GB2051795A - Process for the preparation of a solution of trichinoyl, its radicals, polymers and chain fragments, also as radicals, with novel therapeutic properties - Google Patents
Process for the preparation of a solution of trichinoyl, its radicals, polymers and chain fragments, also as radicals, with novel therapeutic properties Download PDFInfo
- Publication number
- GB2051795A GB2051795A GB8017369A GB8017369A GB2051795A GB 2051795 A GB2051795 A GB 2051795A GB 8017369 A GB8017369 A GB 8017369A GB 8017369 A GB8017369 A GB 8017369A GB 2051795 A GB2051795 A GB 2051795A
- Authority
- GB
- United Kingdom
- Prior art keywords
- barium
- solution
- radicals
- trichinoyl
- polymers
- 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.)
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/298—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with manganese derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/64—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of functional groups containing oxygen only in singly bound form
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Catalysts (AREA)
Abstract
The invention relates to a process for the preparation of a solution of trichinoyl, its radicals, polymers and chain fragments, also as radicals, and a medicament prepared according to this process, whereby the compounds rhodizonic acid and trichinoyl and their polymers preparable in accordance with the invention form an oxidoreduction equilibrium if they are in correct proportions with respect to one another. They can also assume the character of free radicals and can therefore decouple electron transfers blocked in the breathing chain of living cells and/or in the intermediary metabolism and can be used for eliminating illnesses or for aiding the cure of patients.
Description
SPECIFICATION
Process for the preparation of a solution of trichinoyl, its radicals, polymers and chain fragments, also as radicals, with novel therapeutic properties
The invention relates to a process for the preparation of a solution of trichinoyl, its radicals, polymers and chain fragments, also as radicals, with novel therapeutic properties.
According to the process of the invention an aqueous solution of inositol is chlorinated in the presence of light at temperature between 40 and 60 C, the reaction products obtained are reacted with barium chloride to barium rhodizonate of formula
and/or to the polymer of the barium rhodizonate of formula
and the barium rhodizonate and its polymers are converted by means of sulphuric acid into rhodizonic acid of formula
and/or into polyrhodizonic acid of formula
and then the rhodizonic acid and its polymers are converted with manganese dioxide into trichinoyl of formula
and/or into the trichinoyl polymer of formula
The invention also relates to a process wherein an aqueous solution of inositol is chlorinated in the presence of light at a temperature between 40 and 60 C, the reaction solution (RL) obtained is filtered, the residue (RI) is mixed with a sodium hydrogen carbonate solution and barium chloride and a precipitate (R4) is obtained with high molecular weight polymerised barium rhodizonate (R4), the filtrate of the reaction solution (RL) is neutralised and the low molecular weight polymerised barium salt compounds (R2) are precipitated with a little barium chloride, barium chloride is again added to the solution filtered from the precipitated low molecular weight polymerised barium rhodizonates (R2) and sulphuric acid is added to the filtered precipitate (R3) (barium rhodizonate) for bonding the barium and for its precipitation as barium sulphate, the barium sulphate is filtered off and a rhodizonic acid-containing solution (II) is obtained and/or the low molecular weight polymerised barium salt compounds (R2) are mixed with dilute sulphuric acid for the purpose of precipitating the barium sulphate, the barium sulphate is filtered off and a low molecular weight polymerised rhodizonic acid-containing solution (III) is obtained, and/orthe residue (R4) is mixed with dilute sulphuric acid for the purpose of precipitating the barium sulphate, the barium sulphate is filtered and high molecular weight polymerised rhodizonic acid-containing solution (IV) is obtained, after which the rhodizonic acid of solution (II) and/or its polymer of solutions (III, IV) is mixed with manganese dioxide to give trichinoyl and/or its polymer.
According to the invention in order to obtain trichinoyl radicals the barium salts of residues (R2 to R4) a) are reacted with aqueous catalytic quantities of nickel, cobalt or molybdenum sulphate or iron, copper
and zinc sulphate and concentrated sulphuric acid or b) with free radical-concentrated sulphuric acid to semitrichinoyl of formula
and/orto the semitrichinoyl polymer of formula
and by ring cleavage to compounds containing chain carbonyl group radicals
It has surprisingly been found that the compounds rhodizonic acid and trichinoyl and their polymers preparable according to the invention form an oxido-reduction equilibrium if they are in correct proportions with respect to one another.In addition, under special conditions they can assume the character of free radicals and therefore decouple electron transfers blocked in the breathing chain of living cells and/or in the intermediary metabolism and can serve to eliminate illnesses orto assist the cure of patients. The solutions obtained of trichinoyl, its radicals, polymers and chain fragments, also in the form of radicals, have a particularly high stability in dilute solution.
The medicament has a content of trichinoyl, semitrichinoyl and series-like carbonyl groups as poly-ketones with at least 4 C-atoms in the chain and as radicals thereof and is used for the oxidative decoupling of ferment blockades in the area of the breathing chain and the energy-producing metabolism, as well as in the cell division region.
The following examples serve to illustrate the process of the invention:
Example 1
Chlorine gas is introduced into a 1% aqueous solution of inositol at a temperature of 40 to 60 C, accompanied by simultaneous exposure by means of a day light lamp and under the action of bright sunlight and this is continued until the reaction mixture temperature has returned to ambient temperature. The reaction solution is stored in the dark until gas production is ended and a black precipitate (residue Ri) has formed and is then filtered.
The residue R1 is mixed with a sodium hydrogen carbonate solution and with barium chloride. The precipitate R4 obtained in this way contains high molecular weight polymerised barium rhodizonate.
The filtrate of the reaction solution is also mixed with a sodium hydrogen carbonate solution and with a little barium chloride. The low molecular weight polymerised barium salt compounds are precipitated as precipitate R2. Barium chloride is again added to the solution filtered from precipitate R2 and sulphuric acid is added to the filtered precipitate R3 (barium rhodizonate) for bonding the barium and for its precipitation as barium sulphate. The barium sulphate is filtered off and the filtrate is solution 11. The clear solution 11 contains rhodizonic acid, showing the positive ketoaldehyde sample.
If the low molecular weight polymerised barium rhodizonate is to be used, the precipitate R2 is mixed with dilute sulphuric acid in a slight excess. Barium sulphate is precipitated and filtered off. The filtrate (solution lil) reacts weakly acid and contains low molecular weight rhodizonic acid polymers.
If the high molecular weight polymerised barium rhodizonate is to be used, the residue R4 is mixed with dilute sulphuric acid and the precipitated barium sulphate is filtered off. The filtrate (solution IV) contains high molecular weight rhodizonic acid polymers.
In order to convert the rhodizonic acid from solution 11 and its polymers from solution Ill and IV into trichinoyl and its polymers solutions II to IV are mixed with manganese dioxide, whose quantity is fixed in such a way that the trichinoyl and/or its polymers formed is not modified or destroyed.
The manganese oxides deposited on the bottom of the reaction vessel and are filtered off. The filtrate from solution II mixed with manganese dioxide contains trichinoyl Il-T and the filtrates from solutions Ill and lV mixed with manganese dioxide contain trichinoyl polymers Ill-T and IV-T.
Example 2
In the preparation of trichinoyl radicals the procedure of Example 1 is adopted when converting the barium rhodizonate and its polymers into rhodizonic acid and its polymers and specifically in the following manner: a) By adding aqueous catalytic quantities of nickel, cobalt or molybdenum sulphate and iron, copper and
zinc sulphate to the barium salts in residues R2 to R4 prior to the addition of concentrated sulphuric acid
weak and relatively unstable radical films are obtained in accordance with the following reaction
diagrams.
Rhodizonic acid Semitrichinoyl Trichinoyl
The solutions are correspondingly designated Il-ST to IV-ST (= semitrichinoyl).
b) However, it is also possible to use a free radical-concentrated sulphuric acid and consequently stimulate
the strengthened formation of stable trichinoyl radicals (semitrichinoyl) by adopting the following
procedure:
Mixture 1: acetaldehyde and ethyl alcohol are mixed together : 5 parts).
Mixture 2: acetaldehydeand ethyl ether are mixed together (1: 8 parts).
Mixture 3: the parts of mixtures 1 and 2 are added to concentrated sulphuric acid and boiled for a few
minutes (1:1:10 parts).
After cooling it is possible to detect in this sulphuric acid 1014 free radicals per cm by electron spin resonance absorption measurements (Bruker ER 400 spectrometer). If this free radical-concentrated sulphuric acid is now used in converting the barium rhodizonates and their polymers into rhodizonic acid and its polymers according to Examples 1 and 2 are used then carbonyl group radicals are formed, also on the rhodizonic acid and called semitrichinoyl, and on its fragments and which occur as chain polyketone radicals with novel therapeutic actions in illnesses with electron transfer or ferment blockades in the intermediary metabolism or in the breathing chain.
The solutions obtained according to Example 2b with the stable free carbonyl group radicals on the trichinoyl and its fragments as polyketone radicals are called IIST CG:IVST CG (ST-CG = semitrichinoyl carbonyl group radicals).
Example 3
Solution Il-T to IV-T obtained according to Example 1 with trichinoyl and its polymers are brought together with solution II (contains rhodizonic acid), solution Ill or IV either individually or mixed. The solutions obtained are called V to XII. All the solutions have vigorously and directly in the cold the reduction sample with Fehling's solution and Benedict's solution. A quantitative examination of solution V (=ll+lI-T) in connection with its reducing power relative to Fehling' solution revealed that it contains approximately 1% of reducing substances.
Example 4
Solution Il-ST obtained according to Example 2 with the trichinoyl and its radical is measured in the
UV-spectrometer and has UV-absorption maxima 1) at X max. 362 nm (rhodizonic acid with weak acid pH) 2) at X max. 335 nm (semitrichinoyl) 3) at X max. 266 nm (trichinoyl).
ESR measurement are disturbed by traces of manganese, so that NMR spectra are also recorded.
Example 5
As the molecular weights of trichinoyl and its polymer are moderately high it is advantageous if the content of oxidizing and/or reducing substances isincreased by substances with low molecular weights, such as glyoxal and methyl glyoxal. For this purpose the solutions of Examples 1 and 2 or 1- ml of solution V (=II+II-T) from Example 3 are diluted to 10 ml with sterile distilled water. Each cubic centimetre of solution then contains about 1 mg of reducing substances. If 1 ml, e.g. of solution V is diluted with one litre of sterile distilled water, each cubic centimetre of solution contains about one microgram of reducing substances.
This solution is called solution XV and the same applies for other solutions.
One litre e.g of solution XV is mixed with 1 mg of glyoxal and 1 mg of methyl glyoxal, as well às 1 mg of p-benzonquinone. This solution XVI offers very favourable steric possibilities for dehydration.
Example 6
It has been found that the cations of certain metals in their higher oxidation stages aid the oxidising and/or reducing forces of carbonyl compounds in the tissue metabolism, there being an electron transfer from the substrate to the carbonyl and from the carbonyl to an electron acceptor on the way to the oxygen. For this purpose e.g. one litre of solution XVI is mixed with one microgram of nickel, cobalt, manganese or molybdenum sulphate and 1 mg of iron, copper or zinc sulphate, the iron, copper or zinc being present in the high oxidation stages. This solution is called solution XVII. The same also applies to the other solutions.
Example 7
Production procedure for ampoule preparations.
The solutions of Examples 1 and/or 2, as well as solutions Vto XIV or XV (optionally as a concentrate) are passed through a sintered bacterial filter made from Pyrex glass and under aseptic conditions are placed in stock ampoules, optionally as a concentrate.
The corresponding active substances are stored in sealed ampoules in the ampoule filling section. It must be very carefully ensured that the active substances are not exposed to atmospheric oxygen and are stored for long periods accompanied by the exclusion of light. It must be ensured that only glass types of commercial grade la are used for storage purposes.
Operating instructions.
After removing the substance from the stock ampoule for the production the concentrate solution is transferred into a new ampoule, which is then sealed for further storage. This is carried out by placing the sterilised parts in a large, round, cylindrical glass vessel which has already been sterilised.
1) an open emptyampoule 2) an Erlenmeyer flask of volume 100 ml 3) a 10 ml injection syringe and cannula 4) the ampoule solution with the concentrate.
The glass vessel is now sealed with a lid and via a hose opening is gassed with sterile nitrogen for 15 minutes. The lid is then carefully opened and the ampoule solution with the concentrate broken open, after which all the solution is removed from the ampoule by means of the syringe and the ampoule is discarded.
Part of the concentrate is now removed in accordance with the mixture quantity and injected into the
Erlenmeyer flask,
The remainder is returned to the open ampoule, ensuring that the concentrate only comes into contact with the bottom and wall of the ampoule to the extent that it is filled. For sealing purposes the stock ampoule is placed in the running ampoule filling and sealing machine which seals it under sterile conditions and with nitrogen gassing.
Erlenmeyer flask with the concentrate solution for the set of ampoules is left in the sterile nitrogen-gassed glass cylinder until the mixture is to be prepared.
The final solution is prepared according td the following procedure. The amount of bidistilled water necessaryforthe mixture is prepared in conventional manner and introduced into a sterilised refined steel tank with inlet and outlet. Part of the water is used to fill the Erlenmeyerflask with concentrate and this solution is now added to the final solution in the refined steel storage tank. Gassing with sterile nitrogen is now performed via-the outlet, so that there is a vigorous intermixing and at the same time an immediate displacement of the atmospheric oxygen. After about 15 minutes the solution is ready for use. The connections on the ampoule filling machine have also been under sterile conditions and laminar flow up to this time and can now be connected to the stock bottle. The filling process can now commence.
Claims (10)
1. A process for the preparation of a solution of trichinoyl, its radicals, polymers and chain fragments, also as radicals, with novel therapeutic properties, wherein an aqueous solution of inositol is chlorinated in the presence of light at a temperature between 40 and 60 C, the reaction products obtained are reacted with barium chloride to barium rhodizonate of formula
and/or to the polymer of the barium rhodizonate of formula
and the barium rhodizonate and its polymers are converted by means of sulphuric acid into rhodizonic acid of formula
and/or the polyrhodizonic acid of formula
and then the rhodizonic acid and its polymers are converted with manganese dioxide into trichinoyl of formula
and/or into the trichinoyl polymer of formula
2.A process according to claim 1, wherein an aqueous solution of inositol is chlorinated in the presence of light at a temperature between 40 and 60 C, the reaction solution (RL) obtained is filtered, the residue (R1 ) is mixed with a sodium hydrogen carbonate solution and barium chloride and a precipitate (R4) is obtained with high molecular weight polymerised barium rhodizonate (R4), the filtrate of the reaction solution (RL) is neutralised and the low molecular weight polymerised barium salt compounds (R2) are precipitated with a little barium chloride, barium chloride is again added to the solution filtered from the precipitated low molecular weight polymerised barium rhodizonate (R2) and sulphuric acid is added to the filtered precipitate (R3) (barium rhodizonate) for bonding the barium and for its precipitation as barium sulphate, the barium sulphate is filtered off and a rhodizonic acid-containing solution (II) is obtained and/or the low molecular weight polymerised barium salt compounds (R2) are mixed with dilute sulphuric acid for the pupose of precipitating the barium sulphate, the barium sulphate is filtered off and a low molecular weight polymerised rhodizonic acid-containing solution (Ill) is obtained, and/or the residue (R4) is mixed with dilute sulphuric acid for the purpose of precipitating the barium sulphate, the barium sulphate is filtered and a high molecular weight polymerised rhodizonic acid-containing solution (IV) is obtained, after which the rhodizonic acid of solution (II) and/or its polymer of solutions (Ill, IV) is mixed with manganese dioxide to give trichinoyl and/or its polymer.
3. A process according to claim 1, wherein the barium salts of residues (R2 to R4) a) are reacted with aqueous catalytic quantities of nickel, cobalt or molybdenum sulphate or iron, copper
and zinc sulphate and concentrated sulphuric acid or b) with free radical-concentrated sulphuric acid to semitrichinoyl of formula
and/or to the semitrichinoyl polymer of formula
and by ring cleavage to compounds containing chain carbonyl group radicals
4. A process according to claim 1, wherein the solutions containing the reaction product are mixed with substances such as glyozal and methyl glyoxal, whose molecular weight is lowerthan the molecular weight of trichinoyl.
5. A process according to claim 1, wherein nickel, cobalt, manganese or molybdenum sulphate and iron, copper or zinc sulphate are added in their higher oxidation stages to the reaction solutions,
6. A process according to claim 1, wherein the reaction solutions are mixed with p-benzoquinone.
7. A medicamentforthe oxidative decoupling of ferment blockades in the region ofthe breathing chain and the energy-producing tissure metabolism, as well as in the region of the cell division, wherein it contains trichinoyl, semitrichinoyl, their polymers and radicals and series-like carbonyl groups as polyketones with at least 4 C-atoms in the chain and their radicals.
8. A process forthe preparation of a solution oftrichinoyl, its radicals, polymers and chain fragments, also as radicals, substantially as hereinbefore described in the Examples.
9. A solution oftrichinoyl, its radicals, polymers and chain fragments, also as radicals, prepared by a process according to any of claims 1 to 6 and 8.
10. A medicament substantially as hereinbefore described with reference to Examples.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792922118 DE2922118A1 (en) | 1979-05-31 | 1979-05-31 | METHOD FOR PRODUCING A SOLUTION OF TRICHINOYL, ITS RADICALS, POLYMERS AND CHAIN-SHAPED PIECES, ALSO AS RADICALS, FOR MEDICINAL PRODUCTS WITH NEW THERAPEUTIC PROPERTIES |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2051795A true GB2051795A (en) | 1981-01-21 |
| GB2051795B GB2051795B (en) | 1983-11-23 |
Family
ID=6072121
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8017369A Expired GB2051795B (en) | 1979-05-31 | 1980-05-27 | Process for the preparation of a solution of trichinoyl its radicals polymers and chain fragments also as radicals withs novel therapeutic properties |
Country Status (6)
| Country | Link |
|---|---|
| CA (1) | CA1154443A (en) |
| CH (1) | CH669189A5 (en) |
| DE (1) | DE2922118A1 (en) |
| FR (2) | FR2472554B1 (en) |
| GB (1) | GB2051795B (en) |
| LU (1) | LU82493A1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0121275B1 (en) * | 1983-03-23 | 1988-06-01 | Organon Teknika B.V. | Macromolecular carbonyl groups-containing material suitable for use as sorbent for urea |
| US5391273A (en) * | 1993-04-16 | 1995-02-21 | Reinstorff; Dieter | Process for the preparation of a solution containing semitrichinoyl |
| WO2020031765A1 (en) * | 2018-08-09 | 2020-02-13 | 日本曹達株式会社 | Method for producing triquinoyl and/or hydrate thereof by electrolytic oxidation |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1618607A1 (en) * | 1966-06-21 | 1971-02-25 | Koch William Frederick Prof Dr | Process for the preparation of the new compound trichinoyl and its polymers |
-
1979
- 1979-05-31 DE DE19792922118 patent/DE2922118A1/en active Granted
-
1980
- 1980-05-23 CA CA000352619A patent/CA1154443A/en not_active Expired
- 1980-05-27 GB GB8017369A patent/GB2051795B/en not_active Expired
- 1980-05-29 CH CH419980A patent/CH669189A5/en not_active IP Right Cessation
- 1980-05-30 FR FR8012130A patent/FR2472554B1/en not_active Expired
- 1980-05-30 LU LU82493A patent/LU82493A1/en unknown
- 1980-11-07 FR FR8023898A patent/FR2469922A1/en active Granted
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0121275B1 (en) * | 1983-03-23 | 1988-06-01 | Organon Teknika B.V. | Macromolecular carbonyl groups-containing material suitable for use as sorbent for urea |
| US4897200A (en) * | 1983-03-23 | 1990-01-30 | Organon Teknika Bv | Macromolecular carbonyl groups containing material suitable for use as sorbent for nitrogen compounds |
| US5391273A (en) * | 1993-04-16 | 1995-02-21 | Reinstorff; Dieter | Process for the preparation of a solution containing semitrichinoyl |
| WO2020031765A1 (en) * | 2018-08-09 | 2020-02-13 | 日本曹達株式会社 | Method for producing triquinoyl and/or hydrate thereof by electrolytic oxidation |
Also Published As
| Publication number | Publication date |
|---|---|
| LU82493A1 (en) | 1980-10-08 |
| FR2469922B1 (en) | 1983-11-18 |
| FR2472554A1 (en) | 1981-07-03 |
| FR2469922A1 (en) | 1981-05-29 |
| DE2922118C2 (en) | 1992-12-03 |
| FR2472554B1 (en) | 1985-08-30 |
| CA1154443A (en) | 1983-09-27 |
| CH669189A5 (en) | 1989-02-28 |
| DE2922118A1 (en) | 1980-12-04 |
| GB2051795B (en) | 1983-11-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PE20 | Patent expired after termination of 20 years |
Effective date: 20000526 |