Patents by Inventor Milton R. Smith, III
Milton R. Smith, III 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).
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Patent number: 10077278Abstract: The disclosure is directed to diboron compounds, related methods of making, and related intermediate boron and diboron compounds used to make the same. The diboron compounds can be used as reagents to prepare chemical intermediates that are used in pharmaceutical, agrochemical, and specialty electronics industries. The disclosed processes and compounds provide simplified synthetic paths that significantly reduce steps, improve scalability, and minimize costs for producing the diboron reagents.Type: GrantFiled: September 29, 2015Date of Patent: September 18, 2018Assignee: BOARD OF TRUSTEES OF MICHIGAN STATE UNIVERSITYInventors: Milton R. Smith, III, Robert E. Maleczka, Jr.
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Publication number: 20180051042Abstract: The disclosure relates to methods for forming at least partially saturated cyclic and heterocyclic borylated hydrocarbons, as well as related compounds, which can be precursor compounds in the synthesis of any of a variety of pharmaceutical or medicinal compounds with a desired structure and/or stereochemistry for drug synthesis or drug candidate evaluation. The methods generally include reduction of an unsaturated cyclic or heterocyclic borylated hydrocarbon having a boron-containing substituent at an sp2-carbon, where such reduction converts the sp2-carbon to an sp3-carbon at the point of attachment of the boron-containing substituent. The methods can exhibit a selectivity for syn-addition during reduction, which can provide stereospecific products, such as when the unsaturated cyclic or heterocyclic reactant is multiply substituted with boron groups and/or other functional groups.Type: ApplicationFiled: August 22, 2017Publication date: February 22, 2018Inventors: Milton R. Smith, III, Timothy M. Shannon, Robert E. Maleczka, JR., Ryan M. Fornwald
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Publication number: 20160090390Abstract: The disclosure is directed to diboron compounds, related methods of making, and related intermediate boron and diboron compounds used to make the same. The diboron compounds can be used as reagents to prepare chemical intermediates that are used in pharmaceutical, agrochemical, and specialty electronics industries. The disclosed processes and compounds provide simplified synthetic paths that significantly reduce steps, improve scalability, and minimize costs for producing the diboron reagents.Type: ApplicationFiled: September 29, 2015Publication date: March 31, 2016Inventors: Milton R. Smith, III, Robert E. Maleczka, JR.
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Publication number: 20150065743Abstract: Methods for the selective borylation of arenes, including arenes substituted with an electron-withdrawing group (e.g., 1-chloro-3-fluoro-2-substituted benzenes) are provided. The methods can be used, in some embodiments, to efficiently and regioselectively prepare borylated arenes without the need for expensive cryogenic reaction conditions.Type: ApplicationFiled: September 5, 2014Publication date: March 5, 2015Inventors: Milton R. Smith, III, Robert E. Maleczka, JR., Hao Li, Chathurika Jayasundara, Jossian Oppenheimer, Dmitrijs Sabasovs
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Patent number: 8927682Abstract: Poly(glycolide) polymers are disclosed. The polymers generally include a polymerized alkynyl-substituted glycolide having a polymer backbone with one or more alkynyl groups appended thereto. The alkynyl groups provide reactive sites for further functionalization of the polymer, for example by reaction with azide derivatives (e.g., azide-substituted organic compounds). Alkynyl and azide groups react via the “click” chemistry mechanism to form functional groups covalently bonded to the polymer via a triazole link. The polymers are biodegradable and can be used to deliver drugs or other therapeutic substances (e.g., large biomolecules such as single strand RNA) at targeted locations in a patient's body and/or at controlled release rates.Type: GrantFiled: August 25, 2008Date of Patent: January 6, 2015Assignee: Board of Trustees of Michigan State UniversityInventors: Gregory L. Baker, Milton R. Smith, III, Xuwei Jiang, Erin B. Vogel
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Patent number: 8394914Abstract: Poly(glycolide) polymers are disclosed. The polymers generally include a glycolide-based polymer backbone that includes one or more functional groups such as alkynyl groups, hydrophilic organic triazole groups, hydrophobic organic triazole groups (also including amphiphilic organic triazole groups), di-triazole organic crosslinking groups, and triazole-substituted drug derivatives. The alkynyl groups provide reactive sites for further functionalization of the polymer, for example by reaction with azide derivatives. The polymers can further encapsulate a drug for delivery to a patient (i.e., as compared to drug derivatives that are covalently attached to the polymer). The polymers can be in the form of thermodynamically stable unimolecular micelles or crosslinked nanoparticles. The polymer compositions are completely biodegradable and hold great potential for use in biomedical applications.Type: GrantFiled: July 22, 2009Date of Patent: March 12, 2013Assignee: Board of Trustees of Michigan State UniversityInventors: Gregory L. Baker, Milton R. Smith, III, Erin Vogel
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Patent number: 7923528Abstract: A homopolymer of 1,4-benzodioxepin-3-cyclohexyl-2,5-dione with a Tg of 120° C. Copolymers are also described. The polymers are useful for surgical and other applications where biodegradability is important.Type: GrantFiled: October 30, 2007Date of Patent: April 12, 2011Assignee: Board of Trustees of Michigan State UniversityInventors: Gregory L. Baker, Feng Jing, Milton R. Smith, III
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Patent number: 7709596Abstract: Cyclic alkyl, particularly cyclohexyl, substituted glycolides and polylactides are described. The polylactides have a high glass transition temperature and improved clarity.Type: GrantFiled: August 24, 2009Date of Patent: May 4, 2010Assignee: Board of Trustees of Michigan State UniversityInventors: Gregory L. Baker, Feng Jing, Milton R. Smith, III
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Patent number: 7709654Abstract: Process for the preparation of oxazole, imidazole, and pyraxole boryl compounds. The compounds are intermediates to functionalized compounds, both natural and synthetic which are cytotoxic, anticancer and antiviral agents.Type: GrantFiled: September 11, 2007Date of Patent: May 4, 2010Assignee: Board of Trustees of Michigan State UniversityInventors: Milton R. Smith, III, Robert E. Maleczka, Jr., Venkata A. Kallepalli, Edith Onyeozili
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Publication number: 20100041902Abstract: Cyclic alkyl, particularly cyclohexyl, substituted glycolides and polylactides are described. The polylactides have a high glass transition temperature and improved clarity.Type: ApplicationFiled: August 24, 2009Publication date: February 18, 2010Applicant: Board of Trustees of Michigan State UniversityInventors: Gregory L. Baker, Feng Jing, Milton R. Smith, III
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Publication number: 20090325292Abstract: Poly(glycolide) polymers are disclosed. The polymers generally include a glycolide-based polymer backbone that includes one or more functional groups such as alkynyl groups, hydrophilic organic triazole groups, hydrophobic organic triazole groups (also including amphiphilic organic triazole groups), di-triazole organic crosslinking groups, and triazole-substituted drug derivatives. The alkynyl groups provide reactive sites for further functionalization of the polymer, for example by reaction with azide derivatives. The polymers can further encapsulate a drug for delivery to a patient (i.e., as compared to drug derivatives that are covalently attached to the polymer). The polymers can be in the form of thermodynamically stable unimolecular micelles or crosslinked nanoparticles. The polymer compositions are completely biodegradable and hold great potential for use in biomedical applications.Type: ApplicationFiled: July 22, 2009Publication date: December 31, 2009Applicant: Board of Trustees of Michigan State UniversityInventors: Gregory L. Baker, Milton R. Smith, III, Erin Vogel
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Patent number: 7579429Abstract: Cyclic alkyl, particularly cyclohexyl, substituted glycolides and polylactides are described. The polylactides have a high glass transition temperature and improved clarity.Type: GrantFiled: December 15, 2006Date of Patent: August 25, 2009Assignee: Board of Trustees of Michigan State UniversityInventors: Gregory L. Baker, Feng Jing, Milton R. Smith, III
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Patent number: 7514563Abstract: A process for producing cyano substituted arene boranes is described. The compounds are useful intermediates to pharmaceutical compounds using the cyano group as a reactant.Type: GrantFiled: June 8, 2006Date of Patent: April 7, 2009Assignee: Board of Trustees of Michigan State UniversityInventors: Milton R. Smith, III, Robert E. Maleczka, Ghayoor A. Chotana
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Publication number: 20090054619Abstract: Poly(glycolide) polymers are disclosed. The polymers generally include a polymerized alkynyl-substituted glycolide having a polymer backbone with one or more alkynyl groups appended thereto. The alkynyl groups provide reactive sites for further functionalization of the polymer, for example by reaction with azide derivatives (e.g., azide-substituted organic compounds). Alkynyl and azide groups react via the “click” chemistry mechanism to form functional groups covalently bonded to the polymer via a triazole link. The polymers are biodegradable and can be used to deliver drugs or other therapeutic substances (e.g., large biomolecules such as single strand RNA) at targeted locations in a patient's body and/or at controlled release rates.Type: ApplicationFiled: August 25, 2008Publication date: February 26, 2009Applicant: Board of Trustees of Michigan State UniversityInventors: Gregory L. Baker, Milton R. Smith, III, Xuwei Jiang, Erin B. Vogel
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Patent number: 7329769Abstract: A process for producing a ring-substituted arene borane which comprises reacting a ring-substituted arene with an HB organic compound in the presence of a catalytically effective amount of an iridium or rhodium complex with three or more substituents, excluding hydrogen, bonded to the iridium or rhodium and a phosphorus organic ligand, which is at least in part bonded to the iridium or rhodium, to form the ring-substituted arene borane. Also provided are catalytic compounds for catalyzing the process comprising an iridium or rhodium complex with three or substituents, excluding hydrogen, bonded to the iridium or rhodium and optionally, a phosphorus organic ligand, which is at least in part bonded to the iridium or rhodium.Type: GrantFiled: March 29, 2005Date of Patent: February 12, 2008Assignee: Board of Trustees of Michigan State UniversityInventor: Milton R. Smith, III
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Patent number: 7148356Abstract: A process for producing organic substituted aromatic or heteroaromatic compounds including biaryl and biheteroaryl compounds in a two-step reaction. In the first step, the aromatic or heteroaromatic compound is borylated in a reaction comprising a borane or diborane reagent (any boron reagent where the boron reagent contains a B—H, B—B or B—Si bond) and an iridium or rhodium catalytic complex. In the second step, a metal catalyst catalyzes the formation of the organic substituted aromatic or heteroaromatic compound from the borylated compound and an electrophile such as an aryl or organic halide, triflate (OSO2CF3), or nonaflate (OSO2C4F9). The steps in the process can be performed in a single reaction vessel or in separate reaction vessels. The present invention also provides a process for synthesis of complex polyphenylenes starting from halogenated aromatic compounds.Type: GrantFiled: March 14, 2005Date of Patent: December 12, 2006Assignee: Board of Trustees of Michigan State UniversityInventors: Milton R. Smith, III, Robert E. Maleczka
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Patent number: 6958420Abstract: A process is described for synthesizing aminoarylboronic esters of the general formula wherein R, R2, and R3 are each an alkyl, aryl, vinyl, alkoxy, carboxylic esters, amides, or halogen; Ar is any variety of phenyl, naphthyl, anthracyl, heteroaryl; and R1 is alkyl, hydrogen, or aryl. The aminoarylboronic esters are produced via the metal-catalyzed coupling of arylboronic esters of the general formula wherein R and R1 are any non-interfering group and X is chloro, bromo, iodo, triflates, or nonaflates to amines (primary and secondary). In particular, a process is described for the synthesis of the aminoarylboronic esters via a step-wise or tandem process in which one catalytic event is a metal-catalyzed borylation and the other catalytic event is a metal-catalyzed amination.Type: GrantFiled: July 18, 2003Date of Patent: October 25, 2005Assignee: Board of Trustees of Michigan State UniversityInventors: Robert E. Maleczka, Jr., Milton R. Smith, III, Daniel Holmes
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Patent number: 6878830Abstract: A process for producing a ring-substituted arene borane which comprises reacting a ring-substituted arene with an HB organic compound in the presence of a catalytically effective amount of an iridium or rhodium complex with three or more substituents, excluding hydrogen, bonded to the iridium or rhodium and a phosphorus organic ligand, which is at least in part bonded to the iridium or rhodium, to form the ring-substituted arene borane. Also provided are catalytic compounds for catalyzing the process comprising an iridium or rhodium complex with three or substituents, excluding hydrogen, bonded to the iridium or rhodium and optionally, a phosphorus organic ligand, which is at least in part bonded to the iridium or rhodium.Type: GrantFiled: July 12, 2002Date of Patent: April 12, 2005Assignee: Board of Trustees of Michigan State UniversityInventor: Milton R. Smith, III
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Patent number: 6867302Abstract: A process for producing organic substituted aromatic or heteroaromatic compounds including biaryl and biheteroaryl compounds in a two-step reaction. In the first step, the aromatic or heteroaromatic compound is borylated in a reaction comprising a borane or diborane reagent (any boron reagent where the boron reagent contains a B—H, B—B or B—Si bond) and an iridium or rhodium catalytic complex. In the second step, a metal catalyst catalyzes the formation of the organic substituted aromatic or heteroaromatic compound from the borylated compound and an electrophile such as an aryl or organic halide, triflate (OSO2CF3), or nonaflate (OSO2C4F9). The steps in the process can be performed in a single reaction vessel or in separate reaction vessels. The present invention also provides a process for synthesis of complex polyphenylenes starting from halogenated aromatic compounds.Type: GrantFiled: July 12, 2002Date of Patent: March 15, 2005Assignee: Board of Trustees of Michigan State UniversityInventors: Milton R. Smith, III, Robert E. Maleczka
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Patent number: 6828466Abstract: A process to synthesize substituted phenols such as those of the general formula RR′R″Ar(OH) wherein R, R′, and R″ are each independently hydrogen or any group which does not interfere in the process for synthesizing the substituted phenol including, but not limited to, halo, alkyl, alkoxy, carboxylic ester, amine, amide; and Ar is any variety of aryl or hetroaryl by means of oxidation of substituted arylboronic esters is described. In particular, a metal-catalyzed C—H activation/borylation reaction is described, which when followed by direct oxidation in a single or separate reaction vessel affords phenols without the need for any intermediate manipulations. More particularly, a process wherein Ir-catalyzed borylation of arenes using pinacolborane (HBPin) followed by oxidation of the intermediate arylboronic ester by OXONE is described.Type: GrantFiled: July 15, 2003Date of Patent: December 7, 2004Assignee: Board of Trustees of Michigan State UniversityInventors: Robert E. Maleczka, Jr., Milton R. Smith, III, Daniel Holmes, Feng Shi