GB1008466A - Improvements in or relating to lysergol derivatives - Google Patents
Improvements in or relating to lysergol derivativesInfo
- Publication number
- GB1008466A GB1008466A GB43625/61A GB4362561A GB1008466A GB 1008466 A GB1008466 A GB 1008466A GB 43625/61 A GB43625/61 A GB 43625/61A GB 4362561 A GB4362561 A GB 4362561A GB 1008466 A GB1008466 A GB 1008466A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- alkoxy
- reacting
- substituted
- lysergic
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention comprises 1-substituted lysergols of general formula <FORM:1008466/C2/1> in which R1 is C1- 14 alkyl, C2- 4 alkenyl or C7- 10 aralkyl and x y signifies <FORM:1008466/C2/2> or <FORM:1008466/C2/3> and the addition salts of these compounds with inorganic or organic acids; and a process for their preparation in which a compound of formula <FORM:1008466/C2/4> in which R2 is alkoxy, aralkoxy or a 3,5-dialkylpyrazolyl-(1) radical, is reduced. In the process, suitable reducing agents are lithium aluminium hydride when x y is a double bond in both the starting material and the product, and sodium in alcohol when x y is saturated in the product. The compounds of Formula II may be produced by (1) alkylating or alkenylating a corresponding ester which is unsubstituted in the 1-position (only when R2 is alkoxy or aralkoxy), (2) converting a corresponding 1-substituted lysergic or dihydrolysergic acid into its halide and esterifying with the desired alcohol, the acid being obtained by alkaline saponification of a 1-substituted ergot alkaloid (only when R2 is alkoxy or aryloxy), (3) reacting with hydrazine a 1-substituted ergot alkaloid, converting the hydrazide with nitrous acid into the azide and reacting the azide with R2OH (only when R2 is alkoxy or aryloxy), and (4) reacting the hydrazide of (3) with an a b -diketone alkyl-CO-CH2CO-alkyl (only when R2 is a 3,5-dialkylpyrazolyl-(1) radical). Detailed examples describe the preparation of compounds of both Formula I and Formula II by the above methods; the preparations of 1-allyl -D-lysergic acid methyl ester and 1-benzyl -D-lysergic acid methyl ester by reacting D-lysergic acid in liquid ammonia with sodium amide and allyl or benzyl bromide and esterifying with diazomethane are also illustrated. The lysergic acid derivatives of the invention, which are stated to exhibit a serotonin inhibiting effect and a beneficial effect on the psyche, rheumatism, allergies, inflammations and migraine, may be made up into pharmaceutical compositions with suitable carriers. Specifications 911,115, 948,203 and 988,001 are referred to.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1438160A CH392537A (en) | 1960-12-23 | 1960-12-23 | Process for the preparation of new heterocyclic alcohols |
| CH1230761 | 1961-10-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1008466A true GB1008466A (en) | 1965-10-27 |
Family
ID=25710011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB43625/61A Expired GB1008466A (en) | 1960-12-23 | 1961-12-06 | Improvements in or relating to lysergol derivatives |
Country Status (3)
| Country | Link |
|---|---|
| AT (1) | AT240530B (en) |
| FR (1) | FR1860M (en) |
| GB (1) | GB1008466A (en) |
-
1961
- 1961-12-06 GB GB43625/61A patent/GB1008466A/en not_active Expired
- 1961-12-21 AT AT967661A patent/AT240530B/en active
-
1962
- 1962-03-20 FR FR891592A patent/FR1860M/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AT240530B (en) | 1965-06-10 |
| FR1860M (en) | 1963-06-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| IE36797L (en) | 1,5-benzodiazepin-2-one derivatives. | |
| GB1008466A (en) | Improvements in or relating to lysergol derivatives | |
| ES454063A1 (en) | Novel benzylalcohol derivatives and processes for preparing the same | |
| GB999589A (en) | ||
| GB1073828A (en) | O-desacetyl-o-carbamoyl-7-acylamino-cephalosporanic acids | |
| GB1139458A (en) | 2-phenylamino-2-oxazolines and their production | |
| GB1319346A (en) | Heterocyclic substituted vinyl phsophates | |
| GB1347598A (en) | Lincomycin derivatives and the manufacture thereof | |
| ES254772A1 (en) | Certain nu-(3, 5-diiodo-4-pyridonealkanoyl)-aminoalkanoic acids | |
| ES8602685A1 (en) | Imidazole derivative and its preparation | |
| GB1173372A (en) | Substituted 3-Aminopyrrolidines | |
| GB961265A (en) | 3,4-dihydroxyphenyl-acetic acid ester derivatives | |
| GB1351526A (en) | Tropan-3-ol derivatives and processes for their preparation | |
| GB1017979A (en) | Improvements in or relating to the preparation of chloro-acetoacetamides and to substituted dioxolan derivatives of acetic acid esters as intermediates in said preparation | |
| GB1088880A (en) | ª‡-cycloalkyleneimino-substituted esters | |
| GB721477A (en) | 4-aminobenzoic acid ester compounds of penicillin | |
| GB1056475A (en) | Process for preparing 4-amino-pyrazolone derivatives | |
| ES345183A1 (en) | Glycyrrhetinic acid derivatives | |
| GB1095185A (en) | Phenylalanine derivatives | |
| GB729331A (en) | Improvements in or relating to thiazole derivatives | |
| GB1138247A (en) | Oleanolic acid derivatives | |
| GB866432A (en) | New carboxylic acid amides substituted at the nitrogen atom and ª--carbon atom | |
| GB922028A (en) | New therapeutically-valuable organic compounds and processes for their preparation | |
| ES387584A1 (en) | Alkyl 1 1a 2 6b-tetrahydrocycloprop(b)indole 1-carboxylates and acids | |
| GB950509A (en) | Improvements in or relating to piperazides |