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  Cycloalkyl, lactam, lactone and related compounds, pharmaceutical compositions comprising same, and methods for inhibiting beta-amyloid peptide release and/or its synthesis by use of such compoundsUSPTO Application #: 20050272666Title: Cycloalkyl, lactam, lactone and related compounds, pharmaceutical compositions comprising same, and methods for inhibiting beta-amyloid peptide release and/or its synthesis by use of such compounds Abstract: Disclosed are compounds which inhibit β-amyloid peptide release and/or its synthesis, and, accordingly, have utility in treating Alzheimer's disease. Also disclosed are pharmaceutical compositions comprising a compound which inhibits β-amyloid peptide release and/or its synthesis as well as methods for treating Alzheimer's disease both prophylactically and therapeutically with such pharmaceutical compositions. (end of abstract)
Agent: Burns Doane Swecker & Mathis L L P - Alexandria, VA, US Inventors: Jing Wu, Jay S. Tung, Eugene D. Thorsett, Michael A. Pleiss, Jeffrey S. Nissen, Jeffrey Neitz, Lee H. Latimer, Varghese John, Stephen Freedman, Thomas C. Britton, James A. Audia, Jon K. Reel, Thomas E. Mabry, Bruce A. Dressman, Cynthia L. Cwi, James J. Droste, Steven S. Henry, Stacey L. McDaniel, William Leonard Scott, Russell D. Stucky, Warren J. Porter USPTO Applicaton #: 20050272666 - Class: 514019000 (USPTO) Related Patent Categories: Drug, Bio-affecting And Body Treating Compositions, Designated Organic Active Ingredient Containing (doai), Peptide Containing (e.g., Protein, Peptones, Fibrinogen, Etc.) Doai, Cyclopeptides, 2 Peptide Repeating Units In Known Peptide Chain The Patent Description & Claims data below is from USPTO Patent Application 20050272666. Brief Patent Description - Full Patent Description - Patent Application Claims
FIELD OF THE INVENTION [0001] The present invention relates to compounds of formula I 2 [0002] wherein R.sup.1-R.sup.4 are as herein defined, and to a process (Mukaiyama Aldol reaction) for the preparation of such compounds. Compounds of formula I are useful intermediates in the synthesis of other products, including, e.g. Dolastatin 10. BACKGROUND OF THE INVENTION [0003] Mukaiyama Aldol reactions are known. Dialkyl acetals are known to be substituted by Mukaiyama aldol reactions with silyl enol ethers or silyl ketene acetals affording .beta.-alkoxy ketones or esters (K. Saigo, M. Osaki, T. Mukaiyama, Chem. Lett. 1976, 769-770; T. Mukaiyama, M. Murakami, Synthesis 1987, 1043-1054; S. Kano, T. Yokomatsu, H. Iwasawa, S. Shibuya, Chem. Lett. 1987, 1531-1534; M. A. Graham, A. H. Wadsworth, M. Thornten-Pett, B.Carrozzini, G. L. Cascarano, C. M. Rayner, Tetrahedron Lett. 2001, 42, 2865-2868; M. A. Graham, A. H. Wadsworth, M. Thornten-Pett, B.Carrozzini, G. L. Cascarano, C. M. Rayner, Org. Biomol. Chem. 2003, 1, 834-849). [0004] Surprisingly, it has now been found that N-benzyl-protected dialkyl acetal derivatives undergo desired aldol reaction with high diastereoselectivity using a Mukaiyama aldol reaction. SUMMARY OF THE INVENTION [0005] In one embodiment, the present invention relates to a process of the preparation of compounds of formula I 3 [0006] comprising reacting a compound of formula II 4 [0007] with a compound of formula III 5 [0008] in the presence of a Lewis acid and an organic solvent; [0009] wherein [0010] R.sup.1 is C.sub.1-4 alkyl, C.sub.3-6 cycloalkyl-C.sub.1-4 alkyl or aryl-C.sub.1-4 alkyl; [0011] R.sup.2 is C.sub.1-4 alkyl, benzyl, substituted benzyl or allyl; [0012] R.sup.3 is C.sub.1-4 alkyl or allyl; [0013] R.sup.4 is C.sub.1-4 alkyl, allyl, benzyl or substituted benzyl; [0014] R.sup.4' is benzyl or substituted benzyl; or alternatively [0015] R.sup.1 and R.sup.4 together with the nitrogen to which they are bound form a pyrrolidine group; and [0016] R.sup.5 is a trialkylsilyl group. [0017] In another embodiment, the invention relates to compounds of formula I as defined above. [0018] In other embodiments, the invention relates to compounds of formula II as described above, and compounds of formula IV and VI as defined below. DETAILED DESCRIPTION OF THE INVENTION [0019] As used herein, the following terms have the following meanings: [0020] "C.sub.1-4 alkyl" denotes straight or branched chain hydrocarbon residues containing 1 to 4 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl. Continue reading... Full patent description for Cycloalkyl, lactam, lactone and related compounds, pharmaceutical compositions comprising same, and methods for inhibiting beta-amyloid peptide release and/or its synthesis by use of such compounds Brief Patent Description - Full Patent Description - Patent Application Claims Click on the above for other options relating to this Cycloalkyl, lactam, lactone and related compounds, pharmaceutical compositions comprising same, and methods for inhibiting beta-amyloid peptide release and/or its synthesis by use of such compounds patent application. ###  How KEYWORD MONITOR works... a FREE service from FreshPatents1. Sign up (takes 30 seconds). 2. Fill in the keywords to be monitored. 3. Each week you receive an email with patent applications related to your keywords. Start now! - Receive info on patent apps like Cycloalkyl, lactam, lactone and related compounds, pharmaceutical compositions comprising same, and methods for inhibiting beta-amyloid peptide release and/or its synthesis by use of such compounds or other areas of interest. ### Previous Patent Application: Anti-inflammatory compositions and methods Next Patent Application: Pyrazole derivatives, medicinal composition containing the same, medicinal use thereof, and intermediate for production thereof Industry Class: Drug, bio-affecting and body treating compositions ### FreshPatents.com Support Thank you for viewing the Cycloalkyl, lactam, lactone and related compounds, pharmaceutical compositions comprising same, and methods for inhibiting beta-amyloid peptide release and/or its synthesis by use of such compounds patent info. IP-related news and info Results in 8.19869 seconds Other interesting Feshpatents.com categories: Daimler Chrysler , DirecTV , Exxonmobil Chemical Company , Goodyear , Intel , Kyocera Wireless , |
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