56030-54-7

Usage

Uses

Used in Medical Applications:
Sufentanil is used as an analgesic for the management of severe pain. Its high potency and therapeutic ratio make it an effective choice for patients requiring strong pain relief, especially in postoperative settings.
Sufentanil is used as an anesthetic/analgesic in open heart surgery for its ability to provide pain relief with fewer cardiac effects and less respiratory depression compared to other opioids.
Used in Research and Forensic Applications:
Sufentanil is used as an analytical reference material for research purposes, aiding in the development and testing of new pharmaceutical compounds and understanding the mechanisms of opioid action.
Sufentanil is also utilized in forensic applications, where it can be used to identify and analyze the presence of the drug in biological samples, such as in cases of drug-related deaths or criminal investigations.

Originator

Jaassen (Belgium)

Manufacturing Process

A mixture of 4.1 parts of N-[4-(methoxymethyl)-4-piperidinyl]-Nphenylpropanamide, 5.3 parts of sodium carbonate and 120 parts of 4- methyl-2-pentanone is stirred and refluxed with water-separator. Then there are added 4.1 parts of 2-thiopheneethanol methanesulfonate ester and stirring at reflux is continued for 18 hours. The reaction mixture is cooled, washed twice with water and evaporated. The oily residue is purified by columnchromatography over silica gel, using a mixture of trichloromethane and 5% of methanol as eluent. The first fraction is collected and the eluent is evaporated. The oily residue is converted into the hydrochloride salt in 2,2'- oxybispropane. The free base is liberated again in the conventional manner. After extraction with 2,2'-oxybispropane, the latter is dried, filtered and evaporated. The oily residue solidifies on triturating in petroleum-ether. The solid product is filtered off and crystallized from petroleum-ether at -20°C, yielding, after drying, N-[4-(methoxymethyl)-1-[2-(2-thienyl)ethyl]-4- piperidinyl]-N-phenylpropanamide; melting point 98.6°C.

Therapeutic Function

Analgesic

InChI:InChI=1/C22H30N2O2S/c1-3-21(25)24(19-8-5-4-6-9-19)22(18-26-2)12-15-23(16-13-22)14-11-20-10-7-17-27-20/h4-10,17H,3,11-16,18H2,1-2H3

Upstream product

• 61380-07-2 2-(thiophen-2-yl)ethyl methanesulfonate 
• 61086-18-8 N-[4-(methoxymethyl)-4-piperidinyl]-N-phenylpropanamide 
• 71195-58-9 alfentanil 
• 79-03-8 propionyl chloride 
• 191339-42-1 2-(2-thiophenylethyl) 4-nitro-benzene sulfonate 
• 1225323-79-4 4-[(1-oxopropyl)phenylamino]-4-methoxymethyl piperidine nosylate 
• 60561-17-3 sufentanil citrate 
• 72996-73-7 4-(Methoxymethyl)-N-phenyl-1-<2-(2-thienyl)ethyl>-4-piperidinamine 
• 62-53-3 aniline 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 1159835-31-0 1-(tert-butoxycarbonyl)-4-(phenylamino)piperidine-4-carboxylic acid 
• 5402-55-1 2-thiophenethanol 

Downstream Products

• 60561-17-3 sufentanil citrate 
• 99759-68-9 desmethylsufentanil 

Relevant academic research and scientific papers

Preparation method of alfentanil and sufentan and compounds used for preparation of sufentanil and alfentan

The invention discloses a preparation method of alfentanil and sufentan and compounds used for preparation of sufentanil and alfentan. Specifically, the method for preparation of a compound shown as formula V includes: carrying out BOC reaction on a compound shown as formula IV to obtain the compound shown as formula V in the specification. The method can conveniently, efficiently and safely prepare an intermediate product for synthesis of alfentanil and sufentan, i.e. the compound shown as formula V. And then, the compound shown as formula V can be effectively used for preparation of alfentanil and sufentan.

PREPARATION OF SUFENTANIL CITRATE AND SUFENTANIL BASE

Provided herein are processes for forming sufentanil citrate from sufentanil base. One process comprises forming sufentanil citrate in the presence of a polar non-aqueous solvent. Other processes comprise forming sufentanil citrate in the presence of water.

Process for the Preparation of Sufentanil Base and Related Compounds

The present disclosure generally related to an improved process for the preparation of various piperidine derivatives. More particularly, the present disclosure related to an improved process for preparing sufentanil base (1) and related compounds, which

IMPROVED METHOD OF MAKING PIPERIDINE DERIVATIVES

The present invention relates to a process for the preparation of piperidine derivatives including sufentanil, and their pharmaceutically acceptable salts, such as the citrate salt.

SUBSTITUTED 4-AMINO-PIPERIDINES

The present invention relates to new substituted 4-amino-piperidine opioid receptor modulators, pharmaceutical compositions thereof, and methods of use thereof

A facile method for preparation of [2H3]-sufentanil and its metabolites

An improved process for the synthesis of sufentanil with an overall yield of 26% is described. The reactive and high yielding N-debenzylation of the piperidine intermediate 7 using a mixture of Pd/C and Pd(OH)2 was applied to other drug intermediates affording free amines in short reaction times. The deuterium-labeled sufentanil and the metabolite desmethylsufentanil were synthesized applying the optimized process.

IMPROVED METHOD OF MAKING SUFENTANIL

The present invention relates to a process for the preparation of piperidine derivatives including sufentanil and its pharmaceutically acceptable salts, such as it citrate salt

Methods for the syntheses of alfentanil sufentanil and remifentanil

Synthetic pathways are disclosed for synthesizing derivatives or analogs of fentanyl. Specifically set out are pathways for synthesizing alfentanil, sufentanil and remifentanil. The disclosed methods require fewer steps and produce a greater yield of prod

Combination of selected opioids with muscarine antagonists for treating urinary incontinence

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.