Serine carbonates

Details Serine carbonates Serine carbonates

2002-08-15

2003-05-27

Qazi, Sabiha (Department: 1616)

Drug, bio-affecting and body treating compositions

Anti-perspirants or perspiration deodorants

C424S066000, C424S068000, C554S101000, C554S107000, C560S158000, C560S159000, C560S160000, C562S561000, C562S563000

Reexamination Certificate

active

06569411

ABSTRACT:

The present invention relates to serine carbonates and the use of serine carbonates as precursors for (a) organoleptic compounds, especially for fragrances, flavors and/or (b) masking agents, and/or (c) antimicrobial compounds and/or (d) alternative substrates for malodor producing enzymes.
A principal strategy currently employed in imparting odors to consumer products is the admixing of a fragrance, masking agent or antimicrobial compound directly into the product to be treated. There are, however, several drawbacks to this strategy. The fragrance material can, for example, 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 loss during storage.
In many consumer products it is desirable for the fragrance to be released slowly over time. Microencapsulation and inclusion complexes, especially with cyclodextrins, have been used to help decrease volatility, improve stability and provide slow-release properties. However, these methods are for a number of reasons often not successful. In addition, cyclodextrins can be too expensive.
In consumer products such as deodorants, the aim is to mask malodor or to block its production and optionally also to provide a pleasant fragrance. Deodorants are generally of three types: odor maskers, antiperspirants, and germicides. Despite the many disclosures in the art pertaining to deodorant compositions, current products are not sufficient to suppress odor in a significant proportion of the population, particularly during periods of stress. There remains a need for new deodorant compositions and methods which are effective, safe and economical.
Carbonate-derived fragrance precursors having mercapto or ether groups useful for laundry, deodorant and other applications are described in EP 816 322.
WO 91/11988 refers to alternative enzyme substrates as deodorants. The substrates are amino acids containing an 0-acyl or 0-thio group.
U.S. Pat. No. 5,431,904 relates to a deodorant composition comprising a compound which is capable of serving as an alternative substrate. Disclosed is a deodorant composition comprising O-acylated serine derivatives which compete with the naturally occurring malodor producing precursor. In a preferred embodiment, the O-acylated serine may generate organoleptic acids in the axilla concomitant with suppressing the malodor.
An object of the present invention is to provide new precursors for organoleptic and/or antimicrobial compounds and/or alternative substrates for malodor producing enzymes.
A further object of the invention is to provide such new precursors which are stable under usual transport and storage conditions. Optionally, the precursors of the present invention may release more than one active component.
It has now been found that serine carbonates of formula I
or a salt thereof
wherein
R
1
is the residue of an organoleptic alcohol, phenol or of the enol form of an organoleptic aldehyde or ketone of formula R
1
OH,
R
2
is hydrogen, metal, ammonium, straight or branched alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, heterocycloalkenyl, aryl or heteroaryl, whereby all organic residues may contain heteroatoms and may carry substituents and if R
2
is hydrogen R
1
is not the residue of benzyl alcohol,
R
3
, R
4
and R
7
are independently hydrogen or lower alkyl and either R
3
and R
4
or R
3
and R
7
or R
4
and R
7
may form together a ring,
R
5
and R
6
are independently hydrogen, straight or branched alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, heterocycloalkyl, an aromatic or hetero aromatic residue, alkylcarbonyl, alkoxycarbonyl, arylcarbonyl, aryloxycarbonyl and R
5
and R
6
may together form a ring, whereby all organic residues may contain heteroatoms and may carry substituents, fulfill the aforementioned tasks and, hence, are useful for the aforementioned purposes.
The compounds of formula I are not limited to any particular stereoisomers, all possible stereoisomers (E/Z isomers, enantiomers, diastereomers) and all mixtures are thus included within the scope of the invention. Salts are also included in the general formula.
The compounds of formula I may be prepared as quaternary salts.
R
2
, R
5
and/or R
6
may contain heteroatoms selected of from the group O, N, S, P and Si.
R
2
, R
5
and/or R
6
may also carry one or more of the following substituents -halogen, -aryl, -heteroaryl, cycloalkyl, -cycloalkenyl, -heterocycloalkenyl, —OH, —OR, —NCOON═CR
2
, —OCOON═CR
2
, —COON═CR
2
—NO
2
, —COR, —C(OR)
2
R, —COOR, —CONR
2
, OCOR, —OCOOR, OCONR
2
, —NR
2
, —SOR, —SO
2
R, —SO
3
R in which R is an organic residue.
R
2
is preferably the residue of an organoleptic alcohol, phenol or of the enol form of an organoleptic aldehyde or ketone. However, compounds of formula I in which R
2
is the residue of a non-organoleptic alcohol, phenol or of the enol form of a non-organoleptic aldehyde or ketone are also useful. R
2
contains generally 1 to 30, preferably 1 to 20 C-atoms.
In particular R
1
can be alkyl, alkenyl, cycloalkyl, cycloalkenyl, alkylcycloalkyl or aralkyl; R
2
hydrogen, alkyl or aralkyl, R
5
and/or R
6
hydrogen, alkyloxycarbonyl, aryloxycarbonyl, arylalkoxycarbonyl or trialkylsilylalkoxycarbonyl.
Further preferred are compounds of formula I with R
2
to R
7
being hydrogen.
The compounds of formula I are mostly or nearly odorless at room temperature, atmospheric conditions and about 20 to 100% relative humidity. However, under activating conditions, they are cleaved and one or more active compounds, alcohols, phenols, aldehyes, and/or ketones, optionally with organoleptic and/or antimicrobial properties are generated.
The activating conditions which lead to cleavage of the precursors and thereby to the liberating of the desired active compound(s) may comprise the presence of skin bacteria, especially axilla bacteria, or of an enzyme such as protease or lipase, or elevated temperature or acidic or alkaline pH-values or a combination of two or more of these activating conditions.
In the specific case of usage as alternative substrates, the mechanism may be quite complex. Axillary malodor is generated by certain skin bacteria in the presence of apocrine secretion. Two strains of bacteria which produce axillary malodor when incubated with human apocrine secretions are Staphylococcus and several Coryneform isolates. Production of human axillary malodor can be assayed from these strains of bacteria by incubating cells with apocrine secretions collected from human axilla that has been sterilized in a phosphate buffer at pH 6.8.
The conversion of the naturally occurring apocrine secretion to axillary malodor occurs within the bacterial cells. Extracts of bacteria are capable of converting the apocrine secretion to the malodor compound in an enzymatic process. One of the malodor forming enzymes has been found to be a pyridoxal phosphate dependent amino acid lyase. The enzyme acts to cleave amino acids with the general structure HOOC—CH(NH
2
)—CH
2
—XR where X is S or O. The products of the reaction are pyruvate, ammonia, and RXH.
The naturally occurring precursor to axillary malodor in the apocrine secretion is a sulfur containing amino acid. The production of axillary malodor is blocked if an alternative substrate for the malodor forming enzyme is provided, so that the alternative substrate is cleaved instead of the apocrine precursor. The alternative substrates produce either a neutral odor or a pleasant odor upon cleavage.
The presence of alternative substrates (in the axilla) leads to competition with the natural precursor, which is present in low quantities, typically about one nanomole/axilla. Such competition almost completely prevents the malodor precursor from being converted. These compounds therefore serve as deodorants.
It has been surprisingly found that compounds of formula I are useful as alternative substrates competing with the naturally occuring malodor precursors.
Further the compounds of formula I, upon cleavage, p

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