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US 6,638,321 B1Granted
Cationic oxidation bases, their use for oxidation dyeing of keratin fibres, dyeing compositions and dyeing methods
AssigneeL'oreal
InventorsAlain Genet, Alain Lagrange
Life of this patent
Estimating the term…
Abstract
The invention relates to novel monobenzene oxidation bases containing at least one cationic group Z, Z being chosen from aliphatic chains containing at least one quaternized unsaturated ring, to their use for the oxidation dyeing of keratin fibers, to dye compositions containing them and to oxidation dyeing processes using them.
Claims36
A compound of formula (I) or an acid addition salt thereof:
- wherein:
- R1, R2 and R3, are identical or different and represent
- a hydrogen atom;
- a halogen atom;
- a group Z;
- a (C1-C6)alkylcarbonyl radical;
- an amino(C1-C6)alkylcarbonyl radical;
- an N—Z-amino(C1-C6)alkylcarbonyl radical;
- an N—(C1-C6)alkylamino(C1-C6)alkylcarbonyl radical;
- an N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl radical;
- an amino(C1-C6)alkylcarbonyl(C1-C6)alkyl radical;
- an N—Z-amino(C1-C6)alkylcarbonyl(C1-C6)alkyl radical;
- an N—(C1-C6)alkylamino(C1-C6)alkylcarbonyl(C1-C6)alkyl radical;
- an N,N—di(C1-C6)alkylamino(C1-C6)alkylcarbonyl(C1-C6)alkyl radical;
- a carboxyl radical;
- a (C1-C6)alkylcarboxyl radical;
- a C1-C6 alkylsuiphonyl radical;
- an aminosulphonyl radical;
- an N—Z-aminosulphonyl radical;
- a C1-C6 N-alkylaminosulphonyl radical;
- an N,N-di(C1-C6)alkylaminosulphonyl radical;
- an aminosulphonyl(C1-C6)alkyl radical;
- an N—Z-aminosulphonyl(C1-C6)alkyl radical;
- an N—(C1-C6)alkylaminosulphonyl(C1-C6)alkyl radical;
- an N,N-di(C1-C6)alkylaminosulphonyl(C1-C6)alkyl radical;
- a carbamyl radical;
- an N—(C1-C6)alkylcarbamyl radical;
- an N,N-di(C1-C6)alkylcarbamyl radical;
- a carbamyl(C1-C6)alkyl radical;
- an N—(C1-C6)alkylcarbamyl(C1-C6)alkyl radical;
- an N,N-di(C1-C6)alkylcarbamyl(C1-C6)alkyl radical;
- a C1-C6 alkyl radical;
- a monohydroxy(C1-C6)alkyl radical;
- a polyhydroxy(C2-C6)alkyl radical;
- a (C1-C6)alkoxy(C1-C6)alkyl radical;
- a trifluoro(C1-C6)alkyl radical;
- a cyano radical;
- a group OR6
- a group SR6;
- an amino group protected with a (C1-C6)alkylcarbonyl, (C1-C6)alkylcarboxyl, trifluoro(C1-C6)alkylcarbonyl, amino(C1-C6)alkylcarbonyl, N—Z-amino(C1-C6)alkylcarbonyl, N—(C1-C6)alkylamino(C1-C6)alkylcarbonyl, N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl, carbamyl, N—(C1-C6)alkylcarbamyl, N,N-di(C1-C6)alkylcarbamyl, C1-C6 alkylsulphonyl, aminosulphonyl, N—Z-amino-sulphonyl, C1-C6 N—alkylaminosulphonyl, N,N-di(C1-C6)alkylaminosulphonyl, thiocarbamyl or formyl radical, or with a group Z;
- an amino(C1-C6)alkyl radical wherein the amine is substituted with one or two identical or different radicals selected from C1-C6 alkyl, monohydroxy(C1-C6)alkyl, polyhydroxy(C2-C6)alkyl, C1-C6 alkylcarbonyl, carbamyl, N—(C1-C6)alkylcarbamyl, N,N-di(C1-C6)alkylcarbamyl, (C1-C6)alkylsulphonyl, formyl, trifluoro(C1-C6)alkylcarbonyl, (C1-C6)alkylcarboxyl and thiocarbamyl radicals, or with a group Z;
- R6 denotes
- a C1-C6 alkyl radical;
- a monohydroxy(C1-C6)alkyl radical;
- a polyhydroxy(C2-C6)alkyl radical;
- a group Z;
- a (C1-C6)alkoxy(C1-C6)alkyl radical;
- an ary radical
- benzyl radical;
- a carboxy(C1-C6)alkyl radical;
- a (C1-C6)alkylcarboxy(C1-C6)alkyl radical;
- a cyano(C1-C6)alkyl radical;
- a carbamyl(C1-C6)alkyl radical;
- an N—(C1-C6)alkylcarbamyl(C1-C6)alkyl radical;
- an N,N-di(C1-C6)alkylcarbamyl(C1-C6)alkyl radical;
- a trifluoro(C1-C6)alkyl radical;
- an aminosulphonyl(C1-C6)alkyl radical;
- an N—Z-aminosulphonyl(C1-C6)alkyl radical;
- an N—(C1-C6)alkylaminosulphonyl(C1-C6)alkyl radical;
- an N,N-di(C1-C6)alkylaminosulphonyl(C1-C6)alkyl radical;
- a (C1-C6)alkylsulphinyl(C1-C6)alkyl radical;
- a (C1-C6)alkylsulphonyl(C1-C6)alkyl radical;
- a (C1-C6)alkylcarbonyl(C1-C6)alkyl radical;
- an amino(C1-C6)alkyl radical;
- an amino(C1-C6)alkyl radical wherein the amine is substituted with one or two identical or different radicals selected from C1-C6 alkyl, monohydroxy(C1-C6)alkyl, polyhydroxy(C2-C6)alkyl, (C1-C6)alkylcarbonyl, formyl, trifluoro(C1-C6)alkylcarbonyl, (C1-C6)alkylcarboxyl, carbamyl, N—(C1-C6)alkylcarbamyl, N,N-di(C1-C6)alkylcarbamyl, thiocarbamyl and C1-C6 alkylsulphonyl radicals, and the group Z;
- A represents a group —NR4R5 or a hydroxyl radical;
- R4 and R5, are identical or different and represent
- a hydrogen atom;
- a group Z;
- a C1-C6 alkyl radical;
- a monohydroxy(C1-C6)alkyl radical;
- a polyhydroxy(C2-C6)alkyl radical;
- a (C1-C6)alkoxy(C1-C6)alkyl radical;
- an aryl radical;
- a benzyl radical;
- a cyano(C1-C6)alkyl radical;
- a carbamyl(C1-C6)alkyl radical;
- an N—(C1-C6)alkylcarbamyl(C1-C6)alkyl radical;
- an N,N-di(C1-C6)alkylcarbamyl(C1-C6)alkyl radical;
- a thiocarbamyl(C1-C6)alkyl radical;
- a trifluoro(C1-C6)alkyl radical;
- a
- a sulpho(C1-C6)alkyl radical;
- a (C1-C6)alkylcarboxy(C1-C6)alkyl radical;
- a (C1-C6)alkylsulphinyl(C1-C6)alkyl radical;
- an aminosulphonyl(C1-C6)alkyl radical;
- an N—Z-aminosulphonyl(C1-C6)alkyl radical;
- an N—(C1-C6)alkylaminosulphonyl(C1-C6)alkyl radical;
- an N,N-di(C1-C6)alkylaminosulphonyl(C1-C6)alkyl radical;
- a (C1-C6)alkylcarbonyl(C1-C6)alkyl radical;
- an amino(C1-C6)alkyl radical;
- an amino(C1-C6)alkyl radical wherein the amine is substituted with one or two identical or different radicals selected from C1-C6 alkyl, monohydroxy(C1-C6)alkyl, polyhydroxy(C2-C6)alkyl, (C1-C6)alkylcarbonyl, carbamyl, N—(C1-C6)alkylcarbamyl, N,N-di(C1-C6)alkylcarbamyl, C1-C6 alkylsulphonyl, formyl, trifluoro(C1-C6)alkylcarbonyl, (C1-C6)alkylcarboxyl and thiocarbamyl radicals, or with a group Z;
- Z is selected from the unsaturated cationic groups of formulae (II) and (III), and the saturated cationic groups of formula (IV):
- wherein:
- D is a divalent linker arm which represents a linear or branched alkyl chain, said alkyl chain being uninterrupted or interrupted by at least one hetero atom, and said alkyl chain being unsubstituted or substituted with at least one hydroxyl or C1-C6 alkoxy radical, and said alkyl chain optionally having at least one ketone function;
- the ring members E, G, J, L and M, are identical or different and represent a carbon, oxygen, sulphur or nitrogen atom;
- n is an integer ranging from 0 and 4 inclusive;
- m is an integer ranging from 0 and 5 inclusive;
- the radicals R, are identical or different and represent
- group Z,
- a halogen atom,
- a hydroxyl radical,
- a C1-C6 alkyl radical,
- a monohydroxy(C1-C6)alkyl radical,
- a polyhydroxy(C2-C6)alkyl radical,
- a nitro radical,
- a cyano radical,
- a cyano(C1-C6)alkyl radical,
- a C1-C6 alkoxy radical,
- a tri(C1-C6)alkylsilane(C1-C6)alkyl radical,
- an amido radical,
- an aldehydo radical,
- a carboxyl radical,
- a (C1-C6)alkylcarbonyl radical,
- a thio radical,
- a thio(C1-C6)alkyl radical,
- a C1-C6 alkylthio radical,
- an amino radical,
- an amino radical protected with a (C1-C6)alkylcarbonyl, carbamyl or C1-C6 alkylsulphonyl radical;
- a group NHRO or NROR wherein RO and R, are identical or different and represent a C1-C6 alkyl radical, a monohydroxy(C1-C6)alkyl radical or a polyhydroxy(C2-C6)alkyl radical;
- R7 represents
- a C1-C6 alkyl radical,
- a monohydroxy(C1-C6)alkyl radical,
- a polyhydroxy(C2-C6)alkyl radical,
- a cyano(C1-C6)alkyl radical,
- a tri(C1-C6)alkylsilane(C1-C6)alkyl radical,
- a (C1-C6)alkoxy(C1-C6)alkyl radical,
- a carbamyl(C1-C6)alkyl radical,
- a (C1-C6)alkylcarboxy(C1-C6)alkyl radical,
- a benzyl radical or
- a group Z of formula (II), (III) or (IV) as defined above;
- R8, R9 and R10, are identical or different and represent
- a C1-C6 alkyl radical,
- a monohydroxy(C1-C6)alkyl radical,
- a polyhydroxy(C2-C6)alkyl radical,
- a (C1-C6)alkoxy(C1-C6)alkyl radical,
- a cyano(C1-C6)alkyl radical,
- an aryl radical,
- a benzyl radical,
- an amido(C1-C6)alkyl radical,
- a tri(C1-C6)alkylsilane(C1-C6)alkyl radical,
- an amino(C1-C6)alkyl radical wherein the amine is protected with a (C1-C6)alkylcarbonyl, carbamyl or C1-C6 alkylsulphonyl radical;
- two of the radicals R8, R9 and R1 can together form, with the nitrogen atom to which they are attached, a saturated 5- or 6-membered ring, wherein said ring may contain at least one additional hetero atom, and further wherein said ring is unsubstituted or substituted with:
- a halogen atom,
- a hydroxyl radical,
- a C1-C6 alkyl radical,
- a monohydroxy(C1-C6)alkyl radical,
- a polyhydroxy(C2-C6)alkyl radical,
- a nitro radical,
- a cyano radical,
- a cyano(C1-C6)alkyl radical,
- a C1-C6 alkoxy radical,
- a tri(C1-C6)alkylsilane(C1-C6)alkyl radical,
- an amido radical,
- an aldehydo radical,
- a carboxyl radical,
- a keto(C1-C6)alkyl radical,
- a thio radical,
- a thio(C1-C6)alkyl radical,
- a C1-C6 alkylthio radical,
- an amino radical or
- an amino radical protected with a (C1-C6)alkylcarbonyl, carbamyl or C1-C6 alkylsulphonyl radical;
- one of the radicals R8, R9 and R10 may represent a second group Z which is identical to or different from the first group Z;
- R11 represents
- a C1-C6 alkyl radical;
- a monohydroxy(C1-C6)alkyl radical;
- a polyhydroxy(C2-C6)alkyl radical;
- an aryl radical;
- a benzyl radical;
- an amino(C1-C6)alkyl radical, p2 an amino(C1-C6)alkyl radical wherein the amine is protected with a (C1-C6)alkylcarbonyl, carbamyl or C1-C6 alkylsulphonyl radical;
- a carboxy(C1-C6)alkyl radical;
- a cyano(C1-C6)alkyl radical;
- a carbamyl(C1-C6)alkyl radical;
- a trifluoro(C1-C6)alkyl radical;
- a tri(C1-C6)alkylsilane(C1-C6)alkyl radical;
- a sulphonamido(C1-C6)alkyl radical;
- a (C1-C6)alkylcarboxy(C1-C6)alkyl radical;
- a (C1-C6)alkylsulphinyl(C1-C6)alkyl radical;
- a (C1-C6)alkylsulphonyl(C1-C6)alkyl radical;
- a (C1-C6)alkylketo(C1-C6)alkyl radical;
- an N—(C1-C6)alkylcarbamyl(C1-C6)alkyl radical;
- an N—(C1-C6)alkylsulphonamido(C1-C6)alkyl radical;
- x and y are integers equal to 0 or 1;
- with the proviso that:
- in the unsaturated cationic groups of formula (II):
- when x=0, the divalent linker arm D is attached to the nitrogen
- atom,
- when x=1, the divalent linker arm D is attached to one of the ring members E G J or L,
- y can take the value 1 only:
- 1) when the ring members E, G, J and L simultaneously represent a carbon atom and when the radical R7 is borne by the nitrogen atom of the unsaturated ring;
- or
- 2) when at least one of the ring members E, G, J and L represents a nitrogen atom to which the radical R7 is attached;
- in the unsaturated cationic groups of formula (III):
- when x=0, the linker arm D is attached to the nitrogen atom,
- when x=1, the linker arm D is attached to one of the ring members E, G, J, L or M,
- y can take the value 1 only when at least one of the ring members E, G, J, L and M represents a divalent atom and when the radical R7 is borne by the nitrogen atom of the unsaturated ring;
- in the cationic groups of formula (IV):
- when x=0, then the linker arm is attached to the nitrogen atom bearing the radicals R8 to R10,
- when x=1, then two of the radicals R8 to R1 form, together with the nitrogen atom to which they are attached, a saturated 5- or 6-membered ring as defined above, and the linker arm D is borne by a carbon atom of said saturated ring;
- X− represents a monovalent or divalent anion;
- further with the provisos that:
- the number of unsaturated cationic groups Z of formula (II) or (III) in said compound or acid addition salt thereof is at least equal to 1;
- when A represents a group —NP4R5, wherein R4 or R5 represents a group Z wherein the divalent linker arm D represents an alkyl chain containing a ketone function, then said ketone function is not directly attached to the nitrogen atom of the group —NR4R5;
- wherein 4-amino-3-methyl-N-ethyl-N-∃-(1-pyridinium)ethylaniline chloride is excluded;
- when:
- A is a hydroxyl radical,
- two of R1, R2 and R3 are hydrogen atoms and one of R1, R2 and R3 is a
- wherein:
- Z is a compound of formula (III), wherein:
- D is CH2,
- x is 0,
- y is 0,
- E, G, J, L and M are carbon atoms, and
- m is 1,
- then, R is not chosen from hydroxy radicals;
- amino radicals;
- a CH2OH radical;
- groups NR′′R′″, wherein R″ and R′″ are each a (C1-C4)alkyl radical;
- (C1-C4) alkyl radicals;
- and fused aromatic rings;
- when:
- A is a hydroxyl radical,
- two of R1, R2 and R3 are hydrogen atoms and one of R1, R2 and R3 is a group Z,
- wherein:
- Z is a compound of formula (III), wherein:
- D is CH2,
- x is 0,
- y is 0,
- E, G, J, L and M are carbon atoms, and
- m is 2,
- then:
- neither R is chosen from hydroxy radicals;
- amino radicals;
- groups NR″R′″ wherein R″ and R′″ are each a (C1-C4)alkyl radical;
- (C1-C4)alkyl radicals;
- and fused aromatic rings;
- and
- when:
- two of R1, R2 and R3 are hydrogen atoms and one of R1, R2 and R3 is a trifluoromethyl radical,
- A is NR4R5, wherein:
- one of R4 and R5 is chosen from a hydrogen atom and C1-C4 alkyl radicals, and
- one of R4 and R5 is a group Z, wherein:
- Z is a compound of formula (II), wherein:
- D is chosen from C1-C3 alkyl chains, and
- one of x, y and n is 1, and two of x, y, and n are 0, and
- two of E, J, G and L are nitrogen atoms such that a 1,2,4-triazolium ring is formed,
- then, R11, R7 and R, if present, are not C1-C4 alkyl radicals and R11 and R7 are not phenyl (C1-C2)alkyl radicals.
244 more elements
A compound of formula (I) or an acid addition salt thereof:
- wherein:
- R1, R2 and R3, are identical or different and represent
- a hydrogen atom;
- a halogen atom;
- a group Z;
- a (C1-C6)alkylcarbonyl radical;
- an amino(C1-C6)alkylcarbonyl radical;
- an N—Z-amino(C1-C6)alkylcarbonyl radical;
- an N—(C1-C6)alkylamino(C1-C6)alkylcarbonyl radical;
- an N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl radical;
- an amino(C1-C6)alkylcarbonyl(C1-C6)alkyl radical;
- an N—Z-amino(C1-C6)alkylcarbonyl(C1 -C6)alkyl radical;
- an N—(C1-C6)alkylamino(C1-C6)alkylcarbonyl(C1-C6)alkyl radical;
- an N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl(C1-C6)alkyl radical;
- a carboxyl radical;
- a (C1-C6)alkylcarboxyl radical;
- a C1-C6 alkylsulphonyl radical;
- an aminosulphonyl radical;
- an N—Z-aminosulphonyl radical;
- a C1-C6 N—alkylaminosulphonyl radical;
- an N,N-di(C1-C6)alkylaminosulphonyl radical;
- an aminosulphonyl(C1-C6)alkyl radical;
- an N—Z-aminosulphonyl(C1-C6)alkyl radical;
- an N—(C1-C6)alkylaminosulphonyl(C1-C6)alkyl radical;
- an N,N-di(C1-C6)alkylaminosulphonyl(C1-C6)alkyl radical;
- a carbamyl radical;
- an N—(C1-C6)alkylcarbamyl radical;
- an N,N-di(C1-C6)alkylcarbamyl radical;
- a carbamyl(C1-C6)alkyl radical;
- an N—(C1-C6)alkylcarbamyl(C1-C6)alkyl radical;
- an N,N-di(C1-C6)alkylcarbamyl(C1-C6)alkyl radical;
- a C1-C6 alkyl radical;
- a monohydroxy(C1-C6)alkyl radical;
- a polyhydroxy(C2-C6)alkyl radical;
- a (C1-C6)alkoxy(C1-C6)alkyl radical;
- a trifluoro(C1-C6)alkyl radical;
- a cyano radical;
- a group OR6
- a group SR6;
- an amino group protected with a (C1-C6)alkylcarbonyl, (C1-C6)alkylcarboxyl, trifluoro(C1-C6)alkylcarbonyl, amino(C1-C6)alkylcarbonyl, N—Z-amino(C1-C6)alkylcarbonyl, N—(C1-C6)alkylamino(C1-C6)alkylcarbonyl, N,N-di(C1-C6)alkylamino(C1-C6)alkylcarbonyl, carbamyl, N—(C1-C6)alkylcarbamyl, N,N-di(C1-C6)alkylcarbamyl, C1-C6 alkylsulphonyl, aminosulphonyl, N—Z-amino-sulphonyl, C1-C6 N—alkylaminosulphonyl, N,N-di(C1-C6)alkylaminosulphonyl, thiocarbamyl or formyl radical, or with a group Z;
- an amino(C1-C6)alkyl radical wherein the amine is substituted with one or two identical or different radicals selected from C1-C6 alkyl, monohydroxy(C1-C6)alkyl, polyhydroxy(C2-C6)alkyl, C1-C6 alkylcarbonyl, carbamyl, N—(C1-C6)alkylcarbamyl, N,N-di(C1-C6)alkylcarbamyl, (C1-C6)alkylsulphonyl, formyl, trifluoro(C1-C6)alkylcarbonyl, (C1-C6)alkylcarboxyl and thiocarbamyl radicals, or with a group Z;
- R6 denotes
- a C1-C6 alkyl radical;
- a monohydroxy(C1-C6)alkyl radical;
- a polyhydroxy(C2-C6)alkyl radical;
- a group Z;
- a (C1-C6)alkoxy(C1-C6)alkyl radical;
- an aryl radical;
- a benzyl radical;
- a carboxy(C1-C6)alkyl radical;
- a (C1-C6)alkylcarboxy(C1-C6)alkyl radical;
- a cyano(C1-C6)alkyl radical;
- a carbamyl(C1-C6)alkyl radical;
- an N—(C1-C6)alkylcarbamyl(C1-C6)alkyl radical;
- an N,N-di(C1-C6)alkylcarbamyl(C1-C6)alkyl radical;
- a trifluoro(C1-C6)alkyl radical;
- an aminosulphonyl(C1-C6)alkyl radical;
- an N—Z-aminosulphonyl(C1-C6)alkyl radical;
- an N—(C1-C6)alkylaminosulphonyl(C1-C6)alkyl radical;
- an N,N-di(C1-C6)alkylaminosulphonyl(C1-C6)alkyl radical;
- a (C1-C6)alkylsulphinyl(C1-C6)alkyl radical;
- a (C1-C6)alkylsulphonyl(C1-C6)alkyl radical;
- a (C1-C6)alkylcarbonyl(C1-C6)alkyl radical;
- an amino(C1-C6)alkyl radical;
- an amino(C1-C6)alkyl radical wherein the amine is substituted with one or two identical or different radicals selected from C1-C6 alkyl, monohydroxy(C1-C6)alkyl, polyhydroxy(C2-C6)alkyl, (C1-C6)alkylcarbonyl, formyl, trifluoro(C1 -C6)alkylcarbonyl, (C1-C6)alkylcarboxyl, carbamyl, N—(C1-C6)alkylcarbamyl, N,N-di(C1-C6)alkylcarbamyl, thiocarbamyl and C1-C6 alkylsulphonyl radicals, and the group Z;
- A represents a group —NR4R5 or a hydroxyl radical;
- R4 and R5, are identical or different and represent
- a hydrogen atom;
- a group Z;
- a C1-C6 alkyl radical;
- a monohydroxy(C1-C6)alkyl radical;
- a polyhydroxy(C2-C6)alkyl radical;
- a (C1-C6)alkoxy(C1-C6)alkyl radical;
- an aryl radical;
- a benzyl radical;
- a cyano(C1-C6)alkyl radical;
- a carbamyl(C1-C6)alkyl radical;
- an N—(C1-C6)alkylcarbamyl(C1-C6)alkyl radical;
- an N,N-di(C1-C6)alkylcarbamyl(C1-C6)alkyl radical;
- a thiocarbamyl(C1-C6)alkyl radical;
- a trifluoro(C1-C6)alkyl radical;
- a sulpho(C1-C6)alkyl radical;
- a (C1-C6)alkylcarboxy(C1-C6)alkyl radical;
- a (C1-C6)alkylsulphinyl(C1-C6)alkyl radical;
- an aminosulphonyl(C1-C6)alkyl radical;
- an N—Z-aminosulphonyl(C1-C6)alkyl radical;
- an N—(C1-C6)alkylaminosulphonyl(C1-C6)alkyl radical;
- an N,N-di(C1-C6)alkylaminosulphonyl(C1-C6)alkyl radical;
- a (C1-C6)alkylcarbonyl(C1-C6)alkyl radical;
- an amino(C1-C6)alkyl radical;
- an amino(C1-C6)alkyl radical wherein the amine is substituted with one or two identical or different radicals selected from C1-C6 alkyl, monohydroxy(C1-C6)alkyl, polyhydroxy(C2-C6)alkyl, (C1-C6)alkylcarbonyl, carbamyl, N—(C1-C6)alkylcarbamyl, N,N-di(C1-C6)alkylcarbamyl, C1-C6 alkylsulphonyl, formyl, trifluoro(C1-C6)alkylcarbonyl, (C1-C6)alkylcarboxyl and thiocarbamyl radicals, or with a group Z;
- Z is selected from the unsaturated cationic groups of formulae (II) and (III), and the saturated cationic groups of formula (IV):
- wherein:
- D is a divalent linker arm which represents a linear or branched alkyl chain, said alkyl chain being uninterrupted or interrupted by at least one hetero atom, and said alkyl chain being unsubstituted or substituted with at least one hydroxyl or C1-C6 alkoxy radical, and said alkyl chain optionally having at least one ketone function;
- the ring members E, G, J, L and M, are identical or different and represent a carbon, oxygen, sulphur or nitrogen atom;
- n is an integer ranging from 0 and 4 inclusive;
- m is an integer ranging from 0 and 5 inclusive;
- the radicals R, are identical or different and represent
- a group Z,
- a halogen atom,
- a hydroxyl radical,
- a C1-C6 alkyl radical,
- a monohydroxy(C1-C6)alkyl radical,
- a polyhydroxy(C2-C6)alkyl radical,
- a nitro radical,
- a cyano radical,
- a cyano(C1-C6)alkyl radical,
- a C1-C6 alkoxy radical,
- a tri(C1-C6)alkylsilane(C1-C6)alkyl radical,
- an amido radical,
- an aldehydo radical,
- a carboxyl radical,
- a (C1-C6)alkylcarbonyl radical,
- a thio radical,
- a thio(C1-C6)alkyl radical,
- a C1-C6 alkylthio radical,
- an amino radical,
- an amino radical protected with a (C1-C6)alkylcarbonyl, carbamyl or C1-C6 alkylsuiphonyl radical;
- a group NHR″ or NR″R wherein R″ and R, are identical or different and represent a C1-C6 alkyl radical, a monohydroxy(C1-C6)alkyl radical or a polyhydroxy(C2-C6)alkyl radical;
- R7 represents
- a C1-C6 alkyl radical,
- a monohydroxy(C1-C6)alkyl radical,
- a polyhydroxy(C2-C6)alkyl radical,
- a cyano(C1-C6)alkyl radical,
- a tri(C1-C6)alkylsilane(C1-C6)alkyl radical,
- a (C1-C6)alkoxy(C1-C6)alkyl radical,
- a carbamyl(C1-C6)alkyl radical,
- a (C1-C6)alkylcarboxy(C1-C6)alkyl radical,
- a benzyl radical or
- a group Z of formula (II), (III) or (IV) as defined above;
- R8, R9 and R10, are identical or different and represent
- a C1-C6 alkyl radical,
- a monohydroxy(C1-C6)alkyl radical,
- a polyhydroxy(C2-C6)alkyl radical,
- a (C1-C6)alkoxy(C1-C6)alkyl radical,
- a cyano(C1-C6)alkyl radical,
- an aryl radical,
- a benzyl radical,
- an amido(C1-C6)alkyl radical,
- a tri(C1-C6)alkylsilane(C1-C6)alkyl radical,
- an amino(C1-C6)alkyl radical wherein the amine is protected with a (C1-C6)alkylcarbonyl, carbamyl or C1-C6 alkylsulphonyl radical;
- two of the radicals R8, R9 and R10 can together form, with the nitrogen atom to which they are attached, a saturated 5- or 6-membered ring, wherein said ring may contain at least one additional hetero atom, and further wherein said ring is unsubstituted or substituted with:
- a halogen atom,
- a hydroxyl radical,
- a C1-C6 alkyl radical,
- a monohydroxy(C1-C6)alkyl radical,
- a polyhydroxy(C2-C6)alkyl radical,
- a nitro radical,
- a cyano radical,
- a cyano(C1-C6)alkyl radical,
- a C1-C6 alkoxy radical,
- a tri(C1-C6)alkylsilane(C1-C6)alkyl radical,
- an amido radical,
- an aldehydo radical,
- a carboxyl radical,
- a keto(C1-C6)alkyl radical,
- a thio radical,
- a thio(C1-C6)alkyl radical,
- a C1-C6 alkylthio radical,
- an amino radical or
- an amino radical protected with a (C1-C6)alkylcarbonyl, carbamyl or C1-C6 alkylsulphonyl radical;
- one of the radicals R8, R9 and R10 may represent a second group Z which is identical to or different from the first group Z;
- R11 represents
- a C1-C6 alkyl radical;
- a monohydroxy(C1-C6)alkyl radical;
- a polyhydroxy(C2-C6)alkyl radical;
- an aryl radical;
- a benzyl radical;
- an amino(C1-C6)alkyl radical,
- an amino(C1-C6)alkyl radical wherein the amine is protected with a (C1-C6)alkylcarbonyl, carbamyl or C1-C6 alkylsulphonyl radical;
- a carboxy(C1-C6)alkyl radical;
- a cyano(C1-C6)alkyl radical;
- a carbamyl(C1-C6)alkyl radical;
- a trifluoro(C1-C6)alkyl radical;
- a tri(C1-C6)alkylsilane(C1-C6)alkyl radical;
- a sulphonamido(C1-C6)alkyl radical;
- a (C1-C6)alkylcarboxy(C1-C6)alkyl radical;
- a (C1-C6)alkylsulphinyl(C1-C6)alkyl radical;
- a (C1-C6)alkylsulphonyl(C1-C6)alkyl radical;
- a (C1-C6)alkylketo(C1-C6)alkyl radical;
- an N—(C1-C6)alkylcarbamyl(C1 -C6)alkyl radical;
- an N—(C1-C6)alkylsulphonamido(C1-C6)alkyl radical;
- x and y are integers equal to 0 or 1;
- with the proviso that:
- in the unsaturated cationic groups of formula (II):
- when x=0, the divalent linker arm D is attached to the nitrogen atom,
- when x=1, the divalent linker arm D is attached to one of the ring members E, G, J or L,
- y can take the value 1 only:
- when the ring members E, G, J and L simultaneously represent a carbon atom and when the radical R7 is borne by the nitrogen atom of the unsaturated ring;
- or
- 2) when at least one of the ring members E, G, J and L represents a nitrogen atom to which the radical R7 is attached;
- in the unsaturated cationic groups of formula (III):
- when x=0, the linker arm D is attached to the nitrogen atom,
- when x=1, the linker arm D is attached to one of the ring members E, G, J, L or M,
- y can take the value 1 only when at least one of the ring members E, G, J, L and M represents a divalent atom and when the radical R7 is borne by the nitrogen atom of the unsaturated ring;
- in the cationic groups of formula (IV):
- when x=0, then the linker arm is attached to the nitrogen atom bearing the radicals R8 to R10,
- when x=1, then two of the radicals R8 to R10 form, together with the nitrogen atom to which they are attached, a saturated 5- or 6-membered ring as defined above, and the linker arm D is borne by a carbon atom of said saturated ring;
- X− represents a monovalent or divalent anion;
- further with the provisos that:
- the number of unsaturated cationic groups Z of formula (II) in said compound or acid addition salt thereof is at least equal to 1;
- when A represents a group —NR4R5, wherein R4 or R5 represents a group Z wherein the divalent linker arm D represents an alkyl chain containing a ketone function, then said ketone function is not directly attached to the nitrogen atom of the group —NR4R5;
- wherein 4-amino-3-methyl-N-ethyl-N-β-(1-pyridinium)ethylaniline chloride is excluded;
- and
- when:
- two of R1, R2 and R3 are hydrogen atoms and one of R1, R2 and R3 is a trifluoromethyl radical,
- A is NR4R5, wherein:
- one of R4 and R5 is chosen from a hydrogen atom and C1-C4 alkyl radicals, and
- one of R4 and R5 is a group Z, wherein:
- Z is a compound of formula (II), wherein:
- D is chosen from C1-C3 alkyl chains, and
- one of x, y and n is 1, and two of x, y, and n are 0, and
- two of E, J, G and L are nitrogen atoms such that a 1,2,4-triazolium ring is formed,
- then, R11, R7 and R, if present, are not C1-C4 alkyl radicals and R11 and R7 are not phenyl(C1-C2)alkyl radicals.
211 more elements
Dependencies are inferred from the claim text.