Title:
DIPEPTIDYL PEPTIDASE INHIBITORS
Document Type and Number:
WIPO Patent Application WO2006019965
Kind Code:
A3
Abstract:
Compounds, pharmaceutical compositions, kits and methods are provided for use with DPP-IV and other S9 proteases that comprise a compound of formula (I) wherein R
Inventors:
FENG JUN (US)
GWALTNEY STEVEN (US)
LAM BETTY (US)
ZHANG ZHIYUAN (US)
GWALTNEY STEVEN (US)
LAM BETTY (US)
ZHANG ZHIYUAN (US)
Application Number:
PCT/US2005/025070
Publication Date:
April 06, 2006
Filing Date:
July 14, 2005
Export Citation:
Assignee:
TAKEDA SAN DIEGO INC (US)
FENG JUN (US)
GWALTNEY STEVEN (US)
LAM BETTY (US)
ZHANG ZHIYUAN (US)
FENG JUN (US)
GWALTNEY STEVEN (US)
LAM BETTY (US)
ZHANG ZHIYUAN (US)
International Classes:
C07D471/04; A61K31/519; C07D471/14
Domestic Patent References:
| WO2004018467A2 | 2004-03-04 | |||
| WO2004050658A1 | 2004-06-17 |
Other References:
TSANN-LONG SU, JAI-TUNG HUANG, JOSEPH H. BURCHENAL, KYOICHI A. WATANABE, JACK J. FOX: "Synthesis and Biological Activities of 5-Deaza Analogues of Aminopterin and Folic Acid", J. MED. CHEM., vol. 29, 1986, pages 709 - 715, XP002362908
J. R. PIPER, G. S. MCCALEB, J. A. MONTGOMERY, R. L. KISLIUK, Y. GAUMONT, F. M. SIROTNAK: "Syntheses and Antifolate Activity of 5-Methyl-5-deaza Analogues of Aminopterin, Methotrexate, Folic Acid and N10-Methylfolic Acid", J. MED. CHEM., vol. 29, 1986, pages 1080 - 1087, XP002362909
JOHN B. HYNES, SHYAM K. SINGH, OLIVER FETZER, BARRY SHANE: "Inhibition of Hog Liver Folylpolyglutamate Synthetase by 5-Substituted 5,8-Deaza Analogues of Folic Acid Bearing a Terminal L-Ornithine Residue", J. MED. CHEM., vol. 35, 1992, pages 4078 - 4085, XP002362910
KAMALJIT SINGH, JASBIR SINGH, HARJIT SINGH: "Carbon Transfer Reactions of Functionalized Oxazolidines and their Open Chain Enamine Tautomers to Enamine Nucleophiles. A Facile Synthesis of Substituted Pyridines and Ring Annulated Derivatives", TETRAHEDRON, vol. 54, 1998, pages 935 - 942, XP002362911
YOSHINORI TOMINAGA, HIROTO OKUDA, SHINYA KOHRA, HISAKO MAZUME: "Reaction of Enaminones with Carbon Disulfide: Synthesis of Heterocycles Using Enamino Dithiocarboxylates", J. HETEROCYCL. CHEM., vol. 28, 1991, pages 1245 - 1255, XP002362912
STANLEY WAWZONEK: "Synthesis of Pyrido[2,3-d]pyrimidine-2,4-diones", J. ORG. CHEM., vol. 41, no. 19, 1976, pages 3149 - 3151, XP002362913
RUMEN RADINOV, CHRISTO CHANEV, MARIETTA HAIMOVA: "Lithiation of Polychloropyrimidines and Dichloropyridines", J. ORG. CHEM., vol. 56, 1991, pages 4793 - 4796, XP002362914
E. DIAZ, H. BARRIOS, D. CORONA, A. GUZMAN, R. DIAZ, A. FUENTES: "2D 1H and 13C NMR evidences of the [2+2] autodimerization of 2-benzyl-5-benzylidene cyclopentanone yielding two different diphenyl, dispiro cyclobutane derivatives", SPECTROCHIMICA ACTA PART A, vol. 58, 2002, pages 2079 - 2087, XP002362915
ABD EL-WARETH A. O. SARHAN, ZEINAB A. HOZIEN, HOSNEY A. H. EL-SHERIEF: "Synthesis, Characterization and Reactions of 2-Deoxo-5-deazaalloxazines", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 9, 2001, pages 2993 - 2998, XP002362916
SHYAM K. SINGH, MELEDATH GOVINDAN, JOHN B. HYNES: "Synthesis of 5-Trifluoromethyl-5,8-dideazafolic Acid and 5-Trifluoromethyl-5,8-dideazaisofolic Acid", J. HETEROCYCL. CHEM., vol. 27, 1990, pages 2101 - 2105, XP002362917
MAGDA N. NASR, MAGDY M. GINEINAH: "Pyrido[2,3-d]pyrimidines and Pyrimido[5',4':5,6]pyrido[2,3-d]pyrimidines as New Antiviral Agents: Synthesis and Biological Activity", ARCH. PHARM. PHARM. MED. CHEM., vol. 6, 2002, pages 289 - 295, XP002362918
EDWARD C. TAYLOR, EDWARD E. GARCIA: "The Synthesis of 4-Aminoisoxazolo[5,4-d]pyrimidines", J. ORG. CHEM., vol. 29, 1964, pages 2116 - 2120, XP002362919
PULAKJYOTI BHUYAN, ROSMEH CHANDRA BORUAH, JAGIR SINGH SANDHU: "Studies on Uracils. 10. A Facile One-Pot Synthesis of Pyrido[2,3-d]- and Pyrazolo[3,4-d]pyrimidines", J. ORG. CHEM., vol. 55, 1990, pages 568 - 571, XP002362920
ROBERT B. NICEWONGER, LORI DITTO, DOUG KERR, LASZLO VARADY: "Synthesis of a Novel, Recyclable", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 12, 2002, pages 1799 - 1802, XP002362921
IPITSA DEVI, B. S. D. KUMAR, PULAK J. BHUYAN: "A novel three-component one-pot synthesis of pyrano[2,3-d]pyrimidines and pyrido[2,3-d]pyrimidines using microwave heating in the solid state", TETRAHEDRON LETTERS, vol. 44, 2003, pages 8307 - 8310, XP002362953
ROBB NICEWONGER, APRIL FOWKE, KATHY NGUYEN, LORI DITTO, JUSTIN CASERTA, MICHELE HARRIS, CARMEN M. BALDINO: "Microwave-assisted acylation of 7-amino-5-aryl-6-cyanopyrido[2,3-d]pyrimidines", MOLECULAR DIVERSITY, vol. 7, 2003, pages 247 - 252, XP002362954
DATABASE ZCAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 2003, YOUSSIF, SHAKER ET AL: "Novel uracil and pyrido[2,3-d]pyrimidine-2,4(1H, 3H)-dione derivatives: synthesis and antimicrobial activity", XP002362972, retrieved from STN Database accession no. 2003:911230
DATABASE ZCAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 1999, YOUSSIF, SHAKER ET AL: "A facile one-pot synthesis of pyrido[2,3-d]pyrimidines and pyrido[2,3-d:6,5-d']dipyrimidines", XP002362973, retrieved from STN Database accession no. 1999:177044
DATABASE ZCAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 1999, GEIES, AHMED A.: "Synthesis of pyrido[2,3-d]pyrimidines via the reaction of activated nitriles with aminopyrimidines", XP002362974, retrieved from STN Database accession no. 1999:158849
DATABASE ZCAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 1998, ELNEAIRY, MOHAMED A. A. ET AL: "2-(2-Benzothiazolyl)ethanethioamides in heterocyclic synthesis: novel synthesis of pyridine, pyrido[2,3-d]pyrimidine, coumarin, thiazolone and triazole derivatives", XP002362975, retrieved from STN Database accession no. 1998:756479
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 1991, SEADA, M. ET AL: "Reactions with 2-amino-3,5-dicyanopyridines", XP002362976, retrieved from STN Database accession no. 1991:81740
DATABASE ZCAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 1985, GOGOI, MUKTI ET AL: "Arylidenemalononitriles in heterocyclic syntheses: a novel synthesis of pyrido[2,3-d]pyrimidines", XP002362977, retrieved from STN Database accession no. 1985:131988
DATABASE CROSSFIRE BEILSTEIN Beilstein Institut zur Förderung der Wissenschaften, Frankfurt am Main, DE; 1994, XP002362978, Database accession no. 6875211 (BRN)
DATABASE CROSSFIRE BEILSTEIN Beilstein Institut zur Förderung der Wissenschaften, Frankfurt am Main, DE; 2000, XP002362979, Database accession no. 8349174 (BRN)
DATABASE CROSSFIRE BEILSTEIN Beilstein Institut zur Förderung der Wissenschaften, Frankfurt am Main, DEcr; 1988, XP002362980, Database accession no. 1231932 (BRN)
DATABASE CROSSFIRE BEILSTEIN Beilstein Institut zur Förderung der Wissenschaften, Frankfurt am Main, DE; 2002, XP002362981, Database accession no. 9010879 (BRN)
DATABASE CROSSFIRE BEILSTEIN Beilstein Institut zur Förderung der Wissenschaften, Frankfurt am Main, DE; 2005, XP002362982, Database accession no. 9955126 (BRN)
DATABASE CROSSFIRE BEILSTEIN Beilstein Institut zur Förderung der Wissenschaften, Frankfurt am Main, DE; 1993, XP002362983, Database accession no. 4598493 (BRN)
DATABASE CROSSFIRE BEILSTEIN Beilstein Institut zur Förderung der Wissenschaften, Frankfurt am Main, DE; 1993, XP002362984, Database accession no. 8353231 (BRN)
DATABASE CROSSFIRE BEILSTEIN Beilstein Institut zur Förderung der Wissenschaften, Frankfurt am Main, DE; 2000, XP002362985, Database accession no. 8360481 (BRN)
DATABASE CROSSFIRE BEILSTEIN Beilstein Institut zur Förderung der Wissenschaften, Frankfurt am Main, DE; 2000, XP002362986, Database accession no. 8345402 (BRN)
J. R. PIPER, G. S. MCCALEB, J. A. MONTGOMERY, R. L. KISLIUK, Y. GAUMONT, F. M. SIROTNAK: "Syntheses and Antifolate Activity of 5-Methyl-5-deaza Analogues of Aminopterin, Methotrexate, Folic Acid and N10-Methylfolic Acid", J. MED. CHEM., vol. 29, 1986, pages 1080 - 1087, XP002362909
JOHN B. HYNES, SHYAM K. SINGH, OLIVER FETZER, BARRY SHANE: "Inhibition of Hog Liver Folylpolyglutamate Synthetase by 5-Substituted 5,8-Deaza Analogues of Folic Acid Bearing a Terminal L-Ornithine Residue", J. MED. CHEM., vol. 35, 1992, pages 4078 - 4085, XP002362910
KAMALJIT SINGH, JASBIR SINGH, HARJIT SINGH: "Carbon Transfer Reactions of Functionalized Oxazolidines and their Open Chain Enamine Tautomers to Enamine Nucleophiles. A Facile Synthesis of Substituted Pyridines and Ring Annulated Derivatives", TETRAHEDRON, vol. 54, 1998, pages 935 - 942, XP002362911
YOSHINORI TOMINAGA, HIROTO OKUDA, SHINYA KOHRA, HISAKO MAZUME: "Reaction of Enaminones with Carbon Disulfide: Synthesis of Heterocycles Using Enamino Dithiocarboxylates", J. HETEROCYCL. CHEM., vol. 28, 1991, pages 1245 - 1255, XP002362912
STANLEY WAWZONEK: "Synthesis of Pyrido[2,3-d]pyrimidine-2,4-diones", J. ORG. CHEM., vol. 41, no. 19, 1976, pages 3149 - 3151, XP002362913
RUMEN RADINOV, CHRISTO CHANEV, MARIETTA HAIMOVA: "Lithiation of Polychloropyrimidines and Dichloropyridines", J. ORG. CHEM., vol. 56, 1991, pages 4793 - 4796, XP002362914
E. DIAZ, H. BARRIOS, D. CORONA, A. GUZMAN, R. DIAZ, A. FUENTES: "2D 1H and 13C NMR evidences of the [2+2] autodimerization of 2-benzyl-5-benzylidene cyclopentanone yielding two different diphenyl, dispiro cyclobutane derivatives", SPECTROCHIMICA ACTA PART A, vol. 58, 2002, pages 2079 - 2087, XP002362915
ABD EL-WARETH A. O. SARHAN, ZEINAB A. HOZIEN, HOSNEY A. H. EL-SHERIEF: "Synthesis, Characterization and Reactions of 2-Deoxo-5-deazaalloxazines", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 9, 2001, pages 2993 - 2998, XP002362916
SHYAM K. SINGH, MELEDATH GOVINDAN, JOHN B. HYNES: "Synthesis of 5-Trifluoromethyl-5,8-dideazafolic Acid and 5-Trifluoromethyl-5,8-dideazaisofolic Acid", J. HETEROCYCL. CHEM., vol. 27, 1990, pages 2101 - 2105, XP002362917
MAGDA N. NASR, MAGDY M. GINEINAH: "Pyrido[2,3-d]pyrimidines and Pyrimido[5',4':5,6]pyrido[2,3-d]pyrimidines as New Antiviral Agents: Synthesis and Biological Activity", ARCH. PHARM. PHARM. MED. CHEM., vol. 6, 2002, pages 289 - 295, XP002362918
EDWARD C. TAYLOR, EDWARD E. GARCIA: "The Synthesis of 4-Aminoisoxazolo[5,4-d]pyrimidines", J. ORG. CHEM., vol. 29, 1964, pages 2116 - 2120, XP002362919
PULAKJYOTI BHUYAN, ROSMEH CHANDRA BORUAH, JAGIR SINGH SANDHU: "Studies on Uracils. 10. A Facile One-Pot Synthesis of Pyrido[2,3-d]- and Pyrazolo[3,4-d]pyrimidines", J. ORG. CHEM., vol. 55, 1990, pages 568 - 571, XP002362920
ROBERT B. NICEWONGER, LORI DITTO, DOUG KERR, LASZLO VARADY: "Synthesis of a Novel, Recyclable", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 12, 2002, pages 1799 - 1802, XP002362921
IPITSA DEVI, B. S. D. KUMAR, PULAK J. BHUYAN: "A novel three-component one-pot synthesis of pyrano[2,3-d]pyrimidines and pyrido[2,3-d]pyrimidines using microwave heating in the solid state", TETRAHEDRON LETTERS, vol. 44, 2003, pages 8307 - 8310, XP002362953
ROBB NICEWONGER, APRIL FOWKE, KATHY NGUYEN, LORI DITTO, JUSTIN CASERTA, MICHELE HARRIS, CARMEN M. BALDINO: "Microwave-assisted acylation of 7-amino-5-aryl-6-cyanopyrido[2,3-d]pyrimidines", MOLECULAR DIVERSITY, vol. 7, 2003, pages 247 - 252, XP002362954
DATABASE ZCAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 2003, YOUSSIF, SHAKER ET AL: "Novel uracil and pyrido[2,3-d]pyrimidine-2,4(1H, 3H)-dione derivatives: synthesis and antimicrobial activity", XP002362972, retrieved from STN Database accession no. 2003:911230
DATABASE ZCAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 1999, YOUSSIF, SHAKER ET AL: "A facile one-pot synthesis of pyrido[2,3-d]pyrimidines and pyrido[2,3-d:6,5-d']dipyrimidines", XP002362973, retrieved from STN Database accession no. 1999:177044
DATABASE ZCAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 1999, GEIES, AHMED A.: "Synthesis of pyrido[2,3-d]pyrimidines via the reaction of activated nitriles with aminopyrimidines", XP002362974, retrieved from STN Database accession no. 1999:158849
DATABASE ZCAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 1998, ELNEAIRY, MOHAMED A. A. ET AL: "2-(2-Benzothiazolyl)ethanethioamides in heterocyclic synthesis: novel synthesis of pyridine, pyrido[2,3-d]pyrimidine, coumarin, thiazolone and triazole derivatives", XP002362975, retrieved from STN Database accession no. 1998:756479
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 1991, SEADA, M. ET AL: "Reactions with 2-amino-3,5-dicyanopyridines", XP002362976, retrieved from STN Database accession no. 1991:81740
DATABASE ZCAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 1985, GOGOI, MUKTI ET AL: "Arylidenemalononitriles in heterocyclic syntheses: a novel synthesis of pyrido[2,3-d]pyrimidines", XP002362977, retrieved from STN Database accession no. 1985:131988
DATABASE CROSSFIRE BEILSTEIN Beilstein Institut zur Förderung der Wissenschaften, Frankfurt am Main, DE; 1994, XP002362978, Database accession no. 6875211 (BRN)
DATABASE CROSSFIRE BEILSTEIN Beilstein Institut zur Förderung der Wissenschaften, Frankfurt am Main, DE; 2000, XP002362979, Database accession no. 8349174 (BRN)
DATABASE CROSSFIRE BEILSTEIN Beilstein Institut zur Förderung der Wissenschaften, Frankfurt am Main, DEcr; 1988, XP002362980, Database accession no. 1231932 (BRN)
DATABASE CROSSFIRE BEILSTEIN Beilstein Institut zur Förderung der Wissenschaften, Frankfurt am Main, DE; 2002, XP002362981, Database accession no. 9010879 (BRN)
DATABASE CROSSFIRE BEILSTEIN Beilstein Institut zur Förderung der Wissenschaften, Frankfurt am Main, DE; 2005, XP002362982, Database accession no. 9955126 (BRN)
DATABASE CROSSFIRE BEILSTEIN Beilstein Institut zur Förderung der Wissenschaften, Frankfurt am Main, DE; 1993, XP002362983, Database accession no. 4598493 (BRN)
DATABASE CROSSFIRE BEILSTEIN Beilstein Institut zur Förderung der Wissenschaften, Frankfurt am Main, DE; 1993, XP002362984, Database accession no. 8353231 (BRN)
DATABASE CROSSFIRE BEILSTEIN Beilstein Institut zur Förderung der Wissenschaften, Frankfurt am Main, DE; 2000, XP002362985, Database accession no. 8360481 (BRN)
DATABASE CROSSFIRE BEILSTEIN Beilstein Institut zur Förderung der Wissenschaften, Frankfurt am Main, DE; 2000, XP002362986, Database accession no. 8345402 (BRN)
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