DE19613972A1 - Injektionsformulierungen von Avermectinen und Milbemycinen auf Basis von Rizinusöl - Google Patents
Injektionsformulierungen von Avermectinen und Milbemycinen auf Basis von RizinusölInfo
- Publication number
- DE19613972A1 DE19613972A1 DE19613972A DE19613972A DE19613972A1 DE 19613972 A1 DE19613972 A1 DE 19613972A1 DE 19613972 A DE19613972 A DE 19613972A DE 19613972 A DE19613972 A DE 19613972A DE 19613972 A1 DE19613972 A1 DE 19613972A1
- Authority
- DE
- Germany
- Prior art keywords
- castor oil
- propylene glycol
- avermectins
- formulations
- weight
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 44
- 238000009472 formulation Methods 0.000 title claims abstract description 30
- 239000005660 Abamectin Substances 0.000 title claims abstract description 20
- 239000004359 castor oil Substances 0.000 title claims abstract description 15
- 235000019438 castor oil Nutrition 0.000 title claims abstract description 15
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 title claims abstract description 15
- 239000007924 injection Substances 0.000 title claims abstract description 13
- 238000002347 injection Methods 0.000 title claims abstract description 13
- 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 title claims abstract description 10
- ZLBGSRMUSVULIE-GSMJGMFJSA-N milbemycin A3 Chemical class O1[C@H](C)[C@@H](C)CC[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 ZLBGSRMUSVULIE-GSMJGMFJSA-N 0.000 title claims abstract description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 22
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 22
- 239000004480 active ingredient Substances 0.000 claims description 13
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 13
- 239000000194 fatty acid Substances 0.000 claims description 13
- 229930195729 fatty acid Natural products 0.000 claims description 13
- -1 fatty acid esters Chemical class 0.000 claims description 11
- 239000006184 cosolvent Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 claims description 4
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 claims description 4
- 229940093471 ethyl oleate Drugs 0.000 claims description 4
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 4
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- GHHURQMJLARIDK-UHFFFAOYSA-N 2-hydroxypropyl octanoate Chemical compound CCCCCCCC(=O)OCC(C)O GHHURQMJLARIDK-UHFFFAOYSA-N 0.000 claims description 3
- 150000005676 cyclic carbonates Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000005846 sugar alcohols Polymers 0.000 claims description 3
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 3
- 235000013311 vegetables Nutrition 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin 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](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 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 claims description 2
- 229940057917 medium chain triglycerides Drugs 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 18
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 13
- 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 description 11
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 10
- 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 description 9
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 9
- 229960002418 ivermectin Drugs 0.000 description 9
- 229960002446 octanoic acid Drugs 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 7
- 229910052740 iodine Inorganic materials 0.000 description 7
- 239000011630 iodine Substances 0.000 description 7
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 6
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 6
- 235000011187 glycerol Nutrition 0.000 description 6
- 235000013772 propylene glycol Nutrition 0.000 description 6
- 238000007127 saponification reaction Methods 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 5
- 150000003626 triacylglycerols Chemical class 0.000 description 5
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 3
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 3
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 3
- 229940043253 butylated hydroxyanisole Drugs 0.000 description 3
- 239000003240 coconut oil Substances 0.000 description 3
- 235000019864 coconut oil Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 229940059574 pentaerithrityl Drugs 0.000 description 3
- 235000010388 propyl gallate Nutrition 0.000 description 3
- 239000000473 propyl gallate Substances 0.000 description 3
- 229940075579 propyl gallate Drugs 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- QHZLMUACJMDIAE-UHFFFAOYSA-N 1-monopalmitoylglycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)CO QHZLMUACJMDIAE-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 229950008167 abamectin Drugs 0.000 description 2
- ZFUKERYTFURFGA-PVVXTEPVSA-N avermectin B1b 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 ZFUKERYTFURFGA-PVVXTEPVSA-N 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 2
- LDVVMCZRFWMZSG-UHFFFAOYSA-N captan Chemical compound C1C=CCC2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C21 LDVVMCZRFWMZSG-UHFFFAOYSA-N 0.000 description 2
- PWEOPMBMTXREGV-UHFFFAOYSA-N decanoic acid;octanoic acid;propane-1,2-diol Chemical compound CC(O)CO.CCCCCCCC(O)=O.CCCCCCCC(O)=O.CCCCCCCCCC(O)=O.CCCCCCCCCC(O)=O PWEOPMBMTXREGV-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 229960003997 doramectin Drugs 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 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 description 2
- 229960004816 moxidectin Drugs 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
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- 238000001556 precipitation Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
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- OVYMWJFNQQOJBU-UHFFFAOYSA-N 1-octanoyloxypropan-2-yl octanoate Chemical compound CCCCCCCC(=O)OCC(C)OC(=O)CCCCCCC OVYMWJFNQQOJBU-UHFFFAOYSA-N 0.000 description 1
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
- OURWLMNRUGYRSC-UHFFFAOYSA-N 12-(1-hydroxypropan-2-yloxy)octadecanoic acid Chemical compound CCCCCCC(OC(C)CO)CCCCCCCCCCC(O)=O OURWLMNRUGYRSC-UHFFFAOYSA-N 0.000 description 1
- WZUNUACWCJJERC-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)butyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(CC)(CO)CO WZUNUACWCJJERC-UHFFFAOYSA-N 0.000 description 1
- FKOKUHFZNIUSLW-UHFFFAOYSA-N 2-Hydroxypropyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(C)O FKOKUHFZNIUSLW-UHFFFAOYSA-N 0.000 description 1
- WITKSCOBOCOGSC-UHFFFAOYSA-N 2-dodecanoyloxypropyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCC(C)OC(=O)CCCCCCCCCCC WITKSCOBOCOGSC-UHFFFAOYSA-N 0.000 description 1
- OSCJHTSDLYVCQC-UHFFFAOYSA-N 2-ethylhexyl 4-[[4-[4-(tert-butylcarbamoyl)anilino]-6-[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)NC(C)(C)C)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 OSCJHTSDLYVCQC-UHFFFAOYSA-N 0.000 description 1
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- 238000012371 Aseptic Filling Methods 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
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- BJXXCOMGRRCAGN-XPWSMXQVSA-N [2,2-bis(hydroxymethyl)-3-[(e)-octadec-9-enoyl]oxypropyl] (e)-octadec-9-enoate Chemical compound CCCCCCCC\C=C\CCCCCCCC(=O)OCC(CO)(CO)COC(=O)CCCCCCC\C=C\CCCCCCCC BJXXCOMGRRCAGN-XPWSMXQVSA-N 0.000 description 1
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- ZJLATTXAOOPYRU-UHFFFAOYSA-N [3-hydroxy-2,2-bis(hydroxymethyl)propyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCC(CO)(CO)CO ZJLATTXAOOPYRU-UHFFFAOYSA-N 0.000 description 1
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- 238000004090 dissolution Methods 0.000 description 1
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- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
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- 229910052757 nitrogen Inorganic materials 0.000 description 1
- FSVSNKCOMJVGLM-UHFFFAOYSA-N octanoic acid;propane-1,2-diol Chemical compound CC(O)CO.CCCCCCCC(O)=O FSVSNKCOMJVGLM-UHFFFAOYSA-N 0.000 description 1
- GOYBREOSJSERKM-ACZMJKKPSA-N oleandrose Chemical compound O=CC[C@H](OC)[C@@H](O)[C@H](C)O GOYBREOSJSERKM-ACZMJKKPSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920001521 polyalkylene glycol ether Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- GHBFNMLVSPCDGN-UHFFFAOYSA-N rac-1-monooctanoylglycerol Chemical compound CCCCCCCC(=O)OCC(O)CO GHBFNMLVSPCDGN-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
-
- 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
- A61K31/365—Lactones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Tropical Medicine & Parasitology (AREA)
- Engineering & Computer Science (AREA)
- Oncology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19613972A DE19613972A1 (de) | 1996-04-09 | 1996-04-09 | Injektionsformulierungen von Avermectinen und Milbemycinen auf Basis von Rizinusöl |
| PCT/EP1997/001569 WO1997037653A1 (de) | 1996-04-09 | 1997-03-27 | Injektionsformulierungen von avermectinen und milbemycinen auf basis von rizinusöl |
| NZ332224A NZ332224A (en) | 1996-04-09 | 1997-03-27 | Injection formulations of avermectins and milbemycins based on castor oil |
| ES97916406T ES2235230T3 (es) | 1996-04-09 | 1997-03-27 | Formulaciones inyectables de avermectinas y milbemicinas basadas en aceite de ricino. |
| CA002251087A CA2251087C (en) | 1996-04-09 | 1997-03-27 | Injection formulations of avermectins and milbemycins based on castor oil |
| PT97916406T PT896534E (pt) | 1996-04-09 | 1997-03-27 | Formulacoes para injeccao de avermectinas e milbemicinas a base de oleo de ricino |
| CN97193700A CN1095662C (zh) | 1996-04-09 | 1997-03-27 | 以蓖麻油为基础的阿凡曼菌素或米尔倍霉素的注射制剂、其制备以及蓖麻油的相关应用 |
| JP53579597A JP4257870B2 (ja) | 1996-04-09 | 1997-03-27 | ヒマシ油を基とする注射用アベルメクチン含有およびミルベマイシン含有調剤 |
| HK99104544.5A HK1019404B (en) | 1996-04-09 | 1997-03-27 | Injection formulations of avermectins or milbemycins based on castor oil, their preparation, and use of castor for preparing the same |
| HU9903596A HU226120B1 (en) | 1996-04-09 | 1997-03-27 | Injection formulations of avermectins or milbemycins based on castor oil |
| EP97916406A EP0896534B1 (de) | 1996-04-09 | 1997-03-27 | Injektionsformulierungen von avermectinen und milbemycinen auf basis von rizinusöl |
| AT97916406T ATE285233T1 (de) | 1996-04-09 | 1997-03-27 | Injektionsformulierungen von avermectinen und milbemycinen auf basis von rizinusöl |
| DE59712134T DE59712134D1 (de) | 1996-04-09 | 1997-03-27 | Injektionsformulierungen von avermectinen und milbemycinen auf basis von rizinusöl |
| BRPI9708540-5A BR9708540B1 (pt) | 1996-04-09 | 1997-03-27 | formulações injetáveis de avermectinas ou milbemicinas à base de óleo de mamona. |
| US09/155,836 US6063394A (en) | 1996-04-09 | 1997-03-27 | Injection formulations of avermectins and milbemycins based on castor oil |
| AU25066/97A AU718807B2 (en) | 1996-04-09 | 1997-03-27 | Injection formulations of avermectins and milbemycins based on castor oil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19613972A DE19613972A1 (de) | 1996-04-09 | 1996-04-09 | Injektionsformulierungen von Avermectinen und Milbemycinen auf Basis von Rizinusöl |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19613972A1 true DE19613972A1 (de) | 1997-10-16 |
Family
ID=7790774
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19613972A Withdrawn DE19613972A1 (de) | 1996-04-09 | 1996-04-09 | Injektionsformulierungen von Avermectinen und Milbemycinen auf Basis von Rizinusöl |
| DE59712134T Expired - Lifetime DE59712134D1 (de) | 1996-04-09 | 1997-03-27 | Injektionsformulierungen von avermectinen und milbemycinen auf basis von rizinusöl |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59712134T Expired - Lifetime DE59712134D1 (de) | 1996-04-09 | 1997-03-27 | Injektionsformulierungen von avermectinen und milbemycinen auf basis von rizinusöl |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6063394A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0896534B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP4257870B2 (cg-RX-API-DMAC7.html) |
| CN (1) | CN1095662C (cg-RX-API-DMAC7.html) |
| AT (1) | ATE285233T1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU718807B2 (cg-RX-API-DMAC7.html) |
| BR (1) | BR9708540B1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2251087C (cg-RX-API-DMAC7.html) |
| DE (2) | DE19613972A1 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2235230T3 (cg-RX-API-DMAC7.html) |
| NZ (1) | NZ332224A (cg-RX-API-DMAC7.html) |
| PT (1) | PT896534E (cg-RX-API-DMAC7.html) |
| WO (1) | WO1997037653A1 (cg-RX-API-DMAC7.html) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999027906A1 (en) * | 1997-12-03 | 1999-06-10 | Merck & Co., Inc. | Long acting injectable formulations containing hydrogenated castor oil |
| US6174540B1 (en) | 1998-09-14 | 2001-01-16 | Merck & Co., Inc. | Long acting injectable formulations containing hydrogenated caster oil |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19638045A1 (de) * | 1996-09-18 | 1998-03-19 | Bayer Ag | Injektionsformulierungen von Avermectinen und Milbemycinen |
| GB9827727D0 (en) * | 1998-12-16 | 1999-02-10 | Pfizer Ltd | Antiparasitic formulations |
| GB0000313D0 (en) | 2000-01-10 | 2000-03-01 | Astrazeneca Uk Ltd | Formulation |
| AU781682B2 (en) * | 2000-03-20 | 2005-06-09 | Zoetis Services Llc | Sustained-release compositions for parenteral administration |
| US20050009762A1 (en) * | 2003-06-06 | 2005-01-13 | Strobel Michael Albert | Application of water and organic solvent soluble ivermectin for topical and oral use |
| CN1275589C (zh) * | 2002-05-31 | 2006-09-20 | 王玉万 | 含抗寄生虫药物的缓释注射剂 |
| US7262214B2 (en) | 2003-02-26 | 2007-08-28 | Merial Limited | 1-N-arylpyrazole derivatives in prevention of arthropod-borne and mosquito-borne diseases |
| US20050271459A1 (en) * | 2004-06-03 | 2005-12-08 | World Wide Stationery Mfg. Co., Ltd. | Interlocking ring tip formations for paired ring members of a ring binder mechanism |
| NZ534939A (en) * | 2004-08-26 | 2007-04-27 | Bomac Research Ltd | Injectable formulation comprising an anthelmintic compound with complexing compound for improved solubility |
| DE102004053964A1 (de) * | 2004-11-09 | 2006-05-11 | Bayer Healthcare Ag | Mittel gegen Demodikose |
| TW200922635A (en) * | 2007-08-31 | 2009-06-01 | Archimedes Dev Ltd | Non-aqueous pharmaceutical compositions |
| US20100022469A1 (en) * | 2008-06-24 | 2010-01-28 | Majid Razzak | Anthelminthic formulations |
| PL2396006T3 (pl) | 2009-02-16 | 2013-06-28 | Zoetis Llc | Preparat zawierający doramektynę w dużej dawce |
| CN101773467B (zh) * | 2010-01-20 | 2015-09-09 | 北京大北农动物保健科技有限责任公司 | 一种美贝霉素或美贝霉素肟的兽用缓释注射液及制备方法 |
| KR101805087B1 (ko) * | 2010-09-16 | 2017-12-05 | 주식회사 엘지화학 | 높은 방부력을 제공하는 오일 주사 제형 |
| US9616044B2 (en) * | 2012-03-13 | 2017-04-11 | Bayer New Zealand Ltd | Long acting compositions |
| US20170232024A1 (en) | 2014-08-04 | 2017-08-17 | Jerry Tan Eye Surgery Pte Ltd | Pharmaceutical compositions for demodex related blepharitis and eyelid crusting |
| CN119157876A (zh) | 2017-12-15 | 2024-12-20 | 塔苏斯制药有限公司 | 用于治疗睑炎的异恶唑啉驱虫剂制剂和方法 |
| AU2020231319A1 (en) * | 2019-03-01 | 2021-10-21 | Boehringer Ingelheim Animal Health USA Inc. | Injectable clorsulon compositions, methods and uses thereof |
| US12502377B2 (en) | 2019-04-04 | 2025-12-23 | Tarsus Pharmaceuticals, Inc. | Method of eradicating ticks that attach to humans using lotilaner formulations |
| US11638714B2 (en) | 2020-11-10 | 2023-05-02 | Mountain Valley Md Inc | Water dissolvable macrocyclic lactone cyclodextrin complexes |
| US11077134B1 (en) | 2020-11-10 | 2021-08-03 | Mountain Valley Md Inc | Water dissolvable macrocyclic lactone cyclodextrin complexes |
| CA3249951A1 (en) * | 2022-01-28 | 2023-08-03 | Rebel Medicine Inc | Injectable pharmaceutical compositions for treating pain |
| CN114642632A (zh) * | 2022-02-25 | 2022-06-21 | 河北科技大学 | 一种莫西克汀注射液及其制备方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4914624A (cg-RX-API-DMAC7.html) * | 1972-06-08 | 1974-02-08 | ||
| SE434277B (sv) * | 1976-04-19 | 1984-07-16 | Merck & Co Inc | Sett att framstella nya antihelmintiskt verkande foreningar genom odling av streptomyces avermitilis |
| US4199569A (en) * | 1977-10-03 | 1980-04-22 | Merck & Co., Inc. | Selective hydrogenation products of C-076 compounds and derivatives thereof |
| NZ197796A (en) * | 1980-08-04 | 1984-11-09 | Merck & Co Inc | Stabilised aqueous formulations containing ivermectin |
| NZ210505A (en) * | 1983-12-22 | 1988-06-30 | Merck & Co Inc | Parasiticidal compositions containing avermectin or milbemycin derivatives |
| DE3727648A1 (de) * | 1987-08-19 | 1989-03-02 | Bayer Ag | Neue avermectin derivate, verfahren zu ihrer herstellung und ihre verwendung |
| US5510117A (en) * | 1989-03-09 | 1996-04-23 | Micro-Pak, Inc. | Entrapment vehicle and method |
| DK0393890T3 (da) * | 1989-04-11 | 1992-09-28 | Pfizer | Injicerbart præparat indeholdende 25-cyclohexyl-avermectin B1 |
| 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 |
| EP0525307B1 (en) * | 1991-07-23 | 1996-03-06 | American Cyanamid Company | Stable compositions for parenteral administration and their use |
| EP0535734B1 (en) * | 1991-09-30 | 1999-06-02 | Merck & Co. Inc. | Long acting injectable formulations containing hydrogenated castor oil |
| WO1994008566A1 (en) * | 1992-10-21 | 1994-04-28 | Micro Vesicular Systems, Inc. | Entrapment vehicle and method |
-
1996
- 1996-04-09 DE DE19613972A patent/DE19613972A1/de not_active Withdrawn
-
1997
- 1997-03-27 BR BRPI9708540-5A patent/BR9708540B1/pt active IP Right Grant
- 1997-03-27 AT AT97916406T patent/ATE285233T1/de active
- 1997-03-27 PT PT97916406T patent/PT896534E/pt unknown
- 1997-03-27 ES ES97916406T patent/ES2235230T3/es not_active Expired - Lifetime
- 1997-03-27 EP EP97916406A patent/EP0896534B1/de not_active Expired - Lifetime
- 1997-03-27 WO PCT/EP1997/001569 patent/WO1997037653A1/de not_active Ceased
- 1997-03-27 CN CN97193700A patent/CN1095662C/zh not_active Expired - Lifetime
- 1997-03-27 CA CA002251087A patent/CA2251087C/en not_active Expired - Lifetime
- 1997-03-27 JP JP53579597A patent/JP4257870B2/ja not_active Expired - Fee Related
- 1997-03-27 AU AU25066/97A patent/AU718807B2/en not_active Expired
- 1997-03-27 US US09/155,836 patent/US6063394A/en not_active Expired - Lifetime
- 1997-03-27 DE DE59712134T patent/DE59712134D1/de not_active Expired - Lifetime
- 1997-03-27 NZ NZ332224A patent/NZ332224A/en not_active IP Right Cessation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999027906A1 (en) * | 1997-12-03 | 1999-06-10 | Merck & Co., Inc. | Long acting injectable formulations containing hydrogenated castor oil |
| HRP20000366B1 (en) * | 1997-12-03 | 2009-08-31 | Merck & Co. Inc. | Long acting injectable formulations containing hydrogenated castor oil |
| US6174540B1 (en) | 1998-09-14 | 2001-01-16 | Merck & Co., Inc. | Long acting injectable formulations containing hydrogenated caster oil |
Also Published As
| Publication number | Publication date |
|---|---|
| HK1019404A1 (en) | 2000-02-11 |
| US6063394A (en) | 2000-05-16 |
| CN1215331A (zh) | 1999-04-28 |
| JP2000508301A (ja) | 2000-07-04 |
| CA2251087A1 (en) | 1997-10-16 |
| AU2506697A (en) | 1997-10-29 |
| ATE285233T1 (de) | 2005-01-15 |
| ES2235230T3 (es) | 2005-07-01 |
| AU718807B2 (en) | 2000-04-20 |
| BR9708540B1 (pt) | 2010-07-27 |
| EP0896534B1 (de) | 2004-12-22 |
| CN1095662C (zh) | 2002-12-11 |
| DE59712134D1 (de) | 2005-01-27 |
| NZ332224A (en) | 2000-06-23 |
| EP0896534A1 (de) | 1999-02-17 |
| PT896534E (pt) | 2005-04-29 |
| JP4257870B2 (ja) | 2009-04-22 |
| WO1997037653A1 (de) | 1997-10-16 |
| BR9708540A (pt) | 1999-08-03 |
| CA2251087C (en) | 2008-01-15 |
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| Date | Code | Title | Description |
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| 8139 | Disposal/non-payment of the annual fee |