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US4048431A Expired / Lapsed US ⏱️ 0.0 years remaining

Alkylated derivatives of antibiotic BM123γ

Assignee: Wyeth Holdings LLC
•
Filing: 1975-11-10
•
Granted: 1977-09-13
•
Expires: 1995-11-10
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Abstract

Abstract This disclosure describes a novel series of potent antibacterial agents derived by reductive alkylation of antibiotic BM123γ with certain classes of aldehydes and ketones.

Inventors

  • 👤 Joseph John Hlavka
  • 👤 Panayota Bitha

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-07 00:35
CPC Classifications
C; C07; C07H; C07H15/00; C07H15/20; C07H15/203; Y; Y10; Y10S; Y10S435/00; Y10S435/803; Y10S435/8215; Y10S435/822; Y10S435/872

Claims Analysis

Total Claims: 38
Claim 1
Independent Claim 78 words
A compound selected from the group consisting of those of the formulae: ##STR6## wherein R is a moiety selected from the group consisting of those of the formulae: ##STR7## R 1 is selected from the group consisting of hydrogen, lower alkyl, halo substituted lower alkyl, lower alkenyl, phenyl, acetamidophenyl, nitrophenyl, mercaptophenyl, anisyl, tolyl, phenyl lower alkyl, 2-furyl, methyl substituted 2-furyl, 2thienyl, methyl substituted 2-thienyl, 2-pyrryl, methyl substituted 2-pyrryl, 2-pyridyl and 2-quinolyl; and the pharmacologically acceptable acid-addition salts thereof.
Claim 2
Dependent Claim 78 words
A compound selected from the group consisting of those of the formulae: ##STR6## wherein R is a moiety selected from the group consisting of those of the formulae: ##STR7## R 1 is selected from the group consisting of hydrogen, lower alkyl, halo substituted lower alkyl, lower alkenyl, phenyl, acetamidophenyl, nitrophenyl, mercaptophenyl, anisyl, tolyl, phenyl lower alkyl, 2-furyl, methyl substituted 2-furyl, 2thienyl, methyl substituted 2-thienyl, 2-pyrryl, methyl substituted 2-pyrryl, 2-pyridyl and 2-quinolyl; and the pharmacologically acceptable acid-addition salts thereof.
Claim 3
Dependent Claim 34 words
A mixture consisting essentially of a compound according to claim 1, formula (I) thereof, wherein R is moiety (V) and a compound according to claim 1, formula (I) thereof, wherein R is moiety (VI).
Claim 4
Dependent Claim 34 words
A mxiture consisting essentially of a compound according to claim 1, formula (II) thereof, wherein R is moiety (V) and a compound according to claim 1, formula (II) thereof, wherein R is moiety (VI).
Claim 5
Dependent Claim 34 words
A mixture consisting essentially of a compound according to claim 1, formula (III) thereof, wherein R is moiety (V) and a compound according to claim 1, formula (III) thereof, wherein R is moiety (VI).
Claim 6
Dependent Claim 34 words
A mixture consisting essentially of a compound according to claim 1, formula (IV) thereof, wherein R is moiety (V) and a compound according to claim 1, formula (IV) thereof, wherein R is moiety (VI).
Claim 7
Dependent Claim 12 words
The mixture in accordance with claim 2 wherein R 1 is hydrogen.
Claim 8
Dependent Claim 12 words
The mixture in accordance with claim 2 wherein R 1 is methyl.
Claim 9
Dependent Claim 12 words
The mixture in accordance with claim 2 wherein R 1 is benzyl.
Claim 10
Dependent Claim 12 words
The mixture in accordance with claim 2 wherein R 1 is 1,1-dimethylpropyl.
Claim 11
Dependent Claim 12 words
The mixture in accordance with claim 2 wherein R 1 is trans-1-methylpropen-1-yl.
Claim 12
Dependent Claim 12 words
The mixture in accordance with claim 3 wherein R 1 is hydrogen.
Claim 13
Dependent Claim 12 words
The mixture in accordance with claim 3 wherein R 1 is methyl.
Claim 14
Dependent Claim 12 words
The mixture in accordance with claim 4 wherein R 1 is hydrogen.
Claim 15
Dependent Claim 12 words
The mixture in accordance with claim 4 wherein R 1 is methyl.
Claim 16
Dependent Claim 12 words
The mixture in accordance with claim 5 wherein R 1 is hydrogen.
Claim 17
Dependent Claim 12 words
The mixture in accordance with claim 5 wherein R 1 is methyl.
Claim 18
Dependent Claim 140 words
A compound selected from the group consisting of those of the formula: ##STR8## wherein R is a moiety selected from the group consisting of those of the formulae: ##STR9## R 2 is selected from the group conisting of lower alkyl, halo substituted lower alkyl and phenyl lower alkyl; R 3 is selected from the group consisting of lower alkyl, halo substituted lower alkyl, lower alkenyl, lower cycloalkyl, phenyl, acetamidophenyl, nitrophenyl, mercaptophenyl, anisyl, tolyl, phenyl lower alkyl, acetamidophenyl lower alkyl, nitrophenyl lower alkyl, mercaptophenyl lower alkyl, anisyl lower alkyl and tolyl lower alkyl; and R 2 and R 3 taken together with the associated methylidyne group is cyclopentyl, mono-lower alkyl substituted cyclopentyl, di-lower alkyl substituted cyclopentyl, tri-lower alkyl substituted cyclopentyl, cyclohexyl, mono-lower alkyl substituted cyclohexyl, di-lower alkyl substituted cyclohexyl or tri-lower alkyl substituted cyclohexyl; and the pharmacologically acceptable acid-addition salts thereof.
Claim 19
Dependent Claim 140 words
A compound selected from the group consisting of those of the formula: ##STR8## wherein R is a moiety selected from the group consisting of those of the formulae: ##STR9## R 2 is selected from the group conisting of lower alkyl, halo substituted lower alkyl and phenyl lower alkyl; R 3 is selected from the group consisting of lower alkyl, halo substituted lower alkyl, lower alkenyl, lower cycloalkyl, phenyl, acetamidophenyl, nitrophenyl, mercaptophenyl, anisyl, tolyl, phenyl lower alkyl, acetamidophenyl lower alkyl, nitrophenyl lower alkyl, mercaptophenyl lower alkyl, anisyl lower alkyl and tolyl lower alkyl; and R 2 and R 3 taken together with the associated methylidyne group is cyclopentyl, mono-lower alkyl substituted cyclopentyl, di-lower alkyl substituted cyclopentyl, tri-lower alkyl substituted cyclopentyl, cyclohexyl, mono-lower alkyl substituted cyclohexyl, di-lower alkyl substituted cyclohexyl or tri-lower alkyl substituted cyclohexyl; and the pharmacologically acceptable acid-addition salts thereof.
Claim 20
Dependent Claim 28 words
A mixture consisting essentially of a compound according to claim 17 wherein R is moiety (A) and a compound according to claim 17 wherein R is moiety (B).
Claim 21
Dependent Claim 20 words
The compound according to claim 17 wherein R is moiety (A), R 2 is methyl, and R 3 is methyl.
Claim 22
Dependent Claim 20 words
The compound according to claim 17 wherein R is moiety (B), R 2 is methyl, and R 3 is methyl.
Claim 23
Dependent Claim 17 words
The mixture in accordance with claim 18 wherein R 2 is methyl and R 3 is methyl.
Claim 24
Dependent Claim 20 words
The compound according to claim 17 wherein R is moiety (A), R 2 is ethyl, and R 3 is methyl.
Claim 25
Dependent Claim 20 words
The compound according to claim 17 wherein R is moiety (B), R 2 is ethyl, and R 3 is methyl.
Claim 26
Dependent Claim 17 words
The mixture in accordance with claim 18 wherein R 2 is ethyl and R 3 is methyl.
Claim 27
Dependent Claim 20 words
The compound according to claim 17 wherein R is moiety (A), R 2 is ethyl, and R 3 is ethyl.
Claim 28
Dependent Claim 20 words
The compound according to claim 17 wherein R is moiety (B) R 2 is ethyl, and R 3 is ethyl.
Claim 29
Dependent Claim 17 words
The mixture in accordance with claim 18, wherein R 2 is ethyl and R 3 is ethyl.
Claim 30
Dependent Claim 17 words
The mixture in accordance with claim 18 wherein R 2 is methyl and R 3 is n-propyl.
Claim 31
Dependent Claim 17 words
The mixture in accordance with claim 18 wherein R 2 is methyl and R 3 is benzyl.
Claim 32
Dependent Claim 17 words
The mixture in accordance with claim 18 wherein R 2 is methyl and R 3 is 2-methylpropyl.
Claim 33
Dependent Claim 17 words
The mixture in accordance with claim 18 wherein R 2 is methyl and R 3 is isopropyl.
Claim 34
Dependent Claim 17 words
The mixture in accordance with claim 18 wherein R 2 is methyl and R 3 is 2,2-dimethylpropyl.
Claim 35
Dependent Claim 17 words
The mixture in accordance with claim 18 wherein R 2 is ethyl and R 3 is butyl.
Claim 36
Dependent Claim 17 words
The mixture in accordance with claim 18 wherein R 2 is methyl and R 3 is 1-methylpropyl.
Claim 37
Dependent Claim 17 words
The mixture in accordance with claim 18 wherein R 2 is methyl and R 3 is 2-phenylethyl.
Claim 38
Dependent Claim 17 words
The mixture in accordance with claim 18 wherein R 2 is methyl and R 3 is 3-methylbutyl.

References Cited (Backward Citations)

GB1033394A Cited
US3350387A Cited
US3784541A Cited
US3978041A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-09-12 1981-03-14 1981-09-13 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-09-12 1985-03-14 1985-09-13 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-09-12 1989-03-14 1989-09-13 $7700.00 Window Closed / Lapsed

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