US 5,668,286 AGranted

Oxazolidinone derivatives and pharmaceutical compositions containing them

AssigneePharmacia & Upjohn Company

InventorsHiroyoshi Yamada, Kiyotaka Munesada, Mikio Taniguchi

Life of this patent

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Abstract

The present invention provides agents having high antimicrobial activity for preventing and treating infectious diseases. Thus, the present invention provides novel oxazolidinone derivatives represented by chemical formula (I), or pharmaceutically acceptable salts thereof, as well as antimicrobial compositions containing said derivatives or salts thereof as active ingredients. ##STR1##

Claims5

Dependent claims

An oxazolidinone derivative represented by the general formula:

##STR61## wherein R is
(a) hydrogen atom,
(b) C.sub.1 -C.sub.8 alkyl,
(c) C.sub.3 -C.sub.6 cycloalkyl,
(d) amino,
(e) C.sub.1 -C.sub.8 alkylamino,
(f) C.sub.1 -C.sub.8 dialkylamino,
(g) C.sub.1 -C.sub.8 alkoxy, or
(h) C.sub.1 -C.sub.8 halogenoalkyl;
R.sup.1 and R.sup.3 are each and independently
(a) hydrogen atom,
(b) halogen atom,
(c) C.sub.1 -C.sub.8 alkyl,
(d) C.sub.3 -C.sub.6 cycloalkyl,
(e) --(CH.sub.2).sub.m --OR.sup.11, or
(f) --C(.dbd.O)--R.sup.41 ;
X and Y are each and independently
(a) hydrogen atom, or
(b) halogen atom;
R.sup.4 and R.sup.5 are each and independently
(a) hydrogen atom,
(b) C.sub.1 -C.sub.8 alkyl,
(c) C.sub.1 -C.sub.8 alkoxy,
(d) C.sub.1 -C.sub.8 alkylthio,
(e) --(CH.sub.2).sub.m --OR.sup.51,
(f) --O--(CH.sub.2).sub.m --OR.sup.51,
(g) --NR.sup.42 R.sup.52,
(h) --N.dbd.CH--NR.sup.44 R.sup.55,
(i) --C(.dbd.O)--NR.sup.42 R.sup.52, or
(j) --(CH.sub.2).sub.m --C(.dbd.A)--R.sup.41,
or they may combine together to form
(k) .dbd.O,
(l) .dbd.NR.sup.43,
(m) .dbd.S,
(n) .dbd.CR.sup.44 R.sup.54, or
(o) an optionally substituted, unsaturated or saturated 5- or 6-membered hetero ring having 1-3 hetero atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom;
R.sup.11 and R.sup.12 are each and independently
(a) hydrogen atom,
(b) C.sub.1 -C.sub.8 alkyl, or
(c) methoxymethyl;
R.sup.41 is
(a) hydrogen atom,
(b) --(CH.sub.2).sub.m --OH,
(c) C.sub.1 -C.sub.8 alkyl,
(d) C.sub.1 -C.sub.8 alkoxy,
(e) --O--CH.sub.2 --O--C(.dbd.O)--R.sup.11, or
(f) --(CH.sub.2).sub.m --C(.dbd.O)--OR.sup.11 ;
R.sup.42 and R.sup.52 are each and independently
(a) hydrogen atom,
(b) --(CH.sub.2).sub.m --OR.sup.11,
(c) C.sub.1 -C.sub.8 alkyl,
(d) --C(.dbd.O)--R.sup.41,
(e) --C(.dbd.O)--NR.sup.11 R.sup.12,
(f) --(CH.sub.2).sub.p -phenyl,
(g) thiazol-2-yl,
or they may combine together to form a pyrrolidino group, a piperidino group, a piperazino group, a morpholino group, or a thiomorpholino group, each of which may be substituted by C.sub.1 -C.sub.8 alkyl or --(CH.sub.2).sub.m --OH;
R.sup.43 is
(a) hydrogen atom,
(b) --OR.sup.51,
(c) C.sub.1 -C.sub.8 alkyl,
(d) C.sub.1 -C.sub.8 alkoxy,
(e) --(CH.sub.2).sub.p -phenyl,
(f) --NR.sup.42 R.sup.52,
(g) --NH--C(.dbd.NH)--NH.sub.2,
(h) [1,2,4]triazol-4-yl, or
(i) cyano;
R.sup.44 and R.sup.54 are each and independently
(a) hydrogen atom,
(b) C.sub.1 -C.sub.8 alkyl,
(c) --C(.dbd.O)--R.sup.41, or
(d) --(CH.sub.2).sub.p -phenyl;
R.sup.51 is
(a) hydrogen atom,
(b) C.sub.1 -C.sub.8 alkyl,
(c) C.sub.1 -C.sub.8 alkyl substituted by one or more hydroxy,
(d) C.sub.2 -C.sub.8 alkenyl,
(e) C.sub.1 -C.sub.8 halogenoalkyl,
(f) --(CH.sub.2).sub.m --OR.sup.11,
(g) --(CH.sub.2).sub.m --C(.dbd.O)--R.sup.41,
(h) --C(.dbd.O)--(CH.sub.2).sub.m --OR.sup.44, or
(i) tosyl;
A is
(a) oxygen atom, or
(b) ethyleneketal;
.sup.... is a double bond or a single bond;
m's are each and independently 0, 1 or 2;
n is 0 or 1;
p's are each and independently 1, 2, 3 or 4;
and C.sub.1 -C.sub.8 alkyl, in each of the above definitions, may be each and independently substituted by one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, C.sub.1 -C.sub.8 alkoxy group, C.sub.1 -C.sub.8 acyloxy group, an amino group, C.sub.1 -C.sub.8 alkylamino group, C.sub.1 -C.sub.8 dialkylamino group, --CN group and a carboxyl group,
or a pharmaceutically acceptable salt thereof.

87 more elements

Dependencies are inferred from the claim text.

Facts

Application: 08/714,117Filed 9 Sep 1996
Priority: JP 6-04394915 Mar 1994
Granted: 16 Sep 1997
Term ends: Not estimatedThe source records don’t support an estimate.

Classification6 codes

C07D 413/10
Containing two hetero rings: linked by a carbon chain containing aromatic rings
C07D 263/38
One oxygen atom: attached in position 2
C07D 413/14
Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms:…
C07D 417/14
Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms,…

Family

No related US applications are recorded in the indexed filing history.

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Abstract

An oxazolidinone derivative represented by the general formula:

##STR61## wherein R is
(a) hydrogen atom,
(b) C.sub.1 -C.sub.8 alkyl,
(c) C.sub.3 -C.sub.6 cycloalkyl,
(d) amino,
(e) C.sub.1 -C.sub.8 alkylamino,
(f) C.sub.1 -C.sub.8 dialkylamino,
(g) C.sub.1 -C.sub.8 alkoxy, or
(h) C.sub.1 -C.sub.8 halogenoalkyl;
R.sup.1 and R.sup.3 are each and independently
(a) hydrogen atom,
(b) halogen atom,
(c) C.sub.1 -C.sub.8 alkyl,
(d) C.sub.3 -C.sub.6 cycloalkyl,
(e) --(CH.sub.2).sub.m --OR.sup.11, or
(f) --C(.dbd.O)--R.sup.41 ;
X and Y are each and independently
(a) hydrogen atom, or
(b) halogen atom;
R.sup.4 and R.sup.5 are each and independently
(a) hydrogen atom,
(b) C.sub.1 -C.sub.8 alkyl,
(c) C.sub.1 -C.sub.8 alkoxy,
(d) C.sub.1 -C.sub.8 alkylthio,
(e) --(CH.sub.2).sub.m --OR.sup.51,
(f) --O--(CH.sub.2).sub.m --OR.sup.51,
(g) --NR.sup.42 R.sup.52,
(h) --N.dbd.CH--NR.sup.44 R.sup.55,
(i) --C(.dbd.O)--NR.sup.42 R.sup.52, or
(j) --(CH.sub.2).sub.m --C(.dbd.A)--R.sup.41,
or they may combine together to form
(k) .dbd.O,
(l) .dbd.NR.sup.43,
(m) .dbd.S,
(n) .dbd.CR.sup.44 R.sup.54, or
(o) an optionally substituted, unsaturated or saturated 5- or 6-membered hetero ring having 1-3 hetero atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom;
R.sup.11 and R.sup.12 are each and independently
(a) hydrogen atom,
(b) C.sub.1 -C.sub.8 alkyl, or
(c) methoxymethyl;
R.sup.41 is
(a) hydrogen atom,
(b) --(CH.sub.2).sub.m --OH,
(c) C.sub.1 -C.sub.8 alkyl,
(d) C.sub.1 -C.sub.8 alkoxy,
(e) --O--CH.sub.2 --O--C(.dbd.O)--R.sup.11, or
(f) --(CH.sub.2).sub.m --C(.dbd.O)--OR.sup.11 ;
R.sup.42 and R.sup.52 are each and independently
(a) hydrogen atom,
(b) --(CH.sub.2).sub.m --OR.sup.11,
(c) C.sub.1 -C.sub.8 alkyl,
(d) --C(.dbd.O)--R.sup.41,
(e) --C(.dbd.O)--NR.sup.11 R.sup.12,
(f) --(CH.sub.2).sub.p -phenyl,
(g) thiazol-2-yl,
or they may combine together to form a pyrrolidino group, a piperidino group, a piperazino group, a morpholino group, or a thiomorpholino group, each of which may be substituted by C.sub.1 -C.sub.8 alkyl or --(CH.sub.2).sub.m --OH;
R.sup.43 is
(a) hydrogen atom,
(b) --OR.sup.51,
(c) C.sub.1 -C.sub.8 alkyl,
(d) C.sub.1 -C.sub.8 alkoxy,
(e) --(CH.sub.2).sub.p -phenyl,
(f) --NR.sup.42 R.sup.52,
(g) --NH--C(.dbd.NH)--NH.sub.2,
(h) [1,2,4]triazol-4-yl, or
(i) cyano;
R.sup.44 and R.sup.54 are each and independently
(a) hydrogen atom,
(b) C.sub.1 -C.sub.8 alkyl,
(c) --C(.dbd.O)--R.sup.41, or
(d) --(CH.sub.2).sub.p -phenyl;
R.sup.51 is
(a) hydrogen atom,
(b) C.sub.1 -C.sub.8 alkyl,
(c) C.sub.1 -C.sub.8 alkyl substituted by one or more hydroxy,
(d) C.sub.2 -C.sub.8 alkenyl,
(e) C.sub.1 -C.sub.8 halogenoalkyl,
(f) --(CH.sub.2).sub.m --OR.sup.11,
(g) --(CH.sub.2).sub.m --C(.dbd.O)--R.sup.41,
(h) --C(.dbd.O)--(CH.sub.2).sub.m --OR.sup.44, or
(i) tosyl;
A is
(a) oxygen atom, or
(b) ethyleneketal;
.sup.... is a double bond or a single bond;
m's are each and independently 0, 1 or 2;
n is 0 or 1;
p's are each and independently 1, 2, 3 or 4;
and C.sub.1 -C.sub.8 alkyl, in each of the above definitions, may be each and independently substituted by one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, C.sub.1 -C.sub.8 alkoxy group, C.sub.1 -C.sub.8 acyloxy group, an amino group, C.sub.1 -C.sub.8 alkylamino group, C.sub.1 -C.sub.8 dialkylamino group, --CN group and a carboxyl group,
or a pharmaceutically acceptable salt thereof.

87 more elements

Facts

Application

08/714,117Filed 9 Sep 1996

Priority

JP 6-04394915 Mar 1994

Granted

16 Sep 1997

Term ends

Not estimatedThe source records don’t support an estimate.

Classification6 codes

C07D 413/10
Containing two hetero rings: linked by a carbon chain containing aromatic rings
C07D 263/38
One oxygen atom: attached in position 2
C07D 413/14
Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms:…
C07D 417/14
Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms,…