Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...
Reexamination Certificate
2006-05-30
2006-05-30
Wilson, James O. (Department: 1624)
Organic compounds -- part of the class 532-570 series
Organic compounds
Unsubstituted hydrocarbyl chain between the ring and the -c-...
C546S082000, C546S141000, C564S164000, C564S194000, C564S197000
Reexamination Certificate
active
07053211
ABSTRACT:
The invention relates to a process for the preparation of α-aminosubstituted carboxylic acid amide compounds and/or their salts comprising reacting a carboxylic acid amide of a primary amine with a nitrosylating agent in the presence of a base followed by hydrolysis to give a hydroxy imino derivative followed by hydrogenation and if necessary converting a base or acid of the α-aminosubstituted carboxylic acid amide into one of its salts.
REFERENCES:
patent: 2851494 (1958-09-01), Erhart et al.
patent: 4619784 (1986-10-01), Locatell, Jr. et al.
patent: 6262068 (2001-07-01), Ferrara et al.
Jonnson and Mikiver, “Synthesis of 2-amino-3-(3,4-dihydroxyphenyl)-3-methylbutryic acid (beta,beta-dimethyl DOPA)” Acta Pharmaceutica Suecica, vol. 13(1), pp. 65-74 (1976).
Mukaiyama et al, “A Novel Method for the Preparation of Optically Active Dipeptide. Chemo- and Stereoselective Reduction of 2-Hydroxyimino Amides with Samarium Diodide” Chemistry Letters, vol. 1, pp. 181-184 (1992).
Tikk et al, “Hydroxyimino-3(2H)-isoquinolineones, II” Acta Chimica Hungarica, vol. 114(1), pp. 69-77 (1983).
Tikk I et al, “Hydroxyiminoisoquinolin-3(2H)-ones, V: Synthesis of 4-Amino-1,2,3,4-tetrahydroisoquinolines,” Acta Chimica Hungarica, 1986, pp. 255-262, vol. 121, No. 3, XP002207335, scheme 1, Akademlai Kiado, Budapest, HU.
Watthey J W H et al, “Synthesis and Biological Properties of (Carboxyalkyl)Amino-Substituted Bicyclic Lactam Inhibitors of Angiotensin Converting Enzyme,” Journal of Medical Chemistry, 1985, pp. 1511-1516, vol. 28, No. 10, XP000942750 ISSN: 0022-2623 Cited in the application Schemata II and III, American Chemical Society, Washington, US.
Stjepan Kukolja et al, “Orally absorbable cephalosporin antibiotics. 2. Structure-activity studies of bicyclic glycine derivatives of 7-aminodeacetoxycephalospo ranic acid,” Journal of Medical Chemistry, 1985, pp. 1896-1903, vol. 28, XP002126291 ISSN: 0022-2623 scheme III examples 6A, 13A, 14A, American Chemical Society, Washington, US.
Kägi H, “Über 7-Pyr-oxindol, 7-Pyr-isatin und 7,7′-Di-pyr-indigo,” Helvetica Chimicata ACTA, 1941, pp. 141E-150E, vol. 24, XP002207336 examples IV, VI, VII.
Tikk I et al, “Hydroxyimino-3(2H)-isoquinolinones, II: A Convenient Method for the Preparation of 4-(Hydroxyimino)-1,4-dihydro-3(2H)-isoquinolinones and their o-Alkyl and o-Acyl Derivatives,” Acta Chimica Hungarica, 1983, pp. 69-77, vol. 114, No. 1, XP002207337, p. 70, Akademial Kiado, Budapest, Hu.
Beyer S K et al, “Notiz Zur Synthese Eines Optisch Aktives Ace-Hemmers Mit Amino-oxo-benzazepin-1-alkansaeure-struktu R Mittels Enantiokonvergierender, Kristallisationsinduzierter Racemat-tremung,” Helvetica Chimica Acta, 1988, pp. 337-343, vol. 71, XP002207338, ISSN: 0743-7463 cited in the application scheme 1.
Watthey J W H et al, “Bicyclic Lactam Inhibitors of Anglotesin Converting Enzyme,” Journal of Medical Chemistry, 1984, pp. 816-818, column 1 examples 5a, 6, vol. 27, XP002217344.
Hino, Katsuhiko et al, “Agents acting on the central nervous system. Synthesis of 3-phenyl-2-piperazinyl-1-benzazocines, 3-substituted-2-piperazinyl-1-benzazepines and related compounds,” Chem. Pharm. Bull (1988), 36(7), 2386-400′ XP002217345 examples 12A, 12B.
Heinin J et al, “Hexahydro-5,6,6A,7,12,14 Isoquino2,3-Bbenzazepine-2 Nouvelle Voice D'Acces,” Journal of Heterocyclic Chemistry, Jul. 1986, pp. 975-979, vol. 23, XP002917685 ISSN: 0022-152X examples 7A-7E, Heterocorporation, Provo, US.
Ito Y et al, “A New Synthetic Method for Preparation of 1,3,4,5-Tetrahydro-2H-1-Benzazepin-2-one Derivatives,” Chemistry Letters, 1980, pp. 487-490, XP001069799 ISSN: 0366-7022 examples 5A-III, Chemical society of Japan, Tokyo, Japan.
Henin, Jaques et al., “Reactivity in Alkaline Medium, of Nitrogen-containing Compounds with the Tetralone skeleton. I. Oxazolidines,” Bull. Soc. Chim. FR. (1977), (1-2, PT. 2), 89-91, XP002217346 example 11A.
Evans, D. et al., “The Schmidt Reaction with Aromatic Ketones,” J. Chem. Soc. (1965), (Sep.), 4806-12, XP002217347 example XIV.
Bauer, Ludwig et al, “The Semmler-Wolff Aromatization and Beckmann Rearrangement of 2-′B-(2-and-4-pyridyl)ethyl!-1-tetralone oximes,” J. Org. Chem. (1962), 27, 3982-5, XP002217348 example IX.
Enke Steffen
Hartig Thorsten
Merck Patent GmbH
Millen White Zelano & Branigan P.C.
Tucker Zachary C.
Wilson James O.
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