GB900572A - Funtumia alkaloids - Google Patents
Funtumia alkaloidsInfo
- Publication number
- GB900572A GB900572A GB30862/58A GB3086258A GB900572A GB 900572 A GB900572 A GB 900572A GB 30862/58 A GB30862/58 A GB 30862/58A GB 3086258 A GB3086258 A GB 3086258A GB 900572 A GB900572 A GB 900572A
- Authority
- GB
- United Kingdom
- Prior art keywords
- funtumine
- funtumidine
- acid
- amino
- plants
- 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
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/24—Apocynaceae (Dogbane family), e.g. plumeria or periwinkle
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G5/00—Alkaloids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medical Informatics (AREA)
- Epidemiology (AREA)
- Biotechnology (AREA)
- Botany (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Pharmacology & Pharmacy (AREA)
- Alternative & Traditional Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
900,572. Funtumia alkaloids and steroids. OLETTA S.A. Sept. 26, 1958 [Sept. 27, 1957; Feb. 22, 1958; June 4, 1958], No. 30862/58. Class 2(3). The invention comprises 3α-amino-allopregnan-20-ol (funtumidine) and 3α-aminoallopregnan-20-one (funtumine) and their acidadditions salts; and a process for their isolation from plants of the genus Funtumia which comprises extracting parts of the plants or whole plants with a water-immiscible solvent, acidifying the extract and if necessary removing any crystals which form, rendering the acid solution alkaline to precipitate a solid and/or washing with aqueous alkali any removed crystals, separating the solid from the solution and/or washings and extracting it with an organic solvent, evaporating the extract to dryness, dissolving the residue in benzene and separating funtumine from funtumidine by chromatographic or ion-exchange methods. (It is stated that after removal of these steroids further elution of the chromatographic column yields a sapogenin of m.p. 260‹C. which is recrystallizable from methanol or ethyl acetate, positive to Liebermann's reaction, contains no nitrogen and shows in the infra-red spectrum an OH band at about 3mÁ and a CO band at about 6mÁ). The plants, which are preferably of the species F.latifolia, F.Africana or F.elastica, may first be crushed, washed with pstroleum ether and left for a number of hours in contact with water or alkali before the initial extraction. The invention also comprises (1) the process of oxidizing funtumidine to funtumine with chromic acid in acetic acid; (2) the process of reducing funtumine to funtumidine, advantageously with sodium in alcohol; (3) the process of producing 20-epifuntumidine (3α-amino-20#-hydroxy-allopregnane) by dissolving funtumine in methanol, adding potassium or sodium borohydride, agitating the mixture, diluting the solution, extracting with an immiscible solvent, and washing, drying and evaporating the extract; (4) a process for the production of allopregnane-3,20-dione which comprises reacting funtumine either with nitrous acid in acetic, tartaric or hydrochloric acid to give a secondary alcohol and oxidizing this with chromic acid in acetic acid or pyridine or by the Oppenauer method, or with hypochlorous acid in ether to form the corresponding chloramine, dechlorinating this with sodium ethoxide and hydrolysing the ketimine with sulphuric acid; (5) a process for producing 3α- amino-androstan-17#-ol by treating funtumine with a peracid and hydrolysing the product (which, when peracetic acid is used, is 17#- acetoxy-3α-amino-androstane); and (6) a process for producing. 3α-amino-androstan-17-one by oxidizing the product of (5). Examples describe the processes of (1), (2) and (3), the second process detailed under (4), and the preparation of 20α- or 20#-hydroxy-allopregnan-3-one from funtumidine or 20-epi-funtumidine by this lastnamed process. The hydrochlorides of funtumine and funtumidine, which are stated to have anaesthetic and antipyretic properties, may be dissolved in aqueous propylene glycol or other solvents such as methyl acetamide to give injection solutions, or may be made up into tablets, an example of which is provided.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE443246 | 1957-09-27 | ||
BE561173T | 1957-09-27 | ||
LU35817 | 1958-02-22 | ||
LU36147 | 1958-06-04 | ||
DES60064A DE1185183B (en) | 1957-09-27 | 1958-09-27 | Process for the extraction and production of cardiac or hormonally active compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
GB900572A true GB900572A (en) | 1962-07-11 |
Family
ID=27507596
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB30862/58A Expired GB900572A (en) | 1957-09-27 | 1958-09-26 | Funtumia alkaloids |
GB5360/60A Expired GB948769A (en) | 1957-09-27 | 1960-02-15 | New alkaloids of the funtumia species and processes for obtaining same |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB5360/60A Expired GB948769A (en) | 1957-09-27 | 1960-02-15 | New alkaloids of the funtumia species and processes for obtaining same |
Country Status (6)
Country | Link |
---|---|
BE (1) | BE561173A (en) |
CH (3) | CH370773A (en) |
GB (2) | GB900572A (en) |
LU (2) | LU36147A1 (en) |
NL (1) | NL231702A (en) |
OA (1) | OA01015A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011127465A3 (en) * | 2010-04-09 | 2012-03-15 | The Research Foundation Of The State University Of New York | Ship inhibitors and uses thereof |
US10702538B2 (en) | 2014-06-17 | 2020-07-07 | The Research Foundation For The State University Of New York | Ship inhibition to induce activation of natural killer cells |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2494696A1 (en) * | 1980-11-21 | 1982-05-28 | Roussel Uclaf | NOVEL PROCESS FOR THE PREPARATION OF 3-AMINO STEROIDS AND THEIR SALTS |
FR2494697A1 (en) * | 1980-11-21 | 1982-05-28 | Roussel Uclaf | NOVEL 3-AMINO-STEROID DERIVATIVES, THEIR SALTS, PROCESS AND PREPARATION INTERMEDIATES, MEDICAMENT APPLICATION AND COMPOSITIONS COMPRISING THE SAME |
-
0
- LU LU35817D patent/LU35817A1/xx unknown
- NL NL231702D patent/NL231702A/xx unknown
- LU LU36147D patent/LU36147A1/xx unknown
-
1957
- 1957-09-27 BE BE561173D patent/BE561173A/xx not_active Expired
-
1958
- 1958-09-25 CH CH6436458A patent/CH370773A/en unknown
- 1958-09-25 CH CH1173261A patent/CH369756A/en unknown
- 1958-09-25 CH CH1173361A patent/CH405305A/en unknown
- 1958-09-26 GB GB30862/58A patent/GB900572A/en not_active Expired
-
1960
- 1960-02-15 GB GB5360/60A patent/GB948769A/en not_active Expired
-
1964
- 1964-12-29 OA OA51120A patent/OA01015A/en unknown
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011127465A3 (en) * | 2010-04-09 | 2012-03-15 | The Research Foundation Of The State University Of New York | Ship inhibitors and uses thereof |
US9447139B2 (en) | 2010-04-09 | 2016-09-20 | The Research Foundation Of State University Of New York | Ship inhibitors and uses thereof |
US11319336B2 (en) | 2010-04-09 | 2022-05-03 | The Research Foundation For The State University Of New York | Ship inhibitors and uses thereof |
US10702538B2 (en) | 2014-06-17 | 2020-07-07 | The Research Foundation For The State University Of New York | Ship inhibition to induce activation of natural killer cells |
Also Published As
Publication number | Publication date |
---|---|
CH405305A (en) | 1966-01-15 |
LU35817A1 (en) | |
CH369756A (en) | 1963-06-15 |
GB948769A (en) | 1964-02-05 |
CH370773A (en) | 1963-07-31 |
LU36147A1 (en) | |
NL231702A (en) | |
BE561173A (en) | 1960-05-20 |
OA01015A (en) | 1968-08-07 |
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