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US 6,476,035 B1Granted
Indole and 2,3-dihydroindole derivatives, their preparation and use
OwnerEjner Knud Moltzen, Jens Kristian Perregaard +2inventors
InventorsEjner Knud Moltzen, Jens Kristian Perregaard, Ivan Mikkelsen, Garrick Paul Smith
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Abstract
The present invention relates to indole and 2,3-dihydroindole derivatives having formula (I) or any of its any of its enantiometers or any mixture thereof, or an acid addition salt thereof, wherein A, R1, R2, R3, W, X, Y and Z are as described in the description. The compounds are potent serotonin reuptake inhibitors and have 5-HT1A receptor antagonistic activity.
Claims16
An indole or 2,3-dihydro-indole derivative having the formula:
- any of its enantiomers or any mixture thereof, or an acid addition salt thereof, wherein
- X is —O— or —S—;
- and
- Y is —CR6R7—, —CR6R7—CR8R9—, or —CR6═CR7—;
- or
- Z is —O— or —S—;
- W is N;
- A is selected from a group of formula (II), (III) and (IV)
- wherein the dotted lines mean an optional bond in formulas (II), (III) and (IV) and are absent in formula (I);
- R1, R2, R3, R12, R13, R14, R15, R16 and R17 are each independently selected from hydrogen halogen, trifluoromethyl, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, hydroxy, formyl, acyl, amino, alkylamino, dialkylamino, acylamino, alkoxycarbonylamino, aminocarbonylamino, alkylaminocarbonylamino, dialkylaminocarbonylamino, nitro and cyano;
- R6, R7, R8 and R9 are each independently selected from hydrogen and alkyl;
- and
- R11 is selected from hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, naphthyl, phenylalkyl, acyl and formyl.
10 more elements
An indole or 2,3-dihydro-indole derivative having the formula:
- any of its enantiomers or any mixture thereof, or an acid addition salt thereof, wherein
- X is —O—, —S—, or —CR4R5—;
- and
- Y is —CR6R7—CR8R9—, or —CR6═CR7—;
- or
- X and Y together form a group —CR4═CR5—, or CR4═CR5—CR6R7—;
- Z is —O—, or —S—;
- W is N and the dotted line is absent;
- A is
- wherein the dotted line in (II) means an optional bond;
- R1, R2, R3, R12, R13, R14, R15, R16 and R17 are each independently selected from hydrogen halogen, trifluoromethyl, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, hydroxy, formyl, acyl, amino, alkylamino, dialkylamino, acylamino, alkoxycarbonylamino, aminocarbonylamino, alkylaminocarbonylamino, dialkylaminocarbonylamino, nitro and cyano;
- R4, R5, R6, R7, R8 and R9 are each independently selected from hydrogen and alkyl;
- and
- R11 is selected from hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, naphthyl, phenylalkyl and formyl.
11 more elements
Dependencies are inferred from the claim text.