CA2741186C - Thioamide compounds, method of making and method of using thereof - Google Patents

Thioamide compounds, method of making and method of using thereof Download PDF

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Publication number
CA2741186C
CA2741186C CA2741186A CA2741186A CA2741186C CA 2741186 C CA2741186 C CA 2741186C CA 2741186 A CA2741186 A CA 2741186A CA 2741186 A CA2741186 A CA 2741186A CA 2741186 C CA2741186 C CA 2741186C
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CA
Canada
Prior art keywords
halo
alkyl
alkoxy
alkylthio
alkylcarbonyl
Prior art date
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Active
Application number
CA2741186A
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English (en)
French (fr)
Other versions
CA2741186A1 (en
Inventor
Loic Patrick Le Hir De Fallois
Hyoung Ik Lee
Philip Reid Timmons
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Boehringer Ingelheim Animal Health USA Inc
Original Assignee
Merial Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Merial Inc filed Critical Merial Inc
Publication of CA2741186A1 publication Critical patent/CA2741186A1/en
Application granted granted Critical
Publication of CA2741186C publication Critical patent/CA2741186C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D249/00Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/16Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C07D249/18Benzotriazoles
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/41921,2,3-Triazoles
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/0012Galenical forms characterised by the site of application
    • A61K9/0019Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/0012Galenical forms characterised by the site of application
    • A61K9/0053Mouth and digestive tract, i.e. intraoral and peroral administration
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00Antiparasitic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00Antiparasitic agents
    • A61P33/10Anthelmintics
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nutrition Science (AREA)
  • Dermatology (AREA)
  • Physiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
CA2741186A 2008-10-21 2009-10-20 Thioamide compounds, method of making and method of using thereof Active CA2741186C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US10711408P 2008-10-21 2008-10-21
US61/107,114 2008-10-21
PCT/US2009/061337 WO2010048191A1 (en) 2008-10-21 2009-10-20 Thioamide compounds, method of making and method of using thereof

Publications (2)

Publication Number Publication Date
CA2741186A1 CA2741186A1 (en) 2010-04-29
CA2741186C true CA2741186C (en) 2016-07-19

Family

ID=41404569

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2741186A Active CA2741186C (en) 2008-10-21 2009-10-20 Thioamide compounds, method of making and method of using thereof

Country Status (15)

Country Link
US (2) US7964621B2 (https=)
EP (1) EP2358687B9 (https=)
JP (1) JP5614853B2 (https=)
KR (2) KR101782308B1 (https=)
CN (1) CN102239151B (https=)
AU (1) AU2009307736B2 (https=)
BR (1) BRPI0920145B8 (https=)
CA (1) CA2741186C (https=)
CL (1) CL2011000917A1 (https=)
EA (1) EA026649B1 (https=)
ES (1) ES2393965T3 (https=)
MX (1) MX2011004217A (https=)
NZ (1) NZ592382A (https=)
WO (1) WO2010048191A1 (https=)
ZA (1) ZA201103033B (https=)

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EP3216448B8 (en) 2012-02-06 2019-06-05 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
NZ723198A (en) 2012-11-20 2018-11-30 Boehringer Ingelheim Animal Health Usa Inc Anthelmintic compounds and compositions and methods of using thereof
CN103073487B (zh) * 2013-01-15 2014-11-19 西华大学 N-双取代硫代乙酰胺类化合物的合成方法
AR094961A1 (es) 2013-03-15 2015-09-09 Lilly Co Eli 1-hidroxi-benzooxaboroles como agentes antiparasitarios
WO2015066277A1 (en) 2013-11-01 2015-05-07 Merial Limited Antiparisitic and pesticidal isoxazoline compounds
CN104610110A (zh) * 2014-03-12 2015-05-13 广东东阳光药业有限公司 一种制备4-取代硫代苯甲酰胺衍生物的方法
EP3131398B1 (en) 2014-04-17 2019-10-23 Boehringer Ingelheim Animal Health USA Inc. Use of malononitrile compounds for protecting animals from parasites
ES2842592T3 (es) 2014-05-19 2021-07-14 Boehringer Ingelheim Animal Health Usa Inc Compuestos antihelmínticos
US10864193B2 (en) 2014-10-31 2020-12-15 Boehringer Ingelheim Animal Health USA Inc. Parasiticidal compositions comprising fipronil at high concentrations
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
LT3298027T (lt) 2015-05-20 2021-08-10 Boehringer Ingelheim Animal Health USA Inc. Antihelmintiniai depsipeptido junginiai
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
WO2018071535A1 (en) 2016-10-14 2018-04-19 Merial, Inc. Pesticidal and parasiticidal vinyl isoxazoline compounds
CA3044038A1 (en) 2016-11-16 2018-05-24 Boehringer Ingelheim Animal Health USA Inc. Anthelmintic depsipeptide compounds
BR112020003217A2 (pt) 2017-08-14 2020-10-06 Boehringer Ingelheim Animal Health USA Inc. compostos pesticidas e parasiticidas de pirazolisoxazolina
AU2019301510B2 (en) 2018-07-09 2024-06-13 Boehringer Ingelheim Pharma Gmbh & Co. Kg Anthelminthic heterocyclic compounds
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
KR102281492B1 (ko) * 2018-12-24 2021-07-26 동인당제약 주식회사 세벨라머 함유 경구투여용 현탁제 조성물 및 그 제조방법
CA3133100A1 (en) 2019-03-19 2020-09-24 Boehringer Ingelheim Animal Health USA Inc. Anthelmintic aza-benzothiophene and aza-benzofuran compounds
KR20230028268A (ko) 2020-05-29 2023-02-28 뵈링거 잉겔하임 애니멀 헬스 유에스에이 인코포레이티드 구충성 헤테로시클릭 화합물
CN111781291A (zh) * 2020-06-23 2020-10-16 广西壮族自治区水产科学研究院 一种水中13种大环内酯类抗生素的高分辨质谱检测方法
WO2022140728A1 (en) 2020-12-21 2022-06-30 Boehringer Ingelheim Animam Health Usa Inc. Parasiticidal collar comprising isoxazoline compounds
JP2025507585A (ja) 2022-02-17 2025-03-21 ベーリンガー インゲルハイム フェトメディカ ゲーエムベーハー 流体製品メーラーを提供する方法及びシステム
CN117837424A (zh) * 2024-02-04 2024-04-09 黄淮学院 一种控制农作物灰飞虱的方法
WO2025257633A1 (en) 2024-06-12 2025-12-18 Boehringer Ingelheim Vetmedica Gmbh Long-acting castor oil-containing injectable formulations and methods of use thereof

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Also Published As

Publication number Publication date
AU2009307736A1 (en) 2010-04-29
KR20110071140A (ko) 2011-06-28
US8314146B2 (en) 2012-11-20
CN102239151B (zh) 2014-07-02
KR101782308B1 (ko) 2017-09-27
NZ592382A (en) 2013-03-28
US7964621B2 (en) 2011-06-21
CL2011000917A1 (es) 2011-09-16
CA2741186A1 (en) 2010-04-29
US20110190231A1 (en) 2011-08-04
BRPI0920145B8 (pt) 2021-05-25
EP2358687B1 (en) 2012-09-19
CN102239151A (zh) 2011-11-09
EA026649B1 (ru) 2017-05-31
ES2393965T3 (es) 2013-01-03
ES2393965T9 (es) 2013-07-19
EP2358687B9 (en) 2013-04-17
BRPI0920145A2 (pt) 2017-06-06
BRPI0920145B1 (pt) 2021-03-30
AU2009307736B2 (en) 2015-02-05
JP5614853B2 (ja) 2014-10-29
EA201100666A1 (ru) 2011-12-30
JP2012506441A (ja) 2012-03-15
KR20170003704A (ko) 2017-01-09
WO2010048191A1 (en) 2010-04-29
US20100130565A1 (en) 2010-05-27
MX2011004217A (es) 2011-06-20
ZA201103033B (en) 2012-02-29
EP2358687A1 (en) 2011-08-24
KR101782311B1 (ko) 2017-09-27

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