33 results about "Dihydrobenzopyrans" patented technology

PCT No. PCT/JP97/01148 Sec. 371 Date Sep. 30, 1998 Sec. 102(e) Date Sep. 30, 1998 PCT Filed Apr. 3, 1997 PCT Pub. No. WO97/37656 PCT Pub. Date Oct. 16, 1997A medicinal composition for the prophylaxis and treatment of cachexia which comprises a compound of the formula: wherein R represents a hydrocarbon group that may be substituted or a heterocyclic group that may be substituted; Y represents a group of the formula -CO-, -CH(OH)-, or -NR3- (R3 represents an alkyl group that may be substituted); m is 0 or 1; n is 0, 1 or 2; X represents CH or N; A represents a bond or a bivalent aliphatic hydrocarbon group having 1 to 7 carbon atoms; Q represents oxygen or sulfur; R1 represents hydrogen or an alkyl group; ring E may have further 1 to 4 substituents, which may form a ring in combination with R1; L and M respectively represent hydrogen or may be combined with each other to form a bond, provided that when m and n are 0, X represents CH, A represents a bond, Q represents sulfur, R1, L and M respectively represent hydrogen, and ring E does not have further substituents, R does not represent dihydrobenzopyranyl; or a salt thereof.

This invention is attributed to the field of organic chemistry and specifically relates to the method to synthesize drug intermediates (R)-2-amino-1-((R)-6-fluoro-3, 4-dihydrochromeno) ethanol and (R)-2-amino-1-((S)-6-fluoro-3, 4-dihydrochromeno) ethanol. The method is that, drug intermediates (2R)-2-[(1R)-4, 4-dimethyl-3, 5-dioxocyclopentyl]-6-fluoro-4-chromanone and (2S)-2-[(1R)-4, 4-dimethyl-3, 5-dioxocyclopentyl]-6-fluoro-4-chromanone are adopted as raw materials and reduced by Clemmensens method with the products reacting with p-toluenesulfonyl chloride in pyridine. The consequent products are dissolved in solvent and dry ammonia is introduced for heating reflux. The total yield can be as much as 32%.

The invention relates to a solid-phase synthesis method of coumarin and an analogue (I) thereof and belongs to the field of organic chemistry. The method comprises the following steps: 1) taking 1% of cross-linked polystyrene resin as a carrier to prepare a polystyrene-supported seleno-succimide reagent (III); 2) using the III to induce phenyl acrylate (V) to perform intramolecular cyclization under the catalysis of trimethylsilyl trifluoromethanesulfonate so as to form 3-polystyrene-supported seleno-3,4-dihydro-benzopyran-2-ketone (VI); and 3) performing oxidation elimination on the VI via an oxidant so as to directly get the coumarin (I) without further separation. When the phenyl acrylate (V) is replaced by N-phenyl acrylamide, the analogue of the coumarin, namely a 2-quinolone compound, can be prepared through the same steps. The solid-phase synthesis method disclosed by the invention has the advantages of easily available raw materials, good product yield, high purity, simplicityand convenience in operation, simple post-treatment and great industrial application prospects.

The present invention relates to one kind of 3, 4-dihydro-1H-2-benzopyran-1-ketone compounds, and provides the preparation process of these compounds. These compounds have LAR and PTPsigma inhibiting effect, and may be used in treating various types of diabetes, obesity and their complication as well as other diseases caused by excessive activity or over expression of PTP-LAR and/or PTPsigma, such as tumor and nervous degenerative disease.

A process of making racemic [2S*[R*[R*[R*]]]] and [2R*[S*[S*[S*]]]]-(±)α,α′-[iminobis(methylene)]bis[6-fluoro-3,4-dihydro-2H-1-benzopyran-2-methanol] of the compound of the formula (I)

and its pure [2S*[R*[R*[R*]]]]- and [2R*[S*[S*[S*]]]]-enantiomer compounds and pharmaceutically acceptable salts thereof.

The present invention provides a method for preparing a 2,3-dihydrobenzopyran-4-one derivative, and the method comprises the following steps: under nitrogen atmosphere at room temperature, dissolvinga 2-allyloxybenzaldehyde derivative represented by formula (I) and a benzoin derivative represented by formula (II) in an organic solvent, adding a photosensitizer, evenly mixing, placing under an ultraviolet lamp for light irradiation reaction, removing the solvent by rotary evaporation, and separating and purifying by silica gel column chromatography to obtain the resulting product 2,3-dihydrobenzopyran-4-one derivative. The preparation method solves the problems of cumbersome steps, low yield and poor environmental protection property of the existing synthesis method, can react under normaltemperature and normal pressure, and has the advantages of mild reaction conditions, no need of transition metal catalysis, simple operation, no pollution, safety, environmental protection, low costand the like. R1 and R2 are hydrogen, halogen or alkyl.

The invention discloses a compound, namely (2R, 3R)-((2-(3,4-dihydroxyphenyl)-5,7-dihydroxyl-4-oxo-2,3-dihydrobenzopyran-3-yl) methylamino) methyl-2-phenylpropionate. The invention also discloses a preparation method for the compound and the application of the compound as a feed additive. When serving as the feed additive, the compound can specifically promote the growth of intestinal mucosa villus of livestocks, promote the growth of intestinal linings, reduce the intestinal tension and inhibit abnormal peristalsis, can reduce the feed discharging speed of intestinal tracts of the livestocks so as to enhance the digestive absorption of the intestinal tracts to nutritional components, and can obviously increase the daily weight increasing of the livestocks. The reduction of the intestinal tension contributes to water absorption in the intestinal tracts, and plays an obvious role of convergence and reducing functional diarrhea. The compound provided by the invention also has an effect of repairing intestinal mucosa, and can also obviously improve the immunity function of intestinal mucosa and disease resistance of the livestocks.

The invention relates to a synthesis method of (R) or (S)-6-fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid and in particular relates to a synthesis method of an intermediate of 2-hydroxyl-2-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)acetonitrile (nebivolol hydrochloride). The method comprises the following steps: using optically pure (R) or (S)-malic acid and the corresponding acyl chloride or anhydride containing R1 groups to react to obtain a compound 3; using the compound 3 and a p-substituted phenol compound to perform a Friedel-Crafts reaction in the presence of an lewis acid to obtain a compound 5; using the compound 5 to perform an intramolecular SN2 substitution reaction under the action of a base and obtain a cyclized product 6; and hydrogenizing the carbonyl groups of the compound 6 in the presence of palladium-charcoal and performing benzyl reduction to obtain the target product 1. The method has the advantages of cheap and available starting material, fewer reaction steps, high synthesis efficiency and the like; and the defects of the prior art can be better overcome.

The invention discloses a preparation method of nebivolol used for preparing medicines for treating hypertension of slight or medium degrees, and an intermediate compound. The preparation method comprises the following steps: taking 6-fluoro-2-(1-hydroxy-2-paratoluensulfonyl oxygroup-ethyl)-3,4-dihydrobenzopyrans as an initial raw material, introducing amino, then coupling with 6- fluoro-3,4-dihydro-2-epoxy ethyl-2H-1-benzopyran, and preparing (S,R,R,R) and (R,S,S,S)-nebivolol. Compared with a prior art, the preparation method has the advantages of novel design, simple operation and high yield, the usage of hazardous reagent such as ssodium azide and sodium hydride can be avoided, a column chromatography purifying method is avoided, so that the preparation method conforms to industrial production.

The invention discloses a substituted 1,4-dihydro-chromene [2, 3-b] pyrrole compound. The structural formula is as shown in specifications. The invention further discloses a preparation method of the substituted 1,4-dihydro-chromene [2, 3-b] pyrrole compound. The preparation method includes the steps that olefine azido compounds and 4-hydroxycoumarin react for 8-12 hours at 80-100 DEG C under the existence of solvent and a metal catalyst; obtained reaction liquid is cooled to indoor temperature, then water and ethyl acetate are used for extraction, and an obtained organic layer is concentrated after being rinsed; obtained concentrate is subjected to silica column chromatography to obtain the substituted 1, 4-dihydro-chromene [2, 3-b] pyrrole compound. The compound is an anti-tumor lead compound.