Title:
NOVEL BETA-AMINOALDEHYDE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND THEIR CHEMICAL USE AS REACTIVE INTERMEDIATES
Document Type and Number:
WIPO Patent Application WO/2012/000608
Kind Code:
A3
Abstract:
The present invention relates to novel beta-aminoaldehyde derivatives of the formulae (I), (II) and (III), in which the substituents R1 to R5 and A have the meaning given in the description, to a novel process for their preparation, to its intermediates, and to uses of these novel beta-aminoaldehyde derivatives, e.g. for (chemical) use as reactive intermediates, for use in medicine, e.g. as peptidomimetic, as coupling agent, etc.
Inventors:
GLUESENKAMP KARL-HEINZ (DE)
MENGEDE CHRISTIAN (DE)
MENGEDE CHRISTIAN (DE)
Application Number:
PCT/EP2011/002923
Publication Date:
March 08, 2012
Filing Date:
June 14, 2011
Export Citation:
Assignee:
GLUESENKAMP KARL-HEINZ (DE)
MENGEDE CHRISTIAN (DE)
MENGEDE CHRISTIAN (DE)
International Classes:
C07C269/06; C07C271/18; C07C271/24; C07D211/58; C07D213/48; C07D223/12; C07D265/06; C07D277/28; C07D307/14; C07D309/14; C07D311/68; C07D317/32; C07D333/22; C07D335/02; C07D493/08
Domestic Patent References:
| WO2004043958A1 | 2004-05-27 | |||
| WO2008006039A1 | 2008-01-10 | |||
| WO2005049033A1 | 2005-06-02 | |||
| WO2005121145A2 | 2005-12-22 | |||
| WO2008043798A1 | 2008-04-17 | |||
| WO2003106399A2 | 2003-12-24 |
Foreign References:
| US20070259888A1 | 2007-11-08 | |||
| US20040014763A1 | 2004-01-22 | |||
| SU1203092A1 | 1986-01-07 | |||
| US20090275627A1 | 2009-11-05 | |||
| US20070191335A1 | 2007-08-16 |
Other References:
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LEE H K ET AL: "Facile conversion of 2-azetidinones to 2-piperidones: application to a formal synthesis of Prosopis and Cassia alkaloids", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 59, no. 34, 18 August 2003 (2003-08-18), pages 6445 - 6454, XP004444220, ISSN: 0040-4020, DOI: 10.1016/S0040-4020(03)01063-9
YOSHIZAWA HIDENORI ET AL: "S-3578, a new broad psectrum parenteral cephalosporin exhibiting potent activity against both methicillin-resistant staphylococcus aureus (MRSA) and pseudomonas aeruginosa. Synthesis and structure-activity relationships", THE JOURNAL OF ANTIBIOTICS, JAPAN ANTIBIOTICS RESEARCH ASSOCIATION, TOKYO, JP, vol. 55, no. 11, 1 January 2002 (2002-01-01), pages 975 - 992, XP002973822, ISSN: 0021-8820
FRANKLIN A. DAVIS ET AL: "Asymmetric Synthesis of cis -5- tert -Butylproline with Metal Carbenoid NH Insertion", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 68, no. 13, 1 June 2003 (2003-06-01), pages 5147 - 5152, XP055015228, ISSN: 0022-3263, DOI: 10.1021/jo030081s
MENDRE C ET AL: "PEPTIDE AND PSEUDOPEPTIDE ANALOGUES OF CHOLECYSTOKININ. CHEMICAL MODIFICATION OF THE MET28-GLY29 REGION", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 44, no. 14, 1 January 1988 (1988-01-01), pages 4415 - 4430, XP001153467, ISSN: 0040-4020, DOI: 10.1016/S0040-4020(01)86144-5
M. RODRIGUEZ ET AL.: ""CARBA" PEPTIDE BOND SURROGATES: SYNTHESIS OF BOC-L-LEU-psi(CH2-CH2)-L-PHE-OH AND BOC-L-LEU-psi(CH2-CH2)-D-PHE-OH THROUGH A HORNER-EMMONS REACTION", TETRAHEDRON LETTERS, vol. 31, no. 50, 1 January 1990 (1990-01-01), Great Britain, pages 7319 - 7322, XP055015226
HIROAKI OHNO ET AL: "Stereoselective Synthesis of 2-Alkenylaziridines and 2-Alkenylazetidines by Palladium-Catalyzed Intramolecular Amination of [alpha]- and [beta]-Amino Allenes", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 66, no. 14, 1 July 2001 (2001-07-01), pages 4904 - 4914, XP055015220, ISSN: 0022-3263, DOI: 10.1021/jo015683v
SZAKONYI Z ET AL: "Regio- and stereoselective synthesis of constrained enantiomeric beta-amino acid derivatives", TETRAHEDRON ASYMMETRY, PERGAMON PRESS LTD, OXFORD, GB, vol. 19, no. 19, 6 October 2008 (2008-10-06), pages 2296 - 2303, XP025609005, ISSN: 0957-4166, [retrieved on 20081022], DOI: 10.1016/J.TETASY.2008.09.026
LEE H K ET AL: "Facile conversion of 2-azetidinones to 2-piperidones: application to a formal synthesis of Prosopis and Cassia alkaloids", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 59, no. 34, 18 August 2003 (2003-08-18), pages 6445 - 6454, XP004444220, ISSN: 0040-4020, DOI: 10.1016/S0040-4020(03)01063-9
YOSHIZAWA HIDENORI ET AL: "S-3578, a new broad psectrum parenteral cephalosporin exhibiting potent activity against both methicillin-resistant staphylococcus aureus (MRSA) and pseudomonas aeruginosa. Synthesis and structure-activity relationships", THE JOURNAL OF ANTIBIOTICS, JAPAN ANTIBIOTICS RESEARCH ASSOCIATION, TOKYO, JP, vol. 55, no. 11, 1 January 2002 (2002-01-01), pages 975 - 992, XP002973822, ISSN: 0021-8820
FRANKLIN A. DAVIS ET AL: "Asymmetric Synthesis of cis -5- tert -Butylproline with Metal Carbenoid NH Insertion", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 68, no. 13, 1 June 2003 (2003-06-01), pages 5147 - 5152, XP055015228, ISSN: 0022-3263, DOI: 10.1021/jo030081s
MENDRE C ET AL: "PEPTIDE AND PSEUDOPEPTIDE ANALOGUES OF CHOLECYSTOKININ. CHEMICAL MODIFICATION OF THE MET28-GLY29 REGION", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 44, no. 14, 1 January 1988 (1988-01-01), pages 4415 - 4430, XP001153467, ISSN: 0040-4020, DOI: 10.1016/S0040-4020(01)86144-5
M. RODRIGUEZ ET AL.: ""CARBA" PEPTIDE BOND SURROGATES: SYNTHESIS OF BOC-L-LEU-psi(CH2-CH2)-L-PHE-OH AND BOC-L-LEU-psi(CH2-CH2)-D-PHE-OH THROUGH A HORNER-EMMONS REACTION", TETRAHEDRON LETTERS, vol. 31, no. 50, 1 January 1990 (1990-01-01), Great Britain, pages 7319 - 7322, XP055015226
HIROAKI OHNO ET AL: "Stereoselective Synthesis of 2-Alkenylaziridines and 2-Alkenylazetidines by Palladium-Catalyzed Intramolecular Amination of [alpha]- and [beta]-Amino Allenes", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 66, no. 14, 1 July 2001 (2001-07-01), pages 4904 - 4914, XP055015220, ISSN: 0022-3263, DOI: 10.1021/jo015683v
SZAKONYI Z ET AL: "Regio- and stereoselective synthesis of constrained enantiomeric beta-amino acid derivatives", TETRAHEDRON ASYMMETRY, PERGAMON PRESS LTD, OXFORD, GB, vol. 19, no. 19, 6 October 2008 (2008-10-06), pages 2296 - 2303, XP025609005, ISSN: 0957-4166, [retrieved on 20081022], DOI: 10.1016/J.TETASY.2008.09.026
Attorney, Agent or Firm:
GRAF VON STOSCH, Andreas et al. (Prinzregentenstrasse 22, München, DE)
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