CH196551A - Method for the preparation of rac. Lysergic acid tyramide. - Google Patents

Method for the preparation of rac. Lysergic acid tyramide.

Info

Publication number
CH196551A
CH196551A CH196551DA CH196551A CH 196551 A CH196551 A CH 196551A CH 196551D A CH196551D A CH 196551DA CH 196551 A CH196551 A CH 196551A
Authority
CH
Switzerland
Prior art keywords
sep
rac
tyramide
acid
lysergic acid
Prior art date
Application number
Other languages
German (de)
Inventor
Sandoz Chemische Fabri Vormals
Original Assignee
Chem Fab Vormals Sandoz
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.)
Filing date
Publication date
Application filed by Chem Fab Vormals Sandoz filed Critical Chem Fab Vormals Sandoz
Publication of CH196551A publication Critical patent/CH196551A/en

Links

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     rag.        Lysergsäure-tyramid.       Gegenstand des vorliegenden     Zusatzpaten-          tes    ist ein Verfahren zur Darstellung von       rac.        Lysergsäure-tyramid,    welches dadurch       gekennzeichnet    ist,     :dass    man     rac.        Lyserg-          säure-azid    mit     Tyramin    umsetzt.  



  Die neue Verbindung vom Typus der       Mutterkornalkaloide    kristallisiert aus     Aceton     in derben, schräg     abgeschnittenen    Prismen,  die bei 205 bis 210   unter Zersetzung     sehmel-          zen.    Sie soll     therapeutische    Verwendung fin  den. Oft werden an Stelle .der     Prismen    auch  dünne Platten mit dem Schmelzpunkt 9,40'       (korr.)    erhalten. Die Verbindung vermag also  in zwei polymorphen     DZodifikationen    aufzu  treten.  



       Beispiel:     8,0 g     rae.        Lysergsäure-hydrazid    werden  in das     Azid    übergeführt und dieses in eine  Lösung von     1,5g        Tyramin    in 110 cm' 0,1  n-Natronlauge bei 0       eingetragen.    Die Sus  pension wird     geschüttelt    bis     praktisch    alles       Azid    in Lösung gegangen ist.

   Die klar fil  trierte Lösung wird bei 0   mit     Kohlensäure            gesättigt,    wobei sich das     Tyramid    der       Lysergsäure    kristallinisch abscheidet. Es  lässt sich durch     Umkristallisieren    aus wenig  Aceton in analysenreinen     Zustand    bringen  und     kristallisiert    aus diesem     Lösungsmittel     in derben, schräg abgeschnittenen     Prismen,     die sich bei 205 bis 2-10'     (korr.)    zersetzen.

    Die Verbindung     ist    sowohl in     verd.    Säure,  wie in     verd.    Lauge     (phenolisches        Hydrogyl)     leicht, löslich. Sie gibt die blaue     gellersche     Farbreaktion, welche für     Mutterkornalkaloide          charakteristisch    ist.  



  Elementaranalyse: C 74,22;     74,03%;     H 6,72:; 6,80% und N 10,96;     10,83%.    Für       Lysergsäure-tyramid        C"H"0,N3        berechnen     sich C     74,3-7/'-    H     6,51%    und N<B>10,85%.</B>



  Procedure for displaying rag. Lysergic acid tyramide. The subject of the present additional patent is a method for the preparation of rac. Lysergic acid tyramide, which is characterized in that: that one rac. Lysergic acid acid reacts with tyramine.



  The new compound of the ergot alkaloids type crystallizes from acetone in coarse, obliquely cut prisms, which silt at 205 to 210 with decomposition. It should find therapeutic use. Often, instead of the prisms, thin plates with a melting point of 9.40 '(corr.) Are obtained. The compound can thus appear in two polymorphic DZodifications.



       Example: 8.0 g rae. Lysergic acid hydrazide are converted into the azide and this is added to a solution of 1.5 g of tyramine in 110 cm of 0.1 N sodium hydroxide solution at 0. The suspension is shaken until practically all of the azide has gone into solution.

   The clear filtered solution is saturated with carbonic acid at 0, the tyramide of the lysergic acid separating out in crystalline form. It can be brought into analytically pure state by recrystallization from a little acetone and crystallizes from this solvent in coarse, obliquely cut prisms, which decompose at 205 to 2-10 '(corr.).

    The compound is easily soluble in both dilute acid and dilute alkali (phenolic hydroyl). It gives the blue Geller color reaction, which is characteristic of ergot alkaloids.



  Elemental analysis: C, 74.22; 74.03%; H 6.72 :; 6.80% and N 10.96; 10.83%. For lysergic acid tyramide C "H" 0, N3, C 74.3-7 / '- H 6.51% and N <B> 10.85%. </B>

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von rac. Lyserg- säure-tyramid, dadurch :gekennzeichnet, dass man rac. Lysergsäure-azid mit Tyramin um setzt. PATENT CLAIM: Process for the representation of rac. Lysergic acid tyramide, characterized in that one rac. Lysergic acid acid with tyramine sets. Die neue Verbindung vom Typus der EMI0002.0001 1-Iutterkornalkaloide <SEP> mit <SEP> der <SEP> Zusammen setzung <SEP> <B>C.-111250.N.</B> <SEP> kristallisiert <SEP> aus <SEP> Aceton <tb> in <SEP> derben, <SEP> schräg <SEP> abgeschnittenen <SEP> Prismen. <tb> die <SEP> bei <SEP> \?05 <SEP> bis <SEP> 210 <SEP> <SEP> unter <SEP> Zersetzung <SEP> schmel zen. <SEP> Das <SEP> ra.c. <SEP> Lyser;sä.ure-ty <SEP> ra.mid <SEP> gibt <SEP> die für die Mutterkornalkaloide typische blaue hellerscho Farbreaktion. Das rac. Lyserbsäure-tyramid soll in der Therapie Verwendung finden. The new connection of the type EMI0002.0001 1-butter grain alkaloids <SEP> with <SEP> the <SEP> composition <SEP> <B> C.-111250.N. </B> <SEP> crystallizes <SEP> from <SEP> acetone <tb> in <SEP> coarse, <SEP> obliquely <SEP> cut <SEP> prisms. <tb> the <SEP> at <SEP> \? 05 <SEP> to <SEP> 210 <SEP> <SEP> under <SEP> decomposition <SEP> melt. <SEP> The <SEP> ra.c. <SEP> Lyser; sä.ure-ty <SEP> ra.mid <SEP> gives <SEP> the blue lighterscho color reaction typical for ergot alkaloids. The rac. Lyserbic acid tyramide should be used in therapy.
CH196551D 1936-06-20 1936-06-20 Method for the preparation of rac. Lysergic acid tyramide. CH196551A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH196551T 1936-06-20
CH191342T 1936-06-20

Publications (1)

Publication Number Publication Date
CH196551A true CH196551A (en) 1938-03-15

Family

ID=4437558

Family Applications (7)

Application Number Title Priority Date Filing Date
CH196551D CH196551A (en) 1936-06-20 1936-06-20 Method for the preparation of rac. Lysergic acid tyramide.
CH196550D CH196550A (en) 1936-06-20 1936-06-20 Process for the preparation of d-lysergic acid-d-isopropanolamide.
CH196552D CH196552A (en) 1936-06-20 1936-06-20 Process for the preparation of d-lysergic acid-l-norepheride.
CH191342D CH191342A (en) 1936-06-20 1936-06-20 Method for the preparation of rac. Lysergic acid ethanolamide.
CH196549D CH196549A (en) 1936-06-20 1936-06-20 Method for the preparation of rac. Lysergic acid isopropanolamide.
CH223015D CH223015A (en) 1936-06-20 1939-06-06 Process for the preparation of d-lysergic acid-d-1-oxy-butyl-amide- (2).
CH223016D CH223016A (en) 1936-06-20 1939-06-06 Process for the preparation of d-lysergic acid-d-1-oxy-butyl-amide- (2).

Family Applications After (6)

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.
CH196552D CH196552A (en) 1936-06-20 1936-06-20 Process for the preparation of d-lysergic acid-l-norepheride.
CH191342D CH191342A (en) 1936-06-20 1936-06-20 Method for the preparation of rac. Lysergic acid ethanolamide.
CH196549D CH196549A (en) 1936-06-20 1936-06-20 Method for the preparation of rac. Lysergic acid isopropanolamide.
CH223015D CH223015A (en) 1936-06-20 1939-06-06 Process for the preparation of d-lysergic acid-d-1-oxy-butyl-amide- (2).
CH223016D CH223016A (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) CH196551A (en)
FR (1) FR825057A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
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
EP0375297A2 (en) * 1988-12-19 1990-06-27 Eli Lilly And Company Improvements in or relating to ergoline derivatives

Families Citing this family (1)

* Cited by examiner, † Cited by third party
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

Cited By (3)

* Cited by examiner, † Cited by third party
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
EP0375297A2 (en) * 1988-12-19 1990-06-27 Eli Lilly And Company Improvements in or relating to ergoline derivatives
EP0375297A3 (en) * 1988-12-19 1991-10-23 Eli Lilly And Company Improvements in or relating to ergoline derivatives

Also Published As

Publication number Publication date
CH196552A (en) 1938-03-15
CH196549A (en) 1938-03-15
FR825057A (en) 1938-02-23
CH223016A (en) 1942-08-15
CH191342A (en) 1937-06-15
CH223015A (en) 1942-08-15
CH196550A (en) 1938-03-15

Similar Documents

Publication Publication Date Title
DE3911322A1 (en) METHOD FOR PRODUCING CEFODIZIM DINATRIUM
CH196551A (en) Method for the preparation of rac. Lysergic acid tyramide.
DE881194C (en) Process for the preparation of thiophosphoric acid esters of 3-halooxycoumarins
DE963872C (en) Process for the preparation of thiophosphoric acid esters
DE608667C (en) Process for the preparation of water-soluble zinc compounds of oxymethanesulfinic acid
DE606084C (en) Process for the production of barbituric acid coagulations
DE680595C (en) Process for the preparation of crystallized citric acid
AT136021B (en) Process for the preparation of N-monoallyl or N. N&#39;-diallyl derivatives of 5,5-disubstituted barbituric acids.
DE634285C (en) Process for the preparation of Abkoemmlingen des 2,4-Dioxotetrahydropyridins
DE512820C (en) Process for the preparation of oxyanthraquinone derivatives, in particular alizarin and its derivatives
DE553784C (en) Process for purifying crude naphthalene
DE628535C (en) Process for producing a quinine salt
DE208593C (en)
DE1227470B (en) Process for the preparation of crystallized p, p&#39;-isopropylidenediphenol with low phenol content
DE730728C (en) Process for the preparation of an acid of dimethanesulfonic acid imide
AT218531B (en) Process for the preparation of the new N- (4-sulfonamidophenyl) -butanesultam
DE586352C (en) Process for the preparation of water-soluble alkyl mercury mercapto compounds
DE802880C (en) Process for the manufacture of sodium penicillin
DE954872C (en) Process for the preparation of dithiocarbamic acid esters
DE647858C (en) Process for the extraction of alumina from aluminum salts
DE266788C (en)
DE597078C (en) Process for the preparation of triarylmethane dyes
DE457060C (en) Process for the preparation of ar-tetrahydro-ª ‰ -naphthol derivatives
DE479669C (en) Process for the preparation of compounds of dialkyl and arylalkyl barbituric acids
AT151662B (en) Process for the preparation of aromatic selenium compounds.