- Synthesis of 4-alkylsulfanylphthalazin-1(2H)-ones via palladium catalyzed sulfanylation of substituted 4-bromophthalazin-1(2H)-ones
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The synthesis of a series of new alkylsulfanyl phthalazinone and phthalazine derivatives is described. The target compounds were efficiently synthesized in a four step sequence, consisting of (1) cyclization of 2-formylbenzoic acid with hydrazine hydrate to form phthalazinone, (2) the direct bromination of phthalazinone core with KBr3, (3) alkylation of the obtained 4-bromolactam (Mitsunobu procedure) to make N- and also O-alkyl derivatives and finally (4) palladium-catalyzed coupling reactions of 2-alkyl-4-bromophthalazinone and 1-alkyloxy-4-bromophthalazine derivatives with aliphatic mercaptanes. Furthermore, the synthesis of 2-methyl-8-(propan-2-yl)sulfanyl-pyrido[3,4-d]pyridazin-1(2H)-one from 2-methyl-pyrido[3,4-d]pyridazin-1(2H)-one via bromination reaction with KBr3and subsequent sulfanylation by isopropyl mercaptan under catalyzed coupling reaction conditions is also described.
- Malinowski, Zbigniew,Fornal, Emilia,Sierocińska, Beata,Czeczko, Renata,Nowak, Monika
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- Reaction of Diazines and their Benzo derivatives with Benzonitrile oxide
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The reaction of diazines 1 and benzodiazines 2 with benzonitrile oxide in refluxing benzene affords regio, site and stereospecific cycloadducts to the diazine ring and/i43or products derived from them.
- Grassi, Giovanni,Risitano, Francesco,Foti, Francesco
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- Inhibitory effects of drugs on the metabolic activity of mouse and human aldehyde oxidases and influence on drug–drug interactions
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As aldehyde oxidase (AOX) plays an emerging role in drug metabolism, understanding its significance for drug–drug interactions (DDI) is important. Therefore, we tested 10 compounds for species-specific and substrate-dependent differences in the inhibitory effect of AOX activity using genetically engineered HEK293 cells over-expressing human AOX1, mouse AOX1 or mouse AOX3. The IC50 values of 10 potential inhibitors of the three AOX enzymes were determined using phthalazine and O6-benzylguanine as substrates. 17β-Estradiol, menadione, norharmane and raloxifene exhibited marked differences in inhibitory effects between the human and mouse AOX isoforms when the phthalazine substrate was used. Some of the compounds tested exhibited substrate-dependent differences in their inhibitory effects. Docking simulations with human AOX1 and mouse AOX3 were conducted for six representative inhibitors. The rank order of the minimum binding energy reflected the order of the corresponding IC50 values. We also evaluated the potential DDI between an AOX substrate (O6-benzylguanine) and an inhibitor (hydralazine) using chimeric mice with humanized livers. Pretreatment of hydralazine increased the maximum plasma concentration (Cmax) and the area under the plasma concentration-time curve (AUC0–24) of O6-benzylguanine compared to single administration. Our in vitro data indicate species-specific and substrate-dependent differences in the inhibitory effects on AOX activity. Our in vivo data demonstrate the existence of a DDI which may be of relevance in the clinical context.
- Takaoka, Naoki,Sanoh, Seigo,Okuda, Katsuhiro,Kotake, Yaichiro,Sugahara, Go,Yanagi, Ami,Ishida, Yuji,Tateno, Chise,Tayama, Yoshitaka,Sugihara, Kazumi,Kitamura, Shigeyuki,Kurosaki, Mami,Terao, Mineko,Garattini, Enrico,Ohta, Shigeru
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- Identification of new potent phthalazine derivatives with VEGFR-2 and EGFR kinase inhibitory activity
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Efforts to develop new antitumor agents are now directed towards multitarget therapies that are believed to have high potency and low tendency to resistance compared to conventional drugs. Herein, we highlighted the synthesis and antitumor activity of five series of phthalazine-based compounds featuring a variety of bioactive chemical fragments at position 1 of the phthalazine nucleus. The antitumor activity of the target compounds was performed against fourteen cancer cell lines where all compounds were active in the nanomolar level. In addition, the mechanism of action of the target compounds was investigated through an enzymatic inhibitory assay against VEGFR-2 and EGFR kinases, revealing potent and preferential activity toward VEGFR-2. Binding mode of the most active compounds was studied using docking experiment.
- Amin, Kamilia M.,Barsoum, Flora F.,Awadallah, Fadi M.,Mohamed, Nehal E.
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- Synthesis of 4-Substituted Phthalazin-1(2H)-ones from 2-Acylbenzoic Acids: Controlling Hydrazine in a Pharmaceutical Intermediate through PAT-Guided Process Development
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A simple one-pot, two-step process for the conversion of 2-acylbenzoic acids to phthalazin-1(2H)-ones was developed. A robust process was required that delivered the final isolated solid with consistently low levels of residual hydrazine, for further processing to the final drug substance. An in situ formed intermediate was critical to control reactivity and allowed for the controlled crystallization that prevented entrainment of hydrazine. Leveraging Process Analytical Technology (PAT), we investigated the reaction profile with in situ IR and Power Compensation Calorimetry (PCC) to aid development prior to a successful scale-up.
- Mennen, Steven M.,Mak-Jurkauskas, Melody L.,Bio, Matthew M.,Hollis, L. Steven,Nadeau, Kelly A.,Clausen, Andrew M.,Hansen, Karl B.
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- Identification of a suitable and selective inhibitor towards aldehyde oxidase catalyzed reactions
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1.Aldehyde oxidase (AO) is a liver cytosolic molybdoflavoprotein enzyme whose importance in drug metabolism is gaining in the recent. The objective of this work is to find a potent and selective inhibitor for AO activity using phthalazine oxidation as a marker reaction. 2. Among organic solvents tested, it was identified that methanol was not a suitable choice for AO activity even at concentrations less than 0.2% v/v. Acetonitrile and DMSO did not show any effect till 0.5% v/v but thereafter activites tend to decrease. 3. For selectivity, 23 compounds were selected and evaluated for their effects on AO and nine CYP450 enzymes. Among the tested compounds chlorpromazine, estradiol, hydralazine, quetiapine and raloxifene were selected based on their potency of inhibition towards AO activity. 4. Raloxifene was found to be a non-specific inhibitor of all major tested CYP450 enzymes and was excluded as a selective inhibitor for AO. Quetiapine also showed a degree of inhibition towards the major CYP450 tested. Hydralazine used as a specific inhibitor during the past for AO activity demonstrated a stimulation of AO activity at high and low concentrations respectively and the inhibition noted to be time dependent while inhibiting other enzymes like monoamine oxidase. 5. Estradiol showed no inhibition towards the tested CYP450 enzymes and thus proved to be a selective and specific inhibitor for AO activity with an uncompetitive mode of inhibition.
- Nirogi, Ramakrishna,Kandikere, Vishwottam,Palacharla, Raghava Choudary,Bhyrapuneni, Gopinadh,Kanamarlapudi, Vijaya Bhargava,Ponnamaneni, Ranjith Kumar,Manoharan, Arun Kumar
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- Investigations of reactions of selected azaarenes with radicals in water. 1. Hydroxyl and sulfate radicals
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The oxidative degradation of binuclear azaarenes is studied in a number of environmentally relevant radical reactions. The comparison between oxidation mechanisms of hydroxyl and sulfate radicals, as well as between dark and photoreactions, is done. Most of the products formed are identified. With the change from dark to photoreactions of quinoline and isoquinoline, a shift of the oxidation center from the benzene to the pyridine rings is observed. The reaction behavior of the benzodiazines can be derived from the reaction patterns of quinoline and isoquinoline. The rate constants of second order are determined for the reactions of the azaarenes with carbonate radicals. The rate constants and the differences in the products formed conformably prove the importance of the inclusion of excited states in the reaction mechanism. The application of the frontier orbital concept allows an easy interpretation. Electron transfer reactions resulting in radical oxygen species are shown to be product determining in direct photolysis, too.
- Beitz, Toralf,Bechmann, Wolfgang,Mitzner, Rolf
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- Synthesis and Investigation of Phthalazinones as Antitubercular Agents
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A series of 2- and 7-substituted phthalazinones was synthesised and their potential as anti-tubercular drugs assessed via Mycobacterium tuberculosis (mc26230) growth inhibition assays. All phthalazinones tested showed growth inhibitory activity (MIC 100 μm), and those compounds containing lipophilic and electron-withdrawing groups generally exhibited better anti-tubercular activity. Several lead compounds were identified, including 7-((2-amino-6-(4-fluorophenyl)pyrimidin-4-yl)amino)-2-heptylphthalazin-1(2H)-one (MIC=1.6 μm), 4-tertbutylphthalazin-2(1H)-one (MIC=3 μm), and 7-nitro-phthalazin-1(2H)-one (MIC=3 μm). Mode of action studies indicated that selected pyrimidinyl-phthalazinones may interfere with NADH oxidation, however, the mode of action of the lead compound is independent of this enzyme. MIC=minimum inhibitory concentration.
- Santoso, Kristiana T.,Cheung, Chen-Yi,Hards, Kiel,Cook, Gregory M.,Stocker, Bridget L.,Timmer, Mattie S. M.
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supporting information
p. 1278 - 1285
(2019/02/24)
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- Tin Powder-Promoted Cascade Condensation/Allylation/Lactamization: Synthesis of Isoindolinones and Pyrazoloisoindol-8-ones
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An efficient tin powder-promoted cascade condensation/allylation/lactamization of 2-formylbenzoic acids, hydrazides, and allyl bromides was developed for the synthesis of isoindolinones in good to excellent yields under mild conditions without any other additives or catalysts. Further manipulation of isoindolinones by iodocyclization process afforded the tricyclic tetrahydro-8H-pyrazolo[5,1-a]isoindol-8-one derivatives, which could be converted into more complicated tetracyclic tetrahydro-4H-azirino[1′,2′:2,3]pyrazolo[5,1-a]isoindol-4-ones.
- Wang, Xiaoping,Huang, Danfeng,Wang, Ke-Hu,Su, Yingpeng,Hu, Yulai
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p. 6946 - 6961
(2019/06/14)
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- A paclitaxel and model phthalazine ketone BTK inhibitor combination pharmaceutical composition and its application (by machine translation)
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The invention provides a joint for paclitaxel and BTK inhibitor pharmaceutical composition comprising an active ingredient and a pharmaceutically acceptable auxiliary material, wherein the active ingredient by the taxol of formula (I) of a BTK inhibitors shown, the active ingredient of taxol in the formula (I) indicated by the molar ratio of BTK inhibitors (0.14 - 0.20): 1. The pharmaceutical composition can be used for preparing the prevention and/or treating the Bruton tyrosine kinase-related disease drug, the treatment effect is good. (by machine translation)
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- A paclitaxel and to phenyl phthalazine ketone BTK inhibitor combination pharmaceutical composition and its application
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The present invention provides a kind of paclitaxel and to phenyl phthalazine ketone BTK inhibitor combination pharmaceutical composition comprising an active ingredient and a pharmaceutically acceptable auxiliary material, wherein the active ingredient by the taxol of formula (I) of a BTK inhibitors shown, the active ingredient of taxol in the formula (I) indicated by the molar ratio of BTK inhibitors (0.14 - 0.20): 1. The pharmaceutical composition can be used for preparing the prevention and/or treating the Bruton tyrosine kinase-related disease drug, the treatment effect is good.
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- Novel pyridazinone BTK inhibitor as well as preparation and application thereof
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The invention belongs to the field of medical chemistry, relates to a novel pyridazinone BTK inhibitor as well as preparation and application thereof, in particular to a pyridazinone BTK inhibitor, apreparation method thereof, a pharmaceutical composition containing the same, and application thereof to treatment of Bruton's tyrosine kinase-related diseases.
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- A taxol and O-phenyl phthalazine ketone BTK inhibitor combination pharmaceutical composition and its application
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The present invention provides a taxol and O-phenyl phthalazine ketone BTK inhibitor combination pharmaceutical composition, comprising an active ingredient and a pharmaceutically acceptable auxiliary material, wherein the active ingredient by the taxol of formula (I) of a BTK inhibitors shown, the active ingredient of taxol in the formula (I) indicated by the molar ratio of BTK inhibitors (0.14 - 0.20): 1. The pharmaceutical composition can be used for preparing the prevention and/or treating the Bruton tyrosine kinase-related disease drug, the treatment effect is good.
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- Pyridazinone BTK inhibitors and application thereof
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The invention relates to the field of medicinal chemistry, relates to pyridazinone BTK inhibitors and an application thereof, and concretely relates to pyridazinone BTK inhibitors represented by formula (I), a preparation method thereof, a medicinal composition containing the compounds, and a use of the compounds or the medicinal composition in the treatment of Bruton's tyrosine kinase-related diseases.
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Paragraph 0042; 0043; 0046; 0047
(2019/01/23)
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- A taxol and taitai qin kind BTK inhibitor combination pharmaceutical composition and its application
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The present invention provides a taxol and taitai qin kind BTK inhibitor combination pharmaceutical composition comprising an active ingredient and a pharmaceutically acceptable auxiliary material, wherein the active ingredient by the taxol of formula (I) of a BTK inhibitors shown, the active ingredient of taxol in the formula (I) indicated by the molar ratio of BTK inhibitors (0.14 - 0.20): 1. The pharmaceutical composition can be used for preparing the prevention and/or treating the Bruton tyrosine kinase-related disease drug, the treatment effect is good.
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Paragraph 0024; 0025; 0028
(2019/04/09)
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- Design and synthesis of phthalazine-based compounds as potent anticancer agents with potential antiangiogenic activity via VEGFR-2 inhibition
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In the designed compounds, either a biarylamide or biarylurea moiety or an N-substituted piperazine motif was linked to position 1 of the phthalazine core. The anti-proliferative activity of the synthesised compounds revealed that eight compounds (6b, 6e, 7b, 13a, 13c, 16a, 16d and 17a) exhibited excellent broad spectrum cytotoxic activity in NCI 5-log dose assays against the full 60 cell panel with GI50 values ranging from 0.15 to 8.41 μM. Moreover, the enzymatic assessment of the synthesised compounds against VEGFR-2 tyrosine kinase showed the significant inhibitory activities of the biarylureas (12b, 12c and 13c) with IC50s of 4.4, 2.7 and 2.5 μM, respectively, and with 79.83, 72.58 and 71.6% inhibition of HUVEC at 10 μM, respectively. Additionally, compounds (7b, 13c and 16a) were found to induce cell cycle arrest at S phase boundary. Compound 7b triggered a concurrent increase in cleaved caspase-3 expression level, indicating the apoptotic-induced cell death.
- Elmeligie, Salwa,Aboul-Magd, Asmaa M.,Lasheen, Deena S.,Ibrahim, Tamer M.,Abdelghany, Tamer M.,Khojah, Sohair M.,Abouzid, Khaled A. M.
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p. 1347 - 1367
(2019/07/29)
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- Preparation method of substituted 2, 3-phthalazinone compound
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The invention provides a preparation method of a substituted 2, 3-phthalazinone compound. The method includes the steps of: (1) adding substituted hydrazine and substituted o-carboxybenzaldehyde intoa reaction container, controlling the reaction temperature at 50DEG C-150DEG C, and carrying out thermal insulation reaction under mechanical mixing; and (2) carrying out TLC or gas phase monitoring reaction, at the end of the reaction, adding a precipitating agent into the reaction system, conducting stirring for 0.5-1.0h, and conducting standing and filtering to obtain a solid crystal, i.e. thesubstituted 2, 3-phthalazinone compound. Starting from cheap and easily available raw materials, the preparation method provided by the invention employs one-pot process for efficient preparation of aseries of highly bioactive substituted 2, 3-phthalazinone compounds with a yield of 90%-99% under a molten state. The method has the characteristics of wide substrate application range, no adding ofcatalyst, no use of solvent and mild conditions, the reaction time is shortened by 95% or more than that of the catalytic preparation method under the traditional solvent condition, and the product purity is very high.
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Paragraph 0057; 0058
(2018/07/30)
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- Access to phthalazinones via palladium-catalyzed three-component cycloamino-carbonylation of 2-formylaryl tosylates, hydrazines and CO
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The palladium-catalyzed three-component cycloaminocarbonylation of 2-formylaryl tosylates with hydrazines and carbon monoxide has been established, which provides an efficient method for synthesis of substituted phthalazinones. In addition, by applying this protocol as the key step, Hydralazine can easily be synthesized in 65% yield.
- Liu, Bin,Zhang, Chunlei,Zhou, Xigeng
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p. 8282 - 8286
(2016/12/02)
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- Highly efficient synthesis of N-substituted isoindolinones and phthalazinones using Pt nanowires as catalysts
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A series of N-substituted isoindolinones have been successfully synthesized through the reductive C-N coupling and intramolecular amidation of 2-carboxybenzaldehyde and amines. This one-pot synthesis gives excellent yields using ultrathin Pt nanowires as catalysts under 1 bar of hydrogen. These unsupported catalysts can also be used for the synthesis of phthalazinones in high yield when hydrazine or phenyl hydrazine is used instead of amines.
- Shi, Linyan,Hu, Lei,Wang, Jiaqing,Cao, Xueqin,Gu, Hongwei
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supporting information; experimental part
p. 1876 - 1879
(2012/06/04)
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- Synthesis, vasorelaxant activity, and molecular modeling study of some new phthalazine derivatives
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New phthalazine-based vasodilators were synthesized through the chloroacylation of the starting compound 1-hydrazinophthalazine 4 to give the two key intermediates 5 and 7. These intermediates were used to alkylate various cyclic amines to furnish the final compounds 6a-h and 8a-h. Compounds were tested for their vasorelaxant activities against nor-adrenaline-induced spasm on thoracic rat aorta rings and compared to the reference drug, prazosin. Seven compounds showed higher activity than prazosin, especially compound 8d having an IC50 = 0.10 mM. Molecular modeling studies, including fitting of the synthesized compounds to a 3D-pharmacophore and their docking into optimized homology model as α1-AR antagonists showed high docking score and fit values. Most vasodilation activities of tested compounds are consistent with their molecular modeling results.
- Awadallah, Fadi M.,El-Eraky, Wafaa I.,Saleh, Dalia O.
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scheme or table
p. 14 - 21
(2012/07/16)
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- Microwave-promoted solid-acid-catalyzed one-pot synthesis of phthalazinones
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A one-pot, solid-acid-catalyzed, microwave-assisted synthesis of phthalazinones is described. The commercially available montmorillonite K-10 effectively catalyzed the condensation and substitution reactions. The approach was based on the direct cyclization of phthalaldehydic acid and opianic acid with substituted hydrazines. The reactions provided excellent yields and high selectivities in very short time (5-35 minutes). Georg Thieme Verlag Stuttgart.
- Outerbridge, Verona M.,Landge, Shainaz M.,Tamaki, Hiroko,Toeroek, Bela
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experimental part
p. 1801 - 1806
(2009/12/29)
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- Synthesis and spectral study of N-2-(3′-phthalidyl)phthalazin-1-one
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N-2-(3′-Phthalidyl)phthalazin-1-one was synthesized by the condensation of 2-carboxybenzaldehyde with hydrazine hydrate using polyphosphoric acid as catalyst and solvent. Its 1H and 13C NMR spectra were completely assigned utilizing the two-dimensional 1H-detected heteronuclear one-bond (HMQC) and multiple-bond (HMBC) techniques together with 1H-1H COSY and NOESY (homonuclear Overhauser and chemical exchange spectroscopy) correlation techniques. These techniques were also valuable in assigning the protons of its hydrazinolysis product, which were previously incompletely reported because of the overlap of proton signals. Copyright
- Chen, Yantao,Hua, Wenting,Lue, Mujian,Pan, Jingqi
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p. 149 - 151
(2007/10/03)
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- Anti-inflammatory phthalazinones
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A compound useful as anti-inflammatory agents in warm-blooded animals of the formula STR1 wherein X is a member of the class of ethylene and ethenyl and is substituted for hydrogen in the sixth or seventh position of the 1(2H)-phthalazinone ring Y is a member of the class of hydrogen and hydroxyl R1 is a member of the class of hydrogen, alkyl, alkoxy, hydroxyl, halogen, nitro, --NR3 R4, --COR5 and --O--A wherein A is a mineral acid residue which with --O-- forms an ester or the alkali metal salt of said ester, R2 is a member of the class of hydrogen, alkyl, phenyl, substituted phenyl, heteroaryl, hydroxyalkylene, polyhydroxyalkylene, aminoalkylene, alkylaminoalkylene, and carboxyalkylene, R3, R4 are independently from the class of hydrogen, alkyl, aminoalkylene or alkylaminoalkylene, R5 is a member of the class of OR3 and STR2 for example hydroxyl, methoxyl, 2-dimethylaminoethoxyl or 2-dimethylaminoethylamino, and wherein by alkyl and alkylene is meant respectively a mono- or divalent saturated aliphatic radical containing up to about eight carbon atoms, wherein the nitrogen of the alkylamino or alkylaminoalkylene may form a heterocycle with the alkyl or alkylene groups, wherein substituted phenyl may be substituted by, for example, alkyl, hydroxyl, alkoxy, halogen, nitro or amino, wherein heteroaryl may be, for example, 2-pyridyl.
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- Synthesis and Reactions of 2,3-Dihydro-oxazoloisoindol-5(9bH)-ones
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The synthesis and reactions with nucleophiles of 2,3-dihydro-oxazoloisoindol-5(9bH)-ones are described.
- Wharton, Clifford J.,Wrigglesworth, Roger
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p. 809 - 814
(2007/10/02)
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- Metabolism of hydralazine in man. Investigation of features relevant to drug safety, Part I
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The metabolite pattern of 1-hydrazinophthalazine hydrochloride (hydralazine hydrochloride, Apresoline) in the 0-24-h urine of hypertensive patients of both slow and fast acetylator phenotype, was studied after administration of an intercurrent oral dose of 14C-labelled hydralazine hydrochloride during chronic treatment with daily doses of either 50 mg b.i.d. or 100 mg b.i.d. hydralazine hydrochloride. Within either group of acetylator phenotype no statistically significant difference of the percentage yields of the individual metabolites between the low- and high-dose regimen could be found. The dominant urinary metabolite in both acetylator phenotypes was found to be 4-(2-acetylhydrazino)-phthalazinone (NAc-HPZ). In slow acetylators 18% and in fast acetylators 33% of the total radioactivity recovered in the urine was identified as NAc-HPZ. Another important metabolite assigned to the acetylation pathway is 3-hydroxymethyl-s-triazolo-[3,4-α] phthalazine (30H-MTP), excreted in conjugated form. Again in the urine of fast acetylators this metabolite was present in higher amounts (19%) than in slow acetylators (8.3%). A possible precursor of 30H-MTP, methyl-s-triazolo-[3,4-α]phthalazine (MTP) was found in low, but about equal, amounts in both acetylator phenotypes (slow: 3.3%; fast: 2.7%). An increased amount of MTP detected after enzymatic hydrolysis is probably due to conversion of hydralazine pyruvic acid hydrazone (HPPAH) into MTP under the applied reaction conditions. An acetylator phenotype related difference was also found for metabolites arising from pathways other than acetylation. s-Triazolo-[3,4-α]phthalazine (TP) was found to represent 0.9% of urinary radioactivity in slow acetylators and 6% in fast acetylators. Conditions of enzymatic hydrolysis reversed the pattern, there being higher amounts of TP in the urine of slow acetylators (10.9%) than in fast acetylators (8.4%). Also higher amounts of phthalazin-1-one (PZ) appeared in the urine of slow acetylators (4.3%) than in the urine of fast acetylators (1.8%). The assay of NAc-HPZ in urine of hypertensive patients will allow to determine their acetylation phenotypes more relevantly to hydralazine treatment than the conventional phenotyping tests can do.
- Schmid,Kueng,Riess,Dollery,Harland
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p. 1143 - 1147
(2007/10/02)
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- Process for producing phthalazinone and derivatives of the same
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1-PHTHALAZINONE AND 1-PHTHALAZINONE DERIVATIVES OF THE FOLLOWING FORMULA: STR1 wherein R1 represents a hydrogen atom, an alkyl group, an aralkyl group, an acyloxyl group, an alkoxyl group, a halogen atom, a nitro group, an amino group or an amido group; and R2 represents a hydrogen atom, an alkyl group or an aryl group. Such can be prepared at good yields by the reaction of a benzoic acid derivative of the following formula: STR2 wherein R1 has the same meanings as defined above; X represents a halogen atom; and Y represents a hydroxyl group, an alkoxyl group or a halogen atom; with hydrazine or a hydrazine derivative of the following formula: wherein R2 has the same meanings as defined above.
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