Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2006-08-29
2006-08-29
Raymond, Richard L. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C514S383000, C514S363000, C514S449000, C514S461000, C548S262200, C549S229000, C549S483000, C549S491000, C549S495000, C549S497000, C549S505000
Reexamination Certificate
active
07098201
ABSTRACT:
A compound of the formula (I):wherein X is hydroxy, protected hydroxy or optionally substituted amino; Y is —COORAwherein RAis hydrogen or ester residue, —CONRBRCwherein RBand RCeach is independently hydrogen or amide residue, optionally substituted aryl or optionally substituted heteroaryl; and A1is optionally substituted heteroaryl; provided that a compound wherein Y and/or A1is optionally substituted indol-3-yl is excluded, a tautomer, a prodrug, a pharmaceutically acceptable salt or a hydrate thereof has an inhibitory activity against an integrase.
REFERENCES:
patent: 3899508 (1975-08-01), Wikel
patent: 3931247 (1976-01-01), Pelosi, Jr.
patent: 4273776 (1981-06-01), Hoehn
patent: 4332735 (1982-06-01), Alaimo et al.
patent: 4336397 (1982-06-01), Cragoe et al.
patent: 4386092 (1983-05-01), Oe et al.
patent: 4423063 (1983-12-01), Rooney et al.
patent: 4637829 (1987-01-01), Schurter et al.
patent: 5112848 (1992-05-01), Brooks et al.
patent: 5292732 (1994-03-01), Rover
patent: 5475109 (1995-12-01), Selnick et al.
patent: 5516797 (1996-05-01), Armistead et al.
patent: 5618830 (1997-04-01), Selnick et al.
patent: 0 418 845 (1991-03-01), None
patent: 658559 (1995-06-01), None
patent: 1 069 111 (2001-01-01), None
patent: 51-75096 (1976-06-01), None
patent: 51-075096 (1976-06-01), None
patent: 61-134346 (1986-06-01), None
patent: 2-38403 (1990-02-01), None
patent: 9616052 (1996-05-01), None
patent: 98/45268 (1998-10-01), None
patent: 99/30699 (1999-06-01), None
patent: 99/48371 (1999-09-01), None
patent: 99/62513 (1999-12-01), None
patent: 99/62520 (1999-12-01), None
patent: 99/62897 (1999-12-01), None
patent: 01/00578 (2001-01-01), None
patent: 100578 (2001-04-01), None
Chemical Abstract DN 67:53943.
Chemical Abstract DN 123:313992, also cited as EP 658559.
Chemical Abstract DN 125:142771, also cited as WO 9616052.
Debnath et al, Structure of Small Molecule Antiviral Compounds, J.Med.Chem.42,3203-9(1999).
PubMed 12462390, also cited as Current Mol. Med. 2/8,691-702(2002).
Floris-Moore et al,PubMed Abstract 14632594, also cited as Ann. Pharmacother. 37/12,1810-3(2003).
Markovitz DM,PubMed Abstract 8380244, also cited as Ann Intern Med., 118/3,211-8(1993).
Sainsbury, Malcolm et al., “Improved synthesis of 6H-pyrido[4,3-b] carbazole derivatives”, J. Chem. Soc., Perkin Trans. 1 (1975), (3), pp. 289-298.
Lesiak, Tadeusz et al., “New β-diketones of furan series”, Rocz. Chem. (1971), 45(5), pp. 903-909.
Kurkovskaya, L. N. et al., “Intramolecular hydrogen bonding in selenophene β-diketones studied by a PMR method”, Teor. Eksp. Khim. (1972), 8(5), pp. 688-691.
Spirkova, K. et al., “Furan derivatives. 202. Nucleophilic substitution reactions of 2-cyano-3-methyl-3-(5-X-2-furyl) acrylonitriles”, Chem. Pap. (1987), 41(6), pp. 787-792, see Compound I, II.
Kazuaki Oda, et al., “Photochemistry of the nitrogen-thiocarbonyl systems. part 24. Photoreactions of thiobenzamide with various substituted furans: regioselective β-benzoylation and transformation of furans to other aromatic compounds”, J. Chem. Soc., Perkin Trans. 1 (1995), (22), pp. 2931-2935.
Zani, C. L. et al., “Efficient directed ortho metalation-based route to cytotoxic furanonaphthoquinone natural products”, Tetrahedron Letter, (1987), 28(52), pp. 6561-6564.
Itahara, Toshio et al., “Arylation of aromatic heterocycles with arenes and palladium (II) acetate”, J. Org. Chem. (1985), 50(25), pp. 5272-5275.
Oleinik, A. F. et al., “Synthesis and antileishmaniasis activity of arylfurylquinoxalines”, Khim.-Farm, Zh. (1978), 12(7), pp. 71-77.
Cernak, Jozef et al., “Electrochemical reduction of para-substituted 2-acyl-5-phenylfurans in dimenthylformamide”, Collect. Czech. Chem. Commun. (1981), 46(2), 498-502.
Sarma, C. R. et al., “Antiinflammatory agents. Part X. Synthesis and antiinflammatory activity of some new [4-[5[formyl(acyl)-2-furyl]oxy]phenyl]alkanoic acid esters”, Indian J. Chem., Sect. B (1989), 28B(11), pp. 993-995.
Koyanagi, Jyunichi et al., “A facile synthesis of 2-acetylnaphthol[2,3-b]furan-4, 9-dione”, J. Heterocycl. Chem. (1995), 32(4), pp. 1289-1291.
Bisagni, Emile et al., “2,3-Disubstituted furans and pyrroles. I. Extension of the Feist-Benary reaction to β-diketones. New synthesis of 3-acylated furans and pyrroles”, Bull. Soc. Chim. Fr. (1967), (8), pp. 2796-2780.
Aly, El-Said Ahmed et al., “A new synthetic route to various 2, 5-distributed furan derivatives”, Proc. Pak. Acad. Sci. (1993), 30(3), pp. 163-167.
Kondrat'eva, G. Ya. et al., “Reaction of oxazoles with acetylenic aldehydes and ketones”, Izv. Akad. Nauk SSSR, Ser. Khim. (1972), (6), pp. 1363-1364.
Ma, Yinmin et al., “Synthesis and ultraviolet-visible spectrum of arylfurylphenylpropenones”, Xibei Daxue Xuebao, Ziran Kexueban (1991), 21(3), pp. 55-59.
Sjoholm, Rainer et al., “Reactions between furylketones and grignard reagents, I. Conjugate additions to 2-acetylfuran”, Acta Acad. Abo., Ser. B (1978), 38(1), p. 9.
Mndzhoyan, A. L. et al., “Furan-derivatives, XXXI. Some acid 2-alkylidene hydrazides and N,N'-diacyl hydrazines as potential antitubercular agents”, Arm. Khim. Zh. (1966), 19 (10), pp. 793-805.
N.S. Prostakov et al. , Lhim, Geterotsikl. Soedin. 1973(2), pp. 230-240.
R.A. Bol'shedvorskaya et al., Zh Organ Khim, 1968, 4(9), pp. 1541-1545.
J. Larkin et al., “Enol Benzoates of β-Diketones”, J. Chem. Soc. Perkin Trans I, 1976, (4), pp. 380-383.
L.N. Kurkovskaya et al., Zh Strukt Khim, 1972, 13(6), pp. 1026-1032.
Khim. Geterotsikl. Soedin. 1973, (11), pp. 519-1522.
T. Gardner et al., “Synthesis of 5-Substituted 3-Isoxazolecarboxylic Acid Hydrazides and Derivatives”, J. Org. Chem., 1961, vol. 26, pp. 1515-1519.
M. Ferles et al., “Synthesis and Reactions of Novel 1,3-dipyridinyl-1,3-Propanediones”, Collect. Czech. Chem., Commun., vol. 55, 1990, pp. 1228-1233.
J. Barluenga et al., “Reactions of N-Unsubstituted 4-Amino-1-azadienes Towards Electrophiles”, Synthesis, Jan. 1996, vol. 1, pp. 133-140.
R.M. Saleh, “Use of ethyl 2-thenoylpyruvate in the synthesis of heterocycles and their derivatives”, Indian Journal of Chemistry, vol. 30B, Mar. 1991, pp. 313-319.
Y. Goldgur et al., “Structure of the HIV-1 integrase catalytic domain complexed with an inhibitor: A platform for antiviral drug design”, Pro. Natl. Acad. Sci. USA, 1999, vol. 96, No. 23, pp. 13040-13043.
K. Oda et al., “Photochemistry of the nitrogen-thiocarbonyl systems. Part. 24. Photoreactions of thiobenzamide with various substituted furans: regioselective β-benzoylation and transormation of furans to other aromatic compounds”, J. Chem. Soc. Perkin Trans. 1, 1995, vol. 22, pp. 2931-2935.
C. L. Zani et al., “Efficient Directed Ortho Metalation-Based Route to Cytotoxic Furanonaphthoquinone Natural Products”, Tetrahedron Letters, vol. 28, No. 52, pp. 6561-6564, 1987.
T. Itahara, “Arylation of Aromatic Heterocycles with Arenes and Palladium (II) Acetate”, J. Org. Chem. 1985, No. 50, pp 5272-5275.
Oleinik, A.F. et al., “nthesis and antileishmaniasis activity of arylfurylquinoxalines”, Khim.-Farm. Zh. 1978, vol. 12, No. 7, pp. 71-77.
J. Cernak et al., “Electrochemical Reduction of para-Substituted 2-Acyl-5-phenylfuranes in Dimethyl-Formamide”, Collection Czechoslovak Chem., Commun., vol. 46, No. 2, 1981, pp. 498-502.
C. R. Sarma et al., “Antiinflammatory agents: Part X +-Synthesis and antiinflammatory activity of some new 4-[5-formyl(acyl)-2-furanoxyl]-phenylalkanoic acid esters”, Indian Journal of Chemistry, vol. 28B, No. 11, Nov. 1989, pp. 993-995.
J. Koyanagi et al., “A Facile Synthesis of 2-Acetylnaphtho[2,3-b]furan-4,9-dione”, J. Heterocycl., Chem. 1995, vol. 32, No. 4, p. 1289-1291.
E. Bisagni et al., “2,3-Disubstituted furans and pyrroles. I.
Fujishita Toshio
Sato Akihiko
Yoshinaga Tomokazu
Patel Sudhaker B.
Raymond Richard L.
Shionogi & Co. Ltd.
Wenderoth , Lind & Ponack, L.L.P.
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