Title:
SUGAR AMINO ACID AND USE THEREOF
Document Type and Number:
WIPO Patent Application WO/2015/111627
Kind Code:
A1
Abstract:
The purpose of the present invention is to provide an amino acid precursor capable of improving the properties (especially water solubility, stability in water, bitterness, and the like) of an amino acid and being converted into an amino acid in vivo, etc. The present invention pertains to an amino acid precursor compound that is a compound represented by formula (I): [the symbols in the formula are as stated in the specification] or a salt thereof.
Inventors:
KUROSAWA WATARU (JP)
UBAGAI RISA (JP)
KATO HIROYUKI (JP)
SUZUKI HIROMI (JP)
UBAGAI RISA (JP)
KATO HIROYUKI (JP)
SUZUKI HIROMI (JP)
Application Number:
PCT/JP2015/051560
Publication Date:
July 30, 2015
Filing Date:
January 21, 2015
Export Citation:
Assignee:
AJINOMOTO KK (JP)
International Classes:
C07H5/06; A61K31/7008; A61K31/7024; A61K31/7056; A61P43/00; C07H13/12
Domestic Patent References:
| WO2007063907A1 | 2007-06-07 | |||
| WO2004067732A2 | 2004-08-12 | |||
| WO2002053572A1 | 2002-07-11 |
Foreign References:
| US20130123485A1 | 2013-05-16 | |||
| JP2004519484A | 2004-07-02 | |||
| JPH09501940A | 1997-02-25 | |||
| JPH05222099A | 1993-08-31 | |||
| JPS5984900A | 1984-05-16 | |||
| JPS57116043A | 1982-07-19 | |||
| JPS61124354A | 1986-06-12 |
Other References:
VIOLETTE,A. ET AL.: "Optimized LC-MS/MS quantification method for the detection of piperacillin and application to the development of charged liposaccharides as oral penetration enhancers", INTERNATIONAL JOURNAL OF PHARMACEUTICS, vol. 351, no. 1-2, 2008, pages 152 - 157, XP022455528
TOLBERT,T.J. ET AL.: "Intein-Mediated Synthesis of Proteins Containing Carbohydrates and Other Molecular Probes", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 122, no. 23, 2000, pages 421 - 5428, XP055214865
SHUTO,S. ET AL.: "Nucleosides and nucleotide. 145. Synthesis of 2'-deoxy and 5'-phosphate derivatives of bredinin. A photochemical imidazole-ring cleavage and subsequent reconstruction of the base moiety", TETRAHEDRON LETTERS, vol. 37, no. 2, 1996, pages 187 - 190, XP004030433
VETTER,D. ET AL.: "A versatile solid-phase synthesis of N-linked glycopeptides", ANGEWANDTE CHEMIE , INTERNATIONAL EDITION IN ENGLISH, vol. 34, no. 1, 1995, pages 60 - 63, XP000578277
MANGER,I.D. ET AL.: "1-N-Glycyl beta-oligosaccharide derivatives as stable intermediates for the formation of glycoconjugate probes", BIOCHEMISTRY, vol. 31, no. 44, 1992, pages 10724 - 10732, XP055214860
SANT,M.E. ET AL.: "Antifolates induce inhibition of amido phosphoribosyltransferase in leukemia cells", JOURNAL OF BIOLOGICAL CHEMISTRY, vol. 267, no. 16, 1992, pages 11038 - 11045, XP055214856
TAMURA,M. ET AL.: "Studies on N-glycopeptides. II. Separation of a- and beta-amide of N-(L- aspartyl) -beta-D-glucopyranosylamine obtained via N-(benzyloxycarbonyl)-L-aspartic anhydride", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, vol. 57, no. 11, 1984, pages 3167 - 3172, XP055214853
SAWAKI,M. ET AL.: "The nephritogenic glycopeptide from rat glomerular-basement membrane. Part IV. Selective cleavage of the amido linkage of glucopyranosylamine derivatives by ion-exchange resin treatment", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 32, no. 9, 1984, pages 3698 - 3701, XP055214845
FUKUKAWA,K. ET AL.: "Synthesis of bredinin from 5-aminoimidazole-4-carboxamide-ribofuranoside (AICA-riboside", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 32, no. 4, 1984, pages 1644 - 1646, XP055214844
BUFFINGTON,L. ET AL.: "Dependence on anomeric configuration of the temperature dependence of the chemical shifts of exchangeable protons of pyranoses and pyranosides", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 105, no. 22, 1983, pages 6745 - 6747, XP055214835
PAUL,B. ET AL.: "Synthesis and biological activity of some 1-N-substituted 2-acetamido-2- deoxy-beta-D-glycopyranosylamine derivatives and related analogs", CARBOHYDRATE RESEARCH, vol. 80, no. 1, 1980, pages 99 - 115, XP055214831
WOODS,R.A. ET AL.: "Accumulation of glycinamide ribotide by ade3 and ade8 mutants of Saccharomyces cerevisiae", BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, vol. 53, no. 3, 1973, pages 787 - 793, XP024831747
COWLEY,D.E. ET AL.: "Syntheses of some aminoacyl derivatives of 2-acetamido-2-deoxy-beta-D- glucopyranosylamine and of 2-amino-1-N-(4-L- aspartyl)-2-deoxy-beta-D-glucopyranosylamine", CARBOHYDRATE RESEARCH, vol. 19, no. 2, 1971, pages 231 - 241, XP055214828
YOSHIMURA,J. ET AL.: "2-Amino-2-deoxy-D-glucose derivatives. XV. Synthesis of 1-N-acyl-2- acylamino-2-deoxy-beta-glucopyranosylamines", CARBOHYDRATE RESEARCH, vol. 5, no. 1, 1967, pages 82 - 92
BOLTON,C.H. ET AL.: "Some further studies on the synthesis of glycopeptide derivatives: 2- Acetamido-2-deoxy-beta-D-glucopyranosylamine derivatives", BIOCHEMICAL JOURNAL, vol. 101, no. 1, 1966, pages 184 - 190, XP000607565
YAMAMOTO,A. ET AL.: "Amino sugars. II. Preparation of 2-acetamido-1-N-[L-a(and beta)- aspartyl]-2-deoxy-beta-D-glucosylamine and 2- acetamido-2-deoxy-N-(L-gamma-glutamyl)-beta-D- glucosylamine", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 13, no. 9, 1965, pages 1041 - 1046
YAMAMOTO,A. ET AL.: "Amino sugars. I. Preparation of N-acyl derivatives of 2-acetamido-2-deoxy-beta- D-glucosylamine", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 13, no. 9, 1965, pages 1036 - 1041
FLETCHER,A.P. ET AL.: "The carbohydrate moiety of egg albumin", BIOCHIMICA ET BIOPHYSICA ACTA, vol. 71, no. 2, 1963, pages 505 - 508, XP024783241
FLETCHER,A.P. ET AL.: "Carbohydrate moiety of egg albumin", BIOCHIMICA ET BIOPHYSICA ACTA, vol. 71, 1963, pages 505 - 508
LEY, J.P . ET AL.: "Synthesis of L-Histidine and (-)-spinacine chitooligosyl amides", CARBOHYDRATE RESEARCH, vol. 15, no. 1, 1996, pages 51 - 64
TOLBERT,T.J. ET AL.: "Intein-Mediated Synthesis of Proteins Containing Carbohydrates and Other Molecular Probes", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 122, no. 23, 2000, pages 421 - 5428, XP055214865
SHUTO,S. ET AL.: "Nucleosides and nucleotide. 145. Synthesis of 2'-deoxy and 5'-phosphate derivatives of bredinin. A photochemical imidazole-ring cleavage and subsequent reconstruction of the base moiety", TETRAHEDRON LETTERS, vol. 37, no. 2, 1996, pages 187 - 190, XP004030433
VETTER,D. ET AL.: "A versatile solid-phase synthesis of N-linked glycopeptides", ANGEWANDTE CHEMIE , INTERNATIONAL EDITION IN ENGLISH, vol. 34, no. 1, 1995, pages 60 - 63, XP000578277
MANGER,I.D. ET AL.: "1-N-Glycyl beta-oligosaccharide derivatives as stable intermediates for the formation of glycoconjugate probes", BIOCHEMISTRY, vol. 31, no. 44, 1992, pages 10724 - 10732, XP055214860
SANT,M.E. ET AL.: "Antifolates induce inhibition of amido phosphoribosyltransferase in leukemia cells", JOURNAL OF BIOLOGICAL CHEMISTRY, vol. 267, no. 16, 1992, pages 11038 - 11045, XP055214856
TAMURA,M. ET AL.: "Studies on N-glycopeptides. II. Separation of a- and beta-amide of N-(L- aspartyl) -beta-D-glucopyranosylamine obtained via N-(benzyloxycarbonyl)-L-aspartic anhydride", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, vol. 57, no. 11, 1984, pages 3167 - 3172, XP055214853
SAWAKI,M. ET AL.: "The nephritogenic glycopeptide from rat glomerular-basement membrane. Part IV. Selective cleavage of the amido linkage of glucopyranosylamine derivatives by ion-exchange resin treatment", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 32, no. 9, 1984, pages 3698 - 3701, XP055214845
FUKUKAWA,K. ET AL.: "Synthesis of bredinin from 5-aminoimidazole-4-carboxamide-ribofuranoside (AICA-riboside", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 32, no. 4, 1984, pages 1644 - 1646, XP055214844
BUFFINGTON,L. ET AL.: "Dependence on anomeric configuration of the temperature dependence of the chemical shifts of exchangeable protons of pyranoses and pyranosides", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 105, no. 22, 1983, pages 6745 - 6747, XP055214835
PAUL,B. ET AL.: "Synthesis and biological activity of some 1-N-substituted 2-acetamido-2- deoxy-beta-D-glycopyranosylamine derivatives and related analogs", CARBOHYDRATE RESEARCH, vol. 80, no. 1, 1980, pages 99 - 115, XP055214831
WOODS,R.A. ET AL.: "Accumulation of glycinamide ribotide by ade3 and ade8 mutants of Saccharomyces cerevisiae", BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, vol. 53, no. 3, 1973, pages 787 - 793, XP024831747
COWLEY,D.E. ET AL.: "Syntheses of some aminoacyl derivatives of 2-acetamido-2-deoxy-beta-D- glucopyranosylamine and of 2-amino-1-N-(4-L- aspartyl)-2-deoxy-beta-D-glucopyranosylamine", CARBOHYDRATE RESEARCH, vol. 19, no. 2, 1971, pages 231 - 241, XP055214828
YOSHIMURA,J. ET AL.: "2-Amino-2-deoxy-D-glucose derivatives. XV. Synthesis of 1-N-acyl-2- acylamino-2-deoxy-beta-glucopyranosylamines", CARBOHYDRATE RESEARCH, vol. 5, no. 1, 1967, pages 82 - 92
BOLTON,C.H. ET AL.: "Some further studies on the synthesis of glycopeptide derivatives: 2- Acetamido-2-deoxy-beta-D-glucopyranosylamine derivatives", BIOCHEMICAL JOURNAL, vol. 101, no. 1, 1966, pages 184 - 190, XP000607565
YAMAMOTO,A. ET AL.: "Amino sugars. II. Preparation of 2-acetamido-1-N-[L-a(and beta)- aspartyl]-2-deoxy-beta-D-glucosylamine and 2- acetamido-2-deoxy-N-(L-gamma-glutamyl)-beta-D- glucosylamine", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 13, no. 9, 1965, pages 1041 - 1046
YAMAMOTO,A. ET AL.: "Amino sugars. I. Preparation of N-acyl derivatives of 2-acetamido-2-deoxy-beta- D-glucosylamine", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 13, no. 9, 1965, pages 1036 - 1041
FLETCHER,A.P. ET AL.: "The carbohydrate moiety of egg albumin", BIOCHIMICA ET BIOPHYSICA ACTA, vol. 71, no. 2, 1963, pages 505 - 508, XP024783241
FLETCHER,A.P. ET AL.: "Carbohydrate moiety of egg albumin", BIOCHIMICA ET BIOPHYSICA ACTA, vol. 71, 1963, pages 505 - 508
LEY, J.P . ET AL.: "Synthesis of L-Histidine and (-)-spinacine chitooligosyl amides", CARBOHYDRATE RESEARCH, vol. 15, no. 1, 1996, pages 51 - 64
Attorney, Agent or Firm:
TAKASHIMA, HAJIME (JP)
Takashima 1 (JP)
Takashima 1 (JP)
Download PDF:
Previous Patent: FLUORESCENT MATERIAL AND LIGHT-EMITTING DEVICE
Next Patent: THERMOELECTRIC CONVERSION MODULE
Next Patent: THERMOELECTRIC CONVERSION MODULE