DK3250556T3 - Fremgangsmåder til fremstilling af forbindelser, såsom 3-arylbutanaler, der kan anvendes til syntese af medetomidin - Google Patents

Fremgangsmåder til fremstilling af forbindelser, såsom 3-arylbutanaler, der kan anvendes til syntese af medetomidin Download PDF

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DK3250556T3
DK3250556T3 DK16706396.5T DK16706396T DK3250556T3 DK 3250556 T3 DK3250556 T3 DK 3250556T3 DK 16706396 T DK16706396 T DK 16706396T DK 3250556 T3 DK3250556 T3 DK 3250556T3
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compound
formula
reaction
reacting
solvent
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DK16706396.5T
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Lars Eklund
Margus Eek
Ramesh Ekambaram
Ants Maasalu
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I Tech 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
    • 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
    • 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
    • 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
    • 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)

Claims (15)

1. Fremgangsmåde til fremstilling afen forbindelse med formel I
i hvor fremgangsmåden omfatter omsætning af en forbindelse med formel II
med et eller flere egnede Vilsmeier-reagenser.
2. Fremgangsmåde ifølge krav 1, hvor Vilsmeier-reagenset omfatter en forbindelse med formel Illa og/eller en forbindelse med formel lllb
hvor: X betegner en modion afledt fra omsætning med en syrechlorid; Y betegner en substituent afledt fra omsætning med en syrechlorid; hvert Ra og Rb uafhængigt betegner H, Ci-3-alkyl eller phenyl, eller Ra og Rb sammen med det nitrogen, hvortil de er knyttet, danner en pyrollidin-, piperidin-, morpholin- eller indolin-enhed.
3. Fremgangsmåde ifølge krav 1 eller krav 2, hvor Vilsmeier-reagenset dannes ved omsætning af dimethylformamid og POCI3, og eventuelt hvor dimethylfor-mamid også fungerer som et opløsningsmiddel.
4. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 3, hvor fremgangsmåden omfatter trinnene: (i) omsætning af forbindelsen med formel II til dannelse afen forbindelse med formel IV
og efterfølgende (ii) omsætning af forbindelsen med formel IV til dannelse af forbindelsen med formel I.
5. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 4, hvor; a) fremgangsmåden udføres som en one-pot-proces og/eller uden isolering af en forbindelse med formel IV; og/eller b) fremgangsmåden omfatter det yderligere trin at isolere og eventuelt oprense forbindelsen med formel I.
6. Fremgangsmåde til fremstilling af en forbindelse med formel V
hvor fremgangsmåden omfatter omsætning afen forbindelse med formel I som defineret i krav 1 med et egnet reduktionsmiddel.
7. Fremgangsmåde ifølge krav 6, hvor fremgangsmåden omfatter trinnene: (i) tilvejebringelse af en forbindelse med formel I under anvendelse af en fremgangsmåde ifølge et hvilket som helst af kravene 1 til 5; og efterfølgende (ii) omsætning af forbindelsen med formel I med et egnet reduktionsmiddel til dannelse af forbindelsen med formel V.
8. Fremgangsmåde ifølge krav 6 eller krav 7, hvor det egnede reduktionsmiddel er hydrogenkilde, og omsætningen udføres i nærvær af en eller flere egnede katalysatorer og eventuelt udføres i nærvær af en eller flere forbindelser, der er egnede at begrænse aktiviteten af katalysatoren.
9. Fremgangsmåde ifølge et hvilket som helst af kravene 6 til 8, hvor; a) fremgangsmåden omfatter det yderligere trin at isolere og eventuelt oprense forbindelsen med formel V; og/eller b) forbindelsen med formel V isoleres som og/eller oprenses via dannelsen af et bisulfitaddukt med formel VI
hvor Z betegner et alkalimetal.
10. Forbindelse med formel VI som defineret i krav 9.
11. Forbindelse til fremstilling af en forbindelse med formel VI som defineret i krav 9, hvor fremgangsmåden omfatter omsætning af en forbindelse med formel V som defineret i krav 6 med en forbindelse med formel ZHSO3, hvor Z er som defineret i forbindelsen med formel VI.
12. Fremgangsmåde ifølge krav 9, forbindelse ifølge krav 10 eller fremgangsmåde ifølge krav 11, hvor Z betegner Na.
13. Fremgangsmåde til fremstilling afen forbindelse med formel VII
eller et egnet salt deraf, hvor fremgangsmåden omfatter trinnene: (i) tilvejebringelse af en forbindelse med formel I under anvendelse af en fremgangsmåde ifølge et hvilket som helst af kravene 1 til 5; eller (ii) tilvejebringelse af en forbindelse med formel V under anvendelse af en fremgangsmåde ifølge et hvilket som helst af kravene 6 til 9.
14. Fremgangsmåde ifølge krav 13, hvor fremgangsmåden omfatter trinnene: (I) fremstilling af en forbindelse med formel V under anvendelse af en fremgangsmåde ifølge et hvilket som helst af kravene 6 til 9; (II) omsætning af forbindelsen med formel V til dannelse afen forbindelse med formel VIII
hvor L1 betegner en egnet leaving-gruppe; og (III) omsætning af forbindelsen med formel VIII i nærvær af (a) en formamidinkilde eller
(b) formamid, til dannelse af forbindelsen med formel VII eller et egnet salt deraf.
15. Fremgangsmåde ifølge krav 13 eller krav 14, hvor fremgangsmåden omfatter det yderligere trin at isolere og eventuelt oprense forbindelsen med formel VIII.
DK16706396.5T 2015-01-30 2016-01-29 Fremgangsmåder til fremstilling af forbindelser, såsom 3-arylbutanaler, der kan anvendes til syntese af medetomidin DK3250556T3 (da)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
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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DK3250556T3 true DK3250556T3 (da) 2019-03-11

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DK16706396.5T DK3250556T3 (da) 2015-01-30 2016-01-29 Fremgangsmåder til fremstilling af forbindelser, såsom 3-arylbutanaler, der kan anvendes til syntese af medetomidin

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

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* Cited by examiner, † Cited by third party
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
MY207535A (en) 2020-10-21 2025-03-03 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
WO2026015064A1 (en) 2024-07-09 2026-01-15 I-Tech Ab Antifouling paint composition with improved in-can stability

Family Cites Families (12)

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Publication number Priority date Publication date Assignee Title
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
WO2010140636A1 (ja) * 2009-06-03 2010-12-09 高砂香料工業株式会社 不斉水素化触媒
TW201223934A (en) 2010-11-26 2012-06-16 Lonza Ag 3-(2,3-dimethylphenyl)-2-butenal and its use as perfume
WO2012098067A1 (en) * 2011-01-19 2012-07-26 Dsm Ip Assets B.V. Preparation of 4-acetoxy-2-methylbutanal by catalytic carbon carbon double bond hydrogenation
WO2012120070A1 (en) 2011-03-10 2012-09-13 Lonza Ltd Method for preparation of 3-(2,3-dimethylphenyl)-2-butenal
ES2665093T3 (es) * 2011-07-22 2018-04-24 Cambrex Karlskoga Ab Nuevos procedimiento de preparación de imidazoles 4-sustituidos
ES2557638T3 (es) * 2012-05-08 2016-01-27 Lonza Ltd Método para la preparación de 2-(2,3-dimetilfenil)-1-propanal
WO2012172120A2 (en) * 2012-05-08 2012-12-20 Lonza Ltd 2-(2,3-dimethylphenyl)-1-propanal and its use as perfume
WO2012172119A2 (en) * 2012-05-08 2012-12-20 Lonza Ltd Method for the preparation of medetomidine

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KR102458638B1 (ko) 2022-10-24
JP2018505179A (ja) 2018-02-22
HRP20190286T1 (hr) 2019-04-05
CN107428648A (zh) 2017-12-01
WO2016120635A1 (en) 2016-08-04
US20180009744A1 (en) 2018-01-11
ES2716748T3 (es) 2019-06-14
EP3250556B1 (en) 2018-12-05
US10053420B2 (en) 2018-08-21
JP6702623B2 (ja) 2020-06-03
HUE042626T2 (hu) 2019-07-29
GB201501593D0 (en) 2015-03-18
PL3250556T3 (pl) 2019-05-31
CN107428648B (zh) 2021-12-10
EP3250556A1 (en) 2017-12-06
TR201902673T4 (tr) 2019-03-21
KR20170108080A (ko) 2017-09-26

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