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WO2015095585A8 - Synthesis of oxycodone hydrochloride - Google Patents

Synthesis of oxycodone hydrochloride Download PDF

Info

Publication number
WO2015095585A8
WO2015095585A8 PCT/US2014/071264 US2014071264W WO2015095585A8 WO 2015095585 A8 WO2015095585 A8 WO 2015095585A8 US 2014071264 W US2014071264 W US 2014071264W WO 2015095585 A8 WO2015095585 A8 WO 2015095585A8
Authority
WO
WIPO (PCT)
Prior art keywords
oxycodone
oxycodone hydrochloride
synthesis
impurity
minimize
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/US2014/071264
Other languages
French (fr)
Other versions
WO2015095585A3 (en
WO2015095585A2 (en
Inventor
Zinovy Itov
Vladimir F. KUZNETSOV
Iouri Voitsekhovski
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.)
Cody Laboratories Inc
Original Assignee
Cody Laboratories Inc
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
Priority claimed from US14/132,825 external-priority patent/US8846923B1/en
Priority claimed from US14/132,737 external-priority patent/US9062062B1/en
Priority claimed from US14/132,910 external-priority patent/US10227354B2/en
Application filed by Cody Laboratories Inc filed Critical Cody Laboratories Inc
Priority to CA2934527A priority Critical patent/CA2934527A1/en
Priority to CN201480075277.9A priority patent/CN106164078A/en
Priority to EP14824727.3A priority patent/EP3083632A2/en
Publication of WO2015095585A2 publication Critical patent/WO2015095585A2/en
Publication of WO2015095585A3 publication Critical patent/WO2015095585A3/en
Publication of WO2015095585A8 publication Critical patent/WO2015095585A8/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
    • C07D489/06—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: with a hetero atom directly attached in position 14
    • C07D489/08—Oxygen atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Synthetic methods are provided for preparation of oxycodone and salts thereof with an improved impurity profile. Thebaine is converted to 14-hydroxycodeinone sulfate intermediate to minimize a 7,8-dihydro-8,14-dihydroxycodeinone impurity. Efficient methods for conversion of oxycodone base to oxycodone hydrochloride are provided to minimize 14-hydroxycodeinone impurity in the final product.
PCT/US2014/071264 2013-12-18 2014-12-18 Sysnthesis of oxycodone hydrochloride Ceased WO2015095585A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CA2934527A CA2934527A1 (en) 2013-12-18 2014-12-18 Synthesis of oxycodone hydrochloride
CN201480075277.9A CN106164078A (en) 2013-12-18 2014-12-18 Synthesis of Oxycodone Hydrochloride
EP14824727.3A EP3083632A2 (en) 2013-12-18 2014-12-18 Sysnthesis of oxycodone hydrochloride

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US14/132,910 2013-12-18
US14/132,825 US8846923B1 (en) 2013-12-18 2013-12-18 Preparation of 14-hydroxycodeinone sulfate
US14/132,737 US9062062B1 (en) 2013-12-18 2013-12-18 Synthesis of oxycodone hydrochloride
US14/132,737 2013-12-18
US14/132,910 US10227354B2 (en) 2013-12-18 2013-12-18 Conversion of oxycodone base to oxycodone hydrochloride
US14/132,825 2013-12-18

Publications (3)

Publication Number Publication Date
WO2015095585A2 WO2015095585A2 (en) 2015-06-25
WO2015095585A3 WO2015095585A3 (en) 2015-08-13
WO2015095585A8 true WO2015095585A8 (en) 2016-02-04

Family

ID=52293289

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2014/071264 Ceased WO2015095585A2 (en) 2013-12-18 2014-12-18 Sysnthesis of oxycodone hydrochloride

Country Status (4)

Country Link
EP (1) EP3083632A2 (en)
CN (1) CN106164078A (en)
CA (1) CA2934527A1 (en)
WO (1) WO2015095585A2 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10316042B2 (en) 2012-07-16 2019-06-11 Rhodes Technologies Process for improved opioid synthesis
UA117226C2 (en) 2012-07-16 2018-07-10 Родес Текнолоджіс Process for improved opioid synthesis
CN106029669B (en) 2014-01-15 2018-04-13 罗德科技公司 Improved Oxymorphone synthetic method
CN106029670A (en) 2014-01-15 2016-10-12 罗德科技公司 Improved method for the synthesis of oxycodone
CN110770238B (en) * 2017-06-20 2022-10-04 庄信万丰股份有限公司 Hydrogenation process for the preparation of oxycodone hydrochloride from 14-hydroxycodeinone

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4795813A (en) 1981-08-17 1989-01-03 The Florida Board Of Regents On Behalf Of The Florida State University Synthesis of derivatives of codeine and other 3-O-alkylmorphines
US4613668A (en) 1983-12-22 1986-09-23 The United States Of America As Represented By The Department Of Health And Human Services Short total synthesis or morphinan compounds which uses cyclization of a cycloalkylcarbonyl compound selected from cyclopropylcarbonyl and cyclobutylcarbonyl
US6067749A (en) 1996-07-11 2000-05-30 Tasmanian Alkaloids Pty. Ltd. Papaver somniferum strain with high concentration of thebaine and oripavine
SK286087B6 (en) * 2004-08-18 2008-03-05 Zentiva, A. S. Method of preparation of oxycodone
GB0421149D0 (en) * 2004-09-23 2004-10-27 Johnson Matthey Plc Preparation of oxycodone
DE602006019246D1 (en) 2005-06-16 2011-02-10 Mallinckrodt Inc SYNTHETIC ROUTE TO 14-HYDROXYLOPIATES OVER 1-HALOGENHEBINE OR ANALOG
EP2377866B1 (en) * 2010-03-23 2014-02-26 Siegfried AG Preparation of low impurity opiates in a continuous flow reactor
UA117226C2 (en) * 2012-07-16 2018-07-10 Родес Текнолоджіс Process for improved opioid synthesis

Also Published As

Publication number Publication date
WO2015095585A3 (en) 2015-08-13
EP3083632A2 (en) 2016-10-26
WO2015095585A2 (en) 2015-06-25
CA2934527A1 (en) 2015-06-25
CN106164078A (en) 2016-11-23

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