CH450414A - Verfahren zur Herstellung von Benzo(a)chinolizinderivaten - Google Patents

Verfahren zur Herstellung von Benzo(a)chinolizinderivaten

Info

Publication number: CH450414A
Authority: CH; Switzerland
Prior art keywords: formula; benzo; dihydro; ethyl; dimethoxy
Prior art date: 1963-06-07

Application number

CH704063A

Other languages

German (de)

English (en)

Inventor

Max Dr Gerecke

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.)

1963-06-07

Filing date

1963-06-07

Publication date

1968-01-31

1963-06-07 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1963-06-07 Priority to CH704063A priority Critical patent/CH450414A/de

1963-06-07 Priority to CH704163A priority patent/CH442316A/de

1964-04-20 Priority to DE19641445895 priority patent/DE1445895C/de

1964-05-06 Priority to NL6405025A priority patent/NL6405025A/xx

1964-05-11 Priority to SE05726/64A priority patent/SE326448B/xx

1964-05-21 Priority to NL6405645A priority patent/NL125065C/xx

1964-06-03 Priority to SE6717/64A priority patent/SE315284B/xx

1964-06-03 Priority to BR159689/64A priority patent/BR6459689D0/pt

1964-06-03 Priority to BR159690/64A priority patent/BR6459690D0/pt

1964-06-03 Priority to FR976838A priority patent/FR1403940A/fr

1964-06-04 Priority to BE648824D priority patent/BE648824A/xx

1964-06-04 Priority to FR976990A priority patent/FR1403941A/fr

1964-06-04 Priority to BE648823D priority patent/BE648823A/fr

1964-06-05 Priority to GB18814/66A priority patent/GB1041699A/en

1964-06-05 Priority to GB46933/65A priority patent/GB1042206A/en

1964-06-05 Priority to GB23336/64A priority patent/GB1041696A/en

1964-06-05 Priority to GB23337/64A priority patent/GB1042205A/en

1964-06-05 Priority to US373043A priority patent/US3359264A/en

1964-06-05 Priority to GB45824/65A priority patent/GB1041697A/en

1964-06-05 Priority to GB45825/65A priority patent/GB1041698A/en

1964-06-06 Priority to ES300712A priority patent/ES300712A1/es

1964-06-08 Priority to DK285264AA priority patent/DK107558C/da

1964-06-08 Priority to DK285364AA priority patent/DK123358B/da

1964-12-26 Priority to OA51056A priority patent/OA00961A/fr

1968-01-31 Publication of CH450414A publication Critical patent/CH450414A/de

Links

238000000034 method Methods 0.000 title claims description 12
238000002360 preparation method Methods 0.000 title claims description 4
RMOYSWDTCQZJGS-UHFFFAOYSA-N 6h-benzo[a]quinolizine Chemical class C1=CC=CN2CC=C(C=CC=C3)C3=C21 RMOYSWDTCQZJGS-UHFFFAOYSA-N 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 7
238000006243 chemical reaction Methods 0.000 claims description 7
238000005984 hydrogenation reaction Methods 0.000 claims description 7
239000007858 starting material Substances 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 6
125000003710 aryl alkyl group Chemical group 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
229910000033 sodium borohydride Inorganic materials 0.000 claims description 6
239000012279 sodium borohydride Substances 0.000 claims description 6
150000001450 anions Chemical class 0.000 claims description 5
239000007795 chemical reaction product Substances 0.000 claims description 4
NKSZCPBUWGZONP-UHFFFAOYSA-N 3,4-dihydroisoquinoline Chemical class C1=CC=C2C=NCCC2=C1 NKSZCPBUWGZONP-UHFFFAOYSA-N 0.000 claims description 3
239000000047 product Substances 0.000 claims description 3
YDZIFJMWOCAKAO-UHFFFAOYSA-N 3-ethyl-9,10-dimethoxy-2-methyl-6,7-dihydrobenzo[a]quinolizin-5-ium Chemical class CC=1C(=C[N+]=2CCC3=C(C2C1)C=C(C(=C3)OC)OC)CC YDZIFJMWOCAKAO-UHFFFAOYSA-N 0.000 claims description 2
QCRCVAMGUZYIKG-UHFFFAOYSA-N 6,7-dihydrobenzo[a]quinolizin-5-ium Chemical class C1=CC=C2CC[N+]3=CC=CC=C3C2=C1 QCRCVAMGUZYIKG-UHFFFAOYSA-N 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
238000003776 cleavage reaction Methods 0.000 claims description 2
230000007017 scission Effects 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 2
125000002471 4H-quinolizinyl group Chemical class C=1(C=CCN2C=CC=CC12)* 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
239000000243 solution Substances 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
239000000706 filtrate Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
239000013078 crystal 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
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 3
VKQSJVGUTKKLAD-UHFFFAOYSA-M quinolizin-5-ium;bromide Chemical compound [Br-].C1=CC=CC2=CC=CC=[N+]21 VKQSJVGUTKKLAD-UHFFFAOYSA-M 0.000 description 3
239000000126 substance Substances 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
CWIBEJSBTZBSCH-UHFFFAOYSA-M [Br-].CC=1C(=C[N+]=2CCC3=C(C2C1)C=C(C(=C3)OC)OC)CC Chemical compound [Br-].CC=1C(=C[N+]=2CCC3=C(C2C1)C=C(C(=C3)OC)OC)CC CWIBEJSBTZBSCH-UHFFFAOYSA-M 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
150000001768 cations Chemical class 0.000 description 2
239000002026 chloroform extract Substances 0.000 description 2
238000006264 debenzylation reaction Methods 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
XXLZPUYGHQWHRN-RPBOFIJWSA-N dehydroemetine Chemical compound COC1=C(OC)C=C2[C@@H]3CC(C[C@@H]4C5=CC(OC)=C(OC)C=C5CCN4)=C(CC)CN3CCC2=C1 XXLZPUYGHQWHRN-RPBOFIJWSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
229910052987 metal hydride Inorganic materials 0.000 description 2
150000004681 metal hydrides Chemical class 0.000 description 2
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
-1 methylenedioxy group Chemical group 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
GUOHRXPYGSKUGT-UHFFFAOYSA-N quinolizinium Chemical class C1=CC=CC2=CC=CC=[N+]21 GUOHRXPYGSKUGT-UHFFFAOYSA-N 0.000 description 2
UWDOBVKRBKUGSJ-UHFFFAOYSA-N 2-benzyl-6,7-dimethoxy-3,4-dihydroisoquinolin-2-ium Chemical class C=1C=2C=C(OC)C(OC)=CC=2CC[N+]=1CC1=CC=CC=C1 UWDOBVKRBKUGSJ-UHFFFAOYSA-N 0.000 description 1
206010001986 Amoebic dysentery Diseases 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
BUXOXCZWTSOYOC-UHFFFAOYSA-M [Br-].C1=CC=C[N+]=2C=CC3=C(C1=2)C=CC=C3 Chemical compound [Br-].C1=CC=C[N+]=2C=CC3=C(C1=2)C=CC=C3 BUXOXCZWTSOYOC-UHFFFAOYSA-M 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000005530 alkylenedioxy group Chemical group 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000003245 coal Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229940127089 cytotoxic agent Drugs 0.000 description 1
125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
238000001035 drying Methods 0.000 description 1
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
ZYCMDWDFIQDPLP-UHFFFAOYSA-N hbr bromine Chemical compound Br.Br ZYCMDWDFIQDPLP-UHFFFAOYSA-N 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
SHLPPXXKRFINFY-UHFFFAOYSA-N isoquinolin-2-ium;bromide Chemical compound Br.C1=NC=CC2=CC=CC=C21 SHLPPXXKRFINFY-UHFFFAOYSA-N 0.000 description 1
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical class C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 1
BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000000203 mixture Substances 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
235000015096 spirit Nutrition 0.000 description 1
QXKXDIKCIPXUPL-UHFFFAOYSA-N sulfanylidenemercury Chemical compound [Hg]=S QXKXDIKCIPXUPL-UHFFFAOYSA-N 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- 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
- C07D455/08—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 having an isoquinolyl-1, a substituted isoquinolyl-1 or an alkylenedioxyisoquinolyl-1 radical linked through only one carbon atom, attached in position 2, e.g. emetine
- 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)

CH704063A 1963-06-07 1963-06-07 Verfahren zur Herstellung von Benzo(a)chinolizinderivaten CH450414A (de)

Priority Applications (24)

Application Number	Priority Date	Filing Date	Title
CH704063A CH450414A (de)	1963-06-07	1963-06-07	Verfahren zur Herstellung von Benzo(a)chinolizinderivaten
CH704163A CH442316A (de)	1963-06-07	1963-06-07	Verfahren zur Herstellung von Benzo(a)chinolizinderivaten
DE19641445895 DE1445895C (de)	1963-06-07	1964-04-20	Verfahren zur Herstellung von 2 Dehydroemetinderivaten
NL6405025A NL6405025A (fr)	1963-06-07	1964-05-06
SE05726/64A SE326448B (fr)	1963-06-07	1964-05-11
NL6405645A NL125065C (fr)	1963-06-07	1964-05-21
SE6717/64A SE315284B (fr)	1963-06-07	1964-06-03
BR159689/64A BR6459689D0 (pt)	1963-06-07	1964-06-03	Processo para a preparacao de derivados de benzo(a)quinolizina
BR159690/64A BR6459690D0 (pt)	1963-06-07	1964-06-03	Processo para a preparacao de derivados de benzo(a)quinolizina
FR976838A FR1403940A (fr)	1963-06-07	1964-06-03	Procédé pour la préparation de dérivés de benzo [a] quinolizine
BE648824D BE648824A (fr)	1963-06-07	1964-06-04
FR976990A FR1403941A (fr)	1963-06-07	1964-06-04	Procédé pour la préparation de dérivés de benzo [a] quinolizine
BE648823D BE648823A (fr)	1963-06-07	1964-06-04
GB18814/66A GB1041699A (en)	1963-06-07	1964-06-05	Novel tetrahydro isoquinolinyl-methyldihydrobenzo[a]quinolizinium salts
GB46933/65A GB1042206A (en)	1963-06-07	1964-06-05	Benzo[a]quinolizine amides and the preparation thereof
GB23336/64A GB1041696A (en)	1963-06-07	1964-06-05	Manufacture of benzo[a]quinolizines
GB23337/64A GB1042205A (en)	1963-06-07	1964-06-05	Manufacture of benzo[a]quinolizines
US373043A US3359264A (en)	1963-06-07	1964-06-05	Benzo[a] quinolizine derivatives and processes for the manufacture thereof
GB45824/65A GB1041697A (en)	1963-06-07	1964-06-05	Novel 6,7-dihydro-benzo[a]quinolizinium salts and a process for the preparation thereof
GB45825/65A GB1041698A (en)	1963-06-07	1964-06-05	Novel 3,4-dihydro-isoquinolinium salts
ES300712A ES300712A1 (es)	1963-06-07	1964-06-06	Procedimiento para la preparación de derivados de benzo[a]quinolizina
DK285264AA DK107558C (da)	1963-06-07	1964-06-08	Fremgangsmåde til fremstilling af benzo(a)quinolizinderivater.
DK285364AA DK123358B (da)	1963-06-07	1964-06-08	Fremgangsmåde til fremstilling af benzo[a]quinolizinderivater.
OA51056A OA00961A (fr)	1963-06-07	1964-12-26	Procédé pour la préparation de dérivés de benzo(a)quinolizine.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH704063A CH450414A (de)	1963-06-07	1963-06-07	Verfahren zur Herstellung von Benzo(a)chinolizinderivaten

Publications (1)

Publication Number	Publication Date
CH450414A true CH450414A (de)	1968-01-31

Family

ID=4318976

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH704063A CH450414A (de)	1963-06-07	1963-06-07	Verfahren zur Herstellung von Benzo(a)chinolizinderivaten

Country Status (4)

Country	Link
CH (1)	CH450414A (fr)
DK (1)	DK107558C (fr)
ES (1)	ES300712A1 (fr)
OA (1)	OA00961A (fr)

1963
- 1963-06-07 CH CH704063A patent/CH450414A/de unknown
1964
- 1964-06-06 ES ES300712A patent/ES300712A1/es not_active Expired
- 1964-06-08 DK DK285264AA patent/DK107558C/da active
- 1964-12-26 OA OA51056A patent/OA00961A/fr unknown

Also Published As

Publication number	Publication date
ES300712A1 (es)	1964-11-16
OA00961A (fr)	1968-08-07
DK107558C (da)	1967-06-12

Publication	Publication Date	Title
DE1445848A1 (de)	1968-11-21	Verfahren zur Herstellung eines neuen Isoxazolderivates
CH558362A (de)	1975-01-31	Verfahren zur herstellung von endoaethano-tetrahydrothebainen bzw. -oripavinen.
CH427795A (de)	1967-01-15	Verfahren zur Herstellung von Pyridinderivaten
DE2225765A1 (de)	1972-12-07	3- eckige Klammer auf 2-(4-Phenyl-lpiperazinyl)-äthyl eckige Klammer zu -indoline
CH450414A (de)	1968-01-31	Verfahren zur Herstellung von Benzo(a)chinolizinderivaten
DE2512673A1 (de)	1975-10-02	7-(hydroxyphenyl)pyrido eckige klammer auf 3,4-d eckige klammer zu pyridazine und verfahren zu ihrer herstellung
DE69006366T2 (de)	1994-08-11	BENZO[b]PHENANTHROLINDERIVATE, IHRE HERSTELLUNG UND IHRE THERAPEUTISCHE VERWENDUNG.
DE2024049C3 (de)	1978-07-20	a-(3,4-Dihydroxyphenyl)-a- (2-piperidinyl)methanol
DE1445895C (de)	1973-04-05	Verfahren zur Herstellung von 2 Dehydroemetinderivaten
DE1445895A1 (de)	1969-11-27	Verfahren zur Herstellung von Benzo[a]chinolizinderivaten
CH521345A (de)	1972-04-15	Verfahren zur Herstellung von Tetrahydroisochinolinverbindungen
DE1958646C3 (de)	1980-03-13	In 4-Stellung substituierte 3,5-DimethyUsoxazole und deren Herstellung
DE1445895B (de)		Verfahren zur Herstellung von 2-Dehydroemetinderivaten
DE1470065C3 (de)	1980-07-17	Verfahren zur Herstellung von Chinolizinderivaten
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