Nitrogen In The Ring Patents (Class 558/289)
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Patent number: 10544347Abstract: A method for formulating a hydraulic fracturing fluid composition with increased viscosity and resistance to degradation at increased temperature and pressure. The method includes preparing an alkanolamine borate formulation compatible for mixing with a hydraulic fracturing fluid comprising polysaccharides; preparing the hydraulic fracturing fluid comprising polysaccharides; and mixing the alkanolamine borate formulation with the hydraulic fracturing fluid, such that the alkanolamine borate formulation causes crosslinking of the hydraulic fracturing fluid.Type: GrantFiled: October 16, 2017Date of Patent: January 28, 2020Assignee: Saudi Arabian Oil CompanyInventors: B. Raghava Reddy, Feng Liang, Leiming Li
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Patent number: 9328102Abstract: A method of performing a chemical reaction includes reacting a compound selected from the group consisting of an organohalide and an organo-pseudohalide, and a protected organoboronic acid represented by formula (I) in a reaction mixture: R1—B-T??(I); where R1 represents an organic group, T represents a conformationally rigid protecting group, and B represents boron having sp3 hybridization. When unprotected, the corresponding organoboronic acid is unstable by the boronic acid neat stability test. The reaction mixture further includes a base having a pKB of at least 1 and a palladium catalyst. The method further includes forming a cross-coupled product in the reaction mixture.Type: GrantFiled: April 14, 2015Date of Patent: May 3, 2016Assignee: The Board of Trustees of the University of IllinoisInventors: Martin D. Burke, David M. Knapp, Eric P. Gillis
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Patent number: 9194853Abstract: The invention concerns the use of cyclic azaboronates as sensitive materials in sensors for the detection of the presence of peroxides, in particular hydrogen peroxide, in a gaseous environment. It further concerns new cyclic azaboronates, as well as sensors comprising these azaboronates as sensitive materials. Applications for the invention include the following: fight against terrorism, monitoring for security purposes of sites in which peroxides or peroxidable compounds are manufactured, stored, and/or used, monitoring of atmospheric pollution, etc.Type: GrantFiled: October 17, 2011Date of Patent: November 24, 2015Assignee: COMMISSARIAT A L'ENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVESInventors: Thomas Caron, Myriam Bouhadid, Eric Pasquinet, Pierre Montmeat, Francoise Serein-Spirau
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Patent number: 9108990Abstract: This disclosure concerns a protected cyclopropylboronic acid comprising a substituted cyclopropyl group and a boronic ester group having a protecting group. The protecting group is an N-methyliminodiacetic acid (MIDA) group or MIDA-based group.Type: GrantFiled: March 27, 2014Date of Patent: August 18, 2015Assignee: Rigel Pharmaceuticals, Inc.Inventors: Matthew Duncton, Rajinder Singh
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Publication number: 20150119364Abstract: This invention relates to compounds useful for treating fungal infections, more specifically topical treatment of onychomycosis and/or cutaneous fungal infections. This invention is directed to compounds that are active against fungi and have properties that allow the compound, when placed in contact with a patient, to reach the particular part of the skin, nail, hair, claw or hoof infected by the fungus. In particular the present compounds have physiochemical properties that facilitate penetration of the nail plate.Type: ApplicationFiled: November 10, 2014Publication date: April 30, 2015Inventors: Stephen J. BAKER, Tsutomu Akama, Michael Richard Kevin Alley, Stephen J. Benkovic, Michael DiPierro, Vincent S. Hernandez, Karin M. Hold, Isaac Kennedy, Igor Likhotvorik, Weimin Mao, Kirk Maples, Jacob J. Plattner, Fernando Rock, Virginia Sanders, Aaron M. Stemphoski, George Petros Yiannikouros, Siead Zegar, Yong-Kang Zhang, Huchen Zhou
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Publication number: 20150080339Abstract: The present disclosure relates to boron-based 4-hydroxytamoxifen and endoxifen prodrugs and the synthesis of the same. Further, the present disclosure teaches the utilization of the boron-based 4-hydroxytamoxifen and endoxifen prodrugs in a treatment for breast cancer.Type: ApplicationFiled: March 5, 2013Publication date: March 19, 2015Inventors: Guangdi Wang, Shilong Zheng, Quan Jiang, Qiu Zhong, Qiang Zhang
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Publication number: 20140296557Abstract: This disclosure concerns a protected cyclopropylboronic acid comprising a substituted cyclopropyl group and a boronic ester group having a protecting group. The protecting group is an N-methyliminodiacetic acid (MIDA) group or MIDA-based group.Type: ApplicationFiled: March 27, 2014Publication date: October 2, 2014Inventors: Matthew Duncton, Rajinder Singh
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Publication number: 20140275601Abstract: Di- and trivalent protecting groups for organoboronic acids including phenyl boronic acids, benzoxaboroles and benzoxaborins, which are prepared from precursor compounds of formula I: where: R1 is a methyl, ethyl or a —(CH2)n—OH group, where n is 2 or 3; R2 and R3 are independently methyl or ethyl groups; R4 and R5 are independently halogens or hydrogens; R6 and R7 are independently hydrogens, halogens, or nitro groups; and R8 and R9 are independently hydrogens, halogens or nitro groups or R8 and R9 together with a portion of the naphthalene ring form a 5-member ring, where when R1 is —CH2—CH2—OH then the protecting group is a trivalent protecting group. Also provided are protected organoboronic acids including protected phenyl boronic acids, benzoxaboroles and benzoxaborins. Also provides are methods for conducting reactions employing protected organoboronic acids.Type: ApplicationFiled: March 14, 2014Publication date: September 18, 2014Applicant: Wisconsin Alumni Research FoundationInventors: Ronald T. Raines, Brett VanVeller, Matthew Aronoff
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Patent number: 8754251Abstract: Provided are protected cyclopropylboronic acids that include a substituted cyclopropyl group and a boronic ester group having a protecting group. The protecting group is a pinene-derived iminodiacetic acid (PIDA) group or PIDA-based group.Type: GrantFiled: June 6, 2013Date of Patent: June 17, 2014Assignee: Rigel Pharmaceuticals, Inc.Inventors: Matthew Duncton, Martin D. Burke
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Patent number: 8722916Abstract: This disclosure concerns a protected cyclopropylboronic acid comprising a substituted cyclopropyl group and a boronic ester group having a protecting group. The protecting group is an N-methyliminodiacetic acid (MIDA) group or MIDA-based group.Type: GrantFiled: December 1, 2011Date of Patent: May 13, 2014Assignee: Rigel Pharmaceuticals, Inc.Inventors: Matthew Duncton, Rajinder Singh
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Publication number: 20140121182Abstract: The invention provides boronic esters of Formula (I) wherein R is H or methyl, and methods for the preparation and purification thereof.Type: ApplicationFiled: June 21, 2012Publication date: May 1, 2014Applicant: Cephalon, Inc.Inventors: Roger P. Bakale, John P. Mallamo, Renee Caroline Roemmele
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Publication number: 20140094615Abstract: Provided are methods for making and using chiral, non-racemic protected organoboronic acids, including pinene-derived iminodiacetic acid (PIDA) boronates, to direct and enable stereoselective synthesis of organic molecules. Also provided are methods for purifying PIDA boronates from solution. Also provided are methods for deprotection of boronic acids from their PIDA ligands. The purification and deprotection methods may be used in conjunction with methods for coupling or otherwise reacting boronic acids. Iterative cycles of deprotection, coupling, and purification can be performed to synthesize chiral, non-racemic compounds. The methods are suitable for use in an automated chemical synthesis process. Also provided is an automated small molecule synthesizer apparatus for performing automated stereoselective synthesis of chiral, non-racemic small molecules using iterative cycles of deprotection, coupling, and purification.Type: ApplicationFiled: April 26, 2012Publication date: April 3, 2014Applicant: The Board of Trustees of the University of IllinoisInventors: Martin D. Burke, Junqi Li, Eric P. Gillis
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Publication number: 20140073785Abstract: Described are methods of forming protected boronic acids that provide in a manner that is straightforward, scalable, and cost-effective a wide variety of building blocks, such as building blocks containing complex and/or pharmaceutically important structures, and/or provide simple or complex protected organoboronic acid building blocks. A first method includes reacting an imino-di-carboxylic acid and an organoboronate salt. A second method includes reacting a N-substituted morpholine dione and an organoboronic acid.Type: ApplicationFiled: September 24, 2013Publication date: March 13, 2014Applicant: The Board of Trustees of the University of IllinoisInventors: Martin D. Burke, Graham R. Dick, David M. Knapp, Eric P. Gillis, Jenna A. Klubnick
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Publication number: 20140057871Abstract: [Problem] To provide a GPR40 activating agent having, as an active ingredient, a novel compound having a GPR40 agonist action, a salt of the compound, a solvate of the salt or the compound, or the like, particularly, an insulin secretagogues and a prophylactic and/or therapeutic agent against diabetes, obesity, or the like. [Means of solving the problem] A compound of Formula (III): (where f is 0 to 2; g is 1 to 4; j is 0 to 3; k is 0 to 2; n is 0 to 2; p is 0 to 4; h is 0 to 3; q1 id 0 to 3; q2 is 0 or 1; r1 is 0 to 2 (with the proviso that q1+q2+r1 is 0 to 5); J1a is —CR11a—, N; J2 is —CR12aR12b—, —CR12c—; T is —CH2—, O, —S(O)i— (i is an integer of 0 to 2) or —NR7—; X is O, S, or —NR7—; ring A?? is a benzene ring, a pyridine ring; ring B? is a benzene ring, a pyridine ring, a pyrimidine ring; and R1 to R14 are specific groups), a salt of the compound, or a solvate of the salt or the compound.Type: ApplicationFiled: April 11, 2012Publication date: February 27, 2014Applicant: MOCHIDA PHARMACEUTICAL CO., LTD.Inventors: Akihiro Okano, Munetaka Ohkouchi, Muneyoshi Makabe
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Publication number: 20130331585Abstract: Provided are protected cyclopropylboronic acids that include a substituted cyclopropyl group and a boronic ester group having a protecting group. The protecting group is a pinene-derived iminodiacetic acid (PIDA) group or PIDA-based group.Type: ApplicationFiled: June 6, 2013Publication date: December 12, 2013Inventors: Matthew Duncton, Michael D. Burke
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Publication number: 20130296573Abstract: A protected organoboronic acid includes a boron having an sp3 hybridization, a conformationally rigid protecting group bonded to the boron, and an organic group bonded to the boron through a boron-carbon bond. A method of performing a chemical reaction includes contacting a protected organoboronic acid with a reagent, the protected organoboronic acid including a boron having an sp3 hybridization, a conformationally rigid protecting group bonded to the boron, and an organic group bonded to the boron through a boron-carbon bond. The organic group is chemically transformed, and the boron is not chemically transformed.Type: ApplicationFiled: October 18, 2012Publication date: November 7, 2013Applicant: The Board of Trustees of the University of IllinoisInventors: Martin D. Burke, Eric P. Gillis, Suk Joong Lee, David M. Knapp, Kaitlyn C. Gray
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Patent number: 8568884Abstract: Disclosed are a compound that emits fluorescence, particularly in its solid state, and is suited to provide a color converting material with various improved performance properties over prior art and a light emitter, a color conversion filter, a color conversion device, and a photoelectric device each containing the compound; particularly a Schiff base type compound of formula (I) and a coloring material, a color conversion layer, a light absorbing layer, a color conversion filter, a light absorbing filter, a color-converting light-emitting device, and a photoelectric device each containing the compound. The definition of the symbols in formula (I) is the same as in the specification.Type: GrantFiled: June 30, 2010Date of Patent: October 29, 2013Assignee: Adeka CorporationInventors: Mitsuhiro Okada, Koichi Shigeno
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Patent number: 8563761Abstract: The present invention relates to boron and aluminum complexes, to the preparation thereof, and to the use thereof for solubilizing ionic compounds. The complexes have one of the following formulae: in which D represents B or Al; R1 represents R, RF, NO2, CN, C(?O)OR, RSO2, or RFSO2; —X1—, —X2—, —X3— and X4 each represent a divalent group >C?O, >C?NC?N, >C?C(C?N)2, >CR2R3 or >SO2; —Y1—, —Y2— and —Y3— each represent a divalent group —O—, >N(C?N), >N(CORF), >N(SO2R4), >NR4, >N(COR4) or >N(SO2RF); R, R2 and R3 each represent H, an alkyl group, an aryl group, an alkylaryl group, an arylalkyl group, an oxaalkyl group or an alkenyl group; R4 represents an alkyl group, an aryl group, an alkylaryl group, a heteroaryl group, an arylalkyl group, an oxaalkyl group, an alkenyl group or an RFCH2— group; RF is a perfluoroalkyl group, a partially fluorinated alkyl group, or a partially or totally fluorinated phenyl group; each of the R?2 and R?3 groups represents R or F.Type: GrantFiled: March 19, 2009Date of Patent: October 22, 2013Assignees: Centre National de la Recherche, Universite de Picardie Jules VerneInventors: Michel Armand, Jean-Marie Tarascon, Nadir Recham, Sylvie Grugeon, Stephane Laruelle, Shanmukaraj Devaraj
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Publication number: 20130243670Abstract: Provided are methods for purifying N-methyliminodiacetic acid (MIDA) boronates from solution. Also provided are methods for deprotection of boronic acids from their MIDA ligands. The purification and deprotection methods can be used in conjunction with methods for coupling or otherwise reacting boronic acids. Iterative cycles of deprotection, coupling, and purification can be performed to synthesize chemical compounds of interest. The methods are suitable for use in an automated chemical synthesis process. Also provided is an automated small molecule synthesizer apparatus for performing automated synthesis of small molecules using iterative cycles of deprotection, coupling, and purification in accordance with methods of the invention.Type: ApplicationFiled: July 22, 2011Publication date: September 19, 2013Inventors: Martin D. Burke, Eric P. Gillis
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Patent number: 8487054Abstract: A polymerization initiator based on boroesters of benzopinacol for curing unsaturated polymers is disclosed. Methods of preparing the benzopinacol boroester initiator and using the initiator in polymerization reactions are additionally disclosed.Type: GrantFiled: June 21, 2012Date of Patent: July 16, 2013Assignee: ELANTAS PDG, Inc.Inventors: Thomas James Murray, David L. Vines
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Patent number: 8349814Abstract: The present invention provide compounds, and pharmaceutical compositions thereof, encompassed by the formulae (I), (II) or (III). The present invention also provides methods for treating an FAAH mediated disease, disorder or condition by administering a therapeutically effective amount of a provided compound of the formulae (I), (II) or (III), or a pharmaceutical composition thereof, to a patient in need thereof. Additionally, the present invention provides methods for inhibiting FAAH in a patient by administering a therapeutically effective amount of a compound of the formulae (I), (II) or (III), or a pharmaceutical composition thereof, to a patient in need thereof.Type: GrantFiled: March 16, 2011Date of Patent: January 8, 2013Assignee: Infinity Pharmaceuticals, Inc.Inventors: Julian Adams, Mark L. Behnke, Alfredo C. Castro, Catherine A. Evans, Louis Grenier, Michael J. Grogan, Tao Liu, Daniel A. Snyder, Thomas T. Tibbitts
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Publication number: 20120329967Abstract: A polymerization initiator based on boroesters of benzopinacol for curing unsaturated polymers is disclosed. Methods of preparing the benzopinacol boroester initiator and using the initiator in polymerization reactions are additionally disclosed.Type: ApplicationFiled: June 21, 2012Publication date: December 27, 2012Applicant: ELANTAS PDG, Inc.Inventors: Thomas James Murray, David L. Vines
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Publication number: 20120142915Abstract: This disclosure concerns a protected cyclopropylboronic acid comprising a substituted cyclopropyl group and a boronic ester group having a protecting group. The protecting group is an N-methyliminodiacetic acid (MIDA) group or MIDA-based group.Type: ApplicationFiled: December 1, 2011Publication date: June 7, 2012Inventors: Matthew Duncton, Rajinder Singh
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Publication number: 20120059184Abstract: A protected organoboronic acid includes a boron having an sp3 hybridization, a conformationally rigid protecting group bonded to the boron, and an organic group bonded to the boron through a boron-carbon bond. A method of performing a chemical reaction includes contacting a protected organoboronic acid with a reagent, the protected organoboronic acid including a boron having an sp3 hybridization, a conformationally rigid protecting group bonded to the boron, and an organic group bonded to the boron through a boron-carbon bond. The organic group is chemically transformed, and the boron is not chemically transformed.Type: ApplicationFiled: July 25, 2011Publication date: March 8, 2012Applicant: The Board of Trustees of the University of IllinoisInventors: Martin D. Burke, Eric P. Gillis, Suk Joong Lee, David M. Knapp, Kaitlyn C. Gray
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Publication number: 20110230440Abstract: The present invention provide compounds, and pharmaceutical compositions thereof, encompassed by the formulae (I), (II) or (III). The present invention also provides methods for treating an FAAH mediated disease, disorder or condition by administering a therapeutically effective amount of a provided compound of the formulae (I), (II) or (III), or a pharmaceutical composition thereof, to a patient in need thereof. Additionally, the present invention provides methods for inhibiting FAAH in a patient by administering a therapeutically effective amount of a compound of the formulae (I), (II) or (III), or a pharmaceutical composition thereof, to a patient in need thereof.Type: ApplicationFiled: March 16, 2011Publication date: September 22, 2011Inventors: Julian Adams, Mark L. Behnke, Alfredo C. Castro, Catherine A. Evans, Louis Grenier, Michael J. Grogan, Tao Liu, Daniel A. Snyder, Thomas T. Tibbitts
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Publication number: 20110201806Abstract: Described are methods of forming protected boronic acids that provide in a manner that is straightforward, scalable, and cost-effective a wide variety of building blocks, such as building blocks containing complex and/or pharmaceutically important structures, and/or provide simple or complex protected organoboronic acid building blocks. A first method includes reacting an imino-di-carboxylic acid and an organoboronate salt. A second method includes reacting a N-substituted morpholine dione and an organoboronic acid.Type: ApplicationFiled: February 18, 2011Publication date: August 18, 2011Inventors: Martin D. Burke, Graham R. Dick, David M. Knapp, Eric P. Gillis, Jenna A. Klubnick
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Publication number: 20110171112Abstract: The present invention relates to boron and aluminum complexes, to the preparation thereof, and to the use thereof for solubilizing ionic compounds. The complexes have one of the following formulae: in which D represents B or Al; R1 represents R, RF, NO2, CN, C(?O)OR, RSO2, or RFSO2; —X1—, —X2—, —X3— and X4 each represent a divalent group >C?O, >C?NC?N, >C?C(C?N)2, >CR2R3 or >SO2; —Y1—, —Y2— and —Y3— each represent a divalent group —O—, >N(C?N), >N(CORF), >N(SO2R4), >NR4, >N(COR4) or >N(SO2RF); R, R2 and R3 each represent H, an alkyl group, an aryl group, an alkylaryl group, an arylalkyl group, an oxaalkyl group or an alkenyl group; R4 represents an alkyl group, an aryl group, an alkylaryl group, a heteroaryl group, an arylalkyl group, an oxaalkyl group, an alkenyl group or an RFCH2— group; RF is a perfluoroalkyl group, a partially fluorinated alkyl group, or a partially or totally fluorinated phenyl group; each of the R?2 and R?3 groups represents R or F.Type: ApplicationFiled: March 19, 2009Publication date: July 14, 2011Inventors: Michel Armand, Jean-Marie Tarascon, Nadir Recham, Sylvie Grugeon, Stephane Laruelle, Shanmukaraj Devaraj
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Patent number: 6630577Abstract: A reagent having the general formula of General Formula I: wherein group Z comprises a spacer selected from an aliphatic chain up to about 6 carbon equivalents in length, an unbranched aliphatic chain of from about 6 to 18 carbon equivalents in length with at least one of an intermediate amide and a disulfide moiety, and a polyethylene glycol chain of from about 3 to 12 carbon equivalents in length; wherein group R is an electrophilic or nucleophilic moiety suitable for reaction of the reagent with a biologically active species; and wherein group Q is one of nothing at all, an amide, a methyl amide, a methylene, an ether, a thioether, a methyl ether, and a methyl thioether moiety. Also, a conjugate, a bioconjugate and a method of conjugating.Type: GrantFiled: June 4, 2001Date of Patent: October 7, 2003Assignee: Prolinx, Inc.Inventors: Mark L. Stolowitz, Guisheng Li, Jean P. Wiley
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Patent number: 6509472Abstract: Prochiral ketones are enantioselectively reduced to chiral secondary alcohols with a compound having the formula I: where, the two R2 groups are identical and are each a substituted or unsubstituted, aryl, alkyl, cycloalkyl or aralkyl group; and R3 is a hydrogen atom or a substituted or unsubstituted, alkyl, aryl, aralkyl or alkoxy group; wherein the substituents on the R2 and R3 groups are substantially non-reactive.Type: GrantFiled: August 30, 2001Date of Patent: January 21, 2003Assignee: Schering CorporationInventor: Richard W. Draper
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Patent number: 6462179Abstract: Reagents suitable for the modification of a bioactive species for the purpose of incorporating one or more phenyldiboronic acid (PDBA) moieties for subsequent conjugation to a different (or the same) bioactive species having one or more pendant boronic compound complexing moieties of the general formula of General Formula I, wherein group R is a reactive electrophilic or nucleophilic moiety suitable for reaction of the PDBA reagent with a bioactive species. Group Z is a spacer selected from a saturated or unsaturated chain up to about 0 to 6 carbon equivalents in length, an unbranched saturated or unsaturated chain of from about 6 to 18 carbon equivalents in length with at least one intermediate amide or disulfide moiety, and a polyethylene glycol chain of from about 3 to 12 carbon equivalents in length. Group Q is a linkage that includes one of amide, ether and thioether moieties.Type: GrantFiled: July 25, 2000Date of Patent: October 8, 2002Assignee: Prolinx, Inc.Inventors: Mark L. Stolowitz, Edward A. Kesicki, Kevin P. Lund, Karin A. Hughes
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Patent number: 6414122Abstract: Embodiments include reagents to modify a bioactive species for incorporating a bifunctional boronic compound complexing moiety for subsequent conjugation to a different or same bioactive species having pendant phenylboronic acid moieties of General Formula I, wherein group R is an electrophilic or nucleophilic moiety suitable for reaction of the putative bifunctional boronic compound complexing reagent with a bioactive species, wherein group R2 is selected from one of H and OH moieties, and wherein group R3 is selected from one of an alkyl and a methylene bearing an electronegative substituent. Group Z is a spacer selected from (CH2)n and CH2O(CH2CH2O)n2, wherein n is an integer of from 1 to 5, and wherein n2 is an integer of from 1 to 4. Group Z2 and Z3 is a spacer and need not be the same.Type: GrantFiled: August 29, 2000Date of Patent: July 2, 2002Assignee: Prolinx, Inc.Inventors: Clarence N. Ahlem, Robert J. Kaiser, Kevin P. Lund, Mark L. Stolowitz
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Publication number: 20020038053Abstract: Prochiral ketones are enantioselectively reduced to chiral secondary alcohols with a compound having the formula I: 1Type: ApplicationFiled: August 30, 2001Publication date: March 28, 2002Inventor: Richard W. Draper
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Patent number: 6355825Abstract: The invention relates to processes for preparing a compound of the formula and the enantiomer of said compound, wherein the benzoic acid moiety is attached at position 6 or 7 of the chroman ring, and R1, R2, and R3 are as defined herein. The invention further relates to intermediates that are useful in the preparation of the compound of formula X above.Type: GrantFiled: March 21, 2001Date of Patent: March 12, 2002Assignee: Pfizer Inc.Inventors: Anthony Piscopio, Joel M. Hawkins, Stephanie Caron, Sarah E. Kelly, Jeffrey W. Raggon, Michael J. Castaldi, Robert W. Dugger, Sally G. Ruggeri
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Patent number: 6248305Abstract: Boron heterocycle steroid mimics are provided that are useful as pharmaceutical agents, particularly in the treatment of estrogen-dependent disorders such as estrogen-dependent cancers. The compounds are also useful in diagnostic techniques such as magnetic resonance imaging (MRI) and magnetic resonance spectroscopy (MRS), in boron neutron capture therapy, and in fluorescence emission-based modalities. Pharmaceutical formulations and methods of using the novel compounds are provided as well.Type: GrantFiled: January 25, 2000Date of Patent: June 19, 2001Assignee: SRI InternationalInventor: Michael P. Groziak
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Patent number: 6197967Abstract: Compounds of the formula (I) are prepared by reacting a compound of the formula (V) with a compound of the formula (X) and hydrolyzing the product; or converting the compound of the formula (V) into the hydrazide, and cyclizing and hydrolyzing the latter to give the oxadiazole. para-Oxadiazolylphenylboronic acids are valuable precursors for active ingredients.Type: GrantFiled: December 13, 1999Date of Patent: March 6, 2001Assignee: Clariant GmbHInventors: Frank Vollmueller, Steffen Haber, Andreas Meudt, Antje Noerenberg, Stefan Scherer
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Patent number: 6156884Abstract: Reagents suitable for the modification of a bioactive species for the purpose of incorporating a bifunctional boronic compound complexing moiety for subsequent conjugation to a different (or the same) bioactive species having pendant phenylboronic acid moieties of General Formula 1, ##STR1## wherein group R is an electrophilic or nucleophilic moiety suitable for reaction of the putative bifunctional boronic compound complexing reagent with a bioactive species, wherein group R.sub.2 is selected from one of H and OH moieties, and wherein group R.sub.3 is selected from one of an alkyl and a methylene bearing an electronegative substituent. Group Z is a spacer selected from (CH.sub.2).sub.n and CH.sub.2 O(CH.sub.2 CH.sub.2 O).sub.n.sbsb.2, wherein n is an integer of from 1 to 5, and wherein n.sub.2 is an integer of from 1 to 4. Each of group Z.sub.2 and Z.sub.3 is a spacer selected from CH.sub.2 Ar, CH.sub.2 CONHCH.sub.2 Ar, CH.sub.2 CONH(CH.sub.2).sub.n.sbsb.3 CO--NHCH.sub.2 Ar, and (CH.sub.2).sub.n.sbsb.Type: GrantFiled: December 29, 1998Date of Patent: December 5, 2000Assignee: Prolinx, Inc.Inventors: Clarence N. Ahlem, Robert J. Kaiser, Kevin P. Lund, Mark L. Stolowitz
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Patent number: 6083936Abstract: Boron heterocycle steroid mimics are provided that are useful as pharmaceutical agents, particularly in the treatment of estrogen-dependent disorders such as estrogen-dependent cancers. The compounds are also useful in diagnostic techniques such as magnetic resonance imaging (MRI) and magnetic resonance spectroscopy (MRS), in boron neutron capture therapy, and in fluorescence emission-based modalities. Pharmaceutical formulations and methods of using the novel compounds are provided as well.Type: GrantFiled: January 25, 1999Date of Patent: July 4, 2000Assignee: SRI InternationalInventor: Michael P. Groziak
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Patent number: 6075126Abstract: Boron compound complexing reagents, boron compound complexes, and methods of synthesizing these reagents and complexes are disclosed. These reagents and complexes include those shown in General Formula CIII, General Formula CIV, and General Formula CVI. In one embodiment, the reagents of General Formula CIII may be used to produce, after condensation with a bioactive species (BAS), the reagent of General Formula CIV. The reagent of General Formula CIV may be used to form a complex with a boron compound, such as a complex shown in General Formula CVI.Type: GrantFiled: August 21, 1998Date of Patent: June 13, 2000Assignee: Prolinx, Inc.Inventors: Mark L. Stolowitz, Edward A. Kesicki, Kevin P. Lund, Karin A. Hughes
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Patent number: 6037505Abstract: The anantoselective borane reduction of prochiral ketones to optically pure alcohols is effectively achieved by performing the reduction in the precence of catalytic amounts of the new and valuable oxazaborolidine compounds of formulas (I) and (II). The compounds of formulas (I) and (II) may be isolated and purified prior to use in the reduction reactions or the compounds of formulas (I) and (II) may be generated in situ.Type: GrantFiled: April 26, 1999Date of Patent: March 14, 2000Assignee: Pfizer Inc.Inventor: George Joseph Quallich
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Patent number: 6005133Abstract: The enantioselective borane reduction of prochiral ketones to optically pure alcohols is effectively achieved by performing the reduction in the presence of catalytic amounts of the new and valuable oxazaborolidine compounds of formulae (I) and (II). The compounds of formulae (I) and (II) may be isolated and purified prior to use in the reduction reactions or the compounds of formulae (I) and (II) may be generated in situ.Type: GrantFiled: October 10, 1995Date of Patent: December 21, 1999Assignee: Pfizer Inc.Inventor: George Joseph Quallich
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Patent number: 5872224Abstract: Boron compound complexing reagents, boron compound complexes, and methods of synthesizing these reagents and complexes are disclosed. These reagents and complexes include those shown in General Formula CIV, and General Formula CVI. In one embodiment, the reagent of General Formula CIV may be used to form a complex with a boron compound, such as a complex shown in General Formula CVI. ##STR1## In one embodiment, group Z comprises a spacer selected from a saturated or unsaturated chain of up to about 6 carbon equivalents in length, an unbranched saturated or unsaturated chain of from about 6 to 18 carbon equivalents in length with at least one of intermediate amide and disulfide moieties, and a polyethylene glycol chain of from about 3 to 12 carbon equivalents in length; group R.sub.3 is selected from one of an H, an alkyl, and a methylene or ethylene moiety with an electronegative substituent; and BAS and BAS* are biologically active species.Type: GrantFiled: October 22, 1997Date of Patent: February 16, 1999Assignee: Prolinx, Inc.Inventors: Mark L. Stolowitz, Robert J. Kaiser, Kevin P. Lund
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Patent number: 5859210Abstract: Boron compound complexing reagents, boron compound complexes, and methods of synthesizing these reagents and complexes are disclosed. These reagents and complexes include those shown in General Formula IV and General Formula VI. In one embodiment, the reagent of General Formula IV may be used to form a complex with a boron compound, such as a complex shown in General Formula VI. ##STR1## In one embodiment, group Z comprises a spacer selected from a saturated or unsaturated chain of up to about 6 carbon equivalents in length, an unbranched saturated or unsaturated chain of from about 6 to 18 carbon equivalents in length with at least one of intermediate amide or disulfide moieties, and a polyethylene glycol chain of from about 3 to 12 carbon equivalents in length; group R.sub.3 is selected from one of an H, an alkyl, and a methylene or ethylene moiety with an electronegative substituent; and BAS and BAS* are biologically active species.Type: GrantFiled: October 22, 1997Date of Patent: January 12, 1999Assignees: Prolinx, Inc., SystemixInventors: Mark L. Stowolitz, Robert J. Kaiser, Kevin P. Lund, Steven M. Torkelson
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Patent number: 5698538Abstract: Novel boronic acid and ester and carboxyl-modified amino acid compounds of the Formula I, which are inhibitors of trypsin-like enzymes, are disclosed :R.sup.1 --Z--CHR.sup.2 --A,where R.sup.1, Z, R.sup.2 arid A are defined within.Type: GrantFiled: July 26, 1996Date of Patent: December 16, 1997Assignee: The DuPont Merck Pharmaceutical CompanyInventors: Eugene Cruz Amparo, William Henry Miller, Gregory James Pacofsky, John Wityak, Patricia Carol Weber, John Jonas Vytautas Duncia, Joseph Basil Santella, III
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Patent number: 5688928Abstract: The present invention relates to a novel class of phenylboronic acid complexing reagents useful for the preparation of bioconjugates, and the method of making and using such reagents. In the present invention, in the place of prior art Avidin-Biotin and Digoxigenin-anti-Digoxigenin systems, phenylboronic acid complexing reagents are utilized in conjunction with phenylboronic acid reagents (many of which are known in the prior art) to facilitate chemical conjugation without the use of intermediary biological macromolecules. Reagents suitable for the modification of bioactive species for the purpose of incorporating a phenylboronic acid complexing moiety for subsequent conjugation to a different bioactive species having pendant phenylboronic acid moieties are of General Formula I or General Formula II. ##STR1## wherein group X is selected from either H, OH, NH.sub.2, NHCH.sub.3, NHOH and NHOCH.sub.Type: GrantFiled: June 7, 1995Date of Patent: November 18, 1997Assignee: Prolinx, Inc.Inventor: Mark L. Stolowitz
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Patent number: 5677431Abstract: The present invention relates to a novel class of phenylboronic acid bioconjugate complexes derived from aminosalicylic acid, and the method of making and using such bioconjugate complexes. The bioconjugate complexes are in the form of the following general formulas; ##STR1## wherein group X is selected from the group consisting of O, NH, N-alkyl, NC.sub.6 H.sub.5, N-aryl, NCH.sub.2 -aryl, NCH.sub.2 CH.sub.2 OH, NCOCH.sub.2 CH.sub.2 OH, NOH, NO-alkyl and NOCH.sub.2 -aryl, wherein alkyl denotes a hydrocarbon moiety of from 1 to 4 carbons in length and which may be linear or branched, wherein aryl is selected from the group consisting of an aromatic ring, a substituted aromatic ring and a fused aromatic ring,wherein group Y is selected from the group consisting of O, S, NH, N-alkyl, N-aryl and NCH.sub.Type: GrantFiled: June 7, 1995Date of Patent: October 14, 1997Assignee: Prolinx, Inc.Inventor: Mark L. Stolowitz
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Patent number: 5668258Abstract: The present invention relates to a novel class of phenylboronic acid complexing reagents useful for the preparation of bioconjugates, and the method of making and using such reagents. In the present invention, in the place of prior art Avidin-Biotin and Digoxigenin-anti-Digoxigenin systems, phenylboronic acid complexing reagents are utilized in conjunction with phenylboronic acid reagents (many of which are known in the prior art) to facilitate chemical conjugation without the use of intermediary biological macromolecules. Reagents suitable for the modification of a bioactive species for the purpose of incorporating a phenylboronic acid complexing moiety for subsequent conjugation to a different bioactive species having pendant phenylboronic acid moieties are of General Formula I or General Formula II. ##STR1## wherein group X is selected from either H, OH, NH.sub.2, NHCH.sub.3, NHOH and NHOCH.sub.Type: GrantFiled: June 7, 1995Date of Patent: September 16, 1997Assignee: Prolinx, Inc.Inventor: Mark L. Stolowitz
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Patent number: 5648470Abstract: The present invention relates to a novel class of phenylboronic acid complexing reagents useful for the preparation of bioconjugates, and the method of making and using such reagents. In the present invention, in the place of prior art Avidin-Biotin and Digoxigenin-anti-Digoxigenin systems, phenylboronic acid complexing reagents are utilized in conjunction with phenylboronic acid reagents (many of which are known in the prior art) to facilitate chemical conjugation without the use of intermediary biological macromolecules. Reagents suitable for the modification of a bioactive species for the purpose of incorporating a phenylboronic acid complexing moiety for subsequent conjugation to a different bioactive species having pendant phenylboronic acid moieties are of General Formula I or General Formula II. ##STR1## wherein group X is selected from either H, OH, NH.sub.2, NHCH.sub.3, NHOH and NHOCH.sub.Type: GrantFiled: June 7, 1995Date of Patent: July 15, 1997Assignee: Prolinx, Inc.Inventor: Mark L. Stolowitz
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Patent number: 5623055Abstract: The present invention relates to a novel class of bioconjugates derived from phenylboronic acid complexes, and the method of making and using such bioconjugate complexes. The complexes are in the form of the following general formulas. ##STR1## wherein group Q is selected from either O, S, NH, N-alkyl and N-aryl, wherein alkyl denotes a hydrocarbon moiety, wherein aryl is selected from either an aromatic ring, a substituted aromatic ring and fused aromatic rings, wherein group R is preferably selected from either O, NH, CH.sub.2, alkyl and aryl, wherein alkyl and aryl are as were previously defined,wherein group X is selected from either H, CH.sub.3 and C.sub.6 H.sub.5, wherein group Y is selected from either O, NH, CH.sub.Type: GrantFiled: January 28, 1994Date of Patent: April 22, 1997Assignee: Prolinx, Inc.Inventor: Mark L. Stolowitz
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Patent number: 5594111Abstract: The present invention relates to a novel class of phenylboronic acid bioconjugate complexes derived from aminosalicylic acid, and the method of making and using such bioconjugate complexes. The bioconjugate complexes are in the form of the following general formulas; ##STR1## wherein group X is selected from the group consisting of O, NH, N-alkyl, NC.sub.6 H.sub.5, N-aryl, NCH.sub.2 -aryl, NCH.sub.2 CH.sub.2 OH, NCOCH.sub.2 CH.sub.2 OH, NOH, NO-alkyl and NOCH.sub.2 -aryl, wherein alkyl denotes a hydrocarbon moiety of from 1 to 4 carbons in length and which may be linear or branched, wherein aryl is selected from the group consisting of an aromatic ring, a substituted aromatic ring and a fused aromatic ring,wherein group Y is selected from the group consisting of O, S, NH, N-alkyl, N-aryl and NCH.sub.Type: GrantFiled: January 28, 1994Date of Patent: January 14, 1997Assignee: Prolinx, Inc.Inventor: Mark L. Stolowitz
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Patent number: 5552548Abstract: The borane reduction of prochiral ketones to optically pure alcohols is effectively achieved by the utilization of catalytic amounts of the new and valuable oxazaborolidine catalysts of formula (I).Type: GrantFiled: October 13, 1994Date of Patent: September 3, 1996Assignee: Pfizer Inc.Inventor: George J. Quallich