DD284875A5 - Verfahren zur herstellung von 1-[(diarylmethoxy)-alkyl]-pyrrolidinen und -piperidinen - Google Patents

Verfahren zur herstellung von 1-[(diarylmethoxy)-alkyl]-pyrrolidinen und -piperidinen Download PDF

Info

Publication number: DD284875A5
Authority: DD; German Democratic Republic
Prior art keywords: pyrrolidine; methoxyphenyl; diphenylmethoxy; solution; ethyl
Prior art date: 1988-09-23

Application number

DD89332899A

Other languages

German (de)

English (en)

Inventor

Gerard Ferrand

Jacques Barbanton

Jean-Claude Depin

Gilles Chavernac

Original Assignee

��@��@��@��k��

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.)

1988-09-23

Filing date

1989-09-22

Publication date

1990-11-28

1989-09-22 Application filed by ��@��@��@��k�� filed Critical ��@��@��@��k��

1990-11-28 Publication of DD284875A5 publication Critical patent/DD284875A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 16
238000002360 preparation method Methods 0.000 title claims abstract 8
150000003053 piperidines Chemical class 0.000 title claims 2
239000003814 drug Substances 0.000 claims abstract description 8
229940127291 Calcium channel antagonist Drugs 0.000 claims abstract description 4
150000003839 salts Chemical class 0.000 claims abstract description 4
-1 aryl pyrrolidine Chemical compound 0.000 claims description 16
MDZWFRVPKYMLPL-UHFFFAOYSA-N 3-(3-methoxyphenyl)pyrrolidine Chemical compound COC1=CC=CC(C2CNCC2)=C1 MDZWFRVPKYMLPL-UHFFFAOYSA-N 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
239000012280 lithium aluminium hydride Substances 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 4
229910000104 sodium hydride Inorganic materials 0.000 claims description 4
XONCWXYGZWWPFZ-UHFFFAOYSA-N 1-(2-benzhydryloxyethyl)-3-(3-methoxyphenyl)pyrrolidine Chemical compound COC1=CC=CC(C2CN(CCOC(C=3C=CC=CC=3)C=3C=CC=CC=3)CC2)=C1 XONCWXYGZWWPFZ-UHFFFAOYSA-N 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
ZIOFREVANSHGDE-UHFFFAOYSA-N 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-3-(3-methoxyphenyl)pyrrolidine Chemical compound COC1=CC=CC(C2CN(CCOC(C=3C=CC(F)=CC=3)C=3C=CC(F)=CC=3)CC2)=C1 ZIOFREVANSHGDE-UHFFFAOYSA-N 0.000 claims description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 2
150000001408 amides Chemical class 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
239000012312 sodium hydride Substances 0.000 claims description 2
CASLHHLEQGBDKK-UHFFFAOYSA-N 1-[1-bromoethoxy-(4-fluorophenyl)methyl]-4-fluorobenzene Chemical compound C=1C=C(F)C=CC=1C(OC(Br)C)C1=CC=C(F)C=C1 CASLHHLEQGBDKK-UHFFFAOYSA-N 0.000 claims 1
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 1
208000019695 Migraine disease Diseases 0.000 claims 1
230000001746 atrial effect Effects 0.000 claims 1
230000002490 cerebral effect Effects 0.000 claims 1
208000035475 disorder Diseases 0.000 claims 1
206010027599 migraine Diseases 0.000 claims 1
230000002093 peripheral effect Effects 0.000 claims 1
238000011321 prophylaxis Methods 0.000 claims 1
150000003235 pyrrolidines Chemical class 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
238000011282 treatment Methods 0.000 claims 1
208000019553 vascular disease Diseases 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 10
230000001225 therapeutic effect Effects 0.000 abstract 2
238000004519 manufacturing process Methods 0.000 abstract 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 63
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 61
239000000243 solution Substances 0.000 description 60
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
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BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 30
239000000203 mixture Substances 0.000 description 29
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 28
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
238000004458 analytical method Methods 0.000 description 22
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
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239000000377 silicon dioxide Substances 0.000 description 17
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PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
229910052938 sodium sulfate Inorganic materials 0.000 description 14
235000011152 sodium sulphate Nutrition 0.000 description 14
238000001914 filtration Methods 0.000 description 13
239000003480 eluent Substances 0.000 description 12
239000000047 product Substances 0.000 description 11
229910000029 sodium carbonate Inorganic materials 0.000 description 11
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 10
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NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
239000002904 solvent Substances 0.000 description 9
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 8
MUKSLGKYFRLGOB-UHFFFAOYSA-N 1-[2-bromoethoxy-(4-fluorophenyl)methyl]-4-fluorobenzene Chemical compound C1=CC(F)=CC=C1C(OCCBr)C1=CC=C(F)C=C1 MUKSLGKYFRLGOB-UHFFFAOYSA-N 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
238000001704 evaporation Methods 0.000 description 7
230000008020 evaporation Effects 0.000 description 7
235000006408 oxalic acid Nutrition 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
239000012429 reaction media Substances 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
238000004821 distillation Methods 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
PXMDLNFRUVGKCU-UHFFFAOYSA-N 2-benzhydryloxyacetyl chloride Chemical compound C=1C=CC=CC=1C(OCC(=O)Cl)C1=CC=CC=C1 PXMDLNFRUVGKCU-UHFFFAOYSA-N 0.000 description 5
HYARBELXZXURQQ-UHFFFAOYSA-N [2-bromoethoxy(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(OCCBr)C1=CC=CC=C1 HYARBELXZXURQQ-UHFFFAOYSA-N 0.000 description 5
230000000694 effects Effects 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
230000010412 perfusion Effects 0.000 description 4
239000012071 phase Substances 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
XTSOHPFZIJWIJK-UHFFFAOYSA-N 1-(2-benzhydryloxyethyl)-3-(3-methoxyphenyl)piperidine;oxalic acid Chemical compound OC(=O)C(O)=O.COC1=CC=CC(C2CN(CCOC(C=3C=CC=CC=3)C=3C=CC=CC=3)CCC2)=C1 XTSOHPFZIJWIJK-UHFFFAOYSA-N 0.000 description 3
ZGNWABHCIIYZFN-UHFFFAOYSA-N 1-(2-benzhydryloxyethyl)-3-phenylpiperidine;oxalic acid Chemical compound OC(=O)C(O)=O.C=1C=CC=CC=1C(C=1C=CC=CC=1)OCCN(C1)CCCC1C1=CC=CC=C1 ZGNWABHCIIYZFN-UHFFFAOYSA-N 0.000 description 3
RWSALXYPUGXDLJ-UHFFFAOYSA-N 1-[3-bromopropoxy-(4-fluorophenyl)methyl]-4-fluorobenzene Chemical compound C1=CC(F)=CC=C1C(OCCCBr)C1=CC=C(F)C=C1 RWSALXYPUGXDLJ-UHFFFAOYSA-N 0.000 description 3
ISIDMZGZFSGSBH-UHFFFAOYSA-N 2-benzhydryloxy-1-(3-phenylpiperidin-1-yl)ethanone Chemical compound C1CCC(C=2C=CC=CC=2)CN1C(=O)COC(C=1C=CC=CC=1)C1=CC=CC=C1 ISIDMZGZFSGSBH-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
BJWBUBPPFLVWPX-UHFFFAOYSA-N [2-bromopropoxy(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(OCC(Br)C)C1=CC=CC=C1 BJWBUBPPFLVWPX-UHFFFAOYSA-N 0.000 description 3
210000001367 artery Anatomy 0.000 description 3
OQROAIRCEOBYJA-UHFFFAOYSA-N bromodiphenylmethane Chemical compound C=1C=CC=CC=1C(Br)C1=CC=CC=C1 OQROAIRCEOBYJA-UHFFFAOYSA-N 0.000 description 3
239000011575 calcium Substances 0.000 description 3
229910052791 calcium Inorganic materials 0.000 description 3
239000013078 crystal Substances 0.000 description 3
SMANXXCATUTDDT-QPJJXVBHSA-N flunarizine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)N1CCN(C\C=C\C=2C=CC=CC=2)CC1 SMANXXCATUTDDT-QPJJXVBHSA-N 0.000 description 3
229960000326 flunarizine Drugs 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000013049 sediment Substances 0.000 description 3
HGUFAMQASNRTCP-UHFFFAOYSA-N 1-(1-benzhydryloxypropan-2-yl)-3-(3-methoxyphenyl)pyrrolidine;oxalic acid Chemical compound OC(=O)C(O)=O.COC1=CC=CC(C2CN(CC2)C(C)COC(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HGUFAMQASNRTCP-UHFFFAOYSA-N 0.000 description 2
PJUQSICNDGZQIR-UHFFFAOYSA-N 1-(2-benzhydryloxyethyl)-3-(3-methoxyphenyl)pyrrolidine;oxalic acid Chemical compound OC(=O)C(O)=O.COC1=CC=CC(C2CN(CCOC(C=3C=CC=CC=3)C=3C=CC=CC=3)CC2)=C1 PJUQSICNDGZQIR-UHFFFAOYSA-N 0.000 description 2
VEBTZBKGJSKRBA-UHFFFAOYSA-N 1-(3-benzhydryloxypropyl)-3-(3-methoxyphenyl)pyrrolidine Chemical compound COC1=CC=CC(C2CN(CCCOC(C=3C=CC=CC=3)C=3C=CC=CC=3)CC2)=C1 VEBTZBKGJSKRBA-UHFFFAOYSA-N 0.000 description 2
RFKYBVKHJCQTRJ-WLHGVMLRSA-N 1-[3-[bis(4-fluorophenyl)methoxy]propyl]-3-(3-methoxyphenyl)pyrrolidine;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.COC1=CC=CC(C2CN(CCCOC(C=3C=CC(F)=CC=3)C=3C=CC(F)=CC=3)CC2)=C1 RFKYBVKHJCQTRJ-WLHGVMLRSA-N 0.000 description 2
HXDAZUSPEXGQSS-UHFFFAOYSA-N 1-[bromo-(4-fluorophenyl)methyl]-4-fluorobenzene Chemical compound C1=CC(F)=CC=C1C(Br)C1=CC=C(F)C=C1 HXDAZUSPEXGQSS-UHFFFAOYSA-N 0.000 description 2
KTJJUKVTVSPXMV-UHFFFAOYSA-N 2-benzhydryloxy-1-(4-phenylpiperidin-1-yl)ethanone Chemical compound C1CC(C=2C=CC=CC=2)CCN1C(=O)COC(C=1C=CC=CC=1)C1=CC=CC=C1 KTJJUKVTVSPXMV-UHFFFAOYSA-N 0.000 description 2
KWGQOJWITMQEOT-UHFFFAOYSA-N 2-benzhydryloxyacetic acid Chemical compound C=1C=CC=CC=1C(OCC(=O)O)C1=CC=CC=C1 KWGQOJWITMQEOT-UHFFFAOYSA-N 0.000 description 2
LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 2
VFZRZRDOXPRTSC-UHFFFAOYSA-N 3,5-Dimethoxybenzaldehyde Chemical compound COC1=CC(OC)=CC(C=O)=C1 VFZRZRDOXPRTSC-UHFFFAOYSA-N 0.000 description 2
KPLSJXSTLNRLAF-UHFFFAOYSA-N 3-(3-propan-2-yloxyphenyl)pyrrolidine Chemical compound CC(C)OC1=CC=CC(C2CNCC2)=C1 KPLSJXSTLNRLAF-UHFFFAOYSA-N 0.000 description 2
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125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 2
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KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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GFZQIBGSJFUBPU-UHFFFAOYSA-N [3-bromopropoxy(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(OCCCBr)C1=CC=CC=C1 GFZQIBGSJFUBPU-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
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IVRZVPSCZNKBDM-UHFFFAOYSA-N 1-(2-benzhydryloxyethyl)-2-(3-methoxyphenyl)pyrrolidine Chemical compound COC1=CC=CC(C2N(CCC2)CCOC(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 IVRZVPSCZNKBDM-UHFFFAOYSA-N 0.000 description 1
PHWZDIJXNWOTLB-UHFFFAOYSA-N 1-(2-benzhydryloxyethyl)-2-phenylpyrrolidine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)OCCN1CCCC1C1=CC=CC=C1 PHWZDIJXNWOTLB-UHFFFAOYSA-N 0.000 description 1
SPIYCHGELGRFNC-UHFFFAOYSA-N 1-(2-benzhydryloxyethyl)-2-phenylpyrrolidine;oxalic acid Chemical compound OC(=O)C(O)=O.C=1C=CC=CC=1C(C=1C=CC=CC=1)OCCN1CCCC1C1=CC=CC=C1 SPIYCHGELGRFNC-UHFFFAOYSA-N 0.000 description 1
FTNQRMDSLZCGQD-UHFFFAOYSA-N 1-(2-benzhydryloxyethyl)-3-(3,4-dimethoxyphenyl)pyrrolidine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=C(OC)C(OC)=CC=C1C1CN(CCOC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 FTNQRMDSLZCGQD-UHFFFAOYSA-N 0.000 description 1
XJRVEEQJMUPJDI-UHFFFAOYSA-N 1-(2-benzhydryloxyethyl)-4-phenylpiperidine;oxalic acid Chemical compound OC(=O)C(O)=O.C=1C=CC=CC=1C(C=1C=CC=CC=1)OCCN(CC1)CCC1C1=CC=CC=C1 XJRVEEQJMUPJDI-UHFFFAOYSA-N 0.000 description 1
RJPYOKIVJCMREB-UHFFFAOYSA-N 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-2-(3-methoxyphenyl)pyrrolidine Chemical compound COC1=CC=CC(C2N(CCC2)CCOC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)=C1 RJPYOKIVJCMREB-UHFFFAOYSA-N 0.000 description 1
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GCUHGOIVROQJRK-UHFFFAOYSA-N 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-3-(3-propan-2-yloxyphenyl)pyrrolidine Chemical compound CC(C)OC1=CC=CC(C2CN(CCOC(C=3C=CC(F)=CC=3)C=3C=CC(F)=CC=3)CC2)=C1 GCUHGOIVROQJRK-UHFFFAOYSA-N 0.000 description 1
BFHUXDKUSMARCA-UHFFFAOYSA-N 1-[3-[bis(4-fluorophenyl)methoxy]propyl]-3-(3-methoxyphenyl)pyrrolidine Chemical compound COC1=CC=CC(C2CN(CCCOC(C=3C=CC(F)=CC=3)C=3C=CC(F)=CC=3)CC2)=C1 BFHUXDKUSMARCA-UHFFFAOYSA-N 0.000 description 1
QGKFYRMABWIOIW-UHFFFAOYSA-N 2-(3-methoxyphenyl)pyrrolidine Chemical compound COC1=CC=CC(C2NCCC2)=C1 QGKFYRMABWIOIW-UHFFFAOYSA-N 0.000 description 1
CHINZSUVUBYWGD-UHFFFAOYSA-N 2-benzhydryloxy-1-[3-(3-methoxyphenyl)piperidin-1-yl]ethanone Chemical compound C1(=CC=CC=C1)C(OCC(=O)N1CC(CCC1)C1=CC(=CC=C1)OC)C1=CC=CC=C1 CHINZSUVUBYWGD-UHFFFAOYSA-N 0.000 description 1
DBTWOTKWIVISQR-UHFFFAOYSA-N 2-bromopropan-1-ol Chemical compound CC(Br)CO DBTWOTKWIVISQR-UHFFFAOYSA-N 0.000 description 1
JUTDHSGANMHVIC-UHFFFAOYSA-N 2-phenylpyrrolidine Chemical compound C1CCNC1C1=CC=CC=C1 JUTDHSGANMHVIC-UHFFFAOYSA-N 0.000 description 1
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
LDHSRVLRYZPWRD-UHFFFAOYSA-N 3-(2-methoxyphenyl)pyrrolidine Chemical compound COC1=CC=CC=C1C1CNCC1 LDHSRVLRYZPWRD-UHFFFAOYSA-N 0.000 description 1
HQHZEQCBQADPSO-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)pyrrolidine Chemical compound C1=C(OC)C(OC)=CC=C1C1CNCC1 HQHZEQCBQADPSO-UHFFFAOYSA-N 0.000 description 1
HAJKRJTVGSUQQF-UHFFFAOYSA-N 3-(3,5-dimethoxyphenyl)pyrrolidine Chemical compound COC1=CC(OC)=CC(C2CNCC2)=C1 HAJKRJTVGSUQQF-UHFFFAOYSA-N 0.000 description 1
LXCUAFVVTHZALS-UHFFFAOYSA-N 3-(3-methoxyphenyl)piperidine Chemical compound COC1=CC=CC(C2CNCCC2)=C1 LXCUAFVVTHZALS-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
NZYBILDYPCVNMU-UHFFFAOYSA-N 3-phenylpiperidine Chemical compound C1CCNCC1C1=CC=CC=C1 NZYBILDYPCVNMU-UHFFFAOYSA-N 0.000 description 1
PRRFFTYUBPGHLE-UHFFFAOYSA-N 3-phenylpyrrolidine Chemical compound C1NCCC1C1=CC=CC=C1 PRRFFTYUBPGHLE-UHFFFAOYSA-N 0.000 description 1
NOBKCEXLDDGYID-UHFFFAOYSA-N 3-propan-2-yloxybenzaldehyde Chemical compound CC(C)OC1=CC=CC(C=O)=C1 NOBKCEXLDDGYID-UHFFFAOYSA-N 0.000 description 1
NONQCMNVMIGQEE-UHFFFAOYSA-N 4-(3-methoxyphenyl)piperidine Chemical compound COC1=CC=CC(C2CCNCC2)=C1 NONQCMNVMIGQEE-UHFFFAOYSA-N 0.000 description 1
QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 description 1
UTBULQCHEUWJNV-UHFFFAOYSA-N 4-phenylpiperidine Chemical compound C1CNCCC1C1=CC=CC=C1 UTBULQCHEUWJNV-UHFFFAOYSA-N 0.000 description 1
PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
UASJZNUESCZOTH-UHFFFAOYSA-N C(C(=O)O)(=O)O.C1(=CC=CC=C1)C(OCCN1CCC(CC1)C1=CC(=CC=C1)OC)C1=CC=CC=C1 Chemical compound C(C(=O)O)(=O)O.C1(=CC=CC=C1)C(OCCN1CCC(CC1)C1=CC(=CC=C1)OC)C1=CC=CC=C1 UASJZNUESCZOTH-UHFFFAOYSA-N 0.000 description 1
IPWWZOITFDOSTP-UHFFFAOYSA-N C(C=CC(=O)O)(=O)O.FC1=CC=C(C=C1)C(OCCN1CC(CC1)C1=CC(=CC=C1)OC)C1=CC=C(C=C1)F Chemical compound C(C=CC(=O)O)(=O)O.FC1=CC=C(C=C1)C(OCCN1CC(CC1)C1=CC(=CC=C1)OC)C1=CC=C(C=C1)F IPWWZOITFDOSTP-UHFFFAOYSA-N 0.000 description 1
XSALHFHTQKQTQX-BTJKTKAUSA-N C(\C=C/C(=O)O)(=O)O.C1(=CC=CC=C1)C(OCCN1CC(CC1)C1=C(C=CC=C1)OC)C1=CC=CC=C1 Chemical compound C(\C=C/C(=O)O)(=O)O.C1(=CC=CC=C1)C(OCCN1CC(CC1)C1=C(C=CC=C1)OC)C1=CC=CC=C1 XSALHFHTQKQTQX-BTJKTKAUSA-N 0.000 description 1
PTOFALCVGBUWTP-UHFFFAOYSA-N C1(=CC=CC=C1)C(OCCN1CC(CC1)C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)C(OCCN1CC(CC1)C1=CC=CC=C1)C1=CC=CC=C1 PTOFALCVGBUWTP-UHFFFAOYSA-N 0.000 description 1
102000014914 Carrier Proteins Human genes 0.000 description 1
108010078791 Carrier Proteins Proteins 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
229910010082 LiAlH Inorganic materials 0.000 description 1
240000007711 Peperomia pellucida Species 0.000 description 1
102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 1
108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
244000309464 bull Species 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Substances OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000000470 constituent Substances 0.000 description 1
230000002999 depolarising effect Effects 0.000 description 1
125000005805 dimethoxy phenyl group Chemical group 0.000 description 1
201000010099 disease Diseases 0.000 description 1
239000008298 dragée Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
229940102223 injectable solution Drugs 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical class II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
231100000926 not very toxic Toxicity 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
230000035515 penetration Effects 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
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
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
BYQADQLDVPAGSR-UHFFFAOYSA-N toluene;hydrobromide Chemical compound Br.CC1=CC=CC=C1 BYQADQLDVPAGSR-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 radicals, substituted by hetero atoms, 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/06—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 radicals, containing only hydrogen and carbon atoms, 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
- C07D211/08—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
- C07D211/10—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 radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—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 radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
- 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
- C07D211/20—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 singly bound oxygen or sulphur atoms
- C07D211/22—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 singly bound oxygen or sulphur atoms by oxygen atoms
- H—ELECTRICITY
- H03—ELECTRONIC CIRCUITRY
- H03H—IMPEDANCE NETWORKS, e.g. RESONANT CIRCUITS; RESONATORS
- H03H7/00—Multiple-port networks comprising only passive electrical elements as network components
- H03H7/01—Frequency selective two-port networks
- H03H7/09—Filters comprising mutual inductance

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Pain & Pain Management (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Pyrrole Compounds (AREA)

DD89332899A 1988-09-23 1989-09-22 Verfahren zur herstellung von 1-[(diarylmethoxy)-alkyl]-pyrrolidinen und -piperidinen DD284875A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR8812430A FR2636946B1 (fr)	1988-09-23	1988-09-23	((diarylmethoxy)alcoyl)-1 pyrrolidines et piperidines, procedes de preparation et medicaments les contenant

Publications (1)

Publication Number	Publication Date
DD284875A5 true DD284875A5 (de)	1990-11-28

Family

ID=9370298

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD89332899A DD284875A5 (de)	1988-09-23	1989-09-22	Verfahren zur herstellung von 1-[(diarylmethoxy)-alkyl]-pyrrolidinen und -piperidinen

Country Status (25)

Country	Link
US (1)	US4957927A (no)
EP (1)	EP0360685B1 (no)
JP (1)	JPH02121964A (no)
AR (1)	AR246255A1 (no)
AT (1)	ATE101132T1 (no)
AU (1)	AU617530B2 (no)
CA (1)	CA1327364C (no)
CZ (1)	CZ279282B6 (no)
DD (1)	DD284875A5 (no)
DE (1)	DE68912860T2 (no)
DK (1)	DK468389A (no)
ES (1)	ES2062071T3 (no)
FR (1)	FR2636946B1 (no)
HU (1)	HU208422B (no)
IE (1)	IE63648B1 (no)
IL (1)	IL91689A0 (no)
MA (1)	MA21631A1 (no)
NO (1)	NO893764L (no)
NZ (1)	NZ230744A (no)
OA (1)	OA09135A (no)
PT (1)	PT91783B (no)
SU (1)	SU1757462A3 (no)
TN (1)	TNSN89103A1 (no)
YU (1)	YU170189A (no)
ZA (1)	ZA897212B (no)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
MX9100517A (es) *	1990-08-06	1992-04-01	Smith Kline French Lab	Compuestos
MX9100513A (es) *	1990-08-06	1992-04-01	Smith Kline French Lab	Compuestos
IE910818A1 (en) *	1990-08-09	1992-02-12	Sankyo Co	(benzhydryloxyethylpiperidyl)aliphatic acid derivatives and¹their use in the treatment of allergies and asthma
GB9113031D0 (en) *	1991-06-17	1991-08-07	Smithkline Beecham Plc	Compounds
US5578639A (en) *	1994-07-01	1996-11-26	Warner-Lambert Company	PLA2 inhibitors and their use for inhibition of intestinal cholesterol absorption
US6153754A (en) *	1995-12-21	2000-11-28	Albany Molecular Research, Inc.	Process for production of piperidine derivatives
US6201124B1 (en)	1995-12-21	2001-03-13	Albany Molecular Research, Inc.	Process for production of piperidine derivatives
US5747523A (en) *	1996-01-24	1998-05-05	Guilford Pharmaceuticals Inc.	Substituted ethyl α,α-diarylmethyl ether derivatives
US6011035A (en) *	1998-06-30	2000-01-04	Neuromed Technologies Inc.	Calcium channel blockers
US6946475B1 (en)	1999-04-07	2005-09-20	University Of Virginia Patent Foundation	Anticancer calcium channel blockers
DE60011755T2 (de) *	1999-04-07	2005-06-30	The University Of Virginia Patent Foundation	Calciumkanalblocker als antikrebsmittel
US6930186B2 (en) *	2001-06-13	2005-08-16	Teva Pharmacetical Industries Ltd.	Process for the preparation of paroxetine substantially free of alkoxy impurities
CA2787673A1 (en)	2010-03-01	2011-09-09	Tau Therapeutics Llc	Cancer diagnosis and imaging

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1545094A (en) *	1976-12-14	1979-05-02	Gist Brocades Nv	Piperazine derivatives

1988
- 1988-09-23 FR FR8812430A patent/FR2636946B1/fr not_active Expired - Lifetime
1989
- 1989-09-06 YU YU01701/89A patent/YU170189A/xx unknown
- 1989-09-19 EP EP89402561A patent/EP0360685B1/fr not_active Expired - Lifetime
- 1989-09-19 IL IL91689A patent/IL91689A0/xx not_active IP Right Cessation
- 1989-09-19 DE DE68912860T patent/DE68912860T2/de not_active Expired - Fee Related
- 1989-09-19 AT AT89402561T patent/ATE101132T1/de not_active IP Right Cessation
- 1989-09-19 ES ES89402561T patent/ES2062071T3/es not_active Expired - Lifetime
- 1989-09-20 MA MA21885A patent/MA21631A1/fr unknown
- 1989-09-20 JP JP1242360A patent/JPH02121964A/ja active Pending
- 1989-09-20 AR AR89314972A patent/AR246255A1/es active
- 1989-09-21 ZA ZA897212A patent/ZA897212B/xx unknown
- 1989-09-22 NZ NZ230744A patent/NZ230744A/en unknown
- 1989-09-22 TN TNTNSN89103A patent/TNSN89103A1/fr unknown
- 1989-09-22 PT PT91783A patent/PT91783B/pt not_active IP Right Cessation
- 1989-09-22 DK DK468389A patent/DK468389A/da not_active Application Discontinuation
- 1989-09-22 HU HU894981A patent/HU208422B/hu not_active IP Right Cessation
- 1989-09-22 CA CA000612673A patent/CA1327364C/fr not_active Expired - Fee Related
- 1989-09-22 US US07/410,705 patent/US4957927A/en not_active Expired - Fee Related
- 1989-09-22 CZ CS895409A patent/CZ279282B6/cs unknown
- 1989-09-22 SU SU894742008A patent/SU1757462A3/ru active
- 1989-09-22 DD DD89332899A patent/DD284875A5/de not_active IP Right Cessation
- 1989-09-22 NO NO89893764A patent/NO893764L/no unknown
- 1989-09-22 OA OA59651A patent/OA09135A/xx unknown
- 1989-09-22 AU AU41690/89A patent/AU617530B2/en not_active Ceased
- 1989-09-22 IE IE305089A patent/IE63648B1/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
IE63648B1 (en)	1995-05-31
CA1327364C (fr)	1994-03-01
EP0360685A1 (fr)	1990-03-28
HU208422B (en)	1993-10-28
ES2062071T3 (es)	1994-12-16
PT91783B (pt)	1995-08-09
SU1757462A3 (ru)	1992-08-23
HUT52049A (en)	1990-06-28
JPH02121964A (ja)	1990-05-09
AR246255A1 (es)	1994-07-29
DE68912860D1 (de)	1994-03-17
AU4169089A (en)	1990-03-29
FR2636946A1 (fr)	1990-03-30
DK468389D0 (da)	1989-09-22
PT91783A (pt)	1990-03-30
CZ279282B6 (cs)	1995-04-12
US4957927A (en)	1990-09-18
NO893764D0 (no)	1989-09-22
YU170189A (en)	1991-02-28
CZ540989A3 (en)	1994-11-16
TNSN89103A1 (fr)	1991-02-04
IL91689A0 (en)	1990-06-10
AU617530B2 (en)	1991-11-28
DE68912860T2 (de)	1994-08-11
NZ230744A (en)	1991-06-25
FR2636946B1 (fr)	1990-11-02
EP0360685B1 (fr)	1994-02-02
OA09135A (fr)	1991-10-31
MA21631A1 (fr)	1990-04-01
DK468389A (da)	1990-03-24
ZA897212B (en)	1991-03-27
NO893764L (no)	1990-03-26
ATE101132T1 (de)	1994-02-15
IE893050L (en)	1990-03-23

Legal Events

Date	Code	Title	Description
1998-07-30	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE69103206T2 (de)	1995-03-09	Neue Derivate des Aminopiperidins, Aminopyrrolidins und des Aminoperhydroazepins, Verfahren zur Herstellung und diese enthaltende Arzneimittel.
DE3787688T2 (de)	1994-02-03	Diamin-Verbindungen.
DE3248160C2 (de)	1993-12-09	2-[4-[(4,4-Dialkyl-2,6-piperidindion-1-yl)-butyl]-1-piperazinyl]pyrimidine, Verfahren zu ihrer Herstellung und pharmazeutische Mittel, die diese Verbindungen enthalten
DE2203373C3 (de)	1978-04-13	Neue 2- [(2- Alkylbenzofuran-3-yl)-methyl] -A2 -imidazoline
DE69116705T2 (de)	1996-09-26	Antiglancoma-Zusammensetzungen enthaltend 3-Arylcarbonyl-1-aminoalkyl-1H-indol
DE602005005456T2 (de)	2009-04-09	Neue azabicyclische derivate, herstellungsverfahren dafür und sie enthaltende pharmazeutische zusammensetzungen
DE3600390A1 (de)	1987-07-16	Diarylalkyl-substituierte alkylamine, verfahren zu ihrer herstellung, ihre verwendung sowie sie enthaltende arzneimittel
EP0136658A2 (de)	1985-04-10	1-Benzyl-aminoalkyl-pyrrolidinone und ihre Säureadditionssalze, Verfahren zu ihrer Herstellung und Arzneimittel
DE69120899T2 (de)	1997-02-27	Neue N-Benzoylprolin-Derivate, Verfahren zur Herstellung und diese enthaltende Arzneimittel
DE69004973T2 (de)	1994-06-23	Piperidine, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel.
DE2363052C2 (no)	1988-07-21
DE68912860T2 (de)	1994-08-11	1-[(Diarylmethoxy)alkyl]-pyrrolidine und -piperidine, Verfahren zu ihrer Herstellung und Arzneimittel, die sie enthalten.
DE2724989A1 (de)	1977-12-15	Guanidinderivate, verfahren zu ihrer herstellung und arzneimittel
CH637130A5 (de)	1983-07-15	Chinazolin-derivate, verfahren zu ihrer herstellung und verwendung dieser derivate in arzneimitteln.
DE69112074T2 (de)	1996-01-11	Disubstituierte arylverbindungen welche eine selektive leukotrien-b4 antagonistische aktivität aufweisen.
CH675418A5 (no)	1990-09-28
DD149071A5 (de)	1981-06-24	Herstellung 2-substituierter trans-5-aryl-2,3,4,4a,5,9b-hexahydro-1h-pyrido eckige klammer auf 4,3-b eckige klammer zu indole
DE68911699T2 (de)	1994-04-28	Diamin-Verbindungen.
DE69116237T2 (de)	1996-07-25	Derivate von Hexahydroazepine, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE3856501T2 (de)	2004-04-29	Schlafverbesserungsmittel
DE2329430A1 (de)	1974-01-03	1-acyl-3-(amino-niedrig-alkyl)-indole
DE69201368T2 (de)	1995-10-05	1-(Alkoxybenzyl)piperazineamide, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammensetzungen.
DE2044172C3 (de)	1975-11-13	Pyrrolderivate, ein Verfahren zu ihrer Herstellung und Arzneimittel
EP0243905B1 (de)	1990-10-10	1(omega-[bis-(Phenyl)-alkoxy]-alkyl)-4-(di-(phenyl)-methyl)- Piperazine, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE69408674T2 (de)	1998-09-10	Phenylpyrrol-derivate und ihre verwendung als dopamin d3 antagonisten