132539-07-2

Usage

Uses

Used in Anesthesia:
Remifentanil Hydrochloride is used as an anesthetic agent for general anesthesia. Its rapid onset (1.6 min) and rapid offset (5.4 min) independent of the duration of administration make it a preferred choice for surgeries where precise control of the depth of anesthesia is required.
Used in Post-operative Pain Management:
Remifentanil Hydrochloride is used as an analgesic for immediate post-operative pain management. Its unique pharmacokinetic properties allow for a quick and effective relief of pain during the initial recovery period following surgery.
Used in Pharmaceutical Research:
Remifentanil Hydrochloride is used as a research compound in the development of new pharmaceuticals targeting the μ-opioid receptor. Its potent and short-acting nature provides valuable insights into the design and optimization of novel analgesic drugs.
Used in Drug Delivery Systems:
Remifentanil Hydrochloride can be utilized in the development of innovative drug delivery systems to improve its bioavailability, stability, and targeted delivery to specific tissues or organs. This may involve the use of various carriers, such as nanoparticles or liposomes, to enhance the drug's therapeutic outcomes and minimize potential side effects.

Originator

Glaxo Wellcome (UK)

Biochem/physiol Actions

Remifentanil hydrochloride is a mu opioid receptor agonist, anesthetic, and analgesic compound. Remifentanil was developed as an ultra-short-acting mu opioid receptor agonist with improved pharmacodynamic properties.

Pharmacokinetics

Remifentanil is much like alfentanil in its pharmacodynamic effects. It is a selective μ opioid agonist with 15 to 20 times greater potency than alfentanil. Remifentanil has an onset of action of 1 to 3 minutes when given intravenously. Its unique property is its rapid offset of action, which is independent of the duration of administration of the compound. Thus, it is very useful for titration of antinociceptive effect, followed by a rapid and predictable recovery time of 3 to 5 minutes. The short duration of action is a result of the ester group, which has been rationally designed into the substituent on the piperidine nitrogen. This ester group is rapidly hydrolyzed to the inactive carboxylic acid by serum and tissue esterases, making the drug's duration of action essentially independent of the liver or renal function of the patient. Remifentanil is used extensively for analgesia associated with general anesthesia procedures. It often is used in combination with injectable general anesthetic agents, such as midazolam or propofol.

InChI:InChI=1/C20H28N2O5.ClH/c1-4-17(23)22(16-8-6-5-7-9-16)20(19(25)27-3)11-14-21(15-12-20)13-10-18(24)26-2;/h5-9H,4,10-15H2,1-3H3;1H

Upstream product

• 132875-61-7 remifentanil 
• 62-53-3 aniline 
• 41979-39-9 4-piperidone hydrochloride 
• 67-56-1 methanol 
• 1225599-16-5 3-(4-oxopiperidin-1-yl)propanenitrile 
• 61085-87-8 methyl 4-[N-(1-oxopropyl)-N-phenylamino]-4-piperidinecarboxylate hydrochloride 
• 292638-85-8 acrylic acid methyl ester 
• 938184-95-3 methyl 3-(4-N-aminophenyl-4-carbomethoxy-piperidino)propionate 
• 79-03-8 propionyl chloride 

Downstream Products

• 132875-61-7 remifentanil 

Relevant academic research and scientific papers

INTERMEDIATES FOR THE PREPARATION OF REMIFENTANIL HYDROCHLORIDE

A new intermediate for synthesizing 1-substituted-4-[phenyl(propanoyl)amino]piperidine-4-carbonitrile derivatives is laid open. Specifically set out is a method for use of this intermediate in the preparation of remifentanil. The enclosed shorter process offers a greater yield of products with higher purity as compared to methods reported in the prior art.

METHOD FOR PRODUCING N-PHENYL-N-(4-PIPERIDINYL) AMIDE SALTS

The invention relates to a method for producing N-phenyl-N-(4-piperidinyl)amide salts, particularly pharmaceutically tolerable addition salts of the compound Remifentanil, in that a compound of the formula (III) is reacted with an acrylic acid alkyl ester of the formula CH2═CH—C(O)—OR: where independently of each other R denotes low-molecular alkyl, preferably (C1-4)alkyl, preferably methyl or ethyl, R1 denotes low-molecular alkyl, preferably (C1-4)alkyl, preferably methyl or ethyl; and HX denotes an inorganic or organic acid, wherein the components are optionally reacted in the presence of a catalyst, preferably at a higher temperature, thereby obtaining the salt of the compound of formula (I).

Alternate Process for Remifentanil Preparation

An alternate process for synthesizing opiate or opioid analgesics and anesthetics, and intermediates thereof is provided. In particular, a process of synthesizing synthetic opiate or opioid compounds such as, for example, remifentanil, carfentanil, sufentanil, fentanyl, and alfentanil are disclosed.

Process for preparing remifentanil, intermediates thereof, use of said intermediates and processes for their preparation

A process for preparing remifentanil by conversion of the nitrile group of a cyanopiperidinyl propanoate derivative to an ester group. Advantageously, with this process the number of steps for preparing remifentanil from commercial products is significantly reduced, compared to the processes known in the art.

CRYSTALLINE FORM OF REMIFENTANIL HYDROCHLORIDE

The present invention relates to a crystalline polymorphic form of remifentanil hydrochloride. The invention also describes methods of preparing a polymorphic form of remifentanil hydrochloride.

PROCESS FOR SYNTHESIZING REMIFENTANIL

A process for synthesizing remifentanil or carfentanil, as well as intermediates for use in the preparation of synthetic opiate or opioid compounds. The process comprising reacting a 4-amino 4-carbamyl piperidine with a base in a closed reaction chamber at elevated temperature and pressure to form to intermediate which may be esterified with an alcohol, alkylated, and acylated to produce a synthetic opiate or opioid compound.