WO2005007634A8 - 3-hydroxy-4-oxo-1,2,3-triazines and derivatives thereof for amide and ester bond formation - Google Patents

3-hydroxy-4-oxo-1,2,3-triazines and derivatives thereof for amide and ester bond formation

Info

Publication number
WO2005007634A8
WO2005007634A8 PCT/IL2004/000652 IL2004000652W WO2005007634A8 WO 2005007634 A8 WO2005007634 A8 WO 2005007634A8 IL 2004000652 W IL2004000652 W IL 2004000652W WO 2005007634 A8 WO2005007634 A8 WO 2005007634A8
Authority
WO
WIPO (PCT)
Prior art keywords
formula
amide
triazines
oxo
hydroxy
Prior art date
Application number
PCT/IL2004/000652
Other languages
French (fr)
Other versions
WO2005007634A1 (en
Inventor
Yaacov Shpernat
Michael Mizhiritskii
Original Assignee
Frutarom Ltd
Yaacov Shpernat
Michael Mizhiritskii
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 Frutarom Ltd, Yaacov Shpernat, Michael Mizhiritskii filed Critical Frutarom Ltd
Publication of WO2005007634A1 publication Critical patent/WO2005007634A1/en
Publication of WO2005007634A8 publication Critical patent/WO2005007634A8/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/08—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
    • C07D253/04—1,2,3-Triazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having three nitrogen atoms as the only ring hetero atoms
    • C07F9/6521—Six-membered rings
    • C07F9/65218—Six-membered rings condensed with carbocyclic rings or carbocyclic ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
    • C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings

Abstract

The present invention relates to the use of a compound of formula I as a coupling reagent in forming amide or ester bonds from a reaction between a carboxylic acid and an amine or an alcohol, respectively. The compounds of formula I are especially useful as coupling reagents in the preparation of peptide bonds during peptide synthesis. In particular, the compounds of formula I are useful in promoting the formation of reactive reaction intermediates, inhibiting side reactions and in suppression of racemization. In addition, the present invention provides novel compounds of Formula I, and salts of N-oxides thereof.
PCT/IL2004/000652 2003-07-18 2004-07-18 3-hydroxy-4-oxo-1,2,3-triazines and derivatives thereof for amide and ester bond formation WO2005007634A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US48796203P 2003-07-18 2003-07-18
US60/487,962 2003-07-18

Publications (2)

Publication Number Publication Date
WO2005007634A1 WO2005007634A1 (en) 2005-01-27
WO2005007634A8 true WO2005007634A8 (en) 2005-03-31

Family

ID=34079399

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IL2004/000652 WO2005007634A1 (en) 2003-07-18 2004-07-18 3-hydroxy-4-oxo-1,2,3-triazines and derivatives thereof for amide and ester bond formation

Country Status (1)

Country Link
WO (1) WO2005007634A1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109336948A (en) * 2018-09-21 2019-02-15 重庆奥舍生物化工有限公司 Application of the novel organophosphorus polypeptide condensing agent in Peptide systhesis
CN109438550A (en) * 2018-09-21 2019-03-08 重庆奥舍生物化工有限公司 Application of the novel carbonium ion polypeptide condensing agent in Peptide systhesis

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7812158B2 (en) 2003-10-31 2010-10-12 University Of Massachusetts Coupling agents for peptide synthesis
WO2008139481A2 (en) * 2007-05-16 2008-11-20 Luxembourg Bio Technologies Ltd. Proton acceptor iminium/carbocation-type coupling agents
CN109336832A (en) * 2018-09-21 2019-02-15 重庆奥舍生物化工有限公司 A kind of polypeptide condensing agent and preparation method thereof for polypeptide drug synthesis
CN109232647A (en) * 2018-09-21 2019-01-18 重庆奥舍生物化工有限公司 Polypeptide condensing agent 1- (diethoxy phosphoryl oxy) -1,2,3- phentriazine -4- ketone and preparation method thereof
CN110845414A (en) * 2019-11-27 2020-02-28 济宁康盛彩虹生物科技有限公司 Preparation method and application of N-bis (dimethylamino) -1, 3-dimethylimidazoline

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5952497A (en) * 1996-07-10 1999-09-14 University Of Georgia Research Foundation N.sup.α -Bpoc amino acid pentafluorophenyl (Pfp) esters and 3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-yl (ODhbt) esters
US6075141A (en) * 1996-07-10 2000-06-13 University Of Georgia Research Foundation, Inc. N.sup.α -α, α-dimethyl-3,5-dialkoxybenzylcarbonyl amino acid 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazin-3-yl and pentafluorophenyl esters

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109336948A (en) * 2018-09-21 2019-02-15 重庆奥舍生物化工有限公司 Application of the novel organophosphorus polypeptide condensing agent in Peptide systhesis
CN109438550A (en) * 2018-09-21 2019-03-08 重庆奥舍生物化工有限公司 Application of the novel carbonium ion polypeptide condensing agent in Peptide systhesis

Also Published As

Publication number Publication date
WO2005007634A1 (en) 2005-01-27

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