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  Epoxycarboxamide compound, azide compound, and amino alcohol compound, and process for preparing alpha-keto amide compound using themUSPTO Application #: 20080058516Title: Epoxycarboxamide compound, azide compound, and amino alcohol compound, and process for preparing alpha-keto amide compound using them Abstract: wherein R1 and R2 each represents alkyl group, alkenyl group, aromatic hydrocarbon group or heterocyclic group; R3 represents alkyl group, alkenyl group, aromatic hydrocarbon group, heterocyclic group, R6—O— or R7—N(R8)—; where R6 represents alkyl group, alkenyl group, aromatic hydrocarbon group or heterocyclic group; R7 and R8 each represents hydrogen atom, alkyl group, alkenyl group, aromatic hydrocarbon group or heterocyclic group, and, R4 and R5 represent the same groups as R7 and R8, respectively, and R4 and R5 optionally form a ring together; and X represents —O— or —N(R9)—, where R9 represents hydrogen atom or alkyl group, and X optionally forms a ring together with R4 or R5, and processes for preparing α-keto amide compound using the same. The present invention is to provide manufacturing intermediates which can be led to useful α-ketoamide compounds having protease-inhibiting activity extremely economically and stereoselectively, and to provide epoxycarboxamide compounds, azide compounds and amino alcohol compounds represented by the following formulae: (end of abstract) Agent: Jordan And Hamburg LLP - New York, NY, US Inventors: Nobuo Kobayashi, Tsuneo Koji, Takashi Fujita, Tomofumi Nishimura, Akihiko Hosoda USPTO Applicaton #: 20080058516 - Class: 544148000 (USPTO) Related Patent Categories: Organic Compounds -- Part Of The Class 532-570 Series, Azo Compounds Containing Formaldehyde Reaction Product As The Coupling Component, Carbohydrates Or Derivatives, Hetero Ring Is Six-membered Having Two Or More Ring Hetero Atoms Of Which At Least One Is Nitrogen (e.g., Selenazines, Etc.), Six-membered Hetero Ring Consists Of Oxygen, Nitrogen And Carbon (e.g., 1,2-oxazines, Etc), 1,4-oxazines, Morpholines (i.e., Fully Hydrogenated 1,4-oxazines, , The Patent Description & Claims data below is from USPTO Patent Application 20080058516. Brief Patent Description - Full Patent Description - Patent Application Claims
[0001] This is a divisional application of Ser. No. 10/331,702, filed Dec. 30, 2002, which is in turn a continuation-in-part application of PCT/JP01/05668 filed on Jun. 29, 2001 claiming priorities of Japanese Patent Applications No. 2000-198089, No. 2000-198090 and No. 2000-198091 all of which were filed on Jun. 30, 2000, now abandoned. The subject matter of the aforementioned prior applications is hereby incorporated herein by reference. FIELD OF THE INVENTION [0002] The present invention relates to an epoxycarboxamide compound, an azide compound, and an amino alcohol compound, and a process for preparing an .alpha.-keto amide compound using them, and more particularly to an epoxycarboxamide compound, an azide compound, and an amino alcohol compound, which can be used as an intermediate product in the preparation of an .alpha.-keto amide compound having a protease inhibiting activity, and a process for preparing an .alpha.-keto amide compound using the above compounds. BACKGROUND ART [0003] It is known that a protease, which is a proteolytic enzyme, is responsible for the onset and progression of various diseases such as hypertension, thrombosis, pancreatitis, cancer, an Alzheimer disease, pulmonary emphysema, a nerve degeneration disease, an allergic disease, muscular dystrophy, a rheumatic disease, osteoporosis and a periodontal disease (Protein, Nucleic Acid, and Enzyme, vol. 42, No. 14 (1997); and Experimental Medicine, vol. 17, No. 15 (1999)), and inhibitor substances of protease, namely, protease inhibitors are expected as a target of medicines. [0004] An .alpha.-keto amide compound, which has been reported (Japanese Provisional Patent Publication No. 149166/1992; Japanese Provisional Patent Publication No. 211648/1992; Japanese PCT Provisional Patent Publication No. 504547/1994; WO9816512; J. Med. Chem., 39, 4089 (1996); and Exp. Opin. Ther. Patents., 8, 1707 (1998)) to have an inhibiting activity with respect to protease, especially serine protease (elastase, tryptase, trypsin, chymotrypsin, and prolyl endopeptidase) and cysteine protease (calpain, cathepsin B, and cathepsin L), is a compound expected to possibly have an inhibiting activity with respect to cathepsin K, which has recently been reported to be closely responsible for bone metabolism. [0005] As a representative synthesis method for a protease inhibitor having an .alpha.-keto amide structure, (A) J. Med. Chem., 36, 3472 (1993) is known, and further, as a representative synthesis method for optically active substances thereof, (B) J. Med. Chem., 37, 2918 (1994) is known. [0006] By the above (A) method, an .alpha.-keto amide compound which is a desired compound cannot be obtained in the form of an optically active substance. Further, the above (B) method has the following problems: (1) an optically active amino acid as a starting material is expensive; (2) since an amino acid is used as a starting material, only a limited substituent can be introduced into the oxirane ring as substituent R.sup.1 (see general formula (I)); and (3) an .alpha.-hydroxy group in the reaction precursor cannot be stereoselectively controlled, and therefore a product is obtained in the form of a diastereomer mixture and satisfactory purification for the product is difficult. Thus, the above methods are not satisfactory as an industrial production process. [0007] The present inventors have conducted extensive and intensive studies with a view toward solving the problems accompanying the prior art. As a result, they have found raw materials (an epoxycarboxamide compound, an azide compound, and an amino alcohol compound) for preparation of an .alpha.-keto amide compound, which are advantageous not only in that substituent R.sup.1 is not restricted by the amino acid structure, but also in that an .alpha.-keto amide compound can be stereoselectively formed, and thus have completed the present invention. DISCLOSURE OF THE INVENTION [0008] Specifically, the epoxycarboxamide compound of the present invention is represented by the following formula (I): [0009] wherein R.sup.1 represents a substituted or unsubstituted, straight, branched or cyclic alkyl group, a substituted or unsubstituted, straight, branched or cyclic alkenyl group, a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted heterocyclic group, where the substituent for the alkyl group, alkenyl group, aromatic hydrocarbon group or heterocyclic group is a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryloxy group or a substituted or unsubstituted arylthio group; and R.sup.2 represents a substituted or unsubstituted, straight, branched or cyclic alkyl group, a substituted or unsubstituted, straight, branched or cyclic alkenyl group, a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted heterocyclic group, where the substituent for the alkyl group, alkenyl group, aromatic hydrocarbon group or heterocyclic group is a hydroxy group, an oxo group, a halogen atom, a substituted or unsubstituted, straight, branched or cyclic alkenyl group having 2 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted heterocyclic group, a nitro group, a substituted or unsubstituted amino group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, an acyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted carbamoyl group, a substituted sulfonamide group, a substituted amide group, a mercapto group, a cyano group or a methylenedioxy group. [0010] Also, the azide compound of the present invention is represented by the following formula (VI): [0011] wherein R.sup.1 and R.sup.2 have the same meanings as defined above. [0012] Moreover, the amino alcohol compound of the present invention is represented by the following formula (IX): [0013] wherein R.sup.1 and R.sup.2 have the same meanings as defined above, R.sup.3 represents a substituted or unsubstituted, straight, branched or cyclic alkyl group, a substituted or unsubstituted, straight, branched or cyclic alkenyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted heterocyclic group, R.sup.6--O-- or R.sup.7--N(R.sup.8)--, where R.sup.6 represents a substituted or unsubstituted, straight, branched or cyclic alkyl group, a substituted or unsubstituted, straight, branched or cyclic alkenyl group, a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted heterocyclic group, R.sup.7 and R.sup.8 may be the same or different from each other, and each represents a hydrogen atom, a substituted or unsubstituted, straight, branched or cyclic alkyl group, a substituted or unsubstituted, straight, branched or cyclic alkenyl group, a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted heterocyclic group, where the substituent for the alkyl group, alkenyl group, aromatic hydrocarbon group or heterocyclic group is a hydroxy group, an oxo group, a halogen atom, a substituted or unsubstituted, straight, branched or cyclic alkenyl group having 2 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted heterocyclic group, a nitro group, a substituted or unsubstituted amino group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, an acyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted carbamoyl group, a substituted sulfonamide group, a substituted amide group, a mercapto group, a cyano group or a methylenedioxy group; R.sup.4 and R.sup.5 represent the same groups as R.sup.7 and R.sup.8, respectively, and R.sup.4 and R.sup.5 optionally form a ring together with the carbon atom through which R.sup.4 and R.sup.5 are bonded; and X represents --O-- or --N(R.sup.9)-- where R.sup.9 represents a hydrogen atom or a substituted or unsubstituted, straight, branched or cyclic alkyl group, and X optionally forms a ring together with R.sup.4 or R.sup.5. [0014] Further, the present invention provides a process for preparing an .alpha.-keto amide compound represented by the following formula (X): [0015] wherein R.sup.1 to R.sup.5 and X have the same meanings as defined above, wherein the process comprises oxidizing an amino alcohol compound represented by the following formula (IX): [0016] wherein R.sup.1 to R.sup.5 and X have the same meanings as defined above. [0017] Further, the present invention provides a process for preparing an .alpha.-keto amide compound represented by the following formula (X): [0018] wherein R.sup.1 to R.sup.5 and X have the same meanings as defined above, wherein the process comprises: reducing an azide compound represented by the following formula (VI): [0019] wherein R.sup.1 and R.sup.2 have the same meanings as defined above, to obtain an amine compound represented by the following formula (VII): [0020] wherein R.sup.1 and R.sup.2 have the same meanings as defined above; condensing the obtained amine compound with a carboxylic acid compound represented by the following formula (VIII): [0021] wherein R.sup.3 to R.sup.5 and X have the same meanings as defined above, to obtain an amino alcohol compound represented by the following formula (IX): Continue reading... 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