CA2225741C - Preparations d'antibiotiques ionophores - Google Patents

Preparations d'antibiotiques ionophores Download PDF

Info

Publication number: CA2225741C
Authority: CA; Canada
Prior art keywords: monensin; agent; formulation; optionally; aqueous
Prior art date: 1995-07-14
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 - Fee Related

Application number

CA002225741A

Other languages

English (en)

Other versions

CA2225741A1 (fr

Inventor

Derek George Moore

Lionel Barry Lowe

Kevin Charles Palmer

Kim Ewing Melville Agnew

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Eli Lilly and Co NZ Ltd

Original Assignee

Eli Lilly and Co NZ Ltd

Priority date (The priority date 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 date listed.)

1995-07-14

Filing date

1996-07-04

Publication date

2006-10-03

1995-07-14 Priority claimed from NZ272574A external-priority patent/NZ272574A/en

1996-07-04 Application filed by Eli Lilly and Co NZ Ltd filed Critical Eli Lilly and Co NZ Ltd

1996-07-04 Priority claimed from PCT/NZ1996/000068 external-priority patent/WO1997003650A1/fr

1997-02-06 Publication of CA2225741A1 publication Critical patent/CA2225741A1/fr

2006-10-03 Application granted granted Critical

2006-10-03 Publication of CA2225741C publication Critical patent/CA2225741C/fr

2016-07-04 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims description 44
238000009472 formulation Methods 0.000 title claims description 21
239000002555 ionophore Substances 0.000 title abstract description 74
230000000236 ionophoric effect Effects 0.000 title abstract description 74
230000003115 biocidal effect Effects 0.000 title abstract description 65
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 abstract description 61
229930191564 Monensin Natural products 0.000 claims abstract description 60
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 abstract description 60
229960005358 monensin Drugs 0.000 claims abstract description 60
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 34
229920001285 xanthan gum Polymers 0.000 claims abstract description 31
239000000230 xanthan gum Substances 0.000 claims abstract description 25
235000010493 xanthan gum Nutrition 0.000 claims abstract description 25
229940082509 xanthan gum Drugs 0.000 claims abstract description 25
239000002518 antifoaming agent Substances 0.000 claims abstract description 22
239000003795 chemical substances by application Substances 0.000 claims abstract description 22
230000002335 preservative effect Effects 0.000 claims abstract description 19
239000003755 preservative agent Substances 0.000 claims abstract description 18
229940083037 simethicone Drugs 0.000 claims abstract description 15
230000003139 buffering effect Effects 0.000 claims abstract description 14
AMTWCFIAVKBGOD-UHFFFAOYSA-N dioxosilane;methoxy-dimethyl-trimethylsilyloxysilane Chemical compound O=[Si]=O.CO[Si](C)(C)O[Si](C)(C)C AMTWCFIAVKBGOD-UHFFFAOYSA-N 0.000 claims abstract description 14
238000009736 wetting Methods 0.000 claims abstract description 14
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 63
XOIQMTLWECTKJL-FBZUZRIGSA-M sodium;(2s,3r,4s)-4-[(2s,5r,7s,8r,9s)-2-[(2r,5s)-5-ethyl-5-[(2r,3s,5r)-5-[(2s,3s,5r,6r)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]oxolan-2-yl]-7-hydroxy-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-3-methoxy-2-methylpentanoate Chemical compound [Na+].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 XOIQMTLWECTKJL-FBZUZRIGSA-M 0.000 claims description 44
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 20
241000283690 Bos taurus Species 0.000 claims description 18
239000000725 suspension Substances 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 17
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 16
239000000600 sorbitol Substances 0.000 claims description 16
235000013336 milk Nutrition 0.000 claims description 13
239000008267 milk Substances 0.000 claims description 13
210000004080 milk Anatomy 0.000 claims description 13
238000002156 mixing Methods 0.000 claims description 11
241000282849 Ruminantia Species 0.000 claims description 10
230000000694 effects Effects 0.000 claims description 10
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims description 9
229910000397 disodium phosphate Inorganic materials 0.000 claims description 9
235000019800 disodium phosphate Nutrition 0.000 claims description 9
230000002265 prevention Effects 0.000 claims description 9
239000000377 silicon dioxide Substances 0.000 claims description 9
235000012239 silicon dioxide Nutrition 0.000 claims description 9
239000001488 sodium phosphate Substances 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 7
238000000034 method Methods 0.000 claims description 7
FFJMLWSZNCJCSZ-UHFFFAOYSA-N n-methylmethanamine;hydrobromide Chemical compound Br.CNC FFJMLWSZNCJCSZ-UHFFFAOYSA-N 0.000 claims description 6
208000003495 Coccidiosis Diseases 0.000 claims description 5
206010023076 Isosporiasis Diseases 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
KDPUQELWHOMNPN-UHFFFAOYSA-M potassium;dihydrogen phosphate;dihydrate Chemical compound O.O.[K+].OP(O)([O-])=O KDPUQELWHOMNPN-UHFFFAOYSA-M 0.000 claims description 5
208000007976 Ketosis Diseases 0.000 claims description 4
102000014171 Milk Proteins Human genes 0.000 claims description 4
108010011756 Milk Proteins Proteins 0.000 claims description 4
239000000654 additive Substances 0.000 claims description 4
229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
230000004140 ketosis Effects 0.000 claims description 4
235000021239 milk protein Nutrition 0.000 claims description 4
239000011707 mineral Substances 0.000 claims description 4
230000004584 weight gain Effects 0.000 claims description 4
235000019786 weight gain Nutrition 0.000 claims description 4
230000000996 additive effect Effects 0.000 claims description 3
235000015278 beef Nutrition 0.000 claims description 3
244000309466 calf Species 0.000 claims description 3
235000013365 dairy product Nutrition 0.000 claims description 2
239000003814 drug Substances 0.000 claims 2
239000007798 antifreeze agent Substances 0.000 abstract description 33
239000003242 anti bacterial agent Substances 0.000 abstract description 27
229940088710 antibiotic agent Drugs 0.000 abstract description 27
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract description 25
241001465754 Metazoa Species 0.000 abstract description 25
238000010790 dilution Methods 0.000 abstract description 24
239000012895 dilution Substances 0.000 abstract description 24
239000000080 wetting agent Substances 0.000 abstract description 22
239000004546 suspension concentrate Substances 0.000 abstract description 20
239000012141 concentrate Substances 0.000 abstract description 18
239000000375 suspending agent Substances 0.000 abstract description 17
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract description 11
239000004094 surface-active agent Substances 0.000 abstract description 11
-1 bloat Chemical compound 0.000 abstract description 6
239000002585 base Substances 0.000 description 21
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 14
235000019333 sodium laurylsulphate Nutrition 0.000 description 14
239000004141 Sodium laurylsulphate Substances 0.000 description 13
150000001875 compounds Chemical class 0.000 description 9
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
239000000872 buffer Substances 0.000 description 8
239000000243 solution Substances 0.000 description 8
239000007788 liquid Substances 0.000 description 7
239000000787 lecithin Substances 0.000 description 6
235000010445 lecithin Nutrition 0.000 description 6
239000000843 powder Substances 0.000 description 6
230000002528 anti-freeze Effects 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 4
238000013019 agitation Methods 0.000 description 4
239000007900 aqueous suspension Substances 0.000 description 4
239000008367 deionised water Substances 0.000 description 4
239000006260 foam Substances 0.000 description 4
LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
239000000047 product Substances 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
229920002907 Guar gum Polymers 0.000 description 3
229930182504 Lasalocid Natural products 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000001913 cellulose Substances 0.000 description 3
229920002678 cellulose Polymers 0.000 description 3
239000000665 guar gum Substances 0.000 description 3
235000010417 guar gum Nutrition 0.000 description 3
229960002154 guar gum Drugs 0.000 description 3
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 description 3
229960000320 lasalocid Drugs 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
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 description 2
PYUBINRDIXNWEP-BSSZEUCBSA-N (2r)-2-[(2s,3s,6r)-6-[(2r,3s)-3-[(2r,5s,6r)-6-[[(2r,3s,6r)-6-[(1r)-1-[(2s,5s)-5-[(2r,5s)-5-[(2r,5r,6s)-6-ethyl-5-hydroxy-5-methyloxan-2-yl]-2-hydroxyoxolan-2-yl]-5-methyloxolan-2-yl]ethyl]-6-hydroxy-3-methyloxan-2-yl]methyl]-6-hydroxy-5-methyloxan-2-yl]-2 Chemical compound C1C[C@](O)(C)[C@H](CC)O[C@H]1[C@H]1O[C@@](O)([C@@]2(C)O[C@@H](CC2)[C@@H](C)[C@]2(O)O[C@H](C[C@]3(O)[C@H](CC[C@@H](O3)[C@@H](C)[C@H](O)C[C@@H]3O[C@@H]([C@@H](C)CC3)[C@@H](C)C(O)=O)C)[C@@H](C)CC2)CC1 PYUBINRDIXNWEP-BSSZEUCBSA-N 0.000 description 2
QFHLVPYVNFSTBE-SMAIMEEGSA-N (2r)-2-hydroxy-2-[(2s,3s,4s,5s,6s)-2-hydroxy-6-[[(2r,3r,4r,5s,6r,7r,9s)-2-[(2r,5s)-5-[(2r,5r)-5-[(2s,3s,4s,5r,6s)-6-hydroxy-4-[(2r,5s,6r)-5-methoxy-6-methyloxan-2-yl]oxy-3,5,6-trimethyloxan-2-yl]oxolan-2-yl]oxolan-2-yl]-3,7-dimethoxy-2,4,6-trimethyl-1,10- Chemical compound O([C@@H]1[C@@H](C)[C@@](C)(O)O[C@@H]([C@H]1C)[C@H]1CC[C@@H](O1)[C@@H]1CC[C@@H](O1)[C@@]1(C)O[C@]2([C@H](C)[C@H]1OC)[C@@H]([C@H](OC)C[C@@H](C[C@H]1[C@]([C@@H](OC)[C@H](C)[C@@](O)([C@@H](O)C(O)=O)O1)(C)OC)O2)C)[C@H]1CC[C@H](OC)[C@@H](C)O1 QFHLVPYVNFSTBE-SMAIMEEGSA-N 0.000 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 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 description 2
XZJAKURZQBNKKX-QFQDJZPHSA-N (3e)-3-[(2s)-1-hydroxy-2-[(1s,2s,6r)-2-[(e)-3-hydroxy-2-[(2r,3r,6s)-6-[(e,3s)-3-[(2r,3s,5r)-5-[(1s)-1-methoxyethyl]-3-methyloxolan-2-yl]but-1-enyl]-3-methyloxan-2-yl]prop-1-enyl]-6-methylcyclohexyl]propylidene]oxolane-2,4-dione Chemical compound O1[C@@H]([C@H](C)OC)C[C@H](C)[C@@H]1[C@@H](C)\C=C\[C@H]1O[C@@H](C(\CO)=C\[C@@H]2[C@H]([C@H](C)CCC2)[C@H](C)C(\O)=C\2C(OCC/2=O)=O)[C@H](C)CC1 XZJAKURZQBNKKX-QFQDJZPHSA-N 0.000 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 description 2
LQFPDTISEHAMNQ-JRSQRZRGSA-N (e,2s,4r,8s)-8-[(2s,5r,6r,7r,9s)-2-[(2r,4s,5r,6r,9r)-2-[(2s,3s,5r,6r)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-4,6-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-7-[(2r,5s,6r)-5-methoxy-6-methyloxan-2-yl]oxy-2,6-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl Chemical compound O1[C@H](C)[C@@H](OC)CC[C@@H]1O[C@H]1[C@@H](C)[C@@]2(O[C@@](C)(CC2)[C@@H]2O[C@@]3([C@H](C[C@@H](O3)[C@@H]3[C@H](C[C@@H](C)[C@](O)(CO)O3)C)C)[C@H](C)CC2)O[C@H]([C@@H](C)\C=C(/C)C(=O)[C@H](C)C[C@H](C)C(O)=O)C1 LQFPDTISEHAMNQ-JRSQRZRGSA-N 0.000 description 2
RHDSQRNKIIRGBB-UHFFFAOYSA-N 2-[2-hydroxy-6-[[2-[5-[5-(6-hydroxy-4-methoxy-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]-5-methoxy-4-(5-methoxy-6-methyloxan-2-yl)oxy-3,5-dimethyloxan-2-yl]propanoic acid Chemical compound COC1C(C)C2(C(C(OC)CC(CC3C(C(OC4OC(C)C(OC)CC4)C(C)C(O)(C(C)C(O)=O)O3)(C)OC)O2)C)OC1(C)C(O1)CCC1C(O1)CCC1C1OC(C)(O)C(C)C(OC)C1C RHDSQRNKIIRGBB-UHFFFAOYSA-N 0.000 description 2
NZHCPUBOSWFGNA-MKODDJJXSA-N 3-chloro-2-[(2s,4r,5s,6s,8r)-8-[(1r,2r,3r,7r,9s,10s,12r,15r)-3-[(2r,4r)-5-ethoxycarbonyl-4-hydroxyoxolan-2-yl]-15-hydroxy-2-methoxy-1,3,10,12-tetramethyl-4,6,8-trioxadispiro[4.1.5^{7}.3^{5}]pentadec-13-en-9-yl]-5-hydroxy-4,6-dimethyl-7-oxononan-2-yl]-6-hy Chemical compound C1[C@@H](O)C(C(=O)OCC)O[C@H]1[C@]1(C)[C@H](OC)[C@@H](C)C2([C@@H](C=C[C@@]3([C@@H](C[C@H](C)[C@@H]([C@@H](C)C(=O)[C@@H](C)[C@@H](O)[C@H](C)C[C@H](C)C=4C(=C(O)C(C)=CC=4Cl)C(O)=O)O3)C)O2)O)O1 NZHCPUBOSWFGNA-MKODDJJXSA-N 0.000 description 2
XZJLJFYPIJKWCY-ANXQGEBNSA-N 6-[(3r,4s,5s,7r)-7-[(2s,3s,5s)-5-ethyl-5-[(2r,5s)-5-ethyl-5-[(1r)-1-hydroxyethyl]oxolan-2-yl]-3-methyloxolan-2-yl]-4-hydroxy-3,5-dimethyl-6-oxononyl]-2-hydroxy-3-methylbenzoic acid 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@@](CC)([C@@H](C)O)O1 XZJLJFYPIJKWCY-ANXQGEBNSA-N 0.000 description 2
206010000060 Abdominal distension Diseases 0.000 description 2
WWDHGOLBPBWCNJ-UHFFFAOYSA-N Alborixin Natural products C1CC(O)(C)C(CC)OC1C1(C)OC(O)(C2(C)OC(CC2)C(O)C2(O)C(CC(C)C(CC3(O)C(CCC(O3)C(C)C(O)CC3C(CC(C)C(C(C)C(O)=O)O3)C)C)O2)C)C(C)C1 WWDHGOLBPBWCNJ-UHFFFAOYSA-N 0.000 description 2
HIYAVKIYRIFSCZ-CVXKHCKVSA-N Calcimycin Chemical compound CC([C@H]1OC2([C@@H](C[C@H]1C)C)O[C@H]([C@H](CC2)C)CC=1OC2=CC=C(C(=C2N=1)C(O)=O)NC)C(=O)C1=CC=CN1 HIYAVKIYRIFSCZ-CVXKHCKVSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 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 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 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 description 2
KRJBAINQJPYZJX-UHFFFAOYSA-N Mutalomycin Natural products COC1C(C)C(CC2OC3(CCC(C)(O3)C4CCC(C)(O4)C5OC(CC5C)C6OC(C)(O)C(C)CC6C)CC(O)C2C)OC(O)(C(C)C(=O)O)C1C KRJBAINQJPYZJX-UHFFFAOYSA-N 0.000 description 2
VHKXXVVRRDYCIK-CWCPJSEDSA-N Narasin Chemical compound C[C@H]1C[C@H](C)[C@H]([C@@H](CC)C(O)=O)O[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 VHKXXVVRRDYCIK-CWCPJSEDSA-N 0.000 description 2
VHKXXVVRRDYCIK-UHFFFAOYSA-N Narasin Natural products CC1CC(C)C(C(CC)C(O)=O)OC1C(C)C(O)C(C)C(=O)C(CC)C1C(C)CC(C)C2(C=CC(O)C3(OC(C)(CC3)C3OC(C)C(O)(CC)CC3)O2)O1 VHKXXVVRRDYCIK-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 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 description 2
239000004189 Salinomycin Substances 0.000 description 2
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 description 2
WWDHGOLBPBWCNJ-GXXSWWTOSA-N alborixin Chemical compound C1C[C@](O)(C)[C@H](CC)O[C@H]1[C@@]1(C)O[C@@](O)([C@@]2(C)O[C@@H](CC2)[C@@H](O)[C@@]2(O)[C@@H](C[C@H](C)[C@@H](C[C@]3(O)[C@H](CC[C@@H](O3)[C@@H](C)[C@H](O)C[C@H]3[C@@H](C[C@H](C)[C@@H]([C@@H](C)C(O)=O)O3)C)C)O2)C)[C@H](C)C1 WWDHGOLBPBWCNJ-GXXSWWTOSA-N 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
208000024330 bloating Diseases 0.000 description 2
230000037396 body weight Effects 0.000 description 2
HHSPVTKDOHQBKF-UHFFFAOYSA-J calcium;magnesium;dicarbonate Chemical compound [Mg+2].[Ca+2].[O-]C([O-])=O.[O-]C([O-])=O HHSPVTKDOHQBKF-UHFFFAOYSA-J 0.000 description 2
238000011260 co-administration Methods 0.000 description 2
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 2
229910000396 dipotassium phosphate Inorganic materials 0.000 description 2
235000019797 dipotassium phosphate Nutrition 0.000 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 description 2
238000011067 equilibration Methods 0.000 description 2
230000001747 exhibiting effect Effects 0.000 description 2
230000008014 freezing Effects 0.000 description 2
238000007710 freezing Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
PGHMRUGBZOYCAA-ADZNBVRBSA-N ionomycin Chemical compound O1[C@H](C[C@H](O)[C@H](C)[C@H](O)[C@H](C)/C=C/C[C@@H](C)C[C@@H](C)C(/O)=C/C(=O)[C@@H](C)C[C@@H](C)C[C@@H](CCC(O)=O)C)CC[C@@]1(C)[C@@H]1O[C@](C)([C@@H](C)O)CC1 PGHMRUGBZOYCAA-ADZNBVRBSA-N 0.000 description 2
PGHMRUGBZOYCAA-UHFFFAOYSA-N ionomycin Natural products O1C(CC(O)C(C)C(O)C(C)C=CCC(C)CC(C)C(O)=CC(=O)C(C)CC(C)CC(CCC(O)=O)C)CCC1(C)C1OC(C)(C(C)O)CC1 PGHMRUGBZOYCAA-UHFFFAOYSA-N 0.000 description 2
229960004561 laidlomycin Drugs 0.000 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 description 2
229910001629 magnesium chloride Inorganic materials 0.000 description 2
239000000395 magnesium oxide Substances 0.000 description 2
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
229910000402 monopotassium phosphate Inorganic materials 0.000 description 2
235000019796 monopotassium phosphate Nutrition 0.000 description 2
WWEDNBWYGGJQOV-RIWLGXEFSA-N mutalomycin Chemical compound O1[C@@](O)([C@H](C)C(O)=O)[C@H](C)[C@@H](OC)[C@@H](C)[C@H]1[C@H](C)[C@@H]1[C@H](C)[C@@H](O)C[C@@]2(O[C@@](C)(CC2)[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@@](C)(O)O2)C)C)O1 WWEDNBWYGGJQOV-RIWLGXEFSA-N 0.000 description 2
229960001851 narasin Drugs 0.000 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 description 2
239000002245 particle Substances 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 2
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
210000004767 rumen Anatomy 0.000 description 2
229960001548 salinomycin Drugs 0.000 description 2
235000019378 salinomycin Nutrition 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
235000015096 spirit Nutrition 0.000 description 2
238000012360 testing method Methods 0.000 description 2
229950002881 tetronasin Drugs 0.000 description 2
239000011573 trace mineral Substances 0.000 description 2
235000013619 trace mineral Nutrition 0.000 description 2
238000002604 ultrasonography Methods 0.000 description 2
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 description 1
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical class CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
IEORSVTYLWZQJQ-UHFFFAOYSA-N 2-(2-nonylphenoxy)ethanol Chemical compound CCCCCCCCCC1=CC=CC=C1OCCO IEORSVTYLWZQJQ-UHFFFAOYSA-N 0.000 description 1
241000156767 Centrolene Species 0.000 description 1
244000260524 Chrysanthemum balsamita Species 0.000 description 1
235000005633 Chrysanthemum balsamita Nutrition 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
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 description 1
241000209082 Lolium Species 0.000 description 1
229920003091 Methocel™ Polymers 0.000 description 1
235000015724 Trifolium pratense Nutrition 0.000 description 1
244000042324 Trifolium repens Species 0.000 description 1
235000013540 Trifolium repens var repens Nutrition 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
229910021502 aluminium hydroxide Inorganic materials 0.000 description 1
239000012223 aqueous fraction Substances 0.000 description 1
235000013405 beer Nutrition 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000010586 diagram Methods 0.000 description 1
239000004205 dimethyl polysiloxane Substances 0.000 description 1
235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
238000009826 distribution Methods 0.000 description 1
239000003651 drinking water Substances 0.000 description 1
235000020188 drinking water Nutrition 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
235000021321 essential mineral Nutrition 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000005187 foaming Methods 0.000 description 1
229910001679 gibbsite Inorganic materials 0.000 description 1
150000002314 glycerols Chemical class 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000001046 green dye Substances 0.000 description 1
239000000416 hydrocolloid Substances 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
239000012263 liquid product Substances 0.000 description 1
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
239000000347 magnesium hydroxide Substances 0.000 description 1
235000012254 magnesium hydroxide Nutrition 0.000 description 1
229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
229960002216 methylparaben Drugs 0.000 description 1
229920000847 nonoxynol Polymers 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
229920001983 poloxamer Polymers 0.000 description 1
229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
244000144977 poultry Species 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
229960003415 propylparaben Drugs 0.000 description 1
239000002994 raw material Substances 0.000 description 1
235000013526 red clover Nutrition 0.000 description 1
239000013049 sediment Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000010257 thawing Methods 0.000 description 1
230000008719 thickening Effects 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
231100000925 very toxic Toxicity 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
150000003722 vitamin derivatives Chemical class 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1

Landscapes

Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

CA002225741A 1995-07-14 1996-07-04 Preparations d'antibiotiques ionophores Expired - Fee Related CA2225741C (fr)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
NZ272574A NZ272574A (en)	1995-07-14	1995-07-14	Aqueous base suspension concentrate containing at least one ionophore antibiotic and wetting agent and/or a surfactant and xanthan gum optionally with a suspension agent, an antifreeze agent and an antifoaming agent; drench for veterinary treatment
NZ272574		1995-07-14
NZ272940		1995-09-06
PCT/NZ1996/000068 WO1997003650A1 (fr)	1995-07-14	1996-07-04	Formulations d'antibiotiques ionophores
NZ27294096		1996-09-06

Publications (2)

Publication Number	Publication Date
CA2225741A1 CA2225741A1 (fr)	1997-02-06
CA2225741C true CA2225741C (fr)	2006-10-03

Family

ID=26651484

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002225741A Expired - Fee Related CA2225741C (fr)	1995-07-14	1996-07-04	Preparations d'antibiotiques ionophores

Country Status (1)

Country	Link
CA (1)	CA2225741C (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP6403242B2 (ja) *	2015-04-28	2018-10-10	エランコ・ユーエス・インコーポレイテッドＥｌａｎｃｏＵＳＩｎｃ．	湿式造粒法によるモネンシン水分散性顆粒

1996
- 1996-07-04 CA CA002225741A patent/CA2225741C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2225741A1 (fr)	1997-02-06

Legal Events

Date	Code	Title	Description
2002-05-30	EEER	Examination request
2012-07-04	MKLA	Lapsed

Publication	Publication Date	Title
US5874103A (en)	1999-02-23	Ionophore antibiotic formulations
CA1039192A (fr)	1978-09-26	Produit et methode pour traiter la diarrhee blanche
US9040571B2 (en)	2015-05-26	Veterinary formulation for administration of a water-insoluble drug to a target animal through a water distribution system
US20090220610A1 (en)	2009-09-03	Suspension Comprising Benzimidazole Carbamate and a Polysorbate
US8777134B2 (en)	2014-07-15	Suspension comprising benzimidazole carbamate and a polysorbate
US6211185B1 (en)	2001-04-03	Concentrate comprising a sulfonamide in solution, a 2,4-diaminopyrimidine in stable suspension within said solution, and a suspending agent
AU702462C (en)	2005-12-15	Ionophore antibiotic formulations
IE840047L (en)	1984-07-12	1,3,5-triazin-2,4,6-trione agent for coccidiosis
CA2225741C (fr)	2006-10-03	Preparations d'antibiotiques ionophores
AU741614B2 (en)	2001-12-06	Ionophore antibiotic formulations
AU774516B2 (en)	2004-07-01	Ionophore antibiotic formulations
US4423043A (en)	1983-12-27	Aqueous liquid formulations for control of bacterial and protozoal diseases
AU2002216503B2 (en)	2006-04-27	Ionophore antibiotic formulations
NZ333479A (en)	2000-07-28	aqueous base suspension concentrate containing at least one ionophore antibiotic
US6800631B2 (en)	2004-10-05	Method of producing a concentrate comprising a sulfonamide in solution, a 2,4-diaminopyrimidine in stable suspension within said solution
KR930001807B1 (ko)	1993-03-13	옥소인산 현탁제
NZ509092A (en)	2003-10-31	Ionophore antibiotic formulations containing a dispersing agent with the ionophore antibiotic having a mean particle size of less than 20 microns
JPH041133A (ja)	1992-01-06	安定なオキソリン酸乳濁液およびその製造方法
RO134360A2 (ro)	2020-08-28	Procedeu de obţinere a unei compoziţii emulsionate pe bază de florfenicol şi praziquantel, cu proprietăţi antibacteriene şi antiparazitare, pentru tratarea peştilor
NZ239212A (en)	1994-09-27	Composition for treatment of bloat comprising at least one detergent useful for preventing or treating bloat and at least one mineral.