US1235278A - Medicament and process of producing the same. - Google Patents

Medicament and process of producing the same. Download PDF

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Publication number
US1235278A
US1235278A US79274113A US1913792741A US1235278A US 1235278 A US1235278 A US 1235278A US 79274113 A US79274113 A US 79274113A US 1913792741 A US1913792741 A US 1913792741A US 1235278 A US1235278 A US 1235278A
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Prior art keywords
antipyretic
acetanilid
citric acid
producing
stimulating
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US79274113A
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Albert Decatur Barr
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D473/00Heterocyclic compounds containing purine ring systems
    • C07D473/02Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
    • C07D473/04Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
    • C07D473/06Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
    • C07D473/12Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1, 3, and 7, e.g. caffeine

Definitions

  • This invention relates to medicaments and processes of producing the same; and it comprises a stimulating, antipyretic, crystalline salt containing as proximate elements an antipyretic derivative of the anilin group of the anilid type, and a vegetable alkaloid of appropriate therapeutic properties; and it also comprises a process of producing such medicament by the treatment of an anilid derivative with an organic acid and the subsequent union of an alkaloid to the body so treated, all as more fully hereinafter set forth and as claimed.
  • acetanilid as the antipyretic salt.
  • the antipyretic salt may be substituted one of the other antipyretic derivatives of the anilin group containing the acetic acid molecule without departing from the spirit and scope of my invention.
  • other elements than calfein may be employed where the citric acid is used in combination, but I prefer caffein in this particular embodiment of the invention, as it gives a better balance between the heartdepressing and heart-stimulating properties of the final product.
  • What I claim is 1.
  • the process of making a stimulating antipyretic comprising mixing acetanilid and an organic acid in solution, heating the product formed, adding a vegetable alkaloid, evaporating the solution and allowing it to crystallize.
  • a stimulating antipyretic composition which comprises mixing a solution of citric acid and an anti pyretic derivative of the anilin group containing the acetyl radical, heating the 111lX-' ture, adding a vegetablealkaloichheating the compound thus formed, and evaporating andcrystallizing the resultant product;
  • a stimulating antipyretic composition which comprises mixing a solution. of an organic acid and an antipyretic derivative of the anilin group containing the acetyl radical, heating the mixture, adding vegetable alkaloid, heat ing the compound thus formed, and evaptiopies ct this giatent may be obtained for five cents each, by addressing the tcmmissioner of Eatents,
  • a stimulating antipyretio saline substance containing chen1ical combination of molecular proportions of i aoietanilid, citric acid and ca'li'ein As a new product, a stimulating antipyretio saline substance containing chen1ical combination of molecular proportions of i aoietanilid, citric acid and ca'li'ein.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

ares
ALBERT DECATUR; BARR, OF .MCHUE, ARKANSAS.
No Drawing.
To aZZ whom it may concern Be it known that I, ALBERT Dnoa'rnn BARR, a citizen of the United States, residing at McHue, county of Independence, State of Arkansas, have invented new and useful Improvements in Medicaments and Processes of Producing the Same, of which the following is a specification.
This invention relates to medicaments and processes of producing the same; and it comprises a stimulating, antipyretic, crystalline salt containing as proximate elements an antipyretic derivative of the anilin group of the anilid type, and a vegetable alkaloid of appropriate therapeutic properties; and it also comprises a process of producing such medicament by the treatment of an anilid derivative with an organic acid and the subsequent union of an alkaloid to the body so treated, all as more fully hereinafter set forth and as claimed.
In my Patent No. 966,786 of August 19th, 1910, I have described a stimulating antipyretic, crystalline saline body and method of producing it and referred to the value of the same. My present invention relates to a similar saline body having similar physiological effects.
I have discovered that upon treating acetanilid with the right amount of an organic acid, such as citric acid, under certain conditions, the acid may be made to enter into combination with the acetanilid and that this combination can be rendered stable by the addition of an alkaloid, specifically caffein, which enters into chemical combination therewith, with the result that there is obtained a definite chemical combination hav ing antipyretic value without concomitant depressing action on the heart.
The process will be readily understood from the following:
To 6598.62- grains of citric acid (H C H O I add about a pint of water and heat to the boiling point. To this solution is added 4458.53 grains of acetanilid (C H Nl-LC H 0) 01' its equivalent and the compound thus formed is boiled for about thirty minutes.
To this is added 7000 grains of caffein (C H NAD and the mass is boiled for two and one-half hours, care being taken to add, from time to time, the water lost by evaporation.
At the end of this time the solution is placed over a water bath and evaporated Specification of Letters Patent.
Patented July 31, 1917.
Application filed October 1, 1913. Serial No. 792,741.
until the compound weighs about 18057.15 grains, at which time it has become a true chemical compound of thick, syrupy consistency. It is then set aside in a cool place, free from dust and allowed to crystallize for about from three to siX weeks. The re sult is a true chemical combination containing acetanilid, citric acid and caffein molecules (C H NHC H O, H C H O (3 H N 0 in the proportions of ten parts acetanilid, 14.81 parts'ofcitric acid and 15.7 parts of catlein. On analysis it yields 24.6852 per cent. acetanilid; 36.5607 per cent. citric acid; and 38.7754 per cent. cafiein. It dissolves in about its own weight of water and is slightly hygroscopic during the warm weather. The medicinal adult dose is, from live to twenty-five grains and it is advantageous in all pathological conditions where there is a rise of temperature above 100.3.
In the foregoing, I have mentioned acetanilid as the antipyretic salt. For it may be substituted one of the other antipyretic derivatives of the anilin group containing the acetic acid molecule without departing from the spirit and scope of my invention. So, too, other elements than calfein may be employed where the citric acid is used in combination, but I prefer caffein in this particular embodiment of the invention, as it gives a better balance between the heartdepressing and heart-stimulating properties of the final product.
What I claim is 1. The process of making a stimulating antipyretic comprising mixing acetanilid and an organic acid in solution, heating the product formed, adding a vegetable alkaloid, evaporating the solution and allowing it to crystallize.
2. The process of manufacturing a stimu lating antipyretic which comprises mixing acetanilid and citric acid in solution, heating the same, adding cafiein and heating the compound thus formed, and evaporating and crystallizing the resultant product.
3. As a new product, a stimulating antipyretic, saline substance containing groups derived from citric acid, acetanilid and catfein in substantially the following proportions: acetanilid, 24.68 per cent; citric acid, 36.56 per cent; cafl ein, 38.74 per cent, said substance being slightly hygroscopic during warm weather and being soluble in about its own weight of water.
4. The process of making a stimulating antipyretic composition which comprises mixing acetanilid and citric acid together in solution, heating the ,rnixture adding an alkaloid to produce a chemical compound of the three, and evaporating andcrystallizing the resultant product.
The process of making a stimulating antipyretic composition which comprises mixing a solution of citric acid and an anti pyretic derivative of the anilin group containing the acetyl radical, heating the 111lX-' ture, adding a vegetablealkaloichheating the compound thus formed, and evaporating andcrystallizing the resultant product;
6. The process of making a stimulating antipyretic composition which comprises mixing a solution. of an organic acid and an antipyretic derivative of the anilin group containing the acetyl radical, heating the mixture, adding vegetable alkaloid, heat ing the compound thus formed, and evaptiopies ct this giatent may be obtained for five cents each, by addressing the tcmmissioner of Eatents,
crating and crystalli zing the resultant product.
'1. As a new product, a stimulating antipyretio saline substance containing chen1ical combination of molecular proportions of i aoietanilid, citric acid and ca'li'ein.
I'IERMAN Gosrow, ALFRED M. HOUGT-ITON.
Washington, 3; '53,
US79274113A 1913-10-01 1913-10-01 Medicament and process of producing the same. Expired - Lifetime US1235278A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4531003A (en) * 1981-04-14 1985-07-23 Nestec S. A. Purification of caffeine
US4758662A (en) * 1981-04-14 1988-07-19 Nestec S. A. Purification of caffeine

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4531003A (en) * 1981-04-14 1985-07-23 Nestec S. A. Purification of caffeine
US4758662A (en) * 1981-04-14 1988-07-19 Nestec S. A. Purification of caffeine

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