CA2892344C - Synthesis of spirocyclic isoxazoline derivatives - Google Patents

Synthesis of spirocyclic isoxazoline derivatives Download PDF

Info

Publication number
CA2892344C
CA2892344C CA2892344A CA2892344A CA2892344C CA 2892344 C CA2892344 C CA 2892344C CA 2892344 A CA2892344 A CA 2892344A CA 2892344 A CA2892344 A CA 2892344A CA 2892344 C CA2892344 C CA 2892344C
Authority
CA
Canada
Prior art keywords
formula
compound
aqueous base
organics
nitro
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
CA2892344A
Other languages
English (en)
French (fr)
Other versions
CA2892344A1 (en
Inventor
Sean D. W. GREENWOOD
Timothy L. Stuk
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.)
Zoetis Services LLC
Original Assignee
Zoetis Services LLC
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 Zoetis Services LLC filed Critical Zoetis Services LLC
Publication of CA2892344A1 publication Critical patent/CA2892344A1/en
Application granted granted Critical
Publication of CA2892344C publication Critical patent/CA2892344C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D491/00Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10Spiro-condensed systems
    • C07D491/107Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00Preparation of sulfones; Preparation of sulfoxides
    • C07C315/04Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D491/00Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10Spiro-condensed systems
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/55Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
CA2892344A 2012-11-21 2013-11-20 Synthesis of spirocyclic isoxazoline derivatives Active CA2892344C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201261729022P 2012-11-21 2012-11-21
US61/729,022 2012-11-21
PCT/US2013/070959 WO2014081800A1 (en) 2012-11-21 2013-11-20 Synthesis of spirocyclic isoxazoline derivatives

Publications (2)

Publication Number Publication Date
CA2892344A1 CA2892344A1 (en) 2014-05-30
CA2892344C true CA2892344C (en) 2017-06-06

Family

ID=49753486

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2892344A Active CA2892344C (en) 2012-11-21 2013-11-20 Synthesis of spirocyclic isoxazoline derivatives

Country Status (11)

Country Link
US (1) US9593126B2 (https=)
EP (2) EP2922854B1 (https=)
JP (1) JP6234471B2 (https=)
CN (1) CN104918944B (https=)
AU (1) AU2013348091B2 (https=)
BR (1) BR112015011740B1 (https=)
CA (1) CA2892344C (https=)
ES (1) ES2916805T3 (https=)
MX (1) MX368078B (https=)
PL (1) PL2922854T3 (https=)
WO (1) WO2014081800A1 (https=)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HK1210472A1 (en) * 2012-09-07 2016-04-22 Zoetis Services Llc Spirocyclic derivatives as antiparasitic agents
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
EP3426660A1 (en) 2016-03-09 2019-01-16 Basf Se Spirocyclic derivatives
ES2903286T3 (es) 2016-04-06 2022-03-31 Boehringer Ingelheim Animal Health Usa Inc Proceso de preparación de compuestos de isoxazolina enriquecidos enantioméricamente y de solvato de tolueno cristalino de (S)-afoxolaner
US10556909B2 (en) 2016-05-20 2020-02-11 Avista Pharma Solutions, Inc. Synthetic process and intermediates
WO2018071535A1 (en) 2016-10-14 2018-04-19 Merial, Inc. Pesticidal and parasiticidal vinyl isoxazoline compounds
WO2018162312A1 (en) * 2017-03-10 2018-09-13 Basf Se Spirocyclic derivatives
BR112020003217A2 (pt) 2017-08-14 2020-10-06 Boehringer Ingelheim Animal Health USA Inc. compostos pesticidas e parasiticidas de pirazolisoxazolina
CA3118033A1 (en) * 2018-11-06 2020-05-14 Basf Se Process for preparation of optically enriched isoxazolines
KR20230043904A (ko) 2020-07-24 2023-03-31 엘랑코 유에스 인코포레이티드 이속사졸린 화합물 및 이의 중간체의 제조 공정
CN116744917A (zh) 2020-09-04 2023-09-12 礼蓝美国公司 适口调配物
CN113548989A (zh) * 2021-07-14 2021-10-26 浙江倍合德制药有限公司 一种4-硝基苯基-2-甲磺酰基乙酸酯的制备工艺及其生产线
EP4384514A1 (en) 2021-08-11 2024-06-19 Elanco Us Inc. Process for making diaryl isoxazoline derivative
WO2026043852A1 (en) 2024-08-20 2026-02-26 Zoetis Services Llc Process for preparing optically enriched isoxazolines

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5091432A (en) * 1990-03-28 1992-02-25 Glasky Alvin J 9-substituted hypoxanthine bi-functional compounds and their neuroimmunological methods of use
EP1641804A1 (en) * 2003-06-20 2006-04-05 Celltech R & D Limited Thienopyridone derivatives as kinase inhibitors
CN103270036B (zh) * 2010-08-05 2015-11-25 佐蒂斯有限责任公司 作为抗寄生物剂的异噁唑啉衍生物
US9167013B2 (en) * 2011-03-10 2015-10-20 Telefonaktiebolaget L M Ericsson (Publ) Method and apparatus for prioritizing media within an electronic conference according to utilization settings at respective conference participants
ME02412B (me) * 2011-03-10 2016-09-20 Zoetis Services Llc Spirociklični derivati izoksazolina kao antiparazitska sredstva
AR086113A1 (es) * 2011-04-30 2013-11-20 Abbott Lab Isoxazolinas como agentes terapeuticos
TWM424868U (en) 2011-09-02 2012-03-21 yi-zhen Huang Baby walker

Also Published As

Publication number Publication date
EP2922854B1 (en) 2022-05-04
AU2013348091A1 (en) 2015-06-04
EP2922854A1 (en) 2015-09-30
JP2016500106A (ja) 2016-01-07
EP4056572A1 (en) 2022-09-14
PL2922854T3 (pl) 2022-07-18
JP6234471B2 (ja) 2017-11-22
CN104918944A (zh) 2015-09-16
WO2014081800A1 (en) 2014-05-30
MX368078B (es) 2019-09-17
CN104918944B (zh) 2017-05-10
BR112015011740B1 (pt) 2020-04-14
US20150291612A1 (en) 2015-10-15
BR112015011740A2 (pt) 2017-07-11
AU2013348091B2 (en) 2017-04-13
CA2892344A1 (en) 2014-05-30
US9593126B2 (en) 2017-03-14
AU2013348091A8 (en) 2015-07-09
MX2015006458A (es) 2015-08-14
ES2916805T3 (es) 2022-07-06

Similar Documents

Publication Publication Date Title
CA2892344C (en) Synthesis of spirocyclic isoxazoline derivatives
TWI597280B (zh) 化合物之晶型、其製備及用途
CN107522698A (zh) 一种曲贝替定的制备方法及其中间体
CN107001350B (zh) 2-(1’h-吲哚-3’-羰基)-噻唑-4-羧酸甲酯及其结构类似物的有效且可扩展的合成
ES2634940T3 (es) Procedimiento para la producción de intermedios de artemisinina
EP3507282A1 (en) Process for preparing indole carboxamide compounds
CN114685520B (zh) 三并环化合物及其药物组合物和应用
CN106045999B (zh) 一种(1s,4s)‑2,5‑二氮杂二环[2.2.2]辛烷及其衍生物的合成方法
CN101522679B (zh) 氟化长春碱衍生物、其制备和其作为长春花二聚生物碱前体的用途
Murakami et al. Synthesis of amide analogs of Arenastatin A
HK1213547B (en) Synthesis of spirocyclic isoxazoline derivatives
WO2010098496A1 (en) Process for producing tetrahydrotriazolopyridine derivative
EP4662326A1 (en) Ligand-enabled transannular c-h functionalization of cycloalkane carboxylic acids
US7423152B2 (en) Process for the manufacture of intermediates in camptothecin production
JP2010013369A (ja) ピラジン誘導体の製造法
Alizadeh et al. One-pot regio-and chemo-selective synthesis of thiaazatricyclododecane
Pelletier et al. A general synthesis of tetrahydropyrazolo [3, 4-d] thiazoles
RU2346947C1 (ru) Способ получения фурилгетарилметанов, содержащих тиено[2,3-b]пиридиновый фрагмент
KR20220044835A (ko) L-에리트로비오프테린류 화합물의 제조방법
Taghizadeh et al. International Journal of Bio-Inorganic Hybrid Nanomaterials
JPWO2018105492A1 (ja) 3−(ピリジル−2−アミノ)プロピオニトリル及びその類縁体の製造方法
CA2995554A1 (en) Tetrahydrooxepinopyridine compound
CA2647655A1 (en) Novel c-1 analogs of pancratistatin and 7-deoxypancratistatin and processes for their preparation
HK1181037A (en) Method for the production of 5-fluoro-1h-pyrazolo[3,4-b]pyridine-3-carbonitrile

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20150521

MPN Maintenance fee for patent paid

Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 11TH ANNIV.) - STANDARD

Year of fee payment: 11

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20241010

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20241010

MPN Maintenance fee for patent paid

Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 12TH ANNIV.) - STANDARD

Year of fee payment: 12

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20251013

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20251013