Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2000-03-07
2001-02-13
Riley, Jezia (Department: 1656)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C548S335500, C548S300100, C548S307700, C548S100000, C540S001000
Reexamination Certificate
active
06187928
ABSTRACT:
BACKGROUND OF THE INVENTION
This invention relates generally to the preparation of novel imidazolium cations, processes for such preparation, and various methods of use for the compounds of the invention.
The Vilsmeier-Haack reaction has been an established method for the formylation of aromatic rings. Such formylation, however is applicable mainly to active substrates, such as amines and phenols, and aromatic hydrocarbons which are much more active than benzene such as azulenes and ferrocenes. Typically, POCl
3
and dimethylformamide are used as the reactants, although other dialkyl amides have been used as well. It is also widely used as a method for chlorinating, especially with thionyl chloride, under similar reaction conditions.
OBJECTS OF THE INVENTION
It is an object of the present invention to provide novel imidazolium cations, and salts thereof, which have a variety of utilities.
It is a further object of the present invention to provide processes for the preparation of the aforesaid imidazolium cations, and their salts under favorable conditions in large quantities.
A still further object of the present invention is to provide methods for using the novel imidazolium cations and their salts produced by the processes of the instant invention. These methods include a variety of applications, both industrial and medical, which result from the properties of the aforesaid imidazolium compounds.
It is thus a further object of the present invention to provide methods of using the compounds of the instant invention as fluorescent dyes for textiles, and for the incorporation into polymer matrices so as to enable their use in as pigments for waterborne paints, films and articles made of polyolefins, e.g. polyethylene or polypropylene.
It is a further object of the present invention to provide compounds useful in the preparation of non-linear optical devices.
Still further, it is an object of the present invention to utilize the compounds of the instant invention for printing fiber materials, for example, polyester, cotton or polyester/cotton blend fabrics.
Another object of the present invention is to utilize the compounds of the present invention as fluorescent tags for biomolecules, so as to enable the labeling of such molecules and the monitoring of the disposition of such molecules by the mammalian body.
A still further object of the present invention involves the use of the compounds of the present invention as components of kits for use in assaying biomolecules tagged with the aforesaid compounds.
Another object of the present invention is to use the process of the invention in combinatorial drug invention systems for labeling and for therapeutic investigation. The instant invention can be used as a linear strategy for combinatorial synthesis.
SUMMARY OF THE INVENTION
The present invention relates to novel imidazolium cations, and to processes for their preparation. More particularly, this invention concerns compounds of the
wherein A is a heteroaromatic ring, which may be optionally substituted by one or more R substituents selected from the group consisting of aryl, heteroaryl, lower alkyl, hydroxy, halo, lower alkylamino, amino, nitro, or carboxy substituents; wherein P or Q are optional substituents, each independently a substituent selected from the group consisting of aryl, heteroaryl, lower alkyl, hydroxy, halo, lower alkylamino, amino, nitro, or carboxy, or P and Q together are a heteroaromatic ring, said P and Q substituents independently or together which may optionally be substituted by one or more R′ substituents selected from the group consisting of aryl, heteroaryl, lower alkyl, hydroxy, halo, lower alkylamino, amino, nitro, or carboxy substituents;
C is an optional substituent which is an aromatic or heteroaromatic ring, which may optionally be substituted by one or more R″″ substituents selected from the group consisting of aryl, heteroaryl, lower alkyl, hydroxy, halo, lower alkylamino, amino, nitro, or carboxy substituents;
R″ is hydrogen, a lower alkyl or aryl group, or together with R′″ and the nitrogen atom to which it is attached, form a heterocyclic ring having from 5 to 7 members, which may optionally contain a sulfur, oxygen, silicon, selenium or an additional nitrogen atom, said ring optionally substituted with at least one lower alkyl group; R′″ is a lower alkyl or aryl group, or together with R″ and the nitrogen atom to which it is attached, form a heterocyclic ring having from 5 to 7 members, which may optionally contain a sulfur, oxygen, silicon, selenium or an additional nitrogen atom, said ring optionally substituted with at least one lower alkyl group; and X is an anion.
The process of the instant invention involves the reaction of a compound of formula II with an N,N-disubstituted-formamide of formula III in the presence of a halogenating agent.
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Donovan Robert J.
Morgan Robert J.
Klauber & Jackson
Riley Jezia
The Rockefeller University
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