Halogenated wang resins for combinatorial chemical synthesis

Details Halogenated wang resins for combinatorial chemical synthesis Halogenated wang resins for combinatorial chemical synthesis

2001-04-12

2002-11-19

Lipman, Bernard (Department: 1713)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Mixing of two or more solid polymers; mixing of solid...

C525S332200, C525S359300

Reexamination Certificate

active

06482898

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to novel halogenated Wang resins for combinatorial chemical synthesis, more specifically to halogenated Wang resins expressed by the following formula 1 useful for the effective tracing of combinatorial chemical synthetic process on solid supports using X-ray photoelectron spectroscopy (XPS) element analysis method.
wherein {circle around (P)} represents polystyrene-divinylbenzene; X and Y represent hydrogen atom or halogen atom, which may be identical or different, their total number being 1-4; and at least one of them is halogen atom.
2. Description of the Related Arts
Combinatorial chemical synthesis (CCS) is one of the important new methodologies developed by academic and industry researchers in the pharmaceutical, agrochemical, and biotechnological industries to reduce the time and cost. It is a useful tool for rapidly optimizing molecular properties, particularly ones that are difficult to design a prior. Within the past several years, a number of reports have appeared that combinatorial chemistry using solid-phase chemical synthesis provides great potential, because solid-phase chemistry have several big advantages to develop combinatorial techniques such as possible to make a lot of libraries in one pot, simple to purify, simple to continuos multi step reaction, and possible to automation of reaction process.
As explained above, CCS is a new synthetic method which overcomes the uneconomicity and ineffectiveness of the conventional synthetic technologies. However, it was seldom applied to organic synthesis because it was difficult to identify the product of each reaction step and to trace the reaction progress with reaction time.
Solid-NMR spectroscopy, mass spectroscopy and IR spectroscopy are mainly used to trace the reaction progress because CCS is generally performed on the solid support. Solid-NMR spectroscopy has the advantage that the entire structure of the product can be elucidated. However, clear data for the extensive analysis of the product on solid support are hardly obtainable at present. Especially, the structure identification of the compound containing hydrogen and carbon in the same spectral range of the solid support and the quantitative analysis of the reaction progress are highly limited. Mass spectroscopy is effective for small amount of sample and qualitative analysis. However, tracing of reaction progress is highly limited and the qualitative analysis of the various compounds on solid support is very difficult as yet. IR spectroscopy is being used the most widely, because qualitative and approximate quantitative analyses are performed easily. However, if more than one identical functional groups exist in the compound, the quantitative analysis is almost impossible.
The above-mentioned spectroscopic analyses can be partly used for the analysis of compound on solid support. However, the quantitative analysis of reaction progress of the entire chemical reaction on solid support was impossible. So, the determination of the termination point of the chemical reactions on solid support was difficult to compare with the liquid-phase chemical reactions. Accordingly, the reaction was terminated just after long time;
SUMMARY OF THE INVENTION
The inventors of the present invention made repeated researches to find a combinatorial chemical approach in organic synthesis and to introduce a high throughput screening (HTS) method. As a result, we found that X-ray photoelectron spectroscopy (XPS) is effective in the analysis of product and reaction progress on solid support. Developing halogenated Wang resin with new structure, which is useful in XPS analysis and provides excellent chemical stability and reactivity, the present invention was completed.
XPS, which has mainly been applied to polymer synthesis, is not suitable for application to CCS on solid support, because the element amount of the solid support cannot be used as standard amount due to the excessively large (1-2 mmol/resin-1 g) difference of the relative element amount of the solid support and that of the active site.
So, we introduced halogen, a heteroatom, to Wang resin, which is one of the solid supports, in consideration of the fact that most bioactive materials contain heteroatoms. As a result, the relative change of heteroatom during the reaction progress could be traced exactly, and XPS became more effective for elemental analysis.
Accordingly, an object of this invention is to provide a novel halogenated Wang resin useful for CCS and preparing method thereof. Another object of this invention is to provide a quantitative method of analyzing the product produced from the CCS by using halogenated Wang resin and XPS.


REFERENCES:
patent: 6150548 (2000-11-01), Koot
patent: 6180718 (2001-01-01), Boehm et al.
patent: WO 97/42230 (1997-11-01), None
patent: WO 98/50438 (1998-11-01), None

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