DE3706585A1 - Aryl- und aryloxy-substituierte tert.-alkylenamine, verfahren zu ihrer herstellung und ihre pharmazeutische verwendung - Google Patents

Aryl- und aryloxy-substituierte tert.-alkylenamine, verfahren zu ihrer herstellung und ihre pharmazeutische verwendung

Info

Publication number: DE3706585A1
Authority: DE; Germany
Prior art keywords: methyl; group; hydroxy; formula; methoxy
Prior art date: 1987-02-25
Legal status (The legal status 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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

DE19873706585

Other languages

German (de)

English (en)

Inventor

Rudolf Dr Albrecht

Klaus Dr Schoellkopf

Manfred Dr Lehmann

Gertrud Dr Schroeder

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer Pharma AG

Original Assignee

Schering AG

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.)

1987-02-25

Filing date

1987-02-25

Publication date

1988-09-08

1987-02-25 Application filed by Schering AG filed Critical Schering AG

1987-02-25 Priority to DE19873706585 priority Critical patent/DE3706585A1/de

1988-02-23 Priority to PCT/DE1988/000100 priority patent/WO1988006580A1/fr

1988-02-23 Priority to EP88901794A priority patent/EP0346367A1/fr

1988-02-23 Priority to JP63501802A priority patent/JPH02502376A/ja

1988-09-08 Publication of DE3706585A1 publication Critical patent/DE3706585A1/de

Status Withdrawn legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 5
238000004519 manufacturing process Methods 0.000 title abstract description 3
-1 4-fluorbenzoyl Chemical group 0.000 claims abstract description 67
239000001257 hydrogen Substances 0.000 claims abstract description 14
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
125000006662 (C2-C4) acyloxy group Chemical group 0.000 claims abstract description 12
239000002253 acid Substances 0.000 claims abstract description 9
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 9
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
101100294106 Caenorhabditis elegans nhr-3 gene Chemical group 0.000 claims abstract description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims abstract description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
150000003839 salts Chemical class 0.000 claims abstract description 5
150000007513 acids Chemical class 0.000 claims abstract description 4
WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical group OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 claims abstract description 3
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims abstract description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 3
125000002619 bicyclic group Chemical group 0.000 claims abstract description 3
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims abstract description 3
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims abstract description 3
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims abstract description 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 3
238000006798 ring closing metathesis reaction Methods 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 46
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 12
239000000460 chlorine Substances 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 10
150000002431 hydrogen Chemical group 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 8
IQZLUWLMQNGTIW-UHFFFAOYSA-N acetoveratrone Chemical compound COC1=CC=C(C(C)=O)C=C1OC IQZLUWLMQNGTIW-UHFFFAOYSA-N 0.000 claims description 8
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 4
150000001555 benzenes Chemical class 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000012280 lithium aluminium hydride Substances 0.000 claims description 3
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
229910010084 LiAlH4 Inorganic materials 0.000 claims description 2
230000010933 acylation Effects 0.000 claims description 2
238000005917 acylation reaction Methods 0.000 claims description 2
239000002168 alkylating agent Substances 0.000 claims description 2
229940100198 alkylating agent Drugs 0.000 claims description 2
150000003862 amino acid derivatives Chemical class 0.000 claims description 2
238000005661 deetherification reaction Methods 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
230000003647 oxidation Effects 0.000 claims description 2
238000007254 oxidation reaction Methods 0.000 claims description 2
ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical group [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
150000003222 pyridines Chemical class 0.000 claims description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 2
CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims 1
239000000969 carrier Substances 0.000 claims 1
239000003153 chemical reaction reagent Substances 0.000 claims 1
229940079593 drug Drugs 0.000 claims 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
125000004356 hydroxy functional group Chemical group O* 0.000 abstract 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 113
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 102
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 67
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 58
238000002844 melting Methods 0.000 description 57
230000008018 melting Effects 0.000 description 57
239000000243 solution Substances 0.000 description 47
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 33
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 25
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 23
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
238000010992 reflux Methods 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
239000000741 silica gel Substances 0.000 description 17
229910002027 silica gel Inorganic materials 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 15
238000001816 cooling Methods 0.000 description 14
239000000047 product Substances 0.000 description 14
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 13
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 12
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 12
238000000354 decomposition reaction Methods 0.000 description 12
239000000203 mixture Substances 0.000 description 12
229960001413 acetanilide Drugs 0.000 description 11
FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical compound OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 0.000 description 10
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical compound CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 description 8
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
239000005457 ice water Substances 0.000 description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
229910000027 potassium carbonate Inorganic materials 0.000 description 8
239000012265 solid product Substances 0.000 description 8
DGAKXCFQCSDXBU-UHFFFAOYSA-N 1-(3-chloropropyl)-4-methylpiperidine Chemical compound CC1CCN(CCCCl)CC1 DGAKXCFQCSDXBU-UHFFFAOYSA-N 0.000 description 7
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 7
239000011777 magnesium Substances 0.000 description 7
229910052749 magnesium Inorganic materials 0.000 description 7
229920000137 polyphosphoric acid Polymers 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
235000017557 sodium bicarbonate Nutrition 0.000 description 7
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
229910000041 hydrogen chloride Inorganic materials 0.000 description 6
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 6
239000011976 maleic acid Substances 0.000 description 6
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
NFINUZCPZMEZBQ-UHFFFAOYSA-N 4-(4-methylpiperidin-1-ium-1-yl)butanoate Chemical compound CC1CCN(CCCC(O)=O)CC1 NFINUZCPZMEZBQ-UHFFFAOYSA-N 0.000 description 5
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
239000007818 Grignard reagent Substances 0.000 description 5
238000009835 boiling Methods 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
RDACSAIDBWLKCA-UHFFFAOYSA-N 1-(3-amino-4-hydroxyphenyl)-4-(4-methylpiperidin-1-yl)butan-1-one Chemical compound C1CC(C)CCN1CCCC(=O)C1=CC=C(O)C(N)=C1 RDACSAIDBWLKCA-UHFFFAOYSA-N 0.000 description 4
AYSNTKNVMWOEJV-UHFFFAOYSA-N 1-(3-amino-4-methoxyphenyl)-4-(4-methylpiperidin-1-yl)butan-1-one Chemical compound C1=C(N)C(OC)=CC=C1C(=O)CCCN1CCC(C)CC1 AYSNTKNVMWOEJV-UHFFFAOYSA-N 0.000 description 4
HSLGIOOHGLUYNX-UHFFFAOYSA-N 1-(4-amino-3-methoxyphenyl)-4-(4-methylpiperidin-1-yl)butan-1-one Chemical compound C1=C(N)C(OC)=CC(C(=O)CCCN2CCC(C)CC2)=C1 HSLGIOOHGLUYNX-UHFFFAOYSA-N 0.000 description 4
UCSIYAINYCFCSP-UHFFFAOYSA-N 2,2-dimethoxy-1-phenylbutan-1-one Chemical compound CCC(OC)(OC)C(=O)C1=CC=CC=C1 UCSIYAINYCFCSP-UHFFFAOYSA-N 0.000 description 4
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 4
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
235000019253 formic acid Nutrition 0.000 description 4
150000004795 grignard reagents Chemical class 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
239000001632 sodium acetate Substances 0.000 description 4
235000017281 sodium acetate Nutrition 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 4
DVVLTABTKVOGCS-UHFFFAOYSA-N 2-chloro-3,4-dimethoxybenzonitrile Chemical compound COC1=CC=C(C#N)C(Cl)=C1OC DVVLTABTKVOGCS-UHFFFAOYSA-N 0.000 description 3
IBBYQNVXKFMSSI-UHFFFAOYSA-N 2-fluoro-4,5-dimethoxybenzaldehyde Chemical compound COC1=CC(F)=C(C=O)C=C1OC IBBYQNVXKFMSSI-UHFFFAOYSA-N 0.000 description 3
QZKGCLSVCWWARO-UHFFFAOYSA-N 2-fluoro-4,5-dimethoxybenzonitrile Chemical compound COC1=CC(F)=C(C#N)C=C1OC QZKGCLSVCWWARO-UHFFFAOYSA-N 0.000 description 3
VRQNOAXKBNUJDH-UHFFFAOYSA-N 3,4-dimethoxy-2-methylbenzonitrile Chemical compound COC1=CC=C(C#N)C(C)=C1OC VRQNOAXKBNUJDH-UHFFFAOYSA-N 0.000 description 3
FYVNQNKFUPQFLQ-UHFFFAOYSA-N 3-chloro-4,5-dimethoxybenzonitrile Chemical compound COC1=CC(C#N)=CC(Cl)=C1OC FYVNQNKFUPQFLQ-UHFFFAOYSA-N 0.000 description 3
OWYLAEYXIQKAOL-UHFFFAOYSA-N 4-(1-pyrrolidinyl)-1-(2,4,6-trimethoxyphenyl)-1-butanone Chemical compound COC1=CC(OC)=CC(OC)=C1C(=O)CCCN1CCCC1 OWYLAEYXIQKAOL-UHFFFAOYSA-N 0.000 description 3
AXZVDCFTHUVNKN-UHFFFAOYSA-N 4-(4-methylpiperidin-1-yl)butanenitrile Chemical compound CC1CCN(CCCC#N)CC1 AXZVDCFTHUVNKN-UHFFFAOYSA-N 0.000 description 3
NJZZHHJHABGARR-UHFFFAOYSA-N 4-chloro-1-(3,4-dimethoxyphenyl)butan-1-one Chemical compound COC1=CC=C(C(=O)CCCCl)C=C1OC NJZZHHJHABGARR-UHFFFAOYSA-N 0.000 description 3
ZGPBIYQLQYUVHD-UHFFFAOYSA-N 7-methoxy-4-[4-(4-methylpiperidin-1-yl)butanoyl]-1,3-dihydroindol-2-one Chemical compound C1=2CC(=O)NC=2C(OC)=CC=C1C(=O)CCCN1CCC(C)CC1 ZGPBIYQLQYUVHD-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
229960001415 buflomedil Drugs 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
239000012043 crude product Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 3
238000001035 drying Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
LFISPVWAQDCLHM-UHFFFAOYSA-N 1-(2-chloro-3,4-dihydroxyphenyl)-4-(4-methylpiperidin-1-yl)butan-1-one Chemical compound C1CC(C)CCN1CCCC(=O)C1=CC=C(O)C(O)=C1Cl LFISPVWAQDCLHM-UHFFFAOYSA-N 0.000 description 2
ZOAVGFZJGUKLQH-UHFFFAOYSA-N 1-(2-fluoro-3,4-dihydroxyphenyl)-4-(4-methylpiperidin-1-yl)butan-1-one Chemical compound C1CC(C)CCN1CCCC(=O)C1=CC=C(O)C(O)=C1F ZOAVGFZJGUKLQH-UHFFFAOYSA-N 0.000 description 2
KWTMTTHADPLZDI-UHFFFAOYSA-N 1-(2-fluoro-4,5-dihydroxyphenyl)-4-(4-methylpiperidin-1-yl)butan-1-one Chemical compound C1CC(C)CCN1CCCC(=O)C1=CC(O)=C(O)C=C1F KWTMTTHADPLZDI-UHFFFAOYSA-N 0.000 description 2
NBUDDVRXHUEMHD-UHFFFAOYSA-N 1-(3,4-dihydroxyphenyl)-3-(4-methylpiperidin-1-yl)propan-1-one Chemical compound C1CC(C)CCN1CCC(=O)C1=CC=C(O)C(O)=C1 NBUDDVRXHUEMHD-UHFFFAOYSA-N 0.000 description 2
BXAMVBLBLQTTKF-UHFFFAOYSA-N 1-(3,4-dihydroxyphenyl)-3-(dipropylamino)propan-1-one Chemical compound CCCN(CCC)CCC(=O)C1=CC=C(O)C(O)=C1 BXAMVBLBLQTTKF-UHFFFAOYSA-N 0.000 description 2
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229920001971 elastomer Polymers 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
QQXQAEWRSVZPJM-UHFFFAOYSA-N ethyl 1h-indole-2-carboxylate Chemical compound C1=CC=C2NC(C(=O)OCC)=CC2=C1 QQXQAEWRSVZPJM-UHFFFAOYSA-N 0.000 description 1
XBPOBCXHALHJFP-UHFFFAOYSA-N ethyl 4-bromobutanoate Chemical compound CCOC(=O)CCCBr XBPOBCXHALHJFP-UHFFFAOYSA-N 0.000 description 1
239000002038 ethyl acetate fraction Substances 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
235000015220 hamburgers Nutrition 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000005259 measurement Methods 0.000 description 1
IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 description 1
NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
LBTPIFQNEKOAIM-UHFFFAOYSA-N n-phenylmethanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC=C1 LBTPIFQNEKOAIM-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
229960002748 norepinephrine Drugs 0.000 description 1
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
150000004885 piperazines Chemical class 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
239000004323 potassium nitrate Substances 0.000 description 1
235000010333 potassium nitrate Nutrition 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000012264 purified product Substances 0.000 description 1
238000009419 refurbishment Methods 0.000 description 1
230000002040 relaxant effect Effects 0.000 description 1
239000005060 rubber Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
235000019254 sodium formate Nutrition 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000000565 sulfonamide group Chemical group 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 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
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
238000001665 trituration Methods 0.000 description 1
230000002792 vascular Effects 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/108—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
- 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
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- 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
- A61P9/12—Antihypertensives
- 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
- C07D211/80—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 two double bonds between ring members or between ring members and non-ring members
- C07D211/82—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 two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Plural Heterocyclic Compounds (AREA)
Indole Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DE19873706585 1987-02-25 1987-02-25 Aryl- und aryloxy-substituierte tert.-alkylenamine, verfahren zu ihrer herstellung und ihre pharmazeutische verwendung Withdrawn DE3706585A1 (de)

Priority Applications (4)

Application Number	Priority Date	Filing Date	Title
DE19873706585 DE3706585A1 (de)	1987-02-25	1987-02-25	Aryl- und aryloxy-substituierte tert.-alkylenamine, verfahren zu ihrer herstellung und ihre pharmazeutische verwendung
PCT/DE1988/000100 WO1988006580A1 (fr)	1987-02-25	1988-02-23	Alkylenamine tert. a substitution aryle et aryloxyle, leur procede de production et leur utilisation en pharmacie
EP88901794A EP0346367A1 (fr)	1987-02-25	1988-02-23	Alkylenamine tert. a substitution aryle et aryloxyle, leur procede de production et leur utilisation en pharmacie
JP63501802A JPH02502376A (ja)	1987-02-25	1988-02-23	アリール‐及びアリールオキシ‐置換ｔ‐アルキレンアミン、その製法及びその製薬学的使用

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19873706585 DE3706585A1 (de)	1987-02-25	1987-02-25	Aryl- und aryloxy-substituierte tert.-alkylenamine, verfahren zu ihrer herstellung und ihre pharmazeutische verwendung

Publications (1)

Publication Number	Publication Date
DE3706585A1 true DE3706585A1 (de)	1988-09-08

Family

ID=6322048

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE19873706585 Withdrawn DE3706585A1 (de)	1987-02-25	1987-02-25	Aryl- und aryloxy-substituierte tert.-alkylenamine, verfahren zu ihrer herstellung und ihre pharmazeutische verwendung

Country Status (4)

Country	Link
EP (1)	EP0346367A1 (fr)
JP (1)	JPH02502376A (fr)
DE (1)	DE3706585A1 (fr)
WO (1)	WO1988006580A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2001005763A3 (fr) *	1999-07-16	2002-01-17	Acadia Pharm Inc	Composes possedant une activite sur les recepteurs muscariniques

Families Citing this family (7)

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Publication number	Priority date	Publication date	Assignee	Title
WO1993022302A1 (fr) *	1992-04-24	1993-11-11	Smithkline Beecham Plc	N-aryloxy(thio)alkyl-azacycloalcanes utiles en tant qu'antagonistes des canaux calciques
KR950704284A (ko) *	1992-12-22	1995-11-17	데이비드 로버츠	칼슘 채널 길항제로서의 피페리딘 유도체(Piperidine Derivatives as Calcium Channel Antagonists)
JP2004107323A (ja) *	2002-07-26	2004-04-08	Nippon Nohyaku Co Ltd	新規なハロアルキルスルホンアニリド誘導体及び除草剤並びにその使用方法
WO2004011429A1 (fr) *	2002-07-26	2004-02-05	Nihon Nohyaku Co., Ltd.	Nouveaux derives d'haloalkylsulfonanilide, herbicides et utilisation de ceux-ci
EP1666464A4 (fr) *	2003-09-25	2008-12-10	Shionogi & Co	Derive de piperidine presentant une activite antagoniste du recepteur ndma
JP2009126785A (ja) *	2007-11-19	2009-06-11	Mitsubishi Gas Chem Co Inc	２−ヨード−３，４−ジメトキシベンゾニトリルの製造方法
JP2009126784A (ja) *	2007-11-19	2009-06-11	Mitsubishi Gas Chem Co Inc	２−ヨード−３，４−ジメトキシベンゾニトリルの製造方法。

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3317538A (en) *	1965-10-22	1967-05-02	American Home Prod	4, 4'-diamino-butyrophenones
DE1618010A1 (de) *	1967-06-15	1970-11-05	Thomae Gmbh Dr K	Verfahren zur Herstellung von neuen Aminoketonen
GB1262965A (en) *	1969-03-21	1972-02-09	Ferrosan As	Butyrophenones
SE7807408L (sv) *	1978-06-30	1979-12-31	Haessle Ab	Hjertaktiva foreningar
US4353900A (en) *	1981-10-19	1982-10-12	Syntex (U.S.A.) Inc.	9-(Arylalkyl or aroylalkyl)-1-oxa-4,9-diazaspiro(5.5)undecan-3-ones
US4613598A (en) *	1984-03-13	1986-09-23	Mitsubishi Chemical Industries Limited	Piperazine derivatives and their acid addition salts

1987
- 1987-02-25 DE DE19873706585 patent/DE3706585A1/de not_active Withdrawn
1988
- 1988-02-23 JP JP63501802A patent/JPH02502376A/ja active Pending
- 1988-02-23 EP EP88901794A patent/EP0346367A1/fr not_active Withdrawn
- 1988-02-23 WO PCT/DE1988/000100 patent/WO1988006580A1/fr not_active Ceased

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6528529B1 (en)	1998-03-31	2003-03-04	Acadia Pharmaceuticals Inc.	Compounds with activity on muscarinic receptors
US7485651B2 (en)	1998-03-31	2009-02-03	Acadia Pharmaceuticals, Inc.	Compounds with activity on muscarinic receptors
WO2001005763A3 (fr) *	1999-07-16	2002-01-17	Acadia Pharm Inc	Composes possedant une activite sur les recepteurs muscariniques

Also Published As

Publication number	Publication date
JPH02502376A (ja)	1990-08-02
WO1988006580A1 (fr)	1988-09-07
EP0346367A1 (fr)	1989-12-20

Publication	Publication Date	Title
DE1493955A1 (de)	1971-08-19	Verfahren zur Herstellung substituierter Sulfonanilide
HU184966B (en)	1984-11-28	Process for producing phenyl-piperazine derivatives of anti-agression activity
US3789072A (en)	1974-01-29	Carboxamides
CH521355A (de)	1972-04-15	Verfahren zur Herstellung von aromatischen Äthern
FI77224B (fi)	1988-10-31	Foerfarande foer framstaellning av nya, terapeutiskt anvaendbara aminopropanolderivat av 2-hydroxi- -fenylpropiofenoner.
DE3706585A1 (de)	1988-09-08	Aryl- und aryloxy-substituierte tert.-alkylenamine, verfahren zu ihrer herstellung und ihre pharmazeutische verwendung
DE3309596A1 (de)	1984-04-05	2-substituierte 1-(3'-aminoalkyl)-1,2,3,4-tetrahydro-ss-carboline, ihre herstellung und verwendung als arzneimittel
EP0008645B1 (fr)	1984-09-05	Alcoxyphénylpyrrolidones, procédé pour leur préparation et médicaments les contenant
DE3114239A1 (de)	1982-02-18	"piperazinderivate"
DE2413937A1 (de)	1974-09-26	Thiazolderivate, verfahren zu ihrer herstellung und ihre verwendung in pharmazeutischen zubereitungen
US4397855A (en)	1983-08-09	4-(Substituted)-α, α-dimethyl-1-piperazine pentanoic acids and derivatives as anti-arteriosclerotic agents and method
EP0072960B1 (fr)	1989-06-07	Composés 1,5-diphénylpyrazolin-3-one, ainsi qu'un procédé et produits intermédiaires pour leur fabrication et médicaments contenant ces composés
EP0243905B1 (fr)	1990-10-10	1(Oméga-[bis-(phényl)alcoxy]-alcoyl)-4-(di-(phényl)-méthyl-pipérazines, leur procédé de préparation et médicaments qui les contiennent
EP0072961B1 (fr)	1985-07-10	Composés 1-phénylindazol-3-one ainsi qu'un procédé et produits intermédiaires pour leur fabrication et médicaments contenant ces composés
US3167556A (en)	1965-01-26	Basic derivatives of anilides
EP0123700A1 (fr)	1984-11-07	Acides picoliniques substitués, leur procédé de préparation, leur application, et les médicaments les contenant
FI78682C (fi)	1989-09-11	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara oximetrar.
DE2623314A1 (de)	1977-12-08	Neue 1-aryloxy-2-hydroxy-3- aminopropane und verfahren zu ihrer herstellung
HU183178B (en)	1984-04-28	Process for preparing new carboxylic acid derivatives
EP0352639B1 (fr)	1994-10-19	Dérivés de p-hydroxyphénone et leur utilisation
CH649758A5 (de)	1985-06-14	1,1,2-triphenyl-propan- und -propen-derivate, verfahren zur herstellung derselben und diese verbindungen enthaltende pharmazeutische praeparate.
AT256816B (de)	1967-09-11	Verfahren zur Herstellung von neuen substituierten 1-Phenyl-2-aminoalkanolen und deren Säureadditionssalzen
US4237141A (en)	1980-12-02	Derivatives of α-methyl-β-aminopropiophenone and use thereof
EP0152556A1 (fr)	1985-08-28	Dérivés d'aminopropanol de 2-hydroxypropiophénones substituées, procédé de préparation et agents thérapeutiques les contenant
US5175174A (en)	1992-12-29	Phenylpiperidinylamines and drugs containing these

Legal Events

Date	Code	Title	Description
1994-02-17	8139	Disposal/non-payment of the annual fee