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Mandelic acid condensation polymers

A mandelic acid, polymer technology, applied in the field of acid condensation polymers, can solve the problem of increased infection risk of the protective skin layer

Active Publication Date: 2014-12-03
RUSH UNIV MEDICAL CENT +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although contact with undamaged and healthy skin is unlikely to result in STD transmission, breaks, cuts, or injuries to the protective skin layer can increase the risk of transmission
[0009] STDs secondary to a variety of infections are treatable, but these infections are increasingly showing resistance to available treatments

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0124]

[0125] Mandelic acid condensation polymers of formula (3a) were prepared by direct reaction of dl-mandelic acid with concentrated sulfuric acid at low temperature. At -35 °C, under vigorous stirring, one-time injection containing concentrated H 2 SO 4(256 grams (g), 4000 millimoles (mmol), 139 ml) of a round bottom flask equipped with a mechanical stirrer was added dl-mandelic acid (30.4 g, 200 mmol). The resulting reaction mixture was stirred at -35°C for 1 hour and then at room temperature for an additional 8 hours. The reaction mixture was then poured into an Erlenmeyer flask containing 3040 ml of ice water and stirred for 1 hour. The solid was isolated and filtered with suction, washed with water (3 x 50ml) and dried in a vacuum desiccator under reduced pressure for 12 hours to give (3a) as an off white solid (28.25g, 100 % yield); melting point (mp) 205-206°C. 1 H NMR (DMSO-d 6 ): δ7.35-7.02(m, ArH), 5.23(br s, CHOH), 5.15-4.75(m, CHCO 2 H), 3.41 (br s, ...

Embodiment 2

[0127] ESI-MS analysis

[0128] The structure of formula (3a) was further confirmed by electrospray ionization (ESI) mass spectrometry (MS). Several samples prepared according to the procedure of Example 1 were evaluated. Such as figure 1 As shown in , the ESI mass spectrum indicates that the product from Example 1 has a polymer composition of repeating units of 134 atomic mass units (amu), which corresponds to the molecular weight of mandelic acid minus water.

Embodiment 3

[0130] The second synthesis of the polymer of formula (3a) was achieved by performing polymerization at -30°C (±5°C). The concentrated sulfuric acid was cooled to -30°C. The temperature was maintained at -30°C (± 5 degrees) as mandelic acid was added in aliquots to the cooled and stirred mixture over a period of time (approximately 30 minutes for a 20 gram reaction). (The ratio of mandelic acid / concentrated sulfuric acid is 20 grams / 100ml). The reaction mixture was then stirred and maintained at -30°C for one hour, then the temperature was allowed to slowly rise to room temperature and stirred for a further 12 hours. The reaction mixture was then poured onto / into a mixture of ice and DI water (500 g / 200 ml). A pale pink precipitate formed and was then vacuum filtered, washed with water and then resuspended in 200 ml of DI water. The precipitate was collected by vacuum filtration and washed by repeated suspensions in DI water (200ml) followed by vacuum filtration until the f...

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PUM

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Abstract

Disclosed herein are compounds and compositions useful for reducing the risk of infection. In particular, disclosed herein are mandelic acid condensation polymers, compositions comprising such compounds, processes for producing such compounds, and methods of using such compounds.

Description

[0001] 【Priority Statement】 [0002] This application claims priority to US Provisional Application Serial No. 61 / 566,441, filed December 2, 2011, which is incorporated herein by reference. [0003] 【Statement of Government Rights】 [0004] This invention was made with government support under contract numbers R43 AI084225-01A2 and P01 HD41763-03 awarded by the National Institutes of Health. The government has certain rights in this invention. technical field [0005] The present invention relates generally to acid condensation polymers, and more particularly to mandelic acid condensation polymers, compositions comprising the compounds, methods of using the compounds and compositions, and processes for making the compounds . Background technique [0006] The HIV / AIDS epidemic has dramatically and dramatically highlighted the threat of STDs to the human population. Until a cure or at least an effective treatment becomes available, the best and possibly only practical solu...

Claims

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Application Information

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IPC IPC(8): C07C63/331C07F1/04C08G63/127
CPCC07C59/48C07C51/353C07C67/465C08G61/02C07C69/616C07C2601/16A61K31/765C07C51/347C07C59/50C08G2261/11C08G2261/1426C08G2261/20C08G2261/3424C08G2261/42C08G2261/90
Inventor R·A·小安德森琱晓慧L·J·D·瑞恩凡德C·J·查尼二世A·柯鲁尼克D·P·渥勒D·L·凡腾S·杰音
Owner RUSH UNIV MEDICAL CENT
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