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US 4,424,230 AGranted
6-(1'-Hydroxyethyl)-3-substituted amino-1-azabicyclo-3.2.0!hept-2-en-7-one-2-carboxylic acid
AssigneeMerck & Co., Inc.
InventorsBurton G. Christensen, Ronald W. Ratcliffe
Life of this patent
Estimating the term…
Abstract
Disclosed are 6-(1'-hydroxyethyl)-3-substituted amino-1-azabicyclo3.2.0!hept-2-en-7-one-2-carboxylic acids (I): ##STR1## wherein R' and R" are independently selected from H, substituted and unsubstituted alkyl and aralkyl groups, or together form a substituted or unsubstituted cyclic group. Such compounds and their O- and carboxyl derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such compounds, pharmaceutical compositions comprising such compounds and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.
Claims4
A compound having the structural formula:
- ##STR69## and the pharmaceutically acceptable salts thereof;
- wherein:
- R.sup.3 is H, or is selected from the group consisting of:
- formyl, acetyl, propionyl, butyryl, chloroacetyl, methoxyacetyl, aminoacetyl, methoxycarbonyl, ethoxycarbonyl, methylcarbamoyl, ethylcarbamoyl, phenylthiocarbonyl, 3-aminopropionyl, 4-aminobutyryl, N-methylaminoacetyl, N,N-dimethylaminoacetyl, 3-(N,N-dimethyl)amino propionyl, guanidinoacetyl, 3-guanidinopropionyl, N.sup.3 -methylguanidinopionyl, hydroxyacetyl, 3-hydroxypropionyl, acryloyl, propynoyl, malonyl, phenoxycarbonyl, amidinoacetyl, acetamidinoacetyl, amidinopropionyl, acetamidinopropionyl, guanylureidoacetyl, guanylcarbamoyl, carboxymethylaminoacetyl, sulfoacetylaminoacetyl, phosphonoacetylaminoacetyl, N.sup.3 -dimethylaminoacetamidinopropionyl, uredocarbonyl, dimethylaminoguanylthioacetyl, 3(5-aminoimidazol-1-yl)-propionyl, 3-sydnonylacetyl, o-aminomethylbenzoyl, o-aminobenzoyl, sulfo, phosphono, ##STR70## and R' and R" are independently selected from the group consisting of hydrogen, substituted with 1-3 substituents and unsubstituted:
- alkyl and cycloalkyl having 1-10 carbon atoms, phenylalkyl and heterocyclyalkyl wherein the alkyl moiety was 1-6 carbon atoms and the heterocyclyl is selected from the group consisting of:
- ##STR71## and the cyclic group formed by the joining of R' and R" is selected from:
- --(CH.sub.2).sub.5 --
- --CH.sub.2 CH.sub.2 --O--CH.sub.2 --CH.sub.2 -- ##STR72## wherein the ring or chain substituent or substituents on R', R" or the cyclic radical formed by their joinder are selected from:
- amino, mono- and dialkylamino (each alkyl having 1-6 carbon atoms), hydroxyl, carboxyl, alkoxyl having 1-6 carbon atoms chloro, bromo, fluoro, nitro, sulfamoyl, phenyl, benzyl, and alkoxylcarbonyl having 1-3 carbon atoms in the alkoxyl moiety.
6 more elements
A compound having the structural formula:
- ##STR74## and the pharmaceutically acceptable salts thereof;
- wherein:
- the 3-substituent --NR'R" is selected from the group consisting of:
- --NH.sub.2,
- --NHCH.sub.2 CH.sub.3,
- --NH(CH.sub.2).sub.2 CH.sub.3,
- --NHCH(CH.sub.3).sub.2,
- --NHCH(CH.sub.3)CH.sub.2 CH.sub.3,
- --NHCH.sub.2 CH(CH.sub.3).sub.2,
- --NH(CH.sub.2).sub.2 CH(CH.sub.3).sub.2,
- --NH(CH.sub.2).sub.2 C(CH.sub.3).sub.3,
- --NHCH(CH.sub.3) (CH.sub.2).sub.4 CH.sub.3,
- --NHCH(CH.sub.3)CH(CH.sub.3).sub.2, ##STR75## --NHCH.sub.2 CH.sub.2 OH, --NHCH(CH.sub.2 CH.sub.3)CH.sub.2 OH,
- --NH(CH.sub.2).sub.4 CH.sub.2 OH,
- --NHCH(CH.sub.3)CH.sub.2 OH,
- --NHCH.sub.2 C(CH.sub.3).sub.2 OH,
- --NH(CH.sub.2).sub.2 CH.sub.2 OH,
- --NH(CH.sub.2).sub.3 CO.sub.2 CH.sub.2 CH.sub.3,
- --NH(CH)CH.sub.3 CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3,
- --NHCH.sub.2 CH.sub.2 OCH.sub.3,
- --NHCH.sub.2 CF.sub.3,
- --NHCH.sub.2 CH.sub.2 N(CH.sub.3).sub.2,
- --NH(CH.sub.2).sub.3 N(CH.sub.3).sub.2,
- --NHCH(CH.sub.3) (CH.sub.2).sub.3 N(C.sub.2 H.sub.5).sub.2, ##STR76## (n=1-3;
- X=H, CH.sub.3, OCH.sub.3, Cl, Br, F, NO.sub.2, OH, SO.sub.2 NH.sub.2), ##STR77## (X=OH, CH.sub.3), --NHCH.sub.2 CH(.phi.).sub.2 (.phi.=phenyl),
- --NHCH.sub.2 CH(.phi.)CH.sub.2 OH ##STR78## --NHCH.sub.3, --N(C.sub.2 H.sub.5).sub.2,
- --N(CH.sub.2 CH.sub.2 CH.sub.3).sub.2,
- --N(CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3).sub.2,
- --N(CH.sub.3) (CH.sub.2 CH.sub.3),
- --N(CH.sub.2 CH.sub.3)CH.sub.2 CH.sub.2 N(C.sub.2 H.sub.5).sub.2,
- --N(CH.sub.3) (CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3), ##STR79## --N(CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3).sub.2, --N(CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3)CH.sub.2 CH.sub.2 OH,
- --N(CH.sub.3)CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2,
- --N(CH.sub.2 CH.sub.3) (CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3),
- --N(CH.sub.2 CH.sub.3) (CH.sub.2 CH.sub.2 OH),
- --N(CH.sub.2 CH.sub.2 OH).sub.2,
- --N(CH.sub.3)CH.sub.2 .phi.
- --N(CH.sub.2 .phi.)CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2,
- --N(CH.sub.2 .phi.)CH.sub.2 CH.sub.2 OH,
- --N(CH.sub.3)CH.sub.2 CH(OH).phi.,
- --N(CH.sub.2 CH.sub.3)CH.sub.2 .phi., ##STR80##
37 more elements
Dependencies are inferred from the claim text.