Tyrosine derivatives as PPAR-γ-modulators

Details Tyrosine derivatives as PPAR-γ-modulators Tyrosine derivatives as PPAR-γ-modulators

2008-09-09

2008-09-09

Eyler, Yvonne (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acids and salts thereof

C562S433000, C562S443000, C562S444000

Reexamination Certificate

active

11658856

ABSTRACT:
Compounds of general formula I, and the salts and solvates thereof, wherein R1 represents the radical 2-benzoylphenylamino; R2 represents —(CH2)s—N(COR3)-A-J-T or —(CH2)s—N(R4)—B-J-T; and s. R3, R4, A, B, J and T have the meanings disclosed in the description. These compounds are PPARγ modulators and, therefore, are useful for the treatment or prevention of a condition or a disease mediated by these receptors.

REFERENCES:
patent: 6274608 (2001-08-01), Sauerberg et al.
patent: 0 875 510 (1998-11-01), None
patent: WO 94/29285 (1994-12-01), None
patent: WO 9429285 (1994-12-01), None
patent: WO 97/31907 (1997-09-01), None
patent: WO 9731907 (1997-09-01), None
patent: WO 01/30343 (2001-05-01), None
patent: WO 02/08188 (2002-01-01), None
patent: WO 03/011814 (2003-02-01), None
patent: WO 03/011834 (2003-02-01), None
patent: WO 03011814 (2003-02-01), None
patent: WO 03011834 (2003-02-01), None
patent: WO 03/053966 (2003-07-01), None
patent: WO 2004/020408 (2004-03-01), None
Cobb et al, “N-(2-Benzoylphenyl)-L-Tyrosine PPARγ Agonists,” J. Med. Chem., vol. 41, No. 25, 1998, pp. 5055-5069, XP002355939.
Li, Y. et al, “T0903131 (T131): A Selective Modulator of PPAR?”, 2004, Abstract No. 659-P, San Francisco, CA.
Reifel-Miller, A. et al, “LY519818: A Novel Non-TZD, PPAR[gamma]-Dominant Agonist with Improved Insulin Sensitization and Unique Co-Factor Recruitment and Response Element Activation Profiles,” 2003, Abstract No. 614-P, Indianapolis, IN; San Diego, CA.
Wright, H. et al, “A Synthetic Antagonist for the Peroxisome Proliferator-activated Receptor γ Inhibits Adipocyte Differentiation,”The Journal of Biological Chemistry, vol. 275, No. 3, Issue of Jan. 21, pp. 1873-1877, 2000, USA; 2000 by The American Society for Biochemistry and Molecular Biology, Inc.
Lehmann, J. et al, “An Antidiabetic Thiazolidinedione Is a High Affinity Ligand for Peroxisome Proliferator-activated Receptor γ (PPARγ),”The Journal of Biological Chemistry, vol. 270, No. 22, Issue of Jun. 2, pp. 12953-12956, 1995; 1995 by The American Society of Biochemistry and Molecular Biologi, Inc., USA.
Harland, P. et al, “Synthesis of Primary Amines via Alkylation of the Sodium Salt of Trifluoroacetamide: An Alternative to the Gabriel Synthesis,”Communications, Nov. 1984, pp. 941-943; Department of Chemistry, University of Lancaster, Great Britain; Lancaster Synthesis, Ltd., Great Britain.
Lin, X. et al, “Utilization of Fukuyama's sulfonamide protecting group for the synthesis ofN-substituted α-amino acids and derivatives,”Tetrahedron Letters 41(2000), pp. 3309-3313, Abstract; 2000 Elsevier Science Ltd.; Chiron Corporation, CA, USA.
Fajas, L. et al, “The Organization, Promoter Analysis, and Expression of the Human PPARγ Gene,”The Journal of Biological Chemistry,vol. 272, No. 30, Issue of Jul. 25, pp. 18779-18789, 1997, USA; 1997 by The American Society for Biochemistry and Molecular Biology, Inc.
Fajas, L. et al, “PPARγ3 mRNA: a distinct PPARγ mRNA subtype transcribed from an independent promoter,”FEBS Letters 438(1998), pp. 55-60, FEBS 21031; 1998 Federation of European Biochemical Societies; Département d' Athérosclérose, France.
Vamecq, J. et al, “Medical significance of peroxisome proliferator-activated receptors,”The Lancet, vol. 354, Jul. 10, 1999, pp. 141-148; Neuropaediatrics Department of Professor Jean-Pierre Nuyts, France; Laboratory of Molecular and Cell Biology, University of Burgundy, Dijon.
Grimaldi, P., “The roles of PPARs in adipocyte differentiation,”Progress in Lipid Research 40(2001), pp. 269-281; 2001 Elsevier Science Ltd.; Centre de Biochimie, University of Nice-Sophia Antipolis, France.
Schiller, P. et al, “Inhibition of Gap-Junctional Communication Induces the Trans-differentiation of Osteoblasts to an Adipocytic Phenotype in Vitro,”The Journal of Biological Chemistry, vol. 276, No. 17, Issue of Apr. 27, pp. 14133-14138, 2001, USA; Published, JBC Papers in Press, Jan. 25, 2001.
Berger, J. et al, “PPARs: therapeutic targets for metabolic disease,”Trends in Pharmacological Sciences, vol. 26, No. 5, May 2005; 2005 Merck Research Laboratories—Published by Elsevier Ltd.
Minoura, H. et al, “Pharmacological characteristrics of a novel nonthiazolidinedione insulin sensitizer, FK614,”European Journal of Pharmacology 494(2004), pp. 273-281; Abstract; 2004 Elsevier B.V.; Research Division, Fujisawa Pharmaceutical Co., Ltd., Japan; Tsukuba Research Center, Daicel Chemical Industries, Ltd., Japan.
Kurtz, T.W., “Treating the metabolic syndrome: telmisartan as a peroxisome proliferator-activated receptor-gamma activator,”Acta Diabetol, 2005, vol. 42, pp. S9-S16; supplied by the British Library—“The world's knowledge; Laboratory of Medicine, San Francisco, CA; supplied by The British Library—The world's knowledge”.
Henke, B. et al, “N-(2-Benzoylphenyl)-L-tyrosine PPARγ Agonists. 1. Discovery of a Novel Series of Potent Antihyperglycemic and Antihyperlipidemic Agents,”Journal of Medicinal Chemistry, 1998, vol. 41, No. 25, pp. 5020-5036; 1998 American Chemical Society; published on Web Nov. 11, 1998.
Collins, J. et al, “N-(2-Benzoylphenyl)-L-tyrosine PPARγ Agonists. 2. Structure-Activity Relationship and Optimization of the Phenyl Alkyl Ether Moiety,”Journal of Medicinal Chemistry, 1998, vol. 41, No. 25, pp. 5037-5054; 1998 American Chemical Society; published on Web Nov. 6, 1998; Published on Web Nov. 6, 1998.
Cobb, J. et al, “N-(2-Benzoylphenyl)-L-tyrosine PPARγ Agonists. 3. Structure-Activitiy Relationship and Optimization of theN-Aryl Substituent,”Journal of Medicinal Chemistry, 1998, vol. 41, No. 25, pp. 5055-5069; 1998 American Chemical Society; published on Web Nov. 7, 1998.
Bal-Tembe, S., et al, “HL 752: A Potent and Long-Acting Antispasmodic Agent,”Bioorganic&Medicinal Chemistry, vol. 5, No. 7, pp. 1381-1387, 1997; 1997 Elsevier Science Ltd., Great Britain.
Cantello, B. et al, “[[ω-(Heterocyclylamino)alkoxy]benzyl]-2,4-thiazolidinediones as Potent Antihyperglycemic Agents,”Journal of Medicinal Chemistry, 1994, vol. 37, No. 23, pp. 3977-3985; 1994 American Chemical Society.
Mitsunobu, Oyo, “The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products,”Synthesis, Jan. 1981, pp. 1-28; 1981 Georg Thieme Verlag, Stuttgart, New York.
Daoud, K.M. et al, “Synthesis of Biologically Active Compounds of Amino Ester Hydrochlorides derived from Substituted-cinchophen,”Journal of the Indian Chemical Society, vol. 66, May 1989, pp. 316-318; supplied by The British Library—“The world's knowledge”.
Hirschmann, R. et al, “De Novo Design and Synthesis of Somatostatin Non-Peptide Peptidomimetics Utilizing β-D-Glucose as a Novel Scaffolding,”Journal of the American Chemical Society, 1993, vol. 115, No. 26, pp. 12550-12568; 1993 American Chemical Society.
Elbrecht, A. et al, “L-764406 Is a Partial Agonist of Human Peroxisome Proliferator-activated Receptor γ,”The Journal of Biological Chemistry, vol. 274, No. 12, Issue of Mar. 19, pp. 7913-7922, 1999, USA; 1999 by The American Society for Biochemistry and Molecular Biology, Inc.

Affiliated with

Also associated with

Rating

Tyrosine derivatives as PPAR-γ-modulators does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Tyrosine derivatives as PPAR-γ-modulators, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Tyrosine derivatives as PPAR-γ-modulators will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3952198