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
Authority
CA
Canada
Prior art keywords
halo
alkyl
alkoxy
alkylthio
alkylcarbonyl
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.)
Active
Application number
CA2741186A
Other languages
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

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C07D249/18—Benzotriazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic 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
    • A61K31/4192—1,2,3-Triazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • 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
    • A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
    • 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
    • A61P33/10—Anthelmintics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic 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
    • C07D471/02—Heterocyclic 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
    • C07D471/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Dermatology (AREA)
  • Nutrition Science (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 (enExample)
EP (1) EP2358687B9 (enExample)
JP (1) JP5614853B2 (enExample)
KR (2) KR101782311B1 (enExample)
CN (1) CN102239151B (enExample)
AU (1) AU2009307736B2 (enExample)
BR (1) BRPI0920145B8 (enExample)
CA (1) CA2741186C (enExample)
CL (1) CL2011000917A1 (enExample)
EA (1) EA026649B1 (enExample)
ES (1) ES2393965T3 (enExample)
MX (1) MX2011004217A (enExample)
NZ (1) NZ592382A (enExample)
WO (1) WO2010048191A1 (enExample)
ZA (1) ZA201103033B (enExample)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH669977A5 (enExample) 1986-02-27 1989-04-28 Bbc Brown Boveri & Cie
WO2012020568A1 (ja) * 2010-08-10 2012-02-16 川崎重工業株式会社 原動機システム及び船舶
HUE042360T2 (hu) 2011-09-12 2019-06-28 Merial Inc Izoxazolin hatóanyagot tartalmazó parazitaellenes készítmények, ezek elõállítása és alkalmazása
AP2014007874A0 (en) 2012-02-06 2014-08-31 Merial Ltd Parasiticidal oral veterinary compositions comprising systemetically- 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
NZ716598A (en) 2012-11-20 2017-02-24 Merial Inc Anthelmintic compounds and compositions and method 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
JP6682719B2 (ja) 2014-04-17 2020-04-15 ベーリンガー インゲルハイム アニマル ヘルス ユーエスエイ インコーポレイテッド 寄生生物から動物を保護するためのマロノニトリル化合物の使用
NZ726874A (en) 2014-05-19 2018-03-23 Merial Inc Anthelmintic compounds
AU2015339096B2 (en) 2014-10-31 2018-08-02 Boehringer Ingelheim Animal Health USA Inc. Parasiticidal composition comprising fipronil
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
RS62130B1 (sr) 2015-05-20 2021-08-31 Boehringer Ingelheim Animal Health Usa Inc Antihelmintička depsipeptidna jedinjenja
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
JP2019535655A (ja) 2016-10-14 2019-12-12 ベーリンガー インゲルハイム アニマル ヘルス ユーエスエイ インコーポレイテッド 殺虫性及び殺寄生虫性ビニルイソオキサゾリン化合物
BR112019009977A2 (pt) 2016-11-16 2019-08-27 Boehringer Ingelheim Animal Health Usa Inc compostos depsipeptídicos anti-helmínticos
MX2020001724A (es) 2017-08-14 2020-07-29 Boehringer Ingelheim Animal Health Usa Inc Compuestos de pirazol-isoxazolina plaguicidas y parasiticidas.
MX2021000293A (es) 2018-07-09 2021-07-15 Boehringer Ingelheim Animal Health Usa Inc Compuestos heterociclicos antihelminticos.
US11773066B2 (en) 2018-11-20 2023-10-03 Boehringer Ingelheim Animal Health USA Inc. Indazolylcyanoethylamino compound, compositions of same, method of making, and methods of using thereof
KR102281492B1 (ko) * 2018-12-24 2021-07-26 동인당제약 주식회사 세벨라머 함유 경구투여용 현탁제 조성물 및 그 제조방법
KR20220002890A (ko) 2019-03-19 2022-01-07 뵈링거 잉겔하임 애니멀 헬스 유에스에이 인코포레이티드 구충성 아자-벤조티오펜 및 아자-벤조푸란 화합물
BR112022024156A2 (pt) 2020-05-29 2023-02-14 Boehringer Ingelheim Animal Health Usa Inc Compostos heterocílicos antelmínticos
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
EP4262789A1 (en) 2020-12-21 2023-10-25 Boehringer Ingelheim Vetmedica GmbH Parasiticidal collar comprising isoxazoline compounds
US12258193B2 (en) 2022-02-17 2025-03-25 Boehringer Ingelheim Vetmedica Gmbh Method and system for providing a fluid product mailer
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

Family Cites Families (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6289076B1 (en) 1997-05-06 2001-09-11 Sumitomo Heavy Industries, Ltd. Transmission system for synchrotron radiation light
US6239077B1 (en) 1998-05-01 2001-05-29 Nihon Nohyaku Co., Ltd. Aminoacetonitrile derivative agricultural and horticultural insecticide containing the same and use thereof
AU2002224942A1 (en) 2000-12-20 2002-07-01 Syngenta Participations Ag N-acyl aminoacetonitriles having pesticidal properties
DE60126838T2 (de) 2000-12-20 2007-11-08 Novartis Ag Amidoacetonitrile zur Bekämpfung von Endoparasiten
AR035531A1 (es) 2001-01-22 2004-06-02 Novartis Ag Composicion para el control de plagas endoparasiticas en ganados y animales domesticos, un metodo para su control y el uso de dicha composicion para la preparacion de medicamentos
RU2284990C2 (ru) 2001-05-15 2006-10-10 Новартис Аг Производные бензамидоацетонитрила, способ их получения, содержащая их композиция для борьбы с нематодами и их применение
AR036054A1 (es) 2001-06-15 2004-08-04 Novartis Ag Uso de compuestos de aminoacetonitrilo para el control de plagas, una composicion y un proceso para dicho control y una composicion farmaceutica contra parasitos
CN1545500A (zh) 2001-10-04 2004-11-10 诺瓦提斯公司 作为抗寄生虫剂的羰氧基-氰基甲基化合物
CN1564809A (zh) 2001-10-04 2005-01-12 诺瓦提斯公司 有机化合物
TW200300140A (en) 2001-11-14 2003-05-16 Novartis Ag Organic compounds
AR037746A1 (es) 2001-12-06 2004-12-01 Novartis Ag Compuestos derivados de amidoacetonitrilo, un procedimiento para su preparacion, un procedimiento para la preparacion de compuestos intermediarios, una composicion para combatir parasitos, un procedimiento para combatir dichos parasitos, y el empleo de dichos derivados para la preparacion de una com
AR038156A1 (es) 2002-01-21 2004-12-29 Novartis Ag Compuestos de amidoacetonitrilo, proceso para su preparacion, composicion para controlar los parasitos, y uso de estos compuestos para preparar una composicion farmaceutica
TW200305556A (en) 2002-03-21 2003-11-01 Novartis Ag Organic compounds
TW200400931A (en) 2002-05-22 2004-01-16 Novartis Ag Organic compounds
AR040082A1 (es) 2002-05-22 2005-03-16 Novartis Ag Derivados de n-acilaminoacetonitrilo y su uso para el control de parasitos
AR039961A1 (es) 2002-06-06 2005-03-09 Novartis Ag Derivados de amidoacetonitrilo y su uso como pesticida
TW200406386A (en) 2002-06-07 2004-05-01 Novartis Ag Organic compounds
TW200400932A (en) 2002-06-19 2004-01-16 Novartis Ag Organic compounds
GB0214117D0 (en) 2002-06-19 2002-07-31 Syngenta Participations Ag N-sulphonylaminoacetonitriles having pesticidal properties
TW200409760A (en) 2002-09-11 2004-06-16 Novartis Ag Organic compounds
GB0402677D0 (en) 2003-11-06 2004-03-10 Novartis Ag Organic compounds
AR046757A1 (es) 2003-12-10 2005-12-21 Novartis Ag Amidoacetonitrilos utiles como pesticidas
TW200613251A (en) 2004-06-10 2006-05-01 Novartis Ag Organic compounds
WO2006043654A1 (ja) 2004-10-22 2006-04-27 Nihon Nohyaku Co., Ltd. アセトニトリル誘導体及び有害生物防除剤並びにその使用方法
ES2388869T3 (es) 2004-11-09 2012-10-19 Novartis Ag Procedimiento para la preparación de enantiómeros de compuestos de amidoacetonitrilo a partir de sus racematos
WO2007017088A1 (en) 2005-07-25 2007-02-15 Novartis Ag Amidonitrile compounds
WO2008062005A1 (en) 2006-11-24 2008-05-29 Novartis Ag The use of aminoacetonitril compounds in the control of endoparasites in warm- blood animals.
US8501950B2 (en) 2006-12-01 2013-08-06 Syngenta Crop Protection Llc N-cyanoalkylanthranilamides as insecticides
US20100027495A1 (en) 2007-02-05 2010-02-04 Nokia Corporation Method and Apparatus for Providing Acknowledgment Signaling
MX2009007482A (es) 2007-02-09 2009-08-13 Pfizer Ltd Agentes antiparasitarios.
PT3088384T (pt) 2007-05-15 2019-03-22 Aventis Agriculture Compostos de ariloazol-2-il-cianoetilamino, método de fabrico e seu método de utilização

Also Published As

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

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