DE3153623C2 - - Google Patents
Info
- Publication number
- DE3153623C2 DE3153623C2 DE3153623A DE3153623A DE3153623C2 DE 3153623 C2 DE3153623 C2 DE 3153623C2 DE 3153623 A DE3153623 A DE 3153623A DE 3153623 A DE3153623 A DE 3153623A DE 3153623 C2 DE3153623 C2 DE 3153623C2
- Authority
- DE
- Germany
- Prior art keywords
- difluoromethyl
- diaminopentanoic acid
- bleomycin
- combination
- diaminopentanoic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/105—Aliphatic or alicyclic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
- A23K20/132—Heterocyclic compounds containing only one nitrogen as hetero atom
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Polymers & Plastics (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Animal Husbandry (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Feed For Specific Animals (AREA)
- Fodder In General (AREA)
Description
Die vorliegende Erfindung betrifft ein synergistisch wirksames Antiprotozoenmittel, insbesondere zur Bekämpfung von Protozoen-Infektionen bei Tieren, auf der Grundlage bekannter Antiprotozoenmittel, welche als Zusatzwirkstoff 2-Difluormethyl-2,5-diaminopentansäure der Formel (I)The present invention relates to a synergistically effective Antiprotozoal agents, in particular for combating Protozoan infections in animals, based known Antiprotozoenmittel which as an additive 2-Difluoromethyl-2,5-diaminopentanoic acid of the formula (I)
enthalten.contain.
Die Herstellung der Verbindung der Formel (I) und verwandter Amine ist in der DE-OS 31 23 295.7 beschrieben. Sie haben sich als wirksames Antiprotozoenmittel sowohl zur Therapie als auch zur Prophylaxe bei Tieren erwiesen.The preparation of the compound of formula (I) and Related amines is described in DE-OS 31 23 295.7. They have proven to be an effective antiprotozoal both for Therapy as well as for the prophylaxis in animals proved.
Dabei werden die obengenannten Diamine, die zur Klasse der irreversiblen Inhibitoren von Ornithincarboxylase gehören, z. B. in Form ihrer nicht toxischen Säureadditionssalze, wie in der DE-OS 31 23 295.7 beschrieben, in Kombination mit pharmazeutisch verträglichen Trägerstoffen oder als medizinisches Tierfutter zur Hemmung des Wachstums von Protozoen in Säugern, Fischen und insbesondere Geflügel eingesetzt. Der Ausdruck "Protozoen" umfaßt dabei die Glieder der Subphyla Sarcomastigophara und Sprozoa des Phylums Protozoen, jedoch nicht Leishmania, Trypanosoma cruzi und Trypanosoma lewisi.The above-mentioned diamines belonging to the class of include irreversible inhibitors of ornithine carboxylase, z. In the form of their non-toxic acid addition salts, such as described in DE-OS 31 23 295.7, in combination with pharmaceutically acceptable carriers or as a medical Animal feed for inhibiting the growth of protozoa used in mammals, fish and especially poultry. The term "protozoa" includes the members of the Subphyla sarcomastigophara and sprozoa of the phylum Protozoa, but not Leishmania, Trypanosoma cruzi and Trypanosoma lewisi.
Als besonders geeignet erwies sich gemäß der DE-OS 31 23 295.7 die Verbindung der Formel (I) bei der Bekämpfung des Erregers der Tsetse-Fliegen-Krankheit oder von Nagana, Eimeria tenella sowie zur Inhibierung des Wachstums von Darmcoccidiose bei kommerziellem Geflügel.Proved particularly suitable according to the DE-OS 31 23 295.7 the compound of formula (I) in the Fighting the pathogen of tsetse-fly disease or from Nagana, Eimeria tenella, as well as to inhibit growth of intestinal coccidiosis in commercial poultry.
Die Verbindung der Formel (I) kann dabei in einer Dosis von 5 mg/kg bis 7 g/kg verabreicht werden. Aufgrund ihrer ausgesprochen geringen Toxizität kann sie auch über das Trinkwasser angewendet werden.The compound of the formula (I) can be administered in a dose of 5 mg / kg to 7 g / kg. Because of her pronounced It can also be low on the drinking water be applied.
Verwandte α-Halomethylsubstituierte Amine sind in der US-PS 41 34 918 beschrieben. Diese werden als Inhibitoren der Ornithindecarboxylase bei verschiedenen Mikroorganismen und abnormen Zellwachstumsvorgängen verwendet. Es wird hier jedoch nicht vorgeschlagen, die genannten Amine zur Bekämpfung von Protozoen-Infektionen einzusetzen.Related α-halomethyl substituted amines are disclosed in US Pat 41 34 918 described. These are called inhibitors of Ornithine decarboxylase in various microorganisms and abnormal cell growth processes used. However, it is not proposed here, the said Amines used to combat protozoan infections.
Überraschend wurde nun gefunden, daß die Wirkung von bekannten Mitteln, die gegenwärtig für die Chemotherapie und Chemoprophylaxe von durch parasitäre Protozoen verursachten Krankheiten eingesetzt werden, durch Kombination mit der Verbindung der Formel (I) erhöht oder sogar potenziert wird, d. h. ein synergistischer Effekt erzielt wird, der zur Folge hat, daß die Menge an verabreichtem Wirkstoff herabgesetzt werden kann.Surprisingly, it has now been found that the effect of known Agents currently used for chemotherapy and Chemoprophylaxis caused by parasitic protozoa Diseases are used by combination with the Compound of formula (I) increased or even potentiated is, d. H. a synergistic effect is achieved, which leads to As a consequence, the amount of active ingredient administered is reduced can be.
Besonders bevorzugt und synergistisch wirkend ist dabei die Kombination von 2-Difluormethyl-2,5-diaminopentansäure gemäß Formel (I) mit den Antiprotozoenmitteln Antricid, Chinapyramin, Pentamidin bzw. Diisäthionat und Amincarbalid. Particularly preferred and synergistic acting is the Combination of 2-difluoromethyl-2,5-diaminopentanoic acid according to formula (I) with the antiprotozoal agents antricid, Chinapyramine, pentamidine or Diisäthionat and Amincarbalid.
Dabei kann die Konzentration der 2-Difluormethyl-2,5-diaminopentansäure um etwa das 4fache verringert werden, wenn sie in Kombination mit subcurativen Dosen (weniger als 1,0 mg/kg) dieser Arzneimittel verwendet wird.The concentration of 2-difluoromethyl-2,5-diaminopentanoic acid be reduced about 4 times, when used in combination with subcurative doses (less than 1.0 mg / kg) of these drugs.
Von besonderem Interesse bei der Behandlung von Trypanosomiasis im allgemeinen und insbesondere bei der Behandlung von Nagana bei Rindvieh, ist die Verwendung des Enzyminhibitors 2-Difluormethyl-2,5-diaminopentansäure in Kombination mit dem Antitumor-Antibiotikum Bleomycin. Dieser besondere Enzyminhibitor scheint mit Bleomycin synergistisch zu wirken. So werden Mäuse, die mit Trypanosoma brucei infiziert worden sind, nach drei Tagen bei täglicher i.p.-Verabreichung von Bleomycin in einer Dosis von 7 mg/kg geheilt. Auf ähnliche Weise werden Trypanosom-Infektionen bei Mäusen durch die Verabreichung von einer 1%igen Lösung 2-Difluormethyl-2,5-diaminopentansäure im Trinkwasser 3 Tage lang geheilt.Of particular interest in the treatment of trypanosomiasis in general and especially in the treatment from Nagana in cattle, is the use of the enzyme inhibitor 2-Difluoromethyl-2,5-diaminopentanoic acid in combination with the antitumor antibiotic bleomycin. This particular enzyme inhibitor seems synergistic with bleomycin to act. This is how mice with Trypanosoma brucei, after three days at daily i.p. administration of bleomycin at a dose of 7 mg / kg healed. Similarly, trypanosome infections in mice by the administration of a 1% solution 2-Difluoromethyl-2,5-diaminopentanoic acid in drinking water for 3 days long healed.
Die Ergebnisse mehrerer Kombinationsversuche zeigen an, daß Heilungen konsequenterweise mit 0,5 mg/kg Bleomycin in Kombination mit 0,5% 2-Difluormethyl-2,5-diaminopentansäure bei Verabreichung über das Trinkwasser erzielt werden. Wahlweise lassen sich Heilungen mit Konzentrationen von 0,25 mg/kg Bleomycin in Kombination mit nur 0,25% 2-Difluormethyl-2,5-diaminopentansäure im Trinkwasser erzielen. Eine Kombination von 0,1 mg/kg Bleomycin und 0,1% 2-Difluormethyl-2,5-diaminopentansäure hat keine Wirkung. Die heilenden Dosierungskombinationen spiegeln eine Reduktion der Bleomycin-Dosierung um 1/2 bis 1/28 der heilenden Dosis des alleine verwendeten Arzneimittels wieder, wenn es in Kombination mit einer subcurativen Dosis von 1/2 bis 1/4 der heilenden Dosis von 2-Difluormethyl-2,5-diaminopentansäure verwendet wird.The results of several combination experiments indicate that Healings consequently with 0.5 mg / kg bleomycin in Combination with 0.5% 2-difluoromethyl-2,5-diaminopentanoic acid be achieved when administered via the drinking water. Optional Cures can be achieved with concentrations of 0.25 mg / kg Bleomycin in combination with only 0.25% 2-difluoromethyl-2,5-diaminopentanoic acid achieve in drinking water. A Combination of 0.1 mg / kg bleomycin and 0.1% 2-difluoromethyl-2,5-diaminopentanoic acid has no effect. The Healing dosage combinations reflect a reduction Bleomycin dosage by 1/2 to 1/28 of the curative dose the drug used alone, if it is in Combination with a subcurative dose of 1/2 to 1/4 the curative dose of 2-difluoromethyl-2,5-diaminopentanoic acid is used.
Granulate, die zur Zugabe zum Trinkwasser von Geflügel geeignet sind, wurden wie folgt hergestellt:Granules for adding to the drinking water of poultry were prepared as follows:
Die 2-Difluormethyl-2,5-diaminopentansäure wurde mit etwa 6 bis 9 g Lactose vermischt und durch eine Strahlmühle oder Micronizer-Mühle geführt, um eine Teilchengröße von 1 bis 25 µm zu erzielen. 35 ml Wasser wurden zu etwa 2,5 g Maisstärke zugesetzt und vermischt, um eine 5%ige Stärkepaste zu erzielen. Das mikronisierte 2-Difluormethyl-2,5-diaminopentansäure-Lactosepulver, die restliche Lactose und die restliche Maisstärke wurden gut vermischt. Die Stärkepaste wurde zugesetzt und vermischt und das dabei entstehende Gemisch durch ein Sieb mit einer lichten Maschenweite von 1,41 mm gegeben. Die dabei entstehenden Granulate wurde bei 38°C auf einen Feuchtigkeitsgehalt von etwa 3% getrocknet, durch ein Sieb mit einer lichten Maschenweite von 1,41 mm gegeben und durch Vermischen mit 0,3 g Zinkstearat gleitend gemacht.The 2-difluoromethyl-2,5-diaminopentanoic acid was treated with about 6 to 9 g of lactose mixed and passed through a jet mill or Micronizer mill to a particle size of 1 to 25 microns to achieve. 35 ml of water became about Add 2.5 g cornstarch and mix to a 5% To achieve starch paste. The micronized 2-difluoromethyl-2,5-diaminopentanoic acid lactose powder, the remaining lactose and the remaining corn starch was mixed well. The Starch paste was added and mixed with it resulting mixture through a sieve with a light Mesh size of 1.41 mm given. The resulting Granules were at 38 ° C to a moisture content dried by about 3%, through a sieve with a light Mesh size of 1.41 mm and by mixing with 0.3 g of zinc stearate made lubricious.
Claims (3)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15997380A | 1980-06-16 | 1980-06-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3153623C2 true DE3153623C2 (en) | 1991-06-27 |
Family
ID=22574910
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19813123295 Granted DE3123295A1 (en) | 1980-06-16 | 1981-06-12 | "USE OF AN (ALPHA) SUBSTITUTED AMINO ACID OR AN (ALPHA) SUBSTITUTED AMINE TO COMBAT PROTOTOE INFECTIONS IN ANIMALS" |
| DE3153623A Expired - Lifetime DE3153623C2 (en) | 1980-06-16 | 1981-06-12 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19813123295 Granted DE3123295A1 (en) | 1980-06-16 | 1981-06-12 | "USE OF AN (ALPHA) SUBSTITUTED AMINO ACID OR AN (ALPHA) SUBSTITUTED AMINE TO COMBAT PROTOTOE INFECTIONS IN ANIMALS" |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS5731613A (en) |
| AT (1) | AT377180B (en) |
| AU (1) | AU544990B2 (en) |
| BE (1) | BE889230A (en) |
| CA (1) | CA1174603A (en) |
| CH (1) | CH651206A5 (en) |
| DE (2) | DE3123295A1 (en) |
| FR (1) | FR2484255A1 (en) |
| GB (1) | GB2078735B (en) |
| IE (1) | IE51300B1 (en) |
| IL (1) | IL63087A (en) |
| IT (1) | IT1171380B (en) |
| NL (1) | NL194153C (en) |
| NZ (1) | NZ197394A (en) |
| PH (1) | PH16634A (en) |
| SE (1) | SE460517B (en) |
| ZA (1) | ZA813953B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58123555U (en) * | 1982-02-17 | 1983-08-23 | 三菱電機株式会社 | In-line electron gun assembly equipment |
| NL8400927A (en) * | 1984-03-23 | 1985-10-16 | Philips Nv | DEVICE AND METHOD FOR MOUNTING AN INTEGRATED ELECTRON CANNON SYSTEM. |
| DE3421384A1 (en) * | 1984-06-08 | 1985-12-12 | Standard Elektrik Lorenz Ag, 7000 Stuttgart | DEVICE FOR ASSEMBLING ELECTRONIC RADIATOR GENERATORS |
| JPS62148462A (en) * | 1985-12-19 | 1987-07-02 | メレルダウフア−マス−テイカルズ インコ−ポレ−テツド | Novel method of controlling growth of protozoa |
| EP0326766B1 (en) * | 1988-02-05 | 1992-06-17 | Merrell Dow Pharmaceuticals Inc. | 5-substituted ornithine derivatives |
| US5455234A (en) * | 1994-03-16 | 1995-10-03 | Ahluwalia; Gurpreet S. | Inhibition of hair growth |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2828739A1 (en) * | 1977-07-11 | 1979-02-01 | Merrell Toraude & Co | ALPHA -HALOGEN METHYL DERIVATIVES OF ALPHA-AMINO ACIDS |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2392958A1 (en) * | 1977-06-01 | 1978-12-29 | Merck & Co Inc | NEW FLUORINE AMINO ACIDS USEFUL AS A MEDICINAL PRODUCT |
| US4088667A (en) * | 1977-07-01 | 1978-05-09 | Merrell Toraude Et Compagnie | Lower alkyl 2-tri-(lower)alkylsilylacetylene-N-carbethoxyglycinates and process for using same |
| US4139563A (en) * | 1977-07-01 | 1979-02-13 | Merrell Toraude Et Compagnie | α-ACETYLENIC DERIVATIVES OF AMINES |
| US4182891A (en) * | 1977-07-01 | 1980-01-08 | Merrell Toraude Et Compagnie | α-Acetylenic derivatives of α-amino acids |
| CA1121375A (en) * | 1977-07-01 | 1982-04-06 | Brian W. Metcalf | Derivatives of amines and amino acids |
| US4134918A (en) * | 1977-09-06 | 1979-01-16 | Merrell Toraude Et Compagnie | Alpha-halomethyl derivatives of amines |
-
1981
- 1981-06-11 NZ NZ197394A patent/NZ197394A/en unknown
- 1981-06-11 CA CA000379588A patent/CA1174603A/en not_active Expired
- 1981-06-11 AU AU71654/81A patent/AU544990B2/en not_active Expired
- 1981-06-11 PH PH25759A patent/PH16634A/en unknown
- 1981-06-11 SE SE8103678A patent/SE460517B/en not_active IP Right Cessation
- 1981-06-11 ZA ZA813953A patent/ZA813953B/en unknown
- 1981-06-12 DE DE19813123295 patent/DE3123295A1/en active Granted
- 1981-06-12 IE IE1308/81A patent/IE51300B1/en not_active IP Right Cessation
- 1981-06-12 IL IL63087A patent/IL63087A/en not_active IP Right Cessation
- 1981-06-12 DE DE3153623A patent/DE3153623C2/de not_active Expired - Lifetime
- 1981-06-15 CH CH3939/81A patent/CH651206A5/en not_active IP Right Cessation
- 1981-06-15 IT IT48684/81A patent/IT1171380B/en active
- 1981-06-15 AT AT0266581A patent/AT377180B/en not_active IP Right Cessation
- 1981-06-15 FR FR8111733A patent/FR2484255A1/en active Granted
- 1981-06-15 NL NL8102863A patent/NL194153C/en not_active IP Right Cessation
- 1981-06-15 JP JP9208181A patent/JPS5731613A/en active Granted
- 1981-06-15 GB GB8118326A patent/GB2078735B/en not_active Expired
- 1981-06-15 BE BE0/205104A patent/BE889230A/en not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2828739A1 (en) * | 1977-07-11 | 1979-02-01 | Merrell Toraude & Co | ALPHA -HALOGEN METHYL DERIVATIVES OF ALPHA-AMINO ACIDS |
Non-Patent Citations (2)
| Title |
|---|
| CA 91, 1979, Nr. 186171p S.S. Cohen, Science, Vol. 205, 7. Sept. 1979, S. 964- 971 * |
| Chemical Abstracts 92, 1980, Nr. 121677j * |
Also Published As
| Publication number | Publication date |
|---|---|
| AU544990B2 (en) | 1985-06-27 |
| IL63087A (en) | 1984-10-31 |
| PH16634A (en) | 1983-12-05 |
| FR2484255B1 (en) | 1984-12-14 |
| JPH0432052B2 (en) | 1992-05-28 |
| FR2484255A1 (en) | 1981-12-18 |
| BE889230A (en) | 1981-12-15 |
| IE51300B1 (en) | 1986-11-26 |
| IT1171380B (en) | 1987-06-10 |
| IT8148684A0 (en) | 1981-06-15 |
| SE8103678L (en) | 1981-12-17 |
| AU7165481A (en) | 1981-12-24 |
| CA1174603A (en) | 1984-09-18 |
| AT377180B (en) | 1985-02-25 |
| NL194153B (en) | 2001-04-02 |
| CH651206A5 (en) | 1985-09-13 |
| NL8102863A (en) | 1982-01-18 |
| ZA813953B (en) | 1982-06-30 |
| NL194153C (en) | 2001-08-03 |
| JPS5731613A (en) | 1982-02-20 |
| DE3123295A1 (en) | 1982-04-29 |
| ATA266581A (en) | 1984-07-15 |
| GB2078735A (en) | 1982-01-13 |
| DE3123295C2 (en) | 1990-07-12 |
| NZ197394A (en) | 1984-09-28 |
| SE460517B (en) | 1989-10-23 |
| GB2078735B (en) | 1985-05-15 |
| IE811308L (en) | 1981-12-16 |
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