GB1586510A - Veterinery compositions containing pleuromutilin derivatives - Google Patents
Veterinery compositions containing pleuromutilin derivatives Download PDFInfo
- Publication number
- GB1586510A GB1586510A GB52715/77A GB5271577A GB1586510A GB 1586510 A GB1586510 A GB 1586510A GB 52715/77 A GB52715/77 A GB 52715/77A GB 5271577 A GB5271577 A GB 5271577A GB 1586510 A GB1586510 A GB 1586510A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- compound
- composition
- group
- ppm
- 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
- 239000000203 mixture Substances 0.000 title claims description 26
- ZRZNJUXESFHSIO-VYTKZBNOSA-N pleuromutilin Chemical class C([C@H]([C@]1(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]2C)OC(=O)CO)C)C[C@]32[C@H]1C(=O)CC3 ZRZNJUXESFHSIO-VYTKZBNOSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 33
- 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 claims description 20
- 229960004885 tiamulin Drugs 0.000 claims description 20
- 239000002460 polyether antibiotic agent Substances 0.000 claims description 18
- 229930191564 Monensin Natural products 0.000 claims description 15
- GAOZTHIDHYLHMS-UHFFFAOYSA-N Monensin A Natural products O1C(CC)(C2C(CC(O2)C2C(CC(C)C(O)(CO)O2)C)C)CCC1C(O1)(C)CCC21CC(O)C(C)C(C(C)C(OC)C(C)C(O)=O)O2 GAOZTHIDHYLHMS-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- BBMULGJBVDDDNI-OWKLGTHSSA-N lasalocid Chemical compound C([C@@H]1[C@@]2(CC)O[C@@H]([C@H](C2)C)[C@@H](CC)C(=O)[C@@H](C)[C@@H](O)[C@H](C)CCC=2C(=C(O)C(C)=CC=2)C(O)=O)C[C@](O)(CC)[C@H](C)O1 BBMULGJBVDDDNI-OWKLGTHSSA-N 0.000 claims description 15
- 229960005358 monensin Drugs 0.000 claims description 15
- GAOZTHIDHYLHMS-KEOBGNEYSA-N monensin A Chemical compound C([C@@](O1)(C)[C@H]2CC[C@@](O2)(CC)[C@H]2[C@H](C[C@@H](O2)[C@@H]2[C@H](C[C@@H](C)[C@](O)(CO)O2)C)C)C[C@@]21C[C@H](O)[C@@H](C)[C@@H]([C@@H](C)[C@@H](OC)[C@H](C)C(O)=O)O2 GAOZTHIDHYLHMS-KEOBGNEYSA-N 0.000 claims description 15
- 229930182504 Lasalocid Natural products 0.000 claims description 13
- 229960000320 lasalocid Drugs 0.000 claims description 13
- 244000144977 poultry Species 0.000 claims description 11
- 239000012141 concentrate Substances 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 6
- 229920000570 polyether Polymers 0.000 claims description 6
- 208000003495 Coccidiosis Diseases 0.000 claims description 5
- 206010023076 Isosporiasis Diseases 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- QZVSDERYSHAHPU-LFEMCTADSA-N (2r)-2-[(2s,3r,4s,5s,6s)-2-hydroxy-6-[[(2r,3r,4r,5s,6r,7r,9s)-2-[(5s)-5-[(2r,5r)-5-[(3s,5r,6s)-6-hydroxy-3,5,6-trimethyloxan-2-yl]oxolan-2-yl]oxolan-2-yl]-3,7-dimethoxy-2,4,6-trimethyl-1,10-dioxaspiro[4.5]decan-9-yl]methyl]-4-methoxy-5-[(2s,5s,6r)-5-metho Chemical compound C1([C@H]2CC[C@@H](O2)[C@@H]2CCC(O2)[C@@]2(C)O[C@]3([C@H](C)[C@H]2OC)[C@@H]([C@H](OC)C[C@@H](C[C@H]2[C@]([C@@H](OC)[C@@H](C)[C@@](O)([C@@H](C)C(O)=O)O2)(C)O[C@@H]2O[C@H](C)[C@@H](OC)CC2)O3)C)O[C@](C)(O)[C@H](C)C[C@@H]1C QZVSDERYSHAHPU-LFEMCTADSA-N 0.000 claims description 4
- SWWGWDNMHHFFCT-UHFFFAOYSA-N Antibiotic A 204A Natural products CCCC(OCC1CCC(O1)C2(C)OC3(OC(CC4OC(O)(C(C)C(=O)O)C(C)C(OC5CCC(OC)C(C)O5)C4(C)OC)CC(OC)C3C)C(C)C2OC)C6OC(C)(O)C(C)C(OC)C6C SWWGWDNMHHFFCT-UHFFFAOYSA-N 0.000 claims description 4
- QZVSDERYSHAHPU-UHFFFAOYSA-N Septamycin Natural products COC1C(C)C2(C(C(OC)CC(CC3C(C(OC)C(C)C(O)(C(C)C(O)=O)O3)(C)OC3OC(C)C(OC)CC3)O2)C)OC1(C)C(O1)CCC1C(O1)CCC1C1OC(C)(O)C(C)CC1C QZVSDERYSHAHPU-UHFFFAOYSA-N 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 4
- 239000003651 drinking water Substances 0.000 claims description 4
- 235000020188 drinking water Nutrition 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- ZITSQIZMRMDQLE-SJSJOXFOSA-N (2R)-2-[(2R,3S,6R)-6-[[(2S,4R,5R,6R,7R,9R)-2-[(2R,5S)-5-[(2R,3S,5R)-5-[(2S,3S,5R,6S)-6-hydroxy-3,5,6-trimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-7-methoxy-2,4,6-trimethyl-1,10-dioxaspiro[4.5]decan-9-yl]methyl]-3-methyloxan-2-yl]propanoic acid Chemical compound CO[C@@H]1C[C@@H](C[C@H]2CC[C@H](C)[C@@H](O2)[C@@H](C)C(O)=O)O[C@]2(O[C@@](C)(C[C@H]2C)[C@H]2CC[C@](C)(O2)[C@@H]2O[C@H](C[C@@H]2C)[C@H]2O[C@](C)(O)[C@H](C)C[C@@H]2C)[C@@H]1C ZITSQIZMRMDQLE-SJSJOXFOSA-N 0.000 claims description 2
- BKZOUCVNTCLNFF-IGXZVFLKSA-N (2s)-2-[(2r,3r,4s,5r,6s)-2-hydroxy-6-[(1s)-1-[(2s,5r,7s,8r,9s)-2-[(2r,5s)-5-[(2r,3s,4r,5r)-5-[(2s,3s,4s,5r,6s)-6-hydroxy-4-methoxy-3,5,6-trimethyloxan-2-yl]-4-methoxy-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-7-methoxy-2,8-dimethyl-1,10-dioxaspiro[4.5]dec Chemical compound O([C@@H]1[C@@H]2O[C@H]([C@@H](C)[C@H]2OC)[C@@]2(C)O[C@H](CC2)[C@@]2(C)O[C@]3(O[C@@H]([C@H](C)[C@@H](OC)C3)[C@@H](C)[C@@H]3[C@@H]([C@H](OC)[C@@H](C)[C@](O)([C@H](C)C(O)=O)O3)C)CC2)[C@](C)(O)[C@H](C)[C@@H](OC)[C@@H]1C BKZOUCVNTCLNFF-IGXZVFLKSA-N 0.000 claims description 2
- ZNBNBTIDJSKEAM-NISBWGIBSA-N (2s,3r,4r)-4-[(2s,5r,7s,8r,9s)-7-hydroxy-2-[(2r,5s)-5-[(2r,3s,5r)-5-[(2s,3s,5r,6r)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2-methyl-3-propanoyloxypentanoic a Chemical compound C1[C@H](O)[C@@H](C)[C@@H]([C@@H](C)[C@@H](OC(=O)CC)[C@H](C)C(O)=O)O[C@]11O[C@](C)([C@@H]2O[C@@](C)(CC2)[C@H]2[C@H](C[C@@H](O2)[C@@H]2[C@H](C[C@@H](C)[C@](O)(CO)O2)C)C)CC1 ZNBNBTIDJSKEAM-NISBWGIBSA-N 0.000 claims description 2
- FELYAZAWTURXNF-KWJIWYEDSA-N (E,2S,4R,8S)-8-[(2S,5R,7S,8R,9R)-7-hydroxy-2-[(2R,4S,5S,7R,9S,10R)-2-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-9-[(2S,5S,6R)-5-methoxy-6-methyloxan-2-yl]oxy-4,10-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2,4,6-trimethyl-5-oxonon-6-enoic acid Chemical compound O1[C@H](C)[C@@H](OC)CC[C@H]1O[C@@H]1[C@@H](C)[C@]2([C@H](C[C@@H](O2)[C@@H]2[C@H](C[C@@H](C)[C@](O)(CO)O2)C)C)O[C@@H]([C@@]2(C)O[C@]3(O[C@@H]([C@H](C)[C@@H](O)C3)[C@@H](C)\C=C(/C)C(=O)[C@H](C)C[C@H](C)C(O)=O)CC2)C1 FELYAZAWTURXNF-KWJIWYEDSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- ZITSQIZMRMDQLE-UHFFFAOYSA-N Grisorixin Natural products O1C2(C(CC(C)(O2)C2OC(C)(CC2)C2C(CC(O2)C2C(CC(C)C(C)(O)O2)C)C)C)C(C)C(OC)CC1CC1CCC(C)C(C(C)C(O)=O)O1 ZITSQIZMRMDQLE-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- RWWSBGHRGAQGJE-UHFFFAOYSA-N Laidlomycin Natural products CC(C(CCC(=O)O)C(C)C(=O)O)C1OC2(CCC(C)(O2)C3CCC(C)(O3)C4OC(CC4C)C5OC(O)(CO)C(C)CC5C)CC(O)C1C RWWSBGHRGAQGJE-UHFFFAOYSA-N 0.000 claims description 2
- BBZNPMRJIHRUOP-UHFFFAOYSA-N Lasalocid B Natural products C=1C=C(CC)C(O)=C(C(O)=O)C=1CCC(C)C(O)C(C)C(=O)C(CC)C(C(C1)C)OC1(CC)C1CCC(O)(CC)C(C)O1 BBZNPMRJIHRUOP-UHFFFAOYSA-N 0.000 claims description 2
- PUHPUNCBWZEKHZ-UHFFFAOYSA-N Lasalocid C Natural products CCC(CCc1ccc(C)c(O)c1C(=O)O)C(O)C(C)C(=O)C(CC)C2OC(CC)(CC2C)C3CCC(O)(CC)C(C)O3 PUHPUNCBWZEKHZ-UHFFFAOYSA-N 0.000 claims description 2
- KCHKLBGNALUYAJ-UHFFFAOYSA-N Lasalocid D Natural products O1C(CC)(C2OC(C)C(O)(CC)CC2)CC(C)C1C(CC)C(=O)C(CC)C(O)C(C)CCC1=CC=C(C)C(O)=C1C(O)=O KCHKLBGNALUYAJ-UHFFFAOYSA-N 0.000 claims description 2
- BKZOUCVNTCLNFF-UHFFFAOYSA-N Lonomycin Natural products COC1C(C)C(C2(C)OC(CC2)C2(C)OC3(OC(C(C)C(OC)C3)C(C)C3C(C(OC)C(C)C(O)(C(C)C(O)=O)O3)C)CC2)OC1C1OC(C)(O)C(C)C(OC)C1C BKZOUCVNTCLNFF-UHFFFAOYSA-N 0.000 claims description 2
- KTQFYFLZDLTLAH-UHFFFAOYSA-N Lysocellin Natural products CCC(O)C1(CC)CC(C)C(O)(O1)C2(C)CC(C)C(O2)C(CC)C(=O)C(C)C(O)C(C)C3OC(O)(CC(=O)O)C(C)CC3C KTQFYFLZDLTLAH-UHFFFAOYSA-N 0.000 claims description 2
- RXCDHVAYLRJHOW-UHFFFAOYSA-N Na salt-Lasalocid E Natural products C=1C=C(C)C(O)=C(C(O)=O)C=1CCC(C)C(O)C(C)C(=O)C(CC)C(C(C1)CC)OC1(CC)C1CCC(O)(CC)C(C)O1 RXCDHVAYLRJHOW-UHFFFAOYSA-N 0.000 claims description 2
- KQXDHUJYNAXLNZ-XQSDOZFQSA-N Salinomycin Chemical compound O1[C@@H]([C@@H](CC)C(O)=O)CC[C@H](C)[C@@H]1[C@@H](C)[C@H](O)[C@H](C)C(=O)[C@H](CC)[C@@H]1[C@@H](C)C[C@@H](C)[C@@]2(C=C[C@@H](O)[C@@]3(O[C@@](C)(CC3)[C@@H]3O[C@@H](C)[C@@](O)(CC)CC3)O2)O1 KQXDHUJYNAXLNZ-XQSDOZFQSA-N 0.000 claims description 2
- 239000004189 Salinomycin Substances 0.000 claims description 2
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims description 2
- 230000003115 biocidal effect Effects 0.000 claims description 2
- UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical class [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 claims description 2
- LLHRMWHYJGLIEV-UHFFFAOYSA-N desoxy Chemical group COC1=CC(CCN)=CC(OC)=C1C LLHRMWHYJGLIEV-UHFFFAOYSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- DANUORFCFTYTSZ-UHFFFAOYSA-N epinigericin Natural products O1C2(C(CC(C)(O2)C2OC(C)(CC2)C2C(CC(O2)C2C(CC(C)C(O)(CO)O2)C)C)C)C(C)C(OC)CC1CC1CCC(C)C(C(C)C(O)=O)O1 DANUORFCFTYTSZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229960004561 laidlomycin Drugs 0.000 claims description 2
- BBMULGJBVDDDNI-UHFFFAOYSA-N lasalocid A Natural products C=1C=C(C)C(O)=C(C(O)=O)C=1CCC(C)C(O)C(C)C(=O)C(CC)C(C(C1)C)OC1(CC)C1CCC(O)(CC)C(C)O1 BBMULGJBVDDDNI-UHFFFAOYSA-N 0.000 claims description 2
- KTQFYFLZDLTLAH-DESDHLEASA-N lysocellin Chemical compound O1[C@]([C@@H](O)CC)(CC)C[C@@H](C)[C@]1(O)[C@@]1(C)O[C@H]([C@@H](CC)C(=O)[C@@H](C)[C@@H](O)[C@H](C)[C@@H]2[C@H](C[C@@H](C)[C@](O)(CC(O)=O)O2)C)[C@@H](C)C1 KTQFYFLZDLTLAH-DESDHLEASA-N 0.000 claims description 2
- DANUORFCFTYTSZ-BIBFWWMMSA-N nigericin Chemical compound C([C@@H]1C[C@H]([C@H]([C@]2([C@@H](C[C@](C)(O2)C2O[C@@](C)(CC2)C2[C@H](CC(O2)[C@@H]2[C@H](C[C@@H](C)[C@](O)(CO)O2)C)C)C)O1)C)OC)[C@H]1CC[C@H](C)C([C@@H](C)C(O)=O)O1 DANUORFCFTYTSZ-BIBFWWMMSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- -1 salimonycin Chemical compound 0.000 claims description 2
- 229960001548 salinomycin Drugs 0.000 claims description 2
- 235000019378 salinomycin Nutrition 0.000 claims description 2
- 238000011282 treatment Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 238000011260 co-administration Methods 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 description 4
- 229940088710 antibiotic agent Drugs 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229920002261 Corn starch Polymers 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 241000223932 Eimeria tenella Species 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 210000000287 oocyte Anatomy 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 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
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
-
- 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)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fodder In General (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Feed For Specific Animals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1625876A CH627940A5 (de) | 1976-12-23 | 1976-12-23 | Kokzidiostatisches kombinationspraeparat. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1586510A true GB1586510A (en) | 1981-03-18 |
Family
ID=4415757
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB52715/77A Expired GB1586510A (en) | 1976-12-23 | 1977-12-19 | Veterinery compositions containing pleuromutilin derivatives |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4148890A (https=) |
| JP (1) | JPS5386038A (https=) |
| BE (1) | BE862145A (https=) |
| CH (1) | CH627940A5 (https=) |
| DE (1) | DE2755339A1 (https=) |
| FR (1) | FR2374903A1 (https=) |
| GB (1) | GB1586510A (https=) |
| IT (1) | IT1143623B (https=) |
| NL (1) | NL7714043A (https=) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4933364A (en) * | 1979-07-11 | 1990-06-12 | International Minerals & Chemical Corp. | Process for promoting growth and feed efficiency of food producing mammals |
| US4356264A (en) * | 1980-04-11 | 1982-10-26 | International Minerals & Chemical Corp. | Zinc-containing antibiotic agents |
| US4378433A (en) * | 1980-04-11 | 1983-03-29 | International Minerals & Chemical Corporation | Method for producing zinc etheromycin from fermentation broths |
| IE49936B1 (en) * | 1979-07-11 | 1986-01-08 | Int Minerals & Chem Corp | Zinc-containing antibiotic agents |
| US4478935A (en) * | 1980-10-08 | 1984-10-23 | International Minerals & Chemical Corp. | Manganese-containing antibiotic agents |
| US4351845A (en) * | 1981-03-12 | 1982-09-28 | Pfizer Inc. | Method of increasing feed efficiency in swine |
| US4761426A (en) * | 1981-08-07 | 1988-08-02 | International Minerals & Chemical Corp. | Lysocellin-containing composition and process for promoting growth and feed efficiency of food producing animals |
| BE902010A (fr) * | 1984-03-28 | 1985-09-25 | Hajdusagi Agraripari Egyesules | Nouvelles combinaisons de medicaments ayant un effet synergique et procede pour les preparer. |
| US4753798A (en) * | 1986-06-30 | 1988-06-28 | American Cyanamid Company | Methods and compositions for controlling protozoal infections in warm-blooded animals |
| AT400674B (de) * | 1991-07-24 | 1996-02-26 | Biochemie Gmbh | Pharmazeutische pleuromutilin-zubereitung |
| ES2205072T3 (es) * | 1996-01-03 | 2004-05-01 | Smithkline Beecham Plc | Derivados carbamoiloxi de mutilina y su uso como agentes antibacterianos. |
| GB0207495D0 (en) * | 2002-03-28 | 2002-05-08 | Biochemie Gmbh | Organic compounds |
| WO2006070671A1 (ja) * | 2004-12-27 | 2006-07-06 | Kyorin Pharmaceutical Co., Ltd. | 12位置換ムチリン誘導体 |
| CA2688008A1 (en) * | 2007-05-24 | 2008-11-27 | Kyorin Pharmaceutical Co., Ltd. | Mutilin derivative having heterocyclic aromatic ring carboxylic acid structure in substituent at 14-position |
| US9149456B2 (en) * | 2008-07-28 | 2015-10-06 | Zoetis Services Llc | Laidlomycin compositions and methods |
-
1976
- 1976-12-23 CH CH1625876A patent/CH627940A5/de not_active IP Right Cessation
-
1977
- 1977-12-12 DE DE19772755339 patent/DE2755339A1/de not_active Withdrawn
- 1977-12-19 NL NL7714043A patent/NL7714043A/xx not_active Application Discontinuation
- 1977-12-19 GB GB52715/77A patent/GB1586510A/en not_active Expired
- 1977-12-20 US US05/862,365 patent/US4148890A/en not_active Expired - Lifetime
- 1977-12-20 IT IT7752277A patent/IT1143623B/it active
- 1977-12-21 BE BE183707A patent/BE862145A/xx not_active IP Right Cessation
- 1977-12-22 FR FR7738768A patent/FR2374903A1/fr active Granted
- 1977-12-22 JP JP16095677A patent/JPS5386038A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NL7714043A (nl) | 1978-06-27 |
| JPS5386038A (en) | 1978-07-29 |
| IT1143623B (it) | 1986-10-22 |
| BE862145A (fr) | 1978-06-21 |
| US4148890A (en) | 1979-04-10 |
| DE2755339A1 (de) | 1978-06-29 |
| CH627940A5 (de) | 1982-02-15 |
| FR2374903B1 (https=) | 1980-08-22 |
| FR2374903A1 (fr) | 1978-07-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |