CH387634A - Verfahren zur Herstellung neuer basischer Indol-Derivate - Google Patents

Verfahren zur Herstellung neuer basischer Indol-Derivate

Info

Publication number: CH387634A
Authority: CH; Switzerland
Prior art keywords: indole; formula; aldehyde; preparation; methyl
Prior art date: 1961-02-01

Application number

CH116061A

Other languages

German (de)

English (en)

Inventor

Albert Dr Hofmann

Franz Dr Troxler

Original Assignee

Sandoz Ag

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.)

1961-02-01

Filing date

1961-02-01

Publication date

1965-02-15

1961-02-01 Application filed by Sandoz Ag filed Critical Sandoz Ag

1961-02-01 Priority to CH116061A priority Critical patent/CH387634A/de

1962-01-16 Priority to GB1520/62A priority patent/GB947461A/en

1962-01-30 Priority to ES0274180A priority patent/ES274180A1/es

1962-01-30 Priority to LU41176D priority patent/LU41176A1/xx

1962-04-27 Priority to FR895978A priority patent/FR2132M/fr

1964-12-08 Priority to OA50773A priority patent/OA00695A/fr

1965-02-15 Publication of CH387634A publication Critical patent/CH387634A/de

Links

150000002475 indoles Chemical class 0.000 title claims description 5
229940054051 antipsychotic indole derivative Drugs 0.000 title claims description 4
238000000034 method Methods 0.000 title claims description 4
238000002360 preparation method Methods 0.000 title claims description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 9
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 8
SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 3
150000002828 nitro derivatives Chemical class 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
238000009833 condensation Methods 0.000 claims description 2
230000005494 condensation Effects 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000004971 nitroalkyl group Chemical group 0.000 claims description 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 13
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 8
239000013078 crystal Substances 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
239000012280 lithium aluminium hydride Substances 0.000 description 5
-1 lithium aluminum hydride Chemical compound 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 4
239000005695 Ammonium acetate Substances 0.000 description 4
229940043376 ammonium acetate Drugs 0.000 description 4
235000019257 ammonium acetate Nutrition 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
239000013067 intermediate product Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
229920002554 vinyl polymer Polymers 0.000 description 3
DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 2
YAYYLLZJMZNDFN-UHFFFAOYSA-N 1-(4-chloro-1h-indol-3-yl)butan-2-amine Chemical compound C1=CC(Cl)=C2C(CC(N)CC)=CNC2=C1 YAYYLLZJMZNDFN-UHFFFAOYSA-N 0.000 description 2
XKHCIOVNXOVPIK-UHFFFAOYSA-N 1-(4-methyl-1h-indol-3-yl)butan-2-amine Chemical compound C1=CC(C)=C2C(CC(N)CC)=CNC2=C1 XKHCIOVNXOVPIK-UHFFFAOYSA-N 0.000 description 2
GRJZJFUBQYULKL-UHFFFAOYSA-N 4-bromo-1h-indole Chemical compound BrC1=CC=CC2=C1C=CN2 GRJZJFUBQYULKL-UHFFFAOYSA-N 0.000 description 2
MSYJFNQAVTYKOP-UHFFFAOYSA-N 4-chloro-1h-indole-3-carbaldehyde Chemical compound ClC1=CC=CC2=C1C(C=O)=CN2 MSYJFNQAVTYKOP-UHFFFAOYSA-N 0.000 description 2
BAEKRCMLZVJLOF-UHFFFAOYSA-N 4-chloro-3-(2-nitrobut-1-enyl)-1H-indole Chemical compound CCC(=CC1=CNC2=CC=CC(Cl)=C12)[N+]([O-])=O BAEKRCMLZVJLOF-UHFFFAOYSA-N 0.000 description 2
IHEQLWPOIBLDCQ-UHFFFAOYSA-N 4-chloro-3-(2-nitroprop-1-enyl)-1H-indole Chemical compound ClC1=C2C(=CNC2=CC=C1)C=C([N+](=O)[O-])C IHEQLWPOIBLDCQ-UHFFFAOYSA-N 0.000 description 2
OXMKZTMGJSTKPG-UHFFFAOYSA-N 4-methyl-1h-indole-3-carbaldehyde Chemical compound CC1=CC=CC2=C1C(C=O)=CN2 OXMKZTMGJSTKPG-UHFFFAOYSA-N 0.000 description 2
JECBWQLVOPJDON-UHFFFAOYSA-N C(C)C(=CC1=CNC2=CC=CC(=C12)C)[N+](=O)[O-] Chemical compound C(C)C(=CC1=CNC2=CC=CC(=C12)C)[N+](=O)[O-] JECBWQLVOPJDON-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
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 2
QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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 2
229960000583 acetic acid Drugs 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 2
229960003147 reserpine Drugs 0.000 description 2
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000011975 tartaric acid Substances 0.000 description 2
235000002906 tartaric acid Nutrition 0.000 description 2
APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 2
SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 1
BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
IPAFHZDRYAWZOB-UHFFFAOYSA-N 4-bromo-1h-indole-3-carbaldehyde Chemical compound BrC1=CC=CC2=C1C(C=O)=CN2 IPAFHZDRYAWZOB-UHFFFAOYSA-N 0.000 description 1
SVLZRCRXNHITBY-UHFFFAOYSA-N 4-chloro-1h-indole Chemical compound ClC1=CC=CC2=C1C=CN2 SVLZRCRXNHITBY-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
206010010904 Convulsion Diseases 0.000 description 1
208000020401 Depressive disease Diseases 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
102000010909 Monoamine Oxidase Human genes 0.000 description 1
108010062431 Monoamine oxidase Proteins 0.000 description 1
CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
235000005811 Viola adunca Nutrition 0.000 description 1
240000009038 Viola odorata Species 0.000 description 1
235000013487 Viola odorata Nutrition 0.000 description 1
235000002254 Viola papilionacea Nutrition 0.000 description 1
244000172533 Viola sororia Species 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
230000001773 anti-convulsant effect Effects 0.000 description 1
230000002082 anti-convulsion Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
238000009835 boiling Methods 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
239000003638 chemical reducing agent Substances 0.000 description 1
230000036461 convulsion Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
229960002715 nicotine Drugs 0.000 description 1
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229960005152 pentetrazol Drugs 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
208000020016 psychiatric disease Diseases 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D209/16—Tryptamines

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Indole Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CH116061A 1961-02-01 1961-02-01 Verfahren zur Herstellung neuer basischer Indol-Derivate CH387634A (de)

Priority Applications (6)

Application Number	Priority Date	Filing Date	Title
CH116061A CH387634A (de)	1961-02-01	1961-02-01	Verfahren zur Herstellung neuer basischer Indol-Derivate
GB1520/62A GB947461A (en)	1961-02-01	1962-01-16	Improvements in or relating to 3-aminoalkyl-indoles
ES0274180A ES274180A1 (es)	1961-02-01	1962-01-30	Procedimiento de obtenciën de nuevos compuestos heterociclicos y de sus sales acidas de adiciën
LU41176D LU41176A1 (fr)	1961-02-01	1962-01-30
FR895978A FR2132M (fr)	1961-02-01	1962-04-27	Médicament a base de tryptamine substituée.
OA50773A OA00695A (fr)	1961-02-01	1964-12-08	Nouveaux dérivés de l'indole et leur préparation.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH116061A CH387634A (de)	1961-02-01	1961-02-01	Verfahren zur Herstellung neuer basischer Indol-Derivate

Publications (1)

Publication Number	Publication Date
CH387634A true CH387634A (de)	1965-02-15

Family

ID=4203870

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH116061A CH387634A (de)	1961-02-01	1961-02-01	Verfahren zur Herstellung neuer basischer Indol-Derivate

Country Status (3)

Country	Link
CH (1)	CH387634A (fr)
ES (1)	ES274180A1 (fr)
OA (1)	OA00695A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2199980A1 (fr) *	1972-09-15	1974-04-19	Siegfried Ag

1961
- 1961-02-01 CH CH116061A patent/CH387634A/de unknown
1962
- 1962-01-30 ES ES0274180A patent/ES274180A1/es not_active Expired
1964
- 1964-12-08 OA OA50773A patent/OA00695A/fr unknown

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2199980A1 (fr) *	1972-09-15	1974-04-19	Siegfried Ag

Also Published As

Publication number	Publication date
ES274180A1 (es)	1962-07-16
OA00695A (fr)	1967-07-15

Publication	Publication Date	Title
DE1618865A1 (de)	1970-04-30	In der 3-Stellung mit aliphatischen Saeureresten substituierte 1-(Phenylsulfonyl)-indolyl-Verbindungen und Verfahren zu ihrer Herstellung
DE2740836A1 (de)	1979-03-22	Anellierte indolderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
CH387634A (de)	1965-02-15	Verfahren zur Herstellung neuer basischer Indol-Derivate
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AT221087B (de)	1962-05-10	Verfahren zur Herstellung neuer, basischer Indol-Derivate
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CH402860A (de)	1965-11-30	Verfahren zur Herstellung neuer basischer Indol-Derivate
DE820735C (de)	1951-11-12	Verfahren zur Herstellung von Harnstoffderivaten
AT349025B (de)	1979-03-12	Verfahren zur herstellung von neuen naphthyridinderivaten und von deren saeureadditionssalzen
AT263026B (de)	1968-07-10	Verfahren zur Herstellung von neuen Phenthiazinderivaten
AT158151B (de)	1940-03-11	Verfahren zur Darstellung von Lysergsäureamiden.
AT251765B (de)	1967-01-25	Verfahren zur Herstellung von neuen Yohimbanderivaten und von deren Salzen
AT226724B (de)	1963-04-10	Verfahren zur Herstellung von neuen 1-Aza-thioxanthen-Derivaten
AT233552B (de)	1964-05-11	Verfahren zur Herstellung von neuen Dibenzocycloheptadien-Derivaten und ihren Salzen
AT236367B (de)	1964-10-26	Verfahren zur Herstellung neuer Indolderivate
CH511840A (de)	1971-08-31	Verfahren zur Herstellung von neuen Indolderivaten
CH414639A (de)	1966-06-15	Verfahren zur Herstellung neuer heterocyclischer Verbindungen
AT258910B (de)	1967-12-27	Verfahren zur Herstellung von Benzo-dihydro-thiadiazin-Derivaten
AT296316B (de)	1972-02-10	Verfahren zur Herstellung von neuen Benzodiazepin-Derivaten und deren N-4-Oxyden

CH387634A - Verfahren zur Herstellung neuer basischer Indol-Derivate - Google Patents

Info

Links

Classifications

Landscapes

Priority Applications (6)

Applications Claiming Priority (1)

Publications (1)

Family

ID=4203870

Family Applications (1)

Country Status (3)

Cited By (1)

Cited By (1)

Also Published As

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