GB2145078A - New salt of oxochromencarboxylic acid - Google Patents
New salt of oxochromencarboxylic acid Download PDFInfo
- Publication number
- GB2145078A GB2145078A GB08322204A GB8322204A GB2145078A GB 2145078 A GB2145078 A GB 2145078A GB 08322204 A GB08322204 A GB 08322204A GB 8322204 A GB8322204 A GB 8322204A GB 2145078 A GB2145078 A GB 2145078A
- Authority
- GB
- United Kingdom
- Prior art keywords
- zinc
- chromoglycate
- acid
- oxochromencarboxylic
- salt
- 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- Withdrawn
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/24—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Zinc chromoglycate of the formula: <IMAGE> has an ulcer-inhibiting activity.
Description
SPECIFICATION
New salt of oxochromencarboxylic acid
The present invention relates to a new derivative of an oxochromencarboxylic acid, and more particularly to the zinc salt of 5. 5'-((2-hidrnxytrimethylene)dioxy)bis(4-oxo-4H. 1 -benzopiran-2- carboxylic) acid which we shall call zinc chromoglycate, having the formula:
Zinc chromoglycate, to which the present invention relates, has a number of advantages with respect to other known salts of alkaline metals.
The protective action of zinc on the gastric mucus has been described in the literature (1).
The protective effect of zinc chromoglycate and disodium chromoglycate on ulcers induced experimentally in rats has been studied.
In order to induce the ulcers the method described by R.J. Levine (2), based on the production of stress by immobilization and low temperatures, was followed in principle.
The test was carried out on three groups of ten animals which were given respectively and orally water (control), disodium chromoglycate (276 mg/kg) and zinc chromoglycate (300 mg/Kg). Table I shows the values of inhibition of the ulcers and the ulcerogenic rates (%).
TABLE I
Ulcerogenic rate and percentage of inhibition of the stress-induced ulcers of disodium and zinc chromoglycate. The values are affected by the mean deviation.
Control Zinc Disodium
Chromoglycate Chromoglycate
100 34.9+8.8t "+ 14.0 (65.1%) (23.8%)
t p(o.o7 Disodium chromoglycate shows a slight decrease in the ulcerogenic rate which is not statistically significant with respect to the control (distribution of t); the zinc chromoglycate shows a great inhibiting effect of the ulcerogenic rate, which effect is statistically significant (p < 0.05) These results show that zinc chromoglycate has an inhibiting effect on gastric ulcers which the sodium salt does not have.
A further test was carried out in which, after subjecting the rats to stress, the stomach was scraped in order to obtain gastric mucus in which hexosamines were determined according to the Elson method modified by Boas (3), total proteins and mucoproteins being obtained according to the Maurowitz method (4) and Minzler method (5). The values obtained are shown in Table II.
TABLE 11 Values of the secretion parameters of the gastric mucus in rats. Treated with disodium chromoglycate and zinc chromoglycate. The values are affected by the mean deviation.
mg total muco- hexosamines
mucus proteins proteins
Control 57.3+ 3.7 4.6±0.3 2.2+0.1 54.3-+ 3.2
Zinc 78.5+4.7 5.5+0.2 3.0t0.1 61.1+1.4 chromoglycate
Disodium 53.3+4.2 4.2+0.2 2.2+0.1 46.0-1.5 chromoglycate f p < 0.05 mg/ml mg/ml S /ml
( < 0.04 As can be seen, zinc chromoglycate produces an increase in mucus, total proteins, mucoproteins and hexosamines which are statistically significant with respect to the control (distribution t. In the case of disodium chromoglycate a significant difference is only shown by the hexosamines in which a decrease may be seen.
It may be concluded from these results that zinc chromoglycate has a protecting effect on the gastric mucus which is greater than that of disodium chromoglycate.
The method according to the present invention is characterized in that the chromoglycic acid itself, or any soluble salt thereof, is made to react with a zinc salt, zinc oxide or hydroxide in stoichiometric amounts, or with a slight excess of the zinc compound, in a polar solvent--or mixtures of solvents preferably water.
The temperature of the reaction may range from ambient temperature to the boiling temperature of the solvent; generally ambient temperature is used and constant stirring is maintained until the precipitation of the zinc chromoglycate is complete. The zinc chromoglycate is obtained by filtration, centrifugation or evaporation of the solvent.
In order to facilitate the explanation, some examples of the manner in which the method according to the invention is carried out will be described hereinafter by way of non-limiting illustration thereof.
EXAMPLE I
46.8 g (0.1 mol) of chromoglycic acid are dissolved in 1 I water; 11.0 g of basic zinc carbonate (0.02 mols) are added and stirred in well; the release of gas is observed; when this has finished the temperature is increased to 40"C for one hour. The resultant white precipitate of zinc chromoglycate is allowed to cool, is filtered, washed with water in order to eliminate carbonates and is dried in a vacuum oven at 150"C. 50.5 g of zinc chromoglycate are obtained.
Analysis: calculated for C23H,401,Zn: %C 51.95% H 2.65; % Zn 12.29. Obtained: %C 51.7; %H 2.8; %Zn 12.1.
Infrared (KBr):2800-3600 (wide band), 1600 (s), 1460 (s), 1390 (m), 1340 (s), 1290 (s),
1250 (m), 1110(m), 1060 (m), 1040 (m), 940 (m) . . . cm-'.
EXAMPLE 2
10.2 g of disodium chromoglycate are dissolved in 250 ml water. A solution of 4.7 g of zinc acetate in 100 ml water is added with vigorous stirring. The stirring is continued for 2 hours at ambient temperature. The white precipitate is filtered in a Gooch filter, washed with water until there is no acetate reaction, and is dried -in a vacuum oven at 1 50,C. 9.6 g zinc chromoglycate are obtained having similar characteristics to those of the zinc chromoglycate obtained in the previous example.
Claims (3)
1. The zinc salt of 5, 5'-(2-hydrnxytrimethylene)dioxyJbis(4-oxo4H-1 -benzopiran-2-carboxy- lic) acid, also referred to as zinc chromoglycate, having the formula:
2. A method for preparing zinc chromoglycate, characterized in that zinc oxide or hydroxide of a zinc salt is reacted with 5,5'-[(2-hydroxytrimethylene)dioxy]bis(4-oxo-4H-1-benzopiran-2- carboxylic) acid or with a soluble salt thereof.
3. A method according to claim 2, wherein the reactants are in approximately stoichiometric porportions, the reaction taking place in a polar solvent at a temperature of the solvent.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES523758A ES8500281A1 (en) | 1983-07-01 | 1983-07-01 | New salt of oxochromencarboxylic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB8322204D0 GB8322204D0 (en) | 1983-09-21 |
| GB2145078A true GB2145078A (en) | 1985-03-20 |
Family
ID=8485947
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08322204A Withdrawn GB2145078A (en) | 1983-07-01 | 1983-08-18 | New salt of oxochromencarboxylic acid |
Country Status (2)
| Country | Link |
|---|---|
| ES (1) | ES8500281A1 (en) |
| GB (1) | GB2145078A (en) |
-
1983
- 1983-07-01 ES ES523758A patent/ES8500281A1/en not_active Expired
- 1983-08-18 GB GB08322204A patent/GB2145078A/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| ES523758A0 (en) | 1984-11-01 |
| GB8322204D0 (en) | 1983-09-21 |
| ES8500281A1 (en) | 1984-11-01 |
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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) |