Benzene Ring And The Lactone Ring Bonded Directly To The Same Acyclic Carbon Patents (Class 549/286)
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Patent number: 11307183Abstract: The disclosure relates to a reversed-phase chromatography method for the determination of at least one of glyphosate or AMPA in a sample. The method includes obtaining the sample comprising the at least one of glyphosate or AMPA in a sample matrix and introducing the sample to a reversed-phase chromatography system. The reversed-phase chromatography system includes a reversed-phase column having a stationary phase material contained inside the column. The stationary phase material includes a phenyl functional group. The method also includes flowing the sample with a mobile phase eluent through the reversed-phase column, wherein the at least one of glyphosate or AMPA is substantially resolved and retained. The mobile phase eluent has a pH between about 1.5 to about 2.5. The at least one of glyphosate or AMPA are detected using a detector.Type: GrantFiled: July 17, 2019Date of Patent: April 19, 2022Assignee: Waters Technologies CorporationInventors: Danilo Augusto Alves Pereira, Mirela Talarico Afonso De Moura, Marcella Fernanda Alves Reis
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Patent number: 10532326Abstract: The present disclosure relates to, inter alia, a modified surface comprising an optically active monomer, a polymeric material having a surface onto which the optically active monomer is covalently bound. In one aspect, a membrane comprising an optically active monomer, a poly(aryl sulfone) membrane having a surface onto which the optically active monomer is covalently bound. The present disclosure also relates to a method of modifying a surface, the method comprising applying sufficient energy to a surface to induce covalent bonding with an optically active monomer, and contacting the optically active monomer with the surface. In one aspect, a method of modifying a surface of a poly(aryl sulfone) membrane is disclosed. In another aspect, a method of synthesizing an optically active monomer is disclosed. In one aspect, a method of filtration of chiral compounds is disclosed.Type: GrantFiled: July 8, 2015Date of Patent: January 14, 2020Assignee: Rensselaer Polytechnic InstituteInventors: Georges Belfort, Joseph Imbrogno
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Patent number: 9023837Abstract: Described herein are pharmaceutical compositions and medicaments, and methods of using such pharmaceutical compositions and medicaments in the treatment of cancer.Type: GrantFiled: April 15, 2011Date of Patent: May 5, 2015Assignee: Colby Pharmaceutical CompanyInventors: Hirak S. Basu, David A. Zarling, George Wilding, Farideh Mehraein-Ghomi, Dawn R. Church
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Publication number: 20140249214Abstract: In various embodiments, the present invention provides methods of treating and/or preventing cardiovascular-related disease and, in particular, a method of reducing triglycerides in a subject on warfarin therapy, the method comprising administering to a subject in need thereof a pharmaceutical composition comprising eicosapentaenoic acid or a derivative thereof.Type: ApplicationFiled: February 28, 2014Publication date: September 4, 2014Applicant: AMARIN PHARMACEUTICALS IRELAND LIMITEDInventors: Rene Braeckman, William Stirtan, Paresh Soni
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Patent number: 8765976Abstract: There is provided crystalline solvate forms of Warfarin potassium, termed APO-I and APO-II, and processes for making APO-I and APO-II. APO-I and APO-II are polymorphic solvate forms of Warfarin potassium.Type: GrantFiled: May 20, 2011Date of Patent: July 1, 2014Assignee: Apotex Pharmachem Inc.Inventors: Prabhudas Bodhuri, Gamini Weeratunga, Keshava K. S. Murthy
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Publication number: 20140073762Abstract: The present invention generally provides a separation matrix comprising at least two stationary phases and a stationary phase comprising at least one chiral modality and at least one achiral modality. Also provided are methods of using the separation matrix or the stationary phase to separate enantiomers of one or more chiral molecules.Type: ApplicationFiled: November 13, 2013Publication date: March 13, 2014Applicant: Board of Trustees of the University of ArkansasInventors: Grover Miller, Drew R. Jones, Gunnar Boysen
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Publication number: 20130210772Abstract: Described herein are pharmaceutical compositions and medicaments, and methods of using such pharmaceutical compositions and medicaments in the treatment of cancer.Type: ApplicationFiled: April 15, 2011Publication date: August 15, 2013Applicant: COLBY PHARMACEUTICAL COMPANYInventors: Hirak S. Basu, David A. Zarling, George Wilding, Farideh Mehraein-Ghomi, Dawn R. Church
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Publication number: 20130143957Abstract: There is provided crystalline solvate forms of Warfarin potassium, termed APO-I and APO-II, and processes for making APO-I and APO-II. APO-I and APO-II are polymorphic solvate forms of Warfarin potassium.Type: ApplicationFiled: May 20, 2011Publication date: June 6, 2013Applicant: APOTEX PHARMACHEM INC.Inventors: Prabhudas Bodhuri, Gamini Weeratunga, Keshava K.S. Murthy
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Patent number: 8445531Abstract: A rodenticidal compound of formula (I): as well as the isomers thereof, in particular enantiomers, diastereoisomers, tautomers or mixtures of isomers in all proportions, where: R1 is: H or (II) or (III) with X?H, OH, Cl, Br, F or N02; R2 is: (IV) or (V) or (VI) with X?H, OH, Cl, Br, F or NO2; R3 is: O or S or (VII) with X?H, OH, Cl, Br, F or N02. Compositions containing such compounds as well as a method of use thereof in controlling harmful rodents are also described.Type: GrantFiled: February 16, 2011Date of Patent: May 21, 2013Assignee: LiphatechInventors: Romain Lasseur, Etienne Benoit, Philippe Berny, Stephane Besse
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Publication number: 20120316231Abstract: A rodenticidal compound of formula (I): as well as the isomers thereof, in particular enantiomers, diastereoisomers, tautomers or mixtures of isomers in all proportions, where: R1 is: H or (II) or (III) with X?H, OH, Cl, Br, F or N02; R2 is: (IV) or (V) or (VI) with X?H, OH, Cl, Br, F or NO2; R3 is: O or S or (VII) with X?H, OH, Cl, Br, F or N02. Compositions containing such compounds as well as a method of use thereof in controlling harmful rodents are also described.Type: ApplicationFiled: February 16, 2011Publication date: December 13, 2012Applicant: LIPHATECHInventors: Romain Lasseur, Etienne Benoit, Philippe Berny, Stephane Besse
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Publication number: 20120226054Abstract: The present invention generally provides a separation matrix comprising at least two stationary phases and a stationary phase comprising at least one chiral modality and at least one achiral modality. Also provided are methods of using the separation matrix or the stationary phase to separate enantiomers of one or more chiral molecules.Type: ApplicationFiled: March 3, 2011Publication date: September 6, 2012Applicant: BOARD OF TRUSTEES OF THE UNIVERSITY OF ARKANSASInventors: Grover Miller, Drew R. Jones, Gunnar Boysen
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Publication number: 20090082430Abstract: The subject invention provides anticoagulant compounds of formula I: and pharmaceutically acceptable salts thereof, wherein R1, R3, n and Ar are as defined herein. The compounds of the subject invention can be used to treat at-risk populations thereby bringing relief of symptoms, improving the quality of life, preventing acute and long-term complications, reducing mortality and treating accompanying disorders. The invention further comprises pharmaceutical compositions comprising the compounds and salts of the invention, as well as methods of using the compounds, salts, and compositions of the invention.Type: ApplicationFiled: November 10, 2008Publication date: March 26, 2009Applicant: ARYx Therapeutics, Inc.Inventors: Pascal Druzgala, Cyrus Becker
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Patent number: 7285671Abstract: The subject invention provides anticoagulant compounds of formula I: and pharmaceutically acceptable salts thereof, wherein R1, R3, n and Ar are as defined herein. The compounds of the subject invention can be used to treat at-risk populations thereby bringing relief of symptoms, improving the quality of life, preventing acute and long-term complications, reducing mortality and treating accompanying disorders. The invention further comprises pharmaceutical compositions comprising the compounds and salts of the invention, as well as methods of using the compounds, salts, and compositions of the invention.Type: GrantFiled: August 28, 2006Date of Patent: October 23, 2007Assignee: ARYx TherapeuticsInventors: Pascal Druzgala, Cyrus Becker
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Patent number: 7259185Abstract: A stable liquid composition comprising warfarin sodium, glycerin, an alcohol such as ethanol, and a pH buffer such as a phosphate buffer providing a pH above 7 is provided. The stability of the composition is characterized by the amount of warfarin sodium in the composition degraded after 1 month at room temperature, which is 5% or less. A method for preparing the composition and a method for providing an anti-coagulant therapy are also disclosed.Type: GrantFiled: June 14, 2006Date of Patent: August 21, 2007Assignee: Morton Grove Pharmaceuticals, Inc.Inventors: Meagan Erica Weldele, David Delmarre, Danchen Gao, Mahmoud Assad El-Khateeb, Carlos-Julian Sison Centeno, Shitalkumar Ratnakar Pathak
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Patent number: 7253208Abstract: The subject invention provides anticoagulant compounds of formula I: and pharmaceutically acceptable salts thereof, wherein R1, R3, n and Ar are as defined herein. The compounds of the subject invention can be used to treat at-risk populations thereby bringing relief of symptoms, improving the quality of life, preventing acute and long-term complications, reducing mortality and treating accompanying disorders. The invention further comprises pharmaceutical compositions comprising the compounds and salts of the invention, as well as methods of using the compounds, salts, and compositions of the invention.Type: GrantFiled: April 8, 2005Date of Patent: August 7, 2007Assignee: Aryx TherapeuticsInventors: Pascal Druzgala, Cyrus Becker
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Patent number: 7179838Abstract: The present invention relates to the albumin-guided development of coumarin analogs and the analogs developed thereby. The coumarin analogs of the present invention are identified and isolated by the fact that they have binding sites to albumin which are different than the binding sites of conventional coumarin analogs such as sodium warfarin, and as a result will be less prone to be displaced since the binding site of sodium warfarin is shared by numerous drugs such as aspirin. The coumarin analogs of the invention are advantageous because they can achieve the effects of the prior coumarin analogs with a minimum of metabolic complications and undesirable side effects.Type: GrantFiled: July 30, 2003Date of Patent: February 20, 2007Assignee: New Century Pharmaceuticals, Inc.Inventor: Daniel C. Carter
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Patent number: 6673944Abstract: The invention provides a method for the direct preparation of pure warfarin sodium from warfarin acid. The reaction is conducted in a polar organic solvent, preferably ethanol, using a volatilizable base, preferably sodium bicarbonate or sodium carbonate, at low temperature. Drying the final product is accomplished at low temperature to avoid decomposition of the final warfarin sodium product.Type: GrantFiled: February 28, 2001Date of Patent: January 6, 2004Assignee: Taro Pharmaceutical Industries, Ltd.Inventors: Michel Ashkar, Sorin Bercovici, Robert Graff
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Patent number: 6512005Abstract: An improved procedure for the purification of warfarin acid. Sodium, potassium and lithium warfarin salts and the corresponding clathrates are prepared in high, pharnacopeial grade purity and good yields from the pure warfarin acid and the respective metal salt bases in suitable media.Type: GrantFiled: February 28, 2001Date of Patent: January 28, 2003Assignee: Taro Pharmaceutical Industries, Ltd.Inventors: Sorin Bercovici, Yuval Evron, Osvaldo Fuxman, Mirela Jakoel, Sbar Sasson, Konstantin Ulanenko
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Patent number: 6344330Abstract: The present invention is directed to novel methods for identifying small molecule ligands that are capable of binding with high affinity to a biological target molecule of interest. High affinity binding ligands identified by the described methods find use, for example, as small molecule lead compounds that may they themselves be, or may give rise to, novel therapeutic drugs. More specifically, the subject invention is directed to methods for identifying a ligand that binds to a target biological molecule of interest, wherein a population of small organic compounds are selected and then “pre-screened” to identify those that are capable of binding to the molecular target.Type: GrantFiled: March 27, 1998Date of Patent: February 5, 2002Assignee: The Regents of the University of CaliforniaInventors: Jonathan A. Ellman, Ingrid Choong
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Patent number: 6344334Abstract: Method for identifying a drug lead compound that inhibits binding of target bioogical molecules (TBM) by contacting TBM with members of a library of candidate cross-linked target binding fragments (CXBF), each CXBF having at least two candidate target bindig fragments (CTBF), which are inhibitors of binding, linked to a cross-linker, and selecting CXBF that inhibit the binding of the TBM to a greater extent than either of the individual CTBF linked to said cross-linker, wherein the library of CXBF is produced by: (a) screening a population of CTBF capable of being chemically cross-linked by a cross-linker to identify a subpopulation of the CTBF that inhibit binding of the TBM; and (b) chemically cross-linking members of the subpopulation of CTBF or structurally related analogs thereof with a cross-linker to provide a library of CXBF, wherein at least one linking group comprises an oxime ether linking group.Type: GrantFiled: March 26, 1999Date of Patent: February 5, 2002Assignee: The Regents of the University of CaliforniaInventors: Jonathan A. Ellman, Ingrid Choong
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Patent number: 6291518Abstract: The present invention relates to novel hydroxy and polyhydroxy derivatives of coumarin fused with dialdehydes and aldehyde acids of the general formulae I, II, III and IV: wherein R1=R2=4-hydroxycoumarin; R1=R2=4,7-dihydroxycoumarin; R1=R2=4,5,7-trihydroxycoumarin; R1=4-hydroxycoumarin, R2=—CH(OH)CH3. An object of the invention are also processes for the preparation of hydroxy and polyhydroxy derivatives of coumarin fused with dialdehydes and aldehyde acids, and the antiviral action thereof. Novel hydroxy and polyhydroxy derivatives of coumarin according to the present invention exhibit antiviral action against HIV-1 virus.Type: GrantFiled: January 3, 2000Date of Patent: September 18, 2001Assignee: Pliva farmaceutska, kemijska, prehrambena i kozmeticka industrija, dionicko drustvoInventors: Mladen Trkovnik, Zrinka Ivezić
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Patent number: 6255277Abstract: A method for preventing adverse effects associated with the use of a medical device in a patient by introducing into the patient a device of which at least a portion includes a prophylactic or therapeutic amount of a nitric oxide adduct. The nitric oxide adduct can be present in a matrix coating on a surface of the medical device; can be coated per se on a surface of the medical device; can be directly or indirectly bound to reactive sites on a surface of the medical device; or at least a portion of the medical device can be formed of a material, such as a polymer, which includes the nitric oxide adduct. Also disclosed is a method for preventing adverse effects associated with the use of a medical device in a patient by introducing the device during a medical procedure and before or during said procedure locally administering a nitric oxide adduct to the site of contact of said device with any internal tissue.Type: GrantFiled: May 10, 1995Date of Patent: July 3, 2001Assignees: Brigham and Women's Hospital, NitroMed, Inc.Inventors: Jonathan Stamler, Joseph Loscalzo, John D. Folts
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Patent number: 5856525Abstract: The present invention provides a novel process for making compounds of formula 2a or 2b or pharmaceutically acceptable salts thereof, ##STR1## wherein R.sub.1 is selected from the group consisting of phenyl and phenyl substituted with at least one group selected from NO.sub.2 and halogen;R.sub.2 is H;R.sub.3 is selected from the group consisting of C.sub.1-4 alkyl, phenyl, and benzyl; and,R.sub.4 is selected from the group consisting of H and halogen;which comprises the steps of:a) oxidizing a racemate of formula 2 or a salt thereof to form a dehydro-compound of formula 3, ##STR2## wherein R.sub.5 is selected from the group consisting of H, CH.sub.3, benzyl, C.sub.2-8 acyl Na, Li and K; and,b) asymmetrically hydrogenating a compound of formula 3 in the presence of a chiral phosphine catalyst to form a compound of formula 2a or 2b.Type: GrantFiled: October 14, 1997Date of Patent: January 5, 1999Assignee: DuPont Pharmaceuticals CompanyInventors: Hui-Yin Li, Andrea Jane Robinson
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Patent number: 5696274Abstract: The present invention provides processes which are flexible, cost effective, and commercially viable methods of manufacturing or producing products from 2-hydroxyacetophenone (2-HAP).Of particular interest of the available products are 4-hydroxycoumarin, warfarin-alkali salt, preferably warfarin sodium and warfarin-alkali salt-isopropyl alcohol (2-propanol) complex, more preferably warfarin-sodium-isopropyl alcohol complex.As is known, these compounds are useful as vitamin K dependent anticoagulants in the treatment of humans and animals. In different doses, they are also useful as rodenticide.The inventive process involves contacting 2-HAP, carbonate ester and effective base followed by treatment with an unsaturated ketone and phase transfer catalyst to ultimately yield product.Type: GrantFiled: May 22, 1996Date of Patent: December 9, 1997Assignee: Hoechst Celanese CorporationInventors: Ibrahim M. Uwaydah, Mohammad Aslam, Charles H. Brown, II, Sharon R. Fitzhenry, Joseph A. McDonough
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Patent number: 5616719Abstract: Photoactive indicator compounds of the formula ##STR1##Type: GrantFiled: May 9, 1995Date of Patent: April 1, 1997Assignee: Behringwerke AGInventors: Dariush Davalian, Rajendra Singh, Edwin F. Ullman
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Patent number: 5580552Abstract: A 7-glycosyloxybenzopyran derivative represented by the following formula (I) ##STR1## wherein, R is a hydrogen atom, an acyl group, an alkyl group, a cycloalkyl group, an alkenyl group or an aralkyl group, R.sub.2 is a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group or an aralkyl group and R.sub.3 is a glycosyl group whose hydroxyl group is protected or not protected, selected from the group consisting of glucosyl, mannosyl and galactosyl groups, and physiologically acceptable salts thereof.Type: GrantFiled: May 19, 1995Date of Patent: December 3, 1996Assignee: Dainippon Ink & Chemicals Inc.Inventors: Hidetsugu Takagaki, Masayoshi Abe, Yasuo Aoki, Mitsuru Sakai, Nobuyuki Kimura
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Patent number: 5418254Abstract: A class of 2,3-substituted cyclopenta-2,4-dienyl compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula II: ##STR1## wherein each of R.sup.1 and R.sup.2 is independently selected from hydrido, lower alkyl, lower hydroxyalkyl, halo, lower haloalkyl, lower alkoxycarbonyl and carboxyl; and wherein each of R.sup.3 through R.sup.12 is independently selected from hydrido, halo, lower alkyl, lower alkylthio, cyano, hydroxyl, mercapto, lower haloalkyl, lower haloalkoxy, lower alkoxy, lower hydroxyalkyl, lower alkoxyalkyl, lower alkylsulfonyl, lower haloalkylsulfonyl and sulfamyl; provided R.sup.5 and R.sup.10 are not both hydrido or methoxy; or a pharmaceutically suitable salt or prodrug thereof.Type: GrantFiled: May 4, 1994Date of Patent: May 23, 1995Assignee: G. D. Searle & Co.Inventors: Horng-Chih Huang, David R. Reitz
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Patent number: 4788297Abstract: Process for selective removal of the cis-isomer and consequent enrichment of a solution with respect to the trans-isomer of a 1-(4-hydroxycoumarin-3-yl)-3-substituted phenyl)tetrahydronaphthalene rodenticide by crystallization from hot solvent.Type: GrantFiled: August 26, 1985Date of Patent: November 29, 1988Assignee: Imperial Chemical Industries PLCInventor: Alan J. Whittle
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Patent number: 4659657Abstract: Compounds of the formula ##STR1## wherein Y is ##STR2## M is hydrogen, or an alkali metal or ammonium ion, X is --O-- or an amino group,R is H, Cl, Br, CN or carbamoyl,R.sup.1 is H or --SO.sub.3 H, andA is one of several particular organic radicals,are especially useful in the photometric or fluorimetric determination of phosphatase or sulphatase activity in a liquid sample.Type: GrantFiled: December 14, 1983Date of Patent: April 21, 1987Assignee: Bayer AktiengesellschaftInventors: Horst Harnisch, Otto S. Wolfbeis
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Patent number: H852Abstract: A method for stabilizing a rodenticidally active material selected from certain (i) indane dione derivatives, (ii) hydroxycoumarin derivatives and (iii) thiocoumarin analogs of (ii), comprising bringing said active material into contact with, and maintaining the active material in contact with, an acidic stabilizer.Type: GrantFiled: October 27, 1988Date of Patent: November 6, 1990Assignee: E. I. Du Pont de Nemours and Company, Inc.Inventors: Alan R. Garden, Malcolm R. Hadler