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US3669953A Expired / Lapsed US ⏱️ 0.0 years remaining

Megalalosamine and esters thereof and methods for their manufacture

Assignee: Merck Sharp & Dohme LLC
•
Filing: 1969-10-13
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Granted: 1972-06-13
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Expires: 1989-10-13
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Abstract

Abstract Megalalosamine and ester derivatives thereof and their pharmaceutically acceptable acid addition salts are novel macrolides exhibiting antibiotic activity. Megalalosamine is prepared by treating one of megalomicin A, megalomicin B, megalomicin C1 and megalomicin C2, or mixtures thereof with aqueous acid. Megalalosamine 2'',4''''-diacylates and megalalosamine 3,2'',4''''-triacylates are prepared by treating megalalosamine in a basic medium with an acylating reagent of a hydrocarbon carboxylic acid or a hydrocarbon sulfonic acid. Megalalosamine 3-monoacylates are prepared by subjecting a megalalosamine 3,2'',4''''-triacylate to mild hydrolysis. Mixed 3,2'',4''''-triacylate esters of megalalosamine are prepared by treating one of megalalosamine, a 3-monoacylate thereof, or a 2'', 4''''-diacylate thereof in a basic medium with an acylating reagent of a hydrocarbon carboxylic acid or a hydrocarbon sulfonic acid. 3-Tetrahydropyranyl-2'',4''''-diacylmegalalosamines are prepared by treating a megalalosamine 2'',4''''-diacylate with dihydropyran in the presence of acid.

Inventors

  • 👤 Alan K Mallams

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 12:41
CPC Classifications
C; C07; C07H; C07H17/00; C07H17/04; C07H17/08

Claims Analysis

Total Claims: 13
Claim 1
Independent Claim 69 words
A compound according to claim 1 wherein R1 is a member selected from the group consisting of tetrahydropyranyl and an acyl radical of an acid selected from the group consisting of a hydrocarbon carboxylic acid having up to eight carbon atoms and a hydrocarbon sulfonic acid having up to seven carbon atoms; and R2 is an acyl radical of a hydrocarbon carboxylic acid having up to eight carbon atoms.
Claim 2
Dependent Claim 10 words
A compound according to claim 2 wherein R1 is propionyl.
Claim 3
Dependent Claim 27 words
A compound according to claim 1 wherein R1 is an acyl radical of a hydrocarbon carboxylic acid having up to eight carbon atoms and R2 is hydrogen.
Claim 4
Dependent Claim 16 words
A compound according to claim 1 wherein R1 and R2 are hydrogen, said compound being megalalosamine.
Claim 5
Dependent Claim 17 words
A compound according to claim 1 wherein R1 and R2 are propionyl, said compound being 3,2'' ,4''''-tripropionylMegalalosamine.
Claim 6
Dependent Claim 18 words
A compound according to claim 1 wherein R1 is propionyl and R2 is hydrogen, said compound being 3-propionylmegalalosamine.
Claim 7
Dependent Claim 16 words
A compound according to claim 1 wherein R1 and R2 are isovaleryl, said compound being 3,2'',4''''-tri-isovalerylmegalalosamine.
Claim 8
Dependent Claim 18 words
A compound according to claim 1 wherein R1 is tetrahydropyranyl and R2 is benzoyl, said compound being 2'',4''''-dibenzoyl-3-tetrahydropyranylmegalalosamine.
Claim 9
Dependent Claim 18 words
A compound according to claim 1 wherein R1 is propionyl and R2 is acetyl, said compound being 2'',4''''-diacetyl-3-propionylmegalalosamine.
Claim 10
Dependent Claim 18 words
A compound according to claim 1 wherein R1 is isovaleryl and R2 is acetyl, said compound being 2'',4''''-diacetyl-3-isovalerylmegalalosamine.
Claim 11
Dependent Claim 18 words
A compound according to claim 1 wherein R1 is methanesulfonyl and R2 is acetyl, said compound being 2'',4''''-diacetyl-3-methanesulfonylmegalalosamine.
Claim 12
Dependent Claim 18 words
A compound according to claim 1 wherein R1 is methanesulfonyl and R2 is benzoyl, said compound being 2'',4''''-dibenzoyl-3-methanesulfonylmegalalosamine.
Claim 13
Dependent Claim 18 words
A compound according to claim 1 wherein R1 is acetyl and R2 is hydrogen, said compound being 3-acetylmegalalosamine.

References Cited (Backward Citations)

US3318866A Cited
US3380994A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1975-06-13 1975-12-13 1976-06-13 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1979-06-13 1979-12-13 1980-06-13 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1983-06-13 1983-12-13 1984-06-13 $7700.00 Window Closed / Lapsed

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