Claims
- 1. A benzazine compound, a geometrical isomer of said benzazine compound, an optical isomer of said benzazine compound, and a pharmaceutically acceptable salt of said benzazine compound, said benzazine compound being represented by formula (I): ##STR11## wherein both R.sup.1 and R.sup.2 represent hydrogen; R.sup.3 and R.sup.4 are the same or different and each represents hydrogen, an alkyl, phenyl or a phenylalkyl, provided that one of R.sup.3 and R.sup.4 represents hydrogen, an alkyl, phenyl or a phenylalkyl and the another represents an alkyl, phenyl or a phenylalkyl when R.sup.9 represents a group of formula (a) or (c) as defined below; R.sup.5 represents hydrogen, an alkyl, or a phenylalkyl; R.sup.6 represents hydrogen, a halogen, an alkoxy, amino, nitro, --S(O).sub.l R.sup.18 (wherein R.sup.18 represents an alkyl, phenyl or a substituted phenyl and l is 0, 1 or 2), or ##STR12## (wherein R.sup.19 and R.sup.20 are the same or different and each represents hydrogen or an alkyl); both R.sup.7 and R.sup.8 represent hydrogen; X represents oxygen or sulfur; Y represents --NH--; and R.sup.9 represents a group of the formula: ##STR13## wherein R.sup.11 represents an alkyl, a phenylalkyl, or a substituted phenylalkyl, ##STR14## wherein t is 0 or 1 and R.sup.13 represents an alkyl, a phenylalkyl, or a substituted phenylalkyl, ##STR15## wherein R.sup.14 and R.sup.15 are bonded to each other to be a group which forms a heterocyclic ring in cooperation with the adjacent nitrogen atom, and v is an integer of 1 to 8, or ##STR16## wherein ring A represents 2-pyrrolidine or 4-morpholine and R.sup.16 represents hydrogen, an alkyl, an alkenyl, an alkynyl, a phenylalkyl, a substituted phenylalkyl, amino, a mono- or dialkyl-substituted amino, or an acylamino.
- 2. The compound of claim 1, wherein said compound is selected from the group consisting of 6-chloro-2,2,4-trimethyl-N-(3-quinuclidinyl)-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide, (R)-6-chloro-2,2,4-trimethyl-N-(3-quinuclidinyl)-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide, (S)-6-chloro-2,2,4-trimethyl-N-(3-quinuclidinyl)-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide, endo-6-chloro-2,2,4-trimethyl-N-(9-methyl-9-azabicyclo[3.3.1]non-3-yl)-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide, N-[(1-butyl-2pyrrolidinyl)methyl]-4-methyl-6-methylthio-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide, (S)-(-)-N-[(1-butyl-2pyrrolidinyl)methyl]-6-chloro-4-methyl-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide, 6-amino-N-[(1-butyl-2pyrrolidinyl)methyl]-4-methyl-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide, 6-chloro-4-methyl-N-[(1-butyl-2-pyrrolidinyl)methyl]-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide, (R)-(+)-6-chloro-4-methyl-N-[(1-nonyl-2-pyrrolidinyl)methyl]-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide, 6-chloro-4-methyl-N-[(1-ethyl-2-pyrrolidinyl)methyl]-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide, (S)-N-[(1-butyl-2-pyrrolidinyl)methyl]-4-methyl-6-methylthio-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide, (R)-N-[(1-butyl-2-pyrrolidinyl)-methyl]-4-methyl-6-methylthio-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide, (S)-N-[{1-(2-phenylethyl)-2-pyrrolidinyl}methyl]-4-methyl-6-nitro-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide, (R)-N-[{1-(2-phenylethyl)-2-pyrrolidinyl}methyl]-4-methyl-6-nitro-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide, (S)-N-[{1-(2-phenylethyl)-2-pyrrolidinyl}methyl]-6-amino-4-methyl-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide and (R)-N-[(1-benzyl-2-pyrrolidinyl)methyl]-4-methyl-6-methylthio-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide and pharmaceutically acceptable salts thereof.
- 3. A benzazine compound, a geometrical isomer of said benzazine compound, an optical isomer of said benzazine compound, and a pharmaceutically acceptable salt of said benzazine compound, said benzazine compound being represented by formula (II): ##STR17## wherein each symbol has the same meaning as that defined in claim 1, or a reactive derivative thereof.
- 4. A pharmaceutical composition comprising the compound of claim 1 and a pharmaceutically acceptable carrier.
- 5. The compound of claim 1, wherein both R.sup.1 and R.sup.2 represent hydrogen; one of R.sup.3 and R.sup.4 represents hydrogen, an alkyl, phenyl or a phenylalkyl and the another represents an alkyl, phenyl or a phenylalkyl; R.sup.5 represents hydrogen, an alkyl, or a phenylalkyl; R.sup.6 represents hydrogen, a halogen, an alkoxy, amino, nitro, --S(O).sub.l R.sup.18 (wherein R.sup.18 represents an alkyl, phenyl or a substituted phenyl and l is 0, 1 or 2), or ##STR18## (wherein R.sup.19 and R.sup.20 are the same or different and each represents hydrogen or an alkyl); both R.sup.7 and R.sup.8 represent hydrogen; X represents oxygen or sulfur; Y represents --NH--; and R.sup.9 represents a group of the formula: ##STR19## wherein t is 0 or 1 and R.sup.13 represents an alkyl, a phenylalkyl, or a substituted phenylalkyl.
- 6. The compound of claim 5, wherein R.sup.6 represents a halogen.
- 7. The compound of claim 5, wherein said compound is selected from the group consisting of 6-chloro-2,2,4-trimethyl-N-(3-quinuclidinyl)-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide, (R)-6-chloro-2,2,4-trimethyl-N-(3-quinucldinyl)-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide, (S)-6-chloro-2,2,4-trimethyl-N-(3-quinuclidinyl)-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide, endo-6-chloro-2,2,4-trimethyl-N-(9-methyl-9-azabicyclo[3.3.1]non-3-yl)-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide, 6-chloro-2,4-dimethyl-N-(3-quinuclidinyl)-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide, endo-6-chloro-2,2,4-trimethyl-N-(8-methyl-8-azabicyclo[3.2.1]oct-3-yl)-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide and pharmaceutically acceptable salts thereof.
- 8. A pharmaceutical composition comprising the compound of claim 5 and a pharmaceutically acceptable carrier.
- 9. The compound of claim 1, wherein both R.sup.1 and R.sup.2 represent hydrogen; R.sup.3 and R.sup.4 are the same or different and each represents hydrogen, an alkyl, phenyl or a phenylalkyl; R.sup.5 represents hydrogen, an alkyl, or a phenylalkyl; R.sup.6 represents hydrogen, a halogen, an alkoxy, amino, nitro, --S(O).sub.l R.sup.18 (wherein R.sup.18 represents an alkyl, phenyl or a substituted-phenyl and l is 0, 1 or 2) or ##STR20## (wherein R.sup.19 and R.sup.20 are the same or different and each represents hydrogen or an alkyl); both R.sup.7 and R.sup.8 represents hydrogen; X represents oxygen or sulfur; Y represents --NH--; and R.sup.9 represents a group of the formula: ##STR21## wherein R.sup.11 represents an alkyl, a phenylalkyl, or a substituted phenylalkyl, ##STR22## wherein R.sup.14 and R.sup.15 are bonded to each other to be a group which forms a heterocyclic ring in cooperation with the adjacent nitrogen atom, and v is an integer of 1 to 8, or ##STR23## wherein ring A represents 2-pyrrolidine or 4-morpholine and R.sup.16 represents hydrogen, an alkyl, an alkenyl, an alkynyl, a phenylalkyl, a substituted phenylalkyl, amino, a mono- or dialkyl-substituted amino, or an acylamino.
- 10. The compound of claim 9, wherein said compound is selected from the group consisting of N-[1-butyl-2-pyrrolidinyl)methyl]-4-methyl-6-methylthio-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide, (S)-(-)-N-[(-butyl-2-pyrrolidinyl)methyl]-6-chloro-4-methyl-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide, 6-amino-N-[(1-butyl-2-pyrrolidinyl)methyl]-4-methyl-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide, 6-chloro-4-methyl-N-[(1-butyl-2-pyrrolidinyl)-methyl]-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide, (R)-(+)-6-chloro-4-methyl-N-[(1-nonyl-2-pyrrolidinyl)methyl]-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide, 6-chloro-4-methyl-N-[(1-ethyl-2-pyrrolidinyl)methyl]-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide, (S)-N-[(1-butyl-2-pyrrolidinyl)-methyl]-4-methyl-6-methylthio-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide, (R)-N-[(1-butyl-2-pyrrolidinyl)-methyl]-4-methyl-6-methylthio-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide, (S)-N-[{1-(2-phenylethyl)-2-pyrrolidinyl}-methyl]-4-methyl-6-nitro-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide, (R)-N-[{1-(2-phenylethyl)-2-pyrrolidinyl}-methyl]-4-methyl-6-nitro-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide, (S)-N-[{1-(2-phenylethyl)-2-pyrrolidinyl}-methyl]-6-amino-4-methyl-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide and (R)-N-[(1-benzyl-2-pyrrolidinyl)methyl]-4-methyl-6-methylthio-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide and pharmaceutically acceptable salts thereof.
- 11. A pharmaceutical composition comprising the compound of claim 9, and a pharmaceutically acceptable carrier.
Priority Claims (2)
Number |
Date |
Country |
Kind |
1-171549 |
Jul 1989 |
JPX |
|
2-60663 |
Mar 1990 |
JPX |
|
Parent Case Info
This is a continuation-in-part application of Ser. No. 07/547,551 filed on Jul. 3, 1990, now abandoned.
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4778792 |
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4826839 |
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May 1989 |
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Jan 1990 |
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4933445 |
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4935511 |
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Jun 1990 |
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4937337 |
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Jun 1990 |
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Number |
Date |
Country |
0234872 |
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EPX |
0313393 |
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EPX |
2509155 |
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DEX |
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
547551 |
Jul 1990 |
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