GB2028310A - Acetylsalicylic acid derivative - Google Patents
Acetylsalicylic acid derivative Download PDFInfo
- Publication number
- GB2028310A GB2028310A GB7922175A GB7922175A GB2028310A GB 2028310 A GB2028310 A GB 2028310A GB 7922175 A GB7922175 A GB 7922175A GB 7922175 A GB7922175 A GB 7922175A GB 2028310 A GB2028310 A GB 2028310A
- Authority
- GB
- United Kingdom
- Prior art keywords
- zinc
- acetyl
- salicyclic acid
- acetylsalicylic acid
- acid derivative
- 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.)
- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/14—Acetic acid esters of monohydroxylic compounds
- C07C69/145—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols
- C07C69/157—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
An acetylsalicylic acid-zinc chelate exhibits improved anti-inflammatory properties with reduced irritation of the gastro-intestinal mucous membrane. The acetylsalicylic acid-zinc chelate is produced by reacting acetylsalicylic acid with zinc hydroxide or sulphate in the presence of a weak base.
Description
SPECIFICATION
An acetyl salicyclic acid derivative and a method of obtaining the same
This invention relates to an acetyl salicylic acid derivative and to a m-ethod of obtaining the same.
Acetyl salicylic acid taken orally by human subjects has remarkable anti-inflammatory effects, though-it has the disadvantage of producing a recurring irritation of the gastro-intestinal mucous membrane.
Zinc salts absorbed orally by human subjects (P.S. SIMKEN, Oral zinc sulphate in rheumatoid arthritis, The Lancet, 11th September 1976) have notable beneficial effects in the treatment of patients suffering from active rheumatoid arthritis.
It has now been found that an acetyl salicylic acid-zinc chelate not only combines certain properties of both compounds but also beneficially increases certain properties of each compound. Thus, for example, the irritating effect of aspirin upon the gastro-intestinal mucous membrane is reduced while its antiinflammatory effect is increased and in addition, as a result of the chelating effect of the acetyl salicylic acid, the gastro-intestinal absorption of the zinc is increased.
Accordingly, the invention resides in an acetyl salicyclic acid-zinc chelate.
In a further aspect, the invention resides in a process for obtaining an acetyl salicylic acid derivative, comprising the step of reacting acetyl salicylic acid and a zinc derivative such that the reaction product is an acetyl salicyclic acid-zinc chelate.
The acetyl sajicyclic acid zinc chelate of the invention has the formula C18H1408Zn but, as discussed below, is not a simple zinc salt.
Comparative tests performed on freshly prepared aqueous solutions having a concentration of 10-3M. of acetyl salicylic acid and the compound of the invention produced the following results:
The UV spectrum of the aqueous solution of acetyl salicyclic acid had a maximum absorption rate at 280 mil whereas the compound of the present invention exhibited only 50% of this absorption rate at the same wave length.
The spectrum of acetyl salicyclic acid exhibits at minimal 260 my whereas the compound of the invention exhibits a shoulder and approximately twice the absorption of acetyl salicyclic acid. It is therefore assumed that the compound of the invention is undissociated in aqueous solution, which suggest an interaction within the acetyl salicyclic acid-zinc compound.
The solid state spectrum of acetyl salicyclic acid between 370 and 210 my using Mg0 as a control exhibits a shoulder at 320 my and a wide band with a fairly marked maximum at 294 m. The acetyl salicyclic acid-zinc compound of the invention shows a maximum at 335 my and a further marked rise at 265 m. This indicates the presence of interactions differing from those to be expected from a simple substitution of hydrogen- by zinc in the acetyl salicyclic acid molecule. This observation is mainly based on the fact that the maximum of 345 mF corresponds to a weak charge transfer absorption between the metal and acetyl salicyclic acid which in principle, cannot be attributed to the oxygen metal bond in a salt.
Comparing the infra-red spectrum of acetyl salicyclic acid and the compound of the invention, it is found that the spectrum of acetyl salicyclic acid-zinc compound does not exhibit the following bands present in the acetyl salicyclic acid spectrum:
The band representing CO in the group -COOH at around 1680 cm-1.
The band representing CO in the group -COOH at around 1300 cm~1.
The band representing C-OH in the group -COOH at around 3000-2500 cm-l.
Taking into account the results previously outlined, itis considered that there is a great-COO-Zn interaction than if the compound were a simple salt, the compound thus obtained being considered as a chelate, with the following structure:
The invention will now be more particularly described with reference to the following Examples.
Example 1
50 g of acetyl salicyclic acid are dissolved in a solution of 24.3 g of sodium bicarbonate in 300 ml of water.
40 g of hydrated zinc sulphate dissolved in 100 ml of water are added slowly to this solution, while the solution is continuously stirred. A white precipitate is thereby formed, which is then separated by filtration, washed with water, and dried at 400C. The product thus obtained has the formula C18H1408Zn and has a melting point of 115cm.
Example 2
50 g of acetyl salicyclic acid are added in small quantities to a solution of 24.3 g of sodium bicarbonate in 300 ml of water, the solution being stirred during the addition. 14 g of freshly prepared zinc hydroxide are added to the solution with the stirring being continued for one hour. The resultant mixture is then filtered and the residue on the filter is subsequently dried at 40"C.
In the above Examples, it is to be appreciated that the aqueous sodium bicarbonate solution is acting as a week base.
Claims (8)
1. An acetyl salicyclic acid-zinc chelate.
2. A compound as claimed in Claim 1 and having the formula:
3. A process for obtaining an acetyl salicyclic acid derivative, comprising the step of reacting acetyl salicyclic acid and a zinc derivative such that the reaction product is an acetyl salicyclic acid-zinc chelate.
4. A process as claimed in Claim 3, wherein the reaction is performed in the presence of a weak base.
5. A process as claimed in Claim 4, wherein the weak base is an aqueous solution of sodium bicarbonate.
6. A process as claimed in any one of Claims 3 to 5, wherein the zinc derivative is zinc sulphate or hydroxide.
7. A process for obtaining an acetyl salicyclic acid derivative substantially as hereinbefore described with reference to the Examples.
8. An acetyl salicylic acid derivative obtained by a process as claimed in any one of Claims 3 to 7.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES471130A ES471130A1 (en) | 1978-06-26 | 1978-06-26 | Acetylsalicylic acid derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2028310A true GB2028310A (en) | 1980-03-05 |
Family
ID=8476359
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7922175A Withdrawn GB2028310A (en) | 1978-06-26 | 1979-06-26 | Acetylsalicylic acid derivative |
Country Status (4)
| Country | Link |
|---|---|
| DE (1) | DE2925718A1 (en) |
| ES (1) | ES471130A1 (en) |
| FR (1) | FR2429773A1 (en) |
| GB (1) | GB2028310A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110872227A (en) * | 2019-12-09 | 2020-03-10 | 荆州市天翼精细化工开发有限公司 | Preparation method of aspirin zinc |
-
1978
- 1978-06-26 ES ES471130A patent/ES471130A1/en not_active Expired
-
1979
- 1979-06-25 FR FR7916258A patent/FR2429773A1/en not_active Withdrawn
- 1979-06-26 DE DE19792925718 patent/DE2925718A1/en not_active Withdrawn
- 1979-06-26 GB GB7922175A patent/GB2028310A/en not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110872227A (en) * | 2019-12-09 | 2020-03-10 | 荆州市天翼精细化工开发有限公司 | Preparation method of aspirin zinc |
Also Published As
| Publication number | Publication date |
|---|---|
| ES471130A1 (en) | 1979-01-16 |
| FR2429773A1 (en) | 1980-01-25 |
| DE2925718A1 (en) | 1980-01-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |