- Regioselective C-2 and C-6 substitution of (S)-nicotine and nicotine derivatives
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(Chemical Equation Presented) Regioselective deprotonations of (S)-nicotine and derivatives at the C-2 and C-6 positions of the pyridine ring were performed in good to excellent yields. These methodologies allow the direct introduction of a plethora of fu
- Fevrier, Florence C.,Smith, Emilie D.,Comins, Daniel L.
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- Synthesis of nornicotine, nicotine and other functionalised derivatives using solid-supported reagents and scavengers
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The sequential use of solid-supported reagents and scavengers has led to an efficient synthesis of the natural products nornicotine 1, nicotine 2 and further fuctionalised derivatives. Also reported is a diastereoselective route to both enantiomers of nicotine 2.
- Baxendale, Ian R.,Brusotti, Gloria,Matsuoka, Masato,Ley, Steven V.
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- 6-Pyridylnicotine and bis-6,6'-nicotine - new chiral 2,2'-bipyridines
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Starting from (-)-nicotine, two new 2,2'-bipyridine ligands 6 and 7 with chiral pyrrolidine side chains have been synthesized. The stoichiometric complexation by palladium(II) or mercury(II) ions gives the bipyridyl complexes 8 and 9.
- Schmidt, Boris,Neitemeier, Vera
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- A five-step synthesis of (S)-macrostomine from (S)-nicotine
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A concise synthesis of (S)-macrostomine has been accomplished in five steps from natural nicotine in 19% overall yield via a pyridyne Diels - Alder cycloaddition reaction as the key step. A Kumada cross-coupling reaction on a 1-chloroisoquinoline intermediate provided the natural product.
- Enamorado, Monica F.,Ondachi, Pauline W.,Comins, Daniel L.
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- Novel and potent 6-chloro-3-pyridinyl ligands for the α4β2 neuronal nicotinic acetylcholine receptor
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1-[(6-Chloro-3-pyridinyl)methyl]-2-imidazolidine (1), the N-desnitro metabolite of the major insecticide imidacloprid, is known to have similar potency to that of (-)-nicotine as an inhibitor of [3H](-)-nicotine binding at the rat recombinant α4β2 neuronal nicotinic acetylcholine receptor (nAChR); IC50 values in the present study are 3.8 nM for (-)-nicotine, 6.0 nM for 1, and 155 nM for imidacloprid. Synthesis of new analogues of 1, modified only in the heterocyclic moiety (five-, six-, or seven-membered rings with NH, S, O, and CH2 substituents), gave compounds varying from 4- fold higher potency (2-iminothiazole analogue 10) to > 6000-fold less active than (-)-nicotine. Other potent N-[(6-chloro-3-pyridinyl)methyl] compounds are those in which the heterocyclic imine is replaced with pyrrolidine (19) (IC50 9 nM) or trimethylammonium (22) (IC50 18 nM). A novel conversion of (-)-nicotine to its 6-chloro analogue increased the potency 2-fold. These 6- chloro-3-pyridinyl compounds are of interest as novel nAChR probes and potential metabolites of candidate insecticides.
- Latli, Bachir,D'Amour, Kevin,Casida, John E.
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- CONJUGATES FOR PREVENTION OR TREATMENT OF NICOTINE ADDICTION
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PROBLEM TO BE SOLVED: To provide nicotine-derived haptens, nicotine-derived hapten-carrier conjugates, and vaccine compositions containing the conjugates, which are useful for enhancing smoking quit rates or reducing smoking relapse rates in smoking cessa
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Paragraph 0136; 0137
(2016/10/09)
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- INHIBITORS OF BRUTON'S TYROSINE KINASE
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This application discloses compounds according to generic Formula I: wherein the variables are defined as described herein, and which inhibit Btk. The compounds disclosed herein are useful to modulate the activity of Btk and treat diseases associated with
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Page/Page column 62; 63
(2013/03/26)
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- Inhibitors of Bruton's Tyrosine Kinase
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This application discloses 6-(2-Hydroxymethyl-phenyl)-2-methyl-2H-pyridazin-3-one derivatives according to generic Formula I: wherein, variables X, R, and Y4, are defined as described herein, which inhibit Btk. The compounds disclosed herein are useful to modulate the activity of Btk and treat diseases associated with excessive Btk activity. The compounds are further useful to treat inflammatory and auto immune diseases associated with aberrant B-cell proliferation, such as rheumatoid arthritis. Also disclosed are compositions containing compounds of Formula I and at least one carrier, diluent or excipient.
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Page/Page column 82
(2012/03/08)
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- CONJUGATES FOR THE PREVENTION OR TREATMENT OF NICOTINE ADDICTION
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The present invention relates in part to nicotine-derived hapten-carrier conjugates of the formula (III): wherein m, n, W, -(spacer)-, X* and Y are as defined in the description. In certain embodiments, said nicotine-derived hapten-carrier conjugates can
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- NICOTINE-BASED COMPOUNDS USEFUL FOR ASYMMETRIC SYNTHESIS
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Chiral amino alcohol and amino phosphine compounds are provided herein, which compounds are useful for asymmetric synthesis.
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Page/Page column 24-27
(2010/04/27)
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- Hydroxyarylketones via Ring-Opening of lactones with aryllithium reagents: An expedient synthesis of ( )-anabasamine
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The regioselective ring-opening of lactones (δ-valerolactone and γ-butyrolactone) with aryllithium reagents is reported for the construction of a series of δ-hydroxy aryl ketones and γ-hydroxy aryl ketones. Application of this method for the expeditious syntheses of ( )-anabasamine and its nicotine-related analogue are also described.
- Miao, Lei,Dimaggio, Stassi C.,Trudell, Mark L.
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experimental part
p. 91 - 97
(2010/06/14)
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- Expedient five-step synthesis of SIB-1508Y from natural nicotine
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Altinicline (SIB-1508Y), an anti-Parkinson's agent, was prepared in five steps from natural nicotine in 32% overall yield via a regioselective substitution of the pyridine ring of (S)-nicotine.
- Wagner, Florence F.,Comins, Daniel L.
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p. 8673 - 8675
(2007/10/03)
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- Regioselective halogenation of nicotine and substituted nicotines
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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 w
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Page/Page column 4
(2008/06/13)
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- Method of producing 6-substituted (s)-Nicotine derivatives and intermediate compounds
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A method of producing a 6-substituted (S)-nicotine derivative with the general formula (III), wherein R is an optionally substituted alkyl, alkenyl, alkynyl, amido or amino group, optionally coupled to a carrier protein, is disclosed. An intermediate comp
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- Renewable functionalized pyridines derived from microbial metabolites of the alkaloid (5)-nicotine
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(S)-Nicotine, which is present in concentrations of 2-8 % in dried leaves of certain tobacco plants, was used as a starting material for the biocatalytic production of renewable functionalized pyridines. Key microbial metabolites of (5)-nicotine, such as 6-hydroxy-(5)-nicotine and 4-[(6-hydroxypyridine)-3-yl]-4-oxobutyrate were used in subsequent chemical steps for the preparation of a wide variety of 2,5-di- or 2,3,5-tri-substituted pyridines.
- Roduit, Jean-Paul,Wellig, Alain,Kiener, Andreas
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p. 1687 - 1702
(2007/10/03)
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