Claims
- 1. A compound of formula I ##STR6## in which R1 is 1-4C-alkyl,
- R2 is hydroxyl, 1-4C-alkoxy, 3-7C-cycloalkoxy, 3-7C-cycloalkylmethoxy or 1-4C-alkoxy which is completely or predominantly substituted by fluorine,
- R3 is hydroxyl, 1-4C-alkoxy, 3-7C-cycloalkoxy, 3-7C-cycloalkylmethoxy or 1-4C-alkoxy which is completely or predominantly substituted by fluorine,
- or in which
- R2 and R3 together are a 1-2C-alkylenedioxy group,
- R4 is a phenyl radical which is substituted by R5 and R6, where
- R5 is hydrogen, hydroxyl, halogen, nitro, 1-4C-alkyl, trifluoromethyl or 1-4C-alkoxy,
- R6 is CO--R7 or CO--R8, where
- R7 is hydroxyl, 1-8C-alkoxy, 3-7C-cycloalkoxy or 3-7C-cycloalkylmethoxy and
- R8 is N(R81)R82, where R81 and R82 independently of one another are hydrogen, 1-7C-alkyl, 3-7C-cycloalkyl or 3-7C-cycloalkylmethyl, or where R81 and R82, together with the nitrogen atom to which both are bonded, are a 1-pyrrolidinyl, 1-piperidyl, 1-hexahydroazepinyl or 4-morpholinyl radical,
- or a salt thereof.
- 2. A compound of formula I according to claim 1, in which
- R1 is 1-4C-alkyl,
- R2 is 1-4C-alkoxy, 3-7C-cycloalkoxy, 3-7C-cycloalkylmethoxy or 1-2C-alkoxy which is completely or predominantly substituted by fluorine,
- R3 is 1-4C-alkoxy, 3-7C-cycloalkoxy, 3-7C-cycloalkylmethoxy or 1-2C-alkoxy which is completely or predominantly substituted by fluorine,
- R4 is a phenyl radical which is substituted by R5 and R6, where
- R5 is hydrogen, hydroxyl, halogen, nitro, 1-4C-alkyl, trifluoromethyl or 1-4C-alkoxy,
- R6 is CO--R7 or CO--R8, where
- R7 is hydroxyl, 1-8C-alkoxy, 3-7C-cycloalkoxy or 3-7C-cycloalkylmethoxy and
- R8 is N(R81)R82, where R81 and R82 independently of one another are hydrogen, 1-7C-alkyl, 3-7C-cycloalkyl or 3-7C-cycloalkylmethyl, or where R81and R82, together with the nitrogen atom to which both are bonded, are a 1-piperidyl, 1-hexahydroazepinyl or 4-morpholinyl radical,
- or a salt thereof.
- 3. A compound of formula I according to claim 1, in which
- R1 is methyl,
- R2 is 1-4C-alkoxy, 3-7C-cycloalkoxy or 1-2C-alkoxy which is completely or predominantly substituted by fluorine,
- R3 is 1-4C-alkoxy, 3-7C-cycloalkoxy or 1-2C-alkoxy which is completely or predominantly substituted by fluorine,
- R4 is a phenyl radical which is substituted by R5 and R6, where
- R5 is hydrogen, hydroxyl, 1-4C-alkyl or 1-4C-alkoxy,
- R6 is CO--R7 or CO--R8, where
- R7 is hydroxyl, 1-8C-alkoxy or 3-7C-cycloalkoxy and
- R8 is N(R81)R82, where R81and R82 independently of one another are hydrogen, 1-7C-alkyl or 3-7C-cycloalkyl, or where R81 and R82, together with the nitrogen atom to which both are bonded, are a 1-piperidyl, 1-hexahydroazepinyl or4-morpholinyl radical,
- or a salt thereof.
- 4. A compound of formula I according to claim 1, in which
- R1 is methyl,
- R2 is methoxy or ethoxy,
- R3 is methoxy or ethoxy,
- R4 is a phenyl radical which is substituted by R5 and R6, where
- R5 is hydrogen,
- R6 is CO--R7 or CO--R8, where
- R7 is hydroxyl or 1-8C-alkoxy and
- R8 is N(R81)R82, where R81 and R82 independently of one another are hydrogen or 1-4C-alkyl or 5--7C-cycloalkyl, or where R81 and R82, together with the nitrogen atom to which both are bonded, are a 1-piperidyl, 1-hexahydroazepinyl or 4-morpholinyl radical,
- or a salt thereof.
- 5. A compound of formula I according to claim 1, in which
- R1 is methyl,
- R2 is ethoxy,
- R3 is methoxy or ethoxy,
- R4 is a phenyl radical which is substituted by R5 and R6, where
- R5 is hydrogen,
- R6 is CO--R7 or CO--R8, where
- R7 is 1-4C-alkoxy and
- R8 is N(R81)R82, where-R81 and R82 independently of one another are 1-4C-alkyl or 5-7C-cycloalkyl, or where R81 and R82, together with the nitrogen atom to which both are bonded, are a 1-piperidyl or 1-hexahydroazepinyl radical,
- or a salt thereof.
- 6. A compound of formula I according to claim 1, in which the hydrogen atoms in positions 4a and 10 b are in the cis position relative to one another, or a salt thereof.
- 7. A compound of formula I according to claim 1, which in the positions 4a and 10b have the same absolute configuration as the compound (-)-cis-4-amino-3-(3,4-dimethoxyphenyl)-1-methylpiperidine dihydrochloride having the optical rotation [.alpha.].sup.22.sub.D -57.1 .degree. (c=1, methanol).
- 8. A compound selected from the group consisting of
- cis-8,9-Diethoxy-6-(4-isopropoxycarbonylphenyl)-2-methyl-1,2,3,4,4a,10b-hexahydrobenzo[c][1,6]naphthyridine;
- cis-8,9-Diethoxy-6-(4-diisopropylaminocarbonylphenyl-2-methyl-1,2,3,4,4a,10b-hexahydrobenzo[c][-1,6]naphthyridine;
- cis-8,9-Diethoxy-6-(4-N-cyclohexyl-N-isopropylaminocarbonylphenyl)-2-methyl-1,2,3,4,4a,10b-hexahydrobenzo[c][1,6]naphthyridine;
- cis-8,9-Diethoxy-6-(4-dibutylaminocarbonylphenyl)-2-methyl-1,2,3,4,4a,10b-hexahydrobenzo[c][-1,6]naphthyridine;
- cis-8,9-Diethoxy-6-[4-(hexahydroazepin-1 -ylcarbonyl)phenyl]-2-methyl-1,2,3,4,4a,10b-hexahydrobenzo[c][1,6]naphthyridine;
- cis-8,9-Diethoxy-6-[4-(piperidin-1 -ylcarbonyl)phenyl]-2-methyl-1,2,3,4,4a,10b-hexahydrobenzo[c][1,6]-naphthyridine;
- cis-9-Ethoxy-8-methoxy-6-(4-diisopropylaminocarbonylphenyl)-2-methyl-1,2,3,4,4a,10b-hexahydrobenzo[c][1,6]naphthyridine;
- cis-9-Ethoxy-8-methoxy-6-(4-dibutylaminocarbonylphenyl)-2-methyl-1,2,3,4,4a,10b-hexahydrobenzo[c][1,6]naphthyridine:
- cis-9-Ethoxy-8-methoxy-6-[4-(hexahydroazepin-1-yl-carbonyl)phenyl]-2-methyl-1,2,3,4,4a,10b-hexahydrobenzo[c][1,6]naphthyridine;
- cis-9-Ethoxy-8-methoxy-6-[4-(piperidin-1 -ylcarbonyl)phenyl]-2-methyl-1,2,3,4,4a,10b-hexahydrobenzo[c][1,6]naphthyridine
- and a salt thereof.
- 9. A medicament composition comprising a customary pharmaceutical auxiliary and/or excipient and an effective amount of a compound of formula I according to claim 1 or a pharmaceutically acceptable salt thereof.
- 10. In a method of producing a medicament composition comprising a customary pharmaceutical auxiliary or excipient and an effective amount of active ingredient for treating an airway disorder or an amenable dermatosis, the improvement wherein the active ingredient is a compound of formula I according to claim 1 or a pharmaceutically acceptable salt thereof.
- 11. In a method for treating an airway disorder or an amenable dermatosis which comprises administering an effective amount of active ingredient to a subject in need of such treatment, the improvement wherein the active ingredient is a compound of formula I according to claim 1 or a pharmaceutically acceptable salt thereof.
- 12. A compound of formula I according to claim 5, in which
- R1 is methyl,
- R2 is ethoxy,
- R3 is methoxy,
- R4 is a phenyl radical which is substituted by R5 and R6, where
- R5 is hydrogen,
- R6 is CO--R8, where
- R8 is N(R81)R82 and
- R81 and R82 are isopropyl, or a salt thereof.
- 13. The compound according to claim 7, which is (-)-cis-9-ethoxy-8-methoxy-6-(4-diisopropylaminocarbonylphenyl)-2-methyl-1,2,3,4,4a,10b-hexahydrobenzo[c][1,6]naphthyridine hydrochloride.
Priority Claims (3)
Number |
Date |
Country |
Kind |
196 46 298 |
Nov 1996 |
DEX |
|
961 18 188 |
Nov 1996 |
DEX |
|
197 39 056 |
Sep 1997 |
DEX |
|
Parent Case Info
This application is the national phase of PCT/EP97/06096, filed Nov. 5, 1997, published as WO 98/21208 on May 22, 1998.
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
102e Date |
371c Date |
PCT/EP97/06096 |
11/5/1997 |
|
|
4/16/1999 |
4/16/1999 |
Publishing Document |
Publishing Date |
Country |
Kind |
WO98/21208 |
|
|
|
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
3899494 |
Ott |
Aug 1975 |
|
Foreign Referenced Citations (2)
Number |
Date |
Country |
247971 |
Dec 1981 |
EPX |
9117991 |
May 1991 |
WOX |