Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Ketone doai
Reexamination Certificate
1999-09-01
2001-07-10
Padmanabhan, Sreeni (Department: 1621)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Ketone doai
C514S678000, C514S679000, C514S690000, C512S010000, C568S308000, C568S325000, C568S328000, C568S329000, C568S331000
Reexamination Certificate
active
06258854
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to new ketones. These ketones are useful as precursors for organoleptic compounds, especially fragrances and masking agents, and antimicrobial compounds.
BACKGROUND OF THE INVENTION
A principal strategy currently employed for imparting odors to consumer products is the admixing of a fragrance directly into the product. There are, however, several drawbacks to this strategy. The fragrance material may be too volatile and/or too soluble, resulting in fragrance loss during manufacturing, storage, and use. Many fragrance materials are also unstable over time. This again results in fragrance loss during storage.
In many consumer products, it is desirable for the fragrance to be released slowly over time. Microencapsulation and inclusion complexes with cyclodextrins have been used to help decrease volatility, improve stability, and provide slow-release properties. These methods, however, are for a number of reasons often not successful. In addition, cyclodextrins may be too expensive.
Fragrance precursors for scenting fabrics washed in the presence of a lipase-containing detergent are described in WO 95/04809. The fragrance precursors contained in a detergent and/or in a fabric softener are cleaved by the lipase and a single odoriferous compound (either an odoriferous alcohol or ketone) is formed. In this way, a prolonged scenting effect on the fabric is obtained.
EP-A-0 816 322 discloses fragrance precursor compositions containing carbonic acid esters or thiocarbonic acid esters. These compositions are used in cosmetic products or in laundry products. Such precursors produce fragrances upon contacting the skin or when used in the presence of lipases (e.g., such as those lipases used in detergents) thus providing a prolongation of the fabric scenting effect.
One object of the present invention is to provide new precursors for compounds with different activities.
A further object of the invention is to provide new compounds which are stable in a variety of applications including detergents, fabric softeners, cleaning products, personal care products, cosmetics, and sun protection products.
A further object of the invention is to provide new compounds that may be cleaved by light, heat, hydrolysis, and/or enzymes into one or more organoleptic compounds.
SUMMARY OF THE INVENTION
One embodiment of the present invention is a ketone of the formula I:
wherein
Y is an optionally substituted alkyl, cycloalkyl, cycloalkylalkyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, alkyloxycarbonyl, cycloalkyloxycarbonyl, aryloxycarbonyl, amide, oximinocarbonyl, alkylthiocarbonyl, cycloalkylthiocarbonyl, wherein each alkyl group is straight or branched and each alkyl and cycloalkyl group is saturated or unsaturated;
R
1
is hydrogen or a C
1-6
alkyl group that is substituted, saturated or unsaturated, straight or branched;
A is a chromophoric aromatic or heteroaromatic ring or ring system, and carries 1 to 8 substituents selected from the group consisting of hydrogen, hydroxy, mercapto, amino, acyl, ester, esterified hydroxy group, cyano, nitro; substituted, saturated or unsaturated, straight or branched alkyl, alkoxy, alkylthio, and arylalkoxy groups; substituted or unsubstituted aryl and heteroaryl groups, and a polymeric group;
n is an integer; and
with the proviso that formula I is not 2-ethoxy-1-phenyl-ethanone, hydroxy-acetic acid 2-oxo-2-phenyl-ethyl ester, acetic acid 1-methyl-2-oxo-2-phenyl-ethyl ester, or p-methoxyphenacyl acetate.
Another embodiment of the invention is a precursor of an active compound that includes a ketone of the formula I:
wherein
Y is an optionally substituted alkyl, cycloalkyl, cycloalkylalkyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, alkyloxycarbonyl, cycloalkyloxycarbonyl, aryloxycarbonyl, amide, oximinocarbonyl, alkylthiocarbonyl, cycloalkylthiocarbonyl, wherein each alkyl group may be straight or branched and each alkyl and cycloalkyl group may be saturated or unsaturated;
R
1
is hydrogen or a C
1-6
alkyl group that may be substituted, saturated or unsaturated, straight or branched;
A is a chromophoric aromatic or heteroaromatic ring or ring system, and A carries 1 to 8 substituents selected from the group consisting of hydrogen, hydroxy, mercapto, amino, acyl, ester, esterified hydroxy group, cyano, nitro; substituted, saturated or unsaturated, straight or branched alkyl, alkoxy, alkylthio and arylalkoxy groups; substituted or unsubstituted aryl and heteroaryl groups, and a polymeric group; and
n is an integer.
Another embodiment is a composition selected from detergents, fabric softeners, personal care products, cleaning compositions, cosmetics, and sun protection products in admixture with the precursor defined above.
Another embodiment is a method of imparting a sustained release odorant and/or an antimicrobial agent into a consumer product that includes mixing the consumer product with at least one compound according to formula I:
wherein
Y is an optionally substituted alkyl, cycloalkyl, cycloalkylalkyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, alkyloxycarbonyl, cycloalkyloxycarbonyl, aryloxycarbonyl, amide, oximinocarbonyl, alkylthiocarbonyl, cycloalkylthiocarbonyl, wherein each alkyl group is straight or branched and each alkyl and cycloalkyl group is saturated or unsaturated;
R
1
is hydrogen or a C
1-6
alkyl group that is substituted, saturated or unsaturated, straight or branched;
A is a chromophoric aromatic or heteroaromatic ring or ring system, and carries 1 to 8 substituents selected from the group consisting of hydrogen, hydroxy, mercapto, amino, acyl, ester, esterified hydroxy group, cyano, nitro; substituted, saturated or unsaturated, straight or branched alkyl, alkoxy, alkylthio, and arylalkoxy groups; substituted or unsubstituted aryl and heteroaryl groups, and a polymeric group;
n is an integer; and
with the proviso that formula I is not 2-ethoxy-1-phenyl-ethanone, hydroxy-acetic acid 2-oxo-2-phenyl-ethyl ester, acetic acid 1-methyl-2-oxo-2-phenyl-ethyl ester, or p-methoxyphenacyl acetate.
In this method, the consumer product is selected from laundry detergents, fabric softeners, fabric softener sheets, cleaning compositions, swimming pool additives, toiletries, and cosmetic products, such as shampoo, conditioners and sunscreens.
In this embodiment, the precursor is activated to form an organoleptic and/or antimicrobial agent. The precursor is activated by exposure to an activating agent selected from the group of light, heat, hydrolysis, and enzymes.
DETAILED DESCRIPTION OF THE INVENTION
The present invention discloses new ketones of the formula I:
wherein
Y is an optionally substituted alkyl, cycloalkyl, cycloalkylalkyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, alkyloxycarbonyl, cycloalkyloxycarbonyl, aryloxycarbonyl, amide, oximinocarbonyl, alkylthiocarbonyl, cycloalkylthiocarbonyl, wherein each alkyl group may be straight or branched and each alkyl and cycloalkyl group may be saturated or unsaturated;
R
1
is hydrogen or a C
1-6
alkyl group that may be substituted, saturated or unsaturated, straight or branched;
A is a chromophoric aromatic or heteroaromatic ring or ring system having 1 to 8 substituents selected from hydrogen, hydroxy, mercapto, amino, acyl, ester, esterified hydroxy group, cyano and nitro; substituted, saturated or unsaturated, straight or branched alkyl, alkoxy, alkylthio and arylalkoxy groups; substituted or unsubstituted aryl and heteroaryl, and a polymeric group;
n is an integer; and
with the proviso that formula I is not 2-ethoxy-1-phenyl-ethanone, hydroxy-acetic acid 2-oxo-2-phenyl-ethyl ester, acetic acid 1-methyl-2-oxo-2-phenyl-ethyl ester, or p-methoxyphenacyl acetate.
As used herein, each group containing the term “alkyl” includes the unsaturated residues thereof, e.g. alkenyl, alkynyl, cycloalkenyl, etc.
In the present invention, the compounds of formula I are not limited to any particular stereoisomers. Accordingly, all possible stereoisomers (E/Z isomers, enantiomers, diastereomers) and mixtures thereof are included withi
Anderson Denise
Frater Georg
Bryan Cave LLP
Givaudan Roure ( International ) SA
Haracz Stephen M.
Padmanabhan Sreeni
Waddell Mark E.
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