HU188170B - Process for producing 3-square bracket-2-bracket-tetra-or hexahydro.4-pyridyl-bracket closed-ethyl-s uare bracket closed-indola derivatives - Google Patents
Process for producing 3-square bracket-2-bracket-tetra-or hexahydro.4-pyridyl-bracket closed-ethyl-s uare bracket closed-indola derivatives Download PDFInfo
- Publication number
- HU188170B HU188170B HU821640A HU164082A HU188170B HU 188170 B HU188170 B HU 188170B HU 821640 A HU821640 A HU 821640A HU 164082 A HU164082 A HU 164082A HU 188170 B HU188170 B HU 188170B
- Authority
- HU
- Hungary
- Prior art keywords
- bracket
- pyridyl
- compound
- formula
- hexahydro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 31
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 28
- 229940076279 serotonin Drugs 0.000 claims description 14
- -1 hexahydro-4-pyridyl Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 230000003578 releasing effect Effects 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- UUEYCHLWAOBOHG-UHFFFAOYSA-N 3-(2-pyridin-4-ylethyl)-1h-indole Chemical class C=1NC2=CC=CC=C2C=1CCC1=CC=NC=C1 UUEYCHLWAOBOHG-UHFFFAOYSA-N 0.000 claims description 3
- 229940054051 antipsychotic indole derivative Drugs 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 230000002460 anti-migrenic effect Effects 0.000 claims 1
- 230000002785 anti-thrombosis Effects 0.000 claims 1
- 239000003146 anticoagulant agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 229940126570 serotonin reuptake inhibitor Drugs 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 230000000697 serotonin reuptake Effects 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 5
- SADQVAVFGNTEOD-UHFFFAOYSA-N indalpine Chemical compound C=1NC2=CC=CC=C2C=1CCC1CCNCC1 SADQVAVFGNTEOD-UHFFFAOYSA-N 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 229950002473 indalpine Drugs 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VTBGWXUNMCQYHV-UHFFFAOYSA-N 3-(2-piperidin-4-ylpropyl)-1h-indole Chemical compound C=1NC2=CC=CC=C2C=1CC(C)C1CCNCC1 VTBGWXUNMCQYHV-UHFFFAOYSA-N 0.000 description 3
- INIQHXXGTRZLAC-UHFFFAOYSA-N 3-(2-pyridin-4-ylpropyl)-1h-indole Chemical compound C=1NC2=CC=CC=C2C=1CC(C)C1=CC=NC=C1 INIQHXXGTRZLAC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- WWPITPSIWMXDPE-UHFFFAOYSA-N para-chloroamphetamine Chemical compound CC(N)CC1=CC=C(Cl)C=C1 WWPITPSIWMXDPE-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- KPBLZPAVDSMKJB-UHFFFAOYSA-N 5-fluoro-3-(2-pyridin-4-ylethyl)-1h-indole Chemical compound C12=CC(F)=CC=C2NC=C1CCC1=CC=NC=C1 KPBLZPAVDSMKJB-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 208000019695 Migraine disease Diseases 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 208000007536 Thrombosis Diseases 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052736 halogen Chemical group 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 238000005984 hydrogenation reaction Methods 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
- 229960004801 imipramine Drugs 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
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 206010027599 migraine Diseases 0.000 description 2
- 210000002569 neuron Anatomy 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 230000004936 stimulating effect Effects 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
- NXDULGCZHXYGSP-UHFFFAOYSA-N 3-(2-piperidin-4-ylpropyl)-1h-indole;hydrochloride Chemical compound Cl.C=1NC2=CC=CC=C2C=1CC(C)C1CCNCC1 NXDULGCZHXYGSP-UHFFFAOYSA-N 0.000 description 1
- NXILFDDNNYWNJC-UHFFFAOYSA-N 3-[2-(1,2,3,6-tetrahydropyridin-4-yl)ethyl]-1h-indole Chemical compound C=1NC2=CC=CC=C2C=1CCC1=CCNCC1 NXILFDDNNYWNJC-UHFFFAOYSA-N 0.000 description 1
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 1
- WFUJCUFNPNKJLK-UHFFFAOYSA-N 5-fluoro-3-[2-(1,2,3,6-tetrahydropyridin-4-yl)ethyl]-1h-indole Chemical compound C12=CC(F)=CC=C2NC=C1CCC1=CCNCC1 WFUJCUFNPNKJLK-UHFFFAOYSA-N 0.000 description 1
- ODFFPRGJZRXNHZ-UHFFFAOYSA-N 5-fluoroindole Chemical compound FC1=CC=C2NC=CC2=C1 ODFFPRGJZRXNHZ-UHFFFAOYSA-N 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Natural products OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940025084 amphetamine Drugs 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000001530 fumaric acid 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
- 210000005260 human cell Anatomy 0.000 description 1
- 230000035873 hypermotility Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000003760 magnetic stirring Methods 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
- 230000001537 neural effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 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
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 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
- 239000012264 purified product Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000000946 synaptic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 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 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000723 toxicological property 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
- 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 |
|---|---|---|---|
| FR8110218A FR2506309A1 (fr) | 1981-05-22 | 1981-05-22 | ((tetra- et hexahydro pyridyl-4)-2 ethyl)-3 indoles et leur utilisation comme medicaments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU188170B true HU188170B (en) | 1986-03-28 |
Family
ID=9258780
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU821640A HU188170B (en) | 1981-05-22 | 1982-05-21 | Process for producing 3-square bracket-2-bracket-tetra-or hexahydro.4-pyridyl-bracket closed-ethyl-s uare bracket closed-indola derivatives |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4478841A (enExample) |
| EP (1) | EP0065907B1 (enExample) |
| JP (1) | JPS57206682A (enExample) |
| AR (1) | AR230836A1 (enExample) |
| AU (1) | AU550236B2 (enExample) |
| CA (1) | CA1185241A (enExample) |
| DE (1) | DE3261440D1 (enExample) |
| DK (1) | DK227182A (enExample) |
| ES (1) | ES512471A0 (enExample) |
| FR (1) | FR2506309A1 (enExample) |
| GR (1) | GR79118B (enExample) |
| HU (1) | HU188170B (enExample) |
| IL (1) | IL65416A (enExample) |
| NO (1) | NO821698L (enExample) |
| PT (1) | PT74792B (enExample) |
| ZA (1) | ZA823490B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3308668A1 (de) * | 1983-03-11 | 1984-09-13 | Merck Patent Gmbh, 6100 Darmstadt | Indolderivate |
| DE3430284A1 (de) * | 1984-08-17 | 1986-02-27 | Troponwerke GmbH & Co KG, 5000 Köln | Neue tryptamin-derivate, ein verfahren zu ihrer herstellung und ihre verwendung |
| US4757079A (en) * | 1986-06-24 | 1988-07-12 | Dynamac Corporaton | Anti-hypertensive piperidine compounds |
| EP0351283A1 (fr) * | 1988-07-12 | 1990-01-17 | Synthelabo | Dérivés de [(pipéridinyl-4) méthyl]-2 dihydro-2,3 1H-isoindole et tétrahydro-2,3,4,5 1H-benzazépines, leur préparation et leur application en thérapeutique |
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 |
| 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 |
| FR2334358A1 (fr) * | 1975-12-12 | 1977-07-08 | Sogeras | Nouveaux medicaments derives de l'indole |
| US4208417A (en) * | 1978-06-29 | 1980-06-17 | Pharmindustrie | Indole derivatives and their use as anxiolytics |
-
1981
- 1981-05-22 FR FR8110218A patent/FR2506309A1/fr active Granted
-
1982
- 1982-04-02 IL IL65416A patent/IL65416A/xx unknown
- 1982-04-05 GR GR67807A patent/GR79118B/el unknown
- 1982-04-23 PT PT74792A patent/PT74792B/pt unknown
- 1982-05-03 US US06/374,364 patent/US4478841A/en not_active Expired - Fee Related
- 1982-05-11 DE DE8282400871T patent/DE3261440D1/de not_active Expired
- 1982-05-11 EP EP82400871A patent/EP0065907B1/fr not_active Expired
- 1982-05-19 DK DK227182A patent/DK227182A/da not_active Application Discontinuation
- 1982-05-19 AR AR289453A patent/AR230836A1/es active
- 1982-05-19 ZA ZA823490A patent/ZA823490B/xx unknown
- 1982-05-21 NO NO821698A patent/NO821698L/no unknown
- 1982-05-21 JP JP57086381A patent/JPS57206682A/ja active Pending
- 1982-05-21 CA CA000403526A patent/CA1185241A/fr not_active Expired
- 1982-05-21 ES ES512471A patent/ES512471A0/es active Granted
- 1982-05-21 HU HU821640A patent/HU188170B/hu unknown
- 1982-05-21 AU AU84041/82A patent/AU550236B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| AU8404182A (en) | 1982-11-25 |
| IL65416A (en) | 1985-03-31 |
| AU550236B2 (en) | 1986-03-13 |
| EP0065907B1 (fr) | 1984-12-05 |
| PT74792A (fr) | 1982-05-01 |
| ES8307241A1 (es) | 1983-07-01 |
| DE3261440D1 (en) | 1985-01-17 |
| NO821698L (no) | 1982-11-23 |
| US4478841A (en) | 1984-10-23 |
| FR2506309B1 (enExample) | 1984-03-23 |
| IL65416A0 (en) | 1982-07-30 |
| FR2506309A1 (fr) | 1982-11-26 |
| DK227182A (da) | 1982-11-23 |
| AR230836A1 (es) | 1984-07-31 |
| CA1185241A (fr) | 1985-04-09 |
| JPS57206682A (en) | 1982-12-18 |
| ZA823490B (en) | 1983-03-30 |
| ES512471A0 (es) | 1983-07-01 |
| GR79118B (enExample) | 1984-10-02 |
| EP0065907A1 (fr) | 1982-12-01 |
| PT74792B (fr) | 1983-11-07 |
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