GB774990A - 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 compounds

Info

Publication number
GB774990A
GB774990A GB20246/55A GB2024655A GB774990A GB 774990 A GB774990 A GB 774990A GB 20246/55 A GB20246/55 A GB 20246/55A GB 2024655 A GB2024655 A GB 2024655A GB 774990 A GB774990 A GB 774990A
Authority
GB
United Kingdom
Prior art keywords
homologues
compounds
synthesis
methyl
relating
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
GB20246/55A
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.)
Eli Lilly and Co
Original Assignee
Eli Lilly and Co
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 Eli Lilly and Co filed Critical Eli Lilly and Co
Publication of GB774990A publication Critical patent/GB774990A/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

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 octahydro-indolo-quinolines (ergolenes) of the formula <FORM:0774990/IV(b)/1> where 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 from (a) the corresponding 9-hydroxy compounds by treatment with boron trifluoride and liquid hydrogen cyanide, or (b) the corresponding 9-chloro or 9-bromo compounds and a metal cyanide. When the 9-hydroxy compound lacks the 4-acyl group this may be introduced (by means of the acid anhydride) before or after the cyano group. The starting materials are described in Specifications 774,988 and 774,989. Examples are given of the preparation of 4-acetyl-9-cyano-7-methyl-10-ergolene by both methods; the hydrochloride is described. Starting materials are mentioned in which R is methyl or phenyl and R1 is methyl, ethyl or n-heptyl. The products are intermediates in the synthesis of lysergic acid and its homologues.
GB20246/55A 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 Expired GB774990A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US774990XA 1954-09-27 1954-09-27

Publications (1)

Publication Number Publication Date
GB774990A true GB774990A (en) 1957-05-15

Family

ID=22138434

Family Applications (1)

Application Number Title Priority Date Filing Date
GB20246/55A Expired GB774990A (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) GB774990A (en)

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