WO1995017418A3 - NOVEL INTERMEDIATES FOR THE SYNTHESIS OF L-ASPARTYL-D-α-AMINOALKANOYL-(S)-N-α-ALKYLBENZYL AMIDES USEFUL AS ARTIFICIAL SWEETENERS - Google Patents

NOVEL INTERMEDIATES FOR THE SYNTHESIS OF L-ASPARTYL-D-α-AMINOALKANOYL-(S)-N-α-ALKYLBENZYL AMIDES USEFUL AS ARTIFICIAL SWEETENERS Download PDF

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Publication number
WO1995017418A3
WO1995017418A3 PCT/US1994/014770 US9414770W WO9517418A3 WO 1995017418 A3 WO1995017418 A3 WO 1995017418A3 US 9414770 W US9414770 W US 9414770W WO 9517418 A3 WO9517418 A3 WO 9517418A3
Authority
WO
WIPO (PCT)
Prior art keywords
aminoalkanoyl
aspartyl
synthesis
artificial sweeteners
novel intermediates
Prior art date
Application number
PCT/US1994/014770
Other languages
French (fr)
Other versions
WO1995017418A2 (en
Inventor
Angelo Lihong D
James G Sweeny
George A King Iii
Original Assignee
Coca Cola Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Coca Cola Co filed Critical Coca Cola Co
Priority to JP7517595A priority Critical patent/JPH09507076A/en
Priority to AU14429/95A priority patent/AU1442995A/en
Priority to EP95906070A priority patent/EP0736037A1/en
Priority to KR1019960703374A priority patent/KR970700201A/en
Publication of WO1995017418A2 publication Critical patent/WO1995017418A2/en
Publication of WO1995017418A3 publication Critical patent/WO1995017418A3/en
Priority to FI962592A priority patent/FI962592A0/en
Priority to NO962620A priority patent/NO962620L/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C237/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D263/18—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06104—Dipeptides with the first amino acid being acidic
    • C07K5/06113—Asp- or Asn-amino acid

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Peptides Or Proteins (AREA)
  • Seasonings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention relates to chemical compounds that are useful for the preparation of artificial sweetener compounds, in particular, chemical intermediates that are useful for the preparation of L-aspartyl-D-α-aminoalkanoyl-(S)-N-α-alkylbenzyl amides.
PCT/US1994/014770 1993-12-22 1994-12-22 NOVEL INTERMEDIATES FOR THE SYNTHESIS OF L-ASPARTYL-D-α-AMINOALKANOYL-(S)-N-α-ALKYLBENZYL AMIDES USEFUL AS ARTIFICIAL SWEETENERS WO1995017418A2 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
JP7517595A JPH09507076A (en) 1993-12-22 1994-12-22 Novel intermediates for the synthesis of L-aspartyl-D-α-aminoalkanoyl- (S) -N-α-alkylbenzylamides useful as artificial sweeteners
AU14429/95A AU1442995A (en) 1993-12-22 1994-12-22 Novel intermediates for the synthesis of l-aspartyl-d-alpha-aminoalkanoyl-(s)-n-alpha-alkylbenzyl amides useful as artificial sweeteners
EP95906070A EP0736037A1 (en) 1993-12-22 1994-12-22 NOVEL INTERMEDIATES FOR THE SYNTHESIS OF L-ASPARTYL-D-$g(a)-AMINOALKANOYL-(S)-N-$g(a)-ALKYLBENZYL AMIDES USEFUL AS ARTIFICIAL SWEETENERS
KR1019960703374A KR970700201A (en) 1993-12-22 1994-12-22 NOVEL INTERMEDIATES FOR THE SYNTHESIS OF L-ASPARTYL-D-ALPHA-ALPHA-ALKYLAMINYLAMIDE FOR THE SYNTHESIS OF EL-ASPARTIL-DI- α-AMINOALKANOYL- (S) -N-α-ALKYLBENZYL AMIDES USEFUL AS ARTIFICIAL SWEETENERS)
FI962592A FI962592A0 (en) 1993-12-22 1996-06-20 New intermediates for the synthesis of L-aspartyl-D-alpha-aminoalkanoyl- (S) -N-alpha-alkylbenzylamides useful as artificial sweeteners
NO962620A NO962620L (en) 1993-12-22 1996-06-20 New intermediates for the synthesis of L-aspartyl-D - aminoalkanoyl- (S) -N - alkylbenzylamides useful as artificial sweeteners

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US17199693A 1993-12-22 1993-12-22
US08/171,996 1993-12-22

Publications (2)

Publication Number Publication Date
WO1995017418A2 WO1995017418A2 (en) 1995-06-29
WO1995017418A3 true WO1995017418A3 (en) 1995-10-19

Family

ID=22625935

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1994/014770 WO1995017418A2 (en) 1993-12-22 1994-12-22 NOVEL INTERMEDIATES FOR THE SYNTHESIS OF L-ASPARTYL-D-α-AMINOALKANOYL-(S)-N-α-ALKYLBENZYL AMIDES USEFUL AS ARTIFICIAL SWEETENERS

Country Status (12)

Country Link
EP (1) EP0736037A1 (en)
JP (1) JPH09507076A (en)
KR (1) KR970700201A (en)
AU (1) AU1442995A (en)
CA (1) CA2179376A1 (en)
FI (1) FI962592A0 (en)
IL (1) IL111990A0 (en)
NO (1) NO962620L (en)
PE (1) PE25195A1 (en)
TW (1) TW282450B (en)
WO (1) WO1995017418A2 (en)
ZA (1) ZA9410199B (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996030381A1 (en) * 1995-03-28 1996-10-03 Novo Nordisk A/S Immunosuppressive agents
US8044173B2 (en) 2005-09-13 2011-10-25 University Of Reading Asymmetric synthesis of peptides
GB0518667D0 (en) * 2005-09-13 2005-10-19 Univ Reading The Method
US9101160B2 (en) 2005-11-23 2015-08-11 The Coca-Cola Company Condiments with high-potency sweetener
US8017168B2 (en) 2006-11-02 2011-09-13 The Coca-Cola Company High-potency sweetener composition with rubisco protein, rubiscolin, rubiscolin derivatives, ace inhibitory peptides, and combinations thereof, and compositions sweetened therewith

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0034876A2 (en) * 1980-01-21 1981-09-02 Pfizer Inc. Branched amides of L-aspartyl-D-amino acid dipeptides and compositions thereof
US4730076A (en) * 1985-12-18 1988-03-08 Nippon Kayaku Kabushiki Kaisha Process for producing α-aspartyl-phenylalanine ester
EP0379917A2 (en) * 1989-01-26 1990-08-01 Bayer Ag Optically active (meth)acrylic-acid derivatives, their preparation, their polymerisation into optically active polymers and their use
AT394854B (en) * 1986-06-12 1992-07-10 Biochemie Gmbh Process for the preparation of N-L-alpha-aspartyl-L- phenylalanine (lower) alkyl esters
WO1994000028A2 (en) * 1992-06-22 1994-01-06 Coca Cola Co L-ASPARTYL-D-α-AMINOALKANOYL-(S)-N-α-ALKYLBENZYL AMIDES USEFUL AS ARTIFICIAL SWEETENERS

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0034876A2 (en) * 1980-01-21 1981-09-02 Pfizer Inc. Branched amides of L-aspartyl-D-amino acid dipeptides and compositions thereof
US4730076A (en) * 1985-12-18 1988-03-08 Nippon Kayaku Kabushiki Kaisha Process for producing α-aspartyl-phenylalanine ester
AT394854B (en) * 1986-06-12 1992-07-10 Biochemie Gmbh Process for the preparation of N-L-alpha-aspartyl-L- phenylalanine (lower) alkyl esters
EP0379917A2 (en) * 1989-01-26 1990-08-01 Bayer Ag Optically active (meth)acrylic-acid derivatives, their preparation, their polymerisation into optically active polymers and their use
WO1994000028A2 (en) * 1992-06-22 1994-01-06 Coca Cola Co L-ASPARTYL-D-α-AMINOALKANOYL-(S)-N-α-ALKYLBENZYL AMIDES USEFUL AS ARTIFICIAL SWEETENERS

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
KAJFEZ, F. ET AL.: "A new synthesis of ampicillin and related investigations", J. HETEROCYCLIC CHEMISTRY, vol. 13, no. 3, pages 561 - 566 *
KIM, N. ET AL.: "HPLC analysis of a back- bone compound, beta-benzyl-N-carbobenzoxy- L-asparty-D-alanine ...", FOOD CHEMISTRY, vol. 47, no. 4, pages 407 - 410 *
SAVRDA, J.: "Étude en RMN de N-acyl-5-oxazolidones: conformation et couplage à longue distance", BULL. SOC. CHIM. FRANCE, vol. 12, pages 2857 - 2860 *
SCHOLZT, J.M. & BARTLETT, P.A.: "A convenient differential protection strategy for functional group manipulation of aspartic and glutamic acids", SYNTHESIS, vol. 89, no. 7, pages 542 - 544 *
SUKEHIRO, M. ET AL.: "Studies on structure-taste relationship of aspartyl ppetide sweeteners. I. Synthesis and properties of L-aspartyl-D-alanine amides", SEIHATSU KAGAKU, vol. 11, no. 1-2, pages 9 - 16 *

Also Published As

Publication number Publication date
FI962592A (en) 1996-06-20
EP0736037A1 (en) 1996-10-09
IL111990A0 (en) 1995-03-15
NO962620L (en) 1996-08-19
FI962592A0 (en) 1996-06-20
TW282450B (en) 1996-08-01
KR970700201A (en) 1997-01-08
ZA9410199B (en) 1995-09-04
PE25195A1 (en) 1995-09-29
JPH09507076A (en) 1997-07-15
CA2179376A1 (en) 1995-06-29
WO1995017418A2 (en) 1995-06-29
AU1442995A (en) 1995-07-10
NO962620D0 (en) 1996-06-20

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