USRE11960E - Salicylic ether of quinin - Google Patents
Salicylic ether of quinin Download PDFInfo
- Publication number
- USRE11960E USRE11960E US RE11960 E USRE11960 E US RE11960E
- Authority
- US
- United States
- Prior art keywords
- quinin
- new
- salicylic ether
- salicylic
- ether
- Prior art date
Links
- GYCKQBWUSACYIF-UHFFFAOYSA-N Ethyl salicylate Chemical compound CCOC(=O)C1=CC=CC=C1O GYCKQBWUSACYIF-UHFFFAOYSA-N 0.000 title description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 8
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N Phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 229960000969 phenyl salicylate Drugs 0.000 description 6
- 229940032330 Sulfuric acid Drugs 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 4
- 229960001860 salicylate Drugs 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 206010037660 Pyrexia Diseases 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000001187 sodium carbonate Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 230000001225 therapeutic Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
Definitions
- My invention relates to the production of the hitherto unknown salicylic ether'of quinin, having most probably the following formula:
- the new quinin derivative thus obtained is tasteless and possesses a great therapeutic value. It is a valuableremedy against fever.
- the average dose employed for this purpose is about one-half gram.
- this solution is shaken with dilute sulfuric acid in order to transform the new quinin derivative contained thereininto its sulfate. .
- the resulting sulfuric-acid solution of the new body is then separated from the chloroform.
- the sulfuric-acid solution is mixed with an excess of sodium carbonate, and from the resulting mixture the free base of quinin salicylate is isolated in the usual way by shaking the mixture with other. From the resulting ethereal solution the new compound separates after some time in the shape of white needles. It is filtered off and dried.
- the new salicylic ether of quinin having most probably the above-given formula is a white crystalline powder melting at 138 centigrade and at 140 centigrade after further purification. It is very readily soluble in chloroform, readily soluble in hot alcohol and what I claim as new, and desire to secure by- Letters Patent, is
Description
UNITE STATES PAT NT OFFICE.
FRITZ HOFMANN, OF ELBERFELD,'-GERMA-NY, ASSIGNOR TO THE FARBEN- FABRIKEN OF ELBERFELD (30., A CORPORATION OF NEW' YORK.
sAucYuc ERTHER OF QUININ.
SPECIFICATION forming part of Reissued Letters Patent No. 11,960, dated January 7, 1902.
Original No. 678,401, dated July 16, 1901. Application for reissue illed December 9, 1901. Serial No. 85,302-
'l'o all whom it may concern: Y
receiver to a crystalline mass.
Be it known that I, FRITZ HOFMANN, doctor of philosophy, chemist, residing at Elherfeld, Germany, (assignor to the FARBENFABRIKEN OFELBERFELD COMPANY, of New York,) have invented a new and useful Improvement-in Pharmaceutical Compounds, and I hereby declare-the following to be a clear and exact description of my invention.
My invention relates to the production of the hitherto unknown salicylic ether'of quinin, having most probably the following formula:
According to my researches this new compound can be easily obtained by heating the alphylethersofsalicylic acid,generallytermed salols, with quinin. On using,forinstance, phenyl salicylate the process proceeds according to the following equation:
phenol and the new quinin salicylate being produced. The new quinin derivative thus obtained is tasteless and possesses a great therapeutic value. It is a valuableremedy against fever. The average dose employed for this purpose is about one-half gram.
In carrying out my new process practically I can proceed as follows, the parts being by.
weight: In a vessel provided with a descending condenser a mixture prepared from three hundred and twenty-four parts of quinin (free ,from water) and two'hundred and fourteen parts of salol (phenyl salicylate) is heated by means of an oil-bath in vacuo to a temperature of from 170 to 190 centigrade. the mixture has melted the distillation of pure phenol begins,.which solidifies in the After the reaction is finished the residue remaining in the vessel is dissolved in chloroform, and the. solution thus obtained is treated with a oneper-cent acetic acid, by which means unchanged quinin is rernoved from the chloro- After form solution. Subsequently this solutionis shaken with dilute sulfuric acid in order to transform the new quinin derivative contained thereininto its sulfate. .The resulting sulfuric-acid solution of the new body is then separated from the chloroform. In order to prepare the free quinin derivative, the sulfuric-acid solution is mixed with an excess of sodium carbonate, and from the resulting mixture the free base of quinin salicylate is isolated in the usual way by shaking the mixture with other. From the resulting ethereal solution the new compound separates after some time in the shape of white needles. It is filtered off and dried. Y
The new salicylic ether of quinin having most probably the above-given formula is a white crystalline powder melting at 138 centigrade and at 140 centigrade after further purification. It is very readily soluble in chloroform, readily soluble in hot alcohol and what I claim as new, and desire to secure by- Letters Patent, is
The herein-described new salicylic ether of.
quinin having most probably the formula:
being a tasteless white crystalline powder name to this specification in the presence of two snbscribin g witnesses.
. FRITZ HOFMANN.
Witnesses: I
O'r'ro Kome,
J. A. RI'rrnRsHAUs.
Family
ID=
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