GB2158353A - Veterinary preparations - Google Patents
Veterinary preparations Download PDFInfo
- Publication number
- GB2158353A GB2158353A GB08510673A GB8510673A GB2158353A GB 2158353 A GB2158353 A GB 2158353A GB 08510673 A GB08510673 A GB 08510673A GB 8510673 A GB8510673 A GB 8510673A GB 2158353 A GB2158353 A GB 2158353A
- Authority
- GB
- United Kingdom
- Prior art keywords
- composition
- acid
- antiprotozoal
- antibacterial
- treatment
- 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.)
- Withdrawn
Links
- 238000002360 preparation method Methods 0.000 title description 8
- 239000000203 mixture Substances 0.000 claims abstract description 17
- KYGZCKSPAKDVKC-UHFFFAOYSA-N Oxolinic acid Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC2=C1OCO2 KYGZCKSPAKDVKC-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229960000321 oxolinic acid Drugs 0.000 claims abstract description 13
- 229960000210 nalidixic acid Drugs 0.000 claims abstract description 12
- MHWLWQUZZRMNGJ-UHFFFAOYSA-N nalidixic acid Chemical compound C1=C(C)N=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 MHWLWQUZZRMNGJ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 230000000241 respiratory effect Effects 0.000 claims abstract description 10
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 10
- 241001465754 Metazoa Species 0.000 claims abstract description 9
- 239000003904 antiprotozoal agent Substances 0.000 claims abstract description 9
- YXQXDXAHCSEVSD-GCYNEOGWSA-N dynamutilin Chemical compound OC(=O)\C=C\C(O)=O.CCN(CC)CCSCC(=O)O[C@@H]1C[C@@](C)(C=C)[C@@H](O)[C@H](C)[C@@]23CC[C@@H](C)[C@]1(C)[C@@H]2C(=O)CC3 YXQXDXAHCSEVSD-GCYNEOGWSA-N 0.000 claims abstract description 9
- 208000015181 infectious disease Diseases 0.000 claims abstract description 9
- 150000007524 organic acids Chemical class 0.000 claims abstract description 9
- 230000002195 synergetic effect Effects 0.000 claims abstract description 9
- 230000002496 gastric effect Effects 0.000 claims abstract description 5
- 235000005985 organic acids Nutrition 0.000 claims abstract description 5
- 239000004480 active ingredient Substances 0.000 claims description 7
- 239000000969 carrier Substances 0.000 claims description 5
- GUBGYTABKSRVRQ-QKKXKWKRSA-N lactose group Chemical group OC1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)[C@H](O2)CO)[C@H](O1)CO GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 5
- 239000002775 capsule Substances 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 239000008101 lactose Substances 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 210000000481 breast Anatomy 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 2
- 239000008158 vegetable oil Substances 0.000 claims description 2
- 230000037396 body weight Effects 0.000 claims 1
- UURAUHCOJAIIRQ-QGLSALSOSA-N tiamulin Chemical compound CCN(CC)CCSCC(=O)O[C@@H]1C[C@@](C)(C=C)[C@@H](O)[C@H](C)[C@@]23CC[C@@H](C)[C@]1(C)[C@@H]2C(=O)CC3 UURAUHCOJAIIRQ-QGLSALSOSA-N 0.000 description 8
- 229960004885 tiamulin Drugs 0.000 description 8
- 241000588724 Escherichia coli Species 0.000 description 6
- 241000282898 Sus scrofa Species 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 241000204031 Mycoplasma Species 0.000 description 5
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 4
- 241000588748 Klebsiella Species 0.000 description 4
- 230000001079 digestive effect Effects 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 210000000056 organ Anatomy 0.000 description 4
- 241000283690 Bos taurus Species 0.000 description 3
- 208000004232 Enteritis Diseases 0.000 description 3
- 241000186779 Listeria monocytogenes Species 0.000 description 3
- 241000191940 Staphylococcus Species 0.000 description 3
- 241000191967 Staphylococcus aureus Species 0.000 description 3
- 241000194017 Streptococcus Species 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 208000001848 dysentery Diseases 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 206010035664 Pneumonia Diseases 0.000 description 2
- 206010046793 Uterine inflammation Diseases 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 244000309466 calf Species 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000012009 microbiological test Methods 0.000 description 2
- 239000002547 new drug Substances 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- 244000144977 poultry Species 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- -1 2-diethylamino-ethyl Chemical group 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- 241000588769 Proteus <enterobacteria> Species 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 1
- 241000589886 Treponema Species 0.000 description 1
- 208000038016 acute inflammation Diseases 0.000 description 1
- 230000006022 acute inflammation Effects 0.000 description 1
- 230000000842 anti-protozoal effect Effects 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 229940064004 antiseptic throat preparations Drugs 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000000721 bacterilogical effect Effects 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 239000000890 drug combination Substances 0.000 description 1
- 239000003640 drug residue Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 208000004396 mastitis Diseases 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 210000002826 placenta Anatomy 0.000 description 1
- WXXVQWSDMOAHHV-UHFFFAOYSA-N quinoline-7-carboxylic acid Chemical compound C1=CC=NC2=CC(C(=O)O)=CC=C21 WXXVQWSDMOAHHV-UHFFFAOYSA-N 0.000 description 1
- 229960002771 retapamulin Drugs 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 1
- 229960001082 trimethoprim Drugs 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
Classifications
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/265—Esters, e.g. nitroglycerine, selenocyanates of carbonic, thiocarbonic, or thiocarboxylic acids, e.g. thioacetic acid, xanthogenic acid, trithiocarbonic acid
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
Abstract
Synergistic antibacterial-antiprotozoal drug compositions useful for the treatment of respiratory, gastrointestinal and urogenital infections of domestic animals comprises tiamulin hydrogen fumarate and microbiologically active organic acids, preferably oxolinic acid and nalidixic acid or a pharmaceutically acceptable water-soluble derivate thereof in a weight ratio of 1:5 to 5:1. The active components are admixed or diluted with a carrier used in veterinary therapy and formulated for oral or parenteral use.
Description
SPECIFICATION
New drug compositions and process for their preparation
The invention relates to new antibacterial and antiprotozoal drug compositions and a process for preparing same.
Oxolinic acid (5-ethyl-5, 8-dihydro-8-oxo-1, 3-dioxolo/4,5g/quinoline-7-carboxylic acid) and nalidixic acid (l-ethyl-l, 4-dihydro-7-methyl-4-oxo-1, 8-naphthyridine-3-carboxylic acid) are well known compounds in human medicine as well as in veterinary therapy. In the field of human medicine they are mainly used as urinary tract antiseptics. In veterinary therapy they are applied to fight infections caused by Gram-negative bacteria.
There are known combinations of oxolinic acid or nalidixic acid with antibiotics and other organic acids, too. Simultaneous application of oxolinic or nalidixic acid with trimethoprim was reported by Bartolini et al. [Bartolini et al., Drug. Exp. Clin. Res. 6, 311-316 (1980)].
Tiamulin (14-desoxy- 14-[(2-diethylamino-ethyl)-mercapto-acetoxy]-mutilin hydrogen fu ma rate) is a relatively new antibiotic in veterinary therapy. It is mainly used in the treatment of disorders of the repiratory and gastrointestinal tract of swine. It successfully cures swine dysentery and pneumonia caused by Mycoplasma [Burch et al., Vet. Rec. 10, 236-237 (1983)].
Tiamulin's effect on Gram-positive bacteria (Staphylococcus, Streptococcus), Mycoplasma and
Treponema is described in British patent specification No. 2,027,590.
The range of tiamulin's activity against Gram-negative bacteria is relatively narrow according to microbiological test results (Forster, J. and Pickles, G., IPVS Congress, Zagreb, June 13-15, 1978).
It is the object of the present invention to produce drug combinations of known antibiotics which, beside considerable reduction of expenses, will exhibit the individual effect of two or more components in a synergistic way.
Now it has been found that when tiamulin hydrogen fumarate is applied together with antibacterial and antiprotozoal organic acids, preferably oxolinic acid and/or nalidixic acid, beside the curing characteristics of the individual compounds differing in range of activity (e.g.
in vitro inhibitory effect on Shreptococci and E. coli) distinct synergism can be observed against certain strains.
Based on these facts the invention relates to new drug compositions of synergistic effect useful for the treatment of respiratory, gastrointestinal and urogenital infections of domestic animals, comprising the antibiotic tiamulin hydrogen fumarate and antibacterial-antiprotozoal organic acids, preferably oxolinic acid or nalidixic acid, or a pharmaceutically acceptable watersoluble derivative thereof in a weight ratio of 1:5 to 5:1, admixed with inert, pharmaceutically acceptable solid or liquid carriers.
The invention relates also to a process for preparing a new synergistic antibacterialantiprotozoal composition useful for the treatment of respiratory, gastrointestinal and urogenital infections of domestic animals, which comprises admixing tiamulin hydrogen fumarate with an antibacterial-antiprotozoal organic acid, preferably oxolinic or nalidixic acid, or a pharmaceutically acceptable water-soluble salt thereof in a weight ratio of 5:1 to 1:5, and with inert, non toxic carriers used in veterinary therapy.
Microbiological tests were carried out to investigate the in vitro inhibitory effect of the active compounds against different strains of bacteria and to state their synergism. For better understanding, the same field isolates of pathogens were used as test organisms. Minimal inhibiting concentrations (MIC) and minimal bactericide concentrations (MBC) of tiamulin and oxolinic or nalidixic acid were determined. The results are shown in Tables I and II. The MIC and MBC values were measured in yg/ml units.
Table I
Intensification of the Antibacterial Activity of the 1:1 Ratio by Weight Combination of Tiamulin
and Oxolinic Acid
Test Organism Tiamulin Oxolinic Acid Combination Grade of
MIC MBC MIC MBC MIC MBC Intensification
Staphylococcus aureus 25 100 25 50 5 25 4 - 10x ------------------------------------------------------------------------------------------------------------
Listeria monocytogenes 50 100 100 100 5 25 8 - 40x -------------------------------------------------------------------------------------------------------------
Salmonells typhi-murium 200 200 1 10 1 1 2 - 400x --------------------------------------------------------------------------------------------------------------
Klebsiella pneumonise 200 200 5 10 5 5 2 - 80x Table II
Intensification of the Antibacterial Activity of the 1::1 Ratio by Weight Combination of Tiamulin and
Nalidixic Acid
Test Organism Tiamulin Nalidixic Acid Combination Grade of Inten
MIC MBC MIC MBC MIC MBC sification
Staphylococcus aureus 25 100 5 200 5 5 4 - 80x ------------------------------------------------------------------------------------------------------------
Listeria monocytogenes 50 100 200 200 50 100 8 - 8x -------------------------------------------------------------------------------------------------------------
Salmonells typhi-murium 200 200 10 10 10 10 2 - 40x --------------------------------------------------------------------------------------------------------------
Klebsiella pneumonise 200 200 50 50 50 50 2 - Bx The in vitro tests prove the synergistic effect of the combination against certain strains of bacteria.The intensification of the effect is clearly shown against Staphylococcus aureus, Listeria monocytogenes, Klebsiella pneumoniae and Salmonella typhi-murium. The grade of intensification is 2 to 8 times in the average, but it can reach even the 400 times level.
Because of their synergistic properties, the preparations of the invention may be applied in lower and more economic doses. As a result of the broadened range of spectrum, the combinations can be successfully used in the therapy of respiratory and other diseases owing to mycoplasma and secondary bacterial complications.
Further advantage of the combinations according to the invention is the reduced possibility of development of toxic side-effects and the shortening of the necessary withdrawal period to prevent drug residues in edible tissues. These advantages originate from the reduced doses of the active components in the combinations.
The preparations of the invention can be produced according to known technics, that is the active ingredients are mixed with or dissolved in carriers used in veterinary therapy.
The formulation of the preparate is chosen according to the given case. It may be applied orally, mixed to the feed or in drinking water, mainly in large scale units, or parenterally for individual or mass treatment.
The parenteral application may be intra-muscular, intrauterin or intracysternal. The preparation for parental use is spread on a carrier, preferably lactose, in 1:1 to 1:50 ratio by weight, and then it is dissolved in a suitable solvent, preferably water, dimethyl formamid or vegetable oil, in a 1:1 to 1:25 ratio by weight.
Favourable effects can be reached with the synergistic drug compositions of the invention in case of enteritis due to Salmonella, Klebsiella and E. coli strains;
-metritis caused by Proteus, E. coli, Streptococcus, Staphylococcus strains;
-mastitis caused by Streptococcus, Staphylococcus, E. coli, Klebsiella and Mycoplasma strains of cattle, calves and dogs; iseases of the digestive and respiratory organs of swine (e.g. E. coli diarrhoea, swine dysentery, pneumonia caused by Mycoplasma); ---diseases of the digestive and respiratory organs of rabbits and poultry (E. coli infections, etc.).
The proposed oral dose of the water-soluble preparation containing 60.0% by weight of active ingredient is -in case of enteritis 400 mg/animal/day for calves 350 mg/liter for piglets -in case of enteritis and urinary infections 200-400 mg/animal/day for dogs.
When the feed is medicated with a premix containing 60.0% of active ingredient, the recommanded dose for a continuous five-day treatment is -in case of infections of the digestive and respiratory organs and swine dysentery 200-400 mg/kg feed for swine -in case of infections of the digestive and respiratory organs 150-250 mg/kg feed for rabbits and 300-400 mg/kg feed for poultry.
For intrauterinal use a daily dose of 5.0g of the mixture containing 60% of active ingredients in capsules is proposed.
The use of the preparations of the invention is not limited against the pathogens or to the treatment of species listed above or in the following examples.
Example 1
1.5 g of tiamulin hydrogen fumarate, 1.5 g of oxolinic acid and 2.0 g of lactose are admixed and filled into an intrauterine capsule. 24 cows were treated intrauterinally with these capsules immediately after calving for 3 consecutive days. Involution quickened, metritis and retention of placenta did not develop. Bacterial infections were prevented by the treatment.
Example 2
0.6 g of tiamulin hydrogen fumarate, 3.0 g of nalidixic acid and 1.4 9 of lactose are admixed. The preparation is suspended in 100 ml of water.
50 piglets of 5 litters were treated orally with 1.0 ml of the suspension. Clinical symptoms disappeared in all of the animals after the first treatment. New cases or relapse did not occur.
Example 3
10.0 g of tiamulin hydrogen fumarate and 2.0 g of oxolinic acid are suspended in 1 00.0 ml of oil for injection.
10 ml of this suspension was infused intracysternally via the teat canal of 5 mastitic cows.
The symptoms of acute inflammations (swollen and warm udder, macroscopic change of the milk secreted etc.) considerably abated after the first treatment. Bacteriological tests carried out a week after the third treatment gave fully negative results.
Claims (9)
1. A synergistic antibacterial-antiprotozoal drug composition useful for the treatment of diseases of respiratory, gastrointestinal and urogenital infections of domestic animals, comprising tiamulin hydrogen fumarate and antibacterial-antiprotozoal organic acids or a pharmaceutically acceptable water-soluble derivative thereof in a weight ratio of 1:5 to 5:1 admixed with inert, non-toxic solid or liquid carriers used in veterinary therapy.
2. A composition as claimed in claim 1, in which the organic acid is oxolinic acid or nalidixic acid.
3. A composition as claimed in claim 1 for oral administration, comprising the active ingredients in a dose of 5-1 5 mg/kg body weight.
4.. A composition as claimed in claim 1, wherein the carrier is lactose.
5. A composition as claimed in claim 4 for intrauterinal application, comprising the active ingredients in a ratio of 60% by weight of the mixture filled in capsule in a daily dose of 5.0 g/animal.
6. A composition as claimed in claim 1, wherein the carrier is purified and sterile vegetable oil acceptable in veterinary therapy.
7. A composition as claimed in claim 6 for intracysternal application, comprising the active ingredients in a quantity of 0.2 to 2.0 g/quarter of udder.
8. A process for preparing a new synergistic antibacterial-antiprotozoal composition useful for the treatment of respiratory, gastrointestinal and urogenital infection of domestic animals, which comprises admixing tiamulin hydrogen fumarate with an antibacterial-antiprotozoal organic acid or a pharmaceutically acceptable water-soluble salt thereof in a weight ratio of 5:1 to 1:5, and with inert, non toxic carriers used in veterinary therapy.
9. A process as claimed in claim 8, wherein oxolinic or nalixidic acid is used as organic acid.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU841681A HU192982B (en) | 1984-04-28 | 1984-04-28 | Process for producing synergetic pharmaceutical compositions containing thiamulin and antibacterial and antiprotozoal organic acids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB8510673D0 GB8510673D0 (en) | 1985-06-05 |
| GB2158353A true GB2158353A (en) | 1985-11-13 |
Family
ID=10955659
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08510673A Withdrawn GB2158353A (en) | 1984-04-28 | 1985-04-26 | Veterinary preparations |
Country Status (11)
| Country | Link |
|---|---|
| AT (1) | AT388669B (en) |
| BE (1) | BE902250A (en) |
| CH (1) | CH666407A5 (en) |
| DE (1) | DE3515185A1 (en) |
| ES (1) | ES8607333A1 (en) |
| GB (1) | GB2158353A (en) |
| HU (1) | HU192982B (en) |
| IT (1) | IT1200461B (en) |
| LU (1) | LU85870A1 (en) |
| NL (1) | NL8501061A (en) |
| SE (1) | SE8502038L (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4041563A1 (en) * | 1990-12-22 | 1992-06-25 | Sanol Arznei Schwarz Gmbh | METHOD FOR PRODUCING ACTIVE MICROPARTICLES FROM HYDROLYTICALLY DEGRADABLE POLYMERS |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2027590A (en) * | 1978-08-14 | 1980-02-27 | Squibb & Sons Inc | Parenteral compositions containing tiamulin |
| GB2035800A (en) * | 1978-10-20 | 1980-06-25 | Ausonia Farma Srl | Pharmaceutical compositions containing anantibiotic and a beta ketoacid |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1208279A (en) * | 1967-05-12 | 1970-10-14 | Ici Ltd | Veterinary compositions containing 4-hydroxy-1,8-naphthyridine derivatives |
| GB2072012B (en) * | 1980-03-14 | 1984-07-25 | Squibb & Sons Inc | Veterinary compositions containing pleuromutilin derivatives |
-
1984
- 1984-04-28 HU HU841681A patent/HU192982B/en not_active IP Right Cessation
-
1985
- 1985-04-11 NL NL8501061A patent/NL8501061A/en not_active Application Discontinuation
- 1985-04-22 BE BE1/011243A patent/BE902250A/en not_active IP Right Cessation
- 1985-04-24 AT AT0122985A patent/AT388669B/en not_active IP Right Cessation
- 1985-04-24 CH CH1749/85A patent/CH666407A5/en not_active IP Right Cessation
- 1985-04-26 GB GB08510673A patent/GB2158353A/en not_active Withdrawn
- 1985-04-26 LU LU85870A patent/LU85870A1/en unknown
- 1985-04-26 SE SE8502038A patent/SE8502038L/en not_active Application Discontinuation
- 1985-04-26 ES ES542610A patent/ES8607333A1/en not_active Expired
- 1985-04-26 IT IT20515/85A patent/IT1200461B/en active
- 1985-04-26 DE DE19853515185 patent/DE3515185A1/en not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2027590A (en) * | 1978-08-14 | 1980-02-27 | Squibb & Sons Inc | Parenteral compositions containing tiamulin |
| GB2035800A (en) * | 1978-10-20 | 1980-06-25 | Ausonia Farma Srl | Pharmaceutical compositions containing anantibiotic and a beta ketoacid |
Also Published As
| Publication number | Publication date |
|---|---|
| CH666407A5 (en) | 1988-07-29 |
| NL8501061A (en) | 1985-11-18 |
| GB8510673D0 (en) | 1985-06-05 |
| SE8502038L (en) | 1985-10-29 |
| AT388669B (en) | 1989-08-10 |
| ATA122985A (en) | 1989-01-15 |
| BE902250A (en) | 1985-10-22 |
| ES542610A0 (en) | 1986-05-16 |
| LU85870A1 (en) | 1986-11-05 |
| ES8607333A1 (en) | 1986-05-16 |
| HUT37347A (en) | 1985-12-28 |
| IT8520515A0 (en) | 1985-04-26 |
| HU192982B (en) | 1987-08-28 |
| SE8502038D0 (en) | 1985-04-26 |
| IT1200461B (en) | 1989-01-18 |
| DE3515185A1 (en) | 1985-11-07 |
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