WO2010028004A3 - Substituted berbines and processes for their synthesis - Google Patents

Substituted berbines and processes for their synthesis Download PDF

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Publication number
WO2010028004A3
WO2010028004A3 PCT/US2009/055676 US2009055676W WO2010028004A3 WO 2010028004 A3 WO2010028004 A3 WO 2010028004A3 US 2009055676 W US2009055676 W US 2009055676W WO 2010028004 A3 WO2010028004 A3 WO 2010028004A3
Authority
WO
WIPO (PCT)
Prior art keywords
synthesis
processes
substituted
berbines
substituted berbines
Prior art date
Application number
PCT/US2009/055676
Other languages
French (fr)
Other versions
WO2010028004A2 (en
Inventor
Peter X. Wang
Frank W. Moser
Gary L. Cantrell
Christopher W. Grote
Original Assignee
Mallinckrodt 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
Application filed by Mallinckrodt Inc. filed Critical Mallinckrodt Inc.
Priority to EP09792152.2A priority Critical patent/EP2331508B1/en
Publication of WO2010028004A2 publication Critical patent/WO2010028004A2/en
Publication of WO2010028004A3 publication Critical patent/WO2010028004A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2282—Unsaturated compounds used as ligands
    • B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
    • C07D217/18—Aralkyl radicals
    • C07D217/20—Aralkyl radicals with oxygen atoms directly attached to the aromatic ring of said aralkyl radical, e.g. papaverine
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/60—Reduction reactions, e.g. hydrogenation
    • B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
    • B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
    • B01J2231/643—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of R2C=O or R2C=NR (R= C, H)
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/821—Ruthenium

Abstract

The present invention provides processes for the synthesis of substituted berbine compounds. Also provided are intermediates used in the synthesis of substituted berbine compounds.
PCT/US2009/055676 2008-09-03 2009-09-02 Substituted berbines and processes for their synthesis WO2010028004A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP09792152.2A EP2331508B1 (en) 2008-09-03 2009-09-02 Substituted berbines and processes for their synthesis

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US9382008P 2008-09-03 2008-09-03
US61/093,820 2008-09-03

Publications (2)

Publication Number Publication Date
WO2010028004A2 WO2010028004A2 (en) 2010-03-11
WO2010028004A3 true WO2010028004A3 (en) 2010-05-06

Family

ID=41328473

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2009/055676 WO2010028004A2 (en) 2008-09-03 2009-09-02 Substituted berbines and processes for their synthesis

Country Status (3)

Country Link
US (2) US9458109B2 (en)
EP (1) EP2331508B1 (en)
WO (1) WO2010028004A2 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110015219A1 (en) * 2009-07-16 2011-01-20 Mallinckrodt Inc. (+)-Morphinans as Antagonists of Toll-Like Receptor 9 and Therapeutic Uses Thereof
JP6577491B2 (en) * 2014-06-11 2019-09-18 スペックジーエックス エルエルシー Oxidative dearomatization of belbin.
FR3052291B1 (en) 2016-06-03 2018-11-23 Stmicroelectronics (Rousset) Sas METHOD FOR MANUFACTURING A DIODE NETWORK, IN PARTICULAR FOR A NONVOLATILE MEMORY, AND CORRESPONDING DEVICE.

Family Cites Families (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3101339A (en) 1958-10-30 1963-08-20 Boehringer Sohn Ingelheim Quaternary salts of normorphine and its acylated derivatives
US4141897A (en) 1976-12-20 1979-02-27 Research Corporation N-dealkylation of N-alkyl-14-hydroxymorphinans and derivatives thereof
US4176186A (en) 1978-07-28 1979-11-27 Boehringer Ingelheim Gmbh Quaternary derivatives of noroxymorphone which relieve intestinal immobility
FR2469413B1 (en) 1979-11-13 1986-04-25 Urpha 6H-DIBENZO (A, G) 5,8,13,13A-TETRAHYDROQUINOLIZINE DERIVATIVES, PROCESS FOR OBTAINING AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
PL124001B1 (en) 1980-01-25 1982-12-31 Inst Przemyslu Zielarskiego Process for preparing quaternary halides of n-alkylor n-aralkyl- derivatives of tropanic and isoquinolylic alkaloids
US4322426A (en) 1980-04-28 1982-03-30 E. I. Du Pont De Nemours And Company 17-Substituted-6-desoxy-7,8-dihydro-6α-methylnoroxymorphone narcotic antagonists
US4727146A (en) 1980-07-03 1988-02-23 The United States Of America As Represented By The Department Of Health And Human Services Synthesis of chiral 1-benzyl-1,2,3,4-tetra-hydroisoquinolines by asymmetric reduction
US4410700A (en) 1980-07-03 1983-10-18 The United States Of America As Represented By The Department Of Health And Human Services Preparation of chiral 1-benzyl-1,2,3,4-tetrahydroisoquinolines by optical resolution
US4368326A (en) 1980-07-03 1983-01-11 Rice Kenner C Short total synthesis of dihydrothebainone, dihydrocodeinone, and nordihydroccodeinone
US4556712A (en) 1981-05-20 1985-12-03 The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services Preparation and racemization of chiral 1-benzyl-1,2,3,4-tetrahydroisoquinolines
US4521601A (en) 1981-05-20 1985-06-04 The United States Of America As Represented By The Department Of Health & Human Services Practical total synthesis unnatural enantiomers of opium-derived morphinans
US4535157A (en) 1983-11-01 1985-08-13 Key Pharmaceuticals, Inc. Process for making 6-desoxy-6-methylenenaloxone and 6-desoxy-6-methylenenaltrexone
JPS60132983A (en) 1983-12-21 1985-07-16 Tanabe Seiyaku Co Ltd Thiazoleacetic acid derivative and its production
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
US5112975A (en) 1984-03-27 1992-05-12 Mallinckrodt Specialty Chemicals Company Preparation of noroxymorphone from morphine
US5668285A (en) 1986-10-31 1997-09-16 The United States Of America As Represented By The Department Of Health And Human Services Total synthesis of northebaine, normophine, noroxymorphone enantiomers and derivatives via N-Nor intermediates
DE4132159A1 (en) 1991-09-27 1993-04-01 Boehringer Ingelheim Kg 14-HYDROXY-N- (2-METHOXYETHYL) -7,8-DIHYDROMORPHINE AND -NORISOMORPHINE, PROCESS FOR THEIR PREPARATION AND THEIR USE AS DRUG
US5574159A (en) 1992-02-03 1996-11-12 Delta Pharmaceuticals, Inc. Opioid compounds and methods for making therefor
US5352680A (en) 1992-07-15 1994-10-04 Regents Of The University Of Minnesota Delta opioid receptor antagonists to block opioid agonist tolerance and dependence
WO1994008599A1 (en) 1992-10-14 1994-04-28 The Regents Of The University Of Colorado Ion-pairing of drugs for improved efficacy and delivery
SE9401728D0 (en) 1994-05-18 1994-05-18 Astra Ab New compounds II
US5869669A (en) 1996-07-26 1999-02-09 Penick Corporation Preparation of 14-hydroxynormorphinones from normorphinone dienol acylates
US5848788A (en) * 1996-09-11 1998-12-15 H&S&K Enterprises Electro-magnetic game board
US5756851A (en) 1996-10-21 1998-05-26 Albemarle Corporation Production of nabumetone or precursors thereof
EP0897726B1 (en) 1996-11-25 2007-04-11 Toray Industries, Inc. Antipruritic agent
ES2121554B1 (en) 1996-12-23 1999-06-16 Univ Santiago Compostela PROCEDURE FOR OBTAINING 14-HYDROXIMOFINONES BY PHOTOOXIDATION OF MORPHINE ALKALOIDS WITH ALCOXIDIENIC SYSTEM IN RING C.
GB9713703D0 (en) 1997-06-30 1997-09-03 Johnson Matthey Plc Preparation of opiates
ES2172376B1 (en) 2000-01-28 2003-11-16 Servier Lab NEW DERIVATIVES OF ISOQUINOLEINS, ITS PREPARATION PROCEDURE AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM.
DE10229842A1 (en) 2002-07-03 2004-02-05 Helmut Prof. Dr. Schmidhammer Morphinane derivatives and their quaternary ammonium salts substituted in position 14, production process and use
CA2500118C (en) 2002-09-25 2011-04-12 Euro-Celtique S.A. N-substituted hydromorphones and the use thereof
AU2003290630B2 (en) 2002-11-08 2009-01-29 SpecGx LLC Process for the preparation of quaternary N-alkyl morphinan alkaloid salts
KR101011460B1 (en) 2004-02-06 2011-01-28 유로-셀띠끄 소시에떼 아노님 Methods for making 3-o-protected morphinones and 3-o-protected morphinone dienol carboxylates
WO2006084389A1 (en) 2005-02-11 2006-08-17 Cilag Ltd. Method for purifying noroxymorphone compounds
AR057035A1 (en) 2005-05-25 2007-11-14 Progenics Pharm Inc SYNTHESIS OF (R) -N-METHYLNTREXONE, PHARMACEUTICAL COMPOSITIONS AND USES
AR057325A1 (en) 2005-05-25 2007-11-28 Progenics Pharm Inc SYNTHESIS OF (S) -N-METHYLNTREXONE, PHARMACEUTICAL COMPOSITIONS AND USES
WO2006138020A2 (en) 2005-06-16 2006-12-28 Mallinckrodt Inc. A synthetic route to 14-hydroxyl opiates through 1-halo-thebaine or analogs

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
BUCHS ET AL.: "69. Aromatization of 1-Benzyltetrahydroisoquinolines: Racemization of (-)-(S)-(N-nor)-Reticuline", HELVETICA CHIMICA ACTA, vol. 64, 1981, pages 681 - 686, XP002560193 *
CHEN ET AL.: "Thalifaurine and Dehydrodiscretine, new Quaternary Protoberberines fron Thalictrum Fauriei", JOURNAL OF PHARMACEUTICAL SCIENCES, vol. 69, no. 9, 1980, pages 1061 - 1065, XP002560196 *
GREWE ET AL.: "Die Synthese der Homoisovanillinsäure und ihre Überführung in 6-Methoxy-isochinolin-Derivate", CHEMISCHE BERICHTE, vol. 96, 1963, pages 1520 - 1528, XP002560192 *
KAMETANI T ET AL: "A MODIFIED SYNTHESIS OF CODAMINE UNDER ESCHWEILER CLARKE CONDITIONS I CORYDALIS-PSEUDOADUNCA-D ALKALOID", JOURNAL OF HETEROCYCLIC CHEMISTRY, HETEROCORPORATION. PROVO, US, vol. 5, no. 6, 1 December 1968 (1968-12-01), pages 753 - 755, XP009126936, ISSN: 0022-152X *
KAMETANI T ET AL: "Studies on the syntheses of heterocyclic compounds", JOURNAL OF THE CHEMICAL SOCIETY, SECTION C: ORGANIC CHEMISTRY, CHEMICAL SOCIETY. LETCHWORTH, GB, 1 January 1969 (1969-01-01), pages 2036 - 2038, XP009126947, ISSN: 0022-4952 *
MUJAHIDIN ET AL.: "Enantioselective Synthesis of (+)-(S)-Laudanosine and (-)-(S)-Xylopinine", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 13, 2005, pages 2689 - 2693, XP002560191 *
SAHA ET AL.: "Synthesis and In Vitro Platelet Aggregation and TP Receptor Binding Studies on Bicyclic 5,8-Ethanooctahydroisoquinolines and 5,8-Ethanotetrahydroisoquinolines", BIOORGANIC AND MEDICINAL CHEMISTRY, vol. 10, 2002, pages 2779 - 2793, XP002560195 *
SPÄTH ET AL.: "Über Alkaloide der Colombowurzel, VII. Mitteil.: Über das 2.3.11.12.13-Pentamethoxy-berbin", CHEMISCHE BERICHTE, vol. 75, 1942, pages 400 - 407, XP002560194 *

Also Published As

Publication number Publication date
WO2010028004A2 (en) 2010-03-11
US9458109B2 (en) 2016-10-04
US20160347747A1 (en) 2016-12-01
US9856251B2 (en) 2018-01-02
EP2331508B1 (en) 2014-11-12
US20100056789A1 (en) 2010-03-04
EP2331508A2 (en) 2011-06-15

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