272130-24-2Relevant 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
, p. 897 - 902 (2004)
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.
3-phenylpyrrolidine alpha-1 adrenergic compounds
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, (2008/06/13)
Compounds having the formula are alpha 1 adrenoreceptor antagonists. Processes for making these compounds, synthetic intermediates employed in these processes and a method for inhibiting alpha 1 adrenoreceptors and treating benign prostatic hyperplasia (also called benign prostatic hypertrophy or BPH) and other urological diseases such as BOO (bladder outlet obstruction), neurogenic bladder and gynecological syndromes such as dysmenorrhea are disclosed.
