NO781896L - 4-fenyl-8-amino-tetrahydroisokinoliner, farmasoeytiske preparater som inneholder disse, fremgangsmaate til fremstilling av disse preparater og deres anvendelse som antidepresjonsmidler - Google Patents
4-fenyl-8-amino-tetrahydroisokinoliner, farmasoeytiske preparater som inneholder disse, fremgangsmaate til fremstilling av disse preparater og deres anvendelse som antidepresjonsmidlerInfo
- Publication number
- NO781896L NO781896L NO78781896A NO781896A NO781896L NO 781896 L NO781896 L NO 781896L NO 78781896 A NO78781896 A NO 78781896A NO 781896 A NO781896 A NO 781896A NO 781896 L NO781896 L NO 781896L
- Authority
- NO
- Norway
- Prior art keywords
- preparations
- amino
- phenyl
- acid
- preparation
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 6
- 239000000825 pharmaceutical preparation Substances 0.000 title claims 3
- 150000001875 compounds Chemical class 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- -1 N-(2-amino-benzyl)-α-methyl-amino-methyl-benzyl Chemical group 0.000 claims description 4
- 230000001430 anti-depressive effect Effects 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 239000000935 antidepressant agent Substances 0.000 claims description 3
- 229940005513 antidepressants Drugs 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 230000003001 depressive effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 150000002431 hydrogen Chemical class 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- WXPTXMBRTPQBEN-UHFFFAOYSA-N 4-phenyl-1,2,3,4-tetrahydroisoquinolin-8-amine Chemical class C1NCC=2C(N)=CC=CC=2C1C1=CC=CC=C1 WXPTXMBRTPQBEN-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 230000013275 serotonin uptake Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- WYECURVXVYPVAT-UHFFFAOYSA-N 1-(4-bromophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Br)C=C1 WYECURVXVYPVAT-UHFFFAOYSA-N 0.000 description 1
- FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical compound OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 0.000 description 1
- WGILVXQNSFDASI-UHFFFAOYSA-N 2-nitro-n-methylbenzylamine Chemical compound CNCC1=CC=CC=C1[N+]([O-])=O WGILVXQNSFDASI-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-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
- 239000005711 Benzoic acid Substances 0.000 description 1
- 101100387923 Caenorhabditis elegans dos-1 gene Proteins 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-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
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- OKJIRPAQVSHGFK-UHFFFAOYSA-N N-acetylglycine Chemical compound CC(=O)NCC(O)=O OKJIRPAQVSHGFK-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229950006191 gluconic acid Drugs 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 230000008517 inhibition of serotonin uptake Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000004540 pour-on Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 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
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
4-fenyl-8-amino-tetrahydroisokinoliner farmasøytis-
ke preparater som inneholder disse, fremgangsmåte til fremstilling av disse preparater og deres anven-del sessiømååntidepre siver.
Fra DOS 1 795 829 er det kjent 4-fenyl-8-amino-tetrahydroisokinoliner med den generelle formel I
hvori R betyr hydrogen, en lavere alkyl- eller benzylgruppe, R 2 betyr hydrogen, metylgruppe, klor- eller fluoratomer, R^, betyr hydrogen, metyl-, metoksy-, hydroksygrupper eller halo-genatomer, R^og R^betyr hydrogen eller en lavere alkylgrup-pe og R^, betyr hydrogen, et kloratom eller en metoksygruppe i 5- eller 6-stilling.
Det er nu overraskende funnet at to hittil ikke kjente forbindelser av ovennevnte forbindelsesklasse med ovennevnte formel I er betraktelig overlegen i deres antidepresive virkning.
Gjenstand for utvelgelsesoppfinnelsen er således for-bindelsen med den generelle formel II hvori enten betyr brom og R^hydrogen eller såvel R^som også R^betyr klor.
De nye forbindelser med den generelle formelen II ut-merker seg blant annet ved en overfor de tidligere kjente for-bindelsesklasser forsterket virkning i serotonin-opptak-hemme-prøven. Mens de tidligere kjente forbindelser med formel I
(med unntak av forbindelser med formel II) først i høyere kon-sentrasjon hemmer serotoninopptaket bevirker forbindelsene med formelen II en serotoninopptakhemming slik man hittil ikke kunne oppnå med forbindelsene med formel I.
Serotoninopptakhemmingen ytrer seg ieén forsterket sjelelig stemningsløftende virkning og har derfor betraktelig betydning for terapien. Forbindelsene med formel II er derfor verdifulle farmasøytika som anvendes til behandling av depre-sive tilstander.
Fremstilling av forbindelsene med formel II foregår etter fremgangsmåten ifølge tysk patent nr. 1 670 694 ved syklisering av tilsvarende N-(2-aminobenzyl)-a-metylaminometyl-benzylal"koholer.
Forbindelsene med formel II kan danne salter såvel
med en som også med to ekvivalenter av en syre. Med hensyn til deres anvendelse som legemiddel kommer det i betrakning for saltdannelse fysiologisk holdbare syrer. Som uorganiske syrer kbmmer eksempelvis i betraktning: halogen, hydrogen, syrer som klorhydrogensyre og bromhydrogensyre samt svovelsyre, fosfor-syre og amidosulfonsyre. Som organiske syrer skal det eksempel-" vil nevnes: maursyre, eddiksyre, pripionsyre, melkesyre, "gly-kolsyre, glykonsyre, maleinsyre, gravsyre, vinsyre, benzosyre, salicylsyre, sitronsyre, acetursyre eller oksyetansulfonsyre.
Eksempel 1.
50 g 3j4-dikloracetofenon bromieres i 300 ml metylenklorid med brom ved værelsetemperatur. Det således dannede !W<i-brom3,4-dikloracetof enon anvendes direkte. I første rekke oppløses U/-bromforbindelsen i 300 ml etanol. Under omrøring lar man ved 6o°C tildryppe oppløsningen av 42,6 g N-metyl-2-nitrobenzylamin og 33>1 S N-etyl-N,N-diisopropyletylamin i 100 mi etanol. Nu omrøres ennu 1 time ved værelsetemperatur deretter 2 timer under kokning, derpå inndamper man til tørr-het. Residuet oppløser man i vann og eter, sistnevnte adskil-les, tørkes med kalsiumkarbonat og inndampes igjen.
Residuet danner metanol/klorhydrogen et salt og man får 19 g N-(3>4-diklorfenacyl)-N-metyl-2-nitro-benzylamin-hydroklorid, smeltepunkt l65°C under spaltning.
Fra hydrokloridet fremstiller man igjen basen som isoleres med metylenklorid som olje (l8g). Karbonyl- og nit-rogrupper hydrogeneres nu i rekkefølge. Karbonylgruppen gir med natriumborhydrid (5 g i 50 mi metanol til 18 g acetofenon-derivat i 250 ml metanol) 15 g av hydroksyforbindelsen, nitro-gruppen hydrerer man nu med Raney-nikkel med normaltrykk og værelsetemperatur. Hydrogenopptaket er som beregnet, man får l4 g N-2-aminobenzyl-a-N-metylamino-metyl-3,4-diklorbenzylal-kohol som oljeaktig produkt.
Til syklisering inndryppes l4 g av den dannede olje
i 100 ml metylenklorid under omrøring ved 5 til 10°C i J, 0 ml svovelsyre (konsentrert).<Man omrører i 1 timer ved værelsetemperatur og heller endelig på knust is. Under ytterligere avkjøling nøytraliseres med konsentrert NaOH idjit reaksjons-produktet fremkommer i oljeaktig form. Man isolerer basen med metylenklorid og får 8 g av isokinolinderivatet som base.
Ved basen oppløses med maleinsyre ( 3 g for 8 g base) i etanol under oppvarmning. Det ved avkjøling utkrystallise-rende maleinat omkrystalliseres fra etanol.
Man får 3,5 g 8-amino-4-(3,4-diklorfenyl)-2-metyl-1,2,3>4-tetrahydroisokinolin-hydrogenmaleinat av smeltepunkt 180 - 183°C
Eksempel 2.
Idet det gås ut fra 4-bromacetofenon får man i hen-hold til den i eksempel 1 omtalte arbeidsmåte 8-amino-4-(4- bromfenyl)-2-metyl-l,2,3,4-tetrahydroisokinolin-hydrogenmale-inat som smelter ved J.89 - 191°C.
Claims (5)
1. k- fenyl-8-amino-tetrahydroisokinolin med formel
hvori enten R^. betyr brom og R£ betyr hydrogen eller såvel R^ som også R^ betyr klor, samt deres salter med fysiologisk tålbare syrer.
2. Farmasøytiske preparater med antidepressivevirkning, karakterisert ved et innhold av forbindelser ifølge krav 1.
3. Fremgangsmåte til fremstilling av farmasøytiske preparater med antidepressiv virkning, karakterisert ved at man bringer en forbindelse ifølge krav 1 eventuelt med vanlig bærestoffer og/eller stabilisatorer en farmasøytisk tålbar anvendelsesform.
4. Anvendelse av forbindelser ifølge krav 1 ved bekjem-pelse av depressive tilstander.
5. Fremgangsmåte til fremstilling av k- fenyl-8-amino-tetrahydroisokinpliner med formel ifølge kravvl, karakterisert ved at de tilsvarende N-(2-amino-benzyl)-a-metyl-amino-metyl-benzyl-alkoholer sykli seres.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772724610 DE2724610A1 (de) | 1977-06-01 | 1977-06-01 | 4-phenyl-8-amino-tetrahydroisochinoline |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO781896L true NO781896L (no) | 1978-12-04 |
Family
ID=6010350
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO78781896A NO781896L (no) | 1977-06-01 | 1978-05-31 | 4-fenyl-8-amino-tetrahydroisokinoliner, farmasoeytiske preparater som inneholder disse, fremgangsmaate til fremstilling av disse preparater og deres anvendelse som antidepresjonsmidler |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4185105A (no) |
| EP (1) | EP0000013B1 (no) |
| JP (1) | JPS543078A (no) |
| AT (1) | AT361482B (no) |
| AU (1) | AU517664B2 (no) |
| CA (1) | CA1093079A (no) |
| DE (2) | DE2724610A1 (no) |
| DK (1) | DK242278A (no) |
| EG (1) | EG13777A (no) |
| ES (1) | ES470226A1 (no) |
| FI (1) | FI781717A (no) |
| HU (1) | HU176978B (no) |
| IL (1) | IL54810A0 (no) |
| IT (1) | IT1094899B (no) |
| NO (1) | NO781896L (no) |
| PT (1) | PT68123A (no) |
| ZA (1) | ZA783122B (no) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4340600A (en) * | 1980-05-22 | 1982-07-20 | Smithkline Corporation | Renal dilating methods and compositions using 4-(3,4-dihydroxyphenyl)-1,2,3,4-tetrahydroisoquinolines |
| PH19604A (en) * | 1982-06-04 | 1986-05-27 | Egyt Gyogyszervegyeszeti Gyar | Isoquinoline derivatives and pharmaceutical compositions containing the same |
| DE3310878A1 (de) * | 1983-03-25 | 1984-09-27 | Hoechst Ag, 6230 Frankfurt | Optische antipoden von 8-amino-4-phenyl-1,2,3,4-tetrahydroisochinolin, verfahren zu ihrer herstellung und sie enthaltende arzneimittel mit antidepressiver wirkung |
| BG45572A1 (en) * | 1986-10-23 | 1989-07-14 | Druzhestven N Izsledovatelski | Antiulcer means |
| AU2004244672B2 (en) * | 2003-06-10 | 2011-02-10 | Resmed Limited | Multiple stage blower and enclosure therefor |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3384640A (en) * | 1966-03-15 | 1968-05-21 | Bristol Myers Co | Amino isoquinolinium salts |
| DE1670694B2 (de) * | 1966-05-05 | 1976-07-22 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von tetrahydroisochinolinen |
-
1977
- 1977-06-01 DE DE19772724610 patent/DE2724610A1/de not_active Withdrawn
-
1978
- 1978-05-26 ES ES470226A patent/ES470226A1/es not_active Expired
- 1978-05-29 EG EG343/78A patent/EG13777A/xx active
- 1978-05-30 IL IL54810A patent/IL54810A0/xx unknown
- 1978-05-30 ZA ZA00783122A patent/ZA783122B/xx unknown
- 1978-05-30 US US05/910,781 patent/US4185105A/en not_active Expired - Lifetime
- 1978-05-30 IT IT23996/78A patent/IT1094899B/it active
- 1978-05-30 FI FI781717A patent/FI781717A/fi not_active Application Discontinuation
- 1978-05-31 HU HU78HO2078A patent/HU176978B/hu unknown
- 1978-05-31 PT PT68123A patent/PT68123A/pt unknown
- 1978-05-31 CA CA304,518A patent/CA1093079A/en not_active Expired
- 1978-05-31 DK DK242278A patent/DK242278A/da not_active Application Discontinuation
- 1978-05-31 AT AT395078A patent/AT361482B/de not_active IP Right Cessation
- 1978-05-31 AU AU36705/78A patent/AU517664B2/en not_active Expired
- 1978-05-31 NO NO78781896A patent/NO781896L/no unknown
- 1978-06-01 EP EP78100025A patent/EP0000013B1/de not_active Expired
- 1978-06-01 DE DE7878100025T patent/DE2860212D1/de not_active Expired
- 1978-06-01 JP JP6499278A patent/JPS543078A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ATA395078A (de) | 1980-08-15 |
| IT7823996A0 (it) | 1978-05-30 |
| EP0000013A1 (de) | 1978-12-20 |
| IT1094899B (it) | 1985-08-10 |
| PT68123A (en) | 1978-06-01 |
| DK242278A (da) | 1978-12-02 |
| CA1093079A (en) | 1981-01-06 |
| DE2724610A1 (de) | 1978-12-14 |
| ZA783122B (en) | 1979-06-27 |
| HU176978B (hu) | 1981-06-28 |
| IL54810A0 (en) | 1978-07-31 |
| FI781717A (fi) | 1978-12-02 |
| AU517664B2 (en) | 1981-08-20 |
| EP0000013B1 (de) | 1980-10-15 |
| JPS543078A (en) | 1979-01-11 |
| DE2860212D1 (en) | 1981-01-22 |
| ES470226A1 (es) | 1979-01-01 |
| AT361482B (de) | 1981-03-10 |
| US4185105A (en) | 1980-01-22 |
| EG13777A (en) | 1982-03-31 |
| AU3670578A (en) | 1979-12-06 |
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