Claims
- 1. A compound represented by the formula (II), or a salt thereof, ##STR20## wherein --R represents
- hydrogen;
- C.sub.1-6 alkyl optionally substituted by halogen, hydroxyl, C.sub.3-7 cycloalkyl or C.sub.1-4 alkoxy;
- phenyl C.sub.1-4 alkyl, of which the hydrogen atoms on the benzene ring may be optionally substituted by halogen, hydroxyl, nitro, C.sub.1-4 alkyl or C.sub.1-4 alkoxy; or
- a protective group of the triazole group;
- --R.sup.2, R.sup.3, R.sup.4 and R.sup.5, which may be the same or different, represent any one of the following (a)-(v):
- (a) hydrogen;
- (b) halogen;
- (c) hydroxyl which may be protected;
- (d) cyano;
- (e) nitro;
- (f) thiol;
- (g) formyl;
- (h) C.sub.1-12 alkyl optionally substituted by halogen, hydroxyl or C.sub.3-7 cycloalkyl;
- (i) phenyl optionally substituted by C.sub.1-4 alkyl;
- (j) phenyl C.sub.1-4 alkyl, of which the hydrogen atoms on the benzene ring may be optionally substituted by halogen, hydroxyl, nitro, amino, sulfonyl, C.sub.1-4 alkyl or C.sub.1-4 alkoxy;
- (k) C.sub.2-12 alkenyl, which includes one or more carbon-carbon double bonds and may be optionally substituted by
- (1) halogen,
- (2) cyano,
- (3) C.sub.3-7 cycloalkyl,
- (4) phenyl,
- (5) a group--COR.sup.9, wherein R.sup.9 represents
- hydrogen,
- C.sub.1-6 alkyl, or
- phenyl optionally substituted by halogen, hydroxyl, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,
- (6) a group--COOR.sup.10, wherein R.sup.10 represents hydrogen or C.sub.1-6 alkyl,
- (7) a group--CONR.sup.11 R.sup.12, wherein R.sup.11 and R.sup.12, which may be the same or different, represent
- (i) hydrogen,
- (ii) C.sub.1-6 alkyl optionally substituted by hydroxyl;
- C.sub.1-4 alkoxy; amino which may be optionally substituted by C.sub.1-4 alkyl, C.sub.1-6 alkylcarbonyl, benzoyl, .alpha.-naphthoyl, .beta.-naphthoyl or sulfonyl;
- phenyl which may be optionally substituted by halogen, hydroxyl, C.sub.1-4 alkyl (which may be optionally substituted by a saturated 5-7 membered heterocyclic ring containing one or two nitrogen atoms, which heterocyclic ring is selected from the group consisting of piperidino, 4-piperidinyl, 1-pyrrolidinyl, piperadinyl and morpholino and which may be optionally substituted by C.sub.1-4 alkyl), C.sub.1-4 alkoxy or carboxyl; or
- a saturated or unsaturated 5-7 membered heterocyclic ring containing one or more of oxygen atoms, nitrogen atoms or sulfur atoms, which heterocyclic ring is selected from the group consisting of pyridine, imidazole, oxazole, thiazole, pyrimidine, furan, thiophene, pyrrole, pyrrolidine, piperidine, tetrahydrofuran, oxazoline, quinoline and isoquinoline and which heterocyclic ring may be optionally substituted by C.sub.1-4 alkyl or phenyl C.sub.1-4 alkyl or may be a bicyclic ring fused with another ring, or
- (iii) phenyl, or
- (iv) a saturated or unsaturated 5-7 membered heterocyclic ring Which is formed by R.sup.11 and R.sup.12 together wish the nitrogen atom R.sup.11 and R.sup.12 attached thereto and may further contain ore or more of oxygen atoms, nitrogen atoms or sulfur atoms, which heterocyclic ring is selected from the group consisting of tetrazole, thiazole, imidazole, pyridine, pyrimidine and pyrazine and which heterocyclic ring may be optionally substituted by C.sub.1-4 alkyl or phenyl C.sub.1-4 alkyl or may be a bicyclic ring fused with another ring;
- (l) C.sub.1-12 alkoxy optionally substituted by
- (1) halogen,
- (2) hydroxyl,
- (3) cyano,
- (4) C.sub.3-7 cycloalkyl,
- (5) epoxy,
- (6) phenyl optionally substituted by halogen, hydroxyl, nitro, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,
- (7) C.sub.1-4 alkoxy,
- (8) phenoxy optionally substituted by halogen, hydroxyl, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or carboxyl,
- (9) amino optionally substituted by C.sub.1-4 alkyl, C.sub.1-6 alkylcarbonyl, benzoyl, .alpha.-naphthoyl, .beta.-naphthoyl or sulfonyl,
- (10) a group--COR.sup.13, wherein R.sup.13 represents
- hydrogen,
- C.sub.1-6 alkyl,
- phenyl optionally substituted by halogen, hydroxyl, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, or
- phenyl C.sub.1-4 alkyl, of which the hydrogen atoms on the benzene ring may be optionally substituted by halogen, hydroxyl, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or carboxyl,
- (11) a group--COOR.sup.14, wherein R.sup.14 represents hydrogen or C.sub.1-6 alkyl,
- (12) a group--CONR.sup.15 R.sup.16, wherein R.sup.15 and R16 may be the same or different and represent
- hydrogen,
- C.sub.1-6 alkyl optionally substituted by hydroxyl, C.sub.1-4 alkoxy, or amino (which may be optionally substituted by C.sub.1-4 alkyl, C.sub.1-6 alkylcarbonyl, benzoyl, .alpha.-naphthoyl, .beta.-naphthoyl or sulfonyl), or phenyl, or
- (13) a saturated or unsaturated 5-7 membered heterocyclic ring containing one or more of oxygen atoms, nitrogen atoms or sulfur atoms, which heterocyclic ring is selected from the group consisting of piperidino, 4-piperidinyl, 1-pyrrolidinyl, piperazinyl and morpholino and which heterocyclic ring may be optionally substituted by C.sub.1-4 alkyl or phenyl C.sub.1-4 alkyl, or may be a bicyclic ring fused with another ring,
- (m) phenoxy optionally substituted by hydroxyl, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or carboxyl;
- (n) C.sub.2-12 alkenyloxy optionally substituted by C.sub.1-4 alkyl or phenyl;
- (o) C.sub.1-12 alkylthio optionally substituted by hydroxyl, C.sub.3-7 cycloalkyl, C.sub.2-4 alkenyl, C.sub.1-4 alkoxy or benzyl;
- (p) a group--C.dbd.N--OR.sup.26, wherein R.sup.6 represents
- hydrogen,
- C.sub.1-6 alkyl,
- phenyl C.sub.1-4 alkyl, or
- phenyl;
- (q) a group--(CH.sub.2).sub.m OR.sup.17, wherein m is an integer of 1-4, and R.sup.17 represents
- hydrogen,
- C.sub.1-6 alkyl optionally substituted by halogen, hydroxyl or C.sub.3-7 cycloalkyl,
- phenyl C.sub.1-4 alkyl, of which the hydrogen atoms of the benzene ring may be optionally substituted by hydroxyl,
- C.sub.1-4 alkyl or C.sub.1-4 alkoxy,
- phenyl, or
- C.sub.1-4 alkylcarbonyl;
- (r) a group--(CH.sub.2).sub.k --COR.sup.18, wherein k is an integer of 1-4, and R.sup.18 represents
- hydrogen,
- C.sub.1-12 alkyl optionally substituted by hydroxyl, C.sub.3-7 cycloalkyl or C.sub.1-4 alkoxy, or
- phenyl optionally substituted by halogen, hydroxyl, nitro, C.sub.1-4 alkyl or C.sub.1-4 alkoxy;
- (s) a group--(CH.sub.2).sub.j --COOR.sup.19, wherein j is an integer of 0-4, and R.sup.19 represents
- hydrogen,
- C.sub.1-12 alkyl optionally substituted by halogen, hydroxyl or
- C.sub.1-4 alkoxy, or
- benzyl, of which the hydrogen atoms on the benzene ring may be optionally substituted by C.sub.3-7 cycloalkyl, C.sub.2-4 alkenyl,
- halogen, hydroxyl, nitro, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, or
- a protective group of carboxyl;
- (t) a group--(CH.sub.2).sub.p --NR .sup.20 R.sup.21, wherein p is an integer of 0-4, and R.sup.20 and R.sup.21 may be the same or different and represent
- (1) hydrogen,
- (2) C.sub.1-6 alkyl optionally substituted by hydroxyl, amino (which may be optionally substituted by C.sub.1-4 alkyl, C.sub.1-6 alkylcarbonyl, benzoyl, .alpha.-naphthoyl, .beta.-naphthoyl or sulfonyl), C.sub.3-7 cycloalkyl or C.sub.1-4 alkoxy,
- (3) phenyl C.sub.1-4 alkyl, of which the hydrogen atoms on the benzene ring may be optionally substituted by halogen, hydroxyl, nitro, cyano, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or carboxyl,
- (4) a group--COR.sup.27, wherein R.sup.27 represents
- hydrogen,
- C.sub.1-4 alkyl optionally substituted by hydroxyl or carboxyl, or
- C.sub.3-7 cycloalkyl optionally substituted by hydroxyl or carboxyl, or
- (5) a group--SO.sub.2 R.sup.28, wherein R.sup.28 represents
- C.sub.1-4 alkyl,
- phenyl optionally substituted by halogen, hydroxyl,
- nitro, cyano, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or carboxyl, or
- amino optionally substituted by C.sub.1-4 alkyl, C.sub.1-6 alkylcarbonyl, benzoyl, .alpha.-naphthoyl, .beta.-naphthoyl or sulfonyl, or
- (6) a saturated or unsaturated 5-7 membered heterocyclic ring formed by R.sup.20 and R.sup.21 together with the nitrogen atom R.sup.20 and R.sup.21 attached thereto, which heterocyclic ring may further contain one or more of oxygen atoms, nitrogen atoms or sulfur atoms, which heterocyclic ring is selected from the group consisting of piperazino, piperidino, morpholino, succinimido, indolyl, isoindolyl, phthalimido and benzothiazolyl and may be optionally substituted by C.sub.1-4 alkyl or carbonyl;
- (u) a group--(CH.sub.2).sub.q --CONR.sup.22 R.sup.23, wherein
- q is an integer of 0-4, and
- R.sup.22 and R.sup.23 may be the same or different and represent hydrogen,
- C.sub.1-6 alkyl (optionally substituted by C.sub.3-7 cycloalkyl),
- C.sub.3-7 cycloalkyl, phenyl (optionally substituted by hydroxyl, C.sub.1-4 alkyl or C.sub.1-4 alkoxy),
- sulfonyl, or
- a saturated or unsaturated 5-7 membered heterocyclic ring formed by R.sup.22 and R.sup.23 together with the nitrogen atom R.sup.22 and R.sup.23 attached thereto, which heterocyclic ring may further contain one or more of oxygen atoms, nitrogen atoms or sulfur atoms, which heterocyclic ring is selected from the group consisting of piperazino, piperidino, morpholino, succinimido, indolyl, isoindolyl, phthalimido and benzothiazolyl and may be optionally substituted by C.sub.1-4 alkyl;
- (v) a group--NR.sup.29 R.sup.30, wherein R.sup.29 and R.sup.30, which may be the same or different, represent
- (1) hydrogen,
- (2) C.sub.1-6 alkyl optionally substituted by
- halogen,
- hydroxyl,
- C.sub.1-4 alkoxy, or
- amino which may be optionally substituted by C.sub.1-4 alkyl, C.sub.1-6 alkylcarbonyl, benzoyl, .alpha.-naphthoyl, .beta.-naphthoyl or sulfonyl,
- (3) phenyl C.sub.1-4 alkyl, of which the hydrogen atoms on the benzene ring may be optionally substituted by halogen, hydroxyl, nitro, cyano, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,
- (4) a group--COR.sup.31, wherein R.sup.31 represents
- hydrogen,
- C.sub.1-6 alkyl optionally substituted by halogen, hydroxyl,
- C.sub.1-4 alkyl or C.sub.1-4 alkoxy, or phenyl optionally substituted by halogen, hydroxyl, nitro, cyano, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,
- (5) a group--COOR.sup.32, ;herein R.sup.32 represents
- C.sub.1-6 alkyl, or
- phenyl which may be optionally substituted by halogen,
- hydroxyl, nitro, cyano, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,
- (6) a group--CONR.sup.34 R.sup.35, wherein R.sup.34 and R.sup.35 may be the same or different and represent
- hydrogen,
- C.sub.1-6 alkyl optionally substituted by C.sub.1-4 alkyl or
- amino which may be optionally substituted by C.sub.1-4
- alkyl, C.sub.1-6 alkylcarbonyl, benzoyl, .alpha.-naphthoyl, .beta.-naphthoyl or sulfonyl, or
- phenyl, or
- (7) a group SO.sub.2 R.sup.36, wherein R.sup.36 represents
- C.sub.1-6 alkyl,
- phenyl optionally substituted by C.sub.1-4 alkyl, C.sub.1-4 alkoxy or halogen, or
- .alpha.- or .beta.-naphthyl, and
- --R.sup.41 represents hydrogen, C.sub.1-6 alkyl which may be optionally substituted, or a protective group of carboxyl.
- 2. A compound represented by the formula (III), or a salt thereof, ##STR21## wherein --R represents
- hydrogen;
- C.sub.1-6 optionally substituted by halogen, hydroxyi, C.sub.3-7 cycloalkyl or C.sub.1-4 alkoxy;
- phenyl C.sub.1-4 alkyl, of which the hydrogen atoms on the benzene ring may be optionally substituted by halogen, hydroxyl, nitro, C.sub.1-4 alkyl or C.sub.1-4 alkoxy; or
- a protective group of the triazole group;
- --R.sup.1 represents
- hydrogen;
- hydroxyl;
- C.sub.1-12 alkyl optionally substituted by halogen, hydroxyl or C.sub.3-7 cycloalkyl;
- phenyl C.sub.1-4 alkyl, of which the hydrogen atoms on the benzene ring may be optionally substituted by halogen, hydroxyl, nitro, C.sub.1-4 alkyl or C.sub.1-4 alkoxy;
- --R.sup.2, R.sup.3, R.sup.4 and R.sup.5, which may be the same or different, represent any one of the following (a)-(v):
- (a) hydrogen;
- (b) halogen;
- (c) hydroxyl which may be protected;
- (d) cyano;
- (e) nitro;
- (f) thiol;
- (g) formyl;
- (h) C.sub.1-12 alkyl optionally substituted by halogen, hydroxyl or C.sub.3-7 cycloalkyl;
- (i) phenyl optionally substituted by C.sub.1-4 alkyl;
- (j) phenyl C.sub.1-4 alkyl, of which the hydrogen atoms on the benzene ring may be optionally substituted by halogen, hydroxyl, nitro, amino, sulfonyl, C.sub.1-4 alkyl or C.sub.1-4 alkoxy;
- (k) C.sub.2-12 alkenyl, which includes one or more carbon-carbon double bonds and may be optionally substituted by
- (1) halogen,
- (2) cyano,
- (3) C.sub.3-7 cycloalkyl,
- (4) phenyl,
- (5) a group--COR.sup.9, wherein R.sup.9 represents
- hydrogen,
- C.sub.1-6 alkyl, or
- phenyl optionally substituted by halogen, hydroxyl, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,
- (6) a group--COOR.sup.10, wherein R.sup.10 represents hydrogen or C.sub.1-6 alkyl,
- (7) a group--CONR.sup.11 R.sup.12, wherein R.sup.11 and R.sup.12, which may be the same or different, represent
- (i) hydrogen,
- (ii) C.sub.1-6 alkyl optionally substituted by hydroxyl;
- C.sub.1-4 alkoxy;
- amino which may be optionally substituted by C.sub.1-4 alkyl, C.sub.1-6 alkylcarbonyl, benzoyl, .alpha.-naphthoyl, .beta.-naphthoyl or sulfonyl;
- phenyl which may be optionally substituted by halogen, hydroxyl, C.sub.1-4 alkyl (which may be optionally substituted by a saturated 5-7 membered heterocyclic ring containing one or two nitrogen atoms, which heterocyclic ring is selected from the group consisting of piperidino, 4-piperidinyl, 1-pyrrolidinyl, piperadinyl and morpholino and which may be optionally substituted by C.sub.1-4 alkyl), C.sub.1-4 alkoxy or carboxyl; or
- a saturated or unsaturated 5-7 membered heterocyclic ring containing one or more of oxygen atoms, nitrogen atoms or sulfur atoms, which heterocyclic ring is selected from the group consisting of pyridine, imidazole, oxazole, thiazole, pyrimidine, furan, thiophene, pyrrole, pyrrolidine, piperidine, tetrahydrofuran, oxazoline, quinoline and isoquinoline and which heterocyclic ring may be optionally substituted by C.sub.1-4 alkyl or phenyl C.sub.1-4 alkyl or may be a bicyclic ring fused With another ring, or
- (iii) phenyl, or
- (iv) a saturated or unsaturated 5-7 membered heterocyclic ring which is formed by R.sup.11 and R.sup.12 together with the nitrogen atom R.sup.11 and R.sup.12 attached thereto and may further contain one or more of oxygen atoms, nitrogen atoms or sulfur atoms, which heterocyclic ring is selected from the group consisting of tetrazole, thiazole, imidazole, pyridine, pyrimidine and pyrazine and which heterocyclic ring may be optionally substituted by C.sub.1-4 alkyl or phenyl C.sub.1-4 alkyl or may be a bicyclic ring fused with another ring;
- (l) C.sub.1-12 alkoxy optionally substituted by
- (1) halogen,
- (2) hydroxyl,
- (3) cyano,
- (4) C.sub.3 -.sub.7 cycloalkyl,
- (5) epoxy,
- (6) phenyl optionally substituted by halogen, hydroxyl, nitro, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,
- (7) C.sub.1-4 alkoxy,
- (8) phenoxy optionally substituted by halogen, hydroxyl, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or carboxyl,
- (9) amino optionally substituted by C.sub.1-4 alkyl, C.sub.1-6 alkylcarbonyl, benzoyl, .alpha.-naphthoyl, .beta.-naphthoyl or sulfonyl,
- (10) a group--COR.sup.13, wherein R.sup.13 represents
- hydrogen,
- C.sub.1-6 alkyl,
- phenyl optionally substituted by halogen, hydroxyl, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, or
- phenyl C.sub.1-4 alkyl, of which the hydrogen atoms on the benzene ring nay be optionally substituted by halogen, hydroxyl, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or carboxyl,
- (11) a group--COOR.sup.14, wherein R.sup.14 represents hydrogen or C.sub.1-6 alkyl,
- (12) a group--CONR.sup.15 R.sup.16, wherein R.sup.15 and R .sup.16 may be the same or different and represent
- hydrogen, C.sub.1-6 alkyl optionally substituted by hydroxyl, C.sub.1-4 alkoxy, or amino (which may be optionally substituted by C.sub.1-4 alkyl, C.sub.1-6 alkylcarbonyl, benzoyl, .alpha.-naphthoyl, .beta.-naphthoyl or sulfonyl), or phenyl, or
- (13) a saturated or unsaturated 5-7 membered heterocyclic ring containing one or more of oxygen atoms, nitrogen atoms or sulfur atoms, which heterocyclic ring is selected from the group consisting of piperidino, 4-piperidinyl, 1-pyrrolidinyl, piperazinyl and morpholino and which heterocyclic ring may be optionally substituted by C.sub.1-4 alkyl or phenyl C.sub.1-4 alkyl, or may be a bicyclic ring fused with another ring,
- (m) phenoxy optionally substituted by hydroxyl, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or carboxyl;
- (n) C.sub.2-12 alkenyloxy optionally substituted by C.sub.1-4 alkyl or phenyl;
- (o) C.sub.1-12 alkylthio optionally substituted by hydroxyl, C.sub.3-7 cycloalkyl, C.sub.2-4 alkenyl, C.sub.1-4 alkoxy or benzyl;
- (p) a group--C.dbd.N--OR.sup.26, wherein R.sup.26 represents
- hydrogen,
- C.sub.1-6 alkyl,
- phenyl C.sub.1-4 alkyl, or
- phenyl;
- (q) a group--(CH.sub.2).sub.m OR.sup.17, wherein m is an integer of 1-4, and R.sup.17 represents
- hydrogen,
- C.sub.1-6 alkyl optionally substituted by halogen, hydroxyl or C.sub.3-7 cycloalkyl, phenyl C.sub.1-4 alkyl, of which the hydrogen atoms of the benzene ring may be optionally substituted by hydroxyl,
- C.sub.1-4 alkyl or C.sub.1-4 alkoxy,
- phenyl, or
- C.sub.1-4 alkylcarbonyl;
- (r) a group--(CH.sub.2).sub.k --COR.sup.18 wherein k is an integer of 1-4, and R.sup.18 represents
- hydrogen,
- C.sub.1-12 alkyl optionally substituted by hydroxyl, C.sub.3-7
- cycloalkyl or C.sub.1-4 alkoxy, or
- phenyl optionally substituted by halogen, hydroxyl, nitro, C.sub.1-4 alkyl or C.sub.1-4 alkoxy;
- (s) a group--(CH.sub.2).sub.j --COOR.sup.19, wherein j is an integer of 0-4, and R.sup.19 represents
- hydrogen,
- C.sub.1-12 alkyl optionally substituted by halogen, hydroxyl or
- C.sub.1-4 alkoxy, or
- benzyl, of which the hydrogen atoms on the benzene ring may be optionally substituted by C.sub.3-7 cycloalkyl, C.sub.2-4 alkenyl,
- halogen, hydroxyl, nitro, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, or
- a protective group of carboxyl;
- (t) a group--(CH.sub.2).sub.p --NR.sup.20 R.sup.21, wherein p is an integer of 0-4, and R.sup.20 and R.sup.21 may be the same or different and represent
- (1) hydrogen,
- (2) C.sub.1-6 alkyl optionally substituted by hydroxyl, amino (which may be optionally substituted by C.sub.1-4 alkyl, C.sub.1-6 alkylcarbonyl, benzoyl, .alpha.-naphthoyl, .beta.-naphthoyl or sulfonyl), C.sub.3-7 cycloalkyl or C.sub.1-4 alkoxy,
- (3) phenyl C.sub.1-4 alkyl, of which the hydrogen atoms on the benzene ring may be optionally substituted by halogen, hydroxyl, nitro, cyano, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or carboxyl,
- (4) a group--CCR.sup.27, wherein R.sup.27 represents hydrogen,
- C.sub.1-4 alkyl optionally substituted by hydroxyl or carboxyl, or
- C.sub.3-7 cycloalkyl optionally substituted by hydroxyl or carboxyl, or
- (5) a group--SO.sub.2 R.sup.28, wherein R.sup.28 represents C.sub.1-4 alkyl,
- phenyl optionally substituted by halogen, hydroxyl, nitro, cyano, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or carboxyl, or
- amino optionally substituted by C.sub.1-4 alkyl, C.sub.1-6 alkylcarbonyl, benzoyl, .alpha.-naphthoyl, .beta.-naphthoyl or sulfonyl, or
- (6) a saturated or unsaturated 5-7 membered heterocyclic ring formed by R.sup.20 and R.sup.21 together with the nitrogen atom R.sup.20 and R.sup.21 attached thereto, which heterocyclic ring may further contain one or more of oxygen atoms, nitrogen atoms or sulfur atoms, which heterocyclic ring is selected from the group consisting of piperazino, piperidino, morpholino, succinimido, indolyl, isoindolyl, phthalimido and benzothiazolyl and may be optionally substituted by C.sub.1-4 alkyl or carbonyl;
- (u) a group--(CH.sub.2).sub.q --CONR.sup.22 R.sup.23, wherein
- q is an integer of 0-4, and
- R.sup.22 and R.sup.23 may be the same or different and represent hydrogen,
- C.sub.1-6 alkyl (optionally substituted by C.sub.3-7 cycloalkyl),
- C.sub.3-7 cycloalkyl,
- phenyl (optionally substituted by hydroxyl, C.sub.1-4 alkyl
- or C.sub.1-4 alkoxy),
- sulfonyl, or
- a saturated or unsaturated 5-7 membered heterocyclic ring formed by R.sup.22 and R.sup.23 together with the nitrogen atom R.sup.22 and R.sup.23 attached thereto, which heterocyclic ring may further contain one or more of oxygen atoms, nitrogen atoms or sulfur atoms, which heterocyclic ring is selected from the group consisting of piperazino, piperidino, morpholino, succinimido, indolyl, isoindolyl, phthalimido and benzothiazolyl and may be optionally substituted by C.sub.1-4 alkyl;
- (v) a group--NR.sup.29 R.sup.30, wherein R.sup.29 and R.sup.30, which may be the same or different, represent
- (1) hydrogen,
- (2) C.sub.1-6 alkyl optionally substituted by
- halogen,
- hydroxyl,
- C.sub.1-4 alkoxy, or
- amino which may be optionally substituted by C.sub.1-4 alkyl, C.sub.1-4 alkylcarbonyl, benzoyl, .alpha.-naphthoyl, .beta.-naphthoyl or sulfonyl,
- (3) phenyl C.sub.1-4 alkyl, of which the hydrogen atoms on the benzene ring may be optionally substituted by halogen, hydroxyl, nitro, cyano, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,
- (4) a group--COR.sup.31, wherein R.sup.31 represents hydrogen,
- C.sub.1-6 alkyl optionally substituted by halogen, hydroxyl, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, or
- phenyl optionally substituted by halogen, hydroxyl, nitro, cyano, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,
- (5) a group--COOR.sup.32, wherein R.sup.32 represents C.sub.1-6 alkyl, or
- phenyl which may be optionally substituted by halogen, hydroxyl, nitro, cyano, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,
- (6) a group--CONR.sup.34 R.sup.35, wherein R.sup.34 and R.sup.35 may be the same or different and represent
- hydrogen,
- C.sub.1-6 alkyl optionally substituted by C.sub.1-4 alkyl or
- amino which may be optionally substituted by C.sub.1-4 alkyl, C.sub.1-6 alkylcarbonyl, benzoyl, .alpha.-naphthoyl, .beta.-naphthoyl or sulfonyl, or phenyl, or
- (7) a group SO.sub.2 R.sup.36, wherein R.sup.36 represents
- C.sub.1-6 alkyl,
- phenyl optionally substituted by C.sub.1-4 alkyl, C.sub.1-4 alkoxy
- or halogen, or
- .alpha.- or .beta.-naphthyl, and
- --R.sup.41 represents hydrogen, C.sub.1-6 alkyl which may be optionally substituted, or a protective group of carboxyl.
- 3. A compound represented by the formula (IV), or a salt thereof, ##STR22## wherein --R represents
- hydrogen;
- C.sub.1-6 alkyl optionally substituted by halogen, hydroxyl, C.sub.3-7 cycloalkyl or C.sub.1-4 alkoxy;
- phenyl C.sub.1-4 alkyl, of which the hydrogen atoms on the benzene ring may be optionally substituted by halogen, hydroxyl, nitro, C.sub.1-4 alkyl or C.sub.1-4 alkoxy; or
- a protective group of the triazole group;
- --R.sup.1 represents
- hydrogen;
- hydroxyl;
- C.sub.1-12 alkyl optionally substituted by halogen, hydroxyl or C.sub.3-7 cycloalkyl;
- phenyl C.sub.1-4 alkyl, of which the hydrogen atoms on the benzene ring may be optionally substituted by halogen, hydroxyl, nitro, C.sub.1-4 alkyl or C.sub.1-4 alkoxy;
- --R.sup.2, R.sup.3, R.sup.4 and R.sup.5, which may be the same or different, represent any one of the following (a)-(v):
- (a) hydrogen;
- (b) halogen;
- (c) hydroxyl which may be protected;
- (d) cyano;
- (e) nitro;
- (f) thiol;
- (g) formyl;
- (h) C.sub.1-12 alkyl optionally substituted by halogen, hydroxyl or C.sub.3-7 cycloalkyl;
- (i) phenyl optionally substituted by C.sub.1-4 alkyl;
- (j) phenyl C.sub.1-4 alkyl, of which the hydrogen atoms on the benzene ring may be optionally substituted by halogen, hydroxyl, nitro, amino, sulfonyl, C.sub.1-4 alkyl or C.sub.1-4 alkoxy;
- (k) C.sub.2-12 alkenyl, which includes one or more carbon--carbon double bonds and may be optionally substituted by
- (1) halogen,
- (2) cyano,
- (3) C.sub.3-7 cycloalkyl,
- (4) phenyl,
- (5) a group--COR.sup.9, wherein R.sup.9 represents
- hydrogen,
- C.sub.1-6 alkyl, or
- phenyl optionally substituted by halogen, hydroxyl, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,
- (6) a group--COOR.sup.10, wherein R.sup.10 represents hydrogen or C.sub.1-6 alkyl,
- (7) a group--CONR.sup.11 R.sup.12, wherein R.sup.11 and R.sup.12, which may be the same or different, represent
- (i) hydrogen,
- (ii) C.sub.1-6 alkyl optionally substituted by hydroxyl;
- C.sub.1-4 alkoxy;
- amino which may be optionally substituted by C.sub.1-4 alkyl, C.sub.1-6 alkylcarbonyl, benzoyl, .alpha.-naphthoyl, .beta.-naphthoyl or sulfonyl;
- phenyl which may be optionally substituted by halogen, hydroxyi, C.sub.1-4 alkyl (which may be optionally substituted by a saturated 5-7 membered heterocyclic ring containing one or two nitrogen atoms, which heterocyclic ring is selected from the group consisting of piperidino, 4-piperidinyl, 1-pyrrolidinyl, piperadinyl and morpholino and which may be optionally substituted by C.sub.1-4 alkyl), C.sub.1-4 alkoxy or carboxyl; or
- a saturated or unsaturated 5-7 membered heterocyclic ring containing one or more of oxygen atoms, nitrogen atoms or sulfur atoms, which heterocyclic ring is selected from the group consisting of pyridine, imidazole, oxazole, thiazole, pyrimidine, furan, thiophene, pyrrole, pyrrolidine, piperidine, tetrahydrofuran, oxazoline, quinoline and isoquinoline and which heterocyclic ring may be optionally substituted by C.sub.1-4 alkyl or phenyl C.sub.1-4 alkyl or may be a bicyclic ring fused with another ring, or
- (iii) phenyl, or
- (iv) a saturated or unsaturated 5-7 membered heterocyclic ring which is formed by R.sup.11 and R.sup.12 together with the nitrogen atom R.sup.11 rand R.sup.12 attached thereto and may further contain one or more of oxygen atoms, nitrogen atoms or sulfur atoms, which heterocyclic ring is selected from the group consisting of tetrazole, thiazole, imidazole, pyridine, pyrimidine and pyrazine and which heterocyclic ring may be optionally substituted by C.sub.1-4 alkyl or phenyl C.sub.1-4 alkyl or may be a bicyclic ring fused with another ring;
- (l) C.sub.1-2 alkoxy optionally substituted by
- (1) halogen,
- (2) hydroxyl,
- (3) cyano,
- (4) C.sub.3-7 cycloalkyl,
- (5) epoxy,
- (6) phenyl optionally substituted by halogen, hydroxyl, nitro, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,
- (7) C.sub.1-4 alkoxy,
- (8) phenoxy optionally substituted by halogen, hydroxyl, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or carboxyl,
- (9) amino optionally substituted by C.sub.1-4 alkyl, C.sub.1-6 alkylcarbonyl, benzoyl, .alpha.-naphthoyl, .beta.-naphthoyl or sulfonyl,
- (10) a group--CR.sup.13, wherein R.sup.13 represents hydrogen,
- C.sub.1-6 alkyl,
- phenyl optionally substituted by halogen, hydroxyl, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, or
- phenyl C.sub.1-4 alkyl, of which the hydrogen atoms on the benzene ring may be optionally substituted by halogen, hydroxyl, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or carboxyl,
- (11) a group--COOR.sup.14, wherein R.sup.14 represents hydrogen or C.sub.1-6 alkyl,
- (12) a group--CONR.sup.15 R.sup.16, wherein R.sup.15 and R.sup.16 may be the same or different and represent
- hydrogen,
- C.sub.1-6 alkyl optionally substituted by hydroxyl, C.sub.1-4 alkoxy, or amino (which may be optionally substituted by C.sub.1-4 alkyl, C.sub.1-6 alkylcarbonyl, benzoyl, .alpha.-naphthoyl, .beta.-naphthoyl or sulfonyl), or
- phenyl, or
- (13) a saturated or unsaturated 5-7 membered heterocyclic ring containing one or more of oxygen atoms, nitrogen atoms or sulfur atoms, which heterocyclic ring is selected from the group consisting of piperidino, 4-piperidinyl, 1-pyrrolidinyl, piperazinyl and morpholino and which heterocyclic ring may be optionally substituted by C.sub.1-4 alkyl or phenyl C.sub.1-4 alkyl, or may be a bicyclic ring fused with another ring,
- (m) phenoxy optionally substituted by hydroxyl, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or carboxyl;
- (n) C.sub.2-12 alkenyloxy optionally substituted by C.sub.1-4 alkyl or phenyl;
- (o) C.sub.1-12 alkylthio optionally substituted by hydroxyl, C.sub.3-7 cycloalkyl, C.sub.2-4 alkenyl, C.sub.1-4 alkoxy or benzyl;
- (p) a group--C.dbd.N--OR.sup.26, wherein R.sup.26 represents
- hydrogen,
- C.sub.1-6 alkyl,
- phenyl C.sub.1-4 alkyl, or
- phenyl;
- (q) a group--(CH.sub.2).sub.m OR.sup.17, wherein m is an integer of 1-4, and R.sup.17 represents
- hydrogen,
- C.sub.1-6 alkyl optionally substituted by halogen, hydroxyl or C.sub.3-7 cycloalkyl,
- phenyl C.sub.1-4 alkyl, of which the hydrogen atoms of the benzene ring may be optionally substituted by hydroxyl, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,
- phenyl, or
- C.sub.1-4 alkylcarbonyl;
- (r) a group--(CH.sub.2).sub.k --COR.sup.18, wherein k is an integer of 1-4, and R.sup.18 represents
- hydrogen,
- C.sub.1-12 alkyl optionally substituted by hydroxyl, C.sub.3-7 cycloalkyl or C.sub.1-4 alkoxy, or
- phenyl optionally substituted by halogen, hydroxyl, nitro, C.sub.1-4 alkyl or C.sub.1-4 alkoxy;
- (s) a group--(CH.sub.2).sub.j --COOR.sup.19, wherein j is an integer of 0-4, and R.sup.19 represents
- hydrogen,
- C.sub.1-12 alkyl optionally substituted by halogen, hydroxyl or
- C.sub.1-4 alkoxy, or
- benzyl, of which the hydrogen atoms on the benzene ring may be optionally substituted by C.sub.3-7 cycloalkyl, C.sub.1-4 alkenyl,
- halogen, hydroxyl, nitro, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, or a protective group of carboxyl;
- (t) a group--(CH.sub.2).sub.p --NR.sup.20 R.sup.21, wherein p is an integer of 0-4, and R.sup.20 and R.sup.21 may be the same or different and represent
- (1) hydrogen,
- (2) C.sub.1-6 alkyl optionally substituted by hydroxyl, amino (which may be optionally substituted by C.sub.1-4 alkyl, C.sub.1-6 alkylcarbonyl, benzoyl, .alpha.-naphthoyl, .beta.-naphthoyl or sulfonyl), C.sub.3-7 cycloalkyl or C.sub.1-4 alkoxy,
- (3) phenyl C.sub.1-4 alkyl, of which the hydrogen atoms on the benzene ring may be optionally substituted by halogen, hydroxyl, nitro, cyano, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or carboxyl,
- (4) a group--COR.sup.27, wherein R.sup.27 represents hydrogen,
- C.sub.1-4 alkyl optionally substituted by hydroxyl or carboxyl, or
- C.sub.3-7 cycloalkyl optionally substituted by hydroxyl or carboxyl, or
- (5) a group--SO.sub.2 R.sup.28, wherein R.sup.28 represents
- C.sub.1-4 alkyl,
- phenyl optionally substituted by halogen, hydroxyl, nitro, cyano, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or carboxyl, or
- amino optionally substituted by C.sub.1-4 alkyl, C.sub.1-6
- alkylcarbonyl, benzoyl, .alpha.-naphthoyl, .beta.-naphthoyl or sulfonyl, or
- (6) a saturated or unsaturated 5-7 membered heterocyclic ring formed by R.sup.20 and R.sup.21 together with the nitrogen atom R.sup.20 and R.sup.21 attached thereto, which heterocyclic ring may further contain one or more of oxygen atoms, nitrogen atoms or sulfur atoms, which heterocyclic ring is selected from the group consisting of piperazino, piperidino, morpholino, succinimido, indolyl, isoindolyl, phthalimido and benzothiazolyl and may be optionally substituted by C.sub.1-4 alkyl or carbonyl;
- (u) a group--(CH.sub.2).sub.q --CONR.sup.22 R.sup.23, wherein
- q is an integer of 0-4, and
- R.sup.22 and R.sup.23 may be the same or different and represent hydrogen,
- C.sub.1-6 alkyl (optionally substituted by C.sub.3-7 cycloalkyl),
- C.sub.3-7 cycloalkyl,
- phenyl (optionally substituted by hydroxyl, C.sub.1-4 alkyl or C.sub.1-4 alkoxy),
- sulfonyl, or
- a saturated or unsaturated 5-7 membered heterocyclic ring formed by R.sup.22 and R.sup.23 together with the nitrogen atom R.sup.22 and R.sup.23 attached thereto, which heterocyclic ring may further contain one or more of oxygen atoms, nitrogen atoms or sulfur atoms, which heterocyclic ring is selected from the group consisting of piperazino, piperidino, morpholino, succinimido, indolyl, soindolyl, phthalimido and benzothiazolyl and may be optionally substituted by C.sub.1-4 alkyl;
- (v) a group--NR.sup.29 R.sup.30, wherein R.sup.29 and R.sup.30 which may be the same or different, represent
- (1) hydrogen,
- (2) C.sub.1-6 alkyl optionally substituted by
- halogen,
- hydroxyl,
- C.sub.1-4 alkoxy, or
- amino which may be optionally substituted by C.sub.1-4 alkyl, C.sub.1-6 alkylcarbonyl, benzoyl, .alpha.-naphthoyl, .beta.-naphthoyl or sulfonyl,
- (3) phenyl C.sub.1-4 alkyl, of which the hydrogen atoms on the benzene ring may be optionally substituted by halogen, hydroxyl, nitro, cyano, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,
- (4) a group--COR.sup.31, wherein R.sup.31 represents
- hydrogen,
- C.sub.1-6 alkyl optionally substituted by halogen, hydroxyl,
- C.sub.1-4 alkyl or C.sub.1-4 alkoxy, or
- phenyl optionally substituted by halogen, hydroxyl,
- nitro, cyano, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,
- (5) a group--COOR.sup.32 wherein R.sup.32 represents
- C.sub.1-6 alkyl, or
- phenyl which may he optionally substituted by halogen,
- hydroxyl, nitro, cyano, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,
- (6) a group--CONR.sup.34 R.sup.35, wherein R.sup.34 and R.sup.35 may be the same or different and represent
- hydrogen,
- C.sub.1-6 alkyl optionally substituted by C.sub.1-4 alkyl or
- amino which may be optionally substituted by C.sub.1-4 alkyl, C.sub.1-6 alkylcarbonyl, benzoyl, .alpha.-naphthoyl, .beta.-naphthoyl or sulfonyl, or phenyl, or
- (7) a group SO.sub.2 R.sup.36, wherein R.sup.36 represents
- C.sub.1-6 alkyl,
- phenyl optionally substituted by C.sub.1-4 alkyl, C.sub.1-4 alkoxy
- or halogen, or .alpha.- or .beta.-naphthyl, and
- --R.sup.41 represents hydrogen, C.sub.1-6 alkyl which may be optionally substituted, or a protective group of carboxyl.
- 4. A compound represented by the formula (V), or a salt thereof, ##STR23## wherein --R represents
- hydrogen;
- C.sub.1-6 alkyl optionally substituted by halogen, hydroxyl, C.sub.3-7 cycloalkyl or C.sub.1-4 alkoxy;
- phenyl C.sub.1-4 alkyl, of which the hydrogen atoms on the benzene ring may be optionally substituted by halogen, hydroxyl,
- nitro, C.sub.1-4 alkyl or C.sub.1-4 alkoxy; or
- a protective group of the triazole group;
- --R.sup.1 represents
- hydrogen;
- hydroxyl;
- C.sub.1-12 alkyl optionally substituted by halogen, hydroxyl or C.sub.3-7 cycloalkyl;
- phenyl C.sub.1-4 alkyl, of which the hydrogen atoms on the benzene ring may be optionally substituted by halogen, hydroxyl, nitro, C.sub.1-4 alkyl or C.sub.1-4 alkoxy;
- --R.sup.2, R.sup.3, R.sup.4 and R.sup.5, which may be the same or different, represent any one of the following (a)-(v):
- (a) hydrogen;
- (b) halogen;
- (c) hydroxyl which may be protected;
- (d) cyano;
- (e) nitro;
- (f) thiol;
- (g) formyl;
- (h) C.sub.1-2 alkyl optionally substituted by halogen, hydroxyl or C.sub.3-7 cycloalkyl;
- (i) phenyl optionally substituted by C.sub.1-4 alkyl;
- (j) phenyl C.sub.1-4 alkyl, or which the hydrogen atoms on the benzene ring may be optionally substituted by halogen, hydroxyl, nitro, amino, sulfonyl, C.sub.1-4 alkyl or C.sub.1-4 alkoxy;
- (k) C.sub.2-12 alkenyl, which includes one or more carbon--carbon double bonds and may be optionally substituted by
- (1) halogen,
- (2) cyano,
- (3) C.sub.3-7 cycloalkyl,
- (4) phenyl,
- (5) a group--COR.sup.9, wherein R.sup.9 represents
- hydrogen,
- C.sub.1-6 alkyl, or
- phenyl optionally substituted by halogen, hydroxyl, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,
- (6) a group--COOR.sup.10, wherein R.sup.10 represents hydrogen or C.sub.1-6 alkyl,
- (7) a group--CONR.sup.11 R .sup.12, wherein R.sup.11 and R .sup.12, which may be the same or different, represent
- (i) hydrogen,
- (ii) C.sub.1-6 alkyl optionally substituted by
- hydroxyl;
- C.sub.1-4 alkoxy;
- amino which may be optionally substituted by C.sub.1-4 alkyl, C.sub.1-6 alkylcarbonyl, benzoyl, .alpha.-naphthoyl, .beta.-naphthoyl or sulfonyl;
- phenyl which may be optionally substituted by halogen, hydroxyl, C.sub.1-4 alkyl (which may be optionally substituted by a saturated 5-7 membered heterocyclic ring containing one or two nitrogen atoms, which heterocyclic ring is selected from the group consisting of piperidino, 4-piperidinyl, 1-pyrrolidinyl, piperadinyl and morpholino and which may be optionally substituted by C.sub.1-4 alkyl), C.sub.1-4 alkoxy or carboxyl; or a saturated or unsaturated 5-7 membered heterocyclic ring containing one or more of oxygen atoms, nitrogen atoms or sulfur atoms, which heterocyclic ring is selected from the group consisting of pyridine, imidazole, oxazole, thiazole, pyrimidine, furan, thiophene, pyrrole, pyrrolidine, piperidine, tetrahydrofuran, oxazoline, quinoline and isoquinoline and which heterocyclic ring may be optionally substituted by C.sub.1-4 alkyl or phenyl C.sub.1-4 alkyl or may be a bicyclic ring fused with another ring, or
- (iii) phenyl, or
- (iv) a saturated or unsaturated 5-7 membered heterocyclic ring which is formed by R.sup.11 and R.sup.12 together with the nitrogen atom R.sup.11 and R.sup.12 attached thereto and may further contain one or more of oxygen atoms, nitrogen atoms or sulfur atoms, which heterocyclic ring is selected from the group consisting of tetrazole, thiazole, imidazole, pyridine, pyrimidine and pyrazine and which heterocyclic ring -may be optionally substituted by C.sub.1-4 alkyl or phenyl C.sub.1-4 alkyl or may be a bicyclic ring fused with another ring;
- (l) C.sub.1-12 alkoxy optionally substituted by
- (1) halogen,
- (2) hydroxyl,
- (3) cyano,
- (4) C.sub.3-7 cycloalkyl,
- (5) epoxy,
- (6) phenyl optionally substituted by halogen, hydroxyl, nitro, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,
- (7) C.sub.1-4 alkoxy,
- (8) phenoxy optionally substituted by halogen, hydroxyl, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or carboxyl,
- (9) amino optionally substituted by C.sub.1-4 alkyl, C.sub.1-6 alkylcarbonyl, benzoyl, .alpha.-naphthoyl, .beta.-naphthoyl or sulfonyl,
- (10) a group--COR.sup.13, wherein R.sup.13 represents
- hydrogen,
- C.sub.1-6 alkyl,
- phenyl optionally substituted by halogen, hydroxyl, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, or
- phenyl C.sub.1-4 alkyl, of which the hydrogen atoms on the benzene ring may be optionally substituted by halogen, hydroxyl, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or carboxyl,
- (11) a group--COOR.sup.14, wherein R.sup.14 represents hydrogen or C.sub.1-6 alkyl,
- (12) a group--CONR.sup.15 R.sup.16, wherein R.sup.15 and R.sup.16 may be the same or different and represent
- hydrogen,
- C.sub.1-6 alkyl optionally substituted by hydroxyl, C.sub.1-4 alkoxy, or amino (which may be optionally substituted by C.sub.1-4 alkyl, C.sub.1-6 alkylcarbonyl, benzoyl, .alpha.-naphthoyl, .beta.-naphthoyl or sulfonyl), or
- phenyl, or
- (13) a saturated or unsaturated 5-7 membered heterocyclic ring containing one or more of oxygen atoms, nitrogen atoms or sulfur atoms, which heterocyclic ring is selected from the group consisting of piperidino, 4-piperidinyl, 1-pyrrolidinyl, piperazinyl and morpholino and which heterocyclic ring may be optionally substituted by C.sub.1-4 alkyl or phenyl C.sub.1-4 alkyl, or may be a bicyclic ring fused with another ring,
- (m) phenoxy optionally substituted by hydroxyl, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or carboxyl;
- (n) C.sub.2-12 alkenyloxy Optionally substituted by C.sub.1-4 alkyl or phenyl;
- (o) C.sub.1-12 alkylthio optionally substituted by hydroxyl, C.sub.3-7 cycloalkyl, C.sub.2-4 alkenyl, C.sub.1-4 alkoxy or benzyl;
- (p) a group--C.dbd.N--OR.sup.26, wherein R.sup.26 represents
- hydrogen,
- C.sub.1-6 alkyl,
- phenyl C.sub.1-4 alkyl, or
- phenyl;
- (q) a group--(CH.sub.2).sub.m OR.sup.17, wherein m is an integer of 1-4, and R.sup.17 represents
- hydrogen,
- C.sub.1-6 alkyl optionally substituted by halogen, hydroxyl or
- C.sub.3-7 cycloalkyl,
- phenyl C.sub.1-4 alkyl, of which the hydrogen atoms of the benzene ring may be optionally substituted by hydroxyl, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,
- phenyl, or
- C.sub.1-4 alkylcarbonyl;
- (r) a group--(CH.sub.2).sub.k --COR.sup.18, wherein k is an integer of 1-4, and R.sup.18 represents
- hydrogen,
- C.sub.1-12 alkyl optionally substituted by hydroxyl, C.sub.3-7
- cycloalkyl or C.sub.1-4 alkoxy, or
- phenyl optionally substituted by halogen, hydroxyl, nitro, C.sub.1-4 alkyl or C.sub.1-4 alkoxy;
- (s) a group--(CH.sub.2).sub.j --COOR.sup.19, wherein j is an integer of 0-4, and R.sup.19 represents
- hydrogen,
- C.sub.1-12 alkyl optionally substituted by halogen, hydroxyl or
- C.sub.1-4 alkoxy, or
- benzyl, of which the hydrogen atoms on the benzene ring may be optionally substituted by C.sub.3-7 cycloalkyl, C.sub.2-4 alkenyl,
- halogen, hydroxyl, nitro, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, or
- a protective group of carboxyl;
- (t) a group--(CH.sub.2).sub.p --NR.sup.20 R.sup.21, wherein p is an integer of 0-4, and R.sup.20 and R.sup.21 may be the same or different and represent
- (1) hydrogen,
- (2) C.sub.1-6 alkyl optionally substituted by hydroxyl, amino (which may be optionally substituted by C.sub.1-4 alkyl, C.sub.1-4 alkylcarbonyl, benzoyl, .alpha.-naphthoyl, .beta.-naphthoyl or sulfonyl), C.sub.3-7 cycloalkyl or C.sub.1-4 alkoxy,
- (3) phenyl C.sub.1-4 alkyl, of which the hydrogen atoms on the benzene ring may be optionally substituted by halogen, hydroxyl, nitro, cyano, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or carboxyl,
- (4) a group--COR.sup.27, wherein R.sup.27 represents
- hydrogen,
- C.sub.1-4 alkyl optionally substituted by hydroxyl or carboxyl, or
- C.sub.3-7 cycloalkyl optionally substituted by hydroxyl or carboxyl, or
- (5) a group--SO.sub.2 R.sup.28, wherein R.sup.28 represents
- C.sub.1-4 alkyl,
- phenyl optionally substituted by halogen, hydroxyl,
- nitro, cyano, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or carboxyl, or
- amino optionally substituted by C.sub.1-4 alkyl, C.sub.1-6 alkylcarbonyl, benzoyl, .alpha.-naphthoyl, .beta.-naphthoyl or sulfonyl, or
- (6) a saturated or unsaturated 5-7 membered heterocyclic ring formed by R.sup.20 and R.sup.21 together with the nitrogen atom R.sup.20 and R.sup.21 attached thereto, which heterocyclic ring may further contain one or more of oxygen atoms, nitrogen atoms or sulfur atoms, which heterocyclic ring is selected from the group consisting of piperazino, piperidino, morpholino, succinimido, indolyl, isoindolyl, phthalimido and benzothiazolyl and may be optionally substituted by C.sub.1-4 alkyl or carbonyl;
- (u) a group--(CH.sub.2).sub.q --CONR.sup.22 R.sup.23, wherein
- q is an integer of 0-4, and
- R.sup.22 and R.sup.23 may be the same or different and represent hydrogen,
- C.sub.1-6 alkyl (optionally substituted by C.sub.3-7 cycloalkyl), C.sub.3-7 cycloalkyl,
- phenyl (optionally substituted by hydroxyl, C.sub.1-4 alkyl or C.sub.1-4 alkoxy),
- sulfonyl, or
- a saturated or unsaturated 5-7 membered heterocyclic ring formed by R.sup.22 and R.sup.23 together with the nitrogen atom R.sup.22 and R.sup.23 attached thereto, which heterocyclic ring may further contain one or more of oxygen atoms, nitrogen atoms or sulfur atoms, which heterocyclic ring is selected from the group consisting of piperazino, piperidino, morpholino, succinimido, indolyl, isoindolyl, phthalimido and benzothiazolyl and may be optionally substituted by C.sub.1-4 alkyl;
- (v) a group--NR.sup.29 R.sup.30, wherein R.sup.29 and R.sup.30, which may be the same or different, represent
- (1) hydrogen,
- (2) C.sub.1-6 alkyl optionally substituted by
- halogen,
- hydroxyl,
- C.sub.1-4 alkoxy, or
- amino which may be optionally substituted by C.sub.1-4 alkyl, C.sub.1-6 alkylcarbonyl, benzoyl, .alpha.-naphthoyl, .beta.-naphthoyl or sulfonyl,
- (3) phenyl C.sub.1-4 alkyl, of which the hydrogen atoms on the benzene ring may be optionally substituted by halogen, hydroxyl, nitro, cyano, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,
- (4) a group--COR.sup.31, wherein R.sup.31 represents
- hydrogen,
- C.sub.1-6 alkyl optionally substituted by halogen, hydroxyl,
- C.sub.1-4 Alkyl or C.sub.1-4 alkoxy, or
- phenyl optionally substituted by halogen, hydroxyl, nitro, cyano, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,
- (5) a group--COOR.sup.32, wherein R.sup.32 represents
- C.sub.1-6 alkyl, or
- phenyl which may be optionally substituted by halogen,
- hydroxyl, nitro, cyano, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,
- (6) a group--CONR.sup.34 R.sup.35, wherein R.sup.34 and R.sup.35 may be the same or different and represent
- hydrogen,
- C.sub.1-6 alkyl optionally substituted by C.sub.1-4 alkyl or
- amino which may be optionally substituted by C.sub.1-4 alkyl, C.sub.1-6 alkylcarbonyl, benzoyl, .alpha.-naphthoyl, .beta.-naphthoyl or sulfonyl, or phenyl, or
- (7) a group SO.sub.2 R.sup.36, wherein R.sup.36 represents
- C.sub.1-6 alkyl,
- phenyl optionally substituted by C.sub.1-4 alkyl, C.sub.1-4 alkoxy
- or halogen, or
- .alpha.- or .beta.-naphthyl, and
- --R.sup.41 represents hydrogen, C.sub.1-6 alkyl which may be optionally substituted, or a protective group of carboxyl.
Priority Claims (2)
Number |
Date |
Country |
Kind |
5-337189 |
Dec 1993 |
JPX |
|
6-202349 |
Aug 1994 |
JPX |
|
Parent Case Info
This is a divisional application of Ser. No. 08/522,263 filed Oct. 26, 1995, which is a national phase application of PCT/JP94/02282 filed Dec. 28, 1994, now U.S. Pat. No. 5,686,442.
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Number |
Name |
Date |
Kind |
4959361 |
Walsea |
Sep 1990 |
|
5481002 |
Fischer et al. |
Jan 1996 |
|
Foreign Referenced Citations (2)
Number |
Date |
Country |
63-10784 |
Jan 1988 |
JPX |
3-294277 |
Dec 1991 |
JPX |
Non-Patent Literature Citations (2)
Entry |
Gurtler et al., Dicarboxylates of 3-methyldidene-.beta.-lactams: addition reactions to the exocyclic double bond, formation of spiro-.beta.-lactams, and reductive ring opening by hydrazines, Helv. Chim. Acta, 76(8), 2958-68, 1993, Dec. 15, 1993. |
Buckle et al., Studies on 1,2,3-Triazoles, J. Med. Chem. 27(2), 223-7, 1984. |
Divisions (1)
|
Number |
Date |
Country |
Parent |
522263 |
Oct 1995 |
|