Drug – bio-affecting and body treating compositions – Anti-perspirants or perspiration deodorants
Reexamination Certificate
1997-12-15
2001-05-29
Dees, Jose G. (Department: 1616)
Drug, bio-affecting and body treating compositions
Anti-perspirants or perspiration deodorants
C424S070100, C424S073000, C424S401000, C512S001000, C512S025000, C562S553000
Reexamination Certificate
active
06238655
ABSTRACT:
BACKGROUND OF THE INVENTION
The invention relates to &agr;-amides of L-amino acids that are precursors of fragrances and which are useful in the formulation of deodorants, antiperspirants, body sprays, and other skin treatment compositions.
In humans, axillary malodors are produced by enzymatic cleavage of malodor precursors found in apocrine secretions. The enzymes that release the malodors are produced by axillary bacteria such as Staphylococcus sp. and Corynebacteria. Typical deodorants mask or decrease this malodor.
SUMMARY OF THE INVENTION
It has now been shown that various &agr;-amides of L-amino acids can be cleaved by axillary bacterial enzymes, releasing pleasant fragrances and/or attenuating malodor. Such amino acid amides, therefore, are useful in skin treatment compositions such as deodorants, antiperspirants, and body sprays. Accordingly, the invention relates to &agr;-amides of L-amino acids that are precursors of fragrances, or which can attenuate or mask malodor.
In one aspect, the invention features a skin treatment composition (e.g., a deodorant composition) for application to human skin; the skin treatment composition includes a dermatologically acceptable vehicle and an &agr;-amide of an L-amino acid having the structure:
wherein R
1
is H, CH
3
, CH
2
OH, or CH(OH)CH
3
; and R
2
is selected so that cleavage of the &agr;-amide of the L-amino acid leaves an R
2
—CO
2
H having a neutral or pleasant odor, or which is useful in attenuating or masking malodor. In general, these &agr;-amides of L-amino acids are cleaved by bacterial enzymes by the reaction shown below.
The &agr;-amide of the L-amino acid is present in an amount sufficient to produce fragrance or attenuate or mask malodor. Preferably, the &agr;-amide of L-amino acid is present in the skin treatment composition at a concentration of 0.01 to 10.0% (preferably 0.1 to 5.0%) by weight. If desired, the skin treatment composition can include an antiperspirant active (e.g., aluminum chlorohydrate)or a deodorant active (e.g., an antimicrobial). In various preferred embodiments, the skin treatment composition is formulated as a lotion, cream, stick, gel, or aerosol.
The composition may be formulated as a skin moisturizer, shampoo, shave preparation, body spray, body wash, soap, and the like.
The invention offers several advantages. For example, when the &agr;-amides of L-amino acids are formulated as skin treatment compositions, fragrance is released slowly over time. Consequently, the fragrance is long-lasting and fading of the scent over time is minimized. In many instances, the &agr;-amide of L-amino acid competes with the malodor precursor and attenuates malodor production over a prolonged period.
Other features and advantages of the invention will be apparent from the following detailed description, and from the claims.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
In preferred &agr;-amides of L-amino acids, R
2
has 1 to 30 carbon atoms and is alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or heterocyclic. These groups may be unsubstituted or substituted with one or more halo, hydroxyl, amino, nitro, amide, alkoxyl, carboxyl, cyano, thio, phosphoro, or other heteroatoms, phenyl or heterocyclic groups. The amino, amide, alkoxyl, carboxyl, thio, phosphoro, phenyl, or heterocyclic groups may be unsubstituted or substituted with one or more halo, hydroxyl, amino, nitro, alkyl, amide, alkoxyl, carboxyl, cyano, thio, or phosphoro groups.
R
2
can be, for example, methyl, ethyl, propyl, isopropyl, tert-butyl, sec-butyl, isobutyl, n-butyl, pentyl, hexyl, heptyl, octyl, 2-octyl, nonyl, 2-nonyl, decyl, 2-decyl, undecyl, 2-undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, or octadecyl, or any mono or poly unsaturated form thereof, cyclopentyl, cyclohexyl, 2-cyclohexylethyl, 2,6-dimethylheptyl, geranyl, neryl, citronellyl, 9-decenyl, 2,6-dimethyl-5-heptenyl, 2,6-dimethyl-1,5-heptadienyl, 8,11-heptadecadienyl, 8-heptadecenyl, cyclopentenyl, cyclohexenyl, phenyl, p-methoxyphenyl, benzyl, 2-phenylethyl, 1-phenylethyl, 2-(p-methoxyophenyl)-ethenyl, 3-(p-methylphenyl)-2-propyl, 3-(p-isopropylphenyl)-2-propyl, 3-(p-tert-butylphenyl)-2-propyl,2,5,8-trioxanonyl, acetonyl, aminomethyl, hydroxymethyl, 1-hydroxyethyl, dimethylaminomethyl, 1-phenyl-1-aminoethyl, carboxymethyl, 2-carboxyethyl, 3-carboxypropyl, 4-carboxybutyl, 5-carboxypentyl, 6-carboxyhexyl, 7-carboxyheptyl, 8-carboxyoctyl, 9-carboxynonyl, 10-carboxy-2,5,8-trioxanonyl, 7-carboxamido-5-carboxy-4-aza-3-oxo-heptyl, 8-carboxamido-6-carboxy-5-aza-4-oxo-octyl, 9-carboxamido-7-carboxy-6-aza-5-oxo-nonyl, 10-carboxamido-8-carboxy-7-aza-6-oxo-decyl, 11-carboxamido-9-carboxy-8-aza-7-oxo-undecyl, 14-carboxamido-12-carboxy-11-aza-10-oxo-tetradecyl, 2-pentyl-cyclopropyl, menthyl, or terpineyl.
Preferred &agr;-amides of L-amino acids for use in the invention include, without limitation, N-methylpentenylserine, N-methylpentenylalanine, N-phenylacetylserine, N-phenylacetylalanine, N-indolacetylserine, N-indolacetylalanine, N-cyclohexylcarboxylserine, N-cyclohexylcarboxylalanine, N-ethylbutyrylserine, N-ethylbutyrylalanine, N-pheylpropionylserine, N-phenylpropionylalanine, N-benzoylserine, N-benzoylalanine, N-cyclohexylacetylserine, N-cyclohexylacetylalanine, N-vanilloylserine, N-vanilloylalanine, N-methylpentenylthreonine, N-methylpentenylglycine, N-phenylacetylthreonine, N-phenylacetylglycine, N-indolacetylthreonine, N-indolacetylglycine, N-cyclohexylcarboxylthreonine, N-cyclohexylcarboxylglycine, N-ethylbutyrylthreonine, N-ethylbutyrylglycine, N-phenylpropionylthreonine, N-phenylpropionylglycine, N-benzoylthreonine, N-benzoylglycine, N-cyclohexylacetylthreonine, N-cyclohexylacetylglycine, N-vanilloylthreonine, N-vanilloylglycine.
The preferred &agr;-amides of L-amino acids generally can be prepared by coupling a carboxylic acid to a protected amino acid by known procedures. The carboxylic acids and protected amino acids generally are known in the art; they generally are either commercially available or can be made by known procedures.
REFERENCES:
patent: 4089942 (1978-05-01), Bore et al.
patent: 4934609 (1990-06-01), Lindauer et al.
patent: 5176903 (1993-01-01), Goldberg et al.
patent: 5223251 (1993-06-01), Nichols
patent: 5380707 (1995-01-01), Barr et al.
patent: 5431904 (1995-07-01), Laney
patent: 5514671 (1996-05-01), Lyon et al.
patent: 5538719 (1996-07-01), Preti et al.
patent: 5626852 (1997-05-01), Suffis et al.
patent: 816 322 (1996-01-01), None
patent: 815 833 (1998-01-01), None
patent: 7-179328 (1995-07-01), None
patent: WO 93/07853 (1993-04-01), None
patent: WO97/30687 (1997-08-01), None
patent: 97/30687 (1997-08-01), None
John D. Pierce, Jr. et al., Cross-adaptation of sweaty-smelling 3-methyl-2-hexenoic acid by its ethyl esters is determined by structural similarity, J. Soc. Cosmet. Chem., 47:363-375 (Nov./Dec. 1996).
Goldman Virginia Streusand
Laney Judith Wolfe
Slife Charles W.
Dees Jos,e G.
Fish & Richardson P.C.
Lamm Marina
The Gillette Company
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