GB674061A - Alcohols and amines containing the lysergic acid ring system and process for their manufacture - Google Patents

Alcohols and amines containing the lysergic acid ring system and process for their manufacture

Info

Publication number
GB674061A
GB674061A GB10515/49A GB1051549A GB674061A GB 674061 A GB674061 A GB 674061A GB 10515/49 A GB10515/49 A GB 10515/49A GB 1051549 A GB1051549 A GB 1051549A GB 674061 A GB674061 A GB 674061A
Authority
GB
United Kingdom
Prior art keywords
manufacture
acid
methyl ester
formula
lysergic acid
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
GB10515/49A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sandoz AG
Original Assignee
Sandoz AG
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 Sandoz AG filed Critical Sandoz AG
Priority to GB10515/49A priority Critical patent/GB674061A/en
Publication of GB674061A publication Critical patent/GB674061A/en
Expired legal-status Critical Current

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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/48—Ergoline derivatives, e.g. lysergic acid, ergotamine
    • 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

Abstract

The invention comprises compounds of the general formula <FORM:0674061/IV (b)/1> (wherein R represents OH or NYZ, Y and Z being H or alkyl), and the manufacture thereof and of their dihydro derivatives by reducing, by means of lithium aluminium hydride or lithium boron hydride in an inert solvent selected from ethers, dioxane and ethyl morpholine, a compound of the general formula <FORM:0674061/IV (b)/2> (wherein X1 is C and X2 is CH, or X1 is CH and X2 is CH2, and R represents OH, O alkyl or NYZ). The products, which form water-soluble salts with organic and inorganic acids, are useful as intermediates for the manufacture of therapeutically-active compounds. Examples describe the reduction of: (1) lysergic acid methyl ester to lysergol (formula (A), R=OH), which yields a tartrate by the action of tartaric acid in alcoholic solution; (2) isolysergic acid methyl ester to isolysergol (a stereoisomer of lysergol); (3) lysergic acid diethylamide to 6 - methyl - 8 - diethylaminomethylergolene (formula (A), R=N(C2H5)2); (4) dihydrolysergic acid methyl ester to dihydrolysergol; (5) and (6) dihydroisolysergic acid (I) and (II) methyl esters to dihydroisolysergol (I) and (II). Additional starting materials specified are the acids corresponding to the esters used in the examples. Reference has been directed by the Comptroller to Specification 670,991.
GB10515/49A 1949-04-20 1949-04-20 Alcohols and amines containing the lysergic acid ring system and process for their manufacture Expired GB674061A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB10515/49A GB674061A (en) 1949-04-20 1949-04-20 Alcohols and amines containing the lysergic acid ring system and process for their manufacture

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB10515/49A GB674061A (en) 1949-04-20 1949-04-20 Alcohols and amines containing the lysergic acid ring system and process for their manufacture

Publications (1)

Publication Number Publication Date
GB674061A true GB674061A (en) 1952-06-18

Family

ID=9969251

Family Applications (1)

Application Number Title Priority Date Filing Date
GB10515/49A Expired GB674061A (en) 1949-04-20 1949-04-20 Alcohols and amines containing the lysergic acid ring system and process for their manufacture

Country Status (1)

Country Link
GB (1) GB674061A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3014909A (en) * 1961-12-26 New basically substituted g-methyx-
US3228939A (en) * 1966-01-11 Methyl and i,g-dimethyl-ergoline ii derivatives
US3228942A (en) * 1966-01-11 Methyl and i,g-dimeti-iyl ergoline i compounds
US3232942A (en) * 1964-06-02 1966-02-01 Sandoz Ltd 1-substituted (+)-lysergol

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3014909A (en) * 1961-12-26 New basically substituted g-methyx-
US3228939A (en) * 1966-01-11 Methyl and i,g-dimethyl-ergoline ii derivatives
US3228942A (en) * 1966-01-11 Methyl and i,g-dimeti-iyl ergoline i compounds
US3232942A (en) * 1964-06-02 1966-02-01 Sandoz Ltd 1-substituted (+)-lysergol

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