CH410007A - Verfahren zur Herstellung von tertiären Aminen - Google Patents

Verfahren zur Herstellung von tertiären Aminen

Info

Publication number: CH410007A
Authority: CH; Switzerland
Prior art keywords: formula; racemic; lower alkyl; quaternary; methyl
Prior art date: 1961-04-21

Application number

CH471261A

Other languages

German (de)

English (en)

Inventor

Arnold Dr Brossi

Alfred Jr Dr Rheiner

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.)

1961-04-21

Filing date

1961-04-21

Publication date

1966-03-31

1961-04-21 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1961-04-21 Priority to CH471261A priority Critical patent/CH410007A/de

1962-04-12 Priority to FR1824DA priority patent/FR1824M/fr

1962-04-13 Priority to BE616393A priority patent/BE616393A/fr

1962-04-17 Priority to GB14803/62A priority patent/GB969077A/en

1962-04-19 Priority to ES276647A priority patent/ES276647A1/es

1966-03-31 Publication of CH410007A publication Critical patent/CH410007A/de

Links

238000000034 method Methods 0.000 title claims description 14
150000003512 tertiary amines Chemical class 0.000 title claims description 6
238000002360 preparation method Methods 0.000 title claims description 4
150000003839 salts Chemical group 0.000 claims description 15
238000006243 chemical reaction Methods 0.000 claims description 10
-1 isoquinoline compound Chemical class 0.000 claims description 10
150000001875 compounds Chemical class 0.000 claims description 9
239000007858 starting material Substances 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 6
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
239000004215 Carbon black (E152) Substances 0.000 claims description 3
239000002168 alkylating agent Substances 0.000 claims description 3
229940100198 alkylating agent Drugs 0.000 claims description 3
229930195733 hydrocarbon Natural products 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
230000003287 optical effect Effects 0.000 claims description 3
ALKOLYNQANQTPH-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenyl)ethyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinoline Chemical compound ClC=1C=C(C=CC1Cl)CCC1N(CCC2=CC(=C(C=C12)OC)OC)C ALKOLYNQANQTPH-UHFFFAOYSA-N 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
238000000926 separation method Methods 0.000 claims description 2
AWJUIBRHMBBTKR-UHFFFAOYSA-N iso-quinoline Natural products C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 1
239000012022 methylating agents‎ Substances 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
238000009835 boiling Methods 0.000 description 11
239000000047 product Substances 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
238000010521 absorption reaction Methods 0.000 description 8
239000002585 base Substances 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
239000000155 melt Substances 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
239000003054 catalyst Substances 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
238000000197 pyrolysis Methods 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
239000005977 Ethylene Substances 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
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000006264 debenzylation reaction Methods 0.000 description 2
239000007857 degradation product Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
229910003446 platinum oxide Inorganic materials 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000005956 quaternization reaction Methods 0.000 description 2
229910001923 silver oxide Inorganic materials 0.000 description 2
239000000126 substance Substances 0.000 description 2
YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 description 1
MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
YBWZASUDKSNFAS-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-6,7-dimethoxy-2-methyl-3,4-dihydro-1h-isoquinoline Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(C)C1C1=CC=C(Cl)C(Cl)=C1 YBWZASUDKSNFAS-UHFFFAOYSA-N 0.000 description 1
BBGKOKJQNAKCQK-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)ethyl]-6,7-dimethoxy-2,3-dimethyl-3,4-dihydro-1h-isoquinoline Chemical compound C1=2C=C(OC)C(OC)=CC=2CC(C)N(C)C1CCC1=CC=C(Cl)C=C1 BBGKOKJQNAKCQK-UHFFFAOYSA-N 0.000 description 1
YOTZTYPLSOOBOH-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-(2-ethenyl-4,5-dimethoxyphenyl)-N,N-dimethylpropan-1-amine Chemical compound C(=C)C1=C(C=C(C(=C1)OC)OC)C(CCC1=CC=C(C=C1)Cl)N(C)C YOTZTYPLSOOBOH-UHFFFAOYSA-N 0.000 description 1
DQCTZVKYKOAZRF-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-(2-ethyl-4,5-dimethoxyphenyl)-N,N-dimethylpropan-1-amine Chemical compound C(C)C1=C(C=C(C(=C1)OC)OC)C(CCC1=CC=C(C=C1)Cl)N(C)C DQCTZVKYKOAZRF-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
HUVIBTWOASODNV-UHFFFAOYSA-N COC=1C=C2CCN(C(C2=CC=1OC)C(C)C1=CC=CC=C1)C Chemical compound COC=1C=C2CCN(C(C2=CC=1OC)C(C)C1=CC=CC=C1)C HUVIBTWOASODNV-UHFFFAOYSA-N 0.000 description 1
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 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
230000003213 activating effect Effects 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001350 alkyl halides Chemical class 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
230000000954 anitussive effect Effects 0.000 description 1
230000003276 anti-hypertensive effect Effects 0.000 description 1
229940124584 antitussives Drugs 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
239000000812 cholinergic antagonist Substances 0.000 description 1
229960004106 citric acid Drugs 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229960001270 d- tartaric acid Drugs 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
150000008050 dialkyl sulfates Chemical class 0.000 description 1
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
229940008406 diethyl sulfate Drugs 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 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
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
229960002598 fumaric acid Drugs 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
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 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000000203 mixture Substances 0.000 description 1
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000003921 oil Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000001294 propane Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
230000002048 spasmolytic effect Effects 0.000 description 1
229960001367 tartaric acid Drugs 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
UWYZHKAOTLEWKK-UHFFFAOYSA-N tetrahydro-isoquinoline Natural products C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 1
150000003526 tetrahydroisoquinolines Chemical class 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
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
238000010792 warming 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/10—Quaternary compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CH471261A 1961-04-21 1961-04-21 Verfahren zur Herstellung von tertiären Aminen CH410007A (de)

Priority Applications (5)

Application Number	Priority Date	Filing Date	Title
CH471261A CH410007A (de)	1961-04-21	1961-04-21	Verfahren zur Herstellung von tertiären Aminen
FR1824DA FR1824M (fr)	1961-04-21	1962-04-12	Médicament a base d'amines tertiaires.
BE616393A BE616393A (fr)	1961-04-21	1962-04-13	Procédé pour la préparation d'amines tertiaires
GB14803/62A GB969077A (en)	1961-04-21	1962-04-17	Novel tertiary amines and a process for the manufacture thereof
ES276647A ES276647A1 (es)	1961-04-21	1962-04-19	Procedimiento para la fabricación de aminas terciarias

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH471261A CH410007A (de)	1961-04-21	1961-04-21	Verfahren zur Herstellung von tertiären Aminen

Publications (1)

Publication Number	Publication Date
CH410007A true CH410007A (de)	1966-03-31

Family

ID=4281191

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH471261A CH410007A (de)	1961-04-21	1961-04-21	Verfahren zur Herstellung von tertiären Aminen

Country Status (5)

Country	Link
BE (1)	BE616393A (fr)
CH (1)	CH410007A (fr)
ES (1)	ES276647A1 (fr)
FR (1)	FR1824M (fr)
GB (1)	GB969077A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2001009101A1 (fr) *	1999-07-29	2001-02-08	EGIS Gyógyszergyár Rt.	Derives d'isoquinoline, compositions pharmaceutiques contenant ces derives et procede de preparation du principe actif

1961
- 1961-04-21 CH CH471261A patent/CH410007A/de unknown
1962
- 1962-04-12 FR FR1824DA patent/FR1824M/fr not_active Expired
- 1962-04-13 BE BE616393A patent/BE616393A/fr unknown
- 1962-04-17 GB GB14803/62A patent/GB969077A/en not_active Expired
- 1962-04-19 ES ES276647A patent/ES276647A1/es not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2001009101A1 (fr) *	1999-07-29	2001-02-08	EGIS Gyógyszergyár Rt.	Derives d'isoquinoline, compositions pharmaceutiques contenant ces derives et procede de preparation du principe actif

Also Published As

Publication number	Publication date
ES276647A1 (es)	1962-10-16
FR1824M (fr)	1963-05-20
GB969077A (en)	1964-09-09
BE616393A (fr)	1962-10-15

Publication	Publication Date	Title
DE1543374C3 (de)	1973-10-04	3,4 Dihydroxyphenylalkanolamine und ihre Saureadditionssalze, Verfahren zu ihrer Herstellung und pharmazeutische Zubereitungen
DE2413102C3 (de)	1980-09-11	Verfahren zur Herstellung von l-(3,5-Dihydroxyphenyl)-t-hydroxy-2- eckige Klammer auf 1-methyl-2-(4-hydroxyphenyl)- äthyl] -aminoäthan
US3138639A (en)	1964-06-23	Tertiary amines and a process for producing same
DE1900948A1 (de)	1970-07-02	Isochinolinderivate
CH410007A (de)	1966-03-31	Verfahren zur Herstellung von tertiären Aminen
CH530401A (de)	1972-11-15	Verfahren zur Herstellung von Phenanthridinderivaten
AT230870B (de)	1963-12-30	Verfahren zur Herstellung von tertiären Aminen und deren salzartigen Abkömmlingen
EP0000013B1 (fr)	1980-10-15	4-Phényl-8-amino-tetrahydroisoquinoléines, compositions pharmaceutiques les contenant et procédé pour préparer ces compositions
DE2061864B2 (de)	1979-06-28	Acylderivate von substituierten Bis-Arylalkylaminen
DE1470065C3 (de)	1980-07-17	Verfahren zur Herstellung von Chinolizinderivaten
DE725535C (de)	1942-10-06	Verfahren zur Herstellung von Tetrahydroisochinolinverbindungen
DE908138C (de)	1954-04-01	Verfahren zur Herstellung von 1-Benzyl-2-alkyl-1,2,3,4,5,6,7,8,-octa-hydroisochinolinen und ihren Salzen
DE1935757B1 (de)	1970-11-12	Verfahren zur Herstellung des N,N'-Bis-[2-(3',4'-dihydroxyphenyl)-2-hydroxyaethyl]-hexamethylendiamins,seiner optisch aktiven Formen und deren Salzen
DE1959562A1 (de)	1971-06-03	Neue Benzodioxanderivate
AT238186B (de)	1965-01-25	Verfahren zur Herstellung neuer Pyrrolidinverbindungen
DE1810341A1 (de)	1969-08-07	Verfahren zur Herstellung von Tetrahydroisochinolin-Derivaten
DE2132810A1 (de)	1972-01-05	Indenopyrrolderivate und ihre Salze,Verfahren zu ihrer Herstellung und Arzneipraeparate
DE927690C (de)	1955-05-16	Verfahren zur Herstellung von 1-(Oxyphenyl)-2-aralkylamino-butanonen-(1)
AT338793B (de)	1977-09-12	Verfahren zur herstellung von neuen benzazocinderivaten
DE1670580C3 (de)	1978-03-30	Verfahren zur Herstellung von sekundären Aminen, die einen Arylalkyl- beziehungsweise Xanthinoalkylrest enthalten
AT257571B (de)	1967-10-10	Verfahren zur Herstellung des neuen N-Benzyl-α,α-dimethyl-β-(p-fluorphenyl)-äthylamins und dessen Salze
DE2351027A1 (de)	1975-04-24	Propanolderivate
AT264526B (de)	1968-09-10	Verfahren zur Herstellung von neuen Tetrahydroisochinolinderivaten sowie von Säureadditionssalzen davon
AT233566B (de)	1964-05-11	Verfahren zur Herstellung von neuen Tetrahydroisochinolin-Derivaten
AT256111B (de)	1967-08-10	Verfahren zur Herstellung der razemischen und der (+)-Form des neuen 1-(2',4',5'-Trichlor-phenäthyl)-2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisochinolins und deren Säureadditionssalze

CH410007A - Verfahren zur Herstellung von tertiären Aminen - Google Patents

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