CN107428648B - 用于制备可用于合成美托咪定的诸如3-芳基丁醛的化合物的方法 - Google Patents

用于制备可用于合成美托咪定的诸如3-芳基丁醛的化合物的方法 Download PDF

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CN107428648B
CN107428648B CN201680012547.0A CN201680012547A CN107428648B CN 107428648 B CN107428648 B CN 107428648B CN 201680012547 A CN201680012547 A CN 201680012547A CN 107428648 B CN107428648 B CN 107428648B
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formula
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palladium
carbon
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CN107428648A (zh
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拉斯·埃克隆德
马古斯·埃克
拉梅什·埃坎巴朗
昂茨·马萨鲁
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TECH I AB
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C249/02—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of compounds containing imino groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/24—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of a carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/86—Use of additives, e.g. for stabilisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/228—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/14—Esters of phosphoric acids containing P(=O)-halide groups
    • C07F9/1403—Esters of phosphoric acids containing P(=O)-halide groups containing the structure Hal-P(=O)-O-unsaturated acyclic group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/228—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde
    • C07C47/232—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde having unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/24—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing halogen

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Plural Heterocyclic Compounds (AREA)
CN201680012547.0A 2015-01-30 2016-01-29 用于制备可用于合成美托咪定的诸如3-芳基丁醛的化合物的方法 Active CN107428648B (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB1501593.6 2015-01-30
GBGB1501593.6A GB201501593D0 (en) 2015-01-30 2015-01-30 New compounds and processes
PCT/GB2016/050204 WO2016120635A1 (en) 2015-01-30 2016-01-29 Processes for the preparation of compounds, such as 3-arylbutanals, useful in the synthesis of medetomidine

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CN107428648A CN107428648A (zh) 2017-12-01
CN107428648B true CN107428648B (zh) 2021-12-10

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US (1) US10053420B2 (OSRAM)
EP (1) EP3250556B1 (OSRAM)
JP (1) JP6702623B2 (OSRAM)
KR (1) KR102458638B1 (OSRAM)
CN (1) CN107428648B (OSRAM)
DK (1) DK3250556T3 (OSRAM)
ES (1) ES2716748T3 (OSRAM)
GB (1) GB201501593D0 (OSRAM)
HR (1) HRP20190286T1 (OSRAM)
HU (1) HUE042626T2 (OSRAM)
PL (1) PL3250556T3 (OSRAM)
TR (1) TR201902673T4 (OSRAM)
WO (1) WO2016120635A1 (OSRAM)

Families Citing this family (3)

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Publication number Priority date Publication date Assignee Title
US12050293B2 (en) 2018-12-19 2024-07-30 Pgs Geophysical As Medetomidine compositions having improved anti-fouling characteristics
WO2022086416A1 (en) 2020-10-21 2022-04-28 I-Tech Ab Antifouling compounds
EP4506340A1 (en) 2022-03-22 2025-02-12 Obshestvo s Ogranichennoj Otvetstvennostju "Vikzdorove Zhivotnyh" Method for producing medetomidine and its derivatives

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012069422A1 (en) * 2010-11-26 2012-05-31 Lonza Ltd 3-(2,3-dimethylphenyl)-2-butenal and its use as perfume
CN103328431A (zh) * 2011-01-19 2013-09-25 帝斯曼知识产权资产管理有限公司 通过催化碳碳双键加氢制备4-乙酰氧基-2-甲基丁醛的方法
CN103748077A (zh) * 2011-07-22 2014-04-23 坎布雷卡尔斯库加公司 用于制备4-取代咪唑类的新方法

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DE2340812C2 (de) 1973-08-11 1982-05-27 Basf Ag, 6700 Ludwigshafen Phenylpropanale sowie ein Verfahren zu deren Herstellung
US4416902A (en) 1982-07-16 1983-11-22 International Flavors & Fragrances Inc. Flavoring with cyclohexenyl-beta-methyl acrolein derivatives
DE19714042A1 (de) * 1997-04-05 1998-10-08 Henkel Kgaa Verfahren zur Herstellung aromatischer Aldehyde
WO2007111630A1 (en) * 2005-07-29 2007-10-04 Flexitral, Inc. Compounds which release an odor on a change in ph
CN102458659B (zh) * 2009-06-03 2014-07-09 高砂香料工业株式会社 不对称氢化催化剂
WO2012120070A1 (en) * 2011-03-10 2012-09-13 Lonza Ltd Method for preparation of 3-(2,3-dimethylphenyl)-2-butenal
WO2012172119A2 (en) * 2012-05-08 2012-12-20 Lonza Ltd Method for the preparation of medetomidine
WO2012172120A2 (en) * 2012-05-08 2012-12-20 Lonza Ltd 2-(2,3-dimethylphenyl)-1-propanal and its use as perfume
ES2557638T3 (es) * 2012-05-08 2016-01-27 Lonza Ltd Método para la preparación de 2-(2,3-dimetilfenil)-1-propanal

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012069422A1 (en) * 2010-11-26 2012-05-31 Lonza Ltd 3-(2,3-dimethylphenyl)-2-butenal and its use as perfume
CN103328431A (zh) * 2011-01-19 2013-09-25 帝斯曼知识产权资产管理有限公司 通过催化碳碳双键加氢制备4-乙酰氧基-2-甲基丁醛的方法
CN103748077A (zh) * 2011-07-22 2014-04-23 坎布雷卡尔斯库加公司 用于制备4-取代咪唑类的新方法

Non-Patent Citations (2)

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Vilsmeier试剂近年来在有机合成中的应用;钱定权 等;《有机化学》;20001231;第20卷(第1期);第30页、第40页 *
用亚硫酸氢钠加成法鉴别醛酮的实验研究;索福喜 等;《化学教育》;20080531(第5期);第68页 *

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US10053420B2 (en) 2018-08-21
JP2018505179A (ja) 2018-02-22
KR20170108080A (ko) 2017-09-26
HRP20190286T1 (hr) 2019-04-05
PL3250556T3 (pl) 2019-05-31
TR201902673T4 (tr) 2019-03-21
ES2716748T3 (es) 2019-06-14
WO2016120635A1 (en) 2016-08-04
CN107428648A (zh) 2017-12-01
GB201501593D0 (en) 2015-03-18
US20180009744A1 (en) 2018-01-11
JP6702623B2 (ja) 2020-06-03
KR102458638B1 (ko) 2022-10-24
DK3250556T3 (en) 2019-03-11
HUE042626T2 (hu) 2019-07-29
EP3250556A1 (en) 2017-12-06
EP3250556B1 (en) 2018-12-05

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