Showing papers on "Benzopyran published in 1989"

3,4-Dihydro-2H-1-benzopyran-2-carboxylic acids and related compounds as leukotriene antagonists

Abstract: Evaluation of a series of 3,4-dihydro-2H-1-benzopyran-2-carboxylic acids linked to the 2-hydroxyacetophenone pharmacophore present in the standard peptidoleukotriene antogonist FPL 55712 (1) has led to the discovery of Ro 23-3544 (7), an antagonist possessing greater potency and duration of action vs LTD4 than the standard (aerosol route of administration, guinea pig bronchoconstriction model). Interestingly, this compound also potently inhibited bronchoconstriction induced by LTB4 whereas 1 did not. Attempts to establish structure--activity relationships in this series involved modifications in the 2-hydroxyacetophenone moiety, the linking chain, and the chroman system. All variations produced analogues which were either inactive or possessed reduced potency relative to acid 7. Optical resolution of 7 was achieved by two methods. Absolute configurations of the enantiomers were determined via X-ray crystallographic analyses of an intermediate as well as a salt of the S enantiomer. Although the enantiomers exhibited similar potencies in in vitro assays and in vivo when administered intravenously, significant differences were observed in the guinea pig bronchoconstriction model vs LTC4 and LTD4 when administered by the aerosol route (S antipode 15-fold more potent). The properties of 7 have been compared with several recently reported leukotriene antagonists.

Lewis acid mediated nucleophilic substitution reactions of 2-alkoxy-3,4-dihydro-2H-1-benzopyrans: regiochemistry and utility in the synthesis of 3,4-dihydro-2H-1-benzopyran-2-carboxylic acids

Abstract: Les substitutions nucleophiles des chromannes du titre avec le [cyano trimethyl] silane sont etudiees. Le catalyseur, TiCl 4 ou SnCl 4 , a une influence sur la regioselectivite des reactions

Studies in [3.3] sigmatropic rearrangement: regioselective synthesis of 1-aryloxymethylpyrano[2,3-c][1]benzopyran-5(3H)-one and 1-aryloxymethyl-2-methylfuro[2,3-c][1]benzopyran-4-one

Abstract: 3-(4-Aryloxybut-2-ynyloxy)[1]benzopyran-2-one (1) in refluxing chlorobenzene gave exclusively 1-aryloxymethylpyrano[2,3-c][1]benzopyran-5(3H)-one (6) by a pericyclic path. Compound (1) when heated in nonpolar solvents or in the presence of acid or base, gave exclusively 1-aryloxymethyl-2-methylfuro[2,3-c][1]benzopyran-4-one (10). Additionally this reaction has been studied in the presence of a radical initiator, viz., azoisobutyronitrile (AIBN), and induced to follow mainly the radical pathway to give the products (10). All the butynes (1) studied so far underwent sigmatropic rearrangements at the 4-coumarin-3-yloxypropynyl function of compound (1) to give product(s)(6) and/or (10).

Use of 4H-1-benzopyran-4-one derivatives, 4H-1-benzopyran-4-one derivatives and medicines containing same

Abstract: Compounds of the formula I in which the substituents R1-R5 and n and m have the said meanings, are suitable for controlling tumours. The present invention relates to the use of 4H-1-benzopyran-4-one derivatives, to 4H-1-benzopyran-4-one derivatives and to medicines containing same. Benzopyran derivatives have already been disclosed in European Patent No. 0137193 and German Offenlegungsschrift 36 12 337. In the latter, compounds of the formula a) are disclosed.

Novel benzopyran derivatives, processes for their preparation and their use and preparations containing the compounds

Abstract: Benzopyran derivatives of the general formula I ##STR1## wherein the substituents are as defined herein are provided. The compounds show vasodilating and vascular spasmolytic activity and are useful in treating hypertension.

Benzopyran derivatives and their use as anti-hypertensives

Abstract: Benzopyran derivatives of formula (I) wherein the substituents are as defined herein are provided. The compounds possess vasodilating activity and are useful in the treatment of hypertension. Pharmaceutical compositions and methods of treating hypertension are also provided.

Benzopyran derivatives and pharmaceutical compositions containing them

Abstract: New benzopyran derivatives of formula: ##STR1## in which R 1 is hydrogen, halogen, hydroxy, alkoxy, nitro, amino, alkylsulphonamido, bis(alkylsulphonyl) amino or acylamino, X is nitrogen or a >CH-radical R is a radical of formula: ##STR2## in which A denotes a single bond or methylene or, when X is nitrogen, A may denote carbonyl, and R 2 and R 3 , which are identical or different, are hydrogen, halogen, hydroxy, alkyl, alkoxy, nitro, amino, alkylsulphonamido, bis(alkylsulphonyl)amino, acylamino, sulphamoyl or cyano, or, when they are adjacent, together form a methylenedioxy or ethylenedioxy radical, or else R is pyridyl or 2(2H)-benzimidazolonyl if X denotes >CH--, and R' and R" are identical and are hydrogen or alkyl, their isomeric forms and mixtures thereof, and their acid addition salts, can be used as antiarrhythmic and antifibrillation agents.

Thermal Isomerization of 1′,3′,3′-Trimethyl-8-nitrospiro[2H-1-benzopyran-2,2′-indoline]-6-carboxylic Acid

Abstract: The rates of thermal isomerization of 1′,3′,3′-trimethyl-8-nitrospiro[2H-1-benzopyran-2,2′-indoline]-6-carboxylic acid (6-COOH-8-NO2-SP) from its spiro form (SP) to its merocyanine form (MC) have been measured in some solvents and at high pressures. The equilibrium constants between these isomers at atmospheric pressure and at 30 °C are in the range of 0.25 to 2.52 depending on solvents. The activation volumes are 0.2–3.4 cm3 mol−1, while the reaction volumes are −7.9–−22.3 cm3 mol−1. Thus the volume profile was found to have a maximum, as predicted previously.

Benzopyran derivatives and antihypertensive use thereof

Abstract: Disclosed herein are novel benzopyrans having pharmacological activity, to a process for preparing them, to pharmaceutical compositions containing them, and to their use in the treatment of hypertension.

Studies on Synthesis and Stereochemistry of 3-Methyloctahydroisocoumarins and 1-Methyloctahydro-3H-2-benzopyran-3-ones

Abstract: Four stereoisomers of 3-methyloctahydroisocoumarins (4a-d)and two 1-methyloctahydro-3H-2-benzopyran-3-ones (10a, b) were synthesized. The stereochemical correlations including the configurations of the ring juncture and the methyl group and also the ring conformations of these six lactones were investigated by chemical means and by nuclear magnetic resonance (NMR) spectrometry, such as two-dimensional(2D) NMR and steady-state 1H-1H nuclear Overhauser effect experiments. It was concluded that the lactone ring of 4b, c, and 10a adopts a boat or a slightly distorted boat conformation in solution.

Use of benzopyran derivatives in the treatment of epilepsy

Abstract: A method for the treatment of epilepsy comprising the administration of a potassium channel activator, such as (-)-6-cyano-3,4-dihydro-2,2-dimethyl- trans -4-­(2-oxo-1-pyrrolidinyl)-2H-benzo[b]pyran-3-ol.

Phenoxyalkoxy-3,4-dihydro-2H-1-benzopyran derivatives

Abstract: Compounds of the formula wherein R¹ is hydrogen or lower alkyl, R² is hydrogen or halogen, R³, R⁴ and R⁵, independently, are hydrogen, acyl or lower alkyl, provided that only one of R³, R⁴ and R⁵ can be acyl, R⁶ is hydrogen or lower alkyl, R⁷ is higher alkyl or benzyl and X is (C₃₋₇)-alkylene, as well as enantiomes thereof, are useful for treating allergic and inflammatory disorders. They can be prepareed according to known methods.

2-benzopyran derivative

Abstract: NEW MATERIAL:A compound of formula I [R1, R2 are H, halogen, alkyl, alkoxy, trihalomethyl, hydroxyl, amino, alkylamino, or incorporate to form alkylenedioxy; n is 1-5; R is H, alkyl, aralkyl; R4 is formula IV (m is 1-5; lis 1, 2; R5 is H, alkyl, aralkyl, diphenylalkyl), diphenylalkyl] and its salt. EXAMPLE:3,4-Dihydro-N-(3,3-diphenylpropyl)-1H-2-benzopyran-1-methylamine monomaleate. USE:It has action to inhibit the formation of activated oxygen and is used as a prophylactic or remedy for radiation injury. PREPARATION:For example, a compound of formula II is allowed to react with a compound of the formula: XCO-R6 (X is halogen, R6 is formula V) or the formula: O(COR6)2 to form a compound of formula III, which is reduced to give the compound of formula I.

Thermal rearrangement of 4-cyano-2,3-dihydro-5-ethoxy-3-methyl-3-(4-oxo-4H-1- benzopyran-3-yl)furans: a reversed alkoxycarbonylcyclopropane → 5-alkoxy-2,3-dihydrofuran transformation

Abstract: The title dihydrofurans (3f, R1= H, Me, and Cl), prepared from the α-cyano-ester (1e) and diazomethane, thermally rearrange to the cyclopropanes (4f) in predominantly Z-isomeric form.

Process for the manufacture of benzopyran derivatives

Abstract: The invention is directed to a process and intermediates for the preparation of benzopyrans such as racemic-6-acetyl-­7-[5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentyloxy]-3,4-­dihydro-2H-1-benzopyran-2-carboxylic acid.

A New Procedure for Regiospecific Syntheses of Benzopyran-1-ones.

Abstract: Synthese a partir d'hydraxy-3 phtolides et de nitro-1 alcanes via des acides nitro-2' alkyl-2 benzoiques

3,4-dihydro-2h-benzopyran derivative and anti-peptic ulcer agent containing thereof as active ingredient

Abstract: NEW MATERIAL:A compound expressed by formula I or salt of said compound (R 1 to R 4 are H, halogen, lower alkyl, OH, lower alkoxy or benzyloxy; m is 0 or 1; n is 0-3) EXAMPLE: 3,4-dihydro-6-hydroxy-2-[2-(2,2,6,6-tetramethylpiperidin-4yl) aminoethyl]-2,5,7,8-tetramethyl-2H-benzopyran USE: Used as anti-peptic ulcer agent having excellent anti-peptic ulcer action and high safety PREPARATION: For instance, 3,4-dihydro-2H-benzopyran derivative expressed by formula II (k is 0-2) is reacted with thionyl chloride to generate acid chloride and reacted with 4-amino-2,2,6,6tetramethylpiperidine expressed by formula III to afford the compound expressed by formula I for m=1 and n=0-2 COPYRIGHT: (C)1990,JPO&Japio

Novel benzopyrane derivative, manufacture and pharmacological composition

Abstract: New benzopyran derivatives of formula: (I) in which R1 is hydrogen, halogen, hydroxy, alkoxy, nitro, amino, alkylsulphonamido, bis(alkylsulphonyl) amino or acylamino, X is nitrogen or a >CH-radical R is a radical of formula: in which A denotes a single bond or methylene or, when X is nitrogen, A may denote carbonyl, and R2 and R3, which are identical or different, are hydrogen, halogen, hydroxy, alkyl, alkoxy, nitro, amino, alkylsulphonamido, bis(alkylsulphonyl)amino, acylamino, sulphamoyl or cyano, or, when they are adjacent, together form a methylenedioxy or ethylenedioxy radical, or else R is pyridyl or 2(2H)-benzimidazolonyl if X denotes >CH-, and R' and R'' are identical and are hydrogen or alkyl, their isomeric forms and mixtures thereof, and their acid addition salts, can be used as antiarrhythmic and antifibrillation agents

Synthesis, structure, and lasing properties of 4-trifluoromethyl-7-hydroxy-2-cyanocarbethoxymethylene-2H-1-benzopyran

Abstract: By condensation of 4-trifluoroacetylresorcinol with cyanoacetic ester, we have obtained 4-trifluoromethyl-7-hydroxy-2-cyanocarbethoxymethylene-2H-1-benzopyran, the structure of which has been proven by an x-ray diffraction investigation. The presence of an elelctron-acceptor group in the 4 position of the benzopyran nucleus leads to a decrease in the degree of charge separation in 2-alkylidenebenzopyrans. We present the lasing characteristics of the compound obtained.

Novel tricyclic azole derivative, its production and agricultural and horticultural fungicide containing said derivative as active component

Abstract: NEW MATERIAL:The compound of formula I (A is N or CH). EXAMPLE:3, 3-Dimethyl-6-chloro-1, 2, 3, 3a, 9, 9a-hexahydro-3a-(1H-1,2,4-triazol-1- ylmethyl)cyclopenta[b][1]-benzopyran. USE:Agricultural and horticultural fungicide. PREPARATION:The compound of formula I can be produced by reacting the compound of formula II with the compound of formula III (M is H or alkali metal) at 0-100 deg.C for 1-3hr.

Structure of (+-)-6-methyl-6,12-methano-6H,12H,13H-[1]benzopyran[4,3-d] [1,3]benzodioxocin-13-one.

Abstract: A derivative of warfarin, racemic C19H14O4, Mr = 306.32, monoclinic, Cc, a = 9.594 (2), b = 20.437 (4), c = 7.793 (2) A, beta = 109.94 (3) degree, V = 1436.4 (11) A3, Z = 4, Dx = 1.416 g cm-3, lambda(CuK alpha) = 1.5418 A, mu = 7.742 cm-1, F(000) = 640, T = 293 K, final R = 0.053 for 1224 observations. The title molecule, formed by spontaneous dehydration of 2'-hydroxy-warfarin, is a cyclic ketal in which the side-chain phenyl is disposed pseudoaxially and is linked through a 2'-oxygen to the ketal carbon in a fixed cis 1,3-diaxial configuration. Two dihydropyran rings are formed; one fused with the benzopyran ring adopts an e,f-diplanar conformation, the other is a chroman and is in a similar conformation.

(D)-6-fluoro-2,3-dihydro-2',5-dioxo-spiro[4H-1-benzopyran-4,4'-imidazolide]-2-carboxamide compounds

Abstract: Hydantoin derivatives of the formula ##STR1## wherein Ra and Rb are same or different, each being hydrogen atom, alkanoyl, substituted or none-substituted aroyl, heteroaroyl, alkoxycarbonyl, substituted or none-substituted aralkoxycarbonyl, aryloxycarbonyl, N-alkylcarbamoyl, N,N-dialkylcarbamoyl, substituted or none-substituted N-aralkylcarbamoyl, alkoxyalkyl, 1-(acyloxy)-alkyl, alkylmercapto, substituted or none-substituted arylmercapto, alkylsulfinyl, substituted or none-substituted arylsulfinyl, alkylsulfonyl or substituted or none-substituted arylsulfonyl, but both of Ra and Rb do not concurrently mean hydrogen atom, a process for the preparation of the derivatives, and use thereof as an agent for preventing and curing chronic complications due to diabetes.

Structure of (.+-.)-6-Methyl-6,12-methano-6H,12H,13H-(1)benzopyran(4,3-d)(1,3)benzodioxocin-# 13-one

Abstract: A derivative of warfarin, racemic C19H14O4, Mr = 306.32, monoclinic, Cc, a = 9.594 (2), b = 20.437 (4), c = 7.793 (2) A, beta = 109.94 (3) degree, V = 1436.4 (11) A3, Z = 4, Dx = 1.416 g cm-3, lambda(CuK alpha) = 1.5418 A, mu = 7.742 cm-1, F(000) = 640, T = 293 K, final R = 0.053 for 1224 observations. The title molecule, formed by spontaneous dehydration of 2'-hydroxy-warfarin, is a cyclic ketal in which the side-chain phenyl is disposed pseudoaxially and is linked through a 2'-oxygen to the ketal carbon in a fixed cis 1,3-diaxial configuration. Two dihydropyran rings are formed; one fused with the benzopyran ring adopts an e,f-diplanar conformation, the other is a chroman and is in a similar conformation.

(d)-6-fluoro-2,3-dihydro-2',5'-dioxo-spiro(4h-1-benzopyran-4,4'-imidazolidine)-2-carboxamide derivatives, manufacturing process and use thereof

Abstract: Hydantoin derivatives of formula (I), wherein Ra and Rb are same or different, each being hydrogen atom, alkanoyl, substituted or non-substituted aroyl, heteroaroyl, alkoxycarbonyl, substituted or non-substituted aralkoxycarbonyl, aryloxycarbonyl, N-alkylcarbomoyl, N,N-dialkylcarbamoyl, substituted or non-substituted N-aralkylcarbamoyl, alkoxyalkyl, 1-(acyloxy)alkyl, alkylmercapto, substituted or non-substituted arylmercapto, alkylsulfinyl, substituted or non-substituted arylsulfinyl, alkylsulfonyl or substituted or non-substituted arylsulfonyl, but both of Ra and Rb do not concurrently mean hydrogen atom, a process for the preparation of the derivatives, and use thereof as an agent for preventing and curing chronic complications due to diabetes.