CA2674424A1 - Hydromorphinone and hydrocodeinone compositions and methods for their synthesis - Google Patents

Hydromorphinone and hydrocodeinone compositions and methods for their synthesis Download PDF

Info

Publication number
CA2674424A1
CA2674424A1 CA002674424A CA2674424A CA2674424A1 CA 2674424 A1 CA2674424 A1 CA 2674424A1 CA 002674424 A CA002674424 A CA 002674424A CA 2674424 A CA2674424 A CA 2674424A CA 2674424 A1 CA2674424 A1 CA 2674424A1
Authority
CA
Canada
Prior art keywords
ketone
narcotic alkaloid
compositions
hydromorphone
hydrogen
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
CA002674424A
Other languages
French (fr)
Other versions
CA2674424C (en
Inventor
William H. Harclerode
Robert Gault
Mark D. Sandison
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.)
Abbott Laboratories
Original Assignee
Abbott Laboratories
William H. Harclerode
Robert Gault
Mark D. Sandison
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=27389009&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CA2674424(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Abbott Laboratories, William H. Harclerode, Robert Gault, Mark D. Sandison filed Critical Abbott Laboratories
Publication of CA2674424A1 publication Critical patent/CA2674424A1/en
Application granted granted Critical
Publication of CA2674424C publication Critical patent/CA2674424C/en
Anticipated expiration legal-status Critical
Expired - Lifetime 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:
    • C07D489/02—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 oxygen atoms attached in positions 3 and 6, e.g. morphine, morphinone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/485—Morphinan derivatives, e.g. morphine, codeine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids

Abstract

A method for the preparation of a ketone from a narcotic alkaloid having an allyl alcohol moiety is disclosed. The method includes mixing the narcotic alkaloid with an acid in the presence of a catalyst wherein the method is carried out in the substantial absence of hydrogen gas. The method is useful for preparing hydromorphone and hydrocodone compositions having novel impurity profiles. Compositions comprising hydromorphone and hydrocodone are also disclosed.

Claims (15)

1. A method of preparing a ketone from a narcotic alkaloid having an allyl alcohol moiety comprising mixing the narcotic alkaloid with an acid in the presence of a catalyst wherein the method is carried out in the substantial absence of hydrogen gas.
2. The method as recited in claim 1, wherein the narcotic alkaloid comprises a compound represented by formula (I):

wherein R is hydrogen or an alcohol protecting moiety.
3. The method of claim 2, wherein said alcohol protecting moiety is alkyl, aralkyl, or aryl.
4. The method of claim 2, wherein R is hydrogen or CH3.
5. The method of claim 1, wherein said narcotic alkaloid is selected from the group consisting of morphine, codeine and salts thereof.
6. The method of claim 1, wherein said narcotic alkaloid is morphine or a salt thereof.
7. The method of claim 1, wherein said narcotic alkaloid is codeine or a salt thereof.
8. The method of claim 2, wherein said ketone is represented by formula II:

9. The method of claim 8, wherein R is hydrogen or CH3.
10. The method of claim 8, wherein said ketone is hydromorphone or one of its salts.
11. The method of claim 10, wherein said ketone is the bisulfite salt of hydromorphone.
12. The method of claim 8, wherein said ketone is hydrocodone or one of its salts.
13. The method of claim 2, wherein said alcohol protecting moiety is removed after the formation of the ketone.
14. The method of any one of claims 1 to 13, wherein said catalyst comprises non-supported palladium.
15. The method of any one of claims 1 to 14, wherein said acid is hydrochloric acid.
CA2674424A 1999-11-09 2000-11-09 Hydromorphinone and hydrocodeinone compositions and methods for their synthesis Expired - Lifetime CA2674424C (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US16436499P 1999-11-09 1999-11-09
US16450599P 1999-11-09 1999-11-09
US16453699P 1999-11-09 1999-11-09
US60/164,536 1999-11-09
US60/164,505 1999-11-09
US60/164,364 1999-11-09
CA002389193A CA2389193A1 (en) 1999-11-09 2000-11-09 Hydromorphone compositions and methods of their synthesis

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CA002389193A Division CA2389193A1 (en) 1999-11-09 2000-11-09 Hydromorphone compositions and methods of their synthesis

Publications (2)

Publication Number Publication Date
CA2674424A1 true CA2674424A1 (en) 2001-05-17
CA2674424C CA2674424C (en) 2012-10-02

Family

ID=27389009

Family Applications (3)

Application Number Title Priority Date Filing Date
CA2854796A Abandoned CA2854796A1 (en) 1999-11-09 2000-11-09 Hydromorphinone and hydrocodeinone compositions and methods for their synthesis
CA002389193A Withdrawn CA2389193A1 (en) 1999-11-09 2000-11-09 Hydromorphone compositions and methods of their synthesis
CA2674424A Expired - Lifetime CA2674424C (en) 1999-11-09 2000-11-09 Hydromorphinone and hydrocodeinone compositions and methods for their synthesis

Family Applications Before (2)

Application Number Title Priority Date Filing Date
CA2854796A Abandoned CA2854796A1 (en) 1999-11-09 2000-11-09 Hydromorphinone and hydrocodeinone compositions and methods for their synthesis
CA002389193A Withdrawn CA2389193A1 (en) 1999-11-09 2000-11-09 Hydromorphone compositions and methods of their synthesis

Country Status (10)

Country Link
US (2) US6512117B1 (en)
EP (3) EP1233966B2 (en)
JP (1) JP4886953B2 (en)
AT (2) ATE402937T1 (en)
AU (1) AU1595701A (en)
CA (3) CA2854796A1 (en)
DE (2) DE60045695D1 (en)
ES (1) ES2309001T5 (en)
MX (1) MXPA02004678A (en)
WO (1) WO2001034608A1 (en)

Families Citing this family (43)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2269587A1 (en) 1999-10-29 2011-01-05 Euro-Celtique S.A. Controlled release hydrocodone formulations
US10179130B2 (en) 1999-10-29 2019-01-15 Purdue Pharma L.P. Controlled release hydrocodone formulations
AU2738302A (en) 2000-10-30 2002-05-15 Euro Celtique Sa Controlled release hydrocodone formulations
US7323565B2 (en) 2002-11-11 2008-01-29 Mallinckrodt Inc. Method for the catalytic production of hydrocodone and hydromorphone
US7321038B2 (en) 2002-11-11 2008-01-22 Mallinckrodt Inc. Method for the catalytic production of hydrocodone and hydromorphone
WO2005016930A2 (en) * 2003-08-08 2005-02-24 Euro-Celtique, S.A. Methods for detecting morphinone
SK286047B6 (en) * 2004-04-13 2008-01-07 Zentiva, A. S. Method for the preparation of 4,5alpha-epoxy-6-oxomorphinane derivatives
US6946556B1 (en) * 2004-05-21 2005-09-20 Acura Pharmaceuticals, Inc. Preparation of opioid analgesics by a one-pot process
US7348430B2 (en) 2005-01-21 2008-03-25 Acura Pharmaceuticals, Inc. Production of opioid analgesics
WO2006104656A1 (en) * 2005-03-28 2006-10-05 Mallinckrodt Inc. Method for the catalytic production of hydrocodone, hydromorphone, and derivatives thereof
WO2006113696A1 (en) * 2005-04-18 2006-10-26 Noramaco Inc. Hydromorphone polymorphs
US20100073766A1 (en) * 2005-10-26 2010-03-25 Angros Lee H Microscope slide testing and identification assembly
US20080069891A1 (en) 2006-09-15 2008-03-20 Cima Labs, Inc. Abuse resistant drug formulation
US8445018B2 (en) 2006-09-15 2013-05-21 Cima Labs Inc. Abuse resistant drug formulation
US7399859B1 (en) 2007-02-06 2008-07-15 Cody Laboratories Inc. Method for catalytic preparation of hydromorphone and hydrocodone
US20080206883A1 (en) * 2007-02-26 2008-08-28 Cody Laboratories, Inc. Hplc method for separation and detection of hydromorphone and related opioid pharmacophores
US7999104B2 (en) 2007-06-29 2011-08-16 Brock University Methods for one-pot N-demethylation/N-acylation of morphine and tropane alkaloids
US8962841B2 (en) 2007-06-29 2015-02-24 Brock University Methods for one-pot N-demethylation/N-functionalization of morphine and tropane alkaloids
GB0802351D0 (en) * 2008-02-08 2008-03-12 Owen Mumford Ltd Injection devices
JP2011511782A (en) 2008-02-12 2011-04-14 アボット・ラボラトリーズ Extended release hydrocodone acetaminophen and related methods and uses
WO2010118274A1 (en) * 2009-04-09 2010-10-14 Mallinckrodt Inc. Preparation of 6-keto, 3-alkoxy morphinans
ES2571232T3 (en) * 2009-04-09 2016-05-24 Mallinckrodt Llc Preparation of saturated ketone morphinan compounds by catalytic isomerization
WO2010118275A1 (en) * 2009-04-09 2010-10-14 Mallinckrodt Inc. Preparation of saturated ketone morphinan compounds
US8383815B2 (en) 2009-09-21 2013-02-26 Mallinckrodt Llc Heterogeneous ruthenium metal catalyst for the production of hydrocodone, hydromorphone or a derivative thereof
EP2568977A1 (en) 2010-05-11 2013-03-20 Cima Labs Inc. Alcohol-resistant metoprolol-containing extended- release oral dosage forms
US8946214B2 (en) 2011-05-06 2015-02-03 Brock University Process for the preparation of morphine analogs via metal catalyzed N-demethylation/functionalization and intramolecular group transfer
TWI560170B (en) * 2011-12-06 2016-12-01 Lundbeck & Co As H Process for recovery of nalmefene hydrochloride
US9155734B2 (en) * 2012-03-07 2015-10-13 Mallinckrodt Llc Stability of hydromorphone hydrochloride solutions
CN103408553B (en) * 2013-08-20 2016-02-03 宜昌人福药业有限责任公司 A kind of process for refining of hydromorphone acid salt
DK3102576T3 (en) 2014-02-03 2019-07-22 Vitae Pharmaceuticals Llc DIHYDROPYRROLOPYRIDINE INHIBITORS OF ROR-GAMMA
PT3207043T (en) 2014-10-14 2019-03-25 Vitae Pharmaceuticals Llc Dihydropyrrolopyridine inhibitors of ror-gamma
US9845308B2 (en) 2014-11-05 2017-12-19 Vitae Pharmaceuticals, Inc. Isoindoline inhibitors of ROR-gamma
US9663515B2 (en) 2014-11-05 2017-05-30 Vitae Pharmaceuticals, Inc. Dihydropyrrolopyridine inhibitors of ROR-gamma
DK3331876T3 (en) 2015-08-05 2021-01-11 Vitae Pharmaceuticals Llc MODULATORS OF ROR-GAMMA
BR112018010018A2 (en) 2015-11-20 2018-11-21 Vitae Pharmaceuticals Inc ror-gamma modulators
TWI757266B (en) 2016-01-29 2022-03-11 美商維它藥物有限責任公司 Modulators of ror-gamma
US9481674B1 (en) 2016-06-10 2016-11-01 Vitae Pharmaceuticals, Inc. Dihydropyrrolopyridine inhibitors of ROR-gamma
WO2018009856A1 (en) 2016-07-08 2018-01-11 Cody Laboratories, Inc. Method for catalytic preparation of hydromorphone, hydrocodone and other opiates
WO2019018975A1 (en) 2017-07-24 2019-01-31 Vitae Pharmaceuticals, Inc. Inhibitors of ror gamma
BR112020001246A2 (en) 2017-07-24 2020-07-21 Vitae Pharmaceuticals, Llc rory inhibitors
CN108164540B (en) * 2017-12-14 2019-08-13 宜昌人福药业有限责任公司 A method of synthesis Hydromorphone
JP2023548356A (en) * 2020-11-02 2023-11-16 ローズ テクノロジーズ Method for purifying noroxymorphone
US20240043447A1 (en) 2020-11-13 2024-02-08 Ferrer Internacional, S.A. Synthesis of hydromorphone base

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE260233C (en)
GB285404A (en)
DE365683C (en) 1921-03-22 1922-12-22 Knoll & Co Chem Fab Process for the preparation of keto derivatives of the morphine series
DE607931C (en) 1934-01-26 1935-01-11 Chemische Fabriken Process for the preparation of dihydromorphinones
US2544291A (en) 1949-04-05 1951-03-06 New York Quinine And Chemical Alkaloid manufacture
US2628962A (en) 1949-10-20 1953-02-17 Mallinckrodt Chemical Works Method for preparing dihydrocodeinone, dihydromorphinone, and codeinone
US2654756A (en) 1949-10-20 1953-10-06 Mallinckrodt Chemical Works Process of preparing codeinone, dihydrocodeinone, and dihydromorphinone
US2649454A (en) 1951-08-20 1953-08-18 Univ California Method for preparing dihydromorphinone, dihydrocodeinone, and dihydropseudocodeinone
GB9616253D0 (en) * 1996-08-01 1996-09-11 Johnson Matthey Plc Preparation of narcotic analgesics

Also Published As

Publication number Publication date
EP1233966B2 (en) 2011-10-19
AU1595701A (en) 2001-06-06
ES2309001T3 (en) 2008-12-16
EP1233966B1 (en) 2008-07-30
JP2003513980A (en) 2003-04-15
WO2001034608A1 (en) 2001-05-17
ATE500257T1 (en) 2011-03-15
DE60045695D1 (en) 2011-04-14
EP2003134B1 (en) 2011-03-02
US6512117B1 (en) 2003-01-28
MXPA02004678A (en) 2005-10-05
EP2003134A2 (en) 2008-12-17
CA2674424C (en) 2012-10-02
CA2854796A1 (en) 2001-05-17
ATE402937T1 (en) 2008-08-15
CA2389193A1 (en) 2001-05-17
EP2338891A3 (en) 2011-10-26
DE60039711D1 (en) 2008-09-11
EP1233966A1 (en) 2002-08-28
ES2309001T5 (en) 2011-12-28
EP2338891A2 (en) 2011-06-29
JP4886953B2 (en) 2012-02-29
US20030045720A1 (en) 2003-03-06
US6589960B2 (en) 2003-07-08
EP2003134A3 (en) 2009-02-25

Similar Documents

Publication Publication Date Title
CA2674424A1 (en) Hydromorphinone and hydrocodeinone compositions and methods for their synthesis
EP1562953B1 (en) Process for the preparation of quaternary n-alkyl morphinan alkaloid salts
EP2428519A3 (en) Process for the preparation of 17-vinyl- triflates as intermediates
US20100022774A1 (en) Process useful in the preparation of morphinan antagonists
CA2657483A1 (en) Macrolide synthesis process
AU2006271645B2 (en) Method for preparing 4beta-amino-4'-demethyl-4-desoxypodophyllotoxin
US20100168427A1 (en) Method for producing n-methylnaltrexone bromide
Campbell et al. The mild and selective N-debenzylation of tertiary alkylamines using β-trimethylsilylethyl chloroformate.
WO2005113557A8 (en) Method for the catalytic production of hydrocodone and hydromorphone
AU2007267439B2 (en) Process for the demethylation of oxycodone and related compounds
KR850002260A (en) Process for preparing substituted 4-alkyl-2 (1H) quinazolinone-1-alkanoic acid derivatives
WO2004037826A3 (en) Preparation of codeine from morphine
RU2145325C1 (en) Method of preparing 9-aminocaptothecin, intermediate products, and method of preparing thereof
CN110229104A (en) The method of luxuriant titanium/bronsted acid catalysis arylamine and α -one Lipase absobed Tetrahydroquinolinesas
CA2507691A1 (en) Method for producing salts of tolperisone
CA2389595C (en) Improved synthesis of n,n-disubstituted-p-phenylenediamine
CA2000565A1 (en) Process for the preparation of 4-acyloxy-2-azetidinone derivatives
CA1218990A (en) 4,5.alpha.EPOXYMORPHINAN-6-SPIRO-2'-(4'-CARBOXY,1',3'- THIAZOLIDINE) DERIVATIVES
EP2148882B1 (en) Process for making topotecan
CA2541477A1 (en) Process for preparing 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
CA2560778A1 (en) A process for the semisynthesis of deserpidine
EP1346971A8 (en) Production method for biarylalanine
CN1032857C (en) Novel diketene imine derivative and process for preparing same
JP2000080078A5 (en)
IL144099A0 (en) Process for the preparation of azoiminoethers and azocarboxylic acid esters and novel azocarboxylic acid mixed esters

Legal Events

Date Code Title Description
EEER Examination request
MKEX Expiry

Effective date: 20201109