CH377348A - Verfahren zur Herstellung von substituierten 1-Phenäthyl-tetrahydroisochinolinen - Google Patents

Verfahren zur Herstellung von substituierten 1-Phenäthyl-tetrahydroisochinolinen

Info

Publication number: CH377348A
Authority: CH; Switzerland
Prior art keywords: sep; dimethoxy; phenethyl; hydrochloride; styryl
Prior art date: 1958-09-04

Application number

CH6358458A

Other languages

German (de)

English (en)

Inventor

Hedwig Dr Besendorf

Arnold Dr Brossi

Otto Dr Schnider

Original Assignee

Hoffmann La Roche

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1958-09-04

Filing date

1958-09-04

Publication date

1964-05-15

1958-09-04 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1958-09-04 Priority to CH6358458A priority Critical patent/CH377348A/de

1959-08-26 Priority to BE582044A priority patent/BE582044A/fr

1959-09-02 Priority to FR804084A priority patent/FR1272493A/fr

1959-09-03 Priority to ES0251894A priority patent/ES251894A1/es

1960-08-11 Priority to FR835578A priority patent/FR170M/fr

1964-05-15 Publication of CH377348A publication Critical patent/CH377348A/de

1964-12-26 Priority to OA51045A priority patent/OA00950A/fr

Links

238000000034 method Methods 0.000 title claims description 9
238000002360 preparation method Methods 0.000 title claims description 4
JIOZLMQZYORGDP-UHFFFAOYSA-N 1-(1-phenylethyl)-1,2,3,4-tetrahydroisoquinoline Chemical class N1CCC2=CC=CC=C2C1C(C)C1=CC=CC=C1 JIOZLMQZYORGDP-UHFFFAOYSA-N 0.000 title description 7
-1 styryl ketone Chemical class 0.000 claims description 19
150000001875 compounds Chemical class 0.000 claims description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
239000011707 mineral Substances 0.000 claims description 5
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 4
150000003526 tetrahydroisoquinolines Chemical class 0.000 claims description 3
UKUJIVVXTYWNIO-UHFFFAOYSA-N 1-(2-phenylethyl)-1,2,3,4-tetrahydroisoquinoline Chemical compound N1CCC2=CC=CC=C2C1CCC1=CC=CC=C1 UKUJIVVXTYWNIO-UHFFFAOYSA-N 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
239000000463 material Substances 0.000 claims description 2
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 2
NKSZCPBUWGZONP-UHFFFAOYSA-N 3,4-dihydroisoquinoline Chemical compound C1=CC=C2C=NCCC2=C1 NKSZCPBUWGZONP-UHFFFAOYSA-N 0.000 claims 1
230000001419 dependent effect Effects 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
238000002844 melting Methods 0.000 description 14
230000008018 melting Effects 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 11
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
239000002585 base Substances 0.000 description 9
239000000203 mixture Substances 0.000 description 9
UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical class C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 7
230000000875 corresponding effect Effects 0.000 description 7
OJDCLDHLPJXFQL-UHFFFAOYSA-N 1-(2-phenylethenyl)-3,4-dihydroisoquinoline Chemical class N=1CCC2=CC=CC=C2C=1C=CC1=CC=CC=C1 OJDCLDHLPJXFQL-UHFFFAOYSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
238000010521 absorption reaction Methods 0.000 description 6
230000001476 alcoholic effect Effects 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
MGFREDWKELGWML-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinolin-2-ium;chloride Chemical compound [Cl-].C1=CC=C2C[NH2+]CCC2=C1 MGFREDWKELGWML-UHFFFAOYSA-N 0.000 description 3
ASHMWTTWGPKMFF-UHFFFAOYSA-N 3,4-dihydroisoquinolin-2-ium;chloride Chemical compound Cl.C1=CC=C2C=NCCC2=C1 ASHMWTTWGPKMFF-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000003795 chemical substances by application Substances 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
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000000155 melt Substances 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
238000007363 ring formation reaction Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
KTKBJXIOEBQKRH-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)ethenyl]-6,7-dimethoxy-3,4-dihydroisoquinoline hydrochloride Chemical compound Cl.ClC1=CC=C(C=CC2=NCCC3=CC(=C(C=C23)OC)OC)C=C1 KTKBJXIOEBQKRH-UHFFFAOYSA-N 0.000 description 2
AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
239000003513 alkali Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000008098 formaldehyde solution Substances 0.000 description 2
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
230000011987 methylation Effects 0.000 description 2
238000007069 methylation reaction Methods 0.000 description 2
YBCPYHQFUMNOJG-UHFFFAOYSA-N metofoline Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(C)C1CCC1=CC=C(Cl)C=C1 YBCPYHQFUMNOJG-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
125000005504 styryl group Chemical group 0.000 description 2
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
QXIWCXBQTCPAFO-UHFFFAOYSA-N 1,1-dimethoxy-2h-isoquinoline Chemical compound C1=CC=C2C(OC)(OC)NC=CC2=C1 QXIWCXBQTCPAFO-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
KZZQNUBLEGEKGG-UHFFFAOYSA-N 1-(2-phenylethenyl)-1,2,3,4-tetrahydroisoquinoline Chemical class N1CCC2=CC=CC=C2C1C=CC1=CC=CC=C1 KZZQNUBLEGEKGG-UHFFFAOYSA-N 0.000 description 1
MCXVMFJDFVWJGX-UHFFFAOYSA-N 1-[2-(4-bromophenyl)ethyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinoline Chemical compound BrC1=CC=C(C=C1)CCC1N(CCC2=CC(=C(C=C12)OC)OC)C MCXVMFJDFVWJGX-UHFFFAOYSA-N 0.000 description 1
LYOMAIRWFRVYLN-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)ethenyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline Chemical compound ClC1=CC=C(C=CC2NCCC3=CC(=C(C=C23)OC)OC)C=C1 LYOMAIRWFRVYLN-UHFFFAOYSA-N 0.000 description 1
FPANOAGJIXLUKT-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)ethyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=2C=C(OC)C(OC)=CC=2CCNC1CCC1=CC=C(Cl)C=C1 FPANOAGJIXLUKT-UHFFFAOYSA-N 0.000 description 1
WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 description 1
KAJZFXZLJBACNX-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-1-phenylprop-2-en-1-one Chemical compound ClC1=CC(Cl)=CC=C1C=CC(=O)C1=CC=CC=C1 KAJZFXZLJBACNX-UHFFFAOYSA-N 0.000 description 1
QWYKPZUFPSREFT-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-1-phenylprop-2-en-1-one Chemical compound C1=C(Cl)C(Cl)=CC=C1C=CC(=O)C1=CC=CC=C1 QWYKPZUFPSREFT-UHFFFAOYSA-N 0.000 description 1
XBFMSIZYORSEPA-UHFFFAOYSA-N 3-(3-chlorophenyl)-1-phenylprop-2-en-1-one Chemical compound ClC1=CC=CC(C=CC(=O)C=2C=CC=CC=2)=C1 XBFMSIZYORSEPA-UHFFFAOYSA-N 0.000 description 1
ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 description 1
238000006407 Bischler-Napieralski reaction Methods 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-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
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
230000006181 N-acylation Effects 0.000 description 1
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical class [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 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
WJGAPUXHSQQWQF-UHFFFAOYSA-N acetic acid;hydrochloride Chemical compound Cl.CC(O)=O WJGAPUXHSQQWQF-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 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
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
150000004800 hydroisoquinoline derivatives Chemical class 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229910052987 metal hydride Inorganic materials 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
239000003960 organic solvent Substances 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
230000002048 spasmolytic effect Effects 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
238000010792 warming Methods 0.000 description 1
238000005406 washing Methods 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
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/18—Aralkyl radicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)

CH6358458A 1958-09-04 1958-09-04 Verfahren zur Herstellung von substituierten 1-Phenäthyl-tetrahydroisochinolinen CH377348A (de)

Priority Applications (6)

Application Number	Priority Date	Filing Date	Title
CH6358458A CH377348A (de)	1958-09-04	1958-09-04	Verfahren zur Herstellung von substituierten 1-Phenäthyl-tetrahydroisochinolinen
BE582044A BE582044A (fr)	1958-09-04	1959-08-26	Procédé pour la préparation de dérivés de tétrahydro-isoquinoléine
FR804084A FR1272493A (fr)	1958-09-04	1959-09-02	Procédé pour la préparation de dérivés de tétrahydroisoquinoléine
ES0251894A ES251894A1 (es)	1958-09-04	1959-09-03	Procedimiento para la fabricaciën de derivados de tetrahidroisoquinolina
FR835578A FR170M (fr)	1958-09-04	1960-08-11	Dérivés de tétrahydroisoquinoléine.
OA51045A OA00950A (fr)	1958-09-04	1964-12-26	Procédé pour la préparation de dérivés de tétrahydroisoquinoléine.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH6358458A CH377348A (de)	1958-09-04	1958-09-04	Verfahren zur Herstellung von substituierten 1-Phenäthyl-tetrahydroisochinolinen

Publications (1)

Publication Number	Publication Date
CH377348A true CH377348A (de)	1964-05-15

Family

ID=4525093

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH6358458A CH377348A (de)	1958-09-04	1958-09-04	Verfahren zur Herstellung von substituierten 1-Phenäthyl-tetrahydroisochinolinen

Country Status (5)

Country	Link
BE (1)	BE582044A (fr)
CH (1)	CH377348A (fr)
ES (1)	ES251894A1 (fr)
FR (2)	FR1272493A (fr)
OA (1)	OA00950A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1199775B (de) *	1960-04-01	1965-09-02	Hoffmann La Roche	Verfahren zur Herstellung von analgetisch, hustenlindernd und spasmolytisch wirksamenTetrahydroisochinolinderivaten

1958
- 1958-09-04 CH CH6358458A patent/CH377348A/de unknown
1959
- 1959-08-26 BE BE582044A patent/BE582044A/fr unknown
- 1959-09-02 FR FR804084A patent/FR1272493A/fr not_active Expired
- 1959-09-03 ES ES0251894A patent/ES251894A1/es not_active Expired
1960
- 1960-08-11 FR FR835578A patent/FR170M/fr not_active Expired
1964
- 1964-12-26 OA OA51045A patent/OA00950A/fr unknown

Also Published As

Publication number	Publication date
ES251894A1 (es)	1960-03-16
FR1272493A (fr)	1961-09-29
OA00950A (fr)	1968-03-22
FR170M (fr)	1961-02-13
BE582044A (fr)	1960-02-26

Publication	Publication Date	Title
EP0110372B1 (fr)	1986-09-10	Dérivés de la 1-phénylisoquinoléine, procédé pour leur préparation, compositions pharmaceutiques contenant ces composés et leur utilisation
NO132979B (fr)	1975-11-10
DE2229695A1 (de)	1974-01-31	2-(heteroaryl-methyl)-5,9 beta-dialkyl6,7-benzomorphane, deren saeureadditionssalze sowie verfahren zu deren herstellung
DE2818403A1 (de)	1979-11-08	Neue isochinolinderivate und verfahren zu ihrer herstellung
DE1445845A1 (de)	1969-02-06	Neue Benzomorphane und Verfahren zu ihrer Herstellung
CH377348A (de)	1964-05-15	Verfahren zur Herstellung von substituierten 1-Phenäthyl-tetrahydroisochinolinen
Battersby et al.	1953	499. The synthesis of emetine and related compounds. Part II. The synthesis of (±)-rubremetinium bromide
AT212832B (de)	1961-01-10	Verfahren zur Herstellung von neuen Tetrahydroisochinolin-Derivaten
Whaley et al.	1953	217. The synthesis and resolution of (±)-corlumine
EP0000013B1 (fr)	1980-10-15	4-Phényl-8-amino-tetrahydroisoquinoléines, compositions pharmaceutiques les contenant et procédé pour préparer ces compositions
DE1014545B (de)	1957-08-29	Verfahren zur Herstellung von N-Alkyl-, N-Alkenyl- oder N-Aralkyl-3-oxymorphinanen
DE2034587A1 (de)	1971-02-11	Neue, insbesondere sympathikolytische pharmazeutische Zusammensetzungen auf der Basis von Isochinolinen und neue substituierte Isochinoline
AT219041B (de)	1962-01-10	Verfahren zur Herstellung von neuen Tetrahydroisochinolin-Derivaten
DE1108222B (de)	1961-06-08	Verfahren zur Herstellung von 1-Phenylaethyl-tetrahydroisochinolin-verbindungen und deren Salzen
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AT200265B (de)	1958-10-25	Verfahren zur Herstellung von dl-Emetin
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CH387633A (de)	1965-02-15	Verfahren zur Herstellung von 1,2,3,4-Tetrahydroisochinolinen
AT222120B (de)	1962-07-10	Verfahren zur Herstellung von neuen Tetrahydroisochinolin-Derivaten
DE1445845C (de)	1971-11-11	5-Phenyl-6,7-benzomorphane
AT376672B (de)	1984-12-27	Verfahren zur herstellung von neuen 2(4-piperidyl)-1-(4-chinolyl)-aethanderivaten und ihren salzen
AT272347B (de)	1969-07-10	Verfahren zur Herstellung von neuen Pyridyl-dihydroisochinolinen und von deren Säureadditionssalzen
AT234692B (de)	1964-07-10	Verfahren zur Herstellung von Isochinolin-Derivaten
AT206441B (de)	1959-11-25	Verfahren zur Herstellung von substituierten 2-Hydroxy-1,2,3,4,6,7-hexahydro-11 bH-benzo[a]chinolizinen
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