NO861897L - Fremgangsmaate for fremstilling av terapeutisk aktive forbindelser. - Google Patents

Fremgangsmaate for fremstilling av terapeutisk aktive forbindelser.

Info

Publication number: NO861897L
Authority: NO; Norway
Prior art keywords: formula; phenyl; mixture; fluoro; compounds
Prior art date: 1985-05-14

Application number

NO861897A

Other languages

English (en)

Norwegian (no)

Inventor

Bernard Gaudilliere

Jean Rousseau

Original Assignee

Synthelabo

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.)

1985-05-14

Filing date

1986-05-13

Publication date

1986-11-17

1986-05-13 Application filed by Synthelabo filed Critical Synthelabo

1986-11-17 Publication of NO861897L publication Critical patent/NO861897L/no

Links

238000000034 method Methods 0.000 title claims description 11
238000002360 preparation method Methods 0.000 title claims description 7
230000001225 therapeutic effect Effects 0.000 title claims 2
150000001875 compounds Chemical class 0.000 claims abstract description 51
-1 4-methoxy - 3,5-dimethylphenyl Chemical group 0.000 claims abstract description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 7
239000002253 acid Substances 0.000 claims abstract description 6
229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
150000003839 salts Chemical class 0.000 claims abstract description 5
229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
150000002576 ketones Chemical class 0.000 claims description 9
125000001424 substituent group Chemical group 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
230000009471 action Effects 0.000 claims description 4
DDRCHUGHUHZNKZ-UHFFFAOYSA-N phenyl(piperidin-4-yl)methanone Chemical compound C=1C=CC=CC=1C(=O)C1CCNCC1 DDRCHUGHUHZNKZ-UHFFFAOYSA-N 0.000 claims description 4
230000009467 reduction Effects 0.000 claims description 4
AGAVKPLLEUXKPI-UHFFFAOYSA-N 1-(1,3-dioxolan-2-yl)piperidine Chemical compound O1CCOC1N1CCCCC1 AGAVKPLLEUXKPI-UHFFFAOYSA-N 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 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
238000006264 debenzylation reaction Methods 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
239000012458 free base Substances 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims 1
150000002118 epoxides Chemical class 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 abstract description 3
239000001257 hydrogen Substances 0.000 abstract description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 2
239000000460 chlorine Substances 0.000 abstract description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
125000005808 2,4,6-trimethoxyphenyl group Chemical group [H][#6]-1=[#6](-[#8]C([H])([H])[H])-[#6](-*)=[#6](-[#8]C([H])([H])[H])-[#6]([H])=[#6]-1-[#8]C([H])([H])[H] 0.000 abstract 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
239000011737 fluorine Substances 0.000 abstract 1
229910052736 halogen Inorganic materials 0.000 abstract 1
150000002367 halogens Chemical class 0.000 abstract 1
150000002431 hydrogen Chemical group 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 67
239000000203 mixture Substances 0.000 description 58
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 41
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 20
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
238000002844 melting Methods 0.000 description 18
230000008018 melting Effects 0.000 description 18
239000002904 solvent Substances 0.000 description 16
238000004587 chromatography analysis Methods 0.000 description 13
239000012074 organic phase Substances 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
229910021529 ammonia Inorganic materials 0.000 description 10
239000000872 buffer Substances 0.000 description 10
229910000027 potassium carbonate Inorganic materials 0.000 description 10
238000010992 reflux Methods 0.000 description 10
239000002585 base Substances 0.000 description 9
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
229910052700 potassium Inorganic materials 0.000 description 8
239000011591 potassium Substances 0.000 description 8
241000699670 Mus sp. Species 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
239000000047 product Substances 0.000 description 7
239000000243 solution Substances 0.000 description 7
230000004083 survival effect Effects 0.000 description 7
GIZSHQYTTBQKOQ-UHFFFAOYSA-N threo-Syringoylglycerol Chemical compound COC1=CC(C(O)C(O)CO)=CC(OC)=C1O GIZSHQYTTBQKOQ-UHFFFAOYSA-N 0.000 description 7
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
239000007787 solid Substances 0.000 description 6
230000027455 binding Effects 0.000 description 5
AKPUJVVHYUHGKY-UHFFFAOYSA-N hydron;propan-2-ol;chloride Chemical compound Cl.CC(C)O AKPUJVVHYUHGKY-UHFFFAOYSA-N 0.000 description 5
150000002924 oxiranes Chemical class 0.000 description 5
230000009870 specific binding Effects 0.000 description 5
239000000725 suspension Substances 0.000 description 5
FIUYIDSZFQWXSI-UHFFFAOYSA-N (4-chlorophenyl)-[1-[1-(4-fluorophenyl)-1-hydroxypropan-2-yl]piperidin-4-yl]methanone Chemical compound C1CC(C(=O)C=2C=CC(Cl)=CC=2)CCN1C(C)C(O)C1=CC=C(F)C=C1 FIUYIDSZFQWXSI-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
238000001035 drying Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
NLZGZUVTOHQCQF-UHFFFAOYSA-N furan-2-yl(thiomorpholin-4-yl)methanone Chemical compound C=1C=COC=1C(=O)N1CCSCC1 NLZGZUVTOHQCQF-UHFFFAOYSA-N 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
238000005406 washing Methods 0.000 description 4
KBHXRVRVUFCBAU-UHFFFAOYSA-N (4-fluorophenyl)-[1-[1-(4-fluorophenyl)-1-hydroxypropan-2-yl]piperidin-4-yl]methanone Chemical compound C1CC(C(=O)C=2C=CC(F)=CC=2)CCN1C(C)C(O)C1=CC=C(F)C=C1 KBHXRVRVUFCBAU-UHFFFAOYSA-N 0.000 description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-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
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
208000035475 disorder Diseases 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
235000019253 formic acid Nutrition 0.000 description 3
238000011534 incubation Methods 0.000 description 3
238000007912 intraperitoneal administration Methods 0.000 description 3
229910001629 magnesium chloride Inorganic materials 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
150000007530 organic bases Chemical class 0.000 description 3
229960001289 prazosin Drugs 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
229950001675 spiperone Drugs 0.000 description 3
238000012360 testing method Methods 0.000 description 3
238000001665 trituration Methods 0.000 description 3
ZZYGXYJNHRFOPR-UHFFFAOYSA-N (4-chlorophenyl)-[1-[2-(4-ethylphenyl)-2-hydroxyethyl]piperidin-4-yl]methanone Chemical compound C1=CC(CC)=CC=C1C(O)CN1CCC(C(=O)C=2C=CC(Cl)=CC=2)CC1 ZZYGXYJNHRFOPR-UHFFFAOYSA-N 0.000 description 2
ZUQLRYTXWPTSNF-UHFFFAOYSA-N (4-fluorophenyl)-[1-(2-hydroxy-2-phenylethyl)piperidin-4-yl]methanone Chemical compound C=1C=CC=CC=1C(O)CN(CC1)CCC1C(=O)C1=CC=C(F)C=C1 ZUQLRYTXWPTSNF-UHFFFAOYSA-N 0.000 description 2
MUILTTIQCFNQMK-UHFFFAOYSA-N (4-fluorophenyl)-[1-[1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]piperidin-4-yl]methanone Chemical compound C1CC(C(=O)C=2C=CC(F)=CC=2)CCN1C(C)C(O)C1=CC=C(O)C=C1 MUILTTIQCFNQMK-UHFFFAOYSA-N 0.000 description 2
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
239000007983 Tris buffer Substances 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
230000031709 bromination Effects 0.000 description 2
238000005893 bromination reaction Methods 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
210000003710 cerebral cortex Anatomy 0.000 description 2
238000006073 displacement reaction Methods 0.000 description 2
238000010828 elution Methods 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
238000002347 injection Methods 0.000 description 2
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208000028867 ischemia Diseases 0.000 description 2
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238000007911 parenteral administration Methods 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
230000008569 process Effects 0.000 description 2
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 2
239000000126 substance Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
230000002792 vascular Effects 0.000 description 2
GCVOWNMNLDEKGO-UHFFFAOYSA-N (4-fluorophenyl)-[1-[2-hydroxy-2-(3-methylphenyl)ethyl]piperidin-4-yl]methanone Chemical compound CC1=CC=CC(C(O)CN2CCC(CC2)C(=O)C=2C=CC(F)=CC=2)=C1 GCVOWNMNLDEKGO-UHFFFAOYSA-N 0.000 description 1
CTVZMRHUKLASEA-UHFFFAOYSA-N (4-fluorophenyl)-[1-[2-hydroxy-2-(4-methoxyphenyl)ethyl]piperidin-4-yl]methanone Chemical compound C1=CC(OC)=CC=C1C(O)CN1CCC(C(=O)C=2C=CC(F)=CC=2)CC1 CTVZMRHUKLASEA-UHFFFAOYSA-N 0.000 description 1
ABERUOJGWHYBJL-UHFFFAOYSA-N (4-fluorophenyl)-piperidin-4-ylmethanone Chemical compound C1=CC(F)=CC=C1C(=O)C1CCNCC1 ABERUOJGWHYBJL-UHFFFAOYSA-N 0.000 description 1
AWMVMTVKBNGEAK-MRVPVSSYSA-N (S)-styrene oxide Chemical compound C1O[C@H]1C1=CC=CC=C1 AWMVMTVKBNGEAK-MRVPVSSYSA-N 0.000 description 1
OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
ARKIFHPFTHVKDT-UHFFFAOYSA-N 1-(3-nitrophenyl)ethanone Chemical compound CC(=O)C1=CC=CC([N+]([O-])=O)=C1 ARKIFHPFTHVKDT-UHFFFAOYSA-N 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
GZHPNIQBPGUSSX-UHFFFAOYSA-N 2-bromo-1-(3-nitrophenyl)ethanone Chemical compound [O-][N+](=O)C1=CC=CC(C(=O)CBr)=C1 GZHPNIQBPGUSSX-UHFFFAOYSA-N 0.000 description 1
XNYSPDGJBPTDDI-UHFFFAOYSA-N 2-bromo-1-(4-ethylphenyl)ethanone Chemical compound CCC1=CC=C(C(=O)CBr)C=C1 XNYSPDGJBPTDDI-UHFFFAOYSA-N 0.000 description 1
QKHHCXOSPQAQQI-UHFFFAOYSA-N 2-bromo-1-(4-fluorophenyl)propan-1-one Chemical compound CC(Br)C(=O)C1=CC=C(F)C=C1 QKHHCXOSPQAQQI-UHFFFAOYSA-N 0.000 description 1
XQJAHBHCLXUGEP-UHFFFAOYSA-N 2-bromo-1-(4-methoxyphenyl)ethanone Chemical compound COC1=CC=C(C(=O)CBr)C=C1 XQJAHBHCLXUGEP-UHFFFAOYSA-N 0.000 description 1
KABSWBAVVVOZDJ-UHFFFAOYSA-N 2-chloro-1-(4-phenylmethoxyphenyl)propan-1-one Chemical compound C1=CC(C(=O)C(Cl)C)=CC=C1OCC1=CC=CC=C1 KABSWBAVVVOZDJ-UHFFFAOYSA-N 0.000 description 1
CKQHAYFOPRIUOM-UHFFFAOYSA-N 3'-Aminoacetophenone Chemical compound CC(=O)C1=CC=CC(N)=C1 CKQHAYFOPRIUOM-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
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AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
QROGIFZRVHSFLM-QHHAFSJGSA-N [(e)-prop-1-enyl]benzene Chemical compound C\C=C\C1=CC=CC=C1 QROGIFZRVHSFLM-QHHAFSJGSA-N 0.000 description 1
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GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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210000003169 central nervous system Anatomy 0.000 description 1
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238000002329 infrared spectrum Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
238000011835 investigation Methods 0.000 description 1
TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000012528 membrane Substances 0.000 description 1
LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
AFZTYHRVDOKRKV-UHFFFAOYSA-N n-(3-acetylphenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(C(C)=O)=C1 AFZTYHRVDOKRKV-UHFFFAOYSA-N 0.000 description 1
IBMUCSJKSQYUIB-UHFFFAOYSA-N n-[3-(2-bromoacetyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C(=O)CBr)=C1 IBMUCSJKSQYUIB-UHFFFAOYSA-N 0.000 description 1
HIBKNGYIGLPHDB-UHFFFAOYSA-N n-[3-[2-[4-(4-fluorobenzoyl)piperidin-1-yl]-1-hydroxyethyl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C(O)CN2CCC(CC2)C(=O)C=2C=CC(F)=CC=2)=C1 HIBKNGYIGLPHDB-UHFFFAOYSA-N 0.000 description 1
125000006501 nitrophenyl group Chemical group 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
NODGRWCMFMEGJH-UHFFFAOYSA-N p-ethylacetophenone Chemical compound CCC1=CC=C(C(C)=O)C=C1 NODGRWCMFMEGJH-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
MRBDMNSDAVCSSF-UHFFFAOYSA-N phentolamine Chemical compound C1=CC(C)=CC=C1N(C=1C=C(O)C=CC=1)CC1=NCCN1 MRBDMNSDAVCSSF-UHFFFAOYSA-N 0.000 description 1
229960001999 phentolamine Drugs 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
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 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 description 1
239000002243 precursor Substances 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012264 purified product Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
230000002295 serotoninergic effect Effects 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
DKGZKTPJOSAWFA-UHFFFAOYSA-N spiperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC2(C(NCN2C=2C=CC=CC=2)=O)CC1 DKGZKTPJOSAWFA-UHFFFAOYSA-N 0.000 description 1
238000010025 steaming Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
230000000153 supplemental effect Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
VFJYIHQDILEQNR-UHFFFAOYSA-M trimethylsulfanium;iodide Chemical compound [I-].C[S+](C)C VFJYIHQDILEQNR-UHFFFAOYSA-M 0.000 description 1
208000009999 tuberous sclerosis Diseases 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
- C07D211/06—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
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
- 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
- C07D211/30—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 with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—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 with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Neurosurgery (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Neurology (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Biomedical Technology (AREA)
Hospice & Palliative Care (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Psychiatry (AREA)
Hydrogenated Pyridines (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Organic Insulating Materials (AREA)
Compositions Of Macromolecular Compounds (AREA)
Steroid Compounds (AREA)

NO861897A 1985-05-14 1986-05-13 Fremgangsmaate for fremstilling av terapeutisk aktive forbindelser. NO861897L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR8507270A FR2581993B1 (fr)	1985-05-14	1985-05-14	Derives de (benzoyl-4 piperidino)-2 phenyl-1 alcanols, leur preparation et leur application en therapeutique

Publications (1)

Publication Number	Publication Date
NO861897L true NO861897L (no)	1986-11-17

Family

ID=9319247

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO861897A NO861897L (no)	1985-05-14	1986-05-13	Fremgangsmaate for fremstilling av terapeutisk aktive forbindelser.

Country Status (18)

Country	Link
US (1)	US4711899A (de)
EP (1)	EP0202164B1 (de)
JP (1)	JPS61260063A (de)
KR (1)	KR860008976A (de)
AT (1)	ATE40684T1 (de)
AU (1)	AU584701B2 (de)
DE (1)	DE3662044D1 (de)
DK (1)	DK220386A (de)
ES (2)	ES8802138A1 (de)
FI (1)	FI861995A (de)
FR (1)	FR2581993B1 (de)
GR (1)	GR861253B (de)
HU (1)	HU195640B (de)
IL (1)	IL78773A (de)
NO (1)	NO861897L (de)
NZ (1)	NZ216145A (de)
PT (1)	PT82569B (de)
ZA (1)	ZA863533B (de)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR910006138B1 (ko) *	1986-09-30	1991-08-16	에자이 가부시끼가이샤	환상아민 유도체
JP2573195B2 (ja) *	1986-09-30	1997-01-22	エーザイ株式会社	環状アミン誘導体
US4870083A (en) *	1987-11-24	1989-09-26	Merrell Dow Pharmaceuticals Inc.	1,4-Disubstituted-piperidinyl compounds useful as analgesics and muscle relaxants
US5166211A (en) *	1987-12-17	1992-11-24	Merrell Dow Pharmaceuticals Inc.	Method of using 1,4-disubstituted piperidinyl compounds in the treatment of coronary vasospasons and variant angina
US5093341A (en) *	1987-12-17	1992-03-03	Merrell Dow Pharmaceuticals Inc.	N-aralkyl piperidine derivatives useful as antithrombolytic agents
US5064838A (en) *	1988-01-21	1991-11-12	Merrell Dow Pharmaceuticals	1,4-disubstituted-piperidinyl compounds as pain relievers
FR2640266B2 (fr) *	1988-07-12	1992-07-10	Synthelabo	Derives de (hydroxy-1 piperidinyl-2 alkyl) indolones-2, quinoleinones-2, benzo(b)azepinones-2 et benzimidazolones-2, leur preparation et leur application en therapeutique
FR2634206B1 (fr) *	1988-07-12	1992-05-15	Synthelabo	Derives de (hydroxy-1 piperidinyl-2 alkyl) indolones-2 et quinoleinones-2, leur preparation et leur application en therapeutique
GB8823776D0 (en) *	1988-10-11	1988-11-16	Scras	New 2-methoxycarbonyl sustituted n n'-di-(trimethoxybenzoyl)piperazines
GB8823775D0 (en) *	1988-10-11	1988-11-16	Scras	New 2-carbonyl substituted n n'-di-(trimethoxybenzoyl)piperazines
US5055470A (en) *	1989-06-01	1991-10-08	Bristol-Myers Squibb Co.	Method of treatment of ischemia in brain
US4994460A (en) *	1989-06-01	1991-02-19	Bristol-Myers Squibb Co.	Agents for treatment of brain ischemia
NZ236501A (en) *	1989-12-21	1992-12-23	Merrell Dow Pharma	Piperidine derivatives and antithrombotic compositions
US5292752A (en) *	1989-12-21	1994-03-08	Merrell Dow Pharmaceuticals Inc.	Antithrombotic compounds
EP0554247B1 (de) *	1990-05-10	2000-04-26	Pfizer Inc.	Neuroprotective indolone und verwandte derivate
US5478846A (en) *	1990-06-07	1995-12-26	Merrell Dow Pharmaceuticals Inc.	1-piperidinyl alkanoylanyl sulfonamides for treatment of cardiac arrhythmia
JP3032294B2 (ja) *	1990-06-07	2000-04-10	メレルダウファーマス―ティカルズインコーポレイテッド	１―ピペリジニルアルカノイルアリールスルホンアミド誘導体類
US5512584A (en) *	1991-04-16	1996-04-30	Basf Aktiengesellschaft	1,3,4-trisubstituted piperidine derivatives, the preparation and use thereof
FR2678269B1 (fr) *	1991-06-27	1995-01-13	Synthelabo	Derives de 1-(4-chlorophenyl)-2-[4-(2-phenylethyl)piperidin-1-yl]ethanol, leur application et leur preparation en therapeutique.
FR2688504B1 (fr) *	1992-03-13	1995-05-05	Synthelabo	Derives de 2-(piperidin-1-yl)ethanol, leur preparation et leur application en therapeutique.
US5436255A (en) *	1992-07-23	1995-07-25	Pfizer Inc.	Method of treating diseases susceptable to treatment by blocking NMDA-receptors
US5498610A (en) *	1992-11-06	1996-03-12	Pfizer Inc.	Neuroprotective indolone and related derivatives
ATE183184T1 (de) *	1994-01-31	1999-08-15	Pfizer	Neuroprotektive chroman verbindungen
FR2737494B1 (fr) *	1995-08-04	1997-08-29	Synthelabo	Derives de benzenesulfonamide, leur preparation et leur application en therapeutique
US6770659B2 (en) *	2002-08-26	2004-08-03	Sk Corporation	Benzoyl piperidine compounds
US20050158270A1 (en) *	2004-01-15	2005-07-21	Seren Frantz	Pearlizer concentrate and its use in personal care compositions

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Publication number	Priority date	Publication date	Assignee	Title
CH492709A (de) *	1968-01-11	1970-06-30	Geigy Ag J R	Verfahren zur Herstellung von neuen Piperidinderivaten
US3632767A (en) *	1968-02-12	1972-01-04	Mallinckrodt Chemical Works	Treatment of depression with 4-substituted piperidines
US3576810A (en) *	1968-06-20	1971-04-27	Robins Co Inc A H	1-substituted-3-(-4)-aroylpiperidines
BE791088A (fr) *	1971-11-09	1973-03-01	Richardson Merrell Inc	Nouveaux derives d'aryl (piperidyl-4) cetone, utiles notamment comme analgesiques et anticoagulants, et leur procede de preparation
US4101662A (en) *	1973-05-03	1978-07-18	A. H. Robins Company, Incorporated	Method for inhibiting emesis and compositions therefor
GB1535791A (en) *	1975-05-07	1978-12-13	Ferrosan Ab	Derivatives of 4-piperidinol
US4035369A (en) *	1975-10-08	1977-07-12	Janssen Pharmaceutica N.V.	1-Benzazolylalkyl-4-substituted-piperidines
CH602642A5 (de) *	1975-11-14	1978-07-31	Orgamol Sa
FR2408602A2 (fr) *	1977-11-15	1979-06-08	Synthelabo	Nouveaux derives de piperidine et leur methode de preparation
US4335127A (en) *	1979-01-08	1982-06-15	Janssen Pharmaceutica, N.V.	Piperidinylalkyl quinazoline compounds, composition and method of use
US4198419A (en) *	1979-01-10	1980-04-15	American Hoechst Corporation	Phenylthiophenylpiperidines
US4443451A (en) *	1981-07-15	1984-04-17	Janssen Pharmaceutica N.V.	Bicyclic pyrimidin-5-one derivatives
FR2534580A1 (fr) *	1982-10-13	1984-04-20	Synthelabo	Derives de phenyl-1 piperidino-2 propanol, leur preparation, et medicaments qui les contiennent
DK159420C (da) *	1983-03-09	1991-03-11	Ciba Geigy Ag	N-(piperidinyl-alkyl)-carboxamider og salte deraf, farmaceutiske praeparater indeholdende disse forbindelser samt anvendelsen af forbindelserne til fremstilling af antipsykotiske farmaceutiske praeparater
US4458076A (en) *	1983-05-31	1984-07-03	Hoechst-Roussel Pharmaceuticals	3-(4-Piperidinyl)-1,2-benzisothiazoles

1985
- 1985-05-14 FR FR8507270A patent/FR2581993B1/fr not_active Expired
1986
- 1986-05-12 DE DE8686401000T patent/DE3662044D1/de not_active Expired
- 1986-05-12 AT AT86401000T patent/ATE40684T1/de active
- 1986-05-12 EP EP86401000A patent/EP0202164B1/de not_active Expired
- 1986-05-13 HU HU861975A patent/HU195640B/hu not_active IP Right Cessation
- 1986-05-13 IL IL78773A patent/IL78773A/xx unknown
- 1986-05-13 DK DK220386A patent/DK220386A/da not_active Application Discontinuation
- 1986-05-13 JP JP61110463A patent/JPS61260063A/ja active Pending
- 1986-05-13 GR GR861253A patent/GR861253B/el unknown
- 1986-05-13 ES ES554895A patent/ES8802138A1/es not_active Expired
- 1986-05-13 AU AU57406/86A patent/AU584701B2/en not_active Ceased
- 1986-05-13 US US06/862,715 patent/US4711899A/en not_active Expired - Fee Related
- 1986-05-13 KR KR1019860003714A patent/KR860008976A/ko not_active Application Discontinuation
- 1986-05-13 FI FI861995A patent/FI861995A/fi not_active Application Discontinuation
- 1986-05-13 NO NO861897A patent/NO861897L/no unknown
- 1986-05-13 ZA ZA863533A patent/ZA863533B/xx unknown
- 1986-05-13 NZ NZ216145A patent/NZ216145A/xx unknown
- 1986-05-13 PT PT82569A patent/PT82569B/pt unknown
1987
- 1987-06-08 ES ES557582A patent/ES8801631A1/es not_active Expired

Also Published As

Publication number	Publication date
DK220386D0 (da)	1986-05-13
PT82569A (fr)	1986-06-01
ES554895A0 (es)	1988-04-01
FR2581993A1 (fr)	1986-11-21
FI861995A (fi)	1986-11-15
ES557582A0 (es)	1988-02-16
ES8802138A1 (es)	1988-04-01
IL78773A0 (en)	1986-08-31
JPS61260063A (ja)	1986-11-18
PT82569B (fr)	1988-04-12
DK220386A (da)	1986-11-15
ES8801631A1 (es)	1988-02-16
GR861253B (en)	1986-09-10
EP0202164B1 (de)	1989-02-08
HUT40790A (en)	1987-02-27
AU5740686A (en)	1986-11-20
HU195640B (en)	1988-06-28
AU584701B2 (en)	1989-06-01
US4711899A (en)	1987-12-08
DE3662044D1 (en)	1989-03-16
ZA863533B (en)	1986-12-30
FI861995A0 (fi)	1986-05-13
EP0202164A1 (de)	1986-11-20
ATE40684T1 (de)	1989-02-15
KR860008976A (ko)	1986-12-19
IL78773A (en)	1990-09-17
FR2581993B1 (fr)	1988-03-18
NZ216145A (en)	1988-10-28

Publication	Publication Date	Title
NO861897L (no)	1986-11-17	Fremgangsmaate for fremstilling av terapeutisk aktive forbindelser.
SU862826A3 (ru)	1981-09-07	Способ получени производных фталазина или их солей с фармацевтически приемлемыми кислотами
EP1499589B1 (de)	2007-05-02	N-¬phenyl(piperidin-2-yl)methyl\|benzamidderivate,verfahren zu ihrer herstellung und ihre therapeutische anwendung
JPS6289679A (ja)	1987-04-24	ピペリジン誘導体
FI92822C (fi)	1995-01-10	Menetelmä uusien terapeuttisesti käyttökelpoisten 4-fenyyli-piperidiiniyhdisteiden valmistamiseksi
US5114952A (en)	1992-05-19	Isoquinolinylsulfonamides as anti-arrhythmic agents
CA1114379A (en)	1981-12-15	Piperidino-phthalazines
JP3269574B2 (ja)	2002-03-25	メタノアントラセン化合物、これを含有する神経精神障害を治療するための調剤学的組成物、およびこの化合物を製造するための方法および中間体
EP0558487B1 (de)	1998-10-07	Piperidin-verbindungen, ihre darstellung und ihre verwendung
IE65125B1 (en)	1995-10-04	Imidazopyridine PAF/H1 antagonists
EP0221376B1 (de)	1990-06-20	N-substituierte Diphenylpiperidine
DE69007126T2 (de)	1994-06-01	Muscarin-rezeptor-antagonisten.
JPS6135175B2 (de)	1986-08-12
US4243666A (en)	1981-01-06	4-Amino-2-piperidino-quinazolines
CA1189858A (en)	1985-07-02	6-fluoro-3-¬3-(1-heterocyclo)propyl\|-1,2- benzisoxazoles, a process for their preparation, pharmaceutical compositions thereof and their use as medicaments
JPH05213751A (ja)	1993-08-24	一連のアレコロンおよびイソアレコロンのニコチン様活性
US5607950A (en)	1997-03-04	Muscarinic receptor antagonists
HU187480B (en)	1986-01-28	Process for producing 1-bracket-4-quinolyl-bracket closed-2-bracket-4-piperidyl-bracket closed-ethanol and 1-bracket-4-quinolyl-bracket closed-3-bracket-4-piperidiyl-bracket closed-propanol and pharmaceutival compositions containing them as active agents
EP0505465B1 (de)	1996-03-20	4-Heterocyclyl-Piperidin Derivate, deren Herstellung und deren Verwendung als Hemmstoffe der Calcium-Akkumulation in Hirnzellen
US4237138A (en)	1980-12-02	Antihypertensive 4-amino-2-[4-(substituted-alkoxy)piperidino)]quinazolines
SU895291A3 (ru)	1981-12-30	Способ получени производных 4-амино-2-пиперидинохиназолина или их солей с фармацевтически приемлимыми кислотами
JP2022505401A (ja)	2022-01-14	ムスカリンｍ１受容体陽性アロステリックモジュレーターとしてのピロロ－ピリダジン誘導体
JPH07100695B2 (ja)	1995-11-01	新規なピペリジン化合物およびその製薬組成物
EP0241292A2 (de)	1987-10-14	Schmerzlindernde, in 4-Stellung substituierte Octahydrochinolizin-Verbindungen und Octahydrochinolizinium Zwischenprodukte
EP0405784A1 (de)	1991-01-02	Neue Benzisochinolin-Derivate