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Details for Patent: 5,559,230

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Details for Patent: 5,559,230

Title: Benzoheterocyclic compounds
Abstract:Novel benzoheterocyclic compounds of the formula: ##STR1## wherein R.sup.1 is H, halogen, alkyl, optionally substituted amino, alkoxy; R.sup.2 is H, halogen, alkoxy, phenyialkoxy, OH, alkyl, optionally substituted amino, carbamoyl-alkoxy, optionally substituted amino-alkoxy, optionally substituted benzoyloxy; R.sup.3 is a group: --NR.sup.4 R.sup.5 or --CO--NR.sup.11 R.sup.12 ; R.sup.4 is H, optionally substituted benzoyl, alkyl; R.sup.5 is a group: ##STR2## [R.sup.16 is halogen, optionally substituted alkyl, OH, alkoxy, alkanoyloxy, alkylthio, alkanoyl, carboxy, alkoxycarbonyl, CN, NO.sub.2, optionally substituted amino, phenyl, cycloalkyl, etc., or a group: --O--A--NR.sup.6 R.sup.7 ; m is 0 to 3], phenyl-alkoxycarbonyl, alkanoyl, phenylalkanoyl, etc.; R.sup.11 is H or alkyl; R.sup.12 is cycloalkyl or optionally substituted phenyl; and W is a group: --(CH.sub.2).sub.p (p is 3 to 5) or --CH.dbd.CH--(CH.sub.2).sub.q (q is 1 to 3), the carbon atom of these groups being optionally replaced by O, S, SO, SO.sub.2 or a group: --N(R).sup.12 and further these groups having optionally 1 to 3 substituents of alkyl, alkoxycarbonyl, carboxy, OH, O, alkanoyloxy, etc., which have excellent vasopressin antagonistic activities and are useful as vasodilator, hypotensive agent, water diuretics, platelet agglutination inhibitor, and a vasopressin antagonistic composition containing the compound as the active ingredient.
Inventor(s): Ogawa; Hidenori (Tokushima-ken, JP), Miyamoto; Hisashi (Kyoto-fu, JP), Kondo; Kazumi (Tokushima-ken, JP), Yamashita; Hiroshi (Tokushima-ken, JP), Nakaya; Kenji (Tokushima-ken, JP), Komatsu; Hajime (Tokushima-ken, JP), Tanaka; Michinori (Tokushima-ken, JP), Kora; Shinya (Nagasaki-ken, JP), Tominaga; Michiaki (Tokushima-ken, JP), Yabuuchi; Yoichi (Tokushima-ken, JP)
Assignee: Otsuka Pharmaceutical Co., Ltd. (Tokyo, JP)
Filing Date:Jun 10, 1993
Application Number:08/076,804
Claims:1. A benzoheterocyclic compound of the following formula: ##STR1173## wherein R.sup.1 is a hydrogen atom, a halogen atom, a lower alkyl, an amino having optionally a lower alkyl substituent, or a lower alkoxy,

R.sup.2 is a hydrogen atom, a halogen atom, a lower alkoxy, a phenyl(lower)alkoxy, hydroxy, a lower alkyl, an amino having optionally a lower alkyl substituent, a carbamoyl-substituted lower alkoxy, an amino-substituted lower alkoxy having optionally a lower alkyl substituent, or a benzoyloxy which has optionally a halogen substituent on the phenyl ring,

R.sup.3 is a group of the formula: ##STR1174## or a group of the formula: ##STR1175## R.sup.4 is a hydrogen atom, a benzoyl which has optionally a halogen substituent on the phenyl ring, or a lower alkyl,

R.sup.5 is a group of the formula: ##STR1176## wherein R.sup.16 is a halogen atom; a lower alkyl which has optionally a substituent selected from a halogen atom and hydroxy; hydroxy; a lower alkoxy; a lower alkanoyloxy; a lower alkylthio; a lower alkanoyl; carboxy; a lower alkoxycarbonyl; cyano; nitro; an amino which has optionally a substituent selected from a lower alkyl and a lower alkanoyl; phenyl; a cycloalkyl having 3 to 8 carbon atoms; a lower alkanoyloxy-substituted lower alkoxy; a carboxy-substituted lower alkoxy; a halogen-substituted lower alkoxy; a carbamoyl-substituted lower alkoxy; a hydroxy-substituted lower alkoxy; a lower alkoxycarbonyl-substituted lower alkoxy; a phthalimido-substituted lower alkoxy; an aminocarbonyl-lower alkoxy having a lower alkyl substituent; or a group of the formula: ##STR1177## wherein A is a lower alkylene, and R.sup.6 and R.sup.7 are the same or different and are each a hydrogen atom, a lower alkyl having optionally a hydroxy substituent, a lower alkanoyl, or benzoyl, or R.sup.6 and R.sup.7 may bind together with the nitrogen atom to which they are bonded to form a 5- or 6-membered saturated heterocyclic group with or without a second nitrogen atom or an oxygen atom wherein said heterocyclic group is selected from the group consisting of pyrrolidinyl, piperidinyl, piperazinyl and morpholino, and wherein the heterocyclic group has optionally a substituent selected from piperidinyl and a lower alkyl; and m is an integer of 0 to 3, a phenyl-lower alkoxycarbonyl, a lower alkanoyl, a phenyl-lower alkanoyl, a cycloalkyl-lower alkanoyl wherein said cycloalkyl group has 3 to 8 carbon atoms, a cycloalkyl-carbonyl wherein said cycloalkyl group has 3 to 8 carbon atoms, tricyclo(3.3.1.1)decanylcarbonyl, naphthylcarbonyl, pyridylcarbonyl, furoyl, thenoyl, a phenoxy-lower alkanoyl which phenyl ring has optionally 1 to 3 substituents selected from a lower alkyl, a lower alkoxy and an amino having optionally a lower alkanoyl substituent, a phthalimido-substituted lower alkanoyl, a lower alkoxycarbonyl-lower alkanoyl, a carboxy-lower alkanoyl, a naphthyloxy-lower alkanoyl, a halogen-substituted lower alkanoyl, a group of the formula: ##STR1178## wherein R.sup.8 is a hydrogen atom, a lower alkyl, a phenyl-lower alkoxycarbonyl, a carbamoyl-lower alkyl, an amino-lower alkanoyl having optionally a lower alkyl substituent, or a lower alkanoyl, an anilinocarbonyl which has optionally a lower alkyl substituent on the phenyl ring, phenoxycarbonyl, a phenylsulfonyl which has optionally a substituent selected from a halogen atom and a lower alkyl on the phenyl ring, quinolylsulfonyl, or a group of the formula: ##STR1179## wherein B is a lower alkylene, n is an integer of 0 or 1, and R.sup.9 and R.sup.10 are the same or different and are each a hydrogen atom, a lower alkyl having optionally a hydroxy substituent, a cycloalkyl having 3 to 8 carbon atoms, a phenyl-lower alkyl, a lower alkanoyl, a lower alkenyl, a phenoxy-lower alkyl, a phenyl which has optionally 1 to 3 substituents selected from an amino-lower alkyl having optionally a lower alkanoyl substituent, a lower alkyl, a lower alkoxy and a halogen atom, a phthalimido-substituted lower alkyl, an amino-lower alkyl having optionally a lower alkanoyl substituent, a lower alkynyl, or an amino-lower alkyl having optionally a lower alkyl substituent, or R.sup.9 and R.sup.10 may bind together with the nitrogen atom to which they are bonded to form a 5- or 6-membered saturated heterocyclic group with or without a second nitrogen atom or an oxygen atom wherein said heterocyclic group is selected from the group consisting of pyrrolidinyl, piperidinyl, piperazinyl and morpholino, and wherein the heterocyclic group has optionally a substituent selected from a lower alkyl, a lower alkoxycarboyl and piperidinyl,

R.sup.11 is a hydrogen atom or a lower alkyl,

R.sup.12 is a cycloalkyl, or a phenyl which has optionally 1 to 3 substituents selected from a lower alkoxy, a lower alkyl and a halogen atom,

W is a group of the formula: --(CH.sub.2).sub.p -- wherein p is an integer of 3 to 5, or a group of the formula: --CH.dbd.CH--(CH.sub.2).sub.q -- wherein q is an integer of 1 to 3, the carbon atom of these groups: --(CH.sub.2).sub.p -- and --CH.dbd.CH--(CH.sub.2).sub.q -- being replaced by a group of the formula: ##STR1180## wherein R.sub.13 is a hydrogen atom, a cycloalkyl having 3 to 8 carbon atoms, or a lower alkyl, and further said --(CH.sub.2).sub.p -- and --CH.dbd.CH--(CH.sub.2).sub.q -- groups having optionally 1 to 3 substituents selected from a lower alkyl having optionally a hydroxy substituent, a lower alkoxycarbonyl, carboxy, hydroxy, oxo, a lower alkanoyloxy having optionally a halogen substituent, an amino-lower alkyl having optionally a substituent selected from a lower alkyl and a lower alkanoyl, a lower alkanoyloxy-substituted lower alkyl, a lower alkyl sulfonyloxy-lower alkyl, an azido-lower alkyl, a group of the formula: ##STR1181## an aminocarbonyloxy having optionally a lower alkyl substituent, a lower alkoxy, a lower alkoxycarbonyl-substituted lower alkoxy, a carboxy-substituted lower alkoxy, an aminocarbonyl-lower alkoxy having optionally a lower alkyl substituent, an amino-lower alkoxy having optionally a substituent selected from a lower alkyl and a lower alkanoyl, a phthalimido-substituted lower alkoxy, hydroxyimino, a lower alkanoyloxy-imino, a lower alkylidene, a halogen atom, azido, sulfoxyimino, a group of the formula: ##STR1182## wherein R.sup.81 is a hydrogen atom or a lower alkyl, hydrazino, pyrrolyl, an amino-lower alkanoyloxy having optionally a lower alkyl substituent, a group of the formula: ##STR1183## wherein A is as defined above, and R.sup.82 and R.sup.83 are the same or different and are each a hydrogen atom, a lower alkyl, a carbamoyl-substituted lower alkyl, a hydroxy-substituted lower alkyl, or a pyridyl-lower alkyl, or R.sup.82 and R.sup.83 may bind together with the nitrogen atom to which they are bonded to form a 5- or 6-membered saturated heterocyclic group with or without a second nitrogen atom, an oxygen atom or a sulfur atom wherein said heterocyclic group is selected from the group consisting of pyrrolidinyl, piperidinyl, piperazinyl, morpholino and thiomorpholino, and wherein the heterocyclic group has optionally a substituent selected from oxo, a lower alkyl, a lower alkanoyl, and carbamoyl, and a group of the formula: ##STR1184## wherein n is as defined above, and R.sup.14 and R.sup.15 are the same or different and are each a hydrogen atom, a lower alkyl, a lower alkenyl, a lower alkanoyl, a cycloalkyl, an oxiranyl-substituted lower alkyl, a lower alkyl having 1 to 2 substituents selected from a lower alkoxy, hydroxy and an amino having optionally a lower alkyl substituent, a phenyl-lower alkyl, a pyridyl-lower alkyl, a lower alkylsulfonyl, benzoyl, a lower alkoxycarbonyl, anilinocarbonyl, an aminocarbonyl having optionally a lower alkyl substituent, a cyano-substituted lower alkyl, a lower alkoxycarbonyl-substituted lower alkyl, a carbamoyl-substituted lower alkyl, a carboxy-substituted lower alkyl, a tetrahydropyranyloxy-substituted lower alkyl, a lower alkanoyloxy-substituted lower alkyl, a piperidinyl having optionally a phenyl-lower alkyl substituent on the piperidinyl ring, a halogen-substituted substituted lower alkanoyl, an imidazolyl-substituted lower alkanoyl, an amino-lower alkanoyl having optionally a substituent selected from a lower alkyl and a lower alkoxycarbonyl, an aminocarbonyl-lower alkyl having optionally a lower alkyl substituent, or a phenyl-lower alkoxycarbonyl, or R.sup.14 and R.sup.15 may bind together with the nitrogen atom to which they are bonded to form a 5- or 6-membered saturated heterocyclic group with or without a second nitrogen atom or an oxygen atom wherein said heterocyclic group is selected from the group consisting of pyrrolidinyl, piperidinyl, piperazinyl and morpholino, and wherein the heterocyclic group may optionally have a substituent selected from a lower alkyl, a phenyl-lower alkyl or a lower alkanoyl, and a pharmaceutically acceptable salt thereof.

2. The compound according to claim 1, wherein R.sup.1 in the formula (1) is hydrogen atom, or a pharmaceutically acceptable salt thereof.

3. The compound according to claim 1, wherein R.sup.1 in the formula (1) is a halogen atom, and a pharmaceutically acceptable salt thereof.

4. The compound according to claim 1, wherein R.sup.1 in the formula (1) is a lower alkyl, an amino having optionally a lower alkyl substituent, or a lower alkoxy, and a pharmaceutically acceptable salt thereof.

5. The compound according to claim 2, wherein R.sup.2 is a hydrogen atom, and a pharmaceutically acceptable salt thereof.

6. The compound according to claim 2, wherein R.sup.2 is a halogen atom, a lower alkoxy, or a lower alkyl, and a pharmaceutically acceptable salt thereof.

7. The compound according to claim 2, wherein R.sup.2 is a phenyl-lower alkoxy; hydroxy; an amino having optionally a lower alkyl substituent; a carbamoyl-substituted lower alkoxy; an amino-substituted lower alkoxy having optionally a lower alkyl substituent; or a benzoyloxy having optionally a halogen substituent on the phenyl ring thereof, and a pharmaceutically acceptable salt thereof.

8. The compound according to claim 3, wherein R.sup.2 is a hydrogen atom, and a pharmaceutically acceptable salt thereof.

9. The compound according to claim 3, wherein R.sup.2 is a halogen atom, a lower alkoxy, or a lower alkyl, and a pharmaceutically acceptable salt thereof.

10. The compound according to claim 3, wherein R.sup.2 is a phenyl-lower alkoxy; a hydroxy; an amino having optionally a lower alkyl substituent; a carbamoyl-substituted lower alkoxy; an amino-substituted lower alkoxy having optionally a lower alkyl substituent; or a benzoyloxy having optionally a halogen substituent on the phenyl ring thereof, and a pharmaceutically acceptable salt thereof.

11. The compound according to claim 4, wherein R.sup.2 is a hydrogen atom, and a pharmaceutically acceptable salt thereof.

12. The compound according to claim 4, wherein R.sup.2 is a halogen atom, a lower alkoxy, or a lower alkyl, and a pharmaceutically acceptable salt thereof.

13. The compound according to claim 4, wherein R.sup.2 is a phenyl-lower alkoxy; a hydroxy; an amino having optionally a lower alkyl substituent; a carbamoyl-substituted lower alkoxy; an amino-substituted lower alkoxy having optionally a lower alkyl substituent; or a benzoyloxy having optionally a halogen substituent on the phenyl ring thereof, and a pharmaceutically acceptable salt thereof.

14. The compound according to claim 5, wherein R.sup.3 is a group of the formula: --NR.sup.4 R.sup.5 (R.sup.4 and R.sup.5 are as defined in claim 1), and a pharmaceutically acceptable salt thereof.

15. The compound according to claim 5, wherein R.sup.3 is a group of the formula: --CO--NR.sup.11 R.sup.12 (R.sup.11 and R.sup.12 are as defined in claim 1), and a pharmaceutically acceptable salt thereof.

16. The compound according to claim 6, wherein R.sup.3 is a group of the formula: --NR.sup.4 R.sup.5 (R.sup.4 and R.sup.5 are as defined in claim 1), and a pharmaceutically acceptable salt thereof.

17. The compound according to claim 6, wherein R.sup.3 is a group of the formula: --CO--NR.sup.11 R.sup.12 (R.sup.11 and R.sup.12 are as defined in claim 1), and a pharmaceutically acceptable salt thereof.

18. The compound according to claim 8, wherein R.sup.3 is a group of the formula: --NR.sup.4 R.sup.5 (R.sup.4 and R.sup.5 are as defined in claim 1), and a pharmaceutically acceptable salt thereof.

19. The compound according to claim 8, wherein R.sup.3 is a group of the formula: --CO--NR.sup.11 R.sup.12 (R.sup.11 and R.sup.12 are as defined in claim 1), and a pharmaceutically acceptable salt thereof.

20. The compound according to claim 9, wherein R.sup.3 is a group of the formula: --NR.sup.4 R.sup.5 (R.sup.4 and R.sup.5 are as defined in claim 1), and a pharmaceutically acceptable salt thereof.

21. The compound according to claim 9, wherein R.sup.3 is a group of the formula: --CO--NR.sup.11 R.sup.12 (R.sup.11 and R.sup.12 are as defined in claim 1), and a pharmaceutically acceptable salt thereof.

22. The compound according to claim 14, wherein R.sup.4 is a hydrogen atom, and R.sup.5 is a group of the formula: ##STR1185## (wherein R.sup.16 and m are as defined in claim 1), and a pharmaceutically acceptable salt thereof.

23. The compound according to claim 14, wherein R.sup.4 is a hydrogen atom and R.sup.5 is a phenyl-lower alkoxycarbonyl, a lower alkanoyl, a phenyl-lower alkanoyl, a cycloalkyl-lower alkanoyl wherein said cycloalkyl group has 3 to 8 carbon atoms, a cycloalkylcarbonyl wherein said cycloalkyl group has 3 to 8 carbon atoms, tricyclo(3.3.1.1)decanylcarbonyl, naphthylcarbonyl, pyridylcarbonyl, furoyl, thenoyl, a phenoxy-lower alkanoyl which phenyl ring has optionally 1 to 3 substituents selected from a lower alkyl, a lower alkoxy and an amino having optionally a lower alkanoyl substituent, a phthalimido-substituted lower alkanoyl, a lower alkoxycarbonyl-lower alkanoyl, a carboxy-lower alkanoyl, a naphthyloxy-lower alkanoyl, a halogen-substituted lower alkanoyl, group of the formula: ##STR1186## wherein R.sup.8 is a hydrogen atom, a lower alkyl, a phenyl-lower alkoxycarbonyl, a carbamoyl-lower alkyl, an amino-lower alkanoyl having optionally a lower alkyl substituent, or a lower alkanoyl, an anilinocarbonyl which has optionally a lower alkyl substituent on the phenyl ring, phenoxycarbonyl, a phenylsulfonyl which has optionally a substituent selected from a halogen atom and a lower alkyl on the phenyl ring, quinolylsulfonyl, or a group of the formula: ##STR1187## wherein B is a lower alkylene, n is an integer of 0 or 1, and R.sup.9 and R.sup.10 are the same or different and are each a hydrogen atom, a lower alkyl having optionally a hydroxy substituent, a cycloalkyl having 3 to 8 carbon atoms, a phenyl-lower alkyl, a lower alkanoyl, a lower alkenyl, a phenoxy-lower alkyl, a phenyl which has optionally 1 to 3 substituents selected from an amino-lower alkyl having optionally a lower alkanoyl substituent, a lower alkyl, a lower alkoxy and a halogen atom, a phthalimido-substituted lower alkyl, an amino-lower alkyl having optionally a lower alkanoyl substituent, a lower alkynyl, or an amino-lower alkyl having optionally a lower alkyl substituent, or R.sup.9 and R.sup.10 may bind together with the nitrogen atom to which they are bonded to form a 5- or 6-membered saturated heterocyclic group with or without a second nitrogen atom or an oxygen atom wherein said heterocyclic group is selected from the group consisting of pyrrolidinyl, piperidinyl, piperazinyl and morpholino, and wherein the heterocyclic group has optionally a substituent selected from a lower alkyl, a lower alkoxycarboyl and piperidinyl, and a pharmaceutically acceptable salt thereof.

24. The compound according to claim 14, wherein R.sup.4 is a lower alkyl, and a pharmaceutically acceptable salt thereof.

25. The compound according to claim 16, wherein R.sup.4 is hydrogen atom, and R.sup.5 is a group of the formula: ##STR1188## (wherein R.sup.16 and m are as defined in claim 1), and a pharmaceutically acceptable salt thereof.

26. The compound according to claim 16, wherein R.sup.4 is a hydrogen atom and R.sup.5 is a phenyl-lower alkoxycarbonyl, a lower alkanoyl, a phenyl-lower alkanoyl, a cycloalkyl-lower alkanoyl wherein said cycloalkyl group has 3 to 8 carbon atoms, a cycloalkylcarbonyl wherein said cycloalkyl group has 3 to 8 carbon atoms, tricyclo(3.3.1.1)decanylcarbonyl, naphthylcarbonyl, pyridylcarbonyl, furoyl, thenoyl, a phenoxy-lower alkanoyl which phenyl ring has optionally 1 to 3 substituents selected from a lower alkyl, a lower alkoxy and an amino having optionally a lower alkanoyl substituent, a phthalimido-substituted lower alkanoyl, a lower alkoxycarbonyl-lower alkanoyl, a carboxy-lower alkanoyl, a naphthyloxy-lower alkanoyl, a halogen-substituted lower alkanoyl, group of the formula: ##STR1189## wherein R.sup.8 is a hydrogen atom, a lower alkyl, a phenyl-lower alkoxycarbonyl, a carbamoyl-lower alkyl, an amino-lower alkanoyl having optionally a lower alkyl substituent, or a lower alkanoyl, an anilinocarbonyl which has optionally a lower alkyl substituent on the phenyl ring, phenoxycarbonyl, a phenysulfonyl which has optionally a substituent selected from a halogen atom and a lower alkyl on the phenyl ring, quinolylsulfonyl, or a group of the formula: ##STR1190## wherein B is a lower alkylene, n is an integer of 0 or 1, and R.sup.9 and R.sup.10 are the same or different and are each a hydrogen atom, a lower alkyl having optionally a hydroxy substituent, a cycloalkyl having 3 to 8 carbon atoms, a phenyl-lower alkyl, a lower alkanoyl, a lower alkenyl, a phenoxy-lower alkyl, a phenyl which has optionally 1 to 3 substituents selected from an amino-lower alkyl having optionally a lower alkanoyl substituent, a lower alkyl, a lower alkoxy and a halogen atom, a phthalimido-substituted lower alkyl, an amino-lower alkyl having optionally a lower alkanoyl substituent, a lower alkynyl, or an amino-lower alkyl having optionally a lower alkyl substituent, or R.sup.9 and R.sup.10 may bind together with the nitrogen atom to which they are bonded to form a 5- or 6-membered saturated heterocyclic group with or without a second nitrogen or an oxygen atom wherein said heterocyclic group is selected from the group consisting of pyrrolidinyl, piperidinyl, piperazinyl and morpholino, and wherein the heterocyclic group has optionally a substituent selected from a lower alkyl, a lower alkoxycarboyl and piperidinyl, and a pharmaceutically acceptable salt thereof.

27. The compound according to claim 16, wherein R.sup.4 is a lower alkyl, and a pharmaceutically acceptable salt thereof.

28. The compound according to claim 7, wherein R.sup.4 is a hydrogen atom, and R.sup.5 is a group of the formula: ##STR1191## (wherein R.sup.16 and m are as defined in claim 1), and a pharmaceutically acceptable salt thereof.

29. The compound according to claim 7, wherein R.sup.4 is a hydrogen atom and R.sup.5 is a phenyl-lower alkoxycarbonyl, a lower alkanoyl, a phenyl-lower alkanoyl, a cycloalkyl-lower alkanoyl wherein said cycloalkyl group has 3 to 8 carbon atoms, a cycloalkylcarbonyl wherein said cycloalkyl group has 3 to 8 carbon atoms, tricyclo(3.3.1.1)decanylcarbonyl, naphthylcarbonyl, pyridylcarbonyl, furoyl, thenoyl, a phenoxy-lower alkanoyl which phenyl ring has optionally 1 to 3 substituents selected from a lower alkyl, a lower alkoxy and an amino having optionally a lower alkanoyl substituent, a phthalimido-substituted lower alkanoyl, a lower alkoxycarbonyl-lower alkanoyl, a carboxy-lower alkanoyl, a naphthyloxy-lower alkanoyl, a halogen-substituted lower alkanoyl, a group of the formula: ##STR1192## wherein R.sup.8 is a hydrogen atom, a lower alkyl, a phenyl-lower alkoxycarbonyl, a carbamoyl-lower alkyl, an amino-lower alkanoyl having optionally a lower alkyl substituent, or a lower alkanoyl, an anilinocarbonyl which has optionally a lower alkyl substituent on the phenyl ring, phenoxycarbonyl, a phenysulfonyl which has optionally a substituent selected from a halogen atom and a lower alkyl on the phenyl ring, quinolylsulfonyl, or a group of the formula: ##STR1193## wherein B is a lower alkylene, n is an integer of 0 or 1, and R.sup.9 and R.sup.10 are the same or different and are each a hydrogen atom, a lower alkyl having optionally a hydroxy substituent, a cycloalkyl having 3 to 8 carbon atoms, a phenyl-lower alkyl, a lower alkanoyl, a lower alkenyl, a phenoxy-lower alkyl, a phenyl which has optionally 1 to 3 substituents selected from an amino-lower alkyl having optionally a lower alkanoyl substituent, a lower alkyl, a lower alkoxy and a halogen atom, a phthalimido-substituted lower alkyl, an amino-lower alkyl having optionally a lower alkanoyl substituent, a lower alkynyl, or an amino-lower alkyl having optionally a lower alkyl substituent, or R.sup.9 and R.sup.10 may bind together with the nitrogen atom to which they bond to form a 5- or 6-membered saturated heterocyclic group with or without a second nitrogen atom or an oxygen atom wherein said heterocyclic group is selected from the group consisting of pyrrolidinyl, piperidinyl, piperazinyl, morpholino and thiomorpholino, and wherein the heterocyclic group has optionally a substituent selected from a lower alkyl, a lower alkoxycarboyl and piperidinyl, and a pharmaceutically acceptable salt thereof.

30. The compound according to claim 7, wherein R.sup.4 is a lower alkyl, and a pharmaceutically acceptable salt thereof.

31. The compound according to claim 18, wherein R.sup.4 is a hydrogen atom, and R.sup.5 is a group of the formula: ##STR1194## (wherein R.sup.16 and m are as defined in claim 1), and a pharmaceutically acceptable salt thereof.

32. The compound according to claim 18, wherein R.sup.4 is a hydrogen atom and R.sup.5 is a phenyl-lower alkoxycarbonyl, a lower alkanoyl, a phenyl-lower alkanoyl, a cycloalkyl-lower alkanoyl wherein said cycloalkyl group has 3 to 8 carbon atoms, a cycloalkylcarbonyl wherein said cycloalkyl group has 3 to 8 carbon atoms, tricyclo(3.3.1.1)decanylcarbonyl, naphthylcarbonyl, pyridylcarbonyl, furoyl, thenoyl, a phenoxy-lower alkanoyl which phenyl ring has optionally 1 to 3 substituents selected from a lower alkyl, a lower alkoxy and an amino having optionally a lower alkanoyl substituent, a phthalimido-substituted lower alkanoyl, a lower alkoxycarbonyl-lower alkanoyl, a carboxy-lower alkanoyl, a naphthyloxy-lower alkanoyl, a halogen-substituted lower alkanoyl, group of the formula: ##STR1195## wherein R.sup.8 is a hydrogen atom, a lower alkyl, a phenyl-lower alkoxycarbonyl, a carbamoyl-lower alkyl, an amino-lower alkanoyl having optionally a lower alkyl substituent, or a lower alkanoyl, an anilinocarbonyl which has optionally a lower alkyl substituent on the phenyl ring, phenoxycarbonyl, a phenylsulfonyl which has optionally a substituent selected from a halogen atom and a lower alkyl on the phenyl ring, quinolylsulfonyl, or a group of the formula: ##STR1196## wherein B is a lower alkylene, n is an integer of 0 or 1, and R.sup.9 and R.sup.10 are the same or different and are each a hydrogen atom, a lower alkyl having optionally a hydroxy substituent, a cycloalkyl having 3 to 8 carbon atoms, a phenyl-lower alkyl, a lower alkanoyl, a lower alkenyl, a phenoxy-lower alkyl, a phenyl which has optionally 1 to 3 substituents selected from an amino-lower alkyl having optionally a lower alkanoyl substituent, a lower alkyl, a lower alkoxy and a halogen atom, a phthalimido-substituted lower alkyl, an amino-lower alkyl having optionally a lower alkanoyl substituent, a lower alkynyl, or an amino-lower alkyl having optionally a lower alkyl substituent, or R.sup.9 and R.sup.10 may bind together with the nitrogen atom to which they are bonded to form a 5- or 6-membered saturated heterocyclic group with or without a second nitrogen atom or an oxygen atom wherein said heterocyclic group is selected from the group consisting of pyrrolidinyl, piperidinyl, piperazinyl and morpholino, and wherein the heterocyclic group has optionally a substituent selected from a lower alkyl, a lower alkoxycarboyl and piperidinyl, and a pharmaceutically acceptable salt thereof.

33. The compound according to claim 18, wherein R.sup.4 is a lower alkyl, and a pharmaceutically acceptable salt thereof.

34. The compound according to claim 20, wherein R.sup.4 is a hydrogen atom, and R.sup.5 is a group of the formula: ##STR1197## (wherein R.sup.16 and m are as defined in claim 1), and a pharmaceutically acceptable salt thereof.

35. The compound according to claim 20, wherein R.sup.4 is a hydrogen atom and R.sup.5 is a phenyl-lower alkoxycarbonyl, a lower alkanoyl, a phenyl-lower alkanoyl, a cycloalkyl-lower alkanoyl wherein said cycloalkyl group has 3 to 8 carbon atoms, a cycloalkylcarbonyl wherein said cycloalkyl group has 3 to 8 carbon atoms, tricyclo(3.3.1.1)decanylcarbonyl, naphthylcarbonyl, pyridylcarbonyl, furoyl, thenoyl, a phenoxy-lower alkanoyl which phenyl ring has optionally 1 to 3 substituents selected from a lower alkyl, a lower alkoxy and an amino having optionally a lower alkanoyl substituent, a phthalimido-substituted lower alkanoyl, a lower alkoxycarbonyl-lower alkanoyl, a carboxy-lower alkanoyl, a naphthyloxy-lower alkanoyl, a halogen-substituted lower alkanoyl, a group of the formula: ##STR1198## wherein R.sup.8 is a hydrogen atom, a lower alkyl, a phenyl-lower alkoxycarbonyl, a carbamoyl-lower alkyl, an amino-lower alkanoyl having optionally a lower alkyl substituent, or a lower alkanoyl, an anilinocarbonyl which has optionally a lower alkyl substituent on the phenyl ring, phenoxycarbonyl, a phenylsulfonyl which has optionally a substituent selected from a halogen atom and a lower alkyl on the phenyl ring, quinolylsulfonyl, or a group of the formula: ##STR1199## wherein B is a lower alkylene, n is an integer of 0 or 1, and R.sup.9 and R.sup.10 are the same or different and are each a hydrogen atom, a lower alkyl having optionally a hydroxy substituent, a cycloalkyl having 3 to 8 carbon atoms, a phenyl-lower alkyl, a lower alkanoyl, a lower alkenyl, a phenoxy-lower alkyl, a phenyl which has optionally 1 to 3 substituents selected from an amino-lower alkyl having optionally a lower alkanoyl substituent, a lower alkyl, a lower alkoxy and a halogen atom, a phthalimido-substituted lower alkyl, an amino-lower alkyl having optionally a lower alkanoyl substituent, a lower alkynyl, or an amino-lower alkyl having optionally a lower alkyl substituent, or R.sup.9 and R.sup.10 may bind together with the nitrogen atom to which they are bonded to form a 5- or 6-membered saturated heterocyclic group with or without a second nitrogen atom or an oxygen atom wherein said heterocyclic group is selected from the group consisting of pyrrolidinyl, piperidinyl, piperazinyl, morpholino and thiomorpholino, and wherein the heterocyclic group has optionally a substituent selected from a lower alkyl, a lower alkoxycarboyl and piperidinyl, and a pharmaceutically acceptable salt thereof.

36. The compound according to claim 20, wherein R.sup.4 is a lower alkyl, and a pharmaceutically acceptable salt thereof.

37. The compound according to claim 10, wherein R.sup.4 is a hydrogen atom, and R.sup.5 is a group of the formula: ##STR1200## (wherein R.sup.16 and m are as defined in claim 1), and a pharmaceutically acceptable salt thereof.

38. The compound according to claim 10, wherein R.sup.4 is a hydrogen atom and R.sup.5 is a phenyl-lower alkoxycarbonyl, a lower alkanoyl, a phenyl-lower alkanoyl, a cycloalkyl-lower alkanoyl wherein said cycloalkyl group has 3 to 8 carbon atoms, a cycloalkylcarbonyl wherein said cycloalkyl group has 3 to 8 carbon atoms, tricyclo(3.3.1.1)decanylcarbonyl, naphthylcarbonyl, pyridylcarbonyl, furoyl, thenoyl, a phenoxy-lower alkanoyl which phenyl ring has optionally 1 to 3 substituents selected from a lower alkyl, a lower alkoxy and an amino having optionally a lower alkanoyl substituent, a phthalimido-substituted lower alkanoyl, a lower alkoxycarbonyl-lower alkanoyl, a carboxy-lower alkanoyl, a naphthyloxy-lower alkanoyl, a halogen-substituted lower alkanoyl, a group of the formula: ##STR1201## wherein R.sup.8 is a hydrogen atom, a lower alkyl, a phenyl-lower alkoxycarbonyl, a carbamoyl-lower alkyl, an amino-lower alkanoyl having optionally a lower alkyl substituent, or a lower alkanoyl, an anilinocarbonyl which has optionally a lower alkyl substituent on the phenyl ring, phenoxycarbonyl, a phenylsulfonyl which has optionally a substituent selected from a halogen atom and a lower alkyl on the phenyl ring, quinolylsulfonyl, or a group of the formula: ##STR1202## wherein B is a lower alkylene, n is an integer of 0 or 1, and R.sup.9 and R.sup.10 are the same or different and are each a hydrogen atom, a lower alkyl having optionally a hydroxy substituent, a cycloalkyl having 3 to 8 carbon atoms, a phenyl-lower alkyl, a lower alkanoyl, a lower alkenyl, a phenoxy-lower alkyl, a phenyl which has optionally 1 to 3 substituents selected from an amino-lower alkyl having optionally a lower alkanoyl substituent, a lower alkyl, a lower alkoxy and a halogen atom, a phthalimido-substituted lower alkyl, an amino-lower alkyl having optionally a lower alkanoyl substituent, a lower alkynyl, or an amino-lower alkyl having optionally a lower alkyl substituent, or R.sup.9 and R.sup.10 may bind together with the nitrogen atom to which they are bonded to form a 5- or 6-membered saturated heterocyclic group with or without a second nitrogen atom or an oxygen atom, wherein said heterocyclic group is selected from the group consisting of pyrrolidinyl, piperidinyl, piperazinyl, morpholino and thiomorpholino, and wherein the heterocyclic group has optionally a substituent selected from a lower alkyl, a lower alkoxycarboyl and piperidinyl, and a pharmaceutically acceptable salt thereof.

39. The compound according to claim 10, wherein R.sup.4 is a lower alkyl, and a pharmaceutically acceptable salt thereof.

40. The compound according to claim 11, wherein R.sup.4 is a hydrogen atom, and R.sup.5 is a group of the formula: ##STR1203## (wherein R.sup.16 and m are as defined in claim 1), and a pharmaceutically acceptable salt thereof.

41. The compound according to claim 11, wherein R.sup.4 is a hydrogen atom and R.sup.5 is a phenyl-lower alkoxycarbonyl, a lower alkanoyl, a phenyl-lower alkanoyl, a cycloalkyl-lower alkanoyl wherein said cycloalkyl group has 3 to 8 carbon atoms, a cycloalkylcarbonyl wherein said cycloalkyl group has 3 to 8 carbon atoms, tricyclo(3.3.1.1)decanylcarbonyl, naphthylcarbonyl, pyridylcarbonyl, furoyl, thenoyl, a phenoxy-lower alkanoyl which phenyl ring has optionally 1 to 3 substituents selected from a lower alkyl, a lower alkoxy and an amino having optionally a lower alkanoyl substituent, a phthalimido-substituted lower alkanoyl, a lower alkoxycarbonyl-lower alkanoyl, a carboxy-lower alkanoyl, a naphthyloxy-lower alkanoyl, a halogen-substituted lower alkanoyl, a group of the formula: ##STR1204## wherein R.sup.8 is a hydrogen atom, a lower alkyl, a phenyl-lower alkoxycarbonyl, a carbamoyl-lower alkyl, an amino-lower alkanoyl having optionally a lower alkyl substituent, or a lower alkanoyl, an anilinocarbonyl which has optionally a lower alkyl substituent on the phenyl ring, phenoxycarbonyl, a phenylsulfonyl which has optionally a substituent selected from a halogen atom and a lower alkyl on the phenyl ring, quinolylsulfonyl, or a group of the formula: ##STR1205## wherein B is a lower alkylene, n is an integer of 0 or 1, and R.sup.9 and R.sup.10 are the same or different and are each a hydrogen atom, a lower alkyl having optionally a hydroxy substituent, a cycloalkyl having 3 to 8 carbon atoms, a phenyl-lower alkyl, a lower alkanoyl, a lower alkenyl, a phenoxy-lower alkyl, a phenyl which has optionally 1 to 3 substituents selected from an amino-lower alkyl having optionally a lower alkanoyl substituent, a lower alkyl, a lower alkoxy and a halogen atom, a phthalimido-substituted lower alkyl, an amino-lower alkyl having optionally a lower alkanoyl substituent, a lower alkynyl, or an amino-lower alkyl having optionally a lower alkyl substituent, or R.sup.9 and R.sup.10 may bind together with the nitrogen atom to which they are bonded to form a 5- or 6-membered saturated heterocyclic group with or without a second nitrogen atom or an oxygen atom wherein said heterocyclic group is selected from the group consisting of pyrrolidinyl, piperidinyl, piperazinyl, morpholino and thiomorpholino, and wherein the heterocyclic group has optionally a substituent selected from a lower alkyl, a lower alkoxycarboyl and piperidinyl, and a pharmaceutically acceptable salt thereof.

42. The compound according to claim 11, wherein R.sup.4 is a lower alkyl, and a pharmaceutically acceptable salt thereof.

43. The compound according to claim 12, wherein R.sup.4 is a hydrogen atom, and R.sup.5 is a group of the formula: ##STR1206## (wherein R.sup.16 and m are as defined in claim 1), and a salt thereof.

44. The compound according to claim 12, wherein R.sup.4 is a hydrogen atom and R.sup.5 is a phenyl-lower alkoxycarbonyl, a lower alkanoyl, a phenyl-lower alkanoyl, a cycloalkyl-lower alkanoyl wherein said cycloalkyl group has 3 to 8 carbon atoms, a cycloalkylcarbonyl wherein said cycloalkyl group has 3 to 8 carbon atoms, tricyclo(3.3.1.1)decanylcarbonyl, naphthylcarbonyl, pyridylcarbonyl, furoyl, thenoyl, a phenoxy-lower alkanoyl which phenyl ring has optionally 1 to 3 substituents selected from a lower alkyl, a lower alkoxy and an amino having optionally a lower alkanoyl substituent, a phthalimido-substituted lower alkanoyl, a lower alkoxycarbonyl-lower alkanoyl, a carboxy-lower alkanoyl, a naphthyloxy-lower alkanoyl, a halogen-substituted lower alkanoyl, a group of the formula: ##STR1207## wherein R.sup.8 is a hydrogen atom, a lower alkyl, a phenyl-lower alkoxycarbonyl, a carbamoyl-lower alkyl, an amino-lower alkanoyl having optionally a lower alkyl substituent, or a lower alkanoyl, an anilinocarbonyl which has optionally a lower alkyl substituent on the phenyl ring, phenoxycarbonyl, a phenylsulfonyl which has optionally a substituent selected from a halogen atom and a lower alkyl on the phenyl ring, quinolylsulfonyl, or a group of the formula: ##STR1208## wherein B is a lower alkylene, n is an integer of 0 or 1, and R.sup.9 and R.sup.10 are the same or different and are each a hydrogen atom, a lower alkyl having optionally a hydroxy substituent, a cycloalkyl having 3 to 8 carbon atoms, a phenyl-lower alkyl, a lower alkanoyl, a lower alkenyl, a phenoxy-lower alkyl, a phenyl which has optionally 1 to 3 substituents selected from an amino-lower alkyl having optionally a lower alkanoyl substituent, a lower alkyl, a lower alkoxy and a halogen atom, a phthalimido-substituted lower alkyl, an amino-lower alkyl having optionally a lower alkanoyl substituent, a lower alkynyl, or an amino-lower alkyl having optionally a lower alkyl substituent, or R.sup.9 and R.sup.10 may bind together with the nitrogen atom to which they are bonded to form a 5- or 6-membered saturated heterocyclic group with or without a second nitrogen atom or an oxygen atom wherein said heterocyclic group is selected from the group consisting of pyrrolidinyl, piperidinyl, piperazinyl, morpholino and thiomorpholino, and wherein the heterocyclic group has optionally a substituent selected from a lower alkyl, a lower alkoxycarboyl and piperidinyl, and a pharmaceutically acceptable salt thereof.

45. The compound according to claim 12, wherein R.sup.4 is a lower alkyl, and a pharmaceutically acceptable salt thereof.

46. The compound according to claim 13, wherein R.sup.4 is a hydrogen atom, and R.sup.5 is a group of the formula: ##STR1209## (wherein R.sup.16 and m are as defined in claim 1), and a pharmaceutically acceptable salt thereof.

47. The compound according to claim 13, wherein R.sup.4 is a hydrogen atom and R.sup.5 is a phenyl-lower alkoxycarbonyl, a lower alkanoyl, a phenyl-lower alkanoyl, a cycloalkyl-lower alkanoyl wherein said cycloalkyl group has 3 to 8 carbon atoms, a cycloalkylcarbonyl wherein said cycloalkyl group has 3 to 8 carbon atoms, tricyclo(3.3.1.1)decanylcarbonyl, naphthylcarbonyl, pyridylcarbonyl, furoyl, thenoyl, a phenoxy-lower alkanoyl which phenyl ring has optionally 1 to 3 substituents selected from a lower alkyl, a lower alkoxy and an amino having optionally a lower alkanoyl substituent, a phthalimido-substituted lower alkanoyl, a lower alkoxycarbonyl-lower alkanoyl, a carboxy-lower alkanoyl, a naphthyloxy-lower alkanoyl, a halogen-substituted lower alkanoyl, a group of the formula: ##STR1210## wherein R.sup.8 is a hydrogen atom, a lower alkyl, a phenyl-lower alkoxycarbonyl, a carbamoyl-lower alkyl, an amino-lower alkanoyl having optionally a lower alkyl substituent, or a lower alkanoyl, an anilinocarbonyl which has optionally a lower alkyl substituent on the phenyl ring, phenoxycarbonyl, a phenylsulfonyl which has optionally a substituent selected from a halogen atom and a lower alkyl on the phenyl ring, quinolylsulfonyl, or a group of the formula: ##STR1211## wherein B is a lower alkylene, n is an integer of 0 or 1, and R.sup.9 and R.sup.10 are the same or different and are each a hydrogen atom, a lower alkyl having optionally a hydroxy substituent, a cycloalkyl having 3 to 8 carbon atoms, a phenyl-lower alkyl, a lower alkanoyl, a lower alkenyl, a phenoxy-lower alkyl, a phenyl which has optionally 1 to 3 substituents selected from an amino-lower alkyl having optionally a lower alkanoyl substituent, a lower alkyl, a lower alkoxy and a halogen atom, a phthalimido-substituted lower alkyl, an amino-lower alkyl having optionally a lower alkanoyl substituent, a lower alkynyl, or an amino-lower alkyl having optionally a lower alkyl substituent, or R.sup.9 and R.sup.10 may bind together with the nitrogen atom to which they are bonded to form a 5- or 6-membered saturated heterocyclic group with or without a second nitrogen atom or an oxygen atom wherein said heterocyclic group is selected from the group consisting of pyrrolidinyl, piperidinyl, piperazinyl, morpholino and thiomorpholino, and wherein the heterocyclic group has optionally a substituent selected from a lower alkyl, a lower alkoxycarboyl and piperidinyl, and a pharmaceutically acceptable salt thereof.

48. The compound according to claim 13, wherein R.sup.4 is a lower alkyl, and a pharmaceutically acceptable salt thereof.

49. The compound according to claim 22, wherein R.sup.16 is a halogen atom, or a lower alkyl having optionally a substituent selected from a halogen atom and a hydroxy, and a pharmaceutically acceptable salt thereof.

50. The compound according to claim 25, wherein R.sup.16 is a halogen atom, or a lower alkyl having optionally a substituent selected from a halogen atom and a hydroxy, and a pharmaceutically acceptable salt thereof.

51. The compound according to claim 31, wherein R.sup.16 is a halogen atom, or a lower alkyl having optionally a substituent selected from a halogen atom and a hydroxy, and a pharmaceutically acceptable salt thereof.

52. The compound according to claim 34, wherein R.sup.16 is a halogen atom, or a lower alkyl having optionally a substituent selected from a halogen atom and a hydroxy, and a pharmaceutically acceptable salt thereof.

53. The compound according to claim 1, wherein W is a group of the formula: --(CH.sub.2).sub.p -- wherein p is an integer of 3 to 5, and the carbon atom of said group is replaced by a group of the formula: ##STR1212## wherein R.sup.13 is a hydrogen atom, a cycloalkyl having 3 to 8 carbon atoms, or a lower alkyl, and further said --(CH.sub.2).sub.p -- group has optionally 1 to 3 substituents selected from a lower alkyl having optionally a hydroxy substituent, a lower alkoxycarbonyl, carboxy, hydroxy, oxo, a lower alkanoyloxy having optionally a halogen substituent, an amino-lower alkyl having optionally a substituent selected from a lower alkyl and a lower alkanoyl, a lower alkanoyloxy-substituted lower alkyl, a lower alkyl sulfonyloxy-lower alkyl, an azido-lower alkyl, a group of the formula: ##STR1213## an aminocarbonyloxy having optionally a lower alkyl substituent, a lower alkoxy, a lower alkoxycarbonyl-substituted lower alkoxy, a carboxy-substituted lower alkoxy, an aminocarbonyl-lower alkoxy having optionally a lower alkyl substituent, an amino-lower alkoxy having optionally a substituent selected from a lower alkyl and a lower alkanoyl, a phthalimido-substituted lower alkoxy, hydroxyimino, a lower alkanoyloxy-imino, a lower alkylidene, a halogen atom, azido, sulfoxyimino, a group of the formula: ##STR1214## wherein R.sup.81 is a hydrogen atom or a lower alkyl, hydrazino, pyrrolyl, an amino-lower alkanoyloxy having optionally a lower alkyl substituent, a group of the formula: ##STR1215## wherein A is as defined above, and R.sup.82 and R.sup.83 are the same or different and are each a hydrogen atom, a lower alkyl, a carbamoyl-substituted lower alkyl, a hydroxy-substituted lower alkyl, or a pyridyl-lower alkyl, or R.sup.82 and R.sup.83 may bind together with the nitrogen atom to which they are bonded to form a 5- or 6-membered saturated heterocyclic group with or without a second nitrogen atom, an oxygen atom or a sulfur atom wherein said heterocyclic group is selected from the group consisting of pyrrolidinyl, piperidinyl, piperazinyl, morpholino and thiomorpholino, and wherein the heterocyclic group has optionally a substituent selected from oxo, a lower alkyl, a lower alkanoyl, and carbamoyl, and a group of the formula: ##STR1216## wherein n is as defined above, and R.sup.14 and R.sup.15 are the same or different and are each a hydrogen atom, a lower alkyl, a lower alkenyl, a lower alkanoyl, a cycloalkyl having 3 to 8 carbon atoms, an oxiranyl-substituted lower alkyl, a lower alkyl having 1 to 2 substituents selected from a lower alkoxy, hydroxy and an amino having optionally a lower alkyl substituent, a phenyl-lower alkyl, a pyridyl-lower alkyl, a lower alkylsulfonyl, benzoyl, a lower alkoxycarbonyl, anilinocarbonyl, an aminocarbonyl having optionally a lower alkyl substituent, a cyano-substituted lower alkyl, a lower alkoxycarbonyl-substituted lower alkyl, a carbamoyl-substituted lower alkyl, a carboxy-substituted lower alkyl, a tetrahydropyranyloxy-substituted lower alkyl, a lower alkanoyloxy-substituted lower alkyl, a piperidinyl having optionally a phenyl-lower alkyl substituent on the piperidinyl ring, a halogen-substituted lower alkanoyl, an imidazolyl-substituted lower alkanoyl, an amino-lower alkanoyl having optionally a substituent selected from a lower alkyl and a lower alkoxycarbonyl, an aminocarbonyl-lower alkyl having optionally a lower alkyl substituent, or a phenyl-lower alkoxycarbonyl, or R.sup.14 and R.sup.15 may bind together with the nitrogen atom to which they are bonded to form a 5- or 6-membered saturated heterocyclic group with or without a second nitrogen atom or an oxygen atom, wherein said heterocyclic group is selected from the group consisting of pyrrolidinyl, piperidinyl, piperazinyl and morpholino, and wherein the heterocyclic group may optionally have a substituent selected from a lower alkyl, a phenyl-lower alkyl or a lower alkanoyl, and a pharmaceutically acceptable salt thereof.

54. The compound according to claim 1, wherein W is a group of the formula: --CH.dbd.CH--(CH.sub.2).sub.q -- wherein q is an integer of 1 to 3, and the carbon atom of said group is replaced by a group of the formula: ##STR1217## wherein R.sup.13 is a hydrogen atom, a cycloalkyl, or a lower alkyl, and further said --(CH.dbd.CH--(CH.sub.2).sub.q -- group has optionally 1 to 3 substituents selected from a lower alkyl having optionally a hydroxy substituent, a lower alkoxycarbonyl, carboxy, hydroxy, oxo, a lower alkanoyloxy having optionally a halogen substituent, an amino-lower alkyl having optionally a substituent selected from a lower alkyl and a lower alkanoyl, a lower alkanoyloxy-substituted lower alkyl, a lower alkyl sulfonyloxy-lower alkyl, an azido-lower alkyl, a group of the formula: ##STR1218## an aminocarbonyloxy having optionally a lower alkyl substituent, a lower alkoxy, a lower alkoxycarbonyl-substituted lower alkoxy, a carboxy-substituted lower alkoxy, an aminocarbonyl-lower alkoxy having optionally a lower alkyl substituent, an amino-lower alkoxy having optionally a substituent selected from a lower alkyl and a lower alkanoyl, a phthalimido-substituted lower alkoxy, hydroxyimino, a lower alkanoyloxy-imino, a lower alkylidene, a halogen atom, azido, sulfoxyimino, a group of the formula: ##STR1219## wherein R.sup.81 is a hydrogen atom or a lower alkyl, hydrazino, pyrrolyl, an amino-lower alkanoyloxy having optionally a lower alkyl substituent, a group of the formula: ##STR1220## wherein A is as defined above, and R.sup.82 and R.sup.83 are the same or different and are each a hydrogen atom, a lower alkyl, a carbamoyl-substituted lower alkyl, a hydroxy-substituted lower alkyl, or a pyridyl-lower alkyl, or R.sup.82 and R.sup.83 may bind together with the nitrogen atom to which they are bonded to form a 5- or 6-membered saturated heterocyclic group with or without a second nitrogen atom, an oxygen atom or a sulfur atom wherein said heterocyclic group is selected from the group consisting of pyrrolidinyl, piperidinyl, piperazinyl and morpholino, and wherein the heterocyclic group has optionally a substituent selected from oxo, a lower alkyl, a lower alkanoyl, and carbamoyl, and a group of the formula: ##STR1221## wherein n is as defined above, and R.sup.14 and R.sup.15 are the same or different and are each a hydrogen atom, a lower alkyl, a lower alkenyl, a lower alkanoyl, a cycloalkyl having 3 to 8 carbon atoms, an oxiranyl-substituted lower alkyl, a lower alkyl having 1 to 2 substituents selected from a lower alkoxy, hydroxy and an amino having optionally a lower alkyl substituent, a phenyl-lower alkyl, a pyridyl-lower alkyl, a lower alkylsulfonyl, benzoyl, a lower alkoxycarbonyl, anilinocarbonyl, an aminocarbonyl having optionally a lower alkyl substituent, a cyano-substituted lower alkyl, a lower alkoxycarbonyl-substituted lower alkyl, a carbamoyl-substituted lower alkyl, a carboxy-substituted lower alkyl, a tetrahydropyranyloxy-substituted lower alkyl, a lower alkanoyloxy-substituted lower alkyl, a piperidinyl having optionally a phenyl-lower alkyl substituent on the piperidinyl ring, a halogen-substituted lower alkanoyl, an imidazolyl-substituted lower alkanoyl, an amino-lower alkanoyl having optionally a substituent selected from a lower alkyl and a lower alkoxycarbonyl, an aminocarbonyl-lower alkyl having optionally a lower alkyl substituent, or a phenyl-lower alkoxycarbonyl, or R.sup.14 and R.sup.15 may bind together with the nitrogen atom to which they are bonded to form a 5- or 6-membered saturated heterocyclic group with or without a second nitrogen atom or an oxygen atom, wherein said heterocyclic group is selected from the group consisting of pyrrolidinyl, piperidinyl, piperazinyl and morpholino, and wherein the heterocyclic group may optionally have a substituent selected from a lower alkyl, a phenyl-lower alkyl or a lower alkanoyl, and a pharmaceutically acceptable salt thereof.

55. The compound according to claim 53, wherein p in the group: --(CH.sub.2).sub.p -- is 3 and the group has no substituent, and a pharmaceutically acceptable salt thereof.

56. The compound according to claim 53, wherein p in the group: --(CH.sub.2).sub.p -- is 4 and the group has no substituent, and a pharmaceutically acceptable salt thereof.

57. The compound according to claim 53, wherein p in the group: --(CH.sub.2).sub.p -- is 5, and a pharmaceutically acceptable salt thereof.

58. The compound according to claim 54, wherein q in the group: --CH.dbd.CH--(CH.sub.2).sub.q -- is 1, and a pharmaceutically acceptable salt thereof.

59. The compound according to claim 54, wherein q in the group: --CH.dbd.CH--(CH.sub.2).sub.q -- is 2, and a pharmaceutically acceptable salt thereof.

60. The compound according to claim 54, wherein q in the group: --CH.dbd.CH.dbd.(CH.sub.2).sub.q -- is 3, and a pharmaceutically acceptable salt thereof.

61. The compound according to claim 53 wherein the heterocyclic group of the formula: ##STR1222## is 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, and a pharmaceutically acceptable salt thereof.

62. 1-[4-(2-Methylbenzoyl amino)benzoyl]-4-methyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine.

63. The compound according to claim 53 wherein the heterocyclic group of the formula ##STR1223## is 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, and a pharmaceutically acceptable salt thereof.
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