NZ543594A - Compositions for treating infection in cattle and swine comprising a fluorinated chloramphenicol or thiamphenicol derivative antibiotic such as florfenicol, and triacetin - Google Patents
Compositions for treating infection in cattle and swine comprising a fluorinated chloramphenicol or thiamphenicol derivative antibiotic such as florfenicol, and triacetinInfo
- Publication number
- NZ543594A NZ543594A NZ543594A NZ54359404A NZ543594A NZ 543594 A NZ543594 A NZ 543594A NZ 543594 A NZ543594 A NZ 543594A NZ 54359404 A NZ54359404 A NZ 54359404A NZ 543594 A NZ543594 A NZ 543594A
- Authority
- NZ
- New Zealand
- Prior art keywords
- composition
- florfenicol
- group
- animal
- medicament
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 94
- AYIRNRDRBQJXIF-NXEZZACHSA-N (-)-Florfenicol Chemical compound CS(=O)(=O)C1=CC=C([C@@H](O)[C@@H](CF)NC(=O)C(Cl)Cl)C=C1 AYIRNRDRBQJXIF-NXEZZACHSA-N 0.000 title claims abstract description 51
- 229960003760 florfenicol Drugs 0.000 title claims abstract description 48
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 title claims abstract description 46
- 208000015181 infectious disease Diseases 0.000 title claims abstract description 25
- 239000001087 glyceryl triacetate Substances 0.000 title claims abstract description 23
- 235000013773 glyceryl triacetate Nutrition 0.000 title claims abstract description 23
- 229960002622 triacetin Drugs 0.000 title claims abstract description 23
- 241000282898 Sus scrofa Species 0.000 title claims abstract description 15
- 241000283690 Bos taurus Species 0.000 title claims description 55
- 230000003115 biocidal effect Effects 0.000 title description 12
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical class ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 title description 6
- OTVAEFIXJLOWRX-NXEZZACHSA-N thiamphenicol Chemical class CS(=O)(=O)C1=CC=C([C@@H](O)[C@@H](CO)NC(=O)C(Cl)Cl)C=C1 OTVAEFIXJLOWRX-NXEZZACHSA-N 0.000 title description 6
- 241001465754 Metazoa Species 0.000 claims abstract description 50
- 238000011282 treatment Methods 0.000 claims abstract description 33
- -1 azidomethyl Chemical group 0.000 claims abstract description 32
- 208000023504 respiratory system disease Diseases 0.000 claims abstract description 31
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- 125000002252 acyl group Chemical group 0.000 claims abstract description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 18
- 208000010801 foot rot Diseases 0.000 claims abstract description 11
- 230000000813 microbial effect Effects 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 208000004396 mastitis Diseases 0.000 claims abstract description 8
- 239000005660 Abamectin Substances 0.000 claims abstract description 7
- 208000031973 Conjunctivitis infective Diseases 0.000 claims abstract description 7
- 201000001028 acute contagious conjunctivitis Diseases 0.000 claims abstract description 7
- 208000004232 Enteritis Diseases 0.000 claims abstract description 6
- 206010046793 Uterine inflammation Diseases 0.000 claims abstract description 6
- AZSNMRSAGSSBNP-UHFFFAOYSA-N 22,23-dihydroavermectin B1a Natural products C1CC(C)C(C(C)CC)OC21OC(CC=C(C)C(OC1OC(C)C(OC3OC(C)C(O)C(OC)C3)C(OC)C1)C(C)C=CC=C1C3(C(C(=O)O4)C=C(C)C(O)C3OC1)O)CC4C2 AZSNMRSAGSSBNP-UHFFFAOYSA-N 0.000 claims abstract description 4
- SPBDXSGPUHCETR-JFUDTMANSA-N 8883yp2r6d Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O[C@@H]([C@@H](C)CC4)C(C)C)O3)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1C[C@H](C)[C@@H]([C@@H](C)CC)O[C@@]21O[C@H](C\C=C(C)\[C@@H](O[C@@H]1O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C1)[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 SPBDXSGPUHCETR-JFUDTMANSA-N 0.000 claims abstract description 4
- 239000005894 Emamectin Substances 0.000 claims abstract description 4
- 230000002141 anti-parasite Effects 0.000 claims abstract description 4
- QLFZZSKTJWDQOS-YDBLARSUSA-N doramectin Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C3CCCCC3)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C QLFZZSKTJWDQOS-YDBLARSUSA-N 0.000 claims abstract description 4
- 229960003997 doramectin Drugs 0.000 claims abstract description 4
- WPNHOHPRXXCPRA-TVXIRPTOSA-N eprinomectin Chemical compound O1[C@@H](C)[C@@H](NC(C)=O)[C@H](OC)C[C@@H]1O[C@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C\C=C/[C@@H]2C)\C)O[C@H]1C WPNHOHPRXXCPRA-TVXIRPTOSA-N 0.000 claims abstract description 4
- 229960002346 eprinomectin Drugs 0.000 claims abstract description 4
- NOOCSNJCXJYGPE-UHFFFAOYSA-N flunixin Chemical compound C1=CC=C(C(F)(F)F)C(C)=C1NC1=NC=CC=C1C(O)=O NOOCSNJCXJYGPE-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229960000588 flunixin Drugs 0.000 claims abstract description 4
- 229960002418 ivermectin Drugs 0.000 claims abstract description 4
- FXWHFKOXMBTCMP-WMEDONTMSA-N milbemycin Natural products COC1C2OCC3=C/C=C/C(C)CC(=CCC4CC(CC5(O4)OC(C)C(C)C(OC(=O)C(C)CC(C)C)C5O)OC(=O)C(C=C1C)C23O)C FXWHFKOXMBTCMP-WMEDONTMSA-N 0.000 claims abstract description 4
- YZBLFMPOMVTDJY-CBYMMZEQSA-N moxidectin Chemical compound O1[C@H](C(\C)=C\C(C)C)[C@@H](C)C(=N/OC)\C[C@@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 YZBLFMPOMVTDJY-CBYMMZEQSA-N 0.000 claims abstract description 4
- 229960004816 moxidectin Drugs 0.000 claims abstract description 4
- AFJYYKSVHJGXSN-KAJWKRCWSA-N selamectin Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1C(/C)=C/C[C@@H](O[C@]2(O[C@@H]([C@@H](C)CC2)C2CCCCC2)C2)C[C@@H]2OC(=O)[C@@H]([C@]23O)C=C(C)C(=N\O)/[C@H]3OC\C2=C/C=C/[C@@H]1C AFJYYKSVHJGXSN-KAJWKRCWSA-N 0.000 claims abstract description 4
- 229960002245 selamectin Drugs 0.000 claims abstract description 4
- IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 IBSREHMXUMOFBB-JFUDTMANSA-N 0.000 claims abstract description 3
- 229950008167 abamectin Drugs 0.000 claims abstract description 3
- 239000003814 drug Substances 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- 230000037396 body weight Effects 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 238000007920 subcutaneous administration Methods 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 230000036470 plasma concentration Effects 0.000 claims description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 12
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical group C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 235000013772 propylene glycol Nutrition 0.000 claims description 5
- 239000003381 stabilizer Substances 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
- 125000000565 sulfonamide group Chemical group 0.000 claims description 4
- MEJYDZQQVZJMPP-ULAWRXDQSA-N (3s,3ar,6r,6ar)-3,6-dimethoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan Chemical compound CO[C@H]1CO[C@@H]2[C@H](OC)CO[C@@H]21 MEJYDZQQVZJMPP-ULAWRXDQSA-N 0.000 claims description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 3
- 239000002202 Polyethylene glycol Substances 0.000 claims description 3
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 239000001069 triethyl citrate Substances 0.000 claims description 3
- 235000013769 triethyl citrate Nutrition 0.000 claims description 3
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 claims description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- RFKSRZIDTYVHLY-UHFFFAOYSA-N 3-(2,3-dihydroxypropoxymethoxy)propane-1,2-diol Chemical compound OCC(O)COCOCC(O)CO RFKSRZIDTYVHLY-UHFFFAOYSA-N 0.000 claims description 2
- 101100496169 Arabidopsis thaliana CLH1 gene Proteins 0.000 claims description 2
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 2
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 2
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 2
- 101100044057 Mesocricetus auratus SYCP3 gene Proteins 0.000 claims description 2
- 101100080600 Schizosaccharomyces pombe (strain 972 / ATCC 24843) nse6 gene Proteins 0.000 claims description 2
- 101150111293 cor-1 gene Proteins 0.000 claims description 2
- 235000011187 glycerol Nutrition 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 101150009274 nhr-1 gene Proteins 0.000 claims 2
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- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 claims 1
- GCKZANITAMOIAR-XWVCPFKXSA-N dsstox_cid_14566 Chemical compound [O-]C(=O)C1=CC=CC=C1.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H]([NH2+]C)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 GCKZANITAMOIAR-XWVCPFKXSA-N 0.000 claims 1
- CXEGAUYXQAKHKJ-NSBHKLITSA-N emamectin B1a Chemical compound C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](NC)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 CXEGAUYXQAKHKJ-NSBHKLITSA-N 0.000 abstract description 3
- 125000001424 substituent group Chemical group 0.000 abstract description 3
- 238000009472 formulation Methods 0.000 description 26
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- 229940088710 antibiotic agent Drugs 0.000 description 8
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- 125000005843 halogen group Chemical group 0.000 description 7
- 244000309466 calf Species 0.000 description 6
- 230000004054 inflammatory process Effects 0.000 description 6
- 238000002560 therapeutic procedure Methods 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 208000035473 Communicable disease Diseases 0.000 description 5
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- 230000001154 acute effect Effects 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 229960005091 chloramphenicol Drugs 0.000 description 5
- 235000013365 dairy product Nutrition 0.000 description 5
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
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- 241000282887 Suidae Species 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
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- 239000004599 antimicrobial Substances 0.000 description 4
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 4
- 208000022362 bacterial infectious disease Diseases 0.000 description 4
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| US11090444B2 (en) | 2018-06-15 | 2021-08-17 | James T. Doubet | Syringe adapter for medication |
| US10709850B2 (en) | 2018-06-15 | 2020-07-14 | James T. Doubet | Syringe adapter for medication |
| US11337894B2 (en) | 2018-06-15 | 2022-05-24 | James T. Doubet | Syringe adapter for animal medication |
| US11097058B2 (en) | 2018-06-15 | 2021-08-24 | James T. Doubet | Syringe adapter for medication |
| US20020035107A1 (en) * | 2000-06-20 | 2002-03-21 | Stefan Henke | Highly concentrated stable meloxicam solutions |
| DE10161077A1 (de) | 2001-12-12 | 2003-06-18 | Boehringer Ingelheim Vetmed | Hochkonzentrierte stabile Meloxicamlösungen zur nadellosen Injektion |
| US6790867B2 (en) * | 2002-05-20 | 2004-09-14 | Schering-Plough Animal Health Corporation | Compositions and method for treating infection in cattle and swine |
| US8992980B2 (en) | 2002-10-25 | 2015-03-31 | Boehringer Ingelheim Vetmedica Gmbh | Water-soluble meloxicam granules |
| UA82359C2 (uk) * | 2003-04-03 | 2008-04-10 | Schering Plough Ltd | Композиція (варіанти) і спосіб лікування мікробних і паразитних інфекцій у великої рогатої худоби і інших тварин |
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| MX2007007528A (es) * | 2004-12-21 | 2007-10-08 | Intervet Int Bv | Composicion veterinaria inyectable. |
| GB0501220D0 (en) * | 2005-01-21 | 2005-03-02 | Norbrook Lab Ltd | Anthelmintic composition |
| MX2009004337A (es) * | 2006-11-01 | 2009-05-22 | Pronova Biopharma Norge As | Compuestos lipidos omega-3. |
| KR101438177B1 (ko) * | 2006-11-01 | 2014-09-05 | 프로노바 바이오파마 너지 에이에스 | 페록시솜 증식자-활성화 수용체의 활성자 또는 조절자인 알파-치환된 오메가-3 지질 |
| CA2672795A1 (en) * | 2006-12-13 | 2008-06-26 | Schering-Plough Ltd. | Water-soluble prodrugs of chloramphenicol, thiamphenicol, and analogs thereof |
| JP2010513487A (ja) * | 2006-12-19 | 2010-04-30 | シェーリング−プラウ・リミテッド | 飲料水系中に添加するためのフロルフェニコールの発泡性処方物 |
| US20090170954A1 (en) * | 2007-12-14 | 2009-07-02 | Schering-Plough Ltd. | Process for Recovering Florfenicol and Florfenicol Analogs |
| FR2925334A1 (fr) * | 2007-12-21 | 2009-06-26 | Ceva Sante Animale Sa | Nouvelles compositions antibacteriennes |
| CN102131772B (zh) * | 2008-07-30 | 2015-03-11 | 英特威国际有限公司 | 用作氟苯尼考的中间体的*唑啉-保护的氨基二醇化合物的制备方法 |
| ES3037313T3 (en) | 2009-10-12 | 2025-09-30 | Boehringer Ingelheim Vetmedica Gmbh | Containers for compositions comprising meloxicam |
| KR101140167B1 (ko) * | 2009-11-04 | 2012-04-24 | 최기동 | 동물용 의약 조성물 및 이를 포함하는 동물용 의약품 |
| BRPI1002021A2 (pt) | 2010-01-21 | 2012-05-22 | Nanocore Biotecnologia S A | composições farmacêuticas para tratamento de infecções bacterianas |
| BRPI1002023A2 (pt) | 2010-03-01 | 2011-10-25 | Nanocore Biotecnologia S A | forma farmacêutica sólida de dissolução rápida para tratamento de infecções bacterianas |
| MX2012010077A (es) | 2010-03-03 | 2012-09-12 | Boehringer Ingelheim Vetmed | Uso de meloxicam para el tratamiento a largo plazo de trastornos musculoesqueleticos en gatos. |
| US9795568B2 (en) | 2010-05-05 | 2017-10-24 | Boehringer Ingelheim Vetmedica Gmbh | Low concentration meloxicam tablets |
| BR112013016231B1 (pt) * | 2010-12-22 | 2021-03-23 | Bayer Intellectual Property Gmbh | Composição imunomoduladora para o tratamento de doença respiratória bovina |
| BR122019025362B1 (pt) * | 2012-11-29 | 2022-07-26 | Cornell University | Uso de uma composição veterinária |
| EA028381B1 (ru) * | 2014-08-08 | 2017-11-30 | Александр Петрович Мерабишвили | Фармацевтический препарат ветеринарного назначения |
| EA028412B9 (ru) * | 2014-08-08 | 2018-03-30 | Александр Петрович Мерабишвили | Фармацевтический препарат ветеринарного назначения |
| RU2563826C1 (ru) * | 2014-08-21 | 2015-09-20 | Общество с ограниченной ответственностью "Научно-внедренческий центр Агроветзащита" | Инъекционная антибактериальная фармацевтическая композиция |
| KR20180021874A (ko) * | 2015-06-26 | 2018-03-05 | 바이엘 애니멀 헬스 게엠베하 | 시토졸 dna 감시 분자의 조절 방법 |
| US10463656B2 (en) * | 2017-01-05 | 2019-11-05 | Iowa State University Research Foundation, Inc. | Methods and compositions for prevention of feedlot bovine respiratory disease |
| US20190388625A1 (en) | 2018-06-15 | 2019-12-26 | James T. Doubet | Syringe adapter for medication |
| USD890925S1 (en) | 2018-06-15 | 2020-07-21 | James T. Doubet | Syringe adapter for medication |
| US12227485B2 (en) * | 2018-06-25 | 2025-02-18 | Intervet Inc. | Compounds useful for the treatment of infection with Mannheimia haemolytica or Histophilus somni |
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| US2671748A (en) * | 1950-05-18 | 1954-03-09 | Parke Davis & Co | Composition of matter |
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| NZ234802A (en) * | 1989-08-14 | 1992-11-25 | Merck & Co Inc | Long acting injectable formulations comprising an avermectin compound and triacetin. treatment for internal and external parasites of animals |
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| WO2003077828A2 (en) * | 2002-03-08 | 2003-09-25 | Schering-Plough, Ltd. | Novel florfenicol-type antibiotics |
| US6790867B2 (en) * | 2002-05-20 | 2004-09-14 | Schering-Plough Animal Health Corporation | Compositions and method for treating infection in cattle and swine |
| CN1507858A (zh) | 2002-12-19 | 2004-06-30 | 王玉万 | 含氟化氯霉素的兽用液体制剂 |
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