CS200250B2 - Process for preparing lysergole and canoclavine - Google Patents

Process for preparing lysergole and canoclavine Download PDF

Info

Publication number: CS200250B2
Authority: CS; Czechoslovakia
Prior art keywords: mixture; solvent; extracted; residue; alkaloids
Prior art date: 1971-08-17

Application number

CS725640A

Other languages

Czech (cs)

English (en)

Inventor

Giorgio Ferrari

Original Assignee

Giorgio Ferrari

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.)

1971-08-17

Filing date

1972-08-14

Publication date

1980-08-29

1972-08-14 Application filed by Giorgio Ferrari filed Critical Giorgio Ferrari

1980-08-29 Publication of CS200250B2 publication Critical patent/CS200250B2/cs

Links

BIXJFIJYBLJTMK-MEBBXXQBSA-N lysergol Chemical compound C1=CC(C2=C[C@@H](CO)CN([C@@H]2C2)C)=C3C2=CNC3=C1 BIXJFIJYBLJTMK-MEBBXXQBSA-N 0.000 title claims abstract description 16
238000004519 manufacturing process Methods 0.000 title claims description 4
238000000034 method Methods 0.000 claims abstract description 19
229930013930 alkaloid Natural products 0.000 claims abstract description 18
BIXJFIJYBLJTMK-UHFFFAOYSA-N Lysergol Natural products C1=CC(C2=CC(CO)CN(C2C2)C)=C3C2=CNC3=C1 BIXJFIJYBLJTMK-UHFFFAOYSA-N 0.000 claims abstract description 15
238000000605 extraction Methods 0.000 claims abstract description 13
239000002904 solvent Substances 0.000 claims abstract description 11
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims abstract description 8
241000207782 Convolvulaceae Species 0.000 claims abstract description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
239000000203 mixture Chemical class 0.000 claims description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
239000000284 extract Substances 0.000 claims description 11
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
239000000706 filtrate Substances 0.000 claims description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
239000011541 reaction mixture Substances 0.000 claims description 4
-1 aliphatic chlorinated hydrocarbon Chemical class 0.000 claims description 3
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
229910021529 ammonia Inorganic materials 0.000 claims description 3
238000002425 crystallisation Methods 0.000 claims description 3
230000008025 crystallization Effects 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
239000002244 precipitate Substances 0.000 claims description 2
238000001953 recrystallisation Methods 0.000 claims description 2
238000005406 washing Methods 0.000 claims description 2
239000000243 solution Substances 0.000 claims 2
244000021685 Mesembryanthemum crystallinum Species 0.000 claims 1
239000003929 acidic solution Substances 0.000 claims 1
150000008064 anhydrides Chemical class 0.000 claims 1
239000011260 aqueous acid Substances 0.000 claims 1
239000004927 clay Substances 0.000 claims 1
239000011877 solvent mixture Substances 0.000 claims 1
241000196324 Embryophyta Species 0.000 abstract description 11
241000207783 Ipomoea Species 0.000 abstract description 4
235000021506 Ipomoea Nutrition 0.000 abstract description 4
240000007218 Ipomoea hederacea Species 0.000 abstract description 4
241000894007 species Species 0.000 abstract description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
239000002585 base Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000012141 concentrate Substances 0.000 description 3
239000012065 filter cake Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000002198 insoluble material Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
241000598138 Ipomoea muricata Species 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
150000003797 alkaloid derivatives Chemical class 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000003814 drug Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
235000013861 fat-free Nutrition 0.000 description 2
238000002955 isolation Methods 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 2
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 2
235000012141 vanillin Nutrition 0.000 description 2
238000005303 weighing Methods 0.000 description 2
244000307697 Agrimonia eupatoria Species 0.000 description 1
206010012735 Diarrhoea Diseases 0.000 description 1
244000061408 Eugenia caryophyllata Species 0.000 description 1
SAHHMCVYMGARBT-UHFFFAOYSA-N Isochanoclavine I Natural products C1=CC(C(C(NC)C2)C=C(C)CO)=C3C2=CNC3=C1 SAHHMCVYMGARBT-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
235000016639 Syzygium aromaticum Nutrition 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000004913 activation Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
230000001754 anti-pyretic effect Effects 0.000 description 1
230000000794 anti-serotonin Effects 0.000 description 1
239000002221 antipyretic Substances 0.000 description 1
239000003420 antiserotonin agent Substances 0.000 description 1
210000001099 axilla Anatomy 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical group 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
235000000125 common agrimony Nutrition 0.000 description 1
230000008094 contradictory effect Effects 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
238000001514 detection method Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
238000009413 insulation Methods 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
239000008141 laxative Substances 0.000 description 1
230000002475 laxative effect Effects 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
210000005259 peripheral blood Anatomy 0.000 description 1
239000011886 peripheral blood Substances 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000000506 psychotropic effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
210000001550 testis Anatomy 0.000 description 1
210000004291 uterus Anatomy 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
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/90—Benzo [c, d] indoles; Hydrogenated benzo [c, d] indoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G5/00—Alkaloids

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Medicines Containing Plant Substances (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Indole Compounds (AREA)

CS725640A 1971-08-17 1972-08-14 Process for preparing lysergole and canoclavine CS200250B2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
BE107138		1971-08-17
BE112886		1972-01-14

Publications (1)

Publication Number	Publication Date
CS200250B2 true CS200250B2 (en)	1980-08-29

Family

ID=25647563

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS725640A CS200250B2 (en)	1971-08-17	1972-08-14	Process for preparing lysergole and canoclavine

Country Status (7)

Country	Link
US (1)	US3920663A (de)
JP (1)	JPS5648509B2 (de)
CH (1)	CH606021A5 (de)
CS (1)	CS200250B2 (de)
DE (1)	DE2240266C2 (de)
ES (1)	ES405905A1 (de)
FR (1)	FR2271746A7 (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2746675C2 (de) *	1977-10-18	1979-10-04	Hermann Heye, 3063 Obernkirchen	Glasformmaschine mit mehreren Stationen
CH674367A5 (de) *	1987-06-16	1990-05-31	Arysearch Arylan Ag
CN102134239B (zh) *	2009-12-15	2012-10-24	戈埃尔·帕万·库马	从裂叶牵牛中提取高纯度麦角醇的方法
WO2017141269A1 (en) *	2016-02-19	2017-08-24	Council Of Scientific & Industrial Research	An eco-friendly process for the isolation of vanillin from ipomea carnea

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2114306A (en) *		1938-04-19		Improved method of separating
US2255124A (en) *	1939-08-21	1941-09-09	Abbott Lab	Extraction process
US2809920A (en) *	1953-04-10	1957-10-15	Saul & Co	Process for the preparation of ergotamine, ergotaminine and ergometrine by saprophytic culture of ergot (claviceps purpurea [fr] tul.) in vitro and isolation of the alkaloids thus produced
CH425088A (de) *	1962-08-30	1966-11-30	Sandoz Ag	Verfahren zur Gewinnung von Lysergsäure-Derivate enthaltenden Alkaloidgemischen
US3224945A (en) *	1963-05-06	1965-12-21	College Of Pharmacy	Process for the production of ergot alkaloids

1972
- 1972-08-07 ES ES405905A patent/ES405905A1/es not_active Expired
- 1972-08-14 CS CS725640A patent/CS200250B2/cs unknown
- 1972-08-14 US US280212A patent/US3920663A/en not_active Expired - Lifetime
- 1972-08-15 CH CH1207772A patent/CH606021A5/xx not_active IP Right Cessation
- 1972-08-16 DE DE2240266A patent/DE2240266C2/de not_active Expired
- 1972-08-17 JP JP8185772A patent/JPS5648509B2/ja not_active Expired
- 1972-08-17 FR FR7229494A patent/FR2271746A7/fr not_active Expired

Also Published As

Publication number	Publication date
DE2240266C2 (de)	1983-07-14
JPS5648509B2 (de)	1981-11-16
DE2240266A1 (de)	1973-03-01
FR2271746A7 (de)	1975-12-12
CH606021A5 (de)	1978-10-13
US3920663A (en)	1975-11-18
ES405905A1 (es)	1976-01-16
JPS4833011A (de)	1973-05-07

Publication	Publication Date	Title
Ewins	1914	Acetylcholine, a new active principle of ergot
Koepfli et al.	1949	Alkaloids of Dichroa febrifuga. I. Isolation and degradative studies
Dutcher	1946	Curare alkaloids from Chondodendron tomentosum Ruiz and Pavon
Dudley	1929	Observations on acetylcholine
Manske	1931	The alkaloids of Senecio species: i. The necines and necic acids from S. retrorsus and S. jacobaea
CS200250B2 (en)	1980-08-29	Process for preparing lysergole and canoclavine
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Synge	1939	Experiments on amino-acids: A method for the isolation of hydroxy-amino-acids from protein hydrolysates
WO2018153310A1 (zh)	2018-08-30	一种环烯醚萜类化合物及其制备方法和应用
SHIBATA et al.	1969	Reexamination on the structure of so-called “Hiviscin”
US2552896A (en)	1951-05-15	Methanol extraction of cascara sagrada bark
Power et al.	1908	LXXXIII.—The constituents of olive leaves
Berlin	1926	The Occurrence of Gentiobiose in the Products of the Commercial Hydrolysis of Corn STARCH2
US4198344A (en)	1980-04-15	Process for the preparation of polyhydroxylated steroids, lysergol and ergolinic alkaloids
US2534250A (en)	1950-12-19	Process of isolating quercitrin
Louw	1952	Transvaalin, a cardiac glycoside isolated from Urginea burkei, BKR.(Transvaal slangkop)
Haas et al.	1933	The metabolism of calcareous algae. I
Pyman	1917	XXXVIII.—The alkaloids of ipecacuanha. Part II
Warren et al.	1950	The Saponins: Part I. The isolation of gitogenin and digitogenin from Cestrum lavigatum
Lamb et al.	1936	107. The glucosides of Strophanthus Emini
PT100819A (pt)	1994-02-28	Farmacos para a preparacao de composicoes e/ou substancias com actividade anti-neoplastica a partir de plantas pertencentes a familia palma, composicoes e substancias assim obtidas e preparacoes farmaceuticas que contem como pelo menos um dos seus principios activos, as composicoes e substancias citadas
Sammons et al.	1941	Studies in detoxication: The conjugation and oxidation of p-hydroxybenzenesulphonamide in the rabbit. The characterization of p-sulphonamidophenylglucuronide
Clarke et al.	1910	CXCVI.—A glucoside from Tephrosia purpurea