- Development of a Dual-Acting Antibacterial Agent (TNP-2092) for the Treatment of Persistent Bacterial Infections
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The clinical management of prosthetic joint infections and other persistent bacterial infections represents a major unmet medical need. The rifamycins are one of the most potent antibiotic classes against persistent bacterial infections, but bacteria can
- Ma, Zhenkun,Lynch, Anthony Simon
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p. 6645 - 6657
(2016/08/05)
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- The design and discovery of novel amide CCR5 antagonists
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The synthesis of a range of novel amine-containing structures and their primary potency as inhibitors of HIV-1 fusion via blocking of the CCR5 receptor is described. The development of the medicinal chemistry strategy and SAR's which led to the identification of the piperidine amide compounds 33 and 36 as excellent leads for further evaluation is described, along with key physicochemical data which highlighted their lead potential.
- Pryde, David C.,Corless, Martin,Fenwick, David R.,Mason, Helen J.,Stammen, Blanda C.,Stephenson, Peter T.,Ellis, David,Bachelor, David,Gordon, David,Barber, Christopher G.,Wood, Anthony,Middleton, Donald S.,Blakemore, David C.,Parsons, Gemma C.,Eastwood, Rachel,Platts, Michelle Y.,Statham, Keith,Paradowski, Kerry A.,Burt, Catherine,Klute, Wolfgang
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supporting information; scheme or table
p. 1084 - 1088
(2009/08/07)
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- METHOD FOR PRODUCTION OF OPTICALLY ACTIVE 3-AMINO-NITROGENATED COMPOUND
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Aiming at production of an optically active 3-amino nitrogen-containing compound which is useful as an intermediate in synthesis of medicines and pesticides, in particular, an optically active 1-protected-3-aminopyrrolidine derivative, from an inexpensive and readily available raw material by a process which is efficient and can be practiced industrially, an optically active 3-amino nitrogen-containing compound is produced by performing a reaction of an optically active 3-substituted nitrogen-containing compound with ammonia, methylamine, ethylamine or dimethylamine in the presence of water. In addition, a 1-protected-3-aminopyrrolidine derivative is produced by performing a reaction of an optically active 1-protected-3-(sulfonyloxy)pyrrolidine derivative with ammonia, methylamine, ethylamine, or dimethylamine in the presence of methanol, ethanol, n-propanol, or isopropanol under a pressure of less than 30 barr.
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Page/Page column 18
(2009/05/29)
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- 8-METHOXY-9H-ISOTHIAZOLO[5,4-B]QUINOLINE-3,4-DIONES AND RELATED COMPOUNDS AS ANTI-INFECTIVE AGENTS
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The invention provides compound and salts of Formula (I) and (II), disclosed herein, which includes compounds of Formula (A) and Formula (B) such compounds possess useful antimicrobial activity. The variables R2, R3, R5, R
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Page/Page column 70
(2010/11/25)
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- Synthesis of beta-proline like derivatives and their evaluation as sodium channel blockers
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(Chemical Equation Presented) A simple and convenient procedure for the preparation of beta-proline like derivatives in their racemic and optically active forms has been reported. The compounds have been screened for their potential activity as sodium cha
- Muraglia, Marilena,Franchini, Carlo,Corbo, Filomena,Scilimati, Antonio,Sinicropi, Maria Stefania,De Luca, Annamaria,De Bellis, Michela,Camerino, Diana Conte,Tortorella, Vincenzo
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p. 1099 - 1103
(2008/09/17)
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- QUINOLONE ANTIBACTERIAL AGENTS
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Compounds of formula (I) wherein A is formula (II), formula (III) or formula (IV), and B is formula (V), formula (VI), or formula (VII), can be used in a variety of applications including use as antibacterial agents.
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Page/Page column 87; 88; 119
(2010/02/12)
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- ANTIBACTERIAL AMINOQUINAZOLIDINEDIONE DERIVATIVES
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Compounds of formula (I) wherein: A is Formula (II), Formula (III), or Formula (IV) and B is Formula (V), Formula (VI), or Formula (VII), can be used in a variety of applications including use as antibacterial agents.
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Page/Page column 115; 116; 147
(2010/02/12)
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- Synthesis of racemic and enantiomeric 3-pyrrolidinyl derivatives of purine and pyrimidine nucleobases
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The present work relates to the synthesis of pyrrolidine nucleoside analogs. Starting from malic acid, we have elaborated a high-yield synthesis of racemic and enantiomeric N-protected 3-pyrrolidinols and their O-mesyl derivatives as key compounds for alk
- Kocalka, Petr,Pohl, Radek,Rejman, Dominik,Rosenberg, Ivan
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p. 805 - 808
(2007/10/03)
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- Cyclization method for the synthesis of pyrrolidine derivative compounds
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A method for preparing pyrrolidine derivatives comprising cyclizing a compound of formula (I): wherein R1 represents a mesyl group, a tosyl group, a nosyl group or a trityl group; R2 and R4, which can be the same or different, represent a hydrogen atom, a halogen atom, a hydroxyl group, an alkyloxy group, an aryloxy group, a mesyl group, a tosyl group, a nosyl group, a trityl group, an alkyl group or together represent a double bond; R3 and R5, which can be the same or different, represent a hydrogen atom, a halogen atom, a hydroxyl group, an alkyloxy group, an aryloxy group, a mesyl group, a tosyl group, a nosyl group, a trityl group, an alkyl group or together represent a saturated or unsaturated C3-9 cycloalkyl group or a C5-10 aryl group, said cycloalkyl or aryl groups are optionally substituted by a C1-5 alkyl group, a halogen atom, a hydroxy group, a C1-5 alkoxy group and optionally have one or more heteroatoms selected from the group consisting of O, N, S and Si; and n is a whole number of 1, 2 or 3, in the presence of: a) a catalyst, b) a primary amine of formula R6NH3 wherein R6 represents a hydrogen atom, an alkyl group, an aryl group or an alkylaryl group and c) a base, in a solvent to obtain pyrrolidine derivative of formula (II) below: wherein R2, R3, R4 R5 and n have the same meanings as in formula (I) and R6 represents a hydrogen atom, an alkyl group, an aryl group or an alkylaryl group.
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- Derivatives of azetidine and pyrrolidine
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The invention relates to a compound having formula (I) wherein A is an optionally unsaturated 5- or 6-membered ring, which may comprise a heteroatom selected from N, O and S and which may be substituted with oxo or (1-6C)alkyl; R1, R2and R3are independently H, (1-6C)alkyl, (1-6C)alkoxy, (1-6C)alkoxy(1-6C)-alkyl, carbo(1-6C)alkoxy or halogen; X is O or S; and n is 1 or 2; or a pharmaceutically acceptable salt thereof, with the exception of 3-(naphth-1-yl-oxy)-pyrolidin and 3-(5,6,7,8-tetmhydro-naphth-1-yl-oxy)-pyrolidin. The compounds of the invention have antidepressant activity and can be used in treating or preventing serotonin-related diseases.
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- Synthesis and structure-activity relationships of naphthamides as dopamine D3 receptor ligands
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A series of naphthamides were synthesized, and the affinities of these compounds were determined for dopamine D2 and D3 receptors using radioligand binding techniques. The naphthamide compounds that were prepared include N-(1- alkylp
- Huang,Luedtke,Freeman,Wu,Mach
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p. 1815 - 1826
(2007/10/03)
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- Process for making 3-amino-pyrolidine derivatives
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The invention is concerned with a process for making a compound of formula STR1 wherein R1 is hydrogen, alkyl, cyclo-alkyl, alkenyl, aryl or an amino protecting group; and R2, R3 each independently is hydrogen, alkyl, cyclo-alkyl, alkenyl or aryl; by reacting a compound of the formula STR2 wherein X is a protected hydroxy group; with R1 NH2 to form a compound of formula STR3 wherein X and R1 are described herein above; and then reacting the compound of formula III with R2 R3 NH under pressure to form the compound of formula I. These compounds are valuable intermediates useful in making cephalosporin derivatives.
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- A practical ex-chiral-pool synthesis of β-proline and homo-β-proline
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Starting from aspartic acid an efficient synthesis of enantiomerically pure β-proline and homo-β-proline is described. The key step of the synthesis includes formation of the 1,4-biselectrophile 6, followed by rearrangement via the aziridinium intermediate 7 and ring closure to give the pyrrolidinium salt 9a which can serve as a common precursor for both target compounds.
- Thomas, Christoph,Orecher, Florian,Gmeiner, Peter
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p. 1491 - 1496
(2007/10/03)
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- Derivatives of azetidine and pyrrolidine
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The invention relates to a compound having the formula I wherein A is an optionally unsaturated 5- or 6-membered ring, which may comprise a heteroatom selected from N, O and S and which may be substituted with oxo or (1-6C)alkyl; R1, R2and R3are independently H, (1-6C)alkyl, (1-6C)alkoxy, (1-6C)alkoxy-(1-6C)alkyl, carbo(1-6C)alkoxy or halogen; X is O or S; and n is 1 or 2; or a pharmaceutically acceptable salt thereof, with the exception of 3-(naphth-1-yl-oxy)-pyrrolidin and 3-(5,6,7,8-tetrahydro-naphth-1-yl-oxy)-pyrrolidin., The compounds of the invention have antidepressant activity and can be used in treating or preventing serotonin-related diseases.
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- Preparative and structural chemistry of chiral 3-(diphenylphosphanyl)pyrrolidines and their palladium(II) complexes
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The preparation of both enantiomers of 3-diphenylphosphanylpyrrolidine (2) and several N-substituted derivatives together with two Pd complexes of this ligand is reported. From L-malic acid and L-hydroxyproline both enantiomers of 3-hydroxypyrrolidine are prepared without any problems due to epimerization. KPPh2 in the presence of LiCl is shown to be the most effective reagent for the synthesis of 2. The reported X-ray structure determinations of PdI2 complexes show a rather rigid bicyclic hetero-norbornane skeleton. The flexibility of the other parts of the molecules is obvious in several polymorphs revealed by this method. This polymorphism is additionally investigated by a 31P-CP-MAS study. From solution 'H-, 13C- and 31P-NMR studies it is concluded that the bicyclic hetero-norbornane skeleton is retained in solution. VCH Verlagsgesellschaft mbH.
- Nagel, Ulrich,Nedden, Hans Guenter
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p. 385 - 397
(2007/10/03)
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- Process for chiral 3-(1-amino-1,1-bisalkylmethyl)-1-substituted-pyrrolidines
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The process for the preparation of chiral 3-(1-amino-1,1-bisalkylmethyl)-1-substituted-pyrrolidines used as key intermediates for the preparation of naphthyridine and quinolone antibacterial agents which comprises reacting readily available chiral 1-subst
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- An Efficient Method for the Synthesis of (R)-3-(1-Amino-1-methylethyl)pyrrolidines for the Antiinfective Agent, PD 138312
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Methylcerium dichloride has been found to undergo bis addition to nitriles to produce tertiary carbinamines with retention of optical purity at the ? position.This result is used in the development of a short, economical synthesis of the 1,8-naphthyridine antiinfective agent, PD 138312.
- Fedij, Victor,Lenoir, Edward A.,Suto, Mark J.,Zeller, James R.,Wemple, James
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p. 1131 - 1134
(2007/10/02)
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