RU96122779A - DERIVATIVES OF BENZOCYCLO-ALKYLAZOLOTION - Google Patents

Claims (23)

1. The compound of formula I or his prepreparat

where n is 0, 1 or 2;
t is 0, 1, 2 or 3;
R ^{1 is} independently halogen, hydroxy or C _1-4 alkyloxy; and
R ^{2 is} attached in the α-, β- or γ-position, preferably in the β- or γ-position, and denotes a group selected from formulas (a), (b) and (c):

where R ⁴ denotes hydrogen, R ³ denotes hydrogen or - (CH ₂ ) _q R ⁹ {where q is 0, 1, 2, 3 or 4 and R ⁹ denotes carboxy, C _1-4 alkyloxycarbonyl, carbamoyl or a group selected from aryl and heteroaryl (and this group is optionally substituted with one or two substituents independently selected from hydroxy, C _1-4 alkyloxy, cyano, 1H-tetrazol-5-yl, carboxy, and C _1-4 alkyloxycarbonyl)}, and R ⁵ is hydrogen or —NHR ¹⁰ {where R ¹⁰ denotes hydrogen, C _1-4 alkanoyl, trifluoro C _1-4 alkanoyl, carbamoyl, C _1-4 alkyloxycarbonyl, C _1-4 alkylcarbamoyl, diC _1-4 alkylcarbamoyl, am inoC _1-4 alkanoyl, C _1-4 alkilaminoC _1-4 alkanoyl, diC _1-4 alkilaminoC _1-4 alkanoyl, a group selected from aroyl and heteroaroyl (which aroyl and said heteroaroyl are optionally substituted with one or two substituents independently selected from hydroxy , C _1-4 alkyloxy, cyano, 1H-tetrazol-5-yl, carboxy and C _1-4 alkyloxycarbonyl), or —C (NR ¹¹ ) NHR ¹² (where R ¹¹ and R ¹² independently denote hydrogen, acetyl or tert- butoxycarbonyl)}; or R ⁴ and R ^{5 are} each hydrogen and R ³ is —NHR ¹⁰ (where R ¹⁰ is as defined above); or R ⁵ is hydrogen, R ³ is hydrogen or - (CH ₂ ) _q R ⁹ (where q and R ⁹ are as defined above) and R ⁴ is C _1-4 alkyl, di C _1-4 alkylaminomethyl, piperidine-1 -methyl, piperidin-1-ylmethyl, morpholin-4-ylmethyl, formyl, 1-hydroxyC _1-4 alkyl or -CH ₂ NHR ¹³ {where R ¹³ denotes hydrogen, C _1-4 alkyl, C _1-4 alkanoyl, trifluoroC _1-4 alkanoyl, carbamoyl, C _1-4 alkyloxycarbonyl, C _1-4 alkylcarbamoyl, diC _1-4 alkylcarbamoyl, aminoC _1-4 alkanoyl, C _1-4 alkilaminoC _1-4 alkanoyl, diC _{1-4 1-4} alkanoyl alkilaminoC , karboksiC _1-4 alkyl, C _1-4 alkiloksikarbonilC _1-4 alkyl karbamoilC _1-4 alkyl group, The selected from aroyl, heteroaroyl, arilC _1-4 alkyl and geteroarilC _1-4 alkyl (wherein said aroyl, heteroaroyl, aryl and heteroaryl are optionally substituted with one or two substituents independently selected from hydroxy, C _1-4 alkyloxy, cyano, 1H-tetrazol -5-yl, carboxy and C _1-4 alkyloxycarbonyl), or -C (NR ¹¹ ) NHR ¹² (where R ¹¹ and R ¹² are as defined above)}; or R ³ denotes hydrogen or - (CH ₂ ) _q R ⁹ (where q and R ⁹ have the meanings indicated above), R ⁴ denotes hydrogen, C _1-4 alkyl or -C (O) R ¹⁴ (where R ¹⁴ denotes amino, hydroxy, C _1-4 alkyloxy, 2- (dimethylamino) ethylamino, 4-methylpiperazin-1-yl, 2- (dimethylamino) ethyl mercapto, 4- (methylsulfonylamino) anilino or 1H-tetrazol-5-ylamino) and R ⁵ denotes cyano, hydroxymethyl, 1H-tetrazol-5-yl, 4,5-dihydroimidazol-2-yl, pyrrolidin-1-ylmetid, piperidin-1-ylmethyl, morpholin-4-ylmethyl, piperazin-1-ylmethyl, 4-C _1-4 alkylpiperazin-1-ylmethyl, -C (O) R ¹⁴ (wherein R ¹⁴ is as defined above), -C (NH) NR ¹⁵ R ¹⁶ (rk R ¹⁵ and R ¹⁶ independently of one another are hydrogen, C _1-4 alkyl or triftorC _1-4 alkyl) or -CH ₂ NR ¹⁰ R ¹⁷ (wherein R ¹⁰ is as defined above and R ¹⁷ is hydrogen or C _{1 -4} alkyl); or R ³ is hydrogen or - (CH ₂ ) _q R ⁹ (where q and R ⁹ have the meanings indicated above) and R ⁴ and R ⁵ simultaneously designate diC _1-4 alkylaminomethyl, piperidin-1-ylmethyl, morpholin-4- ylmethyl or hydroxymethyl;
R ⁶ is hydrogen, 2-carboxyethyl, 2-carbamoylethyl or 2-C _1-4 alkyloxycarbonylethyl,
R ⁷ is hydrogen, pyrrolidin-1-ylmethyl, piperidin-1-ylmethyl, morpholin-4-ylmethyl, piperazin-1-ylmethyl, 4-C _1-4 alkylpiperazin-1-ylmethyl or -CH ₂ NR ¹⁰ R ¹⁷ (where R ¹⁰ and R ¹⁷ are as defined above); and R ⁸ is hydrogen, 2-carboxyethyl, 2-carbamoylethyl, 2-C _1-4 alkyloxycarbonylethyl or —NHR ¹⁰ (where R ¹⁰ is as defined above); and its pharmaceutically acceptable salts, individual isomers and mixtures of isomers. 2. The compound according to claim 1, where R ² denotes a group of formula (a), (b) or (c) and is attached in the β-position. 3. The compound according to claim 2, wherein R ² denotes a group of formula (a) attached at the β position, n is 0 or 1 and R ⁵ denotes di C _1-4 alkylaminomethyl, pyrrolidin-1-ylmethyl, piperidin-1-ylmethyl , morpholin-4-ylmethyl, piperazin-1-ylmethyl, 4-C _1-4 alkylpiperazin-1-ylmethyl or -CH ₂ NHR ¹⁰ (preferably ureidomethyl, aminomethyl or acetylaminomethyl). 4. The compound according to claim 3, where n is 1, t is 2 and each R ¹ denotes fluorine, preferably in position 5 and 7. 5. The compound according to claim 4,
where R ⁵ denotes aminomethyl, namely, 5-aminomethyl-1- (5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -1,3-dihydroimidazole-2-thion and its pharmaceutically acceptable salts, preferably (S) -5-aminomethyl-1- (5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -1,3-dihydroimidazole-2-thione hydrochloride; or
where R ⁵ denotes ureidomethyl, namely, 5-ureidomethyl-1- (5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -1,3-dihydroimidazole-2-thione and its pharmaceutically acceptable salts, preferably (S) -5-ureidomethyl-1- (5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -1,3-dihydroimidazol-2-thion; or
where R ⁵ denotes acetylaminomethyl, namely, N- [3- (5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-thioxo-2,3-dihydro-1H-imidazole- 4-ylmethyl] acetamide and its pharmaceutically acceptable salts, preferably (S) -N- [3- (5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-thioxo-2,3 -dihydro-1H-imidazol-4-ylmethyl] acetamide. 6. The compound according to claim 2, wherein R ² denotes a group of formula (b) attached at the β position, n is 0 or 1 and R ⁷ denotes di C _1-4 alkylaminomethyl, pyrrolidin-1-ylmethyl, piperidin-1-ylmethyl , morpholin-4-ylmethyl, piperazin-1-ylmethyl, 4-C _1-4 alkylpiperazin-1-ylmethyl or -CH ₂ NHR ¹⁰ . 7. The compound according to claim 6, where n is 1, t is 2 and each R ¹ denotes fluorine, preferably in position 5 and 7. 8. A compound according to claim 7, wherein R ⁶ is hydrogen and R ⁷ is aminomethyl, namely, 5-aminomethyl-4- (5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl) - 2,4-dihydro [1,2,4] triazole-3-thion and its pharmaceutically acceptable salts, preferably (S) -5-aminomethyl-4- (5,7-difluoro-1,2,3,4- hydrochloride tetrahydronaphthalen-2-yl) -2,4-dihydro [1,2,4] triazole-3-thione. 9. The compound according to claim 2, where R ² denotes a group of formula (c) attached at the β-position, n is 0 or 1 and R ⁸ denotes amino. 10. The compound according to claim 9, where n is 1, t is 2 and each R ¹ denotes fluorine, preferably in position 5 and 7, namely, 4-amino-2- (5,7-difluoro-1,2, 3,4-tetrahydronaphthalen-2-yl) -2,4-dihydro [1,2,4] triazol-3-thion, preferably (S) -4-amino-2- (5,7-difluoro-1,2 , 3,4-tetrahydronaphthalen-2-yl) -2,4-dihydro [1,2,4] triazol-3-thione. 11. The prepreparation according to claim 1, which is a compound of formula II

where n is 0, 1 or 2;
t is 0, 1, 2 or 3;
R ^{1 is} independently halogen, hydroxy or C _1-4 alkyloxy; and
R ^{18 is} attached in the α, β or γ position and represents a group selected from the formulas (d), (e) and (f), preferably a group of the formula (d) attached in the β position;

where R ²⁰ denotes hydrogen, R ¹⁹ denotes hydrogen or - (CH ₂ ) _q R ⁹ {where q is 0, 1, 2, 3 or 4 and R ⁹ denotes carboxy, C _1-4 alkyloxycarbonyl, carbamoyl or a group selected from aryl and heteroaryl (and this group is optionally substituted with one or two substituents independently selected from hydroxy, C _1-4 alkyloxy, cyano, 1H-tetrazol-5-yl, carboxy and C _1-4 alkyloxycarbonyl)}, and R ²¹ means - NR ²⁵ R ²⁶ (where R ²⁵ denotes hydrogen or C _1-4 alkyl and R ²⁶ denotes L-alanyl, L-arginyl, L-asparaginyl, L-α-aspartyl,

aspartyl, L-cysteinyl, L-glutaminyl, L-α-glutamyl, L-γ-glutamyl, NC _1-4 alkanoyl-L-α-glutamyl, NC _1-4 alkanoyl-L-γ-glutamyl, glycyl, L- histidyl, L-isoleucyl, L-leucyl, L-lysyl, L-methionyl, L-ornithinyl, L-phenylalanil, L-prolyl, L-seril, L-threonyl, L-tryptophyl, L-tyrosyl, L-valyl, 1-aminocyclopropylcarbonyl, 1-aminocyclobutylcarbonyl, 1-aminocyclopentylcarbonyl or 1-aminocyclohexylcarbonyl); or R ²⁰ and R ^{21 are} each hydrogen and R ¹⁹ is —NR ²⁵ R ²⁶ (wherein R ²⁵ and R ²⁶ are as defined above); or R ²¹ is hydrogen, R ¹⁹ is hydrogen or - (CH ₂ ) _q R ⁹ (where q and R ⁹ are as defined above) and R ²⁰ is —CH ₂ NR ²⁵ R ²⁶ (where R ²⁵ and R ²⁶ have the values specified above); or R ¹⁹ denotes hydrogen or - (CH ₂ ) _q R ⁹ (where q and R ⁹ have the meanings indicated above), R ²⁰ denotes hydrogen, C _1-4 alkyl or -C (O) R ¹⁴ (where R ¹⁴ denotes amino, hydroxy, C _1-4 alkyloxy, 2- (dimethylamino) ethylamino, 4-methylpiperazin-1-yl, 2- (dimethylamino) ethylmercapto, 4- (methylsulfonylamino) anilino or 1H-tetrazol-5-ylamino) and R ²¹ is —CH ₂ NR ²⁵ R ²⁶ (where R ²⁵ and R ²⁶ are as defined above); and R ²² is hydrogen, 2-carboxyethyl, 2-carbamoylethyl or 2-C _1-4 alkyloxycarbonylethyl; R ²³ is —CH ₂ NR ²⁵ R ²⁶ (where R ²⁵ and R ²⁶ are as defined above); and R ²⁴ is —NR ²⁵ R ²⁶ , (wherein R ²⁵ and R ²⁶ are as defined above); and its pharmaceutically acceptable salts, individual isomers and mixtures of isomers. 12. The compound according to claim 11, wherein R ¹⁸ represents a group of formula (d) attached at the β-position, n is 0 or 1, t is 2, each R ¹ is fluorine and R ²¹ is -CH ₂ NHR ²⁶ . 13. A compound according to claim 12, wherein R ¹ is fluorine in position 5 and 7 and R ²⁶ is L-arginyl, L-α-aspartyl, L-β-aspartyl, L-histidyl or L-ornithinyl. 14. The compound according to claim 13, wherein R ²⁶ is L-α-aspartyl, namely, 3S-amino-N- [3- (5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl ) -thioxo-2,3-dihydro-1H-imidazol-4-ylmethyl] succinamic acid and its pharmaceutically acceptable salts, preferably 3S-amino-N- [3- (5,7-difluoro-1,2,3, hydrochloride, 4-tetrahydronaphthalen-2S-yl) -2-thioxo-2,3-dihydro-1H-imidazol-4-ylmethyl] succinamic acid; or where R ²⁶ denotes L-histidinyl, namely, 2S-amino-3- (3H-imidazol-4-yl) -N- [3- (1,2,3,4-tetrahydronaphthalen-2-yl) -2 -thioxo-2,3-dihydro-1H-imidazol-1-yl] propionamide and its pharmaceutically acceptable salts, preferably 2S-amino-3- (3H-imidazol-4-yl) -N- [3- (1, 2,3,4-tetrahydronaphthalen-2S-yl) -2-thioxo-2,3-dihydro-1H-imidazol-1-yl] propionamide; or where R ²⁶ denotes L-ornithinyl, namely, 2S, 5-diamino-N- [3- (5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-thioxo-2 , 3-dihydro-1H-imidazol-4-ylmethyl] amide of valeric acid and its pharmaceutically acceptable salts, preferably 2S, 5-diamino-N- [3 (5,7-difluoro-1,2,3,4-tetrahydronaphthalene) hydrochloride -2S-yl) -2-thioxo-2,3-dihydro-1H-imidazol-4-ylmethyl] amide of valeric acid. 15. The prepreparation according to claim 1, which is a compound of formula III

where n is 0, 1 or 2;
t is 0, 1, 2 or 3;
R ^{1 is} independently halogen, hydroxy or C _1-4 alkyloxy; and
R ^{27 is} attached at the α-, β- or γ-position and denotes a group selected from formulas (g), (h) and (i), preferably a group of formula (g) attached at β-position:

where R ⁴ denotes hydrogen and R ⁵ denotes hydrogen or -NHR ¹⁰ {where R ¹⁰ denotes hydrogen, C _1-4 alkanoyl, trifluoroC _1-4 alkanoyl, carbamoyl, C _1-4 alkyloxycarbonyl, C _1-4 alkylcarbamoyl, diC _{1- 4} alkylcarbamoyl, aminoC _1-4 alkanoyl, C _1-4 alkilaminoC _1-4 alkanoyl, diC _1-4 alkilaminoC _1-4 alkanoyl, a group selected from aroyl and heteroaroyl (which aroyl and said heteroaroyl are optionally substituted with one or two substituents independently selected from hydroxy, C _1-4 alkyloxy, cyano, 1H-tetrazol-5-yl, carboxy and C _1-4 alkyloxycarbonyl) or -C (NR ¹¹⁾ NHR ¹² (where R ¹¹ and R ¹² independent mo hydrogen, acetyl or tert-butoxycarbonyl)}; or R ⁵ is hydrogen and R ⁴ is C _1-4 alkyl, diC _1-4 alkylaminomethyl, piperidin-1-ylmethyl, morpholin-4-ylmethyl, 1-hydroxyC _1-4 alkyl or -CH ₂ NHR ¹³ {where R ¹³ denotes hydrogen, C _1-4 alkyl, C _1-4 alkanoyl, trifluoroC _1-4 alkanoyl, carbamoyl, C _1-4 alkyloxycarbonyl, C _1-4 alkylcarbamoyl, C _1-4 alkylcarbamoyl, aminoC _1-4 alkanoyl, C _{1- 4} alkylamino C _1-4 alkanoyl, diC _1-4 alkylamino C _1-4 alkanoyl, carboxy C _1-4 alkyl, C _1-4 alkyloxycarbonyl C _1-4 alkyl, carbamoyl C _1-4 alkyl, a group selected from arooyl, heteroaroyl, arylC _{1- 4} alkyl and heteroarylC _1-4 alkyl (and the specified aroyl, hetero aroyl, aryl and heteroaryl are optionally substituted with one or two substituents independently selected from hydroxy, C _1-4 alkyloxy, cyano, 1H-tetrazol-5-yl, carboxy and C _1-4 alkyloxycarbonyl) or -C (NR ¹¹ ) NHR ¹² (where R ¹¹ and R ¹² are as defined above)}; or R ⁴ denotes hydrogen, C _1-4 alkyl or —C (O) R ¹⁴ (where R ¹⁴ denotes amino, hydroxy, C _1-4 alkyloxy, 2- (dimethylamino) ethylamino, 4-methylpiperazin-1-yl, 2 - (dimethylamino) ethyl mercapto, 4- (methylsulfonylamino) anilino or 1H-tetrazol-5-ylamino) and R ⁵ denotes hydroxymethyl, 1H-tetrazol-5-yl, 4,5-dihydroimidazol-2-yl, pyrrolidin-1-ylmethyl piperidin-1-ylmethyl, morpholin-4-ylmethyl, piperazin-1-ylmethyl, 4-C _1-4 alkylpiperazin-1-ylmethyl, -C (O) R ¹⁴ (where R ¹⁴ is as defined above), - C (NH) NR ¹⁵ R ¹⁶ (wherein R ¹⁵ and R ¹⁶ independently of one another are hydrogen, C _1-4 alkyl or _1-4 triftorC Alki l) or -CH ₂ NR ¹⁰ R ¹⁷ (where R ¹⁰ is as defined above, and R ¹⁷ is hydrogen or C _1-4 alkyl); or R ⁴ and R ⁵ at the same time mean diC _1-4 alkylaminomethyl, piperidin-1-ylmethyl, morpholin-4-ylmethyl or hydroxymethyl;
R ⁶ is hydrogen, 2-carboxyethyl. 2-carbamoylethyl or 2-C _1-4 alkyloxycarbonylethyl;
R ⁷ is hydrogen, pyrrolidin-1-ylmethyl, piperidin-1-ylmethyl, morpholin-4-ylmethyl, piperazin-1-ylmethyl, 4-C _1-4 alkylpiperazin-1-ylmethyl or -CH ₂ NR ¹⁰ R ¹⁷ (where R ¹⁰ and R ¹⁷ are as defined above); and
R ²⁸ denotes C _2-6 alkyl {and alkyl substituted by one or two substituents independently selected from -N (R ²⁹ ) ₂ , -C (O) OR ³⁰ , -PO (OR ³⁰ ) ₂ , -SO ₃ R ³⁰ , -SO ₂ NHR ³⁰ and -OR ³⁰ (where each R ^{29 is} independently hydrogen, acetyl or trifluoroacetyl and each R ^{30 is} independently hydrogen or C _1-5 alkyl)};
and its pharmaceutically acceptable salts, individual isomers and mixtures of isomers. 16. The compound according to claim 15, wherein R ²⁷ denotes a group of formula (g) attached at the β-position, n is 0 or 1, t is 2 and each R ¹ denotes fluorine, preferably at position 5 and 7. 17. The compound according to claim 16, wherein R ²⁸ represents a group selected from ethyl, 1,1-dimethylethyl and propyl (this group is substituted by one or two substituents independently selected from carboxy, methoxycarbonyl, amino and trifluoroacetylamino), preferably (R ) -2-amino-2-methoxycarbonylethyl, (R) -2-amino-2-carboxyethyl, (R) -2-trifluoroacetylamino-2-methoxycarbonylethyl, 2-aminoethyl, (S) -2-amino-2-carboxy- 1,1-dimethylethyl or 3-amino-3-carboxyprop-1-yl.  18. A pharmaceutical composition comprising a therapeutically effective amount of a compound according to claims 1, 2, 11, 14 or 15. 19. A method of treating a disease state that can be alleviated with a drug that inhibits dopamine-β-hydroxylase in an animal in need of such treatment, in particular congestive heart failure, comprising administering to the animal a therapeutically effective amount of a compound of formula I or its preparation

where n is 0, 1 or 2;
t is 0, 1, 2 or 3;
R ^{1 is} independently halogen, hydroxy or C _1-4 alkyloxy;
R ^{2 is} attached in the α-, β- or γ-position and denotes a group selected from formulas (a), (b) and (c):

where R ⁴ denotes hydrogen, R ³ denotes hydrogen or - (CH ₂ ) _q R ⁹ {where q is 0, 1, 2, 3 or 4 and R ⁹ denotes carboxy, C _1-4 alkyloxycarbonyl, carbamoyl or a group selected from aryl and heteroaryl (and this group is optionally substituted with one or two substituents independently selected from hydroxy, C _1-4 alkyloxy, cyano, 1H-tetrazol-5-yl, carboxy, and C _1-4 alkyloxycarbonyl)}, and R ⁵ is hydrogen or —NHR ¹⁰ {where R ¹⁰ denotes hydrogen, C _1-4 alkanoyl, trifluoroC _1-4 alkanoyl, carbamoyl, C _1-4 alkyloxycarbonyl, C _1-4 alkylcarbamoyl. diC _1-4 alkylcarbamoyl, aminoC _1-4 alkanoyl, C _1-4 alkilaminoC _1-4 alkanoyl, diC _1-4 alkilaminoC _1-4 alkanoyl, a group selected from aroyl and heteroaroyl (which aroyl and said heteroaroyl are optionally substituted with one or two substituents independently selected from hydroxy, C _1-4 alkyloxy, cyano, 1H-tetrazol-5-yl, carboxy, and C _1-4 alkyloxycarbonyl), or -C (NR ¹¹ NHR ¹² (where R ¹¹ and R ¹² independently represent hydrogen , acetyl or t-butoxycarbonyl)}; or R ⁴ and R ^{5 are} each hydrogen and R ³ is —NHR ¹⁰ (where R ¹⁰ is as defined above); or R ⁵ is in hydrogen, R ³ denotes hydrogen or - (CH ₂ ) _q R ⁹ (where q and R ⁹ have the meanings indicated above) and R ⁴ denotes C _1-4 alkyl, di C _1-4 alkylaminomethyl, piperidin-1-ylmethyl, morpholine -4-ylmethyl, formyl, 1-hydroxyC _1-4 alkyl or -CH ₂ NHR ¹³ {where R ¹³ denotes hydrogen, C _1-4 alkyl, C _1-4 alkanoyl, trifluoroC _1-4 alkanoyl, carbamoyl, C _{1- 4} alkyloxycarbonyl, C _1-4 alkylcarbamoyl, diC _1-4 alkylcarbamoyl, aminoC _1-4 alkanoyl, C _1-4 alkilaminoC _1-4 alkanoyl, diC _1-4 alkilaminoC _1-4 alkanoyl karboksiC _1-4 alkyl, C _{1- 4} alkiloksikarbonilC _1-4 alkyl karbamoilC _1-4 alkyl, a group selected from aroyl, heteroaroyl, ari C _1-4 alkyl and geteroarilC _1-4 alkyl (wherein said aroyl, heteroaroyl, aryl and heteroaryl are optionally substituted with one or two substituents independently selected from hydroxy, C _1-4 alkyloxy, cyano. 1H-tetrazol-5-yl, carboxy and C _1-4 alkyloxycarbonyl), or —C (NR ¹¹ ) NHR ¹² (where R ¹¹ and R ¹² are as defined above)}; or R ³ denotes hydrogen or - (CH ₂ ) _q R ⁹ (where q and R ⁹ have the meanings indicated above), R ⁴ denotes hydrogen, C _1-4 alkyl or -C (O) R ¹⁴ (where R ¹⁴ denotes amino, hydroxy, C _1-4 alkyloxy, 2- (dimethylamino) ethylamino, 4-methylpiperazin-1-yl, 2- (dimethylamino) ethyl mercapto, 4- (methylsulfonylamino) anilino or 1H-tetrazol-5-ylamino) and R ⁵ denotes cyano, hydroxymethyl, 1H-tetrazol-5-yl, 4,5-dihydroimidazol-2-yl, pyrrolidin-1-ylmethyl, piperidin-1-ylmethyl, morpholin-4-ylmethyl, piperazin-1-ylmethyl, 4-C _1-4 alkylpiperazin-1-ylmethyl, -C (O) R ¹⁴ (where R ¹⁴ is as defined above), -C (NH) NR ¹⁵ R ¹⁶ (where R ¹⁵ and R ¹⁶ independently of one another denote hydrogen, C _1-4 alkyl or trifluoroC _1-4 alkyl) or -CH ₂ NR ¹⁰ R ¹⁷ (where R ¹⁰ is as defined above, and R ¹⁷ denotes hydrogen or C _{1 -4} alkyl); or R ³ denotes hydrogen or - (CH ₂ ) _q R ⁹ (where q and R ⁹ have the meanings indicated above) and R ⁴ and R ⁵ simultaneously denote diC _{1-> 4} alkylaminomethyl, piperidin-1-ylmethyl, morpholine-4 -methyl or hydroxymethyl;
R ⁶ is hydrogen, 2-carboxyethyl, 2-carbamoylethyl or 2-C _1-4 alkyloxycarbonylethyl;
R ⁷ is hydrogen, pyrrolidin-1-ylmethyl, piperidin-1-ylmethyl, morpholin-4-ylmethyl, piperazin-1-ylmethyl, 4-C _1-4 alkylpiperazin-1-ylmethyl or -CH ₂ NR ¹⁰ R ¹⁷ (where R ¹⁰ and R ¹⁷ are as defined above); and
R ⁸ is hydrogen, 2-carboxyethyl, 2-carbamoylethyl, 2-C _1-4 alkyloxycarbonylethyl or —NHR ¹⁰ (where R ¹⁰ is as defined above); or its pharmaceutically acceptable salt, single isomer or mixture of isomers. 20. The method according to claim 19, in which the compound is
5-aminomethyl-1- (5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -1,3-dihydroimidazol-2-tione or its pharmaceutically acceptable salt; or
5-ureidomethyl-1- (5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -1,3-dihydroimidazole-2-thione; or
N- [3- (5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-thioxo-2,3-dihydro-1H-imidazol-4-ylmethyl] acetamide; or
5-aminomethyl-4- (5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2,4-dihydro [1,2,4] triazol-3-thione or its pharmaceutically acceptable salts ; or
4-amino-2- (5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2,4-dihydro [1,2,4] triazol-3-thione; or
A prepreparation selected from the group consisting of compounds according to claims 11 and 15, such as:
3S-amino-N- [3- (5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-thioxo-2,3-dihydro-1H-imidazol-4-ylmethyl] succinam acid or its pharmaceutically acceptable salts; or
2S-amino-3- (3H-imidazol-4-yl) -N- [3- (1,2,3,4-tetrahydronaphthalen-2-yl) -2-thioxo-2,3-dihydro-1H-imidazole -1-yl] propionamide or its pharmaceutically acceptable salts; or
2S, 5-diamino-N- [3- (5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl) -2-thioxo-2,3-dihydro-1H-imidazol-4-ylmethyl valeric acid amide or pharmaceutically acceptable salts thereof.  21. The method of obtaining the compounds of formula I or its prodrug
 

 where n is 0, 1 or 2;
 t is 0, 1, 2 or 3;
 R^one independently denotes halogen, hydroxy or C_1-4alkyloxy; and
 R² is attached in the α-, β- or γ-position and denotes a group selected from formulas (a), (b) and (c):
 

 

 where r^four denotes hydrogen, R³ is hydrogen or - (CH₂)_qR⁹ {where q is 0, 1, 2, 3 or 4 and R⁹ denotes carboxy, C_1-4alkyloxycarbonyl, carbamoyl or a group selected from aryl and heteroaryl (and this group is optionally substituted with one or two substituents independently selected from hydroxy, C_1-4alkyloxy, cyano, 1H-tetrazol-5-yl, carboxy and C_1-4alkyloxycarbonyl)}, and R^five denotes hydrogen or -NHR^ten {where R^ten denotes hydrogen, C_1-4alkanoyl, trifluoro C_1-4alkanoyl, carbamoyl, C_1-4alkyloxycarbonyl, C_1-4alkylcarbamoyl, diC_1-4alkylcarbamoyl, aminoC_1-4alkanoyl, C_1-4alkylaminoC_1-4alkanoyl, di C_1-4alkylaminoC_1-4alkanoyl, a group selected from aryl and heteroaroyl (wherein said aroyl and heteroaroyl are optionally substituted with one or two substituents independently selected from hydroxy, C_1-4alkyloxy, cyano, 1H-tetrazol-5-yl, carboxy and C _1-4alkyloxycarbonyl), or -C (NR^eleven) NHR¹² (where R^eleven and R¹² independently represent hydrogen, acetyl or t-butoxycarbonyl)}; or r^four and R^five each denotes hydrogen and R³ denotes -NHR^ten (where R^ten has the meaning indicated above); or R^five denotes hydrogen, R³ is hydrogen or - (CH₂)_qR⁹ (where q and R⁹ as defined above) and R^four denotes C_1-4alkyl, diC_1-4alkylaminomethyl, piperidin-1-ylmethyl, morpholin-4-ylmethyl, formyl, 1-hydroxyC_1-4alkyl or -CH₂NHR¹³ {where R¹³ denotes hydrogen, C_1-4alkyl, C_1-4alkanoyl, trifluoroC_1-4alkanoyl, carbamoyl, C_1-4alkyloxycarbonyl, C_1-4alkylcarbamoyl, diC_1-4alkylcarbamoyl, aminoC_1-4alkanoyl, C_1-4alkylaminoC_1-4alkanoyl, diC_1-4alkylaminoC_1-4alkanoyl, carboxyC_1-4alkyl, C_1-4alkyloxycarbonylC_1-4alkyl, carbamoylC_1-4alkyl, a group selected from aroyl, heteroaroyl, arylC_1-4alkyl and heteroarylC_1-4alkyl (wherein said aroyl, heteroaroyl, aryl, and heteroaryl are optionally substituted with one or two substituents independently selected from hydroxy, C_1-4alkyloxy, cyano, 1H-tetrazol-5-yl, carboxy and C_1-4alkyloxycarbonyl), or -C (NR^eleven) NHR¹² (where R^eleven and R¹² have the meanings specified above)}; or r³ is hydrogen or - (CH₂)_qR⁹ (where q and R⁹ as defined above), R^four denotes hydrogen, C_1-4alkyl or -C (O) R¹⁴ (where R¹⁴ denotes amino, hydroxy, C_1-4alkyloxy, 2- (dimethylamino) ethylamino, 4-methylpiperazin-1-yl, 2- (dimethylamino) ethyl mercapto, 4- (methylsulfonylamino) anilino or 1H-tetrazol-5-ylamino) and R^five denotes cyano, hydroxymethyl, 1H-tetrazol-5-yl, 4,5-dihydroimidazol-2-yl, pyrrolidin-1-ylmethyl, piperidin-1-ylmethyl, morpholin-4-ylmethyl, piperazin-1-ylmethyl, 4-C_1-4alkylpiperazin-1-ylmethyl, -C (O) R¹⁴ (where R¹⁴ as defined above), -C (NH) NR¹⁵R^sixteen (where R¹⁵ and R^sixteen independently of one another denote hydrogen, C_1-4alkyl or trifluoroC_1-4alkyl) or -CH₂NR^tenR¹⁷ (where R^ten as defined above, and R¹⁷ denotes hydrogen or C_1-4alkyl); or r³ is hydrogen or - (CH₂)_qR⁹ (where q and R⁹ as defined above) and R^four and R^five simultaneously designate C_1-4alkylaminomethyl, piperidin-1-ylmethyl, morpholin-4-ylmethyl or hydroxymethyl;
 R⁶ denotes hydrogen, 2-carboxyethyl, 2-carbamoylethyl or 2-C_1-4alkyloxycarbonylethyl;
 R⁷ denotes hydrogen, pyrrolidin-1-ylmethyl, piperidin-1-ylmethyl, morpholin-4-ylmethyl, piperazin-1-ylmethyl, 4-C_1-4alkyl piperazin-1-ylmethyl or-CH₂NR^tenR¹⁷ (where R^ten and R¹⁷ have the meanings specified above); and R^eight denotes hydrogen, 2-carboxyethyl, 2-carbamoylethyl, 2-C_1-4alkyloxycarbonylethyl or -NHR^ten (where R^ten has the meanings indicated above); and its pharmaceutically acceptable salts, individual isomers and mixtures of isomers, including:
 (a) the interaction of the compounds of formula 3
 

 where each of n, t and r^one is as defined for formula I above, with dialkyloxy acetaldehyde in the presence of a chemical reducing agent or catalytic hydrogenation and subsequent treatment with thiocyanic acid to obtain the compound of formula I, where R² denotes a group of formula (a) in which R³R^four and R^five each is hydrogen; or
 (b) the interaction of the compounds of formula 3 or its acid additive salts, where each of n, t and R^one as defined for formula I, with thiocyanic acid and dihydroxyacetone, followed by optional treatment of the reaction mixture with sulfuric acid to obtain the compound of formula I, where R³ and R^four denote hydrogen and R^five denotes hydroxymethyl; or
 (C) the interaction of the compounds of formula 5
 

 where each of n, t and r^one as defined above for formula I, with the 1,2,4-triazol-4-ylamino group and subsequent sulfurization to obtain the compound of formula I, where R² denotes a group of formula (c) in which R^eight is amino; or
 (g) the interaction of the compounds of formula 7
 

 where each of n, t and r^one as defined above for formula I, with 2,2-dialkyloxyethylamine in the presence of a chemical reducing agent or catalytic hydrogenation and subsequent treatment with thiocyanic acid to obtain the compound of formula I, where R² denotes a group of formula (a), in which R³R^four and R^five each is hydrogen; or
 (d) the interaction of the compounds of formula 9
 

 where each of n, t and r^one as defined above for formula I, with 2,2-dialkyloxyethylamine and subsequent acid treatment to obtain the compound of formula I, where R² denotes a group of formula (a), in which R³R^four and R^five each is hydrogen; or
 (e) the interaction of the compounds of formula 9 with amino-acetonitrile hydrochloride and subsequent treatment with a base to obtain the compounds of formula I, where R² denotes a group of formula (a), in which R³ and R^four each denotes hydrogen and R^five is amino; or
 (g) the interaction of the compounds of formula 9 with D - (+) - glucosamine and subsequent oxidation to obtain the compounds of formula I, where R² denotes a group of formula (a), in which R³ and R^five each denotes hydrogen and R^four denotes formyl; or
 (h) the interaction of the compounds of formula 9 with a hydrazide of the formula H₂NHNC (O) R³⁴ (where R³⁴ denotes hydrogen, aminomethyl, C_1-4alkylaminomethyl, diC_1-4alkylaminomethyl, pyrrolidin-1-ylmethyl, piperidin-1-ylmethyl, morpholin-4-ylmethyl, piperazin-1-ylmethyl or 4-C_1-4alkylpiperazin-1-ylmethyl) or its protected derivative and subsequent treatment with a base and, if necessary, removal of the protective group to obtain a compound of formula I, where R² denotes a group of formula (b) in which R⁶ denotes hydrogen and R⁷ denotes hydrogen, aminomethyl, C_1-4alkylaminomethyl, diC_1-4alkylaminomethyl, pyrrolidin-1-ylmethyl, piperidin-1-ylmethyl, morpholin-4-ylmethyl, piperazin-1-ylmethyl or 4-C_1-4alkyl piperazin-1-ylmethyl; or
 (i) the interaction of the compounds of formula 11
 

 where each of n, t, r^oneR^four and R^five has the values indicated above for formula I, with a strong base and subsequent sulfurization to obtain the compounds of formula I, where R³ is hydrogen; or
 (k) the interaction of the compounds of formula 11, where each of n, t and R^oneR^four and R^five as defined above for formula I, with a compound of formula L- (CH₂)_qR⁹where L denotes the leaving group and each of q and R⁹ has the meaning specified above for formula I, and subsequent sulfurization to obtain the compounds of formula I, where R² denotes a group of formula (a), in which R³ denotes - (CH₂)_qR⁹; or
 (l) the interaction of the compounds of formula 11, where R^four and R^five each denotes hydrogen and each of n, t and R^one as defined above for formula I, with an aminoaryl or alkylsulfonate to form a compound of formula I, wherein R² denotes a group of formula (a), in which R³ is amino; or
 (m) alkylation of compounds of formula 11, where R^four and R^five each denotes hydrogen and each of n, t and R^one is as defined above for formula I, as appropriate for N, N-disubstituted methylene ammonium salt and subsequent sulfurization to obtain compounds of formula I, where R² denotes a group of formula (a), in which R^five denotes diC_one-C_fouralkylaminomethyl, piperidin-1-ylmethyl or morpholin-4-ylmethyl; or
 (n) the interaction of the compounds of formula 16
 

 where r³² denotes cyano or C_one-C_fouralkyloxycarbonyl and each of n, t and R^one as defined above for formula I, with a compound of formula R³³C (O) L and subsequent treatment with thiocyanic acid to obtain the compound of formula I, where R² denotes a group of formula (a), in which R³ denotes hydrogen, R^five denotes cyano or C_one-C_fouralkyloxycarbonyl and R^four denotes hydrogen, C_one-C_fouralkyloxycarbonyl or C_one-C_fouralkyl; or
 (o) the interaction of the compounds of formula 24
 

 where each of n, t and r^one as defined above for formula I, with isothiocyanate and subsequent treatment with a base to obtain a compound of formula I, where R² denotes a group of formula (c) in which R^eight is hydrogen; or
 (p) the interaction of the compounds of formula I, where R^five denotes hydroxymethyl, with a compound of the formula H₂N (O) R³¹ or with the ammonium salt of the formula

 (where R³¹ denotes hydrogen, C_1-4alkyl or trifluoroC_1-4alkyl) to obtain the compounds of formula I, where R^five denotes formylaminomethyl, C_1-4alkylcarbonylaminomethyl or trifluoroC_1-4alkylcarbonylaminomethyl with the compound, and this compound may then optionally be subjected to hydrolysis to obtain an acid additive salt of the compound of formula I, where R³ and R^four each denotes hydrogen and R^five denotes aminomethyl; or
 (p) the interaction of the compounds of formula I, where R^five denotes hydroxymethyl, with urea to obtain the compounds of formula I, where R^five means ureidomethyl; or
 (c) the interaction of the compounds of formula I, where R^five denotes cyano, with a derivative of nitrous acid to obtain the compounds of formula I, where R^five is 1H-tetrazol-5-yl; or
 (t) reduction of a compound of formula I, where R^five denotes cyano, to obtain the compounds of formula I, where R^five denotes aminomethyl; or
 (y) hydrolysis of compounds of formula I, where R^five denotes cyano, to obtain the compounds of formula I, where R^five is carbamoyl; or
 (f) the interaction of the compounds of formula I, where R^five is cyano, with ethylenediamine to produce a compound of formula I, where R^five is 4,5-dihydroimidazol-2-yl; or
 (x) the interaction of the compounds of formula I, where R^five is cyano, with a compound of the formula (CH₃)₂Alnr¹⁵R^sixteen to obtain the compounds of formula I, where R^five is —C (NH) NR¹⁵R^sixteenwhere R¹⁵ and R^sixteen have the meanings indicated above for formula I; or
 (v) reduction of a compound of formula I, where R^five or r^four and R^five both are ethoxycarbonyl, to obtain compounds of formula I, where R^five or r^four and R^five both are hydroxymethyl; or
 (h) the conversion of compounds of formula I, where R^five denotes hydroxymethyl, a compound of formula 28 NH $\genfrac{}{}{0ex}{}{\text{+ -}}{\text{four}}$ OC (O) R³
 where L denotes a leaving group and n, t and R^one have the meanings indicated above for formula I, and the interaction of the compounds of formula 28 with the amine of the formula HNR³⁶R³⁷where R³⁶ and R³⁷ independently denote C_one-C_fouralkyl or together denote - (CH₂)_four-, - (CH₂)_five-, - (CH₂)₂O (CH₂)₂- or - (CH₂)₂NR³⁸(CH₂)₂- where R³⁸ denotes hydrogen or C_1-4alkyl, to obtain the compounds of formula I, where R^five denotes aminomethyl, C_1-4alkylaminomethyl, di C_1-4alkylaminomethyl, pyrrolidin-1-ylmethyl, piperidin-1-ylmethyl, morpholin-4-ylmethyl, piperazin-1-ylmethyl or 4-C_1-4alkyl piperazin-1-ylmethyl; or
 (w) the interaction of the compounds of formula I, where R^four is formyl, with hydroxylamine hydrochloride and subsequent reduction to produce the compound of formula I, where R^four denotes aminomethyl; or
 (y) the interaction of the compounds of formula I, where R^four is formyl, with an amine of formula NH₂R^ten in the presence of a chemical reducing agent or catalytic hydrogenation to obtain a compound of formula I, where R^four is -CH₂NHR^tenwhere R^ten as defined above for formula I; or
 (s) alkylation of compounds of formula I, where R^four denotes formyl, to obtain the compounds of formula I, where R^four denotes 1-hydroxyC_1-4alkyl; or
 (e) the interaction of the compounds of formula I, where R³R^five or r⁶ denotes amino or R^fourR^five or r^eight denotes aminomethyl, with an appropriately substituted amidine to obtain the corresponding compounds of formula I, where R³R^five or r⁶ denotes -NHC (NR^eleven) NHR¹² either R^fourR^five or r^eight is -CH₂NHC (NR^eleven) NHR¹²where R^eleven denotes hydrogen, acetyl or t-butoxycarbonyl and R¹² is acetyl or t-butoxycarbonyl; or
 (w) treatment of compounds of formula I, where R³R^five or r⁶ denotes -NHC (NR^eleven) NHR¹² either R^fourR^five or r^eight is -CH₂NHC (NR^eleven) NHR¹²where R^eleven denotes hydrogen, acetyl or t-butoxycarbonyl and R¹² is acetyl or t-butoxycarbonyl, with an acid to produce a compound of formula I, where R³R^five or r⁶ denotes -NHC (NH) NH₂ either R^fourR^five or r^eight is -CH₂NHC (NH) NH₂; or
 (i) acylation of a compound of formula I, where R³R^five or r⁶ denotes amino or R^fourR^five or r^eight denotes aminomethyl, a corresponding acylating agent or a protected derivative thereof and, if necessary, subsequent removal of the protective group to obtain the corresponding compound of formula I, where R³R^five or r⁶ denotes -NHR^ten either R^fourR_five or r^eight is -CH₂NHR^tenwhere R^ten denotes C_1-4alkanoyl, trifluoroC_1-4 alkanoyl, carbamoyl, C_1-4alkyloxycarbonyl, C_1-4alkylcarbamoyl, diC_1-4alkylcarbamoyl, aminoC_1-4alkanoyl, C_1-4alkylaminoC_1-4alkanoyl, diC_1-4alkylaminoC_1-4alkanoyl or a group selected from aroyl and heteroaroyl (said aroyl and heteroaroyl being optionally substituted with one or two substituents independently selected from C_1-4alkyloxy, cyano, carboxy and C_1-4alkyloxycarbonyl); or
 (aa) the interaction of the compounds of formula I, where R³R^five or r⁶ denotes amino or R^fourR^five or r^eight denotes aminomethyl, with C_1-4alkyl isocyanate to obtain the compounds of formula I, where R³R^five or r⁶ denotes -NHR^ten or r^fourR^five or r^eight is -CH₂NHR^tenwhere R^ten denotes C_1-4alkylcarbamoyl; or
 (bb) alkylation of compounds of formula I, where R³R^four and R^five each is hydrogen, suitably N, N-disubstituted methylene ammonium salt to produce a compound of formula I, where R³ and R^five each denotes hydrogen and R^four denotes diC_1-4alkylaminomethyl, piperidin-1-ylmethyl or morpholin-4-ylmethyl; or
 (cv) alkylation of a compound of formula I, where R^four denotes hydrogen and R³ different from hydrogen, as appropriate with N, N-disubstituted methylene ammonium salt to obtain the corresponding compound of formula I, where R^five denotes diC_1-4alkylaminomethyl, piperidin-1-ylmethyl or morpholin-4-ylmethyl; or
 (yy) protecting the compound of formula I, where R³ is hydrogen, a thiol protecting group, alkylation with an appropriately N, N-disubstituted methylene ammonium salt and the subsequent removal of the protecting group to obtain a compound of formula I, where R³ and R^four each denotes hydrogen and R^five denotes diC_1-4alkylaminomethyl, piperidin-1-ylmethyl or morpholin-4-ylmethyl, or where R is³ denotes hydrogen and R^four and R^five both represent C_1-4alkylaminomethyl, piperidin-1-ylmethyl or morpholin-4-ylmethyl; or
 (dd) the interaction of the compounds of formula I, where R^five or r^four and R^five both are carboxy or its acid derivative, with an appropriate amine or thiol to obtain the compound of formula I, where R^five or r^four and R^five both represent 1H-tetrazol-5-ylcarbamoyl, 2- (dimethylamino) ethylcarbamoyl, 4-methylpiperazin-1-ylcarbonyl or 2- (dimethylamino) ethyl mercapto; or
 (e) interaction of a compound of formula I, where R³R⁶ or r^eight denotes hydrogen, with C_1-4alkylacrylate to obtain the compounds of formula I, where R³R⁶ or r^eight denotes 2-C_1-4alkyloxycarbonylethyl; or
 (LJ) hydrolysis of compounds of formula I, where R³R^fourR^fiveR⁶R⁷ or r^eight denotes C_1-4alkyloxycarbonyl or a group which is further substituted by C_1-4alkyloxycarbonyl Deputy, to obtain the compounds of formula I, where R³R^fourR^fiveR⁶R⁷ or r^eight denotes a carboxy or group that is further substituted by a carboxyl substituent; or
 (3) amination of the compound of formula I, where R³R^fourR^fiveR⁶R⁷ or r^eight denotes a carboxy or group that is additionally substituted by a carboxyl substituent, to obtain the compounds of formula I, where R³R^fourR^fiveR⁶R⁷ or r^eight means carbamoyl or a group that is further substituted with a carbamoyl substituent; or
 (ii) the interaction of the compounds of formula I, where R³R^fourR^fiveR⁶R⁷ or r^eight denotes a carboxy or group that is additionally substituted by a carboxyl group, with C_1-4alcohol to obtain the compounds of formula I, where R³R^fourR^fiveR⁶R⁷ or r^eight denotes C_1-4alkyloxycarbonyl or a group which is further substituted by C_1-4alkyloxycarbonyl group; or
 (kk) demethylation of a compound of formula I, where R^one denotes methoxy and / or where R³R^fourR^fiveR⁶R⁷ or r^eight denotes a group selected from aroyl, heteroaroyl, arylC_1-4alkyl and heteroaryl C_1-4alkyl (wherein said aroyl, heteroaroyl, aryl, and heteroaryl are optionally substituted with one or two methoxy groups) to form a compound of formula I, where R^one denotes hydroxy and / or where R³R^fourR^fiveR⁶R⁷ or r^eight denotes a group selected from aroyl, heteroaroyl, arylC_1-4alkyl and heteroarylC_1-4alkyl (wherein said aroyl, heteroaroyl, aryl, and heteroaryl are optionally substituted with one or two hydroxy groups); or
 (ll) the interaction of the compounds of formula I, where R³R^fiveR⁶ or r^eight denotes -NHR^ten or where R^fourR^five or r⁷ is -CH₂NHR^tenwhere R^ten denotes a group selected from aroyl, heteroaroyl, arylC_1-4alkyl and heteroarylC_1-4alkyl (wherein said aroyl, heteroaroyl, aryl, and heteroaryl are optionally substituted with cyano), with a hydrochloric acid derivative to form a compound of formula I, where R^ten denotes a group selected from aroyl, heteroaroyl, arylC_1-4alkyl and heteroarylC_1-4alkyl (wherein said aroyl, heteroaroyl, aryl and heteroaryl are optionally substituted with 1H-tetrazol-5-yl); or
 (mm) reacting the corresponding compound of formula I in non-salt form with a pharmaceutically acceptable inorganic or organic acid or base to form a pharmaceutically acceptable salt; or
 (nn) the reaction of a compound of formula I in the form of an appropriate acid addition salt or base addition salt with a suitable base or acid for this purpose, respectively, to obtain the free acid or free base; or
 (oo) separating a mixture of stereoisomers of the compound of formula I to form a single stereoisomer; or
 (PP) the interaction of the protected derivative of L-amino acids with the compound of the formula I
 

 or its pharmaceutically acceptable salt, individual isomer or mixture of isomers, where each of n, t and R^one as defined above for formula II as defined in claim 11, and R² is attached in the α-, β- or γ-position and denotes a group selected from formulas (a). (b) and (c):
 

 

 where r^four denotes hydrogen, R³ is hydrogen or - (CH₂)_qR⁹ (where q and R⁹ have the meanings given above) and R^five denotes -NHR^ten (where R^ten denotes hydrogen or C_1-4alkyl); or r^four and R^five each denotes hydrogen and R³ denotes -NHR^ten (where R^ten has the meanings indicated above); or r^five denotes hydrogen, R³ is hydrogen or - (CH₂)_qR⁹ (where q and R⁹ as defined above) and R^four is -CH₂NHR^ten (where R^ten has the meanings indicated above); or r³ is hydrogen or - (CH₂)_qR⁹ (where q and R⁹ as defined above), R^four denotes hydrogen, C_1-4alkyl or -C (O) R¹⁴ (where R¹⁴ denotes amino, hydroxy, C_1-4alkyloxy, 2- (dimethylamino) ethylamino, 4-methylpiperazin-1-yl, 2- (dimethylamino) ethyl mercapto, 4- (methylsulfonylamino) anilino or 1H-tetrazol-5-ylamino) and R^five is -CH₂NHR^ten (where R^ten has the meanings indicated above); and
 R⁶ denotes hydrogen, 2-carboxyethyl, 2-carbamoylethyl or 2-C_1-4alkyloxycarbonylethyl;
 R⁷ is -CH₂NHR^ten (where R^ten has the meanings indicated above); and
 R^eight denotes -NHR^ten (where R^ten as defined above) to prepare a prodrug of formula II as defined in claim 11, and further optionally reacting the corresponding non-salt form of the compound of formula II with a pharmaceutically acceptable inorganic or organic acid or base to form a pharmaceutically acceptable salt; or additionally, optionally, reacting a compound of formula II in the form of an appropriate acid addition salt or base addition salt with a suitable base or acid for the preparation of the free acid or free base, respectively; or additionally optionally separating a mixture of stereoisomers of the compound of formula II to obtain a single stereoisomer; or
 (pp) the interaction of the compounds of formula 47
 

 or its protected derivative, where R²⁸ as defined above for formula III, with a compound of formula I
 

 or with its pharmaceutically acceptable salt, single isomer or mixture of isomers, where n, t and R^one as defined above, and R² is attached in the α-, β- or γ-position and denotes a group selected from formulas (a), (b) and (c):
 

 

 where r³R⁷ and R^eight denote hydrogen and R^fourR^five and R⁶ have the meanings indicated above for formula III; and, if necessary, removal of the protective group to obtain the prodrug of formula III according to claim 15, and additionally optionally, reacting the corresponding non-salt form of the compound of formula III with a pharmaceutically acceptable inorganic or organic acid or base to form a pharmaceutically acceptable salt; or optionally, reacting the compound of formula III in the form of an appropriate acid addition salt or base addition salt with a suitable base or acid for the preparation of the free acid or the free base, respectively; or additionally, optionally separating a mixture of steroisomers of the compound of formula III to obtain a single stereoisomer. 22. The compound of the formula

namely, (S) -5,7-difluoro-12,3,4-tetrahydronaphthalen-2-ylamine. 23. The method of obtaining the S-enantiomer of formula 3 (a)

where t is 0, 1, 2 or 3, preferably 2; and
R ^{1 is} independently halogen, hydroxy or C _1-4 alkyloxy, preferably fluorine in position 5 and 7;
including:
(a) recovery of the compounds of formula 7 (b)

in the presence of 2S-dimethylamino-1R-phenylpropanol and 2-ethylaminopyridine to obtain the (R) -enantiomer of formula 6 (c)

(b) treating the (R) -enantiomer of formula 6 (c) with a methanesulfonyl chloride and then reacting with azide to obtain the (S) -enantiomer of formula 4 (a)

and
(c) recovery.