Patent MY-110517-A (MY)
Title: Indoline derivatives carrying an amide functional group their preparation and the pharmaceutical compositions in which they are present.
Inventor: DINO NISATO
IPC: A61K31/495
Filed: 1992-07-31
Abstract: THE INVENTION RELATES TO COMPOUNDS OF FORMULA(FORMULA I)IN WHICH -R1 IS A HALOGEN ATOM, A C1-C4 ALKYL, A HYDROXYL, A C1-C4 ALKOXY, A BENZYLOXY GROUP, A CYANO GROUP, A TRIFLUOROMETHYL GROUP, NITRO GROUP OR AN AMINO GROUP; -R2 IS A C1-C6 ALKYL, A C3-C7 CYCLOALKYL, A C5-C7 CYCLOALKENE OR A PHENYL WHICH IS UNSUBSTITUTED OR MONOSUBSTITUTED OR POLYSUBSTITUTED BY A C1-C4 ALKYL, A C1-C4 ALKOXY, A HALOGEN, A TRIFLUOROMETHYL GROUP OR AN AMINO GROUP, OR R2 IS NITROPHENYL WHICH IS UNSUBSTITUTED OR MONOSUBSTITUTED BY A TRIFLUOROMETHYL GROUP OR MONOSUBSTITUTED OR POLYSUBSTITUTED BY A C1-C4 ALKYL OR A HALOGEN; -R3 IS A HYDROGEN ATOM; -R4 IS A CARBAMOYL GROUP OF FORMULA CONR6R7; -R5 IS A C1-C4 ALKYL; A 1-NAPTHTYL; A 2-NAPTHYL; A 5-DIMETHYLAMINO-1-NAPHTHYL; A PHENYL WHICH IS UNSUBSTITUTED OR SUBSTITUTED BY ONE OR MORE SUBSTITUENTS SELECTED FROM A HALOGEN ATOM, A C1-C4 ALKYL, A TRIFLUOROMETHYL GROUP, AN AMINO GROUP WHICH IS FREE OR SUBSTITUTED BY ONE OR 2 C1-C4 ALKYLS, A HYDROXYL, A C1-C4 ALKOXY, A C2-C4 ALKENOXY, A C1-C4 ALKYLTHIO, A TRIFLUOROMETHOXY GROUP, A BENZYLOXY GROUP, A CYANO GROUP, A CARBOXYL GROUP, A C1-C4 ALKOXYCARBONYL GROUP, A CARBAMOYL GROUP WHICH IS FREE OR SUBSTITUTED BYONE OR TWO C1-C4 ALKYLS OR A C1-C4 ALKYLAMIDO GROUP, OR R5 IS A NITROPHENYL WHICH IS UNSUBSTITUTED OR MONOSUBSTITUTED BY A TRIFLUOROMETHYL GROUP OR A C2-C4 ALKENOXY OR MONO- OR POLY-SUBSTITUTED BY AHALOGEN, A C1-C4 ALKYL, A C1-C4 ALKOXY, A C1-C4 ALKYLTHIO, A TRIFLUOROMETHOXY GROUP OR A BENZYLOXY GROUP; -R6 IS A C1-C6 ALKYL OR R6 IS SIMILAR TO R7; -R7 IS A 4-PIPERIDYL GROUP OR A 3-AZETIDINYL GROUP, THE SAID GROUPS BEING SUBSTITUTED OR UNSUBSTITUTED ON THE NITROGEN BY A C1-C4 ALKYL, BY A BENZYLOXYCARBONYL OR BY A C1-C4 ALKOXYCARBONYL; A GROUP (CH2)R WHICH IS ITSELF SUBSTITUTED BY A 2-, 3- OR 4- PYRIDYL GROUP, BY A HYDROXYL GROUP OR BY AN AMINO GROUP WHICH IS FREE OR SUBSTITUTED BY ONE OR TWO C1-C4 ALKYLS, A CARBOXYL GROUP, A C1-C4 ALKOXYCARBONYL GROUP, A BENZYLOXYCARBONYL GROUP OR A CA RBAMOYL GROUP WHICH IS FREE OR SUBSTITUTED BY ONE OR 2 C1-C4 ALKYLS; OR R6 AND R7 TOGETHER, WITH THE NITROGEN ATOM TO WHICH THEY ARE CONNECTED, FORM A HETEROCYCLE SLECTED FROM: . MORPHOLINE, . THIOMORPHOLINE, . THIAZOLIDINE OR 2, 2-DIMETHYLTHIAZOLIDINE, UNSUBSTITUTED OR SUBSTITUTED BY R8 . PIPERAZINE, UNSUBSTITUTED OR SUBSTITUTED AT THE 4-POSITION BY A GROUP R''''8, . AN UNSATURATED, 5-MEMBERED RING CONTAINING A SINGLE NITROGEN ATOM AND SUBSTITUTED BY R8 OR A SATURATED, 3-, 4-, 6- OR 7-MEMBERED RING CONTAINING A SINGLE NITROGEN ATOM AND SUBSTITUTED BY R8 AND R9; -R8 IS R''8 OR A GROUP (CH2)R WHICH ITSELF SUBSTITUTED BY A HYDROXYL OR BY AN AMINO WHICH IS FREE OR SUBSTITUTED BY ONE OR 2 C1-C4 ALKYLS; -R''8 IS A GROUP (CH2)Q WHICH IS ITSELF SUBSTITUTED BY A CARBOXYL GROUP, A C1-C4 ALKOXYCARBONYL GROUP, A BENZYLOXYCARBONYL GROUP, A CARBAMOYL GROUP WHICH IS FREE OR SUBSTITUTED BY A HYDROXYL OR BY ONE OR 2 C1-C4 ALKYLS OR AN AMINOCARBOTHIOYL GROUP WHICH IS FREE OR SUBSTITUTED BY ONE OR 2 C1-C4 ALKYLS; -R''''8 IS R''8 OR A GROUP (CH2)2NH2 WHICH IS FREE OR SUBSTITUTED BY ONE OR TWO C1-C4 ALKYLS; -R9 IS HYDROGEN, A HALOGEN, A GROUP (CH2)ROR10, A GROUP (CH2)RNR11R12, A GROUP (CH2)SCONR11R''11 OR AN AZIDO GROUP; -R10 IS HYDROGEN , A C1-C4 ALKYL, A MESYL OR A TOSYL; -R11, R''11 AND R12 ARE EACH HYDROGEN OR A C1-C4 ALKYL OR R11 IS HYDROGEN AND R12 IS A BENZYLOXYCARBONYL OR A C1-C4 ALKOXYCARBONYL; -N IS O, 1, 2 OR 3; -M IS 0, 1 OR 2; -Q IS 0,1,2 OR 3; -R IS O,1,2 OR 3, WITH THE LIMITATION THAT R IS NOT ZERO WHEN R8 OR R9 IS AT THE ALPHA-POSITION OF THE INTRACYCLIC AMIDE NITROGEN; -S ISO OR 1; AS WELL AS ITS POSSIBLE SALTS. THESE COMPOUNS ARE USEFUL IN THE TREATMENT OF COMPLAINTS OF THE CENTRAL NERVOUS SYSTEM AND THE GASTRIC SPHERE IN HUMANS AND ANIMALS.