CH380741A - Verfahren zur Herstellung von Toxiferinen - Google Patents

Verfahren zur Herstellung von Toxiferinen

Info

Publication number: CH380741A
Authority: CH; Switzerland
Prior art keywords: nordihydrotoxiferin; caracurin; acid; glacial acetic; production
Prior art date: 1959-01-30

Application number

CH6897259A

Other languages

German (de)

English (en)

Inventor

Karl Dr Bernauer

Karrer Paul Dr Prof

Schmid Hans Dr Prof

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.)

1959-01-30

Filing date

1959-01-30

Publication date

1964-08-15

1959-01-30 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1959-01-30 Priority to CH6897259A priority Critical patent/CH380741A/de

1960-01-16 Priority to DE1960H0038396 priority patent/DE1164420B/de

1960-01-27 Priority to BE586986A priority patent/BE586986A/fr

1960-01-29 Priority to ES0255383A priority patent/ES255383A1/es

1964-08-15 Publication of CH380741A publication Critical patent/CH380741A/de

Links

238000000034 method Methods 0.000 title claims description 9
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 10
CIRUUTNLDXXBKU-UHFFFAOYSA-N (19E,19'E)-17beta,18;17'beta,18'-diepoxy-[1,17';17,1']bicurane-19,19'-diene Natural products C1C2C3C4N(C=5C6=CC=CC=5)C5OCC=C7CN8CCC9(C%10=CC=CC=C%10%10)C8CC7C5C9N%10C3OCC=C2CN2C1C46CC2 CIRUUTNLDXXBKU-UHFFFAOYSA-N 0.000 claims description 9
150000003839 salts Chemical group 0.000 claims description 6
229910000042 hydrogen bromide Inorganic materials 0.000 claims description 5
229910000039 hydrogen halide Inorganic materials 0.000 claims description 4
239000012433 hydrogen halide Substances 0.000 claims description 4
238000007327 hydrogenolysis reaction Methods 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
229960000583 acetic acid Drugs 0.000 description 10
239000012362 glacial acetic acid Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
KJHAQFGXJGTJHM-SJVAQDHQSA-N dihydrotoxiferin Chemical compound C12C/3=C\N(C4\5)C6=CC=CC=C6C4(CC[N+]4(C)C\C6=C/C)C4CC6C/5=C/N1C1=CC=CC=C1C21CC[N+]2(C)C\C(=C/C)C\3CC21 KJHAQFGXJGTJHM-SJVAQDHQSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
235000002639 sodium chloride Nutrition 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
230000007717 exclusion Effects 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000000047 product Substances 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
229930013930 alkaloid Natural products 0.000 description 1
150000003797 alkaloid derivatives Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
-1 alkylene halides Chemical class 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
210000000653 nervous system Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
238000004816 paper chromatography Methods 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000005956 quaternization reaction Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CH6897259A 1959-01-30 1959-01-30 Verfahren zur Herstellung von Toxiferinen CH380741A (de)

Priority Applications (4)

Application Number	Priority Date	Filing Date	Title
CH6897259A CH380741A (de)	1959-01-30	1959-01-30	Verfahren zur Herstellung von Toxiferinen
DE1960H0038396 DE1164420B (de)	1959-01-30	1960-01-16	Verfahren zur Herstellung von Nor-dihydro-toxiferin, von seinen Salzen mit Säuren und von seinen in 3- und/oder 3'-Stellung quaternisierten Derivaten.
BE586986A BE586986A (fr)	1959-01-30	1960-01-27	Procédé pour la préparation de composés de carbazole.
ES0255383A ES255383A1 (es)	1959-01-30	1960-01-29	Procedimiento para la fabricacion de compuestos carbazolicos

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH6897259A CH380741A (de)	1959-01-30	1959-01-30	Verfahren zur Herstellung von Toxiferinen

Publications (1)

Publication Number	Publication Date
CH380741A true CH380741A (de)	1964-08-15

Family

ID=4529136

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH6897259A CH380741A (de)	1959-01-30	1959-01-30	Verfahren zur Herstellung von Toxiferinen

Country Status (4)

Country	Link
BE (1)	BE586986A (fr)
CH (1)	CH380741A (fr)
DE (1)	DE1164420B (fr)
ES (1)	ES255383A1 (fr)

1959
- 1959-01-30 CH CH6897259A patent/CH380741A/de unknown
1960
- 1960-01-16 DE DE1960H0038396 patent/DE1164420B/de active Pending
- 1960-01-27 BE BE586986A patent/BE586986A/fr unknown
- 1960-01-29 ES ES0255383A patent/ES255383A1/es not_active Expired

Also Published As

Publication number	Publication date
BE586986A (fr)	1960-07-27
ES255383A1 (es)	1960-07-01
DE1164420B (de)	1964-03-05

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