WO2016202808A3 - NEW SYNTHESIS OF TAPENTADOL-HCl INTERMEDIATES - Google Patents

NEW SYNTHESIS OF TAPENTADOL-HCl INTERMEDIATES Download PDF

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Publication number
WO2016202808A3
WO2016202808A3 PCT/EP2016/063648 EP2016063648W WO2016202808A3 WO 2016202808 A3 WO2016202808 A3 WO 2016202808A3 EP 2016063648 W EP2016063648 W EP 2016063648W WO 2016202808 A3 WO2016202808 A3 WO 2016202808A3
Authority
WO
WIPO (PCT)
Prior art keywords
tapentadol
intermediates
hcl
new synthesis
synthesis
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.)
Ceased
Application number
PCT/EP2016/063648
Other languages
French (fr)
Other versions
WO2016202808A2 (en
Inventor
Roman Gerber AESCHBACHER
Christian Manfred FRECH
Thomas Maier
Frank Porstmann
Jian-Ge CHEN
Xiongwei Shi
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.)
Azad Pharma AG
Original Assignee
Azad Pharmaceutical Ingredients AG
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 Azad Pharmaceutical Ingredients AG filed Critical Azad Pharmaceutical Ingredients AG
Publication of WO2016202808A2 publication Critical patent/WO2016202808A2/en
Publication of WO2016202808A3 publication Critical patent/WO2016202808A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
    • C07C217/62—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
    • C07C215/54—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/16—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/76—Unsaturated compounds containing keto groups
    • C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D307/32—Oxygen atoms
    • C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention relates to a process for the synthesis of tapentadol intermediates comprising the following route of synthesis: (I) → (II) → (III) → (IV) → (V).
PCT/EP2016/063648 2015-06-16 2016-06-14 NEW SYNTHESIS OF TAPENTADOL-HCl INTERMEDIATES Ceased WO2016202808A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB1510544.8A GB2539442A (en) 2015-06-16 2015-06-16 New synthesis of tapentadol-HCI intermediates
GB1510544.8 2015-06-16

Publications (2)

Publication Number Publication Date
WO2016202808A2 WO2016202808A2 (en) 2016-12-22
WO2016202808A3 true WO2016202808A3 (en) 2017-01-26

Family

ID=53784810

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2016/063648 Ceased WO2016202808A2 (en) 2015-06-16 2016-06-14 NEW SYNTHESIS OF TAPENTADOL-HCl INTERMEDIATES

Country Status (2)

Country Link
GB (1) GB2539442A (en)
WO (1) WO2016202808A2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113214195B (en) * 2021-04-28 2024-05-10 云南民族大学 Method for asymmetrically synthesizing dihydrofuran 2- (3H) -ketone compound by nickel catalysis
CN118388329B (en) * 2024-05-16 2024-11-15 江苏海洋大学 Tapentadol Process for the preparation of intermediates

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0271287A2 (en) * 1986-12-11 1988-06-15 Merck Frosst Canada Inc. Quinoline dioic acids and amides
EP2671878A1 (en) * 2011-01-31 2013-12-11 Shanghai Institute Materia Medica, Chinese Academy Of Sciences Substituted n-pentanamide compounds, preparation methods and uses thereof

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1397189B1 (en) * 2009-12-01 2013-01-04 Archimica Srl NEW PROCESS FOR THE PREPARATION OF TAPENTADOL AND ITS INTERMEDIATES.
IN2013MU03670A (en) * 2013-11-21 2015-07-31 Unimark Remedies Ltd
AU2015287663B2 (en) * 2014-07-10 2019-02-28 SpecGx LLC Process for preparing substituted phenylalkanes

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0271287A2 (en) * 1986-12-11 1988-06-15 Merck Frosst Canada Inc. Quinoline dioic acids and amides
EP2671878A1 (en) * 2011-01-31 2013-12-11 Shanghai Institute Materia Medica, Chinese Academy Of Sciences Substituted n-pentanamide compounds, preparation methods and uses thereof

Also Published As

Publication number Publication date
WO2016202808A2 (en) 2016-12-22
GB2539442A (en) 2016-12-21
GB201510544D0 (en) 2015-07-29

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