124980-94-5

Usage

Uses

Used in Pharmaceutical Industry:
(R)-Flurbiprofen is used as an analgesic and anti-inflammatory agent for the treatment of various conditions characterized by pain and inflammation. It is particularly effective for conditions such as rheumatoid arthritis, osteoarthritis, and menstrual pain, providing relief by reducing the levels of prostaglandins in the body.
Used in Pain Management:
(R)-Flurbiprofen is utilized as a pain management tool, helping to alleviate discomfort associated with different types of arthritis and other inflammatory conditions. Its mechanism of action involves the inhibition of cyclooxygenase (COX) enzymes, which are responsible for the synthesis of prostaglandins.
Used in Cardiovascular Risk Management:
Although (R)-Flurbiprofen, like other NSAIDs, may increase the risk of serious cardiovascular events, its use is carefully managed under the guidance of healthcare professionals. This ensures that the benefits of pain relief and inflammation reduction are balanced against potential cardiovascular risks.

InChI:InChI=1/C9H9FO3/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8,11H,5H2,(H,12,13)/t8-/m1/s1

Upstream product

• 51-65-0 4-Fluorophenylalanine 
• 7761-30-0 sodium 3-(4-fluorophenyl)-2-oxopropionate 
• 459-57-4 4-fluorobenzaldehyde 
• 1132-68-9 L-4-fluorophenylalanine 
• 18125-46-7 (R)-4-fluorophenylalanine 
• 125772-83-0 (Z)-4-(4-fluorobenzylidene)-2-methyloxazol-5(4H)-one 

Downstream Products

• 124980-98-9 (R)-methyl 3-(4-fluorophenyl)-2-hydroxypropanoate 

Relevant academic research and scientific papers

Development of a continuous enzymatic process for the preparation of (R)-3-(4-fluorophenyl)-2-hydroxy propionic acid

While many methods have been reported for the synthesis of chiral 2-hydroxy acids, few of them have proven to be reliable toward the synthesis of the title compound in terms of overall yield and enantioselectivity. Herein we describe a continuous enzymatic process for an efficient synthesis of (R)-3-(4-fluorophenyl)-2-hydroxy propionic acid at multikilogram scale with a high space-time yield (560 g/(L·d)) using a membrane reactor. The product was generated in excellent enantiomeric excess (ee > 99.9%) and good overall yield (68-72%).

Fluorinated tropane alkaloids generated by directed biosynthesis in transformed root cultures of Datura stramonium

2′-, 3′- and 4′-Fluorophenyl-(RS)-lactic acids were administered to transformed root cultures of Datura stramonium to determine their abilities as substrates for incorporation into the phenyllactoyl and tropoyl ester moieties of the tropane alkaloids, littorine and hyoscyamine respectively. In the event, all of the fluorinated phenyllactates generated the corresponding fluorinated littorine and hyoscyamine analogues. The efficiency of conversion for the isomerisation of the fluorinated littorines (F-lit) to fluorinated hyoscyamines was 3′-F-lit > 4′-F-lit ? 2′-F-lit.

ANTHELMINTIC DEPSIPEPTIDE COMPOUNDS

The present invention provides cyclic depsipeptide compounds of formula (I) wherein the stereochemical configuration of at least one carbon atom bearing the groups Cy1, Cy2, R1, R2, R3, R4, Ra and Rb is inverted compared with the naturally occurring cyclic depsipeptide PF1022A. The invention also provides compositions comprising the compounds that are effective against parasites that harm animals. The compounds and compositions may be used for combating parasites in or on mammals and birds. The invention also provides for an improved method for eradicating, controlling and preventing parasite infestation in birds and mammals.

ANTHELMINTIC DEPSIPEPTIDE COMPOUNDS

The present invention provides cyclic depsipeptide compounds of formula (I) and compositions comprising the compounds that are effective against parasites that harm animals. The compounds and compositions may be used for combating parasites in or on mammals and birds. The invention also provides for an improved method for eradicating, controlling and preventing parasite infestation in birds and mammals.

SERINE/THREONINE KINASE INHIBITORS

Compounds of Formula I or a stereoisomer, tautomer or pharmaceutically acceptable salt thereof are provided, which are useful for the treatment of diseases. Methods of using compounds of Formula I or a stereoisomer, tautomer or pharmaceutically acceptable salt thereof, for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such diseases, or associated pathological conditions are disclosed.

AMINOPYRIDINE DERIVATIVES AS KALLIKREIN INHIBITORS

The present invention provides compounds of formula (I): compositions comprising such compounds; the use of such compounds in therapy (such as asthma or COPD); and methods of treating patients with such compounds; wherein R1 - R10 and A1 are as defined herein.

Enantioselective hydrogenation of α-aryloxy and α-alkoxy α,β-unsaturated carboxylic acids catalyzed by chiral spiro iridium/phosphino-oxazoline complexes

The iridium-catalyzed highly enantioselective hydrogenation of α-aryloxy and α-alkoxy-substituted α,β-unsaturated carboxylic acids was developed. By using chiral spiro phosphino-oxazoline ligands, the hydrogenation proceeded smoothly to produce various α-aryloxy- and α-alkoxy-substituted carboxylic acids with extremely high enantioselectivities (ee up to 99.8%) and reactivities (TON up to 10 000) under mild conditions. The hydrogenation of R-benzyloxy-substituted α,β-unsaturated acids provided an efficient alternative for the synthesis of chiral R-hydroxy acids after an easy deprotection. A mechanism involving a catalytic cycle between IrI and IrIII was proposed on the basis of the coordination model of the unsaturated acids with the iridium metal center. The rationality of the catalytic cycle, with an olefin dihydride complex as the key intermediate, was supported by the deuterium-labeling studies. The X-ray diffraction analysis of the single crystal of catalyst revealed that the rigid and sterically hindered chiral environment created by the spiro phosphino-oxazoline ligands is the essential factor that permits the catalyst to obtain excellent chiral discrimination. A chiral induction model was suggested on the basis of the catalyst structure and the product configuration.

Biocatalytic racemization of aliphatic, arylaliphatic, and aromatic α-hydroxycarboxylic acids

Biocatalytic racemization of a range of aliphatic, (aryl)aliphatic, and aromatic α-hydroxycarboxylic acids was accomplished by using whole resting cells of a range of Lactobacillus spp. The mild (physiological) reaction conditions ensured an essentially "clean" isomerization in the absence of side reactions, such as elimination or decomposition. Whereas straight-chain aliphatic 2-hydroxy-carboxylic acids were racemized with excellent rates (up to 85% relative to lactate), steric hindrance was observed for branched-chain analogues. Good rates were observed for aryl-alkyl derivatives, such as 3-phenyllactic acid (up to 59%) and 4-phenyl-2-hydroxybutanoic acid (up to 47%). In addition, also mandelate and its o-chloro analogue were accepted at a fair rate (45%). This biocatalytic racemization represents an important tool for the deracemization of a number of pharmaceutically important building blocks.

Highly enantioselective stereo-inverting sec-alkylsulfatase activity of hyperthermophilic Archaea

rac-sec-Alkyl sulfate esters 1a-8a were resolved in low to excellent enantioselectivities with E-values up to > 200 using whole cells of aerobically-grown hyperthermophilic sulfur-metabolizers, such as Sulfolobus solfataricus DSM 1617, Sulfolobus shibatae DSM 5389 and, most notably, Sulfolobus acidocaldarius DSM 639. Significantly enhanced selectivities were obtained using cells grown on sucrose-enriched Brock-medium. The stereochemical course of this biohydrolysis was shown to proceed with strict inversion of configuration, thus the preferred (R)-enantiomers were converted into the corresponding (S)-sec-alcohols to furnish a homochiral product mixture. The Royal Society of Chemistry 2005.

AMINO ACID DERIVATIVE

The present invention relates to an amino acid derivative having an angiotensin I-converting enzyme inhibition activity, a vasopressin antagonism and an atrial natriuretic peptide hydrolase inhibition activity.This amino acid derivative is represented by the following general formula (I): STR1 wherein R 1 represents a hydrogen atom or an acyl group; R 2 represents a hydrogen atom, a lower alkyl group, a cycloalkyl group, an ary group which may have a substituent, a heteroaryl group which may have a substituent, an arylalkyl group which may have a substituent or a heteroarylalkyl group which may have a substituent;m and n represent each independently an integer of 0, 1 or 2 and J represents a cyclic group having an angiotensin I-converting enzyme inhibition activity.