- Palladium-catalyzed double carbonylation reactions of o-dihaloarenes with amines in phosphonium salt ionic liquids
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Palladium-catalyzed double carbonylation of o-dihaloarenes with amines in phosphonium salt ionic liquids proceeds efficiently to give the corresponding N-substituted phthalimides. This process can tolerate a wide array of functional groups and affords products in excellent yields. The recyclability of the catalytic system was also investigated.
- Cao, Hong,Alper, Howard
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- Unmasking Amides: Ruthenium-Catalyzed Protodecarbonylation of N-Substituted Phthalimide Derivatives
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The unprecedented transformation of a wide range of synthetically appealing phthalimides into amides in a single-step operation has been achieved in high yields and short reaction times using a ruthenium catalyst. Mechanistic studies revealed a unique, homogeneous pathway involving five-membered ring opening and CO2 release with water being the source of protons.
- Yuan, Yu-Chao,Kamaraj, Raghu,Bruneau, Christian,Labasque, Thierry,Roisnel, Thierry,Gramage-Doria, Rafael
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- Palladium-catalyzed carbonylative synthesis of phthalimides from 1,2-dibromoarenes with molybdenum hexacarbonyl as carbon monoxide source
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We describe here a convenient and mild, carbon monoxide gas-free palladium-catalyzed procedure to obtain N-substituted phthalimides with molybdenum hexacarbonyl as carbon monoxide precursor. These conditions tolerate a number of functional groups on the benzene ring as well as a number of amines and give the corresponding phthalimides in good to excellent yields. Copyright
- Wu, Xiao-Feng,Oschatz, Stefan,Sharif, Muhammad,Flader, Anika,Krey, Lisa,Beller, Matthias,Langer, Peter
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- “On water” nano-Cu2O-catalyzed CO-free one-pot multicomponent cascade cyanation-annulation-aminolysis reaction toward phthalimides
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An efficient nano-Cu2O-catalyzed cascade multicomponent reaction of 2-halobenzoic acids and trimethylsilyl cyanide with diverse amines was developed using water as a solvent, affording versatileN-substituted phthalimide derivatives in moderate to excellent yields. This novel strategy features carbon monoxide gas-free, environmentally benign, one-pot multistep transformation, commercially available reagents, a cheap catalyst without any additives, wide functional group tolerance, and operational convenience.
- Wen, Xiaowei,Liu, Xiaojuan,Yang, Zhiqi,Xie, Menglan,Liu, Yuxi,Long, Lipeng,Chen, Zhengwang
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supporting information
p. 1738 - 1743
(2021/03/14)
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- Nitrile Synthesis by Aerobic Oxidation of Primary Amines and in situ Generated Imines from Aldehydes and Ammonium Salt with Grubbs Catalyst
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Herein, a Grubbs-catalyzed route for the synthesis of nitriles via the aerobic oxidation of primary amines is reported. This reaction accommodates a variety of substrates, including simple primary amines, sterically hindered β,β-disubstituted amines, allylamine, benzylamines, and α-amino esters. Reaction compatibility with various functionalities is also noted, particularly with alkenes, alkynes, halogens, esters, silyl ethers, and free hydroxyl groups. The nitriles were also synthesized via the oxidation of imines generated from aldehydes and NH4OAc in situ. (Figure presented.).
- Utsumi, Tatsuki,Noda, Kenta,Kawauchi, Daichi,Ueda, Hirofumi,Tokuyama, Hidetoshi
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supporting information
p. 3583 - 3588
(2020/08/05)
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- COMBINATION TREATMENTS COMPRISING ADMINISTRATION OF 1H-PYRAZOLO[4,3-B]PYRIDINES
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The present invention provides 1H-pyrazolo[4,3-b]pyridin-7-amines of formula (I) as PDE1 inhibitors together with a second compound useful in the treatment of a neurodegenerative disorder and their combined use as a medicament, in particular for the treatment of neurodegenerative and/or cognitive disorders.
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Page/Page column 109
(2019/07/19)
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- 1H-PYRAZOLO[4,3-B]PYRIDINES AS PDE1 INHIBITORS
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The present invention provides 1H-pyrazolo[4,3-b]pyridines of formula (I) as PDE1 inhibitors and their use as a medicament, in particular for the treatment of neurodegenerative disorders and psychiatric disorders.
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Paragraph 0514-0515
(2019/07/10)
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- COMBINATION TREATMENTS COMPRISING ADMINISTRATION OF 1H-PYRAZOLO[4,3-B]PYRIDINES
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The present invention provides 1H-pyrazolo[4,3-b]pyridin-7-amines of formula (I) as PDE1 inhibitors together with a second compound which compound is useful in the treatment of a psychiatric disorder and their combined use as a medicament, in particular for the treatment of psychiatric and/or cognitive disorders.
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Page/Page column 106
(2019/07/19)
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- 6-aminomethyl-1,1-dioxo-1,2-benzothiazol-3-one intermediate and synthetic method thereof
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The invention provides a 6-aminomethyl-1,1-dioxo-1,2-benzothiazol-3-one intermediate. The chemical name of the intermediate is 2-(1,1-dioxo-1,2-benzothiazol-3-keto-6-ylmethyl)-1H-isoindole-1,3-dione,and the structural formula of the intermediate is shown in the specification (intermediate 3). The invention further provides a synthetic method of the 6-aminomethyl-1,1-dioxo-1,2-benzothiazol-3-one intermediate. The intermediate 3 provided by the invention provides a novel method and a novel synthetic route for synthesizing a mesosulfuron-methyl intermediate that is 6-aminomethyl-1,1-dioxo-1,2-benzothiazol-3-one. The novel synthetic route does not need hydrogenation reduction reaction, mainly comprises substitution reaction and oxidation reaction, is mild in reaction condition, easily available in various raw materials and high in yield, can effectively reduce the production cost, and has a relatively strong industrial application prospect.
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Paragraph 0047-0052; 0073; 0087
(2019/12/02)
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- Synthesis method of 6-aminomethyl-1,1-dioxo-1,2-benzothiazol-3-one
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The invention provides a preparation method of 6-aminomethyl-1,1-dioxo-1,2-benzothiazol-3-one. The method comprises following steps of: synthesizing 2-(3-sulfo-4-methylbenzyl)-1H-isoindole-1,3-dione;2-(3-chlorosulfonyl-4-methylbenzyl)-1H-isoindole-1,3-dione; synthesizing 2-(3-aminosulfonyl-4-methylbenzyl)-1H-isoindole-1,3-dione; synthesizing 2-(1,1-dioxo-1,2-benzothiazol-3-keto-6-ylmethyl)-1H-isoindole-1,3-dione; and synthesizing the target compound. The synthetic method is a novel synthetic method of a mesosulfuron-methyl intermediate that is methyl 4-(methylsulfonamidomethyl)-2-sulfamoylbenzoate. The method does not need a hydrogenation reduction, reaction conditions are mild, various raw materials are easy to obtain, the yield is high, the production cost can be effectively reduced, and the method has a relatively strong industrial application prospect.
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Paragraph 0043-0046; 0066-0069; 0080-0083
(2019/12/02)
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- 2-(4-methylbenzyl)-1H-isoindole-1,3-dione derivative and synthesis method thereof
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The invention provides a 2-(4-methylbenzyl)-1H-isoindole-1,3-dione derivative, wherein the structural formula is defined in the specification, and the group R1 in the structural formula is hydroxyl, chloro or amino. The invention further provides a synthesis method of the 2-(4-methylbenzyl)-1H-isoindole-1,3-dione derivative. According to the invention, the 2-(4-methylbenzyl)-1H-isoindole-1,3-dionederivative can be used as the intermediate of 6-aminomethyl-1,1-dioxo-1,2-benzothiazole-3-one, the new method and the new synthetic route are provided in the synthesis of a mesosulfuron-methyl intermediate 6-aminomethyl-1,1-dioxo-1,2-benzothiazole-3-one, and the new synthetic route does not need hydrogenation reduction reaction, and has characteristics of mild reaction conditions, easily available raw materials, high yield, effectively reduced production cost and strong industrial application prospect.
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Paragraph 0040; 0044; 0064; 0067; 0078; 0081
(2020/01/12)
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- 1H-PYRAZOLO[4,3-B]PYRIDINES AS PDE1 INHIBITORS
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The present invention provides 1H-pyrazolo[4,3-b]pyridin-7-amines of formula (I) as PDE1 inhibitors and their use as a medicament, in particular for the treatment of neurodegenerative disorders and psychiatric disorders.
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Page/Page column 100; 101
(2018/09/25)
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- Alkoxide-Catalyzed Hydrosilylation of Cyclic Imides to Isoquinolines via Tandem Reduction and Rearrangement
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An alkoxide-catalyzed hydrosilylation of cyclic imides to isoquinolines was realized via tandem reduction and rearrangement. Using TMSOK as the catalyst and (EtO)2MeSiH as the reductant, a series of cyclic imides containing different functional groups were reduced to the corresponding 3-aryl isoquinolines in moderate to good yields. The scenario of the reaction pathway was supposed to involve the reduction of imides to ω-hydroxylactams, which underwent rearrangement in the presence of a base catalyst, and then the carbonyl reduction, followed by siloxy elimination.
- Wu, Xiaoyu,Ding, Guangni,Yang, Liqun,Lu, Wenkui,Li, Wanfang,Zhang, Zhaoguo,Xie, Xiaomin
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supporting information
p. 5610 - 5613
(2018/09/12)
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- Mechanochemical N-alkylation of imides
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The mechanochemical N-alkylation of imide derivatives was studied. Reactions under solvent-free conditions in a ball mill gave good yields and could be put in place of the classical solution conditions. The method is general and can be applied to various imides and alkyl halides. Phthalimides prepared under ball milling conditions were used in a mechanochemical Gabriel synthesis of amines by their reaction with 1,2-diaminoethane.
- Bri?, Anamarija,Dud, Mateja,Margeti?, Davor
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supporting information
p. 1745 - 1752
(2017/09/27)
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- Synthetic method for N-substituted imide
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The invention provides a synthetic method for N-substituted imide. According to the method, aromatic ketone and amine are used as substrates, air or oxygen is used as an oxygen source, and cyclic imide is produced under liquid phase conditions under the action of a catalyst. The method is mild in conditions, high in oxidation efficiency and high in product yield; and since the method uses air or oxygen as the oxygen source, the method is economic and environment-friendly and has good application prospect.
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Paragraph 0016; 0028; 0029; 0030; 0031
(2017/04/20)
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- Potassium Hydroxide-Catalyzed Chemoselective Reduction of Cyclic Imides with Hydrosilanes: Synthesis of ω-Hydroxylactams and Lactams
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Potassium hydroxide-catalyzed hydrosilylation exhibits excellent activity and chemoselectivity for the reduction of cyclic imides under mild reaction conditions. The chemoselectivity of the reduction system may be readily tuned by changing the identity an
- Ding, Guangni,Li, Chengjun,Shen, Yifan,Lu, Bin,Zhang, Zhaoguo,Xie, Xiaomin
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supporting information
p. 1241 - 1250
(2016/04/26)
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- Reactant cum solvent water: Generation of transient λ3-hypervalent iodine, its reactivity, mechanism and broad application
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An outstanding amidation/imidation process is demonstrated under metal-free benign reaction conditions by grafting terminal alkynes with varied amines and reactant cum solvent water. We explored diverse substrate scope in the nonconventional approach for synthesis of several classes of valuable compounds bearing amide linkages such as N-tosyl, N-aminotosyl, N-oxobenzyl, N-alkylated sugar-based secondary and tertiary chiral amides and also exploiting it for synthesis of valuable cyclic imides through simultaneous activation of triple bond and sp2C-H of aldehyde. The in situ-generated powerful reagent PhI(OH)2 enables selective cleavage and functionalization of terminal C-C triple bonds through simultaneous construction of C-N and C=O bonds. A measurable breakthrough in time-resolved ATR-MIR spectroscopy of the ongoing λ3-hypervalent iodine controlled reaction revealed formation of the unknown intermediates. The ATR-MIR technology is used for identifying infrared (IR) spectra of the individual intermediate/component present in the reaction mixture, which contains several compounds. The structures of the intermediates and their IR spectra were determined by DFT study. This unprecedented combination of experimental results and theoretical prediction provided useful information regarding the reaction insights such as the cleavage of triple bond, amination and amidation in the complex reaction process involving λ3-hypervalent iodine-bearing labile intermediates to the desired amide. The NMR and labelling (2H and 18O) studies supported the DFT-IR predicted reaction pathway.
- Khamarui, Saikat,Maiti, Rituparna,Mondal, Ramij R.,Maiti, Dilip K.
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p. 106633 - 106643
(2016/01/08)
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- An unprecedented approach to the Gabriel amine synthesis utilizing tosylhydrazones as alkylating agents
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A new and one-pot version of the Gabriel phthalimide amine synthesis utilizing carbonyl compounds as alkylating agents via their tosylhydrazone surrogates is disclosed. The alkylation involves copper catalysed carbene insertion into the N-H bond of phthalimide. Basically, the protocol also offers a powerful tool for deoxygenative hydroamination of carbonyl compounds.
- Yadav, Arvind K.,Yadav, Lal Dhar S.
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p. 34764 - 34767
(2014/11/08)
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- Chitosan: An efficient recyclable catalyst for transamidation of carboxamides with amines under neat conditions
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A novel chitosan-catalyzed transamidation of carboxamides with amines under solvent-free conditions is described. A series of amide derivatives as well as more challenging aryl and alkyl amines with long-chain alkyl substituents could be selectively converted into the corresponding transamidation products, which are frequently found in biologically active compounds and pharmaceuticals. Under similar reaction conditions benzo[d]heterocycles were also obtained via a one-pot synthesis through transamidation and subsequent dehydration. Recyclability of chitosan was demonstrated, with quantitative yields of products obtained without any loss of catalytic activity. the Partner Organisations 2014.
- Nageswara Rao, Sadu,Chandra Mohan, Darapaneni,Adimurthy, Subbarayappa
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supporting information
p. 4122 - 4126
(2014/10/15)
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- Metal-free, highly efficient organocatalytic amination of benzylic C-H bonds
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A new synthetic approach toward direct C-N bond formation through sp 3 C-H activation has been developed under metal-free conditions. Both primary and secondary benzylic C-H substrates could react smoothly with various amines to give only mono-amination products with good to excellent yields. The Royal Society of Chemistry 2013.
- Xue, Qicai,Xie, Jin,Li, Huamin,Cheng, Yixiang,Zhu, Chengjian
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supporting information
p. 3700 - 3702
(2013/05/09)
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- Synthesis and cross-coupling reactions of imidomethyltrifluoroborates with aryl chlorides
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Potassium imidomethyltrifluoroborate salts were efficiently synthesized. Potassium phthalimidomethyltrifluoroborate was successfully used in Suzuki-Miyaura-like cross-coupling reactions with a variety of aryl chlorides.
- Devulapally, Rammohan,Fleury-Brégeot, Nicolas,Molander, Gary A.,Seapy, Dave G.
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supporting information; experimental part
p. 1051 - 1055
(2012/03/26)
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- meta-directing cobalt-catalyzed diels-alder reactions
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(Chemical Equation Presented) Overcoming the ortho/para rule? The regioselectivity of Diels-Alder reactions with neutral electron demand between 1,3-dienes with alkynes can be controlled by simple cobalt diimine complexes so that the meta-substituted cycloadducts are generated in good yields and excellent regioselectivity (see scheme; DDQ=2,3-dichloro-5,6-dicyano-1,4- benzoquinone).
- Hilt, Gerhard,Janikowski, Judith,Hess, Wilfried
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p. 5204 - 5206
(2007/10/03)
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- Synthesis, dual fluorescence, and fluoroionophoric behavior of dipyridylaminomethylstilbenes
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The synthesis, dual fluorescence, and fluoroionophoric behavior of two donor-σ spacer-acceptor (D-s-A) compounds, trans-4-(N,N-bis(2-pyridyl) amino)methylstilbene (1H) and trans-4-(N,N-bis(2-pyridyl)amino)methyl-4′- cyanostilbene (1CN), are reported and compared to that of trans-4-(N,N-bis(2- pyridyl)amino)methyl-4′-(N,N-dimethylammo)stilbene (1DPA). To gain insights into the dual fluorescence properties for 1H and 1CN in polar but not in nonpolar solvents, model compounds resulting from a replacement of the stilbene group by alkyl (2R) or xylyl (2X) groups or from a replacement of the dipyridylamino (dpa) group by dianisoleamino (3AA), diethylamino (SEE), methylanilino (3MP), or diphenylamino (3PP) groups also have been investigated. In addition to 1H and 1CN, all four compounds of 3 display dual fluorescence. The locally excited (LE) fluorescence mainly results from the stilbene group and the ICT fluorescence from the through-bond interactions between the amino donor and the stilbene acceptors. In the presence of transition metal ions such as Zn(II), Ni(II), Cu(II), and Cd(II), the ICT processes are switched from dpa → stilbene (A) in 1H and 1CN to stilbene (D) → dpa/metal ion (A) in their complexes. Whereas the ICT states for the complexes are generally nonfluorescent, an exception was found for the case of 1H/Zn(II). As a result, substituent-dependent fluoroionophoric behavior has been demonstrated by 1H, 1CN, and 1DPA in response to Zn(II).
- Yang, Jye-Shane,Lin, Yan-Duo,Chang, Ya-Ho,Wang, Shin-Shin
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p. 6066 - 6073
(2007/10/03)
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- Benzylphthalimides and phenethylphthalimides with thalidomide-like activity on the production of tumor necrosis factor α
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Benzylphthalimide analogs (P1P's) and phenethylphthalimide analogs (P2P's) have been found to exhibit thalidomide-like activity on the production of tumor necrosis factor (TNF)-α by the human leukemia cell line, HL-60, stimulated by 12-O-tetradecanoylphorbol-13-acetate (TPA). Structure-activity relationships are discussed on the basis of the TNF-α production-enhancing activity. Benzylphthalimide (P1P-00) exhibited activity which is weaker than that of thalidomide, but introduction of a methyl group at the ortho-position of the benzyl moiety (P1P-10) resulted an increase to a level comparable with that of thalidomide. Phenethylphthalimide (P2P-00) is more potent than thalidomide, and its fluorinated derivative, 2-phenethyl-4,5,6,7-tetrafluoro- 1H-isoindole-1,3-dione (FP2P-00), exhibited potent activity at very low concentrations.
- Sasaki,Shibata,Hashimoto,Iwasaki
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p. 1228 - 1233
(2007/10/03)
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- Amidine derivatives and cardiotonic compositions
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Amidine derivatives of the formula STR1 wherein R1 and R2, which may be the same or different, represent each a hydrogen atom or a lower alkyl group, or R1 and R2 together with an intermediary carbon atom and/or hetero atom may form a ring; X represents STR2 (wherein R8 represents a hydrogen atom, a lower alkyl group, or --CH2 COOR9, where R9 represents a hydrogen atom or a lower alkyl group; Z represents a single bond, --CH2 --, --CH2 CH2 --, or --CH=CH--); R3 represents a hydrogen or chlorine atom, methoxy group, nitro group, or amino group; Y represents --CH2 CH2 --, --CH=CH--, --CH2 O--, or --OCH2 --; R4 represents a hydrogen atom, methoxy group, benzoyl group, nitro group, or amino group; and R5, R6 and R7, which may be the same or different, represent each a hydrogen atom, lower alkyl group, cycloalkyl group, aralkyl group, substituted alkyl group, substituted aralkyl group, or amino group, or R5 and R7 may form a ring, or salts thereof have an excellent cardiotonic activity and can be used as cardiotonics.
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