16196-82-0

Usage

Uses

Intermediate in the preparation of Buprenorphine derivatives and analgesic compounds.

Upstream product

• 16196-83-1 7α-acetyl-6,14-endoethanotetrahydrothebaine 
• 76-57-3 codeine 
• 60342-45-2 N-(ethoxycarbonyl)norcodeinone 
• 162333-22-4 (S)-1-(4,5α-epoxy-3,6-dimethoxy-17-methyl-6α,14α-ethano-morphinan-7α-yl)-ethanol 
• 16180-14-6 (S)-1-(4,5α-epoxy-3,6-dimethoxy-17-methyl-6α,14α-etheno-morphinan-7α-yl)-ethanol 
• 36397-12-3 N-desmethyl-N-carboethoxycodeine 
• 757950-17-7 N-carboethoxythebaine 
• 115-37-7 thebaine 
• 15358-22-2 thevinone 

Downstream Products

• 14357-78-9 diprenorphine 
• 14357-76-7 Dihydroetorphine 
• 22152-80-3 [5α,7α]-α-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-3,6-dimethoxy-α,17-dimethyl-6,14-ethenomorphinan-7-methanol 
• 52485-79-7 Buprenorphine 
• 152427-77-5 N-cylcopropylmethyl-6,14-endo-ethanonorthevinone 
• 1429120-69-3 C₃₃H₄₇NO₄ 
• 1429173-80-7 (2′R,5α,6R,7R,14α)-2′-(4,5-epoxy-7,8-dihydro-3-hydroxy-6-methoxy-17-cyclopropylmethyl-6,14-ethano-morphinan-7-yl)-4′-cyclohexyl-butan-2′-ol 
• 736131-85-4 (2′R,5α,6R,7R,14α)-2′-(4,5-epoxy-7,8-dihydro-3-hydroxy-6-methoxy-17-cyclopropylmethyl-6,14-ethano-morphinan-7-yl)-3′-cyclohexyl-propan-2′-ol 
• 84712-92-5 (2S)-2-[(5R,6R,7R,14S)-N-cyclopropanoyl-4,5-epoxy-6,14-ethano-3-hydroxy-6-methoxymorphinan-7-yl]-3,3-dimethylbutan-2-ol 
• 78715-23-8 norbuprenorphine 
• 136232-95-6 buprenorphine hydrochloride 
• 136232-95-6 (+)-Buprenorphine hydrochloride 
• 136232-95-6 Buprenorphin Hydrochlorid 

Relevant academic research and scientific papers

A highly selective κ-opioid receptor agonist with low addictive potential and dependence liability

Buprenorphine analogs have been synthesized. In the studies of analgesic and addictive effects in mice and [35S]GTPγS binding assay in human brain tissue, an analog of buprenorphine where the tert-butyl is replaced by a cyclobutyl moiety (16) has been identified as a selective κ-partial agonist which gives antinociceptive effects, but has low abuse potential. The results may lead to lower degrees of dysphoria than full κ-agonists.

PROCESS FOR THE SYNTHESIS OF BUPRENORPHINE

The present invention relates to a novel route of synthesis for the opioid receptor antagonist Buprenorphine or a pharmaceutically acceptable salt thereof, starting from thebaine, wherein the route comprises the reaction of the baine with a dienophile; forming an alkylated reaction product by reaction with a Grignard-reagent; formation of an cyanamide; deprotection of the cyanamide- and the phenolic-oxygen-moiety, wherein the cleavage of one or both groups is performed in the presence of an alkali or alkaline earth sulfide; followed by derivatization with a cyclopropyl-halogen and hydrogenation to yield Buprenorphine.

DEUTERATED COMPOUND AND MEDICAL USE THEREOF

The present invention relates to a compound represented by formula I and a non-toxic pharmaceutically acceptable salt thereof. In formula (I), R1 is H, CH3 or deuterated methyl (CD3); R2 is CH3 or CH2CH3; R3, R4 and R5 are each independently H or deuterium (D); when R1 is H or CH3, at least one of R3, R4 and R5 is D.

PROCESS FOR THE PREPARATION OF OPIOID COMPOUNDS

The present invention is directed to a process for the preparation of opioid compounds such as buprenorphine, naltrexone, naloxone, nalbuphone, nalbuphine, and the like.

Industrial process for the preparation of buprenorphine and its intermediates

There is provided an efficient industrial process for the preparation of 21-cyclopropyl-7a-(2-hydroxy-3,3-dimethyl-2-butyl)-6,14-endo-ethano-6,7,8,14-tetrahydro-oripavine,i.e. buprenorphine of Formula- I in high yield and purity, with enhanced safety and eco-friendly norms. The invention further relates to an improved process for preparation of intermediates thereof in high yield and purity.

A facile synthesis and structural verification of etorphine and dihydroetorphine from codeine

In this study, an improved process for the synthesis of etorphine and dihydroetorphine from codeine with an overall yield of 2.7% and 1.5% respectively is described. The structure of 19-propylthevinol 7 was verfied by X-ray structure analysis. This result is promising for synthesizing various morphine-based drugs.

PROCESSES FOR THE PRODUCTION OF BUPRENORPHINE WITH REDUCED IMPURITY FORMATION

The present invention provides process for the production of opiate alkaloids. In particular, the present invention provides processes for the production of buprenorphine or a derivative of buprenorphine that minimizes the formation of impurities.

Processes for synthesis of opiate alkaloid derivatives

The present invention provides processes for the synthesis of opiate alkaloids. In particular, the opiate alkaloids produced by the process of the invention are typically intermediate compounds that may be utilized to produce a variety of biologically active alkaloids including buprenorphine and diprenorphine.

AN IMPROVED PROCESS FOR THE PREPARATION OF MORPHINANE ANALOGUES

The present invention relates to an improved process for preparing morphinane analogues of formula (1) wherein the substituents R1, R2, R2a, R3, R4, R5 and Y have the meanings as defined in the specifications.

BUPRENORPHINE DERIVATIVES AND PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF

The present invention relates to a buprenorphine derivative or a pharmaceutically acceptable salt thereof which is an effective analgesic having a much reduced level of addictiveness and an analgesic composition comprising same as an active ingredient.