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ES2121554A1 - Process for obtaining 14-hydroxymorphines by the photo- oxidation of morphine alkaloids with an alkoxydiene system in the C ring - Google Patents

Process for obtaining 14-hydroxymorphines by the photo- oxidation of morphine alkaloids with an alkoxydiene system in the C ring

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Publication number
ES2121554A1
ES2121554A1ES09602718AES9602718AES2121554A1ES 2121554 A1ES2121554 A1ES 2121554A1ES 09602718 AES09602718 AES 09602718AES 9602718 AES9602718 AES 9602718AES 2121554 A1ES2121554 A1ES 2121554A1
Authority
ES
Spain
Prior art keywords
alkoxydiene
photo
oxidation
ring
alkaloids
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.)
Granted
Application number
ES09602718A
Other languages
Spanish (es)
Other versions
ES2121554B1 (en
Inventor
Vega Ricardo Riguera
Cabana Emilio Quinoa
Souto Ma Dolores Lopez
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.)
Universidade de Santiago de Compostela
Original Assignee
Universidade de Santiago de Compostela
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 Universidade de Santiago de CompostelafiledCriticalUniversidade de Santiago de Compostela
Priority to ES9602718ApriorityCriticalpatent/ES2121554B1/en
Publication of ES2121554A1publicationCriticalpatent/ES2121554A1/en
Application grantedgrantedCritical
Publication of ES2121554B1publicationCriticalpatent/ES2121554B1/en
Anticipated expirationlegal-statusCritical
Expired - Lifetimelegal-statusCriticalCurrent

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Abstract

Process for obtaining 14-hydroxymorphines by the photo- oxidation of morphine alkaloids with an alkoxydiene system in the C ring. The photo-oxidation of morphine alkaloids with an alkoxydiene system in the C ring (general structure II), such as tebain and oripavin, in acid medium produces alkaloids which are oxygenated in the C-6 and C-14 positions of general structure I, such as salts of 14- hydroxycodeinone and 14-hydroxymorphinone. The compounds of general structure I are also prepared by acid treatment of the corresponding endoperoxides III, obtained by photo-oxidation of salts of the alkaloids tebain, oripavin and similar alkaloids having an alkoxydiene system in the C-ring.
ES9602718A1996-12-231996-12-23 PROCEDURE FOR OBTAINING 14-HYDROXIMOFINONES BY PHOTOOXIDATION OF MORPHINE ALKALOIDS WITH ALCOXIDIENIC SYSTEM IN RING C.Expired - LifetimeES2121554B1 (en)

Priority Applications (1)

Application NumberPriority DateFiling DateTitle
ES9602718AES2121554B1 (en)1996-12-231996-12-23 PROCEDURE FOR OBTAINING 14-HYDROXIMOFINONES BY PHOTOOXIDATION OF MORPHINE ALKALOIDS WITH ALCOXIDIENIC SYSTEM IN RING C.

Applications Claiming Priority (1)

Application NumberPriority DateFiling DateTitle
ES9602718AES2121554B1 (en)1996-12-231996-12-23 PROCEDURE FOR OBTAINING 14-HYDROXIMOFINONES BY PHOTOOXIDATION OF MORPHINE ALKALOIDS WITH ALCOXIDIENIC SYSTEM IN RING C.

Publications (2)

Publication NumberPublication Date
ES2121554A1true ES2121554A1 (en)1998-11-16
ES2121554B1 ES2121554B1 (en)1999-06-16

Family

ID=8297120

Family Applications (1)

Application NumberTitlePriority DateFiling Date
ES9602718AExpired - LifetimeES2121554B1 (en)1996-12-231996-12-23 PROCEDURE FOR OBTAINING 14-HYDROXIMOFINONES BY PHOTOOXIDATION OF MORPHINE ALKALOIDS WITH ALCOXIDIENIC SYSTEM IN RING C.

Country Status (1)

CountryLink
ES (1)ES2121554B1 (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication numberPriority datePublication dateAssigneeTitle
EP1730151A4 (en)*2004-03-302007-05-23Euro Celtique Sa PROCESS FOR THE PREPARATION OF OXYCODONE HYDROCHLORIDE HAVING LESS THAN 25 PPM OF 14-HYDROXYCODEINONE
WO2008109156A3 (en)*2007-03-062008-11-20Mallinckrodt IncProcess for the preparation of quaternary n-alkyl morphinan alkaloid salts
US8115002B2 (en)2006-09-202012-02-14Mallinckrodt LlcPreparation of substituted morphinan-6-ones and salts and intermediates thereof
US8148528B2 (en)2008-05-272012-04-03Mallinckrodt LlcProcesses and compounds for the preparation of normorphinans
US8703950B2 (en)2010-07-022014-04-22Johnson Matthey Public Limited Co.Low ABUK oxycodone, its salts and methods of making same
US9040726B2 (en)2007-03-062015-05-26Mallinckrodt LlcProcess for the preparation of quaternary N-alkyl morphinan alkaloid salts
US9062062B1 (en)2013-12-182015-06-23Cody Laboratories, Inc.Synthesis of oxycodone hydrochloride
US9090620B2 (en)2013-12-182015-07-28Cody Laboratories, Inc.Preparation of 14-hydroxycodeinone sulfate
US9458109B2 (en)2008-09-032016-10-04Mallinckrodt LlcSubstituted berbines and processes for their synthesis
US10227354B2 (en)2013-12-182019-03-12Cody Laboratories, Inc.Conversion of oxycodone base to oxycodone hydrochloride

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DOLORES LOPEZ, EMILIO QUIÐOA y RICARDO RIGUERA. Photooxidation of Thebaine. A Route to 14-Hydroxymorphinones and Hydrodibenzofuran Analogs of Methadone. Tetrahedron Letters, 1994, Vol. 35, N‘ 31, pßginas 5727-5730, en particular, esquema 1, ruta III. Esquema 1, ruta IV.*
FREUND, M y SPEYER, E. œber die Umwandlung von Thebain in Oxycodeinon und dessen Derivate. J. Prakt. Chem., (2) 94. 1916, pßgina 159*

Cited By (32)

* Cited by examiner, † Cited by third party
Publication numberPriority datePublication dateAssigneeTitle
US10689389B2 (en)2004-03-302020-06-23Purdue Pharma L.P.Process for preparing oxycodone compositions
US9777011B2 (en)2004-03-302017-10-03Purdue Pharma L.P.Process for preparing oxycodone compositions
US7674799B2 (en)2004-03-302010-03-09Purdue Pharma L.P.Oxycodone hydrochloride having less than 25 ppm 14-hydroxycodeinone
US7674798B2 (en)2004-03-302010-03-09Purdue Pharma L.P.Oxycodone hydrochloride having less than 25 ppm 14-hydroxycodeinone
US7674800B2 (en)2004-03-302010-03-09Purdue Pharma L.P.Oxycodone hydrochloride having less than 25 PPM 14-hydroxycodeinone
US7683072B2 (en)2004-03-302010-03-23Purdue Pharma L.P.Oxycodone hydrochloride having less than 25 ppm 14-hydroxycodeinone
US10407434B2 (en)2004-03-302019-09-10Purdue Pharma L.P.Process for preparing oxycodone compositions
EP1730151A4 (en)*2004-03-302007-05-23Euro Celtique Sa PROCESS FOR THE PREPARATION OF OXYCODONE HYDROCHLORIDE HAVING LESS THAN 25 PPM OF 14-HYDROXYCODEINONE
US10259819B2 (en)2004-03-302019-04-16Purdue Pharma L.P.Process for preparing oxycodone compositions
US9522919B2 (en)2004-03-302016-12-20Purdue Pharma L.P.Oxycodone compositions
US11236098B2 (en)2004-03-302022-02-01Purdue Pharma L.P.Process for preparing oxycodone hydrochloride having less than 25 ppm 14-hydroxycodeinone
US8822687B2 (en)2004-03-302014-09-02Purdue Pharma L.P.8a,14-dihydroxy-7,8-dihydrocodeinone
US10696684B2 (en)2004-03-302020-06-30Purdue Pharma L.P.Process for preparing oxycodone hydrochloride having less than 25 PPM 14-hydroxycodeinone
US12060361B2 (en)2004-03-302024-08-13Purdue Pharma L.P.Process for preparing oxycodone hydrochloride having less than 25 ppm 14-hydroxycodeinone
US9073933B2 (en)2004-03-302015-07-07Purdue Pharma L.P.Oxycodone hydrochloride having less than 25 PPM 14-hydroxycodeinone
US11384091B2 (en)2004-03-302022-07-12Purdue Pharma L.P.Process for preparing oxycodone hydrochloride having less than 25 ppm 14-hydroxycodeinone
US8115002B2 (en)2006-09-202012-02-14Mallinckrodt LlcPreparation of substituted morphinan-6-ones and salts and intermediates thereof
EP2147920A3 (en)*2007-03-062010-03-24Mallinckrodt Inc.Process for the preparation of quaternary n-alkyl morphinan alkaloid salts
US9040726B2 (en)2007-03-062015-05-26Mallinckrodt LlcProcess for the preparation of quaternary N-alkyl morphinan alkaloid salts
US9415044B2 (en)2007-03-062016-08-16Mallinckrodt LlcProcess for the preparation of quaternary N-alkyl morphinan alkaloid salts
US8669366B2 (en)2007-03-062014-03-11Mallinckrodt LlcProcess for the preparation of quaternary N-alkyl morphinan alkaloid salts
WO2008109156A3 (en)*2007-03-062008-11-20Mallinckrodt IncProcess for the preparation of quaternary n-alkyl morphinan alkaloid salts
US8148528B2 (en)2008-05-272012-04-03Mallinckrodt LlcProcesses and compounds for the preparation of normorphinans
US9458109B2 (en)2008-09-032016-10-04Mallinckrodt LlcSubstituted berbines and processes for their synthesis
US9856251B2 (en)2008-09-032018-01-02Mallinckrodt LlcSubstituted berbines and processes for their synthesis
US8703950B2 (en)2010-07-022014-04-22Johnson Matthey Public Limited Co.Low ABUK oxycodone, its salts and methods of making same
US9108976B2 (en)2013-12-182015-08-18Cody Laboratories, Inc.Preparation of 14-hydroxycodeinone sulfate
US10227354B2 (en)2013-12-182019-03-12Cody Laboratories, Inc.Conversion of oxycodone base to oxycodone hydrochloride
US9309257B2 (en)2013-12-182016-04-12Cody Laboratories, Inc.Preparation of oxycodone base form 14-hydroxycodeinone sulfate
US9233972B2 (en)2013-12-182016-01-12Cody Laboratories, Inc.Preparation of 14-hydroxycodeinone sulfate
US9090620B2 (en)2013-12-182015-07-28Cody Laboratories, Inc.Preparation of 14-hydroxycodeinone sulfate
US9062062B1 (en)2013-12-182015-06-23Cody Laboratories, Inc.Synthesis of oxycodone hydrochloride

Also Published As

Publication numberPublication date
ES2121554B1 (en)1999-06-16

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