GB789870A - Alkaloid derivatives - Google Patents
Alkaloid derivativesInfo
- 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
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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (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 (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.
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)
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 |
-
1956
- 1956-10-09 GB GB30772/56A patent/GB789870A/en not_active Expired
Cited By (9)
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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