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Polyethylene glycol aldehydesRelated Patent Categories: Synthetic Resins Or Natural Rubbers -- Part Of The Class 520 Series, Polymer Derived From Nitrile, Conjugated Diene And Aromatic Co-monomers, , Reactant Contains Nitrogen As A Ring Member Of A Heterocyclic Ring, From Organic Oxygen-containing ReactantPolyethylene glycol aldehydes description/claimsThe Patent Description & Claims data below is from USPTO Patent Application 20070167606, Polyethylene glycol aldehydes. Brief Patent Description - Full Patent Description - Patent Application Claims
PRIORITY TO RELATED APPLICATIONS [0001] This application is a division of U.S. application Ser. No.10/623,978, filed Jul. 21, 2003, now pending; which claims the benefit of the U.S. Provisional Application 60/398,196 filed on Jul. 24, 2002. FIELD OF THE INVENTION [0002] The present invention relates to polyethylene glycol aldehydes, and to related methods of making and using such derivatives, such as in the pegylation of polypeptides and other biomolecules. BACKGROUND OF THE INVENTION [0003] Polyethylene glycol ("PEG") is a linear or branched, neutral polyether, available in a variety of molecular weights. The structure of PEG is HO--(CH.sub.2--CH.sub.2--O).sub.n--H, where n indicates the number of repeats of the ethylene oxide unit in the PEG. [0004] PEG and PEG derivatives have been employed to modify a variety of biomolecules. When attached to such molecules, PEG increases their solubility and increases their size, but has little effect on desirable properties. [0005] Advantageously, PEG conjugated biomolecules may exhibit increased retention and delayed metabolism in the body. [0006] A variety of PEG derivatives has been developed for such applications. Such PEG derivatives are described, for example, in U.S. Pat. Nos. 5,252,714; 5,672,662; 5,959,265; 5,990,237; and 6,340,742. [0007] Two general approaches have been used for the functionalization of PEG: (1) changing the terminal hydroxyl group, through a series of reactions, to a more active functional group and/or (2) reaction of the PEG under controlled conditions with difunctional compounds so that one of its functional groups reacts with the PEG polymer and the other remains active. In most cases, several steps must be conducted to achieve the desired PEG derivatives. The desired PEG derivatives are often produced in low yields and require a complicated purification process to isolate. In addition, PEG derivatives may show nonspecific binding to the biomolecules of interest, which can result in multiple PEGs attached to a single biomolecule and/or PEG attachment at the active site. Multiple PEG attachments may cause difficulty in purification of the pegylated biomolecule. Multiple PEG attachments, and/or pegylation at the active site, can also lead to decreased activity of the biomolecule. [0008] It would, therefore, be advantageous to provide improved PEG derivatives suitable for conjugation with a variety of other molecules, including polypeptides and other biomolecules containing an .alpha.-amino group. There remains a need to provide PEG derivatives that can be produced in high yield and purity, and that can be conjugated to provide biomolecules having improved performance characteristics. [0009] These and other objects of the present invention are described in greater detail below. SUMMARY OF THE INVENTION [0010] The compounds of the invention are aldehyde derivatives of polyethylene glycol, having the general formula (I): R.sub.1--(CH.sub.2CH.sub.2O).sub.n--CH.sub.2CH.sub.2--X--Y--NH--(CH.sub.2- ).sub.p--CHO (I) wherein R.sub.1 is a capping group, X is O or NH, Y is selected from the group consisting of Z is a side chain of an amino acid, m is from 1 to 17, n is from 10 to 10,000, and p is from 1 to 3. [0011] The present invention also provides a compound of formula (II): wherein R.sub.1, m, n, and p are defined as above. [0012] Another preferred embodiment of the present invention provides a bifunctional polyethylene glycol aldehyde compound of formula (VIII): wherein m, n, and p are is defined as above. [0013] The present invention also provides intermediate compounds of formula (IX): wherein R.sub.1, X, Y, Z, m, n, and p are defined as above. [0014] The present invention further provides intermediate compounds of formula (X): wherein R.sub.1, m, n, and p are defined as above. [0015] Also provided is an intermediate compound of formula (XI): wherein each m, n, and p is the same or different and is defined as above. [0016] The present invention further provides a method of making a polyethylene glycol aldehyde comprising hydrolyzing a compound of formula (IX): R.sub.1--(CH.sub.2--CH.sub.2--O).sub.n--CH.sub.2CH.sub.2--X--Y--NH-- -(CH.sub.2).sub.p--CH--(OCH.sub.2--CH.sub.3).sub.2 (IX) to produce a polyethylene glycol aldehyde of formula (I): R.sub.1--(CH.sub.2CH.sub.2O).sub.n--CH.sub.2CH.sub.2--X--Y--NH--(CH.sub.2- ).sub.p--CHO (I) wherein R.sub.1, X, Y, Z, m, n, and p are defined as above. [0017] The present invention also provides a method of making a polyethylene glycol aldehyde comprising hydrolyzing a compound of formula (X): to produce a polyethylene glycol aldehyde of formula (11): wherein R.sub.1, m, n, and p are defined as above. [0018] The present invention provides a method of making a polyethylene glycol aldehyde comprising hydrolyzing a compound of formula (XVII): to produce a polyethylene glycol aldehyde of formula (VIII): wherein m, n, and p are defined as above. DETAILED DESCRIPTION OF THE INVENTION [0019] The present invention provides a variety of compounds and chemical intermediates and methods which may be used in connection with the pegylation of polypeptides and other biomolecules. The present invention provides a new chemical structure for polyethylene glycol aldehydes. Continue reading about Polyethylene glycol aldehydes... Full patent description for Polyethylene glycol aldehydes Brief Patent Description - Full Patent Description - Patent Application Claims Click on the above for other options relating to this Polyethylene glycol aldehydes patent application. ###  How KEYWORD MONITOR works... a FREE service from FreshPatents1. Sign up (takes 30 seconds). 2. Fill in the keywords to be monitored. 3. Each week you receive an email with patent applications related to your keywords. Start now! - Receive info on patent apps like Polyethylene glycol aldehydes or other areas of interest. ### Previous Patent Application: Unsaturated poly(ester-amide) biomaterials Next Patent Application: Nanoscale array biomolecular bond enhancer device Industry Class: Synthetic resins or natural rubbers -- part of the class 520 series ### FreshPatents.com Support Thank you for viewing the Polyethylene glycol aldehydes patent info. 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