- Protecting-Group-Directed Regio- and Stereoselective Oxymercuration-Demercuration: Synthesis of Piperidine Alkaloids Containing 1,2- and 1,3-Amino Alcohol Units
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An efficient synthesis of naturally occurring 1,2- and 1,3-amino alcohol unit containing 2-substituted piperidine alkaloids and their analogues has been developed from l -pipecolinic acid. The protocol describes the regio- and stereoselective oxymercuration-demercuration of 2-alkenyl piperidines based on protecting groups to give piperidine alkaloids as a key step.
- Bugde, Sandesh T.,Volvoikar, Prajesh S.,Tilve, Santosh G.
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p. 1113 - 1122
(2017/12/06)
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- 2-(1,2,3-TRIAZOL-2-YL)BENZAMIDE AND 3-(1,2,3-TRIAZOL-2-YL)PICOLINAMIDE DERIVATIVES AS OREXIN RECEPTOR ANTAGONISTS
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The present invention relates to 2-(1,2,3-triazol-2-yl)benzamide and 3-(1,2,3-triazol-2-yl)picolinamide derivatives of formula (I) wherein Ar1, Q, and R1 to R5 are as described in the description, to their preparation, to
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Paragraph 0516; 0517
(2015/06/17)
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- 2-(1,2,3-TRIAZOL-2-YL)BENZAMIDE AND 3-(1,2,3-TRIAZOL-2-YL)PICOLINAMIDE DERIVATIVES AS OREXIN RECEPTOR ANTAGONISTS
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The present invention relates to 2-(1,2,3-triazol-2-yl)benzamide and 3-(1,2,3-triazol-2- yl)picolinamide derivatives of formula (I) Formula (I) wherein Ar1, Q, and R1 to R5 are as described in the description, to their pre
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Page/Page column 90
(2013/05/23)
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- A concise diastereoselective approach to (+)-dexoxadrol, (-)-epi-dexoxadrol, (-)-conhydrine and (+)-lentiginosine from (-)-pipecolinic acid
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A new diastereoselective pathway for the total synthesis of (+)-dexoxadrol, first asymmetric synthesis of (-)-epi-dexoxadrol and formal synthesis of conhydrine and (+)-lentiginosine is presented using commercially available (-)-pipecolinic acid. The key reactions utilized are Sharpless asymmetric dihydroxylation and Wittig reaction. The paper further describes the study of effect of protecting groups on dihydroxylation of a terminal olefin in piperidine ring system.
- Bhat, Chinmay,Tilve, Santosh G.
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p. 10876 - 10883
(2014/01/06)
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- Henry-Nef reaction: A practical and versatile chiral pool route to 2-substituted pyrrolidine and piperidine alkaloids
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The paper describes the synergistic protocol developed by combinatorial Henry and Nef reaction for the synthesis of 2-substituted pyrrolidine and piperidine alkaloids containing 1,3-aminoketone and 1,3-amino alcohol units. The utility of the protocol is demonstrated by asymmetric synthesis of 12 natural products of which asymmetric synthesis of (-)-N-methylpelletierine is presented for the first time. The one-carbon homologation described also provides an alternate route for the synthesis of key intermediates homoprolinol and homopipecolinol used as synthetic precursors for several alkaloids and construction of β-amino acids from α-amino acids.
- Bhat, Chinmay,Tilve, Santosh G.
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p. 6129 - 6143
(2013/07/27)
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- Stereoselective syntheses of L-pipecolic acid and (2S,3S)-3- hydroxypipecolic acid from a chiral n-imino-2-phenyl-1,2-dihydropyridine intermediate
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"Chemical Equation Presented" Stereoselective syntheses of L-pipecolic acid and (2S,3S)3-hydroxypipecolic acid were achieved from a chiral AMmino-2-phenyl-l,2-dihydropyridine intermediate. The 3-hydroxy substituent of the latter amino acid was introduced, by hetero-Diels-Alder reaction of singlet, oxygen with the 1,2-dihydropyridine.
- Lemire, Alexandre,Charette, Andre B.
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supporting information; experimental part
p. 2077 - 2080
(2010/06/16)
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- Substituted Pyrimidine and Triazine Compounds
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Substituted pyrimidine and triazine compounds corresponding to formula I wherein R1, R2, R3, R4a, R4b, R5a, R5b, R7, R8, R9a, R9b, R10, R11, A, a, b, s, t, V, W1, W2 and W3 have defined meanings, pharmaceutical compositions comprising such compounds, a process for preparing such compounds, and the use of such compounds and compositions to treat or inhibit pain and/or other disorders or disease states.
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Page/Page column 34
(2010/07/10)
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- Substituted Spiroamine Compounds
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Substituted spiroamine compounds corresponding to the formula (I) In which m, n, o, p, Q, r, s, t, R1, R2, R3, R4a, R4b, R5a, R5b, R6a, R6b, R7, R8, R9, R10 and R11 have defined meanings; a process for the preparation of such compounds, pharmaceutical compositions containing such compounds and the use of substituted spiroamines for the treatment or inhibition of pain and/or other conditions mediated by the bradykinin 1 receptor.
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Page/Page column 30
(2010/05/13)
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- Substituted Sulfonamide Compounds
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Substituted sulfonamide compounds corresponding to the formula I: processes for the preparation thereof, pharmaceutical composition containing these compounds and the use of substituted sulfonamide compounds for the preparation of pharmaceutical compositions.
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Page/Page column 46-47
(2009/10/17)
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- Substituted Sulfonamide Compounds
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Substituted sulfonamide compounds corresponding to formula I: a process for their preparation, pharmaceutical compositions comprising such compounds, and the use of such substituted sulfonamide compounds in pharmaceutical compositions for the treatment of pain or other disorders or diseases that are mediated at least in part by B1R receptors.
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Page/Page column 77
(2009/10/30)
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- SUBSTITUTED SULFONAMIDE COMPOUNDS
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Substituted sulfonamide compounds corresponding to formula I processes for the preparation thereof, pharmaceutical compositions containing these compounds, and the use of such substituted sulfonamide compounds in pharmaceutical compositions for the treatment and/or inhibition of pain and other conditions at least partly mediated by the bradykinin 1 receptor
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Page/Page column 86-87
(2009/10/30)
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- SUBSTITUTED SULFONAMIDE DERIVATIVES
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The invention relates to substituted sulfonamide derivatives, processes for the preparation thereof, medicaments containing these compounds and the use of substituted sulfonamide derivatives for the preparation of medicaments.
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Page/Page column 100-101
(2009/11/29)
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- SUBSTITUTED SULFONAMIDE DERIVATIVES
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The invention relates to substituted sulfonamide derivatives of the general formula (I'); processes for their preparation, medicaments containing these compounds, and the use of substituted sulfonamide derivatives for the preparation of medicaments
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Page/Page column 96; 97
(2009/08/16)
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- A short synthesis of conformationally constrained unnatural bicyclic amino acids containing a nitrogen atom at the ring juncture: (9aR)- and (9aS)-octahydropyrido[1,2-a]pyrazine-(3S)-carboxylic acids (Opc)
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A short and efficient route to conformationally constrained amino acid analogues, (9aR)- and (9aS)-octahydropyrido[1,2-a]pyrazine-(3S)-carboxylate (Opc) has been developed. The new bicyclic amino acid derivatives can be stored and utilized as a modular unit for the construction of unnatural oligopeptides using conventional peptide coupling methods. Georg Thieme Verlag Stuttgart.
- Soon, Mog So,Yeom, Chang-Eun,Seong, Mi Cho,Soo, Young Choi,Young, Keun Chung,Kim, B. Moon
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p. 702 - 706
(2008/12/20)
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- 1-Hydroxyalkyl-3-phenylthioureas as novel HDL-elevating agents
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A series of 1-hydroxyalkyl-3-phenylthiourea analogs were prepared and evaluated as HDL-and Apo A-I-elevating agents. Derivatives 5h, 7j, 7n, and 7o were found to be as effective or superior to gemfibrozil (1).
- Coppola, Gary M.,Damon, Robert E.,Eskesen, J. Bruce,France, Dennis S.,Paterniti Jr., James R.
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p. 809 - 812
(2007/10/03)
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- QUINAZOLINE DERIVATIVES AS ANTITUMOR AGENTS
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A quinazoline derivative of the formula (I): (A chemical formula should be inserted here - please see paper copy enclosed) Formula I wherein the substituents are as defined in the text for use in the production of an anti proliferative effect which effect is produced alone or in part by inhibiting erbB2 receptor tyrosine kinase in a warm blooded animal such as man.
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Page/Page column 122
(2008/06/13)
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- Efficient Synthesis of Chiral Isoquinoline and Pyrido[1,2-b]-isoquinoline Derivatives via Intramolecular Heck Reactions
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The palladium(0)-catalyzed reaction of derivatives of γ-amino-α,β-unsaturated esters bearing an N-(2-iodobenzoyl) substituent results in an intramolecular Heck reaction, the outcome of which depends on the structure of the substrate as well as on the expe
- Sanchez-Sancho, Francisco,Mann, Enrique,Herradon, Bernardo
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p. 360 - 368
(2007/10/03)
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- A general synthesis of enantiopure 1,2-aminoalcohols via chiral morpholinones
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Eleven optically active 1,2-aminoalcohols 20a-i and 26b-c were prepared from D-phenylglycine via cyclic imines 7b-i (or enamine 7a). The key step of the strategy is the diastereoselective reduction of chiral oxazinones 7a-i.
- Segat-Dioury, Fabienne,Lingibé, Olivier,Graffe, Bernadette,Sacquet, Marie-Claude,Lhommet, Gérard
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p. 233 - 248
(2007/10/03)
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- Asymmetric Synthesis with Chiral Hydrogenolysable Amines: A New Route to Enantiopure Cyclic β-Amino Alcohols
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Enantiopure prolinol and pipecolinol have been obtained via diastereoselective chemical reduction of chiral 2,3-dihydro-6H-1,4-oxazin-2-ones (5).
- Lingibe, Olivier,Graffe, Bernadette,Sacquet, Marie-Claude,Lhommet, Gerard
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p. 1931 - 1934
(2007/10/02)
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- A NEW SYNTHESIS OF OPTICALLY ACTIVE β-MERCAPTOCARBOXYLIC ACID ESTERS
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Synthesis of optically active β-mercaptocarboxylic acid esters has been achieved by a new method utilizing optically active N-methoxycarbonylpiperidine derivative as a template which can be prepared from L-lysine by anodic oxidation.
- Shono, Tatsuya,Matsumura, Yoshihiro,Fujita, Tetsuhiro
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p. 6723 - 6726
(2007/10/02)
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- ENZYME-MEDIATED ENANTIOSELECTIVE ACYLATION OF SECONDARY AMINES IN ORGANIC SOLVENTS
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Porcine pancreatic lipase (PPL) and lipase Amano P catalyze the enantioselective acylation of cyclic 1,2- and 1,3-amino alcohol derivatives in organic solvents.The enantiomeric excesses (ee's) were shown to depend on the enzyme, reaction time, temperature and type of substrate.
- Asensio, Gregorio,Andreu, Cecilia,Marco, J. Alberto
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p. 4197 - 4198
(2007/10/02)
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