208993-91-3Relevant articles and documents
A scaleable synthesis of fiduxosin
Haight, Anthony R.,Bailey, Anne E.,Baker, William S.,Cain, Michael H.,Copp, Richard R.,Demattei, John A.,Ford, Kelley L.,Henry, Rodger F.,Hsu, Margaret C.,Keyes, Robert F.,King, Steven A.,McLaughlin, Maureen A.,Melcher, Laura M.,Nadler, William R.,Oliver, Patricia A.,Parekh, Shyamal I.,Patel, Hemant H.,Seif, Louis S.,Staeger, Mike A.,Wayne, Gregory S.,Wittenberger, Steven J.,Zhang, Weijiang
supporting information, p. 897 - 902 (2013/09/03)
Fiduxosin (1) has been under development at Abbott Laboratories for the treatment of benign prostatic hyperplasia. A convergent strategy required methodologies for preparation of an enantiomerically pure 3,4-cis-disubstituted pyrrolidine and a 2,3,5-trisubstituted thienopyrazine in a regiospecific manner. A [3+2] cycloaddition of an enantiopure azomethine ylide followed by a diastereoselective crystallization was employed to prepare the benzopyranopyrrolidine in high diastereomeric and enantiomeric purity. Conditions for reduction of an O-aryl lactone susceptible to epimerization were developed, and cyclization of the alcohol/phenol to the ether was accomplished in high yield. The thienopyrazine was prepared by condensation of methyl thioglycolate and a regiospecifically prepared 2-bromo-3-cyano-5-phenylpyrazine. Conditions for effective halogen substitutive deamination to prepare regiospecific trisubstituted pyrazines will be described.
Benzopyranopyrrole and benzopyranopyridine α-1 adenergic compounds
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, (2008/06/13)
The present invention relates to a compound of the formula STR1 and the pharmaceutically acceptable salts thereof wherein W is a bicyclic heterocyclic ring system. The compounds are α-1 adrenergic antagonists and are useful in the treatment of BPH; also disclosed are α-1 antagonist compositions and a method for antagonizing α-1 adrenoreceptors and tr
