GB2260268A - Injectable veterinary compositions comprising sulfamethoxazole and trimethoprim - Google Patents
Injectable veterinary compositions comprising sulfamethoxazole and trimethoprim Download PDFInfo
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- GB2260268A GB2260268A GB9221114A GB9221114A GB2260268A GB 2260268 A GB2260268 A GB 2260268A GB 9221114 A GB9221114 A GB 9221114A GB 9221114 A GB9221114 A GB 9221114A GB 2260268 A GB2260268 A GB 2260268A
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- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
An injectable veterinary composition that is free from toxic side effects contains 0.8 - 6 parts by weight of 2,4-diamino-- 5-[3',4',5'-trimethoxybenzyl]-pyrimidine 4 to 30 parts by weight of 3-[4-aminophenylsulfonamido]-5-methylisoxazole 25 to 65 parts by weight of one or more organic solvent(s) being miscible with water, 1 to 40 parts by weight of water, 3 to 12 parts by weight of one or more solubilising agent(s), 2 to 10 parts by weight of urea and 0.2 to 4 parts by weight of one or more additive(s).
Description
An injectable veterinary composition being free from toxic side effects and a process for the preparation thereof
The invention relates to an injectable veterinary composition being free from toxic side effects, wherein the active substance consists of 2,4-diemino-5-/3,4,5-trimetho=y- benzyl/-pyrimidine and 3-/4-aminophenylsulfonamido/-5-methyl- isoxazole, and a process for the preparation of the composition.
The injectable veterinary composition of the invention can be employed in the veterinary therapy for the treatment of various infections of bacterial origin.
It is well knovni that the ection of sulfonedes is pctentiated by 2,4-diamino-5-/3',4',5,-trimethoxybenzyl/ -pyrimidine /trimethoprim/ t3ritish Patent Specification No.
1 176 395 . A sulfonamide employed very often is 3-/4-aminophenylsulfonamido/-5-methylisoxezole /sulfamethoxazole/, and pharmaceutical compositions comprising trimethoprim and sulfamethoxazole that can be administered orally are rather wiQe -spread.
In the veterinary medicine, especially for the treatment of animals of big body such as cattle, pig and sheep, injectable compositions are needed. It is a basic requirement that the injectable composition should be free from toxic side effects, i.e. it should not cause irreversible changes at the plece of injection or in the vicinity thereof.
In the preparatior. of stable solutions comprising triretho prim and sulfamethoxazole as the active substance, it is a serious problem that a weak acid /i.e. sulfamethoxazole/ is to be combined with a weak base /i.e. trimethoprim/ usually in a ratio other then the one require by stoichiometry.
According to the 3ritish Patent Specification No. 1 176 395 it was turfed to solve the problem by adding the aqueous solution of a salt of sulfamethoxazole to a solution of tri methoprzz in an organic acid e.g. ethanol, poly/ethylene glycol/ or dinethyl acetamide. However, the pM value of the solution obtained is 8 to 11, thus, the tissue is injured by this known injectable solution after administration.
ashen the pH of the solution is adjusted to a lower value near the neutral one, an insoluble complex compound consisting of sulfamethoxazole and trimethoprim may separate from the solution. Cn the other hand, in case of sterilizing the solution of basic pE value, the sulfonamide is often oxidized due to the application of heat. To avoid the above deficiencies a solution having a pM value of 4 to 6, preferably 4.5 to 5.5 was prepared according to British Patent Specification No.
1 469 521. For this purpose, the active substances are dissolved in a mixture of various organic solvents in the presence of an organic acid. However, the injectable composition obtained is also toxic to the tissue.
In accordance with the published European Patent Applicatio: No. 37501, a water-soluble salt of sulfamethoxazole and trimethoprim are dissolved in water together with an eldehyde such as formaldehyde. A complex is formed in the solution having a pM value of 8.6 to 9.6. This value is also too high, the physiologically acceptable value being equivalent to about 7.4, thus, the tissue of the animal is irritated by this known injectable solution, too.
According to the publisl:ed German patent Application No.
25 38 678 lyophilized trnmethopnii is dissolved, directly before use, in a solution of sulf2-.etho^2zo'e in an organic acid comprising poly/vinylpyrrolidone/, too. Although a solution having a pn value of 7.2 to 7.6 is obtaned, it is stable only for a sort tire, thus, the solution cannot be stored for a longer time than 12 hours, in general.
According to the British Patent Specification No.
2 066 068 the active substances are dissolved in N,N-dimethylacetamide, and to the solution obtained poly/ethylene glycol/ and ethyl oleate are added. Although the injectable solution obtained has a pTh value of 7,5 to 8 and possesses a rather prolonged action due to the presence of ethyl oleate, it has the drawback of comprising N,N-dimethylacetamide that is toxic to the tissue. Thus, in the area of administration of the in:ectable solution a bloody infla=natory focus is developped which is necrotized or an abscess is formed. The lesion is accompanied by string pain and results in reducing the growth and weight gein of the animal. In addition, the lesion of the muscle has serious consequences from meat hygienic point of view.
The aim of the invention to produce an injectable veterinary composition comprising sulfamethoxezole and tri methoprin and being practically free from the above toxic side effects.
It has been found that the above aim is achieved by the corposition of the invention comprising 0.8 to 6 parts by weight of 2,4-diamino-5-/3',4',5'-trimethoxabenzyl/-pyrimidine, 4 to 30 parts by weight of 3-/4-aminophenylsulfonnnido/-5 -methylisoxazole, 25 to 65 parts by weight of one or more organic solvent/s/ being miscible with water, 1 to 40 parts by weight oi water, 3 to 12 parts by weight of one or more solubilizing agent/s/, 2 to 1C parts by weight of urea end
C.2 to 4 parts by weight of one or more addsstive/s/.
in the composition of the invention the organic solvent being miscible with water is preferably ethanol and/or poly /ethylene glycol/. Preferred solubilizing agent is poly/vinylpyrrolidone/ and/or hexamethylene tetramine. In general, the additive is an antioxidant such as potassium pyrosulfite, glutathione in reduced fon gamma-L-glutaml--cysteinyl- glycine 7 etc. and/or a mono-, di- or tricarboxylic acid having 3 to 6 carbon atoms and substituted by a hydroxyl or amino group e.g. lactic acid, citric acid, glutamic acid, epsilon aminocaproic acid etc. The composition of the invention can comprise more then one antioxidants and more than one organic acid of the above category, too.
A preferred composition of the invention comprises 1.5 to 5.5 parts by weight of 2,4-diamino-5-/3',4',5'-trimethoxy- benzyl/-pyrimidine, 8 to 27 parts by weight of 3-/4-amino- phenylsulfamido/-5-methylisoxazole, 8 to 10 parts by weight of ethanol, 48 to 55 parts by weight of poly/ethylene glycol/, 1 to 40 parts by weight of water, 4 to 10 parts by weight of poly/vinylpyrrolidone/, 0.7 to 1.1 parts by weight of hexamethylene tetramine, 3 to 10 parts by weight of urea, 0.08 to 0.3 parts by weigh of an antioxidant and C.4 to 1.5 parts by weight of a mono-, di- or tricarboxylic acid having 3 to 6 carbon atoms and substituted by a hydroxyl or amino group.
The composition of the invention is prepared by blending the ingredients thereof. Thus, 0.8 to 6 parts by weight of 2,4-diamino-5-/3',4',5'-trimethoxybenzal/-pyrimidine, 4 to 30 parts by weight of 3-/4-aminophenylsulfonamido/-5-methyl- -soxazole, 25 to 65 parts by weight of one or more organic solvent/s/ being Lvascible with water, 1 to 40 parts by weight of water, 3 to 12 parts by weight of one or more stabilizing agent/s/, 2 to 10 parts by weight of urea and 0.2 to 4 parts by weight of one or more additive/s/ are blended, and the mixture obtained is transformed into an injectable veterinary composition.
It is preferred to dissolve the solubilizing agent or a part thereof, e.g. the poly/vinylpyrrolidone/, furthermore the organic acid in water. Then, the organic solvent being miscible .t:: waTer or a part thereof is added to the aqueous solution obtained. The trimethoprim is dissolved in the mixture obtained, ten the antioxidant, urea, sulfamethoxazole and the remaining part of the solubilizing agent are added to the solution. \fE.en dissolution is complete, the solution is filtered, the clear filtrate is filled into bottles or ampouls which are sealed and sterilized by means of heat.
The order of addition of certain components can be changed, however, it is preferred to dissolve trimethoprim at first, and to add sulfamethoxazole to the aqueous solution comprising the organic solvent/s/ and trimethoprim.
A preferred composition of the invention is prepared by blending 1.5 to 5.5 parts by weight of 2,4-diamino-5-/3',4',5'- -trimethoxybenzyl/-pyrimidine, 8 to 27 parts by weight of 3-/4-aminophenylsulfonamido/-5-methylisoxazole, 8 to 10 parts by weight of ethanol, 48 to 55 parts by weight of poly/ethylene glycol/, 1 to 4C parts by weight of water, 4 to 10 parts by weight of poly/vinylpyrrolidone/, C.7 to 1.1 pert by weight of he abeth~olene tetramre, 3 to 10 parts by weight of urea, 0.8 to 0.3 parts by weight of an antioxidant and 0,4 to 1,5 parts bt; ieg::- a a mono-, ~ cr tricarboxylic acid having 3 to 6 carbon atoms and substituted by a hydroxyl or amino group, and transforming the mixture obtained into an injectable veterinary conpostion.
The composition of the invention has a pH value of 6 to 7.
The injectable veterinary composition of the invention was examined from the point of view of tissue injury, and, surprisingly, it was found that extremely weak tissue injuries are experienced in contrast to the known injectable veterinary compositions causing even tissue necrosis.
Thus, healthy white meat type pigs of 24 to 34 kg body weight were treated intramuscularly with the composition of
Example 1 of the invention. The reference substance was the composition of Example 1 of the Erltish Patent Specification
Nr. 2 066 068 comprising identical quantities of the active ingredients. Does of 1 ml/16 kg body weight were injected into the longissimus muscle of thorax. The animals were observed for 14 days after the treatment, then bleeded to death. The longissimus muscles of thorax were sliced up transversally, and the areas indicating alterations were examined histologicall
In case of injecting the composition of the invention, after 6 hours, a small alteration of about a lentil's area was observed. The elteration did not increase in the next days.
After 14 days, the alterations became completely organized leaving a tendinous scar tissue.
In case of injecting the Knows composition used as the reference, after 6 hours, a necrotised area of about a bean's growth was observed. On the first day, the necrotise: area increased. On 14 ays, te r..ucle neurosis developped did not organize, thus, te above tests clearly indicate that the injectable vet erinar:: composition of te invention practically does not injure the viss~es a t:a place cf inject or ano in the vicinity thereof.
The injectable veterinary composition of the invention is ckaracterized by a relatively prolonged elimination, i.e. the therapeutic activity lasts for a longer time, however, elimination fro the organism comes about in a short time. These characteristics of the conposition of the invention were tested on sucking calf. The composition of Example 1 was administered intramuscularly in a dose of 1 ml/10 kg body weight, and blood samples ere taken from the animals in predetermined time intervals, the sulfamethoxazole and trimethoprim levels were determined, then the elimination half time of the active ingredients and the value of residue in the 6th day after administration were calculated. The data obtained are shown in Table 1.
Table 1
elimination half time and residue on sucking calf
Elimination Residue on the 6th day
Active ingredient half time after administration
in minutes in mg/kg
Sulfamethoxazole 850 0.1
Trimethoprim 485 0.05 Drom Table 1 it can be seen tat the intramuscular inject of the veterinary composition of the invention produces therapeutic action for a relatively long time since half of the amount of the active ingredients administered leaves the organism in as muck as 1t and 8 hours, respectively.In the same time, after the therapeutic action the active ingredients are cu~crlz eliminated as shown b the quantity of residue on the t day being onl about one hun-edth of the amount injected originally.
Thus, the injectable veterinary composition of the invention is free from any significant acute or chronic side effect, dpes not reduce either the growth or the weight gain of the animals and no unfavourable consequences are experienced from the hygienic point of view of the meat when the treated animals are cut. The composition of the invention can be prepared in a simple way without the use of special carriers.
The invention is further elucidated by means of the following Examples.
Example 1
To 20 g of distilled water 5 g of poly/vinylpyrrolidone/, 1.4 g of lactic acid and 10 g of 96 per cent ethanol are added and in the mixture obtained 4 g of trimethoprim are dissolved.
To the clear solution 49.8 g of poly/ethylene glycol/ having a polymerization degree of 300, 0.15 g of reduced glutathipne, 0.05 g of potassium pyrosulfite and 3 g of urea are added, and in the mixture obtained 20 g of sulfamethoxazole and 0.75 g of hexamethylene tetramine are dissolved. The solution obtained is filtered, filled into bottles or ampouls that are sealed and sterilized at 120 C for 20 minutes.
Ampouls prepared in this way has been stored at roon temperature for 2 years. No opalescence, discolouration or setaration on of matter has been observed.
xa=ple 2
6 g of poly/vinylpyrrolidone/ end 0.42 g of citric acid are dissolved in 30 g of distilled water. 8 g of 96 per cent ethanol and 55 g of poly/ethylene glycol having a polymerizatic degree of 200 ere added and in the mixture obtained 1.6 g of trimethoprim are dissolved. In the clear solution obtained 4 g of urea, 0.08 g of reduced glutathione, 0.1 g of potassium pyrosulfite, 8 g of sulfamethoxazole and 0.9 g of hexamethylene tetramine are dissolved. Then, the procedure described in example 1 is followed.
example 3
1.4 g of lectic acid are dissolved in 4 g of d st lled water, 4 g of poly/vinylpyrrolidone/, 55 g of poly/ethalene glycol/ having a polymerization degree of 300 and 10 g of 96 per cent ethanol are added and in the solution obtained 5.3 g of trimethoprim are dissolved. To the clear solution 0.05 g of potassium pyrosulfite, 6.5 g of urea, 0,25 g of reduced glutathione, 26.5 g of sulfamethoxazole and 1.1 g of hexamethylene tetramine are added. Then, the procedure described in
Example 1 is followed.
Example 4
go 54 g of poly/ethylene glycol/ having a polymerization degree of 300 1 g of epsilon-aminocaproic acid, 6 ml of distilled water, 8 g of poly/vinylpyrrolidone/ and 10 g of 96 per cent ethanol are added, in the mixture obtained 4 g of trimethoprim are dissolved and to the solutIon obtained 0,1 g of reduced glutathione, 1G g of urrea, C,C8 g of potassium pyrosulfite, 20 g of sulfamethoxazole and 0.9 g of hexamethylene tetramine are added. Then, the procedure given in Example 1 is followed.
Example 5
0.8 g of glutamic acid and 10 g of polY/vinalpyrrol done/ are dissolved in 12 g of distilled water and 53.1 g of poly /ethylene glycol/ having a polymerization degree of 200 and 10 g of 96 per cent ethanol are added. In the solution obtained 4 g of trimethoprim are dissolved, then 0.08 g of potassium pyrosulfite, 0,15 g of reduced glutathione, 3 g of urea, 20 g of sulfamethoxazole and 1 g of hexamethylene tetramine are added, and the procedure given in Example 1 is followed.
Claims (12)
1. An injectable veterinary composition being free fe toc side effects, wherein te active substance consists of 2,4-diamino-5-/3',4',5'-trimethoxybenzyl/-pyrimidine end 3-/4-aminophenylsulfonamido/-5-methylisoxazole, comprising 0.8 to 6 parts by weight of 2,4-diamino-5-/3',4',5' -trimethoxybenzyl/-pyrinidine, 4 to 30 parts by weight of 3-/4-aninophenylsulfonanido/-5-methylisoxazole, 25 to 65 parts by weight of one or more organic solvent/s/ being miscible with water, 1 to 40 parts by weight of water, 3 to 12 parts by weight of one or more solubilizing egent/s/, 2 to 10 parts by weight of urea end C.2 to 4 parts by weight of one or more additive/s/.
2. An injectable veterinary composition as claimed in Clam 1, in which the organic solvent consists of ethanol and/or poly/ethylene glycol/.
3. An ingectable veterinary composition as claimed in
Claim 1 or 2, in which the solubilizing agent consists of poly/vinylpyrrolidone/ and/or hexamethylene tetramine.
4. An injectable veterinary composition as claimed in any of Claims 1 to 3, in which the additive consists of an antioxidant anchor a mono-, di- dr tricarboxylic ecid having 3 to 6 carbon atoms end substituted by a hydroxy or amino group.
5. An inectable veterinary composition as claimed in any of Claims 1 to 4 comprising 1.5 to 5.5 parts bg weight of 2,4-diamino-5-/3',4',5'-t-imethoxybenzyl/-pyrimid 8 to 27 parts by weight of 3-/4-aminophenylsulfonamido/-5-methyl- isoxazole, 8 to 1C parts by weight cf ethanol, 48 to 55 parts b weight of poly/ethylene glycol/, 1 to 4C parts by tight of water, 4 to 10 parts by weight of poly/vinylpyrrolidone/, 0.7 to 1.1 parts b weight of hexamethylene tetramine, 3 to 10 parts b eight of urea, C.C8 to 0.3 parts 5 weight of an antioxidant and 0.4 to 1.5 parts by weight of a mono-, di- or tricarboxylic acid having 3 to 6 carbon atoms and substituted by a hydroxyl or amino group.
6. A process for the preparation of an injectable veterinary composition being free from toxic side effects, wherein the active substance consists of 2,4-diamino-5-/3',4',5' -trimetho ybenzyl/-pyrimidine and 3-/4-aminophenylsulfonamido/- -5-methyllsoxazole, in which 0.8 to 6 parts by weight of 2,4-diamino-5-/3',4',5'- -trimethoxybenzyl/-pyrimidine, 4 to 30 parts by weight of 3-/4-aminophenylsulfonamido/-5-methylisoxazole, 25 to 65 parts by weight of one or more organic solvent/s/ being miscible with water, 1 to 40 parts by weight of water, 3 to 12 parts by weight of one or more solubilizing agent/s/, 2 to 10 parts by weight of urea and 0.2 to 4 parts by weight of one or more additive/s/ are blended and the mixture obtained is transformed into en injectable veterinary composition.
7. A process as claimed in Claim 6, in which the organic solvent consists of ethanol and/or poly/ethylene glycol/.
8. A process as claImed in Claim 6 or 7, in which the solubilizing agent consists of poly/vinylpyrrolidone/ and/or hexamethylene tetramine.
9. A process as claimed in any of Claims 6 to 8, in which The additive consists of an antioxidant and/or a mono-, dior tricarboxylic acid having 3 to 6 carbon atoms and substituted by a hydroxy or amino group.
C. A process as claimed en z o C12~.-.S 6 to 9, in which 1.5 to 5.5 parts by eght of 2,4-:iamino-5-/3',A',5'-tr - methoxybenzyl/-pyrimidine, 8 to 27 parts by weight of 3-/4- -aminophenylsulfonamido/-5-methylisosazole, 8 to
10 parts by weight of ethanol, 48 to 55 parts by weight of poly/ethylene glycol/, 1 to 40 parts by weight of water, 4 to 10 parts by weight of poly/vinylpyrrolidone/, 0.7 to 1.1 parts by weight of hexamethylene tetramine, 3 to 10 parts by weight of urea, 0,C8 to 0.3 parts by weight of an antioxidant and 0.4 to 1.5 parts by weight of a mono-, di- or tricarboxylic acid having 3 to 6 carbon atoms and substituted by a hydroxyl or amino group are blended and the mixture obtained is transformed into an injectable veterinary composition.
11. An injectable composition substantially as hereinbefore described in any one of Examples 1 to 5.
12. A method as claimed in claim 6, substantially as hereinbefore described in any one of Examples 1 to 5.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU322291A HU210693B (en) | 1991-10-11 | 1991-10-11 | Process for producing pharmaceutical compositions for injections without tissue damages, containing sulfamethoxazol and trimetoprime |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB9221114D0 GB9221114D0 (en) | 1992-11-18 |
| GB2260268A true GB2260268A (en) | 1993-04-14 |
| GB2260268B GB2260268B (en) | 1995-06-07 |
Family
ID=10963176
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9221114A Expired - Fee Related GB2260268B (en) | 1991-10-11 | 1992-10-07 | Injectable veterinary compositions comprising sulfamethoxazole and trimethoprim |
Country Status (11)
| Country | Link |
|---|---|
| CN (1) | CN1035468C (en) |
| BR (1) | BR9203951A (en) |
| CZ (1) | CZ309392A3 (en) |
| GB (1) | GB2260268B (en) |
| HU (1) | HU210693B (en) |
| LT (1) | LT3063B (en) |
| MX (1) | MX9205808A (en) |
| RO (1) | RO112241B1 (en) |
| RU (1) | RU2059408C1 (en) |
| SK (1) | SK309392A3 (en) |
| YU (1) | YU91492A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7201928B1 (en) | 1999-09-21 | 2007-04-10 | Rutgers, The State University Of New Jersey | Extracts of orange peel for prevention and treatment of cancer |
| RU2603623C2 (en) | 2014-06-06 | 2016-11-27 | Олег Ильич Эпштейн | Veterinary composition and method for improving viability of animals, stimulation of body weight gain in mammals and birds, increasing efficiency of immunising, preventing and/or treating infectious diseases (versions) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0022342A2 (en) * | 1979-07-05 | 1981-01-14 | Pfizer Inc. | Sulfonamide solutions |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2538678A1 (en) | 1975-08-30 | 1977-03-03 | Boehringer Mannheim Gmbh | Injectable solns. contg. trimethoprim and sulphamethoxazole - of physiologically tolerable pH and contg. only small amts. of organic solvents |
| US4303643A (en) * | 1979-07-05 | 1981-12-01 | Pfizer Inc. | Sulfonamide compositions |
| HU180740B (en) * | 1979-11-27 | 1983-04-29 | Egyt Gyogyszervegyeszeti Gyar | Process for producing sulfonamide-containing,injectable pharmaceutical composition of prolongated activity |
| JPS57109713A (en) * | 1980-12-26 | 1982-07-08 | Shionogi & Co Ltd | Pharmaceutical preparation of combined agent of sulfamethoxazole and trimethoprim for medication through celom |
-
1991
- 1991-10-11 HU HU322291A patent/HU210693B/en not_active IP Right Cessation
-
1992
- 1992-10-07 GB GB9221114A patent/GB2260268B/en not_active Expired - Fee Related
- 1992-10-09 CZ CS923093A patent/CZ309392A3/en unknown
- 1992-10-09 MX MX9205808A patent/MX9205808A/en unknown
- 1992-10-09 RU SU5052925 patent/RU2059408C1/en active
- 1992-10-09 RO RO9201296A patent/RO112241B1/en unknown
- 1992-10-09 SK SK309392A patent/SK309392A3/en unknown
- 1992-10-09 YU YU91492A patent/YU91492A/en unknown
- 1992-10-09 BR BR929203951A patent/BR9203951A/en not_active Application Discontinuation
- 1992-10-12 LT LTIP165A patent/LT3063B/en not_active IP Right Cessation
- 1992-10-12 CN CN92111683A patent/CN1035468C/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0022342A2 (en) * | 1979-07-05 | 1981-01-14 | Pfizer Inc. | Sulfonamide solutions |
Also Published As
| Publication number | Publication date |
|---|---|
| SK309392A3 (en) | 1995-03-08 |
| CZ309392A3 (en) | 1994-02-16 |
| LTIP165A (en) | 1994-03-25 |
| CN1035468C (en) | 1997-07-23 |
| MX9205808A (en) | 1993-07-01 |
| YU91492A (en) | 1995-12-04 |
| HU913222D0 (en) | 1992-01-28 |
| HU210693B (en) | 1995-06-28 |
| GB2260268B (en) | 1995-06-07 |
| RO112241B1 (en) | 1997-07-30 |
| BR9203951A (en) | 1993-04-27 |
| LT3063B (en) | 1994-10-25 |
| GB9221114D0 (en) | 1992-11-18 |
| RU2059408C1 (en) | 1996-05-10 |
| CN1071576A (en) | 1993-05-05 |
| HUT64839A (en) | 1994-03-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19981007 |