CS228110B2 - Způsob výroby nových derivátů 3-(4-fenoxymethylpiperidino)propanolu - Google Patents

Způsob výroby nových derivátů 3-(4-fenoxymethylpiperidino)propanolu Download PDF

Info

Publication number: CS228110B2
Authority: CS; Czechoslovakia
Prior art keywords: propoxy; hydroxy; group; hydrogen; phenoxymethylpiperidino
Prior art date: 1976-11-12

Application number

CS785461A

Other languages

Czech (cs)

English (en)

Inventor

Wolfgang Dr Kampe

Walter Gunar Dr Friebe

Fritz Dr Wiedemann

Gisbert Dr Sponer

Wolfgang Dr Bartsch

Karel Dietmann

Original Assignee

Boehringer Mannheim Gmbh

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1976-11-12

Filing date

1978-08-21

Publication date

1984-05-14

1976-11-12 Priority claimed from DE19762651574 external-priority patent/DE2651574A1/de

1977-08-20 Priority claimed from DE19772737630 external-priority patent/DE2737630A1/de

1977-11-08 Priority claimed from CS777291A external-priority patent/CS228106B2/cs

1978-08-21 Application filed by Boehringer Mannheim Gmbh filed Critical Boehringer Mannheim Gmbh

1978-08-21 Priority to CS785461A priority Critical patent/CS228110B2/sk

1984-05-14 Publication of CS228110B2 publication Critical patent/CS228110B2/sk

Links

-1 2-hydroxy-3- [4- (phenoxymethyl) piperidino] propoxy Chemical group 0.000 claims description 48
150000001875 compounds Chemical class 0.000 claims description 35
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 34
239000001257 hydrogen Substances 0.000 claims description 22
229910052739 hydrogen Inorganic materials 0.000 claims description 22
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 17
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 17
125000004432 carbon atom Chemical group C* 0.000 claims description 16
150000002431 hydrogen Chemical class 0.000 claims description 14
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
238000000034 method Methods 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 5
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 5
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 4
125000005042 acyloxymethyl group Chemical group 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 claims description 4
125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 4
125000001589 carboacyl group Chemical group 0.000 claims description 3
239000007795 chemical reaction product Substances 0.000 claims description 3
230000007062 hydrolysis Effects 0.000 claims description 3
238000006460 hydrolysis reaction Methods 0.000 claims description 3
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
ZRZLIXKKYZCXKZ-UHFFFAOYSA-N 3-[4-(phenoxymethyl)piperidin-1-yl]propan-1-ol Chemical class O(C1=CC=CC=C1)CC1CCN(CC1)CCCO ZRZLIXKKYZCXKZ-UHFFFAOYSA-N 0.000 claims description 2
JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 claims description 2
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
125000004185 ester group Chemical group 0.000 claims description 2
150000002825 nitriles Chemical class 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
238000003419 tautomerization reaction Methods 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
125000005041 acyloxyalkyl group Chemical group 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
150000002460 imidazoles Chemical class 0.000 claims 1
125000004430 oxygen atom Chemical group O* 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 36
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 26
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
239000000203 mixture Substances 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 11
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 10
239000002904 solvent Substances 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
239000002253 acid Substances 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 5
PGZVFRAEAAXREB-UHFFFAOYSA-N 2,2-dimethylpropanoyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC(=O)C(C)(C)C PGZVFRAEAAXREB-UHFFFAOYSA-N 0.000 description 5
YPYSERZXQBYPNJ-UHFFFAOYSA-N ethyl 4-[2-hydroxy-3-[4-(phenoxymethyl)piperidin-1-yl]propoxy]-1h-indole-2-carboxylate Chemical compound C1=CC=C2NC(C(=O)OCC)=CC2=C1OCC(O)CN(CC1)CCC1COC1=CC=CC=C1 YPYSERZXQBYPNJ-UHFFFAOYSA-N 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 4
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
OXHUYOXGBYDMQM-UHFFFAOYSA-N 1-[(6-methyl-1h-indol-4-yl)oxy]-3-[4-(phenoxymethyl)piperidin-1-yl]propan-2-ol Chemical compound C=12C=CNC2=CC(C)=CC=1OCC(O)CN(CC1)CCC1COC1=CC=CC=C1 OXHUYOXGBYDMQM-UHFFFAOYSA-N 0.000 description 3
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
239000005711 Benzoic acid Substances 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000002252 acyl group Chemical group 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
235000010233 benzoic acid Nutrition 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000000796 flavoring agent Substances 0.000 description 3
235000013355 food flavoring agent Nutrition 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
239000007787 solid Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
RGQAACOCUCKZGG-UHFFFAOYSA-N 1-(1h-benzimidazol-4-yloxy)-3-[4-(phenoxymethyl)piperidin-1-yl]propan-2-ol Chemical compound C=1C=CC=2N=CNC=2C=1OCC(O)CN(CC1)CCC1COC1=CC=CC=C1 RGQAACOCUCKZGG-UHFFFAOYSA-N 0.000 description 2
ARFNSMYWLYZEPU-UHFFFAOYSA-N 1-(1h-indol-4-yloxy)-3-[4-(phenoxymethyl)piperidin-1-yl]propan-2-ol Chemical compound C=1C=CC=2NC=CC=2C=1OCC(O)CN(CC1)CCC1COC1=CC=CC=C1 ARFNSMYWLYZEPU-UHFFFAOYSA-N 0.000 description 2
PFOVRLZFVUZAAA-UHFFFAOYSA-N 1-(2h-benzotriazol-4-yloxy)-3-[4-(phenoxymethyl)piperidin-1-yl]propan-2-ol;hydrochloride Chemical compound Cl.C=1C=CC=2NN=NC=2C=1OCC(O)CN(CC1)CCC1COC1=CC=CC=C1 PFOVRLZFVUZAAA-UHFFFAOYSA-N 0.000 description 2
VPLIYRLGJUFEJR-UHFFFAOYSA-N 1-[[6-(hydroxymethyl)-1h-indol-4-yl]oxy]-3-[4-(phenoxymethyl)piperidin-1-yl]propan-2-ol Chemical compound C=12C=CNC2=CC(CO)=CC=1OCC(O)CN(CC1)CCC1COC1=CC=CC=C1 VPLIYRLGJUFEJR-UHFFFAOYSA-N 0.000 description 2
OYSPHZXMAJRFAZ-UHFFFAOYSA-N 1-[[6-(hydroxymethyl)-5-methyl-1H-indol-4-yl]oxy]-3-[4-(phenoxymethyl)piperidin-1-yl]propan-2-ol Chemical compound OC(COC1=C2C=CNC2=CC(=C1C)CO)CN1CCC(CC1)COC1=CC=CC=C1 OYSPHZXMAJRFAZ-UHFFFAOYSA-N 0.000 description 2
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
HFYYHLKSHSXIDG-UHFFFAOYSA-N [1-(1h-indol-4-yloxy)-3-[4-(phenoxymethyl)piperidin-1-yl]propan-2-yl] 2,2-dimethylpropanoate Chemical compound C=1C=CC=2NC=CC=2C=1OCC(OC(=O)C(C)(C)C)CN(CC1)CCC1COC1=CC=CC=C1 HFYYHLKSHSXIDG-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000000654 additive Substances 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
125000003435 aroyl group Chemical group 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
229920006158 high molecular weight polymer Polymers 0.000 description 2
239000007788 liquid 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
229910052987 metal hydride Inorganic materials 0.000 description 2
150000004681 metal hydrides Chemical class 0.000 description 2
229910000510 noble metal Inorganic materials 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
239000000725 suspension Substances 0.000 description 2
OLENANGIJWDOPG-UHFFFAOYSA-N (2-chlorobenzoyl) 2-chlorobenzoate Chemical compound ClC1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1Cl OLENANGIJWDOPG-UHFFFAOYSA-N 0.000 description 1
LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
BJMLLSSSTGHJJE-UHFFFAOYSA-N (4-methylbenzoyl) 4-methylbenzoate Chemical compound C1=CC(C)=CC=C1C(=O)OC(=O)C1=CC=C(C)C=C1 BJMLLSSSTGHJJE-UHFFFAOYSA-N 0.000 description 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
RKUKNWAWXPCTEO-UHFFFAOYSA-N 1-(1H-indol-4-yloxy)-3-[4-[(4-phenylmethoxyphenoxy)methyl]piperidin-1-yl]propan-2-ol Chemical compound C=1C=CC=2NC=CC=2C=1OCC(O)CN(CC1)CCC1COC(C=C1)=CC=C1OCC1=CC=CC=C1 RKUKNWAWXPCTEO-UHFFFAOYSA-N 0.000 description 1
ZMYWQGNLHHILTC-UHFFFAOYSA-N 1-(1H-indol-5-yloxy)-3-[4-(phenoxymethyl)piperidin-1-yl]propan-2-ol Chemical compound OC(COC=1C=C2C=CNC2=CC=1)CN1CCC(CC1)COC1=CC=CC=C1 ZMYWQGNLHHILTC-UHFFFAOYSA-N 0.000 description 1
RLEPYMXVKJWNIM-UHFFFAOYSA-N 1-(1H-indol-6-yloxy)-3-[4-(phenoxymethyl)piperidin-1-yl]propan-2-ol Chemical compound OC(COC1=CC=C2C=CNC2=C1)CN1CCC(CC1)COC1=CC=CC=C1 RLEPYMXVKJWNIM-UHFFFAOYSA-N 0.000 description 1
MOYSKNAMCCSLAO-UHFFFAOYSA-N 1-(1h-indazol-4-yloxy)-3-[4-(phenoxymethyl)piperidin-1-yl]propan-2-ol Chemical compound C=1C=CC=2NN=CC=2C=1OCC(O)CN(CC1)CCC1COC1=CC=CC=C1 MOYSKNAMCCSLAO-UHFFFAOYSA-N 0.000 description 1
WBAXSQUIGRIDCS-UHFFFAOYSA-N 1-(oxiran-2-ylmethyl)-4-(phenoxymethyl)piperidine Chemical compound C1CN(CC2OC2)CCC1COC1=CC=CC=C1 WBAXSQUIGRIDCS-UHFFFAOYSA-N 0.000 description 1
RFIQLGKXBMUYIK-UHFFFAOYSA-N 1-[(2-methyl-1h-indol-4-yl)oxy]-3-[4-(phenoxymethyl)piperidin-1-yl]propan-2-ol Chemical compound C1=CC=C2NC(C)=CC2=C1OCC(O)CN(CC1)CCC1COC1=CC=CC=C1 RFIQLGKXBMUYIK-UHFFFAOYSA-N 0.000 description 1
RPPPPVYOQULVQH-UHFFFAOYSA-N 1-[(2-methyl-1h-indol-4-yl)oxy]-3-[4-[(2-methylphenoxy)methyl]piperidin-1-yl]propan-2-ol Chemical compound C1=CC=C2NC(C)=CC2=C1OCC(O)CN(CC1)CCC1COC1=CC=CC=C1C RPPPPVYOQULVQH-UHFFFAOYSA-N 0.000 description 1
OAAYZSLGIOZJDJ-UHFFFAOYSA-N 1-[(3-methyl-2h-indazol-4-yl)oxy]-3-[4-(phenoxymethyl)piperidin-1-yl]propan-2-ol Chemical compound C=12C(C)=NNC2=CC=CC=1OCC(O)CN(CC1)CCC1COC1=CC=CC=C1 OAAYZSLGIOZJDJ-UHFFFAOYSA-N 0.000 description 1
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RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
230000000304 vasodilatating effect Effects 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CS785461A 1976-11-12 1978-08-21 Způsob výroby nových derivátů 3-(4-fenoxymethylpiperidino)propanolu CS228110B2 (sk)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CS785461A CS228110B2 (sk)	1976-11-12	1978-08-21	Způsob výroby nových derivátů 3-(4-fenoxymethylpiperidino)propanolu

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
DE19762651574 DE2651574A1 (de)	1976-11-12	1976-11-12	Ein neues aminopropanol-derivat und verfahren zu dessen herstellung
DE19772737630 DE2737630A1 (de)	1977-08-20	1977-08-20	Neue aminopropanolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
CS777291A CS228106B2 (en)	1976-11-12	1977-11-08	Production of novel derivatives of 3-/4-phenoxymethylpiperidino/-propanol
CS785461A CS228110B2 (sk)	1976-11-12	1978-08-21	Způsob výroby nových derivátů 3-(4-fenoxymethylpiperidino)propanolu

Publications (1)

Publication Number	Publication Date
CS228110B2 true CS228110B2 (sk)	1984-05-14

Family

ID=27179547

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS785461A CS228110B2 (sk)	1976-11-12	1978-08-21	Způsob výroby nových derivátů 3-(4-fenoxymethylpiperidino)propanolu

Country Status (1)

Country	Link
CS (1)	CS228110B2 (sk)

1978
- 1978-08-21 CS CS785461A patent/CS228110B2/sk unknown

Publication	Publication Date	Title
JP4700017B2 (ja)	2011-06-15	ピペリジン類およびピペラジン類
US4904676A (en)	1990-02-27	Amino-oxazole compounds having dopaminergic activity
US4680296A (en)	1987-07-14	Piperidine derivatives and pharmaceutical compositions containing them
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US5182280A (en)	1993-01-26	Derivatives of benzimidazole and their use as antihistamines
CA1086740A (en)	1980-09-30	Piperidinopropyl derivatives and the preparation thereof
JPH04295464A (ja)	1992-10-20	複素環式ヒドロキシルアミン
US5330986A (en)	1994-07-19	Indole-7-carboxamide derivatives
CA1115703A (en)	1982-01-05	Piperidinopropyl derivatives
DE2737630C2 (sk)	1987-11-05
JPS6019305B2 (ja)	1985-05-15	ジヒドロベンゾフラン誘導体
SU1041033A3 (ru)	1983-09-07	Способ получени производных аминопропанола или их солей
US3491097A (en)	1970-01-20	3-(piperazinoalkyl)-pyrazoles
CS228110B2 (sk)	1984-05-14	Způsob výroby nových derivátů 3-(4-fenoxymethylpiperidino)propanolu
US5344927A (en)	1994-09-06	Tetrahydrobenzimidazole derivatives and pharmaceutical compositions containing same
US4859700A (en)	1989-08-22	2-(2,3-dihydro-2-oxo-3-benzofuranyl)acetic acid compounds having antihypoxic and nootropic effects
CS228109B2 (cs)	1984-05-14	Způsob výroby nových derivátů 3-(4-fenoxymethylpiperidino)propanolu
EP0287971B1 (en)	1993-02-24	Benzimidazole derivatives and process for their preparations
JPS6212757A (ja)	1987-01-21	桂皮酸アミド誘導体
JPS62267269A (ja)	1987-11-19	ピラゾ−ル−３−アミン類
EP0427860A1 (en)	1991-05-22	New imidazole derivatives, production thereof, and uses thereof as medicines
SU527134A3 (ru)	1976-08-30	Способ получени производных бензиламина или их солей
CA1258070A (en)	1989-08-01	1-aminoalkylindoles useful as analgesic agents or as intermediates and their production processes
CA2008815C (en)	1998-06-30	Tetrahydrobenzimidazole derivatives
US3725432A (en)	1973-04-03	Biphenylyl pyrazole compounds