Nicotine, Per Se, Or Its Salts Patents (Class 546/279.4)
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Patent number: 11407730Abstract: The present invention relates to a method of preparing racemic nicotine comprising: (i) reacting ethyl nicotinate and N-vinylpyrrolidone in the presence of an alcoholate base to 3-nicotinoyl-1-vinylpyrrolidin-2-one; (ii) reacting the 3-nicotinoyl-1-vinylpyrrolidin-2-one with an acid to myosmine; (iii) reducing the myosmine to nornicotine using a reducing agent; and (iv) methylating the nornicotine to obtain the racemic nicotine.Type: GrantFiled: December 18, 2018Date of Patent: August 9, 2022Assignees: Siegfried AG, Contraf-Nicotex-Tobacco GmbHInventors: Beat Theodor Weber, Christian Lothschütz, Ben Pan
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Patent number: 11279685Abstract: The present invention relates to a method of separating racemic nicotine of Formula (1-a) as a mixture of the (R)- and (S)-enantiomers into the enantiomerically pure (S)- and (R)-nicotine represented by Formula (1-b) and (1-c), by adding a mixture of the L- and the D-enantiomer of a O,O?-disubstituted tartaric acid, wherein the molar ratio of the L- to the D-enantiomer is from 80:20 to 95:5, and obtaining the (S)-nicotine of formula (1-b), or by adding O,O?-dibenzoyl-D-tartaric acid and obtaining the (R)-nicotine of formula (1-c).Type: GrantFiled: December 18, 2018Date of Patent: March 22, 2022Assignees: SIEGFRIED AG, CONTRAF-NICOTEX-TOBACCO GMBHInventors: Beat Theodor Weber, Ben Pan
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Patent number: 11136305Abstract: The invention provides certain nicotine salts, co-crystals, and salt co-crystals and provides novel polymorphic forms of certain nicotine salts. In particular, nicotine salts with mucic acid, 3,5-dihydroxybenzoic acid, and 2,3-dihydroxybenzoic acid, and crystalline polymorphic forms of nicotine 4-acetamidobenzoate, nicotine gentisate, and nicotine 1-hydroxy-2-naphthoate are described. The invention further provides methods of preparation and characterization of such nicotine salts, co-crystals, and salt co-crystals and polymorphic forms thereof. In addition, tobacco products, including smoking articles, smokeless tobacco products, and electronic smoking articles comprising nicotine salts, co-crystals, and/or salt co-crystals are also provided.Type: GrantFiled: January 10, 2020Date of Patent: October 5, 2021Assignee: R.J. Reynolds Tobacco CompanyInventors: Gary M. Dull, Andrew Carr, Emma Sharp
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Patent number: 11091458Abstract: The present invention relates to a method of preparing racemic nicotine comprising: (i) reacting ethyl nicotinate and N-vinylpyrrolidone in the presence of an alcoholate base to 3-nicotinoyl-1-vinylpyrrolidin-2-one; (ii) reacting the 3-nicotinoyl-1-vinylpyrrolidin-2-one with an acid to myosmine; (iii) reducing the myosmine to nornicotine using a reducing agent; and (iv) methylating the nornicotine to obtain the racemic nicotine.Type: GrantFiled: December 18, 2018Date of Patent: August 17, 2021Assignees: Siegfried AG, Contraf-Nicotex-Tobacco GmbHInventors: Beat Theodor Weber, Christian Lothschütz, Ben Pan
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Patent number: 10913962Abstract: A process for synthetically producing (S)-nicotine ([(S)-3-(1-methylpyrrolidin-2-yl) pyridine]) is provided.Type: GrantFiled: March 12, 2019Date of Patent: February 9, 2021Assignee: ZANOPRIMA LIFESCIENCES LIMITEDInventors: Raymond McCague, Ashok Srinivasan Narasimhan
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Patent number: 10865192Abstract: The invention provides certain nicotine salts, co-crystals, and salt co-crystals and provides novel polymorphic forms of certain nicotine salts. In particular, nicotine salts with orotic acid are described. The invention further provides methods of preparation and characterization of such nicotine salts. In addition, tobacco products, including smoking articles, smokeless tobacco products, and electronic smoking articles comprising nicotine salts, co-crystals, and/or salt co-crystals are also provided.Type: GrantFiled: October 10, 2019Date of Patent: December 15, 2020Assignee: R.J. Reynolds Tobacco CompanyInventors: Gary M. Dull, Andrew Carr, Emma Sharp
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Patent number: 10759776Abstract: The present disclosure generally relates to methods of preparing nicotine and resolving R,S nicotine to enrich the (S)(?) enantiomer. The method may comprise combining N-methyl-2-pyrrolidone or a salt thereof with a nicotinate compound in the presence of a solvent and a strong base to form 1-methyl-3-nicotinoyl-2-pyrrolidone or a salt thereof; and reducing the 1-methyl-3-nicotinoyl-2-pyrrolidone or salt thereof in solution with Na2S2O4 to produce racemic nicotine or salt thereof. Resolving the racemic nicotine (or other enantiomeric mixture) may comprise combining the nicotine with (?)-O,O?-di-p-toluoyl-L-tartaric acid (L-PTTA).Type: GrantFiled: May 15, 2019Date of Patent: September 1, 2020Assignee: NJOY, LLCInventors: Bert Willis, Mohammed Moinuddin Ahmed, Wesley Freund, Douglas Sawyer
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Patent number: 10556880Abstract: The invention provides certain nicotine salts, co-crystals, and salt co-crystals and provides novel polymorphic forms of certain nicotine salts. In particular, nicotine salts with mucic acid, 3,5-dihydroxybenzoic acid, and 2,3-dihydroxybenzoic acid, and crystalline polymorphic forms of nicotine 4-acetamidobenzoate, nicotine gentisate, and nicotine 1-hydroxy-2-naphthoate are described. The invention further provides methods of preparation and characterization of such nicotine salts, co-crystals, and salt co-crystals and polymorphic forms thereof. In addition, tobacco products, including smoking articles, smokeless tobacco products, and electronic smoking articles comprising nicotine salts, co-crystals, and/or salt co-crystals are also provided.Type: GrantFiled: August 8, 2017Date of Patent: February 11, 2020Assignee: R.J. Reynolds Tobacco CompanyInventors: Gary M. Dull, Andrew Carr, Emma Sharp
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Patent number: 10508096Abstract: The invention provides certain nicotine salt co-crystals and provides novel polymorphic forms of certain nicotine salts. In particular, certain nicotine salt-co-crystals are described, including nicotine and two different coformers. The invention further provides methods of preparation and characterization of nicotine salts, co-crystals, and salt co-crystals. In addition, tobacco products, including smoking articles, smokeless tobacco products, and electronic smoking articles comprising nicotine salts, co-crystals, and/or salt co-crystals are also provided.Type: GrantFiled: September 5, 2017Date of Patent: December 17, 2019Assignee: R.J. Reynolds Tobacco CompanyInventors: Gary M. Dull, Susana del Rio Gancedo, Judit Galcera Julia
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Patent number: 10464917Abstract: The invention provides certain nicotine salts, co-crystals, and salt co-crystals and provides novel polymorphic forms of certain nicotine salts. In particular, nicotine salts with orotic acid are described. The invention further provides methods of preparation and characterization of such nicotine salts. In addition, tobacco products, including smoking articles, smokeless tobacco products, and electronic smoking articles comprising nicotine salts, co-crystals, and/or salt co-crystals are also provided.Type: GrantFiled: February 1, 2018Date of Patent: November 5, 2019Assignee: R.J. Reynolds Tobacco CompanyInventors: Gary M. Dull, Andrew Carr, Emma Sharp
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Patent number: 10329271Abstract: The present disclosure generally relates to methods of preparing nicotine and resolving R,S nicotine to enrich the (S)(?) enantiomer. The method may comprise combining N-methyl-2-pyrrolidone or a salt thereof with a nicotinate compound in the presence of a solvent and a strong base to form 1-methyl-3-nicotinoyl-2-pyrrolidone or a salt thereof; and reducing the 1-methyl-3-nicotinoyl-2-pyrrolidone or salt thereof in solution with Na2S2O4 to produce racemic nicotine or salt thereof. Resolving the racemic nicotine (or other enantiomeric mixture) may comprise combining the nicotine with (?)-O,O?-di-p-toluoyl-L-tartaric acid (L-PTTA).Type: GrantFiled: October 6, 2017Date of Patent: June 25, 2019Assignee: NJOY, LLCInventors: Bert Willis, Mohammed Moinuddin Ahmed, Wesley Freund, Douglas Sawyer
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Patent number: 9896429Abstract: The invention provides certain nicotine salts, co-crystals, and salt co-crystals and provides novel polymorphic forms of certain nicotine salts. In particular, nicotine salts with orotic acid are described. The invention further provides methods of preparation and characterization of such nicotine salts. In addition, tobacco products, including smoking articles, smokeless tobacco products, and electronic smoking articles comprising nicotine salts, co-crystals, and/or salt co-crystals are also provided.Type: GrantFiled: November 25, 2015Date of Patent: February 20, 2018Assignee: R.J. Reynolds Tobacco CompanyInventors: Gary M. Dull, Andrew Carr, Emma Sharp
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Patent number: 9738622Abstract: The invention provides certain nicotine salts, co-crystals, and salt co-crystals and provides novel polymorphic forms of certain nicotine salts. In particular, nicotine salts with mucic acid, 3,5-dihydroxybenzoic acid, and 2,3-dihydroxybenzoic acid, and crystalline polymorphic forms of nicotine 4-acetamidobenzoate, nicotine gentisate, and nicotine 1-hydroxy-2-naphthoate are described. The invention further provides methods of preparation and characterization of such nicotine salts, co-crystals, and salt co-crystals and polymorphic forms thereof. In addition, tobacco products, including smoking articles, smokeless tobacco products, and electronic smoking articles comprising nicotine salts, co-crystals, and/or salt co-crystals are also provided.Type: GrantFiled: May 26, 2015Date of Patent: August 22, 2017Assignee: R.J. Reynolds Tobacco CompanyInventors: Gary M. Dull, Andrew Carr, Emma Sharp
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Patent number: 9107453Abstract: The invention provides a tobacco composition for use in a smoking article or a smokeless tobacco composition that comprises an extract derived from a component of a plant of the Nicotiana species. The invention also provides smoking articles and smokeless tobacco compositions that include the extracts described herein, and methods for preparing extracts derived from a component of a plant of the Nicotiana species for addition to a tobacco composition.Type: GrantFiled: January 28, 2011Date of Patent: August 18, 2015Assignee: R.J. REYNOLDS TOBACCO COMPANYInventors: Michael Francis Dube, William Monroe Coleman, III
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Publication number: 20150020818Abstract: This document provides methods and systems for stabilizing nicotine and incorporating nicotine into one or more oral products. This document also provides oral products. Nicotine can be stabilized by mixing liquid nicotine with cellulosic fiber such that the liquid nicotine absorbs into pores of the cellulosic fiber to form a cellulosic fiber-nicotine mixture. In some cases, a cellulosic fiber-nicotine mixture can be combined with one or more binders and molded into an oral product.Type: ApplicationFiled: July 17, 2014Publication date: January 22, 2015Inventors: Feng Gao, Shuzhong Zhuang, Diane L. Gee
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Publication number: 20140331993Abstract: Processes for recovering sugars and nicotine from a tobacco biomass include feeding a biomass of tobacco plants and subcritical water to a reactor, hydrolyzing the biomass of tobacco plants with the subcritical water at a temperature between about 150° C. and 305° C. and recovering a liquid product and a solid product from the reactor, wherein the liquid product contains water-soluble sugars and nicotine.Type: ApplicationFiled: May 6, 2014Publication date: November 13, 2014Applicants: OLD DOMINION UNIVERSITY RESEARCH FOUNDATION, TYTON BIOSCIENCESInventors: Sandeep KUMAR, Jose Luis Garcia MOSCOSO, Iulian BOBE, Peter MAJERANOWSKI
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Patent number: 8884021Abstract: Provided is a process for preparing racemic nicotine from 1-methyl-3-nicotinoyl-2-pyrrolidone or a salt thereof using one-pot process. The process comprises the following steps: 1) in a reaction vessel, reacting 1-methyl-3-nicotinoyl-2-pyrrolidone or a salt thereof in the presence of a suitable solvent and a strong acid by heat; after the reaction is complete, cooling the same and adjusting the pH to 7-8 with alkali; and 2) directly adding a reductant into the above vessel, and after the reaction, purifying the product so as to obtain high purity racemic nicotine or a salt thereof.Type: GrantFiled: January 20, 2012Date of Patent: November 11, 2014Assignees: Topharman Shanghai Co., Ltd., Topharman Shandong Co., Ltd.Inventors: Guanghui Tian, Guan Wang, Xiaoguang Kong, Rongxia Zhang, Weiming Chen, Jingshan Shen
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Publication number: 20140274940Abstract: The use of pectins and/or polymers to prevent nicotine oxidation in tobacco containing products is disclosed. These polymers may be naturally occurring anionic polymers or synthetic polymers. These pectins and/or polymers prevent nicotine from oxidizing into cotinine, nicotine-cis-N-oxide, nicotine-trans-N-oxide, and/or nicotine-1,1-di-N-oxide. Molluscicides, algaecides, pesticides, and stabilized nicotine compositions comprising nicotine and pectin, anionic polymers, or combinations thereof are disclosed.Type: ApplicationFiled: March 12, 2014Publication date: September 18, 2014Applicant: Altria Client Services Inc.Inventors: Munmaya K. Mishra, Jason Flora, Georgios D. Karles, Christophe Claude Galopin, Diane Gee, John B. Paine, III, Douglas Antonio Fernandez
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Publication number: 20140031554Abstract: Provided is a process for preparing racemic nicotine from 1-methyl-3-nicotinoyl-2-pyrrolidone or a salt thereof using one-pot process. The process comprises the following steps: 1) in a reaction vessel, reacting 1-methyl-3-nicotinoyl-2-pyrrolidone or a salt thereof in the presence of a suitable solvent and a strong acid by heat; after the reaction is complete, cooling the same and adjusting the pH to 7-8 with alkali; and 2) directly adding a reductant into the above vessel, and after the reaction, purifying the product so as to obtain high purity racemic nicotine or a salt thereof.Type: ApplicationFiled: January 20, 2012Publication date: January 30, 2014Applicants: TOPHARMAN SHANGHAI CO., LTD., TOPHARMAN SHANDONG CO., LTD., SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCESInventors: Guanghui Tian, Guan Wang, Xiaoguang Kong, Rongxia Zhang, Weiming Chen, Jingshan Shen
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Patent number: 8624083Abstract: Plant metabolism and alkaloid levels can be regulated by transcription factors that regulate the nicotinic alkaloid biosynthetic pathway.Type: GrantFiled: May 4, 2012Date of Patent: January 7, 2014Assignee: National Research Council of CanadaInventors: Jonathan Page, Andrea T. Todd
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Publication number: 20130324503Abstract: The present invention relates to methods of treatment for Parkinson Disease (PD) in a person by identifying gene variants which may indicate a more favorable response to specific medicaments, thereby allowing for personalized or individualized treatment. The present invention relates to a method of screening for a genetic predisposition to PD in a person. The present invention is also directed to a method of testing a person for the presence of particular gene variants, wherein the presence of a gene variant indicates a higher predisposition to PD, and the absence of a gene variant indicates a lower predisposition to PD, compared to a control sample. The present invention further relates to methods and kits for treating, or inhibiting the development of, PD in a person. The present invention is also directed to a method of identifying the heritage of an individual based on the genetic profile of the individual.Type: ApplicationFiled: October 19, 2012Publication date: December 5, 2013Applicants: Health Research Inc., Emory University School of Medicine, National Institute of Environmental Health Sciences, Veterans Affairs Puget Sound Health Care System, Oregon Health & Science UniversityInventors: Haydeh Payami, Taye H. Hamza, Stewart A. Factor, John Nutt, Cyrus Zabetian, Honglei Chen, Erin Hill Burns
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Publication number: 20130318661Abstract: The gene encoding N-methylputrescine oxidase (MPO) and constructs comprising such DNA are provided, including methods of regulating MPO expression independently or with other alkaloid biosynthesis genes to modulate alkaloid production in plants and host cells. MPO genes or fragments thereof are useful for reducing pyrrolidine or tropane alkaloid production in plants, for increasing pyrrolidine or tropane alkaloid production in plants, and for producing an MPO enzyme in host cells.Type: ApplicationFiled: February 22, 2013Publication date: November 28, 2013Applicant: National Research Council of CanadaInventor: National Research Council of Canada
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Patent number: 8378111Abstract: (R,S)-Nicotine was resolved through diastereomeric salt formation using dibenzoyl-d-tartaric acid and dibenzoyl-l-tartaric acid to obtain enantiomerically pure (S)-nicotine and (R)-nicotine.Type: GrantFiled: April 6, 2011Date of Patent: February 19, 2013Assignee: Divi's Laboratories, Ltd.Inventors: Murali Krishna Prasad Divi, Gundu Rao Padakandla, Mysore Aswatha Narayana Rao, Hari Babu Katta
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Patent number: 8367837Abstract: A process for (R,S)-nicotine is described. Condensation of 1-(but-1-enyl)pyrrolidin-2-one with nicotinic acid ester gave 1-(but-1-enyl)-3-nicotinoylpyrrolidin-2-one which on treatment with an acid and a base gave myosmine. Myosmine was converted to (R,S)-nicotine by reduction followed by N-methylation.Type: GrantFiled: April 6, 2011Date of Patent: February 5, 2013Assignee: Divi's Laboratories, Ltd.Inventors: Murali Krishna Prasad Divi, Gundu Rao Padakandla, Mysore Aswatha Narayana Rao, Hari Babu Katta
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Publication number: 20120232111Abstract: The invention provides a parakeratosis inhibitor, pore-shrinking agent, or rough skin preventing/ameliorating agent that has a function such as parakeratosis inhibition, pore shrinkage, or rough skin—inhibition/abatement, poses no safety problems such as sensory irritation, and is very safe, and further provides an external composition for skin to which a compound having the above-mentioned function has been added. The parakeratosis inhibitor, pore-shrinking agent, or rough skin preventing/ameliorating agent comprises one or more compounds selected from the group consisting of ?-alanine derivatives and salts thereof. The external composition for skin comprises the one or more compounds selected from the group consisting of ?-alanine derivatives and salts thereof as the above-mentioned parakeratosis inhibitor, pore-shrinking agent, or rough skin preventing/ameliorating agent.Type: ApplicationFiled: April 28, 2006Publication date: September 13, 2012Applicant: Shiseido Company, Ltd.Inventors: Mikiko Kaminuma, Masaru Suetsugu, Toshii Iida, Shinji Inomata
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Publication number: 20120209006Abstract: A process for (R,S)-nicotine is described. Condensation of 1-(but-1-enyl)pyrrolidin-2-one with nicotinic acid ester gave 1-(but-1-enyl)-3-nicotinoylpyrrolidin-2-one which on treatment with an acid and a base gave myosmine. Myosmine was converted to (R,S)-nicotine by reduction followed by N-methylation.Type: ApplicationFiled: April 6, 2011Publication date: August 16, 2012Applicant: Divi's Laboratories LimitedInventors: Murali Krishna Prasad Divi, Gundu Rao Padakandla, Mysore Aswatha Narayana Rao, Hari Babu Katta
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Patent number: 8241680Abstract: Nutraceutical compositions containing anatabine and Yerba maté extract are efficacious for temporarily reducing the desire to smoke, reducing nicotine cravings, the treatment of smoking cessation, tobacco withdrawal symptoms, tobacco dependence, weight loss, and/or related disorders.Type: GrantFiled: June 30, 2010Date of Patent: August 14, 2012Assignee: Rock Creek Pharmaceuticals, Inc.Inventors: Jonnie R. Williams, Curtis Wright
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Publication number: 20120192880Abstract: The invention provides a tobacco composition for use in a smoking article or a smokeless tobacco composition that comprises an extract derived from a component of a plant of the Nicotiana species. The invention also provides smoking articles and smokeless tobacco compositions that include the extracts described herein, and methods for preparing extracts derived from a component of a plant of the Nicotiana species for addition to a tobacco composition.Type: ApplicationFiled: January 28, 2011Publication date: August 2, 2012Inventors: Michael Francis Dube, William Monroe Coleman, III
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Publication number: 20120197022Abstract: (R,S)-Nicotine was resolved through diastereomeric salt formation using dibenzoyl-d-tartaric acid and dibenzoyl-l-tartaric acid to obtain enantiomerically pure (S)-nicotine and (R)-nicotine.Type: ApplicationFiled: April 6, 2011Publication date: August 2, 2012Applicant: Divi's Laboratories LimitedInventors: Murali Krishna Prasad Divi, Gundu Rao Padakandla, Mysore Aswatha Narayana Rao, Hari Babu Katta
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Publication number: 20120152265Abstract: The invention provides a tobacco composition for use in a smoking article or a smokeless tobacco composition that comprises a syrup derived from the stalk of a plant of the Nicotiana species. The invention also provides smoking articles and smokeless tobacco compositions that include the syrups described herein, and methods for preparing syrups derived from the stalk of a plant of the Nicotiana species for addition to a tobacco composition.Type: ApplicationFiled: December 17, 2010Publication date: June 21, 2012Inventors: Michael Francis Dube, William Monroe Coleman, III, Anthony Richard Gerardi
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Publication number: 20120145170Abstract: A method and a system for preparing a tobacco extract for use in an electronic smoking device are provided. A tobacco extract and an electronic smoking device are also provided. The method includes grinding tobacco into granulated particles, and heating purified water. The method further includes injecting the heated purified water through the granulated particles of the tobacco for a predetermined period of time to produce an aqueous solution, and adding purified water to the aqueous solution. Further, the method includes heating the aqueous solution, and injecting the heated aqueous solution through ground tobacco for the predetermined period of time to produce a tobacco extract for use in the electronic smoking device.Type: ApplicationFiled: February 15, 2012Publication date: June 14, 2012Applicant: GLOBAL VAPOR TRADEMARKS, INC.Inventor: Thomas O'Connell
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Publication number: 20110294859Abstract: The present invention provides salt adducts comprising at least one positively charged moiety being a pyridoxine or a derivative thereof and at least one carboxylated 5- to 7-membered lactam ring, optionally additionally substituted, methods of their preparation, and pharmaceutical compositions and medicaments comprising them. Salt adducts of the invention and compositions comprising them may be used to in the treatment of diseases or disorders associated with or inflicted by alcohol consumption.Type: ApplicationFiled: July 29, 2009Publication date: December 1, 2011Applicant: ALCOBRA LTD.Inventors: Rina Yamin, Dalia Megiddo
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Publication number: 20110245493Abstract: The present invention relates to the delivery of drug amines through an inhalation route. Specifically, it relates to aerosols containing drug amines that are used in inhalation therapy. In one aspect of the present invention, a method of delivering an amine drug in an aerosol form is provided. The method comprises: a) heating a coating, which includes an amine drug salt on a substrate contained in a device to a temperature sufficient to volatilize the amine drug from the coating, h) by said heating, forming an amine drug vapor, and c) during said heating, drawing air through said device, condensing said vapor to form aerosol particles containing less than 10% degradation products of the compound.Type: ApplicationFiled: April 1, 2011Publication date: October 6, 2011Applicant: ALEXZA PHARMACEUTICALS, INC.Inventors: Joshua D. RABINOWITZ, Alejandro C. Zaffaroni
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Publication number: 20110237627Abstract: Anatabine is obtained by reacting benzophenoneimine with 3-aminomethyl pyridine to form benzylhydrylidene-pyridin-3-yl-methyl-amine. The benzylhydrylidene-pyridin-3-yl-methyl-amine is treated with a non-nucleophilic base and a dielectrophile, such as cis-1,4-dichloro-2-butene, followed by acidification, then basification, to provide anatabine. The resulting anatabine is substantially free from contaminants and displays good stability. In an alternative embodiment, the benzylhydrylidene-pyridin-3-yl-methyl-amine may be used in the synthesis of other alkaloids such as anabasine, nornicotine, N-methylanabasine, and anabaseine.Type: ApplicationFiled: March 23, 2010Publication date: September 29, 2011Applicant: ROCK CREEK PHARMACEUTICALS, INC.Inventors: Tom Thomas Puthiaparampil, Thomas Kanathkunn David, Muppala Sarveswara Raju
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Publication number: 20110207782Abstract: A nicotine-containing product comprising a pharmaceutically acceptable polymeric substrate, which is able to bind cations, nicotine or a pharmaceutically acceptable nicotine derivative, and pharmaceutically acceptable inorganic cations. It further pertains to a method for the preparation of such a nicotine-containing product and to the use thereof for the preparation of a pharmaceutical product.Type: ApplicationFiled: December 10, 2009Publication date: August 25, 2011Applicant: SIEGFRIED LTD.Inventor: Alexander Franz
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Publication number: 20110136209Abstract: A process for preparing a nicotine-based hapten of formula I or a salt or solvate thereof, wherein n, R1 and R2 have the meanings as indicated in the specification. The nicotine-based hapten forms part of a smoking cessation vaccine.Type: ApplicationFiled: August 6, 2009Publication date: June 9, 2011Inventor: Benjamin Martin
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Patent number: 7888512Abstract: Methods of synthesizing nicotine analogs and derivatives are described. In some embodiments the methods utilize an alkyl or aryl silyl-substituted nicotine analog intermediate. Intermediates useful for the synthesis of nicotine and nicotine analogs are also described.Type: GrantFiled: May 27, 2009Date of Patent: February 15, 2011Assignee: North Carolina State UniversityInventors: Daniel L. Comins, Emilie Despagnet Smith
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Patent number: 7875724Abstract: Methods of synthesizing nicotine analogs and derivatives are described. The methods are particularly useful for the regioselective production of enantiomerically pure nicotine analogs having substituents at the C4 position. Intermediates useful for the synthesis of such compounds are also described.Type: GrantFiled: January 15, 2010Date of Patent: January 25, 2011Assignee: North Carolina State UniversityInventors: Laura S. King, Emilie Smith, Daniel L. Comins
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Publication number: 20100331323Abstract: The present invention provides active compounds for modulating nicotinic acetylcholine receptors and methods of making the same. The methods of preparing the active compounds utilize different intermediate compounds.Type: ApplicationFiled: September 10, 2010Publication date: December 30, 2010Inventors: Daniel L. Comins, Florence F. Wagner, Pauline Ondachi
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Publication number: 20100247653Abstract: The present invention relates to nanoparticles containing nicotine and/or cotinine. The present invention further relates to dispersions containing these nanoparticles. The invention relates in particular to corresponding novel transdermal pharmaceuticals containing nicotine and cotinine in nanoparticulate form, and use thereof for smoking cessation.Type: ApplicationFiled: April 11, 2007Publication date: September 30, 2010Inventors: Hans Lautenschlager, Ilan Elias
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Publication number: 20100113785Abstract: Methods of synthesizing nicotine analogs and derivatives are described. The methods are particularly useful for the regioselective production of enantiomerically pure nicotine analogs having substituents at the C4 position. Intermediates useful for the synthesis of such compounds are also described.Type: ApplicationFiled: January 15, 2010Publication date: May 6, 2010Inventors: Laura S. King, Emilie Smith, Daniel L. Comins
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Publication number: 20100069350Abstract: The present invention relates to certain new pyridin analogues of Formula (I), to processes for preparing such compounds, to their utility as P2Y12 inhibitors and as anti-trombotic agents etc, their use as medicaments in cardiovascular diseases as well as pharmaceutical compositions containing them.Type: ApplicationFiled: July 2, 2007Publication date: March 18, 2010Applicant: ASTRAZENECA ABInventors: Thomas Antonsson, Peter Bach, David Brown, Ruth Bylund, Fabrizio Giordanetto, Lotta Jakobsson, Johan Johansson
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Patent number: 7671209Abstract: Methods of synthesizing nicotine analogs and derivatives are described. The methods are particularly useful for the regioselective production of enantiomerically pure nicotine analogs having substituents at the C4 position. Intermediates useful for the synthesis of such compounds are also described.Type: GrantFiled: October 26, 2007Date of Patent: March 2, 2010Assignee: North Carolina State UniversityInventors: Laura S. King, Emilie Smith, Daniel L. Comins
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Publication number: 20090234129Abstract: Methods of synthesizing nicotine analogs and derivatives are described. In some embodiments the methods utilize an alkyl or aryl silyl-substituted nicotine analog intermediate. Intermediates useful for the synthesis of nicotine and nicotine analogs are also described.Type: ApplicationFiled: May 27, 2009Publication date: September 17, 2009Inventors: Daniel L. Comins, Emilie Despagnet Smith
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Publication number: 20090196886Abstract: The present invention provides a hapten in the form of a novel nicotine derivative that may suitably be conjugated with an appropriate carrier to yield an effective vaccine against nicotine addiction. More particularly, the invention relates to a nicotine derivative of the following formula (I): The present invention also relates to a hapten-carrier conjugate derived from the aforementioned nicotine derivative and a vaccine composition comprising said hapten-carrier conjugate.Type: ApplicationFiled: April 20, 2007Publication date: August 6, 2009Applicant: De Staat Der Nederlanden, Vert. Door De Minister Van VWSInventors: Peter Hoogerhout, Gijsbert Zomer
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Patent number: 7547712Abstract: The present invention relates methods for reducing the adverse effects of nicotine. This application describes the use of nicotine carrier conjugates in decreasing the toxic effects of nicotine on a fetus.Type: GrantFiled: February 26, 2007Date of Patent: June 16, 2009Assignees: Nabi Biopharmaceuticals, United States of America as Represented by the Secretary, DHHS Office of Technology Transfer, National Institutes of HealthInventors: Sofiane Ennifar, Scott Winston, James Terrill, Steve Fuller
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Patent number: 7501520Abstract: A first aspect of the present invention is a method for of making a compound of Formula Ia or Formula Ib: wherein X is halo, by (a) metalating a precursor compound to form an organometallic intermediate, and then reacting the organometallic intermediate with a halogenating agent to produce the compound of Formula Ia or Formula Ib.Type: GrantFiled: January 16, 2007Date of Patent: March 10, 2009Assignee: North Carlina State UniversityInventors: Daniel L. Comins, Florence Fevrier, Emilie Despagnet Smith
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Patent number: 7452541Abstract: The present invention provides compositions comprising a conjugate of a hapten with a carrier in an ordered and repetitive array, and methods of making such compositions. The conjugates and compositions of the invention may comprise a variety of haptens, including hormones, toxins and drugs, especially drugs of addiction such as nicotine. Compositions and conjugates of the invention are useful for inducing immune responses against haptens, which can use useful in a variety of therapeutic, prophylactic and diagnostic regimens. In certain embodiments, immune responses generated using the conjugates, compositions and methods of the present invention are useful to prevent or treat addiction to drugs of abuse and the resultant diseases associated with drug addiction.Type: GrantFiled: May 10, 2005Date of Patent: November 18, 2008Assignee: Cytos Biotechnology AGInventors: Martin F. Bachmann, Patrik Maurer
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Publication number: 20080221085Abstract: Nicotine receptor agonists or analogs or derivatives thereof for treating inflammatory pulmonary diseases, and pharmaceutical compositions including nicotine receptor agonists or analogs or derivatives thereof. Compounds of formula wherein R1, R2, Xa and Ya are as defined herein are also provided.Type: ApplicationFiled: July 15, 2005Publication date: September 11, 2008Applicant: Universite LavalInventors: Yvon Cormier, Evelyne Israel-Assayag, Marie-Renee Blanchet, Rene C. Gaudreault, Philippe Labrie
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Patent number: 7390907Abstract: Compounds having the general structure and compositions containing them, for the treatment of acute, inflammatory and neuropathic pain, dental pain, general headache, migraine, cluster headache, mixed-vascular and non-vascular syndromes, tension headache, general inflammation, arthritis, rheumatic diseases, osteoarthritis, inflammatory bowel disorders, inflammatory eye disorders, inflammatory or unstable bladder disorders, psoriasis, skin complaints with inflammatory components, chronic inflammatory conditions, inflammatory pain and associated hyperalgesia and allodynia, neuropathic pain and associated hyperalgesia and allodynia, diabetic neuropathy pain, causalgia, sympathetically maintained pain, deafferentation syndromes, asthma, epithelial tissue damage or dysfunction, herpes simplex, disturbances of visceral motility at respiratory, genitourinary, gastrointestinal or vascular regions, wounds, burns, allergic skin reactions, pruritus, vitiligo, general gastrointestinal disorders, gastric ulceration, dType: GrantFiled: September 30, 2004Date of Patent: June 24, 2008Assignee: Amgen Inc.Inventors: Ning Chen, Thomas Nixey, Mark H. Norman