DE69000252T2 - Injizierbare arzneizubereitungen, die 25-cyclohexylavermectin b1 enthalten. - Google Patents
Injizierbare arzneizubereitungen, die 25-cyclohexylavermectin b1 enthalten.Info
- Publication number
- DE69000252T2 DE69000252T2 DE9090303716T DE69000252T DE69000252T2 DE 69000252 T2 DE69000252 T2 DE 69000252T2 DE 9090303716 T DE9090303716 T DE 9090303716T DE 69000252 T DE69000252 T DE 69000252T DE 69000252 T2 DE69000252 T2 DE 69000252T2
- Authority
- DE
- Germany
- Prior art keywords
- cyclohexylavermectin
- sesame oil
- ethyl oleate
- compound
- formulations
- 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 - Fee Related
Links
- 229940126601 medicinal product Drugs 0.000 title 1
- 239000000243 solution Substances 0.000 claims description 18
- 229940093471 ethyl oleate Drugs 0.000 claims description 17
- 239000008159 sesame oil Substances 0.000 claims description 17
- 235000011803 sesame oil Nutrition 0.000 claims description 17
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 claims description 16
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 claims description 16
- 241001465754 Metazoa Species 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 10
- 238000010255 intramuscular injection Methods 0.000 claims description 7
- 239000007927 intramuscular injection Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 238000010254 subcutaneous injection Methods 0.000 claims description 5
- 239000007929 subcutaneous injection Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 208000030852 Parasitic disease Diseases 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 32
- 238000009472 formulation Methods 0.000 description 26
- 150000001875 compounds Chemical class 0.000 description 23
- 239000005660 Abamectin Substances 0.000 description 16
- 238000002347 injection Methods 0.000 description 13
- 239000007924 injection Substances 0.000 description 13
- 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 description 11
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 241000283690 Bos taurus Species 0.000 description 7
- 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 6
- 241000238876 Acari Species 0.000 description 6
- 239000003096 antiparasitic agent Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000006184 cosolvent Substances 0.000 description 4
- 229940102223 injectable solution Drugs 0.000 description 4
- 230000007794 irritation Effects 0.000 description 4
- 229940007210 ivomec Drugs 0.000 description 4
- 244000045947 parasite Species 0.000 description 4
- 244000105624 Arachis hypogaea Species 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 229940125687 antiparasitic agent Drugs 0.000 description 3
- 244000078703 ectoparasite Species 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 230000003902 lesion Effects 0.000 description 3
- 238000007920 subcutaneous administration Methods 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- 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 2
- 235000003911 Arachis Nutrition 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000283086 Equidae Species 0.000 description 2
- 241000244206 Nematoda Species 0.000 description 2
- 241000238680 Rhipicephalus microplus Species 0.000 description 2
- 241000244174 Strongyloides Species 0.000 description 2
- 241000243774 Trichinella Species 0.000 description 2
- 230000002141 anti-parasite Effects 0.000 description 2
- 235000012343 cottonseed oil Nutrition 0.000 description 2
- 239000002385 cottonseed oil Substances 0.000 description 2
- 229940074076 glycerol formal Drugs 0.000 description 2
- 229960002418 ivermectin Drugs 0.000 description 2
- 231100000241 scar Toxicity 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 241001147657 Ancylostoma Species 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 241000244186 Ascaris Species 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 241000257161 Calliphoridae Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000253350 Capillaria Species 0.000 description 1
- 241000243990 Dirofilaria Species 0.000 description 1
- 241000498256 Enterobius Species 0.000 description 1
- 241000288105 Grus Species 0.000 description 1
- 208000006968 Helminthiasis Diseases 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 241000498271 Necator Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241001674048 Phthiraptera Species 0.000 description 1
- 241000207961 Sesamum Species 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- 241000258242 Siphonaptera Species 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 241001489151 Trichuris Species 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 229940124339 anthelmintic agent Drugs 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000013057 ectoparasiticide Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 244000079386 endoparasite Species 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 244000000050 gastrointestinal parasite Species 0.000 description 1
- 244000000013 helminth Species 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005374 membrane filtration Methods 0.000 description 1
- 230000001617 migratory effect Effects 0.000 description 1
- 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 description 1
- 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 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 208000014837 parasitic helminthiasis infectious disease Diseases 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Saccharide Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB898908071A GB8908071D0 (en) | 1989-04-11 | 1989-04-11 | Antiparasitic formulations |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69000252D1 DE69000252D1 (de) | 1992-09-17 |
| DE69000252T2 true DE69000252T2 (de) | 1993-01-07 |
Family
ID=10654763
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE9090303716T Expired - Fee Related DE69000252T2 (de) | 1989-04-11 | 1990-04-06 | Injizierbare arzneizubereitungen, die 25-cyclohexylavermectin b1 enthalten. |
Country Status (24)
| Country | Link |
|---|---|
| AR (1) | AR247096A1 (fr) |
| AT (1) | ATE79263T1 (fr) |
| BG (1) | BG60543B1 (fr) |
| CA (1) | CA2014157C (fr) |
| CZ (1) | CZ180190A3 (fr) |
| DD (1) | DD293497A5 (fr) |
| DE (1) | DE69000252T2 (fr) |
| GB (1) | GB8908071D0 (fr) |
| HU (2) | HU208252B (fr) |
| IE (1) | IE62933B1 (fr) |
| IL (1) | IL94006A0 (fr) |
| IN (1) | IN173967B (fr) |
| MA (1) | MA21803A1 (fr) |
| MX (1) | MX20250A (fr) |
| MY (1) | MY107092A (fr) |
| NZ (1) | NZ233263A (fr) |
| PE (1) | PE24891A1 (fr) |
| PH (1) | PH26970A (fr) |
| PT (1) | PT93697B (fr) |
| RO (1) | RO105648B1 (fr) |
| SK (1) | SK180190A3 (fr) |
| UA (1) | UA18250A (fr) |
| YU (1) | YU47912B (fr) |
| ZA (1) | ZA902737B (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19826091A1 (de) * | 1998-06-12 | 1999-12-16 | Alcatel Sa | Verfahren zum gesicherten Ändern von in einer Datenbank gespeicherten Daten, Datenbanksystem und damit ausgestattetes Netzelement |
-
1989
- 1989-04-11 GB GB898908071A patent/GB8908071D0/en active Pending
-
1990
- 1990-04-02 PH PH40310A patent/PH26970A/en unknown
- 1990-04-04 IL IL94006A patent/IL94006A0/xx not_active IP Right Cessation
- 1990-04-06 AT AT90303716T patent/ATE79263T1/de not_active IP Right Cessation
- 1990-04-06 RO RO144746A patent/RO105648B1/ro unknown
- 1990-04-06 DE DE9090303716T patent/DE69000252T2/de not_active Expired - Fee Related
- 1990-04-09 MX MX2025090A patent/MX20250A/es unknown
- 1990-04-09 AR AR90316585A patent/AR247096A1/es active
- 1990-04-09 PE PE1990167632A patent/PE24891A1/es not_active Application Discontinuation
- 1990-04-09 MY MYPI90000572A patent/MY107092A/en unknown
- 1990-04-09 BG BG91699A patent/BG60543B1/bg unknown
- 1990-04-09 CA CA002014157A patent/CA2014157C/fr not_active Expired - Lifetime
- 1990-04-09 IN IN353DE1990 patent/IN173967B/en unknown
- 1990-04-09 PT PT93697A patent/PT93697B/pt not_active IP Right Cessation
- 1990-04-09 MA MA22062A patent/MA21803A1/fr unknown
- 1990-04-10 SK SK1801-90A patent/SK180190A3/sk not_active IP Right Cessation
- 1990-04-10 NZ NZ233263A patent/NZ233263A/xx unknown
- 1990-04-10 YU YU70490A patent/YU47912B/sh unknown
- 1990-04-10 IE IE128590A patent/IE62933B1/en not_active IP Right Cessation
- 1990-04-10 DD DD90339625A patent/DD293497A5/de unknown
- 1990-04-10 ZA ZA902737A patent/ZA902737B/xx unknown
- 1990-04-10 CZ CS901801A patent/CZ180190A3/cs not_active IP Right Cessation
- 1990-04-11 HU HU902255A patent/HU208252B/hu not_active IP Right Cessation
- 1990-04-11 UA UA4743681A patent/UA18250A/uk unknown
-
1995
- 1995-05-19 HU HU95P/P00135P patent/HU211528A9/hu unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19826091A1 (de) * | 1998-06-12 | 1999-12-16 | Alcatel Sa | Verfahren zum gesicherten Ändern von in einer Datenbank gespeicherten Daten, Datenbanksystem und damit ausgestattetes Netzelement |
Also Published As
| Publication number | Publication date |
|---|---|
| HU211528A9 (en) | 1995-11-28 |
| ATE79263T1 (de) | 1992-08-15 |
| BG91699A (bg) | 1993-12-24 |
| PE24891A1 (es) | 1991-08-17 |
| DD293497A5 (de) | 1991-09-05 |
| GB8908071D0 (en) | 1989-05-24 |
| SK281618B6 (sk) | 2001-05-10 |
| YU47912B (sh) | 1996-05-20 |
| PH26970A (en) | 1992-12-28 |
| PT93697A (pt) | 1990-11-20 |
| IE62933B1 (en) | 1995-03-08 |
| ZA902737B (en) | 1991-11-27 |
| MA21803A1 (fr) | 1990-12-31 |
| IE901285L (en) | 1990-10-11 |
| MX20250A (es) | 1993-11-01 |
| CZ285736B6 (cs) | 1999-10-13 |
| YU70490A (en) | 1992-05-28 |
| NZ233263A (en) | 1991-08-27 |
| CA2014157C (fr) | 1996-05-07 |
| MY107092A (en) | 1995-09-30 |
| RO105648B1 (ro) | 1992-11-30 |
| UA18250A (uk) | 1997-12-25 |
| HUT54272A (en) | 1991-02-28 |
| SK180190A3 (en) | 2001-05-10 |
| AR247096A1 (es) | 1994-11-30 |
| BG60543B1 (bg) | 1995-08-28 |
| HU208252B (en) | 1993-09-28 |
| HU902255D0 (en) | 1990-08-28 |
| CZ180190A3 (cs) | 1999-10-13 |
| CA2014157A1 (fr) | 1990-10-11 |
| IL94006A0 (en) | 1991-03-10 |
| IN173967B (fr) | 1994-08-13 |
| PT93697B (pt) | 1996-08-30 |
| DE69000252D1 (de) | 1992-09-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |