- Partially bio-based polyimides from isohexide-derived diamines
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Abstract Novel partially bio-based polyimides were prepared from 2, 5-diamino-2, 5-dideoxy-1, 4: 3, 6-dianhydrosorbitol (diaminoisosorbide, DAIS) dihydrochloride, 2, 5-diamino-2, 5-dideoxy-1, 4: 3, 6-dianhydroiditol (diaminoisoidide, DAII) dihydrochloride
- Ji, Xiaodong,Wang, Zikun,Yan, Jingling,Wang, Zhen
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- NOVEL AZABENZIMIDAZOLE HEXAHYDROFURO[E,2-B]FURAN DERIVATIVES
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Novel compounds of the structural formula (I) are activators of AMP-protein kinase and may be useful in the treatment, prevention and suppression of diseases mediated by the AMPK activated protein kinase. The compounds of the present invention may be usef
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Paragraph 0601
(2015/10/28)
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- MONOFLUORINATED DERIVATIVES OF DIANHYDROHEXITOLS AND PROCESSES FOR MAKING THE SAME
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Novel monofluoro analogs of isosorbide, isomannide and isoidide are described, together with processes for making such monofluoro analogs.
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Paragraph 0041; 0042
(2014/01/08)
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- Dianhydrohexitols: New tools for organocatalysis. Application in enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes
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A series of hydrogen bonding organocatalysts was synthesized from dianhydrohexitol and was used for the first time in organocatalysis for Friedel-Crafts alkylation of indoles with nitroalkenes. Moderate yields and enantioselectivities were achieved. ARKAT
- Chen, Ling-Yan,Guillarme, Stephane,Saluzzo, Christine
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p. 227 - 244
(2013/06/27)
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- Renewable rigid diamines: Efficient, stereospecific synthesis of high purity isohexide diamines
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We report an efficient three-step strategy for synthesizing rigid, chiral isohexide diamines derived from 1,4:3,6-dianhydrohexitols. These biobased chiral building blocks are presently the subject of several investigations (in our and several other groups
- Thiyagarajan, Shanmugam,Gootjes, Linda,Vogelzang, Willem,Van Haveren, Jacco,Lutz, Martin,Van Es, Daan S.
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experimental part
p. 1823 - 1829
(2012/04/04)
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- New chiral imidazolium ionic liquids from isomannide
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New chiral bis and mono-imidazolium ionic liquids derived from isomannide were synthesized. The structural features of the chiral organic cations impart a special arrangement of the chiral cavity. The new chiral chloride salts of isomannide derivatives ar
- Gomes Da Silva,Pereira, M. Manuela A.
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body text
p. 197 - 202
(2011/03/18)
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- Novel, fully biobased semicrystalline polyamides
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Novel, semicrystalline polyamides and co(polyamides) were synthesized from biobased sebacic acid (SA), 2,5-diamino-2,5-dideoxy-1,4;3,6-dianhydroiditol (diaminoisoidide, DAII) as well as from 1,4-diaminobutane (DAB), also known as putrescine in nature. Low
- Jasinska, Lidia,Villani, Maurizio,Wu, Jing,Van Es, Daan,Klop, Enno,Rastogi, Sanjay,Koning, Cor E.
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experimental part
p. 3458 - 3466
(2012/03/26)
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- ISOMANNIDE DERIVATIVES AND THEIR USE AS TASTANTS
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The present invention provides isomannide derivatives having structural formula (I) as shown below and certain subgenera or species thereof, as flavoring agents or tastants, flavor or taste modifiers, and/or flavor/taste enhancers, particularly, savory ("
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Page/Page column 40-41
(2011/02/24)
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- Chiral building blocks from biomass: 2,5-diamino-2,5-dideoxy-1,4-3,6- dianhydroiditol
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An efficient route towards the synthesis of 2,5-diamino-2,5-dideoxy-1,4-3, 6-dianhydroiditol 4 has been developed resulting in significant improvements in both isolated yields and purity when compared to literature procedures. As a consequence, resin-grad
- Thiyagarajan, Shanmugam,Gootjes, Linda,Vogelzang, Willem,Wu, Jing,Van Haveren, Jacco,Van Es, Daan S.
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experimental part
p. 383 - 389
(2011/03/18)
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- Chiral silver and gold rings: Synthesis and structural, spectroscopic, and photophysical properties of Ag and Au metallamacrocycles of bridging NHC ligands
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The synthesis and silver(I) and gold(I) coordination chemistry of a new chiral, bidentate N-heterocyclic carbene (NHC) dehydrohexitol derivative (3) are reported. The imidazolium salt [H23][PF6]2 reacts with Ag2
- Carcedo, Cristina,Knight, James C.,Pope, Simon J. A.,Fallis, Ian A.,Dervisi, Athanasia
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experimental part
p. 2553 - 2562
(2011/06/27)
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- Structure-properties relationship of biosourced stereocontrolled polytriazoles from click chemistry step growth polymerization of diazide and dialkyne dianhydrohexitols
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The design of dialkyne and diazide functionalized dianhydrohexitol stereoisomers (1-6) afforded a new family of starch-based polytriazoles (7-15) with defined stereochemistry through A2 + B2 CuAAC step growth polymerization. The pres
- Besset, Celine,Pascault, Jean-Pierre,Fleury, Etienne,Drockenmuller, Eric,Bernard, Julien
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scheme or table
p. 2797 - 2803
(2011/11/07)
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- Pseudo-peptides derived from isomannide: Inhibitors of serine proteases
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In this paper, we describe the synthesis of a novel class of pseudo-peptides derived from isomannide and several oxazolones as potential inhibitors of serine proteases as well as preliminary pharmacological assays for hepatitis C. Hepatitis C, dengue and West Nile fever are among the most important flaviviruses that share one important serine protease enzyme. Serine proteases belong to the most studied class of proteolytic enzymes and are a primary target in the drug development field. Several pseudo-peptides were obtained in good yields from the reaction of isomannide and oxazolones, and their anti-HCV potential using the HCV replicon-based assay was shown.
- Barros, Thalita G.,Pinheiro, Sergio,Williamson,Tanuri, Amilcar,Gomes Jr.,Pereira, Helena S.,Brindeiro,Neto, Jose B. A.,Antunes,Muri, Estela M. F.
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experimental part
p. 701 - 709
(2010/08/05)
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- Isosorbide-based cholinesterase inhibitors; replacement of 5-ester groups leading to increased stability
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Isosorbide-2-carbamate-5-esters are highly potent and selective butyrylcholinesterase inhibitors with potential utility in the treatment of Alzheimer's Disease (AD). They are stable in human plasma but in mouse plasma they undergo hydrolysis at the 5-ester group potentially attenuating in vivo potency. In this paper we explore the role of the 5-position in modulating potency. The focus of the study was to increase metabolic stability while preserving potency and selectivity. Dicarbamates and 5-keto derivatives were markedly less potent than the ester class. The 2-benzylcarbamate-5-benzyl ether was found to be potent (IC50 52 nM) and stable in the presence of mouse plasma and liver homogenate. The compound produces sustained moderate inhibition of mouse butyrylcholinesterase at 1 mg/kg, IP.
- Dillon, Gerald P.,Gaynor, Joanne M.,Khan, Denise,Carolan, Ciaran G.,Ryder, Sheila A.,Marquez, Juan F.,Reidy, Sean,Gilmer, John F.
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scheme or table
p. 1045 - 1053
(2010/04/26)
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- COMPOUNDS
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A compound of formula (I), or a pharmaceutically acceptable salt, hydrate, complex or pro-drug thereof, wherein one of R1 and R2 is H, and the other is selected from C1-8-alkyl, C3-6-cycloalkyl and C1-8/su
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Page/Page column 81-82; 105
(2009/09/04)
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- COMPOUNDS
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A first aspect of the invention relates to a compound of formula (I), or a pharmaceutically acceptable salt, hydrate, complex or pro-drug thereof, wherein: R3 is selected from cyclopentyl and cyclohexyl; R9 is a substituted 5 or 6-me
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Page/Page column 63
(2009/10/22)
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- FURO [3, 2-B] PYRR0L-3-0NES AS CATHEPSIN S INHIBITORS
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A first aspect of the invention relates to a compound of formula (I), or a pharmaceutically acceptable salt, hydrate, complex or pro-drug thereof, wherein: one of R3 and R4 is H, and the other is selected from C1-6-alkyl,
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Page/Page column 62-63
(2009/10/22)
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- TETRAHYDROFURO [3, 2-B] PYRROL-3-ONE DERIVATIVES AS INHIBITORS OF CYSTEINE PROTEASES
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A compound of formula (I), or a pharmaceutically acceptable salt, hydrate, complex or pro-drug thereof, wherein one of R1 and R2 is H, and the other is selected fromC1-8-alkyl, C3-6-cycloalkyl and C1-8/sub
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Page/Page column 87
(2009/12/27)
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- Stereospecific method for the preparation of dioxa-bicyclooctane compounds
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This invention relates to a new method for the stereospecific thiocarboxylation of organic compounds for the preparation of compounds according to formula (I): wherein a compound of formula (II): is reacted with a compound of formula (IIIa) or (IIIb): the
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Page/Page column 24
(2009/12/27)
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- TETRAHYDROFURO [3, 2 -B] PYRR0L-3-ONES AS CATHEPSIN K INHIBITORS
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The present invention relates to compounds of formula (I), and pharmaceutically acceptable salts thereof, wherein: X is CH or N; one of R1 and R2 is H, and the other is selected from from OR6, SR6, NR6/sup
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Page/Page column 106; 127
(2008/06/13)
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- FURO [3,2-B] PYRROL-3-ONE DERIVATIVES AND THEIR USE AS CYSTEINYL PROTEINASE INHIBITORS
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The present invention relates to compounds of formula (I), and pharmaceutically acceptable salts thereof (I), wherein: R3 is cyclopentyl or cyclohexyl; X is CH or N; and R4 is optionally substituted C1-8 alkyl or optionall
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Page/Page column 45; 58
(2008/06/13)
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- TETRAHYDROFURO (3, 2-B) PYRROL-3-ONE DERIVATIVES AS INHIBITORS OF CYSTEINE PROTEINASES
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Compounds of formula (I) and the use of such compounds in the treatment of a disease selected from osteoporosis, Paget' s disease, Chagas's disease, malaria, gingival diseases, hypercalaemia, metabolic bone disease, diseases involving matrix or cartilage
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Page/Page column 89
(2008/06/13)
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- TETRAHYDROFURO [3, 2-B] PYRR0L-3-ONES AS CATHEPSIN K INHIBITORS
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The present invention relates to compounds of formula (I), and pharmaceutically acceptable salts thereof, wherein: X is CH or N; one of R1 and R2 is H, and the other is selected from H, OR6, SR6, NR6R
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Page/Page column 101
(2008/06/13)
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- TETRAHYDROFURO [3, 2-B] PYRR0L-3-0NE INTERMEDIATES
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The present invention relates to a process for preparing a compound of formula (Ia), (Ib), (Ic) or (Id), or a pharmaceutically acceptable salt, hydrate, solvate, complex or prodrug thereof, said process comprising the steps of: (A) (i) treating a compound
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Page/Page column 90-91
(2008/06/13)
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- FURO [3,2-B] PYRROL-3-ONE DERIVATIVES AND THEIR USE AS CYSTEINYL PROTEINASE INHIBITORS
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The present invention relates to compounds of formula (I), and pharmaceutically acceptable salts thereof, A compound of formula (I), or a pharmaceutically acceptable salt, hydrate, complex or pro-drug thereof (I), wherein: one of R1 and R2 is H, and the other is selected from F and Cl, or R1 and R2 are both F; R3 is selected from cyclopentyl and cyclohexyl; R4 is an optionally substituted 5- or 6-membered monocyclic or an 8- to 10-membered bicyclic aryl or heteroaryl ring which includes up to four heteroatoms. The invention further relates to pharmaceutical compositions comprising compounds of formula (I), and the use of such compounds in the treatment of a disease selected from osteoporosis, Paget's disease, Chagas's disease, malaria, gingival diseases, hypercalaemia, metabolic bone disease, diseases involving matrix or cartilage degradation, and bone cancer disorders such as bone metastases and associated pain.
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Page/Page column 55; 73
(2008/06/13)
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- FURO[3,2-B]PYRROL-3-ONE DERIVATIVES AND THEIR USE AS CYSTEINYL PROTEINASE INHIBITORS
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The present invention relates to compounds of formula (I), and pharmaceutically acceptable salts thereof: wherein: X is CH or N; and R4 is optionally substituted C3-8 alkyl or optionally substituted C3-8 cycloalkyl. The in
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Page/Page column 56
(2008/06/13)
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- FURO [3, 2-B] PYRROL DERIVATIVES
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The present invention relates to compounds of formula (I), and pharmaceutically acceptable salts thereof, wherein: R3 is tert-butylmethyl, sec-butyl or tert-butyl; X is CH or N; and R4 is optionally substituted C1-8 alkyl
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Page/Page column 59
(2008/06/13)
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- Novel carbohydrate-based chiral ammonium ionic liquids derived from isomannide
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This report describes the synthesis and characterization of novel carbohydrate-based chiral ammonium ionic liquids using isomannide as a biorenewable substrate. The diastereomeric interactions of these chiral ammonium ionic liquids with racemic Mosher's a
- Kumar, Vineet,Pei, Cao,Olsen, Carl E.,Schaeffer, Susan J.C.,Parmar, Virinder S.,Malhotra, Sanjay V.
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p. 664 - 671
(2008/09/20)
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- Synthesis and applications of novel bis(ammonium) chiral ionic liquids derived from isomannide
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Carbohydrate-based novel bis(ammonium) chiral ionic liquids have been synthesized by following a straightforward protocol using isomannide as the substrate. Their applications in chiral discrimination and optical resolution of racemates have been establis
- Kumar, Vineet,Olsen, Carl E.,Schaeffer, Susan J. C.,Parmar, Virinder S.,Malhotra, Sanjay V.
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p. 3905 - 3908
(2008/02/11)
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- Synthesis and structure of 1,4:3,6-dianhydro-2-O-p-tosyl-D-mannitol
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1,4:3,6-Dianhydro-2-O-p-tosyl-D-mannitol (3) has been isolated from the reaction of 1,4:3,6-dianhydro-D-mannitol (2) and p-toluenesulfonyl chloride (1:2 mole ratio) in pyridine in 19% yield after fractional crystallization. It crystallizes in the orthorhombic space group P212121 (Z = 4) with a = 6.064(2), b = 8.347(1) and c = 26.455(16) A. Disorder associated with the unsubstituted furanose ring provides two arrangements, rings B and C, with two sets of sites for both the hydroxyl group and a ring carbon atom: the relative occupancy of ring B: ring C = 0.53(1):0.47(1). Distinct H-bonding situations (both intra- and inter-molecular) are associated with the two arrangements. The conformations of the unsubstituted furanose ring with the weaker intramolecular H-bonding (ring B) and the tosyl-substituted ring (ring A) are very similar, being 1:2 mixtures of envelope [3E] and twist forms [3T4]: the stronger H-bonding in ring C results instead in a conformation made up from a 30:70 mixture of E0 and 4T0 forms. The 1H-NMR spectrum for 3 indicates that the average solution conformation is also a mixture of envelope and twist forms and is similar to that of the A/B solid-state arrangement.
- Marr, Andrew,Wardell, James L.,Cox, Philip J.
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p. 161 - 166
(2007/10/03)
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- Dihydro- and Tetrahydrofuran Building Blocks from 1,4:3,6-Dianhydrohexitols. 2. Synthesis of Acetal, Alcohol, Diol, Epoxide, Hydrocarbon, and Lactone Pheromones
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The potential of building blocks 1-3 for synthesis of enantiopure substances is illustrated by their transformation to various insect pheromones featuring functionalities specified in the title.A convenient synthesis of building block 3 from sorbitol is described.
- Paolucci, Claudio,Mazzini, Claudio,Fava, Antonio
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p. 169 - 175
(2007/10/02)
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- Dihydro- and Tetrahydrofuran Building Blocks from 1,4:3,6-Dianhydromannitol. 1. Synthesis of (1S,5R,7R)-endo-(-)- and (1S,5R,7S)-(-)-exo-Brevicomin and (R)-(+)-Dodecanolide
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The eliminative ring fission of iodides derived from 1,4:3,6-dianhydromannitol has been exploited for preparing three enantiomerically pure species, 1-3, which feature a di- or tetrahydrofuran moiety and one or two stereogenic centers.These species are extremely versatile building blocks for the construction of natural products.Their potential was demonstrated by the synthesis of the title insect pheromones.
- Cere, Vanda,Mazzini, Claudio,Paolucci, Claudio,Pollicino, Salvatore,Fava, Antonino
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p. 4567 - 4571
(2007/10/02)
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- 1,4:3,6-DIANHYDRO-2,5-DIDEOXY-2,5-BIS(DIPHENYLPHOSPHINO)-L-IDITOL. A NEW CHIRAL LIGAND FOR ASYMMETRIC HYDROGENATION WITH RHODIUM COMPLEXES AS CATALYSTS
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A new chiral 1,4-diphosphine, 1,4:3,6-dianhydro-2,5-dideoxy-2,5-bis(diphenylphosphino)-L-iditol, has been prepared from D-mannitol.Rhodium complexes of this ligand are asymmetric homogeneous hydrogenation catalysts for dehydroamino acids, giving (S)-amino acids in 21-58percent optical yields.
- Bakos, Jozsef,Heil, Balint,Marko, Laszlo
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p. 249 - 252
(2007/10/02)
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