Triazole compounds with dopamine-D3-receptor affinity

Abstract

The invention relates to triazole compounds of formula (I), in which R1, R2, A and B have the meanings given in the description. The compounds provided for in the invention have a high affinity for the dopamine-D3-receptor and can therefore be used for the treatment of diseases which respond to the influence of dopamine-D3-ligands.

Description

The invention relates to triazole compounds and to the use of these compounds. These compounds possess valuable therapeutic properties and can be used for treating diseases which respond to the influence of dopamine D 3 receptor ligands.

Compounds of the type which is under discussion here and which possess physiological activity are already known. Thus, WO 94/25013; 96/02520; 97/43262; 97/47602; 98/06699; 98/49145; 98/50363; 98/50364 and 98/51671 describe compounds which act on the dopamine receptors. DE 44 25 144 A, WO 96/30333, WO 97/25324, WO 97/40015, WO 97/47602, WO 97/17326, EP 887 350, EP 779 284 A and Bioorg. & Med. Chem. Letters 9 (1999) 2059-2064 disclose further compounds which possess activity as dopamine D 3 receptor ligands. U.S. Pat. Nos. 4,338,453; 4,408,049 and 4,577,020 disclose triazole compounds which possess antiallergic or antipsychotic activity. WO 93/08799 and WO 94/25013 describe compounds of the type which is under discussion here and which constitute endothelin receptor antagonists. Additional triazole compounds, which inhibit blood platelet aggregation and which have a hypotensive effect are described in Pharmazie 46 (1991), 109-112. Further triazole compounds which possess physiological activity are disclosed in EP 691 342, EP 556 119, WO 97/10210, WO 98/24791, WO 96/31512 and WO 92/20655.

Neurons obtain their information by way of G protein-coupled receptors, inter alia. There are a large number of substances which exert their effect by way of these receptors. One of them is dopamine.

A number of facts about the presence of dopamine, and its physiological function as a neurotransmitter, are known with certainty. Disturbances of the dopaminergic transmitter system result in diseases such as schizophrenia, depression and Parkinson's disease. These, and other, diseases are treated with drugs which interact with the dopamine receptors.

By 1990, two subtypes of dopamine receptor had been clearly defined pharmacologically, namely the D 1 and D 2 receptors.

More recently, a third subtype has been found, namely the D 3 receptor, which appears to mediate some of the effects of the antipsychotic and anti-Parkinson agents (J. C. Schwartz et al., The Dopamine D 3 Receptor as a Target for Antipsychotics, in Novel Antipsychotic Drugs, H. Y. Meltzer, Ed. Raven Press, New York 1992, pages 135-144; M. Dooley et al., Drugs and Aging 1998, 12, 495-514).

Since D 3 receptors are chiefly expressed in the limbic system, it is assumed that while a selective D 3 ligand would probably have the properties of known antipsychotic agents, it would not have their dopamine D 3 receptor-mediated neurological side-effects (P. Sokoloff et al., Localization and Function of the D 3 Dopamine Receptor, Arzneim. Forsch./Drug Res . 42(1), 224 (1992); P. Sokoloff et al. Molecular Cloning and Characterization of a Novel Dopamine Receptor (D 3 ) as a Target for Neuroleptics, Nature , 347, 146 (1990)).

Surprisingly, it has now been found that certain triazole compounds exhibit a high affinity for the dopamine D 3 receptor and a low affinity for the D 2 receptor. These compounds are consequently selective D 3 ligands.

The present invention relates, therefore, to the compounds of the formula I:

where

R 1 is H, C 1 -C 6 -alkyl, which may be substituted by OH, OC 1 -C 6 -alkyl, halogen or phenyl, C 3 -C 6 -cycloalkyl or phenyl;

R 2 is H, C 1 -C 6 -alkyl, which may be substituted by OH, OC 1 -C 6 -alkyl, halogen or phenyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, halogen, CN, COOR 3 , CONR 3 R 4 , NR 3 R 4 , SO 2 R 3 , SO 2 NR 3 R 4 , or an aromatic radical which is selected from phenyl, naphthyl and a 5- or 6-membered heterocyclic radical having 1, 2, 3 or 4 heteroatoms which are selected, independently of each other, from O, N and S, with it being possible for the aromatic radical to have one or two substituents which are selected, independently of each other, from C 1 -C 6 -alkyl, which may be substituted by OH, OC 1 -C 6 -alkyl, halogen or phenyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, halogen, CN, COR 3 , NR 3 R 4 , NO 2 , SO 2 R 3 , SO 2 NR 3 R 4 and phenyl which may be substituted by one or two radicals which are selected, independently of each other, from C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, NR 3 R 4 , CN, CF 3 , CHF 2 or halogen;

R 3 and R 4 are, independently of each other, H, C 1 -C 6 -alkyl, which may be substituted by OH, OC 2 -C 6 -alkyl, halogen or phenyl, or phenyl;

A is C 4 -C 10 -alkylene or C 3 -C 10 -alkylene which comprises at least one group Z which is selected from O, S, CONR 3 , COO, CO, C 3 -C 6 -cycloalkyl and a double or triple bond;

B is a radical of the following formulae (a) and (b):

X is CH 2 or CH 2 CH 2 ;

Y is CH 2 or O;

R 6 and R 7 are, independently of each other, selected from H, C 1 -C 6 -alkyl, which may be substituted by halogen, OH, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, halogen, CN, NO 2 , SO 2 R 3 , SO 2 NR 3 R 4 , CONR 3 R 4 , NHSO 2 R 3 and NR 3 R 4 ;

and the salts thereof with physiologically tolerated acids.

The compounds according to the invention are selective dopamine D 3 receptor ligands which act in the limbic system in a regioselective manner and which, as a result of their low affinity for the D 2 receptor, have fewer side-effects than do the classic neuroleptic agents, which are D 2 receptor antagonists. The compounds can therefore be used for treating diseases which respond to dopamine D 3 ligands, i.e. they are effective for treating those diseases in which affecting (modulating) the dopamine D 3 receptors leads to an improvement in the clinical picture or to the disease being cured. Examples of such diseases are diseases of the cardiovascular system and the kidneys, diseases of the central nervous system, in particular schizophrenia, affective disorders, neurotic stress and somatoform disorders, psychoses, parkinsonism, attention deficit disorders, hyperactivity in children, epilepsy, amnesic and cognitive disorders such as learning and memory impairment (impaired cognitive function), anxiety states, dementia, delirium, personality disorders, sleep disturbances (e.g. restless legs syndrome), disorders of sex life (male impotence), eating disorders and addictive disorders. Moreover they are useful in the treatment of stroke.

Addictive disorders include the psychological disorders and behavioral disturbances caused by abuse of psychotropic substances such as pharmaceuticals or drugs, and other addictive disorders such as compulsive gambling (impulse control disorders not elsewhere classified). Addictive substances are, for example: opioids (e.g. morphine, heroin, codeine); cocaine; nicotine; alcohol; substances which interact with the GABA chloride channel complex, sedatives, hypnotics or tranquilizers, e.g. benzodiazepines; LSD; cannabinoids; psychomotor stimulants such as 3,4-methylenedioxy-N-methylamphetamine (ecstasy); amphetamine and amphetamine-like substances such as methylphenidate or other stimulants including caffeine. Addictive substances of particular concern are opioids, cocaine, amphetamine or amphetamine-like substances, nicotine and alcohol.

The compounds according to the invention are preferably employed for treating affective disorders; neurotic, stress and somatoform disorders and psychoses, e.g. schizophrenia.

Within the context of the present invention, the following expressions have the meanings given in conjunction with them:

Alkyl (also in radicals such as alkoxy, alkylthio, alkylamino etc.) is a straight-chain or branched alkyl group having from 1 to 6 carbon atoms and, in particular from 1 to 4 carbon atoms. The alkyl group can have one or more substituents which are selected, independently of each other, from OH, OC 1 -C 6 -alkyl, halogen or phenyl. In the case of a halogen substituent, the alkyl group can, in particular, encompass, 1, 2, 3 or 4 halogen atoms which can be located on one or more C atoms, preferably in the α or ω position. CF 3 , CHF 2 , CF 2 Cl or CH 2 F are particularly preferred.

Examples of an alkyl group are methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, t-butyl, etc.

Cycloalkyl is, in particular, C 3 -C 6 -cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

Alkylene radicals are straight-chain or branched. If A does not have a group Z, A then comprises from 4 to 10 carbon atoms, preferably from 4 to 8 carbon atoms. The chain between the triazole nucleus and group B then has at least four carbon atoms. If A has at least one of said Z groups, A then comprises from 3 to 10 carbon atoms, preferably from 3 to 8 carbon atoms.

If the alkylene groups comprise at least one of the Z groups, this or these groups can then be arranged in the alkylene chain at an arbitrary site or in position 1 or 2 of the A group (seen from the triazole radical). The radicals CONR 2 and COO are preferably arranged such that the carbonyl group is in each case facing the triazole ring. Particular preference is given to the compounds of the formula I in which A is —Z—C 3 -C 6 -alkylene, in particular —Z—CH 2 CH 2 CH 2 —, —Z—CH 2 CH 2 CH 2 CH 2 —, —Z—CH 2 CH═CHCH 2 —, —Z—CH 2 C(CH 3 )═CHCH 2 —,

—Z—CH 2 CH(CH 3 )CH 2 —or a linear —Z—C 7 -C 10 -alkylene radical, with Z being bonded to the triazole ring. Z is preferably CH 2 , O and in particular S. Preference is additionally given to A being —(CH 2 ) 4 —, —(CH 2 ) 5 —, —CH 2 CH 2 CH═CHCH 2 —,

—CH 2 CH 2 C(CH 3 )═CHCH 2 — or —CH 2 CH 2 CH(CH 3 )CH 2 —.

Halogen is F, Cl, Br or I, preferably F or Cl.

R 1 is preferably H, C 1 -C 6 -alkyl or C 3 -C 6 -cycloalkyl.

If R 2 is an aromatic radical, this radical is then preferably one of the following radicals:

where

R 9 to R 11 are H or the abovementioned substituents of the aromatic radical,

R 12 is H, C 1 -C 6 -alkyl or phenyl, and

T is N or CH.

If the phenyl radical is substituted, the substituents are preferably in the m position or the p position.

The aromatic radical is particularly preferably a group of the formula:

where R 9 , R 10 and R 12 have the abovementioned meanings. The indicated phenyl, pyridyl, thiazolyl and pyrrole radicals are particularly preferred.

The radicals R 9 to R 11 are preferably H, C 1 -C 6 alkyl, OR 3 , CN, phenyl, which may be substituted by C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy or halogen, CF 3 and halogen, and are, in particular, H, C 1 -C 6 -alkyl, OR 3 and halogen. In this context, R 3 has the abovementioned meanings.

Particularly preferably, R 2 is H, C 1 -C 6 -alkyl, NR 3 R 4 (R 3 and R 4 are, independently of each other, H or C 1 -C 6 -alkyl), phenyl or a 5-membered aromatic heterocyclic radical which has 1 or 2 heteroatoms which are independently selected from N, S and O. The heterocyclic radical is preferably a pyrrole radical or a pyridine radical.

X and/or Y are preferably CH 2 .

A is preferably C 4 -C 10 -alkylene or C 3 -C 10 -alkylene which comprises at least one group Z which is selected from O, S, COO, CO and a double bond.

Preferably, at least one of the radicals R 6 , R 7 and R 8 is H.

The radicals R 6 and R 7 are preferably, and independently of each other, selected from H, C 1 -C 6 -alkyl, OH, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio-C 1 -C 6 -alkyl, halogen, CN, NO 2 , SO 2 R 3 , SO 2 NR 3 R 4 and CONR 3 R 4 . Particularly preferably, the phenyl group has one or two substituents, i.e. one or two of the radicals R 6 and R 7 is/are C 1 -C 6 -alkyl, OH, halogen, CN, SO 2 NR 3 R 4 1 NO 2 or CF 3 .

Particular preference is given to the compounds of formula I where

R 1 is H, C 1 -C 6 -alkyl or phenyl,

R 2 is H, C 1 -C 6 -alkyl, phenyl, thienyl, furanyl, pyridyl, pyrrolyl, thiazolyl or pyrazinyl,

A is —SC 3 -C 10 -alkylene which can comprise a double bond, and

R 6 and R 7 are selected from H, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, halogen, SO 2 NR 3 R 4 ; CN, NO 2 and CF 3 .

The invention also encompasses the acid addition salts of the compounds of the formula I with physiologically tolerated acids. Examples of suitable physiologically tolerated organic and inorganic acids are hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid, oxalic acid, maleic acid, fumaric acid, lactic acid, tartaric acid, adipic acid or benzoic acid. Other acids which can be used are described in Fortschritte der Arzneimittelforschung [Advances in pharmaceutical research], Volume 10, pages 224 ff., Birkhäuser Verlag, Basle and Stuttgart, 1966.

The compounds of the formula I can exhibit one or more centers of asymmetry. The invention therefore includes not only the racemates but also the relevant enantiomers and diastereomers.

The respective tautomeric forms are also included in the invention.

The process for preparing the compounds of the formula I consist in

a) reacting a compound of the formula (II)

 where Y 1 is a customary leaving group, such as Hal, alkylsulfonyloxy, arylsulfonyloxy, etc., with a compound of the formula (III)

HB  (III);

 or

b) reacting a compound of the formula (IV)

 where Z 1 is O or S, and A 1 is C 1 -C 10 -alkylene or a bond, with a compound of the formula (V),

Y 1 —A 2 —B  (V)

where Y 1 has the abovementioned meaning and A 2 is C 2 -C 10 -alkylene, with A 1 and A 2 together having from 3 to 10 C atoms and A 1 and/or A 2 where appropriate comprising at least one group Z; or

c) reacting a compound of the formula (VI)

 where Y 1 and A 1 have the abovementioned meanings, with a compound of the formula (VII)

H—Z 1 —A—B  (VII)

where Z 1 has the abovementioned meanings; or

d) reversing the polarity of a compound of the formula (VIII)

 using reagents which are known from the literature, such as 1,3-propanedithiol, KCN/water, TMSCN (trimethylsilyl cyanide) or KCN/morpholine, as described, for example, in

Albright Tetrahedron , 1983, 39, 3207 or

D. Seebach Synthesis 1969, 17 und 1979, 19 or

H. Stetter Angew. Chem. Int. Ed . 1976, 15, 639 or

van Niel et al. Tetrahedron 1989, 45, 7643

Martin et al. Synthesis 1979, 633,

 to give the products (VIIIa) (using 1,3-propanedithiol by way of example)

 and then chain-elongating with compounds of the formula (IX)

Y 1 —A 3 —B  (IX)

where Y 1 has the abovementioned meaning and A 3 is C 3 -C 9 -alkylene which can contain a group Z,

 with compounds of the formula (Ia)

 where Z 2 is CO or a methylene group, and Z 2 and A 2 have together from 4 to 10 C atoms, being obtained after deprotecting or reducing, or

e) reacting a compound of the formula (VIII) with a compound of the formula (X)

Y 2 —A—B  (X)

 where Y 2 is a phosphorane or a phosphonic ester, in analogy with customary methods, as described, for example, in Houben Weyl “ Handbuch der Organischen Chemie ” [Textbook of Organic Chemistry], 4th Edition, Thieme Verlag Stuttgart, Volume V/lb p. 383 ff, or Vol. V/1c p. 575 ff, or

f) reacting a compound of the formula (XI)

 where Q is H or OH, with a compound of the formula III under reductive conditions in analogy with methods known from the literature, for example as described in J. Org. Chem . 1986, 50, 1927; or WO 92/20655.

The process for preparing a compound of the formula I where A comprises the groups COO or CONR 3 consists in reacting a compound of the formula (XII)

 where Y 3 is OH, OC 1 -C 4 -alkyl, Cl or, together with CO, an activated carboxyl group, and A 4 is C 0 -C 9 -alkylene, with a compound of the formula (XIII)

B—A—Z 3   (XIII)

where Z 3 is OH or NHR 3 .

Compounds of the type (XIV)

can be synthesized by alkylating compounds of the formula (IV) with compounds of the formula (XV),

to give compounds of the formula (XVI),

subsequently carrying out hydrazinolysis to give compounds of the type (XVII)

Compounds of the formula XVII (or XIV) can also be obtained by reacting compounds of the formula II with azides, such as sodium azide, and then reducing, as described, for example, in H. Staudinger, Helv. Chim. Acta 1985, 2, 635 or R. Carrie, Bull. Chem. Soc. Fr. 1985, 815.

Compounds of the general formulae B-H can be prepared as described, for example, in

S. Smith et al., Bioorg. Med. Chem. Lett . 1998, 8, 2859;

WO 97/47602, WO 920655 and W098/24791, or

J. Med. Chem . 1987, 30, 2111 and 2208.

The compounds of the formula (IV) type are either known or can be prepared using known methods, as described, for example, in A. R. Katritzky, C. W. Rees (ed.) “Comprehensive Heterocyclic Chemistry”, Pergamon Press, or “The Chemistry of Heterocyclic Compounds” J. Wiley & Sons Inc. N.Y. and the literature which is cited therein, or in S. Kubota et al. Chem. Pharm. Bull . 1975, 23, 955 or Vosilevskii et al. Izv. Akad. Nauk. SSSR Ser. Khim. 1975, 23, 955.

In the above formulae, R 1 , R 2 , R 6 , R 7 , A, B, X and Y have the meanings given in connection with formula I.

The compounds according to the invention, and the starting materials and the intermediates, can also be prepared in analogy with the methods which are described in the patent publications which were mentioned at the outset.

The above-described reactions are generally effected in a solvent at temperatures of between room temperature and the boiling temperature of the solvent employed. Examples of solvents which can be used are esters, such as ethyl acetate, ethers, such as diethyl ether or tetrahydrofuran, dimethylformamide, dimethyl sulfoxide, dimethoxyethane, toluene, xylene, acetonitrile, ketones, such as acetone or methyl ethyl ketone, or alcohols, such as ethanol or butanol.

If desired, the reactions can be carried out in the presence of an acid-binding agent. Suitable acid-binding agents are inorganic bases, such as sodium carbonate or potassium carbonate, or sodium hydrogencarbonate or potassium hydrogencarbonate, sodium methoxide, sodium ethoxide, sodium hydride, or organometallic compounds, such as butyl lithium or alkyl magnesium compounds, or organic bases, such as triethylamine or pyridine. The latter can also simultaneously serve as the solvent.

Process (f) is effected under reducing conditions, e.g. using sodium borohydride, sodium cyanoborohydride or triacetoxy borohydride, where appropriate in an acid medium or in the presence of a Lewis acid, such as zinc chloride, or by way of catalytic hydrogenation.

The crude product is isolated in a customary manner, for example by means of filtering, distilling off the solvent or extracting from the reaction mixture, etc. The resulting compounds can be purified in a customary manner, for example by recrystallization from a solvent, by chromatography or by converting into an acid addition compound.

The acid addition salts are prepared in a customary manner by mixing the free base with the corresponding acid, where appropriate in solution in an organic solvent, for example a lower alcohol, such as methanol, ethanol or propanol, an ether, such as methyl tert-butyl ether, a ketone, such as acetone or methyl ethyl ketone, or an ester, such as ethyl acetate.

For treating the abovementioned diseases, the compounds according to the invention are administered orally or parenterally (subcutaneously, intravenously, intramuscularly or intraperitoneally) in a customary manner. The administration can also be effected through the nasopharyngeal space using vapors or sprays.

The dosage depends on the age, condition and weight of the patient and on the type of administration. As a rule, the daily dose of active compound is from about 10 to 1000 mg per patient and day when administered orally and from about 1 to above 500 mg per patient and day when administered parenterally.

The invention also relates to pharmaceuticals which comprise the compounds according to the invention. In the customary pharmacological administration forms, these pharmaceuticals are present in solid or liquid form, for example as tablets, film tablets, capsules, powders, granules, sugar-coated tablets, suppositories, solutions or sprays. In this context, the active compounds can be worked up together with the customary pharmacological auxiliary substances, such as tablet binders, fillers, preservatives, tablet disintegrants, flow-regulating agents, plasticizers, wetting agents, dispersants, emulsifiers, solvents, retarding agents, antioxidants and/or propellent gases (cf. H. Sucker et al., Pharmazeutische Technologie, Thieme-Verlag, Stuttgart, 1978). The resulting administration forms normally comprise the active compound in a quantity of from 1 to 99% by weight.

The following examples serve to explain the invention without limiting it.

EXAMPLE 1

(cis/trans) 9-Bromo-3-{3-[(4-methyl-5-phenyl-4H-1,2,4-triazol-3-yl)sulfanyl]propyl}-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indole

Synthesis of the Starting Materials

1A Methyl (8-bromo-2-oxo-1,2,3,4-tetrahydronaphthalen-1-yl)-acetate

33 ml of 2M lithiumdiisopropylamide were added to a solution of 13.5 g (60 mmol) of 8-bromotetralone in 470 ml of THF at −30° C. under a protective gas atmopshere and, after stirring, a solution of 11 g (72.mmol) of methylbromoacetate in 100 ml of THF was added dropwise. The mixture was worked up after 18 h at room temperature by adding 10 ml of concentrated hydrochloric acid at 0° C. The solvent was removed in vacuo, and the residue was taken up in water and extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated; the residue was purified by column chromatography (silica gel, mobile phase: methylene chloride).

Yield: 13.7 g (46 mmol); 77% of theory C 13 H 13 BrO 3 (297.2) MS: 296/298 [M + ]

1B (cis/trans) 9-Bromo-3-{3-[(4-methyl-5-phenyl-4H-1,2,4-triazol-3-yl)sulfanyl]propyl}-1,3,3a,4,5,9b-hexahydro-2H-benzo[e]indol-2-one

To a solution of 0.9 g (3.6 mmol) of 3-[(4-methyl-5-phenyl-4H-1,2,4-triazol-3-yl)sulfanyl]propylamine and 0.7 g (2.4 mmol) of the above compound in 10 ml of THF/methanol=1/1 at 0° C. were added 0.8 ml of glacial acetic acid (pH 4-5) and then 0.2 mg (2.4 mmol) of sodium cyanoborohydride, and the mixture was stirred at room temperature for 72 hours. Workup entailed addition of 20% strength sodium hydroxide solution, concentration in vacuo and taking out the residue with dichloromethane. The organic phase was washed with water, dried over sodium sulfate, filtered and concentrated, after which the residue was purified by column chromatography (silica gel, mobile phase: methylene chloride with 3-5% methanol).

Yield: 0.6 g(1.1mmol); 47% of theory 1 H-NMR (CDC13): δ=1.8-2.3 (m, 6H); 2,7 (mbr, 2H); 3.1-3.4 (m, 4H); 3.6 (s, 3H); 3.8-4.0 (m, 2H); 4.1 (m, 1H); 7.1 (m, 2H); 7.4 (d, 1H); 7.5 (m, 3H);. 7.7 (m, 2H).

C 24 H 25 BrN 4 OS (497.5).

Preparation of the Final Product

560 mg (1.1 mmol) of the compound prepared in 1B and dissolved in 2 ml of THF were added to 1.9 ml of a 1M borane/THF solution while cooling in ice and under protective gas, and the mixture was heated to boiling for 1 hour. After the reaction was complete, 1 ml of 10% strength hydrochloric acid was added, the mixture was concentrated, the residue was taken up in water and, after making alkaline, extracted with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and concentrated. The crude product was purified by chromatography (silica gel, mobile phase: methylene chloride with 3-5% methanol).

Yield: 40 mg (0.1 mmol); 8% of theory 1 H-NMR (CDC13): δ=1.3-1.5 (m, 2H); 1.9 (m, 1H); 2.0 (m, 2H); 2.2 (m, 1H); 2.4-2.5 (m, 2H); 2.6 (m, 1H); 2.8-3.0 (m, 3H); 3.1 (t, 1H);,3.2-3.4 (2m, 2H); 3.6 (m, 4H); 6.9 (t, 1H); 7.0 (d, 1H); 7.4 (d, 1H); 7.5 (m, 3H); 7.7 (m, 2H). C 24 H 27 BrN 4 S (482.9).

The following was prepared in an analogous manner in principle:

EXAMPLE 2

(cis/trans) 7-tert-Butyl-3-{3-[(4-methyl-5-phenyl-4H-1,2,4-triazol-3-yl)sulfanyl]propyl}-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indole

C 28 H 36 N 4 S (460.7) MS: 461 [M + ]

EXAMPLE 3

(cis/trans) 9-Bromo-3-{3-[(4-methyl-5-(thien-3-yl)-4H-1,2,4-triazol-3-yl)sulfanyl]propyl}-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indole

EXAMPLE 4

(cis/trans) 3-{3-[(4-methyl-5-phenyl-4H-1,2,4-triazol-3-yl)-butyl}-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indole

The following compounds can be prepared in an analogous way in principle:

TABLE 1
Ex.	R 1	R 2	A	Y	R 6	R 7 *
5	Et	2,5-Di-methyl-furanyl-3-	S—(CH 2 ) 3 —	CH 2	7-tert-butyl	H
6	Me	2-Pyrazinyl-	O—(CH 2 ) 3 —	CH 2	H
7	Propyl	3-Br-Pyridin-5-yl-	S—(CH 2 ) 3 —	CH 2	7-carboxamido
8	Phenyl	Cyano	S—(CH 2 ) 3 —	CH 2	H
9	Ethyl	3-Jod-phenyl	(CH 2 ) 4 —	O	7-tert-butyl
10	Me	3-Pyrrolyl	S—(CH 2 ) 3 —	CH 2	8-fluoro
11	butyl	2,5-Di-methyl-furanyl-3-	S—(CH 2 ) 3 —	CH 2	7-methoxy	8-methoxy
12	Me	2-Pyrazinyl-	S—(CH 2 ) 3 —	CH 2	7-tert-butyl
13	cycPropyl	Pyridin-4-yl-	S—(CH 2 ) 3 —	CH 2	8-fluoro
14	Ethyl	4-Methylthiazol-5-yl	S—CH 2 —C(CH 3 )═CH—CH 2 —	CH 2	7-tert-butyl
15	Me	4-Methoxyphenyl	(CH 2 ) 4 —	CH 2	9-fluoro
16	Me	4-Jod-phenyl	S—(CH 2 ) 3 —	CH 2	7-tert-butyl
17	Me	2-Thienyl	(CH 2 ) 4 —	CH 2	H
18	Propyl	4-Imidazolyl-	S—(CH 2 ) 3 —	CH 2	7-carboxamido
19	Me	2,5-Di-methyl-furanyl-3-	S—(CH 2 ) 3 —	CH 2	H
20	Propyl	4-Methylthiazol-5-yl	CONH—(CH 2 ) 4 —	CH 2	7-methyl
21	Me	Phenyl	S—CH 2 —C(═CH 2 )—CH 2	O	8-bromo
22	Me	N-Methyl-2-Pyrrolyl-	(CH 2 ) 4 —	O	9-methyl
23	Me	Tetrazolyl-	S—(CH 2 ) 3 —	CH 2	8-fluoro
24	Me	2-Me-4-Oxazolyl-	S—(CH 2 ) 3 —	O	7-tert-butyl
25	Me	Oxadiazol-2-yl	S—(CH 2 ) 3 —	CH 2	H
26	Me	3-Cyano-phenyl	S—(CH 2 ) 3 —	CH 2	6-methoxy
27	isoPropyl	3-Br-Pyridin-5-yl-	S—(CH 2 ) 3 —	CH 2	8-trifluoromethoxy
28	Me	2-Thienyl	S—CH 2 —C(═CH 2 )—CH 2	CH 2	8-fluoro
29	Me	2-Aminothiazol-4yl-	S—(CH 2 ) 3 —	CH 2	6-methoxy
30	Me	3-Cyano-phenyl	S—(CH 2 ) 3 —	O	H
31	Me	3-Thienyl	S—(CH 2 ) 3 —	CH 2	7-tert-butyl
32	Me	4-Methylthiazol-5-yl	S—(CH 2 ) 3 —	O	7-nitro
33	Me	Cyclohexyl-	S—(CH 2 ) 3 —	CH 2	8-fluoro
34	isoPropyl	2-Aminothiazol-4yl-	S—(CH 2 ) 3 —	CH 2	8-trifluoromethoxy
35	Me	3-Jod-phenyl	(CH 2 ) 4 —	O	7-tert-butyl
36	butyl	Pyridin-4-yl-	S—(CH 2 ) 3 —	CH 2	7-methoxy	8-methoxy
37	Me	4-Methoxyphenyl	S—(CH 2 ) 3 —	CH 2	7-cyano
38	Hexyl	4-Imidazolyl-	S—(CH 2 ) 3 —	CH 2	6-methoxy
39	Ethyl	Pyridin-3-yl-	S—(CH 2 ) 6 —	CH 2	7-tert-butyl
40	Me	4-Methoxyphenyl	(CH 2 ) 4 —	O	9-fluoro
41	Propyl	N-Methyl-2-Pyrrolyl-	CONH—(CH 2 ) 4 —	CH 2	8-trifluoromethoxy
42	cycPropyl	4-Methoxyphenyl	S—(CH 2 ) 3 —	CH 2	8-fluoro
43	Me	N-Methyl-2-Pyrrolyl-	S—(CH 2 ) 3 —	CH 2	7-nitro
44	Me	3-Jod-phenyl	O—(CH 2 ) 3 —	O	H
45	Me	N-Propyl-tetrazolyl-	S—(CH 2 ) 3 —	O	H
46	isoButyl	Oxadiazol-2-yl	S—(CH 2 ) 3 —	O	7-tert-butyl
47	Ethyl	Pyridin-3-yl-	(CH 2 ) 4 —	O	H
48	Me	2-Thienyl	S—(CH 2 ) 3 —	O	7-nitro
49	Me	Phenyl	CO—CH 2 —C(═CH 2 )—CH 2	O	7-tert-butyl
50	Me	Pyridin-3-yl-	S—(CH 2 ) 3 —	CH 2	6-methoxy
51	Me	N-Methyl-2-Pyrrolyl-	S—(CH 2 ) 3 —	CH 2	H
52	Me	Pyridin-3-yl-	S—(CH 2 ) 3 —	O	7-cyano
53	butyl	3-Cyano-phenyl	S—(CH 2 ) 3 —	CH 2	7-methoxy	8-methoxy
54	Me	2-Thienyl	S—(CH 2 ) 8 —	O	6-methoxy
55	Me	2-Pyrazinyl-	S—(CH 2 ) 3 —	O	7-nitro
56	Ethyl	2-Thienyl	(CH 2 ) 4 —	O	H
57	Ethyl	Phenyl	S—CH 2 —C(CH 3 )═CH—CH 2 —	O	7-tert-butyl
58	Me	4-Methoxyphenyl	S—(CH 2 ) 3 —	CH 2	7-tert-butyl
59	Me	3-Br-Pyridin-5-yl-	S—(CH 2 ) 3 —	CH 2	H
60	Me	N-Methyl-2-Pyrrolyl-	S—(CH 2 ) 3 —	O	H
61	Me	N-Propyl-tetrazolyl-	S—(CH 2 ) 3 —	CH 2	8-trifluoromethoxy
62	butyl	3-Br-Pyridin-5-yl-	S—(CH 2 ) 3 —	CH 2	7-methoxy	8-methoxy
63	Ethyl	Phenyl	S—CH 2 —C(CH 3 )═CH—CH 2 —	O	7-sulfonamido
64	Me	2-Thienyl	S—(CH 2 ) 3 —	CH 2	7-sulfonamido
65	Me	Pyridin-3-yl-	S—(CH 2 ) 8 —	CH 2	8-trifluoromethoxy
66	Me	3-Jod-phenyl	S—(CH 2 ) 3 —	CH 2	8-fluoro
67	Me	Phenyl	O—(CH 2 ) 4 —	O	8-iod
68	Me	Pyridin-3-yl-	S—(CH 2 ) 8 —	O	8-trifluoromethoxy
69	isoPropyl	3-Cyano-phenyl	S—(CH 2 ) 3 —	CH 2	8-trifluoromethoxy
70	butyl	N-Propyl-tetrazolyl-	S—(CH 2 ) 3 —	CH 2	7-methoxy	8-methoxy
71	Ethyl	Pyridin-3-yl-	S—CH 2 —CH═CH—CH 2 —	CH 2	8-fluoro
72	Me	3-Br-Pyridin-5-yl-	S—(CH 2 ) 3 —	O	H
73	Phenyl	Methylamino	S—(CH 2 ) 3 —	CH 2	8-fluoro
74	Ethyl	Phenyl	CO—(CH 2 ) 3 —	O	H
75	Me	Phenyl	S—(CH 2 ) 10 —	CH 2	7-methyl
76	cycPropyl	4-Imidazolyl-	S—(CH 2 ) 3 —	CH 2	8-fluoro
77	Me	2-Thienyl	S—(CH 2 ) 3 —	O	H
78	Me	3-Jod-phenyl	O—(CH 2 ) 3 —	CH 2	H
79	Et	3-Benzthienyl-	S—(CH 2 ) 3 —	CH 2	7-tert-butyl
80	Me	4-Methoxyphenyl	S—(CH 2 ) 3 —	CH 2	7-nitro
81	Ethyl	Phenyl	S—(CH 2 ) 3 —	O	7-nitro
82	Ethyl	2-Thienyl	CO—(CH 2 ) 3 —	CH 2	H
83	cycPropyl	3-Cyano-phenyl	S—(CH 2 ) 3 —	CH 2	8-fluoro
84	Propyl	Phenyl	CONH—(CH 2 ) 5 —	CH 2	7-methyl
85	Me	2,5-Di-methyl-furanyl-3-	S—(CH 2 ) 3 —	O	H
86	Et	N-Propyl-tetrazolyl-	S—(CH 2 ) 3 —	CH 2	7-tert-butyl
87	Ethyl	2-Aminothiazol-4yl-	S—(CH 2 ) 3 —	O	H
88	Me	Tetrazolyl-	S—(CH 2 ) 3 —	CH 2	H
89	Propyl	Phenyl	COO—(CH 2 ) 4 —	CH 2	7-methyl
90	Propyl	2-Pyrazinyl-	COO—(CH 2 ) 4 —	CH 2	8-trifluoromethoxy
91	Propyl	Pyridin-3-yl-	CONH—(CH 2 ) 4 —	CH 2	7-methyl
92	Me	Oxadiazol-2-yl	S—(CH 2 ) 3 —	CH 2	8-fluoro
93	butyl	3-Benzthienyl-	S—(CH 2 ) 3 —	CH 2	7-methoxy	8-methoxy
94	Me	4-Methylthiazol-5-yl	(CH 2 ) 4 —	CH 2	9-methyl
95	Me	4-Methylthiazol-5-yl	(CH 2 ) 4 —	O	9-methyl
96	Me	3-Jod-phenyl	S—(CH 2 ) 3 —	CH 2	H
97	Me	2-Thienyl	(CH 2 ) 4 —	O	H
98	isoPropyl	5-Methyl imidazol-4-yl-	S—(CH 2 ) 3 —	O	8-trifluoromethoxy
99	Me	N-Methyl-2-Pyrrolyl-	S—(CH 2) 3 —	O	7-cyano
100	Me	Phenyl	S—(CH 2 ) 3 —	CH 2	7-cyano
101	isoButyl	Tetrazolyl-	S—(CH 2 ) 3 —	O	H
102	Me	Phenyl	CO—CH 2 —C(═CH 2 )—CH 2	CH 2	7-tert-butyl
103	Me	2-Pyrazinyl-	S—(CH 2 ) 3 —	CH 2	6-methoxy
104	Me	2-Pyrazinyl-	S—(CH 2 ) 3 —	CH 2	7-nitro
105	Ethyl	Pyridin-3-yl-	S—CH 2 —CH═CH—CH 2 —	O	8-fluoro
106	Me	4-Methylthiazol-5-yl	S—(CH 2 ) 3 —	O	H
107	Me	2-Pyrazinyl-	(CH 2 ) 4 —	O	7-methyl
108	Phenyl	4-Imidazolyl-	S—(CH 2 ) 3 —	O	H
109	Me	Pyridin-4-yl-	S—(CH 2 ) 3 —	CH 2	8-trifluoromethoxy
110	Me	2-Thienyl	S—(CH 2 ) 7 —	CH 2	8-trifluoromethoxy
111	Hexyl	3-Benzthienyl-	S—(CH 2 ) 3 —	CH 2	6-methoxy
112	cycPropyl	Amino	S—(CH 2 ) 3 —	CH 2	8-fluoro
113	Me	2-Thienyl	S—(CH 2 ) 3 —	O	7-cyano
114	Me	Oxadiazol-2-yl	S—(CH 2 ) 3 —	CH 2	7-tert-butyl
115	Ethyl	4-Methylthiazol-5-yl	S—CH 2 —C(═CH 2 )—CH 2	O	7-sulfonamido
116	Me	2-Thienyl	S—(CH 2 ) 3 —	CH 2	8-fluoro
117	Me	Methylamino	S—(CH 2 ) 3 —	CH 2	H
118	Me	3-Pyrrolyl	S—(CH 2 ) 3 —	CH 2	7-tert-butyl
119	Me	N-Methyl-2-Pyrrolyl-	S—(CH 2 ) 3 —	CH 2	7-sulfonamido
120	butyl	2-Aminothiazol-4yl-	S—(CH 2 ) 3 —	CH 2	7-methoxy	8-methoxy
121	Me	N-Methyl-2-Pyrrolyl-	S—(CH 2 ) 3 —	O	7-nitro
122	isoPropyl	Phenyl	S—(CH 2 ) 3 —	O	7-sulfonamido
123	Me	2-Me-4-Oxazolyl-	S—(CH 2 ) 3 —	CH 2	6-methoxy
124	cycPropyl	Methylamino	S—(CH 2 ) 3 —	CH 2	7-tert-butyl
125	isoPropyl	Cyano	S—(CH 2 ) 3 —	CH 2	6-methoxy
126	Me	Phenyl	S—(CH 2 ) 3 —	CH 2	6-methoxy
127	Propyl	3-Cyano-phenyl	S—(CH 2 ) 3 —	CH 2	7-carboxamido
128	Propyl	Phenyl	CONH—(CH 2 ) 5 —	O	7-methyl
129	Ethyl	3-Jod-phenyl	S—(CH 2 ) 3 —	CH 2	7-methoxy	8-methoxy
130	Ethyl	4-Methylthiazol-5-yl	S—(CH 2 ) 6 —	O	7-cyano
131	Me	N-Methyl-2-Pyrrolyl-	S—(CH 2 ) 3 —	CH 2	7-methoxy	8-methoxy
132	Me	2-Aminothiazol-4yl-	S—(CH 2 ) 3 —	CH 2	H
133	Me	Oxadiazol-2-yl	S—(CH 2 ) 3 —	CH 2	7-methoxy	8-methoxy
134	Me	2-Me-4-Oxazolyl-	S—(CH 2 ) 3 —	CH 2	7-methoxy	8-methoxy
135	Me	Pyridin-3-yl-	(CH 2 ) 4 —	CH 2	H
136	Ethyl	Phenyl	S—CH 2 —C(CH 3 )═CH—CH 2 —	CH 2	7-tert-butyl
137	Me	Phenyl	(CH 2 ) 4 —	O	H
138	Et	4-Imidazolyl-	S—(CH 2 ) 3 —	CH 2	7-tert-butyl
139	isoPropyl	3-Benzthienyl-	S—(CH 2 ) 3 —	CH 2	8-trifluoromethoxy
140	Me	2-Pyrazinyl-	S—(CH 2 ) 3 —	O	7-cyano
141	Hexyl	Amino	S—(CH 2 ) 3 —	CH 2	6-methoxy
142	Me	5-Methyl imidazol-4-yl-	S—(CH 2 ) 3 —	CH 2	6-methoxy
143	Me	Pyridin-3-yl-	S—(CH 2 ) 3 —	CH 2	7-tert-butyl
144	Me	Pyridin-3-yl-	S—(CH 2 ) 3 —	CH 2	8-fluoro
145	cycPropyl	N-Propyl-tetrazolyl-	S—(CH 2 ) 3 —	CH 2	8-fluoro
146	Me	2-Me-4-Oxazolyl-	S—(CH 2 ) 3 —	CH 2	H
147	Me	3-Jod-phenyl	S—(CH 2 ) 3 —	CH 2	7-nitro
148	Propyl	4-Methoxyphenyl	COO—(CH 2 ) 3 —	CH 2	7-sulfonamido
149	Me	Pyridin-3-yl-	(CH 2 ) 4 —	OH	H
150	Me	2-Thienyl	O—(CH 2 ) 4 —	CH 2	7-tert-butyl
151	butyl	5-Methyl imidazol-4-yl-	S—(CH 2 ) 3 —	CH 2	7-methoxy	8-methoxy
152	isoButyl	Methylamino	S—(CH 2 ) 3 —	O	H
153	Hexyl	N-Propyl-tetrazolyl-	S—(CH 2 ) 3 —	CH 2	6-methoxy
154	Phenyl	Amino	S—(CH 2 ) 3 —	O	H
155	Me	Phenyl	CO—CH 2 —C(═CH 2 )—CH 2	O	7-tert-butyl
156	Me	2-Pyrazinyl-	S—(CH 2 ) 3 —	O	H
157	Me	3-Pyrrolyl	S—(CH 2 ) 3 —	CH 2	6-methoxy
158	Me	2-Me-4-Oxazolyl-	S—(CH 2 ) 3 —	CH 2	8-fluoro
159	Me	Phenyl	S—(CH 2 ) 3 —	O	H
160	Ethyl	Pyridin-3-yl-	S—(CH 2 ) 6 —	O	7-tert-butyl
161	Me	3-Jod-phenyl	S—(CH 2 ) 3 —	CH 2	7-sulfonamido
162	Me	3-Pyrrolyl	S—(CH 2 ) 3 —	O	H
163	isoPropyl	3-Pyrrolyl	S—(CH 2 ) 3 —	CH 2	8-trifluoromethoxy
164	Me	Pyridin-3-yl-	S—(CH 2 ) 3 —	O	7-tert-butyl
165	Me	2-Thienyl	S—(CH 2 ) 3 —	O	7-nitro
166	butyl	4-Imidazolyl-	S—(CH 2 ) 3 —	CH 2	7-methoxy	8-methoxy
167	Me	Tetrazolyl-	S—(CH 2 ) 3 —	CH 2	7-tert-butyl
168	Me	Phenyl	O—(CH 2 ) 4 —	CH 2	7-tert-butyl
169	Me	Phenyl	S—(CH 2 ) 3 —	CH 2	7-methoxy	8-methoxy
170	Me	N-Methyl-2-Pyrrolyl-	(CH 2 ) 4 —	CH 2	9-methyl
171	Me	3-Jod-phenyl	(CH 2 ) 4 —	CH 2	7-tert-butyl
172	Me	5-Methyl imidazol-4-yl-	S—(CH 2 ) 3 —	CH 2	8-fluoro
173	Me	2-Aminothiazol-4yl-	S—(CH 2 ) 3 —	CH 2	7-tert-butyl
174	Me	4-Methoxyphenyl	S—(CH 2 ) 3 —	O	7-nitro
175	Me	Pyridin-4-yl-	S—(CH 2 ) 3 —	O	H
176	Me	2-Thienyl	S—(CH 2 ) 3 —	CH 2	7-cyano
177	Me	2-Thienyl	S—(CH 2 ) 3 —	CH 2	7-methoxy	8-methoxy
178	Me	2-Pyrazinyl-	O—(CH 2 ) 3 —	O	H
179	isoPropyl	5-Methyl imidazol-4-yl-	S—(CH 2 ) 3 —	CH 2	8-trifluoromethoxy
180	Me	Pyridin-3-yl-	S—(CH 2 ) 3 —	O	7-nitro
181	Me	Phenyl	S—CH 2 —C(═CH 2 )—CH 2	CH 2	8-bromo
182	Me	Tetrazolyl-	S—(CH 2 ) 3 —	CH 2	7-methoxy	8-methoxy
183	Propyl	2-Aminothiazol-4yl-	S—(CH 2 ) 3 —	CH 2	7-carboxamido
184	Me	3-Br-Pyridin-5-yl-	S—(CH 2 ) 3 —	CH 2	8-fluoro
185	Me	N-Methyl-2-Pyrrolyl-	S—CH 2 —CH═CH—CH 2 —	CH 2	8-fluoro
186	Propyl	2-Thienyl	COO—(CH 2 ) 4 —	CH 2	6-methoxy
187	Me	2-Thienyl	S—(CH 2 ) 3 —	CH 2	6-methoxy
188	Propyl	3-cyano-phenyl	CONH—(CH 2 ) 5 —	CH 2	7-methyl
189	Propyl	Pyridin-4-yl-	S—(CH 2 ) 3 —	CH 2	7-carboxamido
190	Me	3-Cyano-phenyl	S—(CH 2 ) 3 —	CH 2	H
191	isoPropyl	4-Methoxyphenyl	S—(CH 2 ) 3 —	O	7-sulfonamido
192	Me	Phenyl	S—(CH 2 ) 3 —	CH 2	8-trifluoromethoxy
193	Me	2-Pyrazinyl-	S—(CH 2 ) 3 —	CH 2	7-sulfonamido
194	Ethyl	Phenyl	S—(CH 2 ) 3 —	CH 2	7-nitro
195	Phenyl	3-Benzthienyl-	S—(CH 2 ) 3 —	CH 2	H
196	Me	2-Pyrazinyl-	S—(CH 2 ) 3 —	CH 2	8-fluoro
197	Me	3-Jod-phenyl	S—(CH 2 ) 3 —	CH 2	7-cyano
198	Ethyl	4-Methylthiazol-5-yl	S—CH 2 —C(═CH 2 )—CH 2	CH 2	7-sulfonamido
199	Me	3-Cyano-phenyl	S—(CH 2 ) 3 —	CH 2	7-tert-butyl
200	cycPropyl	2-Me-4-Oxazolyl-	S—(CH 2 ) 3 —	CH 2	7-tert-butyl
201	Me	3-Jod-phenyl	S—(CH 2 ) 3 —	CH 2	6-methoxy
202	Me	2,5-Di-methyl-furanyl-3-	S—(CH 2 ) 3 —	CH 2	8-fluoro
203	Propyl	3-Jod-phenyl	COO—(CH 2 ) 4 —	CH 2	8-trifluoromethoxy
204	isoPropyl	4-Methoxyphenyl	S—(CH 2 ) 3 —	CH 2	7-sulfonamido
205	Me	N-Methyl-2-Pyrrolyl-	S—(CH 2 ) 3 —	CH 2	7-cyano
206	Ethyl	Pyridin-3-yl-	S—CH 2 —C(CH 3 )═CH—CH 2 —	O	7-tert-butyl
207	cycPropyl	3-Benzthienyl-	S—(CH 2 ) 3 —	CH 2	8-fluoro
208	Me	Pyridin-3-yl-	S—(CH 2 ) 3 —	CH 2	7-sulfonamido
209	Phenyl	4-Imidazolyl-	S—(CH 2 ) 3 —	CH 2	H
210	Propyl	Phenyl	S—(CH 2 ) 3 —	O	7-carboxamido
211	Me	Phenyl	S—(CH 2 ) 7 —	O	7-tert-butyl
212	Me	4-Methoxyphenyl	S—(CH 2 ) 3 —	O	7-cyano
213	Me	3-Br-Pyridin-5-yl-	S—(CH 2 ) 3 —	CH 2	7-tert-butyl
214	Hexyl	4-Methoxyphenyl	S—(CH 2 ) 3 —	CH 2	6-methoxy
215	isoPropyl	Methylamino	S—(CH 2 ) 3 —	CH 2	6-methoxy
216	Me	2,5-Di-methyl-furanyl-3-	S—(CH 2 ) 3 —	CH 2	6-methoxy
217	Me	N-Methyl-2-Pyrrolyl-	S—(CH 2 ) 3 —	CH 2	7-tert-butyl
218	Me	Phenyl	O—(CH 2 ) 3 —	CH 2	7-sulfonamido
219	Me	Pyridin-3-yl-	S—(CH 2 ) 3 —	CH 2	7-methoxy	8-methoxy
220	Ethyl	N-Methyl-2-Pyrrolyl-	(CH 2 ) 4 —	O	9-methyl
221	isoPropyl	Tetrazolyl-	S—(CH 2 ) 3 —	CH 2	6-methoxy
222	Me	4-Methylthiazol-5-yl	S—(CH 2 ) 3 —	CH 2	7-sulfonamido
223	Me	N-Methyl-2-Pyrrolyl-	S—(CH 2 ) 3 —	O	7-cyano
224	Me	5-Methyl imidazol-4-yl-	S—(CH 2 ) 3 —	CH 2	7-tert-butyl
225	Me	Phenyl	S—(CH 2 ) 7 —	CH 2	7-tert-butyl
226	Ethyl	2-Thienyl	CO—(CH 2 ) 3 —	O	H
227	Me	Methylamino	S—(CH 2 ) 3 —	CH 2	7-methoxy	8-methoxy
228	isoPropyl	3-Benzthienyl-	S—(CH 2 ) 3 —	O	8-trifluoromethoxy
229	Me	4-Methylthiazol-5-yl	S—(CH 2 ) 3 —	O	7-cyano
230	Propyl	Phenyl	S—(CH 2 ) 3 —	CH 2	7-carboxamido
231	Me	Phenyl	S—(CH 2 ) 3 —	CH 2	H
232	isoPropyl	Phenyl	S—(CH 2 ) 3 —	CH 2	7-sulfonamido
233	Me	3-Jod-phenyl	O—(CH 2 ) 3 —	O	7-nitro
234	Me	4-Methylthiazol-5-yl	S—(CH 2 ) 3 —	CH 2	7-nitro
235	Me	Phenyl	S—(CH 2 ) 3 —	O	7-cyano
236	Me	2-Thienyl	S—(CH 2 ) 3 —	CH 2	H
237	Et	Amino	S—(CH 2 ) 3 —	CH 2	7-tert-butyl
238	Me	4-Methylthiazol-5-yl	S—(CH 2 ) 3 —	CH 2	6-methoxy
239	Me	N-Methyl-2-Pyrrolyl-	S—(CH 2 ) 3 —	CH 2	6-methoxy
240	cycPropyl	Cyclohexyl-	S—(CH 2 ) 3 —	CH 2	7-tert-butyl
241	Ethyl	Phenyl	CO—(CH 2 ) 3 —	CH 2	H
242	Me	Pyridin-3-yl-	S—(CH 2 ) 3 —	CH 2	H
243	Me	4-Methoxyphenyl	S—(CH 2 ) 3 —	O	H
244	Me	N-Propyl-tetrazolyl-	S—(CH 2 ) 3 —	CH 2	H
245	Me	2-Pyrazinyl-	S—(CH 2 ) 3 —	CH 2	H
246	Ethyl	4-Methylthiazol-5-yl	S—CH 2 —C(CH 3 )═CH—CH 2 —	O	7-tert-butyl
247	Me	2-Thienyl	S—(CH 2 ) 3 —	CH 2	7-nitro
248	Me	4-Methylthiazol-5-yl	S—(CH 2 ) 3 —	CH 2	8-fluoro
249	Phenyl	3-Benzthienyl-	S—(CH 2 ) 3 —	O	H
250	Me	3-Jod-phenyl	S—(CH 2 ) 3 —	O	7-tert-butyl
251	Me	N-Methyl-2-Pyrrolyl-	S—(CH 2 ) 3 —	CH 2	8-fluoro
252	Et	Pyridin-4-yl-	S—(CH 2 ) 3 —	CH 2	7-tert-butyl
253	Phenyl	Carboxamido	S—(CH 2 ) 3 —	CH 2	8-fluoro
254	Ethyl	Phenyl	S—(CH 2 ) 3 —	O	7-nitro
255	Me	3-Pyrrolyl	S—(CH 2 ) 3 —	CH 2	7-carboxamido
256	isoPropyl	3-Pyrrolyl	S—(CH 2 ) 3 —	O	8-trifluoromethoxy
257	Me	Amino	S—(CH 2 ) 3 —	CH 2	7-methoxy	8-methoxy
258	Propyl	Phenyl	COO—(CH 2 ) 4 —	O	7-methyl
259	Me	Oxadiazol-2-yl	S—(CH 2 ) 3 —	O	7-methoxy	8-methoxy
260	Me	2-Aminothiazol-4yl-	S—(CH 2 ) 3 —	CH 2	8-fluoro
261	Phenyl	Amino	S—(CH 2 ) 3 —	CH 2	H
262	Me	Phenyl	S—(CH 2 ) 10 —	O	7-methyl
263	Me	Phenyl	S—(CH 2 ) 3 —	CH 2	8-fluoro
264	Me	Pyridin-4-yl-	S—(CH 2 ) 3 —	CH 2	H
265	Ethyl	4-Methylthiazol-5-yl	S—(CH 2 ) 6 —	O	7-cyano
266	Hexyl	Pyridin-4-yl-	S—(CH 2 ) 3 —	CH 2	6-methoxy
267	Me	5-Methyl imidazol-4-yl-	S—(CH 2 ) 3 —	O	H
268	butyl	Cyano	S—(CH 2 ) 3 —	CH 2	7-methoxy	8-methoxy
269	Me	4-Methylthiazol-5-yl	S—(CH 2 ) 3 —	CH 2	7-methoxy	8-methoxy
270	Me	2-Pyrazinyl-	(CH 2 ) 4 —	CH 2	7-methyl
271	Me	4-Methylthiazol-5-yl	S—(CH 2 ) 3 —	CH 2	H
272	Me	Cyclohexyl-	S—(CH 2 ) 3 —	CH 2	6-methoxy
273	Me	4-Methoxyphenyl	S—(CH 2 ) 3 —	O	7-methoxy	8-methoxy
274	Me	2-Thienyl	S—(CH 2 ) 7 —	O	8-trifluoromethoxy
275	Phenyl	Cyano	S—(CH 2 ) 3 —	O	H
276	Me	Pyridin-3-yl-	S—(CH 2 ) 3 —	CH 2	7-cyano
277	Me	Phenyl	(CH 2 ) 4 —	CH 2	H
278	butyl	3-Pyrrolyl	S—(CH 2 ) 3 —	CH 2	7-methoxy	8-methoxy
279	Me	Phenyl	S—(CH 2 ) 7 —	O	7-tert-butyl
280	Me	4-Methylthiazol-5-yl	S—(CH 2 ) 3 —	CH 2	7-cyano
281	Me	2-Thienyl	S—CH 2 —C(═CH 2 )—CH 2	O	8-fluoro
282	Me	4-Methoxyphenyl	S—(CH 2 ) 3 —	CH 2	7-methoxy	8-methoxy
283	Me	5-Methyl imidazol-4-yl-	S—(CH 2 ) 3 —	CH 2	H
284	Me	4-Methylthiazol-5-yl	S—(CH 2 ) 3 —	O	7-cyano
285	Me	2-Pyrazinyl-	S—(CH 2 ) 3 —	CH 2	7-cyano
286	Me	3-Jod-phenyl	S—(CH 2 ) 3 —	O	7-nitro
287	Me	2-Thienyl	S—(CH 2 ) 8 —	CH 2	6-methoxy
288	isoPropyl	Oxadiazol-2-yl	S—(CH 2 ) 3 —	CH 2	6-methoxy
289	Me	3-Br-Pyridin-5-yl-	S—(CH 2 ) 3 —	CH 2	6-methoxy
290	Me	Pyridin-3-yl-	S—(CH 2 ) 3 —	CH 2	7-nitro
291	Me	4-Methoxyphenyl	S—(CH 2 ) 3 —	CH 2	H
292	Ethyl	4-Methylthiazol-5-yl	S—(CH 2 ) 6 —	CH 2	7-cyano
293	Me	2-Pyrazinyl-	S—(CH 2 ) 3 —	CH 2	7-methoxy	8-methoxy
294	Me	3-Pyrrolyl	S—(CH 2 ) 3 —	CH 2	H
295	Me	4-Methoxyphenyl	O—(CH 2 ) 3 —	CH 2	H
296	Me	3-Jod-phenyl	S—(CH 2 ) 3 —	O	7-cyano
297	Ethyl	Pyridin-3-yl-	S—CH 2 —C(CH 3 )═CH—CH 2 —	CH 2	7-tert-butyl
*If no meaning is given, R 7 is hydrogen.

Here and in the following tables is:

Me=methyl

Et=ethyl

cycPropyl=cyclopropyl

The following compounds can be prepared in an analogous way in principles:

TABLE 2
Ex.	R 1	R 2	A	Y	R 6	R 7 *
298	Me	N-Methyl-2-Pyrrolyl-	(CH 2 ) 4 —	CH 2	10-methyl
299	Ethyl	2-Aminothiazol-4yl-	S—(CH 2 ) 3 —	O	H
300	Me	3-Jod-phenyl	S—(CH 2 ) 3 —	O	8-nitro
301	Me	Amino	S—(CH 2 ) 3 —	CH 2	8-tert-butyl
302	Me	5-Methyl imidazol-4-yl-	S—(CH 2 ) 3 —	CH 2	H
303	Me	Cyclohexyl-	S—(CH 2 ) 3 —	CH 2	8-tert-butyl
304	Me	4-Methoxyphenyl	S—(CH 2 ) 3 —	O	H
305	Ethyl	Pyridin-3-yl-	S—(CH 2 ) 6 —	O	8-tert-butyl
306	Me	3-Jod-phenyl	(CH 2 ) 4 —	O	8-tert-butyl
307	Me	5-Methyl imidazol-4-yl-	S—(CH 2 ) 3 —	CH 2	8-tert-butyl
308	Me	2-Thienyl	(CH 2 ) 4 —	O	H
309	Me	2-Me-4-Oxazolyl-	S—(CH 2 ) 3 —	CH 2	9-methyl
310	Me	2,5-Di-methyl-furanyl-3-	S—(CH 2 ) 3 —	CH 2	7-methoxy
311	Me	4-Methylthiazol-5-yl	S—(CH 2 ) 3 —	O	8-cyano
312	Propyl	4-Methoxyphenyl	COO—(CH 2 ) 3 —	CH 2	8-sulfonamido
313	Propyl	N-Methyl-2-Pyrrolyl-	CONH—(CH 2 ) 4 —	CH 2	9-trifluoromethoxy
314	Me	2-Thienyl	S—(CH 2 ) 7 —	CH 2	9-trifluoromethoxy
315	Me	Pyridin-3-yl-	S—(CH 2 ) 3 —	CH 2	9-methyl
316	Me	N-Propyl-tetrazolyl-	S—(CH 2 ) 3 —	CH 2	9-trifluoromethoxy
317	Me	3-Br-Pyridin-5-yl-	S—(CH 2 ) 3 —	CH 2	8-tert-butyl
318	Me	3-Cyano-phenyl	S—(CH 2 ) 3 —	CH 2	7-methoxy
319	Phenyl	Amino	S—(CH 2 ) 3 —	O	H
320	Butyl	2,5-Di-methyl-furanyl-3-	S—(CH 2 ) 3 —	CH 2	8-methoxy	9-methoxy
321	Phenyl	3-Benzthienyl-	S—(CH 2 ) 3 —	O	H
322	Me	N-Methyl-2-Pyrrolyl-	S—(CH 2 ) 3 —	CH 2	8-tert-butyl
323	Propyl	3-cyano-phenyl	CONH—(CH 2 ) 5 —	CH 2	8-methyl
324	Me	3-Jod-phenyl	S—(CH 2 ) 3 —	CH 2	8-sulfonamido
325	Me	Phenyl	O—(CH 2 ) 3 —	CH 2	8-sulfonamido
326	Me	4-Methylthiazol-5-yl	(CH 2 ) 4 —	CH 2	10-methyl
327	Me	3-Pyrrolyl	S—(CH 2 ) 3 —	CH 2	7-methoxy
328	Butyl	3-Cyano-phenyl	S—(CH 2 ) 3 —	CH 2	8-methoxy	9-methoxy
329	Ethyl	4-Methylthiazol-5-yl	S—(CH 2 ) 6 —	O	8-cyano
330	Me	Pyridin-4-yl-	S—(CH 2 ) 3 —	O	H
331	Butyl	2-Aminothiazol-4yl-	S—(CH 2 ) 3 —	CH 2	8-methoxy	9-methoxy
332	Propyl	4-Imidazolyl-	S—(CH 2 ) 3 —	CH 2	8-carboxamido
333	isoPropyl	Tetrazolyl-	S—(CH 2 ) 3 —	CH 2	7-methoxy
334	Me	Pyridin-3-yl-	S—(CH 2 ) 3 —	O	8-cyano
335	Me	N-Methyl-2-Pyrrolyl	S—(CH 2 ) 3 —	O	8-nitro
336	Et	Amino	S—(CH 2 ) 3 —	CH 2	H
337	Phenyl	Methylamino	S—(CH 2 ) 3 —	CH 2	9-methyl
338	Me	4-Methylthiazol-5-yl	(CH 2 ) 4 —	O	10-methyl
339	Me	4-Methylthiazol-5-yl	S—(CH 2 ) 3 —	CH 2	8-sulfonamido
340	Me	Methylamino	S—(CH 2 ) 3 —	CH 2	8-tert-butyl
341	Et	3-Cyano-phenyl	S—(CH 2 ) 3 —	CH 2	H
342	Me	4-Methylthiazol-5-yl	S—(CH 2 ) 3 —	O	8-nitro
343	Me	3-Jod-phenyl	(CH 2 ) 4 —	CH 2	8-tert-butyl
344	Me	4-Methylthiazol-5-yl	S—(CH 2 ) 3 —	CH 2	H
345	Me	3-Br-Pyridin-5-yl-	S—(CH 2 ) 3 —	CH 2	H
346	Propyl	Pyridin-4-yl-	S—(CH 2 ) 3 —	CH 2	8-carboxamido
347	Me	4-Methoxyphenyl	S—(CH 2 ) 3 —	CH 2	8-cyano
348	isoPropyl	3-Benzthienyl-	S—(CH 2 ) 3 —	CH 2	9-trifluoromethoxy
349	Butyl	3-Benzthienyl-	S—(CH 2 ) 3 —	CH 2	8-methoxy	9-methoxy
350	Ethyl	Pyridin-3-yl-	(CH 2 ) 4 —	O	H
351	Propyl	2-Aminothiazol-4yl-	S—(CH 2 ) 3 —	CH 2	8-carboxamido
352	Me	Cyclohexyl-	S—(CH 2 ) 3 —	CH 2	9-methyl
353	Ethyl	Phenyl	S—(CH 2 ) 3 —	O	8-nitro
354	Me	4-Methoxyphenyl	S—(CH 2 ) 3 —	O	8-methoxy	9-methoxy
355	Propyl	Phenyl	COO—(CH 2 ) 4 —	O	8-methyl
356	Me	2,5-Di-methyl-furanyl-3-	S—(CH 2 ) 3 —	CH 2	9-methyl
357	Me	3-Jod-phenyl	S—(CH 2 ) 3 —	CH 2	H
358	Me	Phenyl	S—(CH 2 ) 3 —	CH 2	H
359	isoPropyl	Oxadiazol-2-yl	S—(CH 2 ) 3 —	CH 2	7-methoxy
360	Me	Phenyl	S—(CH 2 ) 7 —	O	8-tert-butyl
361	Propyl	2-Pyrazinyl-	COO—(CH 2 ) 4 —	CH 2	9-trifluoromethoxy
362	Me	3-Pyrrolyl	S—(CH 2 ) 3 —	CH 2	8-carboxamido
363	Propyl	Phenyl	S—(CH 2 ) 3 —	CH 2	8-carboxamido
364	Me	2-Pyrazinyl-	O—(CH 2 ) 3 —	CH 2	H
365	Me	Phenyl	S—(CH 2 ) 7 —	O	8-tert-butyl
366	Me	Pyridin-3-yl-	S—(CH 2 ) 3 —	CH 2	8-sulfonamido
367	Me	3-Jod-phenyl	S—(CH 2 ) 3 —	CH 2	8-cyano
368	Me	2-Thienyl	S—(CH 2 ) 3 —	CH 2	9-methyl
369	isoPropyl	Methylamino	S—(CH 2 ) 3 —	CH 2	7-methoxy
370	Ethyl	3-Jod-phenyl	S—(CH 2 ) 3 —	CH 2	8-methoxy	9-methoxy
371	Ethyl	Phenyl	CO—(CH 2 ) 3 —	O	H
372	Phenyl	4-Imidazolyl-	S—(CH 2 ) 3 —	O	H
373	Ethyl	4-Methylthiazol-5-yl	S—(CH 2 ) 6 —	CH 2	8-cyano
374	Me	3-Jod-phenyl	S—(CH 2 ) 3 —	CH 2	7-methoxy
375	Hexyl	4-Imidazolyl-	S—(CH 2 ) 3 —	CH 2	7-methoxy
376	Me	Phenyl	S—(CH 2 ) 3 —	CH 2	9-trifluoromethoxy
377	Me	3-Jod-phenyl	O—(CH 2 ) 3 —	O	8-nitro
378	Me	5-Methyl imidazol-4-yl-	S—(CH 2 ) 3 —	CH 2	7-methoxy
379	Ethyl	Pyridin-3-yl-	S—CH 2 —C(CH 3 )═CH—CH 2 —	O	8-tert-butyl
380	Me	N-Methyl-2-Pyrrolyl-	S—(CH 2 ) 3 —	CH 2	7-methoxy
381	Ethyl	Phenyl	S—CH 2 —C(CH 3 )═CH—CH 2 —	CH 2	8-tert-butyl
382	Me	Pyridin-3-yl-	S—(CH 2 ) 8 —	O	9-trifluoromethoxy
383	Me	2-Thienyl	S—(CH 2 ) 3 —	O	8-nitro
384	Me	2-Pyrazinyl-	(CH 2 ) 4 —	O	8-methyl
385	Butyl	3-Br-Pyridin-5-yl-	S—(CH 2 ) 3 —	CH 2	8-methoxy	9-methoxy
386	Me	2-Pyrazinyl-	S—(CH 2 ) 3 —	CH 2	8-methoxy	9-methoxy
387	Me	Phenyl	S—(CH 2 ) 3 —	O	8-cyano
388	Me	4-Methoxyphenyl	S—(CH 2 ) 3 —	O	8-nitro
389	Me	Cyclohexyl-	S—(CH 2 ) 3 —	CH 2	7-methoxy
390	Me	Phenyl	CO—CH 2 —C(═CH 2 )—CH 2	O	8-tert-butyl
391	Me	N-Methyl-2-Pyrrolyl-	(CH 2 ) 4 —	O	10-methyl
392	Me	Oxadiazol-2-yl	S—(CH 2 ) 3 —	CH 2	9-methyl
393	Me	2-Pyrazinyl-	S—(CH 2 ) 3 —	CH 2	H
394	Ethyl	Phenyl	S—(CH 2 ) 3 —	CH 2	8-nitro
395	Me	Pyridin-3-yl-	S—(CH 2 ) 3 —	CH 2	8-nitro
396	Me	2-Me-4-Oxazolyl-	S—(CH 2 ) 3 —	CH 2	7-methoxy
397	Me	Pyridin-3-yl	S—(CH 2 ) 3 —	CH 2	8-tert-butyl
398	Ethyl	Phenyl	CO—(CH 2 ) 3 —	CH 2	H
399	Me	3-Cyano-phenyl	S—(CH 2 ) 3 —	O	H
400	Me	Pyridin-3-yl-	(CH 2 ) 4 —	O	H
401	Me	4-Jod-phenyl	S—(CH 2 ) 3 —	CH 2	8-tert-butyl
402	Butyl	3-Pyrrolyl	S—(CH 2 ) 3 —	CH 2	8-methoxy	9-methoxy
403	Me	N-Methyl-2-Pyrrolyl-	S—(CH 2 ) 3 —	O	8-cyano
404	Me	2-Me-4-Oxazolyl-	S—(CH 2 ) 3 —	CH 2	8-tert-butyl
405	isoButyl	Methylamino	S—(CH 2 ) 3 —	O	H
406	Me	2-Thienyl	S—(CH 2 ) 3 —	O	8-nitro
407	Me	2-Thienyl	S—(CH 2 ) 7 —	O	9-trifluoromethoxy
408	Me	4-Methylthiazol-5-yl	S—(CH 2 ) 3 —	O	8-cyano
409	Me	2-Me-4-Oxazolyl-	S—(CH 2 ) 3 —	O	8-tert-butyl
410	Me	2-Thienyl	S—CH 2 —C(═CH 2 )—CH 2	CH 2	9-fluoro
411	Me	N-Methyl-2-Pyrrolyl-	S—(CH 2 ) 3 —	O	8-cyano
412	Me	Phenyl	S—(CH 2 ) 3 —	CH 2	9-methyl
413	Me	3-Jod-phenyl	S—(CH 2 ) 3 —	CH 2	9-methyl
414	Me	Pyridin-3-yl-	S—(CH 2 ) 3 —	O	8-tert-butyl
415	Ethyl	2-Thienyl	(CH 2 ) 4 —	O	H
416	Me	Tetrazolyl-	S—(CH 2 ) 3 —	CH 2	9-methyl
417	Me	2-Thienyl	S—(CH 2 ) 8 —	CH 2	7-methoxy
418	Me	Pyridin-4-yl-	S—(CH 2 ) 3 —	CH 2	9-trifluoromethoxy
419	Me	Phenyl	S—CH 2 —C(═CH 2 )—CH 2	CH 2	9-bromo
420	Me	Phenyl	S—(CH 2 ) 10 —	O	8-methyl
421	Me	Oxadiazol-2-yl	S—(CH 2 ) 3 —	CH 2	H
422	Me	Oxadiazol-2-yl	S—(CH 2 ) 3 —	O	8-methoxy	9-methoxy
423	Butyl	4-Imidazolyl-	S—(CH 2 ) 3 —	CH 2	8-methoxy	9-methoxy
424	isoPropyl	3-Pyrrolyl	S—(CH 2 ) 3 —	O	9-trifluoromethoxy
425	isoPropyl	3-Cyano-phenyl	S—(CH 2 ) 3 —	CH 2	9-trifluoromethoxy
426	Butyl	N-Propyl-tetrazolyl-	S—(CH 2 ) 3 —	CH 2	8-methoxy	9-methoxy
427	Me	Pyridin-3-yl-	S—(CH 2 ) 8 —	CH 2	9-trifluoromethoxy
428	cycPropyl	4-Methoxyphenyl	S—(CH 2 ) 3 —	CH 2	9-methyl
429	Me	Phenyl	CO—CH 2 —C(═CH 2 )—CH 2	CH 2	8-tert-butyl
430	Me	3-Br-Pyridin-5-yl-	S—(CH 2 ) 3 —	CH 2	9-methyl
431	Me	2-Pyrazinyl-	(CH 2 ) 4 —	CH 2	8-methyl
432	Me	Phenyl	CO—CH 2 —C(═CH 2 )—CH 2	O	8-tert-butyl
433	Me	N-Methyl-2-Pyrrolyl-	S—(CH 2 ) 3 —	CH 2	8-cyano
434	Me	2-Thienyl	S—(CH 2 ) 3 —	CH 2	8-methoxy	9-methoxy
435	Ethyl	Pyridin-3-yl-	S—CH 2 —C(CH 3 )═CH—CH 2 —	CH 2	8-tert-butyl
436	Me	Methylamino	S—(CH 2 ) 3 —	CH 2	8-methoxy	9-methoxy
437	Me	2-Me-4-Oxazolyl-	S—(CH 2 ) 3 —	CH 2	8-methoxy	9-methoxy
438	isoPropyl	Phenyl	S—(CH 2 ) 3 —	O	8-sulfonamido
439	Ethyl	Phenyl	S—CH 2 —C(CH 3 )═CH—CH 2 —	O	8-tert-butyl
440	Me	3-Br-Pyridin-5-yl-	S—(CH 2 ) 3 —	CH 2	7-methoxy
441	Me	Cyano	S—(CH 2 ) 3 —	CH 2	H
442	Me	3-Br-Pyridin-5-yl-	S—(CH 2 ) 3 —	O	H
443	Me	N-Methyl-2-Pyrrolyl-	S—(CH 2 ) 3 —	CH 2	8-nitro
444	Me	N-Propyl-tetrazolyl-	S—(CH 2 ) 3 —	CH 2	8-tert-butyl
445	Me	4-Methoxyphenyl	S—(CH 2 ) 3 —	CH 2	8-methoxy	9-methoxy
446	Me	2-Pyrazinyl-	S—(CH 2 ) 3 —	CH 2	8-sulfonamido
447	Me	Phenyl	S—(CH 2 ) 3 —	CH 2	8-methoxy	9-methoxy
448	Me	4-Methoxyphenyl	(CH 2 ) 4 —	CH 2	10-fluoro
449	Me	2-Thienyl	S—(CH 2 ) 3 —	CH 2	8-sulfonamido
450	isoPropyl	5-Methyl imidazol-4-yl-	S—(CH 2 ) 3 —	CH 2	9-trifluoromethoxy
451	Ethyl	3-Jod-phenyl	(CH 2 ) 4 —	O	8-tert-butyl
452	Me	2-Pyrazinyl-	S—(CH 2 ) 3 —	CH 2	8-cyano
453	isoPropyl	2-Aminothiazol-4yl-	S—(CH 2 ) 3 —	CH 2	9-trifuormethoxy
454	cycPropyl	3-Cyano-phenyl	S—(CH 2 ) 3 —	CH 2	9-methyl
455	isoPropyl	3-Pyrrolyl	S—(CH 2 ) 3 —	CH 2	9-trifluoromethoxy
456	Me	2-Aminothiazol-4yl-	S—(CH 2 ) 3 —	CH 2	7-methoxy
457	Me	Pyridin-3-yl-	S—(CH 2 ) 3 —	CH 2	7-methoxy
458	Me	2-Aminothiazol-4yl-	S—(CH 2 ) 3 —	CH 2	H
459	Me	Phenyl	O—(CH 2 ) 4 —	O	9-iod
460	Me	2-Thienyl	S—(CH 2 ) 3 —	O	8-cyano
461	Ethyl	Pyridin-3-yl-	S—CH 2 —CH═CH—CH 2 —	O	9-fluoro
462	Propyl	4-Methylthiazol-5-yl	CONH—(CH 2 ) 4 —	CH 2	8-methyl
463	Phenyl	4-Imidazolyl-	S—(CH 2 ) 3 —	CH 2	H
464	Hexyl	3-Benzthienyl-	S—(CH 2 ) 3 —	CH 2	7-methoxy
465	Ethyl	Pyridin-3-yl-	S—(CH 2 ) 6 —	CH 2	8-tert-butyl
466	Me	3-Pyrrolyl	S—(CH 2 ) 3 —	O	H
467	cycPropyl	2-Thienyl	S—(CH 2 ) 3 —	CH 2	H
468	Ethyl	Phenyl	S—CH 2 —C(CH 3 )═CH—CH 2 —	O	8-sulfonamido
469	Me	2-Aminothiazol-4yl-	S—(CH 2 ) 3 —	CH 2	8-tert-butyl
470	isoPropyl	3-Benzthienyl-	S—(CH 2 ) 3 —	O	9-trifuormethoxy
471	Me	Pyridin-3-yl-	S—(CH 2 ) 3 —	O	8-nitro
472	Ethyl	2-Thienyl	CO—(CH 2 ) 3 —	CH 2	H
473	Me	N-Methyl-2-Pyrrolyl-	S—(CH 2 ) 3 —	CH 2	H
474	Propyl	Phenyl	CONH—(CH 2 ) 5 —	O	8-methyl
475	isoPropyl	5-Methyl imidazol-4-yl-	S—(CH 2 ) 3 —	O	9-trifluoromethoxy
476	Me	4-Methoxyphenyl	S—(CH 2 ) 3 —	CH 2	8-tert-butyl
477	Me	N-Methyl-2-Pyrrolyl-	S—(CH 2 ) 3 —	CH 2	8-methoxy	9-methoxy
478	cycPropyl	N-Propyl-tetrazolyl-	S—(CH 2 ) 3 —	CH 2	9-methyl
479	Et	2,5-Di-methyl-furanyl-3-	S—(CH 2 ) 3 —	CH 2	H
480	isoButyl	Oxadiazol-2-yl	S—(CH 2 ) 3 —	O	8-tert-butyl
481	Hexyl	N-Propyl-tetrazolyl-	S—(CH 2 ) 3 —	CH 2	7-methoxy
482	Propyl	2-Thienyl	COO—(CH 2 ) 4 —	CH 2	7-methoxy
483	Phenyl	Cyano	S—(CH 2 ) 3 —	O	H
484	Me	2-Thienyl	S—CH 2 —C(═CH 2 )—CH 2	O	9-fluoro
485	Me	Pyridin-4-yl-	S—(CH 2 ) 3 —	CH 2	8-tert-butyl
486	Me	2-Pyrazinyl-	S—(CH 2 ) 3 —	O	8-cyano
487	Butyl	5-Methyl imidazol-4-yl-	S—(CH 2 ) 3 —	CH 2	8-methoxy	9-methoxy
488	Ethyl	2-Thienyl	CO—(CH 2 ) 3 —	O	H
489	Me	Oxadiazol-2-yl	S—(CH 2 ) 3 —	CH 2	8-tert-butyl
490	isoPropyl	Cyano	S—(CH 2 ) 3 —	CH 2	7-methoxy
491	Me	Amino	S—(CH 2 ) 3 —	CH 2	8-methoxy	9-methoxy
492	Me	N-Methyl-2-Pyrrolyl-	S—CH 2 —CH═CH—CH 2 —	CH 2	9-fluoro
493	Me	Phenyl	S—(CH 2 ) 7 —	CH 2	8-tert-butyl
494	Me	2-Pyrazinyl-	O—(CH 2 ) 3 —	O	H
495	Me	Phenyl	S—(CH 2 ) 10 —	CH 2	8-methyl
496	Butyl	Pyridin-4-yl-	S—(CH 2 ) 3 —	CH 2	8-methoxy	9-methoxy
497	Ethyl	4-Methylthiazol-5-yl	S—(CH 2 ) 6 —	O	8-cyano
498	Me	4-Methoxyphenyl	S—(CH 2 ) 3 —	O	8-cyano
499	Me	3-Pyrrolyl	S—(CH 2 ) 3 —	CH 2	9-methyl
500	isoPropyl	Phenyl	S—(CH 2 ) 3 —	CH 2	8-sulfonamido
501	Me	Tetrazolyl-	S—(CH 2 ) 3 —	CH 2	8-methoxy	9-methoxy
502	Phenyl	2-Pyrazinyl-	S—(CH 2 ) 3 —	CH 2	8-tert-butyl
503	isoPropyl	4-Methoxyphenyl	S—(CH 2 ) 3 —	CH 2	8-sulfonamido
504	Phenyl	Carboxamido	S—(CH 2 ) 3 —	CH 2	9-methyl
505	Me	4-Methylthiazol-5-yl	S—(CH 2 ) 3 —	O	H
506	Me	3-Cyano-phenyl	S—(CH 2 ) 3 —	CH 2	8-tert-butyl
507	Pentyl	Phenyl	CH 2 —CH 2 —CH═CH—CH 2 —	O	H
508	Me	N-Methyl-2-Pyrrolyl-	S—(CH 2 ) 3 —	CH 2	9-methyl
509	Me	Pyridin-3-yl-	S—(CH 2 ) 3 —	CH 2	8-methoxy	9-methoxy
510	Me	4-Methoxyphenyl	O—(CH 2 ) 3 —	CH 2	H
511	Me	2-Pyrazinyl-	S—(CH 2 ) 3 —	CH 2	9-methyl
512	Phenyl	3-Benzthienyl-	S—(CH 2 ) 3 —	CH 2	8-tert-butyl
513	Me	Phenyl	O—(CH 2 ) 4 —	CH 2	8-tert-butyl
514	Me	3-Jod-phenyl	O—(CH 2 ) 3 —	O	H
515	Me	3-Thienyl	S—(CH 2 ) 3 —	CH 2	8-tert-butyl
516	cycPropyl	Pyridin-3-yl-	S—(CH 2 ) 3 —	CH 2	H
517	Me	Pyridin-3-yl-	S—(CH 2 ) 3 —	CH 2	8-cyano
518	Me	4-Methylthiazol-5-yl	S—(CH 2 ) 3 —	CH 2	8-nitro
519	Me	Phenyl	S—CH 2 —C(═CH 2 )—CH 2	O	9-bromo
520	Me	Pyridin-3-yl-	(CH 2 ) 4 —	CH 2	H
521	Me	2-Thienyl	S—(CH 2 ) 3 —	CH 2	7-methoxy
522	Propyl	Phenyl	CONH—(CH 2 ) 5 —	CH 2	8-methyl
523	Me	N-Propyl-tetrazolyl-	S—(CH 2 ) 3 —	O	H
524	Ethyl	Phenyl	S—(CH 2 ) 3 —	O	8-nitro
525	Me	Phenyl	(CH 2 ) 4 —	CH 2	H
526	Propyl	3-Cyano-phenyl	S—(CH 2 ) 3 —	CH 2	8-carboxamido
527	Me	Oxadiazol-2-yl	S—(CH 2 ) 3 —	CH 2	8-methoxy	9-methoxy
528	Me	4-Methoxyphenyl	S—(CH 2 ) 3 —	CH 2	8-nitro
529	Me	Phenyl	(CH 2 ) 4 —	O	H
530	isoPropyl	3-Br-Pyridin-5-yl-	S—(CH 2 ) 3 —	CH 2	9-trifluoromethoxy
531	Ethyl	4-Methylthiazol-5-yl	S—CH 2 —C(═CH 2 )—CH 2	CH 2	8-sulfonamido
532	Me	Tetrazolyl-	S—(CH 2 ) 3 —	CH 2	H
533	Me	4-Methylthiazol-5-yl	S—(CH 2 ) 3 —	CH 2	8-methoxy	9-methoxy
534	Propyl	Phenyl	COO—(CH 2 ) 4 —	CH 2	8-methyl
535	Propyl	3-Br-Pyridin-5-yl-	S—(CH 2 ) 3 —	CH 2	8-carboxamido
536	Me	2-Pyrazinyl-	S—(CH 2 ) 3 —	O	H
537	Me	2-Thienyl	S—(CH 2 )8—	O	7-methoxy
538	Me	3-Jod-phenyl	O—(CH 2 ) 3 —	CH 2	H
539	Me	Phenyl	S—(CH 2 ) 3 —	O	H
540	Hexyl	Pyridin-4-yl-	S—(CH 2 ) 3 —	CH 2	7-methoxy
541	Me	2-Thienyl	(CH 2 ) 4 —	CH 2	H
542	cycPropyl	Pyridin-4-yl-	S—(CH 2 ) 3 —	CH 2	9-methyl
543	cycPropyl	Amino	S—(CH 2 ) 3 —	CH 2	9-methyl
544	Me	3-Jod-phenyl	S—(CH 2 ) 3 —	O	8-tert-butyl
545	Ethyl	4-Methylthiazol-5-yl	S—CH 2 —C(CH 3 )═CH—CH 2 —	CH 2	8-tert-butyl
546	Me	3-Pyrrolyl	S—(CH 2 ) 3 —	CH 2	H
547	Propyl	Phenyl	S—(CH 2 ) 3 —	O	8-carboxamido
548	Me	4-Imidazolyl-	S—(CH 2 ) 3 —	CH 2	8-tert-butyl
549	Propyl	Pyridin-3-yl-	CONH—(CH 2 ) 4 —	CH 2	8-methyl
550	isoPropyl	4-Methoxyphenyl	S—(CH 2 ) 3 —	O	8-sulfonamido
551	Me	2-Me-4-Oxazolyl-	S—(CH 2 ) 3 —	CH 2	H
552	Me	3-Jod-phenyl	S—(CH 2 ) 3 —	O	8-cyano
553	Me	2-Thienyl	S—(CH 2 ) 3 —	O	H
554	cycPropyl	3-Benzthienyl-	S—(CH 2 ) 3 —	CH 2	9-methyl
555	Me	4-Methylthiazol-5-yl	S—(CH 2 ) 3 —	CH 2	9-methyl
556	Hexyl	Amino	S—(CH 2 ) 3 —	CH 2	7-methoxy
557	isoButyl	Tetrazolyl-	S—(CH 2 ) 3 —	O	H
558	Et	4-Methoxyphenyl	S—(CH 2 ) 3 —	CH 2	H
559	cycPropyl	4-Imidazolyl-	S—(CH 2 ) 3 —	CH 2	9-methyl
560	Me	Phenyl	S—(CH 2 ) 3 —	CH 2	8-cyano
561	Me	2-Thienyl	O—(CH 2 ) 4 —	CH 2	8-tert-butyl
562	Me	2-Aminothiazol-4yl-	S—(CH 2 ) 3 —	CH 2	9-methyl
563	Butyl	Cyano	S—(CH 2 ) 3 —	CH 2	8-methoxy	9-methoxy
564	Me	5-Methyl imidazol-4-yl-	S—(CH 2 ) 3 —	CH 2	9-methyl
565	Me	Phenyl	S—(CH 2 ) 3 —	CH 2	7-methoxy
566	Me	2-Pyrazinyl-	S—(CH 2 ) 3 —	CH 2	8-nitro
567	Phenyl	3-Benzthienyl-	S—(CH 2 ) 3 —	CH 2	H
568	Me	2,5-Di-methyl-furanyl-3-	S—(CH 2 ) 3 —	O	H
569	Et	Pyridin-4-yl-	S—(CH 2 ) 3 —	CH 2	H
570	Me	Tetrazolyl-	S—(CH 2 ) 3 —	CH 2	8-tert-butyl
571	Me	2-Thienyl	S—(CH 2 ) 3 —	CH 2	8-cyano
572	Me	4-Methylthiazol-5-yl	S—(CH 2 ) 3 —	CH 2	8-cyano
573	Me	N-Methyl-2-Pyrrolyl-	S—(CH 2 ) 3 —	CH 2	8-sulfonamido
574	Hexyl	4-Methoxyphenyl	S—(CH 2 ) 3 —	CH 2	7-methoxy
575	Me	2-Pyrazinyl-	S—(CH 2 ) 3 —	O	8-nitro
576	Et	N-Propyl-tetrazolyl-	S—(CH 2 ) 3 —	CH 2	H
577	Me	3-Pyrrolyl	S—(CH 2 ) 3 —	CH 2	8-tert-butyl
578	Me	2-Pyrazinyl-	S—(CH 2 ) 3 —	CH 2	7-methoxy
579	Me	4-Methoxyphenyl	(CH 2 ) 4 —	O	10-fluoro
580	Ethyl	Pyridin-3-yl	S—CH 2 —CH═CH—CH 2 —	CH 2	9-fluoro
581	Ethyl	N-Methyl-2-Pyrrolyl-	(CH 2 ) 4 —	O	10-methyl
582	Me	5-Methyl imidazol-4-yl-	S—(CH 2 ) 3 —	O	H
583	Ethyl	4-Methylthiazol-5-yl	S—CH 2 —C(═CH 2 )—CH 2	O	8-sulfonamido
584	Me	2,5-Di-methyl-furanyl-3-	S—(CH 2 ) 3 —	CH 2	8-tert-butyl	H
585	Me	3-Jod-phenyl	S—(CH 2 ) 3 —	CH 2	8-nitro
586	Me	N-Methyl-2-Pyrrolyl-	S—(CH 2 ) 3 —	O	H
587	Me	2-Thienyl	S—(CH 2 ) 3 —	CH 2	8-nitro
588	cycPropyl	Methylamino	S—(CH 2 ) 3 —	CH 2	H
589	Me	4-Methylthiazol-5-yl	S—(CH 2 ) 3 —	CH 2	7-methoxy
590	Ethyl	4-Methylthiazol-5-yl	S—CH 2 —C(CH 3 )═CH—CH 2 —	O	8-tert-butyl
591	Propyl	3-Jod-phenyl	COO—(CH 2 ) 4 —	CH 2	9-trifluoromethoxy
*If no meaning is given, R 7 is hydrogen.

The following compounds can be prepared in an analogous way in principles:

TABLE 3
Ex.	R 1	R 2	A	R 6
592	Me	Tetrazolyl-	S—(CH 2 ) 3 —	7-tert-butyl
593	Me	3-Jod-phenyl	O—(CH 2 ) 3 —	7-nitro
594	Me	4-Methoxyphenyl	S—CH 2 —CH═CH—CH 2 —	6-methoxy
595	Me	Amino	S—CH 2 —C(CH 3 )═CH—CH 2 —	7-tert-butyl
596	Me	Methylamino	S—(CH 2 ) 3 —	7-tert-butyl
597	Propyl	4-Methoxyphenyl	S—(CH 2 ) 3 —	7-nitro
598	Me	3-Pyrrolyl	S—(CH 2 ) 3 —	7-tert-butyl
599	Me	3-Jod-phenyl	S—(CH 2 ) 4 —	6-methoxy
600	Me	2-Pyrazinyl-	S—(CH 2 ) 3 —	7-nitro
601	isoPropyl	2-Thienyl	CONH—(CH 2 ) 4 —	H
602	Me	4-Methylthiazol-5-yl	S—(CH 2 ) 3 —	6-chloroo
603	Me	2-Pyrazinyl-	S—(CH 2 ) 3 —	6-chloroo
604	Butyl	Oxadiazol-2-yl	S—(CH 2 ) 3 —	7-tert-butyl
605	cycPropyl	Phenyl	(CH 2 ) 4 —	6-methyl
606	Me	4-Imidazolyl-	S—(CH 2 ) 3 —	7-tert-butyl
607	Phenyl	3-Benzthienyl-	S—(CH 2 ) 3 —	7-tert-butyl
608	Propyl	2-Thienyl	S—CH 2 —CH═CH—CH 2 —	6-methoxy
609	Hexyl	Phenyl	(CH 2 ) 4 —	6-methyl
610	Propyl	Phenyl	S—CH 2 —C(CH 3 )═CH—CH 2 —	6-methyl
611	isoPropyl	Phenyl	S—CH 2 —C(═CH 2 )—CH 2	6-methyl
612	Me	N-Methyl-2-Pyrrolyl-	S—(CH 2 ) 3 —	6-methoxy
613	Me	4-Jod-phenyl	S—CH 2 —CH═CH—CH 2 —	7-tert-butyl
614	Me	Pyridin-3-yl-	S—CH 2 —CH═CH—CH 2 —	7-tert-butyl
615	Propyl	Phenyl	S—(CH 2 ) 3 —	6-methoxy
616	Me	3-Jod-phenyl	S—(CH 2 ) 3 —	6-chloroo
617	Me	3-Thienyl	S—(CH 2 ) 3 —	7-tert-butyl
618	Ethyl	Phenyl	(CH 2 ) 8 —	H
619	Me	Cyclohexyl-	S—(CH 2 ) 3 —	7-tert-butyl
620	Me	Pyridin-3-yl-	S—(CH 2 ) 3 —	H
621	Me	Phenyl	S—(CH 2 )3—	7-cyano
622	Ethyl	Phenyl	S—(CH 2 ) 3 —	6-methyl
623	Me	Pyridin-4-yl-	O—(CH 2 ) 3 —	7-tert-butyl
624	Ethyl	4-Methylthiazol-5-yl	S—CH 2 —C(CH 3 )═CH—CH 2 —	7-cyano
625	Me	2-Pyrazinyl-	S—(CH 2 ) 3 —	6-methoxy
626	Ethyl	Phenyl	S—(CH 2 ) 3 —	6-chloroo
627	Ethyl	3-Jod-phenyl	S—CH 2 —C(CH 3 )═CH—CH 2 —	7-cyano
628	Me	2-Thienyl	S—(CH 2 ) 3 —	7-nitro
629	Ethyl	Pyridin-3-yl-	S—(CH 2 ) 3 —	7-cyano
630	Me	N-Methyl-2-Pyrrolyl-	S—(CH 2 ) 3 —	6-chloroo
631	Me	N-Methyl-2-Pyrrolyl-	S—(CH 2 ) 3 —	7-tert-butyl
632	isoPropyl	4-Methoxyphenyl	S—(CH 2 ) 3 —	7-tert-butyl
633	Me	3-Br-Pyridin-5-yl-	S—CH 2 —C(CH 3 )═CH—CH 2 —	7-tert-butyl
634	isoPropyl	3-Cyano-phenyl	O—(CH 2 ) 8 —	7-tert-butyl
635	Ethyl	Phenyl	S—(CH 2 ) 3 —	7-nitro
636	Me	5-Methyl imidazol-4-yl-	S—(CH 2 ) 3 —	7-tert-butyl
637	Ethyl	N-Methyl-2-Pyrrolyl-	S—(CH 2 ) 3 —	7-cyano
638	Me	Pyridin-3-yl-	S—(CH 2 ) 3 —	6-chloroo
639	Me	4-Methylthiazol-5-yl	S—(CH 2 ) 3 —	6-methoxy
640	Phenyl	2-Pyrazinyl-	S—CH 2 —C(CH 3 )═CH—CH 2 —	7-tert-butyl
641	Hexyl	Phenyl	(CH 2 ) 4 —	6-methyl
642	Me	4-Methoxyphenyl	S—(CH 2 ) 3 —	6-chloroo
643	Me	N-Methyl-2-Pyrrolyl-	S—(CH 2 ) 3 —	7-nitro
644	Me	2,5-Di-methyl-furanyl-3-	S—(CH 2 ) 3 —	7-tert-butyl
645	Propyl	Phenyl	COO—(CH 2 ) 4 —	H
646	cycPropyl	Phenyl	O—(CH 2 ) 3 —	6-methyl
647	Me	2-Thienyl	S—(CH 2 ) 7 —	6-chloro
648	isoPropyl	2-Aminothiazol-4y1-	S—(CH 2 ) 3 —	7-tert-butyl
649	Butyl	Phenyl	(CH 2 ) 4 —	6-methyl
650	Me	2-Pyrazinyl-	S—(CH 2 ) 3 —	7-cyano
651	Me	4-Methoxyphenyl	S—CH 2 —CH═CH—CH2—	H
652	Me	N-Propyl-tetrazolyl-	S—(CH 2 ) 3 —	7-tert-butyl
653	Me	Pyridin-3-yl-	S—(CH 2 ) 3 —	6-methoxy
654	Butyl	Phenyl	CO—(CH 2 ) 3 —	6-methyl
655	Me	2-Me-4-Oxazolyl-	S—CH 2 —CH═CH—CH 2 —	7-tert-butyl
656	Me	4-Methylthiazol-5-yl	S—(CH 2 ) 9 —	7-nitro
657	Me	2-Thienyl	S—(CH 2 ) 3 —	7-cyano

The following compounds can be prepared in an analogous way in principles:

TABLE 4
Ex.	R 1	R 2	A	R 6
658	Me	N-Methyl-2-Pyrrolyl-	S—(CH 2 ) 3 —	7-methoxy
659	Me	2-Pyrazinyl-	S—(CH 2 ) 3 —	7-methoxy
660	Me	Amino	S—CH 2 —C(CH 3 )═CH—CH 2 —	8-tert-butyl
661	Me	4-Methylthiazol-5-yl	S—(CH 2 ) 9 —	8-nitro
662	Me	4-Imidazolyl-	S—(CH 2 ) 3 —	8-tert-butyl
663	Ethyl	Pyridin-3-yl-	S—(CH 2 ) 3 —	8-cyano
664	Me	Pyridin-3-yl-	S—(CH 2 ) 3 —	7-chloro
665	Me	N-Methyl-2-Pyrrolyl-	S—(CH 2 ) 3 —	H
666	Ethyl	Phenyl	(CH 2 ) 8 —	H
667	Me	3-Jod-phenyl	O—(CH 2 ) 3 —	8-nitro
668	Ethyl	Phenyl	S—(CH 2 ) 3 —	7-methyl
669	Me	Pyridin-4-yl-	S—CH 2 —C(CH 3 )═CH—CH 2 —	8-tert-butyl
670	Me	4-Methoxyphenyl	S—CH 2 —CH═CH—CH 2 —	7-methoxy
671	Me	Pyridin-3-yl-	S—CH 2 —CH═CH—CH 2 —	8-tert-butyl
672	Propyl	4-Methoxyphenyl	S—(CH 2 ) 3 —	8-nitro
673	Me	3-Pyrrolyl	S—(CH 2 ) 3 —	8-tert-butyl
674	Propyl	2-Thienyl	S—CH 2 —CH═CH—CH 2 —	7-methoxy
675	Me	N-Methyl-2-Pyrrolyl-	S—(CH 2 ) 3 —	8-nitro
676	Butyl	Phenyl	CO—(CH 2 ) 3 —	7-methyl
677	Me	2-Aminothiazol-4y1-	S—(CH 2 ) 3 —	8-tert-butyl
678	Me	Pyridin-3-yl-	S—(CH 2 ) 3 —	H
679	Ethyl	N-Methyl-2-Pyrrolyl-	S—(CH 2 ) 3 —	8-cyano
680	Me	2-Thienyl	S—(CH 2 ) 3 —	8-cyano
681	isoPropyl	5-Methyl imidazol-4-yl-	S—(CH 2 ) 3 —	8-tert-butyl
682	Butyl	Oxadiazol-2-yl	S—CH 2 —C(CH 3 )═CH—CH 2 —	8-tert-butyl
683	Me	4-Methylthiazol-5-yl	S—(CH 2 ) 3 —	H
684	Hexyl	Phenyl	(CH 2 ) 4 —	7-methyl
685	Me	3-Br-Pyridin-5-yl-	S—CH 2 —C(CH 3 )═CH—CH 2 —	8-tert-butyl
686	Propyl	Phenyl	S—CH 2 —C(CH 3 )═CH—CH 2 —	7-methyl
687	Me	2-Pyrazinyl-	S—(CH 2 ) 3 —	8-nitro
688	Me	2-Thienyl	S—(CH 2 ) 3 —	8-nitro
689	Me	Phenyl	S—(CH 2 ) 3 —	8-cyano
690	Me	3-Jod-phenyl	S—(CH 2 ) 4 —	7-methoxy
691	Me	Tetrazolyl-	S—(CH 2 ) 3 —	8-tert-butyl
692	Me	2-Pyrazinyl-	S—(CH 2 ) 3 —	H
693	Me	2-Pyrazinyl-	S—(CH 2 ) 3 —	8-cyano
694	Me	2,5-Di-methyl-furanyl-3-	S—(CH 2 ) 3 —	8-tert-butyl
695	Me	4-Methylthiazol-5-yl	S—(CH 2 ) 3 —	7-methoxy
696	Phenyl	3-Benzthienyl-	S—(CH 2 ) 3 —	8-tert-butyl
697	Propyl	Phenyl	COO—(CH 2 ) 4 —	H
698	isoPropyl	Phenyl	S—CH 2 —C(═CH 2 )—CH 2	7-methyl
699	Ethyl	3-Jod-phenyl	S—CH 2 —C(CH 3 )═CH—CH 2 —	8-cyano
700	Phenyl	2-Pyrazinyl-	O—(CH 2 ) 3 —	8-tert-butyl
701	Me	2-Me-4-Oxazolyl-	S—CH 2 —CH═CH—CH 2 —	8-tert-butyl
702	isoPropyl	Cyclohexyl-	O—(CH 2 ) 8 —	8-tert-butyl
703	Phenyl	3-Cyano-phenyl	S—(CH 2 ) 3 —	8-tert-butyl
704	Me	Pyridin-3-yl-	S—(CH 2 ) 3 —	7-methoxy
705	Me	4-Methoxyphenyl	S—(CH 2 ) 3 —	8-tert-butyl
706	Me	N-Propyl-tetrazolyl-	S—(CH 2 )3—	8-tert-butyl
707	Me	4-Methoxyphenyl	S—(CH 2 ) 3 —	7-chloro
708	Propyl	Phenyl	S—(CH 2 ) 3 —	7-methoxy
709	Me	2-Thienyl	S—(CH 2 ) 7 —	H
710	cycPropyl	Phenyl	(CH 2 ) 4 —	7-methyl
711	Ethyl	Phenyl	S—(CH 2 ) 3 —	8-nitro
712	cycPropyl	Phenyl	O—(CH 2 ) 3 —	7-methyl
713	Me	4-Jod-phenyl	S—CH 2 —CH═CH—CH 2 —	8-tert-butyl
714	Ethyl	4-Methylthiazol-5-yl	S—CH 2 —C(CH 3 )═CH—CH 2 —	8-cyano
715	Me	4-Methoxyphenyl	S—CH 2 —CH═CH—CH 2 —	H
716	Me	Methylamino	S—(CH 2 ) 3 —	8-tert-butyl
717	isoPropyl	3-Thienyl	S—(CH 2 ) 3 —	8-tert-butyl
718	Me	3-Jod-phenyl	S—(CH 2 )3—	7-chloro
719	Butyl	Phenyl	(CH 2 ) 4 —	7-methyl
720	Hexyl	Phenyl	(CH 2 ) 4 —	7-methyl
721	isoPropyl	2-Thienyl	CONH—(CH 2 ) 4 —	H
722	Me	N-Methyl-2-Pyrrolyl-	S—(CH 2 ) 3 —	8-tert-butyl
723	Ethyl	Phenyl	S—(CH 2 ) 3 —	7-chloroo

Examples of Pharmaceutical Administration Forms

A) Tablets

Tablets of the following composition were pressed on a tabletting machine in the customary manner

40 mg of the substance from Example 1

120 mg of corn starch

13.5 mg of gelatin

45 mg of lactose

2.25 mg of Aerosil® (chemically pure silicic acid in a submicroscopically fine dispersion)

6.75 mg of potato starch (as a 6% paste)

B) Sugar-coated Tablets

20 mg of the substance from Example 1

60 mg of core composition

70 mg of sugar-coating composition

The core composition consists of 9 parts of corn starch, 3 parts of lactose and 1 part of vinylpyrrolidone-vinyl acetate 60:40 copolymer. The sugar-coating composition consists of 5 parts of cane sugar, 2 parts of corn starch, 2 parts of calcium carbonate and 1 part of talc. The sugar-coated tablets which have been prepared in this way are then provided with enteric coating.

Biological Investigations—receptor binding studies

1) D 3 Binding Test

Cloned human D 3 -receptor-expressing CCL 1,3 mouse fibroblasts, obtainable from Res. Biochemicals Internat. One Strathmore Rd., Natick, Mass. 01760-2418 USA, were used for the binding studies.

Cell Preparation

The D 3 -expressing cells were multiplied in RPMI-1640 containing 10% fetal calf serum (GIBCO No. 041-32400 N); 100 U of penicillin/ml and 0.2% streptomycin (GIBO BRL, Gaithersburg, Md., USA). After 48 h, the cells were washed with PBS and incubated for 5 min with 0.05% trypsin-containing PBS. After that, the solution was neutralized with medium and the cells were collected by centrifuging at 300 g. In order to lyse the cells, the pellet was washed briefly with lysis buffer (5 mM Tris-HCl, pH 7.4, containing 10% glycerol) and after that incubated, at 4° C. for 30 min, at a concentration of 10 7 cells/ml of lysis buffer. The cells were centrifuged at 200 g for 10 min and the pellet was stored in liquid nitrogen.

Binding Tests

For the D 3 -receptor binding test, the membranes were suspended in incubation buffer (50 mM Tris-HCl, pH 7.4, containing 120 mM NaCl, 5 mM KC1, 2 mM CaCl 2 , 2 mM MgCl 2 , 10 μM quinolinol, 0.1% ascorbic acid and 0.1% BSA), at a concentration of approx. 10 6 cells/250 μl of test mixture, and incubated at 30° C. for 0.1 nM 125 iodosulpiride in the presence and absence of the test substance. The nonspecific binding was determined using 10 −6 M spiperone.

After 60 min, the free radioligand and the bound radioligand were separated by filtering through GF/B glass fiber filters (Whatman, England) on a Skatron cell harvester (Skatron, Lier, Norway), and the filters were washed with ice-cold Tris-HCl buffer, pH 7.4. The radioactivity which had collected on the filters was quantified using a Packard 2200 CA liquid scintillation counter.

The K i values were determined by means of nonlinear regression analysis using the LIGAND program. The compound of example 1 has a K i value for the binding toward the D 3 receptor of K i =50 nM.

2) D 2 Binding Test

Cell Culture

HEK-293 cells possessing stably expressed human dopamine D2A receptors were cultured in RPMI 1640 containing Glutamix I™ and 25 mM HEPES containing 10% fetal calf serum albumin. All the media contained 100 units of penicillin per mol and 100 μg/ml of streptomycin/ml. The cells were maintained at 37° C. in a moist atmosphere containing 5% Co 2 .

The cells were prepared for the binding studies by trypsinizing them (0.05% solution of trypsin) at room temperature for 3-5 minutes. After that, the cells were centrifuged at 250 g for 10 minutes and treated with lysis buffer (5 mM Tris-HCl, 10% glycerol, pH 7.4) at 4° C. for 30 minutes. After centrifuging at 250 g for 10 minutes, the residue was stored at −20° C. until used.

Receptor Binding Tests

Low affinity state dopamine D 2 receptor using 125 I-spiperone (81 TBq/mmbl, Du Pont de Nemours, Dreieich)

The test mixtures (1 ml) consisted of 1×10 5 cells in incubation buffer (50 mM Tris, 120 mM NaCl, 5 mM KCl, 2 MM MgCl 2 and 2 mM CaCl 2 , pH 7.4 with HCl) and 0.1 mM 125 I-spiperone (total binding) or additionally 1 μM haloperidol (nonspecific binding) or test substance.

After the test mixtures had been incubated at 25° C. for 60 minutes, they were filtered through GM/B glass filters (Whatman, England) on a Skatron cell harvester (from Zinsser, Frankfurt), and the filters were washed with ice-cold 50 mM Tris-HCl buffer, pH 7.4. The radioactivity: which had collected on the filters was quantified using a Packard 2200 CA liquid scintillation counter.

The results were evaluated as described in a).

The K i values were determined by way of nonlinear regression analysis using the LIGAND program or by converting the IC 50 values using the Cheng and Prusoff formula.

In these tests, the compounds according to the invention exhibit very good affinities for the D 3 receptor (<1 μmolar, in particular <200 nmolar) and bind selectively to the D 3 receptor.

Claims

1. A triazole compound of the formula I whereR1 is H, C1-C6-alkyl, which may be substituted by OH, OC1-C6-alkyl, halogen or phenyl, C3-C6-cycloalkyl or phenyl; R2 is H, C1-C6-alkyl, which may be substituted by OH, OC1-C6-alkyl, halogen or phenyl, C1-C6-alkoxy, C1-C6-alkylthio, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, halogen, CN, COOR3, CONR3R4, NR3R4, SO2R3, SO2NR3R4 or an aromatic radical which is selected from phenyl, naphthyl and a 5- or 6-membered heterocyclic radical having 1, 2, 3 or 4 heteroatoms which are selected, independently of each other, from O, N and S, with it being possible for the aromatic radical to have one or two substituents which are selected, independently of each other, from OH, C1-C6-alkyl, which may be substituted by OH, OC1-C6-alkyl, halogen or phenyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, halogen, CN, COR3, NR3R4, NO2, SO2R3, SO2NR3R4 and phenyl which may be substituted by one or two radicals which are selected, independently of each other, from C1-C6-alkyl, C1-C6-alkoxy, NR3R4, CN, CF3, CHF2 or halogen; R3 and R4 are, independently of each other, H, C1-C6-alkyl, which may be substituted by OH, OC1-C6-alkyl, halogen or phenyl, or phenyl; A is C4-C10-alkylene or C3-C10-alkylene which comprises at least one group Z which is selected from O, S, CONR3, COO, CO, C3-C6-cycloalkyl and a double or triple bond; B is a radical of the following formulae (a) or (b): X is CH2 or CH2CH2; Y is CR2 or O; R6 and R7 are, independently of each other, selected from H, C1-C6-alkyl, which may be substituted by halogen, C1-C6-alkylthio-C1-C6-alkyl, OH, C1-C6-alkoxy, C2-C6-alkenyl, halogen, CN, NO2, SO2R3, SO2NR3R4 and CONR3R4, or a salt thereof with a physiologically tolerated acid.

2. A compound as claimed in claim 1 of the formula I, where X and/or Y are CH2.

3. A compound as claimed in claim 1 of the formula I, where A is C4-C10-alkylene or C3-C10-alkylene which comprises at least one group Z which is selected from O, S, COO, CO, a double bond or triple bond and C3-C6-cycloalkyl.

4. A compound as claimed in claim 1 of the formula I where A is C4-C10-alkylene or C3-C10-alkylene which comprises at least one group Z which is selected from O, S, a double bond and cyclohexyl.

5. A compound as claimed in claim 1 of the formula I, where R2 is an aromatic radical which is unsubstituted or has one or two substituents which are selected, independently of each other, from C1-C6-alkyl, OH, C1-C6-alkoxy, phenyl, CN and halogen.

6. A compound as claimed in claim 1 of the formula I, where R2 is H, C1-C6-alkyl, phenyl, thienyl, furanyl, pyridyl, pyrrolyl, thiazolyl or pyrazinyl.

7. A compound as claimed in claim 1 of the formula I, where R1 is H, C1-C6-alkyl or C3-C6-cycloalkyl.

8. A compound as claimed in claim 1 of the formula I, where R6 and R7 are selected, independently of each other, from H, C1-C6-alkylthio-C1-C6-alkyl, halogen, CN, NO2, So2R3, SO2NR3R4 and CONR3R4.

9. A compound as claimed in claim 1 of the formula I, whereR1 is H, C1-C6-alkyl or phenyl, R2 is H, C1-C6-alkyl, phenyl, thienyl, furanyl, tetrazolyl, pyrrolyl, thiazolyl or pyrazinyl, A is -SC3-C10-alkylene which may comprise a double bond, and R6 and R7 are selected from H, C1-C6-alkyl, C1-C6-alkoxy, halogen, SO2NR3R4, CN, NO2 and CF3.

10. A pharmaceutical which comprises at least one compound as claimed in claim 1, where appropriate together with physiologically acceptable excipients and/or adjuvants.

11. A triazole compound of formula I whereR1 is H, C1-C6-alkyl, which may be substituted by OH, OC1-C6-alkyl, halogen or phenyl, C3-C6-cycloalkyl or phenyl; R2 is H, C1-C6-alkyl, which may be substituted by OH, OC1-C6-alkyl, halogen or phenyl, C1-C6-alkoxy, C1-C6-alkylthio, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, halogen, CN, COOR3, CONR3R4, NR3R4, SO2R3, SO2NR3R4 or an aromatic radical which is selected from phenyl, naphthyl and a 5- or 6-membered heterocyclic radical having 1, 2, 3 or 4 heteroatoms which are selected, independently of each other, from O, N and S, with it being possible for the aromatic radical to have one or two substituents which are selected, independently of each other, from OH, C1-C6-alkyl, which may be substituted by OH, OC1-C6-alkyl, halogen or phenyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, halogen, CN, COR3, NR3R4, NO2, SO2R3, SO2NR3R4 and phenyl which may be substituted by one or two radicals which are selected, independently of each other, from C1-C6-alkyl, C1-C6-alkoxy, NR3R4, CN, CF3, CHF2 or halogen; R3 and R4 are, independently of each other, H, C1-C6-alkyl, which may be substituted by OH, OC1-C6-alkyl, halogen or phenyl, or phenyl; A is C4-C10-alkylene or C3-C10-alkylene which comprises at least one group Z which is selected from O, S, CONR3, COO, CO, C3-C6-cycloalkyl and a double or triple bond; B is a radical of the following formulae (a) or (b): X is CH2 or CH2CH2; Y is CH2; R6 and R7 are, independently of each other, selected from H, C1-C6-alkyl, which may be substituted by halogen, C1-C6-alkylthio-C1-C6-alkyl, OH, C1-C6-alkoxy, C2-C6-alkenyl, halogen, CN, NO2, SO2R3, SO2NR3R4 and CONR3R4, or a salt thereof with a physiologically tolerated acid.

12. The compound defined in claim 11, wherein X is CH2.

13. The compound defined in claim 11, wherein A is C4-C10-alkylene or C3-C10-alkylene which comprises at least one group Z which is selected from O, S, COO, CO, a double bond or triple bond and C3-C6-cycloalkyl.

14. A compound as claimed in claim 11, wherein A is C4-C10-alkylene or C3-C10-alkylene which comprises at least one group Z which is selected from O, S, a double bond and cyclohexyl.

15. A compound as claimed in claim 11, wherein R2 is an aromatic radical which is unsubstituted or has one or two substituents which are selected, independently of each other, from C1-C6-alkyl, OH, C1-C6-alkoxy, phenyl, CN and halogen.

16. A compound as claimed in claim 11, wherein R2 is H, C1-C6-alkyl, phenyl, thienyl, furanyl, pyridyl, pyrrolyl, thiazolyl or pyrazinyl.

17. A compound as claimed in claim 11, wherein R1 is H, C1-C6-alkyl or C3-C6-cycloalkyl.

18. A compound as claimed in claim 11, wherein R6 and R7 are selected, independently of each other, from H, C1-C6-alkylthio-C1-C6-alkyl, halogen, CN, NO2, SO2R3, SO2NR3R4 and CONR3R4.

19. A compound as claimed in claim 11, whereinR1 is H, C1-C6-alkyl or phenyl, R2 is H, C1-C6-alkyl, phenyl, thienyl, furanyl, tetrazolyl, pyrrolyl, thiazolyl or pyrazinyl, A is —SC3-C10-alkylene which may comprise a double bond, and R6 and R7 are selected from H, C1-C6-alkyl, C1-C6-alkoxy, halogen, SO2NR3R4, CN, NO2 and CF3.

20. A pharmaceutical which comprises at least one compound as claimed in claim 11, optionally together with physiologically acceptable excipients and/or adjuvants.