CA1212325A - Antibacterial pharmaceutical composition and/or fodder premix and a process for the preparation thereof - Google Patents
Antibacterial pharmaceutical composition and/or fodder premix and a process for the preparation thereofInfo
- Publication number
- CA1212325A CA1212325A CA000450423A CA450423A CA1212325A CA 1212325 A CA1212325 A CA 1212325A CA 000450423 A CA000450423 A CA 000450423A CA 450423 A CA450423 A CA 450423A CA 1212325 A CA1212325 A CA 1212325A
- Authority
- CA
- Canada
- Prior art keywords
- fodder
- pharmaceutical composition
- chloro
- dimethylaminopropyl
- phenothiazine
- 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
Links
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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fodder In General (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Feed For Specific Animals (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
A b s t r a c t The invention relates to a novel antibacterial pharmaceutical composition which can be used especially in the veterinary medicine, and/or a fodder premix having antibacterial activity.
The novel pharmaceutical composition and/or fodder premix comprise 2-chloro-10-(3-dimethylamino-propyl)phenothiazine or a pharmacologically acceptable acid addition salt thereof, 2,4-diamino-5-(3',4',5'-trimethoxybenzyl)pyrimidine and 2-methyl-5,7-dicholor-8-hydroxyquinoline, furthermore carrier(s) employed in pharmaceutical compositions and/or fodder premixes.
The pharmaceutical compositions and/or fodder premixes of the invention ensure the efficient treatment of bacterial infections, especially the colitoxemia and enteritis of calf and enterotoxemia of weaned pig-lets, even in the case of bacterial which became resistant to antibiotics.
The novel pharmaceutical composition and/or fodder premix comprise 2-chloro-10-(3-dimethylamino-propyl)phenothiazine or a pharmacologically acceptable acid addition salt thereof, 2,4-diamino-5-(3',4',5'-trimethoxybenzyl)pyrimidine and 2-methyl-5,7-dicholor-8-hydroxyquinoline, furthermore carrier(s) employed in pharmaceutical compositions and/or fodder premixes.
The pharmaceutical compositions and/or fodder premixes of the invention ensure the efficient treatment of bacterial infections, especially the colitoxemia and enteritis of calf and enterotoxemia of weaned pig-lets, even in the case of bacterial which became resistant to antibiotics.
Description
~OYEL AN~I3ACTERIAL PHA~ACEUTICAL C01~PO~ITION AND/OP.
~ODD~R PREMIX AND A PROCESS OR T;~E PREPARATION THE~EO~
The invention relates to a novel antibacterial pharmaceutical composition which can be used esp2cially in the veterinary medicine, and/or to a fodder premiæ
having antibacterial activity.
The invention relate further to a process or preparing the said pharmaceutical composition and/or odder premix.
Serious economical problem3 arise from the bacterial injection of ~ew-born animal in the animal husbandry. Example of such infections are the coli-toxemia and enteritis ox calf and the e~terotoæemi~
and the Jo called oedem~ disease of weaned piglet In general, for the treatment of colito~emi~ ox calf and weaned piglet pharmaceutical compo3ition~ are used which contain sul~onamide~, lone or together with trimethoprim, or antibiotics t nitrofur~e or nitroimid-azole derivative a active gent, However, gr~du~
a reliance ha been developped against the known composition, therefore only moderate re~ult~ can`be achieYed whey using them. Similarly, treatments with vaccine are not ~ucce~ful, either.
It it desirable that in the treatment ox the infl~mm~tions of the digestive org~n~ it addition to - killing the bacteria causing the disease it que~tion7 ". ~LZ~Z~
~ODD~R PREMIX AND A PROCESS OR T;~E PREPARATION THE~EO~
The invention relates to a novel antibacterial pharmaceutical composition which can be used esp2cially in the veterinary medicine, and/or to a fodder premiæ
having antibacterial activity.
The invention relate further to a process or preparing the said pharmaceutical composition and/or odder premix.
Serious economical problem3 arise from the bacterial injection of ~ew-born animal in the animal husbandry. Example of such infections are the coli-toxemia and enteritis ox calf and the e~terotoæemi~
and the Jo called oedem~ disease of weaned piglet In general, for the treatment of colito~emi~ ox calf and weaned piglet pharmaceutical compo3ition~ are used which contain sul~onamide~, lone or together with trimethoprim, or antibiotics t nitrofur~e or nitroimid-azole derivative a active gent, However, gr~du~
a reliance ha been developped against the known composition, therefore only moderate re~ult~ can`be achieYed whey using them. Similarly, treatments with vaccine are not ~ucce~ful, either.
It it desirable that in the treatment ox the infl~mm~tions of the digestive org~n~ it addition to - killing the bacteria causing the disease it que~tion7 ". ~LZ~Z~
- 2 -~11 the physiological and biochemical proceaaes influenced by the pathogen germ or the producta, i,e, loin : thereof in an abnormal way should be re~tor~d to a normal level.
the invention aim at the elaboration of a pharma-ceutical composition a~d/or a fodder premix which enaure the e~ficie~t treatment of the di~eaaea listed above.
~urpri~in~ly9 it way found that the above objective i9 fulfilled by a pharmaceutical composition a~d/or a fodder premix comprising a active ~ent~ 2-chloro-10-~(3-dimeth~laminoprop~ phenothiflzine or a pharm~
cologic~ acceptable acid addition Walt thereof, further 2,4-diamino-5-(3',4',5'-trimetho~ybenzyl)pyrimidinne and ~-methyl-597-dichloro-8-hydro~yquinoline, In our experime~t~ a potentiated antibacterial action WQ~ experienced in vitro when using 2-chloro-10 (3-dimethylaminopropyl)phe~othiazi~e (chloroprom~zine) 9 2,4-diamino-5 (3',49,5'-trimetho~yben2yl~p~rimidine (trimethoprim) and 5,7-dichloro-2-methyl-8-hydro~y-: 20 qui~oline (chloroqui~aldol) ~imultaneousl~. The minimal inhibiting concentration ~MIC valuea) of the above compounda alone as well a ox the composition comprising all the three compound wers determined in a medium cont~ini~g phenolred and glucose (said medium it manufactured by Difco) gait the bacteria E~cherichia got 494, ~ordatella bro~chiseptica~ Staphylococcus aureu~
and ~i~teria monoc~toge~e~, The values given it Table I
in mg./l. correspond to the minimal co~centration~
inhibiting the growth of bacteria for 24 hours Table I
MIC value in mgO/l, in cave of Compound tested bacteria A B C
chloropromazine 50 200 25 25 trimethoprim 25 50 100 50 chloroquinaldol 200 5 5 5 a composition comprising 0.5 mg1o~
chloroprom~zine~
5 mg,of trimethoprim and chloroquin~ldol 25 0,5 0,5 0,5 A = Escherichia coli 494, reliant to chloramphenicol = 30rdatella bronchi~eptica C - Staphylococcus cures D = wisteria monocytogenes rom table I it can be teen that each ox the active substance inhibit the growth of the tested bacteria in a relatively high concentration. However, toe some inhibiting action it obtained with the qynergistic composition of the invention which comprise chloro-promazine in one hundredth ox the original concentration, trimethoprim it one filth ox the original concentration and chloroquin~ldol in one eigth to owe tenth of the original concentration. Alto the growth ox E~cherichia coli 494 reliant to chloramphenicol it inhibited by the ~2~L~3 synergistic composition ox the invention.
In addition to the active agent the pharmaceutic31 composition and/sr fodder premix ox the invention compri~e~
earner employed usually in pharmaceutical compo3itions and/or odder premi2es.
Preferred pharmaceutical compo~ition~ are the powder and the ~uspe~sions.
Suitable carriers in the powder of the invention are glucose; nicotin~mide; he~amethylene tetramine, polyvinyl p~rrolidone; ~ilicate~ such ~9 aluminium silicate or alumi~ium m~gne~ium trisilicate; silica; ~alicylic acid derivative such as acet~l ~alicylic acid or bismuth ~ub~alicylate etc.
: The carriers employed in the ~uspen~ion~ ox the inYention include, in general9 water and/or organic solvent; emulsifier; dispersing agent; suspending agent wetting agent; antioxidant; stabilizator; sweetenIng agent etch The carrier in the fodder premi~e~ of the i~ention include, in general, solid carrier such as wheat meal (fodder grade; whet barn, rice barn (free of oil); corn meal; ~oy~ meal; kqolin; zeolite; calcium carbonate; or liquid carriers, or e~mple water; saline;
organic solvents such as polyethylene glycols; furthermore emulsifier; di~per~i~g agent; upending agent; wetting agent; antioxidantp trace element, vitamins; inorganic salts etc.
2~3~S
The pharm~ceuticql compo~ition~ and/or fodder premixes of the invention comprise the chloropromazine or its pharmacologically acceptable acid addition salt, preferably the hydrochloride, the trimethoprim and the chloroquinaldol genera in a weight ratio of 1 : 6 : 6 to 1 : 50 : 100. The amount of the active agent in the pharmaceutical composition and/or odder premix ox the invention is suitably 1 to 90~per cent by weight, preferably 5 to 20 per cent by weight.
In general, 5 to 150 mg~ ox the mixture of the three active agents are employed or each ~g. of body weight during the treatment ox the animal, daily.
According to the proce~ ox the invention, the active agent, iOe~ the chloropromazine or a pharma-colo~ically acceptable acid addition salt thereof9 thetrimethoprim and the chloroquinaldol are admixed to one or more carrier, and the mixture obtained it trans-wormed unto a pharmaceutical composition and/or a fodder premix in a manner known per Leo It desired, the m xture of the active ~ubstance3 and the carrier groundedg especially in the preparation ox powders end premixesO
~u~pen~ions can be prepared directly before use by suspending the po~der~ in suitable liquid diluen~s, The active agent ox the pharmaceutical composi-tion and/or odder premix of toe invention aye known, , commercially available compou~d~
In ge~eral9 the pharmaceutical compo~ition~ ox the . . .
_ 6 _ invention are given or to the animal3, The fodder premix of the invention it admixed to the feed~tuff or drinking water in an amount that provides the daily dot required for the successful treatment, The pharmaceutical compositions and/or fodder premixes of the invention en.sure the efficient treatment of bacteriql in~ectio~, e~peciall~ the colitogemia and enteriti~ of calf and the enterotogemia of weaned pig-let, even it case of bacteria that became resistant to antibiotic further detail ox the invention are illustrated by means of the following ~on-limiting examples.
Example 1 0~5 g. of chloroprom~zine hydrochloride, 15 g. of trimethoprim? 15 g. of chloroquinaldol, 60 g, of acetyl ~alicylic acid, 50 gO of gluco2e, 20 g, ox nicotinamide, 35.5 g, of starch and 4 g, of silica are mixed and the mixture it ground in a hammer mill Calve hazing a body weight of 50 kg~ and : 20 ~uf~ering from enteriti~ are treated twice do with 5 g, of the powdered ml~ture suspended in 0.5 litre of c~momhle tea, each time The well stirred suspension it given orally to the a~imal~. The treatment it continued for 3 days.
Piglets hiving a body weight of 5 kg. are treated oral1y with 1 g. of the powdered mixture upended in ~5 ml. of water ~Z~L~325 Example 2 0,5 g. of chloropromazine hydrochloride, 55 g, of trimethoprim, 15 g. of chloroquinaldol, 40 g, of bismuth subsalicylate, 50 go of glucose, 20 g. of nicotinamide~
45.5 go of aluminium silicate, 10 g. of hexamethylene tetramine and 4 go of silica are mixed and ground in a ball mill, Before treatment, the powdered mi2ture is suspended in camomile tea or wqter a described in Example 1.
.,
the invention aim at the elaboration of a pharma-ceutical composition a~d/or a fodder premix which enaure the e~ficie~t treatment of the di~eaaea listed above.
~urpri~in~ly9 it way found that the above objective i9 fulfilled by a pharmaceutical composition a~d/or a fodder premix comprising a active ~ent~ 2-chloro-10-~(3-dimeth~laminoprop~ phenothiflzine or a pharm~
cologic~ acceptable acid addition Walt thereof, further 2,4-diamino-5-(3',4',5'-trimetho~ybenzyl)pyrimidinne and ~-methyl-597-dichloro-8-hydro~yquinoline, In our experime~t~ a potentiated antibacterial action WQ~ experienced in vitro when using 2-chloro-10 (3-dimethylaminopropyl)phe~othiazi~e (chloroprom~zine) 9 2,4-diamino-5 (3',49,5'-trimetho~yben2yl~p~rimidine (trimethoprim) and 5,7-dichloro-2-methyl-8-hydro~y-: 20 qui~oline (chloroqui~aldol) ~imultaneousl~. The minimal inhibiting concentration ~MIC valuea) of the above compounda alone as well a ox the composition comprising all the three compound wers determined in a medium cont~ini~g phenolred and glucose (said medium it manufactured by Difco) gait the bacteria E~cherichia got 494, ~ordatella bro~chiseptica~ Staphylococcus aureu~
and ~i~teria monoc~toge~e~, The values given it Table I
in mg./l. correspond to the minimal co~centration~
inhibiting the growth of bacteria for 24 hours Table I
MIC value in mgO/l, in cave of Compound tested bacteria A B C
chloropromazine 50 200 25 25 trimethoprim 25 50 100 50 chloroquinaldol 200 5 5 5 a composition comprising 0.5 mg1o~
chloroprom~zine~
5 mg,of trimethoprim and chloroquin~ldol 25 0,5 0,5 0,5 A = Escherichia coli 494, reliant to chloramphenicol = 30rdatella bronchi~eptica C - Staphylococcus cures D = wisteria monocytogenes rom table I it can be teen that each ox the active substance inhibit the growth of the tested bacteria in a relatively high concentration. However, toe some inhibiting action it obtained with the qynergistic composition of the invention which comprise chloro-promazine in one hundredth ox the original concentration, trimethoprim it one filth ox the original concentration and chloroquin~ldol in one eigth to owe tenth of the original concentration. Alto the growth ox E~cherichia coli 494 reliant to chloramphenicol it inhibited by the ~2~L~3 synergistic composition ox the invention.
In addition to the active agent the pharmaceutic31 composition and/sr fodder premix ox the invention compri~e~
earner employed usually in pharmaceutical compo3itions and/or odder premi2es.
Preferred pharmaceutical compo~ition~ are the powder and the ~uspe~sions.
Suitable carriers in the powder of the invention are glucose; nicotin~mide; he~amethylene tetramine, polyvinyl p~rrolidone; ~ilicate~ such ~9 aluminium silicate or alumi~ium m~gne~ium trisilicate; silica; ~alicylic acid derivative such as acet~l ~alicylic acid or bismuth ~ub~alicylate etc.
: The carriers employed in the ~uspen~ion~ ox the inYention include, in general9 water and/or organic solvent; emulsifier; dispersing agent; suspending agent wetting agent; antioxidant; stabilizator; sweetenIng agent etch The carrier in the fodder premi~e~ of the i~ention include, in general, solid carrier such as wheat meal (fodder grade; whet barn, rice barn (free of oil); corn meal; ~oy~ meal; kqolin; zeolite; calcium carbonate; or liquid carriers, or e~mple water; saline;
organic solvents such as polyethylene glycols; furthermore emulsifier; di~per~i~g agent; upending agent; wetting agent; antioxidantp trace element, vitamins; inorganic salts etc.
2~3~S
The pharm~ceuticql compo~ition~ and/or fodder premixes of the invention comprise the chloropromazine or its pharmacologically acceptable acid addition salt, preferably the hydrochloride, the trimethoprim and the chloroquinaldol genera in a weight ratio of 1 : 6 : 6 to 1 : 50 : 100. The amount of the active agent in the pharmaceutical composition and/or odder premix ox the invention is suitably 1 to 90~per cent by weight, preferably 5 to 20 per cent by weight.
In general, 5 to 150 mg~ ox the mixture of the three active agents are employed or each ~g. of body weight during the treatment ox the animal, daily.
According to the proce~ ox the invention, the active agent, iOe~ the chloropromazine or a pharma-colo~ically acceptable acid addition salt thereof9 thetrimethoprim and the chloroquinaldol are admixed to one or more carrier, and the mixture obtained it trans-wormed unto a pharmaceutical composition and/or a fodder premix in a manner known per Leo It desired, the m xture of the active ~ubstance3 and the carrier groundedg especially in the preparation ox powders end premixesO
~u~pen~ions can be prepared directly before use by suspending the po~der~ in suitable liquid diluen~s, The active agent ox the pharmaceutical composi-tion and/or odder premix of toe invention aye known, , commercially available compou~d~
In ge~eral9 the pharmaceutical compo~ition~ ox the . . .
_ 6 _ invention are given or to the animal3, The fodder premix of the invention it admixed to the feed~tuff or drinking water in an amount that provides the daily dot required for the successful treatment, The pharmaceutical compositions and/or fodder premixes of the invention en.sure the efficient treatment of bacteriql in~ectio~, e~peciall~ the colitogemia and enteriti~ of calf and the enterotogemia of weaned pig-let, even it case of bacteria that became resistant to antibiotic further detail ox the invention are illustrated by means of the following ~on-limiting examples.
Example 1 0~5 g. of chloroprom~zine hydrochloride, 15 g. of trimethoprim? 15 g. of chloroquinaldol, 60 g, of acetyl ~alicylic acid, 50 gO of gluco2e, 20 g, ox nicotinamide, 35.5 g, of starch and 4 g, of silica are mixed and the mixture it ground in a hammer mill Calve hazing a body weight of 50 kg~ and : 20 ~uf~ering from enteriti~ are treated twice do with 5 g, of the powdered ml~ture suspended in 0.5 litre of c~momhle tea, each time The well stirred suspension it given orally to the a~imal~. The treatment it continued for 3 days.
Piglets hiving a body weight of 5 kg. are treated oral1y with 1 g. of the powdered mixture upended in ~5 ml. of water ~Z~L~325 Example 2 0,5 g. of chloropromazine hydrochloride, 55 g, of trimethoprim, 15 g. of chloroquinaldol, 40 g, of bismuth subsalicylate, 50 go of glucose, 20 g. of nicotinamide~
45.5 go of aluminium silicate, 10 g. of hexamethylene tetramine and 4 go of silica are mixed and ground in a ball mill, Before treatment, the powdered mi2ture is suspended in camomile tea or wqter a described in Example 1.
.,
Claims (6)
1. A pharmaceutical composition and/or a fodder premix having antibacterial activity comprising 2-chloro-10-(3-dimethylaminopropyl)phenthiazine or a pharmacologically acceptable acid addition salt thereof, 2,4-diamino-5-(3',4',5'-trimethoxybenzyl)pyrimidine and 2-methyl-5,7-dichloro-8-hydroxyquinoline, further-more carrier(s) employed in pharmaceutical compositions and/or fodder premixes.
2. A pharmaceutical composition and/or a fodder premix as claimed in Claim 1 in which the pharmacolo-gically acceptable acid addition salt of 2-chloro-10-(3-dimethylaminopropyl)phenothiazine is 2-chloro-10-(3-dimethylaminopropyl)phenothiazine hydrochloride.
3. A pharmaceutical composition and/or a fodder premix as claimed in Claim 1 comprising 2-chloro-10-(3-dimethylaminopropyl-phenothiazine or a pharmacologic-ally acceptable acid addition salt thereof, 2,4-diamino--5-(3',4',5'-trimethoxybenyl)pyrimidine and 2-methyl-5,7-dichloro-8-hydroxyquinolins in a weight ratio of 1 : 6 : 6 to 1 : 50 : 100.
4. A process for preparing a pharmaceutical composition and/or a fodder premix having antibacterial activity in which 2-chloro-10-(3-dimethylaminopropyl)-phenothiazine or a pharmacologically acceptable acid addition salt thereof, 2,4-diamino-5-(3',4'.5'-trimethoxy-benzyl)pyrimidine and 2-methyl-5,7-dichloro-8-hydroxy-quinoline are admixed to carrier(s) and the mixture obtained is transformed into a pharmaceutical composition and/or a fodder premix.
5. A process as claimed in Claim 4 in which the pharmacologically acceptable acid addition salt of 2-chloro-10-(3-dimethylaminopropyl)phenothiazine is 2-chloro-10-(3-dimethylaminopropyl)phenothiazine hydro-chloride.
6. A process as claimed in Claim 4 in which 2-chloro-10-(3-dimethylaminopropyl)phenothiazine or a pharmacologically acceptable salt thereof, 2,4-diamino-5-(3 ,4 ,5 -trimethoxybenzyl)pyrimidine and 2-methyl-5,7-dichloro-8-hydroxyquinoline are employed in a weight ratio of 1 : 6 : 6 to 1 : 50 : 100.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU1011/83 | 1983-03-25 | ||
| HU831011A HU190078B (en) | 1983-03-25 | 1983-03-25 | Process for producing new antibacterial pharmaceutical composition and/or food-premix |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1212325A true CA1212325A (en) | 1986-10-07 |
Family
ID=10952443
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000450423A Expired CA1212325A (en) | 1983-03-25 | 1984-03-23 | Antibacterial pharmaceutical composition and/or fodder premix and a process for the preparation thereof |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0123157B1 (en) |
| JP (1) | JPS59210023A (en) |
| AT (1) | ATE27912T1 (en) |
| AU (1) | AU564187B2 (en) |
| CA (1) | CA1212325A (en) |
| DE (1) | DE3464331D1 (en) |
| ES (1) | ES8507346A1 (en) |
| HU (1) | HU190078B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11209206A (en) * | 1998-01-22 | 1999-08-03 | Takeda Chem Ind Ltd | Industrial antimicrobial agent |
| EP0951902A1 (en) * | 1998-03-31 | 1999-10-27 | Edmund J.H. Campion | A feed mixture |
| CN1976723B (en) * | 2004-04-30 | 2010-12-29 | Bkg制药有限公司 | Use of preparing medicine for treating or preventing infectious diseases |
-
1983
- 1983-03-25 HU HU831011A patent/HU190078B/en not_active IP Right Cessation
-
1984
- 1984-03-22 JP JP59053669A patent/JPS59210023A/en active Granted
- 1984-03-22 ES ES530884A patent/ES8507346A1/en not_active Expired
- 1984-03-23 CA CA000450423A patent/CA1212325A/en not_active Expired
- 1984-03-23 AU AU26068/84A patent/AU564187B2/en not_active Ceased
- 1984-03-26 AT AT84103280T patent/ATE27912T1/en not_active IP Right Cessation
- 1984-03-26 DE DE8484103280T patent/DE3464331D1/en not_active Expired
- 1984-03-26 EP EP84103280A patent/EP0123157B1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU2606884A (en) | 1984-09-27 |
| DE3464331D1 (en) | 1987-07-30 |
| AU564187B2 (en) | 1987-08-06 |
| JPS59210023A (en) | 1984-11-28 |
| EP0123157A1 (en) | 1984-10-31 |
| ES530884A0 (en) | 1985-10-01 |
| JPH0441127B2 (en) | 1992-07-07 |
| ATE27912T1 (en) | 1987-07-15 |
| EP0123157B1 (en) | 1987-06-24 |
| HU190078B (en) | 1986-08-28 |
| ES8507346A1 (en) | 1985-10-01 |
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Legal Events
| Date | Code | Title | Description |
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| MKEX | Expiry |