Production of bitter principle derivatives
AssigneeJulius-Maximilians-Universitaet
InventorsRalf Wyrwa, Claudia Rode, Thomas Seemann, Lorenz Meinel, Jennifer Ritzer, Matthias Schnabelrauch
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Abstract
It is an object of the present invention to introduce carboxylic acid-functionalities suitable for coupling into the denatonium structure by means of simple synthesis, namely the synthesis of bitter principle derivatives based on the denatonium structure according to formula 1: For example, according to the invention, lidocaine derivatives may be reacted with carboxylated benzyl halogenides. The carboxylated denatonium derivatives of the present invention are especially applied in medicine, biology, medical engineering as well as cosmetics, the pharmaceutical, chemical, and foodstuff industry.
Claims3
A compound of general formula 1
- wherein:
- (i) X− represents halogenide, sulphate, benzoate, acetate, trifluoroacetate, hydroxide, saccharinate, or capsaicinate,
- (ii) R1-R10 independently represent:
- (a) hydrogen,
- (b) halogen,
- (c) C1-C5 alkyl,
- (d) C1-C4 alkoxy,
- (e) C1-C20 alkoxycarbonyl
- (f) —NH—P or —O—P, wherein P is a hydrogen
- or a residue consisting of 1-30 amino acids selected from the group consisting of D-amino acids, L-amino acids and unnatural amino acids, wherein said amino acids are optionally modified for coupling,
- (g) —(Y)n—COOM with M=Na, K, or [N(R12)4]+, or
- (h) —(Y)n—C(O)NR14R15, further wherein Y represents an organic residue selected from the group consisting of:
- —CH2, —CH(CH3)—, —CH2—CH2—, —(CH2)3—, —CH═CH—, —C≡C—, —O—CH2—CH2—, —O—CH2—CH2—O—CH2—CH2—, and —NH—CH2—CH2— and n=0 or 1,
- (iii) R14 and R15 represent hydrogen, a C1-C12 alkyl, or a residue consisting of 1-30 amino acids selected from the group consisting of D-amino acids, L-amino acids and unnatural amino acids, and
- (iv) at least one of the residues R1-R10 is a (a) —(Y)n—COOM or (b) —(Y)n—C(O)NR14R15, wherein Y, M, R14, and R15 are as defined above, and
- (v) R11 and R12 independently represent hydrogen or a C1-C10 alkyl residue.
Dependencies are inferred from the claim text.