Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2009-02-27
2011-11-01
Nolan, Jason M (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S407000, C548S364100, C546S133000
Reexamination Certificate
active
08048893
ABSTRACT:
The present invention relates to the novel derivatives of formula (I) in whichA is, if it is present, a (C1-C6) alkyl, a (C3-C6) alkenyl, a (C3-C6) alkynyl, a (C3-C7) cycloalkyl or a (C5-C7) cycloalkenyl, R1 is an NR6R7, (C4-C7) azacycloalkyl, (C5-C7) azacycloalkenyl, (C5-C9) azabicycloalkyl or (C5-C9) azabicycloalkenyl group; A-R1 is such that the nitrogen of R1 and the nitrogen in the 1-position of the pyrazole are necessarily separated by at least two carbon atoms, R3 is an H, halogen, OH, SH, NH2, ORc, SRc, SORa, SO2Ra, NHCHO, NRaRb, NHC(O)Ra, NHC(S)Ra or NHSO2Ra, R4 is an aryl or heteroaryl; and R5 is an H, halogen, CF3, CHF2, CH2F, linear or branched (C1-C6) alkyl or (C3-C7) cycloalkyl, to their racemates, enantiomers and diastereoisomers and to their mixtures, their tautomers and to their pharmaceutically acceptable salts.
REFERENCES:
patent: 5409946 (1995-04-01), Garvey et al.
patent: 5939436 (1999-08-01), Carling et al.
patent: 1 938 546 (1970-03-01), None
patent: 0427390 (1991-05-01), None
patent: 0525879 (1993-02-01), None
patent: 1 002 871 (2000-05-01), None
patent: 1004592 (2000-05-01), None
patent: WO 2004/048386 (2004-06-01), None
Aracava et al. The Journal of Pharmacology and Experimental Therapeutics 2005, 312(2), 1195-1205.
Moore et al. Biorg. Med. Chem. Lett. 1999, 9(9), 1285-1290.
J. G. Cannon, Chapter Nineteen in Burger's Medicinal Chemistry and Drug Discovery, Fifth Edition, vol. I: Principles and Practice, Wiley-Interscience 1995, pp. 783-802.
Schafer et al. Drug Discovery Today 2008, 13 (21/22), 913-916.
Horig et al. Journal of Translational Medicine 2004, 2(44).
Kishimoto et al. Chem. Pharm. Bull. 1976, 24(12), 3001-3010.
Haydar et al. Bioorganic & Medicinal Chemistry 2009, 17, 5247-5258.
Amundsen et al, Beta-Dialkylaminoethyl Bromide Hydrobromides and Beta-Dialkylaminoethylamines, J. Am. Chem. Soc., 1941, 63 (1), pp. 305-307.
Cheng, et al, Relationship Between the Inhibition Constant (KI) and the Concentation of Inhibitor Which Causes 50 Per Cent Inhibition (I50) of an Enzymatic Reaction, Biochem. Pharmacol. (1973), 22, 3099-3108.
Dahlbom et al, Some 2-bromobenzyl and 2,6-dimethylphenoxy-ethyl substituted sterically hindered amines, Acta Pharm. Suecica, 1969 (6) pp. 413-418.
Davies et al, Characterisation of the binding of [3H]methyllycaconitine: a new radioligand for labelling alpha7-type neuronal nicotinic acetylcholine receptors, Neuropharmacology 1999 (38) pp. 670-690.
H Plumpe et al., Archiv Der Pharmazie Und Berichte Der Deutschen Pharmazeutischen Gesellschaft , Einige Neue in 4-Stellung Substituierte Pyrazole, (1967, pp. 704-708, vol. 388(8).
Hacksell et al, 3-Lithioquinuclidin-2-ene: A novel intermediate for the synthesis of muscarinic agonists and antagonists, Bioorganic & Med. Chem. Letters, 1994 (4)24, pp. 2837-2840.
Hartwig, John, Transition Metal Catalyzed Synthesis of Arylamines and Aryl Ethers from Aryl Halides and Triflates: Scope and Mechanism, Angew. Chem. (Int. Ed.) 1998, 37, 2046-2067.
Jenkins et al, Substituent Variation in Azabicyclic Triazole- and Tetrazole-Based Muscarinic Receptor Ligands, J. Med. Chem. 1992 (35) pp. 2392-2406.
Kabalka et al, A New Route to Iodine-Labeled N-Isopropyl Iodoamphetamine via Organoboranes, Tetrahedron Letters, 1986 (27) 33, pp. 3843-3844.
Kotha et al, Recent applications of the Suzuki-Miyaura cross-coupling reaction in organic synthesis, Tetrahedron 2002 (58) pp. 9633-9695.
Lamba et al, Imine-Bridged Planar Poly(p-phenylene) Derivatives for Maximization of Extended pi-Conjugation. The Common Intermediate Approach, J. Am. Chem. Soc., 1994 (116) pp. 11723-11736.
Lang et al, Synthesis of 4-(4-Phenyl-3-pyrazolyl)-4H-1,2,4-triazoles, J. Heterocyclic Chem., 1977 (14) 65 pp. 65-69.
Malpass et al, Reaction of Chlorosulphonyl Isocyanate with 1,3-Dienes. Control of 1,2-and 1,4-Addition Pathways and the Synthesis of Aza- and Oxa-bicyclic Systems, J.C.S. Perkin I, 1977 (8) pp. 874-884.
Muller et al, Syntheses of Phenothiazinylboronic Acid Derivatives—Suitable Starting Points for the Construction of Redox Active Materials, Synthesis, 2002 (9), pp. 1163-1170.
Selwood et al, Synthesis and Biological Evaluation of Novel Pyrazoles and Indazoles as Activators of the Nitric Oxide Receptor, Soluble Guanylate Cyclase, J. Med. Chem., 2001 (44) 1 pp. 78-93.
Villalgordo et al, A New Class of Fused Imidazoles by Intramolecular Nucleophillic ipso-Substitution in 2-Alkylsulfonylimidazoles: Synthesis of 2,3-Dihydroimidazo[2,1-b][1,3]oxazoles, Synthesis 1999 (9) pp. 1613-1624.
Wang et al, A General Synthesis of Beta-Aryl and Heteroarylpyrroles by Palladium-catalyzed Coupling Reaction of Beta-Tributylstannylpyrrole with Aryl and Heteroaryl Halides, Tetrahedron Letters, 1996 (37) 19 pp. 3247-3250.
Wong et al, Synthesis of Extended Chromogenic Tetra-(p-substituted-phenyl)-tetraethoxycalix[4]arenes, Tetrahedron Letters, 1993 (34) 51 pp. 8237-8240.
Yasuhara et al, Deprotection of N-Sulfonyl Nitrogen-Heteroaromatics with Tetrabutylammonium Fluoride, Tetrahedron Letters, 1998 (39) pp. 595-596.
Yokota et al, Isoquinuclidine-based expectorants. Synthesis and biological activities of N-alkoxybenzylisoquinuclidines, Eur. J. Med. Chem., 1997 (32) pp. 377-384.
Chemical Abstracts, CAS Registry No. 56824-22-7, Nov. 16, 1984.
Parham et al, 3-Amino-4-phenylpyrazole as an Intermediate, J. of Organic Chem., 1960 (25)7 pp. 1259-1260.
Bohme Andrees
Bouquerel Jean
Doerflinger Gilles
El-Ahmad Youssef
Evers Michel
Aventis Pharma SA
Bender Kelly L.
Nolan Jason M
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