HU188171B - Process for producing new 3-square bracket-2-bracket-4-piperidyl-bracket closed-1-alkyl-ethyl-squre bracket closed-indole derivatives - Google Patents
Process for producing new 3-square bracket-2-bracket-4-piperidyl-bracket closed-1-alkyl-ethyl-squre bracket closed-indole derivatives Download PDFInfo
- Publication number
- HU188171B HU188171B HU821641A HU164182A HU188171B HU 188171 B HU188171 B HU 188171B HU 821641 A HU821641 A HU 821641A HU 164182 A HU164182 A HU 164182A HU 188171 B HU188171 B HU 188171B
- Authority
- HU
- Hungary
- Prior art keywords
- bracket
- formula
- closed
- piperidyl
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 229940054051 antipsychotic indole derivative Drugs 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 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
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 229910052987 metal hydride Inorganic materials 0.000 claims description 2
- 150000004681 metal hydrides Chemical group 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 26
- 229940076279 serotonin Drugs 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 230000000697 serotonin reuptake Effects 0.000 description 10
- 239000000243 solution Substances 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- -1 aluminum lithium hydride Chemical compound 0.000 description 6
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 6
- SADQVAVFGNTEOD-UHFFFAOYSA-N indalpine Chemical compound C=1NC2=CC=CC=C2C=1CCC1CCNCC1 SADQVAVFGNTEOD-UHFFFAOYSA-N 0.000 description 6
- 229950002473 indalpine Drugs 0.000 description 5
- 238000012360 testing method Methods 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
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 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 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 229960004801 imipramine Drugs 0.000 description 2
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 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
- 150000002475 indoles Chemical class 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 2
- 230000001537 neural effect Effects 0.000 description 2
- 210000002569 neuron Anatomy 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
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 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 description 1
- YFNOTMRKVGZZNF-UHFFFAOYSA-N 2-piperidin-1-ium-4-ylacetate Chemical compound OC(=O)CC1CCNCC1 YFNOTMRKVGZZNF-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- 108090000190 Thrombin Proteins 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
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940025084 amphetamine Drugs 0.000 description 1
- 208000022531 anorexia Diseases 0.000 description 1
- 230000001430 anti-depressive effect Effects 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
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012458 free base 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
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical compound [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 description 1
- 229910001641 magnesium iodide Inorganic materials 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 230000013275 serotonin uptake Effects 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000003756 stirring Methods 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
- 238000010998 test method Methods 0.000 description 1
- 229960004072 thrombin Drugs 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 230000006442 vascular tone Effects 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (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)
- 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 |
|---|---|
| HU188171B true HU188171B (en) | 1986-03-28 |
Family
ID=9258784
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU821641A HU188171B (en) | 1981-05-22 | 1982-05-21 | Process for producing new 3-square bracket-2-bracket-4-piperidyl-bracket closed-1-alkyl-ethyl-squre bracket closed-indole derivatives |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4416888A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0065909B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JPS57200384A (cg-RX-API-DMAC7.html) |
| AR (1) | AR231445A1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU551047B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA1183137A (cg-RX-API-DMAC7.html) |
| DE (1) | DE3261524D1 (cg-RX-API-DMAC7.html) |
| DK (1) | DK220882A (cg-RX-API-DMAC7.html) |
| ES (1) | ES8307790A1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2506311A1 (cg-RX-API-DMAC7.html) |
| GR (1) | GR75841B (cg-RX-API-DMAC7.html) |
| HU (1) | HU188171B (cg-RX-API-DMAC7.html) |
| IL (1) | IL65474A (cg-RX-API-DMAC7.html) |
| MA (1) | MA19482A1 (cg-RX-API-DMAC7.html) |
| NO (1) | NO821699L (cg-RX-API-DMAC7.html) |
| PT (1) | PT74917B (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA823492B (cg-RX-API-DMAC7.html) |
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 |
|---|---|---|---|---|
| GB925429A (en) * | 1960-04-01 | 1963-05-08 | Irwin Neisler & Co | Indole derivatives |
| FR1289690A (fr) * | 1960-04-01 | 1962-04-06 | Irwin | Dérivés de l'indole |
| 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 DE DE8282400873T patent/DE3261524D1/de not_active Expired
- 1982-05-11 EP EP82400873A patent/EP0065909B1/fr 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 AR AR289455A patent/AR231445A1/es active
- 1982-05-19 ZA ZA823492A patent/ZA823492B/xx unknown
- 1982-05-20 MA MA19688A patent/MA19482A1/fr unknown
- 1982-05-21 HU HU821641A patent/HU188171B/hu unknown
- 1982-05-21 NO NO821699A patent/NO821699L/no unknown
- 1982-05-21 CA CA000403514A patent/CA1183137A/fr not_active Expired
- 1982-05-21 ES ES512473A patent/ES8307790A1/es not_active Expired
- 1982-05-21 AU AU84043/82A patent/AU551047B2/en not_active Ceased
- 1982-05-21 JP JP57086382A patent/JPS57200384A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DK220882A (da) | 1982-11-23 |
| PT74917A (fr) | 1982-06-01 |
| EP0065909B1 (fr) | 1984-12-12 |
| JPS57200384A (en) | 1982-12-08 |
| AU8404382A (en) | 1982-11-25 |
| FR2506311A1 (fr) | 1982-11-26 |
| AU551047B2 (en) | 1986-04-17 |
| NO821699L (no) | 1982-11-23 |
| ZA823492B (en) | 1983-03-30 |
| IL65474A (en) | 1985-08-30 |
| PT74917B (fr) | 1983-12-07 |
| AR231445A1 (es) | 1984-11-30 |
| EP0065909A1 (fr) | 1982-12-01 |
| ES512473A0 (es) | 1983-08-01 |
| US4416888A (en) | 1983-11-22 |
| GR75841B (cg-RX-API-DMAC7.html) | 1984-08-02 |
| IL65474A0 (en) | 1982-07-30 |
| MA19482A1 (fr) | 1982-12-31 |
| CA1183137A (fr) | 1985-02-26 |
| DE3261524D1 (en) | 1985-01-24 |
| ES8307790A1 (es) | 1983-08-01 |
| FR2506311B1 (cg-RX-API-DMAC7.html) | 1983-12-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4423044A (en) | 3,4-Dihydro-5H-2,3-benzodiazepine derivatives and pharmaceutical use thereof | |
| JPS62129280A (ja) | 新規化合物、その製法及びそれを含む医薬組成物 | |
| US4224329A (en) | 2-Substituted-trans-5-aryl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indoles | |
| JPS6289679A (ja) | ピペリジン誘導体 | |
| JPS6012350B2 (ja) | 新規アリ−ルピペリジン誘導体の製造方法 | |
| US4336268A (en) | Cyclohexene derivative analgesics | |
| PT91783B (pt) | Processo para a preparacao de {(diarilmetoxi) alquil}-1-pirrolidinas e piperidinas | |
| EP0104632A2 (en) | 1'-(3-(1,2-Benzisoxazol-3-yl)propyl)spiro-(benzofuran-2-(3H),3' or 4'-piperidine or 3'-pyrrolidines), a process for their preparation and their use as medicaments | |
| US3557127A (en) | Substituted cyclohexenes,derivatives thereof and processes for obtaining same | |
| US3253034A (en) | Amino-phenylethanols | |
| US4010202A (en) | 5,6-Dihydroxy aminotetralol compounds | |
| US3312733A (en) | Optically active naphthylethanolamines and the salts thereof | |
| HU188171B (en) | Process for producing new 3-square bracket-2-bracket-4-piperidyl-bracket closed-1-alkyl-ethyl-squre bracket closed-indole derivatives | |
| HU187480B (en) | Process for producing 1-bracket-4-quinolyl-bracket closed-2-bracket-4-piperidyl-bracket closed-ethanol and 1-bracket-4-quinolyl-bracket closed-3-bracket-4-piperidiyl-bracket closed-propanol and pharmaceutival compositions containing them as active agents | |
| FR2687146A1 (fr) | Nouveaux derives de pyrrolidine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. | |
| EP0073645B1 (en) | 2-cyclic amino-2-(1,2-benzisoxazol-3-yl)acetic acid ester derivatives, process for the preparation thereof and composition containing the same | |
| JPS60132962A (ja) | Ｎ−置換イソキノリン誘導体 | |
| Bell et al. | Stereochemical studies on medicinal agents. 15. Absolute configurations and analgetic potecies of enantiomeric diastereomers of 3-allyl-1-methyl-4-phenyl-4-propionoxypiperidine | |
| US4252812A (en) | 2-Substituted-trans-5-aryl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indoles | |
| US4716172A (en) | 4-substituted octahydroquinolizine analgesic compounds and octahydroquinolizinium intermediates | |
| US4267331A (en) | Process for the production of 2-substituted pyrido[4,3-b]-indoles | |
| HU187675B (en) | Process for preparing new indole derivatives and pharmaceutical compositions containing such compounds | |
| US4435410A (en) | 3-[2-(3-Alkyl and alkenyl-4-piperidyl)-ethyl]-indoles for inhibiting serotonin uptake and for releasing serotonin | |
| US4104402A (en) | 5,6-Dihydroxy aminotetralol compounds | |
| US3565899A (en) | Oxy-substituted benzo quinolizinium compounds |