Amorphous...

Details Amorphous... Amorphous...

1999-11-19

2001-12-18

Geist, Gary (Department: 1623)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

C560S041000

Reexamination Certificate

active

06331646

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention is related to amorphous N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester (neotame). The invention is also directed to processes of preparing amorphous neotame, such as by melt-processing. Amorphous neotame is advantageous compared to other forms of neotame because of improved solubility and dissolution.
2. Related Background Art
Neotame is a known sweetener that has a sweetening potency that is about 40 times that of aspartame and about 8,000 times that of sucrose. N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester may be prepared from aspartame as described in U.S. Pat. Nos. 5,480,668, 5,510,508 and 5,728,862, all of which are incorporated by reference herein.
As described in those patents, neotame is crystallized from a methanol/water solution to provide neotame monohydrate, i.e., one molecule of water and one molecule of neotame. The crystal structure of neotame monohydrate is known. See e.g., “Neotame, an alkylated dipeptide and high intensity sweetener”, Acta Cryst. (1999) C55, 1365-1368.
SUMMARY OF THE INVENTION
This invention relates to amorphous N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester (amorphous neotame). As used herein, the term amorphous is defined as a non-crystalline solid material. In one embodiment of this invention the amorphous neotame may be prepared by the process comprising the steps of (i) melting N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester and (ii) cooling the melt to produce a melt-processed neotame, i.e., amorphous neotame.
Another embodiment of this invention is directed to the process of preparing amorphous neotame by milling, most preferably by ball milling. Yet another embodiment of this invention is directed to the process of preparing amorphous neotame by dissolving neotame in an organic solvent and recovering amorphous neotame from the solvent. Generally, the amorphous neotame is recovered by evaporation of the solvent or separating the amorphous neotame from the solvent by, for example, filtration.
Preferably, the neotame that is used to prepare amorphous neotame by the techniques described above can be any hydrated form, such as a monohydrate (about 4.0% to 4.5% H
2
O), an intermediate hydrate (about 1.0% to 4.0% H
2
O) or an anhydrate (less than about 1.0% H
2
O) or combinations thereof. In addition, it is also possible for the neotame to contain excess water, i.e., greater than about 4.5% H
2
O. Most preferably the neotame is the monohydrate form. The amorphous neotame of this invention is characterized by an x-ray diffraction pattern as depicted in FIG.
1
.


REFERENCES:
patent: 5480668 (1996-01-01), Nofre et al.
patent: 5510508 (1996-04-01), Claude et al.
patent: 5728862 (1998-03-01), Prakash
D.J. Wink et al., “Neotame, an Alkylated Dipeptide and High Intensity Sweetener,” C55Acta Cryst.1365-1368 (1999).

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