Patents by Inventor Rawle I. Hollingsworth

Rawle I. Hollingsworth has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Publication number: 20020019561
    Abstract: Processes for the preparation of pyrrolidones (7 and 8) and pyrrolidines (9 and 10) from tri-O-acetyl-D-erythro-4-pentulosonic acid esters are described. The compounds are aza sugar analogs of D-ribofuranoside and are intermediates to drugs which regulate nucleoside and nucleic acid synthesis.
    Type: Application
    Filed: September 4, 2001
    Publication date: February 14, 2002
    Applicant: Board of Trustees operating Michigan State University
    Inventor: Rawle I. Hollingsworth
  • Publication number: 20020016448
    Abstract: A process for the preparation of 1,5-dideoxy -1,5-imino hexitols of a hexose sugars from novel hydroxyl protected oxime intermediates. The process includes formation of a lactam which is reduced to the hexitol. The hexitols are useful as drugs.
    Type: Application
    Filed: October 4, 2001
    Publication date: February 7, 2002
    Applicant: Board of Trustees Operating Michigan State University
    Inventors: Rawle I. Hollingsworth, Gabriela Pistia-Brueggeman
  • Publication number: 20020016447
    Abstract: A process for the preparation of 1,5-dideoxy-1,5-imino hexitols of a hexose sugars from novel hydroxyl protected oxime intermediates. The process includes formation of a lactam which is reduced to the hexitol. The hexitols are useful as drugs.
    Type: Application
    Filed: October 4, 2001
    Publication date: February 7, 2002
    Applicant: Board of Trustees operating Michigan State University
    Inventors: Rawle I. Hollingsworth, Gabriela Pistia-Brueggeman
  • Publication number: 20010049443
    Abstract: A process for the preparation of 1,5-dideoxy —1,5-imino hexitols of a hexose sugars from novel hydroxyl protected oxime intermediates. The process includes formation of a lactam which is reduced to the hexitol. The hexitols are useful as drugs.
    Type: Application
    Filed: March 28, 2001
    Publication date: December 6, 2001
    Applicant: Board of Trustees operating Michigan State University
    Inventors: Rawle I. Hollingsworth, Gabriela Pistia-Brueggeman
  • Patent number: 6288238
    Abstract: A process for preparing 5-hydroxymethyl-2-oxazolidinone (1), preferably optically active, in one step from 3,4-boronic acid ester protected 3,4-dihydroxybutyramides (2) is described. The oxazolidinone is important in the pharmaceutical industry especially in the areas of antimicrobials and behavioral disorders.
    Type: Grant
    Filed: September 19, 2000
    Date of Patent: September 11, 2001
    Assignee: Board of Trustees operating Michigan State University
    Inventors: Rawle I. Hollingsworth, Guijun Wang
  • Patent number: 6288244
    Abstract: A process for the preparation of 3,4-dihydroxybutanoic acid (I) and 3-hydroxy-&ggr;-butyrolactone (V) thereof from a 3-leaving group substituted pentose source is described. In particular, the process relates to the synthesis of (R)-3,4-dihydroxybutanoic acid and (R)-3-hydroxy-&ggr;-butyrolactone from a 3-leaving group substituted L-pentose sugars. The process uses a base and a peroxide to convert the pentose source to the chiral 3,4-dihydroxybutanoic acid compound. The chiral 3,4-dihydroxybutanoic acid can be further converted to 3-hydroxy-&ggr;-butyrolactone by acidification. The chiral compound is useful as a chemical intermediate to the synthesis of various drugs and other products.
    Type: Grant
    Filed: September 21, 2000
    Date of Patent: September 11, 2001
    Assignee: Board of Trustees operating Michigan State University
    Inventor: Rawle I. Hollingsworth
  • Patent number: 6288239
    Abstract: A method for preparing protected, preferably chiral, 5-trityloxymethyl-oxazolidinone in one step directly from optically active 3-hydroxy-4-trityloxy butyramide is described. Oxazolidinones are an important class of molecules in the pharmaceutical industry especially in the areas of antimicrobials and behavioral disorders.
    Type: Grant
    Filed: September 19, 2000
    Date of Patent: September 11, 2001
    Assignee: Board of Trustees operating Michigan State University
    Inventors: Rawle I. Hollingsworth, Guijun Wang
  • Patent number: 6274144
    Abstract: A method for depolymerizing polysaccharides containing into saccharide fragments using ozonolysis is described.
    Type: Grant
    Filed: January 21, 2000
    Date of Patent: August 14, 2001
    Assignee: The Brigham and Women's Hospital, Inc.
    Inventors: Ying Wang, Rawle I. Hollingsworth, Dennis L. Kasper
  • Patent number: 6239311
    Abstract: An improved process for the preparation of 3,4-dihydroxybutanoic acid (1) and salts thereof from a D- or L-hexose source is described. The process uses an alkali metal or alkaline earth metal hydroxide and peroxide oxidizing agent to convert the D- or L-hexose source to (1) by maintaining a low concentration of base and oxidizing agent in the reaction mixture at any one time and by maintaining a temperature between about 25° C. and 80° C. Upon acidification of the reaction mixture the 3-hydroxylactone is produced. The compound (1) is useful as a chemical intermediate to naturally occurring fatty acids and is used to prepare 3,4-dihydroxybutanoic acid-gamma-lactone (2) and furanone (3), particularly stereoisomers of these compounds.
    Type: Grant
    Filed: April 24, 2000
    Date of Patent: May 29, 2001
    Assignee: Board of Trustees operating Michigan State University
    Inventor: Rawle I. Hollingsworth
  • Patent number: 6235930
    Abstract: A process for the preparation of 3,4-dihydroxybutanoic acid (I) and 3-hydroxy-&ggr;-butyrolactone (V) thereof from a 3-leaving group substituted pentose source is described. In particular, the process relates to the synthesis of (R)-3,4-dihydroxybutanoic acid and (R)-3-hydroxy-&ggr;-butyrolactone from a 3-leaving group substituted L-pentose sugars. The process uses a base and a peroxide to convert the pentose source to the chiral 3,4-dihydroxybutanoic acid compound. The chiral 3,4-dihydroxybutanoic acid can be further converted to 3-hydroxy-&ggr;-butyrolactone by acidification. The chiral compound is useful as a chemical intermediate to the synthesis of various drugs and other products.
    Type: Grant
    Filed: March 31, 1999
    Date of Patent: May 22, 2001
    Assignee: Board of Trustees operating Michigan State University
    Inventor: Rawle I. Hollingsworth
  • Patent number: 6194529
    Abstract: Polyacetylene compounds and process for the preparation thereof from a chiral dihydroxy amide are described. The compounds preferably have diacyl groups attached to the amide. The compounds are useful for making films which are electrically conductive, near infrared absorbing, polarizing, and have the characteristic optical and other properties of polyacetylenes.
    Type: Grant
    Filed: March 19, 1999
    Date of Patent: February 27, 2001
    Assignee: Board of Trustees operating Michigan State University
    Inventors: Rawle I. Hollingsworth, Guijun Wang
  • Patent number: 6153724
    Abstract: Polymers and processes for synthesizing the polymers from .alpha.,.beta.-unsaturated lactones, particularly 2(5H)-furanone, and amines with side chains. The polymers are used as hydrogels, as polymers that can bind metals and form complexes that are soluble in organic solvents, as polymers useful as flocculants in water purification, as polymers useful on non-fouling surfaces for biofilm suppression, polymers for use on non-thrombogenic surfaces, and polymers with uses as thin conductive films for microchips and other electronic devices. The process is a polymerization reaction involving the cyclic .alpha.,.beta.-unsaturated lactone and a primary amine or primary ammonium compound.
    Type: Grant
    Filed: September 24, 1998
    Date of Patent: November 28, 2000
    Assignee: Board of Trustees Operating Michigan State University
    Inventor: Rawle I. Hollingsworth
  • Patent number: 6114566
    Abstract: Novel 4-cyano-3-hydroxybutanoyl hydrazides (10), particularly R-chiral intermediates are described. The intermediates are useful in preparing (R)-3-hydroxy-4-trimethylaminobutyric acid (L-carnitine) and R-4-amino-3-hydroxybutyric acid (GABOB) and chiral chemical intermediates which are medically useful.
    Type: Grant
    Filed: May 24, 1999
    Date of Patent: September 5, 2000
    Assignee: Board of Trustees Operating Michigan State University
    Inventors: Rawle I. Hollingsworth, Guijun Wang
  • Patent number: 6084131
    Abstract: A process for the preparation of protected dihydroxypropyl trialkylammonium salts, particularly in chiral form is described. In particular, a process for the preparation of (2,2-dimethyl-1,3-dioxolan-4-ylmethyl)trialkylammonium salts, particularly in chiral form is described. Furthermore, a process is described wherein the (2,2-dimethyl-1,3-dioxolan-4ylmethyl)trialkylammonium salts is a 2,2-dimethyl-1,3-dioxolan-4-ylmethyl trimethylammonium salt, preferably in chiral form. The protected dihydroxypropyl trialkylammonium salts lead to L-carnitine (9) when in chiral form (5).
    Type: Grant
    Filed: May 27, 1999
    Date of Patent: July 4, 2000
    Assignee: Board of Trustees operating Michigan State University
    Inventors: Rawle I. Hollingsworth, Guijun Wang
  • Patent number: 6040464
    Abstract: A process for producing protected 3-amino-1,2-dihydroxypropane acetal, particularly in chiral forms, for use as an intermediate in the preparation of various 3-carbon compounds which are chiral. In particular, the present invention relates to the process for preparation of 3-amino-1,2-dihydroxypropane isopropylidene acetal. The protected 3-amino-1,2-dihydroxypropane acetal is a key intermediate to the preparation of chiral 3-carbon compounds which in turn are intermediates to various pharmaceuticals.
    Type: Grant
    Filed: May 27, 1999
    Date of Patent: March 21, 2000
    Assignee: Board of Trustees operating Michigan State University
    Inventors: Rawle I. Hollingsworth, Guijun Wang
  • Patent number: 6027733
    Abstract: A method for depolymerizing polysaccharides containing into saccharide fragments using ozonolysis is described.
    Type: Grant
    Filed: March 26, 1998
    Date of Patent: February 22, 2000
    Assignee: The Brigham and Women's Hospital, Inc.
    Inventors: Ying Wang, Rawle I. Hollingsworth, Dennis L. Kasper
  • Patent number: 5851807
    Abstract: A process for providing vicinal dimethyl long chain between alkyl groups of organic compounds is described. The process uses intact or disrupted cells of various species of bacteria, particularly Thermoanaerobacter sp., Sarcina sp. and Butyrivibrio sp. The process can be conducted in an aqueous reaction mixture at room temperatures.
    Type: Grant
    Filed: January 17, 1997
    Date of Patent: December 22, 1998
    Assignee: Board of Trustees operating Michigan State University
    Inventors: Rawle I. Hollingsworth, Seunho Jung, Carol A. Mindock
  • Patent number: 5808107
    Abstract: Preparation of 4-hydroxy substituted butyrolactones is described. A process for the preparation of 3-hydroxybutyrolactone, 1,2,4-trihydroxybutane and 3,4-dihydroxy acid methyl ester from malic acid is particularly described. The preparation of 4-hydroxymethyl-4-hydroxybutyric acid -1-methyl ester and 4-hydroxymethyl butyrolactone is particularly described. The compounds are intermediates to various pharmaceutical and agricultural products.
    Type: Grant
    Filed: October 31, 1997
    Date of Patent: September 15, 1998
    Assignee: Board of Trustees operating Michigan State University
    Inventor: Rawle I. Hollingsworth
  • Patent number: 5374773
    Abstract: A process for the preparation of 3,4-dihydroxybutanoic acid (1) and salts thereof from a glucose source containing 1,4-1inked glucose as a substituent is described. The process uses an alkali metal hdyroxide and hydrogen peroxide to convert the glucose source to (1). The compound (1) is useful as a chemical intermediate to naturally occurring fatty acids and is used to prepare 3,4-dihydroxybutanoic acid-gamma-lactone (2) and furanone (3), particularly stereoisomers of these compounds.
    Type: Grant
    Filed: October 27, 1993
    Date of Patent: December 20, 1994
    Assignee: Board of Trustees operating Michigan State University
    Inventor: Rawle I. Hollingsworth
  • Patent number: 5319110
    Abstract: A process for the preparation of 3,4-dihydroxybutanoic acid (1) and salts thereof from a glucose source containing 1,4-linked glucose as a substituent is described. The process uses an alkali metal hdyroxide and hydrogen peroxide to convert the glucose source to (1). The compound (1) is useful as a chemical intermediate to naturally occurring fatty acids and is used to prepare 3,4-dihydroxybutanoic acid-gamma-lactone (2) and furanone (3), particularly stereoisomers of these compounds.
    Type: Grant
    Filed: October 26, 1992
    Date of Patent: June 7, 1994
    Assignee: Board of Trustees operating Michigan State University
    Inventor: Rawle I. Hollingsworth