5"-Amino-3',5"-dideoxybutirosin A and derivatives
First Claim
1. A member of the class consisting of O-2,6-diamino-2,3,6-trideoxy-α
- -D-ribo-hexopyranosyl-(1→
4)-O-[5-amino-5-deoxy-β
-D-xylofuranosyl-(1→
5)]-N1 -[(S)-4-amino-2-hydroxy-1-oxobutyl]-2-deoxystreptamine and pharmaceutically acceptable acid addition salts thereof.
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Abstract
O-2,6-diamino-2,3,6-trideoxy-α-D-ribo-hexo-pyranosyl-(1→4)-O-[5-amino-5-deoxy-β-D-xylofuranosyl-(1→5)]-N1 -[(S)-4-amino-2-hydroxy-1-oxobutyl]-2-deoxystreptamine), also named 5"-amino-3'"'"',5"-dideoxybutirosin A and acid addition salts of said compounds. These compounds exhibit a wide spectrum of antibacterial activity.
The above compounds can be produced from O-2,6-dideoxy-2,6-bis(Z-amino)-α-D-glucopyranosyl-(1→4)-O-[2,3-di-O-acetyl-5-deoxy-5-(Z-amino)-β-D-xylofuranosyl-(1→ 5)]-6-O-acetyl-N1 -[(S)-2-acetyloxy-1-oxo-4-(Z-amino)butyl]-2-deoxy-N.sup. 3 -streptamine, also named protected 5"-amino-deoxybutirosin A by treating said compound with trifluoromethanesulfonic anhydride and pyridine to yield the 3'"'"'-O-(trifluoromethanesulfonyl) compound. The product is reacted with the sodium salt of an arylmercaptan and the resulting 3'"'"'-arylthio compound is purified and treated with ammonia, thus deprotecting the four hydroxy groups. Lastly, the five amino groups are deprotected and the arylthio group is removed by a reductive cleavage.
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2 Claims
-
1. A member of the class consisting of O-2,6-diamino-2,3,6-trideoxy-α
- -D-ribo-hexopyranosyl-(1→
4)-O-[5-amino-5-deoxy-β
-D-xylofuranosyl-(1→
5)]-N1 -[(S)-4-amino-2-hydroxy-1-oxobutyl]-2-deoxystreptamine and pharmaceutically acceptable acid addition salts thereof. - View Dependent Claims (2)
- -D-ribo-hexopyranosyl-(1→
Specification
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- Resources
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Current AssigneeParke Davis & Company Limited (Pfizer Inc.)
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Original AssigneeParke Davis & Company Limited (Pfizer Inc.)
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InventorsHaskell, Theodore Herbert, Kee Woo, Peter Wing
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Primary Examiner(s)Brown, Johnnie R.
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Application NumberUS05/569,129Time in Patent Office460 DaysField of Search260/210 AB, 260/210 KUS Class Current536/13.5CPC Class CodesC07H 15/23 with only two saccharide ra...Y02P 20/55 Design of synthesis routes,...
