Suprofen

Lipase-catalyzed kinetic resolutions are often practical for the preparation of optically active pharmaceuticals (61). For example, suprofen [40828-46-4] (45), which is a nonsteroidal antiinflamatory dmg, can be resolved by Candida glindracea]i 2Lse in >95% ee at 49% conversion (61). Moreover, hpase-based processes for the resolution of naproxen [22204-53-1] and ibuprofen [15687-27-1] (61) have also been developed. 

QH5F 462-06-6) see Bromperidol Flubendazole Haloperidol Suprofen 4-fluorobenzenesulfonyl chloride (CftH4ClF02S 349-88-2) see Ramatroban 4-fluorobenzonitrile... 

CNNa 143-33-9) see Alclofenac Alpidem Amphetaminil Atorvastatin calcium Azatadine Calcium pantothenate Carnitine Clopidogrel hydrogensulfate Clortermine Dexrazoxane Diclofenac Diloxanide Edetic acid Epinastine hydrochloride Ethosuximide Ethotoin Fenoprofen Ibuprofen Irbesartan Ketoprofen Lonazolac Mephenytoin Mepindolol Montelukast sodium Nabilone Oxymetazoline Paramethadione Pentorex Saquinavir Suprofen Thiamphenicol Tolmetin Trimazosin Zolpidem sodium cyanoborohydride... 

C5H3CIOS 5271-67-0) see Stepronin Suprofen Tenonitrozole Tienilic acid 2-(2-then6ylthio)propionic acid (CjHg03S2 81466-67-3) see Stepronin... 

C4H4S 110-02-1). see Clopidogrel hydrogensulfate Oxitefonium bromide Penthienate methobromide Suprofen 2-Thiophenecarboxylic acid Tiaprofenic acid Ticlopidine Tiemonium iodide Tienilic acid... 

Lin, C.N. and Tsai, S.W., Dynamic kinetic resolution of suprofen thioester via coupled triocty-lamine and lipase catalysis. Biotechnol. Bioeng., 2000, 69, 31-38. 

A side aspect was also demonstrated. If required, the column length and thus the peak capacity can be easily amplified by coupling several enantioselective monolithic columns in series [75]. The actual plate count for a single 10-cm-long monolith was about 7,000 for suprofen and it amounted to about 30,000 for six columns in series. Concomitantly, the resolution was improved from 2.1 to 3.5 while the backpressure of the 60-cm-long column was with 45 bar still quite acceptable (opposed to six bar for a single 10-cm-long column). 

Analysis of non-steroidal anti-inflammatory drugs (ibuprofen, ketoprofen, naproxen, fenoprofen, flurbiproen, and suprofen) Impurity profiling of ketorolac, a chiral nonsteroidal antiinflammatory drug Impurity profiling of a non-steroidal analgesic drug... 

The thiophene ring has also been incorporated into a number of drugs which have diverse toxicities associated with them (Figure 8.24). Ticlopidine, a platelet function inhibitor, is associated with agranulocytosis in patients [25]. Suprofen, a non-... 

Fig. 8.24 Structures of suprofen and ticlopidine, compounds containing a thiophene ring and associated with diverse toxicities in patients.

Asymmetric Hydroformylation of Vinylarenes a-Arylpropanals, the products of asymmetric hydroformylation of vinylarenes, serve as useful intermediates for pharmaceutical drugs. For example, (5)-2-arylpropanals can be oxidized to the corresponding (5)-2-arylpropanoic acids, such as (5)-ibuprofen (Ar = 4-isobutylphe-nyl), (5)-naproxen (Ar = 6-methoxynaphthalen-2-yl), and (5)-suprofen (Ar = 4-(2-thienylcarbonyl)phenyl) (see later in chapter. Scheme 4.4). Styrene is thus one of the most popular substrates used to test new catalyst systems. Representative ligands and their use as Pt or Rh complexes in the asymmetric hydroformylation are summarized in Figure 4.1 and Table 4.1. (See also Scheme 4.3.)... 

Carprofen, flurbiprofen, keto-profen, naproxen, suprofen, benzoin, methylether benzoin CD-NH2, TM-/3... 

Lelievre and Gareil (31) studied chiral separations of nonsteroidal anti-inflammatory drugs (carprofen, flurbiprofen, indoprofen, ketoprofen, naproxen, propafenone, and suprofen) and determined the acidity and inclusion complex formation constants of these chiral compounds with different neutral CDs (/3-CD, HP-/3-CD, DM-/3-CD, TM-/3-CD, and HP-y-CD). In... 

Apart from the salicylates NSAIDs include several classes of weak acids like propionic acid derivatives such as ibuprofen, carprofen, fenbufen, fenoprofen, flurbiprofen, ketorolac, loxoprofen, naproxen, oxaprozin, tiaprofenic acid and suprofen. Phenylbutazone is the most important representative of the pyrazolon derivatives which have a bad reputation for their risk of potentially fatal bone-marrow toxicity. To the acetic acid derivatives belong in-domethacin, diclofenac and sulindac. Sulindac is a pro-drug with less toxicity than indomethacin. The enolic acids include piroxicam, droxicam and tenoxicam. Meloxicam is an analog of piroxicam and has a high selectivity for COX-2. 

An analgesic with greater antiinflammatory and antipyretic activity than Naproxen is a-methyl-4-(2-thienylcarbonyl)benzeneacetic acid, Suprofen.63 This compound has been tested only as a racemic mixture, and any difference in the activity of the enantiomers is not known. Hydroformylation of 4-(2-thienylcarbonyl)styrene (entry 3, Table 4) to the 2-aiylpropanal was achieved in 78% ee for the branched aldehyde [(-t-)-enantiomer in excess], which can be converted to Suprofen by oxidation. 

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