GB774989A - Improvements in or relating to novel chemical compounds useful in the synthesis of lysergic acid and its homologues and process for preparing such compounds - Google Patents
Improvements in or relating to novel chemical compounds useful in the synthesis of lysergic acid and its homologues and process for preparing such compoundsInfo
- Publication number
- GB774989A GB774989A GB20245/55A GB2024555A GB774989A GB 774989 A GB774989 A GB 774989A GB 20245/55 A GB20245/55 A GB 20245/55A GB 2024555 A GB2024555 A GB 2024555A GB 774989 A GB774989 A GB 774989A
- Authority
- GB
- United Kingdom
- Prior art keywords
- homologues
- synthesis
- compounds
- relating
- preparing
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention comprises halogenated octahydro-indolo-quinolines (ergolenes) of the formula <FORM:0774989/IV(b)/1> where X is chlorine or bromine, R is C1-C8 alkyl, monocyclic aryl or monocyclic aralkyl having 1-8 carbon atoms in the side chain, and R1 is C1-C8 alkyl, and acid addition salts thereof. These are made by halogenating the compounds (X=OH)-see Specification 774,988 -to replace the hydroxy group by halogen. If desired, the starting materials (which are used in the form of their salts) may be treated with a strong acid to invert the stereo-configuration of the hydroxyl group. Examples are given of the preparation of 4-acetyl-9-chloro-7-methyl-10-ergolene from the hydroxy compound and thionyl chloride, isolated as hydrochloride; the 9-bromo compound is made similarly. R may also be phenyl and R1 may be ethyl or propyl. The products are intermediates in the synthesis of lysergic acid and its homologues.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US774989XA | 1954-09-27 | 1954-09-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB774989A true GB774989A (en) | 1957-05-15 |
Family
ID=22138430
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB20245/55A Expired GB774989A (en) | 1954-09-27 | 1954-10-25 | Improvements in or relating to novel chemical compounds useful in the synthesis of lysergic acid and its homologues and process for preparing such compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB774989A (en) |
-
1954
- 1954-10-25 GB GB20245/55A patent/GB774989A/en not_active Expired
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