- 5-Substituted Benzothiophenes: Synthesis, Mechanism, and Kinetic Studies
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The kinetics of the reaction of 4-methoxythiophenoxyacetaldehyde diethyl acetal, 4-nitrothiophenoxyacetaldehyde diethyl acetal, and 3-methoxythiophenoxyacetaldehyde diethyl acetal in polyphosphoric acid has been explained. The kinetic behavior has been ex
- Cerminara, Iole,D'Alessio, Luciano,D'auria, Maurizio,Funicello, Maria,Guarnaccio, Ambra
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p. 384 - 392
(2016/06/01)
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- 2-ARYLBENZOTHIOPHENE DERIVATIVES OR PHARCEUTICALLY ACCEPTABLE SALTS THEREOF, PREPARATION METHOD THEREOF, AND PHARCEUTICAL COMPOSITION FOR THE DIAGNOSIS OR TREATMENT OF DEGENERATIVE BRAIN DISEASE CONTAINING THE SAME AS ACTIVE INGREDIENT
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2-arylbenzothiophene derivatives or pharmaceutically acceptable salts thereof, a preparation method thereof, and a pharmaceutical composition for the diagnosis or treatment of degenerative brain disease containing the same as an active ingredient. Since the 2-arylbenzothiophene derivatives of Formula 1 have a relatively high binding affinity for β-amyloid, they can be used as diagnostic reagents for diagnosing Alzheimer's disease at an early stage by non-invasive techniques when they are labeled with radioisotopes: wherein R1-R4, V, W, X, Y and Z are as defined in the Detailed Descript of the specification. Further, when the pharmaceutical composition containing the 2-arylbenzothiophene derivative binds with a low-molecular weight β-amyloid peptide binding compound, generation of malignant high-molecular weight β-amyloid deposits is minimized. Accordingly, the pharmaceutical composition can be used as a therapeutic agent of degenerative brain disease such as Alzheimer's disease.
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Page/Page column 17
(2010/11/03)
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- FARNESOID X RECEPTOR AGONISTS
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The present invention relates to famesoid X receptors (FXR, NR1H4) FXR is a member of the nuclear receptor class of ligand-activate transcription factors More particularly, the present invention relates to compounds useful as agonists for FXR, pharmaceutical formulations comprising such compounds, and therapeutic use of the same Novel isoxazole compounds are disclosed as part of pharmaceutical compositions for the treatment of a condition mediated by decreased FXR activity, such as obesity, diabetes, cholestatic liver disease, liver fibrosis, and metabolic syndrome
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Page/Page column 177-178
(2009/03/07)
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- FARNESOID X RECEPTOR AGONISTS
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The present invention relates to famesoid X receptors (FXR, NR1 H4) FXR is a member of the nuclear receptor class of ligand-activated transcription factors More particularly, the present invention relates to compounds useful as agonists for FXR, pharmaceu
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Page/Page column 93-94
(2009/01/23)
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- SULFAMATE BENZOTHIOPHENE DERIVATIVES AS STEROID SULFATASE INHIBITORS
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The present invention relates to sulfamate benzothiophene compounds of the formula: (I) wherein R1, R2, R3, m and n are as defined in the specification. The invention also relates to pharmaceutical compositions containing
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- Application of directed metalation in synthesis. Part 4: Expedient synthesis of substituted benzo[b]thiophene and naphthothiophene
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A short, simple and inexpensive synthesis of several diversely substituted benzo[b]thiophenes and one naphthothiophene is described. The method involves introduction of methylsulfanyl group ortho- to the amide function of readily available N,N-diethylamides of aryl carboxylic acid by directed metalation. Thioindoxyls, obtained in high yields through side-chain deprotonation and cyclisation in one pot, are reduced to benzo[b]thiophene or napthothiophene.
- Mukherjee, Chandrani,Kamila, Sukanta,De, Asish
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p. 4767 - 4774
(2007/10/03)
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- Novel spla2 inhibitors
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A class of novel benzo(b)thiophene is disclosed together with the use of such compounds for inhibiting sPLA2 mediated release of fatty acids for treatment of Inflammatory Diseases such as septic shock.
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- Smiles rearrangement for the synthesis of 5-amino-substituted [1]benzothieno[2,3-b]pyridine
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The Smiles rearrangement was successfully applied to 4-hydroxybenzo[b]thiophene furnishing a facile entry to the 4-amino derivative. The rearrangement was extended to 5-methoxy-4-methoxycarbonyl[1]benzothieno[2,3-b]pyridine obtained via aza-Wittig/electrocyclization reaction of novel N-(4-methoxybenzothiophen-2-yl)iminomethyldiphenylphosphorane with methyl trans-4-oxo-2-pentenoate. The preparation of a novel 5-amino-4-methoxycarbonyl[1]benzothieno[2,3-b]pyridine, which is of interest as a potential secondary peptide structure mimic, was successfully achieved.
- Bonini, Carlo,Funicello, Maria,Scialpi, Rosanna,Spagnolo, Piero
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p. 7515 - 7520
(2007/10/03)
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- Application of directed metallation in synthesis, part 2: An expedient synthesis of methoxybenzo[b]thiophenes
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A short, simple and expedient synthesis of substituted benzo[b]thiophenes involving directed ortho lithiation-side-chain deprotonation-cyclisation-reduction is described. This method is a valuable improvement over earlier syntheses of the same class of compounds, both with respect to the number of steps and overall yields.
- Mukherjee, Chandrani,De, Asish
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p. 325 - 327
(2007/10/03)
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- Dibasic benzo[b]thiophene derivatives as a novel class of active site directed thrombin inhibitors: 4. SAR studies on the conformationally restricted C3-side chain of hydroxybenzo[b]thiophenes
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A novel series of benzo[b]thiophene diamine thrombin inhibitors with a conformationally restricted C3-side chain 3 was investigated. The constrained C3-side chain by a cyclohexyl ring contributed to not only an additive but also a synergistic effect on the thrombin inhibitory activity. The SAR studies resulted in the discovery of a potent thrombin inhibitor 27 that was over 750-fold more potent than the initial lead compound 1.
- Takeuchi, Kumiko,Kohn, Todd J.,Sall, Daniel J.,Denney, Michael L.,McCowan, Jefferson R.,Smith, Gerry F.,Gifford-Moore, Donetta S.
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p. 759 - 764
(2007/10/03)
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- Studies in sulfur heterocycles. Part 14. Application of heteroatom directed ortho-metallation in functionalisation of benzo[b]thiophene derivatives
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Heteroatom directed ortho-metallation of 2-tert-butyldimethylsilyl-4-methoxybenzo[b]thiophene and 2-tert-butyldimethylsilyl-4-carbamoyloxybenzo[b]thiophene has been followed by quenching with electrophiles. Anionic ortho-Fries rearrangement has been carri
- Mandal, Sasanka Sekhar,Samanta, Subhendu Sekhar,Deb, Chaitali,De, Asish
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p. 2559 - 2562
(2007/10/03)
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- An improved synthesis of benzo[b]thiophene and its derivatives using modified montmorillonite clay catalysts
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Methods for the preparation of benzothiophene (3) and its derivatives by cyclization of phenylthioacetals (1) over ZnCl2-promoted montmorillonite clay are described. Reactions in solution resulted in only moderate (ca. 50%) yields of 3 and the formation of diphenyl disulfide (4) and uncharacterized products. The production of 4 was explained by coordination of 1 via its oxygen atom to active sites of the catalyst and subsequent bimolecular processes. Good to excellent yields (67-98%) of 3 and its derivatives were obtained using vapor phase techniques at 200-300°C to promote the desired intramolecular cyclizations.
- Clark,Kirk,Yee
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p. 1936 - 1938
(2007/10/02)
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- ALKYLATION OF THIOPHENES AND PREPARATION OF BENZOTHIOPHENES USING MODIFIED MONTMORILLONITE CLAY CATALYSTS
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Regioselective benzylation of thiophene and benzothiophene using benzyl chloride and a ZnCl2-promoted montmorillonite catalysts is described.An improved process for the cyclization of (arylthio)acetaldehyde dialkyl acetals to benzothiophenes using the same catalyst is also documented.
- Clark, Peter D.,Kirk, Andrew,Mesher, Shaun T.,Yee, James G.K.
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p. 441 - 444
(2007/10/02)
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- Topically Active Carbonic Anhydrase Inhibitors. 2. Benzothiophenesulfonamide Derivatives with Ocular Hypotensive Activity
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Derivatives of benzothiophene-2-sulfonamide were prepared to investigate their potential utility as topically active inhibitors of ocular carbonic anhydrase.Such an agent would be useful in the treatment of glaucoma.Among the compounds described are 6-hydroxybenzothiophene-2-sulfonamide (16) and its acetate ester (23), which are among the most potent ocular hypotensive agents in this class, as assessed in the α-chymotrypsinized rabbit.These compounds were selected for clinical evaluation.
- Graham, Samuel L.,Shepard, Kenneth L.,Anderson, Paul S.,Baldwin, John J.,Best, Darryl B.,et al.
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p. 2548 - 2554
(2007/10/02)
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- The Synthesis of Thiophenium and Oxazolium Salts from Diazoketones
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4-Diazoacetylthianthren with perchloric acid in acetonitrile gave 2-oxo-1,2-dihydrothieno-thianthrenium perchlorate which gave the corresponding enol ether with diazomethane.This ether was compared with 3-methoxy-1-methylbenzothiophenium perchlorate, prepared from 3-methoxythiophen, and which was much more stable to solvolysis than the demethoxy-analogue.In contrast to the 4-diazoacetylthianthren, 7-diazoacetyl-2-methylbenzothiophen with acetonitrile and perchloric acid cyclized in an alternative mode to give a new synthesis of 2-methyl-4-substituted oxazolium perchlorates.
- Acheson, R. Morrin,Cooper, Martin W.
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p. 1185 - 1193
(2007/10/02)
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