4-aminobut-2-ynecarboxylic acid derivatives

Details 4-aminobut-2-ynecarboxylic acid derivatives 4-aminobut-2-ynecarboxylic acid derivatives

2001-12-13

2004-06-01

Nazario-Gonzalez, Porfirio (Department: 1621)

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

Organic compounds

Carboxylic acid esters

C560S155000, C562S433000, C562S553000, C562S574000

Reexamination Certificate

active

06743940

ABSTRACT:

The present invention relates to selected 4-aminobut-2-ynecarboxylic acid derivatives, to the preparation of such compounds, to the use of such compounds in the antimicrobial treatment of surfaces, as antimicrobial active ingredients against gram-positive and gram-negative bacteria, yeasts and fungi and in preserving cosmetics, household products, textiles, plastics and for use in disinfectants.
The compounds according to the invention correspond to the formula
wherein
R
1
and R
2
are each independently of the other hydrogen, C
1
-C
20
alkyl; C
3
-C
12
cycloalkyl; unsubstituted or C
1
-C
5
alkyl-, C
3
-C
12
cycloalkyl-, C
1
-C
5
alkoxy-, C
3
-C
12
cycloalkoxy-, halo-, oxo-, carboxy-, carboxy-C
1
-C
7
alkyl ester-, carboxy-C
3
-C
12
cycloalkyl ester-, cyano-, trifluoromethyl-, pentafluoroethyl-, amino-, N,N-mono- or di-C
1
-C
20
alkylamino- or nitro-substituted phenyl, phenyl-C
1
-C
5
alkyl, naphthyl or naphthyl-C
1
-C
5
alkyl,
R
3
is hydrogen; C
1
-C
20
alkyl; or C
3
-C
12
cycloalkyl; there not being included compounds of formula (1) wherein
a) R
1
and R
2
are each independently of the other C
1
-C
3
alkyl; and
R
3
is hydrogen; and
b) R
1
is methyl;
R
2
is phenyl; or chloro-substituted phenyl; and
R
3
is hydrogen, methyl or ethyl.
The invention preferably relates to compounds of formula (1) wherein
R
1
and R
2
are each independently of the other hydrogen; C
1
-C
20
alkyl; C
1
-C
5
alkoxy; unsubstituted or C
1
-C
5
alkyl- or halo-substituted phenyl or phenyl-C
1
-C
5
alkyl; and
R
3
is hydrogen; or C
1
-C
5
alkyl;
and especially to compounds of formula (1) wherein
R
1
and R
2
are each independently of the other hydrogen; C
1
-C
20
alkyl; C
1
-C
5
alkoxy; unsubstituted or C
1
-C
5
alkyl- or halo-substituted phenyl; and
R
3
is hydrogen; or C
1
-C
5
alkyl.
Special preference is given to compounds of formula (1) wherein
R
1
is C
2
-C
20
alkyl; C
3
-C
12
cycloalkyl; unsubstituted or C
1
-C
5
alkyl-, C
3
-C
12
cycloalkyl-, C
1
-C
5
-alkoxy-, C
3
-C
12
cycloalkoxy-, halo-, oxo-, carboxy-, carboxy-C
1
-C
7
alkyl ester-, carboxy-C
3
-C
12
cycloalkyl ester-, cyano-, trifluoromethyl-, pentafluoroethyl-, amino-, N,N-mono- or di-C
1
-C
20
alkylamino- or nitro-substituted phenyl, phenyl-C
1
-C
5
alkyl, naphthyl or naphthyl-C
1
-C
5
alkyl;
R
2
is unsubstituted or C
1
-C
5
alkyl-, C
3
-C
12
cycloalkyl-, C
1
-C
5
alkoxy-, C
3
-C
12
cycloakloxy-, halo-, oxo-, carboxy-, carboxy-C
1
-C
7
alkyl ester-, carboxy-C
3
-C
12
cycloalkyl ester-, cyano-, trifluoromethyl-, pentafluoroethyl-, amino-, N,N-mono- or di-C
1
-C
20
alkylamino- or nitro-substituted phenyl, phenyl-C
1
-C
5
alkyl, naphthyl or naphthyl-C
1
-C
5
alkyl; and
R
3
is hydrogen; C
1
-C
20
alkyl; or C
3
-C
12
cycloalkyl.
Special preference is given to compounds of formula (1) wherein
R
1
is C
2
-C
20
alkyl; and
R
2
is unsubstituted or C
1
-C
5
alkyl-, C
1
-C
5
alkoxy-, halo-, trifluoromethyl- or pentafluoroethyl-substitute phenyl,
and especially to compounds of formula (1) wherein
R
1
and R
2
are each independently of the other hydrogen; or C
4
-C
20
alkyl.
Examples of especially preferred compounds according to the invention correspond to the formulae
The 4-aminobut-2-ynecarboxylic acid derivatives according to the invention are prepared in a manner known per se by reacting an amine compound of formula (5) with propargyl bromide and, in a second reaction step, reacting the metallized acetylene with chloroformic acid esters or CO
2
in accordance with the following Reaction scheme:
In that Reaction scheme
R
1
and R
2
are each independently of the other hydrogen, C
1
-C
20
alkyl; C
3
-C
12
cycloalkyl; unsubstituted or C
1
-C
5
alkyl-, C
3
-C
12
cycloalkyl-, C
1
-C
5
alkoxy-, C
3
-C
12
cycloalkoxy-, halo-, oxo-, carboxy-, carboxy-C
1
-C
7
alkyl ester-, carboxy-C
3
-C
12
cycloalkyl ester-, cyano-, triflutrifluoromethyl-, pentafluoroethyl-, amino-, N,N-mono- or di-C
1
-C
20
alkylamino- or nitro-substituted phenyl or phenyl-C
1
-C
5
alkyl, naphthyl, naphthyl-C
1
-C
5
alkyl; and
R
3
is hydrogen; C
1
-C
20
alkyl; or C
3
-C
12
cycloalkyl.
The invention relates also to the process for the preparation of the 4-aminobut-2-ynecarboxylic acid derivatives according to the invention.
The 4-aminobut-2-ynecarboxylic acid derivatives, according to the invention, of formula
wherein
R
1
and R
2
are each independently of the other hydrogen, C
1
-C
20
alkyl; C
3
-C
12
cycloalkyl; unsubstituted or C
1
-C
5
alkyl-, C
3
-C
12
cycloalkyl-, C
1
-C
5
alkoxy-, C
3
-C
12
cycloalkoxy-, halo-, oxo-, carboxy-, carboxy-C
1
-C
7
alkyl ester-, carboxy-C
3
-C
12
cycloalkyl ester-, cyano-, trifluoromethyl-, pentafluoroethyl-, amino-, N,N-mono- or di-C
1
-C
20
alkylamino- or nitro-substituted phenyl, phenyl-C
1
-C
5
alkyl, naphthyl or naphthyl-C
1
-C
5
alkyl,
R
3
is hydrogen; C
1
-C
20
alkyl; or C
3
-C
12
cycloalkyl; exhibit pronounced antimicrobial activity, especially against gram-positive and gram-negative bacteria and against bacteria of skin flora, and also against yeasts and moulds. They are accordingly suitable especially in the disinfection, deodorisation and general and antimicrobial treatment of the skin and mucosa and of integumentary appendages (hair), more especially in the disinfection of hands and of wounds.
They are therefore suitable as antimicrobial active ingredients and as preservatives in personal care preparations, for example shampoos, bath additives, hair-care products, liquid and solid soaps (based on synthetic surfactants and salts of saturated and/or unsaturated fatty acids), lotions and creams, deodorants, other aqueous or alcoholic solutions, e.g. cleansing solutions for the skin, moist cleansing cloths, oils or powders.
The invention accordingly relates also to a personal care preparation comprising at least one compound of formula (1) and cosmetically tolerable carriers or adjuvants.
The personal care preparation according to the invention comprises from 0.01 to 15% by weight, preferably from 0.1 to 10% by weight, based on the total weight of the composition, of the compound of formula (1) and cosmetically tolerable adjuvants.
Depending upon the form of the personal care preparation, it will comprise, in addition to the 4-aminobut-2-ynecarboxylic acid derivative of formula (1), further constituents, for example sequestering agents, colourings, perfume oils, thickening or solidifying (consistency regulator) agents, emollients, UV absorbers, skin-protective agents, antioxidants, additives that improve mechanical properties, such as dicarboxylic acids and/or Al, Zn, Ca and Mg salts of C
14
-C
22
fatty acids, and optionally preservatives.
The personal care preparation according to the invention may be formulated as a water-in-oil or oil-in-water emulsion, as an alcoholic or alcohol-containing formulation, as a vesicular dispersion of an ionic or non-ionic amphiphilic lipid, as a gel, a solid stick or as an aerosol formulation.
As a water-in-oil or oil-in-water emulsion the cosmetically tolerable adjuvant preferably comprises from 5 to 50% of an oily phase, from 5 to 20% of an emulsifier and from 30 to 90% water. The oily phase may contain any oil suitable for cosmetic formulations, e.g. one or more hydrocarbon oils, a wax, a natural oil, a silicone oil, a fatty acid ester or a fatty alcohol. Preferred mono- or poly-ols are ethanol, isopropanol, propylene glycol, hexylene glycol, glycerol and sorbitol.
Cosmetic formulations according to the invention are used in various fields. For example, the following preparations especially come into consideration:
skin-care preparations, e.g. skin-washing and cleansing preparations in the form of tablet-form or liquid soaps, synthetic detergents or washing pastes,
bath preparations, e.g. liquid (foam baths, milks, shower preparations) or solid bath preparations, e.g. bath cubes and bath salts;
skin-care preparations, e.g. skin emulsions, multi-emulsions or skin oils;
cosmetic personal care preparations, e.g. facial make-up in the form of day creams or powder creams, face powder (loose or pressed), rouge or cream make-up, eye-care preparations, e.g. eyeshadow preparations, mascara, eyel

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