GB2048063A - Sulphonamide and Potentiator Solutions - Google Patents
Sulphonamide and Potentiator Solutions Download PDFInfo
- Publication number
- GB2048063A GB2048063A GB7915514A GB7915514A GB2048063A GB 2048063 A GB2048063 A GB 2048063A GB 7915514 A GB7915514 A GB 7915514A GB 7915514 A GB7915514 A GB 7915514A GB 2048063 A GB2048063 A GB 2048063A
- Authority
- GB
- United Kingdom
- Prior art keywords
- solution
- sulphonamide
- potentiator
- mixture
- water
- 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.)
- Granted
Links
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 229940124530 sulfonamide Drugs 0.000 title claims abstract description 18
- 239000000203 mixture Substances 0.000 claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000002253 acid Substances 0.000 claims abstract description 12
- 150000002772 monosaccharides Chemical class 0.000 claims abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 9
- 238000003756 stirring Methods 0.000 claims abstract description 9
- 239000003960 organic solvent Substances 0.000 claims abstract description 8
- 238000010438 heat treatment Methods 0.000 claims abstract description 5
- 239000000243 solution Substances 0.000 claims description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
- 238000001802 infusion Methods 0.000 claims description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 6
- 238000002347 injection Methods 0.000 claims description 6
- 239000007924 injection Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical group C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 claims description 6
- 229960004306 sulfadiazine Drugs 0.000 claims description 6
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical group COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 claims description 6
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 239000000600 sorbitol Substances 0.000 claims description 5
- JLKIGFTWXXRPMT-UHFFFAOYSA-N sulphamethoxazole Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 JLKIGFTWXXRPMT-UHFFFAOYSA-N 0.000 claims description 5
- 229960001082 trimethoprim Drugs 0.000 claims description 5
- 229960005404 sulfamethoxazole Drugs 0.000 claims description 4
- 239000004475 Arginine Substances 0.000 claims description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical group OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 3
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 3
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 3
- 239000011877 solvent mixture Substances 0.000 claims description 3
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 2
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004472 Lysine Substances 0.000 claims description 2
- 229930195725 Mannitol Natural products 0.000 claims description 2
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims description 2
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims description 2
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 2
- 239000000594 mannitol Substances 0.000 claims description 2
- 235000010355 mannitol Nutrition 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 229960003104 ornithine Drugs 0.000 claims description 2
- 239000012153 distilled water Substances 0.000 claims 2
- 239000007788 liquid Substances 0.000 abstract description 2
- 150000003456 sulfonamides Chemical class 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229920001308 poly(aminoacid) Polymers 0.000 description 3
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 2
- 229930064664 L-arginine Natural products 0.000 description 2
- 235000014852 L-arginine Nutrition 0.000 description 2
- NHUHCSRWZMLRLA-UHFFFAOYSA-N Sulfisoxazole Chemical compound CC1=NOC(NS(=O)(=O)C=2C=CC(N)=CC=2)=C1C NHUHCSRWZMLRLA-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 235000009697 arginine Nutrition 0.000 description 2
- LDBTVAXGKYIFHO-UHFFFAOYSA-N diaveridine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=CN=C(N)N=C1N LDBTVAXGKYIFHO-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- DZHKPVJNIUOWTI-UHFFFAOYSA-N 2-amino-4,6-dimethoxy-n-pyrimidin-2-ylbenzenesulfonamide Chemical compound COC1=CC(OC)=CC(N)=C1S(=O)(=O)NC1=NC=CC=N1 DZHKPVJNIUOWTI-UHFFFAOYSA-N 0.000 description 1
- IMSKSJKAEYLZJH-UHFFFAOYSA-N 2-amino-4,6-dimethyl-n-pyrimidin-2-ylbenzenesulfonamide Chemical compound NC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=NC=CC=N1 IMSKSJKAEYLZJH-UHFFFAOYSA-N 0.000 description 1
- QQWZAGKPIHSPRN-UHFFFAOYSA-N 2-amino-n-(4-methylpyrimidin-2-yl)benzenesulfonamide Chemical compound CC1=CC=NC(NS(=O)(=O)C=2C(=CC=CC=2)N)=N1 QQWZAGKPIHSPRN-UHFFFAOYSA-N 0.000 description 1
- PYXGYXVXXFBFAT-UHFFFAOYSA-N 2-amino-n-pyrimidin-2-ylbenzenesulfonamide Chemical compound NC1=CC=CC=C1S(=O)(=O)NC1=NC=CC=N1 PYXGYXVXXFBFAT-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229950000246 diaveridine Drugs 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- ZZORFUFYDOWNEF-UHFFFAOYSA-N sulfadimethoxine Chemical compound COC1=NC(OC)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 ZZORFUFYDOWNEF-UHFFFAOYSA-N 0.000 description 1
- 229960000654 sulfafurazole Drugs 0.000 description 1
- QPPBRPIAZZHUNT-UHFFFAOYSA-N sulfamerazine Chemical compound CC1=CC=NC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 QPPBRPIAZZHUNT-UHFFFAOYSA-N 0.000 description 1
- 229960002597 sulfamerazine Drugs 0.000 description 1
- ASWVTGNCAZCNNR-UHFFFAOYSA-N sulfamethazine Chemical compound CC1=CC(C)=NC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 ASWVTGNCAZCNNR-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic 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
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/63—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide
- A61K31/635—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide having a heterocyclic ring, e.g. sulfadiazine
-
- 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
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
- A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A clear solution of a sulphonamide and a potentiator comprises the sulphonamide and potentiator in a 5:1 weight ratio together with a polyamino acid and a non-reducing monosaccharide in a mixture of solvents, at least 50% of which is water, and the remainder consists of water-miscible organic solvents. The solvents are mixed, and monosaccharide and polyamino acid are first dissolved in the liquid mixture, after which the sulphonamide and potentiator are dissolved with stirring at room temperature or by slight heating.
Description
SPECIFICATION
Solutions of Sulphonamides and Potentiators for same, and their Production
This invention relates to solutions, for injection and infusion purposes, containing a sulphonamide and a potentiator for the same, and to the production of such solutions.
It is well-known that the therapeutic effect of sulphonamides can be increased by means of certain organic compounds, so-called potentiators, generally used in the ratio of 5 parts by weight of sulphonamide to 1 part by weight of the potentiator
When several active components are to be used for injection or infusion, it is preferred to combine them in a single preparation in order to ensure an optimal dosage of the individual components, and this creates problems in the case of sulphonamides and potentiators for the same.
The sulphonamides, such as for instance 4,6dimethyl-2-sulphanilamido-pyrimidine (sulphamethazine), 2-sulphanilamido-pyrimidine (sulphadiazine), 5-methyl-3-sulphanilamidoisoxazole (sulphamethoxazole), 2,4-dimethoxy-6sulphanilamido-pyrimidine (sulphadimethoxine), 3,4-dimethyl-5-sulphanilamido-isoxazole (sulphafurazole), and 2-sulphanilamido-4methylpyrimidine (sulphamerazine) are only very slightly soluble in water and form suitable salts only with bases.
On the other hand, the organic compounds, having a potentiating effect on sulphonamides, are basically reacting compounds, such as for instance 2,4-diamino-5-(3,4-dimethoxybenzyl)pyrimidine (diaveridine) and 2,4-diamino-(3,4,5 trimethoxybenzyl)-pyrimidine (trimetho-prim), which form suitable water-soluble salts only with acids.
Mixing aqueous solutions of the two components in the form of such salts, therefore, would result in a precipitation of one or both of the components.
A typical way of solving the problem of combining a sulphonamide and a potentiator is to dissolve one of the components as a salt in water, whereas the other component is dissolved in a water-miscible organic solvent or mixture of solvents.
Thus, according to the British Patent
Specification No. 1,176,395, an aqueous solution of a sulphonamide salt is mixed with a solution of a potentiator in a medicinally acceptable water missile organic solvent.
As shown by the Examples of the said specification, the organic solvents form the major portion of the combined solvents, and heating to 50-750C appears necessary for dissolving the components.
The resulting solutions are strongly basic reacting, and any attempts of reducing the pH of the solutions will result in precipitation, which means, for instance, that the solutions cannot be infused together with other infusion liquids which
are usually of neutral to slightly acid reaction.
Reducing of the pH may also in some cases
result in the formation of insoluble complexes
between the sulphonamide and the potentiator.
The object of the present invention is to
overcome the difficulties presented by the
differences in solubility of sulphonamides and
potentiators, and with this object in mind a totally
new approach to the problem is suggested,
namely the use of a polyamino acid as solubilizer
for the sulphonamide as well as the potentiator.
Owing to their properties of being both acids
and bases, the polyamino acids should be well
suited as solubilizers for the sulphonamides
dissolving under basic conditions as well as for
the potentiators dissolving under acid conditions.
However, it was found that the polyamino
acids by themselves were not able to solubilize
the two components, but that addition of a further
solubilizer in the form of a non-reducing
monosaccharide was successful.
Accordingly, a solution of a sulphonamide and
a potentiator as provided by the present invention
comprises a sulphonamide and a potentiator in
the weight ratio 5:1, a polyamino acid and a non
reducing monosaccharide dissolved in a solvent
mixture, at least 50% by weight of which is water,
the remainder being a mixture of watermiscible
organic solvents.
Preferred sulphonamides are sulphadiazine and
sulphamethoxazole, and the preferred potentiator
is trimethoprim.
Examples of the polyamino acids are arginine,
ornithine, and lysine, with arginine as the
preferred one.
Examples of the non-reducing
monosaccharides are sorbitol and mannitol,
sorbitol being preferred.
In the solvent mixture, the water content
usually amounts to 5075%. The preferred
organic solvent mixture is either a 1:1 mixture of
ethanol and benzyl alchohol, or a 1:1:2 mixture of
ethanol, benzyl alcohol and propylene glycol.
In the production of the solutions according to the invention, water and the organic solvents are
mixed, and the monosaccharide and the
polyamino acid are dissolved in the mixture, after which the sulphonamide and the potentiator are
added and the mixture is stirred, possibly under slight heating, until a clear solution has formed, which is then sterile-filtered and autoclaved to form the final product.
In order to prevent a possible oxidation of the sulphonamide, the process is carried out under nitrogen.
The following Examples are illustrative of the products of the invention and their production.
Example 1
Preparation of a potentiated sulphonamide solution for infusion purposes
A mixture is prepared from 6000 g of redistilled water, 1000 g of 96% ethanol, and 1000 g of benzyl alcohol, and 500 g of sorbitol are dissolved in the mixture by stirring at room temperature. To the resulting solution, 800 g of sulphamethoxazole, 160 g of trimethoprim, and 800 g of L-arginine are added with stirring at room temperature, and stirring is continued until all solids are dissolved.
The resulting solution is sterile filtered and autoclaved at 121 CC, after which it is ready for use.
The whole preparation is carried out in a nitrogen atmosphere to avoid oxidation problems.
Example 2
Preparation of an injectable composition
A mixture is prepared from 4000 g of redistilled water, 1000 g of 96% ethanol, 1 000g of benzyl alcohol, and 2000 g of propylene glycol, and 500 g of sorbitol are dissolved in this mixture with stirring. Then, 1 50 g of L-arginine are dissolved in the solution, after which 1 50 g of sulphadiazine and 300 g of trimethoprim are dissolved in the solution by stirring with heating to 400--420C. Additionally, 1350 g of sulphadiazine are suspended in the warm solution, and 465 g of a 50% aqueous sodium hydroxide solution are slowly added with stirring to dissolve the suspended sulphadiazine.
The resulting solution is sterile filtered and autoclaved at 121 OC to make the final injection solution.
All of the preparative steps are carried out under nitrogen.
Claims (9)
1. A clear solution for injection and infusion purposes, which comprises a sulphonamide and a potentiator in the weight ratio 5:1, a polyamino acid, and a non-reducing monosaccharide, dissolved in a solvent mixture, at least 50% by weight of which is water, the remainder being a mixture of water-miscible organic solvents.
2. A solution as set forth in claim 1, in which the sulphonamide is sulphadiazine or sulphamethoxazole, and the potentiator is trimethoprim.
3. A solution as set forth in claim 1 or claim 2, in which the polyamino acid is arginine, ornithine, or lysine.
4. A solution as set forth in any of claims 1 to 3, in which the non-reducing monosaccharide is sorbitol or mannitol.
5. A solution for infusion purposes as set forth in any of claims 1 to 4, in which the solvents are a mixture of distilled water, 96% ethanol, and benzyl alcohol in a weight ratio of 6:1:1.
6. A solution for injection purposes as set forth in any of claims 1 to 4, in which the solvents are a mixture of distilled water, 96% ethanol, benzyl alcohol, and propylene glycol in a weight ratio of 4:1:1:2.
7. A process for the preparation of a solution as set forth in any of claims 1 to 6, which process comprises mixing the water and organic solvents, dissolving the monosaccharide and the polyamino acid in the mixture with stirring, after which the sulphonamide and the potentiator are dispersed in the solution with stirring until a clear solution has formed, which is finally sterile filtered and autoclaved.
8. A process as claimed in Claim 7, in which the sulphonamide and the potentiator are dissolved in the said solution with heating.
9. A clear solution for injection and infusion purposes and a process for its preparation substantially as herein described with reference to the examples.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7915514A GB2048063B (en) | 1979-05-03 | 1979-05-03 | Sulphonamide and potentiator solutions |
| NL8002488A NL8002488A (en) | 1979-05-03 | 1980-04-29 | SOLUTION OF SULPHONAMIDE AND POTENTIATOR, AND METHOD FOR PREPARING SUCH SOLUTION. |
| DK184880A DK184880A (en) | 1979-05-03 | 1980-04-29 | PROCEDURE FOR THE PREPARATION OF SOLUTON AMAMID SOLUTIONS AND POTENTIATORS FOR THESE |
| DE19803017032 DE3017032A1 (en) | 1979-05-03 | 1980-05-02 | A CLEAR INJECTION OR INFUSION SOLUTION CONTAINING A SULPHONAMIDE AND A POTENTIAL |
| IE901/80A IE49780B1 (en) | 1979-05-03 | 1980-05-02 | Solutions of sulphonamides and potentiators for same and their production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7915514A GB2048063B (en) | 1979-05-03 | 1979-05-03 | Sulphonamide and potentiator solutions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2048063A true GB2048063A (en) | 1980-12-10 |
| GB2048063B GB2048063B (en) | 1983-03-16 |
Family
ID=10504946
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7915514A Expired GB2048063B (en) | 1979-05-03 | 1979-05-03 | Sulphonamide and potentiator solutions |
Country Status (5)
| Country | Link |
|---|---|
| DE (1) | DE3017032A1 (en) |
| DK (1) | DK184880A (en) |
| GB (1) | GB2048063B (en) |
| IE (1) | IE49780B1 (en) |
| NL (1) | NL8002488A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU212498B (en) | 1992-11-06 | 1996-07-29 | Egyt Gyogyszervegyeszeti Gyar | Process for producing water-soluble pharmaceutical compositions, containing sulfachlorpyridazin-sodium and trimethoprim |
-
1979
- 1979-05-03 GB GB7915514A patent/GB2048063B/en not_active Expired
-
1980
- 1980-04-29 NL NL8002488A patent/NL8002488A/en not_active Application Discontinuation
- 1980-04-29 DK DK184880A patent/DK184880A/en not_active Application Discontinuation
- 1980-05-02 IE IE901/80A patent/IE49780B1/en unknown
- 1980-05-02 DE DE19803017032 patent/DE3017032A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| DK184880A (en) | 1980-11-04 |
| GB2048063B (en) | 1983-03-16 |
| IE49780B1 (en) | 1985-12-11 |
| DE3017032A1 (en) | 1980-11-13 |
| IE800901L (en) | 1980-11-03 |
| NL8002488A (en) | 1980-11-05 |
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