ES2565087T3 - Procedimiento de preparación de derivados de 1-alquiltetrazolil oxima 5-sustituidos - Google Patents

Procedimiento de preparación de derivados de 1-alquiltetrazolil oxima 5-sustituidos Download PDF

Info

Publication number
ES2565087T3
ES2565087T3 ES11727461.3T ES11727461T ES2565087T3 ES 2565087 T3 ES2565087 T3 ES 2565087T3 ES 11727461 T ES11727461 T ES 11727461T ES 2565087 T3 ES2565087 T3 ES 2565087T3
Authority
ES
Spain
Prior art keywords
alkyl
formula
halogen atoms
substituted
cycloalkyl
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
ES11727461.3T
Other languages
English (en)
Inventor
Christian Beier
David Bernier
Pierre-Yves Coqueron
Philippe Desbordes
Christophe Dubost
Norbert Lui
Sergii Pazenok
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.)
Bayer Intellectual Property GmbH
Original Assignee
Bayer Intellectual Property GmbH
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 Bayer Intellectual Property GmbH filed Critical Bayer Intellectual Property GmbH
Application granted granted Critical
Publication of ES2565087T3 publication Critical patent/ES2565087T3/es
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72Nitrogen atoms
    • C07D213/75Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10Antimycotics
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Communicable Diseases (AREA)
  • Animal Behavior & Ethology (AREA)
  • Oncology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Procedimiento de preparación de derivados de 1-alquiltetrazolil oxima 5-sustituidos de fórmula general (I)**Fórmula** en la que R1 es alquilo o fenilo opcionalmente monosustituido con halógeno, ciano, nitro, alquilo C1-C8, alcoxi C1-C8, metilsulfonilo, trifluorometilo o arilo, R2 es alquilo C1-C12, haloalquilo C1-C12 o un alcoxialquilo de fórmula -[A-O]m-B, A es alcanodiilo (alquileno) C2-C4, B es alquilo C1-C6, m 1 o 2, R3 es un grupo piridinilo (Het1) o un grupo tiazolilo (Het2)**Fórmula** en las que R es hidrógeno o halógeno, Z es hidrógeno, halógeno, alquilo C1-C8, cicloalquilo C3-C8, alquenilo C2-C8, alquinilo C2-C8, no sustituido o sustituido en cada caso, o el grupo -N(Ra)C(>=O)Q, Q es hidrógeno, alquilo C1-C8, cicloalquilo C3-C8, cicloalquenil C3-C8-alquilo C1-C8, halocicloalquilo C3-C8 con de 1 a 5 átomos de halógeno, cicloalquil C3-C8-alquilo C1-C8, cicloalquenilo C3-C8, alquenilo C2-C8, haloalquenilo C2-C8 con de 1 a 5 átomos de halógeno, alquinilo C3-C8, haloalquinilo C2-C8 con de 1 a 5 átomos de halógeno, alcoxi C1-C8, haloalcoxi C1-C8 con de 1 a 5 átomos de halógeno, haloalcoxialquilo C1-C8 con de 1 a 5 átomos de halógeno, alqueniloxi C2-C8, haloalqueniloxi C2-C8 con de 1 a 5 átomos de halógeno, alquiniloxi C3-C8, haloalquiniloxi C3-C8 con de 1 a 5 átomos de halógeno, alquil C1-C8-amino, (alcoxi C1-C6-imino)-alquilo C1-C6, (alqueniloxi C1-C6-imino)-alquilo C1-C6, (alquiniloxi C1-C6-imino)-alquilo C1- C6, (benciloxi-imino)-alquilo C1-C6, alquil C1-C8-sulfenilo, arilsulfenilo, tri(alquil C1-C8)silil-alquilo C1-C8, tri(alquil C1-C8)sililoxi, tri(alquil C1-C8-silil)cicloalquilo C3-C8, arilo, fenoxi, fenoxialquilo, benciloxi, heterocicliclo, bicicloalquilo C5-C12, bicicloalquenilo C5-C12, carbociclilo C5-C12 benzo-condensado, no sustituido o sustituido en cada caso, Ra es hidrógeno, alquilo C1-C8, cicloalquilo C3-C8, alquenilo C2-C8, alquinilo C2-C8, arilo, heterocicliclo, no sustituido o sustituido en cada caso, caracterizado porque (1) en una primera etapa, una oxima de fórmula general (II)**Fórmula** en la que R1 tiene los significados dados anteriormente, se convierte, usando una base, en la sal de la oxima y después se hace reaccionar con un compuesto de fórmula general (III)**Fórmula** en la que R3 tiene los significados dados anteriormente, y Y es cloro, bromo, yodo, mesilato o tosilato, y los éteres de oxima de fórmula general (IV) obtenidos de este modo**Fórmula** en la que R1 y R3 tiene los significados dados anteriormente, (2) se hacen reaccionar en una segunda etapa con azidas de fórmula R5-N3, en las que R5 es sodio, potasio, tetrabutilamonio, trimetilsililo o difenilfosforilo, y los derivados de tetrazolil oxima 5-sustituidos de fórmula (V) obtenidos de este modo**Fórmula** en la que R1 y R3 tiene los significados dados anteriormente, (3) se hacen reaccionar en una tercera etapa con un agente alquilante de fórmula (VI)**Fórmula** en la que R2 tiene los significados dados anteriormente y L es cloro.

Description

imagen1
imagen2
imagen3
imagen4
imagen5
imagen6
imagen7
imagen8

Claims (1)

  1. imagen1
    imagen2
    imagen3
ES11727461.3T 2010-06-28 2011-06-27 Procedimiento de preparación de derivados de 1-alquiltetrazolil oxima 5-sustituidos Active ES2565087T3 (es)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US359064P 2002-02-20
US35906410P 2010-06-28 2010-06-28
EP10167449 2010-06-28
EP10167449 2010-06-28
PCT/EP2011/060675 WO2012000918A1 (en) 2010-06-28 2011-06-27 Process for the preparation of 5-substituted 1-alkyltetrazolyl oxime derivatives

Publications (1)

Publication Number Publication Date
ES2565087T3 true ES2565087T3 (es) 2016-03-31

Family

ID=42988324

Family Applications (1)

Application Number Title Priority Date Filing Date
ES11727461.3T Active ES2565087T3 (es) 2010-06-28 2011-06-27 Procedimiento de preparación de derivados de 1-alquiltetrazolil oxima 5-sustituidos

Country Status (10)

Country Link
US (1) US8940899B2 (es)
EP (1) EP2585449B1 (es)
JP (1) JP5834076B2 (es)
KR (1) KR20130088133A (es)
CN (1) CN103108872B (es)
DK (1) DK2585449T3 (es)
ES (1) ES2565087T3 (es)
MX (1) MX2012014605A (es)
TW (1) TWI511965B (es)
WO (1) WO2012000918A1 (es)

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2019A (en) * 1841-03-29 goedes
US3209008A (en) * 1963-02-08 1965-09-28 Edward J Poziomek Preparation of aromatic glyoxylonitrile oximes
DE2825565A1 (de) 1978-06-10 1979-12-20 Bayer Ag Verfahren zur herstellung von 2-oximinophenylacetonitril
US4748186A (en) 1986-06-30 1988-05-31 Fmc Corporation S-trifluorobutenyl derivatives and pesticidal uses thereof
UA73307C2 (uk) * 1999-08-05 2005-07-15 Куміаі Кемікал Індастрі Ко., Лтд. Похідна карбамату і фунгіцид сільськогосподарського/садівницького призначення
US6610701B2 (en) * 2001-02-09 2003-08-26 Merck & Co., Inc. Thrombin inhibitors
TW577883B (en) * 2001-08-20 2004-03-01 Dainippon Ink & Chemicals Tetrazoyloxime derivative and agricultural chemical comprising the same as active ingredient
MX2010013900A (es) 2008-07-04 2011-02-15 Bayer Cropscience Ag Derivados de hidroximoil-tetrazol fungicidas.
MX2012014607A (es) 2010-06-22 2013-02-21 Bayer Ip Gmbh Proceso para preparacion de derivados de 1-alquiltetrazolil oxima 5-sustituidos.

Also Published As

Publication number Publication date
EP2585449A1 (en) 2013-05-01
JP5834076B2 (ja) 2015-12-16
US20130102786A1 (en) 2013-04-25
EP2585449B1 (en) 2016-01-06
TW201209048A (en) 2012-03-01
MX2012014605A (es) 2013-02-21
JP2013529662A (ja) 2013-07-22
TWI511965B (zh) 2015-12-11
US8940899B2 (en) 2015-01-27
KR20130088133A (ko) 2013-08-07
WO2012000918A1 (en) 2012-01-05
DK2585449T3 (en) 2016-03-29
CN103108872B (zh) 2015-07-22
CN103108872A (zh) 2013-05-15

Similar Documents

Publication Publication Date Title
ES2536918T3 (es) Compuestos de benzoilpirazol y herbicidas que los contienen
RU2331643C2 (ru) Пиразолопиримидины и средство, обладающее фунгицидной и бактерицидной активностью для борьбы с вредными организмами, на их основе
EA201070323A1 (ru) Замещенное производное пиразола
NO20053974L (no) Tienopyrimidinforbindelser og anvendelse derav.
RU2009139920A (ru) Изоксазолиновые соединения и их применение в борьбе с вредителями
RU2007146513A (ru) Фунгицидные производные 2-пиридилметиленкарбоксамида
RU2009141611A (ru) Способ получения амидного соединения
AR054981A1 (es) Control de parasitos en animales mediante el uso de nuevos derivados de trifluorometansulfonanilida oxima eter
CO6210770A2 (es) Compuestos 2-aril-5-heterociclil-ciclohexan-1, 3 diona y su uso como herbicidas
EA201170096A1 (ru) Замещенные производные пиримидона
PE20090992A1 (es) Derivados de fenil-amino-pirimidina como agentes inhibidores de cinasa
PE20120732A1 (es) Agonistas del receptor de esfingosina-1-fosfato
WO2010053583A3 (en) Small molecule cd4 mimetics and uses thereof
AR083399A1 (es) Proceso para la preparacion de cicloheptapiridina como antagonista del receptor de cgrp
NO20074718L (no) BCRP/ABCG2 inhibitor
EA200701035A1 (ru) Замещенные n-сульфониламинобензил-2-феноксиацетамидные соединения
MA32642B1 (fr) Amides utiles en therapie
PE20091401A1 (es) Procedimientos para preparar eteres aromaticos
RU2013125326A (ru) Гетероциклические соединения в качестве зондов для визуализации tau-патологии
RU2011108404A (ru) Новые ациламинобензамидные производные
MX2010007019A (es) Compuestos de bencimidazol.
RU2014107744A (ru) Амидиновое соединение или его соль
BR112014004210B1 (pt) processo para a preparação de derivados de diamida do ácido antranílico substituídos com tetrazole por reação de benzoxazinonas com aminas
TW200628446A (en) Substituted pyrrole derivative
RU2014129937A (ru) Способы и промежуточные соединения для получения фармацевтических агентов