Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2005-08-30
2005-08-30
Raymond, Richard L. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S227800, C514S235800, C514S252140, C544S060000, C544S295000, C544S315000, C544S330000, C544S122000
Reexamination Certificate
active
06936616
ABSTRACT:
Selective MMP-13 inhibitors are pyrimidine derivatives of the formulaor a pharmaceutically acceptable salt thereof,wherein:R2is hydrogen, halo, hydroxy, C1-C6alkyl, C1-C6alkoxy, C2-C6alkenyl, C2-C6alkynyl, NO2, NR4R5, CN, or CF3;E is independently O or S;A and B independently are OR4or NR4R5;R4and R5independently are H, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, (CH2)naryl, (CH2)ncycloalkyl, (CH2)nheteroaryl, or R4and R5when taken together with the nitrogen to which they are attached complete a 3- to 8-membered ring containing carbon atoms and optionally containing a heteroatom selected from O, S, or NH, and optionally substituted or unsubstituted;n is an integer of from 0 to 6.
REFERENCES:
patent: 3118754 (1964-01-01), Nickell
patent: 4031104 (1977-06-01), Bossert et al.
patent: 5068337 (1991-11-01), Archibald et al.
patent: 5130317 (1992-07-01), Baader et al.
patent: 5260323 (1993-11-01), Baader et al.
patent: 5516775 (1996-05-01), Zimmermann et al.
patent: 5519038 (1996-05-01), Baader et al.
patent: 5948780 (1999-09-01), Peterson, Jr. et al.
patent: 6008243 (1999-12-01), Bender et al.
patent: 6080750 (2000-06-01), Hisaki et al.
patent: 2002/0156061 (2002-10-01), Barvian et al.
patent: 2002/0161000 (2002-10-01), Barvian et al.
patent: 2003/0078276 (2003-04-01), Adrianjara et al.
patent: 2003/0087924 (2003-05-01), Sorenson
patent: 2003/0144274 (2003-07-01), Bunker et al.
patent: 2003/0229103 (2003-12-01), Weithmann et al.
patent: 2004/0167120 (2004-08-01), Klingler et al.
patent: 2005/0004111 (2005-01-01), Klinger et al.
patent: 2082076 (1993-05-01), None
patent: 0 260 057 (1988-03-01), None
patent: 0418797 (1991-03-01), None
patent: 0 418 797 (1991-03-01), None
patent: 0463592 (1992-01-01), None
patent: 0935963 (1999-08-01), None
patent: 1138680 (2001-10-01), None
patent: 04 840783 (1973-06-01), None
patent: 08 151380 (1996-06-01), None
patent: 0009485 (2000-02-01), None
patent: 0112611 (2001-02-01), None
patent: WO 01/63244 (2001-08-01), None
patent: 0234726 (2002-05-01), None
patent: 0234753 (2002-05-01), None
patent: WO02/064568 (2002-08-01), None
patent: 02064568 (2002-08-01), None
patent: WO02/064571 (2002-08-01), None
patent: WO02/064080 A2 (2002-08-01), None
patent: WO02/064547 A2 (2002-08-01), None
patent: WO03/032999 (2003-04-01), None
patent: 03049738 (2003-06-01), None
Takahashi et. al. Chemical Abstract, 1975, vol. 83, No. 21, p. 491, Abstract #178072b.
Neunhoffer et. al., Chemical Abstract, 1974, vol. 81, No. 25, p. 545, Abstract #169499c.
Prikazchikova.et. al., Chemical Abstract, 1974, vol. 81, No. 16, p. 150, Abstract #100677s.
Matsumoto et. al., Chemical Abstract, 1973, vol. 79, No. 10, p. 454, Abstract #66394u.
Titov et. al., Chemical Abstract, 1972, vol. 77, No. 13, p. 478, Abstract #94976n.
Mermann et. al., Chemical Abstract, 1967, vol. 67, No. 13, Abstract #69036s.
U.S. Appl. No. 10/075,918, Barvian et al., filed Feb. 13, 2002.
U.S. Appl. No. 10/075,069, Adrianjara et al., filed Feb. 13, 2002.
U.S. Appl. No. 10/071,073, Barvian et al., filed Feb. 8, 2002.
U.S. Appl. No. 10/224,234, Sorenson, filed Aug. 20, 2002.
U.S. Appl. No. 10/264,764, Bunker et al., filed Oct. 4, 2002.
U.S. Appl. No. 10/634,531, Johnson, filed Aug. 5, 2003.
U.S. Appl. No. 10/634,709, O'Brien, filed Aug. 5, 2003.
U.S. Appl. No. 10/634,419, Hicks et al., filed Aug. 5, 2003.
U.S. Appl. No. 10/634,713, Picard, filed Aug. 5, 2003.
U.S. Appl. No. 10/739,261, Bunker et al., filed Aug. 5, 2003.
PCT International Search Report for PCT/IB02/00190 filed Jan. 18, 2002.
Chemical Abstracts, vol. 125, No. 13, 1996, Abstract No. 167964d, Fukuda et. al., XP-002198554.
Database Crossfire Bulletin 'Online, Database accession No. 786662, XP-002198556, Beilstein, 1988.
Shkurko, et al, Khim. Geterotsikl. Soedin., 1977; 6; pp 821824—Hard Copy to Follow.
Database Crossfire Bulletin 'Online, Databaase accession No. 7297869, XP-002198557, Beilstein, 1988.
Yamamoto, et al, “Direct Introduction of Acyl and Ethoxycarbonyl, Groups Into Pyrimidine Ring Through the Trimethyl-Stannyl Derivatives” Heterocycles, 1995; 41(6); pp 1275-1290.
Database Crossfire Bulletin 'Online, Database accession No. 139954, XP-002198558, Beilstein, 1988.
J. Chem. Soc., 1959; pp 525-530, Hunt et. al.
Database Crossfire Bulletin 'Online, Database accession No. 791572 XP-002198559, Beilstein, 1988.
Sakasai, et al, “Studies in Pyrimidine Derivatives. XVII. Synthesis of Pyrimidine-4-Carboxylic Esters”, Heterocycles, 1979; 13; pp 235-236.
Chemical Abstracts, vol. 79, No. 11, Abstract No. 663944 XP-002198555.
Montana, John, et al, “The design of selective non-substrate-based matrix metalloproteinase inhibitors”, Current Opinion in Drug Discovery & Development, 2000; pp 353-361.
Clark, Ian, et al, “Matrix metalloproteinase inhibitors in the treatment of arthritis”, Current Opinions in Anti-inflammatory & Immunomodulatory Investigational Drugs, 2000; 2(1), pp 16-25.
Chen, James, et al, “Structure-Based Design of a Novel, Potent, and Selective Inhibitor for MMP-13 Utilizing NMR Spectroscopy and Computer-Aided Molecular Design”, J. Am. Chem. Soc., 2000, 122; pp 9648-9654.
Hirota, et al., “Novel Synthesis of Pyrido[3,4-d]pyrimidines, Pyrido[2,3-d]-pyrimidines, and Quinazolines via Palladium-Catalyzed Oxidative coupling”, Heterocycles, 1994; 37(1):563-570.
Ye, et al., “Catalytic Domains of Matrix Metalloproteinases: A Molecular Biology Approach to Drug Discovery”, Curr.Med.Chem., 1996; 3:407-418.
Lovejoy, et al., “Crystal structures of MMP-1 and -13 reveal the structural basis for selectivity of collagenase inhibitors”, Nature Structural Biol., 1999; 6:217-221.
Moy, et al., High-resolution solution structure of the catalytic fragment of human collagenase-3 (MMP-13) complexed with a hydroxamic acid inhibitor, J. Mol. Biol., 2000; 302:671-689.
Mitchell, et al., “Cloning, Expression, and Type II Collagenolytic Activity of Matrix Metalloproteinase-13 from Human Osteoarthritic Cartilage”, J. Clin. Invest., 1996: 97(3):761-768.
Neuhold, et al., “Postnatal expression in hyaline cartilage of constitutively active human collagenase-3 (MMP-13) induces osteoarthritis in mice”, J. Clin, Invest., 2001; 107:35-44.
Dahlberg, et al., Selective Enhancement of Collagenase-Mediated Cleavage of Resident Type II Collagen in Cultured Osteoarthritic Cartilage and Arrest with a Synthetic Inhibitor that Spares Collagenase I (Matrix Metalloproteinase 1), Arthrit. & Rheum., 2000; 43(3):673-682.
Billinghurst, et al., “Comparison of the Degradation of Type II Collagen and Proteoglycan in Nasal and Articular Cartilages Induced by Interleuken-1 and the Selective Inhibition of Type II Collagen Cleavage by Collagenase”, Arthrit. & Rheum., 2000; 43(3):664-672.
Billinghurst, et al., “Enhanced Cleavage of Type II Collagen by Collagenases in Osteoarthritic Articular Cartilage”, J. Clin. Invest., 1997; 99:1534-1545.
Office Action mailed Jun. 16, 2003, in U.S. 10/264,764, McKenzie.
Barvian Nicole Chantel
Patt William Chester
Ashbrook Charles W.
Grissey Todd M.
Purchase, Jr. Claude F.
Raymond Richard L.
Truong Tamthom N.
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