65369-22-4

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 44, p. 3292, 1979 DOI: 10.1021/jo01333a003

InChI:InChI=1/C7H8O3S/c1-9-6-4-11-3-5(6)7(8)10-2/h3-4H,1-2H3

Upstream product

• 64269-79-0 Carbonyldiimidazole 
• 71050-40-3 4-methoxy-3-thiophenecarboxylic acid 
• 186581-53-3 diazomethane 
• 78071-37-1 4-bromo-3-thiophenecarboxylic acid methyl ester 
• 124-41-4 sodium methylate 
• 22097-91-2 methyl 2,5-dihydro-4-methoxythiophene-3-carboxylate 

Downstream Products

• 71050-40-3 4-methoxy-3-thiophenecarboxylic acid 
• 125605-39-2 4-methoxythiophene-3-carbohydrazide 

Relevant academic research and scientific papers

Synthesis and biological activity of various derivatives of a novel class of potent, selective, and orally active prostaglandin D2 receptor antagonists. 2. 6,6-dimethylbicyclo[3.1.1]heptane derivatives

In an earlier paper, we reported that novel prostaglandin D2 (PGD2) receptor antagonists having the bicyclo[2.2.1]heptane ring system as a prostaglandin skeleton were a potent new class of antiallergic agents and suppressed various allergic inflammatory responses such as those observed in conjunctivitis and asthma models. In the present study, we synthesized PGD2 receptor antagonists having the 6,6-dimethylbicyclo [3.1.1]heptane ring system. These derivatives have the amide moiety, in contrast to those with the bicyclo[2.2.1]heptane ring system, which have the sulfonamide group. The derivatives having the 6,6-dimethylbicyclo[3.1.1]heptane ring also exhibited strong activity in PGD2 receptor binding and cAMP formation assays. In in vivo assays such as allergic rhinitis, conjunctivitis, and asthma models, these series of derivatives showed excellent pharmacological profiles. In particular, compound 45 also effectively suppressed eosinophil infiltration in allergic rhinitis and asthma models. This compound (45, S-5751) is now being developed as a promising alternative antiallergic drug candidate.

Organic compounds and their use as pharmaceuticals

A pharmaceutical compound of the formula STR1 in which R1, R2 and R3 independently are hydrogen, hydroxy, halo, nitro, amino, C2-5 acylamino, C1-4 alkyl, --CHO, --CH2 OH, --CH2 OC1-4 alkyl, --COOH, --COC1-3 alkyl, --CH(OH)C1-3 alkyl, C1-4 alkoxy, C2-4 alkenyloxy, C1-4 alkylthio, C1-4 alkylsulphinyl, C1-4 alkylsulphonyl, N-substituted heterocyclyl, optionally substituted phenyl, optionally substituted phenylthio, optionally substituted phenylsulphinyl, optionally substituted phenylsulphonyl or optionally substituted phenylsulphonamido, or R1 and R2 together form a C3-5 alkylene bridge; provided that at least one of R2 and R3 is C1-4 alkoxy or C2-4 alkenyloxy; and X is (i) --(CH2)n N(R4)2 where each R4 independently is C1-4 alkyl, C2-4 alkenyl or optionally substituted C6 H5 CH2 --, and n is 1, 2 or 3, or (ii) a 5- to 8-membered alicyclic group containing one or two nitrogen atoms and directly attached to the amido nitrogen or attached by a C1-3 alkylene chain; and salts and esters thereof.

Hypoglycemic 5-substituted oxazolidine-2,4-diones

Hypoglycemic 5-furyl and 5-thienyl derivatives of oxazolidine-2,4-dione and the pharmaceutically-acceptable salts thereof; certain 3-acylated derivatives thereof; and intermediates useful in the preparation of said compounds.

Thiophene compounds and their manufacture

New thiophene compounds and a new process for the manufacture of thiophene compounds by dehydrogenating dihydrothiophene with certain halogen compounds. The products are starting materials for the manufacture of pharmaceuticals, dyes and plant protection agents and, in particular, for the manufacture of additives to foodstuffs, feeds, beverages and pharmaceuticals.

Aromatization of Dihydrothiophenes. Thiophenesaccharin: A Sweet Surprise

Sulfuryl chloride has been shown to be highly effective in the dehydrogenation of 3,4-disubstituted-2,5-dihydrothiophenes and 2,3-disubstituted-4,5-dihydrothiophenes, in which the 3,4 and 2,3 substitutents are part of a β-keto carbonyl functionality or it