Abstract: The present invention relates to methods for preparing 2,2-dimethyl-5-acyloxy-10-propyl-2H,8H-benzo[1,2-b:3,4-b′]dipyran-8-one (5) and 2,2-dimethyl-5-hydroxy-10-propyl-2H,8H-benzo[1,2-b:3,4-b′]dipyran-8-one (6) and their use as intermediates for the synthesis of antiviral calanolide compounds. For example, Fries rearrangement on compound 5 or Friedel-Crafts reaction on 6, yields intermediate 2,2-dimethyl-5-hydroxy-6-propionyl-10-propyl-2H,8H-benzo[1,2-b:3,4-b′]dipyran-8-one (4), which, in turn, can be converted to (+)-calanolide A and (−)-calanolide B. The coupling of compound 6 with the appropriate chiral molecule under Mitsunobu or nucleophilic displacement leads to the asymmetric synthesis of antiviral calanolide compounds.
Type:
Grant
Filed:
April 25, 2000
Date of Patent:
April 9, 2002
Assignee:
Sarawak Medichem Pharmaceuticals, Inc.
Inventors:
Ze-Qi Xu, Hongwei Yuan, Jennifer Crabb, Raghu Samy, Ailing Li, Hua Cao
Abstract: This invention provides a series of substituted propanamines useful as tachykinin receptor antagonists. This invention also provides methods employing these substituted propanamines as well as pharmaceutical formulations comprising these compounds.
Type:
Grant
Filed:
January 27, 2000
Date of Patent:
January 15, 2002
Assignee:
Eli Lilly and Company
Inventors:
James E Fritz, Philip A Hipskind, Stephen W Kaldor, Karen L Lobb, James A Nixon
Abstract: A process for the preparation of the phosphonium compound of formula (1), which comprises reacting N-phenylpyrrolidinone (II), with pyridinium bromide perbromide, in the presence of a tertiary organic base and a suitable lewis acid and then treating the resultant bromo derivative (III) with the phosphine (IV, R1R2R1P) and the use of compound (I) when so prepared for the preparation of the glycine antagonist.
Type:
Grant
Filed:
September 7, 1999
Date of Patent:
May 29, 2001
Assignee:
Glaxo Wellcome SpA
Inventors:
Simon Charles Dolan, Paolo Maragni, Alcide Perboni
Abstract: The invention relates to a compound of formula (I):
wherein:
A represents an optionally substituted benzene ring,
B represents an imidazoline ring of formula (Ia) or (Ib):
and medicinal products containing the same/are useful in treating or in preventing depression, obesity, panic attacks, anxiety, obsessive-compulsive disorders, cognitive disorders, phobias, impulsive disorders associated with the abuse of drugs and withdrawal therefrom, sexual dysfunctions, and Parkinson's disease.
Type:
Grant
Filed:
December 17, 1999
Date of Patent:
January 9, 2001
Assignee:
Adir et Compagnie
Inventors:
Alex Cordi, Mark Millan, Adrian Newman-Tancredi, Mauricette Brocco