Cyclic amine bace-1 inhibitors having a heterocyclic...

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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C514S254010, C514S254050

Reexamination Certificate

active

07910590

ABSTRACT:
Disclosed are novel compounds of the formulaor a pharmaceutically acceptable salt or solvate thereof, whereinR1isX is —O—, —C(R14)2— or —N(R)—;Z is —C(R14)2— or —N(R)—;t is 0, 1, 2 or 3;each R and R2is independently H, alkyl, cycloalkyl, cycloalkylalkyl, aryl, heteroaryl, heterocycloalkyl, arylalkyl, heteroarylalkyl, heterocycloalkylalkyl, alkenyl or alkynyl;each R14is H, alkyl, alkenyl, alkynyl, halo, —CN, haloalkyl, cycloalkyl, cycloalkylalkyl, aryl, heteroaryl, heterocycloalkyl, arylalkyl, heteroarylalkyl, heterocycloalkylalkyl, —OR35, —N(R24)(R25) or —SR35;R41is alkyl, cycloalkyl, —SO2(alkyl), —C(O)-alkyl, —C(O)-cycloalkyl or -alkyl-NH—C(O)CH3;and the remaining variables are as defined in the specification.Also disclosed are pharmaceutical compositions comprising the compounds of formula I and methods of treating cognitive or neurodegenerative diseases with compounds of formula I.Also disclosed are pharmaceutical compositions and methods of treatment comprising compounds of formula I in combination with other agents useful in treating cognitive or neurodegenerative diseases.

REFERENCES:
patent: 6683091 (2004-01-01), Asberom et al.
patent: 2004/0171614 (2004-09-01), Pissarnitski et al.
patent: WO 8903842 (1989-05-01), None
patent: WO 9518104 (1995-06-01), None
patent: WO 0007995 (2000-02-01), None
patent: WO 0050391 (2000-08-01), None
patent: WO 0056335 (2000-09-01), None
patent: WO 0202505 (2002-01-01), None
patent: WO 0202506 (2002-01-01), None
patent: WO 0202512 (2002-01-01), None
patent: WO 0202518 (2002-01-01), None
patent: WO 0202520 (2002-01-01), None
patent: WO 02088101 (2002-11-01), None
patent: WO 03013527 (2003-02-01), None
patent: WO 03018543 (2003-03-01), None
patent: WO 03027068 (2003-04-01), None
patent: WO 03045913 (2003-06-01), None
patent: WO 03066592 (2003-08-01), None
Hamada et al. Expert Opin.Drug Discov. 4(4), p. 391-416 (2009).
Baltaïef et al, (Z)-Dimethyl α-(Bromomethyl)fumarate, an Efficient Intermediate for the Selective Synthesis of Dimethyl 3-Alkyl Itaconates and 2-Alkyl 3-Carbomethoxy-γ-Lactams, Tetrahedron, vol. 55, pp. 3949-3958 (1999).
Bellier et al, “Synthesis and Biological Properties of New Constrained CCK-B Antagonists: Discrimination of Two Affinity States of the CCK-B Receptor on Transfected CHO Cells”, J. Med. Chem., vol. 40, pp. 3947-3956 (1997).
Berg et al, “Pharmaceutical Salts”, Journal of Pharmaceutical Sciences, vol. 66, pp. 1-19 (1977).
Chackalamannil et al, “Total Synthesis of (+)-Himbacine and (+)-Himbeline”, J. Org. Chem., vol. 64, pp. 1932-1940 (1999).
Danielmeier et al, “Efficient Pathways to (R)- and (S)-5-Hydroxymethyl-2-oxazolidinone and Some Derivatives”, Tetrahedron: Asymmetry, vol. 6, No. 5, pp. 1181-1190 (1995).
Dinsmore et al, “3,8-Diazabicyclo[3.2.1]octan-2-one Peptide Mimetics: Synthesis of a Conformationally Restricted Inhibitor of Farnesyltransferase”, Organic Letters, vol. 3, pp. 865-868 (2001).
Ezquerra et al, “Stereoselective Double Alkylation of EthylN-Boc-pyroglutmate”, J. Org. Chem., vol. 59, pp. 4327-4331 (1994).
Gould, Salt Selection for Basic Drugs, International Journal of Pharmaceutics, vol. 33, pp. 201-217 (1986).
Hanessian et al, “The Power of Visual Imagery in Synthesis Planning. Stereocontrolled Approaches to CGP-60536B, a Potent Renin Inhibitor”, J. Org. Chem., vol. 67, pp. 4261-4274 (2002).
Hayashi et al, “Studies on Angiotensin Converting Enzyme Inhibitors. 4. Synthesis and Angiotensin Converting Enzyme Inhibitory Activities of 3-Acyl-1-alkyl-2-oxoimidazolidine-4-carboxylic Acid Derivatives”, J. Med. Chem., vol. 32, pp. 289-297 (1989).
Hock et al, “Generation of Antibodies Specific for β-amyloidby Vaccination of Patients with Alzheimer Disease”, Nature Medicine, vol. 8, pp. 1270-1275 (2002).
Hom, “Bicyclic Aminoimidazolone BACE1 Inhibitors”, Expert Opin. Ther. Patents, vol. 17, No. 6, pp. 737-740 (2007).
Itoh et al, “Asymmetric Synthesis of (−)-Adaline”, Organic Letters, vol. 4, No. 15, pp. 2469-2472 (2002).
Kruse et al, “Multisubstrate Inhibitors of Dopamine β-Hydroxylase. 2. Structure-Activity Relationships at the Phenethylamine Binding Site”, J. Med. Chem., vol. 30, pp. 486-494 (1987).
Lowe et al, “Amino Acid Bearing Nucleobases for the Synthesis of Novel Peptide Nucleic Acids”, J. Chem. Soc., Perkin Trans. 1, pp. 539-546 (1997).
MacDonald et al, “Discovery of Further Pyrrolidinetrans- Lactams as Inhibitors of Human Neutrophil Elastase (HNE) with Potential as Development Candidates and the Crystal Structure of HNE Complexed with an Inhibitor (GW475151)”, J. Med. Chem., vol. 45, pp. 3878-3890 (2002).
McGaughey et al, “Structure-Guided Design of β-Secretase (BACE-1) Inhibitors”, Expert Opin. Drug Discovery, vol. 2, No. 8, pp. 1129-1138 (2007).
Melnikova, “Therapies for Alzheimer's Disease”, Nature Review Drug Discovery, vol. 6, pp. 341-342 (2007).
Pettit et al, “The Dolastatins; 18: Stereospecific Synthesis of Dolaproine”, Synthesis, pp. 719-725 (1996).
Pfeiffer et al, “A Short Synthesis of 4-Imidazolidinone”, Liebigs Ann. Chem., pp. 993-995 (1988).
Roggo, “Inhibition of BACE, A Promising Approach to Alzheimer's Disease Therapy”, Current Topics in Medicinal Chemistry, vol. 2, pp. 359-370 (2002).
Tian et al, “An Efficient Scalable Process for teh Synthesis of N-Boc-2-tert-butyldimethylsiloxypyrrole”, Organic Process Research & Development, vol. 6, pp. 416-418 (2002).
Stahl, Handbook of Pharmaceutical Salts: Selection, and Use, Int'l. Union of Pure and Applied Chemistry, pp. 330-331 (2002).
Vippagunta et al, “Crystalline Solids”, Advanced Drug Delivery Reviews, vol. 48, pp. 3-26 (2001).
Webb et al, “Conformationally Restricted Arginine Analogues”, J. Org. Chem., vol. 56, pp. 3009-3016 (1991).
International Search Report for International Application No. PCT/US2004/025018, mailed Aug. 22, 2005.

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