Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
  • C07D213/84—Nitriles
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
  • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
  • A23L27/30—Artificial sweetening agents
  • A23L27/31—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives
  • A23L27/32—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives containing dipeptides or derivatives
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
  • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
  • C07C275/42—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
  • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
  • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

• New sweetening agents derived from N- (4-cyanophenylcarbamoyl 2-cyanopyrid-5-ylcarbamoyl) -L-asnartic or L-glutamic ⁇ -3,4-disubstituted amino acids.
• the present invention relates to new sweetening agents derived from N- (4-cyanophenylcarbamoyl or 2-cyanopyrid-5-ylcarbamoyl) -L-aspartic or L-glutamic ⁇ -benzene acids.
• These new sweetening agents of very high sweetening intensity are particularly useful for sweetening various products, and in particular carbonated drinks, food, confectionery, pastries, chewing gum, hygiene products, cosmetics, articles toiletries, pharmaceutical and veterinary products and their equivalents.
• a sweetening agent to be usable on an industrial scale, must in particular have an intense sweetening power, making it possible to limit its cost of use.
• the new compounds according to the present invention exhibit extremely high sweetening activities since they are, on a weight basis, up to 50,000 times more powerful than sucrose (table sugar).
• the most used is a dipeptide derivative, NL- ⁇ -aspartyl-L-phenylalanine 1-methyl ester, better known under the name of aspartame (US 3,492,131).
• the main advantages of this compound are its excellent organoleptic properties and its chemical constitution based on two natural amino acids, L-aspartic acid and L-phenylalanine.
• the extremely high sweetening intensity of the compounds of the invention has the advantage of making them low cost sweeteners.
• the preferred sweeteners of the present invention are in fact, on a weight basis, up to 50,000 times sweeter than sugar, which amounts to saying that 1 gram of the preferred compounds of the invention is sufficient to replace up to 50 kilograms of sugar. Since the preferred sweeteners of the present invention are approximately 250 to 400 times more powerful than aspartame itself, their cost of use will therefore be very low compared to aspartame, which makes it advantageous to envisage their industrial application.
• R 1 and R 3 are hydrogen or halogen atoms, or groups CN, NO 2 , R '(R' being an alkyl group of 1 to 6 carbon atoms), COOR “, R” CO, halomethyl , R “O, CONHR”, SO 2 R “or SOR” (R “being an alkyl group of 1 to 4 carbon atoms);
• R 2 is an oxygen or sulfur atom
• n 0, 1 or 2; and the configuration of the carbon atom indicated C *, carrying an amino group, being L or DL.
• Y is a CH group or a nitrogen atom
• A is an oxygen atom
• n 1 or 2
• R is a 3,4-disubstituted phenyl radical chosen from the groups:
• a particularly advantageous embodiment of the invention is N- (4-cyanophenylcarbamoyl) -L-aspartic- ⁇ -3,4-di thylbenzenamide acid of formula:
• Another particularly advantageous embodiment of the invention is N- (2-cyanopyrid-5- acid ylcarbamoyl) -L-aspartic- ⁇ -3,4-dimethylbenzenamide of formula:
• N- (4-cyanophenylcarbamoyl) -L-aspartic- ⁇ -3,4-methylenedioxy benzenide N- acid (2-cyanopyrid-5-ylcarbamoyl) -L-aspartic- ⁇ -3,4-methylenedioxybenzenamide
• N- (4-cyanophenylcarbamoyl) -L-aspartic- ⁇ -3-hydroxy-4-methoxybenzenamide N- (2-cyanopyrid-5-ylcarbamoyl) -L-aspartic- ⁇ -3-hydroxy-4-methoxybenzenamide
• the compounds of the invention are therefore distinguished from the compounds described in document JP 86-260052 by the very specific nature and the position of the substituents attached to the benzene group. Indeed, in this prior document, the benzene cycle of the benzene group of the compounds described and claimed is monosubstituted, and, for the examples mentioned, only in position 4 (para).
• the phenyl group R is simultaneously substituted in positions 3 (meta) and 4 (para) by specific groups.
• the choice in the compounds of the invention of this new group R results in a spectacular increase in the sweetening power, which can reach 10 (ten) times that of the compounds of the prior art, and consequently a significant reduction in the cost of use of such compounds.
• the sweetening agents of the present invention can be added to any edible product in which it is desired to provide a sweet taste, provided that they are added in sufficient proportions to reach the desired level of sweetness.
• the optimal concentration of use of the sweetening agent will depend on various factors such as, for example, the sweetness of the sweetening agent, the conditions of storage and use of the products, the particular constituents of the products and the level of desired sweetness. Any qualified person can easily determine the optimal proportion of sweetening agent to be used to obtain an edible product by performing routine sensory analyzes.
• the sweetening agents of the present invention will, in general, be added to the edible products in proportions ranging, depending on the sweetening power of the compound, from 0.5 mg to 50 mg of sweetening agent per kilogram or per liter of edible product.
• the concentrated products will obviously contain higher amounts of sweetening agent, and will then be diluted according to the final intentions of use.
• the sweetening agents of the present invention can be added in pure form to the products to be sweetened, but, because of their high sweetening power, they are generally mixed with a carrier ("carrier”) or with a bulking agent (“bulking agent”). ”) appropriate.
• the appropriate carriers or bulking agents are chosen from the group consisting of polydextrose, starch, maltodextrins, cellulose, methylcellulose, carboxymethylcellulose and other derivatives of cellulose, sodium alginate, pectins, gums, lactose, maltose, glucose, leucine, glycerol, mannitol, sorbitol, sodium bicarbonate, phosphoric, citric, tartaric, fumaric, benzoic, sorbic, propionic acids, and their sodium salts , potassium and calcium, and their equivalents.
• the sweetening agents in accordance with the invention may, in an edible product, be used alone, as the sole sweetening agent, or in combination with other sweetening agents such as sucrose, corn syrup, fructose, derivatives or the like sweetened dipeptides (aspartame, alitame), neohesperidin dihydrochalcone, hydrogenated isomaltulose, stevioside, sugars L, glycyrrhizin, xylitol, sorbitol, mannitol, acesulfame, saccharin and its sodium salts, potassium, ammonium and calcium, cyclamic acid and its sodium, potassium and calcium salts, sucralose, monellin, thaumatin, and their equivalents.
• sweetening agents such as sucrose, corn syrup, fructose, derivatives or the like sweetened dipeptides (aspartame, alitame), neohesperidin dihydrochalcone
• the compounds of the invention can also be used either in their acid form or in their salt form obtained using physiologically acceptable inorganic or organic bases, which has the effect of increasing their solubility.
• these compounds are salified in the form of sodium, potassium, ammonium, calcium or magnesium salts.
• the preparation of the compounds of the invention uses in particular the methods commonly used for peptide synthesis (see for example M. Bodansky and A. Bodansky, The Practice of Peptide Synthesis, Springer Verlag, Berlin, 1984).
• the purification of the compounds of the invention is carried out according to standard techniques such as recrystallization or chromatography. Their structure and purity have been controlled by conventional techniques (thin layer chromatography, high performance liquid chromatography, infrared spectrometry, nuclear magnetic resonance, elementary analysis).
• the sweetening power of the compounds described in the examples was evaluated by a group of eight experienced people. For this, the compounds, in aqueous solution at variable concentrations, are compared, in terms of taste, to a 2% sucrose control solution. The sweetening power of the compound, tested relative to sucrose, then corresponds to the weight ratio which exists between the compound and sucrose at equal sweetening intensity, that is to say when the sweet flavors of the solution of the tested compound and of the sucrose control solution is considered, by a majority of people, to have the same sweetening intensity.
• N- (4-cyanophenylcarbamoyl) -L-aspartic- ⁇ - 3,4-dimethylbenzenamide has a sweetening power which is, on a weight basis, 50,000 times higher than that of sucrose compared to a sucrose solution at 2%.
• the sweetening power of other compounds according to the invention obtained according to an experimental protocol similar to that described above and which those skilled in the art will easily find, is given in Table 1.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• Proteomics, Peptides & Aminoacids (AREA)
• Health & Medical Sciences (AREA)
• Nutrition Science (AREA)
• Engineering & Computer Science (AREA)
• Food Science & Technology (AREA)
• Polymers & Plastics (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Seasonings (AREA)
• Peptides Or Proteins (AREA)

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• 1995
  • 1995-01-26 FR FR9500878A patent/FR2729950B1/fr not_active Expired - Lifetime
• 1996
  • 1996-01-25 JP JP8522682A patent/JPH10512872A/ja active Pending
  • 1996-01-25 CA CA002209922A patent/CA2209922A1/en not_active Abandoned
  • 1996-01-25 WO PCT/FR1996/000124 patent/WO1996022971A1/fr not_active Application Discontinuation
  • 1996-01-25 EP EP96901851A patent/EP0805799A1/de not_active Withdrawn
  • 1996-01-25 AU AU46267/96A patent/AU689698B2/en not_active Expired - Fee Related

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