Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2005-03-22
2005-03-22
Berch, Mark L. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C514S397000, C514S398000, C514S400000, C514S217090, C514S218000, C514S235800, C514S243000, C514S249000, C514S252020, C514S252030, C514S252050, C514S252100, C514S254050, C514S262100, C514S212030, C514S226500, C514S263200, C514S266230, C514S322000, C514S326000, C514S300000, C514S307000, C514S314000, C544S139000, C544S120000, C544S122000, C544S124000, C544S125000, C544S128000, C544S130000, C544S003000, C544S256000, C544S257000, C544S238000, C544S353000, C544S357000, C544S370000, C544S405000, C544S049000, C544S
Reexamination Certificate
active
06869945
ABSTRACT:
This application is directed to compounds useful as inhibitors of PDE4 in the treatment of diseases regulated by the activation and degranulation of eosinophils, especially asthma, chronic bronchitis, and chronic obstructuive pulmonary disease, of the formula:where Y is ═C(R1a)— or —[N→(O)k]— where k is 0 or 1;G1is a saturated or unsaturated carbon ring system that is a 3- to 7-membered monocyclic, or that is a 7- to 12-membered, fused polycyclic; provided that G1is not a discontinuous or restricted biaryl moiety as defined under G2; where optionally one carbon atom may be replaced by a heteroatom selected from N, O, and S; where optionally a second carbon atom thereof, and further optionally a third carbon atom thereof may be replaced by N; -G2is a saturated or unsaturated carbon ring system that is a 3- to 7-membered monocyclic; or that is a 7- to 12-membered, fused polycyclic; or that is a 7- to 18-membered discontinuous or restricted biaryl moiety; wherein for each of the carbon ring systems recited, optionally one carbon atom of said carbon ring system may be replaced by a heteroatom selected from N, O, and S; where optionally a second carbon atom thereof, and further optionally a third carbon atom thereof may be replaced by N; E is selected from:and all other substituents shown above are as defined in the specification.
REFERENCES:
patent: 4270946 (1981-06-01), Gutman
patent: 4692185 (1987-09-01), Michaely
patent: 4861891 (1989-08-01), Saccomano et al.
patent: 5552438 (1996-09-01), Christensen, IV
patent: 5602157 (1997-02-01), Christensen, IV
patent: 5614540 (1997-03-01), Christensen, IV
patent: 5863926 (1999-01-01), Christensen, IV et al.
patent: 5922557 (1999-07-01), Pon
patent: 6380218 (2002-04-01), Marfat et al.
patent: 0550900 (1992-12-01), None
patent: 0773024 (1997-05-01), None
patent: 0500989 (1998-12-01), None
patent: 2140772 (1973-01-01), None
patent: 2327675 (1999-02-01), None
patent: 7304775 (1995-11-01), None
patent: WO9500139 (1995-01-01), None
patent: WO9818796 (1998-05-01), None
patent: WO9845268 (1998-10-01), None
patent: WO9845628 (1998-10-01), None
patent: WO9918793 (1999-04-01), None
patent: WO9920280 (1999-04-01), None
patent: WO9920625 (1999-04-01), None
patent: WO0157025 (2001-08-01), None
patent: WO0157036 (2001-08-01), None
Trophy, Theodore J. et al, “Phosphodiesterase IV Inhibitors as Therapy for Eosinophil-induced Lung Injury in Asthma,” Environmental Health Perspectives, vol. 102 Suppl. 10, Dec. 1994, pp 79-84.
Duplantier, Allen J., et al., “Biarylcarboxylic Acids and -amides: Inhibition of Phosphodiesterase Type IV versus [3H]Rolipram Binding Activity and Their Relationship to Emetic Behavior in the Ferret, Journal of Medicinal Chemistry,” 1996, vol. 39, No. 1, pp 120-125.
Schneider, Herbert H, et al, “Discriminative Stimulus Properties of the Stereoisomers of the Phosphodiesterase Inhibitor Rolipram.” Pharmacology Biochemistry and Behavior, vol. 50, No. 2, 1995, pp. 211-217.
Banner, Katherine H., et. al., “Acute versus chronic administration of phosphodiesterase inhibitors on allergen-induced pulmonary cell influx in sensitized guinea-pigs, ” British Journal of Pharmacology, 114, 1995, pp. 93-98.
Barnette, Mary S., et al., “The Ability of Phosphodiesterase IV Inhibitors to Suppress Superoxide Production in Guinea Pig Eosinophils Is Correlated with Inhibition of Phosphodiesterase IV Catalytic Activity,” The Journal of Pharmacology and Experimental Therapeutics, 273, 1995 pp. 674-679.
Wright, Kathryn, F., et al., “Differential in vivo and in vitro bronchorelaxant activities of CP-80,633, a selective phosphodiesterase 4 inhibitor, ”Can. J. Physiol. Pharmacol. 75, 1997, pp. 1001-1008.
Manabe, Haruhiko, “Anti-inflammatory and Bronchodilator Properties of KF19514, a Phosphodiesterase 4 and 1 Inhibitor,” European Journal of Pharmacology, 332, 1997, pp. 97-107.
Ukita, Tatsuzo, et. al., Novel, Potent, and Selective Phosphodiesterase-4 Inhibitors as Antiasthmatic Agents: Synthesis and Biological Activities of a Series of 1-Pyridylnaphthalene Derivatives, J. Med. Chem, 48, 1999, pp. 1088-1099.
Compton, CH, et. al., The Efficacy of Ariflo™ (SB 207499, A Second Generation, Oral PDE4 Inhibitor, In Patients with COPD, Am. J. Respir. Crit. Care Med., 159, 1999.
Leeman, Marc M.D., et. al., “Reduction in Pulmonary Hypertension and in Airway Resistances by Enoximone (MDL 17,043) in Decompensated COPD*”, Chest, 91, 1987, pp. 662-666.
Rabe, K.F., et. al., “Identification of PDE Isozymes in Human Pulmonary Artery and Effect of Selective PDE Inhibitors,” Am. J. Physiol, 266 (LCMP 10), 1994, pp. L536-L543.
Hughes, Bernadette, et. al., PDE 4 inhibitors: the use of molecular cloning in the design and development of novel drugs, Drug Discovery Today, Science Direct, 2(3), 1997 pp. 89-101.
Banner, K.H., et. al., “The Effect of Selective Phosphodiesterase Inhibitors in Comparison with other Anti-asthma Drugs on Allergen-induced Eosinophilia in Guinea-pig Airways,” Pulmonary Pharmacology, 8, 1995, pp. 37-42.
Raebum, David, et.al., “Anti-inflammatory and bronchodilator properties of RP 73401, a novel and selective phosphodiesterase typed IV inhibitor,” Br, J. Pharmacol., 113, 1994, pp. 1423-1431.
Karlsson, J.A., et. al., “Anti-Inflammatory Effects of the Novel Phosphodiesterase IV Inhibitor RP 73401,” Int. Arch Allergy Immunol, 107, 1995, pp. 425-426.
Escott, K.J., et. al., Pharmacological Profiling of Phosphodiesterase, 4 (PDE4) Inhibitors and Analysis of the Therapeutic Ratio in Rats and Dogs, Br. J. Pharmacol, 123 (Proc suppl.) 1998 40P.
Landells, L.J., et. al., “Oral Administration of the Phosphodiesterase (PDE) 4 Inhibitor, V11294A Inhibits Ex-Vivo Agonist-induced Cell Activation,” Eur. Resp. J., 12 (Suppl. 28), 362s, 1998, P2393.
Gale, D.D., et. al., “Pharmacodynamic-Pharmacokinetic (PD/PK) Profile of the Phosphodiesterase (PDE)4 Inhibitor, V11294A, in Human Volunteers,” Am. J. Respir. Crit Care Med., 159, A611, 1999, pp A108.
Montana, J., et. al., “Activity of D4418, A Novel Phosphodiesterase 4 (PDE4) Inhibitor, Effects in Cellular and Animal Models of Asthma and Early Clinical Studies,” Am. J. Respir. Crit., Care Med., 159, A108, 1999, pp A624.
Cavalla, D., et. al., “Activity of V11294A, A Novel Phosphodiesterase 4 (PDE4) Inhibitor, In Cellular and Animal Models of Asthma,” Am. J. Respir. Crit. Care Med. 155, 1997, pp A660.
Pascal, Y., et. al., “Synthesis and Structure,-activity Relationships of 4-oxo-1 pheyl-3,4,5,7-Tetrahydro-[1,4]Diazepino[6,7,1-HI]Indolines: Novel PDE4 Inhibitors,” 215thACS, MEDI, 50, 1998.
Burnouf, C., et. al., “Pharmacology of the Novel Phosphodiesterase Type 4 Inhibitor, Cl-1018,” 215thACS, MEDL 008, 1998.
Mueller, George W., et. al., N-Phthaloyl-β- Aryl- β- Amino Derivatives Potent TNF-α And PDE4 Inhibitors, MEDI, 299, 1999.
Mueller, George W., et. al., “Thalidomide Analogs and PDE4 Inhibition,” Bioorganic & Medicinal Chemistry Letters, 8, 1998 pp. 2669-2674.
Takayama, K., “Synthetic Studies on Selective Type IV Phosphodiesterase (PDE IV) Inhibitors,” MEDI 245, 1997.
Gordon, T., et. al., “Anti-Inflammatory Effects of a PDE4 Inhibitor in a Rat Model of Chronic Bronchitis,” Am. J. Respir. Crit. Care Med., 159, A33, 1999.
Perrier, Helene, et. al., “Substituted Furans as Inhibitors of the PDE4 Enzyme,” Bioorganic & Medicinal Chemistry Letters 9, 1999, pp. 323-326.
Groneberg, Robert D., et. al., “Dual inhibition of Phosphodiesterase 4 and Matrix Metalloproteinases by an (Arylsulfonyl)hydroxamic Acid Template,” Journal of Medicinal Chemistry, 1999, vol. 42, No. 4, pp. 541-544.
Fujimura, Masaki, et. al. Bronchoprotective Effects of KF-19514 and Cilostazol in Guinea Pigs in Vivo, European Journal of Pharmacology, 327, 1997, pp. 57-63.
Manabe, Haruhiko, et. al.,
Marfat Anthony
McKechney Michael William
Benson Gregg C.
Berch Mark L.
Habte Kahsay
Pfizer Inc
Richardson Peter C.
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