# US 9,750,676 B2 · Basic amino acid derivative that demonstrates a gelling ability in a water system > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,750,676 B2 - Document ID: US9750676B2 - Status: Granted - Kind: B2 - Application number: 14/453,036 - Filed: 2014-08-06 - Published: 2014-11-27 - Granted: 2017-09-05 - Earliest claimed: 2012-02-09 - Assignees: Ajinomoto Co., Inc. - Applicants: Ajinomoto Co., Inc. - Inventors: Kenji Hanabusa; Masahiro Suzuki; Takanori Sugimoto - Web page: https://patentgrep.com/patent/US9750676B2 ## CPC - A61K 8/44: Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof - A61K 8/042: {Gels} - A61K 8/442: {substituted by amido group(s)} - A61Q 5/00: Preparations for care of the hair - A61Q 19/00: Preparations for care of the skin - A61Q 19/10: Washing or bathing preparations - C07C 231/12: by reactions not involving the formation of carboxamide groups - C07C 237/12: having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups (peptides C07K) - C07C 309/14: containing amino groups bound to the carbon skeleton - A61Q 5/12: Preparations containing hair conditioners - A61Q 17/04: Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) - A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS ## Abstract Provided is a compound capable of gelling various aqueous compositions containing salt, acid and the like. An amphoteric ion-type basic amino acid derivative represented by the formula (1A): wherein each substituent is as defined in DESCRIPTION, or a salt thereof. ## Claims ### Claim 1 A compound represented by formula (1 A): wherein R1—CO— is an acyl group derived from an optionally substituted saturated or unsaturated fatty acid having 6 to 18 carbon atoms; R2 and R3 are each independently an optionally substituted saturated or unsaturated, straight chain or branched chain hydrocarbon group having 1 to 6 carbon atoms, or R2 and R3 form, together with the nitrogen atom to which they are bonded, an optionally substituted heterocycle; R4, R5, and R6 are each independently a hydrogen atom or an optionally substituted saturated or unsaturated, straight chain or branched chain hydrocarbon group having 1 to 6 carbon atoms; m is an integer of 1 to 20; n is an integer of 1 to 4; X is a sulfonic acid group or a carboxylic acid group; and Y is an optionally substituted saturated or unsaturated, straight chain or branched chain divalent hydrocarbon group having 1 to 8 carbon atoms, or a salt thereof. ### Claim 2 (depends on 1) The compound according to claim 1, wherein R1—CO— is an acyl group derived from a saturated or unsaturated fatty acid having 6 to 18 carbon atoms; R2 and R3 are each independently a saturated or unsaturated, straight chain or branched chain hydrocarbon group having 1 to 6 carbon atoms, or R2 and R3 form, together with the nitrogen atom to which they are bonded, a heterocycle; R4, R5, and R6 are each independently a hydrogen atom or a saturated or unsaturated, straight chain or branched chain hydrocarbon group having 1 to 6 carbon atoms; and Y is a saturated or unsaturated, straight chain or branched chain divalent hydrocarbon group having 1 to 8 carbon atoms, or a salt thereof. ### Claim 3 (depends on 1) The compound according to claim 1, which is represented by formula (1): wherein R1—CO— is an acyl group derived from an optionally substituted saturated or unsaturated fatty acid having 6 to 18 carbon atoms; R2 and R3 are each independently an optionally substituted saturated or unsaturated, straight chain or branched chain hydrocarbon group having 1 to 6 carbon atoms, or R2 and R3 form, together with the nitrogen atom to which they are bonded, an optionally substituted heterocycle; R4 is a hydrogen atom or an optionally substituted saturated or unsaturated, straight chain or branched chain hydrocarbon group having 1 to 6 carbon atoms; m is an integer of 1 to 20; n is an integer of 1 to 4; o is an integer of 1 to 8; and X is a sulfonic acid group or a carboxylic acid group, or a salt thereof. ### Claim 4 (depends on 3) The compound according to claim 3, wherein R1—CO— is an acyl group derived from a saturated or unsaturated fatty acid having 6 to 18 carbon atoms; R2 and R3 are each independently a saturated or unsaturated, straight chain or branched chain hydrocarbon group having 1 to 6 carbon atoms; R4 is a hydrogen atom or a saturated or unsaturated, straight chain or branched chain hydrocarbon group having 1 to 6 carbon atoms; m is an integer of 1 to 12; and o is an integer of 1 to 6, or a salt thereof. ### Claim 5 (depends on 1) The compound according to claim 1, wherein R1—CO— is a lauroyl group and n is 4, or a salt thereof. ### Claim 6 (depends on 2) The compound according to claim 2, wherein R1—CO— is a lauroyl group and n is 4, or a salt thereof. ### Claim 7 (depends on 3) The compound according to claim 3, wherein R1—CO— is a lauroyl group and n is 4, or a salt thereof. ### Claim 8 (depends on 4) The compound according to claim 4, wherein R1—CO— is a lauroyl group and n is 4, or a salt thereof. ### Claim 9 (depends on 1) The compound according to claim 1, wherein X is a sulfonic acid group, and R2 and R3 are methyl groups, or a salt thereof. ### Claim 10 (depends on 2) The compound according to claim 2, wherein X is a sulfonic acid group, and R2 and R3 are methyl groups, or a salt thereof. ### Claim 11 (depends on 3) The compound according to claim 3, wherein X is a sulfonic acid group, and R2 and R3 are methyl groups, or a salt thereof. ### Claim 12 (depends on 4) The compound according to claim 4, wherein X is a sulfonic acid group, and R2 and R3 are methyl groups, or a salt thereof. ### Claim 13 (depends on 5) The compound according to claim 5, wherein X is a sulfonic acid group, and R2 and R3 are methyl groups, or a salt thereof. ### Claim 14 (depends on 1) A gelling agent, comprising at least one compound according to claim 1 or a salt thereof. ### Claim 15 (depends on 1) A gel composition, comprising at least one compound according to claim 1 or a salt thereof, and water. ### Claim 16 (depends on 15) A cosmetic agent, comprising a gel composition according to claim 15. ### Claim 17 A method of producing a compound represented by formula (1A): wherein R1—CO— is an acyl group derived from an optionally substituted saturated or unsaturated fatty acid having 6 to 18 carbon atoms; R2 and R3 are each independently an optionally substituted saturated or unsaturated, straight chain or branched chain hydrocarbon group having 1 to 6 carbon atoms, or R2 and R3 form, together with the nitrogen atom to which they are bonded, an optionally substituted heterocycle; R4, R5, and R6 are each independently a hydrogen atom or an optionally substituted saturated or unsaturated, straight chain or branched chain hydrocarbon group having 1 to 6 carbon atoms; m is an integer of 1 to 20; n is an integer of 1 to 4; X is a sulfonic acid group or a carboxylic acid group; and Y is an optionally substituted saturated or unsaturated, straight chain or branched chain divalent hydrocarbon group having 1 to 8 carbon atoms, or a salt thereof, said method comprising converting a compound represented by formula (2): wherein R1—CO— is an acyl group derived from an optionally substituted saturated or unsaturated fatty acid having 6 to 18 carbon atoms; R2 and R3 are each independently an optionally substituted saturated or unsaturated, straight chain or branched chain hydrocarbon group having 1 to 6 carbon atoms, or R2 and R3 form, together with the nitrogen atom to which they are bonded thereto, an optionally substituted heterocycle; R4 is a hydrogen atom or an optionally substituted saturated or unsaturated, straight chain or branched chain hydrocarbon group having 1 to 6 carbon atoms; m is an integer of 1 to 20; and n is an integer of 1 to 4, or a salt thereof, into said compound represented by formula (1A). ### Claim 18 (depends on 1) The compound according to claim 1, wherein R1—CO— is an acyl group derived from an unsubstituted, saturated or unsaturated fatty acid having 6 to 18 carbon atoms, or a salt thereof. ### Claim 19 (depends on 1) The compound according to claim 1, wherein R1—CO— is an acyl group selected from the group consisting of a lauroyl group, a myristoyl group, a palmitoyl group, and a stearoyl group, or a salt thereof. ### Claim 20 A compound, which is selected from the group consisting of: Nα-(11-(N-(3-sulfopropyl)-N,N-dimethylamino)-undecanoyl)-Nε-lauroyl-L-lysine ethyl ester, Nα-(11-(N-(3-sulfopropyl)-N,N-dimethylamino)-undecanoyl)-Nε-lauroyl-L-lysine methyl ester, Nα-(11-(N-(4-sulfopropyl)-N,N-dimethylamino)-undecanoyl)-Nε-lauroyl-L-lysine methyl ester, Nα-(11-(N-(4-sulfobutyl)-N,N-dimethylamino)-undecanoyl)-Nε-lauroyl-L-lysine ethyl ester, Nα-(11-(N-(carboxymethyl-N,N-dimethylamino)-undecanoyl)-Nε-lauroyl-L-lysine ethyl ester, Nα-(11-(N-(2-carboxyethyl)-N ,N -dimethylamino)-undecanoyl)-N ε-lauroyl-L-lysine ethyl ester, Nα-(11-(N-(3-carboxypropyl)-N,N-dimethylamino)-undecanoyl)-Nε-lauroyl-L-lysine ethyl ester, and Nα-(11-(N-(4-carboxybutyl)-N,N-dimethylamino)-undecanoyl)-Nεlauroyl-L-lysine ethyl ester, or a salt thereof.