IL44850A - Pharmaceutical preparations containing 1-methyl-4-(2-benzofuranyl)-piperidine - Google Patents

Pharmaceutical preparations containing 1-methyl-4-(2-benzofuranyl)-piperidine

Info

Publication number: IL44850A
Authority: IL; Israel
Prior art keywords: benzofuranyl; methyl; piperidine; pharmaceutical preparations; solution
Prior art date: 1973-05-25

Application number

IL44850A

Other languages

English (en)

Other versions

IL44850A0 (en

Original Assignee

Ciba Geigy 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.)

1973-05-25

Filing date

1974-05-17

Publication date

1977-03-31

1974-05-17 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1974-07-31 Publication of IL44850A0 publication Critical patent/IL44850A0/xx

1977-03-31 Publication of IL44850A publication Critical patent/IL44850A/en

Links

239000000825 pharmaceutical preparation Substances 0.000 title claims description 9
MNWKXFHVRMBQKO-UHFFFAOYSA-N 4-(1-benzofuran-2-yl)-1-methylpiperidine Chemical compound C1CN(C)CCC1C1=CC2=CC=CC=C2O1 MNWKXFHVRMBQKO-UHFFFAOYSA-N 0.000 title description 3
150000003839 salts Chemical class 0.000 claims description 15
238000002360 preparation method Methods 0.000 claims description 6
208000020401 Depressive disease Diseases 0.000 claims description 4
201000003102 mental depression Diseases 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 3
150000007522 mineralic acids Chemical class 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
238000007911 parenteral administration Methods 0.000 claims description 3
239000000463 material Substances 0.000 claims 2
239000000243 solution Substances 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
239000013543 active substance Substances 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
239000001828 Gelatine Substances 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
229920000159 gelatin Polymers 0.000 description 7
235000019322 gelatine Nutrition 0.000 description 7
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 7
239000000126 substance Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000002253 acid Substances 0.000 description 6
239000002775 capsule Substances 0.000 description 6
239000000203 mixture Substances 0.000 description 6
239000000829 suppository Substances 0.000 description 6
239000008298 dragée Substances 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
239000008187 granular material Substances 0.000 description 5
239000000454 talc Substances 0.000 description 5
235000012222 talc Nutrition 0.000 description 5
229910052623 talc Inorganic materials 0.000 description 5
-1 2-benzofuranyl Chemical group 0.000 description 4
LGTULKCVKOMQDR-UHFFFAOYSA-N 4-(1-benzofuran-2-yl)pyridine Chemical class O1C2=CC=CC=C2C=C1C1=CC=NC=C1 LGTULKCVKOMQDR-UHFFFAOYSA-N 0.000 description 4
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
239000008101 lactose Substances 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
239000000155 melt Substances 0.000 description 4
230000000144 pharmacologic effect Effects 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
229920001592 potato starch Polymers 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
229920002261 Corn starch Polymers 0.000 description 3
235000019759 Maize starch Nutrition 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002585 base Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
WCJAFOKWZXCOOQ-UHFFFAOYSA-N 2-(pyridin-4-ylmethoxy)benzaldehyde Chemical compound O=CC1=CC=CC=C1OCC1=CC=NC=C1 WCJAFOKWZXCOOQ-UHFFFAOYSA-N 0.000 description 2
PWGXETSPNUBPGV-UHFFFAOYSA-N 4-(1-benzofuran-2-yl)piperidine Chemical group C1CNCCC1C1=CC2=CC=CC=C2O1 PWGXETSPNUBPGV-UHFFFAOYSA-N 0.000 description 2
244000215068 Acacia senegal Species 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
229920000084 Gum arabic Polymers 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
235000021355 Stearic acid Nutrition 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
239000000205 acacia gum Substances 0.000 description 2
235000010489 acacia gum Nutrition 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
229940075614 colloidal silicon dioxide Drugs 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000001816 cooling Methods 0.000 description 2
235000013681 dietary sucrose Nutrition 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
239000012188 paraffin wax Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
241000894007 species Species 0.000 description 2
239000008117 stearic acid Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000007920 subcutaneous administration Methods 0.000 description 2
229960004793 sucrose Drugs 0.000 description 2
239000004408 titanium dioxide Substances 0.000 description 2
150000003626 triacylglycerols Chemical class 0.000 description 2
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
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 1
ZDHKVKPZQKYREU-UHFFFAOYSA-N 4-(chloromethyl)pyridine;hydron;chloride Chemical compound Cl.ClCC1=CC=NC=C1 ZDHKVKPZQKYREU-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
229920000945 Amylopectin Polymers 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
241000207199 Citrus Species 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
239000004150 EU approved colour Substances 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
241001466453 Laminaria Species 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
102000004316 Oxidoreductases Human genes 0.000 description 1
108090000854 Oxidoreductases Proteins 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
229920001800 Shellac Polymers 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
239000003708 ampul Substances 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
238000001949 anaesthesia Methods 0.000 description 1
238000010171 animal model Methods 0.000 description 1
230000001430 anti-depressive effect Effects 0.000 description 1
239000000935 antidepressant agent Substances 0.000 description 1
229940005513 antidepressants Drugs 0.000 description 1
230000000949 anxiolytic effect Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
229940125717 barbiturate Drugs 0.000 description 1
HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
229940050390 benzoate Drugs 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229940001468 citrate Drugs 0.000 description 1
235000020971 citrus fruits Nutrition 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000004040 coloring Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
229950005627 embonate Drugs 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000008098 formaldehyde solution Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000012458 free base Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
230000000155 isotopic effect Effects 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
230000006742 locomotor activity Effects 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229940049920 malate Drugs 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
229910052757 nitrogen Inorganic materials 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
229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003791 organic solvent mixture Substances 0.000 description 1
229940049953 phenylacetate Drugs 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
239000004208 shellac Substances 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
239000004296 sodium metabisulphite Substances 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

IL44850A 1973-05-25 1974-05-17 Pharmaceutical preparations containing 1-methyl-4-(2-benzofuranyl)-piperidine IL44850A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH752773		1973-05-25

Publications (2)

Publication Number	Publication Date
IL44850A0 IL44850A0 (en)	1974-07-31
IL44850A true IL44850A (en)	1977-03-31

Family

ID=4326548

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL44850A IL44850A (en)	1973-05-25	1974-05-17	Pharmaceutical preparations containing 1-methyl-4-(2-benzofuranyl)-piperidine

Country Status (10)

Country	Link
US (1)	US3890441A (fr)
BE (1)	BE815505A (fr)
CA (1)	CA1030069A (fr)
DE (1)	DE2423835A1 (fr)
FR (1)	FR2230359B1 (fr)
GB (1)	GB1465167A (fr)
IE (1)	IE39264B1 (fr)
IL (1)	IL44850A (fr)
NL (1)	NL7406534A (fr)
ZA (1)	ZA743343B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH592656A5 (fr) *	1973-03-02	1977-10-31	Ciba Geigy Ag
CH609054A5 (en) *	1975-11-26	1979-02-15	Ciba Geigy Ag	Process for the preparation of a novel piperidine derivative
EP0006524A1 (fr) *	1978-06-22	1980-01-09	Ciba-Geigy Ag	Dérivés de tétrahydropyridine et de tétrahydropipéridine, leurs sels d'addition acides, procédés pour leur préparation et compositions pharmaceutiques les contenant
US6303627B1 (en)	1998-06-19	2001-10-16	Eli Lilly And Company	Inhibitors of serotonin reuptake

1974
- 1974-05-13 IE IE1013/74A patent/IE39264B1/xx unknown
- 1974-05-15 NL NL7406534A patent/NL7406534A/xx not_active Application Discontinuation
- 1974-05-16 DE DE2423835A patent/DE2423835A1/de active Pending
- 1974-05-17 IL IL44850A patent/IL44850A/en unknown
- 1974-05-21 FR FR7417638A patent/FR2230359B1/fr not_active Expired
- 1974-05-22 US US472332A patent/US3890441A/en not_active Expired - Lifetime
- 1974-05-23 GB GB2309074A patent/GB1465167A/en not_active Expired
- 1974-05-23 CA CA200,606A patent/CA1030069A/fr not_active Expired
- 1974-05-24 ZA ZA00743343A patent/ZA743343B/xx unknown
- 1974-05-24 BE BE144722A patent/BE815505A/fr unknown

Also Published As

Publication number	Publication date
US3890441A (en)	1975-06-17
IE39264B1 (en)	1978-08-30
BE815505A (fr)	1974-11-25
CA1030069A (fr)	1978-04-25
NL7406534A (fr)	1974-11-27
GB1465167A (en)	1977-02-23
IL44850A0 (en)	1974-07-31
FR2230359A1 (fr)	1974-12-20
FR2230359B1 (fr)	1977-11-10
AU6931174A (en)	1975-11-27
DE2423835A1 (de)	1974-12-19
IE39264L (en)	1974-11-25
ZA743343B (en)	1975-05-28

Publication	Publication Date	Title
CH616674A5 (fr)	1980-04-15
JPS6372657A (ja)	1988-04-02	新規な薬剤
US4145427A (en)	1979-03-20	N- 1-(3-Benzoyl-propyl)-4-piperidyl!-sulfonic acid amides and salts thereof
US3717641A (en)	1973-02-20	Derivatives of dibenzo cycloocten-5,11-imine
DE2408476C2 (fr)	1990-12-06
IL55115A (en)	1981-09-13	3-indolyl-tert-butylamino-propanol derivatives,their preparation and pharmaceutical compositions containing them
IL44850A (en)	1977-03-31	Pharmaceutical preparations containing 1-methyl-4-(2-benzofuranyl)-piperidine
AU619344B2 (en)	1992-01-23	Tetrahydronaphthalene and indane derivatives
US4000193A (en)	1976-12-28	Pharmacologically active compounds
DE1940566A1 (de)	1971-02-11	1-(2-Nitrilophenoxy)-2-hydroxy-3-aethylaminopropan und dessen Salze
DE2435169A1 (de)	1975-02-06	1-aryl-2- eckige klammer auf (subst.amino)alkanoyl eckige klammer zu -1,2,3,4-tetrahydroisochinoline
DE2105580A1 (en)	1972-09-07	3-aryl-benzisothiazole 1,1-dioxide derivs - which ar e non -hyperglycaemic hypotensives
US3963756A (en)	1976-06-15	Derivatives of 6-methyl-2H-pyran-2,4(3H)-dione
US3810986A (en)	1974-05-14	Novel method and composition
JPS60120853A (ja)	1985-06-28	１−（４′−アルキルチオフエニル）−２−アミノ−１，３−プロパンジオ−ルｎ−置換誘導体
DE1901750A1 (de)	1969-09-04	Neue heterocyclische Verbindungen und Verfahren zu deren Herstellung
US4098901A (en)	1978-07-04	Trifluoromethyl substituted compounds having antidepressive activity
EP0591486A1 (fr)	1994-04-13	Action immunostimulante et par consequent antivirale des composes 4- 3-(aminosubst.)-2-hydroxypropoxy]-1,2,5-thiadiazol
CH482697A (de)	1969-12-15	Verfahren zur Herstellung von neuen, kondensierten heterocyclischen Verbindungen
DE2533567A1 (de)	1976-02-19	Piperidin-derivate und verfahren zu ihrer herstellung
US4495352A (en)	1985-01-22	Heterocyclic substituted aryloxy 3-indolyl-tertiary butylaminopropanols
US3542927A (en)	1970-11-24	Reduction of blood sugar levels with aminomethylindoles
US3998820A (en)	1976-12-21	10'-[ω-N-/1,4-diazabicyclo(4,m,o)-alkanyl/-acyl]-phenothiazines, their acidic addition salts and quaternary salts, process for producing same and use
US4548947A (en)	1985-10-22	1-(Substituted-aryl)-dihydro-1H-pyrrolizine-3,5-[2H,6H-]diones and use for reversing amnesia
DE2611118A1 (de)	1976-10-07	Verbindungen mit antidepressiver wirkung