US1632306A - Preparation of solutions of compounds insoluble or sparingly soluble in water - Google Patents
Preparation of solutions of compounds insoluble or sparingly soluble in water Download PDFInfo
- Publication number
- US1632306A US1632306A US749046A US74904624A US1632306A US 1632306 A US1632306 A US 1632306A US 749046 A US749046 A US 749046A US 74904624 A US74904624 A US 74904624A US 1632306 A US1632306 A US 1632306A
- Authority
- US
- United States
- Prior art keywords
- solutions
- preparation
- water
- sparingly soluble
- phenylacetylene
- 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
- 150000001875 compounds Chemical class 0.000 title description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title description 3
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 18
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 12
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 7
- 241000723346 Cinnamomum camphora Species 0.000 description 7
- 229960000846 camphor Drugs 0.000 description 7
- 229930008380 camphor Natural products 0.000 description 7
- HVYWMOMLDIMFJA-UHFFFAOYSA-N 3-cholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 HVYWMOMLDIMFJA-UHFFFAOYSA-N 0.000 description 4
- 235000012000 cholesterol Nutrition 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- XNERWVPQCYSMLC-UHFFFAOYSA-N phenylpropiolic acid Chemical compound OC(=O)C#CC1=CC=CC=C1 XNERWVPQCYSMLC-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- 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
Definitions
- the invention relates to the preparation of solutions of compounds insoluble or sparingly soluble in Water byusiug phenylacetylene as a solvent.
- phenylacetylene is capable in a high degree of dissolving certain therapeutic compounds, especially camphor or mixtures of camphor With lipoids, such. as for instance cholesterin or esters of saturated or unsaturated organic acids with cholesterin, and the like, and that the solutions thus obtained may be injected subcutaneously or intramuscularly Without causing any irritation.
- the solutions may also be employed for per-cutaneous use according to the properties of the dissolved compounds.
- Analogous solutions may be obtained with 50 parts of phenylacetylene, 50 parts of camphor and from 610 parts of the cholesterol other of phenylpropiolic acid or crotonic acid, 'or other unsaturated organic acids.
- cholesterin ether instead of a cholesterin ether in this example cholesterin itself or another lipeid may be employed.
Description
Patented June 14, 1927.
WALTER IVIINNICH, O13 MONTREUX, SWITZERLAND, ASSIG'NOR TO SOCIETY OF CHEML GAL INDUSTRY IN BASLE, F BASEL, SVTITZERLAND.
PREPARATION OF SOLUTIONS OF COMPOUNDS INSOL'UBLE OE SPAEI'NGLY SOLUBLE I1\T WATER.
.No Drawing. Application filed November 10, 19%, Serial No. 749,046, and in Switzerland November 19,
The invention relates to the preparation of solutions of compounds insoluble or sparingly soluble in Water byusiug phenylacetylene as a solvent.
5 I have found that phenylacetylene is capable in a high degree of dissolving certain therapeutic compounds, especially camphor or mixtures of camphor With lipoids, such. as for instance cholesterin or esters of saturated or unsaturated organic acids with cholesterin, and the like, and that the solutions thus obtained may be injected subcutaneously or intramuscularly Without causing any irritation. The solutions may also be employed for per-cutaneous use according to the properties of the dissolved compounds.
The solutions obtained according to the present invention are thus useful for a large variety of purposes, particularly in human or veterinary medicine.
Example 1.
50 parts of phenylacetylene are introduced into 50 parts of camphor. The eamphor readily dissolves completely. The mobile solution thus obtained is filtered, if necessary, and may be employed for injections without any further treatment.
Err/ample 2.
Analogous solutions may be obtained with 50 parts of phenylacetylene, 50 parts of camphor and from 610 parts of the cholesterol other of phenylpropiolic acid or crotonic acid, 'or other unsaturated organic acids. Of course, instead of a cholesterin ether in this example cholesterin itself or another lipeid may be employed.
hat I claim is: i
1. As an article of manufacture, solutions of camphor 'in phenylacetylene.
2. As an article ofmanufacture solutions of camphor and lipoids in phenylacetylene.
8. As an article of'manufacture, solutions of camphor and cholesterol in phenylacetylene.
. 4-. As an article of manufacture, solutions of cainphor and esters of cholesterol. in phenylacetylene.
5. As an article of manufacture, solutions of. caniphor and unsaturated acid esters of cholesterol in phenylacetylene.
In Witness whereof I have hereunto signed my name this 27 day of October 1924.
VJALTER MINNICH.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1632306X | 1923-11-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1632306A true US1632306A (en) | 1927-06-14 |
Family
ID=4565714
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US749046A Expired - Lifetime US1632306A (en) | 1923-11-19 | 1924-11-10 | Preparation of solutions of compounds insoluble or sparingly soluble in water |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1632306A (en) |
-
1924
- 1924-11-10 US US749046A patent/US1632306A/en not_active Expired - Lifetime
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