NO821699L - 3-(2-(4-piperidyl)-1-alkyl-etyl)-indoler. - Google Patents
3-(2-(4-piperidyl)-1-alkyl-etyl)-indoler.Info
- Publication number
- NO821699L NO821699L NO821699A NO821699A NO821699L NO 821699 L NO821699 L NO 821699L NO 821699 A NO821699 A NO 821699A NO 821699 A NO821699 A NO 821699A NO 821699 L NO821699 L NO 821699L
- Authority
- NO
- Norway
- Prior art keywords
- serotonin
- formula
- piperidyl
- ether
- indole
- Prior art date
Links
- -1 4-piperidyl Chemical group 0.000 title description 5
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 38
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 31
- 229940076279 serotonin Drugs 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 14
- 238000004064 recycling Methods 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 1
- 230000002460 anti-migrenic effect Effects 0.000 claims 1
- 230000002785 anti-thrombosis Effects 0.000 claims 1
- 229910052987 metal hydride Inorganic materials 0.000 claims 1
- 150000004681 metal hydrides Chemical class 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 210000001772 blood platelet Anatomy 0.000 description 6
- SADQVAVFGNTEOD-UHFFFAOYSA-N indalpine Chemical compound C=1NC2=CC=CC=C2C=1CCC1CCNCC1 SADQVAVFGNTEOD-UHFFFAOYSA-N 0.000 description 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- 229950002473 indalpine Drugs 0.000 description 4
- 210000002569 neuron Anatomy 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- ZMIXNEGXLMFWFK-UHFFFAOYSA-N 3-(1-piperidin-4-ylpropan-2-yl)-1h-indole Chemical compound C=1NC2=CC=CC=C2C=1C(C)CC1CCNCC1 ZMIXNEGXLMFWFK-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 208000019695 Migraine disease Diseases 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000009977 dual effect Effects 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- YXFSJHIKSHCRDI-UHFFFAOYSA-N iodomethane;magnesium Chemical compound [Mg].IC YXFSJHIKSHCRDI-UHFFFAOYSA-N 0.000 description 2
- 206010027599 migraine Diseases 0.000 description 2
- WWPITPSIWMXDPE-UHFFFAOYSA-N para-chloroamphetamine Chemical compound CC(N)CC1=CC=C(Cl)C=C1 WWPITPSIWMXDPE-UHFFFAOYSA-N 0.000 description 2
- 210000002381 plasma Anatomy 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 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 description 1
- YFNOTMRKVGZZNF-UHFFFAOYSA-N 2-piperidin-1-ium-4-ylacetate Chemical compound OC(=O)CC1CCNCC1 YFNOTMRKVGZZNF-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- SYQFWWGYYWTPDK-UHFFFAOYSA-N [Mg].CCl Chemical compound [Mg].CCl SYQFWWGYYWTPDK-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 239000002269 analeptic agent Substances 0.000 description 1
- 208000022531 anorexia Diseases 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 1
- 229960004676 antithrombotic agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- PSZQPESLSOKKES-UHFFFAOYSA-N benzyl 4-(2-chloro-2-oxoethyl)piperidine-1-carboxylate Chemical compound C1CC(CC(=O)Cl)CCN1C(=O)OCC1=CC=CC=C1 PSZQPESLSOKKES-UHFFFAOYSA-N 0.000 description 1
- VBHKQULFAYUASH-UHFFFAOYSA-N benzyl 4-[2-(1h-indol-3-yl)-2-oxoethyl]piperidine-1-carboxylate Chemical compound C=1NC2=CC=CC=C2C=1C(=O)CC(CC1)CCN1C(=O)OCC1=CC=CC=C1 VBHKQULFAYUASH-UHFFFAOYSA-N 0.000 description 1
- XMUXTPYQZLXXEF-UHFFFAOYSA-N benzyl 4-[2-[1-(4-methylphenyl)sulfonyloxyindol-3-yl]-2-oxoethyl]piperidine-1-carboxylate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)ON1C2=CC=CC=C2C(C(=O)CC2CCN(CC2)C(=O)OCC=2C=CC=CC=2)=C1 XMUXTPYQZLXXEF-UHFFFAOYSA-N 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000002898 effect on depression Effects 0.000 description 1
- 230000000695 effect on serotonin Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 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
- 125000005842 heteroatom Chemical group 0.000 description 1
- 210000005260 human cell Anatomy 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000035873 hypermotility Effects 0.000 description 1
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 1
- 229960004801 imipramine Drugs 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 231100000926 not very toxic Toxicity 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 229940001470 psychoactive drug Drugs 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000000697 serotonin reuptake Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000000946 synaptic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000006442 vascular tone Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8110220A FR2506311A1 (fr) | 1981-05-22 | 1981-05-22 | ((piperidyl-4)-2 alkyl-1 ethyl)-3 indoles et leur utilisation comme medicaments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO821699L true NO821699L (no) | 1982-11-23 |
Family
ID=9258784
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO821699A NO821699L (no) | 1981-05-22 | 1982-05-21 | 3-(2-(4-piperidyl)-1-alkyl-etyl)-indoler. |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4416888A (show.php) |
| EP (1) | EP0065909B1 (show.php) |
| JP (1) | JPS57200384A (show.php) |
| AR (1) | AR231445A1 (show.php) |
| AU (1) | AU551047B2 (show.php) |
| CA (1) | CA1183137A (show.php) |
| DE (1) | DE3261524D1 (show.php) |
| DK (1) | DK220882A (show.php) |
| ES (1) | ES512473A0 (show.php) |
| FR (1) | FR2506311A1 (show.php) |
| GR (1) | GR75841B (show.php) |
| HU (1) | HU188171B (show.php) |
| IL (1) | IL65474A (show.php) |
| MA (1) | MA19482A1 (show.php) |
| NO (1) | NO821699L (show.php) |
| PT (1) | PT74917B (show.php) |
| ZA (1) | ZA823492B (show.php) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0429341A3 (en) * | 1989-11-20 | 1991-11-13 | Rhone-Poulenc Sante | Heterocyclic derivatives, their preparation and pharmaceuticals containing them |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1289690A (fr) * | 1960-04-01 | 1962-04-06 | Irwin | Dérivés de l'indole |
| GB925429A (en) * | 1960-04-01 | 1963-05-08 | Irwin Neisler & Co | Indole derivatives |
| US3136770A (en) * | 1960-04-01 | 1964-06-09 | Neisler Lab Inc | Indolyl substituted piperidines |
| GB1023781A (en) * | 1962-02-01 | 1966-03-23 | Benger Lab Ltd | Substituted indoles and their preparation |
| US3462440A (en) * | 1965-12-03 | 1969-08-19 | American Home Prod | 1,4-bis(2-indol-3-ylethyl)piperidines |
| US4208417A (en) * | 1978-06-29 | 1980-06-17 | Pharmindustrie | Indole derivatives and their use as anxiolytics |
-
1981
- 1981-05-22 FR FR8110220A patent/FR2506311A1/fr active Granted
-
1982
- 1982-04-12 IL IL65474A patent/IL65474A/xx unknown
- 1982-05-03 US US06/374,365 patent/US4416888A/en not_active Expired - Fee Related
- 1982-05-04 GR GR68057A patent/GR75841B/el unknown
- 1982-05-11 EP EP82400873A patent/EP0065909B1/fr not_active Expired
- 1982-05-11 DE DE8282400873T patent/DE3261524D1/de not_active Expired
- 1982-05-17 DK DK220882A patent/DK220882A/da not_active Application Discontinuation
- 1982-05-18 PT PT74917A patent/PT74917B/pt unknown
- 1982-05-19 ZA ZA823492A patent/ZA823492B/xx unknown
- 1982-05-19 AR AR289455A patent/AR231445A1/es active
- 1982-05-20 MA MA19688A patent/MA19482A1/fr unknown
- 1982-05-21 HU HU821641A patent/HU188171B/hu unknown
- 1982-05-21 ES ES512473A patent/ES512473A0/es active Granted
- 1982-05-21 JP JP57086382A patent/JPS57200384A/ja active Pending
- 1982-05-21 NO NO821699A patent/NO821699L/no unknown
- 1982-05-21 AU AU84043/82A patent/AU551047B2/en not_active Ceased
- 1982-05-21 CA CA000403514A patent/CA1183137A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GR75841B (show.php) | 1984-08-02 |
| ES8307790A1 (es) | 1983-08-01 |
| AR231445A1 (es) | 1984-11-30 |
| HU188171B (en) | 1986-03-28 |
| ZA823492B (en) | 1983-03-30 |
| IL65474A (en) | 1985-08-30 |
| JPS57200384A (en) | 1982-12-08 |
| EP0065909A1 (fr) | 1982-12-01 |
| ES512473A0 (es) | 1983-08-01 |
| FR2506311A1 (fr) | 1982-11-26 |
| AU551047B2 (en) | 1986-04-17 |
| CA1183137A (fr) | 1985-02-26 |
| EP0065909B1 (fr) | 1984-12-12 |
| PT74917A (fr) | 1982-06-01 |
| US4416888A (en) | 1983-11-22 |
| PT74917B (fr) | 1983-12-07 |
| IL65474A0 (en) | 1982-07-30 |
| DE3261524D1 (en) | 1985-01-24 |
| AU8404382A (en) | 1982-11-25 |
| MA19482A1 (fr) | 1982-12-31 |
| DK220882A (da) | 1982-11-23 |
| FR2506311B1 (show.php) | 1983-12-16 |
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