Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2005-04-12
2005-04-12
Raymond, Richard L. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C514S295000, C514S395000, C514S415000, C514S712000, C544S106000, C544S253000, C544S283000, C544S282000, C546S183000, C548S306400, C549S362000, C549S469000
Reexamination Certificate
active
06878700
ABSTRACT:
The present invention relates to novel cinnamide compounds that are useful for treating inflammatory and immunune diseases, to pharmaceutical compositions containing these compounds, and to methods of inhibiting inflammation or suppressing immune response in a mammal.
REFERENCES:
patent: 4808582 (1989-02-01), Platel et al.
patent: 4973599 (1990-11-01), Gilman et al.
patent: 5028629 (1991-07-01), Hite et al.
patent: 5208253 (1993-05-01), Boschelli et al.
patent: 5776951 (1998-07-01), Arrowsmith et al.
patent: 5817862 (1998-10-01), Poetsch et al.
patent: 5883106 (1999-03-01), Stevens et al.
patent: 5883133 (1999-03-01), Schwark et al.
patent: 5912266 (1999-06-01), Perez
patent: 6110922 (2000-08-01), Link et al.
patent: 6329362 (2001-12-01), Archibald et al.
patent: 2123383 (1971-12-01), None
patent: 4030041 (1992-03-01), None
patent: 0081321 (1983-06-01), None
patent: 0219756 (1986-10-01), None
patent: 722928 (1996-07-01), None
patent: 835 867 (1998-04-01), None
patent: 887 340 (1998-12-01), None
patent: 2 117 760 (1983-10-01), None
patent: 12072766 (2000-03-01), None
patent: 9813347 (1998-04-01), None
patent: 9822423 (1998-05-01), None
patent: WO9839303 (1998-09-01), None
patent: 9854207 (1998-12-01), None
patent: 9911258 (1999-03-01), None
patent: WO9920617 (1999-04-01), None
patent: WO9920618 (1999-04-01), None
patent: WO9949856 (1999-10-01), None
patent: WO0015604 (2000-03-01), None
patent: WO0015645 (2000-03-01), None
patent: WO0021920 (2000-04-01), None
patent: WO0048989 (2000-08-01), None
patent: WO0106984 (2001-02-01), None
patent: WO0107052 (2001-02-01), None
Chemical Abstract DN 117:111634, also cited as DE 4030041.*
Chemical Abstract DN 129:40990, also cited as WO 9822423.*
Chemical Abstract DN 125:167598, also cited as EP 722928.*
Franke et al,Helkvetica Chimica Acta,58/1,268-78(1975), also cited as Chemical Abstract Dn 82:124989. See CAS RN # 54875 53-5.*
Kelly et al.,PubMed Abstr.:10553036;also cited as J Immunol, 163/10,5173-7(1999).*
Zhou et al,PubMed Abstr.:11776041;also cited as Chin Med J 113/7,654-6(2000).*
Pillinger et al,PubMed Abstr.:9826736; also cited as Proc Natl Acad Sci. USA,95/24, 14540-5(1998).*
Emond et al,PubMed.Abstr.:11881994;also cited as J Med Chem.,45/6,1253-8(2002).*
Fujita et al.,PubMed Abst.:11408364;also cited as Drug Metab Dispos, 19/7,983-9(2001).*
Franke et al:“Synthetische Juvenilhormone”; Helv. Chim. Acta vol. 58 Fasc. 1 p 268-278 (1975).*
U.S. Appl. No. 09/285,477, filed Apr. 2, 1999, Staunton et al.
U.S. Appl. No. 09/285,325, filed Apr. 2, 1999, Fowler et al.
U.S. Appl. No. 09/606,770, filed Jun. 29, 2000, Link et al.
U.S. Appl. No. 09/606,717, filed Jun. 29, 2000, Wang et al.
U.S. Appl. No. 09/695,040, filed Oct. 24, 2000, Gunawardana.
Ali, R. et al.,Mechanisms of inflammation and Leukocyte Activation,Med. Clin. North America (1997) 81:1-28.
Bella, J., et al.,The Structure of the Two Amino-terminal Domains of Human ICAM-1 Suggests How it Functions as a Rhinovirus Receptor and As An LFA-1 Integrin Ligand,Proc. Natl. Acad. Sci., USA (1998) 95:4140-4145.
Binnerts, M.E., et al.,How LFA-1 Binds to Different Ligands,Immunol. Today (1999) 20:240-245.
Boschelli, D.H., et al.,Inhibition of E-Selectin-, ICAM-1-, and VCAM-1-Mediated Cell Adhesion by Benzo(b)thiophene-, Benzofuran-, Indole-, and Naphthalene-2-Carboxamides: Identification of PD 144795 as an Antiinflammatory Agent,J. Med. Chem. (1995) 38:4597-4614.
Carlos, T.M.,Leukocyte-Endothelial Adhesion Molecules,Blood (1994) 84:2068-2101.
Edwards, C.P. et al.,Mapping the Intercellular Adhesion Molecule-1 and -2 Binding Site on the Inserted Domain of Leukocyte Function-associated Antigen-1,J. Biol. Chem. (1998) 273:28937-28944.
Emeigh, J.E., et al.,Small Molecule Antagonists of LFA-1-Mediated Cell Adhesion,221st ACS National Meeting, San Diego, CA, USA (2001) MEDI 256.
Fisher, K.L., et al.,Identification of the Binding Site in Intercellular Adhesion Molecule 1 for its Receptor, Leukocyte Function associated Antigen 1,Mol. Biol. Cell (1997) 8:501-515.
Gadek, T.R., et al.,Identification and Characterization of Antagonists of the LFA-1/1CAM-1 Protein-Protein Interaction as Novel Immunomodulatory Agents,220th ACS National Meeting, Washington, D.C., USA (2000) MEDI 177.
Gahmberg, C.G.,Leukocyte Adhesion: CD11/CD18 Integrins and Intercullular Adhesion Molecules,Curr. Opin. Cell Biol. (1997) 9:643-650.
Gahmberg, C.G.,Leukocyte Adhesion: Structure and Function of Human Leukocyte β2-integrins and Their Cellular Ligands,Eur. J. Biochem. (1997) 245:215-232.
Green, J.M.,T Cell Receptor Stimulation, But Not CD28 Costimulation, Is Dependent on LFA-1-Mediated Events,Eur. J. Immunology (1994) 24:265-272.
Hamilton, G.S., et al.,Fluorenylalkanoic and Benzoic Acids as Novel Inhibitors of Cell Adhesion Processes in Leukocytes,J. Med. Chem. (1995) 38:1650-1656.
Henricks, P.A.,Pharmacological modulation of cell adhesion molecules,Eur. J. Pharmcol. (1998) 344:1-13.
Huang, C.,A Binding Interface on the I Domain of Lymphocyte Function-associated Antigen-1(LFA-1)Required for Specific Interaction with Intercellular Adhesion Molecule 1(ICAM-1), J. Biol. Chem. (1995) 270:19008-19016.
Huth, J.R.,NMR and Mutagenesis Evidence for an I Domain Allosteric Site That Regulates Lymphocyte Function-associated Antigen 1 Ligand Binding.Proc. Natl. Acad. Sci,, USA (2000) 97:5231-5236.
Kallen, J., et al.,Structural Basis for LFA-1 Inhibition upon Lovastatin Binding to the CD1 1a I-Domain,J. Mol. Biol. (1999) 292-1-9.
Kelly, T.A.,Cutting Edge: A Small Molecule Antagonist of LFA-1-Mediated Cell Adhesion,J. Immunol. (1999) 163:5173-5177.
Kishimoto, T.K.,Integrins, ICAMs and Selectins: Role and Regulation of Adhesion Molecules in Neutrophil Recruitment to Inflammatory Sites,Adv. Pharmacol. (1994) 25:117-169.
Landis, R.C.,Involvement of The “I” domain of LFA-1 in Selective Binding to Ligands ICAM-I and ICAM-3,J. Cell Biol. (1994) 126:529-537.
Link, J.T., et al.,Discovery and SAR of Diarylsulfide Cyclopropylamide LFA-1/ICAM-1 Interaction Antagonists,Bioorg. Med. Chem Lett. (2001) 11:973-976.
Liu, G.,Small Molecule Antagonists of the LFA-1/CAM-1 Interaction as Potential Therapeutic Agents,Expert Opin. Ther. Patents (2001) 11(9):1383-1393.
Liu, G., et al.,Discovery of Novel P-arylthio Cinnamides as Antogonists of Leukocyte Function-associated Antigen-1/intracellular Adhesion Molecule-1 Interaction, 1. Identification of an Additional Binding Pocket Based on an Anilino Diaryl Sulfide Lead.J. Med. Chem. (2000) 43:4025-4040.
Liu, G., et al.,Novel P-arylthio Cinnamides as Antagonists of Leukocyte Function-associated Antigen-1/intracellular Adhesion Molecule-1 Interaction. 2. Mechanism of Inhibition and Structure-based Improvement of Pharmaceutical Properties.(2001) J. Med. Chem. 44:1202-1210.
Lu, C., et al.,An Isolated, Surface-expressed I Domain of the Integrin Alβ2 Is Sufficient for Strong Adhesive Function When Locked in the Open Conformation with a Disulfide Bond.Proc. Natl. Acad. Sci. USA (2001) 98-2387-2392.
Nakano, T., et al.,Adxanthromycins A and B, New Inhibitors of ICAM-1/ILFA-1 Mediated Cell Adhesion Molecule from Streptomyces sp. NA-148,J. Antibos. (Tokyo) (2000) 53:12-18.
Pei, Z., et al.,Discovery of Potent Antagonists of Leukocyte Function-associated Antigen-1/intercellular Adhesion Molecule-1 Interaction. 3. Amide(C-ring)Structure-activity Relationship and Improvement of Overall Properties of Arylthio Cinnamides.J. Med. Chem. (2001) 44:2913-2920.
Qu, A., et al.,The Role of the Divalent Cation in the Structure of the I Domain from the CD11a/CD18 Integrin,Structure (1996) 4:931-942.
Sanfilippo, P.J.,Novel Thiazole Based Heterocycles as Inhibitors of LFA-1/ICAM-1 Mediated Cell Adhesion,J. Med. Chem. (1995) 38:1057-1059.
Springer, T.A.,Adhesion Receptors of the Immune System,Nature (1990) 346:425-434.
Stanley, P., et al.,The I Domain of Integrin LFA-1 interacts with ICAM-1 Domain 1 at Residue Glu-34 But Not GIn-73,J. Biol. Chem. (1998) 273:3358-3362.
Winn, Martin et al.,Discovery of Novel p-Arylthio Cinnamides as Antagolists of Leukocyte Function-Associated Antigen-1/Intercellular Adhesion Mol
Boyd Steven A.
Freeman Jennifer C.
Geldern Tom von
Gunawardana Indrani W.
Jae Hwan-Soo
Abbott Laboratories
Finnegan Henderson Farabow Garrett & Dunner LLP
LandOfFree
Cell adhesion-inhibiting antiinflammatory and... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Cell adhesion-inhibiting antiinflammatory and..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Cell adhesion-inhibiting antiinflammatory and... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3429224