- Novel degradable poly(ethylene glycol) hydrogels for controlled release of protein
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Hydrogels have become increasingly important in the biomedical field. This paper describes synthesis and characterization of two types of novel degradable poly(ethylene glycol) (PEG) hydrogels with potential utility as delivery carriers for bioactive drug
- Zhao,Harris
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- Stereoselective Synthesis of cis-2,5-Disubstituted Tetrahydrofuran-3-ones via an Acyl Radical Cyclization
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Treatment of the acyl selenide 7 with triphenyltin hydride and triethylborane generates the acyl radical which undergoes 5-exo trigonal cyclization to afford the 2,5-disubstituted tetrahydrofuran-3-ones 10a/b in 97percent yield as a 94:6 mixture of diastereoisomers.
- Andrew Evans, P.,Roseman, Jamine D.
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- CARRIER-LINKED PRODRUGS HAVING REVERSIBLE CARBOXYLIC ESTER LINKAGES
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The invention provides a carrier-linked prodrugs, wherein the biologically active moieties comprise at least one carboxylic acid and wherein the linkage between the drug moiety and linker is in the form of an ester wherein the hydroxyl group required for ester formation is provided by the linker moiety and the carboxyl group required for ester formation is provided by the drug moiety. The hydroxyl group of the linker is sterically hindered by the presence of an alkyl or aryl group on the carbon directly bound to or adjacent to the carbon carrying the hydroxyl group (a-carbon). The steric effect of the alkyl or aryl group enables greater control of the rate of hydrolytic degradation of such carrier-linked prodrugs.
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Paragraph 0267-0268
(2020/05/30)
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- Sustained release composition of prostacyclin
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The present invention relates to sustained release compositions of prostacyclin, as well as uses thereof, in particular for the prevention and/or treatment of pulmonary arterial hypertension.
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Page/Page column 63; 64
(2018/03/28)
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- Carrier-linked treprostinil prodrugs
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The present invention relates to prodrugs or a pharmaceutically acceptable salt thereof comprising a covalent treprostinil carrier conjugate as well as pharmaceutical composition comprising said compounds. The compounds may be used as medicaments, especially for diseases or disorders which can be treated by treprostinil, such as pulmonary arterial hypertension (PAH).
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Page/Page column 95; 96
(2017/02/28)
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- SUSTAINED RELEASE COMPOSITION OF PROSTACYCLIN
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The present invention relates to sustained release compositions of prostacyclin, as well as uses thereof, in particular for the prevention and/or treatment of pulmonary arterial hypertension.
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Page/Page column 87
(2013/03/26)
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- CARRIER-LINKED TREPROSTINIL PRODRUGS
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The present invention relates to prodrugs or a pharmaceutically acceptable salt thereof comprising a covalent treprostinil carrier conjugate as well as pharmaceutical composition comprising said compounds. The compounds may be used as medicaments, especially for diseases or disorders which can be treated by treprostinil, such as pulmonary arterial hypertension (PAH).
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Page/Page column 119; 120
(2013/03/26)
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- CARRIER-LINKED PRODRUGS HAVING REVERSIBLE CARBOXYLIC ESTER LINKAGES
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The invention provides a carrier-linked prodrugs, wherein the biologically active moieties comprise at least one carboxylic acid and wherein the linkage between the drug moiety and linker is in the form of an ester wherein the hydroxyl group required for ester formation is provided by the linker moiety and the carboxyl group required for ester formation is provided by the drug moiety. The hydroxyl group of the linker is sterically hindered by the presence of an alkyl or aryl group on the carbon directly bound to or adjacent to the carbon carrying the hydroxyl group (α-carbon). The steric effect of the alkyl or aryl group enables greater control of the rate of hydrolytic degradation of such carrier-linked prodrugs.
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Page/Page column 84
(2013/03/26)
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- Selective esterifications of primary alcohols in a water-containing solvent
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Oxyma and an oxyma derivative, (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 2-cyano-2-(hydroxyimino)acetate (5b), displayed a remarkable effect on selective esterifications of primary alcohols. A wide range of carboxylic acids could be esterified with primary alcohols by using EDCI, NaHCO3, and Oxyma or Oxyma derivative 5b in 5% H2O-CH3CN. Oxyma derivative 5b is particularly useful, since it could be removed after the reaction via a simple basic or an acidic aqueous workup procedure.
- Wang, Yong,Aleiwi, Bilal A.,Wang, Qinghui,Kurosu, Michio
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supporting information
p. 4910 - 4913,4
(2012/12/12)
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- Selective esterifications of primary alcohols in a water-containing solvent
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Oxyma and an oxyma derivative, (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 2-cyano-2-(hydroxyimino)acetate (5b), displayed a remarkable effect on selective esterifications of primary alcohols. A wide range of carboxylic acids could be esterified with primary alcohols by using EDCI, NaHCO3, and Oxyma or Oxyma derivative 5b in 5% H2O-CH3CN. Oxyma derivative 5b is particularly useful, since it could be removed after the reaction via a simple basic or an acidic aqueous workup procedure.
- Wang, Yong,Aleiwi, Bilal A.,Wang, Qinghui,Kurosu, Michio
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supporting information
p. 4910 - 4913
(2013/01/15)
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- Deracemisation of β-hydroxy esters using immobilised whole cells of Candida parapsilosis ATCC 7330: substrate specificity and mechanistic investigation
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Deracemisation of aryl substituted β-hydroxy esters by immobilised whole cells of Candida parapsilosis ATCC 7330 gave >99% ee and up to 75% yield of their corresponding (S)-enantiomers. Mechanistic investigation of the deracemisation reaction carried out using a deuterated substrate, ethyl 3-deutero-3-hydroxy-3-phenyl propanoate revealed that while the (S)-enantiomer remains unreacted the (R)-enantiomer undergoes enantioselective oxidation to its corresponding ketoester, which on complementary enantiospecific reduction gives the (S)-enantiomer in high yield and % ee.
- Padhi, Santosh Kumar,Titu,Pandian, N. Ganesh,Chadha, Anju
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p. 5133 - 5140
(2007/10/03)
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- Nonactin biosynthesis: The initial committed step is the condensation of acetate (malonate) and succinate
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Nonactin is a macrotetrolide antibiotic produced by Streptomyces griseus subsp. griseus ETH A7796 that has shown activity against the P170-glycoprotein efflux pump associated with multiple drug resistant cancer cells. Nonactin is a polyketide, albeit a highly atypical one. The structure is composed of two units of each of the enantiomers of nonactic acid, arranged in a macrocycle, so that the molecule has S4 symmetry and is achiral. The monomer units, (+)- and (-)-nonactic acid, are derived from acetate, succinate, and propionate, although the exact details of the assembly process are quite unclear. We have used feeding experiments with a series of multiple stable isotope labeled precursors to elucidate the details of the first committed step of nonactic acid biosynthesis. We have found that the 13C label from 3-ketoadipate is incorporated specifically into both nonactic acid and its homologue, homononactic acid. The data conclusively show that the first committed step of nonactin biosynthesis is the coupling of a succinate derivative with either acetate or malonate. The differentiation into either nonactate or homononactate occurs after the initial condensation; the homologues are not derived from use of a different "starter unit" by the nonactate polyketide synthase. The first step of nonactin biosynthesis involves achiral intermediates; differentiation between the known enantiocomplementary biosynthesis pathways to form each enantiomer of the precursor monomer units likely occurs after the initial condensation reaction.
- Nelson, Michael E.,Priestley, Nigel D.
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p. 2894 - 2902
(2007/10/03)
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- Reduction of ketones to alcohols using a decaborane/pyrrolidine/cerium(III) chloride system in methanol
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Decaborane was found to be an effective agent for the chemoselective reduction of ketones to alcohols in the presence of pyrrolidine and cerium(III) chloride heptahydrate in methanol.
- Bae, Jong Woo,Lee, Seung Hwan,Jung, Yeon Joo,Yoon, Choon-Ock Maing,Yoon, Cheol Min
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p. 2137 - 2139
(2007/10/03)
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- 2-[1-(1,3-thiazolin-2-yl)azetidin-3-yl]thio-carbapenem derivatives
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Novel carbapenem compounds, (1R,5S,6S)-2-[1-(1,3-thiazolin-2-yl)azetidin-3-yl]thio-6-[(R)-1-hydroxyethyl]-1-methyl-carbapen-2-em-3 -carboxyic acid derivatives. These carbapenem compounds are represented by the following formula having a beta-coordinated methyl group introduced at the 1-position and a [1-(1,3-thiazolin-2-yl)azetidin-3-yl]thio group introduced at the 2-position. STR1 In the formula, R is hydrogen; lower alkyl group which is unsubstituted or substituted by hydroxy, lower alkoxy or lower alkoxy-lower alkoxy group; group --COOR1 (R1 is hydrogen or lower alkyl group); or group --CONR2 R3 (R2 and R3 are, independently each other, hydrogen or lower alkyl), and Y is carboxy, --COO? or protected carboxy. These compounds are useful antibiotics for prevention and treatment of bacterial infections.
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- Stereoselective synthesis of cyclopropanone ketals via silyl chloride promoted cyclization of β-zinciopropionates
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Alkyl, allyl, and propargyl β-iodopropionates undergo a cyclopropanation by the reaction with zinc-copper couple and TBDMSCI in THF to give 1-alkoxy-, 1-allyloxy- and 1-propargyloxy-1-tert-butyldimethylsiloxycyclopropanes in moderate or good yields. β-Iodo-α-methylpropionates 2 and 6 provide trans-5 and trans-8 selectively, which β-iodobutyrates 3 and 7 furnish cis-5 and cis-8 selectively.
- Yasui, Keigo,Tanaka, Shuji,Tamaru, Yoshinao
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p. 6881 - 6900
(2007/10/02)
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- Katalytische Hydrierung und Hydrokupplung von Acetessigsaeureamiden und -estern mit dem Clusteranion - als Katalysator
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The cluster anion - was found to catalyze the hydrogenation of the β-keto function in acetacetic amides and esters.The reaction of acetacetic amides yields the corresponding β-hydroxy derivatives, whereas acetacetic esters are converted in a consecutive coupling step into new diester derivatives.In the case of benzyl acetacetate both the hydrogenation and the hydrocoupling products were obtained.
- Schmidt, Gerhard F.,Reiner, Josef,Suess-Fink, Georg
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p. 379 - 384
(2007/10/02)
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