CH341161A - Verfahren zur Herstellung von substituierten 2-Hydroxy-benzo [ a ] chinolizinen - Google Patents
Verfahren zur Herstellung von substituierten 2-Hydroxy-benzo [ a ] chinolizinenInfo
- Publication number
- CH341161A CH341161A CH341161DA CH341161A CH 341161 A CH341161 A CH 341161A CH 341161D A CH341161D A CH 341161DA CH 341161 A CH341161 A CH 341161A
- Authority
- CH
- Switzerland
- Prior art keywords
- benzo
- hydroxy
- quinolizine
- hexahydro
- hydrogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- HPNOEHPRGBNPSI-UHFFFAOYSA-N 6H-benzo[a]quinolizin-2-ol Chemical class OC=1C=CN2CC=C3C(=C2C=1)C=CC=C3 HPNOEHPRGBNPSI-UHFFFAOYSA-N 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- -1 lithium aluminum hydride Chemical compound 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- GANUIJNXRUUOPR-UHFFFAOYSA-N benzo[a]quinolizin-2-one Chemical class C1=CC=C2C3=CC(=O)C=CN3C=CC2=C1 GANUIJNXRUUOPR-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 239000012279 sodium borohydride Substances 0.000 claims 1
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
- 238000002844 melting Methods 0.000 description 25
- 230000008018 melting Effects 0.000 description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 6
- BOBCQOOZINHVMK-UHFFFAOYSA-N 3-Ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizin-2-one Chemical compound C1CC2=CC(OC)=C(OC)C=C2C2N1CC(CC)C(=O)C2 BOBCQOOZINHVMK-UHFFFAOYSA-N 0.000 description 5
- LYDWUTUOAGCHNM-UHFFFAOYSA-N 3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1h-benzo[a]quinolizin-2-ol Chemical compound C1CC2=CC(OC)=C(OC)C=C2C2N1CC(CC)C(O)C2 LYDWUTUOAGCHNM-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical class [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- NFMGJPQXTFCOOK-UHFFFAOYSA-N 3-butyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1h-benzo[a]quinolizin-2-ol Chemical compound C1CC2=CC(OC)=C(OC)C=C2C2N1CC(CCCC)C(O)C2 NFMGJPQXTFCOOK-UHFFFAOYSA-N 0.000 description 3
- CBWGPPPRRXQRJI-UHFFFAOYSA-N 3-ethyl-9,10-dihydroxy-1,3,4,6,7,11b-hexahydrobenzo[a]quinolizin-2-one hydrobromide Chemical compound Br.O=C1C(CN2CCC3=C(C2C1)C=C(C(=C3)O)O)CC CBWGPPPRRXQRJI-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 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
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CXDIPZOEHIFPBF-UHFFFAOYSA-N 3-butyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydrobenzo[a]quinolizin-2-one Chemical compound C1CC2=CC(OC)=C(OC)C=C2C2N1CC(CCCC)C(=O)C2 CXDIPZOEHIFPBF-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N malonic acid group Chemical group C(CC(=O)O)(=O)O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 125000004043 oxo group Chemical group O=* 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- GTXWEEQMXHSWSX-UHFFFAOYSA-N 3-benzyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizin-2-ol Chemical compound OC1C(CN2CCC3=C(C2C1)C=C(C(=C3)OC)OC)CC3=CC=CC=C3 GTXWEEQMXHSWSX-UHFFFAOYSA-N 0.000 description 1
- JPCZEIBFGHTUAZ-UHFFFAOYSA-N 3-butyl-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizine-2,9,10-triol Chemical compound OC1C(CN2CCC3=C(C2C1)C=C(C(=C3)O)O)CCCC JPCZEIBFGHTUAZ-UHFFFAOYSA-N 0.000 description 1
- FDFIXBQYRWADST-UHFFFAOYSA-N 3-butyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydrobenzo[a]quinolizin-2-one;hydrochloride Chemical compound Cl.C1CC2=CC(OC)=C(OC)C=C2C2N1CC(CCCC)C(=O)C2 FDFIXBQYRWADST-UHFFFAOYSA-N 0.000 description 1
- FVDINOYNMDSPJZ-UHFFFAOYSA-N 3-ethyl-2,3,4,6,7,12b-hexahydro-1H-[1,3]benzodioxolo[6,5-a]quinolizin-2-ol Chemical compound OC1C(CN2CCC3=C(C2C1)C=C1C(=C3)OCO1)CC FVDINOYNMDSPJZ-UHFFFAOYSA-N 0.000 description 1
- OBCSDBBOKFZULP-UHFFFAOYSA-N 4H-benzo[a]quinolizin-2-ol Chemical class C1=CC=C2C3=CC(O)=CCN3C=CC2=C1 OBCSDBBOKFZULP-UHFFFAOYSA-N 0.000 description 1
- TYLDXYDHKOORNN-UHFFFAOYSA-N 9,10-dimethoxy-3-(oxolan-2-ylmethyl)-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizin-2-ol Chemical compound OC1C(CN2CCC3=C(C2C1)C=C(C(=C3)OC)OC)CC1CCCO1 TYLDXYDHKOORNN-UHFFFAOYSA-N 0.000 description 1
- FDOJFNIZVPVTQE-UHFFFAOYSA-N CCCCCCC(CN(CC1)C(C2)C(C=C3OC)=C1C=C3OC)C2O Chemical compound CCCCCCC(CN(CC1)C(C2)C(C=C3OC)=C1C=C3OC)C2O FDOJFNIZVPVTQE-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
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 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
- 239000003513 alkali Substances 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- WEQLWGNDNRARGE-UHFFFAOYSA-N b-Dihydrotetrabenazine Chemical compound C1CN2CC(CC(C)C)C(O)CC2C2=C1C=C(OC)C(OC)=C2 WEQLWGNDNRARGE-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
-
- 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
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
- C07D455/06—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine containing benzo [a] quinolizine ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH341161T | 1956-02-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH341161A true CH341161A (de) | 1959-09-30 |
Family
ID=4505675
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH341161D CH341161A (de) | 1956-02-08 | 1956-02-08 | Verfahren zur Herstellung von substituierten 2-Hydroxy-benzo [ a ] chinolizinen |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT196875B (da) |
| BE (1) | BE554816A (da) |
| CH (1) | CH341161A (da) |
| DE (1) | DE1082912B (da) |
| DK (1) | DK89401C (da) |
| ES (1) | ES233470A1 (da) |
| FR (1) | FR1231641A (da) |
| GB (1) | GB800969A (da) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU175890B (en) * | 1977-06-15 | 1980-11-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing new 1,2,3,4,6,7-hexahydro-11-b-alpha-benzo-square bracket-a-square brecket closed-quinolyzine derivatives |
| WO2011019956A2 (en) | 2009-08-12 | 2011-02-17 | Biovail Laboratories International (Barbados) S.R.L. | Pharmaceutical compositions |
| GB2463452A (en) * | 2008-09-08 | 2010-03-17 | Cambridge Lab | Desmethyl derivatives of tetrabenazine and pharmaceutical compositions thereof |
| CN110691596A (zh) * | 2017-04-01 | 2020-01-14 | 阿德普蒂奥制药有限公司 | 药物组合物 |
| GB201705304D0 (en) | 2017-04-01 | 2017-05-17 | Adeptio Pharmaceuticals Ltd | Pharmaceutical compositions |
| GB201705305D0 (en) | 2017-04-01 | 2017-05-17 | Adeptio Pharmaceuticals Ltd | Pharmaceutical compositions |
| GB201705303D0 (en) | 2017-04-01 | 2017-05-17 | Adeptio Pharmaceuticals Ltd | Pharmaceutical compositions |
| GB201705302D0 (en) | 2017-04-01 | 2017-05-17 | Adeptio Pharmaceuticals Ltd | Pharmaceutical compositions |
| GB201705306D0 (en) | 2017-04-01 | 2017-05-17 | Adeptio Pharmaceuticals Ltd | Pharmaceutical compositions |
| GB201808464D0 (en) | 2018-05-23 | 2018-07-11 | Adeptio Pharmaceuticals Ltd | Pharmaceutical compounds for use in treating huntington's disease |
-
1956
- 1956-02-08 CH CH341161D patent/CH341161A/de unknown
-
1957
- 1957-01-31 AT AT196875D patent/AT196875B/de active
- 1957-01-31 DE DEH29179A patent/DE1082912B/de active Pending
- 1957-02-04 GB GB3722/57A patent/GB800969A/en not_active Expired
- 1957-02-06 FR FR731133A patent/FR1231641A/fr not_active Expired
- 1957-02-07 BE BE554816A patent/BE554816A/fr unknown
- 1957-02-07 ES ES0233470A patent/ES233470A1/es not_active Expired
- 1957-02-08 DK DK47057A patent/DK89401C/da active
Also Published As
| Publication number | Publication date |
|---|---|
| ES233470A1 (es) | 1957-10-16 |
| BE554816A (fr) | 1960-02-12 |
| GB800969A (en) | 1958-09-03 |
| FR1231641A (fr) | 1960-09-30 |
| AT196875B (de) | 1958-03-25 |
| DK89401C (da) | 1960-07-25 |
| DE1082912B (de) | 1960-06-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH341161A (de) | Verfahren zur Herstellung von substituierten 2-Hydroxy-benzo [ a ] chinolizinen | |
| DE3026534A1 (de) | 3,1-benzoxazin-2-one, ihre herstellung und verwendung | |
| DE1294961B (de) | Verfahren zur Herstellung von 22-Azacholestanderivaten und deren Saeureadditionssalzen | |
| CH530401A (de) | Verfahren zur Herstellung von Phenanthridinderivaten | |
| DE948979C (de) | Verfahren zur Herstellung von anticholinergisch wirksamen Salzen quaternaerer Ammonium- und Piperidiniumbasen | |
| DE930329C (de) | Verfahren zur Herstellung von Alkyl- bzw. Alkoxalkylaminobenzoesaeureestern | |
| DE963517C (de) | Verfahren zur Herstellung von antipyretisch und analgetisch wirksamen, basisch substituierten Phenyldimethylpyrazolon-Derivaten | |
| DE936571C (de) | Verfahren zur Herstellung von 4-Aminochromanen | |
| AT206439B (de) | Verfahren zur Herstellung von neuen, racemischen oder optisch aktiven Piperidyl-(2)-arylmethanoläthern | |
| DE1445895C (de) | Verfahren zur Herstellung von 2 Dehydroemetinderivaten | |
| AT267527B (de) | Verfahren zur Herstellung neuer substituierter Aminopyridine, von deren Salzen und optisch aktiven Isomeren | |
| DE725535C (de) | Verfahren zur Herstellung von Tetrahydroisochinolinverbindungen | |
| AT235280B (de) | Verfahren zur Herstellung neuer Indolderivate | |
| AT239209B (de) | Verfahren zur Herstellung von neuen bicyclisch substituierten Aminoalkanen sowie deren Salzen und quaternären Ammoniumverbindungen | |
| AT214427B (de) | Verfahren zur Herstellung neuer basischer Phenoläther | |
| DE2503156A1 (de) | Verfahren zur herstellung neuer heterocyclischer verbindungen | |
| AT200136B (de) | Verfahren zur Herstellung von neuen tertiären Aminen der Tetrahydrofuranreihe | |
| AT237601B (de) | Verfahren zur Herstellung von 2-Phenyläthylaminderivaten | |
| AT216485B (de) | Verfahren zur Herstellung neuer tertiärer Amine | |
| AT215999B (de) | Verfahren zur Herstellung von neuen Pyridylmethylaminen | |
| AT212314B (de) | Verfahren zur Herstellung von neuen, in threo- oder erythro-Form, als Racemat oder als optisch aktive Verbindungen vorliegenden Derivaten des Piperidyl-(2)-phenylmethanols | |
| CH295534A (de) | Verfahren zur Herstellung eines 1-Azabicycloalkanol-Derivates. | |
| AT333735B (de) | Verfahren zur herstellung von neuen carbonsaureestern von 3-(4-biphenylyl)-1-butanolen und 3-(4-biphenylyl)-2-buten-1-olen | |
| DE1620436C (de) | Carboxamidoalkyl 1,3 benzoxazin 2 on derivate und Verfahren zu deren Her stellung | |
| DE1204682B (de) | Verfahren zur Herstellung blutdruckwirksamer Amine |