- SYNTHESIS, STRUCTURE, AND ACTION OF SOME GOSSYPOL DERIVATIVES ON THE PEROXIDATION OF THE LIPIDS OF BIOSUBSTRATES
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The synthesis has been effected of new gossypol derivatives using piperidino- and morpholinoethylamines.According to their PMR spectra, these substances exist in the keto-amine form.Their action on the peroxidation of lipids (POL) of various biosubstrates has been studied.Gossypol bis(piperidinoethylimine) and bis(morpholinoethylimine) in concentrations of 1*1E-7 - 5*1E-6 mM exert a pronounced antioxidant action on human blood serum and rat brain synaptosomes.In the same concentrations, these substances suppressed the POL in enzymatic and nonenzymatic systems of the oxidation of rat liver microsomes.
- Dalimov, D. N.,Mukhamedzhanova, E. N.,Shneivais, V. B.,Biktimirov, L.,Ismailov, A. I.,Kamaev, F. G.
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Read Online
- Preparation method of N-(2-aminoethyl) morpholine
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The invention provides a preparation method of N-(2-aminoethyl) morpholine, which comprises the following steps: S1, adding ethanolamine into dichloromethane to fully dissolve, dropwise adding benzyl chloroformate into the solution, and reacting under alkaline conditions to generate an intermediate 1; S2, adding the intermediate 1 into dichloromethane, fully dissolving, dropwise adding 4toluenesulfonyl chloride, and reacting under an alkaline condition to generate an intermediate 2; S3, adding the intermediate 2 into acetonitrile to be fully dissolved, adding morpholine into the acetonitrile to generate an intermediate 3, wherein the structural formula of the intermediate 3 is shown as the following formula (3); and S4, adding the intermediate 3 into methanol, fully dissolving, and carrying out a catalytic hydrogenation reaction under the action of a catalyst to generate N-(2-aminoethyl)morpholine. According to the N-(2-aminoethyl)morpholine preparation method provided by the embodiment of the invention, the raw materials used in the reaction are cheap and easily available, the toxicity is low, the operation is simple and convenient, and the method has less three wastes and is more environment-friendly.
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Paragraph 0062; 0069-0072; 0073; 0080-0083
(2021/04/21)
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- COMPOUND INHIBITING BUTYRYLCHOLINESTERASE
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The invention concerns a compound according to formula (I), wherein 3 n 11, wherein R comprises or consists of a heterocycle comprising one tertiary amino group providing the binding of R to the rest of the molecule and at least three carbon atoms, wherein all carbon atoms of the heterocycle are unsubstituted or wherein R is a fused bicyclic compound comprising the heterocycle and one further cyclic compound.
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Page/Page column 9
(2020/07/31)
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- New pyrido[3,4-g]quinazoline derivatives as CLK1 and DYRK1A inhibitors: synthesis, biological evaluation and binding mode analysis
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Cdc2-like kinase 1 (CLK1) and dual specificity tyrosine phosphorylation-regulated kinase 1A (DYRK1A) are involved in the regulation of alternative pre-mRNA splicing. Dysregulation of this process has been linked to cancer progression and neurodegenerative diseases, making CLK1 and DYRK1A important therapeutic targets. Here we describe the synthesis of new pyrido[3,4-g]quinazoline derivatives and the evaluation of the inhibitory potencies of these compounds toward CDK5, CK1, GSK3, CLK1 and DYRK1A. Introduction of aminoalkylamino groups at the 2-position resulted in several compounds with low nanomolar affinity and selective inhibition of CLK1 and/or DYRK1A. Their evaluation on several immortalized or cancerous cell lines showed varying degree of cell viability reduction. Co-crystal structures of CLK1 with two of the most potent compounds revealed two alternative binding modes of the pyrido[3,4-g]quinazoline scaffold that can be exploited for future inhibitor design.
- Tazarki, Helmi,Zeinyeh, Wael,Esvan, Yannick J.,Knapp, Stefan,Chatterjee, Deep,Schr?der, Martin,Joerger, Andreas C.,Khiari, Jameleddine,Josselin, Béatrice,Baratte, Blandine,Bach, Stéphane,Ruchaud, Sandrine,Anizon, Fabrice,Giraud, Francis,Moreau, Pascale
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p. 304 - 317
(2019/02/07)
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- Highly Selective Butyrylcholinesterase Inhibitors with Tunable Duration of Action by Chemical Modification of Transferable Carbamate Units Exhibit Pronounced Neuroprotective Effect in an Alzheimer's Disease Mouse Model
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In this study, the carbamate structure of pseudo-irreversible butyrylcholinesterase (BChE) inhibitors was optimized with regard to a longer binding to the enzyme. A set of compounds bearing different heterocycles (e.g., morpholine, tetrahydroisoquinoline, benzimidazole, piperidine) and alkylene spacers (2 to 10 methylene groups between carbamate and heterocycle) in the carbamate residue was synthesized and characterized in vitro for their binding affinity, binding kinetics, and carbamate hydrolysis. These novel BChE inhibitors are highly selective for hBChE over human acetycholinesterase (hAChE), yielding short-, medium-, and long-acting nanomolar hBChE inhibitors (with a half-life of the carbamoylated enzyme ranging from 1 to 28 h). The inhibitors show neuroprotective properties in a murine hippocampal cell line and a pharmacological mouse model of Alzheimer's disease (AD), suggesting a significant benefit of BChE inhibition for a disease-modifying treatment of AD.
- Hoffmann, Matthias,Stiller, Carina,Endres, Erik,Scheiner, Matthias,Gunesch, Sandra,Sotriffer, Christoph,Maurice, Tangui,Decker, Michael
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p. 9116 - 9140
(2019/11/03)
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- A lysosome-specific near-infrared fluorescent probe for: In vitro cancer cell detection and non-invasive in vivo imaging
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Near-infrared (NIR) fluorescent probes have been developed as potential bio-materials having profound applications in diagnosis and clinical practice. Herein, we wish to disclose a highly photostable ultra-bright NIR probe for the specific detection of lysosomes in numerous cell lines. Furthermore, the applicability of the developed NIR probe was evaluated for in vivo imaging.
- Mengji, Rakesh,Acharya, Chiranjit,Vangala, Venugopal,Jana, Avijit
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supporting information
p. 14182 - 14185
(2019/12/02)
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- Bicyclic alkaloid compound, preparation method and applications thereof
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The present invention relates to a bicyclic alkaloid compound, or a tautomer, a stereoisomer, a racemate, the non-equal mixture of enantiomers, a geometric isomer, a solvate, a pharmaceutically acceptable salt or a prodrug thereof, and a pharmaceutical composition containing the compound. The invention further discloses uses of the compounds and the pharmaceutical composition thereof as drugs, especially as anti-inflammatory drugs and anti-fibrotic drugs.
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Paragraph 0151; 0152; 0231; 0232
(2018/11/03)
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- NITROGENOUS HETEROCYCLIC DERIVATIVES AND THEIR APPLICATION IN DRUGS
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The invention relates to the field of medicine, discloses new nitrogen heterocyclic derivatives, preparation method thereof and as medicament in particular as the treatment and prevention of treating tissue fibrosis of the medicament. The invention also discloses a pharmaceutically acceptable compound of the present invention comprise a pharmaceutical composition and methods for using the composition for the treatment of the human or animal tissue fibrosis of diseases, in particular for treating the human or animal renal interstitial fibrosis, glomerular sclerosis, hepatic fibrosis, pulmonary fibrosis, peritoneal fibrosis, myocardial fibrosis, skin fibrosis, after the operation of adhering, benign prostate hypertrophy, bone-myocardial, scleroderma, multiple sclerosis, pancreas fibrosis, liver cirrhosis, myosarcoma, neurofibromatosis, interstitial pulmonary fibrosis, diabetic nephropathy, Alzheimer's disease or vascular fibrosis disease in use. (by machine translation)
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Page/Page column 146
(2018/06/01)
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- In a fixed bed reactor with continuous synthetic N-aminoethyl morpholine
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The invention relates to a method for continuously synthesizing N-aminoethylmorpholine in a fixed-bed reactor, belonging to the technical field of chemical industry. Morpholine and monoethanolamine used as raw materials are subjected to heterogeneous catalysis reaction in the fixed-bed reactor by using HZSM-5 as a catalyst to continuously synthesize the N-aminoethylmorpholine product. The green technique has the characteristics of efficient and stable catalyst performance, low raw material consumption, flexible and adjustable product scheme, and favorable effects of the catalyst and continuous separation technique. The technique has the advantages of simple and reasonable process, low pollution, easily available raw materials and lower cost, is convenient to operate and convenient for continuous production, and has favorable industrialization application prospects.
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Paragraph 0039-0050
(2019/02/02)
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- HIV INTEGRASE INHIBITORS
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The present invention features compounds that are HIV integrase inhibitors and therefore are useful in the inhibition of HIV replication, the prevention and/or treatment of infection by HIV, and in the treatment of AIDS and/or ARC.
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- Nitrogenous Heterocyclic Derivatives And Their Application In Drugs
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The present invention relates to the field of medicine, provided herein are novel nitrogenous heterocyclic compounds, their preparation methods and their uses as drugs, especially for treatment and prevention of tissue fibrosis. Also provided herein are pharmaceutically acceptable compositions comprising the nitrogenous heterocyclic compounds and the uses of the compositions in the treatment of human or animal tissue fibrosis, especially for human or animal renal interstitial fibrosis, glomerular sclerosis, liver fibrosis, pulmonary fibrosis, peritoneal fibrosis, myocardial fibrosis, dermatofibrosis, postsurgical adhesion, benign prostatic hyperplasia, skeletal muscle fibrosis, scleroderma, multiple sclerosis, pancreatic fibrosis, cirrhosis, myosarcoma, neurofibroma, pulmonary interstitial fibrosis, diabetic nephropathy, alzheimer disease or vascular fibrosis.
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Paragraph 0650
(2015/03/31)
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- NITROGENOUS HETEROCYCLIC DERIVATIVES AND THEIR APPLICATION IN DRUGS
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The present invention relates to the field of medicine, provided herein are novel nitrogenous heterocyclic compounds, their preparation methods and their uses as drugs, especially for treatment and prevention of tissue fibrosis. Also provided herein are pharmaceutically acceptable compositions comprising the nitrogenous heterocyclic compounds and the uses of the compositions in the treatment of human or animal tissue fibrosis, especially for human or animal renal interstitial fibrosis, glomerular sclerosis, liver fibrosis, pulmonary fibrosis, peritoneal fibrosis, myocardial fibrosis, dermatofibrosis, postsurgical adhesion, benign prostatic hyperplasia, skeletal muscle fibrosis, scleroderma, multiple sclerosis, pancreatic fibrosis, cirrhosis, myosarcoma, neurofibroma, pulmonary interstitial fibrosis, diabetic nephropathy, alzheimer disease or vascular fibrosis.
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Paragraph 00363
(2014/02/15)
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- Synthesis and biological evaluation of 2,4-diaminoquinazoline derivatives as novel heat shock protein 90 inhibitors
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Novel 2,4-diaminoquinazoline derivatives originating from a virtual screening approach were designed, synthesized and their biological activities as heat shock protein 90 (Hsp90) inhibitors were evaluated. The prepared compounds exhibited significant anti-proliferative activities against DU-145, HT-29, HCT-116, A375P and MCF-7 cancer cell lines. The selected compounds were tested against Her2, a client protein of Hsp90, and showed significant reduction in Her2 protein expression. Compound 6b was found the most potent, reduced Her2 protein expression levels and induced Hsp70 protein expression levels significantly.
- Thorat, Dhanaji Achyutrao,Doddareddy, Munikumar Reddy,Seo, Seon Hee,Hong, Tae-Joon,Cho, Yong Seo,Hahn, Ji-Sook,Pae, Ae Nim
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scheme or table
p. 1593 - 1597
(2011/05/05)
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- An improved procedure for the synthesis of 2-morpholinoethanamine
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2-Morpholinoethanamine is prepared rapidly mainly in aqueous conditions from inexpensive and commercially accessible starting materials. The process development of an effective synthetic route by utilizing morpholine as the starting material via Michael addition, hydrazinolysis, and Curtius rearrangements was undertaken. The optimal conditions were selected in the experiments. The total yield was 81.8% and it was a convenient process. Springer Science+Business Media B.V. 2010.
- Yao, Ri-Sheng,Wu, Sheng-Hua,Jiang, Lai-En,Deng, Sheng-Song,Yu, San-Xi
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scheme or table
p. 523 - 528
(2011/11/30)
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- Azepinoindole derivatives as pharmaceutical agents
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Compounds, compositions and methods for modulating the activity of receptors are provided. In particular, compounds and compositions are provided for modulating the activity of receptors and for the treatment, prevention, or amelioration of one or more symptoms of disease or disorder directly or indirectly related to the activity of the receptors.
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- Phenyl derivatives
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Novel compounds of the formula I in which W, X, Y, T, R1 and R2 are as defined in Patent claim 1, are inhibitors of coagulation factor Xa and can be employed for the prophylaxis and/or therapy of thromboembolic disorders.
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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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- Novel multicyclic compounds and the use thereof
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The present invention is directed to novel multicyclic molecules that mediate enzymatic activity. In particular, the compounds may be effective in the treatment of diseases or disease states related to the activity of PARP, VEGFR2, and MLK3 enzymes, including, for example, neurodegenerative diseases, inflammation, ischemia, and cancer.
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- Pyrazolopyrimidines as therapeutic agents
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The present invention provides compounds of Formula I, including pharmaceutically acceptable salts and/or prodrugs thereof, where G, R2, and R3 are defined as described herein.
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- 2-aminobenzoxazole derivatives and combinatorial libraries thereof
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The present invention relates to novel 2-aminobenzoxazole derivative compounds of the following formula: wherein R1 to R4 and Z have the meanings provided herein. The invention further relates to combinatorial libraries containing two or more such compounds, as well as methods of preparing 2-aminobenzoxazole 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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- 2-aminopyridine derivatives and combinatorial libraries thereof
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The present invention relates to novel 2-aminopyridine derivative compounds of the following formula: wherein R1to R5have the meanings provided herein. The invention further relates to combinatorial libraries containing two or more such compounds, as well as methods of preparing 2-aminopyridine derivative compounds.
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- Benzothiazole derivatives with activity as adenosine receptor ligands
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The present invention relates to substituted benzothiazole derivitives and to their pharmaceutically acceptable salts useful for the treatment of diseases related to the adenosine receptor.
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- New isomeric classes of topically active ocular hypotensive carbonic anhydrase inhibitors: 5-Substituted thieno[2,3-b]thiophene-2-sulfonamides and 5-substituted theio[3,2-b]thiophene-2-sulfonamides
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A series of 5-substituted thieno[2,3-b]- and thieno[3,2-b]thiophene-2-sulfonamides was prepared and evaluated for topical ocular hypotensive activity in glaucoma models. The 5-substituents were varied to maximize both inhibitory potency against carbonic anhydrase and water solubility. At the same time, these substituents were varied in order to obtain compounds with the appropriate pK(a) to minimize pigment binding in the iris. All of these variables were optimized in the best compound, 5-[[(methoxyethyl)](methoxyethyl)ethyl]amino]methyl]thieno[2,3-b] thiophene-2-sulfonamide hydrochloride (55).
- Prugh,Hartman,Mallorga,McKeever,Michelson,Murcko,Schwam,Smith,Sondey,Springer,Sugrue
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p. 1805 - 1818
(2007/10/02)
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- 3-amino-5-methyl-1H-pyrazole-4-carboxylic acids and esters thereof as anticonvulsants, muscle relaxants and anxiolytics
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A novel method of controlling epilepsy, muscle tension, muscular spasticity, and anxiety in living animal bodies by administering compounds of the formula: STR1 wherein: R1 is hydrogen, loweralkyl or a pharmaceutically acceptable cation; R2 and R3, same or different, are hydrogen, loweralkyl, aryl, cycloalkyl, loweralkenyl, 1-adamantyl, heterocyclicaminoalkyl, diloweralkylaminoloweralkyl, or R2 with R3 and adjacent nitrogen may form a heterocyclic ring structure; and the pharmaceutical acceptable acid salts, and tautomeric isomers thereof; and novel pharmaceutical compositions therefor are disclosed.
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- N-(amino)alkyl)-1-pyrrolidine, 1-piperidine and 1-homopiperidinecarboxamides (and thiocarboxamides) with sulfur linked substitution in the 2, 3 or 4-positions
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Novel pyrrolidine, piperidine and homopiperidinecarboxamide and thiocarboxamide compounds having the formula: STR1 wherein X is --S--, --S(O)-- or --S(O)2 --; A is a loweralkalene chain and A1 and A2 are alkalene chains when p and d are one; R, R1 and R2 are hydrogen, loweralkyl, phenyl cycloalkyl or phenylalkyl and R1 and R2 may form a heterocyclic residue with the adjacent nitrogen atom; Q is a selected aromatic radical, and the pharmaceutically acceptable acid addition salts useful as cardiac antiarrhythmia agents are disclosed. Novel chemical intermediates, unsubstituted on pyrrolidine, piperidine and homopiperidine nitrogen but with --(A2)p --X--(A2)d --Q side chain are also disclosed.
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- 1-[(aminoalkyl and aminoalkylamino)carbonyl and thiocarbonyl]-α,α-diarylpyrrolidine, piperidine and homopiperidineacetamides and acetonitriles
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Novel 1-[(aminoalkyl and aminoalkylamino)carbonyl and thiocarbonyl]-α,α-diaryl-pyrrolidine, piperidine and homopiperidineacetamides and acetonitriles having the formula: STR1 wherein; n is zero, one or two; X is oxygen or sulfur; Z is STR2 p is 0 to 5 inclusive with the proviso that when Z is STR3 p is at least one; Y is aminocarbonyl or cyano; Ar1 and Ar2 are 2, 3 or 4-pyrido, phenyl or substituted phenyl; R is hydrogen or loweralkyl; R1, R2 and R3 are hydrogen, cycloalkyl, loweralkyl, phenyl, substituted phenyl, phenylloweralkyl, and R2 and R3 taken with the adjacent nitrogen may form a heterocyclic residue, and diastereoisomers when possible and pharmaceutical salts; and the method and pharmaceutical compositions for treating cardiac arrhythmias therewith are disclosed.
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- Substituted sulfonamidobenzamides and method of treating arrhythmias
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Novel substituted sulfonamidobenzamides are described as useful antiarrhythmic agents. Their use in the treatment of cardiac arrhythmias, especially re-entrant arrhythmias, via the prolongation of the action potential of cardiac tissue is provided. Pharmaceutical formulations containing such compounds are also disclosed.
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- N-[(amino)alkyl]-1-pyrrolidine, 1-piperidine and 1-homopiperidinecarboxamides (and thiocarboxamides) with sulfur linked substitution in the 2, 3 or 4-position
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Novel pyrrolidine, piperidine and homopiperidinecarboxamide and thiocarboxamide compounds having the formula: STR1 wherein X is --S--, --S(O)-- or --S(O)2 --; A is a loweralkalene chain and A1 and A2 are alkalene chains when p and d are one; R, R1 and R2 are hydrogen, loweralkyl, phenyl cycloalkyl or phenylalkyl and R1 and R2 may form a heterocyclic residue with the adjacent nitrogen atom; Q is a selected aromatic radical, and the pharmaceutically acceptable acid addition salts useful as cardiac antiarrhythmia agents are disclosed. Novel chemical intermediates, unsubstituted on pyrrolidine, piperidine and homopiperidine nitrogen but with --(A2)p --X--(A2)d --Q side chain are also disclosed.
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- Substituted sulfonamidobenzamides, antiarrhythmic agents and compositions thereof
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Novel substituted sulfonamidobenzamides are described as useful antiarrhythmic agents. Their use in the treatment of cardiac arrhythmias, especially re-entrant arrhythmias, via the prolongation of the action potential of cardiac tissue is provided. Pharmaceutical formulations containing such compounds are also disclosed.
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- Aryloxy-N-(aminoalkyl)-1-pyrrolidine and piperidine carboxamides and carbothioamides having antiarrhythmic activity
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Pharmaceutical compositions comprised of aryloxy-N-(aminoalkyl)-1-pyrrolidine and piperidine carboxamides and carbothioamides are provided of the formula: STR1 wherein Ar is selected from the group consisting of 1-naphthyl, 2-naphthyl, 2,3-dihydro-1H-inden-4-yl, 2,3-dihydro-1H-inden-5-yl, phenyl, substituted phenyl wherein the substituents are selected from lower alkyl of from 1 to 8 carbon atoms, lower alkyloxy of from 1 to 8 carbon atoms, halogen and trifluoromethyl; m and n are 1 or 2 but are never 2 at the same time; p is 1, 2, 3 or 4; R is selected from hydrogen or lower alkyl of from 1 to 3 carbon atoms; R1 and R2 are selected from hydrogen, lower alkyl of from 1 to 8 carbon atoms, phenyl, phenyl lower alkyl of from 7 to 9 carbon atoms, and cycloalkyl of from 3 to 8 carbon atoms, and R1 and R2 taken together with the adjacent atom may form a heterocyclic residue selected from 4-morpholino, 1-pyrrolidino, 1-piperidino, 1-piperazino and 4-lower alkyl piperazin-1-yl; X is oxygen or sulfur; and the pharmaceutically acceptable acid addition salts thereof having antiarrhythmic activity.
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- INTRAMOLECULAR GENERAL-BASE CATALYSIS OF SCHIFF-BASED HYDROLYSIS BY TERTIARY AMINO GROUPS.
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Hydrolysis of a series of Schiff bases derived from benzophenone and various amines has been studied kineticlly in aqueous solution. A linear correlation of the log of the rate constants for the water reaction with the Schiff base pK//a (slope minus 0. 70) shows large positive deviations for Schiff bases derived from (2-aminoethyl)diethylamine, N-(2-aminoethyl)morpholine, N-(2-aminoethyl)piperazine and 2-(aminomethyl)pyridine (1i) but small deviations for Schiff bases from N-(3-aminopropyl)morpholine and 2-(2-aminoethyl)pyridine. The deviations found are attributed to intramolecular general-base catalysis of the water reaction by the internal tertiary amino groups. Magnitudes of the rate enhancement are correlated well with pK//a//l of the internal catalyst ( beta equals 0. 49). Effective concentrations of the internal bases are estimated to range from 340 (1e) to 40 M.
- Okuyama,Shibuya,Fueno
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p. 730 - 736
(2007/10/02)
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- Pyridazine derivatives in alleviating depressive states
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A class of pyridazine derivatives useful as antidepressants and mood elevators when used in medicine of the formula: STR1 wherein R1 is a hydrogen atom or a lower alkyl group; R2 is an aryl group such as phenyl or naphthyl or substituted phenyl and N is 2 or 3. Y and Z may be the same or different lower alkyl groups or taken together with the nitrogen atom form a heterocyclic ring wherein Z and Y are lower alkylene radicals cyclized in a ring which contains an oxygen atom linked between them and the other ends of the alkylene chain link to the nitrogen atom. The invention also includes non-toxic acid addition salts thereof suitable for pharmaceutical use and methods for their administration and use as therapeutic agents for humans.
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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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- Amine bisulfites
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This invention relates to the amine bisulfites which are useful as a combination corrosion inhibitor/oxygen scavenger. This is illustrated by heterocyclic amine bisulfites such as pyridine bisulfites.
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