Phenylalanine derivatives

Details Phenylalanine derivatives Phenylalanine derivatives

2005-06-28

2005-06-28

McKane, Joseph K. (Department: 1625)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C514S354000, C514S323000, C514S344000, C514S346000, C514S349000, C514S350000, C514S351000, C546S287000, C546S288000, C546S290000, C546S291000, C546S293000, C546S300000, C546S301000, C546S304000, C546S305000, C546S329000, C546S349000

Reexamination Certificate

active

06911451

ABSTRACT:
Phenylalanine derivatives of formula (1) are described:whereinL1is a linker atom or group;X1is a group selected from —N(R3)CO—, —N(R3)SO2—, —N(R3)C(O)O— or—N(R3)CON(R3a)—; andR is a carboxylic acid or a derivative thereof.The compounds are able to inhibit the binding of a 4 integrins to their ligands and are of use in the prophylaxis and treatment of diseases or disorders involving inflammation.

REFERENCES:
patent: 4470973 (1984-09-01), Natarajan et al.
patent: 4554273 (1985-11-01), Bayssat et al.
patent: 4987132 (1991-01-01), Mase et al.
patent: 5164372 (1992-11-01), Matsuo et al.
patent: 5206373 (1993-04-01), Chung et al.
patent: 5260277 (1993-11-01), McKenzie
patent: 5296486 (1994-03-01), Lazer et al.
patent: 5399585 (1995-03-01), Alig et al.
patent: 5510346 (1996-04-01), Martin et al.
patent: 5698691 (1997-12-01), Yukimasa et al.
patent: 6093696 (2000-07-01), Head et al.
patent: 6596752 (2003-07-01), Lobl et al.
patent: 23 16 881 (1973-10-01), None
patent: 28 37 264 (1979-03-01), None
patent: 196 54 483 (1998-01-01), None
patent: 0 144 230 (1985-06-01), None
patent: 0 498 268 (1992-08-01), None
patent: 0 596 406 (1994-05-01), None
patent: 0 710 657 (1996-05-01), None
patent: 0 710 659 (1996-05-01), None
patent: 0 842 943 (1998-05-01), None
patent: 0 842 945 (1998-05-01), None
patent: 56 090045 (1981-07-01), None
patent: 61083161 (1986-04-01), None
patent: 03 135962 (1991-06-01), None
patent: 63233963 (1995-04-01), None
patent: 63-233963 (1999-09-01), None
patent: WO 93/00095 (1993-01-01), None
patent: WO 93/08174 (1993-04-01), None
patent: WO 93/09795 (1993-05-01), None
patent: 9316994 (1993-09-01), None
patent: WO 94/29285 (1994-12-01), None
patent: WO 9509828 (1995-04-01), None
patent: WO 95/19356 (1995-07-01), None
patent: WO 96/26190 (1996-08-01), None
patent: WO 97/12866 (1997-04-01), None
patent: 9724122 (1997-07-01), None
patent: WO 97/24124 (1997-07-01), None
patent: WO 97/36859 (1997-10-01), None
patent: WO 98/00395 (1998-01-01), None
patent: WO 98/42662 (1998-10-01), None
patent: WO 98/54207 (1998-12-01), None
patent: 9906435 (1999-02-01), None
patent: WO 99/35163 (1999-07-01), None
patent: WO 99/37618 (1999-07-01), None
patent: WO 99/43642 (1999-09-01), None
patent: WO 99/48879 (1999-09-01), None
patent: WO 00/31067 (2000-06-01), None
patent: WO 00/35855 (2000-06-01), None
Bolin, et. al., Structure-activity studies on the vasoactive intestinal peptide pharmacophore, Int. J. Peptide Res. 46, pp. 279-289, 1995.
Ca 124:56589, “Polymer-supported Mitsunobo ether formation and its use in combinatorial chemistry”, Krchnak et. al., p. 1.
Ca 86:107036, “Amino-acids and peptides. Part XL. Protection removable by electrolytic reduction: the use of S-4-picolyl-L-cystene and O-4-picolyl-L-tyrosine in synthesis.”, p. 1.
Chung et. al., “A Practical Synthesis of Fibrinogen Receptor Antagonist MK-383. Selective Functionalization of (S)-Tyrosine”, Tetrahedron, vol. 49, No. 26, pp. 5767-5776.
Azzouny, A.E., et al., “Synthesis of some N-substituted salicylamides structurally related to certain antimicrobials,”Pharmazie,1977, 32(6), 318-323 (abstract).
Badshah, A., et al., “Catalytic reduction of azlactones in alkaline media. Synthesis of amino acids,”J. of Organic Chemistry,1972, 37(18), 2916-2918.
Tous, G., et al., “O'-(Epoxyalkyl) tyrosines and (Epoxyalkyl) phenylalanine as irreversible inactivators of serine proteases: synthesis and inhibition mechanism,”J. of Medicinal Chemistry,1990, 33(6), 1620-1634.
Rico, J.G. et al., “A highly stereoselective michael addition to an α, β-unsaturated ester as the crucial step in the synthesis of a novel beta-amino acid-containing fibrinogen receptor antagonist”,J. Org. Chem,1993, vol. 58, pp. 7948-7951.
Zablocki, J.A. et al., “Potent in vitro and in vivo inhibitors of platelet aggregation based upon the Arg-Gly-Asp sequences of fibrinogen”,J. Med. Chem.,1995, vol. 38, pp. 2378-2394.
Bach et al., “Anomalous optical rotation and circular dichroism of N-thioacylated.alpha.-amino acids and deriva,”Acta Chem. Scand.,1966, 20(10), 2781-2794.
Barrett, G.C., “Circular dichroism of N-thiobenzoly-1-α-amino acids. III. Their circular dichroism through the near-ultraviolet wavelength range,”J. Chem. Soc.,1967,Section C,1-5.
Chemical Abstracts,“N-[4-Thiazolidinyl)carbonyl]amino acid derivatives,” 1981, 95(19), Abstract No. 169173f, 1 page.
Cornforth, J. W., “Oxazoles and Oxazolones,”Chem. Penicillin,Princeton Book Review, 1949, pp. 688, 799, and 800.
Fu, H. et al., “Preliminary study on synthesis and antitumor activity in vitro of derivatives of timonacic,”Chemicals Abstracts,1988, 108(17), Abstract No. 150358k, 1 page.
Harris, R.L.N. et al.,Aust. J. Chem.,“Potential wool growth inhibitors. 2(1H)-Pyridone analogs of mimosine,” 1977, 30(3), 649-655.
Hartke, K. et al., “Dithio and thiono esters. Part 61. Synthesis of α-amino dithioesters and endothiodipeptides,”,J. Prakt. Chem.1996, 338(3), 251-256.
Jaynes, B.H. et al., “Synthesis and In Vivo Antibacterial Activity of Hygromycin a Analogs Modified at the C4′ Aryl Position,”Bioorg. Med. Chem. Letts.,1993, 3(8), 1531-1536.
Jepson, J.B. et al., “Reactions of α-Thioacylamino-acids. Their conversion into Thiazolones and Derivatives Thereof,”J. Chem. Soc.,1955, 1791-1797.
Masahiko, N., Japanese Patent No. 57-080370 published May 19, 1982, “Alpha-Methylcinnamic Acid Derivative, its Preparation and Antilipemic Agent Containing The Same,”Patent Abstracts of Japan,1982, 1 page.
Noike, Y., “Synthesis of Quinolizine Derivatives. VI. Synthesis of 3-Aminoquinolizines. (1). Synthesis of dl-3-Amino-, dl-3-epi-Amino-, and dl-3-epi-Dimethylaminoquinolizidines,”Yakugaku Zasshi,1959, 79(12), 1514-1518 (English summary included).
Ohki, S. et al., “Synthesis of quinolizine derivatives. V. Studies on Diastereoisomer of Ethyl 3-Quinolizidinecarboxylate,”Chem. Pharm. Bull.,1959, 7(6), 708-712.
Schultz, Von O.-E. et al., “Analogos of nuleic acid based as antimetabolites,”Arzneimittel Forschung. Drug Res.,1967, 17(8), 1060-1064 (English summary included).
Tsunematsu, H. et al., “Hydrolysis of phenylthiazolones of p-guanidinophenylalanine and arginine by trypsin and related enzymes,”J. Biochem.,1983, 94(4), 1119-1125.
Whitlock, B.J. et al., “Structure and synthesis of lathyrine,”J. Org. Chem.,1965, 30, 115-118.
Hammadi, A., et al., “Diastereoselective hydrogenation of monodehydro enkephalins controlled by chiral rhodium catalysts,”Tetrahedron: Asymmetry,1992, 3(10), XP002106601, 1247-1262.
Nunami, K., et al., “A novel synthesis of methyl 1,5-disubstituted imidazole-4-carboxylates using 3-bromo-2-isocyanoacrylates,”J. Org. Chem.,1994, 59, XP002106602, 7635-7642.
Shimohigashi, Y., et al., “Dehydro-enkephalins,”Int. J. Peptide Protein Res.,1983, 21, XP002106600, 202-208.
Strange, P.G., et al., “Studies of enzyme-mediated reactions. Part II. Stereochemistry of the elimination of ammonia form L-tyrosine catalysed by the enzyme from maize,”J. Chem. Soc., Perkin I,1972, 18, XP002106603, 2364-2372.
WPI/Derwent No. XP002106604, Japanese Patent No. JP 60 190749 (Mitsui Toatsu Chem. Inc.), Sep. 28, 1985, 1 page, Abstract only.
Buckle, D.R., et al., “Non Thiazolidinedione Antihyperglycaemic Agents. 1: α-Heteroatom Substituted α-Phenylpropanoic Acids,”Bioorg. Med. Chem. Lett.,1996, 6(17), 2121-2126.
Keenan, R.M. et al., “Discovery of Potent Nonpeptide Vitronectin Receptor (avβ3) Antagonists,”J. Med. Chem.,1997, 40(15), 2289-2292.
McDowell, R.S. et al., “From Peptide to Non-Peptide. 2. Thede NovoDesign of Potent, Non-Peptidal Inhibitors of Platelet Aggregation Based on a Benzodiazepinedione Scaffold,”J. Am. Chem. Soc.,1994, 11

Affiliated with

Also associated with

Rating

Phenylalanine derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.

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

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3469399