PH27027A - Composition for controlling parasites in productive livestock - Google Patents
Composition for controlling parasites in productive livestock Download PDFInfo
- Publication number
- PH27027A PH27027A PH36667A PH36667A PH27027A PH 27027 A PH27027 A PH 27027A PH 36667 A PH36667 A PH 36667A PH 36667 A PH36667 A PH 36667A PH 27027 A PH27027 A PH 27027A
- Authority
- PH
- Philippines
- Prior art keywords
- group
- subst
- tuted
- sting
- halogen
- Prior art date
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- 244000045947 parasite Species 0.000 title abstract description 11
- 244000144972 livestock Species 0.000 title abstract description 4
- 239000000203 mixture Substances 0.000 title description 38
- -1 hydroxy, benzyloxy Chemical group 0.000 claims abstract description 116
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- 229910052736 halogen Inorganic materials 0.000 claims abstract description 67
- 150000002367 halogens Chemical class 0.000 claims abstract description 62
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 61
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 57
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 55
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 49
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 49
- 125000001424 substituent group Chemical group 0.000 claims abstract description 49
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 42
- 239000001257 hydrogen Substances 0.000 claims abstract description 34
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- 241000607479 Yersinia pestis Species 0.000 claims abstract description 8
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- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
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- 239000008101 lactose Substances 0.000 description 1
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- 230000002045 lasting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
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- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 235000012439 matzos Nutrition 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical class COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 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
- BWCRYQGQPDBOAU-WZBVPYLGSA-N milbemycin D Chemical compound C1C[C@H](C)[C@@H](C(C)C)O[C@@]21O[C@H](C\C=C(C)\C[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 BWCRYQGQPDBOAU-WZBVPYLGSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012764 mineral filler Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 230000001459 mortal effect Effects 0.000 description 1
- LHMUZCNPQGLQPE-UHFFFAOYSA-N n-pyrrolidin-1-ylpyridin-4-amine Chemical compound C1CCCN1NC1=CC=NC=C1 LHMUZCNPQGLQPE-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
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- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
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- 239000004540 pour-on Substances 0.000 description 1
- 101150069548 ppan gene Proteins 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
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- 102220102088 rs878853592 Human genes 0.000 description 1
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- 229910000077 silane Inorganic materials 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
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- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
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- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 150000008334 thiadiazines Chemical class 0.000 description 1
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 description 1
- 235000019157 thiamine Nutrition 0.000 description 1
- 229960003495 thiamine Drugs 0.000 description 1
- 239000011721 thiamine Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
-
- 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
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Molecular Biology (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Fodder In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH111787 | 1987-03-24 | ||
| CH487887 | 1987-12-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PH27027A true PH27027A (en) | 1993-02-01 |
Family
ID=25686704
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PH36667A PH27027A (en) | 1987-03-24 | 1988-03-21 | Composition for controlling parasites in productive livestock |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US4871719A (xx) |
| EP (1) | EP0284563B1 (xx) |
| JP (1) | JP2683583B2 (xx) |
| KR (1) | KR960004533B1 (xx) |
| AT (1) | ATE107307T1 (xx) |
| AU (1) | AU614509B2 (xx) |
| CA (1) | CA1300609C (xx) |
| DE (1) | DE3850160D1 (xx) |
| DK (1) | DK167682B1 (xx) |
| ES (1) | ES2054862T3 (xx) |
| FI (1) | FI92831C (xx) |
| HU (1) | HUT46322A (xx) |
| IE (1) | IE63143B1 (xx) |
| IL (1) | IL85810A (xx) |
| NZ (1) | NZ223970A (xx) |
| PH (1) | PH27027A (xx) |
| PT (1) | PT87033B (xx) |
| ZW (1) | ZW2788A1 (xx) |
Families Citing this family (69)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4906619A (en) * | 1988-07-22 | 1990-03-06 | Merck & Co., Inc. | Alkyl avermectin derivatives |
| NZ232422A (en) * | 1989-02-16 | 1992-11-25 | Merck & Co Inc | 13-ketal milbemycin derivatives and parasiticides |
| US6001822A (en) * | 1989-04-11 | 1999-12-14 | Pfizer Inc. | Antiparasitic formulations |
| US6514951B1 (en) | 1989-12-15 | 2003-02-04 | American Cyanamid Company | Pour-on formulations effective for the control of internal and external parasites of homothermic animals |
| JP3804072B2 (ja) * | 1991-08-07 | 2006-08-02 | 日産化学工業株式会社 | 水性懸濁状農薬製剤 |
| IL128235A (en) * | 1996-08-05 | 2004-03-28 | Bayer Ag | Transformed 2 and 5,2-phenylactuanols, processes for their preparation and preparations containing them for the treatment of nematodes and arthropods |
| KR970014851A (ko) * | 1997-01-03 | 1997-04-28 | 김동규 | 음식물 쓰레기의 건조발효방법 및 그 건조발효장치 |
| ATE249206T1 (de) * | 1997-12-03 | 2003-09-15 | Merck & Co Inc | Langwirkende, injizierbare, formulierungen enthaltend rizinusöl |
| US6733767B2 (en) * | 1998-03-19 | 2004-05-11 | Merck & Co., Inc. | Liquid polymeric compositions for controlled release of bioactive substances |
| US7229447B1 (en) | 1998-08-25 | 2007-06-12 | Advanced Photodynamics Technologies, Inc. | Photodynamic therapy utilizing a solution of photosensitizing compound and surfactant |
| US6787342B2 (en) | 2000-02-16 | 2004-09-07 | Merial Limited | Paste formulations |
| JP2003531828A (ja) | 2000-02-26 | 2003-10-28 | アドバンスト フォトダイナミック テクノロジーズ， インコーポレイテッド | 光感光性物質および界面活性剤を使用する、光力学的な細胞および無細胞生物の根絶 |
| US20060205681A1 (en) * | 2002-06-21 | 2006-09-14 | Maryam Moaddeb | Homogenous paste formulations |
| US7001889B2 (en) * | 2002-06-21 | 2006-02-21 | Merial Limited | Anthelmintic oral homogeneous veterinary pastes |
| US20040077703A1 (en) * | 2002-10-02 | 2004-04-22 | Soll Mark D. | Nodulisporic acid derivative spot-on formulations for combating parasites |
| US7531186B2 (en) | 2003-12-17 | 2009-05-12 | Merial Limited | Topical formulations comprising 1-N-arylpyrazole derivatives and amitraz |
| 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 |
| BRPI0714194A2 (pt) | 2006-07-05 | 2012-12-25 | Aventis Agriculture | compostos derivados de 1-aril-5-alquilpirazol, processos para fazÊ-los e mÉtodos para seus usos |
| PT3428148T (pt) | 2007-05-15 | 2020-10-13 | Aventis Agriculture | Compostos de ariloazol-2-il-cianoetilamino, método de fabrico e seu método de utilização |
| CA2706448C (en) | 2007-11-26 | 2016-08-16 | Merial Limited | Solvent systems for pour-on formulations for combating parasites |
| AU2009271299B2 (en) * | 2008-06-24 | 2014-09-11 | Boehringer Ingelheim Animal Health USA Inc. | Anthelminthic formulations |
| ES2729854T3 (es) | 2008-11-14 | 2019-11-06 | Merial Inc | Compuestos de ariloazol-2-ilcianoetilamino parasiticidas enriquecidos enantioméricamente |
| 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 |
| CN102282154B (zh) | 2008-12-04 | 2015-07-01 | 梅瑞尔公司 | 二聚的阿佛菌素和米尔倍霉素衍生物 |
| MX2012001170A (es) | 2009-07-30 | 2012-07-20 | Merial Ltd | Compuestos de 4-amino-tieno [2,3-d]pirimidina insecticidas y metodos para su uso. |
| US8846569B2 (en) | 2009-12-04 | 2014-09-30 | Merial Limited | Pesticidal bis-organosulfur compounds |
| ES2894036T3 (es) | 2009-12-17 | 2022-02-11 | Boehringer Ingelheim Animal Health Usa Inc | Compuestos de dihidroazol antiparasitarios y composiciones que los comprenden |
| BR112012014933B1 (pt) | 2009-12-17 | 2020-10-27 | Merial, Inc. | composições que compreendem compostos lactonas macrocíclicas e spirodioxepinoindóis |
| UA108641C2 (uk) | 2010-04-02 | 2015-05-25 | Паразитицидна композиція, яка містить чотири активних агенти, та спосіб її застосування | |
| DK2568980T3 (en) | 2010-05-12 | 2015-11-30 | Merial Inc | INJECTABLE PARASITICIDE FORMULATIONS OF LEVAMISOL AND MACROCYCLIC LACTONS |
| DK2640728T3 (en) | 2010-11-16 | 2016-11-28 | Merial Inc | NEW MONENSINDERIVATER FOR TREATMENT AND PREVENTION OF protozoal INFECTIONS |
| NZ612185A (en) | 2010-12-07 | 2015-10-30 | Merial Inc | Topical combination formulations of macrocyclic lactones with synthetic pyrethroids |
| US20120329832A1 (en) | 2011-06-27 | 2012-12-27 | Jean Delaveau | Novel Insect-Repellent Coumarin Derivatives, Syntheses, and Methods of Use |
| ES2618813T3 (es) | 2011-06-27 | 2017-06-22 | Merial, Inc. | Compuestos y composiciones de éter amido-piridílico y uso contra los parásitos |
| SG11201400558YA (en) | 2011-09-12 | 2014-04-28 | Merial Ltd | Parasiticidal compositions comprising an isoxazoline active agent, methods and uses thereof |
| WO2013044118A2 (en) | 2011-09-23 | 2013-03-28 | Merial Limited | Indirect modeling of new repellent molecules active against insects, acarids, and other arthropods |
| US9173404B2 (en) | 2011-11-17 | 2015-11-03 | Merial, Inc. | Compositions comprising an aryl pyrazole and a substituted imidazole, methods and uses thereof |
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| NZ746271A (en) | 2012-02-06 | 2020-05-29 | Boehringer Ingelheim Animal Health Usa Inc | Parasiticidal oral veterinary compositions comprising systemically-acting active agents, methods and uses thereof |
| JO3626B1 (ar) | 2012-02-23 | 2020-08-27 | Merial Inc | تركيبات موضعية تحتوي على فيبرونيل و بيرميثرين و طرق استخدامها |
| CA3059936A1 (en) | 2012-04-20 | 2013-10-24 | Boehringer Ingelheim Animal Health USA Inc. | Parasiticidal compositions comprising benzimidazole derivatives, methods and uses thereof |
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| US10045979B2 (en) | 2014-05-19 | 2018-08-14 | Merial Inc. | Anthelmintic compounds |
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| 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 |
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| DK3298027T3 (da) | 2015-05-20 | 2021-08-09 | Boehringer Ingelheim Animal Health Usa Inc | Anthelmintiske depsipeptidforbindelser |
| 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 |
| 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 |
| WO2018039508A1 (en) | 2016-08-25 | 2018-03-01 | Merial, Inc. | Method for reducing unwanted effects in parasiticidal treatments |
| 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 |
| WO2019005700A1 (en) | 2017-06-26 | 2019-01-03 | Merial, Inc. | DOUBLE-ACTING PARASITICIDE GRANULATE COMPOSITIONS, METHODS AND USES THEREOF |
| WO2019036407A1 (en) | 2017-08-14 | 2019-02-21 | Merial, Inc. | PYRAZOLE-ISOXAZOLINE COMPOUNDS WITH PESTICIDE AND PARASITICIDE ACTIVITY |
| WO2019157241A1 (en) | 2018-02-08 | 2019-08-15 | Boehringer Ingelheim Animal Health USA Inc. | Parasiticidal compositions comprising eprinomectin and praziquantel, methods and uses thereof |
| CN112996788B (zh) | 2018-07-09 | 2024-07-16 | 勃林格殷格翰动物保健美国公司 | 驱蠕虫的杂环化合物 |
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| AU2020208145B2 (en) | 2019-01-16 | 2023-02-02 | Boehringer Ingelheim Vetmedica Gmbh | Topical compositions comprising a neonicotinoid and a macrocyclic lactone, methods and uses thereof |
| CN113507922A (zh) | 2019-03-01 | 2021-10-15 | 勃林格殷格翰动物保健美国公司 | 可注射的氯舒隆组合物、其方法和用途 |
| WO2020191091A1 (en) | 2019-03-19 | 2020-09-24 | Boehringer Ingelheim Animal Health USA Inc. | Anthelmintic aza-benzothiophene and aza-benzofuran compounds |
| MX2022000843A (es) | 2019-07-22 | 2022-02-10 | Intervet Int Bv | Forma de dosificacion blanda masticable de uso veterinario. |
| WO2021242581A1 (en) | 2020-05-29 | 2021-12-02 | Boehringer Ingelheim Animal Health USA Inc. | Anthelmintic heterocyclic compounds |
| WO2022140728A1 (en) | 2020-12-21 | 2022-06-30 | Boehringer Ingelheim Animam Health Usa Inc. | Parasiticidal collar comprising isoxazoline compounds |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3950360A (en) * | 1972-06-08 | 1976-04-13 | Sankyo Company Limited | Antibiotic substances |
| US4173571A (en) * | 1977-12-19 | 1979-11-06 | Merck & Co., Inc. | 13-Halo and 13-deoxy derivatives of C-076 compounds |
| US4328335A (en) * | 1979-08-13 | 1982-05-04 | Merck & Co., Inc. | Process 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 |
| US4457920A (en) * | 1981-09-03 | 1984-07-03 | Merck & Co., Inc. | 4a-Substituted avermectin compounds |
| EP0165900A3 (de) * | 1984-06-08 | 1986-05-28 | Ciba-Geigy Ag | Neue Lactone, Verfahren zu ihrer Herstellung und ihre Verwendung in der Schädlingsbekämpfung |
| FR2570390B1 (fr) * | 1984-09-14 | 1987-11-27 | Glaxo Group Ltd | Nouveaux composes antibiotiques et procede de preparation |
| HUT39739A (en) * | 1984-12-04 | 1986-10-29 | Ciba Geigy Ag | Process for production of derivatives of 13,3-milbemycin and medical preparatives containing thereof |
| ES8802229A1 (es) * | 1985-04-30 | 1988-04-16 | Glaxo Group Ltd | Un procedimiento para preparar nuevos derivados lactonicos macrociclicos. |
| US4778809A (en) * | 1985-08-23 | 1988-10-18 | Ciba-Geigy Corporation | 5-esters of milbemycins for controlling parasitic pests |
| US4833168A (en) * | 1986-10-03 | 1989-05-23 | Merck & Co., Inc. | Avermectin reformatsky adducts |
-
1988
- 1988-03-16 US US07/168,766 patent/US4871719A/en not_active Expired - Fee Related
- 1988-03-18 DE DE3850160T patent/DE3850160D1/de not_active Expired - Fee Related
- 1988-03-18 EP EP88810175A patent/EP0284563B1/de not_active Expired - Lifetime
- 1988-03-18 ES ES88810175T patent/ES2054862T3/es not_active Expired - Lifetime
- 1988-03-18 AT AT88810175T patent/ATE107307T1/de not_active IP Right Cessation
- 1988-03-21 FI FI881328A patent/FI92831C/fi not_active IP Right Cessation
- 1988-03-21 PH PH36667A patent/PH27027A/en unknown
- 1988-03-22 CA CA000562065A patent/CA1300609C/en not_active Expired - Lifetime
- 1988-03-22 IL IL85810A patent/IL85810A/xx not_active IP Right Cessation
- 1988-03-22 ZW ZW27/88A patent/ZW2788A1/xx unknown
- 1988-03-22 PT PT87033A patent/PT87033B/pt active IP Right Grant
- 1988-03-22 NZ NZ223970A patent/NZ223970A/xx unknown
- 1988-03-23 JP JP63069204A patent/JP2683583B2/ja not_active Expired - Lifetime
- 1988-03-23 HU HU881498A patent/HUT46322A/hu unknown
- 1988-03-23 AU AU13502/88A patent/AU614509B2/en not_active Ceased
- 1988-03-23 DK DK157188A patent/DK167682B1/da not_active IP Right Cessation
- 1988-03-23 IE IE87188A patent/IE63143B1/en not_active IP Right Cessation
- 1988-03-24 KR KR88003168A patent/KR960004533B1/ko not_active IP Right Cessation
-
1989
- 1989-07-13 US US07/380,844 patent/US4973711A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| KR880011169A (ko) | 1988-10-27 |
| CA1300609C (en) | 1992-05-12 |
| ES2054862T3 (es) | 1994-08-16 |
| PT87033B (pt) | 1992-06-30 |
| PT87033A (pt) | 1988-04-01 |
| AU1350288A (en) | 1988-09-22 |
| FI92831C (fi) | 1995-01-10 |
| DE3850160D1 (de) | 1994-07-21 |
| IL85810A0 (en) | 1988-09-30 |
| US4973711A (en) | 1990-11-27 |
| EP0284563A2 (de) | 1988-09-28 |
| ATE107307T1 (de) | 1994-07-15 |
| DK157188D0 (da) | 1988-03-23 |
| US4871719A (en) | 1989-10-03 |
| FI92831B (fi) | 1994-09-30 |
| JPS63255286A (ja) | 1988-10-21 |
| EP0284563A3 (en) | 1989-10-25 |
| FI881328A (fi) | 1988-09-25 |
| JP2683583B2 (ja) | 1997-12-03 |
| IL85810A (en) | 1992-06-21 |
| DK157188A (da) | 1988-09-25 |
| HUT46322A (en) | 1988-10-28 |
| EP0284563B1 (de) | 1994-06-15 |
| IE63143B1 (en) | 1995-03-22 |
| IE880871L (en) | 1988-09-24 |
| AU614509B2 (en) | 1991-09-05 |
| ZW2788A1 (en) | 1988-11-16 |
| FI881328A0 (fi) | 1988-03-21 |
| NZ223970A (en) | 1990-05-28 |
| KR960004533B1 (en) | 1996-04-06 |
| DK167682B1 (da) | 1993-12-06 |
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