
163.degree.-165.degree. is obtained. 
In analogy, the following are obtained using the appropriate 
4-Ar-1,2,3,6-tetrahydropyridines: 
3-(4-p-butoxyphenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-1,2,3,4-tetrahydroc 
arbazole, 
3-(4-p-methylthiophenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-1,2,3,4-tetrahy 
drocarbazole, 
3-(4-p-butylthiophenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-1,2,3,4-tetrahyd 
rocarbazole, 
3-(4-p-methylsulfinylphenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-1,2,3,4-tet 
rahydrocarbazole and 
3-(4-p-methylsulfonylphenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-1,2,3,4-tet 
rahydrocarbazole. 
EXAMPLE 4 
A mixture of 2.0 g of 3-aminomethyl-1,2,3,4-tetrahydrocarbazole (obtainable 
by reaction of 3-bromomethyl-1,2,3,4-tetrahydrocarbazole with potassium 
phthalimide followed by hydrolysis) and 2.15 g of 
1,5-dichloro-3-phenyl-2-pentene (obtainable by reduction of diethyl 
3-phenyl-2-pentene-1,5-dioate with LiAlH.sub.4 followed by reaction with 
SOCl.sub.2) in 40 ml of acetone and 40 ml of water is boiled for 24 hours 
and worked up as usual. "P" of m.p. 163.degree.-165.degree. is obtained. 
In analogy, the other compounds of the formula I indicated in Examples 1, 2 
and 3 are obtained from the appropriate amines and the appropriate 
1,5-dichloro-3-Ar-2-pentenes. 
EXAMPLE 5 
1 g of NaBH.sub.4 in 20 ml of water is added, with stirring, to a solution 
of 4.19 g of 1-(1,2,3,4-tetrahydro-3-carbazolylmethyl)-4-phenylpyridinium 
bromide (obtainable from 3-bromomethyl-1,2,3,4-tetrahydrocarbazole and 
4-phenylpyridine) in 50 ml of 1N NaOH, and the mixture is then stirred at 
60.degree. for 3 hours. After the usual work-up, "P" of m.p. 
163.degree.-165.degree. is obtained. 
In analogy, the other compounds of the formula I indicated in Examples 1, 2 
and 3 are obtained by reduction of the appropriate pyridinium bromides. 
EXAMPLE 6 
A solution of 3.56 g of 
3-(4-phenyl-1,2,3,6-tetrahydropyridylcarbonyl)-1,2,3,4-tetrahydrocarbazole 
(Rf 0.9; obtainable from 1,2,3,4-tetrahydrocarbazole-3-carboxylic acid and 
4-phenyl-1,2,3,6-tetrahydropyridine in the presence of carbonyldiimidazole 
in THF at 20.degree.) in 10 ml of THF is added dropwise, with stirring, to 
a suspension of 0.3 g of LiAlH.sub.4 in 10 ml of THF. After the reaction 
has subsided, 5 ml of ethyl acetate are added, the mixture is worked up as 
usual and "P" of m.p. 163.degree.-165.degree. is obtained. 
In analogy, from the appropriate amides, for example: 
3-(4-phenyl-1,2,3,6-tetrahydropyridylcarbonyl)-6-methoxy-1,2,3,4-tetrahydro 
carbazole (m.p. 210.degree.-212.degree.), 
3-(4-phenyl-1,2,3,6-tetrahydropyridylcarbonyl)-7-methoxy-1,2,3,4-tetrahydro 
carbazole (Rf 0.2, CH.sub.2 Cl.sub.2 /methanol 98:2) 
3-(4-phenyl-1,2,3,6-tetrahydropyridylcarbonyl)-6-hydroxy-1,2,3,4-tetrahydro 
carbazole (m.p. 210.degree.-212.degree.), 
3-(4-phenyl-1,2,3,6-tetrahydropyridylcarbonyl)-6,7-dimethoxy-1,2,3,4-tetrah 
ydrocarbazole (m.p. 143.degree.-145.degree.), 
3-(4-phenyl-1,2,3,6-tetrahydropyridylcarbonylmethyl)-1,2,3,4-tetrahydrocarb 
azole (Rf 0.8, toluene/CH.sub.3 OH/triethylamine 7:2:1), 
3-(4-phenyl-1,2,3,6-tetrahydropyridylcarbonylmethyl)-6-methoxy-1,2,3,4-tetr 
ahydrocarbazole (Rf 0.85), 
3-(4-phenyl-1,2,3,6-tetrahydropyridylcarbonylmethyl)-7-methoxy-1,2,3,4-tetr 
ahydrocarbazole (Rf 0.6), 
3-(4-phenyl-1,2,3,6-tetrahydropyridylcarbonylmethyl)-6-hydroxy-1,2,3,4-tetr 
ahydrocarbazole (Rf 0.85), 
3-(4-phenyl-1,2,3,6-tetrahydropyridylcarbonylmethyl)-7-chloro-1,2,3,4-tetra 
hydrocarbazole (Rf 0.9) and 
3-(4-phenyl-1,2,3,6-tetrahydropyridylcarbonylmethyl)-6,7-dimethoxy-1,2,3,4- 
tetrahydrocarbazole (Rf 0.85), 
the other compounds of the formula I indicated in Examples 1 to 3 are 
obtained. 
EXAMPLE 7 
4.82 g of 
9-benzenesulfonyl-3-(4-phenyl-1,2,3,6-tetrahydropyridylmethyl)-1,2,3,4-tet 
rahydrocarbazole (obtainable from 
9-benzenesulfonyl-3-chloromethyl-1,2,3,4-tetrahydrocarbazole and 
4-phenyl-1,2,3,6-tetrahydropyridine) are boiled with 1 g of KOH in 7 ml of 
water and 14 ml of ethanol for 16 hours, the mixture is concentrated, 
worked up as usual and "P" of m.p. 163.degree.-165.degree. is obtained. 
EXAMPLE 8 
3.74 g of 
3-(4-hydroxy-4-phenyl-1-piperidylmethyl)-9-methyl-1,2,3,4-tetrahydrocarbaz 
ole (obtainable by reaction of 
3-bromomethyl-9-methyl-1,2,3,4-tetrahydrocarbazole with 4-piperidone 
followed by reaction with C.sub.6 H.sub.5 Li and hydrolysis) are heated 
with 40 ml of 1N hydrochloric acid at 50.degree. for 2 hours, the mixture 
is worked up as usual and 
3-(4-phenyl-1,2,3,6-tetrahydropyridylmethyl)-9-methyl-1,2,3,4-tetrahydroca 
rbazole is obtained. 
EXAMPLE 9 
6 ml of 30% H.sub.2 O.sub.2 are added to a boiling solution of 3.88 g of 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-7-methylthio-1,2,3,4-tetra 
hydrocarbazole in 50 ml of ethanol and the mixture is then boiled for 3 
hours. After addition of a further 4 ml of the oxidizing agent, the 
mixture is boiled for 9 hours, cooled, worked up as usual and 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-7-methylsulfinyl-1,2,3,4-t 
etrahydrocarbazole is obtained. 
EXAMPLE 10 
9 ml of 30% H.sub.2 O.sub.2 are added to a solution of 3.88 g of 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-7-methylthio-1,2,3,4-tetra 
hydrocarbazole in 20 ml of acetic acid and the mixture is boiled for 90 
minutes. After the usual work-up, 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-7-methylsulfonyl-1,2,3,4-t 
etrahydrocarbazole is obtained. 
EXAMPLE 11 
A mixture of 4.19 g of 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-6-methoxy-1,2,3,4-tetrahyd 
rocarbazole hydrochloride and 3.5 g of pyridine hydrochloride is stirred at 
160.degree. for 3 hours. After the usual work-up, 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-6-hydroxy-1,2,3,4-tetrahyd 
rocarbazole, Rf 0.2 (toluene/triethylamine 9:1), is obtained. 
EXAMPLE 12 
In analogy to example 6, the following are obtained from the appropriate 
amides: 
3-[4-(2-thienyl)-1,2,3,6-tetrahydro-1-pyridylmethyl]-1,2,3,4-tetrahydrocarb 
azole 
3-(4-phenylpiperidinomethyl)-1,2,3,4-tetrahydrocarbazole 
3-(4-phenylpiperidinomethyl)-6-hydroxy-1,2,3,4-tetrahydrocarbazole 
3-(4-phenylpiperidinomethyl)-7-hydroxy-1,2,3,4-tetrahydrocarbazole 
3-(4-m-methoxyphenylpiperidinomethyl)-1,2,3,4-tetrahydrocarbazole 
3-(4-m-hydroxyphenylpiperidinomethyl)-1,2,3,4-tetrahydrocarbazole 
3-(3-phenyl-1,2,5,6-tetrahydro-1-pyridylmethyl)-1,2,3,4-tetrahydrocarbazole 
3-(3-phenyl-1,2,5,6-tetrahydro-1-pyridylmethyl)-6-hydroxy-1,2,3,4-tetrahydr 
ocarbazole 
3-(3-phenyl-1,2,5,6-tetrahydro-1-pyridylmethyl)-7-hydroxy-1,2,3,4-tetrahydr 
ocarbazole 
3-(3-m-methoxyphenyl-1,2,5,6-tetrahydro-1-pyridylmethyl)-1,2,3,4-tetrahydro 
carbazole 
3-(3-m-hydroxyphenyl-1,2,5,6-tetrahydro-1-pyridylmethyl)-1,2,3,4-tetrahydro 
carbazole 
-(3-phenylpiperidinomethyl)-1,2,3,4-tetrahydrocarbazole3-(3-phenylpiperidin 
omethyl)-6-hydroxy-1,2,3,4-tetrahydrocarbazole 
3-(3-phenylpiperidinomethyl)-7-hydroxy-1,2,3,4-tetrahydrocarbazole 
3-(3-m-methoxyphenylpiperidinomethyl)-1,2,3,4-tetrahydrocarbazole, Rf 0.65 
(CH.sub.2 Cl.sub.2 /methanol 9:1) 
3-(3-m-methoxyphenylpiperidinomethyl)-6-methoxy-1,2,3,4-tetrahydrocarbazole 
, Rf 0.7 (CH.sub.2 Cl.sub.2 /methanol 9:1) 
3-(3-m-hydroxyphenylpiperidinomethyl)-1,2,3,4-tetrahydrocarbazole, m.p. 
128.degree.-130.degree. 
3-(3-m-hydroxyphenylpiperidinomethyl)-6-hydroxy-1,2,3,4-tetrahydrocarbazole 
, m.p. 123.degree.-125.degree.. 
EXAMPLE 13 
A solution of 1 g of 
3-(3-m-hydroxyphenol-1,2,5,6-tetrahydro-1-pyridylmethyl)-1,2,3,4-tetrahydr 
ocarbazole in 15 ml of methanol is hydrogenated in 1 g of 5% Pd-C under 1 
bar and at 20.degree. C. The mixture is filtered, evaporated, and 
3-(3-m-hydroxyphenylpiperidinomethyl)-1,2,3,4-tetrahydrocarbazole, m.p. 
128.degree.-130.degree., is obtained. 
The examples which follow relate to pharmaceutical formulations which 
contain amines of the formula I or their acid addition salts: 
EXAMPLE A 
Tablets 
A mixture of 1 kg of 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-1,2,3,4-tetrahydrocarbazol 
e, 4 kg of lactose, 1.2 kg of potato starch, 0.2 kg of talc and 0.1 kg of 
magnesium stearate is compressed to form tablets in a customary manner so 
that each tablet contains 10 mg of active compound. 
EXAMPLE B 
Coated tablets 
Tablets are formed by compression in analogy to Example A and these are 
then coated in a customary manner with a coating of sucrose, potato 
starch, talc, tragacanth and colorant. 
EXAMPLE C 
Capsules 
2 kg of 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-6-hydroxy-1,2,3,4-tetrahyd 
rocarbazole are filled into hard gelatine capsules in a customary manner so 
that each capsule contains 20 mg of the active compound. 
EXAMPLE D 
Ampoules 
A solution of 1 kg of 
3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridylmethyl)-7-hydroxy-1,2,3,4-tetrahyd 
rocarbazole hydrochloride in 30 liters of double distilled water is 
sterilized by filtration, filled into ampoules, freeze-dried under sterile 
conditions and sealed sterile. Each ampoule contains 10 mg of active 
compound. 
In analogy, tablets, coated tablets, capsules and ampoules can be obtained 
which contain one or more of the other active compounds of the formula I 
and/or their physiologically acceptable acid addition salts. 
The preceding examples can be repeated with similar success by substituting 
the generically or specifically described reactants and/or operating 
conditions of this invention for those used in the preceding examples. 
From the foregoing description, one skilled in the art can easily 
ascertain the essential characteristics of this invention, and without 
departing from the spirit and scope thereof, can make various changes and 
modifications of the invention to adapt it to various usages and 
conditions.