GB789870A - Alkaloid derivatives - Google Patents

Alkaloid derivatives

Info

Publication number
GB789870A
GB789870A GB30772/56A GB3077256A GB789870A GB 789870 A GB789870 A GB 789870A GB 30772/56 A GB30772/56 A GB 30772/56A GB 3077256 A GB3077256 A GB 3077256A GB 789870 A GB789870 A GB 789870A
Authority
GB
United Kingdom
Prior art keywords
ibogaine
voacangine
hydrochloride
demethyl
product
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
GB30772/56A
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.)
GOBEY LAB
Original Assignee
GOBEY LAB
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 GOBEY LAB filed Critical GOBEY LAB
Publication of GB789870A publication Critical patent/GB789870A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed systems contains four or more hetero rings
    • 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
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole

Abstract

The invention comprises (1) O-demethylibogaine (R = R1 = H) and its salts; (2) the production thereof from ibogaine (R = H, R1 = CH3) or voacangine (R = COOCH3, R1 = CH3) by heating with hydrobromic acid in acetic acid; (3) the production of ibogaine from voacangine by hydrolysis and heating the product to 30-50 DEG C. in an acid medium; (4) the toluene - p - sulphonic ester of O - demethylibogaine and salts thereof. <FORM:0789870/IV (b)/1> In the examples: (1) voacangine is heated with hydrobromic acid in acetic acid in an inert atmosphere and then evaporated to dryness; O-demethyl-ibogaine is isolated as its hydrochloride; (2) voacangine is boiled with potassium hydroxide in methanol and then acidified and evaporated to dryness at 35-45 DEG C.; ibogaine is obtained as hydrochloride which is converted to the free base; (3) ibogaine is treated as in (1) to give the same product; (4) O-demethyl-ibogaine is obtained from its hydrochloride; (5) O-demethyl-ibogaine is esterified with toluene-p-sulphonyl chloride in the presence of a tertiary base such as pyridine; the product is converted into its hydrochloride.
GB30772/56A 1955-10-10 1956-10-09 Alkaloid derivatives Expired GB789870A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR789870X 1955-10-10

Publications (1)

Publication Number Publication Date
GB789870A true GB789870A (en) 1958-01-29

Family

ID=9220342

Family Applications (1)

Application Number Title Priority Date Filing Date
GB30772/56A Expired GB789870A (en) 1955-10-10 1956-10-09 Alkaloid derivatives

Country Status (1)

Country Link
GB (1) GB789870A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103857397A (en) * 2011-09-15 2014-06-11 德莫科斯公司 Noribogaine salt ansolvates

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103857397A (en) * 2011-09-15 2014-06-11 德莫科斯公司 Noribogaine salt ansolvates
EP2755658A2 (en) * 2011-09-15 2014-07-23 DemeRx, Inc. Noribogaine salt ansolvates
EP2755658A4 (en) * 2011-09-15 2015-03-18 Demerx Inc Noribogaine salt ansolvates
US9040520B2 (en) 2011-09-15 2015-05-26 Demerx, Inc. Noribogaine salt ansolvates
CN105949193A (en) * 2011-09-15 2016-09-21 德莫科斯公司 Noribogaine salt ansolvates
US9617265B2 (en) 2011-09-15 2017-04-11 Demerx, Inc. Noribogaine salt ansolvates
AU2012308274B2 (en) * 2011-09-15 2017-08-17 Demerx, Inc. Noribogaine salt ansolvates
KR20200115661A (en) * 2011-09-15 2020-10-07 데메알엑스, 인크. Noribogaine salt ansolvates
KR102381792B1 (en) 2011-09-15 2022-04-01 데메알엑스, 인크. Noribogaine salt ansolvates

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