1,3,4-trisubstituted piperidine derivatives, the preparation and use thereof
AssigneeBASF SE
InventorsGerd Steiner, Liliane Unger, Hans P. Hofmann, Hans-Juergen Teschendorf, Berthold Behl, Rudolf Binder
Life of this patent
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Abstract
Compounds of the formula ##STR1## where A-B-D, R.sup.1, R.sup.2 and R.sup.3 have the meanings stated in the description, and their preparation are described. The compounds are suitable for controlling diseases.
Claims9
A 1,3,4-trisubstituted piperidine compound selected from formula I ##STR7## where R.sup.1 is hydrogen, fluorine or chlorine,
- R.sup.2 is hydroxyl or p-fluorophenyl,
- R.sup.3 is hydrogen, or
- R.sup.2 and R.sup.3 together are oxygen,
- n is 1, 2 or 3, and
- A-B-D is ##STR8## where R.sup.4 is methyl, ethyl, phenyl, p-fluorophenyl or 2-thienyl,
- R.sup.5 is hydrogen or hydroxyl,
- R.sup.6 is hydrogen,
- R.sup.7 is hydroxyl, or
- R.sup.6 and R.sup.7 together are oxygen with the proviso that when A-B-D is ##STR9## R.sup.4 is methyl ethyl or 2-thienyl, and its salt with physiologically tolerated acid.
A 1,3,4-trisubstituted piperidine compound selected from formula I ##STR10## where R.sup.1 is hydrogen or chlorine,
- R.sup.2 is hydroxyl or p-fluorophenyl,
- R.sup.3 is hydrogen, or
- R.sup.2 and R.sup.3 together are oxygen,
- n is 1, 2 or 3, and
- A-B-D is ##STR11## where R.sup.4 is methyl, phenyl or p-fluorophenyl,
- R.sup.5 is hydrogen or hydroxyl,
- R.sup.6 is hydrogen,
- R.sup.7 is hydroxyl, or
- R.sup.6 and R.sup.7 together are oxygen with the proviso that when A-B-D is, ##STR12## R.sup.4 is methyl, ethyl or 2-thienyl and its salt with physiologically tolerated acid.
A compound selected from the group consisting of
- 1-(4-Fluorophenyl)-4- 4-hydroxy-trans-3-phenyl(hydroxy)methyl-4-phenyl-1-pi peridinyl!-1-butanone, 1-(4-fluorophenyl)-4- trans-(3-phenyl-hydroxymethyl-4-phenyl)-4-hydroxy-pi peridin-1-yl!-butan-1-ol, 1-phenyl-3- trans-(3-phenyl-hydroxymethyl-4-phenyl)-4-hydroxy-piperidin-1- yl!-propan-1-one, 1-(4-fluorophenyl)-4-(3-benzoyl-4-phenyl-.DELTA..sup.4 -dehydro-piperidin-1-yl)-butan-1-one, 1-(4-fluorophenyl)-4-(3-benzoyl-4-phenyl-.DELTA..sup.3 -dehydro-piperidin-1-yl)-butan-1-one, 1-(bis-4-fluorophenyl)-4- trans-(3-phenyl-hydroxymethyl-4-phenyl)-4-hydrox y-piperidin-1-yl!butane, 1-(4-fluorophenyl)-4- trans-(3-p-fluorophenyl-hydroxymethyl-4-p-fluorophen yl-4-hydroxypiperidin-1-yl!butan-1-one, 1-(4-fluorophenyl)-4- trans-(3-p-fluorophenyl-hydroxymethyl-4-p-fluorophen yl-4-hydroxypiperidin-1-yl!-butan-1-ol, 1-(4-fluorophenyl)-4- trans-(3-acetyl-4-methyl)-4-hydroxy-piperidin-1-yl!- butan-1-one, 1-(4-fluorophenyl)-4- trans-(3-acetyl-4-methyl)-4-hydroxypiperidin-1-yl!-b utan-1-ol, 1-(4-fluorophenyl)-4-(3-acetyl-4-methyl-.DELTA..sup.3 -dehydropiperidin-1-yl)-butan-1-one, 1-(4-fluorophenyl)-4-(3-acetyl-4-methyl-.DELTA..sup.3 -dehydropiperidin-1-yl)-butan-1-ol, 1-(bis-4-fluorophenyl)-4-(3-acetyl-4-methyl-.DELTA..sup.3 -dehydro-piperidin-1-yl)-butane.
A method for the treatment of strokes which comprises administering to a host in need thereof an effective amount of a 1,3,4-trisubstituted piperidine compound selected from formula I ##STR13## where R.sup.1 is hydrogen, fluorine, chlorine or bromine,
- R.sup.2 is hydrogen, hydroxyl, or phenyl which is unsubstituted or substituted by fluorine, chlorine or bromine,
- R.sup.3 is hydrogen, or
- R.sup.2 and R.sup.3 together are oxygen,
- n is 1, 2 or 3, and
- A-B-D is ##STR14## where R.sup.4 is C.sub.1-3 -alkyl or is phenyl or thienyl which can be substituted by fluorine or chlorine,
- R.sup.5 is hydrogen or hydroxyl,
- R.sup.6 is hydrogen,
- R.sup.7 is hydroxyl, or
- R.sup.6 and R.sup.7 together are oxygen, and
- n is 1, 2 or 3, and its salt with physiologically tolerated acid.
A method for the treatment of anxiety states which comprises administering to a host in need thereof an effective amount of a 1,3,4-trisubstituted piperidine compound selected from formula I ##STR15## where R.sup.1 is hydrogen, fluorine, chlorine or bromine,
- R.sup.2 is hydrogen, hydroxyl, or phenyl which is unsubstituted or substituted by fluorine, chlorine or bromine,
- R.sup.3 is hydrogen, or
- R.sup.2 and R.sup.3 together are oxygen,
- n is 1, 2 or 3, and
- A-B-D is ##STR16## where R.sup.4 is C.sub.1-3 -alkyl or is phenyl or thienyl which can be substituted by fluorine or chlorine,
- R.sup.5 is hydrogen or hydroxyl,
- R.sup.6 is hydrogen,
- R.sup.7 is hydroxyl, or
- R.sup.6 and R.sup.7 together are oxygen, and
- n is 1, 2 or 3, and its salt with physiologically tolerated acid.
A method for the treatment of sleep disturbances which comprises administering to a host in need thereof an effective amount of a 1,3,4-trisubstituted piperidine compound selected from formula I ##STR17## where R.sup.1 is hydrogen, fluorine, chlorine or bromine,
- R.sup.2 is hydrogen, hydroxyl, or phenyl which is unsubstituted or substituted by fluorine, chlorine or bromine,
- R.sup.3 is hydrogen, or
- R.sup.2 and R.sup.3 together are oxygen,
- n is 1, 2 or 3, and
- A-B-D is ##STR18## where R.sup.4 is C.sub.1-3 -alkyl or is phenyl or thienyl which can be substituted by fluorine or chlorine,
- R.sup.5 is hydrogen or hydroxyl,
- R.sup.6 is hydrogen,
- R.sup.7 is hydroxyl, or
- R.sup.6 and R.sup.7 together are oxygen, and
- n is 1, 2 or 3, and its salt with physiologically tolerated acid.
Dependencies are inferred from the claim text.