Claims
- 1. A compound of formula I whereinR1 is R2-substituted methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, nonyl or decyl, R2-substituted 2-propenyl, 2-butenyl, 3-methyl-2-propenyl, 1-propenyl, 1-butenyl or vinyl, R2-substituted ethynyl, 1-propynyl, 2-propynyl or 1-butynyl, R2-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl, —(CH2)n-phenyl-(CH2)n-naphthyl, —(CH2)n-biphenylyl or —(CH2)n-indenyl substituted by R2 in the aryl or in the alkyl residue, or —(CH2)n-pyrazolyl, —(CH2) imidazolyl, —(CH2)n-pyrazinyl, —(CH2)n-pyridinyl, —(CH2)n-pyrimidinyl, —(CH2)n-pyridazinyl or —(CH2)n-triazinyl substituted by R2 in the hetaryl or alkyl residue, R4 is hydrogen or R2-substituted methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, nonyl or decyl, R2-substituted 2-propenyl, 2-butenyl, 3-methyl-2-propenyl, 1-propenyl, 1-butenyl or vinyl, R2-substituted ethynyl, 1-propynyl, 2-propynyl or 1-butynyl, R2-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl, —(CH2)n-phenyl-(CH2) naphthyl, —(CH2)n-biphenylyl or —(CH2)n-indenyl substituted by R2 in the aryl or in the alkyl residue, or —(CH2)n-pyrazolyl, —(CH 2)n-imidazolyl, —(CH2)n-pyrazinyl, —(CH2)n-pyridinyl, —(CH2)n-pyrimidinyl, —(CH2)n-pyridazinyl or —(CH2)- triazinyl substituted by R2 in the hetaryl or alkyl residue, R5, R6, R7 and R8 are each independently hydrogen, halogen, nitro, NHCOR11, SO2R12, C3-7-cycloalkyloxy, COR13, cyano, CF3, C1-6-alkyl, C1-4-alkoxy, or imidazolyl optionally substituted by cyano, C1-4-alkyl or —COO—C1-6-alkyl, R2 is —CO—R3 and is present once or twice, n is 0, 1, 2, 3, 4 or 5, R3 is hydroxy, C1-6-alkoxy or NR9R10, R9 and R10 are each independently hydrogen, C1-4-alkyl, or jointly with the nitrogen form a saturated 5- or 6-membered heterocycle which is piperidine, pyrrolidine, morpholine, thiomorpholine or piperazine, R11 is C1-6-alkyl or phenyl, R12 is hydrogen, C1-4-alkyl, NH2, N(C1-4-alkyl)2, R13 is hydroxy, C1-6-alkoxy, C1-6-alkyl or NR9R10, or a tautomer, optical isomer, or a racemic or enantiomeric mixture thereof, or a physiologically acceptable salt thereof, and wherein, if R1 is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, nonyl or decyl substituted by —COR3, then at least one of R5, R6, R7 or R8 is not hydrogen and at least three of R5, R6, R7 or R8 are not halogen; if R1 is —CH2—COOH, then R6 and R7 are not simultaneously CH3, R6 is not NO2 wherein R5, R7 and R8 are each hydrogen, and R7 is not NO2 where R5, R6 and R8 are each hydrogen; if R1 is —CH2—COOC2H5, then R6 is not NO2 where R5, R7 and R8 are each hydrogen, R7 is not NO2 where R5, R6 and R8 are each hydrogen; and if R1 is —COR3 substituted methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, nonyl or decyl or —(CH2)-phenyl, —(CH2)-naphthyl, —(CH2)-biphenylyl or —(CH2)-indenyl substituted by —COR3 in the aryl or in the alkyl residue and R4 is H, then at least one of R5, R6, R7 or R8 is NHCOR11, SO2R12, C3-7-cycloalkyloxy or COR13, and if R1 is —COR3-substituted methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, nonyl or decyl, then R5, R6, R7 and R8 are not imidazolyl nor NO2.
- 2. A compound of formula I whereinR1 is R2-substituted methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, nonyl or decyl, R4 is R2-substituted methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, nonyl or decyl, R2-substituted 2-propenyl, 2-butenyl, 3-methyl-2-propenyl, 1-propenyl, 1-butenyl or vinyl, R2-substituted ethynyl 1-propynyl, 2-propynyl or 1-butynyl, R2-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl, —(CH2)n-phenyl, —(CH2)n-naphthyl, —(CH2)n-biphenylyl or —(CH2)n-indenyl substituted by R2 in the aryl or in the alkyl residue, or —(CH2)n-pyrazolyl, —(CH2)n-imidazolyl, —(CH2)n-pyrazinyl, —(CH2)n-pyridinyl, —(CH2)n-pyrimidinyl, —(CH2)n-pyridazinyl or —(CH2)-triazinyl substituted in the hetaryl or alkyl residue, R5, R6, R7 and R8 are each independently hydrogen, NHCOR11, SO2R12, C3-7-cycloalkyloxy, COR13, cyano, CF3, C1-6-alkyl or C1-4-alkoxy, R2 is —CO—R3 and is present once or twice, n is 0, 1, 2, 3, 4 or 5, R3 is hydroxy, C1-6-alkoxy or NR9R10, R9 and R10 are each independently hydrogen, C1-4-alkyl, or jointly with the nitrogen form a saturated 5- or 6-membered heterocycle which is piperidine, pyrrolidine, morpholine, thiomorpholine or piperazine, R11 is C1-6-alkyl or phenyl, R12 is hydrogen, C1-4-alkyl, NH2, N(C1-4-alkyl)2, R13 is hydroxy, C1-6-alkoxy, C1-6-alkyl or NR9R10, or a tautomer, optical isomer, or a racemic or enantiomeric mixture thereof, or a physiologically acceptable salt thereof, wherein at least one of R5, R6, R7 or R8 is not hydrogen; if R1 is —CH2—COOH, then R6 and R7 are not simultaneously CH3.
- 3. A compound of formula I whereinR4 is hydrogen, R1 is R2-substituted methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, nonyl or decyl, —(CH2)n-phenyl —(CH2)n-naphthyl, —(CH2)n-biphenylyl or —(CH2)n-indenyl substituted by R2 in the aryl or in the alkyl residue, R5, R6, R7 and R8 are each selected from the group consisting of NHCOR11, SO2R12, C3-7-cycloalkyloxy, COR13, cyano or CF3, hydrogen, halogen, nitro, C1-6-alkyl, C1-4-alkoxy, or imidazolyl optionally substituted by cyano, C1-4-alkyl and —COO—C1-6-alkyl; wherein at least one of R5, R6, R7 or R8 is NHCOR11, SO2R12, C3-7-cycloalkyloxy, or COR13, R2 is —CO—R3 and is present once or twice, n is 0, 1, 2, 3, 4 or 5, R3 is hydroxy, C1-6-alkoxy or NR9R10, R9 and R10 are each independently hydrogen, C1-4-alkyl, or jointly with the nitrogen form a saturated 5- or 6-membered heterocycle which is piperidine, pyrrolidine, morpholine, thiomorpholine or piperazine, R11 is C1-6-alkyl or phenyl, R12 is hydrogen, C1-4-alkyl, NH2, N(C1-4-alkyl)2, and R13 is hydroxy, C1-6-alkoxy, C1-6-alkyl or NR9R10, or a tautomer, optical isomer, or a racemic or enantiomeric mixture thereof, or a physiologically acceptable salt thereof.
- 4. A compound of formula I whereinR4 is hydrogen, R1 R2-substituted 2-propenyl, 2-butenyl, 3-methyl-2-propenyl, 1-propenyl, 1-butenyl or vinyl, R2-substituted ethynyl, 1-propynyl, 2-propynyl or 1-butynyl, R2-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl, or —(CH2)n-pyrazolyl, —(CH2)n-imidazolyl, —(CH2)n-pyrazinyl, —(CH2)n-pyridinyl, —(CH2)n-pyrimidinyl, —(CH2)n-pyridazinyl or —(CH2)-triazinyl substituted by R2 in the hetaryl or alkyl residue, R5, R6, R7 and R8 are each independently NHCOR11, SO2R12, C3-7-cycloalkyloxy, COR13, cyano or CF3, hydrogen, halogen, nitro, C1-6-alkyl, C1-4-alkoxy, or imidazolyl optionally substituted by cyano, C1-4-alkyl or —COO—C1-6-alkyl; R2 is —CO—R3 and is present once or twice, n is 0, 1, 2, 3, 4 or 5 R3 is hydroxy, C1-6-alkoxy, or NR9R10, R9 and R10 are each independently hydrogen, C1-4-alkyl, or jointly with the nitrogen form a saturated 5- or 6-membered heterocycle which is piperidine, pyrrolidine, morpholine, thiomorpholine or piperazine, R11 is C1-6-alkyl or phenyl, R12 is hydrogen, C1-4-alkyl, NH2, N(C1-4-alkyl)2, and R13 is hydroxy, C1-6-alkoxy, C1-6-alkyl or NR9R10, or a tautomer, optical isomer, or a racemic or enantiomeric mixture thereof, or a physiologically acceptable salt thereof.
- 5. A compound selected from the group consisting of3-(6-Nitro-2,3-dioxo-1,2,3,4-tetrahydroquinoxalin-1-ylmethyl)benzoic acid methyl ester, 2-{4-(2-ethoxycarbonylbenzyl)-6-nitro-2,3-dioxo-1,2,3,4-tetrahydroquinoxalin-1-ylmethyl}benzoic acid ethyl ester, and 4-(6-nitro-2,3-dioxo-1,2,3,4-tetrahydroquinoxalin-1-yl)benzoic acid ethyl ester.
- 6. A pharmaceutical composition comprising a compound of claim 1 and a physiologically acceptable carrier.
- 7. A pharmaceutical composition comprising a compound of claim 2 and a physiologically acceptable carrier.
- 8. A pharmaceutical composition comprising a compound of claim 3 and a physiologically acceptable carrier.
- 9. A pharmaceutical composition comprising a compound of claim 4 and a physiologically acceptable carrier.
Priority Claims (2)
Number |
Date |
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41 35 871 |
Oct 1991 |
DE |
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42 24 200 |
Jul 1992 |
DE |
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CROSS-REFERENCE TO RELATED APPLICATIONS
This application is a continuation of U.S. application Ser. No. 08/462,763, filed Jun. 5, 1995, now U.S. Pat. No. 6,057,304 which is a continuation of U.S. application Ser. No. 08/208,058, filed Mar. 9, 1994, now abandoned, which is a continuation of U.S. application Ser. No. 07/966,470, filed Oct. 26, 1992, now abandoned.
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Foreign Referenced Citations (3)
Number |
Date |
Country |
315959 |
Nov 1988 |
EP |
WO 9113878 |
Sep 1991 |
WO |
9207847 |
May 1992 |
WO |
Non-Patent Literature Citations (8)
Entry |
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Epperson et al, Bioorganic & Medicinal Chemistry Letters, vol. 3, pp. 2801-2804, 1993.* |
Acheson et al., J. Chem. Soc. (C), p. 2218 (1996). |
Meldrum, Brian S., Current Science Ltd., Current Opinion in Neurology and Neurosurgery, vol. 5, 1992, pp. 508-513. |
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Continuations (3)
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09/102649 |
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08/208058 |
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07/966470 |
Oct 1992 |
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08/208058 |
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