DE3244116A1 - Zusammensetzung zur bekaempfung von endoparasiten - Google Patents
Zusammensetzung zur bekaempfung von endoparasitenInfo
- Publication number
- DE3244116A1 DE3244116A1 DE19823244116 DE3244116A DE3244116A1 DE 3244116 A1 DE3244116 A1 DE 3244116A1 DE 19823244116 DE19823244116 DE 19823244116 DE 3244116 A DE3244116 A DE 3244116A DE 3244116 A1 DE3244116 A1 DE 3244116A1
- Authority
- DE
- Germany
- Prior art keywords
- composition according
- levamisole
- composition
- weight
- acid
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims description 91
- 244000079386 endoparasite Species 0.000 title claims description 7
- HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 claims description 40
- 229960001614 levamisole Drugs 0.000 claims description 39
- 241001465754 Metazoa Species 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 14
- 241001494479 Pecora Species 0.000 claims description 12
- 239000012458 free base Substances 0.000 claims description 12
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000006184 cosolvent Substances 0.000 claims description 8
- 239000004540 pour-on Substances 0.000 claims description 8
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- 244000045947 parasite Species 0.000 claims description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 4
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 claims description 3
- 241000283690 Bos taurus Species 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 claims description 2
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical group CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 claims description 2
- QMAQLCVJIYANPZ-UHFFFAOYSA-N 2-propoxyethyl acetate Chemical compound CCCOCCOC(C)=O QMAQLCVJIYANPZ-UHFFFAOYSA-N 0.000 claims description 2
- 206010061217 Infestation Diseases 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 241000581364 Clinitrachus argentatus Species 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000009472 formulation Methods 0.000 description 24
- 210000002268 wool Anatomy 0.000 description 13
- 238000000034 method Methods 0.000 description 12
- 150000007513 acids Chemical class 0.000 description 7
- 230000037396 body weight Effects 0.000 description 7
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000000699 topical effect Effects 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 230000000590 parasiticidal effect Effects 0.000 description 4
- 239000002297 parasiticide Substances 0.000 description 4
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical group [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- -1 B. Xylene Chemical class 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- 239000007972 injectable composition Substances 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 230000036765 blood level Effects 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- ALOUNLDAKADEEB-UHFFFAOYSA-N dimethyl sebacate Chemical compound COC(=O)CCCCCCCCC(=O)OC ALOUNLDAKADEEB-UHFFFAOYSA-N 0.000 description 2
- 210000004209 hair Anatomy 0.000 description 2
- 244000000013 helminth Species 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- KIUMMUBSPKGMOY-UHFFFAOYSA-N 3,3'-Dithiobis(6-nitrobenzoic acid) Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(SSC=2C=C(C(=CC=2)[N+]([O-])=O)C(O)=O)=C1 KIUMMUBSPKGMOY-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241001147667 Dictyocaulus Species 0.000 description 1
- VIZORQUEIQEFRT-UHFFFAOYSA-N Diethyl adipate Chemical compound CCOC(=O)CCCCC(=O)OCC VIZORQUEIQEFRT-UHFFFAOYSA-N 0.000 description 1
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000243976 Haemonchus Species 0.000 description 1
- 206010061291 Mineral deficiency Diseases 0.000 description 1
- 241000244206 Nematoda Species 0.000 description 1
- 241001137882 Nematodirus Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000510960 Oesophagostomum Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 150000001243 acetic acids Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000003113 alkalizing effect Effects 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 229940014772 dimethyl sebacate Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- KSCKTBJJRVPGKM-UHFFFAOYSA-N octan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-] KSCKTBJJRVPGKM-UHFFFAOYSA-N 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000004672 propanoic acids Chemical class 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000009528 severe injury Effects 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 230000037380 skin damage Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 210000002105 tongue Anatomy 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
- A61K9/0017—Non-human animal skin, e.g. pour-on, spot-on
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Dermatology (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Zoology (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPF173181 | 1981-11-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3244116A1 true DE3244116A1 (de) | 1983-07-07 |
| DE3244116C2 DE3244116C2 (en, 2012) | 1993-02-18 |
Family
ID=3769280
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19823244116 Granted DE3244116A1 (de) | 1981-11-27 | 1982-11-29 | Zusammensetzung zur bekaempfung von endoparasiten |
Country Status (7)
| Country | Link |
|---|---|
| DE (1) | DE3244116A1 (en, 2012) |
| ES (1) | ES8500713A1 (en, 2012) |
| FR (1) | FR2517205B1 (en, 2012) |
| GB (1) | GB2110090B (en, 2012) |
| IE (1) | IE54306B1 (en, 2012) |
| NZ (1) | NZ202526A (en, 2012) |
| ZA (1) | ZA828525B (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ208992A (en) * | 1983-08-12 | 1987-03-06 | Ici Australia Ltd | Endoparasiticidal compositions for topical administration,containing ether or glycol carboxylate ester |
| NZ209100A (en) * | 1983-08-22 | 1987-01-23 | Ici Australia Ltd | Topical compositions for control of endoparasites |
| DE19516522A1 (de) * | 1995-05-05 | 1996-11-07 | Bayer Ag | Neue Flüssigformulierungen |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2408736A1 (de) * | 1973-02-23 | 1974-08-29 | Fisons Ltd | Anthelmintische mittel |
| DE2331793A1 (de) * | 1973-06-22 | 1975-01-16 | Bayer Ag | Pour on-formulierung von tetramisol |
| DE2614841A1 (de) * | 1976-04-06 | 1977-10-20 | Bayer Ag | Neue pour-on-formulierungen von anthelmintika |
| EP0061806A1 (en) * | 1981-03-24 | 1982-10-06 | Janssen Pharmaceutica N.V. | Non-irritating tetramisole- or levamisole pour-on compositions |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4278684A (en) * | 1980-06-17 | 1981-07-14 | Janssen Pharmaceutica N.V. | Non-toxic anthelminthic pour-on composition |
-
1982
- 1982-11-17 NZ NZ202526A patent/NZ202526A/en unknown
- 1982-11-18 ZA ZA828525A patent/ZA828525B/xx unknown
- 1982-11-24 IE IE2800/82A patent/IE54306B1/en not_active IP Right Cessation
- 1982-11-26 ES ES82517710A patent/ES8500713A1/es not_active Expired
- 1982-11-26 FR FR8219882A patent/FR2517205B1/fr not_active Expired
- 1982-11-26 GB GB08233717A patent/GB2110090B/en not_active Expired
- 1982-11-29 DE DE19823244116 patent/DE3244116A1/de active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2408736A1 (de) * | 1973-02-23 | 1974-08-29 | Fisons Ltd | Anthelmintische mittel |
| DE2331793A1 (de) * | 1973-06-22 | 1975-01-16 | Bayer Ag | Pour on-formulierung von tetramisol |
| DE2614841A1 (de) * | 1976-04-06 | 1977-10-20 | Bayer Ag | Neue pour-on-formulierungen von anthelmintika |
| EP0061806A1 (en) * | 1981-03-24 | 1982-10-06 | Janssen Pharmaceutica N.V. | Non-irritating tetramisole- or levamisole pour-on compositions |
Non-Patent Citations (2)
| Title |
|---|
| Chem. Abstr. 91: 103511a * |
| Chem. Abstr. 95: 121164b * |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2517205A1 (fr) | 1983-06-03 |
| ZA828525B (en) | 1983-09-28 |
| GB2110090B (en) | 1985-04-17 |
| NZ202526A (en) | 1985-10-11 |
| DE3244116C2 (en, 2012) | 1993-02-18 |
| ES517710A0 (es) | 1984-11-01 |
| ES8500713A1 (es) | 1984-11-01 |
| IE54306B1 (en) | 1989-08-16 |
| GB2110090A (en) | 1983-06-15 |
| IE822800L (en) | 1983-05-27 |
| FR2517205B1 (fr) | 1987-06-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |