CH619935A5 - - Google Patents
Download PDFInfo
- Publication number
- CH619935A5 CH619935A5 CH172277A CH172277A CH619935A5 CH 619935 A5 CH619935 A5 CH 619935A5 CH 172277 A CH172277 A CH 172277A CH 172277 A CH172277 A CH 172277A CH 619935 A5 CH619935 A5 CH 619935A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- product
- derivative
- radical
- addition salts
- Prior art date
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 32
- -1 alkyl radical Chemical class 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 14
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 239000011707 mineral Substances 0.000 claims description 13
- 150000007522 mineralic acids Chemical class 0.000 claims description 13
- 150000007524 organic acids Chemical class 0.000 claims description 13
- 235000005985 organic acids Nutrition 0.000 claims description 12
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 239000011777 magnesium Substances 0.000 claims description 9
- 229910052749 magnesium Inorganic materials 0.000 claims description 9
- ZZFGPEUHZFDVLP-UHFFFAOYSA-N 1-phenyl-3-(trifluoromethyl)piperidine Chemical class C1C(C(F)(F)F)CCCN1C1=CC=CC=C1 ZZFGPEUHZFDVLP-UHFFFAOYSA-N 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- MLEGMEBCXGDFQT-UHFFFAOYSA-N 1-benzylpiperidin-2-one Chemical compound O=C1CCCCN1CC1=CC=CC=C1 MLEGMEBCXGDFQT-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 150000004768 bromobenzenes Chemical class 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- 150000002680 magnesium Chemical class 0.000 claims description 5
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
- 150000008065 acid anhydrides Chemical class 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- KRTGJZMJJVEKRX-UHFFFAOYSA-N 2-phenylethan-1-yl Chemical compound [CH2]CC1=CC=CC=C1 KRTGJZMJJVEKRX-UHFFFAOYSA-N 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- HDRXZJPWHTXQRI-BHDTVMLSSA-N diltiazem hydrochloride Chemical compound [Cl-].C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CC[NH+](C)C)C2=CC=CC=C2S1 HDRXZJPWHTXQRI-BHDTVMLSSA-N 0.000 claims description 3
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 3
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical group O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 239000012024 dehydrating agents Substances 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 claims 2
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical group C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- 239000000047 product Substances 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 11
- NAAXALWMZKHEHY-UHFFFAOYSA-N 3-[3-(trifluoromethyl)phenyl]piperidine Chemical compound FC(F)(F)C1=CC=CC(C2CNCCC2)=C1 NAAXALWMZKHEHY-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 6
- RUABMLQEAISSGG-UHFFFAOYSA-N 3-[3-(trifluoromethyl)phenyl]piperidine;hydrochloride Chemical compound Cl.FC(F)(F)C1=CC=CC(C2CNCCC2)=C1 RUABMLQEAISSGG-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- SIYWTPMDRMFZJQ-UHFFFAOYSA-N 1-methyl-3-[3-(trifluoromethyl)phenyl]piperidine Chemical compound C1N(C)CCCC1C1=CC=CC(C(F)(F)F)=C1 SIYWTPMDRMFZJQ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
- 229940086542 triethylamine Drugs 0.000 description 4
- NPNJUOWWNAUFTK-UHFFFAOYSA-N 1-benzyl-3-[3-(trifluoromethyl)phenyl]piperidin-3-ol Chemical compound C1C(O)(C=2C=C(C=CC=2)C(F)(F)F)CCCN1CC1=CC=CC=C1 NPNJUOWWNAUFTK-UHFFFAOYSA-N 0.000 description 3
- JCWIIBHQRXFNGB-UHFFFAOYSA-N 1-benzyl-3-[3-(trifluoromethyl)phenyl]piperidine Chemical compound FC(F)(F)C1=CC=CC(C2CN(CC=3C=CC=CC=3)CCC2)=C1 JCWIIBHQRXFNGB-UHFFFAOYSA-N 0.000 description 3
- UKJIJMWSRNPIGU-UHFFFAOYSA-N 1-benzyl-5-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CN(CC=3C=CC=CC=3)CCC=2)=C1 UKJIJMWSRNPIGU-UHFFFAOYSA-N 0.000 description 3
- GXWQJOUHTZUDAZ-UHFFFAOYSA-N 1-propan-2-yl-3-[3-(trifluoromethyl)phenyl]piperidine Chemical compound C1N(C(C)C)CCCC1C1=CC=CC(C(F)(F)F)=C1 GXWQJOUHTZUDAZ-UHFFFAOYSA-N 0.000 description 3
- AIRXYJJAHZIPHG-UHFFFAOYSA-N 3-[3-(trifluoromethyl)phenyl]piperidine-1-carbaldehyde Chemical compound FC(F)(F)C1=CC=CC(C2CN(CCC2)C=O)=C1 AIRXYJJAHZIPHG-UHFFFAOYSA-N 0.000 description 3
- 208000020401 Depressive disease Diseases 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229910001923 silver oxide Inorganic materials 0.000 description 3
- NNMBNYHMJRJUBC-UHFFFAOYSA-N 1-bromo-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(Br)=C1 NNMBNYHMJRJUBC-UHFFFAOYSA-N 0.000 description 2
- OLAXMKMQCSWQTF-UHFFFAOYSA-N 1-methyl-3-[3-(trifluoromethyl)phenyl]piperidine;hydrochloride Chemical compound Cl.C1N(C)CCCC1C1=CC=CC(C(F)(F)F)=C1 OLAXMKMQCSWQTF-UHFFFAOYSA-N 0.000 description 2
- GBOLYPGBMMGDGB-UHFFFAOYSA-N 1-propyl-3-[3-(trifluoromethyl)phenyl]piperidine Chemical compound C1N(CCC)CCCC1C1=CC=CC(C(F)(F)F)=C1 GBOLYPGBMMGDGB-UHFFFAOYSA-N 0.000 description 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical group [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 2
- NZYBILDYPCVNMU-UHFFFAOYSA-N 3-phenylpiperidine Chemical class C1CCNCC1C1=CC=CC=C1 NZYBILDYPCVNMU-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 241001342522 Vampyrum spectrum Species 0.000 description 2
- LTUIADKAANGOEG-UHFFFAOYSA-N [1-benzyl-3-[3-(trifluoromethyl)phenyl]piperidin-3-yl] acetate Chemical compound C1C(OC(=O)C)(C=2C=C(C=CC=2)C(F)(F)F)CCCN1CC1=CC=CC=C1 LTUIADKAANGOEG-UHFFFAOYSA-N 0.000 description 2
- SXDSISDTCUMJAQ-UHFFFAOYSA-N [1-benzyl-3-[3-(trifluoromethyl)phenyl]piperidin-3-yl] acetate;hydrochloride Chemical compound Cl.C1C(OC(=O)C)(C=2C=C(C=CC=2)C(F)(F)F)CCCN1CC1=CC=CC=C1 SXDSISDTCUMJAQ-UHFFFAOYSA-N 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- BIDDYVAFUFGUDW-UHFFFAOYSA-N oxalic acid;1-propyl-3-[3-(trifluoromethyl)phenyl]piperidine Chemical compound OC(=O)C(O)=O.C1N(CCC)CCCC1C1=CC=CC(C(F)(F)F)=C1 BIDDYVAFUFGUDW-UHFFFAOYSA-N 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- UXTFKIJKRJJXNV-UHFFFAOYSA-N 1-$l^{1}-oxidanylethanone Chemical compound CC([O])=O UXTFKIJKRJJXNV-UHFFFAOYSA-N 0.000 description 1
- AQZIMFXVNAIZRY-UHFFFAOYSA-N 1-benzyl-3-[3-(trifluoromethyl)phenyl]piperidine;hydrochloride Chemical compound Cl.FC(F)(F)C1=CC=CC(C2CN(CC=3C=CC=CC=3)CCC2)=C1 AQZIMFXVNAIZRY-UHFFFAOYSA-N 0.000 description 1
- BBQQULRBTOMLTC-UHFFFAOYSA-N 1-benzylpiperidin-3-one Chemical compound C1C(=O)CCCN1CC1=CC=CC=C1 BBQQULRBTOMLTC-UHFFFAOYSA-N 0.000 description 1
- SRLGWTWTXWKNFL-UHFFFAOYSA-N 1-propan-2-yl-3-[3-(trifluoromethyl)phenyl]piperidine;hydrochloride Chemical compound Cl.C1N(C(C)C)CCCC1C1=CC=CC(C(F)(F)F)=C1 SRLGWTWTXWKNFL-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- IXVJKFCFNGQJTG-UHFFFAOYSA-N 3-oxopropanoyl 3-oxopropanoate Chemical compound O=CCC(=O)OC(=O)CC=O IXVJKFCFNGQJTG-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 208000020925 Bipolar disease Diseases 0.000 description 1
- 241001331845 Equus asinus x caballus Species 0.000 description 1
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 description 1
- 229930184093 Furanether Natural products 0.000 description 1
- ILACEZQKVDMRMW-UHFFFAOYSA-N Furanether A Natural products C1C2=COC=C2C2C3CC(C)(C)CC3C1(C)O2 ILACEZQKVDMRMW-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 1
- 230000001539 anorectic effect Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000000648 anti-parkinson Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000000939 antiparkinson agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 229940007550 benzyl acetate Drugs 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 208000028683 bipolar I disease Diseases 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical class C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- HZHMMLIMOUNKCK-UHFFFAOYSA-N dipropyl oxalate Chemical compound CCCOC(=O)C(=O)OCCC HZHMMLIMOUNKCK-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 208000016253 exhaustion Diseases 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- BIWOSRSKDCZIFM-UHFFFAOYSA-N piperidin-3-ol Chemical compound OC1CCCNC1 BIWOSRSKDCZIFM-UHFFFAOYSA-N 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- DITHIFQMPPCBCU-UHFFFAOYSA-N propa-1,2-diene Chemical compound [CH]=C=C DITHIFQMPPCBCU-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/42—Oxygen atoms attached in position 3 or 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/02—Magnesium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7603933A FR2340734A1 (fr) | 1976-02-13 | 1976-02-13 | Nouveaux derives de la m-trifluoromethylphenyl piperidine et leurs sels, procede de preparation et application a titre de medicaments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH619935A5 true CH619935A5 (fi) | 1980-10-31 |
Family
ID=9169059
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH172277A CH619935A5 (fi) | 1976-02-13 | 1977-02-11 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4259337A (fi) |
| JP (1) | JPS52116476A (fi) |
| AT (1) | AT358036B (fi) |
| BE (1) | BE851350A (fi) |
| CA (1) | CA1087192A (fi) |
| CH (1) | CH619935A5 (fi) |
| DE (1) | DE2705416A1 (fi) |
| DK (1) | DK58677A (fi) |
| FR (1) | FR2340734A1 (fi) |
| GB (1) | GB1530061A (fi) |
| IE (1) | IE44627B1 (fi) |
| LU (1) | LU76753A1 (fi) |
| NL (1) | NL7701507A (fi) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4352432A (en) * | 1977-06-13 | 1982-10-05 | Smith Terrance R | Bicycle storage rack |
| US4387229A (en) | 1977-09-13 | 1983-06-07 | Pfizer Inc. | 3-[2-Hydroxy-4-(substituted)phenyl]azacycloalkanols and derivatives thereof |
| FI792076A (fi) * | 1978-07-05 | 1980-01-06 | Ciba Geigy Ag | Foerfarande foer framstaellning av nya fenylpiperidinderivat |
| FR2440353A1 (fr) * | 1978-11-03 | 1980-05-30 | Science Union & Cie | Nouveaux arylethanols, leurs procedes d'obtention et leur emploi comme medicament |
| EP0030526B1 (en) * | 1979-12-05 | 1985-02-27 | Astra Läkemedel Aktiebolag | New phenyl-azacycloalkanes, processes for preparation and pharmaceutical preparations for such compounds |
| FR2501506A1 (fr) * | 1981-03-11 | 1982-09-17 | Sanofi Sa | Compositions pharmaceutiques a action anorexigene contenant des derives de la tetrahydropyridine |
| US4626593A (en) * | 1983-11-18 | 1986-12-02 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Vinyl stilbazoles |
| GB8929331D0 (en) * | 1989-12-29 | 1990-02-28 | Shell Int Research | Piperidine derivatives |
| CA2105666C (en) * | 1991-04-17 | 2006-02-14 | Kjell Anders Ivan Svensson | New centrally acting substituted phenylazacycloalkanes |
| BRPI0511481A (pt) * | 2004-05-25 | 2007-12-26 | Pfizer Prod Inc | uso |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2891066A (en) * | 1957-08-14 | 1959-06-16 | Parke Davis & Co | 4,o-substituted phenyl 1 alkanol piperidines and esters thereof |
-
1976
- 1976-02-13 FR FR7603933A patent/FR2340734A1/fr active Granted
-
1977
- 1977-02-09 DE DE19772705416 patent/DE2705416A1/de not_active Withdrawn
- 1977-02-10 JP JP1314077A patent/JPS52116476A/ja active Pending
- 1977-02-11 CA CA271,549A patent/CA1087192A/fr not_active Expired
- 1977-02-11 CH CH172277A patent/CH619935A5/fr not_active IP Right Cessation
- 1977-02-11 BE BE174874A patent/BE851350A/xx not_active IP Right Cessation
- 1977-02-11 DK DK58677A patent/DK58677A/da unknown
- 1977-02-11 LU LU76753A patent/LU76753A1/xx unknown
- 1977-02-11 NL NL7701507A patent/NL7701507A/xx not_active Application Discontinuation
- 1977-02-11 IE IE307/77A patent/IE44627B1/en unknown
- 1977-02-11 GB GB5736/77A patent/GB1530061A/en not_active Expired
- 1977-02-14 AT AT97277A patent/AT358036B/de not_active IP Right Cessation
- 1977-05-12 US US05/796,317 patent/US4259337A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| IE44627B1 (en) | 1982-02-10 |
| AT358036B (de) | 1980-08-11 |
| GB1530061A (en) | 1978-10-25 |
| ATA97277A (de) | 1980-01-15 |
| CA1087192A (fr) | 1980-10-07 |
| NL7701507A (nl) | 1977-08-16 |
| US4259337A (en) | 1981-03-31 |
| JPS52116476A (en) | 1977-09-29 |
| DK58677A (da) | 1977-08-14 |
| DE2705416A1 (de) | 1977-08-18 |
| LU76753A1 (fi) | 1977-08-19 |
| FR2340734B1 (fi) | 1978-11-10 |
| BE851350A (fr) | 1977-08-11 |
| FR2340734A1 (fr) | 1977-09-09 |
| IE44627L (en) | 1977-08-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1115277A (fr) | Procede de preparation de nouveaux derives du tetrahydro pyridinyl-indole et de leurs sels | |
| CA1103676A (fr) | Procede de preparation de nouveaux derives du piperidyl-indole et leurs sels | |
| FR2534257A1 (fr) | Nouveaux derives de la 6-amino 7-hydroxy 4,5,6,7-tetrahydro-imidazo/4,5,1-j-k/ /1/ benzazepin-2(1h)-one, leurs sels, application a titre de medicaments, compositions les renfermant et un intermediaire | |
| CH617923A5 (fi) | ||
| CH641438A5 (fr) | Derives du 3-(aminoethyl)phenol et leurs sels, leur procede de preparation et medicaments les renfermant. | |
| CH619935A5 (fi) | ||
| EP0004494B1 (fr) | Nouveaux dérivés de 1,3-dihydro 3-(1-(2-(2,3-dihydro 1,4-benzo-dioxin-2-yl)2-hydroxy éthyl)pipéridin-4-yl)2H-indol 2-one, leur procédé de préparation, leur application comme médicaments et les compositions pharmaceutiques les renfermant | |
| CA1088070A (fr) | Procede de preparation de nouveaux derives de l'aminobenzocycloheptene | |
| EP0022705B1 (fr) | Nouveaux dérivés du tétrahydropyridinyl-indole et leurs sels, leur préparation, leur application comme médicaments et les compositions les renfermant | |
| BE1008622A3 (fr) | Derives de l'epi-epibatidine. | |
| EP0021924A2 (fr) | Dérivés de l'indole, procédé pour leur préparation, leur application comme médicaments et compositions pharmaceutiques les contenant | |
| FR2625502A1 (fr) | Nouveaux derives du 3-piperidine carbaldehyde oxime, leur procede de preparation et leur application comme medicaments | |
| EP0176444B1 (fr) | Nouveau procédé de préparation de dérivés du 4 H-1,2-4-triazole, nouveaux triazoles ainsi obtenus, leur applicication comme médicaments et les compositions pharmaceutiques les renfermant | |
| EP0230179B1 (fr) | Nouveaux dérivés du 4-morpholinyl 1H-indole, leurs sels, procédé et intermédiaires de préparation, application à titre de médicaments, compositions les renfermant | |
| EP0105776B1 (fr) | Nouveaux dérivés de la C-homo 9-oxaergoline, leurs sels, procédé de préparation et intermédiaires de préparation, application à titre de médicaments et compositions les renfermant | |
| CA1060020A (fr) | Procede de preparation de nouveaux derives de la dibenzo/b,c/ thiepine et leurs sels | |
| CA1076117A (fr) | Procede d'obtention de nouveaux ethers aryliques et les produits en resultant | |
| CH622771A5 (fi) | ||
| EP0034989B1 (fr) | Nouveaux dérivés du cycloheptindolol et leurs sels avec les acides, leur préparation, leur application comme médicaments et les compositions les renfermant | |
| FR2526797A1 (fr) | Nouveaux derives de l'acide 9-oxalysergique, leurs sels, procede de preparation, application a titre de medicaments et compositions les renfermant | |
| CH617661A5 (fi) | ||
| FR2476649A1 (fr) | Nouveaux derives du cycloheptindole, leurs sels, procede de preparation, application a titre de medicaments et compositions les renfermant | |
| EP0157762B1 (fr) | Nouvelles piperidinoguanidines substituees, leur procede de preparation et les compositions pharmaceutiques en renfermant | |
| BE874322R (fr) | Nouveaux composes heterocycliques, leur preparation et leur application comme medicaments | |
| FR2458550A1 (fr) | Nouveaux derives du tetrahydropyridinyl-indole, leurs sels, procede de preparation, application a titre de medicaments et compositions les renfermant |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |