CH495993A - Verfahren zur Herstellung von Indolyl-Vindolinen - Google Patents

Verfahren zur Herstellung von Indolyl-Vindolinen

Info

Publication number: CH495993A
Authority: CH; Switzerland
Prior art keywords: group; alk; indole; formula; reaction
Prior art date: 1964-06-18

Application number

CH765965A

Other languages

German (de)

English (en)

Inventor

Gorman Marvin

Carl Kornfeld Edmund

Original Assignee

Lilly Co Eli

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.)

1964-06-18

Filing date

1965-06-01

Publication date

1970-09-15

1965-06-01 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1970-09-15 Publication of CH495993A publication Critical patent/CH495993A/de

Links

125000001041 indolyl group Chemical group 0.000 title claims abstract description 5
229930013930 alkaloid Natural products 0.000 title abstract description 6
239000000543 intermediate Substances 0.000 title abstract description 3
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
125000000217 alkyl group Chemical group 0.000 claims abstract description 7
238000000034 method Methods 0.000 claims description 31
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
150000002475 indoles Chemical class 0.000 claims description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 9
150000001875 compounds Chemical class 0.000 claims description 9
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 9
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 9
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 8
-1 carbenium ion Chemical class 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 7
230000002378 acidificating effect Effects 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
239000007858 starting material Substances 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 4
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 4
HZRZXZZTSRUSLH-WUADLFQHSA-N methyl (1S,12R,14R,15Z,18R)-15-ethylidene-12-hydroxy-17-methyl-10,17-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8-tetraene-18-carboxylate Chemical compound O=C(OC)[C@H]1[C@H]2N(C)C/C(=C\C)/[C@@H]1C[C@@H](O)c1[nH]c3c(c1C2)cccc3 HZRZXZZTSRUSLH-WUADLFQHSA-N 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
URFWOTYPRGLZFU-PEMUAGBOSA-N perivinol Chemical compound C1C(C2=CC=CC=C2N2)=C2[C@@H](O)C[C@H]2\C(=C/C)CN[C@@H]1C2C(=O)OC URFWOTYPRGLZFU-PEMUAGBOSA-N 0.000 claims description 4
RUEQYTQFZQYPGF-UHFFFAOYSA-N vobasinol Natural products COC(=O)C1C2CC3C4CCCCC4NC3C(O)CC1C(=CC)CN2C RUEQYTQFZQYPGF-UHFFFAOYSA-N 0.000 claims description 4
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
239000012442 inert solvent Substances 0.000 claims description 3
XKLNOVWDVMWTOB-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazole Chemical group N1C2=CC=CC=C2C2=C1CCCC2 XKLNOVWDVMWTOB-UHFFFAOYSA-N 0.000 claims description 2
239000012454 non-polar solvent Substances 0.000 claims description 2
235000005074 zinc chloride Nutrition 0.000 claims description 2
239000011592 zinc chloride Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
DNBLHHKTWUDMHE-UHFFFAOYSA-N 2,3-dihydrocyclopenta[b]indole Chemical group C1=CC=C2C3=CCCC3=NC2=C1 DNBLHHKTWUDMHE-UHFFFAOYSA-N 0.000 claims 1
230000001419 dependent effect Effects 0.000 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 abstract description 4
238000003786 synthesis reaction Methods 0.000 abstract description 2
JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical class C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 abstract description 2
125000002947 alkylene group Chemical group 0.000 abstract 1
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 abstract 1
239000000243 solution Substances 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
WVTGEXAIVZDLCR-UHFFFAOYSA-N Vindoline Natural products CC1C2CN3CCCC14CCC5Nc6ccccc6C25C34 WVTGEXAIVZDLCR-UHFFFAOYSA-N 0.000 description 8
GKWYINOZGDHWRA-UHFFFAOYSA-N catharanthine Natural products C1C(CC)(O)CC(CC2C(=O)OC)CN1CCC1=C2NC2=CC=CC=C12 GKWYINOZGDHWRA-UHFFFAOYSA-N 0.000 description 8
239000002904 solvent Substances 0.000 description 8
238000004519 manufacturing process Methods 0.000 description 7
CXBGOBGJHGGWIE-IYJDUVQVSA-N vindoline Chemical compound CN([C@H]1[C@](O)([C@@H]2OC(C)=O)C(=O)OC)C3=CC(OC)=CC=C3[C@]11CCN3CC=C[C@]2(CC)[C@@H]13 CXBGOBGJHGGWIE-IYJDUVQVSA-N 0.000 description 7
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
230000008020 evaporation Effects 0.000 description 6
239000000203 mixture Substances 0.000 description 6
239000000284 extract Substances 0.000 description 5
238000000926 separation method Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
239000010410 layer Substances 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
238000004809 thin layer chromatography Methods 0.000 description 4
238000004566 IR spectroscopy Methods 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
OWAQXCQNWNJICI-UHFFFAOYSA-N benzene;chloroform Chemical compound ClC(Cl)Cl.C1=CC=CC=C1 OWAQXCQNWNJICI-UHFFFAOYSA-N 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
229930005303 indole alkaloid Natural products 0.000 description 3
ZDKMPOJNYNVYLA-PEGGBQQISA-N 17-O-deacetylvindoline Chemical compound CN([C@H]1[C@](O)([C@@H]2O)C(=O)OC)C3=CC(OC)=CC=C3[C@@]11CCN3CC=C[C@]2(CC)[C@@H]13 ZDKMPOJNYNVYLA-PEGGBQQISA-N 0.000 description 2
GXUZLXNKCOCTLH-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazol-1-ol Chemical compound N1C2=CC=CC=C2C2=C1C(O)CCC2 GXUZLXNKCOCTLH-UHFFFAOYSA-N 0.000 description 2
DQNVJWKDCCSMLW-UHFFFAOYSA-N 2-methylideneindole Chemical compound C1=CC=CC2=NC(=C)C=C21 DQNVJWKDCCSMLW-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
238000005727 Friedel-Crafts reaction Methods 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
150000003797 alkaloid derivatives Chemical class 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
239000011877 solvent mixture Substances 0.000 description 2
KFWYCGGJKBFGRT-UHFFFAOYSA-N (+)-20R-15,20-dihydro-cleavamine Natural products C1C(CC)CC(CC2)CN1CCC1=C2NC2=CC=CC=C12 KFWYCGGJKBFGRT-UHFFFAOYSA-N 0.000 description 1
VMCGAPHZNWKXAX-UHFFFAOYSA-N 1-chloro-2,3,4,9-tetrahydro-1h-carbazole Chemical compound N1C2=CC=CC=C2C2=C1C(Cl)CCC2 VMCGAPHZNWKXAX-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 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
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
238000003309 Hoesch reaction Methods 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
241000605411 Lloydia Species 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
230000001800 adrenalinergic effect Effects 0.000 description 1
WYTGDNHDOZPMIW-RCBQFDQVSA-N alstonine Chemical compound C1=CC2=C3C=CC=CC3=NC2=C2N1C[C@H]1[C@H](C)OC=C(C(=O)OC)[C@H]1C2 WYTGDNHDOZPMIW-RCBQFDQVSA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
230000000840 anti-viral effect Effects 0.000 description 1
229940054051 antipsychotic indole derivative Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000000903 blocking effect Effects 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
210000003169 central nervous system Anatomy 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 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
ZMQCYQNIMQXFOW-SSBHFPSFSA-N dihydrovindoline Chemical compound CN([C@H]1[C@](O)([C@@H]2OC(C)=O)C(=O)OC)C3=CC(OC)=CC=C3C11CCN3CCC[C@]2(CC)[C@@H]13 ZMQCYQNIMQXFOW-SSBHFPSFSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
239000000047 product Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D519/02—Ergot alkaloids of the cyclic peptide type

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Indole Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH765965A 1964-06-18 1965-06-01 Verfahren zur Herstellung von Indolyl-Vindolinen CH495993A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US37625864A	1964-06-18	1964-06-18

Publications (1)

Publication Number	Publication Date
CH495993A true CH495993A (de)	1970-09-15

Family

ID=23484285

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH765965A CH495993A (de)	1964-06-18	1965-06-01	Verfahren zur Herstellung von Indolyl-Vindolinen

Country Status (4)

Country	Link
CH (1)	CH495993A (fr)
DE (1)	DE1545768A1 (fr)
FR (1)	FR1435519A (fr)
GB (1)	GB1115930A (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2434172A1 (fr) *	1978-08-24	1980-03-21	Anvar	Nouveaux composes intermediaires utiles dans la synthese de derives bis-indoliques et procede pour leur preparation
US4307100A (en) *	1978-08-24	1981-12-22	Agence Nationale De Valorisation De La Recherche (Anvar)	Nor bis-indole compounds usable as medicaments
FR2461714A1 (fr) *	1979-07-17	1981-02-06	Anvar	Nouvelle classe de composes bis-indoliques utiles comme medicaments et procede pour leur preparation

1965
- 1965-05-31 DE DE19651545768 patent/DE1545768A1/de active Pending
- 1965-06-01 FR FR19015A patent/FR1435519A/fr not_active Expired
- 1965-06-01 CH CH765965A patent/CH495993A/de not_active IP Right Cessation
- 1965-06-04 GB GB2399365A patent/GB1115930A/en not_active Expired

Also Published As

Publication number	Publication date
DE1545768A1 (de)	1969-11-27
FR1435519A (fr)	1966-04-15
GB1115930A (en)	1968-06-06

Legal Events

Date	Code	Title	Description
1979-03-15	PL	Patent ceased

Publication	Publication Date	Title
DE1795613A1 (de)	1972-03-30	Indolylessigsaeuren,Verfahren zu ihrer Herstellung und Arzneipraeparate
DE2739624A1 (de)	1978-04-06	Neue rifamyzin-verbindungen (i)
CH649295A5 (de)	1985-05-15	Optisch aktive oder razemische brom-e-homo-eburanderivate.
CH495993A (de)	1970-09-15	Verfahren zur Herstellung von Indolyl-Vindolinen
DE2155578B2 (de)	1978-05-03	Verfahren zur Herstellung von 8,9-Didehydro-10-alkoxy-ergolenderivaten
DE2057840C3 (de)	1980-05-29	Verfahren zur Herstellung von Indolderivaten
CH644606A5 (de)	1984-08-15	Verfahren zur isomerisierung von 9,10-dihydrolysergsaeurederivaten.
CH507264A (de)	1971-05-15	Verfahren zur Herstellung von Dihydrovinblastin, Dihydrovincristin und Dihydrodesmethylvinblastin sowie Verwendung des Dihydrodesmethylvinblastin
DE69323418T2 (de)	1999-09-09	VERFAHREN ZU HERSTELLUNG VON ARENO[e]INDOLE
DE2731456A1 (de)	1978-01-19	2-phenylindolderivate, deren herstellung und verwendung
DD144269A5 (de)	1980-10-08	Verfahren zur herstellung von steroidverbindungen
CH667092A5 (de)	1988-09-15	Verfahren zur herstellung von 2-brom-alpha-ergokryptin.
DE2318329A1 (de)	1973-10-18	Verfahren zur herstellung neuer heterocyclischer verbindungen
CH535236A (de)	1973-03-31	Verfahren zur Herstellung neuer reaktionsträger Lysergsäurederivate
DE2928022C2 (de)	1986-11-27	Verfahren zur Herstellung von 2,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridin-3,5-dicarbonsäure-3-[2-(N-benzyl-N-methylamino)-ethyl]-ester-5-ethylester
DE764598C (de)	1953-04-16	Verfahren zur Herstellung von analgetisch wirksamen Derivaten des 1-Oxyphenyl-3-aminobutans
DE2148552A1 (de)	1972-04-06	Verfahren zur Herstellung neuer heterocyclischer Verbindungen
DE810459C (de)	1951-08-09	Verfahren zur Herstellung von photographischen Farbbildern
DE2331044A1 (de)	1974-01-10	Diphenylmethan-derivate und verfahren zu deren herstellung
DE2134592C3 (de)	1974-12-19	Verfahren zur Herstellung von 3-(beta-Morpholinoäthoxy)-lH-indazol,3-(gamma,Morpholinopropoxy)-1 H-indazol und 3-(beta-Morpholinoäthoxy)-4,5,6,7tetrahydro-2H-indazol
DE960538C (de)	1957-03-21	Verfahren zur Herstellung von 5-Benzyloxy-ª, 2-dinitrostyrolen
AT278261B (de)	1970-01-26	Verfahren zur Herstellung von in 4- bzw. 6-Stellung acylierten Δ<4>-3-Ketosteroiden
AT241463B (de)	1965-07-26	Verfahren zur Herstellung neuer Dibenzocycloheptanderivate
AT281303B (de)	1970-05-25	Verfahren zur herstellung neuer derivate von bufadienolidglykosiden
CH477447A (de)	1969-08-31	Verfahren zur Herstellung neuer Derivate von Dihydro-D-lysergsäure- und 1-Methyl-dihydro-D-lysergsäure-a-hydroxyäthylamid