CH630902A5 - Process for preparing novel derivatives of 1,2,3,4,4a,10b-hexahydrobenzo(f)isoquinoline. - Google Patents
Process for preparing novel derivatives of 1,2,3,4,4a,10b-hexahydrobenzo(f)isoquinoline. Download PDFInfo
- Publication number
- CH630902A5 CH630902A5 CH82077A CH82077A CH630902A5 CH 630902 A5 CH630902 A5 CH 630902A5 CH 82077 A CH82077 A CH 82077A CH 82077 A CH82077 A CH 82077A CH 630902 A5 CH630902 A5 CH 630902A5
- Authority
- CH
- Switzerland
- Prior art keywords
- carbon atoms
- formula
- group
- compounds
- alkyl
- Prior art date
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- ACTXSHOKTHONRW-UHFFFAOYSA-N 1,2,3,4,4a,10b-hexahydrobenzo[f]isoquinoline Chemical class C1=CC=C2C3CCNCC3C=CC2=C1 ACTXSHOKTHONRW-UHFFFAOYSA-N 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 239000007858 starting material Substances 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- GPVPDRHTRGTSIH-UHFFFAOYSA-N isoquinolin-6-ol Chemical compound C1=NC=CC2=CC(O)=CC=C21 GPVPDRHTRGTSIH-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 230000016571 aggressive behavior Effects 0.000 description 2
- 230000037007 arousal Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- -1 lithium aluminum hydride Chemical compound 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RJAQRZMCFUMCIL-UHFFFAOYSA-N 1,2,3,4-tetrahydrobenzo[f]isoquinoline Chemical compound C1=CC2=CC=CC=C2C2=C1CNCC2 RJAQRZMCFUMCIL-UHFFFAOYSA-N 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- MXBHKIXAINECLQ-UHFFFAOYSA-N 2-(1-methyl-4-phenylpiperidin-3-yl)acetonitrile Chemical compound N#CCC1CN(C)CCC1C1=CC=CC=C1 MXBHKIXAINECLQ-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
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- ZOPRZPCFDOOXNP-UHFFFAOYSA-N 3,6-dimethyl-2,4,5,6-tetrahydro-1H-benzo[f]isoquinoline Chemical compound CN1CC=2CC(C3=C(C=2CC1)C=CC=C3)C ZOPRZPCFDOOXNP-UHFFFAOYSA-N 0.000 description 1
- ABHKKBIJWBLTIJ-UHFFFAOYSA-N 3-(chloromethyl)-1-methyl-4-phenylpiperidine hydrochloride Chemical compound Cl.ClCC1CN(CCC1C1=CC=CC=C1)C ABHKKBIJWBLTIJ-UHFFFAOYSA-N 0.000 description 1
- BSJAANDMNOOMPM-UHFFFAOYSA-N 3-methyl-2,4,5,6-tetrahydro-1h-benzo[f]isoquinoline Chemical compound C1=CC=C2C(CCN(C3)C)=C3CCC2=C1 BSJAANDMNOOMPM-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 206010001488 Aggression Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 208000036626 Mental retardation Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 206010037218 Psychopathic personality Diseases 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 208000012761 aggressive behavior Diseases 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000002539 anti-aggressive effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- LEXDNMDBXBZONN-UHFFFAOYSA-N ethyl 2-(1-methyl-4-phenylpiperidin-3-yl)acetate Chemical compound C(C)OC(CC1CN(CCC1C1=CC=CC=C1)C)=O LEXDNMDBXBZONN-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-M fumarate(1-) Chemical compound OC(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-M 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052740 iodine Chemical group 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/10—Aza-phenanthrenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Priority Applications (28)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH82077A CH630902A5 (en) | 1977-01-24 | 1977-01-24 | Process for preparing novel derivatives of 1,2,3,4,4a,10b-hexahydrobenzo(f)isoquinoline. |
| CH191081A CH633270A5 (en) | 1977-01-24 | 1978-01-01 | Derivatives of 1,2,3,4,4a,10b-hexahydrobenz[f]isoquinoline and their use |
| DE19782801576 DE2801576A1 (de) | 1977-01-24 | 1978-01-14 | Neue organische verbindungen, ihre herstellung und verwendung |
| SE7800452A SE7800452L (sv) | 1977-01-24 | 1978-01-16 | Nya organiska foreningar, deras framstellning och anvendning |
| FI780130A FI780130A7 (fi) | 1977-01-24 | 1978-01-16 | Nya organiska foereningar deras framstaellning och anvaendning |
| DK19278A DK19278A (da) | 1977-01-24 | 1978-01-16 | Fremgangsmaade til fremstilling af isoquinolinderivater |
| IT7847687A IT7847687A0 (it) | 1977-01-24 | 1978-01-18 | Derivati della benzo(f)isochinolina loro preparazione e loro applicazione quali medicamenti |
| NZ186279A NZ186279A (en) | 1977-01-24 | 1978-01-20 | 1,2,3,4a,10b-hexahiydrobenz(f)isoquinolines |
| NL7800719A NL7800719A (nl) | 1977-01-24 | 1978-01-20 | Nieuwe cyclische verbindingen en werkwijzen voor het bereiden en toepassen van deze verbindingen. |
| IL53869A IL53869A (en) | 1977-01-24 | 1978-01-23 | 1,2,3,4,4a,10b-hexahydro-benz(f)isoquinoline derivatives,their production and pharmaceutical compositions containing them |
| PT67562A PT67562B (fr) | 1977-01-24 | 1978-01-23 | Procede pour la preparation d'une composition pharmaceutique contenant de nouveaux composes organiques |
| BE184555A BE863215A (fr) | 1977-01-24 | 1978-01-23 | Nouveaux derives de la benzo (f) isoquinoleine, leur preparation et leur application comme medicaments |
| IE151/78A IE46381B1 (en) | 1977-01-24 | 1978-01-23 | 1,2,3,4,4a,10b-hexahydro-benz(f)isoquinolines |
| PH20696A PH14194A (en) | 1977-01-24 | 1978-01-23 | 1,2,3,4,4a,10b-hexahydro-benz(f)isoquinolines and composition containing the same |
| AT0045478A AT367405B (de) | 1977-01-24 | 1978-01-23 | Verfahren zur herstellung von neuen 1,2,3,4,4a, 10b-hexahydro-benz(f)-isochinolinderivaten und ihren saeureadditionssalzen |
| JP534678A JPS5392778A (en) | 1977-01-24 | 1978-01-23 | Improvement in organic compound |
| ES466245A ES466245A1 (es) | 1977-01-24 | 1978-01-23 | Procedimiento para preparar derivados de isoquinolina |
| CA295,458A CA1105468A (en) | 1977-01-24 | 1978-01-23 | 1,2,3,4,4a,10b-hexahydro-benz¬f|isoquinoline compounds |
| GB2603/78A GB1596170A (en) | 1977-01-24 | 1978-01-23 | 1,2,3,4,4a,10b-hexahydro-benz(f)isouqinolines |
| AU32654/78A AU514089B2 (en) | 1977-01-24 | 1978-01-23 | 1, 2, 3, 4, 4a, 10b-hexahydro-benz(f) isoquinolines |
| SU782571448A SU852172A3 (ru) | 1977-01-24 | 1978-01-23 | Способ получени производныхизОХиНОлиНА или иХ СОлЕй |
| ZA00780430A ZA78430B (en) | 1977-01-24 | 1978-01-24 | Improvements in or relating to organic compounds |
| FR7801860A FR2378015A1 (fr) | 1977-01-24 | 1978-01-24 | Nouveaux derives de la benzo(f)isoquinoleine, leur preparation et leur application comme medicaments |
| ES475587A ES475587A1 (es) | 1977-01-24 | 1978-11-30 | Procedimiento para preparar derivados de isoquinolina |
| AT0400180A AT367406B (de) | 1977-01-24 | 1980-08-01 | Verfahren zur herstellung von neuen 1,2,3,4,4a, 10b-hexahydro-benz(f)isochinolinderivaten und ihren saeureadditionssalzen |
| AT0400080A AT367404B (de) | 1977-01-24 | 1980-08-01 | Verfahren zur herstellung von neuen 1,2,3,4,4a, 10b-hexahydro-benz(f)isochinolinderivaten und ihren saeureadditionssalzen |
| CH190881A CH630903A5 (en) | 1977-01-24 | 1981-03-20 | Process for preparing novel derivatives of 1,2,3,4,4a,10b-hexahydrobenzo(f)isoquinoline. |
| CH190981A CH630904A5 (en) | 1977-01-24 | 1981-03-20 | Process for preparing novel derivatives of 1,2,3,4,4a,10b-hexahydrobenzo(f)isoquinoline. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH82077A CH630902A5 (en) | 1977-01-24 | 1977-01-24 | Process for preparing novel derivatives of 1,2,3,4,4a,10b-hexahydrobenzo(f)isoquinoline. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH630902A5 true CH630902A5 (en) | 1982-07-15 |
Family
ID=4195950
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH82077A CH630902A5 (en) | 1977-01-24 | 1977-01-24 | Process for preparing novel derivatives of 1,2,3,4,4a,10b-hexahydrobenzo(f)isoquinoline. |
| CH190981A CH630904A5 (en) | 1977-01-24 | 1981-03-20 | Process for preparing novel derivatives of 1,2,3,4,4a,10b-hexahydrobenzo(f)isoquinoline. |
| CH190881A CH630903A5 (en) | 1977-01-24 | 1981-03-20 | Process for preparing novel derivatives of 1,2,3,4,4a,10b-hexahydrobenzo(f)isoquinoline. |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH190981A CH630904A5 (en) | 1977-01-24 | 1981-03-20 | Process for preparing novel derivatives of 1,2,3,4,4a,10b-hexahydrobenzo(f)isoquinoline. |
| CH190881A CH630903A5 (en) | 1977-01-24 | 1981-03-20 | Process for preparing novel derivatives of 1,2,3,4,4a,10b-hexahydrobenzo(f)isoquinoline. |
Country Status (21)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE8302361D0 (sv) * | 1983-04-27 | 1983-04-27 | Astra Laekemedel Ab | New tricyclic amines |
| GB8917333D0 (en) * | 1989-07-28 | 1989-09-13 | Merck Sharp & Dohme | Therapeutic agents |
| US5294618A (en) * | 1989-07-28 | 1994-03-15 | Merck Sharp & Dohme Limited | Octahydrobenzisoquinoline derivatives as antipsychotic agents |
| EP0539209A1 (en) * | 1991-10-24 | 1993-04-28 | The Upjohn Company | Benzo-isoquinoline derivatives and analogs and their use in therapeutics |
| JPH07500333A (ja) * | 1991-10-24 | 1995-01-12 | ジ・アップジョン・カンパニー | ベンゾ−イソキノリン誘導体 |
| TW357143B (en) * | 1995-07-07 | 1999-05-01 | Novartis Ag | Benzo[g]quinoline derivatives |
| AT407636B (de) * | 1999-07-09 | 2001-05-25 | Martin Dr Kratzel | Diels-alder-produkte von tetrahydropyridin-dienen mit naphthochinonen und deren oxidationsprodukte, verfahren zu ihrer herstellung und ihre verwendung zur herstellung von arzneimitteln |
-
1977
- 1977-01-24 CH CH82077A patent/CH630902A5/de not_active IP Right Cessation
-
1978
- 1978-01-14 DE DE19782801576 patent/DE2801576A1/de not_active Withdrawn
- 1978-01-16 SE SE7800452A patent/SE7800452L/xx unknown
- 1978-01-16 FI FI780130A patent/FI780130A7/fi not_active Application Discontinuation
- 1978-01-16 DK DK19278A patent/DK19278A/da not_active Application Discontinuation
- 1978-01-18 IT IT7847687A patent/IT7847687A0/it unknown
- 1978-01-20 NZ NZ186279A patent/NZ186279A/xx unknown
- 1978-01-20 NL NL7800719A patent/NL7800719A/xx not_active Application Discontinuation
- 1978-01-23 BE BE184555A patent/BE863215A/xx not_active IP Right Cessation
- 1978-01-23 GB GB2603/78A patent/GB1596170A/en not_active Expired
- 1978-01-23 IL IL53869A patent/IL53869A/xx unknown
- 1978-01-23 PH PH20696A patent/PH14194A/en unknown
- 1978-01-23 AT AT0045478A patent/AT367405B/de not_active IP Right Cessation
- 1978-01-23 PT PT67562A patent/PT67562B/pt unknown
- 1978-01-23 ES ES466245A patent/ES466245A1/es not_active Expired
- 1978-01-23 JP JP534678A patent/JPS5392778A/ja active Pending
- 1978-01-23 CA CA295,458A patent/CA1105468A/en not_active Expired
- 1978-01-23 SU SU782571448A patent/SU852172A3/ru active
- 1978-01-23 IE IE151/78A patent/IE46381B1/en unknown
- 1978-01-24 ZA ZA00780430A patent/ZA78430B/xx unknown
- 1978-01-24 FR FR7801860A patent/FR2378015A1/fr active Granted
- 1978-11-30 ES ES475587A patent/ES475587A1/es not_active Expired
-
1981
- 1981-03-20 CH CH190981A patent/CH630904A5/de not_active IP Right Cessation
- 1981-03-20 CH CH190881A patent/CH630903A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IT7847687A0 (it) | 1978-01-18 |
| DK19278A (da) | 1978-07-25 |
| FR2378015A1 (fr) | 1978-08-18 |
| IL53869A (en) | 1981-05-20 |
| IE46381B1 (en) | 1983-05-18 |
| BE863215A (fr) | 1978-07-24 |
| PH14194A (en) | 1981-03-26 |
| DE2801576A1 (de) | 1978-07-27 |
| JPS5392778A (en) | 1978-08-15 |
| CH630904A5 (en) | 1982-07-15 |
| ATA45478A (de) | 1981-11-15 |
| AT367405B (de) | 1982-07-12 |
| SU852172A3 (ru) | 1981-07-30 |
| ES466245A1 (es) | 1980-12-16 |
| NL7800719A (nl) | 1978-07-26 |
| FR2378015B1 (enrdf_load_stackoverflow) | 1980-08-22 |
| NZ186279A (en) | 1980-05-27 |
| CA1105468A (en) | 1981-07-21 |
| IL53869A0 (en) | 1978-04-30 |
| IE780151L (en) | 1978-07-24 |
| SE7800452L (sv) | 1978-07-25 |
| CH630903A5 (en) | 1982-07-15 |
| PT67562B (fr) | 1980-11-03 |
| ZA78430B (en) | 1979-09-26 |
| AU3265478A (en) | 1979-08-02 |
| PT67562A (fr) | 1978-02-01 |
| ES475587A1 (es) | 1980-02-16 |
| FI780130A7 (fi) | 1978-07-25 |
| GB1596170A (en) | 1981-08-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |