Claims
- 1. A compound of the formula ##STR280## wherein R.sup.1 and R.sup.2 are the same or different, and independently are methyl or methoxy, or R.sup.1 and R.sup.2 together represent --CH.dbd.CH--CH.dbd.CH--,
- R.sup.4 is (a) a phenyl, (b) a naphthyl, (c) a thienyl or (d) a furyl, each of (a), (b), (c) or (d) being unsubstituted or substituted by 1 to 5 substituents selected from the group consisting of hydroxyl, a halogen, an alkyl having 1 to 3 carbon atoms, an alkoxy having 1 to 3 carbon atoms, acetyl, phenyl, p-tolyl, m-tolyl, a pyridyl, 3-pyridlmethyl, benzoyl, methylenedioxy, trimethylene, 1-imidazolyl and 1-imidazolylmethyl,
- R.sup.5 is
- methoxy,
- hydroxymethyl,
- nitroxymethyl,
- aminocarbonyloxymethyl,
- methylaminocarbonyloxymethyl,
- ethylaminocarbonyloxymethyl,
- dimethylaminocarbonyloxymethyl,
- phenylaminocarbonyloxymethyl,
- morpholinocarbonyloxymethyl,
- piperidinocarbonyloxymethyl,
- aminocarbonyl,
- a mono- or di-alkylaminocarbonyl having 2 to 4 carbon atoms,
- benzylaminocarbonyl,
- .alpha.- or .beta.-phenethylaminocarbonyl,
- 1-(.alpha.-naphthyl)ethylaminocarbonyl,
- aminocarbonyl substituted by phenyl or naphthyl, whose phenyl or naphthyl may be further substituted by hydroxy, amino, nitro, halogen, methyl or methoxy,
- hydroxyaminocarbonyl,
- N-hydroxy-N-methylaminocarbonyl,
- N-hydroxy-N-phenylaminocarbonyl,
- an amino acid residue-carbonyl whose amino acid is one selected from the group consisting of glycine, arginine, histidine, aspartic acid, proline, phenylalanine, methionine, alanine, and leucine, or
- a cyclic aminocarbonyl, selected from the group consisting of morpholinocarbonyl, piperidinocarbonyl, piperazinocarbonyl and pyrrolidinocarbonyl, the cyclic aminocarbonyl being unsubstituted or substituted by methyl, ethyl, propyl, pyrrolidinecarbonylmethyl, 4-fluorophenylcarbonylpropyl, phenyl, naphthyl, 2-methoxyphenyl, 4-methylphenyl, 4-bromophenyl, benzyl, 2-phenylethyl, 4-fluorophenylmethyl, 4-methoxyphenylmethyl, 3,4,5-trimethoxyphenylmethyl, diphenylmethyl, aminocarbonyl, 6-(9-.beta.-D-ribofuranoside)adenyl or 4-amino-6,7-dimethoxyquinazolinyl,
- and
- n is an integer of 2 to 10,
- or the hydroquinone form of said compound.
- 2. A compound as claimed in claim 1, wherein R.sup.4 is phenyl or a phenyl having an halogen at meta or para p-position on the phenyl ring.
- 3. A compound as claimed in claim 1, wherein
- R.sup.4 is (a) a phenyl or (b) a naphthyl, each of (a) or (b) being unsubstituted or substituted by 1 to 5 substituents selected from the group consisting of hydroxyl, a halogen, an alkyl having 1 to 3 carbon atoms, an alkoxy having 1 to 3 carbon atoms, acetyl, phenyl, p-tolyl, m-tolyl, a pyridyl, 3-pyridylmethyl, benzoyl, methylenedioxy, trimethylene, 1-imidazolyl and 1-imidazolylmethyl.
- 4. A compound as claimed in claim 1, wherein
- R.sup.5 is
- aminocarbonyl,
- a mono- or di-alkylaminocarbonyl having 2 to 4 carbon atoms,
- benzylaminocarbonyl,
- .alpha.- or .beta.-phenethylaminocarbonyl,
- 1-(.alpha.-naphthyl)ethylaminocarbonyl,
- aminocarbonyl substituted by phenyl or naphthyl, whose phenyl or naphthyl may be further substituted by hydroxy, amino, nitro, halogen, methyl or methoxy,
- hydroxyaminocarbonyl,
- N-hydroxy-N-methylaminocarbonyl,
- N-hydroxy-N-phenylaminocarbonyl,
- an amino acid residue-carbonyl whose amino acid is one selected from the group consisting of glycine, arginine, histidine, aspartic acid, proline, phenylalanine methionine, alanine, and leucine, or
- a cyclic aminocarbonyl selected from a group consisting of morpholinocarbonyl, piperidinocarbonyl, piperazinocarbonyl and pyrrolidinocarbonyl, the cyclic aminocarbonyl being unsubstituted or substituted by methyl, ethyl, propyl, pyrrolidinecarbonylmethyl, 4-fluorophenylcarbonylpropyl, phenyl, naphthyl, 2-methoxyphenyl, 4-methylphenyl, 4-bromophenyl, benzyl, 2-phenylethyl, 4-fluorophenylmethyl, 4-methoxyphenylmethyl, 3,4,5-trimethoxyphenylmethyl, diphenylmethyl, aminocarbonyl, 6-(9-.beta.-D-ribofuranoside)adenyl or 4-amino-6,7-dimethoxyquinazolinyl.
- 5. A compound as claimed in claim 1, wherein
- R.sup.5 is
- methoxy,
- hydroxymethyl,
- nitroxymethyl,
- aminocarbonyloxymethyl,
- methylaminocarbonyloxymethyl,
- ethylaminocarbonyloxymethyl,
- dimethylaminocarbonyloxymethyl,
- phenylaminocarbonyloxymethyl,
- morpholinocarbonyloxymethyl, or
- piperidinocarbonyloxymethyl.
- 6. A compound as claimed in claim 1, wherein
- R.sup.4 is (a) a phenyl or (b) a naphthyl, each of (a) or (b) being unsubstituted or substituted by 1 to 5 substituents selected from the group consisting of hydroxyl, a halogen, an alkyl having 1 to 3 carbon atoms, an alkxoy having 1 to 3 carbon atoms, acetyl, phenyl, p-tolyl, m-tolyl, pyridyl, 3-pyridylmethyl, benzoyl, methylenedioxy, trimethylene, 1-imidazolyl and 1-imidazolylmethyl,
- and
- R.sup.5 is
- aminocarbonyl,
- a mono- or di-alkylaminocarbonyl having 2 to 4 carbon atoms,
- benzylaminocarbonyl,
- .alpha.- or .beta.-phenethylaminocarbonyl,
- 1-(.alpha.-naphthyl)ethylaminocarbonyl,
- aminocarbonyl substituted by phenyl or naphthyl, whose phenyl or naphthyl may be further substituted by hydroxy, amino, nitro, halogen, methyl or methoxy,
- hydroxyaminocarbonyl,
- N-hydroxy-N-methylaminocarbonyl,
- N-hydroxy-N-phenylaminocarbonyl,
- an amino acid residue-carbonyl whose amino acid is one selected from the group consisting of glycine, arginine, histidine, aspartic acid, proline, phenylalanine methionine, alanine, and leucine, or
- a cyclic aminocarbonyl selected from a group consisting of morpholinocarbonyl, piperidinocarbonyl, piperazinocarbonyl and pyrrolidinocarbonyl, the cyclic aminocarbonyl being unsubstituted or substituted by methyl, ethyl, propyl, pyrrolidinecarbonylmethyl, 4-fluorophenylcarbonylpropyl, phenyl, naphthyl, 2-methoxyphenyl, 4-methylphenyl, 4-bromophenyl, benzyl, 2-phenylethyl, 4-fluorophenylmethyl, 4-methoxyphenylmethyl, 3,4,5-trimethoxyphenylmethyl, diphenylmethyl, aminocarbonyl, 6-(9-.beta.-D-ribofuranoside)adenyl or 4-amino-6,7-dimethoxyquinazolinyl.
- 7. A compound as claimed in claim 1, wherein
- R.sup.4 is (a) a phenyl or (b) a naphthyl, each of (a) or (b) being unsubstituted or substituted by 1 to 5 substituents selected from the group consisting of hydroxyl, a halogen, an alkyl having 1 to 3 carbon atoms, an alkxoy having 1 to 3 carbon atoms, acetyl, phenyl, p-tolyl, m-tolyl, pyridyl, 3-pyridylmethyl, benzoyl, methylenedioxy, trimethylene, 1-imidazolyl and 1-imidazolylmethyl,
- and
- R.sup.5 is
- methoxy,
- hydroxymethyl,
- nitroxymethyl,
- aminocarbonyloxymethyl,
- methylaminocarbonyloxymethyl,
- ethylaminocarbonyloxymethyl,
- dimethylaminocarbonyloxymethyl,
- phenylaminocarbonyloxymethyl,
- morpholinocarbonyloxymethyl, or
- piperidinocarbonyloxymethyl.
- 8. A compound as claimed in claim 1, wherein
- R.sup.4 is a thienyl or a furyl, each of which is unsubstituted or substituted by 1 to 5 substituents selected from the group consisting of hydroxyl, a halogen, an alkyl having 1 to 3 carbon atoms, an alkoxy having 1 to 3 carbon atoms, acetyl, phenyl, p-tolyl, m-tolyl, a pyridyl, 3-pyridylmethyl, benzoyl, methylenedioxy, trimethylene, 1-imidazolyl and 1-imidazolylmethyl.
- 9. A compound as claimed in claim 1, wherein
- R.sup.4 is a thienyl or a furyl, each of which is unsubstituted or substituted by 1 to 5 substituents selected from the group consisting of hydroxyl, a halogen, an alkyl having 1 to 3 carbon atoms, an alkoxy having 1 to 3 carbon atoms, acetyl, phenyl, p-tolyl, m-tolyl, a pyridyl, 3-pyridylmethyl, benzoyl, methylenedioxy, trimethylene, 1-imidazolyl and 1-imidazolylmethyl, and
- R.sup.5 is
- aminocarbonyl,
- a mono- or di-alkylaminocarbonyl having 2 to 4 carbon atoms,
- benzylaminocarbonyl,
- .alpha.- or .beta.-phenethylaminocarbonyl,
- 1-(.alpha.-naphthyl)ethylaminocarbonyl,
- aminocarbonyl substituted by phenyl or naphthyl, whose phenyl or naphthyl may be further substituted by hydroxy, amino, nitro, halogen, methyl or
- methoxy,
- hydroxyaminocarbonyl,
- N-hydroxy-N-methylaminocarbonyl,
- N-hydroxy-N-phenylaminocarbonyl,
- an amino acid residue-carbonyl whose amino acid is one selected from the group consisting of glycine, arginine, histidine, aspartic acid, proline, phenylalanine methionine, alanine, and leucine, or
- a cyclic aminocarbonyl selected from a group consisting of morpholinocarbonyl, piperidinocarbonyl, piperazinocarbonyl and pyrrolidinocarbonyl, the cyclic aminocarbonyl being unsubstituted or substituted by methyl, ethyl, propyl, pyrrolidinecarbonylmethyl, 4-fluorophenylcarbonylpropyl, phenyl, naphthyl, 2-methoxyphenyl, 4-methylphenyl, 4-bromophenyl, benzyl, 2-phenylethyl, 4-fluorophenylmethyl, 4-methoxyphenylmethyl, 3,4,5-trimethoxyphenylmethyl, diphenylmethyl, aminocarbonyl, 6-(9-.beta.-D-ribofuranoside)adenyl or 4-amino-6,7-dimethoxyquinazolinyl.
- 10. A compound as claimed in claim 1, wherein
- R.sup.4 is a thienyl or a furyl, each of which is unsubstituted or substituted by 1 to 5 substituents selected from the group consisting of hydroxyl, a halogen, an alkyl having 1 to 3 carbon atoms, an alkoxy having 1 to 3 carbon atoms, acetyl, phenyl, p-tolyl, m-tolyl, a pyridyl, 3-pyridylmethyl, benzoyl, methylenedioxy, trimethylene, 1-imidazolyl and 1-imidazolylmethyl,
- R.sup.5 is
- methoxy,
- hydroxymethyl,
- nitroxymethyl,
- aminocarbonyloxymethyl,
- methylaminocarbonyloxymethyl,
- ethylaminocarbonyloxymethyl,
- dimethylaminocarbonyloxymethyl,
- phenylaminocarbonyloxymethyl,
- morpholinocarbonyloxymethyl, or
- piperidinocarbonyloxymethyl.
- 11. A compound as claimed in claim 1, wherein the compound is 7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptanol.
- 12. A compound as claimed in claim 1, wherein the compound is 7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptanamide.
- 13. A compound as claimed in claim 1, wherein the compound is 7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptanoglycine.
- 14. A compound as claimed in claim 1, wherein the compound is 1-[7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptanoyl] 4-(2-phenylethyl)piperadine.
- 15. A pharmaceutical composition which comprises a pharmaceutically effective amount of a compound as claimed in claim 1 or its hydroquinone form in association with a pharmaceutically acceptable carrier therefor.
Parent Case Info
This application is a division of application Ser. No. 07/001,893, filed Jan. 9, 1987, now U.S. Pat. No. 5,180,742 , which application is a continuation-in-part of application Ser. No. 823,298, filed Jan. 28, 1986, now abandoned which in turn is a continuation-in-part of application Ser. No. 760,504, filed Jul. 30, 1985, now abandoned.
US Referenced Citations (7)
Divisions (1)
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Date |
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Parent |
1893 |
Jan 1987 |
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Continuation in Parts (2)
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823298 |
Jan 1986 |
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760504 |
Jul 1985 |
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