MXPA00003047A - Tricyclic triazolobenzazepine derivatives, process for producing the same, and antiallergic - Google Patents

Abstract

Tricyclic triazolobenzazepine derivatives in the form of a prodrug. The compounds are ones represented by general formula (I) and pharmacologically acceptable salts and solvates thereof. They are useful as an antiallergic and have excellent bioavailability. In formula (I), R1 represents hydrogen, OH, alkyl, or phenylalkyl;R2, R3, R4, and R5 each represents hydrogen, halogeno, optionally protected hydroxyl, formyl, optionally substituted alkyl, alkenyl, alkoxy, etc.;and Q represents a group selected among groups (i) to (iv), halogeno, or alkoxy.

Description

TRICIACLIC DERIVATIVES OF TRIAZOLOBENZACEPINA, PROCEDURE FOR THEIR PRODUCTION, AND ANTIALERGIC AGENTS BACKGROUND OF THE INVENTION FIELD OF THE INVENTION The present invention relates to a tricyclic triazolobenzazepine derivative having an antiallergic activity as a prodrug, an intermediate for the synthesis thereof, a process for the production thereof, and an antiallergic agent. BACKGROUND OF THE ART In recent years, it has been discovered that allergic reactions induced by various stimuli such as, for example, immunoreactions can be divided into two reactions, i.e., an immediate reaction that occurs immediately after the stimulus and a delayed reaction that occurs several hours after the stimulus (see, for example, "Laie Asth atic Responses," PM O'byrne, J. Dolovich and FE Hargreave, Am. Rev. Respir. Dis., 1987; 136: 740-751). Especially, the control of the second reaction has become important. Clinical studies show that there are few drugs that are really effective in inhibiting the delayed allergic reaction. Thus, the development of therapeutically effective drugs to treat both the immediate reaction and the delayed reaction has been expected in the art.

Sodium cromoglycate is known as a representative drug to inhibit immediate and delayed allergic reactions. This drug is administered clinically by inhalation because it is not useful when administered orally. Administration by inhalation, however, presents a disadvantage insofar as it is difficult to administer the drug appropriately to infants, infants, and children and that it is difficult to continuously administer the drug to patients highly sensitive to stimuli by inhalation. Thus, the development of oral drugs that can inhibit both the immediate allergic reaction and the delayed allergic reaction and which have excellent efficacy has been expected in the art. In recent years, many studies on antiallergic agents and therapeutic agents for asthma were performed in the art. Tricyclic compounds containing a seven-membered ring that have been studied include dibenzoxepin derivatives (Japanese Patent Nos. 10784/1988 and 78292/1993 and Journal of Chemical &Pharmaceutical Bulletin, vol.39, No. 10, page 2724 and page 2729 (1991)), dibenzoxacepin derivatives (Japanese U.S. Patent Nos. 184963/1991, 211071/1992, and 65257/1993 and EP 5180720), as well as dibenzocycloheptene derivatives (WO 93/13068). In addition, tricyclic benzazepine derivatives and tricyclic benzothiazepine derivatives are presented in EP 0686636, WO 95/18130, and Meanwhile, a prodrug technique is known as a way to improve the bioavailability of a drug (Kei or Toyo Seizai No Sekkei To Kyoka (Design and Test of Oral Preparation): edited by Mitsuru Hashida, Yakugyo Jiho Co., Ltd., pages 216-231 (1995)). A chemical modification of a carboxyl, hydroxyl, amino or other group of the drug through an ester, amido, acetal or other bond can improve the bioavailability of the drug. However, modified 1,2,3-triazole prodrug has not been reported in the art. SUMMARY OF THE INVENTION The present inventors have synthesized a tricyclic triazolobenzazepine derivative having a chemically modified triazole ring and have found that a derivative has superior bioavailability as compared to the corresponding triazolobenzazepine. In one aspect of the present invention, tricyclic triazolobenzazepine derivatives are provided as a prodrug represented by formula (I) and pharmacologically acceptable salts and solvates thereof: where R1 represents a hydrogen atom, a hydroxyl group, C? -4 alkyl, or phenylalkyl C? -C; R2, R3, R4, and R5, which may be the same or different, represent any of the following (a) to (n): (a) a hydrogen atom; (b) a halogen atom; (c) an optionally protected hydroxyl group; (d) formyl; (e) C 1 -C 2 alkyl which may be substituted by a halogen atom; (f) C2-C2 alkenyl having one or more carbon-carbon double bonds and can be substituted by (1) a halogen atom, (2) cyano, (3) -COR9 where R9 represents a hydrogen atom or Alkyl C? -C6 (4) -COOR10 where R10 represents a hydrogen atom or Ci-e alkyl, (5) -CONR11R12 where R11 and R12, which may be the same or different, represent (i) a hydrogen atom (ii) C6_6 alkyl which may be substituted by amino optionally substituted by C4_4alkyl, phenyl optionally substituted by C1-4alkyl which may be substituted by a five to seven membered heterocyclic ring containing one or two atoms of nitrogen (the nitrogen atoms may be substituted by Ci-4 alkyl), or a saturated or unsaturated five to seven membered heterocyclic ring, (iii) phenyl which may be substituted by carboxyl, or (iv) a heterocyclic ring from five to seven saturated or unsaturated members, (6) a ring five to seven membered saturated or unsaturated tertiary cyclic which may be substituted by C1-4alkyl or may form a bicyclic ring fused to another ring; (g) C1-12 alkoxy which may be substituted by (1) a halogen atom, (2) a hydroxyl group, (3) cyano, (4) C3_7 cycloalkyl, (5) phenyl, (6) C1-4 alkoxy , (7) phenoxy, (8) amino which may be substituted by C? _4 alkyl, (9) -COR13 where R13 represents a hydrogen atom, C? -6 alkyl, phenyl optionally substituted by a halogen atom or alkoxy C? -4 / or phenylalkyl C? _4, (10) -COOR14 where R14 represents a hydrogen atom or C? -6 alkyl, (11) -CONR15R16 where R15 and R16, which may be the same or different represent a hydrogen atom or alkyl C? _6 which may be substituted by a saturated or unsaturated five to seven membered heterocyclic ring, or (12) a heterocyclic ring of five to seven unsaturated members which may be substituted by C1-4alkyl or phenylalkylC? -4; (h) -C = N-OR16 where R16 represents a hydrogen atom, C? -6 alkyl phenylalkyl C? -4 / or phenyl; (i) - (CH2) mOR17 where m is an integer from 1 to 4 and R17 represents a hydrogen atom, C? -6 alkyl, or C? -4 phenylalkyl, wherein one or more hydrogen atoms in the ring of benzene can be substituted by C? _4 alkyl; (j) - (CH2) k-COR18 where k is an integer from 1 to 4, and R18 represents a hydrogen atom or C? -4 alkyl; (k) - (CH2) j-COOR19 where j is an integer from 0 to 4, and R19 represents a hydrogen atom or Ci- = alkyl; (1) - (CH2) p-NR > 20tR-, 2l where p is an integer from 1 to 4, and R and R > 21, which may be the same or different, represent (1) a hydrogen atom, (2) C? -6 alkyl which may be substituted by amino optionally substituted by C? -4 alkyl, (3) phenylalkyl C1-4, (4) -COR22 where R22 represents a hydrogen or C1-4 alkyl which may be substituted by carboxyl, or (5) -S02R23 wherein R23 represents C? - alkyl or phenyl which may be substituted by a halogen atom; (m) - (CH2) q-C0NR24R25 where q is an integer from 0 to 4, and R24 and R25, which may be the same or different, represent a hydrogen atom, a saturated or unsaturated five to seven membered heterocyclic ring or alternatively C alquilo _6 alkyl which may be substituted by a saturated or unsaturated five to seven membered heterocyclic ring, or alternatively R 24 and R 25 may form a five to seven membered heterocyclic ring saturated or unsaturated together with a nitrogen to which they are attached (the heterocyclic ring may further contain at least one oxygen, nitrogen or sulfur atom, may form a bicyclic ring fused to another ring, or may be substituted by C? -4 alquilo alkyl), and (n) -NR26R27 wherein R26 and R27 which may be the same or different, represent a hydrogen atom or -COR28 where R28 represents a hydrogen atom, C? _6 alkyl, or phenyl which may be substituted by C? _4 alkyl or alkoxy C? _ 6 optionally substituted by phenyl; R31 and R32, which may be the same or different, represent a hydrogen atom or C? _6 alkyl which may be substituted by a halogen atom; and Q represents a group selected from the following groups (i) to (iv) or a halogen atom or C? _6 alkoxy: where R33 represents C6_6alkyl which may be substituted by C6_6alkoxy optionally substituted by C6_6alkoxy, phenyl optionally substituted by C6_6alkoxy, amino, or nitro or a saturated or unsaturated five to seven membered heterocyclic ring optionally substituted by Ci-β, amino, or nitro alkoxy, phenyl may be substituted by C?-aminoalkoxy, or nitro, or a saturated or unsaturated five to seven membered heterocyclic ring which may be substituted by C alco alkoxy β, amino, or nitro, or R33 can form C? -4 -4 alkylene together with R31 or R32, R34 represents C?-C 6 alkyl which can be substituted by a halogen atom, carboxyl, phenyl, optionally substituted by C alco alkoxy? -6, amino, or nitro, or a saturated or unsaturated five to seven membered heterocyclic ring optionally substituted by C6-6 alkoxy, amino, or nitro, phenyl may be substituted by C6-alkoxy, amino, or nitro, or well a heterocyclic ring of five to seven members sa tured or unsaturated which may be substituted by C?-β, β-amino, or nitro alkoxy, R 35 and R 36, which may be the same or different, represent a hydrogen atom or C alquilo _ alquilo alkyl which may be substituted by amino optionally substituted by C 1 alkyl or R 35 and R 36 can form a saturated or unsaturated five to seven membered heterocyclic ring together with a nitrogen atom to which they are attached, and R 37 and R 38 which may be the same or different, represent C 1 -C 6 alkyl . In another aspect of the present invention, tricyclic benzazepine derivatives are provided as a prodrug represented by formula (la) and pharmacologically acceptable salts and solvates thereof: where R41 and R42 which may be the same or different, represent a hydrogen atom, optionally protected hydroxyl, C6-alkoxy which may be substituted by a halogen atom, or Ci-β alkyl which may be substituted by a carbon atom. Halogen and R31, R32, and Q are in accordance with that defined above: The tricyclic triazolobenzazepine derivatives according to the present invention are useful for the treatment of allergic diseases. In another aspect of the present invention, there is provided a pharmaceutical composition comprising as an active ingredient the compound represented by the formula (I) or (la) or a pharmacologically acceptable salt or a solvate thereof. In a further aspect of the present invention, intermediates are provided for the synthesis of the compounds represented by the formulas (I) and (la). Specifically, an intermediate compound according to the present invention is a compound represented by the formula (II) or a salt or solvate thereof: where R51 represents nitro or amino, R52 represents a hydrogen atom or a protective group for carboxyl, and Q, R2 to R5, R, and R > 32 are in accordance with what is defined above. Another intermediate compound according to the present invention is a compound represented by the formula (II ') or a salt or solvate thereof: (»') Where Q, R2 to R5, R31, R32, R51, and R52 are in accordance with what is defined above. An additional intermediate product according to the present invention is a compound represented by the formula (VI) or a salt or solvate thereof: where Q, R a R, R31, R, and R5Z are in accordance with what is defined above. An additional intermediate compound according to the present invention is a compound represented by the formula (VI ') or a salt or solvate thereof: (SAW') where Q, R2 to R5, R31, R32, and R52 are in accordance with what is defined above. An additional intermediate compound according to the present invention is a compound represented by the formula (VII) or a salt or solvate thereof: where R2 to R5, and R52 are in accordance with what is defined above. An additional intermediate compound according to the present invention is a compound represented by the formula (VIII) or a salt or solvate thereof: (VIII) where R61 represents a protecting group for triazole and R2 to R5, and R52 are in accordance with that defined above. An additional intermediate compound according to the present invention is a compound represented by the formula (IXa) or a salt or solvate thereof: where R41 to R42, and R52 are in accordance with the above defined, provided that R41 and / or R42 do not represent a hydrogen atom. An additional intermediate compound according to the present invention is a compound represented by the formula (XVIa) or a salt or solvent thereof: (XVIa) where R41 to R42, R51, and R52 are in accordance with what is defined above. These intermediate compounds are useful for producing the compounds represented by the formulas (I) and (Ia). DETAILED DESCRIPTION OF THE INVENTION DEFINITION As used herein, the term "alkyl" or "alkoxy" as a group or part of a group refers to straight or branched alkyl or alkoxy, branched or cyclic. Alkyl C? -C3 in accordance with that employed herein include straight chain alkyls, such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, and n-hexyl, branched alkyls such as, for example, isopropyl, isobutyl, tert-butyl, and 3-pentyl, and cyclic alkyls such as for example cyclopropyl, cyclobutyl, cyclopentyl, and cyclo-exyl. Alkoxys Ci-Ce as used herein include straight chain alkoxies having from 1 to 6 carbon atoms, such as for example methoxy, ethoxy, n-propoxy, n-butoxy, n-pentyloxy, and n-hexyloxy, branched alkoxys such as for example isopropyloxy, isobutyloxy, and tert-butyloxy, and cyclic alkoxys, such as for example cyclopropyloxy and cyclohexyloxy. Alkyls C? -C26 in accordance with what is used here include, in addition to the above C? -C6 alkyls, alkyls having from 7 to 16 carbon atoms, such as for example 1-methylhexyl, 5-methylhexyl, heptyl, octyl, nonyl, decyl, undecyl, and pentadecyl. The term "halogen atom" as used herein refers to a fluorine, chlorine, bromine or iodine atom. The term "dissimilar atom" as used herein refers to an oxygen, nitrogen or sulfur atom. The term "saturated or unsaturated five to seven membered heterocyclic ring" as used herein refers to a heterocycle containing one or more heteroatoms selected from oxygen, nitrogen and sulfur atoms. Examples of heterocyclic rings include pyridine, imidazole, oxazole, thiazole, pyrimidine, furan, thiophene, pyrrole, pyrrolidine, piperidine, tetrahydrofuran, and oxazoline. COMPOUNDS In the formula (I), R2, R3, R4, and R5 independently represent each of the groups (a) to (n). Examples of protecting groups for the hydroxyl group (c) include acetyl, chloroacetyl, dichloroacetyl, trichloroacetyl, benzoyl, 4-nitrobenzoyl, 3-oxobutyryl, benzyl, diphenylmethyl, triphenylmethyl, 4-methoxybenzyl, 3,4-dimethoxybenzyl, methoxymethyl, methoxyethoxy ethyl , benzyloxymethyl, trimethylsilyl, tert-butyldimethylsilyl, triphenylsilyl, 2-tetrahydropyranyl, and trimethylsilylethoxymethoxy. (e) C 1 -C 2 alkyl is preferably Ci-Ce alkyl, especially C 1 -C 4 alkyl. (f) the C2-C12 alkenyl is preferably C2-C6 alkenyl, more preferably C2-C4 alkenyl especially vinyl. At least one hydrogen atom in the alkenyl may be substituted by (1) a halogen atom, (2) cyano, (3) -CHR9, (4) -COOR10, (5) -CONRnR12, or (6) a five to seven membered heterocyclic ring saturated or unsaturated. In (5) -CONR ^ R12, R 11 and R, which may be the same or different, represent a hydrogen atom or C? -C6 alkyl (preferably C1-C4 alkyl), phenyl, or a heterocyclic ring of five to seven members saturated or unsaturated. In this case, this alkyl may be further substituted by amino, phenyl, or a saturated or unsaturated five to seven membered heterocyclic ring. In addition, one or two hydrogen atoms in this amino can be substituted by C 1 -C 4 alkyl. This phenyl may also be substituted by C 1 -C 4 alkyl.

In this case, this C 1 -C 4 alkyl can be substituted by a saturated five to seven membered heterocyclic ring containing one or two nitrogen atoms optionally substituted by C 1 -C 4 alkyl. Preferred examples include piperidino, 4-piperidyl, 1-pyrrolidinyl, piperazinyl, 4-alkylpiperazinyl C? -C4, and morpholino. (g) C 1 -C 6 alkoxy is preferably C 1 -C 6 alkoxy, more preferably C 1 -C 4 alkoxy. This alkoxy can be substituted by (9) -COR13_ where R13 represents a hydrogen atom, Ci-Cß alkyl (preferably C 1 -C 4 alkyl), phenyl, or C 1 -C 4 phenylalkyl. In this case, this phenyl may be substituted by a halogen atom or C1-C4 alkoxy. Even though the position of the substituent is not particularly limited, position 2 or position 4 on the phenyl ring is preferred. (g) the C 1 -C 2 alkoxy can be substituted by a saturated or unsaturated five to seven membered heterocyclic ring as a substituent (12). This heterocyclic ring is preferably a five or six membered heterocyclic saturated ring containing one or two nitrogen atoms, for example, piperidine, 4-piperidinyl, 1-pyrrolidinyl, piperazinyl, and morpholino. One or several hydrogen atoms in the heterocyclic ring can be further substituted by C 1 -C 4 alkyl or phenyl C 1 -C 4 alkyl. Preferred examples of phenyl C 1 -C 4 alkyl include benzyl such as benzyl, 4-methylbenzyl, 4-chlorobenzyl, 4-hydroxybenzyl, 4-nitrobenzyl, 4-methoxybenzyl, and 4-carboxybenzyl, phenethyl, 3-phenylpropyl, and 4-phenylbutyl. In (i) - (CH2) mOR17, m is an integer from 1 to 4, preferably an integer of 1 or 2. In (j) -CH2) kCOR18, k is an integer from 0 to 4, of preference 0, 1, or 2. In (k) - (CH2) jCOOR19, j is an integer from 0 to 4, preferably 0, 1, or 2. In (m) - (CH2) qCONR24R25, q is an integer from 0 to 4, preferably 0, 1, or 2. R24 and R25 can form a saturated or unsaturated five to seven membered heterocyclic ring together with a nitrogen atom to which they are attached. This heterocyclic ring may also contain one or more oxygen, nitrogen, or sulfur atoms. The heterocyclic ring can be substituted by C 1 -C 4 alkyl. Preferred examples of heterocyclic ring include piperazino, piperidino, N-methylpiperazino, morpholino, succinimide, indolyl, 4-methylindolyl, 5-methylindolyl, isoindolyl, phthalimido, 4-methylphthalimido, and 1, l-dioxo-2-benzothiazolyl. In the formula (I) and (la), Q can represent a halogen atom, Ci-Cβ alkoxy (preferably C 1 -C 4 alkoxy), or any of groups (i) to (iv). In group (i), one or more hydrogen atoms in this Ci-Cß alkyl represented by R 33 may be substituted by Ci-Ce alkoxy, phenyl, or a saturated or unsaturated five to seven membered heterocyclic ring (preferably a six-member heterocycle containing a heteroatom).

In addition, one or several hydrogen atoms in this C?-C6 alkoxy may be substituted by d-C6 alkoxy. One or more hydrogen atoms in this phenyl and in the heterocyclic ring may be substituted by C? -C6 alkoxy, amino or nitro. Preferred examples of C 1 -C 6 alkyls represented by R 33 include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, isopropyl, isobutyl, tert-butyl, 3-pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl , 1,3-diethoxy-2-propyl, 2-isopropoxyethyl, phenethyl, 3-pyridylmethyl, 4-methoxyphenethyl, and 2- (2-methoxyethoxy) ethoxy.

R 33 can represent phenyl. This phenyl may be substituted by C 1 -C 6 alkoxy, amino or nitro, preferably nitro. Preferred examples of phenyls represented by R33 include 4-nitrophenyl. In addition, R33 may represent a saturated or unsaturated five to seven membered heterocyclic ring (preferably a six membered heterocycle containing a heteroatom). At least one hydrogen atom in the heterocyclic ring may be substituted by Ci-Cß alkoxy, amino, or nitro, preferably nitro. Preferred examples of saturated or unsaturated five to seven membered heterocyclic ring represented by R33 include 4-piperazyl, 4-piperidyl, and 4-tetrahydropyranyl. In addition, R33 can form C 1 -C 4 alkylene together with any of R 31 and R 32. Preferred examples of C? -C4 alkyl include methylene. When R forms methylene together with R or R and R or R that is not attached to R represents a hydrogen atom, then -CQR31R32 represents 4- (2-oxo) -1,3-dioxolyl. In group (ii), one or more hydrogen atoms in Ci-Cie alkyl represented by R34 may be substituted by a halogen atom, carboxyl, phenyl, or a saturated or unsaturated five to seven membered heterocyclic ring (preferably a six-membered heterocyclic ring containing a heteroatom). In addition, one or several hydrogen atoms in the phenyl and in the heterocycle may be substituted by Ci-Cß alkoxy, amino, or nitro. Preferred examples of Ci-Cie alkars represented by R34 include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, isopropyl, isobutyl, tert-butyl, 3-pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl , 1-methylhexyl, 5-methylhexyl, heptyl, octyl, nonyl, decyl, undecyl, pentadecyl, chloromethyl, 3-chloropropyl, 2-carboxyethyl, morpholinomethyl, 4-methoxybenzyl and 4-piperazinylmethyl. R34 can represent phenyl. The phenyl may be substituted by C 1 -C 6 alkoxy, amino, or nitro, preferably amino. Preferred examples of phenyls represented by R34 include 4-aminophenyl. In addition, R34 may represent a saturated or unsaturated five to seven membered heterocyclic ring (preferably a six-membered heterocyclic ring containing a heteroatom). One or several hydrogen atoms in the heterocyclic ring may be substituted by Ci-Ce, amino, or nitro alkoxy, preferably amino. Preferred examples of five to seven saturated or unsaturated heterocyclic rings represented by R34 include 3-pyridyl and 4-pyridyl. In group (iii), one or several hydrogen atoms in Ci-Cß alkyl represented by R35 and R36 may be substituted by amino. Preferred examples of Ci-Cß alkyls represented by R35 and R36 include 2- (N, N-dimethylamino) ethyl. Preferred examples of five to seven saturated or unsaturated heterocyclic rings formed by the combination of R35 with R36 include 1-morpholino, 1-imidazolyl, and 4-piperazinyl. A group of preferred compounds represented by formula (I) include: a group of compounds wherein R 1, R 2, R 3, R 4, and R 5 represent a hydrogen atom or (g) C 1 -C 12 alkoxy (preferably C 1 -C 6 alkoxy) ) and Q represents a group (i) (preferably R33 represents C1-C4 alkyl optionally substituted by C1-C4 alkoxy); a group of compounds wherein R1 represents a hydrogen atom, R, R3, R4, and R represent a hydrogen atom or (g) C? -C? 2 alkoxy (preferably C? -C6 alkoxy), and Q represents a group (i) (preferably R33 represents alkyl C1-C4 optionally substituted by C1-C4 alkoxy); a group of compounds wherein R1, R2, and R5 represent a hydrogen atom, R3 and R4 represent a hydrogen atom or (g) C1-C12 alkoxy (preferably Ci-Cβ alkoxy), and Q represents a group (i) ) (preferably, R 33 represents C 1 -C 4 alkyl optionally substituted by C 1 -C 4 alkoxy); a group of compounds wherein R1, R2, and R5 represent a hydrogen atom, R3 and R4 represent a hydrogen atom or (f) C2-C2 alkenyl and Q represents a group (i) (preferably, R33 represents C alquilo-C alkyl optionally substituted by C?-C4 alkoxy); a group of compounds wherein R1, R2, and R5 represent a hydrogen atom, R3 and R4 represent a hydrogen atom or (e) C? -C? 2 alkyl, and Q represents a group (i) (preferably, R 33 represents C 1 -C 4 alkyl optionally substituted by C 1 -C 4 alkoxy); a group of compounds wherein R1, R2, and R5 represent a hydrogen atom, R3 and R4 represent a hydrogen atom or (j) a group - (CH2) kCOR18, (1) - (CH2) pNR20R21, () ( CH2) qC0NR22R23, or (n) -NR29R30, and Q represents a group (i) (preferably, R33 represents C? -C4 alkyl optionally substituted by C1-C4 alkoxy); a group of compounds wherein R 1, R 2, R 4 and R 5 represent a hydrogen atom, R 3 represents (g) C 1 -C 2 alkoxy (preferably Ci-Ce alkoxy), and Q represents a group (i) (preferably , R33 represents C? -C4 alkyl optionally substituted by C? -C4 alkoxy); and a group of compounds wherein R 1, R 2, R 3 and R 5 represent a hydrogen atom, R 4 represents (g) C 1 -C 2 alkoxy (preferably Ci-Ce alkoxy), and Q represents a group (i) (from Preferably, R 33 represents C 1 -C 4 alkyl optionally substituted by C 1 -C 4 alkoxy). In formulas (I) and (a), -CR31R32Q is preferably located at position 2 in the triazole ring. One or more hydrogen atoms in Ci-Ce alkyl represented by R31 and R32 in the formulas (I) and (Ia) and one or more hydrogen atoms in the Ci-Cß alkyl and in the Ci-Cß alkoxy in their alkyl portion represented by R41 and R42 in the formula (la) may be substituted by a halogen atom. Examples of substituted alkyls and alkyl portions include trifluoromethyl, 2-fluoroethyl, difluoromethyl, 2,2,2-trifluoroethyl, trichloromethyl, 2-chloroethyl, dichloromethyl, 2,2,2-trichloroethyl, tribromethyl, 2-bromoethyl, dibromomethyl, 2, 2, 2-tribromoethyl, pentafluoroethyl, fluoromethyl, 3, 3, 3-trifluoropropyl, 4, 4-trichlorobutyl, 5, 5, 5-trifluoropentyl and 6,6-, 6-trifluorohexyl. Protecting groups for optionally protected hydroxyl which may be represented by R41 and R42 include acetyl, chloroacetyl, dichloroacetyl, trichloroacetyl, benzoyl, 4-nitrobenzoyl, 3-oxobutyryl, benzyl, diphenylmethyl, triphenyl ethyl, 4-methoxybenzyl, 3,4-dimethoxybenzyl, methoxymethyl, methoxyethoxymethyl, benzyloxymethyl, trimethylsilyl, tert-butyldimethylsilyl, triphenylsilyl, 2-tetrahydropyranyl and trimethylsilylethoxymethoxy. R 41 and R 42 preferably represent C 1 -C 4 alkoxy, more preferably methoxy or isopropyl. With even greater preference, R41 represents methoxy, and R42 represents methoxy or isopropyl. A group of preferred compounds represented by formula (la) includes a group of compounds wherein R41 and R42 represent Ci-Cβ alkoxy (preferably C?-C4 alkoxy, especially methoxy or isopropyl), and Q represents a group (i) ( preferably, R 33 represents C 1 -C 4 alkyl optionally substituted C 1 -C 4 alkoxy). Among the compounds according to the present invention, particularly preferred compounds include 2- (l-isopropoxycarbonyloxy-2-methylpropyl) -7,8-dimethoxy-4 (5H), 10-dioxo-2H-1, 2, 3- triazolo [4, 5-c] [l] benzazepine, 2- (1- (1,3-diethoxy-2-propoxycarbonyloxy) -2-methylpropyl) -7,8-dimethoxy-4 (5H), 10-dioxo- 2H-1, 2, 3-triazolo [4, 5-c] [l] benzazepine, 2- (1- (1,3-diethoxy-2-propoxycarbonyloxy) -2-methylpropyl) -8-isopropoxy-7-methoxy -4 (5H), 10-dioxo-2H-1, 2, 3-triazolo [4, 5, c] [1] benzazepine, and 8-isopropoxy-2- (1-isopropoxycarbonyloxy-2-methylpropyl) -7- methoxy-4 (5H), 10-dioxo-2H-1, 2, 3-triazolo [4, 5-c] [l] benzazepine. In the present invention, protective groups for carboxyl represented by R52 include, for example, methyl, ethyl, tert-butyl, benzyl, 4-methoxybenzyl, diphenylmethyl, 4-nitrobenzyl, tert-butyldimethylsilyl, triphenylsilyl, 2-phenylsulfonylethyl, 2-methoxycarbonylethyl. , 2-cyanoethyl, and 2-trimethylsilylethyl. In the present invention, "protecting groups for triazole" represented by R61 include, for example, benzyl optionally substituted by a halogen atom, hydroxyl, nitro, Ci-Cß alkyl, or Ci-Ce alkoxy, diphenylmethyl, triphenylmethyl, 4-methoxybenzyl, 3,4-dimethoxybenzyl, 3,4,5-trimethoxybenzyl, trimethylsilyl, tert-butyldimethylsilyl, methoxymethyl, benzyloxymethyl, and methoxyethoxy. A group of intermediates represented by the formulas (II), (II '), (VI), and (VI') include compounds wherein R2 and R5 represent a hydrogen atom, R3 and R4 each independently represent a hydrogen atom , optionally protected hydroxyl, optionally substituted C 1 -C alkoxy optionally substituted C 1 -C 6 alkyl (preferably optionally substituted C 1 -C 6 alkoxy) and Q represents a group (i) (preferably, R 33 represents C 1 -C 4 alkyl optionally substituted by C1-C4 alkoxy).

A group of preferred intermediate compounds represented by formulas (VII) and (VIII) includes compounds wherein R2 and R5 represent a hydrogen atom and R3 and R4 each independently represent an optionally protected hydroxy, optionally protected hydroxyl, Ci-Ce alkoxy substituted, and optionally substituted C6-C6 alkyl (preferably, optionally substituted C6-C6 alkoxy). Preferred examples of compounds represented by the formulas (VI) and (VI ') include 5- (3,4-dimethoxybenzoyl) -2- (1-isopropoxycarbonyloxy-2-methylpropyl) -2H-1,2,3-triazole-4 ethyl-carboxylate, 2- (l-isopropoxycarbonyloxy-2-methylpropyl) -5- (3-isopropoxy-4-methoxybenzoyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester, 5- (3, 4-dimethoxybenzoyl) -2- (1- (1,3-diethoxy-2-propoxy) carbonyloxy-2-methylpropyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester, and 2- (1- (1,3-diethoxy-2-propoxy) carbonyloxy-2-methylpropyl) -5- (3-isopropoxy-4-methoxybenzoyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester. Examples of preferred compounds represented by the formula (VII) include methyl 5- (3, -dimethoxybenzoyl) -1 H-1,2,3-triazole-4-carboxylate, 5- (3,4-dimethoxybenzoyl) -1H-1 , Ethyl 2, 3-triazole-4-carboxylate, methyl 5- (3-isopropoxy-4-methoxybenzoyl) -1 H-1,2,3-triazole-4-carboxylate, and 5- (3-isopropoxy-4) -methoxybenzoyl) -1 H-1,2,3-triazole-4-carboxylic acid ethyl ester. Examples of preferred compounds represented by the formula (IX) include methyl 4- (3, 4-dimethoxyphenyl) -4-oxo-2-butinoate, 4- (3,4-dimethoxyphenyl) -4-oxo-2-butinoate of ethyl, methyl 4- (3-isopropoxy-4-methoxyphenyl) -4-oxo-2-butinoate and ethyl 4- (3-isopropoxy-4-methoxyphenyl) -4-oxo-2-butinoate.

Examples of preferred compounds represented by the formula (XVI) include ethyl 4- (4,5-dimethoxy-2-nitrophenyl) -4-oxa-2-butynate and 4- (5-isopropoxy-4-methoxy-2-nitrophenyl) Ethyl) -4-oxo-2-butinoate. In the compounds according to the present invention, tautomers and positional isomers derived from the triazole ring, cis-trans isomers derived from alkenyl as a substituent, and enantiomers derived from the group -CQR33R34 may exist, and any of the isomers and mixtures of the same fall within the scope of the present invention.

The compounds according to the present invention can be formed into pharmacologically acceptable salts thereof. Such salts include non-toxic salts. Preferred salts include alkali metal salts and ferrous alkali metal salts, such as, for example, sodium, potassium and calcium salts, hydrohalogenic acid salts, such as, for example, hydrochloride salts, hydrochloride salts, hydrobromide salts, and hydroiodide salts , salts of inorganic acids, such as, for example, nitric acid salts, perchloric acid salts, sulfuric acid salts, and phosphoric acid salts, lower alkylsulfonic acid salts, such as, for example, methanesulfonic acid salts, trifluoromethanesulfonic acid salts, salts of ethanesulfonic acid, salts of arylsulfonic acid such as, for example, benzenesulfonic acid salts and salts of p-toluenesulfonic acid, salts of organic acid, such as, for example, fumaric acid salts, succinic acid salts, citric acid salts, tartaric acid salts , salts of oxalic acid, and salts of maleic acid, amino acid salts such as, for example, salts of acid and salts of aspartic acid. Solvates of the compounds according to the present invention include ethanol hydrates and solvates. PRODUCTION OF THE COMPOUNDS The compounds according to the present invention can be synthesized through the following processes 1 or 2. < Process 1 > The compound represented by the formula (I) can be produced by the reaction of a compound represented by J_a formula (III) where R1 to R5 are in accordance with what is defined above, with a compound represented by the formula (IV) Hal (IV) R31 ~ R32 where Q, R31 and R32 are in accordance with what is defined above and Hal represents a halogen atom, in a solvent not involved in the reaction (eg water, ethanol, isopropyl alcohol, tetrahydrofuran, diisopropyl ether, methylene chloride, ketone, N, N-dimethylformamide, dimethylsulfoxide) in the presence of a base at a temperature within a range from 0 to 150 ° C for 1 to 48 hours. The bases employed herein include organic bases such as for example pyridine and triethylamine, as well as inorganic bases such as for example potassium carbonate, sodium carbonate, cesium carbonate, sodium hydrogencarbonate, sodium hydroxide, and potassium hydroxide. Preferably, the compound can be prepared by reaction in N, N-dimethylformamide in the presence of sodium hydrogencarbonate at a reaction temperature of 20 to 100 ° C for 1 to 24 hours. The compound represented by the formula (I) is produced as a mixture of triazole substituted in 1, triazole substituted in 2, and triazole substituted in 3 in any proportion. The compound represented by the formula (III) can be produced by processes described, for example, in WO 95/18130 and WO 97/00258. The compound represented by the formula (I) can be purified by conventional purification methods, for example, recrystallization, reprecipitation, extraction in solvent, column chromatography on silica gel, or column chromatography on adsorption resin. <Process 2 > The compound represented by the formula (I) can be produced by reduction of the compound of the formula (Ha) where Q, R2 to R5, R31, R32 and R52 are in accordance with that defined above, to prepare a compound represented by the formula (IIb) where Q, R a to R 3, R 31 and R, 5 ° 2 are in accordance with what is defined above, and then subjecting the compound represented by the formula (Ilb) to cycles. Conventional catalytic reductions (preferably in the presence of a nickel or palladium catalyst in a solvent, for example, ethyl acetate, an alcohol solvent such as for example ethanol, water, or a mixture thereof) or reduction using a metal such as for example iron or zinc, for example, reduction in a zinc-acetic acid system, and the like can be used for the reduction reaction. The reduction can be carried out at a temperature of 10 to 100 ° C for 0.1 to 10 hours. The cyclization can be carried out by reacting the compound represented by the formula (IIb) with a strong base such as, for example, sodium hydride, potassium hydride, sodium methoxide, sodium ethoxide, or potassium tert-butoxide, in a solvent not involved in the reaction (for example, an alcohol such as methanol, ethanol, or isopropyl alcohol, toluene, N, N-dimethylformamide, dimethyl sulfoxide, dioxane, tetrahydrofuran, or a mixture of two or more of these solvents) at a temperature of 0 to 100 ° C for 1 to 48 hours, generally 5 to 24 hours. The cyclization reaction can also be carried out in an acetic acid or trifluoroacetic acid solvent by reacting the compound represented by the formula (IIb) at a temperature comprised between 20 and 100 ° C, for 1 to 24 hours. After crystallization, Q can be converted additionally into another substituent. In both aforementioned reduction and cyclization reactions, isomerization of the position of the substituent in the triazole is not observed. When a compound represented by the formula (lya ') is used alone, the compound represented by the formula (I) is obtained in the form of a single compound.

The compound represented by the formula (I) can be purified by conventional purification methods such as, for example, recrystallization, reprecipitation, extraction in solvent, column chromatography on silica gel, or column chromatography on adsorption resin. The compound represented by the formula (lia) can be synthesized according to the following scheme. In the scheme, M represents lithium, magnesium chloride, magnesium bromide, magnesium iodide, zinc bromide, zinc iodide, cadmium bromide, or copper, R62 represents sodium, Ci-Cß alkylsilyl (for example trimethylsilyl), or alkyltin C? -C6, and Q, Hal, R2 to R5, R31, R32, R52 and R61 are in accordance with that described above. (lia) Synthesis (1) of the compound of the formula (lia) The compound represented by the formula (lia) can be produced from a compound represented by the formula (V) through the following process A, B, C or D.

In accordance with process B, C, or D, the compound represented by the formula (lia) having the substituents -CQR31R32 (represented by the formula (lia 'can be prepared, where the substituent is introduced into the triazole ring at its position 2. <Process A> The compound represented by the formula (lia) can be prepared by the reaction of the compound represented by the formula (V): where Q, R2 to R5, and R52 are in accordance with that defined above, with the compound represented by the formula (IV) according to the process 1. As in the case of the compound (I) prepared by the process 1, the The compound represented by the formula (lia) prepared in this way is a mixture of three types of isomers. For example, the compound represented by the formula (V) can be prepared according to a process described in WO 95/18130. < Process B > where Q, R a R, R 31 R 32 R 52 are in accordance with what is defined above. The compound represented by the formula (V) reacts with a ketone or an aldehyde represented by the formula R31R32 C = 0 in a solvent not involved in the reaction (e.g., methylene chloride, ethyl acetate, or acetonitrile) at a temperature comprised within a range of -78 to 100 ° C, preferably -20 ° C to 50 ° C for 0.1 to 24 hours, generally for 0.1 to 1 hour. In this case, a hemiacetal represented by a compound (V) is produced in the reaction system. This reaction is promoted by the addition of an acid catalyst. Preferred acid catalysts employed herein include protonic acids, such as for example p-toluenesulfonic acid, p-pyridinium salt of p-toluenesulfonic acid, D - (+) - camphorsulfonic acid, trifluoroacetic acid, sulfuric acid, hydrochloric acid, perchloric acid, and acid phosphoric, as well as Lewis acids such as boron-diethyl ether trifluoride complex, aluminum chloride, and titanium tetrachloride. Q in the formula (lia ') can be introduced by the addition of several reagents to the compound represented by the formula (V). The compound represented by the formula (lia ') wherein Q is any of groups (i) to (iv), a halogen atom, or a Ci-Cβ alkoxy can be synthesized in accordance with the following. (1) The compound represented by the formula (lia ') wherein Q is a group (i) can be prepared by reaction of the reaction solution containing the compound represented by the formula (V) with a compound represented by the formula R71 -C (= 0) -R72 (where R71 and R72, independently of each other, represent a chlorine atom, 4-nitrophenyl, or l-Lmidazolyl) including 1,1 '-carbonyldiimidazole, phosgene, p-nitrophenyl chloroformate, or bis (p-nitrophenyl) carbonate, optionally in the presence of a base such as for example pyridine, to prepare a compound represented by the formula (lia ') wherein Q represents -OCOR71 (where R71 represents a chlorine atom, 4-nitrophenyl or 1-imidazolyl) and then by reaction of the resulting compound with an alcohol represented by the formula R33OH (where R33 is in accordance with that defined above). The substituent Q can be additionally converted into another substituent. (2) The compound represented by the formula (lia ') wherein Q represents (ii) can be prepared by the addition of an acylating agent represented by R34COHal (where Hal and R34 are as defined above) or (R34CO 20 (where R 34 is in accordance with that defined above) to the reaction solution containing the compound represented by the formula (V), optionally in the presence of a base such as for example pyridine. The compound represented by the formula (lía ') where Q represents a group (ii) can also be prepared by melting the compound represented by the formula (V) with a compound represented by the formula R34COOH (where R34 is in accordance with the definition above) . Preferred condensation agents employed herein include active esterification agents such as dicyclohexylcarbodiimide, pyridine derivatives, and phosphoric acid derivatives, as well as dehydration agents such as thionyl chloride and phosphorus oxychloride. The compound can also be prepared by the reaction of the compound (lia ') (where the substituent Q represents a halogen atom, which can be synthesized by a process described in process (4), with a sodium or potassium salt of an acid carboxylic represented by the formula R3COOH (where R34 is in accordance with that defined above) in a solvent not involved in the reaction in the presence of tetra-n-butylammonium bromide, Q can be further converted into another substituent. represented by the formula (lia ') wherein Q represents a group (iii) can be prepared by the reaction of the compound, produced in the process (1), represented by the formula (lia') (wherein R2 to R5, R31, R32, and R52 are in accordance with what is defined above and Q represents -OCOR71 (where R71 is in accordance with that defined above)), optionally after isolation, with an amine represented by R35R36NH (where R35 and R36 are in accordance with what is defined riba). (4) The compound represented by the formula (lia ')wherein Q represents a group (iv), a halogen atom, or Ci-Cβ alkoxy, can be prepared by the addition of a chlorophosphoric ester represented by (R370) (R380) P0C1, an alcohol represented by R73OH (where R73 represents Ci-Cß alkyl) or a halogenating agent such as, for example, thionyl chloride or thionyl bromide, to the reaction solution containing the compound (V). The reaction can be carried out generally at a temperature of -20 to 100 ° C for 0.1 to 48 hours. All the compounds represented by the formula (lia ') synthesized by the process through the hemiacetal represented by the compound (V) are obtained as triazoles substituted at position 2. <; Process C > The compound represented by the formula (lia '), wherein Q represents a group (i), can be prepared by reacting the compound represented by the formula (V) with a compound represented by R31R32C = 0 (where R31 and R32 are in accordance with the above defined) (for example, isobutylaldehyde) in an organic solvent such as acetone, acetonitrile, or ethyl acetate, at a temperature comprised within a range of -20 to 100 ° C, preferably 22 to 28 ° C, to prepare a compound represented by the formula (V) and then by reacting the compound represented by the formula (V) in the same solution with a compound represented by HalCOOR33 (where Hal and R33 are in accordance with that defined above (for example, isopropyl chlorocarbonate), together with an alkali metal carbonate such as, for example, sodium carbonate or potassium carbonate, and an alkali metal iodide, such as, for example, sodium iodide or potassium iodide, at a temperature within a range of 25 to 60 ° C, subsequently treating the product, and crystallizing the treated product. Solvents used for crystallization include lower alcohols such as methanol, ethanol, as well as isopropyl alcohol. These solvents can be used together with water. All the compounds represented by the formula (lia ') synthesized by this process are obtained in the form of substituted triazoles in the 2-position. The above process is advantageous insofar as 1,1' -carbonyldiimidazole, which is expensive and unstable, it is not used as a reactant, the byproducts derived from 1,1'-carbonyldiimidazole are not produced, and the compounds represented by the formula (lia ') where Q represents the group (i) are obtained with a high purity and a high yield. < Process D > The compound represented by the formula (Ilia '), where Q represents a group (i), can also be prepared by direct reaction of the compound represented by the formula (V) with the compound represented by the formula (IV) (e.g. l-chloro-2-methylpropyl-isopropyl carbonate). More specifically, the compound represented by the formula (V) can be reacted with the compound represented by the formula (IV) in an organic solvent such as acetone, acetonitrile, ethyl acetate, or N, N-dimethylformamide, together with a inorganic base such as for example sodium carbonate, potassium carbonate, cesium carbonate, or sodium hydroxide, and an alkali metal iodide such as for example sodium iodide, or potassium iodide, at a temperature within a range of 25 to 60 ° C for 1 to 70 hours. The compound represented by the formula (lia ') can be purified by conventional purification methods, for example, solvent extraction, crystallization, or column chromatography on silica gel. All the compounds represented by the formula (lia ') synthesized by the above process can be advantageously obtained as triazoles substituted in the 2-position. This seems to be due to the addition of the iodide of the alkali metal to the reaction system. The process is further advantageous insofar as the compounds represented by the formula (lia ') can be produced simply from the compound represented by the formula (V) in a single step. An additional advantage of the process is that the formation of by-product derived from impurities contained in an acetone or an aldehyde (eg, isobutyric acid in isobutyl aldehyde) represented by R31R32C = 0 which reacts with the compound represented by the formula (V) can be avoided. in process B and C and high purity compounds represented by the formula (lía ') can be obtained. Synthesis (2) of compound of the formula (lia) The compound represented by the formula (lia) can be produced by nitration of the compound represented by the formula (VI). The nitration can be carried out in the presence of a nitrating agent such as nitric acid (concentrate) or smoked nitric acid without solvent or in a solvent not involved in the reaction (for example, acetic anhydride, concentrated sulfuric acid, methylene chloride, or chloroform) at a temperature comprised within a range of 10 to 50 ° C for 10 minutes to 24 hours. The compound represented by the formula (VI) can be prepared by the introduction of -CQR31R32 into the triazole group of the compound represented by the formula (VII). The substituent -CQR31R32 can be introduced according to process A, B, C or D. The compound represented by the formula (VII) can be prepared by deprotection of the compound represented by the formula (VIII). The deprotection can be carried out according to a method described in D.R. Loop and C.J.M. Rockell, J. Chem. Soc, Perkin Trans. I, 627 (1982), 1693 (1985). Specifically, when R61 represents a benzyl, diphenylmethyl, triphenylmethyl, 4-methoxybenzyl, 3,4,5-trimethoxybenzyl, benzyloxymethyl, or trimethylsilyl, the deprotection can be carried out by the reaction of the compound represented by the formula (VIII) with a mineral acid such as for example diluted hydrochloric acid or dilute sulfuric acid, either an organic acid such as for example trifluoroacetic acid as such or after dilution with a solvent not involved in the reaction (for example, methylene chloride or toluene) a temperature comprised within a range of 15 to 80 ° C for 1 to 24 hours. The compound represented by the formula (VIII) can also be prepared by the reaction of the compound represented by the formula (XII) with the compound represented by the formula (XIII ') in a solvent not involved in the reaction (for example, tetrahydrofuran, diethyl ether, diisopropyl ether, tert-butyl methyl ether, or toluene) at a temperature within a range of -78 to 100 ° C for a period of 15 minutes to 24 hours. The compound represented by the formula (XIII ') can be easily produced by the reaction of metal azide compounds such as for example sodium azide represented by the formula (X'), various alkylsilyl azides, and various alkyltin azides, with an acetylenedicarboxylic diester. The compound represented by the formula (VII) can also be prepared by the reaction of the compound represented by the formula (IX) with the metal azide compound represented by the formula (X ') in a solvent not involved in the reaction ( for example, water, ethanol, isopropyl alcohol, tetrahydrofuran, diisopropyl ether, methylene chloride, acetone, toluene, ethyl acetate, dimethylformamide, or dimethylsulfoxide) at a temperature within a range of 0 to 120 ° C for a period of 1 to 24 hours. Synthesis of the compound represented by the formula (VIII) The compound represented by the formula (VIII) can be prepared by the reaction of the compound represented by the formula (IX) with the organic compound of azide represented by the formula (X) as for example p-methoxybenzyl azide. The reaction can be carried out by the reaction of the compound represented by the formula (IX) with the compound represented by the formula (X '). The compound represented by the formula (IX) can be prepared by the reaction of the compound represented by the formula (XI) with chlorine, bromine or iodine in a solvent not involved in the reaction (for example, water, ethanol, isopropyl alcohol, tetrahydrofuran, diisopropyl ether, methylene chloride, acetic acid, dimethylformamide, or dimethylsulfoxide) at a temperature within a range of -10 to 30 ° C for a period of 10 minutes to 24 hours and then by reacting the resultant halide with an organic base such as triethylamine, diisopropylethylamine, triisopropylamine, pyridine, picoline, lutidine, collidine or quinoline, or an inorganic base such as potassium carbonate, sodium carbonate, cesium carbonate, hydrogencarbonate of potassium, or sodium hydrogencarbonate in the absence of solvent or in a solvent not involved in the reaction (for example, water, ethane, isopropyl alcohol co, tetrahydrofuran, diisopropyl ether, methylene chloride, acetone, toluene, dimethylformamide, or dimethylsulfoxide) at a temperature which is within a range of 0 to 50 ° C over a period of 1 to 24 hours.

The compound represented by the formula (XI) can be prepared by a method described, for example, in Eur. J. Med. Chem., 23, 45 (1988) or in the North American Patent No. 4,562,068. The compound represented by the formula (VIII) can also be prepared by the conversion of a halobenzene represented by the formula (XIV) into an organometal compound represented by the formula (XII) (for example, M represents lithium, magnesium chloride, bromide of magnesium, magnesium iodide, zinc bromide, zinc iodide, cadmium bromide, cadmium iodide, copper or the like) and then by reaction of the compound represented by the formula (XII) with the compound represented by the formula (XIII) in a solvent which is not involved in the reaction (eg, tetrahydrofuran, diethyl ether, diisopropyl ether, tert-butylmethylether, or toluene) at a temperature set within a range determined 78-100 ° C for a period from 15 minutes to 24 hours. The compound represented by the formula (XIII) can be easily prepared by the reaction of an azide compound (X) synthesized, for example, by a method described in J. Heterocyclic Chem., 21, 1669 (1984) with an acetylenedicarboxylic diester. . Synthesis of the compound of the formula (V) The compound represented by the formula (V) can be prepared by deprotection of the compound represented by the formula (XV). The deprotection can be carried out by the method described with respect to the deprotection of the compound represented by the formula (VIII) to produce the compound represented by the formula (VII). The compound represented by the formula (V) can also be produced by the reaction of the compound represented by the formula (XVI) with the compound represented by the formula (X '). The reaction can be carried out by the method described above in relation to the reaction of the compound represented by the formula (IX) with the compound represented by the formula (X '). The compound represented by the formula (V) can also be produced by nitration of the compound represented by the formula (VII). The nitration can be carried out by the method described above with respect to the nitration of the compound represented by the formula (VI) to produce the compound represented by the formula (lia). The compound represented by the formula (XV) can be produced by the reaction of the compound represented by the formula (XVI) with the compound represented by the formula (X) The reaction can be carried out by the method described above in relation to the reaction of the compound represented by the formula (IX) with the compound represented by the formula (X). The compound represented by the formula (XVI) can be produced from the compound represented by the formula (XVII) by the method described above with respect to the production of the compound represented by the formula (IX) from the compound represented by the formula (XI). The compound represented by the formula (XVII) can be produced by a method described, for example, in Eur. J. Med. Chem., 23, 45 (1988) or in the North American Patent No. 4,562,068. The compound represented by the formula (XV) can also be produced by nitration of the compound represented by the formula (VIII). The nitration can be carried out by the method described above with respect to the nitration of the compound represented by the formula (VI) to produce the compound represented by the formula (lia). In addition, the compound represented by the formula (XV) can also be produced, for example, by a method described in WO 95/18130. Pharmaceutical composition _ The oral administration of the compound represented by the formula (I) according to the present invention to experimental animals showed that the compound represented by the formula (III) is detected in a higher plasma concentration compared to the administration of the compound represented by the formula (III) alone. WO 95/18130 as well as WO 97/00258 disclose the use of the compound represented by the formula (III) as a therapeutic agent for allergic diseases. The compound represented by the formula (I), after its passage through several mucous membranes, including the digestive tract, is converted in vivo into the compound represented by the formula (III) which develops an antiallergic activity. The compound according to the present invention can be used as therapeutic agents for allergic diseases, for example, bronchial asthma, urticaria, allergic gastroenteritis, allergic rhinitis as well as allergic conjunctivitis. The term "therapy" or "treatment" includes "prevention" or "prophylaxis". When administered orally, the compound according to the present invention can be formulated using conventional pharmaceutically acceptable excipients (eg, lactose, crystalline cellulose, starch, and calcium phosphate) binders (eg, starch, carmellose sodium, and hydroxypropylcellulose) , disintegrants (calcium carmellose, calcium carbonate, and the like), as well as lubricants (magnesium stearate, talc and the like) in tablets, capsules, granules, dry syrups, and various liquid preparations commonly employed in medical treatment by conventional methods . In addition, these preparations may also be prolonged-release preparations that release the ingredient over a long period of time. In accordance with the pharmacological activities, including the antiallergic action of the compound represented by the formula (III), the compound according to the present invention can be applied to several treatments through routes of administration other than oral administration. Dosage forms for this purpose include, but are not limited to, sublingual tablets, suppositories, inhalants, nose drops, eye drops, as well as percutaneous absorption preparations, eg, patches or ointments / creams. Although the content of the compound according to the present invention in the pharmaceutical composition depends on the preparations, it is usually within the range of 1 to 70% by weight, preferably approximately 5 to 50% by weight, based on the entire composition. The dose for the treatment of allergic diseases can be appropriately determined individually taking into account the instructions for use, the age and sex of the patients, the severity of the symptoms and the like. In the case of oral preparations, sublingual tablets or suppositories, however, the compound according to the present invention or the salt or solvate thereof can be administered in a dose that is within a range of 0.05 to 5 g / day , preferably from 0.1 to 1.0 g / day, once or several times divided. As for other dosage forms, the dose may be increased or decreased appropriately according to the intended use. EXAMPLES The present invention is further illustrated by the following examples which are not intended to limit the present invention. Synthesis Example 1 __ 7, 8-dimethoxy-4 (5H), 10-dioxo-lH-1, 2, 3-triazolo [4,5-c] [1] benzazepine _ (a) Butyllithium 1.5 N ( 26.8 ml, 40.2 mmol) was added to a solution of diisopropylamine (6.0 ml, 42.8 mmol) in tetrahydrofuran (75 ml) under an argon atmosphere at a temperature of -78 ° C. The mixture was stirred for 1 hour. Ethyl propiolate (3.4 ml, 33.5 mmol) and a solution of 4,5-dimethoxy-2-nitrobenzaldehyde (5.0 g, 23.7 mmol) in tetrahydrofuran (50 ml) were added in this order, and the mixture was stirred at a temperature -78 ° C for an additional 1.5 hours. A solution of acetic acid (7.0 ml, 122 mmol) in tetrahydrofuran (20 ml) was added, followed by the addition of water. The mixture was extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid, water, a saturated aqueous solution of sodium hydrogencarbonate, and a saturated brine solution, in this order. The organic layer was then dried in anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give ethyl 4-hydroxy-4- (4,5-dimethoxy-2-nitrophenyl) -2-butynate as an oil (8.59 g). The resulting ethyl 4-hydroxy-4- (4,5-dimethoxy-2-nitrophenyl) -2-butinoate was dissolved in toluene (80 ml). 4-Methoxybenzyl azide (11.6 g, 71.1 mmol) was added to the solution. The mixture was heated to a temperature of 100 ° C with stirring overnight. The reaction solution was cooled to room temperature and then purified by column chromatography on silica gel (hexane: ethyl acetate = 2: 1). The precipitate created in the eluted product was collected by filtration to provide a 1: 5 mixture (2.60 g, 23%) of 4- (hydroxy- (4,5-dimethoxy-2-nitrophenyl) ethyl) -1- (4- methoxy-benzyl) -1 H-1, 2, 3-triazole-5-carboxylic acid ethyl ester (a-1: low polar product (LP)) as well as 5- (hydroxy- (4,5-dimethoxy-2-nitrophenyl) methyl) -1- (4-methoxybenzyl) -1H-1,2,3-triazole-4-carboxylic acid ethyl ester (a-2: high polar product (MP)). On the other hand, the filtrate was concentrated under reduced pressure in order to provide a 2.5: 1 mixture (4.68 g, 42%) of the compound (a-1: LP)) and the compound (a-2: (MP)) . Mixture 2.5: 1 of a ^ l (LP) and a-2 (MP): ^ -NM (CDC13): d 1.38 (15 / 7H, t), 1.39 (6 / 7H, t), 3.56 (6 / 7H , s), 3.72 (6 / 7H, s), 3.78 (15 / 7H, s), 3.91 (6 / 7H, s), 3.97 (15 / 7H, s), 3.99 (15 / 7H, s), 4.41 (4 / 7H, q), 4.44 (10 / 7H, q), 4. 97 (5 / 7H, d), 5.07 (2 / 7H, d) 5.48 (2 / 7H, d), 5.78 (5 / 7H, • d), 5.71 (2 / 7H, d), 5.84 (5 / 7H, d), 6.32 (2 / 7H, s), 6.83 (10 / 7H, d), 6.67 (4 / 7H, d), 6.99 (4 / 7H, d), 7.07 (2 / 7H, d), 7. 21 (10 / 7H, d), 7.48 (2 / 7H, s), 7.51 (5 / 7H, s), 7.71 (5 / 7H, s). EIMS: m / z 472 (M +). (b) Manganese dioxide (14 g) was added to a solution of the mixture of 2.5: 1 (4.63 g, 9.80 mmol) of compound a-1 and compound a-2 prepared in step a) in methylene chloride (100 ml). The mixture was stirred at room temperature overnight. Manganese dioxide added (4.6 g), and the mixture was stirred at room temperature for 8 hours. The reaction solution was filtered through Celite, followed by washing with ethyl acetate. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 2: 1) to give l- (4-methoxybenzyl) -4- (4,5-dimethoxy-2-nitrobenzoyl) -1 H-1,2,3-triazole-5-carboxylic acid ethyl ester in the form of a brown crystalline powder (b-1: LP) (2.75 g, 60%) and 1- (4-methoxybenzyl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -1H-1, 2, Ethyl 3-triazole-4-carboxylate in the form of a brown crystalline powder (b-2: MP) (1.12 g, 24%). b-1 (LP): 1H-NMR (CDC13): d 1.38 (3H, t), 3.78 (3H, s), 3.98 (3H, s), 4.02 (3H, s), 4.43 (2H, q), 5.72 (2H, s), 6.85 (2H, d), 6.99 (1H, s), 7.24 (2H, d), 7.69 (1H, s). SIMS: m / z 471 (M +). b-2 (MP): 1 H-NMR (CDCl 3): d 1.19 (3H, t), 3.79 (3H, s), 3.91 (3H, s), 4.00 (3H, s), 4.10 (2H, q), 5.79 (2H, s), 6.80 (1H, s), 6.88 (2H, d), 7.42 (2H, d), 7.52 (1H, s). EIMS: m / z 470 (M +). (c) A solution of 1N aqueous sodium hydroxide (13 ml) was added to a solution of 1- (4-methoxybenzyl) -4- (4,5-dimethoxy-2-nitrobenzoyl) -1H-1, 2, 3-Triazole-5-carboxylic acid ethyl ester (b-1) (3.04 g, 6.46 mmol), prepared in step (b), in tetrahydrofuran (40 ml). The mixture was stirred at room temperature for 3.5 hours. The reaction solution was diluted with ether, and water was added. An aqueous layer was acidified with hydrochloric acid and extracted with ethyl acetate, followed by washing with water and a saturated brine solution. The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give 1- (4-methoxybenzyl) -4- (4,5-dimethoxy-2-nitrobenzoyl) -1H-1,2,3-triazole-5-carboxylic acid in the form of an oil. light yellow (c-1 ': LP) (2.55 g, 89%). The resulting 1- (4-methoxybenzyl) -4- (4,5-dimethoxy-2-nitrobenzoyl) -1H-1,2,3-triazole-5-carboxylic acid (c-1 ': LP) (1.07 g, 2.42 mmol) was dissolved in mixed solvent composed of ethanol (50 ml) and ethyl acetate (50 ml). Palladium-carbon 10% (129 mg) was added. The mixture was stirred under an atmosphere of hydrogen at room temperature for 4 hours. Methylene chloride was added to the reaction solution to dissolve in precipitated crystal, followed by filtration through Celite. The filtrate was concentrated under reduced pressure to provide 4- (2-amino-4,5-dimethoxybenzoyl) -1- (4-methoxybenzyl) -1H-1,2,3-triazole-5-carboxylic acid (c-1: LP) (1.06 g, 100%). c-1 '(LP): 1 H-NMR (CDCl 3): d 3.78 (3H, s), 3.99 (3H, s), 4.06 (3H, s), 6.02 (2H, s), 6.84 (2H, d) , 6.94 (1H, s), 7.40 (2H, d), 7.76 (1H, s), 13.80 (1H, brs). SIMS: m / z 443 (M ++ l). c-1 (LP); 1 H-NMR (CDCl 3): d 3.78 (3 H, s), 3.88 (3 H, s), 3.94 (3 H, s), 6.06 (2 H, s), 6.11 (1 H, s), 6.86 (2 H, d), 7.45 (2H, d), 8.58 (1H, s). SIMS: m / z 413 (M ++ l). In the same manner, 1- (4-methoxybenzyl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -1 H-1,2,3-triazole-4-carboxylic acid ethyl ester (b-2) was hydrolysed ( 3.12 g, 6.63 mmol) prepared in step (b) in a solution of tetrahydrofuran (100 ml) with a 1 N aqueous sodium hydroxide solution (13 ml) at room temperature for 3.5 hours. Thus, 1- (4-methoxybenzyl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -1H-1,2,3-triazole-4-carboxylic acid was obtained (c-2 ': MP) (2.32 g, 79%) in the form of a yellow crystalline powder. c-2 '(MP); ^ - MR (CDCI3): d 3.80 (3H, s), 3.94 (3H, s), 4.00 (3H, s), 5.79 (2H, s), 6.89 (1H, s), 6.91 (2H, d), 7.47 (2H, d), 7.54 (1H, s). SIMS: m / z 443 (M ++ l). (d) Tributylamine (0.64 ml, 2.69 mmol), p-toluenesulfonate of 2-f luoro-1-methylpyridinium (793 mg, 2.80 mmol), and 3,4-dihydro-2H-pyrido [1,2-a] were added. ] pyrimidin-2-one (453 mg, 3.06 mmol) in this order to a solution of 4- (2-amino-4,5-dimethoxybenzoyl) -1- (4-methoxybenzyl) -1H-1, 2, 3 -triazole-5-carboxylic acid (c-1) (1.05 g, 2.55 mmol) in methylene chloride (30 ml) in an argon atmosphere under ice-cooling. The mixture was stirred under ice-cooling during and then stirred at room temperature for 2 hours. Water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with dilute hydrochloric acid, water, a saturated aqueous sodium hydrogencarbonate solution, and a saturated brine solution. The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The resulting precipitate was collected by filtration, washed with diethyl ether and water, and dried to provide 7,8-dimethoxy-3- (4-methoxybenzyl) -4 (5H), 10-dioxo-3H-1,2,3-triazolo [4, 5-c] [1] benzazepine in the form of a light yellow crystalline powder (dl: LP) (477 mg, 48%). d ^ l (LP): ^? - NMR (DMSO-d6): d 3.72 (3H, s), 3.84 (6H, s), 6.09 (2H, s), 6.90 (2H, d), 7.16 (1H, s), 7.30 (2H, d), 7.67 (1H, s), 11 33 (1H, s). EIMS: m / z 394 (M +). (e) Anisole (0.5 ml) and trifluoroacetic acid (5.0 ml) were added to 7,8-dimethoxy-3- (4-methoxybenzyl) -4 (5H), 10-dioxo-3H-1,2,3-triazole [4, 5-c] [ljbenzacepin (dl) (471 mg, 1.19 mmol). The mixture was stirred at a temperature of 60 ° C for 3 hours. Then, the solvent was evaporated under reduced pressure. The resulting precipitate was collected by filtration, washed with diethyl ether, and water, and then dried to provide the title compound 7,8-dimethoxy-4 (5H), 10-dioxo-lH-1, 2, 3-triazolo [4 , 5-c] [1] benzazepine (e) in the form of a yellow powder (319 mg, 98%). 7,8-dimethoxy-4 (5H), 10-dioxo-lH-1, 2, 3-triazolo [4,5-c] [1] benzazepine (e_) (238 mg, 0.867 mramol) was dissolved in an aqueous solution of 1 N sodium hydroxide. The solution was purified in Diaion.

HP-20 (water: acetone = 9: 1) to provide the title compound: a sodium salt of 7,8-dimethoxy-4 (5H), 10-dioxo-lH-1,2,3-triazolo [4, 5-c] [1] benzazepine (e_ ') in the form of a yellow powder (231 mg, 90%). e: 1H-NMR (DMSO-de): d 3.85 (3H, s), 3.86 (3H, s), 7.22 (1H, s), 7.70 (1H, s), 11.23 (1H, s). SIMS: m / z 275 (M ++ l).

FDMS: m / z 274 (M + -Na + 1). Synthesis Example 2 5- (4,5-dimethoxy-2-nitrobenzoyl) -1 H-1,2,3-triazole-4-carboxylic acid ethyl ester Anisole (1 ml) was added to a solution of a mixture of approximately 1: 1 (4.4 g) of ethyl 1- (4-methoxybenzyl) -4- (4,5-dimethoxy-2-nitrobenzoyl) -1 H-1,2,3-triazole-5-carboxylate (synthesis example 1, b) -1) and ethyl 1- (4-methoxybenzyl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -1 H-1,2,3-triazole-4-carboxylate (synthesis example 1, b-2) ) in trifluoroacetic acid (10 ml), and the mixture was stirred at a temperature of 60 ° C for 10 hours. After allowing the mixture to stand to cool, the solvent was evaporated under reduced pressure, followed by azeotropic evaporation using toluene. The resulting crystal was collected by filtration washed with diethyl ether, and then dried to give ethyl 5- (4,5-dimethoxy-2-nitrobenzoyl) -1 H-1,2,3-triazole-4-carboxylate (3.12 g, 95%). %). ^ -NMR (CDC13): d 1.42 (3H, t), 4.00 (3H, s), 4.03 (3H, s), 4.47 (2H, q), 7.02 (1H, s), 7.67 (1H, s). Synthesis Example 3 4- (5-isopropoxy-4-methoxy-2-nitrobenzoyl) -1- (4-methoxybenzyl) -1 H-1,2,3-triazole-5-carboxylic acid ethyl ester and 5- (5-isopropoxy) -4-methoxy-2-nitrobenzoyl) -1- (4-methoxybenzyl) -1H-1,2,3-triazole-4-carboxylic acid ethyl ester __ __ _ (a) Butyllithium 1.5 N (22.6 ml, 33.8 mmol ) to a solution of diisopropylamine (5.0 ml, 36.0 mmol) in tetrahydrofuran (75 ml) under an argon atmosphere at a temperature of -78 ° C., and the mixture was stirred for one hour. Ethyl propiolate (2.9 ml, 28.2 mmol) and a solution of 5-isopropoxy-4-methoxy-2-nitrobenzaldehyde (4.5 g, 18.8 mmol) in tetrahydrofuran (50 ml) were added there, in that order, and the mixture was added. was stirred at a temperature of -78 ° C for an additional 1.5 hours. A solution of acetic acid (5.9 ml, 102 mmol) in tetrahydrofuran (20 ml) was added to the reaction solution. Water was then added, followed by extraction with ethyl acetate. The organic layer was washed with dilute hydrochloric acid, water, a saturated aqueous sodium hydrogencarbonate solution, and a saturated brine solution. The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give ethyl 4- (5-isopropoxy-4-methoxy-2-nitrophenyl) -4-hydroxy-2-butynate (7.27 g). The resulting ethyl 4- (5-isopropoxy-4-methoxy-2-nitrophenyl) -4-hydroxy-2-butinoate was dissolved in toluene (60 ml). 4-Methoxybenzyl azide (9.2 g, 56.4 mmol) was added to the solution. The mixture was heated to a temperature of 100 ° C with stirring overnight. The reaction solution was cooled to room temperature. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane: ethyl acetate = 1: 2) to provide a mixture 1: 1 (7.01 g, 75%) of 4- (1-hydroxy- (5-isopropoxy-4-methoxy-2-nitrophenyl) methyl) -1- (4-methoxybenzyl) -1H-1, 2, 3- ethyl triazole-5-carboxylate (a-1: low polar product (LP)) and 5- (l-hydroxy- (5-isopropoxy-4-methoxy-2-nitrophenyl) methyl) -1- (4-methoxybenzyl) -1 H-1, 2, 3-triazole-4-carboxylic acid ethyl ester (a-2: high polar product (MP)). Mixture 1: 1 of a-1 (LP), a-2 (MP): 1H-NMR (CDC13): d 1.34-1.55 (9H, m), 3.59 (1H, d), 3.77 (3H, s), 3.92 (3H, s), 4.41 (2H, q), 4.69 - 4.76 (1H, m), 5.81 (1H, s), 5.83 (1H, s), 6.82 (2H, d), 6.93 (1H, d), 7.20 (2H, d), 7.43 (1H, s), 7.67 (1H, s). SIMS: m / z 501 (M ++ l). (b) Active manganese dioxide (24 g) was added to a solution of the 1: 1 mixture (7.01 g, 14.02 mmol) of the compound (a-1) and compound (a-2), prepared in the previous step (a), in methylene chloride (160 ml), and the mixture was stirred at room temperature overnight. The reaction solution was filtered through Celite and washed with methylene chloride. The solvent was then evaporated under reduced pressure to provide a 1: 1 mixture (6.98 g, 100%) of 4- (5-isopropoxy-4-methoxy-2-nitrobenzoyl) -1- (4-methoxybenzyl) -1H-1 , 2, 3-triazole-5-carboxylic acid ethyl ester (b-1: LP) and 5- (5-isopropoxy-4-methoxy-2-nitrobenzoyl) -1- (4-methoxybenzyl) -1H-1, 2, Ethyl 3-triazole-4-carboxylate (b-2: MP) in the form of a foam. Mixture 1: 1 of b-1 (LP), b-2 (MP): 1 H-NMR (CDCI 3): d 1.17 (3 / 2H, t), 1.37 - 1.43 (9 / 2H, m), 3.78 (3H , s), 3.97 (3 / 2H, s), 3.99 (3 / 2H, s), 4.08 (1H, q), 4.42 (1H, q), 4.55 - 4.60 (1 / 2H, m), 4.67 - 4.72 (1 / 2H, m), 5.70 (1H, s), 5.78 (1H, s), 6.79 (1 / 2H, s), 6.84 - 6.8B (2H, m), 6.97 (1 / 2H, s), 7.24 (1H, d), 7.42 (1H, d), 7.52 (1 / 2H, s), 7.67 (1 / 2H, s). EIMS: m / z 498 (M +). Intermediate 1: Methyl 4- (3, 4-dimethoxyphenyl) -4-oxo-2-butinoate A solution of bromine (0.05 ml) in methylene chloride (5 ml) was added dropwise to a solution of 4- Methyl (3,4-dimethoxyphenyl) -4-oxo-2-butenoate (201 mg, 0.8 mmol) in methylene chloride (5 ml) under ice-cooling for a period of 20 minutes. The mixture was stirred under cooling with ice for 1 hour. The temperature of the reaction was then raised to room temperature. The reaction solution was treated via a conventional method to provide methyl 2,3-dibromo-4- (3,4-dimethoxyphenyl) -4-oxobutanoate (332 mg, 100%) as a diastere mixture ( mixing = 61:39) in the form of a colorless foam. The diastere mixture was used in the next reaction without separation. Main component: 1H-NMR (CDC13): d 3.74 (3H, s), 3.92 (3H, s), 3.95 (3H, s), 4.83 (1H, d), 5.44 (1H, d), 6.91 (1H, d), 7.49 (1H, d), 7.64 (1H, dd). EIMS: m / z 411 (M ++ l).

Minor component: 1H-NMR (CDC13): d 3.88 (3H, s), 3.94 (3H, s), 3.96 (3H, s), 4.96 (1H, d), 5.62 (1H, d), 5.62 (1H, d), 6.92 (1H, d), 7.57 (1H, d), 7.64 (1H, dd). EIMS: m / z 411 (M ++ l). A solution of triethylamine (27 mg) in methylene chloride (0.5 ml) was added to a solution of 2,3-dibromo-4- (3,4-dimethoxyphenyl) -4-oxobutanoate methyl (49 mg, 0.1 mmol) , prepared above, in methylene chloride (0.5 ml). The mixture was stirred at room temperature for 15 minutes and then heated under reflux with stirring for 2 hours. The mixture was then treated by a conventional method and the crude product was purified by column chromatography on silica gel (hexane / ethyl acetate) to give the title compound as a yellow crystal (21 mg, 71% ). 1 H-NMR (CDCl 3): d 3.89 (3H, s), 3.95 (3H, s), 3.99 (3H, s), 6. 94 (1H, d), 7.56 (1H, d), 7.82 (1H, dd). EIMS: m / z 248 (M +). Intermediate 2j ethyl 4- (3, 4-dimethoxyphenyl) -4-oxo-2-butynoate The procedure described above was repeated in relation to intermediate 1 to prepare 2,3-dibromo-4- (3,4-dimethoxyphenyl) Ethyl-4-oxobutanoate (7.3 g, 95%) as a diastere mixture as a colorless foam (mixing ratio = 63: 37) from a solution of 4- (3, -dimethoxyphenyl) -4 ethyl -oxo-2-butenoate (4.8 g, 18 mmol) in methylene chloride (500 ml) and a solution of bromine (1.1 ml) in methylene chloride (100 ml). The diastere mixture was used in the next reaction without separation. Main component: ^ -NMR (CDC13): d 1.24 (3H, t), 3.94 (3H, s), 3.97 (3H, s), 4.20 (2H, q), 4.84 (1H, d), 5.46 (1H, d), 6.93 (1H, d), 7.51 (1H, d), 7.66 ( 1H, dd). EIMS: m / z 424 (M +). Minor component: ^? - NMR (CDC13): d 1.38 (3H, t), 3.96 (3H, s), 3.98 (3H, s), 4.36 (1H, q), 4.97 (1H, d), 5.65 (1H , d), 6.94 (1H, d), 7.59 (1H, d), 7.67 (1H, dd). EIMS: m / z 424 (M ++ l). A solution of ethyl 2, 3-dibromo-4- (3, 4-dimethoxyphenyl) -4-oxobutanoate (4.76 g, 11.2 mmol), prepared above, in methylene chloride (20 ml) and a solution of triethylamine (4g) in methylene chloride (5 ml) were subjected to reaction and treatment in the same manner as described above in relation to intermediate 1. The crude product was purified by column chromatography on silica gel (hexane / ethyl acetate). ethyl) to provide the title compound (2.4 g, 82%) as a yellow crystal. 1H-NMR (CDC13): d 1.37 (3H, t), 3.94 (3H, s), 3.98 (3H, s), 4.35 (2H, q), 6.95 (1H, d), 7.57 (1H, d), 7.83 (1H, dd). EIMS: m / z 262 (M +).

Intermediate 3: Ethyl 4- (4,5-dimethoxy-2-nitrophenyl) -4-oxo-2-butynate The procedure described above was repeated in relation to intermediate 1 to prepare 2,3-dibromo-4- ( Ethyl 4,5-dimethoxy-2-nitrophenyl) -4-oxobutanoate (337 mg, 100%) as a diastere mixture as a light brown oil (mixing ratio = 2: 1) from a solution of ethyl 4- (4,5-dimethoxy-2-nitrophenyl) -4-oxo-2-butenoate (199 mg, 0.6 mmol) in methylene chloride (10 ml) and a solution of bromine (0.04 ml) in chloride of methylene (5 ml). The diastere mixture was used in the next reaction without separation. Main component: ^ - MR (CDC13): d 1.32 (3H, t), 4.01 (6H, s), 4.31 (2H, q), 5.03 (1H, d), 5.52 (1H, d), 6.99 (1H, s), 7.63 (1H, s). Minor component: ^ -NMR (CDCl3): d 1.34 (3H, t), 4.01 (6H, s), 4.31 (2H, q), 4.91 (1H, d), 5.25 (1H, d), 7.02 (1H, s), 7.65 (1H, s). Diisopropylethylamine (74 L) was allowed to act on the prodact (90 mg, 0.2 mmol), prepared above, in methylene chloride (1 mL). The crude product was purified by column chromatography on silica gel (hexane / ethyl acetate) to give the title compound (17 mg, 29%) as a yellow crystalline powder. This compound can also be produced by the oxidation of ethyl 4-hydroxy-4- (4,5-dimethoxy-2-nitrophenyl) -2-butinoate described in Synthesis Example 1 in methylene chloride with active manganese dioxide under conventional reaction conditions (for example, at room temperature for 10 hours). 1H-NMR (CDC13): d 1.36 (3H, t), 4.01 (3H, s), 4.02 (3H, s), 4.27 (2H, q), 7.06 (1H, s), 7.55 (1H, s). Intermediate 4_: 5- (3,4-dimethoxybenzoyl) -1- (4-methoxybenzyl) -1H-1,2,3-triazole-4-carboxylic acid methyl ester and 4- (3,4-dimethoxybenzoyl) -3- (4-methoxybenzyl) -1 H-1,2,3-triazole-5-carboxylic acid methyl ester. A solution of 4-methoxybenzyl azide (37 mg, 0.2 mmol) in toluene (1 ml) was added to a solution of 4-methoxybenzyl. Methyl (3,4-dimethoxyphenyl) -4-oxo-2-butinoate (47 mg, 0.2 mmol) (intermediate 1) in toluene (1 ml). The mixture was stirred at a temperature of 100 ° C for 18 hours. The reaction solution was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane / ethyl acetate) to give the title compound (colorless oil of low polarity (30 mg, 39%) and high polarity compound in the form of a light yellow foam (40 mg, 51%)). Low polarity compound: • -H-NMR (CDCI3): d 3.71 (3H, s), 3.72 (3H, s), 3.87 (3H, s), 3.88 (3H, s), 5.75 (2H, s), 6.80 (2H, d), 6.82 (1H, d), 7.26 (2H, d), 7.58 (1H, dd), 7.62 (1H, d). EIMS: m / z 411 (M +). High polarity compound: 1H-NMR (CDC13): d 3.60 (3H, s), 3.64 (3H, s), 3.81 (3H, s), 3.85 (3H, s), 5.43 (2H, s), 6.57 ( 2H, d), 6.60 (1H, d), 6.77 (1H, d), 6.99 (2H, d), 7.25 (1H, d). EIMS: m / z 412 (M ++ l). Itermediate product 5: 5- (3,4-dimethoxybenzoyl) -1H-1, 2, 3-triazole-4-carboxylate ethyl In the same way as in intermediate 4, a solution of 4-methoxybenzyl azide was added (1.8 g) in toluene (10 ml) was added to a solution of ethyl 4- (3, 4-dimethoxyphenyl) -4-oxo-2-butinoate (intermediate 2) (2.4 g, 9.2 mmol) in toluene (80 ml). The mixture was stirred at a temperature of 100 ° C for 18 hours. The reaction solution was concentrated under reduced pressure to provide a mixture of 5- (3,4-dimethoxybenzoyl) -1- (4-methoxybenzyl) -1 H-1,2,3-triazole-4-carboxylate of ethylene and 4- (3,4-dimethoxybenzoyl) -3- (4-methoxybenzyl) -1 H-1,2,3-triazole-5-carboxylic acid ethyl ester in the form of an oil. The oil was used in the next reaction without purification. Main component: -NMR (CDC13): d 1.08 (3H, t), 3.68 (3H, s), 3.88 (3H, s), 3.92 (3H, s), 4.18 (2H, q), 5.51 (2H, s), 6.64 (2H, d), 6.67 (1H, d), 6.86 ( 2H, d), 7.07 (1H, dd), 7.31 (1H, d).

Minor component: 1H-NMR (CDC13): d 1.14 (3H, t), 3.80 (3H, s), 3.94 (3H, s), 3.95 (3H, s), 4.24 (2H, q), 5.82 (2H, s), 6.85-6.90 (3H, m), 7.33 (2H, d), 7.63 (1H, dd), 7.68 (1H, d). A mixture of the above crude product, trifluoroacetic acid (7.9 ml), and anisole (1.2 g) was heated with stirring at a temperature of 90 ° C for 2 hours. The reaction mixture was concentrated under reduced pressure. Ethyl acetate was added to the residue. The mixture was extracted with a saturated aqueous solution of sodium hydrogencarbonate. The aqueous layer was neutralized with hydrochloric acid and extracted again with ethyl acetate. The organic layer was washed with a brine solution and dried over anhydrous magnesium sulfate. The solvent was evaporated to give the title compound as a light yellow solid (2.9 g, 91% in two steps). 1H-NR (CDCl 3): d 1.23 (3H, s), 3.95 (3H, s), 3.96 (3H, s), 4.31 (2H, q), 5.59 (2H, s), 6.87 (1H, d), 7.41 (1H, dd), 7.62 (1H, d). Intermediate 6: 5 (or 4) - (3,4-dimethoxybenzoyl) -1- (4-methoxybenzyl) -1H-1,2,3-triazole-4 (or 5) -ethylcarboxylate (a) A solution of butyllithium in hexane (1.58 M, 0. 24 ml, 0.39 mmol) at a temperature of -78 ° C to a solution of 4-bromoveratrol (50 l 0.35 mmol) in tetrahydrofuran (1.5 ml) under an argon atmosphere. After 15 minutes, this solution was added at a temperature of -78 ° C to a solution of diethyl 1- (4-methoxybenzyl) -1 H-1,2,3-triazole-4,5-dicarboxylate (117 mg, 0.35 mmol) in tetrahydrofuran (1 ml). The mixture was stirred for 40 minutes. A saturated aqueous solution of ammonium chloride was added to the reaction solution. The mixture was extracted with ethyl acetate. The organic layer was washed with a saturated and dried brine solution. The solvent was evaporated. The residue was purified by column chromatography on silica gel (ethyl acetate / hexane) to give the title compound as a single compound (60 mg, 40%). The Rf value of silica gel thin-layer chromatography on silica gel and the 1H-NMR spectrum were the same as those observed for the main component of the mixture of isomers in position two obtained by the conversion of intermediate 5 into a triazole compound. 1H-NMR (CDC13): d 1.08 (3H, t), 3.68 (3H, s), 3.88 (3H, s), 3.92 (3H, s), 4.18 (2H, q), 5.51 (2H, s), 6.64 (2H, d), 6.67 (1H, d), 6.86 (2H, d), 7.07 (1H, dd), 7.31 (1H, d). EIMS: m / z 425 (M +). (b) A solution of 4-bromoveratrol (183 mg, 0.84 mmol) in tetrahydrofuran (1 ml) was added to a mixture of magnesium (33 mg, 1.36 mg atom) in tetrahydrofuran (1 ml) at room temperature under an atmosphere of argon. After 20 minutes, the reaction solution was heated under reflux for 30 minutes. A smaller amount of iodine was added, followed by stirring for an additional 20 minutes. The reaction solution was added to a solution of diethyl 1- (4-methoxybenzyl) -1H-1,2,3-triazole-4,5-dicarboxylate (218 mg, 0.84 mmol) in tetrahydrofuran (1 ml) under cooling with ice. The temperature of the reaction solution was high, and the reaction solution was then stirred at room temperature for 3 days. A saturated aqueous solution of ammonium chloride was added to the reaction solution to stop the reaction. The reaction mixture was treated in the same manner as in step (a) and purified by column chromatography on silica gel to provide the title compound (68 mg, 19%) Intermediate 7: 5- (4, 5-dimethoxy-2-nitrobenzoyl) -1- (4-methoxybenzyl) -1H-1,2,3-triazole-4-carboxylic acid ethyl ester and 4- (4,5-dimethoxy-2-nitrobenzoyl) -1- ( Ethyl 4-methoxybenzyl) -1 H-1,2,3-triazole-5-carboxylate In the same manner as in the case of intermediate 4, 4-methoxybenzyl azide (19 mg) was added to a solution of 4-methoxybenzyl. (4,5-dimethoxy-2-nitroyl) -4-oxo-2-butynoate (17 mg, 0.055 mmol), synthesized in accordance with that described above in relation to intermediate 3, in toluene (1 ml). The mixture was stirred at a temperature of 60 ° C for 20 hours. The reaction solution was concentrated. The residue was purified by column chromatography on silica gel (hexane / ethyl acetate) to give the yellow crystalline powder (low polarity product: high polarity product = 2: 3 mixture) (19 mg, 75%) . The Rf value of thin-layer chromatography on silica gel and the spectrum ""? -NMR (CDCI3) were the same as those obtained for the compounds b-1 (high polarity product) and b-2 (low product). polarity] prepared in the synthesis example 1. Intermediate product 8: 5- (3,4-dimethoxybenzoyl) -2- (1-isopropoxycarbonyloxy-2-methylpropyl) -2H-1,2,3-triazole-4-carboxylate of ethyl p-Toluenesulfonic acid monohydrate (482 mg, 2.5 mmol) as well as isobutylaldehyde (3.4 ml, 37 mmol) was added to a solution of 5- (3,4-dimethoxybenzoyl) -1H-1,2,3-triazole Ethyl 4-carboxylate (7.7 g, 25 mmol), prepared according to that described above in relation to intermediate 5, in methylene chloride (115 ml) under an argon atmosphere at a temperature of -20 ° C. The mixture was stirred at a temperature of -20 ° C for 1 hour, carbonyldiimidazole (6.2 g, 38 mmol) was added followed by stirring at a temperature of -20 ° C for an additional 1 hour. He mixed isopropyl alcohol (20 ml). The mixture was cooled to a temperature of -30 ° C. Trifluoroacetic acid (5.8 ml, 75 mmol) was added. The mixture was stirred at room temperature for 18 hours. The reaction solution was treated by a conventional method and purified by column chromatography on silica gel (hexane / ethyl acetate) to give the title compound as a colorless liquid (10.9 g, 93.4%). ^ -NMR (CDC13): d 0.87 (3H, d), 1.15 (3H, d), 1.27 (3H, t), 1.28 (3H, d), 1.33 (3H, d), 2.76 (1H, m), 3.94 (3H, s), 3.96 (3H, s), 4.34 (2H, q), 4.90 (1H, sept), 6.54 (1H, d), 6.89 (1H, d), 7.47 (1H, d), 7.64 (1H, s). TSPMS: m / z 464 (M ++ l). Intermediate 9: 5- (4,5-dimethoxy-2-nitrobenzoyl) -2- (1-isopropoxycarbonyloxy-2-methylpropyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester - - 70% nitric acid (1 ml) to 5- (3,4-dimethoxybenzoyl) -2- (1-isopropoxycarbonyloxy-2-methylpropyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (86 mg , 0.19 mmol) as intermediate 8 under cooling with ice. The mixture was stirred at this temperature for 30 minutes. The reaction solution was poured on ice and then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated brine solution in this order, and dried over anhydrous magnesium sulfate. The solvent was evaporated to give the title compound as a single compound (49 mg, 52%). The Rf value of thin-layer chromatography on silica gel and the spectrum "-" - NMR were the same as those observed in the case of the title compound of example 20 (a). ^? - MR (CDC13): d 0.72 (3H, d), 1.05 (3H, d), 1.25 (3H, d), 1.28 (3H, d), 1.44 (3H, t), 2.56 (1H, m), 4.00 (3H, s), 4.08 (3H, s), 4.49 (2H, q), 4.85 (1H, m), 6.35 (1H, d), 7.06 (1H, s), 7.62 (1H, s). Example 1 1- 1- (1-isopropoxycarbonyloxyethyl) -7,8-dimethoxy-4 (5H), 10-dioxo-1H-1,2,3-triazolo [4,5-c] [l] benzazepine (substituted in position 1), 2- (1-isopropoxycarbonyloxyethyl) -7,8-dimethoxy- (5H), 10-dioxo-2H-1, 2,3, -triazolo [4, 5-c] [1] benzazepine (substituted in position 2), and 3- (1-isopropoxycarbonyloxyethyl) -7,8-dimethoxy-4 (5H), 10-dioxo-3H-1,2,3-triazolo [4,5-c] [1] benzazepine (substituted on position 1-Iodoethylisopropyl carbonate (2.82 g) and sodium hydrogencarbonate (919 mg) were added to a solution of 7,8-dimethoxy-4 (5H), 10-dioxo-lH-1, 2,3-triazole [4, 5-c] [1] benzazepine (Synthesis example 1) (1.00 g) in N, N-dimethylformamide (20 ml) under an argon atmosphere. A mixture was stirred at a temperature of 60 ° C for 18 hours. The solvent was evaporated under reduced pressure. Water and ethyl acetate were added. The organic layer was separated. The organic layer was washed with water and a saturated brine solution, in this order, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The resulting mixture was purified repeatedly by column chromatography on silica gel (hexane / ethyl acetate). As a result, the substituted compound in the 3-position (275 mg), the substituted compound in the 2-position (55 mg), and the substituted compound in the 1-position (66 mg) each were obtained in the form of a colored powder yellow in the order of circumvention. 1- (1-isopropoxycarbonyloxyethyl) -7,8-dimethoxy-4 (5H), 10-dioxo-1H-1,2,3-triazolo [4,5-c] [1] benzazepine (substituted in position 1) 1H -NMR (CDC13): d 1.24 (3H, d), 1.29 (3H, d), 2.14 (1H, d), 3.98 (3H, s), 4.08 (3H, s), 4.80 - 4.90 (2H, m) , 7.10 (1H, s), 7.74 (1H, s), 7.80 (1H, q), 11.07 (1H, s). 2-1-isopropoxycarbonyloxyethyl) -7,8-dimethoxy-4 (5H), 10-dioxo-2H-1,2,3-triazolo [4,5-c] [1] benzazepine (substituted in position 2) 1H- NMR (CDCI3): d 1.27 (3H, d), 1.31 (3H, d), 2.06 (1H, d), 4.00 (3H, s), 4.06 (3H, s), 4.85-4.95 (2H, m), 6.85 (1H, s), 7.13 (1H, q), 787 (1H, s), 9.97 (1H, s). 3- (1-isopropoxycarbonyloxyethyl) -7,8-dimethoxy-4 (5H), 10-dioxo-3H-1,2,3-triazolo [4,5-c] [l] benzazepine (substituted in 3-position) 1H -NR (CDCI3): d 1.21 (3H, d), 1.29 (3H, d), 2.12 (1H, d), 4.00 (3H, s), 4.01 (3H, s), 4.75 - 4.85 (2H,), 6.57 (1H, s), 7.90 (1H, s), 7.91 (1H, q), 8.86 (1H, s). Example 2 7, 8-dimethoxy-4 (5H), 10-dioxo-l- (pivaloyloxymethyl) -1H-1, 2, 3-triazolo [4,5-c] [1] benzazepine (substituted in position 1), 7, 8-dimethoxy-4 (5H), 10-dioxo-2- (pivaloyloxymethyl) -2H-1, 2, 3-triaz lo [4,5-c] [ljbenzacepin (substituted in position 2), and 7, 8-dimethoxy-4 (5H), 10-dioxo-3- (pivaloyloxymethyl) -3H-1,2,3-triazolo [4,5-c] [1] benzazepine (substituted in position 3) The title compound ( 345 mg, 89%) was prepared in the form of a mixture of three compounds of 7,8-dimethoxy-4 (5H), 10-dioxo-lH-1,2,3-triazolol [4, 5-c] [1 ] benzazepine (Synthesis Example 1) (296 mg) in the same manner as in Example 1, except that pivaloyloxymethyl chloride and sodium iodide were used in place of 1-iodoethylisopropyl carbonate. This was purified by column chromatography on silica gel (hexane / ethyl acetate) to separate three isomers as yellow powders. 7, 8-dimethoxy-4 (5H), 10-dioxo-l- (pivaloyloxymethyl) -1H-1, 2, 3-triazolo [4, 5-c] [1] benzazepine (substituted in position 1) 1H-NMR (DMSO-d6): d 1.13 (9H, s), 3.85 (6H, s), 6.74 (2H, s), 7.18 (1H, s), 7.70 (1H, s), 11.48 (1H, s) ). 7, 8-dimethoxy-4 (5H), 10-dioxo-2- (pivaloyloxymethyl) -2H-1, 2, 3-triazolo [4,5-c] [1] benzazepine (substituted in position 2) ^ -NMR (DMSO-de): d 1.16 (9H, s), 3.84 (3H, s), 3.85 (3H, s), 6.54 (2H, s), 7.17 (1H, s), 7.64 (1H, s), 11.17 (1H, s). 7,8-dimethoxy- (5H), 10-dioxo-3- (pivaloyloxymethyl) -3H-1,2,3-triazolo [4,5-c] [1] benzazepine (substituted in position 3) XH-NMR ( DMSO-de): d 1.12 (9H, s), 3.83 (3H, s), 3.86 (3H, s), 6.70 (2H, s), 7.20 (1H, s), 7.59 (1H, s), 11.29 ( 1H, s). Example 3 '2- (Ethoxycarbonyloxymethyl) -7,8-dimethoxy-4 (5H), 10-dioxo-2H-1, 2,3-triazolo [4,5-c] [1] benzazepine (3a) were suspended (4,5-dimethoxy-2-nitrobenzoyl) -1 H-2,3-triazole-4-carboxylic acid ethyl ester (Synthesis example 2) (70 mg) and p-toluenesulfonic acid monohydrate (17 mg) in methylene chloride (10 ml) under an atmosphere of, argon. Paraformaldehyde (6 mg) was added. The mixture was stirred at room temperature for 30 minutes. Pyridine (0.05 ml) and ethyl chloroformate (0.04 ml) were added and the mixture was stirred at room temperature for 1 hour. further, pyridine (0.02 ml) and ethyl chloroformate (0.04 ml) were added, and the mixture was stirred for 10 minutes. The solvent was evaporated under reduced pressure. Ethyl acetate (15 ml) and a saturated aqueous solution of sodium hydrogencarbonate (10 ml) were added, followed by separation. The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate (10 ml) and a saturated brine solution (10 ml) in this order, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give ethyl 2- (ethoxycarbonyloxymethyl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylate as a foam. light yellow color (48 mg, 53%). "-H-NMR (CDC13): d 1.31 (3H, t), 1.44 (3H, t), 4.01 (3H, s), 4.03 (3H, s), 4.25 (2H, q), 4.49 (2H, q ), 6.21 (2H, s), 7.02 (1H, s), 7.66 (1H, s). EIMS: m / z 452 (M +). (3b) 2- (Ethoxycarbonyloxymethyl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (45 mg) prepared in step (3a) was dissolved in ethyl acetate (1 ml). Palladium hydroxide (15 mg) was added to the solution. The mixture was stirred under an atmosphere of hydrogen at room temperature for 15 hours. The reaction solution was filtered through Celite. The filtrate was concentrated under reduced pressure to give ethyl 5- (2-amino-4,5-dimethoxybenzoyl) -2- (ethoxycarbonyloxymethyl) -2H-1,2,3-triazole-4-carboxylate as a yellow oil (40 mg, 95%). ^ -NMR (CDCI3): d 1.27 (3H, t), 1.33 (3H, t), 3.66 (3H, s), 3.90 (3H, s), 4.27 (2H, q), 4.34 (2H, q), 6.15 (1H, s), 6.38 (2H, s), 6.49 (2H, brs), 6.76 (1H, s). EIMS: m / z 422 (M +) (3c) 5- (2-amino-4,5-dimethoxybenzoyl) -2- (ethoxycarbonyloxymethyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (40 mg ) prepared in step (3b) was dissolved in acetic acid (2 ml). The solution was stirred at a temperature of 100 ° C for 2 hours. The solution was then allowed to cool, and the solvent was evaporated under reduced pressure. Water was added to the residue. The resulting precipitate was collected by filtration, washed with a saturated aqueous solution of sodium hydrogencarbonate and water, and dried to provide the title compound as a yellow crystalline powder (20 mg, 56%). ^ -NMR (DMSO-de): d 1.23 (3H, t), 3.84 (3H, s), 3.86 (3H, s), 4.22 (2H, q), 6.56 (2H, s), 7.18 (1H, s) ), 7.65 (1H, s), 11.2 (1H, brs). EIMS: m / z 376 (M +) Example 4 2- (isobutoxycarbonyloxymethyl) -7,8-dimethoxy-4 (5H), 10-dioxo-2H-1,2,3-triazolo [4,5-c] [l ] benzazepine (4a) in the same manner as in Example 3 (3a), provided that isobutyl chloroformate was used in place of ethyl chloroformate, 2- (isobutoxycarbonyloxymethyl) -5- (4,5-dimethoxy) was prepared 2-nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (172 mg, 90%) as a light yellow oil from 5- (4,5-dimethoxy-2-nitrobenzoyl) -1H Ethyl-1, 2, 3-triazole-4-carboxylate (Synthesis example 2) (140 mg). ^ -NMR (CDC13): d 0.92 - 0.96 (6H, m), 1.44 (3H, t), 1.93 -2.04 (1H, m), 3.90 - 3.98 (2H, m), 4.00 (3H, s), 4.03 (3H, s), 4.50 (2H, q), 6.21 (2H, s), 7.01 (1H, s), 7.65 (1H, s). EIMS; m / z 480 (M +). (4b) In the same manner as in Example 3 (3b), 5- (2-amino-4,5-dimethoxybenzoyl) -2- (isobutoxycarbonyloxymethyl) -2H-1,2,3-triazole-4- was prepared ethyl carboxylate (148 mg, 94%) as a yellowish brown oil from 2- (isobutoxycarbonyloxymethyl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1,2,3-triazole; 4-ethyl carboxylate (170 mg) prepared in step (4a). ^ -H-NMR (CDC13): d 0.93-0.96 (6H,), 1.27 (3H, t), 1.95 -2.02 (1H, m), 3.65 (3H, s), 3.90 (3H, s), 3.90 ( 3H, s), 3.99 (2H, d), 4.34 (2H, q), 6.15 (1H, s), 6.38 (2H, s), 6.49 (2H, brs), 6.76 (1H, s). EIMS: m / z 450 (M +). (4c) In the same manner as in Example 3 (3c), the title compound (45 mg, 31%) was prepared as a yellow powder from 5- (2-amino-4,5-dimethoxybenzoyl) ) -2- (isobutoxycarbonyloxymethyl) 2 H-1,2,3-triazole-4-carboxylic acid ethyl ester (143 mg) prepared in step (4b). 1H-NMR (DMSO-de): d 0.87 (3H, d), 0.89 (3H, d), 1.88 - 1.95 (1H, m), 3.83 (3H, s), 3.85 (3H, s), 3.98 (2H, dd), 6.57 (2H, s), 7.18 (1H, s), 7.65 (1H, s), 11.16 ( 1H, brs). EIMS: m / z 404 (M +). Example 5 2- (Hexyloxycarbonyloxymethyl) -7,8-dimethoxy-4 (5H), 10-dioxo-2H-1,2,3-triazolo [4,5-c] [ljbenzazepine (5a) In the same manner as in Example 3 (3a), provided that hexyl chloroformate (0.2 ml) was used instead of ethyl chloroformate, 2- (hexyloxycarbonyloxymethyl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -2H- was prepared 1, 2, 3-triazole-4-carboxylic acid ethyl ester (168 mg, 83%) in the form of a light yellow oil from 5- (4,5-dimethoxy-2-nitrobenzoyl) -1H-1, 2, Ethyl 3-triazole-4-carboxylate (Synthesis example 2) (140 mg). 1H-MR (CDC13): d 0.86 - 0.90 (3H, m), 1.20 - 1.32 (6H, m), 1.44 (3H, t), 1.58 - 1.67 (2H, m), 4.00 (3H, s), 4.03 (3H, s), 4.18 (2H, t), 4.50 (2H, q), 6.20 (2H, s), 7.01 (1H, s), 7.65 (1H, s). EIMS: m / z 508 (M +). (5b) In the same manner as in Example 3 (3b), 5- (2-amino-4,5-dimethoxybenzoyl) -2- (hexyloxycarbonyloxymethyl) 2 H -1,2,3-triazole-4-carboxylate was prepared of ethyl (149 mg, 96%) as a yellow oil from 2- (hexyloxycarbonyloxymethyl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1,2,3-triazole-4- ethyl carboxylate (165 mg) prepared in step (5a). 1 H-NMR (CDCl 3): d 0.80 (3 H, t), 1.27 (3 H, t), 1.31 - 1.43 (6 H, m), 1.62 - 1.69 (2 H, m), 3.66 (3 H, s), 3.90 (3 H , s), 4.20 (2H, t), 4.34 (2H, q), 6.15 (1H, s), 6.37 (2H, s), 6.50 (2H, brs), 6.77 (1H, s). EIMS: m / z 478 (M +). (5c) In the same manner as in Example 3 (3c), a title compound (88 mg, 68%) was prepared in the form of a yellow powder from 5- (2-amino-4,5-dimethoxybenzoyl) ) -2- (hexyloxycarbonyloxymethyl) 2 H-1,2,3-triazole-4-carboxylic acid ethyl ester (145 mg) prepared in step (3b). XH-NMR (DMSO-de): d 0.83 (3H, t), 1.24-1.28 (6H, m), 1.58-1.62 (2H, m), 3.84 (3H, s), 3.86 (3H, s), 4.17 (2H, t), 6.56 (2H, s), 7.18 (1H, s), 7.65 (1H, s), 11.16 (1H, brs). EIMS: m / z 432 (M +). Example 6 2- (n-butoxycarbonyloxymethyl) -7,8-dimethoxy- (5H), 10-dioxo-2H-1,2,3-triazolo [4,5-c] [1] benzazepine (6a) thereof As in Example 3 (3a), provided that n-butyl chloroformate (0.26 ml) is emplaced instead of ethyl chloroformate, 2- (n-butoxycarbonyloxymethyl) -5- (4,5-dimethoxy) is prepared. 2-Nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (166 mg, 86%) as a yellow oil from 5- (4,5-dimethoxy-2-nitrobenzoyl) - Ethyl 1H-1, 2, 3-triazole-4-carboxylate(Synthesis example 2) (140 mg). 1H-NMR (CDC13): d 0.94 (3H, t), 1.35-1.41 (2H, m), 1.44 (3H, t), 1.61-1.68 (2H, m), 4.00 (3H, s), 4.03 (3H , s), 4.19 (2H, t), 4.50 (2H, q), 6.20 (2H, s), 7.02 (1H, s), 7.66 (1H, EIMS: m / z 480 (M +). (6b) In the same manner as in Example 3 (3b), 5- (2-amino-4,5-dimethoxybenzoyl) -2- (n-butoxycarbonyloxymethyl) -2H-1,2,3-triazole-4-carboxylate was prepared from ethyl (150 mg, 100%) as a yellow oil from 2- (n-butoxycarbonyloxymethyl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1, 2,3-triazole- 4-ethyl carboxylate (160 mg) prepared in step (6a) XH-NMR (CDC13): d 0.83 (3H, t), 1.27 (3H, t), 1.36-1.42 (2H, m 1.63 1.69 (2H) , m) 3.66 (3H, 3.91 (3H, s), 4.20 (2H, t), 4.34 (2H, q), 6.15 (1H, s), 6.38 (2H, s), 6.50 (2H, brs), 6.76 (1H, s). EIMS: m / z 450 (M +). (6c) In the same manner as in Example 3 (3c), the title compound (78 mg, 64%) was prepared as a yellow powder from 5- (2-amino-4,5-dimethoxybenzoyl) ) -2- (n-butoxycarbonyloxymethyl) 2 H-1,2,3-triazole-4-carboxylic acid ethyl ester (150 mg) prepared in step (6b). ^ -NMR (DMSO-de): d 0.87 (3H, t), 1.28-1.36 (2H, m), 1.55 -1.62 (2H, m), 3.84 (3H, s), 3.85 (3H, s), 4.18 (2H, t), 6.56 (2H, s), 7.17 (1H, s), 7.64 (1H, s), 11.16 (1H, brs). EIMS: m / z 404 (M +). Example 7 2- (Isopropoxycarbonyloxymethyl) -7,8-dimethoxy-4 (5H), 10-dioxo-2H-1,2,3-triazolo [4,5-c] [1] benzazepine (7a) In the same manner than in example 3 (3a), provided that a solution of 1M toluene (6 ml) of isopropyl chloroformate was used instead of ethyl chloroformate, a 2: 1 mixture (906 mg) of (2-isopropoxycarbonyloxymethyl) - 5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester and 2- (isopropoxycarbonyl) -5- (4,5-dimethoxy-2-nitrobenzoyl) - Ethyl 2H-1, 2, 3-triazole-4-carboxylate was prepared as a light yellow foam from 5- (4,5-dimethoxy-2-nitrobenzoyl) -1H-1,2,3-triazole Ethyl 4-carboxylate (Synthesis example 2) (700 mg). ^ -H-NMR (CDC13): d 1.29 (6H, d), 1.43-1.50 (3H, m), 4.01 -4.04 (6H, m), 4.47-4.55 (2 / 3H, m), 5.28-5.35 ( 1 / 3H, m), 6.19 (4 / 3H, s), 7.01 (2 / 3H, s), 7.04 (1 / 3H, s), 7.65 (2 / 3H, s), 7.67 (1 / 3H, s ). (7b) The 2: 1 mixture (870 mg) of 2- (isopropoxycarbonyloxymethyl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester and - (ethyl isopropoxycarbonyl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylate prepared in step (7a) reacted in the same manner as in the example 3 (3a). The reaction product was purified by column chromatography on silica gel (hexane / ethyl acetate) to give a 4: 1 mixture (612 mg) of 5- (2-amino-4,5-dimethoxybenzoyl) -2- ( isopropoxycarbonyloxymethyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester and 5- (2-amino-4,5-dimethoxybenzoyl) -2- (isopropoxycarbonyl) -2H-1,2,3-triazole-4 ethyl carboxylate in the form of a light yellow foam. 1H-NMR (DMSO-de): d 1.25-1.30 (3H, m), 1.31 (6H, d), 3.66 (3H, s), 3.90 (3H, s), 4.32-4.39 (2H, m), 4.90 - 4.96 (4 / 5H, m), 5.30 - 5.46 (1 / 5H, m), 6.14 (1H, s), 6.36 (8 / 5H, s), 6.49 (2H, brs), 6.77 (lH, s) . (7c) In the same manner as in Example 3 (3c), the title compound (450 mg, 75%) was prepared as a light yellow powder from the mixture 4: 1 (610 mg) of - (2-amino-4,5-dimethoxybenzoyl) -2- (isopropoxycarbonyloxymethyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester and 5- (2-amino-4,5-dimethoxybenzoyl) -2 - (ethyl isopropoxycarbonyl) -2H-1,2,3-triazole-4-carboxylate prepared in step (7b). 1 H-NMR (DMSO-de): d 1.25 (6H, d), 3.84 (3H, s), 3.85 (3H, s), 4.83-4.88 (1H, m), 6.66 (2H, s), 7.18 (1H , s), 7.65 (1H, s), 11.18 (1H, s). EXAMPLE 8 2- (Benzoyloxymethyl) -7,8-dimethoxy-4- (5H), 10-dioxo-2H-1, 2, 3-triazolo [4,5-c] [1] benzazepine (8a) thereof As in Example 3 (3a), provided that benzoyl chloride (0.28 ml) was used instead of ethyl chloroformate, a crude product of 2- (benzoyloxymethyl) -5- (4,5-dimethoxy) Nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (230 mg) as light yellow oil from 5- (4,5-dimethoxy-2-nitrobenzoyl) -1H-1, 2, 3 ethyl -triazole-4-carboxylate (synthesis example 2) (210 mg). (8b) In the same manner as in Example 3 (3b), a crude product of 5- (2-amino-4,5-dimethoxybenzoyl) -2- (benzoyloxymethyl) -2H-1, 2, 3- was prepared ethyl triazole-4-carboxylate (195 mg) as a yellow oil from the crude product of 2- (benzoyloxymethyl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylate. ethyl (230 mg) prepared in step (8a). (8c) In the same manner as in Example 3 (3c), the title compound (40 mg, three step yield 56%) was prepared as a yellow powder from the crude product of 5- (2- amino-4, 5-dimethoxybenzoyl) -2- (benzoyloxymethyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester prepared in step (8b). 1 H-NMR (DMSO-de): d 3.82 (3H, s), 3.84 (3H, s), 6.80 (2H, s), 7.14 (1H, s), 7.56 (2H, t), 7.62 (1H, s) ), 7.72 (1H, t), 8.01 (2H, d), 11. 14 (1H, brs). Example 9 2-lauroyloxymethyl) -7, 8-dimethoxy-4 (5H), 10-dioxo-2H-1,2,3, triazolo [4, 5-c] [1] benzazepine (9a) In the same way than in Example 3 (3a), provided that lauroyl chloride (0.37 ml) was used instead of ethyl chloroformate. Accordingly, ethyl 2- (lauroyloxymethyl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylate (190 mg, 85%) was prepared in the form of a light yellow oil from 5- (4,5-dimethoxy-2-nitrobenzoyl) -1 H-1,2,3-triazole-4-carboxylic acid ethyl ester (Synthesis Example 2) (140 mg). XH-NMR (CDC13): d 0.88 (3H, t), 1.20-1.30 (16H, m), 1.44 (3H, t), 1.55 - 1.65 (2H, m), 2.35 (2H, t), 4.01 (3H, s), 4.03 (3H, s), 4.50 (2H, q), 6.19 (2H, s), 7.03 (1H, s), 7.65 (1H, s). EIMS: m / z 562 (M +). (9b) In the same manner as in Example 3 (3b), 5- (2-amino-4,5-dimethoxybenzoyl) -2- (lauroyloxymethyl) -2H-1,2,3-triazole-4-carboxylate of ethyl (157 mg, 96%) was prepared as a yellow oil from ethyl 2-lauroyloxymethyl-5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylate (172 mg) prepared in step (9a). 1 H-NMR (CDCl 3): d 0.86 (3H, t), 1.24-1.29 (16H, m), 1.27 (3H, t), 1.55 - 1.65 (2H, m), 2.38 (2H, t), 3.66 (3H, s), 3.90 (3H, s), 4.34 (2H, q), 6.15 (1H, s), 6.36 (2H, s), 6.50 (2H, brs), 6.75 (1H, s). EIMS: m / z 532 (M +). (9c) In the same manner as in Example 3 (3c), the title compound (95 mg, 70%) was prepared as a yellow powder from 5- (2-amino-4,5-dimethoxybenzoyl) ) -2- (lauroyloxymethyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (150 mg) prepared in step (9b). 1 H-NMR (DMSO-de): d 0.83 (3H, t), 1.15-1.20 (16H, m), 1.51 (2H, m), 2.41 (2H, t), 3.84 (3H, s), 3.85 (3H, s), 6.54 (2H, s), 7.18 (1H, s), 7.65 (1H, s), 11.17 ( 1H, brs). EIMS: m / z 486 (M +). Example 10 7, 8-dimethoxy-4 (5H), 10-dioxo-2- (palmitoyloxymethyl) -2H-1, 2, 3-triazolo [4,5-c] [1] benzazepine (10a) In the same way than in example 3 (3a), provided that palmitoyl chloride (0.49 ml) was used instead of ethyl chloroformate, 5- (4,5-dimethoxy-2-nitrobenzoyl) -2- (palmitoyloxymethyl) was prepared -2H-1, 2, 3-triazole-4-carboxylic acid ethyl ester (194 mg, 79%) as a light yellow oil from 5- (4,5-dimethoxy-2-nitrobenzoyl) -lH-1 ^ Ethyl 2, 3-triazole-4-carboxylate (Synthesis example 2) (140 mg). 1H-NMR (CDC13): d 0.88 (3H, t), 1.20-1.30 (24H, m), 1.44 (3H, t), 1.55 - 1.59 (2H, m), 2.35 (2H, t), 4.01 (3H, s), 4.03 (3H, s), 4.50 (2H, q), 6.19 (2H, s), 7.03 (1H, s), 7.65 (1H, s). EIMS: m / z 618 (M +). (10b) In the same manner as in Example 3 (3b), 5- (2-amino-4,5-dimethoxybenzoyl) -2- (palmitoyloxymethyl) -2H-1,2,3-triazole-4- was prepared ethyl carboxylate (158 mg, 88%) in from a yellow oil from 5- (4,5-dimethoxy-2-nitrobenzoyl) -2- (palmitoyloxymethyl) -2H-1,2,3-triazole-4 ethyl carboxylate (190 mg) prepared in step (10a). 1H-NMR (CDC13): d 0.88 (3H, t), 1.24-1.29 (24H, m), 1.27 (3H, t), 1.60 - 1.65 (2H, m), 2.38 (2H, t), 3.66 (3H, s), 3.91 (3H, s), 4.34 (2H, q), 6.15 (1H, s), 6.36 (2H, s), 6.50 (2H, brs), 6.76 (1H, s). EIMS: m / z 588 (M +). (10c) In the same manner as in Example 3 (3c), the title compound (117 mg, 82%) was prepared as a yellow powder from 5- (2-amino-4,5-dimethoxybenzoyl) ) -2- (palmitoyloxymethyl) -2H-1,2,3-triazole-4-carboxylate ethyl (155 mg) prepared in step (10b). 1H-NR (DMSO-de): d 0.84 (3H, t), 1.14-1.21 (24H, m), 1.51 (2H, m), 2.41 (2H, t), 3.84 (3H, s), 3.85 (3H, s), 6.54 (2H, s), 7.18 (1H, s), 7.65 (1H, s), 11.18 ( 1H, brs). EIMS: m / z 542 (M +). Example 11 2- (4-chlorobutyryloxymethyl) -7,8-dimethoxy-4 (5H), 10-dioxo-2H-1,2,3-triazolo [4,5-c] [1] benzazepine (lia) In the same manner as in example 3 (3a), provided that 4-chlorobutyryl chloride (0.36 ml) is used instead of ethyl chloroformate, 2- (4-chlorobutyryloxymethyl) -5- (4,5-dimethoxy) was prepared -2-nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (312 mg, 80%) as a light yellow foam from 5- (4,5-dimethoxy-2-nitrobenzoyl) ) Ethyl -1 H-1, 2, 3-triazole-4-carboxylate (Synthesis example 2) (280 mg). 1H-NMR (CDC13): d 1.45 (3H, t), 2.05 - 2.14 (2H, m), 2.55 -2.64 (2H, m), 3.55 - 3.60 (2H, m), 4.02 (3H, s), 4.03 (3H, s), 4.50 (2H, q), 6.22 (2H, s), 7.03 (1H, s), 7.65 (1H, s), EIMS: m / z 484 (M +). (llb) In the same manner as in Example 3 (3b), 5- (2-amino-4,5-dimethoxybenzoyl) -2- (4-chlorobutyryloxymethyl) -2H-1,2,3-triazole was prepared. 4-ethyl carboxylate (270 mg, 91%) as a yellow oil from 2- (4-chlorobutyryloxymethyl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1, 2, 3 Ethyltriazole-4-carboxylate (315 mg). 1 H-NMR (CDCl 3): d 1.24-1.29 (3H, m), 2.12 (2H, m), 2.60 (2H, t), 3.58-3.61 (2H, m), 3.65 (3H, s), 3.91 (3H , s), 4.34 (2H, q), 6.15 (1H, s), 6.38 (2H, s), 6.51 (2H, brs), 6.74 (1H, s). EIMS: m / z 454 (M +). (11c) In the same manner as in Example 3 (3c), the title compound (180 mg, 74%) was prepared as a yellow powder from 5- (2-amino-4,5-dimethoxybenzoyl) ) -2- (ethyl 4-chlorobutyryloxymethyl-2H-l, 2,3-triazole-4-carboxylate) (270 mg). 1 H-NMR (DMSO-de): d 1.96-2.03 (2H, m), 2.38 (2H, t), 3.66 (2H, t), 3.83 (3H, s), 3.85 (3H, s), 6.54 (2H, s), 7.15 (1H, s), 11.34 (1H, brs).

EIMS: m / z 408 (M +). Example 12 2- (4-aminobenzoyloxymethyl) -7,8-dimethoxy-4 (5H), 10-dioxo-2H-1,2,3-triazolo [4,5-c] [1] benzazepine (12a) From the In the same manner as in Example 3 (3a), provided that p-nitrobenzoyl chloride (223 mg) was used instead of ethyl chloroformate, 5- (4,5-dimethoxy-2-nitrobenzoyl) -2- was prepared. (4-Nitrobenzoyloxymethyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (118 mg, 56%) as a light yellow foam from 5- (4,5-dimethoxy-2-nitrobenzoyl) ) -1 H-1, 2, 3-triazole-4-carboxylic acid ethyl ester (Synthesis Example 2) (140 mg). 1H-NMR (CDC13): d 1.45 (3H, t), 4.00 (3H, s), 4.03"(3H, s), 4.51 (2H, q), 6.48 (2H, s), 7.06 (1H, s) , 7.62 (1H, s), 8.20 (2H, d), 8.30 (2H, d), EIMS: m / z 529 (M +) .12 (b) In the same way as in example 3 (3b), prepared 5- (2-amino-4, 5-dimethoxybenzoyl) -2- (4-aminobenzoyloxymethyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (100 mg, 98%) as an oil yellowish coffee from ethyl 5- (4,5-dimethoxy-2-nitrobenzoyl) -2- (4-nitrobenzoyloxymethyl) -2H-1,2,3-triazole-4-carboxylate (115 mg) prepared in step (12b) XH-NMR (CDCI3): d 1.29 (3H, t), 3.54 (3H, s), 3.89 (3H, s), 4.15 (2H, brs), 4.33 (2H, q), 6.14 (1H) , s), 6.40 (2H, brs), 6.56 (2H, s), 6.56 - 6.67 (2H,), 6.76 (1H, s), 7.83 - 7.91 (2H, m). EIMS: m / z 469 (M +). (12c) In the same manner as in Example 3 (3c), the title compound (54 mg, 59%) was prepared as a yellow powder from 5- (2-amino-4,5-dimethoxybenzoyl) ) -2- (4-aminobenzoyloxymethyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (102 mg) prepared in step (12b). 1H-NR (DMSO-de): d 3.86 (3H, s), 3.85 (3H, s), 6.21 (2H, s), 6.56 (2H, d), 6.68 (2H, s), 7.16 (1H, s) ), 7.64 (1H, s), 7.67 (2H, d), 11.14 (1H, brs). EIMS: m / z 423 (M +). Example 13 7,8-dimethoxy-4 (5H), 10-dioxo-2- (3-pyridylcarbonyloxymethyl) -2H-1, 2,3-triazolo [4,5-c] [1] benzazepine __ (13a) De In the same manner as in Example 3 (3a), provided that thionyl chloride (0.06 ml) was used instead of ethyl chloroformate, 2-chloromethyl-5- (4,5-dimethoxy-2-nitrobenzoyl) was prepared. -2H-1, 2, 3-triazole-4-carboxylic acid ethyl ester (146 mg, 92%) in the form of a light yellow foam from 5- (4,5-dimethoxy-2-nitrobenzoyl) -1H-1 , Ethyl 2, 3-triazole-4-carboxylate (Synthesis example 2) (140 mg). 1H-NMR (CDC13): d 1.45 (3H, t), 4.00 (3H, s), 4.03 (3H, s), 5.98 (2H, s), 7.04 (1H, s), 7.66 (1H, s). EIMS: m / z 398 (M +). (13b) In the same manner as in Example 3 (3b), 5- (2-amino-4,5-dimethoxybenzoyl) -2-chloromethyl-2H-1,2,3-triazole-4-carboxylate was prepared from Ethyl (120 mg, 93%) as a light yellow oil from 2-chloromethyl-5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylate. ethyl (140 mg) prepared in step (13a). XH-NMR (CDC13): d 1.28 (3H, t), 3.66 (3H, s), 3.91 (3H, s), 4.34 (2H, q), 6.15 (3H, s), 6.42 (2H, brs), 6.73 (1H, s). EIMS: m / z 368 (M +). (13c) In the same manner as in Example 3 (3c), 2-chloromethyl-7,8-dimethoxy-4 (5H), 10-dioxo-2H-1, 2, 3-triazolo [4, 5] was prepared c] [1] benzazepine (66 mg, 66%) as a light yellow powder from 5- (2-amino-4,5-dimethoxybenzoyl) -2-chloromethyl-2H-1, 2,3-triazole Ethyl 4-carboxylate (114 mg) prepared in step (13b). 1H-MRi (DMSO-de): d 3.84 (3H, s), 3.85 (3H, s), 6.68 (2H, s), 7.17 (1H, s), 7.64 (1H, s), 11.16 (1H, brs ). EIMS: m / z 322 (M +). (13d) 2-Chloromethyl-7,8-dimethoxy-4 (5H), 10-dioxo-2H-1,2,3-triazolo [4,5-c] [1] benzazepine (47 mg) prepared in step (13c) in N, N-dimethylformamide (5 ml). Tetra-n-butylammonium bromide (10.5 mg), nicotinic acid, was added (20 mg), and potassium carbonate (34 mg) to the solution. The mixture was stirred at a temperature of 70 ° C for 1.5 hours. After allowing the mixture to stand for cooling, the reaction solution was subsequently treated with a conventional method and subjected to separation and purification to provide the title compound (41 mg, 67%) as a light yellow powder). XH-NMR (DMSO-de): d 3.84 (3H, s), 3.85 (3H, s), 6.83 (2H, s), 7. 16 (1H, s), 7.60 (1H, dd), 7.64 (1H, s), 8.35 (1H, ddd), 8.86 (1H, dd), 9.12 (1H, d), 11.16 (1H, brs). FABMS: m / z 410 (M ++ l). Example 14 7, 8-dimethoxy-4 (5H), 10-dioxo-2- (4-pyridylcarbonyloxymethyl) -2H-1, 2,3-triazolo [4,5-c] [1] benzazepine (14a). In the same manner as in example 13 (13d), provided that isonicotinic acid (24 mg) was used in place of nicotinic acid, the title compound (30 mg, 46%) was prepared as a light yellow powder from of 2-chloromethyl-7,8-dimethoxy-4 (5H), 10-dioxo-2H-1, 2, 3-triazolo [4,5-c] [l] benzazepine (52 mg) prepared in step (13c) ). ^ -H-NMR (DMSO-de): d 3.83 (3H, s), 3.85 (3H, s), 6.84 (2H, s), 7. 17 (1H, s), 7.64 (1H, s), 7.87 (2H, d), 8.83 (2H, d), 11.18 (1H, brs). FABMS: m / z 410 (M ++ l). Example 15 2- (1-isobutyryloxyethyl) -7,8-dimethoxy-4 (5H), 10-dioxo-2H-1, 2, 3-triazolo [4,5-c] [1] benzazepine (15a) From the In the same manner as in Example 3 (3a), provided that acetaldehyde (0.13 ml) and thionyl chloride (0.7 ml) were used respectively instead of paraformaldehyde and ethyl chloroformate, 2- (1-chloroethyl) -5 was prepared Ethyl (4,5-dimethoxy-2-nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylate (736 mg, 74%) in the form of a light yellow foam from 5- (4 , 5-dimethoxy-2-nitrobenzoyl) -1 H-1,2,3-triazole-4-carboxylic acid ethyl ester (Synthesis example 2) (840 mg). ^ -NMR (CDC13): d 1.45 (3H, t), 2.14 (3H, d), 4.01 (3H, s), 4.03 (3H, s), 4.50 (2H, q), 6.42 (1H, q), 7.06 (1H, s), 7.64 (1H, s). LCMS: m / z 413 (M ++ l). (15b) In the same manner as in Example 3 (3b), 5- (2-amino-4,5-dimethoxybenzoyl) -2- (1-chloroethyl) -2H-1,2,3-triazole- was prepared. 4-ethyl carboxylate (545 mg, 80%) as a light yellow foam from 2- (1-chloroethyl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1, Ethyl 2,3-triazole-4-carboxylate (735 mg) prepared in step (15a). 1 H-NMR (CDCl 3): d 1.28 (3H, t), 2.28 (3H, d), 3.65 (3H, s), 3.91 (3H, s), 4.35 (2H, q), 6.15 (1H, s), 6.51 (2H, brs), 6.6 (1H, s). LCMS: m / z 383 (M ++ l). (15c) In the same manner as in Example 3 (3c), 2- (1-chloroethyl) -7,8-dimethoxy-4 (5H), 10-dioxo-2H-1,2,3-triazolo was prepared [4, 5-c] [1] benzazepine (426 mg, 90%) as a light yellow powder from 5- (2-amino-4,5-dimethoxybenzoyl) -2- (1-chloroethyl) ) -2H-12, 3-triazole-4-carboxylic acid ethyl ester (540 mg) prepared in step (15b). 1 H-NMR (DMSO-de): d 2.20 (3H, d), 3.84 (3H, s), 3.86 (3H, s), 7.18 (1H, s), 7.21 (1H, q), 7.65 (1H, s) ), 11.19 (1H, s). FABMS: m / z 337 (M ++ l). (15d) In the same manner as in example 13 (13d), provided that isobutyric acid (0.023 ml) was used instead of ethyl chloroformate. Thus, the title compound (32 mg, 41%) was prepared in the form of a powder of a light yellow color from 2- (1-chloroethyl) -7,8-dimethoxy-4 (5H), 10-dioxo -2H-1, 2, 3-triazolo [4,5-c] [1] benzazepine - (67 mg) prepared in step (15c). 1 H-NMR (DMSO-de): d 1.05 (3 H, d), 1.10 (3 H, d), 1.88 (3 H, d), 2.60 - 2.67 (1 H, m), 3.84 (3 H, s), 3.85 (3 H , s), 7.18 (1H, s), 7.23 (1H, q), 7.65 (1H, s), 11.16 (1H, brs). LCMS: "m / z 389 (M ++ 1) Example 16 7,8-dimethoxy-2- (4-methoxyphenylacetoxymethyl) -4 (5H), 10-dioxo-2H-1,2,3-triazolo [4 , 5-c] [1] benzazepine (16a) Same as in Example 3 (3a), provided that a solution of methylene chloride of acid chloride prepared from p-methoxyphenylacetic acid (400 mg) was used and thionyl chloride (0.88 ml) instead of ethyl chloroformate, 5- (4,5-dimethoxy-2-nitrobenzoyl) -2- (4-methoxyphenylacetoxymethyl) -2H-1,2,3-triazole-4 was prepared ethyl carboxylate (210 mg, 66%) as a light yellow oil from 5- (4,5-dimethoxy-2-nitrobenzoyl) -1 H-1,2,3-triazole-4-carboxylate ethyl (example of synthesis 2) (210 mg). ^ -NMR (CDC13): d 1.45 (3H, t), 3.61 (2H, s), 3.79 (3H, s), 4.00 (3H, s), 4.03 (3H, s), 4.50 (2H, q), 6.20 (2H, s), 6.84 (2H, d), 7.03 (1H, s), 7.14 (2H, d), 7.64 (1H, s). LCMS: m / z 528 (M +). (16b) In the same manner as in Example 3 (3b), 5- (2-amino-4,5-dimethoxybenzoyl) -2- (4-methoxyphenylacetoxymethyl) -2H-1,2,3-triazole was prepared. 4-ethyl carboxylate (180 mg, 95%) as a yellow oil of ~ 5- (4,5-dimethoxy-2-nitrobenzoyl) -2- (4-methoxyphenylacetoxymethyl) -2H-1, 2, Ethyl 3-triazole-4-carboxylate (200 mg) prepared in step (16a). ^ -NMR (CDCI3): d 1.28 (3H, t), 3.60 (3H, s), 3.64 (2H, s), 3.79 (3H, s), 3.91 (3H, s), 4.35 (2H, q), 6.15 (1H, s), 6.37 (2H, s), 6.50 (2H, brs), 6.73 (1H, s), 6.84 (2H, d), 7.17 (2H, d). LCMS: m / z 499 (M ++ l). (16c) In the same manner as in Example 3 (3c), the title compound (118 mg, 75%) was prepared as a yellow powder from 5- (2-amino-4,5-dimethoxybenzoyl) ) -2- (4-methoxyphenylacetoxymethyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (175 mg) prepared in step (16b). ^ -NMR (DMSO-de): d 3.71 (3H, s), 3.74 (3H, s), 3.85 (3H, s), _ 6.56 (2H, s), 6.85 (2H, d), 7.18 (1H, s), 7.18 (2H, d), 7.65 (1H, s), 11.17 (1H, brs). LCMS: m / z 453 (M ++ l). Example 17 7,8-dimethoxy-2- (N- (2- (N, N-dimethylamino) ethyl) carbamoyloxymethyl) -4 (5H), 10-dioxo-2H-1, 2, 3-triazolo [4, 5 -c] [1) benzazepine (17a) In the same manner as in example 3 (3a), provided that p-nitrophenyl chloroformate (806 mg) was used instead of ethyl chloroformate, 5- (4 , 5-dimethoxy-2-nitrobenzoyl) -2- (4-nitrophenoxycarbonyloxymethyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (778 mg, 71%) from 5- (4,5) ethyl dimethoxy-2-nitrobenzoyl) -1 H-1,2,3-triazole-4-carboxylate (Synthesis example 2) (700 mg). 1H-NMR (CDC13): d 1.46 (3H, t), 4.01 (3H, s), 4.03 (3H, s), 4.52 (2H, q), 6.34 (2H, s), 7.05 (1H, s), 7.40 (2H, d), 7.64 (1H, s), 8.30 (2H, d). (17b) N, -dimethylethylenediamine (0.02 ml) was added to a solution of 5- (4,5-dimethoxy-2-nitrobenzoyl) -2- (4-nitrophenoxycarbonyloxymethyl) -2H-1,2,3-triazole-4. ethyl carboxylate (83 mg), prepared in step (17a), in a methylene chloride solution (1.5 ml) under ice-cooling. The mixture was stirred for 2 hours. The reaction solution was subsequently treated by a conventional method and subjected to separation and purification to provide 5- (4,5-dimethoxy-2-nitrobenzoyl) -2- (N- (2- (N, N-dimethylamino) ethyl) carbamoyloxymethyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (64 mg, 85%). ^ -NMR (CDC13): d 1.43 (3H, t), 2.21 (6H, s), 2.41 (2H, t), 3.20 - 3.30 (2H, m), 4.00 (3H, s), 4.03 (3H, s ), 4.49 (2H, q), 5.49 (1H, s), 6.18 (2H, s), 7.02 (1H, s), 7.65 (1H, s). (17c) In the same manner as in Example 3 (3b), 5- (2-amino-4,5-dimethoxybenzoyl) -2- (N- (2- (N, N-dimethylamino) ethyl) carbamoyloxymethyl was prepared ) -2H-1, 2, 3-triazole-4-carboxylic acid ethyl ester (56 mg, 100%) from 5- (4,5-dimethoxy-2-nitrobenzoyl) -2- (N- (2- ( N, N-dimethylamino) ethyl) carbamoyloxymethyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (59 mg) prepared in step (17b). ^ -H-NMR (CDCl 3): d 1.25 (3H, t), 2.75 (6H, s), 3.05-3.15 (2H, m), 3.58-3.68 (2H, m), 3.67 (3H, s), 3.90 (3H, s), 4.32 (2H, q), 6.15 (1H, s), 6.37 (2H, s), 6.50 (2H, brs), 6.75 (1H, s). FABMS: m / z 465 (M ++ l). (17d) In the same manner as in Example 3 (3c), the title compound (28 mg, 56%) was prepared as a white powder from 5- (2-amino-4,5-dimethoxybenzoyl) ) -2- (N- (2- (N, N-dimethylamino) ethyl) carbamoyloxymethyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (56 mg) prepared in step (17c). 1 H-NMR (DMSO-de): d 2.77 (6H, s), 3.10 - 3.20 (2H, m), 3.35 -3.45 (2H, m), 3.84 (3H, s), 3.86 (3H, s), 6.49 (2H, s), 7.20 (1H, s), 7.65 (1H, s), 7.98 (1H, t), 11.16 (1H, s). EIMS: m / z 418 (M ++ l). Example 18 2- (diethoxyphosphoryloxymethyl) -7,8-dimethoxy-4 (5H), 10-dioxo-2H-1,2,3-triazolo [4,5-c] [1] benzazepine (18a) In the same way in example 3 (3a), provided that diethyl chlorophosphate (0.12 ml) is placed in place of ethyl chloroformate, a crude product of ethyl 2- (diethoxyphosphoryloxymethyl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylate (205 mg) from 5 was prepared. Ethyl (4,5-dimethoxy-2-nitrobenzoyl) -1 H-1,2,3-triazole-4-carboxylate (Synthesis example 2) (255 mg). (18b) In the same manner as in Example 3 (3b), a crude product of 5- (2-amino-4,5-dimethoxybenzoyl) -2- (diethoxyphosphoryloxymethyl) -2H-1, 2, 3- was prepared Ethyl triazole-4-carboxylate (186 mg) from the crude product of 2- (diethoxyphosphoryloxymethyl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -1H-1,2,3-triazole-4-carboxylate of ethyl (205 mg) prepared in step (18a). (18c) In the same manner as in Example 3 (3c), the title compound (73 mg, three step yield 41%) was prepared from the crude product of 5- (2-amino-4, 5- dimethoxybenzoyl) -2- (diethylphosphoryloxymethyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (179 mg) prepared in step (18b). 1 H-NMR (DMSO-de): d 1.20 (6H, t), 3.84 (3H, s), 3.86 (3H, s), 4.00-4.10 (4H, m), 6.41 (2H, d), 7.19 (1H , s), 7.66 (1H, s), 11.18 (1H, s). FABMS: m / z 441 (M ++ l). Example 19 7,8-dimethoxy-4 (5H), 10-dioxo-2- (1- (3-pentyloxycarbonyloxy) propyl) -2H-1,2,3-triazolo [4,5-cj [1] benzazepine ( 19a) 5- (4,5-dimethoxy-2-nitrobenzoyl) -1 H-1,2,3-triazole-4-carboxylic acid ethyl ester (synthesis example 2) (2.1 g) and p-toluenesulfonic acid monohydrate were suspended. (23 mg) in methylene chloride (60 ml) under an argon atmosphere. Propionaldehyde (0.48 ml) was added to the suspension. The mixture was stirred at room temperature for 3 minutes. 1, 1'-Carbonyldiimidazole (1.07 g) was added and the mixture was stirred at room temperature for 10 minutes. The mixture was subsequently treated by a conventional method and then subjected to separation and purification to provide 2- (1-imidazolylcarbonyloxy) propyl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1, 2, 3- ethyl triazole-4-carboxylate (2.35 g, 78%) as a light yellow foam. ^ -NMR (CDC13): d 0.95 (3H, t), 1.45 (3H, t), 2.34-2.46 (2H, m), 4.01 (3H, s), 4.05 (3H, s), 4.50 (2H, q ), 6.94 (1H, t), 7.08 (1H, m), 7.09 (1H, s), 7.39-7.40 (1H, m), 7.60 (1H, s), 8.12 (1H, m). (19b) 2- (1- (Imidazolylcarbonyloxy) propyl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (377 mg) prepared in step (19a) in toluene (12 ml). 3-pentanol (1.6 mol) was added to the solution. The mixture was heated under reflux for 20 hours. The mixture was subsequently treated by a conventional method and subjected to separation and purification to provide 5- (4,5-dimethoxy-2-nitrobenzoyl) -2- (1- (3-pentyloxycarbonyloxy) propyl) -2H-1, 2, Ethyl 3-triazole-4-carboxylate (280 mg) in the form of a light yellow oil. ^ -NMR (CDC13): d 0.82 - 0.99 (9H, m), 1.44 (3H, t), 1.56 -1.79 (4H, m), 2.18-2.29 (2H, m), 4.00 (3H, s), 4.03 (3H, s), 4.50 (2H, q), 4.54 - 4.60 (1H, m), 6.62 (1H, t), 7.04 (1H, s), 7.62 (1H, s). LCMS: m / z 522 (M +). (19c) In the same manner as in Example 3 (3b), 5- (2-amino-4,5-dimethoxybenzoyl) -2- (1- (3-pentyloxycarbonyloxy) propyl) -2H-1, 2 was prepared , Ethyl 3-triazole-4-carboxylate (185 mg, 50% two-step yield) in the form of a light yellow oil from 5- (4,5-dimethoxy-2-nitrobenzoyl) -2- ( 1- (3-pentyloxycarbonyloxy) propyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (270 mg) prepared in step (19b). XH-NMR (CDC13): d 0.85 (3H, t), 0.92 (3H, t), 0.97 (3H, t), 1. 28 (3H, t), 1.57 - 1.67 (4H, m), 2.30 - 2.49 (2H, m), 3.64 (3H, s), 3.90 (3H, s), 4.34 (2H, q), 4.56 - 4.62 ( 1H, m), 6. 14 (1H, s), 6.48 (2H, brs), 6.77 (1H, t), 6.78 (1H, s). LCMS: m / z 493 (M ++ l). (19d) In the same manner as in Example 3 (3c), the title compound (135 mg, 83%) was prepared as a light yellow powder from 5- (2-amino-4, 5-dimethoxybenzoyl) -2- (1- (3-pentyloxycarbonyloxy) ropil) -2H- 1, 2, 3-triazole-4-carboxylic acid ethyl ester (180 mg) prepared in step (19c). ^ • H-NMR (CDCl 3): d 0.84 (3H, t), 0.92 (3H, t), 0.98 (3H, t), 1.55 - 1.67 (4H, m), 2.39 - 2.50 (2H,), 4.00 ( 3H, s), 4.05 (3H, s), 4.60 (1H, quintet), 6.75 (1H, s), 6.92 (1H, t), 7. 88 ~ (1H, s), 9.54 (1H, s). LCMS: m / z 447 (M +). Example 20 2- (l-isopropoxycarbonyloxy-2-methylpropyl) -7,8-dimethoxy- (5H), 10-dioxo-2H-1, 2,3-triazolo [4,5-c] [ljbenzazepine (20a) suspended 5- (4,5-dimethoxy-2-nitrobenzoyl) -1 H-1,2,3-triazole-4-carboxylic acid ethyl ester (synthesis example 2) (1.07 g) and p-toluenesulfonic acid monohydrate (53 mg) in methylene chloride (10 ml) under an argon atmosphere. Isobutylaldehyde (330 mg) was added to the suspension. The mixture was stirred at room temperature for 25 minutes. 1, 1'-Carbonyldiimidazole (744 mg) and methylene chloride (5.0 ml) were added, and the mixture was stirred at room temperature for 25 minutes. Isopropyl alcohol was added (920 mg), and the mixture was stirred at room temperature for 3 hours, and then refluxed for 21 hours. The mixture was subsequently treated by a conventional method and subjected to separation and purification to provide 2- (1-isopropoxycarbonyloxy-2-methylpropyl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1, 2, 3 -triazole-4-carboxylic acid ethyl ester (in the form of a light yellow foam (520 mg, 34%) -? - NR (CDC13): d 0.72 (3H, d), 1.05 (3H, d), 1.25 (3H, d), 1.28 (3H, d), 1.44 (3H, t), 2.56 (1H, m), 4.00 (3H, s), 4.08 (3H, s), 4.49 (2H, q), 4.85 (1H, m), 6.35 (1H, d), 7.06 (1H, s), 7.62 (1H, s). (20a ') 5- (4,5-dimethoxy-2-nitrobenzoyl) -1H-1,2,3-triazole-4-carboxylic acid ethyl ester (Synthesis example 2) (50 g) in ethyl acetate was suspended ( 500 ml). Isobutylaldehyde (20 ml) was added to the suspension at a temperature of 25 ° C under a stream of nitrogen. The mixture was stirred at this temperature for 20 minutes. Then, sodium iodide (21.4 g) and potassium carbonate (78.9 g) were added. In addition, 50 ml of isopropyl chloroformate was added and the reaction was allowed to proceed with stirring at a temperature of 60 ° C for 45 hours. Ethyl acetate (100 ml) was added to the reaction solution. The mixture was washed twice with 750 ml of water and then washed with a 20% aqueous sodium chloride solution (500 ml). The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was crystallized from aqueous methanol to provide 2- (l-isopropoxycarbonyloxy-2-methylpropyl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylate of ethyl (70.2 g, 96.7%). The XH-NMR spectrum of this compound was the same as the spectrum of the compound prepared in step (20a). (20a ") 5- (4,5-Dimethoxy-2-nitrobenzoyl) -1 H-1,2,3-triazole-4-carboxylic acid ethyl ester (Synthesis Example 2) (5.00 g) in ethyl acetate ( 50 ml). 1-Chloro-2-methylpropylisopropyl carbonate (8.34 g), sodium iodide (2.14 g), and potassium carbonate (7.89 g) were added to the suspension at a temperature of 25 ° C under a stream of water. The reaction was allowed to proceed with stirring at a temperature of 60 ° C for 96 hours Ethyl acetate (10 ml) was added to the reaction solution The mixture was washed twice with water (75 ml) and then washed with a 20% aqueous sodium chloride solution (50 ml) The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, the residue was purified by column chromatography on silica gel (n- hexane / ethyl acetate) to provide 2- (1-isopropoxycarbonyloxy-2-methylpropyl) -5- (4, 5-dimethoxy-2-nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (0.89 g, 12.3%). The 1H-NMR spectrum of this compound was the same as the spectrum of the compound prepared in step (20a). (20b) In the same manner as in Example 3 (3b), 5- (2-amino-4,5-dimethoxybenzoyl) -2- (l-isopropoxycarbonyloxy-2-methylpropyl) -2H-1, 2 was prepared, Ethyl 3-triazole-4-carboxylate (485 mg, 99%) as a light yellow foam from 2- (l-isopropoxycarbonyloxy-2-methylpropyl) -5- (4,5-dimethoxy-2) -nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (520 mg) prepared in step (20a). ^ - MR (CDC13): d 0.85 (3H, d), 1.14 (3H, d), 1.26 (3H, d), 1.28 (3H, t), 1.31 (3H, d), 2.75 (1H, m), 3.81 (3H, s), 3.90 (3H, s), 4.34 (2H, q), 4.86 (1H, m), 6.14 (1H, s), 6.49 (2H, brs), 6.51 (1H, d), 6.77 (1H, s). (20c) In the same manner as in Example 3 (3c), the title compound (273 mg, 62%) was prepared as a light yellow powder from 5- (2-amino-4, 5-dimethoxybenzoyl) -2- (1-isopropoxycarbonyloxy-2-methylpropyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (485 mg) prepared in step (20b). 1 H-NMR (CDCl 3): d 0.85 (3 H, d), 1.15 (3 H, d), 1.25 (3 H, d), 1.31 (3 H, d), 2.80 (1 H, m), 4.00 (3 H, s), 4.05 (3H, s), 4.86 (1H, m), 6.68 (1H, d), 6.73 (1H, s), 7.88 (1H, s), 9.47 (1H, brs). LCMS: m / z 433 (M ++ l). EXAMPLE 21 2- (Acetoxymethyl) -7,8-dimethoxy-4 (5H), 10-dioxo-2H-1, 2, 3-triazolo [4,5-c] [1] benzazepine _ __ ___ (21a) in the same manner as in Example 19 (a), provided that paraformaldehyde (45 mg) and acetic anhydride (0.3 ml) respectively were used instead of propionaldehyde and 1,1 '-carbonyldiimidazole, 2- (acetoxymethyl) - 5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (618 mg, 98%) in the form of a light yellow foam from 5- (4,5-dimethoxy-2-nitrobenzoyl) -1 H-1,2,3-triazole-4-carboxylic acid ethyl ester (Synthesis example 2) (525 mg). 1H-NMR (CDC13): d 1.45 (3H, t), 2.12 (3H, s), 4.01 (3H, s), 4.03 (3H, s), 4.50 (2H, q), 6.19 (2H, s), 7.04 (1H, s), 7.65 (1H, s). EIMS: m / z 422 (M +). (21b) In the same manner as in Example 3 (3b), 2- (acetoxymethyl) -5- (2-amino-4,5-dimethoxybenzoyl) -2H-1,2,3-triazole-4- was prepared ethyl carboxylate (510 mg, 90%) as a yellow oil from 2- (acetoxymethyl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1,2,3-triazole-4 ethyl carboxylate (610 mg) prepared in step (21a). ^ • H-NMR (CDCI3): d 1.27 (3H, t), 2.15 (3H, s), 3.66 (3H, s), 3.91 (3H, s), 4.34 (2H, q), 6.15 (1H, s ), 6.35 (2H, s), 6.50 (2H, brs), 6.75 (1H, s). EIMS: m / z 392 (M +). (21c) In the same manner as in example 3 (3c), the title compound (360 mg, 84%) was prepared as a yellow powder from 2- (acetoxymethyl) -5- (2 amino-4, 5-dimethoxybenzoyl) -2H-1, 2, 3-triazole-4-carboxylic acid ethyl ester (492 mg) prepared in step (21b). 1H-NMR (DMSO-de): d 2.12 (3H, s), 3.83 (3H, s), 3.84 (3H, s), 6.52 (2H, s), 7.14 (1H, s), 7.63 (1H, s ), 11.2 (1H, brs). EIMS: m / z 346 (M +). Example 22 2- (isobutyryloxymethyl) -7,8-dimethoxy-4 (5H), 10-dioxo-2H-1, 2, 3-triazolo [4,5-c] [1] benzazepine (22a) In the same way than in Example 19 (19a), provided that paraformaldehyde (12 mg) and isobutyric anhydride (0.17 ml) respectively were used instead of propionaldehyde and 1,1'-carbonyldiimidazole, 2- (isobutyryloxymethyl) -5- ( 4, 5-dimethoxy-2-nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (178 mg, 99%) as a light yellow oil from 5- (4, 5-dimethoxy-2-nitrobenzoyl) -1 H-1,2,3-triazole-4-carboxylic acid ethyl ester (Synthesis example 2) (140 mg). 1 H-NMR (CDCl 3): d 1.15 (3H, d), 1.21 (3H, d), 1.45 (3H, t), 2.57-2.68 (1H, m), 4.01 (3H, s), 4.03 (3H, s ), 4.50 (2H, q), 6.20 (2H, s), 7.03 (1H, s), 7.65 (1H, s). (22b) In the same manner as in Example 3 (3b), 5- (2-amino-4,5-dimethoxybenzoyl) -2- (isobutyryloxymethyl) -2H- 1, 2, 3-triazole-4- was prepared ethyl carboxylate (510 mg, 90%) as a yellow oil from 2- (isobutyryloxymethyl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1,2,3-triazole Ethyl 4-carboxylate (610 mg) prepared in step (22a). 1 H-NMR (CDCl 3): d 1.18 (6H, d), 1.28 (3H, t), 2.61-2.66 (1H,), 3.65 (3H, s), 3.90 (3H, s), 4.34 (2H, q) , 6.15 (1H, s), 6.36 (2H, s), 6.50 (2H, brs), 6.75 (1H, s). EIMS: m / z 420 (M +). (22c) In the same manner as in Example 3 (3c), the title compound (360 mg, 84%) was prepared as a yellow powder from 5- (2-amino-4,5). -dimethoxybenzoyl) -2- (isobutyryloxymethyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (492 mg) prepared in step (22b). 1H-NR (DMSO-de): d 1.10 (6H, d), 2.62 - 2.69 (1H, m), 3.84 (3H, s), 3.85 (3H, s), 6.54 (2H, s), 7.18 (1H, s), 7.64 (1H, s), 11.16 ( 1H, brs). EIMS: m / z 374 (M +). Example 23 2- (n-butyryloxymethyl) -7,8-dimethoxy-4 (5H), 10-dioxo-2H-1, 2,3-triazole [4,5-c] [1] benzazepine (23a) In the same manner as in Example 19 (19a), provided that formaldehyde (12 mg) and butyric anhydride (0.13 ml) were used instead of propionaldehyde and 1,1 '-carbonyldiimidazole, 2- (n-butyryloxymethyl) was prepared ) -5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (178 mg, 99%) in the form of a light yellow foam from 5- (4,5-Dimethoxy-2-nitrobenzoyl) -1 H-1,2,3-triazole-4-carboxylic acid ethyl ester (Synthesis Example 2) (140 mg). ^ • H-NMR (CDC13): d 0.92 (3H, t), 1.44 (3H, t), 1.61-1.71 (2H, m), 2.44 (2H, t), 4.01 (3H, s), 4.03 (3H , s), 4.50 (2H, q), 6.20 (2H, s), 7.03 (1H, s), 7.65 (1H, s). EIMS: m / z 450 (M +). (23b) In the same manner as in Example 3 (3b), 5- (2-amino-4,5-dimethoxybenzoyl) -2- (n-butyryloxymethyl) -2H-1,2,3-triazole was prepared. 4-ethyl carboxylate (126 mg, 83%) as a yellow oil from 2- (n-butyroxymethyl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1, 2 , Ethyl 3-triazole-4-carboxylate (160 mg) prepared in step (23a). XH-NMR (CDCl 3): d 0.95 (3H, t), 1.27 (3H, t), 1.64-1.70 (2H, m), 2.37 (2H, t), 3.65 (3H, s), 3.91 (3H, s ), 4.34 (2H, q), 6.15 (1H, s), 6.36 (2H, s), 6.50 (2H, brs), 6.75 (1H, s). EIMS: m / z 420 (M +). (23c) In the same manner as in Example 3 (3c), the title compound (86 mg, 80%) was prepared as a yellow powder from 5- (2-amino-4,5-dimethoxybenzoyl) ) -2- (n-butyryloxymethyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (120 mg) prepared in step (23b). 1 H-NMR (DMSO-de): d 0.87 (3H, t), 1.51-1.60 (2H, m), 2.43 (2H, t), 3.84 (3H, s), 3.85 (3H, s), 6.54 (2H, s), 7.17 (1H, s), 7.64 (1H, s), 11.3 (1H, brs). EIMS: m / z 374 (M +). Example 24 2- (3-carboxypropionyloxymethyl) -7,8-dimethoxy-4 (5H), 10-dioxo-2H-1,2,3-triazolo [4,5-c] [1] benzazepine (24a) same as in Example 19 (19a), provided that paraformaldehyde (15 mg) and a solution of methylene chloride of an acid chloride prepared from a monobenzyl ester of succinic acid (520 mg) and sodium chloride were used. thionyl (0.91 ml) respectively instead of propionaldehyde and 1,1'-carbonyldiimidazole, 2- (3- (benzyloxycarbonyl) propionyloxymethyl) -5- (-4,5-dimethoxy-2-nitrobenzoyl) -2H-1 was prepared, Ethyl 2,3-triazole-4-carboxylate (148 mg, 58%) from ethyl 5- (4,5-dimethoxy-2-nitrobenzoyl) -1 H-1,2,3-triazole-4-carboxylate (example of synthesis 2) (175 mg). -NMR (CDC13): d 1.44 (3H, t), 2.69 (4H, s), 3.99 (3H, s), 4.02 (3H, s), 4.49 (2H, q), 5.11 (2H, s), 6.19 (2H, s), 7.03 (1H, s), 7.30-7.40 (5H, m), 7.63 (1H, s). (24b) In the same manner as in example 3 (3b) and (3c), the title compound (7 mg, 26%) was prepared from 2- (3- (benzyloxycarbonyl) propionyloxymethyl) -5- ( 4,5-dimethoxy-2-nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (100 mg) prepared in step (24a). 1H-NMR (DMS0-d6): d 2.60 (4H, m), 3.83 (3H, s), 3.85 (3H, s), 6.54 (2H, s), 7.17 (1H, s), 7.64 (1H, s) ), 11.16 (1H, s), 12.54 (1H, brs). FABMS: m / z 405 (M ++ l). Example 25 2- (Cyclohexylcarbonyloxymethyl) -7,8-dimethoxy-4 (5H), 10-dioxo-2H-1,2,3-triazolo [4,5-c] [ljbenzazepine (25a) In the same manner as in Example 19 (19a), provided paraformaldehyde (15 mg) and cyclohexylcarbonyl chloride (0.54 ml) were used instead of propionaldehyde and 1,1'-carbonyldiimidazole, respectively, 2- (cyclohexylcarbonyloxyethyl) -5- ( 4, 5-dimethoxy-2-nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (416 mg) from 5- (4,5-dimethoxy-2-nitrobenzoyl) -1H-1 Ethyl 2, 3-triazole-4-carboxylate (Synthesis example 2) (175 mg). ^? - NMR (CDC13): d 1.20 - 2.00 (10H, m), 1.44 (3H, t), 2.35 (1H, m), 4.00 (3H, s), 4.03 (3H, s), 4.49 (2H, q), 6.19 (2H, s), 7.03 (1H, s), 7.65 (1H, s).

FABMS: m / z 491 (M ++ l). (25b) In the same manner as in example 3 (3b) and (3c), the title compound (32 mg, 18%) was prepared from 2- (cyclohexylcarbonyloxymethyl) -5- (4,5-dimethoxy) -2-nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (a) (200 mg) prepared in step (25a). 1 H-NMR (DMSO-de): d 1.16-1.90 (10H, m), 2.45 (1H, m), 3.85 (3H, s), 6.51 (2H, s), 7.16 (1H, s), 7.64 (1H , s), 11.15 (1H, s). FABMS: m / z 415 (M ++ l). Example 26 7,8-dimethoxy-2- (3-methoxypentan-3-yl) -4 (5H), 10-dioxo-2H-1, 2, 3-triazolo [4,5-c] [1] benzazepine ( 26a) p-Toluenesulfonic acid monohydrate (20 mg) was added a solution of 3-pentanone (3.1 ml) and trimethyl orthoformate (3.3 ml) in methylene chloride (10 ml). The mixture was heated for 1 hour with stirring. This solution (4 ml) was added to a solution of ethyl 5- (4,5-dimethoxy-2-nitrobenzoyl) -1 H-1,2,3-triazole-4-carboxylate (synthesis example 2) (140 mg ) in methylene chloride (2 ml). The mixture was stirred at room temperature for 1 hour, and then triethylamine (0.05 ml) was added. The mixture was subsequently treated by a conventional method and subjected to separation and purification to provide 5- (4,5-dimethoxy-2-nitrobenzoyl) -2- (3-methoxypentan-3-yl) -2H-1, 2, 3 Ethyltriazole-4-carboxylate (140 mg, 78%) as a yellow powder. 1H-NMR (CDC13): d 0.75-0.79 (6H, m), 1.45 (3H, t), 2.19 -2.25 (4H, m), 2.97 (3H, s), 4.01 (3H, s), 4.04 (3H, s), 4.49 (2H, q), 7.10 (1H, m), 7.60 ( 1H, s). FABMS: m / z 451 (M ++ l). (26b) In the same manner as in Example 3 (3b), 5- (2-amino-4,5-dimethoxybenzoyl) -2- (3-methoxypentan-3-yl) -2H-1, 2 was prepared, Ethyl 3-triazole-4-carboxylate (110 mg, 91%) from 5- (4,5-dimethoxy-2-nitrobenzoyl) -2- (3-methoxypentan-3-yl) -2H-1, 2 , Ethyl 3-triazole-4-carboxylate (130 mg) prepared in step (26a). ^? - NMR (CDCl 3): d 0.87 (6H, t), 1.26 (3H, t), 2.33-2.45 (4H, m), 3.13 (3H, s), 3.61 (3H, s), 3.90 (3H, s), 4.33 (2H, q), 6.15 (1H, s), 6.49 (2H, brs), 6.74 (1H, s). FABMS: m / z 421 (M ++ l). (26c) 5- (2-Amino-4,5-dimethoxybenzoyl) -2- (3-methoxypentan-3-yl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester was dissolved (80 mg) in isopropyl alcohol (1.5 ml) under an argon atmosphere. Potassium tert-butoxide (25 mg) was added to the solution. The mixture was stirred at room temperature for 15 minutes. The mixture was subsequently treated by a conventional method and subjected to separation and purification to provide the title compound (35 mg, 49%) as a yellow powder. 1 H-NMR (CDCl 3): d 0.87 (6H, t), 2.42 (2H, q), 2.53 (2H, q), 3.13 (3H, s), 4.00 (3H, s), 4.03 (3H, s), 6.66 (1H, s), 7.90 (1H, s), 9.14 (1H, brs). FABMS: m / z 374 (M +). Example 27 2- (4-Ethoxyheptan-4-yl) -7,8-dimethoxy-4 (5H), 10-dioxo-2H-1, 2, 3-triazolo [4,5-c] [1] benzazepine __ (27a) 5- (4,5-Dimethoxy-2-nitrobenzoyl) -1 H-1,2,3-triazole-4-carboxylic acid ethyl ester (Synthesis Example 2) (140 mg) and p_- monohydrate were suspended. toluenesulfonic (2 mg) in methylene chloride (2 ml) under an argon atmosphere. 4-heptane (0.14 ml) and triethyl orthoformate (0.17 ml) were added to the suspension. The mixture was stirred at room temperature for 2 hours. In addition, p_-toluenesulfonic acid monohydrate (4.5 mg) was added. The mixture was stirred at room temperature for 2 hours. The mixture was subsequently treated by a conventional method - and subjected to separation and purification to provide 2- (4-ethoxyheptan-4-yl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1, 2, Ethyl 3-triazole-4-carboxylate (160 mg, 82%) as a yellow powder. 1 H-NMR (CDCl 3): d 0.90 (6H, t), 1.00-1.15 (2H, m), 1.04 (3H, t), 1.26-1.28 (2H, m), 1.44 (3H, t), 2.05-2.21 (4H, m), 3.10 (2H, q), 4.01 (3H, s), 4.04 (3H, s), 4.48 (2H, q), 7.08 (1H, s), 7.61 (1H, s).

EIMS: m / z 492 (M +). (27b) In the same way as in Example 3 (3b), it was prepared - (2-Amino-4, 5-dimethoxybenzoyl) -2- (4-ethoxyheptan-4-yl) -2H- 1, 2, 3-triazole-4-carboxylic acid ethyl ester (160 mg, 90%) in the form of a yellow oil from ethyl 2- (4-ethoxyheptan-4-yl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylate (190 mg) prepared in step (27a). XH-NMR (CDC13): d 0.95 (6H, t), 1.10-1.19 (2H,), 1.11 (3H, t), 1.25 (3H, t), 1.35-1.38 (2H, m), 2.24-2.42 ( 4H, m), 3.25 (2H, q), 3.61 (3H, q), 3.90 (3H, s), 4.32 (2H, q), 6.15 (1H, s), 6.50 (2H, brs), 6.74 (1H, s). EIMS: m / z 462 (M +). (27c) In the same manner as in example 26 (26c), the title compound (75 mg, 60%) was prepared as a yellow crystalline powder from 5- (2-amino-4, 5-dimethoxybenzoyl) -2- (4-ethoxyheptan-4-yl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (143 mg) prepared in step (27b). 1 H-NMR (CDCl 3): d 0.96 (6H, t), 1.11-1.19 (2H, m), 1.13 (3H, t), 1.34-1.43 (2H, m), 2.30-2.38 (2H, m), 2.44. - 2.52 (2H, m), 3.28 (2H, q), 4.00 (3H, s), 4.05 (3H, s), 6.80 (1H, s), 7.90 (1H, s), 9.68 (1H, brs). FABMS: m / z 417 (M ++ l). Example 28 2- (ethoxymethyl) -7,8-dimethoxy-4 (5H), 10-dioxo-2H-1, 2, 3-triazolo [4,5-c] [1] benzazepine (28a) were suspended 5- (4,5-dimethoxy-2-nitrobenzoyl) -1 H-1,2,3-triazole-4-carboxylic acid ethyl ester (synthesis example 2) (210 mg) and p-toluenesulfonic acid monohydrate (62 mg) in methylene chloride (5 ml) under an argon atmosphere. Diethoxymethane (0.5 ml) was added to the suspension. The mixture was stirred at a temperature of 80 ° C for 2 hours. The mixture was subsequently treated by a conventional method and subjected to separation and purification to provide 2- (ethoxymethyl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylate. of ethyl (242 mg, 99%) as a yellow powder. 1H-NMR (CDC13): d 1.17 (3H, t), 1.45 (3H, t), 3.55 (2H, q), 4.00 (3H, s), 4.03 (3H, s), 4.49 (2H, q), 5.62 (2H, s), 7.05 (1H, s), 7.64 (1H, s). EIMS: m / z 408 (M +). (28b) In the same manner as in Example 3 (3b), 5- (2-amino-4,5-dimethoxybenzoyl) -2- (ethoxymethyl) -2H-1,2,3-triazole-4- was prepared ethyl carboxylate (178 mg, 88%) as a yellow oil from 2- (ethoxymethyl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1,2,3-triazole -4-ethyl carboxylate (220 mg) prepared in step (28a). 1 H-NMR (CDCl 3): d 1.21 (3H, t), 1.26 (3H, t), 3.63 (3H, s), 3.70 (2H, q), 3.90 (3H, s), 4.43 (2H, q), 5.78 (2H, s), 6.15 (1H, s), 6.50 (2H, brs), 6.73 (1H, s). EIMS: m / z 378 (M +). (28c) In the same manner as in example 26 (26c), the title compound (116 mg, 92%) was prepared as a yellow powder from 5- (2-amino-4,5-dimethoxybenzoyl) ) -2- (Ethoxymethyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (142 mg) prepared in step (28b). XH-NMR (DMSO-de): d 1.12 (3H, t), 3.64 (2H, q), 3.83 (3H, s), 3.85 (3H, s), 5.94 (2H, s), 7.13 (1H, s) ), 7.65 (1H, s), 11.2 (1H, brs). EIMS: m / z 332 (M +). Example 29 2- (isopropoxymethyl) -7,8-dimethoxy-4 (5H), 10-dioxo-2H-1, 2,3-triazolo [4,5-c] [1] benzazepine (29a) In the same way that in Example 19 (19a), paraformaldehyde (42 mg) and isopropyl alcohol (0.092 ml) were used respectively instead of propionaldehyde and 1,1'-carbonyldiimidazole. Thus, 2- (isopropoxymethyl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (215 mg, 85%) was prepared in the form of a light yellow oil from 5- (4,5-dimethoxy-2-nitrobenzoyl) -1 H-1,2,3-triazole-4-carboxylic acid ethyl ester (Synthesis example 2) (210 mg). 1H-NMR (CDC13): d 1.17 (6H, d), 1.45 (3H, t), 3.74-3.80 (1H, m), 4.00 (3H, s), 4.03 (3H, s), 4.49 (2H, q ), 5.63 (2H, s), 7.04 (1H, s), 7.64 (1H, s). EIMS: m / z 422 (M +). (29) In the same manner as in Example 3 (3b), 5- (2-amino-4,5-dimethoxybenzoyl) -2- (isopropoxymethyl) -2H-1,2,3-triazole-4- was prepared ethyl carboxylate (190 mg) in the form of a yellow oil from 2- (isopropoxymethyl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1,2,3-triazole-4- ethyl carboxylate (200 mg) prepared in step (29a). 1H-NMR (CDC13): d 1.17 (6H, d), 1.26 (3H, t), 3.63 (3H, s), 3.80-3.90 (1H, m), 3.90 (3H, s), 4.43 (2H, q ), 5.80 (2H, s), 6.16 (1H, s), 6.50 (2H, brs), 6.72 (1H, s). EIMS: m / z 392 (M +). (29c) In the same manner as in example 26 (26c), the title compound (110 mg, 70%) was prepared as a yellow powder from 5- (2-aminino-4,5). -dimethoxybenzoyl) -2- (isopropoxymethyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (180 mg) prepared in step (26b). 1 H-NMR (DMSO-de): d 1.12 (6H, d), 3.84 (3H, s), 3.85 (3H, s), 3.93-3.95 (1H, m), 5.96 (2H, s), 7.18 (1H , s), 7.66 (1H, s), 11.1 (1H, brs). EIMS: m / z 346 (M +). EXAMPLE 30 2- (1- (1,3-diethoxy-2-propoxycarbonyloxy) -2-methylpropyl) -7,8-dimethoxy-4 (5H), 10-dioxo-2H-1, 2, 3-triazolo [4 , 5-c] [1] benzazepine (30a) In the same manner as in example 19 (19a), provided that isobutylaldehyde (0.078 ml) was used instead of propionaldehyde, 2- (1- (1-) imidazolylcarbonyloxy) -2-methylpropyl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (252 mg, 61%) from 5 ( 4, 5-dimethoxy-2-nitrobenzoyl) -1 H-1,2,3-triazole-4-carboxylic acid ethyl ester (Synthesis Example 2) (280 mg). ^ -H-NMR (CDC13): d 0.82 (3H, d), 1.12 (3H, d), 1.44 (3H, t), 2.64-2.81 (1H, m), 4.01 (3H, s), 4.04 (3H , s), 4.50 (2H, q), 6.67 (1H, d), 7.08 (2H, m), 7.41 (1H, s), 7.59 (1H, s), 8 .14 (1H, m). LCMS: m / z 517 (M ++ l). (30b) In the same manner as in example 19 (19b), provided that 1, 3-diethoxy-2-propanol (0.6 ml) was used instead of 3-pentanol, 2- (1- (1 , 3-diethoxy-2-propoxycarbonyloxy) -2-methylpropyl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (165 mg, 44% ) in the form of a light yellow oil from 2- (1- (1-imidazolylcarbonyloxy) -2-methylpropyl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1, 2, 3 Ethyltriazole-4-carboxylate (325 mg) prepared in step (30a). 1 H-NMR (CDCl 3): d 0.71 (3H, d), 1.08-1.25 (9H, m), 1.45 (3H, t), 2.49- 2.61 (1H, m), 3.38-3.63 (8H, m), 4.01 (3H, s), 4.04 (3H, s), 4.50 (2H, q), 4.92 - 4.94 (1H, m), 6.38 (1H, d), 7.06 (1H, s), 7.62 (1H, s). LCMS: m / z 597 (M ++ l). (30c) In the same manner as in Example 3 (3b), 5- (2-amino-4,5-dimethoxybenzoyl) -2- (1- (1,3-diethoxy-2-propoxycarbonyloxy) -2 was prepared -methylpropyl) -2H-1, Ethyl 2, 3-triazole-4-carboxylate (177 mg, 78%) as a light yellow oil from 2- (1- (1,3-diethoxy-2-propoxycarbonyloxy) -2- methylpropyl) -5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (240 mg) prepared in step (30b). ^ -H-NMR (CDC13): d 0.85 (3H, d), 1.08-1.21 (9H, m), 1.29 (3H, t), 2.75-2.81 (1H, m), 3.40-3.72 (11H, m) , 3.91 (3H, s), 4.34 (2H, q), 4.92 - 4.97 (1H, m), 6.15 (1H, s), 6.50 (2H, brs), 6.54 (1H, d), 6.79 (1H, s ). LCMS: m / z 567 (M ++ l). (30d) In the same manner as in Example 3 (3c), the title compound (65 mg, 40%) was prepared as a pale yellow crystalline powder from 5- (2-amino-4) , 5-dimethoxybenzoyl) -2- (1- (1,3-diethoxy-2-propoxycarbonyloxy) -2-methylpropyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (175 mg) prepared in the step (30c). ^ -H-NMR (CDCl 3): d 0.85 (3H, t), 1.09 (3H, t), 1.16-1.19 (6H, m), 2.75-2.85 (1H, m), 3.38-3.66 (8H, m) , 4.00 (3H, s), 4.04 (3H, s), 4.88 - 4.93 (1H, m), 6.68 (1H, s), 6.70 (1H, d), 7.88 (1H, s), 9.31 (1H, s) ). FABMS: m / z 521 (M ++ l). EXAMPLE 31 7,8-dimethoxy-2- (1- (2- (2-methoxyethoxy) ethoxycarbonyloxy) -2-methylpropyl) -4 (5H), 10-dioxo-2H-1, 2, 3-triazolo [4, 5-c] [1] enzazepine (31a) In the same manner as in example 19 (19b), provided that diethylene glycol monomethyl ether was used (3.6 ml) instead of 3-pentanol and provided that trifluoroacetic acid (3.8 ml) was added, 2- (1- (2- (2-methoxyethoxy) ethoxycarbonyloxy) -2-methylpropyl) -5- (4, Ethyl 5-dimethoxy-2-nitrobenzoyl) -2H-1, 2, 3-triazole-4-carboxylate (8.82 g, 52%) from 2- (1- (1-imidazolylcarbonyloxy) -2-methylpropyl) - 5- (4,5-dimethoxy-2-nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (13.0 g) prepared in step (30a) 1 H-NMR (CDC13): d 0.72 (3 H, d), 1.07 (3 H, d), 1.44 (3 H, t), 2.50 - 2.65 (1 H, m), 3.36 (3 H, s), 3.50 - 3.55 (2 H , m), 3.60 - 3.65 (2H, m), 3.65 - 3.75 (2H, m), 4.01 (3H, s), 4.04 (3H, s), 4.20 - 4.35 (2H, m), 4.49 (2H, q), 6.35 (1H , d), 7.07 (1H, s), 7.62 (1H, s). (31b) In the same manner as in Example 3 (3b), 5- (2-amino-4,5-dimethoxy) -2- (1- (2- (2-methoxyethoxy) ethoxycarbonyloxy) -2- was prepared methylpropyl) -2H-1, 2, 3-triazole-4-carboxylic acid ethyl ester (1.14 g, 100%) from 2- (1- (2- (2-methoxyethoxy) ethoxycarbonyloxy) -2-methylpropyl) -5 Ethyl (4,5-dimethoxy-2-nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylate (1.15 g) prepared in step (31a).

XH-NMR (CDCl 3): d 0.85 (3H, d), 1.15 (3H, d), 1.29 (3H, t), 2. 70 - 2.85 (1H,), 3.36 (3H, s), 3.50 - 3.55 (2H,), 3.60 - 3.65 (2H, m), 3.64 (3H, s), 3.69 - 3.75 (2H, m), 3.90 ( 3H, s), 4.35 (2H, q), 4.20-4.40 (2H, m), 6.14 (1H, s), 6.49 (2H, s), 6.53 (1H, d), 6.78 (1H, s). (31c) In the same manner as in Example 3 (3c), the title compound (750 mg, 75%) was prepared as a light yellow crystalline powder from 5- (2-amino) 4, 5-dimethoxy) -2- (1- (2- (2-methoxyethoxy) -ethoxycarbonyloxy) -2-methylpropyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (1.11 mg) prepared in step (31b). 1 H-NR (CDCl 3): d 0.86 (3 H, d), 1.17 (3 H, d), 2.75 - 2.90 (1 H, m), 3.35 (3 H, s), 3.50 - 3.55 (2 H, m), 3.60 - 3.65 (2H,), 3. 71 (2H, t), 4.00 (3H, s), 4.07 (3H, s), 4.26 (1H, dt), 4.34 (1H, s), 6.68 (1H, d), 6.85 (1H, s), 7.88 (1H, s), 9.94 (1H, s). EXAMPLE 32 2- (1- (1,3-diethoxy-2-propoxycarbonyloxy) -2-methylpropyl) -8-isopropoxy-7-methoxy-4 (5H), 10-dioxo-2H-1, 2, 3-triazolo [4,5-c] [1] benzazepine (32a) In the same manner as in Synthesis Example 2, 5- (5-isopropoxy-4-methoxy-2-nitrobenzoyl) -1H-1, 2 was prepared, Ethyl 3-triazole-4-carboxylate (1.47 g, 78%) from a mixture of about 1: 1 (2.49 g) of 4- (5-isopropoxy-4-methoxy-2-nitrobenzoyl) -1- ( 4-methoxybenzyl) -1 H-1,2,3-triazole-5-carboxylic acid ethyl ester (synthesis example 3, b-1) and 5- (5-isopropoxy-4-methoxy-2-nitrobenzoyl) -1- ( 4-methoxybenzyl) -1 H-1,2,3-triazole-4-carboxylic acid ethyl ester (synthesis example 3, b-2). XH-NMR (CDC13): d 1.43 (9H, d), 4.00 (3H, s), 4.47 (2H, q), 4.65-4.80 (1H, m), 7.00 (1H, s), 7.66 (1H, s) ). (32b) p-Toluenesulfonic acid monohydrate (57 mg) and isobutylaldehyde (0.41 ml) were added to a solution of 5- (5-isopropoxy-4-methoxy-2-nitrobenzoyl) -1H-1,2,3-triazole Ethyl 4-carboxylate (1.14 g), prepared in step (32a), in methylene chloride solution (17 ml) at a temperature of -20 ° C. The mixture was stirred at this temperature for 1 hour. 1, 1'-Carbonyldiimidazole (732 mg) was added to the reaction solution. In addition, one hour after this, 1,3-diethoxy-2-propanol (4.70 ml) was added. The reaction solution was cooled to a temperature of -30 ° C. Trifluoroacetic acid (0.70 ml) was added. The temperature was raised to room temperature, followed by stirring for 25 hours. Hydrochloric acid at 0.5 M was added to the reaction solution under cooling with ice to stop the reaction, and separation was then carried out. The organic layer was washed 5 times with an aqueous solution of 7% sodium hydrogencarbonate. The solvent was evaporated under reduced pressure. Diethyl ether and water were added to the residue. The organic layer after separation was successfully washed twice with water, with 0.5 M hydrochloric acid, twice with water, and then with a 20% saline solution. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate / hexane) to give a crude product of 2- (1- (1, 3-diethoxy-2-propoxycarbonyloxy) -2-methylpropyl) -5- (5-isopropoxy-4-methoxy-2-nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (1.15 g) . 1H-NMR (CDC13): d 0.71 (3H, d), 1.07 (3H, d), 1.10 (3H, t), 1.15 (3H, t), 1.41-1.47 (9H, m), 2.54-2.65 (1H , m), 3.40 - 3.64 (8H, m), 4.01 (3H, s), 4.49 (2H, q), 4.68 - 4.76 (1H, m), 4.90 - 4.96 (1H, m), 6.39 (1H, d), 7.03 (1H , s), 7.61 (1H, s). (32b) In the same manner as in Example 3 (3b), 5- (2-amino-5-isopropoxy-4-methoxybenzoyl) -2- (1- (1,3-diethoxy-2-propoxycarbonyloxy) was prepared Ethyl 2-methylpropyl) -2H-1,2,3-triazole-4-carboxylate (1.08 g, 100%) from 2- (1- (1,3-diethoxy-2-propoxycarbonyloxy) -2- methylpropyl) -5- (5-isopropoxy-4-methoxy-2-nitrobenzoyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (1.12 g) prepared in step (32a). 1 H-NMR (CDCl 3): d 0.85 (3 H, d), 1.13 (3 H, t), 1.18 (3 H, t), 1.23 (6 H, 2 d), 1.26 (3 H, t), 1.49 (3 H, d), 2.73 - 2.82 (1H, m), 3.40 - 3.68 (8H, m), 4.09 - 4.17 (1H, m), 4.33 (2H, q), 4.93 - 5.00 (1H, m), 6.13 (1H, s), 6.46 (2H, s), 6.56 (1H, d), 6.83 (1H, s).

EIMS: m / z 594 (M +). (32c) In the same manner as in Example 3 (3c), the title compound (634 mg, 65% in two steps) was prepared from 5- (2-amino-5-isopropoxy-4-methoxybenzoyl) -2- (1- (1,3-diethoxy-2-propoxycarbonyloxy) -2-methylpropyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester (1.08 g) prepared in step (32b). ^ -NMR (CDC13): d 0.85 (3H, d), 1.08 (3H, t), 1.17 (3H, d), 1.18 (3H, t), 1.42 (6H, d), 2.78-2.90 (1H, m ), 3.36 - 3.66 (8H, m), 4.03 (3H, s), 4.68 - 4.79 (1H, m), 4.90 - 5.00 (1H, m), 6.70 (1H, d), 6.79 (1H, s), 7.90 (1H, s), 9.74 (1H, s). EIMS: m / z 548 (M +). Example 33 8-isopropoxy-2- (1-isopropoxycarbonyloxy-2-methylpropyl) -7-methoxy-4 (5H), 10-dioxo-2H-1, 2,3-triazolo [4,5-c] [1] benzazepine (33a) Isobutylaldehyde (2.9 ml), sodium iodide were added (3.18, g), potassium carbonate (11.69 g), and isopropyl chloroformate (7.2 ml) in this order under an atmosphere of argon at room temperature to a solution of 5- (5-isopropoxy-4-methoxy-2- nitrobenzoyl) -1 H-1,2,3-triazole-4-carboxylic acid ethyl ester (8.01 g), prepared in step (32a), in acetone (150 ml). The mixture was stirred at this temperature for 19.5 hours. Water was added to the reaction mixture to stop the reaction. The mixture was extracted with ethyl acetate. The organic layer was washed with a 20% saline solution and dried over anhydrous magnesium sulfate. The solvent was evaporated. The resulting mixture was purified by column chromatography on silica gel (hexane / ethyl acetate) to provide 2- (1-isopropoxycarbonyloxy-2-methylpropyl) -5- (5-isopropoxy-4-methoxy-2-nitrobenzoyl) - 2 H-1,2,3-triazole-4-carboxylic acid ethyl ester (10.12 g, 89%). 1H-NMR (CDC13): d 0.72 (3H, d), 1.05 (3H, t), 1.26 (3H, d), 1.28 (3H, d), 1.44 (3H, t), 2.57 (1H, m), 4.00 (3H, s), 4.49 (2H, q), 4.72 (1H,), 4.85 (1H, sept.), 6.36 (1H, d), 7.01 (1H, s), 7.60 (1H, s). TSPMS: m / z 537 (M ++ l). (33b) In the same manner as in Example 3 (3b), 5- (2-amino-5-isopropoxy-4-methoxybenzoyl) -2- (1-isopropoxycarbonyloxy-2-methylpropyl) -2H-1 was prepared, 2, 3-triazole-4-carboxylic acid ethyl ester from 2- (1-isopropoxycarbonyloxy-2-methylpropyl) -5- (5-isopropoxy-4-methoxy-2-nitrobenzoyl) -2H-1, 2, 3- ethyl triazole-4-carboxylate (10.12 g) prepared in step (33a). ^ • H-NMR (CDCl 3): d 0.85 (3H, d), 1.15 (3H, d), 1.22 (6H, d), 1.2-1.4 (9H, m), 2.76 (1H, d), 3.87 (3H , s), 4.10 (1H, m), 4.30 (2H, m), 4.88 (1H, sept.), 6.13 (1H, s), 6.53 (1H, d), 6.81 (1H, s). TSPMS: m / z 507 (M ++ l). (33c) A solution of 5- (2-amino-5-isopropoxy-4-methoxybenzoyl) -2- (1-isopropoxycarbonyloxy-2-methylpropyl) -2H-1,2,3-triazole-4-carboxylic acid ethyl ester, prepared in step (33b), in acetic acid (100 ml) was stirred at a temperature of 90 ° C for 3.5 hrs under an argon atmosphere. The reaction mixture was concentrated. Toluene was added to the concentrate, and the solution was concentrated again. The concentrate was extracted with methylene chloride followed by washing twice with an aqueous solution of sodium hydrogencarbonate 7% and once with a 10% saline solution. The organic layer was concentrated. The solvent was evaporated. The resulting mixture was washed twice with isopropyl alcohol and purified by column chromatography (chloroform / ethyl acetate) to give the title compound (4.02 g., 45% in two stages). 1H-NMR (CDC13): d 0.85 (3H, s), 1.16 (3H, d), 1.26 (3H, d), 1.31 (3H, d), 1.42 (6H, d), 2.81 (1H, m), 4.03 (3H, s), 4.74 (1H, sept.), 4.86 (1H, sept.), 6.68 (1H, d), 6.76 (1H, s), 7.90 (1H, s), 9.64 (1H, brs) . FABMS: m / z 461 (M ++ l). The title compounds of Examples 1 to 33 have the following respective chemical formulas.

Table 1 E j us R31 (or RJ 32) 'R32 (or R31) Q 1 H CH3 OC02CH (CH3) 2 2 H H OCOC (CH3) 3 Table 2 Example R "R 3J11 (or R> 3J2 (or R 33) R32) R31) 3 OCH3 H H CH2CH3 4 OCH3 H H CH2CH (CH3) 2 OCH3 H H (CH2) 5CH3 6 OCH3 H H (CH2) 3CH3 7 OCH3 H H CH (CH3) 2 17a OCH3 H H C6H4N02-p 19 OCH3 H CH2CH3 CH (CH2CH3.) 2 OCH3 H CH (CH3) 2 CH (CH3) 2 OCH3 H CH (CH3) 2 CH (CH2OCH2CH3) 2 31 OCH3 H CH (CH3) 2 (CH2CH20) 2CH3 32 OCH (CH 3) 2 H CH (CH 3) 2 CH (CH 2 CH 2 CH 3) 2 33 OCH (CH3) 2 H CH (CH3) 2 CHCH3) 2 Table 3 Example R31 (R32) R32 (R31) R34 8 H H C6H5 9 H H (CH2) 10CH3 10 H H (CH2) 14CH3 11 H H (CH2) 3C1 12 H H C6H4NH2-p 13 H H 14 H H - 15 H CH 3 CH (CH 3) 2 16 H H CH 2 C 6 H 4 OCH 3 -p 21 H H CH 3 22 H H CH (CH 3) 2 23 H H (CH2) 2CH3 24 H H (CH2) 2C02H H H Table 4 Example R31 (R32) R32 (R31) Q 13c H H Cl 15c H CH 3 Cl 17 H H OCONH (CH 2) 2 N (CH 3) 2) 18 H H 0P0 (0CH2CH3) 2 CH2CH3 CH2CH3 OCH3 27 (CH2) 2CH3 (CH2) 2CH3 0CH2CH3 28 HH OCH2CH3 29 HH 0CH (CH3) 2 Preparation example 1: Tablet preparation The compound of Example 20 (50.0 g), lactose (139.0 g), hydroxypropyl cellulose ( HPC-SL: 6.0 g), calcium carmellose (4.0 g), and purified water (9.0 g) were intimately mixed together. The mixture was granulated, dried, and subjected to granule size regulation. Magnesium stearate (1.0 g) was added and intimately mixed with the granule, followed by the formation of tablets to prepare tablets containing 50 mg of the compound, prepared in Example 20, per tablet. Preparation Example 2: Preparation of the Succinized Granule The compound of Example 20 (50.0 g), lactose (420 g), hydroxypropyl cellulose (HPC-SL: 15 g), calcium carmellose (10 g), and purified water (30 g) They were intimately mixed among them. The mixture was granulated, dried, subjected to regulation of granule sizes, and sieved. Magnesium stearate (5.0 g) was added and intimately mixed to prepare subtleized granules containing 100 mg of the compound of Example 20 per g of preparation. Pharmacological test example The compound of Synthesis Example 1, the compound of Example 7, and the compound of Example 20 were suspended or dissolved in an aqueous solution of 0.5% methylcellulose. The resulting solutions were administered orally in an equimolar amount to dogs and rats. After administration, the amount of each compound contained in the plasma of each individual animal was determined quantitatively by HPLC. The results are summarized in Table 5. Absorption of each sample was assayed by the area under the plasma drug level versus time curve (AUC). As a result, the AUCs obtained by the compounds of examples 7 and 20 as prodrugs were 3 to 4 times higher for the dog and 3 to 7 times higher for the rat compared to the compound of the synthesis example 1 as a body activator. Table 5 AUC Compound dog (μmol.hr / L) rat (μmol.hr / L) Example of 0.3 + 0.1 0.2 + 0.1 synthesis 1 example 7 0.9 ± 0.1 0.6 ± 0.1 example 20 1.210.3 1.4 + 0.1 Acute toxicity test by single administration _ The compound of Example 20 was suspended homogeneously in an aqueous solution of 0.5% methylcellulose. The suspension was orally administered in a forced manner to male ICR mice (5 weeks old). As a result, all mice survived and did not develop any abnormality at a dose of 2 g / kg of the compound of Example 20.

Claims (1)

1. CLAIMS A compound represented by the formula (I) or a physiologically acceptable salt or solvate thereof: R 1 represents a hydrogen atom, a hydroxyl group, C 1 - alkyl or phenyl-C 1 -C 4 alkyl; R 2, R 3, R 4, and R 5, which may be the same or different, represent any of the following (a) a (n): (a) a hydrogen atom, (b) a halogen atom, (c) an optionally protected hydroxyl group, (d) formyl, (e) C? -C? 2 alkyl which may be substituted by a halogen atom; (f) C2-C2 alkenyl having one or more carbon-carbon double bonds and can be substituted by (1) a halogen atom, (2) cyano, (3) -COR9 where R9 represents a hydrogen atom or C? -C6 alkyl, (4) -COOR10 where R10 represents a hydrogen atom or C? -6 alkyl, (5) -CONR? R12 where R11 and R12, which may be the same or different, they represent (i) a hydrogen atom, (ii) C alquilo _alkyl which may be substituted by amino optionally substituted by C alquilo _alkyl, phenyl optionally substituted by C alquilo-alkyl which may be substituted by an ani five to seven membered heterocyclic ring containing one or two nitrogen atoms (the nitrogen atoms may be substituted by C 4 -4 alkyl), or a saturated or unsaturated five to seven membered heterocyclic ring, (iii) phenyl which may be substituted by carboxyl, or (v) a saturated or unsaturated five to seven membered heterocyclic ring, (6) a saturated or unsaturated five to seven membered heterocyclic ring which may be substituted by C 1-4 alkyl or may form a bicyclic ring fused with another ring; (g) C 1 - 2 alkoxy which may be substituted by (1) a halogen atom, (2) a hydroxyl group, (3) cyano, (4) C 3-7 cycloalkyl, (5), phenyl, (6) C 1-4 alkoxy, (7) phenoxy, (8) amino which may be substituted by C 1-4 alkyl, (9) -COR 13 where R 13 represents a hydrogen atom, Ci-e alkyl, phenyl optionally substituted by a halogen or C1-4 alkoxy, or phenylalkyl C? _, (10) -COOR14 where R14 represents a hydrogen atom or C? _6 alkyl, (11) -CONR15R16 where R15 and R16, which may be the same or different they represent a hydrogen atom or Ci-e alkyl which may be substituted by a saturated to unsaturated five to seven membered heterocyclic ring, or (12) a five to seven unsaturated heterocyclic ring which may be substituted by Ci-alkyl 4 or phenylalkyl C1-4; (h) -C = N-0R16 wherein R16 represents a hydrogen atom, Ci-β alkyl, C 1-4 phenylalkyl, or phenyl; (i) - (CH2) mOR17 where m is an integer from 1 to 4 and R17 represents a hydrogen atom, Ci-β alkyl or phenylalkyl C? _4, wherein one or more hydrogen atoms in the benzene ring can be substituted by C? -4 alkyl; (j) - (CH2) k-COR18 where k is an integer from 1 to 4, and R18 represents a hydrogen atom or alkyl C? _ (k) - (CH2) j-COOR > 19 where j is an integer from 0 to 4, and R represents a hydrogen atom or C-alkyl: 6 / (1) - (CH2) p-NR20R21 where p is an integer from 1 to 4, and R20 and R21, which may be the same or different, represent (1) a hydrogen atom, (2) Ci-alkyl ß which may be substituted by amino optionally substituted by C? _4 alkyl, (3) phenylalkyl C? -, (4) -COR22 where R22 represents a hydrogen atom or C? _4 alkyl which may be substituted by carboxyl, or (5) -S02R23 where R23 represents C1-4 alkyl or phenyl it may be substituted by a halogen atom; (m) - (CH2) q-CONR24R25 where q is an integer from 0 to 4, and R24 and R25, which may be the same or different, represent a hydrogen atom, a saturated or unsaturated five to seven membered heterocyclic ring or alternatively C? -6 alkyl which may be substituted by a saturated to unsaturated five to seven membered heterocyclic ring, or alternatively R24 and R25 may form a saturated or unsaturated five to seven membered heterocyclic ring together with a nitrogen atom to which they are attached (the heterocyclic ring can also contain at least one oxygen, nitrogen or sulfur atom, can form a bicyclic ring fused with another ring, or can be substituted by C? _4 alkyl); and (n) -NR26R27 wherein R26 and R27 which may be the same or different, represent a hydrogen atom or -COR28 where R28 represents a hydrogen atom, Ci-β alkyl, or phenyl which may be substituted by C alquilo alkyl; 4 or C 1 -C 6 alkoxy optionally substituted by phenyl; R31 and R32, which may be the same or different, represent a hydrogen atom or Ci-e alkyl which may be substituted by a halogen atom; and Q represents a group selected from the following groups (i) to (iv) or a halogen atom or C? -6 alkoxy: ') where R33 represents C? _6 which may be substituted by alkoxy C? -6 alkoxy optionally substituted by Ci-ß phenyl optionally substituted by alkoxy C? -ß, amino, or nitro or a heterocyclic ring five- to seven-membered saturated or unsaturated optionally substituted alkoxy C? -6 / amino, or nitro, phenyl may be substituted by alkoxy C? _6, amino, or nitro, or a heterocyclic ring five- to seven-membered saturated or unsaturated may be substituted by alkoxy C? _6, amino, or nitro, or R33 can form C? -4 alkylene together with R31 or R32, R34 represents C? -? 6 alkyl which may be substituted by a halogen atom, carboxyl, phenyl, optionally substituted by alkoxy C? -6 / amino, or nitro, or a saturated or unsaturated five to seven membered heterocyclic ring optionally substituted by C? -6 / amino alkoxy, or nitro, phenyl may be substituted by C? -6 alkoxy, amino, or nitro, or a heterocyclic ring of five to seven membered saturated or unsaturated bros that can be substituted by C6-alkoxy, amino, or nitro, R35 and R36, which may be the same or different, represent a hydrogen atom or C? _6 alkyl which may be substituted by optionally substituted amino alkyl C_4 or R35 and R36 may form a heterocyclic ring five- to seven-membered saturated or unsaturated together with a nitrogen atom to which they are attached, and R37 and R38 which can be identical or different, represent C? _6, to condition that the group -CR31R32Q does not represent Ci-6 alkyl substituted by a halogen atom or C? -6 alkoxy. A compound according to claim 1, wherein R1 represents a hydrogen atom and R2, R3, R4, and R5 represent a hydrogen atom or (g) C? -C? 2 alkoxy. A compound according to claim 1, wherein R1, R2, and R5 represent a hydrogen atom and R3 and R4 represent a hydrogen atom or (g) C? -C? 2 alkoxy. A compound according to claim 1, wherein R1, R2, R4, and R5, represent a hydrogen atom and R3 represents (g) C? -C? 2 alkoxy. A compound according to claim 1, wherein R1, R2, R3, and R5, represent a hydrogen atom and R4 represents (g) C? -C? 2 alkoxy. A compound represented by the formula (Ia) or a pharmacologically acceptable salt or solvate thereof: where R41 and R42, which may be identical or different, represent a hydrogen atom, optionally protected hydroxyl, C6-6 alkoxy which may be substituted by a halogen atom, or C6-6 alkyl which may be substituted by an atom of halogen and R31, R32, and Q "are in accordance with that defined in claim 1, provided that the group -CR31R32Q does not represent C? -C6 alkyl substituted by a halogen atom or Ci-C? alkoxy. according to claim 6, wherein R4- and R42 represent C6-C6 alkoxy and Q represents a group (i) • 8. 2- (l-isopropoxycarbonyloxy-2-methylpropyl) -7,8-dimethoxy-4 (5H) ), 10-dioxo-2H-1, 2, 3-triazolo [4, 5-c] [l] benzazepine, 2- (1- (1,3-diethoxy-2-propoxycarbonyloxy) -2-methylpropyl) -7 , 8-dimethoxy-4 (5H), 10-dioxo-2H-1, 2, 3-triazolo [4,5-c] [l] benzazepine, 2- (1- (1,3-diethoxy-2-propoxycarbonyloxy) ) -2-methylpropyl) -8- isopropoxy-7-dimethoxy-4 (5H), 10-dioxo-2H-1, 2, 3-triazolo [4, 5-c] [ 1] benzazepine, or 8-isopropoxy-2- (l-isopropoxycarbonyloxy-2-methylpropyl) -7- methoxy-4 (5H), 10-dioxo-2H-l, 2, 3-triazolo [4, 5- c ] [1] benzazepine, or a salt or solvate thereof. 9. A pharmaceutical composition comprising the compound according to any of claims 1 to 8 or a pharmacologically acceptable salt or solvate thereof. 10. A pharmaceutical composition according to claim 9 for use in the treatment of allergic diseases. 11. A method for the treatment of an allergic disease, comprising administration to mammals of the compound according to any one of claims 1 to 8 or a pharmacologically acceptable salt or solvate thereof together with a pharmaceutically acceptable carrier. 12. The use of the compound according to any of claims 1 to 8 or a pharmacologically acceptable salt or solvate thereof for the preparation of a therapeutic agent for allergic diseases. . A compound represented by the formula (II) or a salt or solvate thereof: wherein R51 represents nitro or amino, R52 represents a hydrogen atom or a protecting group for carboxyl, and Q, R2 to R5, R31, and R32 are defined in accordance with claim 1, provided that the group does not -CR31R32Q represents C? -C6 alkyl substituted by a halogen atom or Ci-Ce alkoxy. A compound represented by the formula (II ') or a salt or solvate thereof: wherein Q, R2 to R5, R31, R32, R51, R52 and are as defined as defined in claims 1 and 13, provided that the group does not represent C -CR31R32Q alkyl? C6 alkyl substituted by a halogen atom or alkoxy Ci-Ce. 15. A compound represented by the formula (VI) or a salt or solvate thereof: where Q, R2 to R5, R31, R32, and R52 are in accordance with that defined in claims 1 and 13. 16. A compound represented by the formula (VI ') or a salt or solvate thereof: where Q, R2 to R5, R31, R32, and R52 are in accordance with that defined in claims 1 and 13.. A compound represented by the formula (VI I) or a salt or solvate thereof: where R a R, and R are in accordance with that defined in claims 1 and 13.. A compound represented by the formula (VIII) or a salt or solvate thereof: wherein R61 represents a protecting group for triazole and R2 to R5, and R52 is in accordance with the definitions of claims 1 and 13. A process for the preparation of a compound represented by the formula (lía '): where Q represents a group (i) in accordance with that defined in claim 1 and R2 to R5, R31, R32, and R52 are in accordance with that defined in claims 1 and 13, comprising the steps of: (1) reacting a compound represented by the formula (V) wherein R2 to R5 and R52 are in accordance with that defined in claims 1 and 13, with a compound represented by the formula R31R32C = 0 wherein R31 and R32 are in accordance with that defined above in claim 1; (2) reacting the compound prepared in step (1) with a compound represented by R71-C (= 0) -R72 where R71 and R72, each independently, represent a chlorine atom, 4-nitrophenyl, or 1-imidazolyl; and (3) reacting the compound prepared in claim (2) with a compound represented by R330H wherein R33 is in accordance with that defined in claim 1. A process for preparing a compound represented by the formula (lía '): where Q represents group (i) in accordance with that defined in claim 1 and R2 to R5, R31, R32, and R52 are in accordance with that defined in the claims 1 and 13, comprising the steps of: (1) reacting a compound represented by the formula (V) wherein R2 to R5 and R52 are in accordance with that defined in claims 1 and 13, with a compound represented by R31R32C = 0 wherein R31 and R32 are in accordance with that defined in claim 1; and (2) reacting the compound prepared in step (1) with a compound represented by HalCOOR33 wherein Hal represents a halogen atom and R33 is under defined in claim 1, in the presence of an alkali metal carbonate and an alkali metal iodide. . A process for the preparation of a compound represented by the formula (lia ') where Q represents a group (i) in accordance with that defined in claim 1 and R2 to R5, R31, R32, and R52 are in accordance with that defined in claims 1 and 13, comprising the step of: reacting a compound represented by the formula (V) wherein R2 to R5 and R52 are in accordance with that defined in claims 1 and 13, with a compound represented by the formula (IV) where Hal represents a halogen atom, Q represents group (i) in accordance with that defined in claim 1, and R31 and R32 are in accordance with that defined above in the presence of an inorganic base and an alkali metal iodide. 22. A process for the production of a compound represented by the formula (VI ') where Q represents group (i) in accordance with that defined in claim 1, R2 to R5, R31, R32, and R52 are in accordance with the definition. in claims 1 and 13, comprising the steps of: (1) reacting a compound represented by the formula (VII) wherein R2 to R5 and R52 are in accordance with that defined in claims 1 and 13, with a compound represented by R31R32C = 0 wherein R31 and R32 are in accordance with that defined in claim 1; (2) reacting the compound prepared in step (1) with a compound represented by R71-C (= 0) -R72 where R71 and R72, each independently, represent a chlorine atom, 4-nitrophenyl, or 1-imidazolyl; and (3) reacting the compound prepared in step (2) with a compound represented by R330H wherein R33 is in accordance with that defined in claim 1. A process for the preparation of a compound represented by the formula (VI ') where Q represents a group (i) in accordance with that defined in claim 1, R2 to R5, R31, R32, and R52 are in accordance with that defined in claims 1 and 13, comprising the steps of: (1) reacting a compound represented by the formula (VII) wherein R2 to R5 and R52 are in accordance with that defined in claims 1 and 13, with a compound represented by R31R32C = 0 wherein R31 and R32 are in accordance with that defined above in claim 1; and (2) reacting the compound prepared in step (1) with a compound represented by HalCOOR33 where Hal represents a halogen atom and R33 is in accordance with that defined in claim 1, in the presence of an alkali metal carbonate and an alkali metal iodide. . A process for the production of a compound represented by the formula (VI ') where Q represents a group (i) in accordance with that defined in claim 1, R2 to R5, R31, R32, and R52 are in accordance with that defined in claims 1 and 13, comprising the step of: reacting a compound represented by the formula (VII) (VII) where R2 to R5 and R52 are in accordance with that defined in claims 1 and 13, with a compound represented by the formula (IV) where Hal represents a halogen atom, Q represents group (i) in accordance with that defined in claim 1, and R31 and R32 are in accordance with that defined above, in the presence of an inorganic base and an alkali metal iodide. 25. A process for the preparation of a compound represented by the formula (VIII) wherein R2 to R5, R52, and R61 are in accordance with that defined in claims 1, 13, and 18, comprising the step of: (a) reacting a compound represented by the formula (IX) wherein R2 to R and R are in accordance with that defined in claims 1 and 13, with a compound represented by the formula (X) R61-N3 (X) wherein R61 is in accordance with that defined in claim 18, or (b) reacting a compound represented by the formula (XII) where M represents lithium, magnesium chloride, magnesium bromide, magnesium iodide, zinc bromide, zinc iodide, cadmium bromide, cadmium iodide, or copper and R: are in accordance with that defined in claim 1, with a compound represented by the formula (XIII) wherein R52 and R61 are in accordance with that defined in claims 13 and 18.. A process according to claim 25, further comprising the step, before the reaction of the compound represented by the formula (IX) with a compound represented by the formula (X) in step (a), of dehydrogenating a compound represented by the formula (XI) (XI) wherein R2 to R5 and R52 are in accordance with that defined in claims 1 and 13, to produce the compound represented by the formula (IX). . A process for the production of a compound represented by the formula (XV) wherein R2 to R5, R52, and R61 are in accordance with that defined in claims 1, 13, and 18, which comprises the step of: reacting a compound represented by the formula (XVI) (XVI) wherein R2 to R5 and R52 are in accordance with that defined in claims 1 and 13, with a compound represented by the formula (X) R61-N3 (X) wherein R61 is in accordance with that defined in claim 18 . A process according to claim 27, further comprising the step, before the reaction of the compound represented by the formula (XVI) with the compound represented by the formula (X), a compound represented by the formula (XVII) where R 2 to R 5 and R 52 are in accordance with that defined in claims 1 and 13, it is dehydrogenated to produce the compound represented by the formula (XVI). A compound represented by the formula (IXa) or a salt or solvate thereof wherein R41, R42, and R52 are in accordance with that defined above in claims 6 and 13, provided that R41 and / or R42 do not represent a hydrogen atom. . A compound represented by the formula (XVIa) or a salt or solvate thereof (XVIaj wherein R41, R42, R51 and R52 are in accordance with that defined above in claims 6 and 13. SUMMARY OF THE INVENTION Tricyclic triazolobenzazepine derivatives are provided in the form of a pro-drug. The compounds according to the present invention are the compounds represented by the formula (I) and pharmacologically acceptable salts and solvates thereof. The compounds are useful as antiallergic agents and exhibit excellent bioavailability; wherein R1 represents hydrogen, OH, alkyl or phenylalkyl, R2, R3, R4 and R5 represent hydrogen, halogen, optionally protected hydroxyl, formyl, optionally substituted alkyl, alkenyl, alkoxy or the like, and Q represents a group selected from the following groups (i) to (iv), halogen, or alkoxy;