cas 847-86-9, HYDROCODONE BITARTRATE RELATED COMPOUND A CII (70 MG) (MORPHINAN-6-ONE, 4-HYDROXY-3-METHOXY-17-METHYL)

Articles about 847-86-9Total 16 be found

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Deconstructive Asymmetric Total Synthesis of Morphine-Family Alkaloid (?)-Thebainone A
Herein, we describe the development of a deconstructive strategy for the first asymmetric synthesis of (?)-thebainone A, capitalizing on an enantioselective C?C bond activation and a C?O bond cleavage reaction. The rhodium-catalyzed asymmetric “cut-and-sew” transformation between sterically hindered trisubstituted alkenes and benzocyclobutenones allowed efficient construction of the fused A/B/C rings and the quaternary center of the natural product. The newly optimized conditions show broad substrate scope and excellent enantioselectivity (up to 99.5:0.5 er). Taking advantage of boron-mediated ether bond cleavage, we completed the synthesis of the morphine alkaloid (?)-thebainone A by two complementary routes.
Hou, Si-Hua,Prichina, Adriana Y.,Dong, Guangbin
p. 13057 - 13064
(2021)
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Codeine analogues. Synthesis of 4a-aryldecahydroisoquinolines containing nitrogen ring functionality and of octahydro-1H-indeno[1,2,3-ef]isoquinolines. A total synthesis of codeine
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Moos,Gless,Rapoport
p. 227 - 238
(1983)
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Bentley,Wain
p. 972,974
(1952)
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MORPHAN AND MORPHINAN ANALOGUES, AND METHODS OF USE
The present application relates to analogues of morphan and morphinan, compositions thereof, and methods for treating a disease or condition comprising administering an effective amount of the compounds or compositions to a subject in need thereof.
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Page/Page column 74

(2014/12/12)

Synthesis and pharmacological evaluation of aminothiazolomorphinans at the Mu and Kappa opioid receptors
Previous studies with aminothiazolomorphinans suggested that this class of opioid ligands may be useful as a potential pharmacotherapeutic to decrease drug abuse. Novel aminothiazole derivatives of cyclorphan were prepared to evaluate a series of aminothiazolomorphinans with varying pharmacological properties at the κ opioid receptor (KOR) and μ opioid receptor (MOR). This study was focused on exploring the regioisomeric analogs with the aminothiazole on the C-ring of the morphinan skeleton. Receptor binding and [35S] GTPγS binding assays were used to characterize the affinity and pharmacological properties of the aminothiazolomorphinans. Intracranial self-stimulation (ICSS) was used to compare the effects of a representative aminothiazolomorphinan with the morphinan mixed-KOR/MOR agonist butorphan (MCL-101) on brain-stimulation reward.
Provencher, Brian A.,Sromek, Anna W.,Li, Wei,Russell, Shayla,Chartoff, Elena,Knapp, Brian I.,Bidlack, Jean M.,Neumeyer, John L.
p. 8872 - 8878
(2013/12/04)

Rapid access to morphinones: removal of 4,5-ether bridge with Pd-catalyzed triflate reduction
A new synthetic method for the removal of the 4,5-bridged ether moiety of several opioids has been developed. This process offers a faster, simpler synthetic route to obtain the morphinone scaffold in high yields without the need for protection of the ketone moiety.
Hupp, Christopher D.,Neumeyer, John L.
scheme or table
p. 2359 - 2361
(2010/06/13)

CONVERSION OF THEBAINE TO MORPHINE DERIVATIVES
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)

One-pot conversion of thebaine to hydrocodone and synthesis of neopinone ketal
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
experimental part
p. 747 - 752
(2009/07/25)

Synthesis and pharmacological evaluation of 6,7-indolo/thiazolo-morphinans - Further SAR of levorphanol
To further extend the structure-activity relationships of levorphanol, two series of novel morphinans were prepared by incorporation of an indole or aminothiazole fragment to the hexyl ring (ring C) in levorphanol. Such morphinans differed from previously reported ligands in that such indole- or aminothiazole-containing morphinans displayed enhanced binding affinity to the δ opioid receptor, while the affinity to κ and μ receptors was slightly reduced.
Zhang, Ao,Li, Fuying,Ding, Chunyong,Yao, Qizhen,Knapp, Brian I.,Bidlack, Jean M.,Neumeyer, John L.
p. 2747 - 2751
(2008/02/07)

4-HYDROXYBENZOMORPHANS
4-Hydroxybenzomorphans containing carboxamide or thiocarboxamide at the 3-position are useful as analgesics, anti-diarrheal agents, anticonvulsants, antitussives and anti-addiction medications.
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Page/Page column 23

(2010/11/30)

Preparation of dihydrocodeine from codeine
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)

Opioid affinity and selectivity of 4-hydroxy-3-methoxyindolomorphinan analogues related to naltrindole
To investigate the effect of the introduction of a 4-phenolic substituent on the δ opioid affinity and selectivity of the indolomorphinans, a range of 4-phenolic analogues of naltrindole were prepared and evaluated in in vitro assays. Although the majority of the ligands displayed poor affinity for all three opioid receptors (μ, κ, δ), 17-cyclopropylmethyl-6,7-didehydro-4-hydroxy-3-methoxy-6,7:2',3'- indolomorphinan (13) was an exception, displaying excellent 5 binding selectivity (δ K(i) = 7 nM, μ/δ = 1900, μ/κ = 1130). GTP-χ-S functional assays showed 13 to be a selective δ antagonist, albeit with lower potency than naltrindole. Although the reason for the unique profile of 13 could not be determined, these results validate our approach of introducing groups into the indolomorphinans that are known to reduce μ activity, to obtain increased δ selectivity.
Coop, Andrew,Rothman, Richard B.,Dersch, Christina,Partilla, John,Porreca, Frank,Davis, Peg,Jacobson, Arthur E.,Rice, Kenner C.
p. 1673 - 1679
(2007/10/03)

Improved synthesis of dihydrothebainone and its 14 β-epimer
An improved synthesis for the preparation of diastereomerically pure dihydrothebainone (1) from thebaine (3) is reported. A 41% overall yield was realized over three steps via direct transformation of dihydrothebaine-Φ (4) to thebainone-A (6) with 6N HCl.
Davidson,Gregg
p. 547 - 558
(2007/10/03)

Formation of brenzcatechine derivatives by reduction of 6-oxo-morphin derivatives at mercury electrodes
Reduction of naloxone (1) and hydrocodone (4) in Britton-Robinson- buffers at the dropping mercury electrode exclusively leads to (-)-17-allyl- 3,4,14-hydroxymorphinan-6-one (2) and (-)-3-hydroxy-4-methoxy-N- methylmorphinan-6-one (5). The structure of 2 was proved by mass spectra and 1H-NMR spectra. The analytical data of 5 correspond tothose in the literature. The reduction process depends on the presence of the 6-oxo- group.
Abu-Khurmah,Oelschlaeger,Volke
p. 524 - 528
(2007/10/03)

The synthesis of 3,4-dimethoxy-6-morphinanone and isomorphinanone. Spectral inspection of the stereochemistry in cis and trans B/C ring fusion
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Fujii,Abe,Mayakawa,Kanematsu
p. 4670 - 4673
(2007/10/02)

On the total synthesis of the naloxones from 1-benzylisoquinolines via 1-bromo-2-(1-phenyltetrazol-5-yloxy)dihydrocodeinone (chemistry of opium alkaloids, Part XVII)
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Crabbendam,Beyerman,Lie,Maat
p. 135 - 139
(2007/10/02)

Formamidinesulfinic acid reduction of dihydrocodeinone derivatives
Treatment of dihydrocodeinone (1f) with formamidinesulfinic acid afforded mixtures of dihydrothebainone (3a) dihydroisothebainol dihydroisothenainol (4a) under both homogeneous and heterogeneous conditions. Similar treatment of 14-hydroxydihydrocodeinone
Brine,Boldt,Coleman,et al.
p. 1555 - 1557
(2007/10/09)