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 PDFInfo
- 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.)
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic 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
- C07D213/02—Heterocyclic 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
- C07D213/04—Heterocyclic 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
- C07D213/60—Heterocyclic 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic 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
- C07D401/02—Heterocyclic 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
- C07D401/12—Heterocyclic 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic 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
- C07D417/02—Heterocyclic 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
- C07D417/12—Heterocyclic 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
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- 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
Claims (1)
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imagen1 imagen2 imagen3
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35906410P | 2010-06-28 | 2010-06-28 | |
| US359064P | 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)
| 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 |
| NZ531160A (en) * | 2001-08-20 | 2005-12-23 | Nippon Soda Co | Tetrazoyl oxime derivative as active ingredient in agricultural chemical to control plant disease |
| WO2010000841A1 (en) | 2008-07-04 | 2010-01-07 | Bayer Cropscience Sa | Fungicide hydroximoyl-tetrazole derivatives |
| JP2013529614A (ja) | 2010-06-22 | 2013-07-22 | バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー | ５−置換された１−アルキルテトラゾリルオキシム誘導体の調製方法 |
-
2011
- 2011-06-22 TW TW100121865A patent/TWI511965B/zh not_active IP Right Cessation
- 2011-06-27 KR KR1020137001298A patent/KR20130088133A/ko not_active Application Discontinuation
- 2011-06-27 EP EP11727461.3A patent/EP2585449B1/en not_active Not-in-force
- 2011-06-27 MX MX2012014605A patent/MX2012014605A/es active IP Right Grant
- 2011-06-27 JP JP2013517219A patent/JP5834076B2/ja not_active Expired - Fee Related
- 2011-06-27 WO PCT/EP2011/060675 patent/WO2012000918A1/en active Application Filing
- 2011-06-27 CN CN201180030893.9A patent/CN103108872B/zh not_active Expired - Fee Related
- 2011-06-27 ES ES11727461.3T patent/ES2565087T3/es active Active
- 2011-06-27 DK DK11727461.3T patent/DK2585449T3/en active
- 2011-06-27 US US13/807,101 patent/US8940899B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN103108872B (zh) | 2015-07-22 |
| EP2585449A1 (en) | 2013-05-01 |
| TWI511965B (zh) | 2015-12-11 |
| TW201209048A (en) | 2012-03-01 |
| DK2585449T3 (en) | 2016-03-29 |
| EP2585449B1 (en) | 2016-01-06 |
| MX2012014605A (es) | 2013-02-21 |
| US20130102786A1 (en) | 2013-04-25 |
| KR20130088133A (ko) | 2013-08-07 |
| US8940899B2 (en) | 2015-01-27 |
| CN103108872A (zh) | 2013-05-15 |
| WO2012000918A1 (en) | 2012-01-05 |
| JP2013529662A (ja) | 2013-07-22 |
| JP5834076B2 (ja) | 2015-12-16 |
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