Claims
- 1. A tricyclic-fused 5-member [6,5,5] ring oxazolidinone of formula (5)
- where
- (I) R.sub.1 is
- --H,
- C.sub.1 -C.sub.12 alkyl optionally substituted with 1-3 Cl,
- C.sub.3 -C.sub.12 cycloalkyl,
- C.sub.5 -C.sub.12 alkenyl containing one double bond,
- -.phi. optionally substituted with 1-3 --OH, --OCH.sub.3, --OC.sub.2 H.sub.5, --NO.sub.2, --F, --Cl, --Br, --COOH and --SO.sub.3 H, --N(R.sub.1-1)(R.sub.1-2) where R.sub.1-1 and R.sub.1-2 are the same or different and are --H, C.sub.1 -C.sub.2 alkyl,
- furanyl,
- tetrahydrofuranyl,
- 2-thiophene,
- pyrrolidinyl,
- pyridinyl,
- --O--R.sub.1-3 where R.sub.1-3 is C.sub.1 -C.sub.4 alkyl,
- --NH.sub.2,
- --NHR.sub.1-4 where R.sub.1-4 is C.sub.1 -C.sub.3 alkyl or -.phi.,
- --NR.sub.1-4 R.sub.1-5 where R.sub.1-5 is C.sub.1 -C.sub.3 alkyl and R.sub.1-4 is as defined above, and where R.sub.1-4 and R.sub.1-5 can be taken together with the attached nitrogen atom to form morpholin-4-yl
- --CH.sub.2 --OH,
- --CH.sub.2 --OR.sub.1-6 where R.sub.1-6 is C.sub.1 -C.sub.4 alkyl or --CO--R.sub.1-7 is C.sub.1 -C.sub.4 alkyl or -.phi.;
- (II) R.sub.2 and R.sub.4 are the same or different and are
- --H,
- --OH,
- --F, --Cl, --Br, --I,
- --O--CO--R.sub.2-1 where R.sub.2-1 is C.sub.1 -C.sub.3 alkyl or -.phi.,
- (III) R.sub.3 is
- --H, --F, --Cl, --Br, --I, --O--CH.sub.3, --O--C.sub.2 H.sub.5,
- --CO--R.sub.3-1 where R.sub.3-1 is C.sub.1 -C.sub.4 alkyl optionally substituted with 1 or 2 --F or --Cl, or 1 --OH,
- --CO--CH.sub.2 --O--CH.sub.2 --.phi.,
- --CO--CH.sub.2 --O--R.sub.3-2 where R.sub.3-2 is C.sub.1 -C.sub.2 alkyl or -.phi.,
- --CO--CH.sub.2 --N.sub.3,
- --CO--CH.sub.2 --NH--CO--R.sub.3-3 where R.sub.3-3 is C.sub.1 -C.sub.2 alkyl or -.phi.,
- --C(CH.sub.3).dbd.N--OH,
- --C(CH.sub.3).dbd.N--O--R.sub.3-4 where R.sub.3-4 is C.sub.1 -C.sub.2 alkyl
- --CO--CH.sub.2 --NR.sub.3-5 R.sub.3-6 where R.sub.3-5 is --H, --CH.sub.3, --C.sub.2 H.sub.5 or -.phi. and where R.sub.3-6 is --H, --CH.sub.3 or --C.sub.2 H.sub.5,
- --SO.sub.2 --CH.sub.3,
- --SO.sub.2 -.phi.,
- --SO--CH.sub.3,
- --SO--.phi.,
- --SO.sub.2 --NH.sub.2,
- --S--R.sub.3-7 where R.sub.3-7 is --H, --CH.sub.3, --C.sub.2 H.sub.5 or -.phi.,
- --CO--CH.sub.2 --O--CO--R.sub.3-8 where R.sub.3-8 is C.sub.1 -C.sub.6 alkyl or -.phi.,
- -.phi. optionally substituted by
- --CN,
- --C.tbd.CH, --C.tbd.C--CH.sub.3, --C.tbd.C--CH.sub.2 --OH,
- --N.sub.3, --NO.sub.2,
- --O--[C.sub.1 -C.sub.4 alkyl],
- --COOH, --SO.sub.2 --OH,
- --F, --Cl, --Br, --I, --OH,
- --NH.sub.2, --N(R.sub.3-9)(R.sub.3-10) where R.sub.3-9 and R.sub.3-10 are the same or different and are selected from the group consisting of --H, C.sub.1 -C.sub.3 alkyl or -.phi.,
- 1-pyrrolidyl,
- --CO--[C.sub.1 -C.sub.4 alkyl], --CO--CH.sub.2 --OH, --CO--CH.sub.2 --N.sub.3,
- --CHOH--[C.sub.1 -C.sub.4 alkyl], --CH.sub.2 --OH,
- --CH.sub.2 --NH.sub.2, --CH.sub.2 --N(R.sub.3-9)(R.sub.3-10) where R.sub.3-9 and R.sub.3-10 are as defined above,
- --CH.sub.2 --N.sub.3,
- --CH.sub.2 --NH--CO--R.sub.3-9 where R.sub.3-9 is as defined above,
- --S--[C.sub.1 -C.sub.4 alkyl], --SO--[C.sub.1 -C.sub.4 alkyl], --SO.sub.2 --[C.sub.1 -C.sub.4 alkyl],
- --(CH.sub.3).dbd.N--OH, --(CH.sub.3).dbd.N--O--[C.sub.1 -C.sub.4 alkyl],
- --NH--COO--[C.sub.1 -C.sub.4 alkyl], --NH--SO.sub.2 --[C.sub.1 -C.sub.4 alkyl],
- --NH--CO--[C.sub.1 -C.sub.4 alkyl], --NH--CO--.phi.,
- --S--CN,
- --.phi. optionally substituted with 1 or 2 --F, --Cl, --OH,
- --CO--N(R.sub.3-9)(R.sub.3-10) where R.sub.3-9 and R.sub.3-10 are as defined above,
- C.sub.1 -C.sub.12 alkyl, C.sub.2 -C.sub.12 alkenyl containing 1, 2 or 3 double bonds,
- with the proviso that at least one of R.sub.2, R.sub.3 and R.sub.4 is --H,
- (IVA) R.sub.7 is R.sub.7-1 :R.sub.7-2 where one of R.sub.7-1 and R.sub.7-2 is taken with R.sub.8 to form a second bond between the carbon atoms to which they are attached and the other of R.sub.7-1 and R.sub.7-2 is --H, C.sub.1 -C.sub.3 alkyl, --Cl, --Br, --I,
- (IVB) R.sub.8 is --H and R.sub.7 is R.sub.7-3 :R.sub.7-4 where R.sub.7-3 and R.sub.7-4 are each --H or --CH.sub.3,
- (IVC) R.sub.8 is --H and R.sub.7 is --CO--,
- (IVD) R.sub.8 is --H and R.sub.7 is R.sub.7-5 :R.sub.7-6 where one R.sub.7-5 and R.sub.7-6 is --OH and the other of R.sub.7-5 and R.sub.7-6 is --H or --CH.sub.3, and pharmaceutically acceptable salts thereof.
- 2. A tricyclic-fused 5-member [6,5,5] ring oxazolidinone (5) according to claim 1 where R.sub.1 is selected from the group consisting of --H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, --OCH.sub.3 and --CHCl.sub.2.
- 3. A tricyclic-fused 5-member [6,5,5] ring oxazolidinone (5) according to claim 1 where R.sub.2 is --H.
- 4. A tricyclic-fused 5-member [6,5,5] ring oxazolidinone (5) according to claim 1 where R.sub.4 is --H.
- 5. A tricyclic-fused 5-member [6,5,5] ring oxazolidinone (5) according to claim 1 where R.sub.3 is --H, --CO--CH.sub.3, --CO--CH.sub.2 --Cl, --CO--CH.sub.2 --OH, --CO--CHF.sub.2 and --CO--CH.sub.2 --N.sub.3.
- 6. A tricyclic-fused 5-member [6,5,5] ring oxazolidinone (5) according to claim 1 where R.sub.7 is --H:--H or --CH.sub.3 :--CH.sub.3.
- 7. A tricyclic-fused 5-member [6,5,5] ring oxazolidinone (5) according to claim 1 where R.sub.8 is --H.
- 8. A tricyclic-fused 5-member [6,5,5] ring oxazolidinone (5) according to claim 1 which is
- (1S,9aS) N-[(9,9a-dihydro-3-oxo-1H,3H-oxazolo[3,4-a]indol-1-yl)methyl]acetamide,
- (1S,9aS) N-[(7-acetyl-9,9a-dihydro-3-oxo-1H,3H-oxazolo[3,4-a]indol-1-yl)methyl]acetamide,
- (1S,9aS)N-[7-(4-cyanophenyl)-9,9a-dihydro-3-oxo-1H,3H-oxazolo[3,4-a]indol-1-yl)methyl]acetamide,
- (1S,9aS)N-[7-(3-cyanophenyl)-9,9a-dihydro-3-oxo-1H,3H-oxazolo[3,4-a]indol-1-yl)methyl]acetamide,
- (1S, 9aS) N-[7-(4-methylsulphonylphenyl)-9,9a-dihydro-3-oxo-1H,3H-oxazolo[3,4-a]indol-1-yl)methyl]acetamide,
- (1S, 9aS) N-[7-(4-hydroxyethylphenyl)-9,9a-dihydro-3-oxo-1H,3H-oxazolo[3,4-a]indol-1-yl)methyl]acetamide,
- (1S,9aS) N-[(7-chloroacetyl-9,9a-dihydro-3-oxo-1H,3H-oxazolo[3,4-a]indol-1-yl)methyl]acetamide,
- (1S,9aS) N-[(7-azidoacetyl-9,9a-dihydro-3-oxo-1H,3H-oxazolo[3,4-a]indol-1-yl)methyl]acetamide.
CROSS REFERENCE TO RELATED APPLICATIONS
The present application is the national phase of PCT/US90/06220, filed Nov. 2, 1990, which is a continuation-in-part of Ser. No. 07/553,795, filed Jul. 13, 1990, now abandoned, which is a continuation-in-part of Ser. No. 07/438,759, filed Nov. 17, 1989, now abandoned.
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Continuation in Parts (2)
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Number |
Date |
Country |
Parent |
553795 |
Jul 1990 |
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Parent |
438759 |
Nov 1989 |
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