US2040848A - Acetyl salicylic acid solution and method of producing the same - Google Patents
Acetyl salicylic acid solution and method of producing the same Download PDFInfo
- Publication number
- US2040848A US2040848A US648442A US64844232A US2040848A US 2040848 A US2040848 A US 2040848A US 648442 A US648442 A US 648442A US 64844232 A US64844232 A US 64844232A US 2040848 A US2040848 A US 2040848A
- Authority
- US
- United States
- Prior art keywords
- salicylic acid
- solution
- acetyl salicylic
- same
- glycerine
- 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.)
- Expired - Lifetime
Links
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 title description 22
- 229960001138 acetylsalicylic acid Drugs 0.000 title description 22
- 238000000034 method Methods 0.000 title description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 28
- 229940079593 drug Drugs 0.000 description 16
- 239000003814 drug Substances 0.000 description 16
- 235000011187 glycerol Nutrition 0.000 description 14
- 239000007787 solid Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 description 5
- 229960000212 aminophenazone Drugs 0.000 description 5
- RLFWWDJHLFCNIJ-UHFFFAOYSA-N Aminoantipyrine Natural products CN1C(C)=C(N)C(=O)N1C1=CC=CC=C1 RLFWWDJHLFCNIJ-UHFFFAOYSA-N 0.000 description 4
- 230000000202 analgesic effect Effects 0.000 description 4
- 239000002221 antipyretic Substances 0.000 description 4
- VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 229960005222 phenazone Drugs 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- 229960004889 salicylic acid Drugs 0.000 description 3
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- 230000001754 anti-pyretic effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- YTRMTPPVNRALON-UHFFFAOYSA-N 2-phenyl-4-quinolinecarboxylic acid Chemical class N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=CC=C1 YTRMTPPVNRALON-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229960005150 glycerol Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical group O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
Definitions
- the present invention embodies an improved acetyl salicylic acid solution and method of producing the same, the invention particularly embodying' an improved solution formed with a solvent or vehicle which facilitates the production of the solution and improves the physical char bodies a solution of acetyl salicylic acid in solvents or vehicles other than water, as suggested I 15 in applicant's copending application, above identified, as one form in which acetyl salicylic acid may be used.
- the solvent or vehicle described herein as particularly suited for use in connection with the present invention is glyce'ine and while other substances of similar nature may be used as the solvent or vehicle, the description of the inventionwwill be given with glycerine as the solvent.
- An object of the invention accordingly is to pro- 25 vide an improved solution of acetyl salicylic acid without changing the chemical properties thereof or impairing its therapeutic value as a drug, the improved solution being stable and of a physical nature rendering the same more readily ad- 30 ministered.
- a further object of the invention is to provide a solution of acetyl salicylic acid with another synergistic drug, the drugs' being held by an improved solvent or vehicle which renders the drugs 35 mutually soluble through a wider range of relative proportions than possible with the drugs alone or in solution with water.
- a further object of the invention is to provide an improved solution of acetyl salicylic acid with 40 a vehicle which improves the taste and smell of the drugs and renders the same more readily administered at the same time preventing hydrolysis of either or any of the drugs upon long standing.
- acetyl salicylic acid solution is formed with water
- hydrolysis of one or more of the drugs may take place in time and it has been found that, upon standing for some time, such solutions frequently have objectionable taste and odor even though the therapeutic action thereof is not appreciably impaired.
- Such hydrolysis produces acetic acid and salicylic acid which impart the objectionable taste and odor above referred to.
- acetyl salicylic acid is put into solution by mixing the same with one of the drugs of the analgesic and antipyretic group and heating gently.
- glycerine is added to the solution and it has been found that a satisfactory mixture may be formed. by using ingredients in the proportion of one gram of acetyl salicylic acid, one gramv of amidopyrine or antipyrine and c.c. of glycerine.
- solution has been used in the speciflcation as well as in the appended claims in its broader sense and includes the mutual solution oi! two solids in each other as well as dlssolution'in a fluid solvent.
- a mutual solution 01' acetyl salicylic acid and melubrine in glycerine.
- the method or preparing a potentlated solution of acetyl salicylic acid which comprises mixing solid acetyl salicylic acid with another solid analgesic and antipyretic drug and with glycerine and applying heat sufllcient to cause mutual solution only.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Description
Patented May 19, 1936- UNITED STATES ACETYL SALICYLIC ACID SOLUTION AND METHOD OF PRODUCING THE SALE Louis Hirschhorn, New York,-N. Y.
No Drawing. Application December 22, 1932,
Serial No. "648,442
9 Claims. The present invention embodies an improved acetyl salicylic acid solution and method of producing the same, the invention particularly embodying' an improved solution formed with a solvent or vehicle which facilitates the production of the solution and improves the physical char bodies a solution of acetyl salicylic acid in solvents or vehicles other than water, as suggested I 15 in applicant's copending application, above identified, as one form in which acetyl salicylic acid may be used. The solvent or vehicle described herein as particularly suited for use in connection with the present invention is glyce'ine and while other substances of similar nature may be used as the solvent or vehicle, the description of the inventionwwill be given with glycerine as the solvent.
An object of the invention accordingly is to pro- 25 vide an improved solution of acetyl salicylic acid without changing the chemical properties thereof or impairing its therapeutic value as a drug, the improved solution being stable and of a physical nature rendering the same more readily ad- 30 ministered.
A further object of the invention is to provide a solution of acetyl salicylic acid with another synergistic drug, the drugs' being held by an improved solvent or vehicle which renders the drugs 35 mutually soluble through a wider range of relative proportions than possible with the drugs alone or in solution with water. v
A further object of the invention is to provide an improved solution of acetyl salicylic acid with 40 a vehicle which improves the taste and smell of the drugs and renders the same more readily administered at the same time preventing hydrolysis of either or any of the drugs upon long standing.
and in this specification to those central nervous 50 system depressants which have a selective effect on the pain and heat regulating centers of the brain. The function andyrop rties of the resulting solution are similar to those described in applicant's copending application above referred ,65 to and, briefly statedare as follows. Byintroducing the acetyl salicylic acid into the system in solution, its potency and eflectiveness are greatly increased, being rapidly, assimilated or absorbed without decomposition and greatly increasing the effectiveness thereof. Moreover, being in 5 liquid form, the drug may be administered more effectively and in a more agreeable fashion than possible with the drug in solid form.
Where the acetyl salicylic acid solution is formed with water, hydrolysis of one or more of the drugs may take place in time and it has been found that, upon standing for some time, such solutions frequently have objectionable taste and odor even though the therapeutic action thereof is not appreciably impaired. Such hydrolysis produces acetic acid and salicylic acid which impart the objectionable taste and odor above referred to.
'In accordance with the present invention and in carrying out the same, acetyl salicylic acid is put into solution by mixing the same with one of the drugs of the analgesic and antipyretic group and heating gently. At the same time, glycerine is added to the solution and it has been found that a satisfactory mixture may be formed. by using ingredients in the proportion of one gram of acetyl salicylic acid, one gramv of amidopyrine or antipyrine and c.c. of glycerine.
The above substances when placed in the glycerine and heated will go into complete solution, 30 stirring assisting suchaction. Varying proportions of acetyl salicylic acid and antipyrine or amidopyrine and glycerine may be used as will be readily apparent. Instead of using antipyrine or amidopyrine, other substances in this group of analgesic antipyretic drugs such as acetanilid, phenacitine, melubrine, quinine, compounds of the phenyl cinchoninic acid series and the like my be used as set forth in the above identified copending application. 40
Since no water is used in the foregoing solution no hydrolysis of the ingredients takes place and it has been found that the drugs are actually soluble through a wider range of relative proportions in the presence of glycerine than with water. For example, it has been found thatacetyl salicylic acid and pyramidon will dissolve in glycerine in the proportions 1-1 whereas this of these compounds. The solution may. be made so that each teaspoon contains the desired quantity oi. each drug. An advantage of this solution is that the glycerine acts as'a preservative and antiseptic in this concentrated state. A further advantage of this solution is that it dissolves in water in all proportions. This property permits of the ready formation of a fresh, agreeably flavored water solution of these drugs when needed by the patient.
The word "solution has been used in the speciflcation as well as in the appended claims in its broader sense and includes the mutual solution oi! two solids in each other as well as dlssolution'in a fluid solvent.
I claim as my invention:
1. A mutual solution of acetyl salicylic acid and a drug of the analgesic and antipyretic group in glycerlne.
2. A mutual solution of acetyl salicylic acid and a drug of the pyrazolon group in glycerine.
3. A'mutual solution of acetyl" salicylic acid and amidopyrine in glycerine.
4. A mutual solution of acetyl salicylic acid and antlpyrine in glycerine.
5. A mutual solution 01' acetyl salicylic acid and melubrine in glycerine.
6. The method or preparing a potentlated solution of acetyl salicylic acid which comprises mixing solid acetyl salicylic acid with another solid analgesic and antipyretic drug and with glycerine and applying heat sufllcient to cause mutual solution only.
7. The method of preparing a potentlated solution of acetyl salicylic acid'which comprises mixing solid acetyl salicylic acid with solid antipyrine and with glycerine and applying heat sufllcient to cause mutual solution only.
8. The method otpreparing a potentlated solution of acetyl salicylic acid which comprises mixing solid acetyl salicylic acid with solid ami-
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US648442A US2040848A (en) | 1932-12-22 | 1932-12-22 | Acetyl salicylic acid solution and method of producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US648442A US2040848A (en) | 1932-12-22 | 1932-12-22 | Acetyl salicylic acid solution and method of producing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2040848A true US2040848A (en) | 1936-05-19 |
Family
ID=24600789
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US648442A Expired - Lifetime US2040848A (en) | 1932-12-22 | 1932-12-22 | Acetyl salicylic acid solution and method of producing the same |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2040848A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3627875A (en) * | 1962-06-12 | 1971-12-14 | Ind Nuclear Investigation Co L | Antipyretic and inflammation combatting compositions |
-
1932
- 1932-12-22 US US648442A patent/US2040848A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3627875A (en) * | 1962-06-12 | 1971-12-14 | Ind Nuclear Investigation Co L | Antipyretic and inflammation combatting compositions |
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