CH196552A - Process for the preparation of d-lysergic acid-l-norepheride. - Google Patents
Process for the preparation of d-lysergic acid-l-norepheride.Info
- Publication number
- CH196552A CH196552A CH196552DA CH196552A CH 196552 A CH196552 A CH 196552A CH 196552D A CH196552D A CH 196552DA CH 196552 A CH196552 A CH 196552A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- lysergic acid
- preparation
- norepheride
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- NCIHPOHJJSIWSC-QMTHXVAHSA-N (6ar,9r)-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-carbonyl azide Chemical compound C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(=O)N=[N+]=[N-])=C3C2=CNC3=C1 NCIHPOHJJSIWSC-QMTHXVAHSA-N 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- DLNKOYKMWOXYQA-CBAPKCEASA-N (-)-norephedrine Chemical compound C[C@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-CBAPKCEASA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- ZAGRKAFMISFKIO-UHFFFAOYSA-N Isolysergic acid Natural products C1=CC(C2=CC(CN(C2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- DLNKOYKMWOXYQA-UHFFFAOYSA-N dl-pseudophenylpropanolamine Natural products CC(N)C(O)C1=CC=CC=C1 DLNKOYKMWOXYQA-UHFFFAOYSA-N 0.000 description 1
- ZAGRKAFMISFKIO-QMTHXVAHSA-N lysergic acid Chemical compound C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-QMTHXVAHSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- DLNKOYKMWOXYQA-APPZFPTMSA-N phenylpropanolamine Chemical compound C[C@@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-APPZFPTMSA-N 0.000 description 1
- 229960000395 phenylpropanolamine Drugs 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D457/00—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid
- C07D457/04—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 8
- C07D457/06—Lysergic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Description
Verfahren zur Darstellung von d-Lysergsäure-l-norepherid. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung von -d-Lyserg- säure-l-no@rephedrid, welches dadurch gekenn zeichnet ist, dass man rac. Lysergsäure-azid mit l-Norephedrin umsetzt und die dabei entstehenden isomeren Verbindungen trennt.
Die rechtsdrehende Komponente des. End produktes, welche ein .spez. Drehvermögen [al<B>l"</B> = + 296 (c = 0,2e3 in Aceton) be sitzt und meist nur in amorphem Zustand erhalten wird, ist @d'-Lysergsiäure-l-norephe- ,drid. Die Zusammensetzung mitspricht der Bruttoformel C"ss"0_#N3.
Die neue Verbindung gibt die blaue Kellersche Farbreaktion und soll für thera peutische Zwecke Verwendung finden.
Beispiel: 1 g frisch hergestelltes rac. Lysergsäure- azid wird in eine Lösung von 1 g l-Nore- phedrin in 210 cmg Alkohol bei 0 eingetra gen. Beim Verreiben tritt rasch Lösung ein.
Das Lösungsmittel wird im Vakuum abge dampft und zur Entfernung von überschüssi- gem Norephedrin der klebrige Rückstand mehrere Male mit je 20 cm' Wasser extra- hiert. Dann wird die trockene, amorphe Sub stanz in 5 em@ absol. Alkohol gelöst und mit. 40 em3 Äther verdünnt.
l-Lysergsäure-l-nore- phedrid scheidet sich sogleich in glitzernden Kristallen in Form der Äther-A@dditionsver- bindung ab. Ausbeute 0,4 g.
Die Mutterlauge wird abgedampft, der Rückstand in 10 cm' Alkohol gelöst und tropfenweise, bis keine weitere Fällung mehr eintritt, alkoholische Phosphorsäure zuge geben. Der Niedersohlag besteht aus dem Phosphat von @d-Lysergsäure-l-norephiedrid, während Spuren von l-Lys,ergsiäurerl-nore- phe,driclphosphat in Lösung bleiben.
Das Phosphat wird abgenutscht, in 30 cm' Was ser gelöste und .durch Zusatz von Natrium- bikarbon:at .das Alkaloid in Freiheit gesetzt. Es scheidet .sich .als in Wasser praktisch un lösliche, weisse, körnige Flocken ab. Aus beute 0,5 g.
d-Lysergsäure-l-norephedrid kann durch Umlösen aus Benzol weiter gereinigt werden.
EMI0002.0001
Es <SEP> schmilzt. <SEP> unscharf <SEP> zwischen <SEP> 110 <SEP> bis <SEP> <B>130'</B>
<tb> (korr.). <SEP> Zusammensetzung <SEP> CZJH=; <SEP> 0.N;.. <SEP> Polari sation: <SEP> 0,0233 <SEP> g <SEP> der <SEP> Verbindung <SEP> zu <SEP> 10,0 <SEP> ein'
<tb> Aoeton <SEP> gelöst, <SEP> drehten <SEP> im <SEP> 1 <SEP> dm-Rohr <SEP> bei <SEP> 20'
<tb> um <SEP> 0,69 <SEP> <SEP> nach <SEP> rechts. <SEP> [a] <SEP> i; <SEP> = <SEP> + <SEP> 296 <SEP> .
<tb>
Die <SEP> neuen <SEP> Verbindungen <SEP> beben <SEP> die <SEP> blaue
<tb> Kellersche <SEP> Farbreaktion, <SEP> welche <SEP> für <SEP> '_Vlutter kornalka.loide <SEP> charakteristisch <SEP> ist.
Process for the preparation of d-lysergic acid-l-norepheride. The present patent is a process for the preparation of -d-lysergic acid-l-no @ rephedrid, which is characterized in that one rac. Lysergic acid acid reacts with l-norephedrine and separates the isomeric compounds that are formed.
The clockwise component of the end product, which is a .spec. Rotational power [al <B> l "</B> = + 296 (c = 0.2e3 in acetone) and is usually only obtained in an amorphous state is @ d'-lysergic acid-l-norephe-, drid Composition corresponds to the gross formula C "ss" 0_ # N3.
The new compound gives the blue cellar color reaction and is intended to be used for therapeutic purposes.
Example: 1 g of freshly made rac. Lysergic acid azide is added to a solution of 1 g of l-norephedrine in 210 cmg of alcohol at 0. When rubbed in, it dissolves quickly.
The solvent is evaporated off in vacuo and the sticky residue is extracted several times with 20 cm of water each time to remove excess norephedrine. Then the dry, amorphous substance is in 5 em @ absol. Alcohol dissolved and with. 40 em3 ether diluted.
L-lysergic acid-l-norephedrid is immediately deposited in glittering crystals in the form of the ether-addition compound. Yield 0.4g.
The mother liquor is evaporated, the residue is dissolved in 10 cm 'of alcohol and alcoholic phosphoric acid is added dropwise until no further precipitation occurs. The lower soil consists of the phosphate of @ d-lysergic acid-l-norephiedrid, while traces of l-lys, ergsic acid-norephe, driclphosphate remain in solution.
The phosphate is sucked off, dissolved in 30 cm of water, and the alkaloid is set free by adding sodium bicarbonate. It separates out as white, granular flakes that are practically insoluble in water. From booty 0.5 g.
d-Lysergic acid-l-norephedride can be further purified by dissolving it from benzene.
EMI0002.0001
It <SEP> melts. <SEP> unset <SEP> between <SEP> 110 <SEP> to <SEP> <B> 130 '</B>
<tb> (corr.). <SEP> Composition <SEP> CZJH =; <SEP> 0.N; .. <SEP> polarization: <SEP> 0.0233 <SEP> g <SEP> of the <SEP> connection <SEP> to <SEP> 10.0 <SEP> on '
<tb> Aoeton <SEP> released, <SEP> turned <SEP> in <SEP> 1 <SEP> dm pipe <SEP> at <SEP> 20 '
<tb> by <SEP> 0.69 <SEP> <SEP> after <SEP> right. <SEP> [a] <SEP> i; <SEP> = <SEP> + <SEP> 296 <SEP>.
<tb>
The <SEP> new <SEP> connections <SEP> quake <SEP> the <SEP> blue ones
<tb> Kellersche <SEP> color reaction, <SEP> which <SEP> for <SEP> '_Vlutter kornalka.loide <SEP> is characteristic <SEP>.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH191342T | 1936-06-20 | ||
| CH196552T | 1936-06-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH196552A true CH196552A (en) | 1938-03-15 |
Family
ID=4437558
Family Applications (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH191342D CH191342A (en) | 1936-06-20 | 1936-06-20 | Method for the preparation of rac. Lysergic acid ethanolamide. |
| CH196552D CH196552A (en) | 1936-06-20 | 1936-06-20 | Process for the preparation of d-lysergic acid-l-norepheride. |
| CH196550D CH196550A (en) | 1936-06-20 | 1936-06-20 | Process for the preparation of d-lysergic acid-d-isopropanolamide. |
| CH196551D CH196551A (en) | 1936-06-20 | 1936-06-20 | Method for the preparation of rac. Lysergic acid tyramide. |
| CH196549D CH196549A (en) | 1936-06-20 | 1936-06-20 | Method for the preparation of rac. Lysergic acid isopropanolamide. |
| CH223016D CH223016A (en) | 1936-06-20 | 1939-06-06 | Process for the preparation of d-lysergic acid-d-1-oxy-butyl-amide- (2). |
| CH223015D CH223015A (en) | 1936-06-20 | 1939-06-06 | Process for the preparation of d-lysergic acid-d-1-oxy-butyl-amide- (2). |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH191342D CH191342A (en) | 1936-06-20 | 1936-06-20 | Method for the preparation of rac. Lysergic acid ethanolamide. |
Family Applications After (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH196550D CH196550A (en) | 1936-06-20 | 1936-06-20 | Process for the preparation of d-lysergic acid-d-isopropanolamide. |
| CH196551D CH196551A (en) | 1936-06-20 | 1936-06-20 | Method for the preparation of rac. Lysergic acid tyramide. |
| CH196549D CH196549A (en) | 1936-06-20 | 1936-06-20 | Method for the preparation of rac. Lysergic acid isopropanolamide. |
| CH223016D CH223016A (en) | 1936-06-20 | 1939-06-06 | Process for the preparation of d-lysergic acid-d-1-oxy-butyl-amide- (2). |
| CH223015D CH223015A (en) | 1936-06-20 | 1939-06-06 | Process for the preparation of d-lysergic acid-d-1-oxy-butyl-amide- (2). |
Country Status (2)
| Country | Link |
|---|---|
| CH (7) | CH191342A (en) |
| FR (1) | FR825057A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1034641B (en) * | 1955-03-07 | 1958-07-24 | Lilly Co Eli | Process for the production of lysergic acid amides |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1096364B (en) * | 1956-08-09 | 1961-01-05 | Miroslav Semonsky Dr Ing | Process for the preparation of pharmacodynamically active substituted amides of d-lysergic acid and their salts |
| US4902691A (en) * | 1988-12-19 | 1990-02-20 | Eli Lilly And Company | Heteroalkylamides of (8-β)-1-alkyl-6-(substituted)ergolines useful for blocking 5HT2 receptors |
-
1936
- 1936-06-20 CH CH191342D patent/CH191342A/en unknown
- 1936-06-20 CH CH196552D patent/CH196552A/en unknown
- 1936-06-20 CH CH196550D patent/CH196550A/en unknown
- 1936-06-20 CH CH196551D patent/CH196551A/en unknown
- 1936-06-20 CH CH196549D patent/CH196549A/en unknown
- 1936-11-16 FR FR825057D patent/FR825057A/en not_active Expired
-
1939
- 1939-06-06 CH CH223016D patent/CH223016A/en unknown
- 1939-06-06 CH CH223015D patent/CH223015A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1034641B (en) * | 1955-03-07 | 1958-07-24 | Lilly Co Eli | Process for the production of lysergic acid amides |
Also Published As
| Publication number | Publication date |
|---|---|
| CH223016A (en) | 1942-08-15 |
| FR825057A (en) | 1938-02-23 |
| CH191342A (en) | 1937-06-15 |
| CH223015A (en) | 1942-08-15 |
| CH196549A (en) | 1938-03-15 |
| CH196551A (en) | 1938-03-15 |
| CH196550A (en) | 1938-03-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH196552A (en) | Process for the preparation of d-lysergic acid-l-norepheride. | |
| DE834989C (en) | Process for the production of 21-iodine-pregnen- (5) -ol- (3) -one- (20) | |
| DE2006484C3 (en) | Process for the production of creatinol-O-dihydrogen phosphate | |
| DE728361C (en) | Process for the preparation of d-lysergic acid-d-1-oxybutylamide- (2) | |
| DE958109C (en) | Process for the production of tetracyclines from their solutions | |
| DE936162C (en) | Process for obtaining a substance mixture with a specific, predominantly spasmolytic effect from Radix liquiritiae | |
| DE515851C (en) | Process for the complete separation of technically pure rubidium (and cesium) salts from those of the alkalis | |
| DE442039C (en) | Process for the preparation of alkali-alkaline earth double salts of aromatic halosulfonamides | |
| DE954415C (en) | Process for the preparation of neutral esters of thiolphosphoric acid | |
| AT251772B (en) | Process for the production of a new ethynyl derivative of 8-iso-oestrone | |
| DE681049C (en) | Process for the preparation of core alkylated, core aralkylated or core arylated compounds of the morphine series | |
| DE1958016C3 (en) | Inosine-3 'to 5'-monophosphate-2'-O-ester | |
| DE883435C (en) | Process for the preparation of dioxyacetone compounds | |
| DE606498C (en) | Process for the preparation of salts from acylaminoarylarsic acids and acridinium compounds | |
| DE439605C (en) | Process for the preparation of a benzoxazolonarsinic acid | |
| DE2365322C3 (en) | Subst.-methyl-phosphonic acid dimethyl ester and a process for their preparation | |
| CH219010A (en) | Process for the preparation of a solid molecular compound containing mercury. | |
| CH288024A (en) | Process for the preparation of pyridyl-3-aldehyde thiosemicarbazone. | |
| CH222491A (en) | Process for the preparation of 3-acetoxybisnorcholanyl-acetoxymethyl-ketone. | |
| CH240068A (en) | Process for the preparation of ampoules containing colorless aqueous solutions of a vitamin K-active compound. | |
| CH283634A (en) | Process for the preparation of a peptide-like derivative of the lysergic acid series. | |
| CH214844A (en) | Process for the preparation of tropic acid benzylamide. | |
| CH307801A (en) | Process for the preparation of a morphine derivative. | |
| DE1005964B (en) | Process for the preparation of new alkoxy mercury compounds | |
| CH243026A (en) | Process for the preparation of a soluble salt of 4,4'-di-amidino-diphenyl ether. |