Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1980-01-23
1981-11-03
Brown, Johnnie R.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
424180, 424181, C07H 1522
Patent
active
042987270
ABSTRACT:
3',4'-Dideoxy derivative and 1-N-((S)-.alpha.-hydroxy-.omega.-aminoalkanoyl)-3',4'-dideoxy derivative of kanamycin A are now synthetized from kanamycin A and show a wider and/or higher antibacterial activity than the parent kanamycin A so that they are useful in therapeutic treatment of infections by gram-negative and gram-positive bacteria, including drug-resistant strains thereof. The production of these new derivatives may be made by preparing a protected kanamycin A derivative having its 3'- and 4'-hydroxyl groups unprotected and having its all or substantially all other functional groups protected from the initial material, kanamycin A, sulfonylating the 3'- and 4'-hydroxyl groups, removing the 3'- and 4'-sulfonyloxy groups from the resulting 3',4'-di-sulfonic acid ester product to give a 3'-eno-kanamycin A derivative, hydrogenating the 3'-eno-kanamycin A derivative to saturate the 3',4'-unsaturated bond and to yield a protected 3',4'-dideoxykanamycin A product, followed by removal of the remainiing protective groups, and optionally further followed by 1-N-acylation of the 1-amino group of the resulting 3',4'-dideoxykanamycin A with an (S)-.alpha.-hydroxy-.omega.-aminoalkanoic acid or its reactive equivalent.
REFERENCES:
patent: Re28647 (1975-12-01), Umezawa et al.
patent: 2931798 (1960-05-01), Umezawa et al.
patent: 3781268 (1973-12-01), Kawaguchi et al.
patent: 3886139 (1975-05-01), Naito et al.
patent: 3904597 (1975-09-01), Naito et al.
patent: 3925353 (1975-12-01), Umezawa et al.
patent: 4001208 (1977-01-01), Umezawa et al.
patent: 4104372 (1978-08-01), Umezawa et al.
patent: 4107424 (1978-08-01), Umezawa et al.
patent: 4120955 (1978-10-01), Umezawa et al.
patent: 4147861 (1979-04-01), Umezawa et al.
patent: 4156078 (1979-05-01), Umezawa et al.
patent: 4169939 (1979-10-01), Umezawa et al.
patent: 4170642 (1979-10-01), Umezawa et al.
Okamoto et al., "Science", vol. 157, pp. 1559-1561, 1967.
Woo et al., "Tetrahedron Letters", No. 28, pp. 2617-2620, 1971.
Kawaguchi et al., "The Journal of Antibiotics", vol. XXV, No. 12, pp. 695-708.
Courvalin et al., "Antimicrobial Agents and Chemotherapy", Apr. 1977, pp. 619-624.
Farmdoc Abstract 46482X, Bristol Myers Co., 09/12/74.
Farmdoc Abstract 41695Y, Zaidan Hojin Biseib 09/12/75.
Tsuchiya et al., "Jour. of Antibiotics", vol. XXXII, No. 12, pp. 1351-1353, 1979.
Jikahara Tomo
Miyake Toshiaki
Tsuchiya Tsutomu
Umezawa Hamao
Umezawa Sumio
Brown Johnnie R.
Taylor, Jr. Herbert W.
Zaidan Hojin Biseibutsu Kagaku KenkyuKai
LandOfFree
3',4'-Dideoxykanamycin A and 1-N-(S)-.alpha.-hydroxy-.omega.-ami does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with 3',4'-Dideoxykanamycin A and 1-N-(S)-.alpha.-hydroxy-.omega.-ami, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and 3',4'-Dideoxykanamycin A and 1-N-(S)-.alpha.-hydroxy-.omega.-ami will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1065525