Patents Assigned to MediChem Research, Inc.
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Patent number: 5948918Abstract: Substantially purified antiviral biflavanoids robustaflavone, hinokiflavone, amentoflavone, agathisflavone, volkensiflavone, morelloflavone, rhusflavanone, succedaneaflavanone, GB-1a, and GB-2a are provided. Antiviral biflavanoid derivatives and salt forms thereof, e.g., robustaflavone tetrasulfate potassium salt, and methods for preparing the same are also disclosed. Pharmaceutical compositions which include the antiviral biflavanoids, derivatives or salts thereof are also provided. Also disclosed is an improved method for obtaining substantially pure robustaflavone from plant material. The biflavanoid compounds, derivatives or salts thereof of the invention may be used in a method for treating and/or preventing viral infections caused by viral agents such as influenza, e.g., influenza A and B; hepatitis, e.g., hepatitis B; human immunodeficiency virus, e.g., HIV-1; Herpes viruses (HSV-1 and HSV-2); Varicella Zoster virus (VZV); and measles.Type: GrantFiled: April 14, 1998Date of Patent: September 7, 1999Assignee: MediChem Research, Inc.Inventors: Yuh-Meei Lin, Michael T. Flavin, Ralph Schure, David E. Zembower, Gen-Xian Zhao
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Patent number: 5874577Abstract: Unprotected adenine, 6-chloropurine, 2,6-diaminopurine, and 2-amino-6-chloropurine have been directly coupled with 2-(diethoxyphosphonomethoxy)ethanol under a disclosed method to provide acyclic phosphonate nucleotide analogues which are intermediates for antiviral agents such as 9-?2-(phosphonomethoxy)ethyl!adenine (PMEA) and its analogues having a structure of formula I: ##STR1## wherein Z represents N or CH; R.sub.1 represents hydrogen, alkyl, aryl, or arylalkyl; R.sub.2 and R.sub.3 are independently selected from H, OH, halo, NH.sub.2, C.sub.6 H.sub.5 CH.sub.2 O, or R.sub.4 R.sub.5 N wherein R.sub.4 and R.sub.5 are independently selected from alkyl, aryl, or arylalkyl.Type: GrantFiled: April 2, 1997Date of Patent: February 23, 1999Assignee: MediChem Research, Inc.Inventors: Wei Chen, Michael T. Flavin, Ze-Qi Xu
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Patent number: 5852198Abstract: Wittig-type reagents and methods of preparation and use thereof for preparing .alpha.,.beta.-unsaturated phosphonate esters from aldehydes and ketones are disclosed. The Wittig-type reagents have the following formulae: ##STR1## wherein X represents triflate, halide, BF.sub.4, SbF.sub.6, or ClO.sub.4 ; R.sub.1 represents alkyl, aryl or arylalkyl; and R.sub.2 represents alkyl, aryl or arylalkyl, provided that R.sub.1 and R.sub.2 not represent phenyl at the same time. The Wittig reagent diethyl phosphono-methylidenetriphenylphosphorane (1b) has been successfully synthesized for the first time via its phosphonium triflate salt (4a), by treating diethyl phosphonomethyltriflate with triphenylphosphine according to the disclosed method. The procedure has been applied to the synthesis of other new Wittig-type reagents such as phosphoranes and phosphonium salts. The new Wittig reagents thus synthesized were treated with various aldehydes and an activated ketone, affording the corresponding .alpha.,.beta.Type: GrantFiled: April 2, 1997Date of Patent: December 22, 1998Assignee: Medichem Research, Inc.Inventors: Yibo Xu, Michael T. Flavin
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Patent number: 5773462Abstract: Substantially purified antiviral biflavanoids robustaflavone, hinokiflavone, amentoflavone, agathisflavone, volkensiflavone, morelloflavone, rhusflavanone, succedaneaflavanone, GB-1a, and GB-2a are provided. Antiviral biflavanoid derivatives and salt forms thereof, e.g., robustaflavone tetrasulfate potassium salt, and methods for preparing the same are also disclosed. Pharmaceutical compositions which include the antiviral biflavanoids, derivatives or salts thereof are also provided. Also disclosed is an improved method for obtaining substantially pure robustaflavone from plant material. The biflavanoid compounds, derivatives or salts thereof of the invention may be used in a method for treating and/or preventing viral infections caused by viral agents such as influenza, e.g., influenza A and B; hepatitis, e.g., hepatitis B; human immunodeficiency virus, e.g., HIV-1; Herpes viruses (HSV-1 and HSV-2); Varicella Zoster virus (VZV); and measles.Type: GrantFiled: June 21, 1996Date of Patent: June 30, 1998Assignee: MediChem Research, Inc.Inventors: Yuh-Meei Lin, Michael T. Flavin, Ralph Schure, David E. Zembower, Gen-Xian Zhao
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Patent number: 5504111Abstract: This invention relates to methods for treating Adult Respiratory Distress Syndrome (ARDS) which involves the administration of 2,3-alkylcarbonyloxybenzoic acid and salts thereof wherein the alkyl group has 2-18 carbon atoms.Type: GrantFiled: December 30, 1994Date of Patent: April 2, 1996Assignee: Medichem Research, Inc.Inventors: Michael T. Flavin, Deanna J. Nelson, Julian F. Borgia, deceased, Gary Jesmok
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Patent number: 5489697Abstract: A method for preparing (.+-.)-calanolide A, 1, a potent HIV reverse transcriptase inhibitor, from chromene 4 is provided. Useful intermediates for preparing (.+-.)-calanolide A and its derivatives are also provided.According to the disclosed method, chromene 4 intermediate was reacted with acetaldehyde diethyl acetal in the presence of an acid catalyst with heating to produce chromanone 7. Reduction of chromene 7 with sodium borohydride, in the presence of cerium trichloride, produced (.+-.)-calanolide A, which was purified chromatographically.Type: GrantFiled: August 3, 1994Date of Patent: February 6, 1996Assignee: MediChem Research, Inc.Inventors: William A. Boulanger, Michael T. Flavin, Alla Kucherenko, Abram K. Sheynkman