- Preparation method of (s)-N-ethyl-2-aminomethylpyrrolidine
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The invention provides a preparation method of (s)-N-ethyl-2-aminomethylpyrrolidine. 2-amino-5-hydroxyvaleric acid used as a raw material undergoes esterification protection to obtain methyl 2-amino-5-hydroxypentanoate, N-ethylation is further achieved through bromoethane, and then the N-ethyl-2-aminomethylpyrrolidine is prepared through hydroxyl halogenation, substitution cyclization, ammonolysisand reduction six-step reaction. High-cost raw materials and an N,O-diethylation reaction are successfully avoided, and the method has the advantages of easiness in implementation of the above reaction route, few byproducts, high yield reaching 64.2%, and suitableness for industrialization.
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- Preparation method for N-ethyl-2-aminomethylpyrrolidine
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The invention relates to a preparation method for N-ethyl-2-aminomethylpyrrolidine. The preparation method comprises the following steps: with furfural as a raw material, subjecting the furfural to acetal protection so as to obtain furfural glycol acetal, allowing the furfural glycol acetal to react with ethylamine so as to generate 2-(1,3-dioxolan-2-yl)-N-ethylpyrrole, allowing the 2-(1,3-dioxolan-2-yl)-N-ethylpyrrole to react with diluted hydrochloric acid so as to generate N-ethylpyrrole-2-carbaldehyde, and subjecting the N-ethylpyrrole-2-carbaldehyde and liquid ammonia to palladium-carbonreductive ammoniation by one step so as to generate the N-ethyl-2-aminomethylpyrrolidine. The preparation method has a synthetic route which is described in the specification. The invention has the following advantages: the preparation method for the N-ethyl-2-aminomethylpyrrolidine provided by the invention starts with the furfural as a raw material to prepare a product through protection, amination and reductive ammoniation, and has the advantages of short reaction route, high yield capable of reaching 85% or above, little pollution and applicability to industrialization.
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Paragraph 0017; 0027-0029
(2018/05/16)
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- SUBSTITUTED BENZAMIDE MODULATORS OF DOPAMINE RECEPTOR
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The present invention relates to new substituted benzamide modulators of dopamine receptor, pharmaceutical compositions thereof, and methods of use thereof.
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Page/Page column 12
(2010/05/13)
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- Tetracyclic benzimidazole derivatives and combinatorial libraries thereof
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The present invention relates to novel tetracyclic benzimidazole derivative compounds of the following formula: wherein R1to R10have the meanings described in here. The invention further relates to combinatorial libraries containing two or more such compounds, as well as methods of preparing tetracyclic benzimidazole derivative compounds.
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- 4-unsubstituted dihydroisoquinolinone derivatives and combinatorial libraries thereof
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The present invention relates to novel dihydroisoquinolinone (DHQ) derivative compounds of the following formula: wherein R1to R7, X, Y, Z, b, c and d have the meanings provided herein. The invention further relates to combinatorial libraries containing two or more such compounds, as well as methods of preparing DHQ derivative compounds.
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- Synthesis and in vitro evaluation of 2,3-dimethoxy-5-(fluoroalkyl)-substituted benzamides: High-affinity ligands for CNS dopamine D2 receptors
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A number of 2,3-dimethoxy-5-(fluoroalkyl)-N-[(1-ethyl-2-pyrrolidinyl)methyl] benzamides (with or without a 6-hydroxy group) were synthesized and evaluated as dopamine D2 receptor ligands. The parent acids were synthesized via the Claisen rearrangement of the appropriate O-allyl ethers, which were derived from o-vanillic acid or 2,3-dimethoxysalicylic acid. A decrease in reactivity was found to be characteristic of pentasubstituted benzoates, and difficulties were encountered with the introduction of fluorine onto the ethyl side chains. The (fluoroethyl)- and (fluoropropyl)salicylamides were 5 times more potent than the corresponding benzamides in inhibiting [3H]spiperone binding to the D2 receptor. These (fluoroalkyl)salicylamides are of potential value for in vivo positron emission tomography (PET) studies upon the basis of their relatively selective, high potency binding affinity for the D2 receptor.
- Bishop,Mathis,Gerdes,Whitney,Eaton,Mailman
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p. 1612 - 1624
(2007/10/02)
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- ORGANIC COMPOUNDS AND THEIR USE AS PHARMACEUTICALS
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A pharmaceutical compound of the formula STR1 in which R. sup.1 is--CHO, CH 2 OH,--CH 2 OC 1-4 alkyl,--COC 1-3 alkyl,--CH(OH)C 1-3 alkyl or--COOH, R 2 is C 1-4 alkyl,--CHO,--CH. sub.2 OH,--CH 2 OC 1-4 alkyl,--COC 1-3 alkyl,--CH(OH)C. sub. 1-3 alkyl or--COOH, R 3 is C 1-4 alkyl and X is pyrrolidinyl or pyrrolidinylmethyl; and salts and esters thereof.
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- POTENTIAL NEUROLEPTICS OF THE ORTHOPRAMIDE SERIES; SYNTHESIS OF N-SUBSTITUTED 5-(AMINOSULFONYL)-2-METHOXYBENZAMIDES
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The mixed anhydride of 5-(aminosulfonyl)-2-methoxybenzoic acid (VII) and monoethyl carbonate reacted with benzylamine, 1-methylpiperazine, and 1-benzylpiperazine to give the 5-(aminosulfonyl)-2-methoxybenzamides II, IV, and V.Heating the ethyl ester X with 4-amino-1-methylpiperidine resulted in the amide III.Reaction of 5-(chlorosulfonyl)-2-methoxybenzoyl chloride (XI) with 1-benzylpiperazine afforded 5-(4-benzylpiperazinosulfonyl)-2-methoxybenzoic acid 4-benzylpiperazide (VI).Compounds II-VI are analogues of the antidopaminergic and antiemetic agent sulpiride (I) but only the benzylpiperazides V and VI showed indications of psychotropic activity of the neuroleptic type.
- Valenta, Vladimir,Protiva, Miroslav
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p. 2095 - 2106
(2007/10/02)
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- Mitomycin analogs
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Antineoplastic compounds of the formula, IIa, STR1 wherein: Y is hydrogen or lower alkyl; and Z is a lower alkoxy substituted quinolinylamino radical, a cyano substituted pyrazolylamino radical or a mono- or di-lower alkyl substituted thiazolamino radical, or a nitrogen-containing heterocyclic radical, or a cyano, phenyl, carboxamido or lower alkoxycarbonyl substituted 1-aziridinyl radical or a lower alkyl, formyl or acetylphenyl substituted 1-piperazinyl radical, or an hydroxy or piperidyl substituted 1-piperidyl radical, or a lower alkoxy, amino or halo substituted pyridylamino radical, or a carboxamido, mercapto or methylenedioxy substituted anilino radical, or a radical of the formula, STR2 wherein R is hydrogen or lower alkyl and R" is a nitrogen-containing heterocyclic radical, or a butyrolactonyl radical, or an adamantyl radical, or a mono- lower alkoxy substituted phenyl radical, or a substituted lower alkyl radical selected from the group consisting of mercapto lower alkyl, carboxy lower alkyl, mono-, di- and tri-lower alkoxy lower alkyl, lower alkyl thio lower alkyl and lower alkoxycarbonyl substituted derivatives thereof, cyano lower alkyl, mono-, di- and tri-lower alkoxy phenyl lower alkyl, phenyl cyclo lower alkyl, 1-pyrrolidinyl lower alkyl, N-lower alkyl pyrrolidinyl lower alkyl, N-morpholinyl lower alkyl, and lower dialkylamino lower alkyl.
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- Substituted 2,3-alkylene bis (oxy) benzamides and derivatives and method of preparation
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Novel substituted 2,3-alkylene bis (oxy) benzamides and derivatives thereof are disclosed. Also disclosed is a method for producing said compounds. The compounds have anxiolytic, psychostimulant, disinhibiting and thymoanaleptic properties useful therapeutically in the psychofunctional field, particularly in gastro-enterology, cardiology, urology, rheumatology and gynaecology.
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- Pyrazine derivatives
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Pyrazine derivatives by the formula STR1 are disclosed. In the above formula, R1 and R2, which may be the same or different, each represents a hydrogen atom, a halogen atom, a hydroxy group, a lower alkoxy group, a phenyl lower alkoxy group, a phenoxy group, a mercapto group, a lower alkylthio group, a phenyl lower alkylthio group, a phenylthio group, an amino group, a substituted amino group, a lower alkyl group, a carbamoyl group or a sulfamoyl group; R3 represents a lower alkoxy group; R4, R5, and R6, which may be the same or different, each represents a hydrogen atom, a lower alkyl group, a cycloalkyl group, a phenyl lower alkyl group, or a phenyl group; and A represents a lower alkylene group; said R4 and A, said R5 and A, said R4 and R5, or said R5 and R6 may form a 5-membered or 6-membered nitrogen-containing heterocyclic ring which may further contain a hetero-atom together with nitrogen atom, and the pharmacologically acceptable non-toxic salts thereof. The compounds of this invention have a strong and selective antiematic activity and an effect of stimulating the gastric motility.
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