Organic compounds -- part of the class 532-570 series – Organic compounds – Chalcogen in the nitrogen containing substituent
Patent
1995-06-05
1997-12-30
Grumbling, Matthew V.
Organic compounds -- part of the class 532-570 series
Organic compounds
Chalcogen in the nitrogen containing substituent
544 92, 544287, 546141, 5142305, 5142272, 514311, C07D26518, A61K 31535
Patent
active
057032343
ABSTRACT:
##STR1## wherein R.sup.1 is H or lower alkyl, R.sup.2 and R.sup.3 combine together with the adjacent nitrogen to form heterocyclic group, and R.sup.4 is protected or unprotected hydroxy-substituted lower alkyl, which comprises ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 are the same as defined above, with a ##STR3## wherein L.sup.1 is a leaving group and R.sup.4 is the same as defined synthetic intermediate for 1-methylcarbapenem derivative having excellent antibacterial activity.
REFERENCES:
patent: 4194047 (1980-03-01), Christensen et al.
patent: 4268510 (1981-05-01), Boyle et al.
patent: 5442055 (1995-08-01), Iwasaki et al.
Kim et al (1987). "Stereoselective Synthesis of 1-.beta.-Methylcarbapenem", Tetrahedron Letters, 28(5):507-510.
Shih et al., Synthetic Carbapenem Antibiotics I. 1-.beta.-Methylcarbapenem, Heterocycles, vol. 21, No. 1, pp. 29-41, 1984.
Fuentes et al., Lewis Acid Mediated Condensation of Chiral Imide Anolates. A General Approach to the Synthesis of Chiral Carbapenem Precursors, Journal of the American Chemical Society, vol. 108, pp. 4675-4676, 1986.
Nagao et al., Highly Diastereoselective Alkylation onto 4-Acetoxy-2-azetidinones Employing Tin (II) Enolates of C4-Chiral 3-Acyl-1,3-thiazolidine-2-thiones, Journal of the American Chemical Society, vol. 108, pp. 4673-4675, 1986.
Moss et al., A Cysteine-Functionalized Micellar Catalyst, Tetrahedron Letters, vol. 28, No. 6, pp. 507-510, 1978.
Martel et al., 2-Picolyl thioesters; a useful synthon for the preparation of 1-.beta.-alkyl carbepenem intermediates, Can. J. Chem., vol. 66, pp. 1537-1539, 1988.
Endo, Synthesis of chiral intermediates of 1-.beta.-methylcarbapenems: vol. 65, pp. 2140-2145, 1987.
Horrom et al., The Condensation of Salicylamide with Aldehydes and Ketones, Journal of the American Chemical Society, vol. 72, pp. 721-724, 1950.
Deziel et al., Synthesis of 1-.beta.-Methylcarbapenem Key Intermediates Involving the Labile Acyl Auxiliary 4, 4-Dimethyl-1,3-Oxazolidine-2-Thione, vol. 30, No. 11, pp. 1345-1348, 1989.
Nagao et al; Diasteroselective Alkylative Discrimination of Racemic 3-Substituted 4-Acetoxyazetidin-2-ones and Its Application to the Synthesis of a Chiral Key Intermediate for Carbapenem Syntheses; Journal of Organic Chemistry; vol. 57; 1992.
Ito et al; A Novel Synthesis of the 1B-Methylcarbapenem Key Intermediate With a 4H-1,3-Dioxin Derivative, Tetrahedron Letters; vol. 30, No. 41, pp. 5631-5634; 1989.
Deziel et al; Simple and Highly Diastereoselective Synthesis of a 1B-Methycarbapenem Key Intermediate Involving Divalent Tin Enolates, Tetrahedron Letters; vol. 27, No. 47, pp. 5687-5690; 1986.
Atsuro et al; Patent Abstracts of Japan, Sumitomo Pharmaceutical Co. Ltd.; vol. 11, No. 398, (C-466); 25 Dec. 1987.
Yamato et al; Reaction of 1,2,3,4-Tetrahydroquinazolin-4-ones with Acid Anhydride. III, Chemical and Pharmaceutical Bulletin; vol. 29, No. 10, pp. 3124-3129; Oct. 1981.
Kawase; Unusal Formation of Tetrahydro-1-isoquinolones from Tetrahydroisoquinoline-1-carboxylic Acids with Carbodiimides and Mechanistic Aspects, Chemical 2 Communications, Journal of the Chemical Society; No. 19; Oct. 1990.
Vaccher et al; A Novel Rearrangement Reaction. A Single-step Conversion of Journal of Heterocyclic Chemistry; vol. 21, No. 3, pp. 1201-1204, Scheme 1, Compounds 2a-2c, May-Jun. 1984.
Yamato et al; Reaction of 1,2,3,4-Tetrahydroquinazolin-4-ones with Acid Anhydride. II Chemical & Pharmaceutical Bulletin; vol. 29, No. 10; Oct. 1981.
Mori et al; A Novel Synthesis Of Cyclic Imides And Quinolone By Use of Palladium Catalyzed Carbonylation, Heterocycles; vol. 13 pp. 329-332; 30 Dec. 1979.
Chemical Abstracts; vol. 59, No. 3; 5 Aug. 1963.
Chemical Abstracts; vol. 63, No. 1; 5 Jul. 1965.
Iwasaki Tameo
Kondo Kazuhiko
Ohmizu Hiroshi
Grumbling Matthew V.
Tanabe Seiyaku Co. Ltd.
LandOfFree
Heterocyclic alkanamide does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Heterocyclic alkanamide, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Heterocyclic alkanamide will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-203630