- Studies on regioselective hydrogenation of thebaine and its conversion to hydrocodone
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Thebaine was subjected to catalytic hydrogenation under a variety of conditions in order to determine the regioselectivity for C-6/C-7 versus C-8/C-14 olefin saturation.
- Leisch, Hannes,Carroll, Robert J.,Hudlicky, Tomas,Cox, D. Phillip
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Read Online
- Selective Olefin Reduction in Thebaine Using Hydrazine Hydrate and O2 under Intensified Continuous Flow Conditions
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Hydrocodone, a high value active pharmaceutical ingredient (API), is usually produced in a semisynthetic pathway from morphine, codeine or thebaine. The latter alkaloid is an attractive precursor as it is not used as a remedy itself. The key step in this production route is a selective olefin reduction forming 8,14-dihydrothebaine which can be subsequently hydrolyzed to yield hydrocodone. Unfortunately, standard hydrogenation procedures cannot be applied due to severe selectivity problems. A transfer hydrogenation using in situ generated diimide is the only known alternative to achieve a selective transformation. The most (atom) economic generation of this highly unstable reducing agent is by oxidizing hydrazine hydrate (N2H4·H2O) with O2. In the past, this route was "forbidden" on an industrial scale due to its enormous explosion potential in batch. A continuous high-temperature/high-pressure methodology allows an efficient, safe, and scalable processing of the hazardous reaction mixture. The industrially relevant reduction was achieved by using four consecutive liquid feeds (of N2H4·H2O) and residence time units, resulting in a highly selective reduction within less than 1 h.
- Pieber, Bartholom?us,Cox, D. Phillip,Kappe, C. Oliver
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- One-pot conversion of thebaine to hydrocodone and synthesis of neopinone ketal
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The ethylene glycol ketal of neopinone was prepared in a one-pot procedure by the reaction of thebaine with ethylene glyocol in the presence of p-toluenesulfonic acid. The ketal is also an intermediate in the conversion of thebaine to hydrocodone with ethylene glycol and Pd(OAc)2, followed by hydrogenation. Additionally, a one-pot procedure for the conversion of thebaine to hydrocodone was achieved by employing palladium catalysis in aqueous medium. Palladium serves a dual purpose in this transformation, first for the activation of the dienol ether of thebaine and second as a hydrogenation catalyst. This procedure was found to be comparable to the two-step protocol which employs diimide reduction of thebaine followed by acid-catalyzed hydrolysis of the resulting 8,14-dihydrothebaine to hydrocodone. Experimental and spectral data are provided for all compounds.
- Carroll, Robert J.,Leisch, Hannes,Rochon, Lena,Hudlicky, Tomas,Cox, D. Phillip
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- 14,17-Cyclonorcodeinone dimethylacetal: A New Codeinon Derivative, II
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In addition to a short communication describing the synthesis of 14,17-cyclonorcodeinone dimethylacetal 1a we wish to present a simple alternative route together with a selection of some reactions depending on the great reactivity of this highly strained small ring system.The structure of 1a is established by X-ray analysis.
- Fleischhacker, W.,Richter, B.,Voellenkle, H.
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- Transition metal-catalyzed redox isomerization of codeine and morphine in water
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A water-soluble rhodium complex formed from commercially available [Rh(COD)(CH3CN)2]BF4 and 1,3,5-triaza-7- phosphaadamantane (PTA) catalyzes the isomerization of both codeine and morphine into hydrocodone and hydromorphone with very high efficiency. The reaction is performed in water, allowing isolation of the final products by simple filtration, which results in very high isolated yields. The reactions can be easily scaled up to 100 g.
- Gomez, Antonio Bermejo,Holmberg, Paer,Baeckvall, Jan-E.,Martin-Matute, Belen
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Read Online
- NOVEL OPIOID COMPOUNDS AND USES THEREOF
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This invention relates to novel opioid derivatives of Formula I: or a pharmaceutically acceptable salt or solvate thereof, wherein R1, R3, R4 and Z are as defined herein in the disclosure. The invention also relates to the use of such compounds for the treatment or prevention of, for example, pain.
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Paragraph 0509-0511
(2019/09/12)
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- PROCESS FOR THE PREPARATION OF BENZHYDROCODONE HYDROCHLORIDE
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The invention is directed to processes for the preparation of benzhydrocodone hydrochloride. More particularly, the invention is directed to processes for a one-pot synthesis of benzhydrocodone hydrochloride of improved yield and/or purity.
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Paragraph 0190-0191
(2018/03/25)
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- SUPPORTED METAL CATALYST FOR THE PRODUCTION OF HYDROCODONE AND HYDROMORPHONE
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The present invention relates to the process for the manufacture of hydrocodone or hydromorphone from their enol derivatives codeine and morphine respectively. Particularly, the invention discloses a metal catalyst that is used in low amount, leads to high yields and can easily be reused.
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Page/Page column 7
(2018/01/15)
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- General, Simple, and Chemoselective Catalysts for the Isomerization of Allylic Alcohols: The Importance of the Halide Ligand
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Remarkably simple IrIIIcatalysts enable the isomerization of primary and sec-allylic alcohols under very mild reaction conditions. X-ray absorption spectroscopy (XAS) and mass spectrometry (MS) studies indicate that the catalysts, with the general formula [Cp*IrIII], require a halide ligand for catalytic activity, but no additives or additional ligands are needed.
- Erbing, Elis,Vázquez-Romero, Ana,Bermejo Gómez, Antonio,Platero-Prats, Ana E.,Carson, Fabian,Zou, Xiaodong,Tolstoy, P?ivi,Martín-Matute, Belén
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supporting information
p. 15659 - 15663
(2016/10/25)
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- PREPARATION OF SATURATED KETONE MORPHINAN COMPOUNDS BY CATALYTIC ISOMERISATION
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There is provided a novel process for the preparation of a compound of formula I, wherein R1, R2 and R3 are as described in the description, by conversion of a corresponding allylic alcohol.
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Page/Page column 46-47; 49-51
(2015/02/19)
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- On the selection of an opioid for local skin analgesia: Structure-skin permeability relationships
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Recent studies demonstrated that post-herpetical and inflammatory pain can be locally managed by morphine gels, empirically chosen. Aiming to rationalize the selection of the most suitable opioid for the cutaneous delivery, we studied the in vitro penetration through human epidermis of eight opioids, evidencing the critical modifications of the morphinan core. Log P, log D, solid-state features and solubility were determined. Docking simulations were performed using supramolecular assembly made of ceramide VI. The modifications on position 3 of the morphinan core resulted the most relevant in determining both physicochemical characteristics and diffusion pattern. The 3-methoxy group weakened the cohesiveness of the crystal lattice structure and increased the permeation flux (J). Computational studies emphasized that, while permeation is essentially controlled by molecule apolarity, skin retention depends on a fine balance of polar and apolar molecular features. Moreover, ChemPLP scoring the interactions between the opioids and ceramide, correlated with both the amount retained into the epidermis (Qret) and J. The balance of the skin penetration properties and the affinity potency for μ-receptors evidenced hydromorphone as the most suitable compound for the induction of local analgesia.
- Musazzi, Umberto M.,Matera, Carlo,Dallanoce, Clelia,Vacondio, Federica,De Amici, Marco,Vistoli, Giulio,Cilurzo, Francesco,Minghetti, Paola
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p. 177 - 185
(2015/05/20)
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- PROCESSES FOR MAKING HYDROCODONE, HYDROMORPHONE AND THEIR DERIVATIVES
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Improved processes for making hydrocodone and hydromorphone as well as their 8,14-dihydrothebaine and 8,14-dihydrooripavine derivatives and salts are disclosed.
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Paragraph 0085; 0086
(2015/09/28)
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- Total synthesis of dihydrocodeine and hydrocodone via a double claisen rearrangement and C-10/C-11 closure strategy
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Dihydrocodeine and hydrocodone were synthesized from bromobenzene in 16 and 17 transformations, respectively. The key steps involved the toluene dioxygenase-mediated dihydroxylation of bromobenzene by whole-cell fermentation with E. coli JM109(pDTG601A), Kazmaier-Claisen rearrangement of glycinate ester, Claisen rearrangement to set the C-13 quaternary center, and C-10-C-11 closure. Experimental procedures are provided for the key steps. Georg Thieme Verlag Stuttgart . New York.
- Varghese, Vimal,Hudlicky, Tomas
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p. 369 - 374
(2013/04/23)
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- Heterogeneous Ruthenium Metal Catalyst for the Production of Hydrocodone, Hydromorphone or a Derivative Thereof
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The present disclosure generally relates to catalytic methods for producing opioid derivatives. More particularly, the present disclosure relates to the preparation of hydrocodone, hydromorphone, or a derivative thereof, by means of a conversion or an isomerization of codeine, morphine, or a derivative thereof, respectively, using a heterogeneous ruthenium metal catalyst.
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Page/Page column 8
(2011/04/18)
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- Methods for Producing Hydrocodone, Hydromorphone or a Derivative Thereof
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The present disclosure generally relates to methods for producing opioid derivatives. More particularly, the present disclosure relates to the preparation of hydromorphone, hydrocodone, or a derivative thereof, by means of a non-catalytic hydrogenation reaction of thebaine, oripavine or a derivative thereof, respectively, using a hydrazide reagent, followed by hydrolysis of the hydrogenated intermediate at a low temperature and for a short period of time. Additionally, the present disclosure relates to a composition comprising the desired hydromorphone, hydrocodone, or a derivative thereof, in combination with a 6-beta compound that is structurally related thereto.
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Page/Page column 12
(2011/04/18)
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- COMPOSITIONS COMPRISING ENZYME-CLEAVABLE OPIOID PRODRUGS AND INHIBITORS THEREOF
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Pharmaceutical compositions and their methods of use are provided, where the pharmaceutical compositions comprise an opioid prodrug that provides enzymatically-controlled release of an opioid, and an enzyme inhibitor that interacts with the enzyme(s) that mediates the enzymatically-controlled release of the opioid from the opioid prodrug so as to attenuate enzymatic cleavage of the opioid prodrug.
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Page/Page column 149-150
(2011/11/06)
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- BENZOIC ACID, BENZOIC ACID DERIVATIVES AND HETEROARYL CARBOXYLIC ACID CONJUGATES OF HYDROCODONE, PRODRUGS, METHODS OF MAKING AND USE THEREOF
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The presently described technology provides compositions comprising aryl carboxylic acids chemically conjugated to hydrocodone (morphinan-6-one, 4,5-alpha-epoxy-3-methoxy-17-methyl) to form novel prodrugs/compositions of hydrocodone, including benzoates and heteroaryl carboxylic acids, which have a decreased potential for abuse of hydrocodone. The present technology also provides methods of treating patients, pharmaceutical kits and methods of synthesizing conjugates of the present technology.
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- PHENYLETHANOIC ACID, PHENYLPROPANOIC ACID AND PHENYLPROPENOIC ACID CONJUGATES AND PRODRUGS OF HYDROCODONE, METHOD OF MAKING AND USE THEREOF
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The presently described technology provides phenylethanoic acid, phenylpropanoic acid, phenylpropenoic acid, a salt thereof, a derivative thereof or a combination thereof chemically conjugated to hydrocodone (morphinan-6-one, 4,5-alpha-epoxy-3-methoxy-17-methyl) to form novel prodrugs or compositions of hydrocodone which have a decreased potential for abuse of hydrocodone. The present technology also provides methods of treating patients, pharmaceutical kits and methods of synthesizing conjugates of the present technology.
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- Preparation of Saturated Ketone Morphinan Compounds by Catalytic Isomerization
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The present invention provides processes for the preparation of saturated ketone morphinan compounds by catalytic isomerization. In particular, the invention provides processes for the conversion of a morphinan comprising an allyl alcohol ring moiety into a morphinan comprising a saturated ketone ring moiety by an isomerization reaction catalyzed by an allyl-transition metal catalyst.
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Page/Page column 8
(2010/11/03)
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- CONVERSION OF THEBAINE TO MORPHINE DERIVATIVES
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The present invention provides methods for the conversion of thebaine to a morphine derivative, such as hydrocodone. Novel ketal intermediates of the conversion are provided. A one-pot procedure for the conversion comprises treating thebaine with an acid in the presence of a metal catalyst.
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Page/Page column 4; 6
(2009/01/24)
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- Method for catalytic preparation of hydromorphone and hydrocodone
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The present invention generally relates to catalysts of formula (III) [in-line-formulae][M(P(Ra)(Rb)N(Rc)(Rd))2Xn]mYp [/in-line-formulae]that selectively convert morphine/codeine to hydromorphone/hydrocodone, and methods of use thereof.
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Page/Page column 7-8
(2008/12/06)
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- PRODRUGS AND METHODS OF MAKING AND USING THE SAME
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Prodrugs of parent drugs and methods of making and using the same are described. The prodrugs comprise an amine-containing parent drug moiety and a prodrug moiety, such as methoxyphosphonic acid or ethoxyphosphonic acid. The prodrugs may be employed in therapy for the treatment of various indications, such as pain, and in methods of decreasing the abuse potential of abuse-prone drugs and/or delaying the onset of parent drug activity and/or prolonging parent drug activity as compared to administration of a parent drug.
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Page/Page column 74
(2008/12/06)
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- 6-monoacetylmorphine derivatives useful in immunoassay
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Analogs of 6-monoacetyl morphine (6-MAM) are described. These include analogs derivatized at either the C-3 position, the C-6 position, or the nor position of the molecule. These analogs allow for elaboration with linkers terminated by a functional group such as an activated ester, the functional groups being useful for attaching the molecule to other entities such as proteins, polysaccharides, and reporter groups.
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Page/Page column 9
(2010/11/28)
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- 6-Monoacetylmorphine derivatives useful in immunoassay
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Analogs of 6-monoacetyl morphine (6-MAM) are described. These include analogs derivatized at either the C-3 position, the C-6 position, or the nor position of the molecule. These analogs allow for elaboration with linkers terminated by a functional group such as an activated ester, the functional groups being useful for attaching the molecule to other entities such as proteins, polysaccharides, and reporter groups.
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- Production of opioid analgesics
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The present invention includes a process for the manufacture of dihydrothebaine, dihydrocodeinone enol acetate, hydrocodone, and analogs thereof by reacting dihydrocodeine or analogs thereof with benzophenone in the presence of potassium tert-alkylate in a hydrocarbon solvent to generate a reaction mixture containing an enolate of the corresponding ketone, followed by addition of the reaction mixture to the electrophilic agent and isolation of the product.
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Page/Page column 6
(2008/06/13)
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- Enantioselective synthesis of (-)-dihydrocodeinone: A short formal synthesis of (-)-morphine
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The radical cyclization approach to the morphine alkaloids has been applied in an asymmetric synthesis of (-)-dihydrocodeinone. A chiral cyclohexenol (R-32), from the CBS reduction of the enone, is the source of chirality. The first key step, tandem closure in which stereochemistry is controlled by geometric constraints, (-)-15b → (+)-16, was followed by an unprecedented reductive hydroamination, completing the synthesis of (-)-dihydroisocodeine ((-)-17) in 13 steps from commercially available materials.
- Parker, Kathlyn A.,Fokas, Demosthenes
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p. 449 - 455
(2007/10/03)
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- Preparation of opioid analgesics by a one-pot process
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A one-pot process for preparing opioid analgesics such as hydrocodone, hydromorphone, and analogues thereof by reacting codeine, morphine, and analogues thereof with hydrogen in a solvent system of benzophenone and neutral solvent in the presence of a metal catalyst followed by oxidation in the presence of potassium tert-alkylate.
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Page column 5,6
(2008/06/13)
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- A METHOD OF PREPARATION OF 4,5α-EPOXY-6-OXOMORPHINAN DERIVATIVES
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A method of preparation of 4,5α-epoxy-6-oxomorphinan derivatives of formula (I), wherein R1 is hydrogen, methyl, or ethyl and R2 is hydrogen, methyl, cyclobutylmethyl or benzyl, in which compounds of formula (II), wherein R1 and R2 are as defined with respect to compounds (I), are isomerized into compounds of formula (I) in the presence of a mixed catalyst containing at least two elements from the group of platinum metals. The method provides the product in high yield and with low contents of impurities.
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Page/Page column 6
(2008/06/13)
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- METHOD FOR THE CATALYTIC PRODUCTION OF HYDROCODONE AND HYDROMORPHONE
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A method for the catalytic conversion of codeine, morphine or analogs thereof into hydrocodone, hydromorphone or analogs thereof utilizing a transition metal complex of a tertiary phosphine halide as catalyst.
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Page/Page column 5-6
(2008/06/13)
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- Method for the catalytic production of hydrocodone and hydromorphone
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A method for the catalytic conversion of codeine, morphine or analogs thereof into hydrocodone, hydromorphone or analogs thereof utilizing a transition metal catalyst of the formula [M(PR3R4R5)nXm]p; wherein R1 is H, alkyl, aryl or acyl; M is a Group VIII transition metal; R3, R4 and R5 are selected from the group consisting of alkyl, aryl, alkoxyl, phenoxyl and combinations thereof; X is a halide or an anion; n is 1, 2, 3 or 4; m is 1 or 2; and p is at least 1.
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- Preparation of dihydrocodeine from codeine
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A process for the preparation of dihydrocodeine by hydrogenating codeine or a salt thereof in aqueous solution in the presence of a catalytic metal and deactivating agent that decreases impurities formation.
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Page/Page column 4; 5
(2008/06/13)
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- Combination of selected opioids with muscarine antagonists for treating urinary incontinence
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Active compound combinations of compounds of group A, particularly opioids, and compounds of group B, particularly anti-muscarine agents and other substances suitable for treatment of an increased urge to urinate or urinary incontinence. Related pharmaceutical formulations and methods of treatment of an increased urge to urinate or urinary incontinence are also provided.
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- Opiod tannate compositions
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A composition comprising the tannate of an opioid. Suitable opioids include alfentanil, buprenorphine, butorphanol, carfentanil, cocaine, codeine, dezocine, diacetylmorphine, dihydrocodeine, dihydromorphine, diphenoxylate, diprenorphine, etorphine, fentanyl, heroin, hydrocodone, hydromorphone, β-hydroxy-3-methylfentanyl, levo-α-acetylmethadol, levorphanol, lofentanil, meperidine, methadone, morphine, nalbuphine, nalmefene, o-methylnaltrexone, naloxone, naltrexone, oxycodone, oxymorphone, pentazocine, pethidine, propoxyphene, remifentanil, sufentanil, tilidine and tramadol. The opioid tannate may be readily prepared by reacting an opioid free base with tannic acid, either neat or in the presence of up to about 30 wt. % water, at a temperature of about 60 to about 150° C. and thereafter recovering the resultant opioid tannate. The opioid tannate may also be prepared by an alternative process that involves reacting the opioid free base with water at a temperature such that not more than about 10 wt. % of the opioid tannate will be decomposed and thereafter removing the water by freeze-drying.
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- Synthesis and biological activity of 8β-substituted hydrocodone indole and hydromorphone indole derivatives
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The 8β-unsubstituted and substituted analogues of hydrocodone indole and hydromorphone indole were synthesized and their binding affinities to opioid receptors were determined. Introduction of an 8β-methyl group into the indolomorphinan nucleus increased
- Yu, Han,Prisinzano, Thomas,Dersch, Christina M.,Marcus, Jamila,Rothman, Richard B.,Jacobson, Arthur E.,Rice, Kenner C.
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p. 165 - 168
(2007/10/03)
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- A rapid, nearly quantitative conversion of codeine to hydrocodone
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A very rapid, two-step, virtually quantitative synthesis of hydrocodone from codeine, via the intermediacy of dihydrocodeine, has been developed.
- Black, T. Howard,Forsee, Jennifer C.,Probst, Donald A.
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p. 3195 - 3201
(2007/10/03)
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- Transformations of morphine, codeine and their analogues by Bacillus sp
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A bacterial strain belonging to the genus Bacillus islolated by enrichment culture technique using morphine as a sole source of carbon transforms morphine and codeine into 14-hydroxymorphinone and 14-hydroxycodeinone as major and 14-hydroxymorphine and 14-hydroxycodeine as minor metabolites, respectively. When the N-methyl group in morphine and codeine are replaced by higher alkyl groups, the organism still retains its ability to carry out 14-hydroxylation as well as oxidation of the C6-hydroxyl group in these N-variants, although the level of metabolites formed are considerably low. The organism readily transforms dihydromorphine and dihydrocodeine into only dihydromorphinone and dihydrocodeinone, respectively, suggesting that the 7,8-double bond is a necessary structural feature to carry out 14-hydroxylation reaction. The cell free extract (20,000 × g supernatant), prepared from morphine grown cells, transforms morphine into 14-hydroxymorphinone in the presence of NAD+, but fails to show activity against testosterone. However, the cell free extract prepared from testosterone grown cells contains significant levels of 17β- hydroxysteroid dehydrogenase but shows no activity against morphine.
- Madyastha,Reddy,Sridhar
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p. 749 - 753
(2007/10/03)
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- Synthesis of enantiomerically pure morphine alkaloids: The hydrophenanthrene route
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A concise, linear, total synthesis of (-)-dihydrocodeinone - a close synthetic precursor of (-)-codeine and (-)-morphine - has been achieved. The carbocyclic core of the alkaloid was provided in the form of a phenanthrenone, which was resolved by chromatography on cellulose triacetate. A cuprate conjugate addition was used to establish the crucial benzylic quaternary stereocenter and to introduce the C2-side chain. Dimeric byproducts provide evidence for a single electron transfer (SET) mechanism. Unusual S(N)2 and radical cyclizations were employed for the formation of the dihydrobenzofuran and the piperidine ring, respectively.
- Trauner, Dirk,Bats, Jan W.,Werner, Andreas,Mulzer, Johann
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p. 5908 - 5918
(2007/10/03)
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- New ventures in the construction of complex heterocycles: Synthesis of morphine and hasubanan alkaloids
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Synthetic approaches to morphine and hasubanan alkaloids involving novel reactions for the formation of their dihydrobenzofuran, piperidine and pyrrolidine ring, respectively, are described. The importance of conformational constraints for the success of these reactions is demonstrated. The syntheses of new dioxepanes, diazepanes, dithiocanes, triazenes and dioxonanes are also reported.
- Trauner, Dirk,Porth, Stefanie,Opatz, Till,Bats, Jan W.,Giester, Gerald,Mulzer, Johann
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p. 653 - 664
(2007/10/03)
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- Formale Totalsynthese von (-)-Morphin ueber konjugierte Cuprataddition
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Keywords: Cuprate; Morphin-Alkaloide; Totalsynthesen
- Mulzer, Johann,Duerner, Gerd,Trauner, Dirk
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p. 3046 - 3048
(2007/10/03)
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- New morphine derivatives having improved analgesic and narcotic properties
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Morphine derivatives having the formula wherein: A1 represents-O-,-S-,-NR?-or-CHR?-; A2 represents-O-,-S-or-NR?-; R1 represents C?-C? alkyl, C?-C? alkenyl or cycloalkylmethyl; R2 represents H, C?-C? alkyl, C?-C? alkenyl, C?-C? acyl or C?-C? hydroxyalkyl; one of X1 and X2 represents H and the other one is a group-A3-R3; A3 represents-CH?-,-CH?CH?-,-OCH?-,-SCH?-,-NR?CH?-,-CO-,-NR?CO-,-SCO-,-SO?-,-NR?SO?-,-O-,-S-or-NR?-; R3 represents an optionally substituted heterocyclic group; R? and R? independently represent H or C?-C? alkyl; whereby the morphinan system may have a further unsaturation, in additon to the benzene ring. These new morphine derivatives have improved analgesic and narcotic properties.
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- Novel opiates and antagonists. 4. 7-Alkanoylhydromorphones
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A series of 7-alkanoyl-substituted hydromorphone derivatives were prepared by acylation of the morpholine enamines. The most potent compound (6i) of the series was found to have agonist activity of the same order of magnitude as that of buprenorphine. The N-cyclopropylmethyl-substituted series was found to exhibit structure-activity relationships for analgesia and narcotic antagonism similar to those of the endo-ethanotetrahydrooripavines.
- Quick,Herlihy,Razdan,Howes
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p. 983 - 986
(2007/10/02)
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- 7,8 and 7-8 Substituted 4,5α-epoxymorphinan-6-one compounds, and methods of treating pain and drug dependence with them
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Disclosed are 7,8 and 7-8 substituted 4,5α-epoxymorphinan-6-one compounds characterized by the structural formula: STR1 In the foregoing formula R1 may be H or methyl, R2 is cyclopropylmethyl, cyclobutylmethyl, allyl or tetrahydrofurfuryl, R3 is H, β-methyl, β-ethyl or α-ethyl and R4 is H or α-methyl. Particular compounds corresponding to the foregoing description are useful as mixed analgesics/narcotic antagonists whereas others have been found to be pure narcotic antagonists.
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