CA1098063A - Substances and process for their production - Google Patents
Substances and process for their productionInfo
- Publication number
- CA1098063A CA1098063A CA276,126A CA276126A CA1098063A CA 1098063 A CA1098063 A CA 1098063A CA 276126 A CA276126 A CA 276126A CA 1098063 A CA1098063 A CA 1098063A
- Authority
- CA
- Canada
- Prior art keywords
- hydroxy
- broken line
- line indicates
- compound
- compounds
- 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
Links
- 238000000034 method Methods 0.000 title claims abstract description 42
- 239000000126 substance Substances 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title description 7
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- 230000004151 fermentation Effects 0.000 claims abstract description 27
- 241001468227 Streptomyces avermitilis Species 0.000 claims abstract description 12
- 235000015097 nutrients Nutrition 0.000 claims abstract description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 16
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/01—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing oxygen
-
- 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
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/44—Preparation of O-glycosides, e.g. glucosides
- C12P19/60—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin
- C12P19/62—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin the hetero ring having eight or more ring members and only oxygen as ring hetero atoms, e.g. erythromycin, spiramycin, nystatin
- C12P19/623—Avermectin; Milbemycin; Ivermectin; C-076
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/886—Streptomyces
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- Molecular Biology (AREA)
- General Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67832876A | 1976-04-19 | 1976-04-19 | |
| US678,328 | 1976-04-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1098063A true CA1098063A (en) | 1981-03-24 |
Family
ID=24722350
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA276,126A Expired CA1098063A (en) | 1976-04-19 | 1977-04-13 | Substances and process for their production |
Country Status (40)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8486995B2 (en) | 2007-06-29 | 2013-07-16 | Bayer Corporation | Acaricidal active substance combinations |
Families Citing this family (269)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ186851A (en) * | 1977-04-11 | 1984-12-14 | Merck & Co Inc | Glycosyloxy derivatives of milbemycin and parasiticidal compositions |
| US4093629A (en) * | 1977-04-11 | 1978-06-06 | Merck & Co., Inc. | Derivatives of antibiotic substance milbemycin and processes therefor |
| NZ188459A (en) * | 1977-10-03 | 1982-09-07 | Merck & Co Inc | Derivatives of c-076 compounds and pesticidal compositions |
| PH15982A (en) | 1977-10-03 | 1983-05-18 | Merck & Co Inc | Selective hydrogenation producta of c-076 compounds and derivatives thereof |
| US4206205A (en) * | 1977-10-03 | 1980-06-03 | Merck & Co., Inc. | Monosaccharide and aglycone derivatives of C-076 |
| PH16612A (en) * | 1977-12-19 | 1983-11-28 | Merck & Co Inc | 13-halo and 13-deoxy derivatives of c-076 compounds |
| US4203976A (en) * | 1978-08-02 | 1980-05-20 | Merck & Co., Inc. | Sugar derivatives of C-076 compounds |
| US4200581A (en) * | 1978-08-04 | 1980-04-29 | Merck & Co., Inc. | Alkyl derivatives of C-076 compounds |
| US4263168A (en) * | 1979-01-10 | 1981-04-21 | Imperial Chemical Industries Limited | Olefine polymerization catalyst |
| US4550160A (en) * | 1979-08-13 | 1985-10-29 | Merck & Co., Inc. | Processes for the interconversion of C-076 compounds |
| JPS5632481A (en) | 1979-08-23 | 1981-04-01 | Sankyo Co Ltd | Antibiotic b-41d, its preparation, and acaricide and anthelminthic agent and repellent containing the same as active constituent |
| US4289760A (en) * | 1980-05-02 | 1981-09-15 | Merck & Co., Inc. | 23-Keto derivatives of C-076 compounds |
| US4285963A (en) * | 1980-08-07 | 1981-08-25 | Merck & Co., Inc. | Novel derivatives of C-076 compounds |
| US4385065A (en) | 1980-10-23 | 1983-05-24 | Merck & Co., Inc. | Novel substances and process for their production |
| US4378353A (en) | 1981-02-17 | 1983-03-29 | Merck & Co., Inc. | Novel C-076 compounds |
| US4333925A (en) | 1981-05-11 | 1982-06-08 | Merck & Co., Inc. | Derivatives of C-076 compounds |
| US4399274A (en) | 1981-07-02 | 1983-08-16 | Merck & Co., Inc. | Isolation of non-ionic lipophilic materials on macroreticular polymeric absorbents |
| US4412991A (en) * | 1981-08-28 | 1983-11-01 | Merck & Co., Inc. | 22-Hydroxy derivatives of C-076 compounds, pharmaceutical compositions and method of use |
| NZ201681A (en) * | 1981-09-03 | 1985-11-08 | Merck & Co Inc | Avermectin derivatives and parasiticidal compositions |
| US4457920A (en) * | 1981-09-03 | 1984-07-03 | Merck & Co., Inc. | 4a-Substituted avermectin compounds |
| US4423211A (en) * | 1981-12-21 | 1983-12-27 | Merck & Co., Inc. | Process for the whole broth extraction of avermectin |
| US4423209A (en) * | 1982-02-26 | 1983-12-27 | Merck & Co., Inc. | Processes for the interconversion of avermectin compounds |
| US4427663A (en) | 1982-03-16 | 1984-01-24 | Merck & Co., Inc. | 4"-Keto-and 4"-amino-4"-deoxy avermectin compounds and substituted amino derivatives thereof |
| NZ204074A (en) * | 1982-05-10 | 1986-05-09 | Merck & Co Inc | Synergistic compositions containing avermectins |
| US4430329A (en) | 1982-05-17 | 1984-02-07 | Merck & Co., Inc. | Synergistic treatment of adult canine heartworm with thiacetarsamide and ivermectin |
| EP0102702B1 (en) * | 1982-07-22 | 1987-07-29 | Imperial Chemical Industries Plc | Methods and compositions of combating pests |
| US4469682A (en) * | 1983-01-28 | 1984-09-04 | Merck & Co., Inc. | Avermectin and milbemycin phosphate esters, pharmaceutical compositions, and method of use |
| EP0125155A1 (en) * | 1983-04-07 | 1984-11-14 | Merck & Co. Inc. | Novel synergistic agricultural insecticidal, pesticidal and acaricidal combinations |
| NZ207655A (en) * | 1983-04-07 | 1986-09-10 | Merck & Co Inc | Synergistic veterinary compositions containing an avermectin compound and clorsulon |
| US4530921A (en) * | 1983-10-03 | 1985-07-23 | Merck & Co., Inc. | Avermectin epoxide derivatives and method of use |
| US4560677A (en) * | 1984-01-31 | 1985-12-24 | Merck & Co., Inc. | Synergistic avermectin combination for treating plant pests |
| US5169956A (en) * | 1984-06-05 | 1992-12-08 | American Cyanamid Company | Macrolide antibiotic compounds |
| US4579864A (en) * | 1984-06-11 | 1986-04-01 | Merck & Co., Inc. | Avermectin and milbemycin 13-keto, 13-imino and 13-amino derivatives |
| GB2166436B (en) * | 1984-09-14 | 1989-05-24 | Glaxo Group Ltd | Antibiotic compounds and their preparation |
| US5182207A (en) * | 1984-09-14 | 1993-01-26 | American Cyanamid Company | Strains of streptomyces thermoarchaensis |
| US4587247A (en) * | 1985-02-25 | 1986-05-06 | Merck & Co., Inc. | Substituted and unsubstituted 13-(alkoxy)methoxy derivatives of the avermectin aglycones, compositions and use |
| US4666937A (en) * | 1985-03-04 | 1987-05-19 | Merck & Co., Inc. | Avermectin bioconversion products |
| US4789684A (en) * | 1985-05-02 | 1988-12-06 | Merck & Co., Inc. | Anthelmintic fermentation products of microorganisms |
| NZ215917A (en) | 1985-05-02 | 1989-10-27 | Merck & Co Inc | 22-oh milbemycin derivatives and parasiticidal compositions |
| US4678774A (en) * | 1985-06-06 | 1987-07-07 | Merck & Co., Inc. | Novel synergistic compositions |
| ES8800986A1 (es) * | 1985-07-27 | 1987-12-01 | Pfizer | Un procedimiento para la produccion de un nuevo derivado de avermectina |
| NZ216908A (en) | 1985-07-29 | 1989-06-28 | Merck & Co Inc | Avermectin derivatives |
| US4668696A (en) * | 1985-07-29 | 1987-05-26 | Merck & Co., Inc. | Novel averonectin fermentation product of a microorganism with anthelmintic activity |
| US4766112A (en) * | 1985-07-29 | 1988-08-23 | Merck & Co. Inc. | Anthelmintic fermentation products of a microorganism |
| US4622313A (en) * | 1985-08-01 | 1986-11-11 | Merck & Co., Inc. | O-sulfate derivatives of avermectins and milbemycins having improved water solubility |
| ES8605582A1 (es) * | 1985-12-11 | 1986-03-16 | Antibioticos Sa | Un procedimiento para la preparacion de avermectinas |
| GB8606116D0 (en) * | 1986-03-12 | 1986-04-16 | Glaxo Group Ltd | Process |
| GB8606120D0 (en) * | 1986-03-12 | 1986-04-16 | Glaxo Group Ltd | Process |
| EP0240274A3 (en) * | 1986-04-03 | 1990-03-14 | Merck & Co. Inc. | Avermectins as growth promotant agents |
| US5840704A (en) * | 1986-07-16 | 1998-11-24 | Pfizer Inc. | Antiparasitic agents and process for their preparation |
| DE3750495T2 (de) * | 1986-07-24 | 1995-02-23 | Beecham Group Plc | Milbemycin-Derivate mit parasitenabtötender Aktivität, ein Verfahren zu ihrer Herstellung und die sie enthaltenden Zusammensetzungen. |
| US4833168A (en) * | 1986-10-03 | 1989-05-23 | Merck & Co., Inc. | Avermectin reformatsky adducts |
| US5077398A (en) * | 1986-11-18 | 1991-12-31 | Merck & Co., Inc. | Process for isolation of avermectin B1 components with improved purity and subsequent isolaton of B2 components |
| US5234831A (en) * | 1987-01-23 | 1993-08-10 | Pfizer Inc | Cultures for production of B avermectins |
| ES2058244T3 (es) * | 1987-01-23 | 1994-11-01 | Pfizer | Procedimiento para produccion de avermectinas y cultivos para el mismo. |
| IN167980B (OSRAM) * | 1987-01-23 | 1991-01-19 | Pfizer | |
| US5077278A (en) * | 1987-01-23 | 1991-12-31 | Pfizer Inc. | Non-natural demethylavermectins compositions and method of use |
| US5238848A (en) * | 1987-01-23 | 1993-08-24 | Pfizer Inc | Cultures for production of avermectins |
| US5525506A (en) * | 1987-01-23 | 1996-06-11 | Pfizer Inc. | Process for production of avermectins and cultures therefor |
| US4806527A (en) * | 1987-03-16 | 1989-02-21 | Merck & Co., Inc. | Avermectin derivatives |
| US4831017A (en) * | 1987-06-29 | 1989-05-16 | Merck & Co., Inc. | Increased litter size in monogastric domestic animals after treatment in mid-gestation of gravid female with avermectin or milbemycin compound |
| US4847243A (en) * | 1987-10-08 | 1989-07-11 | Merck & Co., Inc. | Treatment for fescue toxicosis in grazing animals |
| ATE89604T1 (de) * | 1987-10-23 | 1993-06-15 | Pfizer | Verfahren zur herstellung von aglykonen von avermectin und sie enthaltende kulturen. |
| US5240850A (en) * | 1987-10-23 | 1993-08-31 | Pfizer Inc. | Cultures for production of avermectin aglycones |
| ES2045146T3 (es) * | 1987-11-09 | 1994-01-16 | Pfizer | Avermectinas etiladas. |
| US4963667A (en) * | 1987-11-10 | 1990-10-16 | Merck & Co., Inc. | Ivermectin derivative compounds and process for preparing the same |
| GB8726730D0 (en) | 1987-11-14 | 1987-12-16 | Pfizer Ltd | Antiparasitic agents |
| US4895837A (en) * | 1988-01-29 | 1990-01-23 | Merck & Co., Inc. | Avermectin derivatives |
| GB8804440D0 (en) * | 1988-02-25 | 1988-03-23 | Pfizer Ltd | Antiparasitic agents |
| US4918097A (en) * | 1988-03-11 | 1990-04-17 | Ciba-Geigy Corporation | Insecticides and parasiticides |
| GB8815967D0 (en) * | 1988-07-05 | 1988-08-10 | Pfizer Ltd | Antiparasitic agents |
| US5015662A (en) * | 1988-10-18 | 1991-05-14 | Merck & Co., Inc. | Anthelmintic bioconversion products |
| US5120646A (en) * | 1988-10-18 | 1992-06-09 | Chen Shieh Shung T | Process for the preparation of anthelmintive bioconversion products |
| US5015630A (en) * | 1989-01-19 | 1991-05-14 | Merck & Co., Inc. | 5-oxime avermectin derivatives |
| US4897383A (en) * | 1989-02-13 | 1990-01-30 | Merck & Co., Inc. | Avermectin derivatives |
| NZ232422A (en) * | 1989-02-16 | 1992-11-25 | Merck & Co Inc | 13-ketal milbemycin derivatives and parasiticides |
| ATE129286T1 (de) * | 1989-03-31 | 1995-11-15 | Merck & Co Inc | Klonierung von streptomyces avermitilis genen zur biosynthese von avermectin und verfahren zu ihrer verwendung. |
| US5030622A (en) * | 1989-06-02 | 1991-07-09 | Merck & Co., Inc. | Avermectin derivatives |
| US5023241A (en) * | 1989-07-31 | 1991-06-11 | Merck & Co., Inc. | Avermectin derivatives |
| US5830875A (en) * | 1989-10-30 | 1998-11-03 | Merck & Co., Inc. | 24-and 25-substituted avermectin and milbemycin derivatives |
| US5055454A (en) * | 1989-10-30 | 1991-10-08 | Merck & Co., Inc. | 13-epi-avermectin derivatives useful as antiparasitic agents |
| JP2888586B2 (ja) * | 1990-03-05 | 1999-05-10 | 社団法人北里研究所 | エバーメクチンの特定成分を選択生産するための微生物およびその選択的製造法 |
| US5114930A (en) * | 1990-05-14 | 1992-05-19 | Merck & Co., Inc. | Avermectin derivatives with a spacer inserted between the disaccharide and the aglycone useful as antiparasitic agents |
| US5188944A (en) * | 1990-06-22 | 1993-02-23 | Merck & Co., Inc. | Process for the glycosylation of avermectin agylcones |
| US5070015A (en) * | 1990-10-15 | 1991-12-03 | Merck & Co., Inc. | Novel avermectins are produced from known microorganisms |
| US5192546A (en) * | 1991-01-15 | 1993-03-09 | Mycogen Corporation | Synergistic pesticidal compositions |
| US5346698A (en) * | 1991-01-15 | 1994-09-13 | Mycogen Corporation | Synergistic pesticidal compositions |
| US5177063A (en) * | 1991-03-11 | 1993-01-05 | Merck & Co., Inc. | Avermectin compounds with a 6,5-spiroketal ring system |
| US5208222A (en) * | 1991-03-28 | 1993-05-04 | Merck & Co., Inc. | 4"-and 4'-alkylthio avermectin derivatives |
| US5189026A (en) * | 1991-06-07 | 1993-02-23 | Fractal Laboratories, Inc. | Treatment of human diseases involving dysregulation or dysfunction of the nervous system |
| US5262400A (en) * | 1991-06-20 | 1993-11-16 | Merck & Co., Inc. | 4α-substituted avermectin derivatives |
| US5192671A (en) * | 1991-06-26 | 1993-03-09 | Merck & Co., Inc. | Process for the glycosylation of avermectin compounds |
| EP0524687A1 (en) * | 1991-07-23 | 1993-01-27 | Merck & Co. Inc. | A process for the glycosylation of avermectin compounds at the 14a-position |
| EP0524686A1 (en) * | 1991-07-23 | 1993-01-27 | Merck & Co. Inc. | A process for the 14a-hydroxylation of avermectin compounds |
| US5240915A (en) * | 1991-10-15 | 1993-08-31 | Merck & Co., Inc. | Avermectin derivatives |
| US5171742A (en) * | 1991-10-15 | 1992-12-15 | Merck & Co., Inc. | Avermectin compounds with a 6,5-spiroketal ring system ad a 23-acyl substituent |
| US5248669A (en) * | 1991-12-17 | 1993-09-28 | Samir Amer | Inhibition of anoxia or hypoxia-induced, endothelium-mediated vasospasm with avermectins |
| GB9205007D0 (en) * | 1992-03-07 | 1992-04-22 | Pfizer Ltd | Antiparasitic agents |
| US5244879A (en) * | 1992-03-18 | 1993-09-14 | Merck & Co., Inc. | 23-nor-23-oxa avermectin analogs are active anthelmintic agents |
| US5162363A (en) * | 1992-03-18 | 1992-11-10 | Merck & Co., Inc. | 23-nor-23-thia avermectin analogs are active anthelmintic agents |
| US5312753A (en) * | 1992-03-23 | 1994-05-17 | Merck & Co., Inc. | Strain of streptomyces avermitilis capable of glycosylating avermectin compounds at the 13- and 14A positions |
| WO1993018779A1 (en) * | 1992-03-23 | 1993-09-30 | Merck & Co., Inc. | A strain of streptomyces avermitilis glycosylates avermectin compounds |
| US5229415A (en) * | 1992-03-24 | 1993-07-20 | Merck & Co., Inc. | Alkylthio alkyl avermectins are active antiparasitic agents |
| US6103504A (en) * | 1992-03-25 | 2000-08-15 | Pfizer Inc. | Process for production of avermectins and cultures therefor |
| IT1255135B (it) * | 1992-05-05 | 1995-10-20 | Principio attivo a base di avermectine, ceppo e procedimento per la sua preparazione e composizione veterinaria che lo contiene. | |
| US5248678A (en) * | 1992-06-30 | 1993-09-28 | Fractal Laboratories, Inc. | Methods for increasing arousal and alertness and for the amelioration of comatose states |
| US5241083A (en) * | 1992-07-01 | 1993-08-31 | Merck & Co., Inc. | Process for converting the 13-α-hydroxy group of avermectin aglycones |
| US5547955A (en) * | 1992-10-22 | 1996-08-20 | The Clorox Company | High fructose insecticide bait compositions |
| US6162825A (en) * | 1992-10-22 | 2000-12-19 | The Clorox Company | High fructose insecticide bait compositions |
| US5292647A (en) * | 1992-11-30 | 1994-03-08 | Eli Lilly And Company | Strain of streptomyces for producing avermectins and processes therewith |
| US5411946A (en) * | 1993-02-24 | 1995-05-02 | Merck & Co., Inc. | Avermectin derivatives |
| US5602107A (en) * | 1993-05-10 | 1997-02-11 | Merck & Co., Inc. | Pour-on formulations consisting of gylcols, glycerides and avermectin compounds |
| PL174488B1 (pl) * | 1993-05-10 | 1998-08-31 | Merck & Co Inc | Preparat do zwalczania pasożytów zwierząt oraz sposób wytwarzania preparatu do zwalczania pasożytów zwierząt |
| JP2828343B2 (ja) * | 1993-07-23 | 1998-11-25 | ファイザー・インコーポレーテッド | 天然アベルメクチンの沈殿方法 |
| PT714400E (pt) * | 1993-08-19 | 2000-05-31 | Merck & Co Inc | Forma cristalina termodinamicamente estavel do sal de acido benzoico de 4"-desoxi-4"-epimetilamino-avermectina b1a/b1b e processos para a sua preparacao |
| US5478929A (en) * | 1993-09-15 | 1995-12-26 | Merck & Co., Inc. | Bioconversion products of 27-hydroxy avermectin |
| US5380838A (en) * | 1993-10-08 | 1995-01-10 | Merck & Co. Inc. | Stable solvates of avermectin compounds |
| US5399582A (en) * | 1993-11-01 | 1995-03-21 | Merck & Co., Inc. | Antiparasitic agents |
| TW327125B (en) * | 1994-02-07 | 1998-02-21 | Merck & Co Inc | Composition and method for protecting against pine exhausted |
| GB9402916D0 (en) * | 1994-02-16 | 1994-04-06 | Pfizer Ltd | Antiparasitic agents |
| US5578581A (en) * | 1994-04-26 | 1996-11-26 | Merck & Co., Inc. | Active avermectin analogue |
| US5550153A (en) * | 1994-11-14 | 1996-08-27 | Kerz; Phillip D. | Method for treating heartworm-infected canines |
| PT810823E (pt) * | 1995-02-24 | 2001-09-28 | Novartis Ag | Composicao para controlo de parasitas |
| NZ305181A (en) * | 1995-03-20 | 1998-11-25 | Merck & Co Inc | Nodulisporic acid derivatives |
| DE19520275A1 (de) * | 1995-06-02 | 1996-12-05 | Bayer Ag | Endoparasitizide Mittel |
| US5674897A (en) * | 1995-10-20 | 1997-10-07 | Mycogen Corporation | Materials and methods for controlling nematodes |
| US6124359A (en) * | 1995-10-20 | 2000-09-26 | Mycogen Corporation | Materials and methods for killing nematodes and nematode eggs |
| DE19613972A1 (de) * | 1996-04-09 | 1997-10-16 | Bayer Ag | Injektionsformulierungen von Avermectinen und Milbemycinen auf Basis von Rizinusöl |
| AUPN933396A0 (en) * | 1996-04-17 | 1996-05-09 | Pfizer Pty Limited | Non-aqueuos oral-drench compositions containing avermectin compounds |
| EP0928136B1 (en) | 1996-06-05 | 2003-10-22 | Ashmont Holdings Limited | Injectable compositions |
| US6114376A (en) * | 1997-04-30 | 2000-09-05 | Mcgill University | Methods for using macrocyclic lactone compounds as multidrug resistance reversing agents in tumor and other cells |
| US6403308B1 (en) | 1997-04-30 | 2002-06-11 | Mcgill University | Methods for detecting and reversing resistance to macrocyclic lactone compounds |
| DK1035835T3 (da) * | 1997-12-03 | 2003-12-08 | Merck & Co Inc | Langtidsvirkende injicerbare formuleringer indeholdende hydrogeneret castorolie |
| KR20040053390A (ko) * | 1998-02-13 | 2004-06-23 | 화이자 프로덕츠 인코포레이티드 | 아베르멕틴의 비2:비1의 비를 제어할 수 있는 스트렙토마이세스 아베르미틸리스 유전자 |
| ES2359973T3 (es) * | 1998-03-19 | 2011-05-30 | MERCK SHARP & DOHME CORP. | Composiciones poliméricas líquidas para la liberación controlada de sustancias bioactivas. |
| GB9825402D0 (en) | 1998-11-19 | 1999-01-13 | Pfizer Ltd | Antiparasitic formulations |
| US6787342B2 (en) | 2000-02-16 | 2004-09-07 | Merial Limited | Paste formulations |
| DE10013914A1 (de) | 2000-03-21 | 2001-09-27 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| US7897559B2 (en) * | 2000-06-29 | 2011-03-01 | Parks L Dean | Dermatological composition and kit containing avermectin compound for treating dermatological conditions |
| US6399651B1 (en) * | 2000-06-29 | 2002-06-04 | L. Dean Parks | Method of treating dermatoses using avermectin compound |
| DE10055941A1 (de) | 2000-11-10 | 2002-05-23 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| DE10059606A1 (de) * | 2000-12-01 | 2002-06-06 | Bayer Ag | Wirkstoffkombinationen |
| AR036872A1 (es) | 2001-08-13 | 2004-10-13 | Du Pont | Compuesto de antranilamida, composicion que lo comprende y metodo para controlar una plaga de invertebrados |
| DE10203688A1 (de) * | 2002-01-31 | 2003-08-07 | Bayer Cropscience Ag | Synergistische insektizide Mischungen |
| PL211693B1 (pl) * | 2002-02-12 | 2012-06-29 | Pfizer Prod Inc | Gen Streptomyces Avermitilis kierujący stosunkiem awermektyn B2:B1 |
| DE10207241A1 (de) * | 2002-02-21 | 2003-09-04 | Bayer Cropscience Ag | Synergistische insektizide Mischungen |
| GB2386066A (en) * | 2002-02-28 | 2003-09-10 | Norbrook Lab Ltd | Long-acting parasiticidal composition with improved bioavailability comprising a salicylanilide, a further anti-parasitic compound & a polymeric species |
| US7001889B2 (en) * | 2002-06-21 | 2006-02-21 | Merial Limited | Anthelmintic oral homogeneous veterinary pastes |
| US20060205681A1 (en) * | 2002-06-21 | 2006-09-14 | Maryam Moaddeb | Homogenous paste formulations |
| US6764999B2 (en) | 2002-07-11 | 2004-07-20 | Stephen E. Bachman | Nasal delivery of parasiticides |
| US20040077703A1 (en) * | 2002-10-02 | 2004-04-22 | Soll Mark D. | Nodulisporic acid derivative spot-on formulations for combating parasites |
| DE10248257A1 (de) * | 2002-10-16 | 2004-04-29 | Bayer Cropscience Ag | Wirkstoffkombinationen im insektiziden und akariziden Eigenschaften |
| GB0229804D0 (en) * | 2002-12-20 | 2003-01-29 | Syngenta Participations Ag | Avermection b1 and avermectin b1 monosaccharide derivatives having an alkoxymethyl substituent in the 4"- or 4'-position |
| GB0316377D0 (en) | 2003-07-12 | 2003-08-13 | Norbrook Lab Ltd | Parasiticidal composition |
| DE10353281A1 (de) | 2003-11-14 | 2005-06-16 | Bayer Cropscience Ag | Wirkstoffkombination mit insektiziden und akariziden Eigenschaften |
| US7531186B2 (en) | 2003-12-17 | 2009-05-12 | Merial Limited | Topical formulations comprising 1-N-arylpyrazole derivatives and amitraz |
| US7671034B2 (en) | 2003-12-19 | 2010-03-02 | Merial Limited | Stabilized formulation of ivermectin feed premix with an extended shelf life |
| US7666444B2 (en) | 2004-02-02 | 2010-02-23 | Wyeth | Antiparasitic composition |
| US7493609B2 (en) * | 2004-08-30 | 2009-02-17 | International Business Machines Corporation | Method and apparatus for automatic second-order predictive commoning |
| MX2007003378A (es) | 2004-09-23 | 2007-05-10 | Schering Plough Ltd | Control de parasitos en animales mediante el uso de nuevos derivados de trifluorometansulfonanilida oxima eter. |
| DE102004053964A1 (de) * | 2004-11-09 | 2006-05-11 | Bayer Healthcare Ag | Mittel gegen Demodikose |
| WO2006055565A2 (en) * | 2004-11-19 | 2006-05-26 | Schering-Plough Ltd. | Control of parasites in animals by the use of parasiticidal 2-phenyl-3-(1h-pyrrol-2-yl) acrylonitrile derivatives |
| GB0501220D0 (en) * | 2005-01-21 | 2005-03-02 | Norbrook Lab Ltd | Anthelmintic composition |
| US8362086B2 (en) | 2005-08-19 | 2013-01-29 | Merial Limited | Long acting injectable formulations |
| US20080027011A1 (en) * | 2005-12-20 | 2008-01-31 | Hassan Nached | Homogeneous paste and gel formulations |
| US8119667B2 (en) * | 2005-12-29 | 2012-02-21 | Schering-Plough Animal Health Corporation | Carbonates of fenicol antibiotics |
| EP1849363A1 (en) * | 2006-03-09 | 2007-10-31 | Cheminova A/S | Synergistic combination of glutamate- and GABA-gated chloride agonist pesticide and at least one of Vitamin E or Niacin |
| US20070238700A1 (en) * | 2006-04-10 | 2007-10-11 | Winzenberg Kevin N | N-phenyl-1,1,1-trifluoromethanesulfonamide hydrazone derivative compounds and their usage in controlling parasites |
| TWI422328B (zh) | 2006-06-19 | 2014-01-11 | Univ California | 結合有殺線蟲之種子塗覆物的生物控制劑 |
| HUE027891T2 (en) | 2006-07-05 | 2016-11-28 | Merial Inc | 1-Aryl-5-alkylpyrazole derivatives and methods for their preparation and use |
| DE102007007750A1 (de) * | 2006-08-17 | 2008-02-21 | Bayer Cropscience Ag | Avermectinderivate |
| FR2906468B1 (fr) * | 2006-09-28 | 2012-09-21 | Galderma Sa | Utilisation de composes de la famille des avermectines pour le traitement de desordres dermatologiques |
| US8044230B2 (en) * | 2006-12-13 | 2011-10-25 | Intervet Inc. | Water-soluble prodrugs of chloramphenicol, thiamphenicol, and analogs thereof |
| WO2008076259A1 (en) * | 2006-12-13 | 2008-06-26 | Schering-Plough Ltd. | Water-soluble prodrugs of florfenicol and its analogs |
| US8901163B2 (en) | 2007-01-03 | 2014-12-02 | Galderma S.A. | Method of treating hyperesthesia, paresthesia, dolor, and pruritus caused by insect stings or noxious weeds or plants using avermectin compound |
| MX2009012082A (es) | 2007-05-15 | 2009-12-01 | Merial Ltd | Compuestos de ariloazol-2-il cianoetilamino, metodo para prepararlos y metodo para utilizarlos. |
| TWI430995B (zh) | 2007-06-26 | 2014-03-21 | Du Pont | 萘異唑啉無脊椎有害動物控制劑 |
| JP6006471B2 (ja) | 2007-06-27 | 2016-10-12 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ | 動物有害生物の防除方法 |
| US8425925B2 (en) * | 2007-06-29 | 2013-04-23 | Y-Tex Corporation | Pesticidal tag |
| MX2010000354A (es) | 2007-06-29 | 2010-06-01 | Y Tex Corp | Etiqueta de oreja plaguicida. |
| TWI556741B (zh) | 2007-08-17 | 2016-11-11 | 英特威特國際股份有限公司 | 異唑啉組成物及其作為抗寄生蟲藥上的應用 |
| EP2039248A1 (de) * | 2007-09-21 | 2009-03-25 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| DE102007045922A1 (de) | 2007-09-26 | 2009-04-02 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| NZ585499A (en) | 2007-11-26 | 2011-12-22 | Merial Ltd | Solvent systems for pour-on formulations for combating parasites |
| ES2584930T3 (es) | 2007-12-21 | 2016-09-30 | Merial Limited | El uso de compuestos de 6-halógeno-(1,2,4)-triazolo-(1,5-a)-pirimidina para combatir plagas en y sobre animales |
| TWI468407B (zh) | 2008-02-06 | 2015-01-11 | Du Pont | 中離子農藥 |
| EP2127522A1 (de) | 2008-05-29 | 2009-12-02 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| WO2010008891A2 (en) * | 2008-06-24 | 2010-01-21 | Merial Limited | Anthelminthic formulations |
| KR20110038723A (ko) * | 2008-07-30 | 2011-04-14 | 인터벳 인터내셔널 비.브이. | 플로르페니콜에 대한 중간체로서 유용한 옥사졸린-보호된 아미노디올 화합물의 제조 방법 |
| CA2675093A1 (en) * | 2008-08-08 | 2010-02-08 | Michael L. Corrado | Treatment of bed mite and bed bug infestations |
| PT3050874T (pt) | 2008-11-14 | 2019-05-09 | Boehringer Ingelheim Animal Health Usa Inc | Compostos parasiticidas de ariloazol-2-il-cianoetilamino enantiomericamente enriquecidos |
| US8683346B2 (en) * | 2008-11-17 | 2014-03-25 | Sap Portals Israel Ltd. | Client integration of information from a supplemental server into a portal |
| NZ592865A (en) | 2008-11-19 | 2013-08-30 | Merial Ltd | Compositions comprising an aryl pyrazole and/or a formamidine, methods and uses thereof |
| US9173728B2 (en) | 2008-11-19 | 2015-11-03 | Merial Inc. | Multi-cavity container having offset indentures for dispensing fluids |
| WO2010065852A1 (en) | 2008-12-04 | 2010-06-10 | Merial Limited | Dimeric avermectin and milbemycin derivatives |
| EP2227951A1 (de) | 2009-01-23 | 2010-09-15 | Bayer CropScience AG | Verwendung von Enaminocarbonylverbindungen zur Bekämpfung von durch Insekten übertragenen Viren |
| BRPI1009345A2 (pt) | 2009-03-17 | 2016-03-08 | Intervet Int Bv | sistema de administracao de droga, uso de um sistema de administracao de droga, e, metodo pata tratar doencas |
| ES2527833T3 (es) | 2009-03-25 | 2015-01-30 | Bayer Cropscience Ag | Combinaciones de principios activos nematicidas que comprenden fluopiram y otro principio activo |
| NZ597929A (en) | 2009-07-30 | 2013-09-27 | Merial Ltd | Insecticidal 4-amino-thieno[2,3-d]-pyrimidine compounds and methods of their use |
| BR112012002519A2 (pt) | 2009-08-05 | 2019-09-24 | Du Pont | "pesticidas mesoiônicos" |
| EP2462125A2 (en) | 2009-08-05 | 2012-06-13 | E. I. du Pont de Nemours and Company | Mesoionic pesticides |
| UA107804C2 (en) | 2009-08-05 | 2015-02-25 | Du Pont | Mixtures of pesticides mezoionnyh |
| UA110924C2 (uk) | 2009-08-05 | 2016-03-10 | Е. І. Дю Пон Де Немур Енд Компані | Мезоіонні пестициди |
| BR112012008185A2 (pt) * | 2009-10-07 | 2016-08-16 | Wyeth Llc | composições que compreendem adjuvante, macrolídeo e antígeno proteináceo, e métodos para uso dessas composições |
| EP2327410A1 (en) | 2009-10-28 | 2011-06-01 | Consiglio Nazionale Delle Ricerche - Infm Istituto Nazionale Per La Fisica Della Materia | Avermectins and milbemycins for the treatment of flavivirus infections |
| WO2011069143A1 (en) | 2009-12-04 | 2011-06-09 | Merial Limited | Pesticidal bis-organosulfur compounds |
| DK2513104T3 (en) | 2009-12-17 | 2016-04-11 | Merial Inc | ANTIPARASITE DIHYDROAZOLE COMPOUNDS AND COMPOSITIONS COMPREHENSIVE THESE |
| NZ600845A (en) | 2009-12-17 | 2014-08-29 | Merial Ltd | Compositions comprising macrocyclic lactone compounds and spirodioxepinoindoles |
| RS55986B1 (sr) * | 2010-01-22 | 2017-09-29 | Bayer Ip Gmbh | Akaricidne i/ili insekticidne kombinacije aktivnih supstanci |
| UY33282A (es) | 2010-03-25 | 2011-09-30 | Novartis Ag | Composiciones endoparasiticidas |
| UA108641C2 (uk) | 2010-04-02 | 2015-05-25 | Паразитицидна композиція, яка містить чотири активних агенти, та спосіб її застосування | |
| EP2382865A1 (de) | 2010-04-28 | 2011-11-02 | Bayer CropScience AG | Synergistische Wirkstoffkombinationen |
| HUE028600T2 (en) | 2010-05-12 | 2016-12-28 | Merial Inc | Injectable parasiticidal formulations of levamisole and macrocyclic lactones |
| UA108881C2 (xx) | 2010-05-27 | 2015-06-25 | Кристалічна форма 4-$5-$3-хлор-5-(трифторметил)феніл]-4,5-дигідро-5-(трифторметил)-3-ізоксазоліл]-n-$2-оксо-2-$(2,2,2-трифторетил)аміно]етил]-1-нафталінкарбоксаміду | |
| AR081970A1 (es) | 2010-06-24 | 2012-10-31 | Intervet Int Bv | Formulacion inyectable de una lactona macrociclica y levamisol, formulacion y uso veterinario |
| RU2578036C2 (ru) | 2010-06-29 | 2016-03-20 | Сева Санте Анимале Са | Новые инъекционные композиции эприномектина |
| CA2811924C (en) | 2010-10-20 | 2015-06-16 | Galderma S.A. | Method of treating hemorrhoids using macrocyclic lactone compound |
| CA2811926A1 (en) | 2010-10-20 | 2012-04-26 | Galderma S.A. | Method of treating otitis externa using macrocyclic lactone compound |
| HUE031125T2 (en) | 2010-11-16 | 2017-07-28 | Merial Inc | New monensin derivatives for the treatment and prevention of protozoal infections |
| NZ627856A (en) | 2010-12-07 | 2016-03-31 | Merial Inc | Topical combination formulations of macrocyclic lactones with synthetic pyrethroids |
| WO2012087630A1 (en) | 2010-12-20 | 2012-06-28 | E.I. Du Pont De Nemours And Company | Pyridine and pyrimidine compounds for controlling invertebrate |
| GB201021836D0 (en) | 2010-12-21 | 2011-02-02 | Norbrook Lab Ltd | Topical Composition |
| US9420799B2 (en) | 2011-04-15 | 2016-08-23 | Syngenta Participations Ag | Method for controlling nematode pests |
| US20120329832A1 (en) | 2011-06-27 | 2012-12-27 | Jean Delaveau | Novel Insect-Repellent Coumarin Derivatives, Syntheses, and Methods of Use |
| CN103717573B (zh) | 2011-06-27 | 2016-02-24 | 梅里亚股份有限公司 | 酰氨基-吡啶基醚化合物和组合物和它们对抗寄生物的用途 |
| CN102356769A (zh) * | 2011-09-02 | 2012-02-22 | 魏振东 | 一种含有机质的可湿性粉剂农药 |
| LT3172964T (lt) | 2011-09-12 | 2020-12-10 | Boehringer Ingelheim Animal Health USA Inc. | Paraziticidinės kompozicijos, apimančios izoksazolino veiklųjį agentą, būdas ir jų panaudojimas |
| US20130079394A1 (en) | 2011-09-23 | 2013-03-28 | Cnrs (Centre National Recherche Scientifique) | Indirect modeling of new repellent molecules active against insects, acarids, and other arthropods |
| JP6249568B2 (ja) | 2011-11-17 | 2017-12-20 | メリアル インコーポレイテッド | アリールピラゾールと置換イミダゾールを含む組成物、その使用方法 |
| MX358476B (es) | 2011-12-02 | 2018-08-22 | Merial Ltd | Formulaciones de moxidectina inyectables de larga acción y formas de cristal de moxidectina novedosas. |
| RS58370B1 (sr) | 2012-02-06 | 2019-03-29 | Merial Inc | Paraziticidne oralne veterinarske kompozicije koje sadrže sistemski delujuća aktivna sredstva, metodi i primene istih |
| JO3626B1 (ar) | 2012-02-23 | 2020-08-27 | Merial Inc | تركيبات موضعية تحتوي على فيبرونيل و بيرميثرين و طرق استخدامها |
| WO2013158422A1 (en) | 2012-04-17 | 2013-10-24 | E. I. Du Pont De Nemours And Company | Heterocyclic compounds for controlling invertebrate pests |
| CA3059936A1 (en) | 2012-04-20 | 2013-10-24 | Boehringer Ingelheim Animal Health USA Inc. | Parasiticidal compositions comprising benzimidazole derivatives, methods and uses thereof |
| ES2689037T3 (es) | 2012-11-20 | 2018-11-08 | Merial, Inc. | Compuestos y composiciones antihelmínticas y procedimiento de utilización de los mismos |
| AU2014212217B2 (en) | 2013-01-31 | 2016-11-10 | Boehringer Ingelheim Animal Health USA Inc. | Method for treating and curing Leishmaniosis using fexinidazole |
| US10307405B2 (en) | 2013-04-12 | 2019-06-04 | Zoetis Services Llc | Stable veterinary combination formulations of macrocyclic lactones and imidazothiazoles |
| JP6484641B2 (ja) | 2013-11-01 | 2019-03-13 | メリアル インコーポレイテッド | 駆虫性かつ殺有害生物性のイソオキサゾリン化合物 |
| EP2886640A1 (en) | 2013-12-18 | 2015-06-24 | Riga Technical University | Process for isolation of milbemycins A3 and A4 |
| WO2015161224A1 (en) | 2014-04-17 | 2015-10-22 | Merial, Inc. | Use of malononitrile compounds for protecting animals from parasites |
| AR100530A1 (es) | 2014-05-19 | 2016-10-12 | Merial Inc | Compuestos antihelmínticos |
| EA030459B1 (ru) | 2014-06-19 | 2018-08-31 | Мериал, Инк. | Паразитицидные композиции, содержащие индольные производные, способы их получения и их применение |
| EP3211998B1 (en) | 2014-10-31 | 2021-04-07 | Boehringer Ingelheim Animal Health USA Inc. | Parasiticidal composition comprising fipronil |
| EP3023092A1 (en) | 2014-11-20 | 2016-05-25 | Ceva Sante Animale | Eprinomectin parenteral compositions |
| UY36570A (es) | 2015-02-26 | 2016-10-31 | Merial Inc | Formulaciones inyectables de acción prolongada que comprenden un agente activo isoxazolina, métodos y usos de las mismas |
| AU2016246598B2 (en) | 2015-04-08 | 2020-07-23 | Boehringer lngelheim Vetmedica GMBH | Extended release injectable formulations comprising an isoxazoline active agent, methods and uses thereof |
| HRP20211041T1 (hr) | 2015-05-20 | 2021-10-01 | Boehringer Ingelheim Animal Health USA Inc. | Anthelmintski depsipeptidni spojevi |
| US20160347829A1 (en) | 2015-05-27 | 2016-12-01 | Merial Inc. | Compositions containing antimicrobial IgY antibodies, for treatment and prevention of disorders and diseases caused by oral health compromising (OHC) microorganisms |
| KR101687973B1 (ko) | 2015-12-08 | 2016-12-21 | 주식회사 씨티씨바이오 | 마이크로필름 코팅을 이용한 동물 사료용 프리믹스 제조방법 |
| UY37137A (es) | 2016-02-24 | 2017-09-29 | Merial Inc | Compuestos antiparasitarios de isoxazolina, formulaciones inyectables de acción prolongada que los comprenden, métodos y usos de los mismos |
| RU2630316C1 (ru) * | 2016-06-24 | 2017-09-07 | Карина Микаилевна Мирзаева | Препарат для борьбы с насекомыми-кератофагами |
| WO2018039508A1 (en) | 2016-08-25 | 2018-03-01 | Merial, Inc. | Method for reducing unwanted effects in parasiticidal treatments |
| WO2018055022A1 (en) | 2016-09-22 | 2018-03-29 | Syngenta Participations Ag | Pesticidal mixtures |
| US10653144B2 (en) | 2016-10-14 | 2020-05-19 | Boehringer Ingelheim Animal Health USA Inc. | Pesticidal and parasiticidal vinyl isoxazoline compounds |
| BR112019009977A2 (pt) | 2016-11-16 | 2019-08-27 | Boehringer Ingelheim Animal Health Usa Inc | compostos depsipeptídicos anti-helmínticos |
| EP3644741B1 (en) | 2017-06-26 | 2023-06-07 | Boehringer Ingelheim Animal Health USA Inc. | Dual active parasiticidal granule compositions, methods and uses thereof |
| AU2018318945A1 (en) | 2017-08-14 | 2020-03-05 | Boehringer Ingelheim Animal Health USA Inc. | Pesticidal and parasiticidal pyrazole-isoxazoline compounds |
| WO2019152808A1 (en) | 2018-02-01 | 2019-08-08 | Yale University | Compositions and methods for inhibition of nuclear-penetrating antibodies |
| WO2019157241A1 (en) | 2018-02-08 | 2019-08-15 | Boehringer Ingelheim Animal Health USA Inc. | Parasiticidal compositions comprising eprinomectin and praziquantel, methods and uses thereof |
| MX2021000293A (es) | 2018-07-09 | 2021-07-15 | Boehringer Ingelheim Animal Health Usa Inc | Compuestos heterociclicos antihelminticos. |
| CN113260419A (zh) | 2018-11-20 | 2021-08-13 | 勃林格殷格翰动物保健美国公司 | 吲唑基氰基乙基氨基化合物、其组合物、其制备方法和其使用方法 |
| NZ776819A (en) | 2019-01-16 | 2023-04-28 | Boehringer Ingelheim Animal Health Usa Inc | Topical compositions comprising a neonicotinoid and a macrocyclic lactone, methods and uses thereof |
| WO2020180635A1 (en) | 2019-03-01 | 2020-09-10 | Boehringer Ingelheim Animal Health USA Inc. | Injectable clorsulon compositions, methods and uses thereof |
| CN119285648A (zh) | 2019-03-19 | 2025-01-10 | 勃林格殷格翰动物保健有限公司 | 驱虫的氮杂-苯并噻吩和氮杂-苯并呋喃化合物 |
| BR112022000982A2 (pt) | 2019-07-22 | 2022-03-08 | Intervet Int Bv | Forma de dosagem veterinária mastigável macia |
| US11964977B2 (en) | 2020-05-29 | 2024-04-23 | Boehringer Ingelheim Animal Health USA Inc. | Anthelmintic heterocyclic compounds |
| WO2022034226A1 (en) | 2020-08-14 | 2022-02-17 | Universidad De Navarra | Avermectin and milbemycin compositions for inhalation |
| CN116897044A (zh) | 2020-12-21 | 2023-10-17 | 勃林格殷格翰动物保健有限公司 | 包含异噁唑啉化合物的杀寄生虫环 |
| US20250017210A1 (en) | 2021-11-25 | 2025-01-16 | Syngenta Crop Protection Ag | Pesticidal compositions |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3950360A (en) * | 1972-06-08 | 1976-04-13 | Sankyo Company Limited | Antibiotic substances |
| JPS4914624A (OSRAM) * | 1972-06-08 | 1974-02-08 | ||
| US4134973A (en) * | 1977-04-11 | 1979-01-16 | Merck & Co., Inc. | Carbohydrate derivatives of milbemycin and processes therefor |
| US4161583A (en) * | 1977-10-03 | 1979-07-17 | Merck & Co., Inc. | Method for the separation and purification of antibiotic macrolides |
| US4160861A (en) * | 1977-10-03 | 1979-07-10 | Merck & Co., Inc. | Method for the separation of antibiotic macrolides |
| US4160083A (en) * | 1977-10-03 | 1979-07-03 | Merck & Co., Inc. | Process for the separation of antibiotic macrolides |
| US4160084A (en) * | 1977-10-11 | 1979-07-03 | Merck & Co., Inc. | Method for the separation of antibiotic macrolides |
-
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8486995B2 (en) | 2007-06-29 | 2013-07-16 | Bayer Corporation | Acaricidal active substance combinations |
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