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WO1992020672A1 - Derives du benzopyranne portant des substituants isoindolyle et isoquinolyle, produits intermediaires et leur procede de fabrication - Google Patents

Derives du benzopyranne portant des substituants isoindolyle et isoquinolyle, produits intermediaires et leur procede de fabrication Download PDF

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Publication number
WO1992020672A1
WO1992020672A1 PCT/DE1992/000357 DE9200357W WO9220672A1 WO 1992020672 A1 WO1992020672 A1 WO 1992020672A1 DE 9200357 W DE9200357 W DE 9200357W WO 9220672 A1 WO9220672 A1 WO 9220672A1
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WO
WIPO (PCT)
Prior art keywords
compounds
formula
benzopyran
dihydro
dimethyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/DE1992/000357
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German (de)
English (en)
Inventor
Ben Armah
Dieter Muster
Gerd Rühter
Theo Schotten
Wolfgang Stenzel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Beiersdorf AG
Beiersdorf Lilly GmbH
Original Assignee
Beiersdorf AG
Beiersdorf Lilly GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Beiersdorf AG, Beiersdorf Lilly GmbH filed Critical Beiersdorf AG
Publication of WO1992020672A1 publication Critical patent/WO1992020672A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems

Definitions

  • the present invention relates to new substituted benzopyran derivatives of the general formula I,
  • R 1 and R 2 may be the same or different and
  • C 1-8 dialkylamino-carbonyloxy means, where the C 1-8 alkyl or alkoxy groups can be both linear and branched, and R 4 represents hydrogen or
  • R 3 and R 4 together form a bond, R 5 forms a heterocycle of the formula A.
  • R 7 represents hydrogen, C 1-6 alkyl, C 1-6 alkoxy, halogen, nitro or mono- or disubstituted C 1-6 alkylamino,
  • Trifluoroethylsulfinyl or Trifluorethylsulfonyl means, with the heterocycle R 5 preferably is in the trans position to the radical R 3 if R 3 and R 4 do not together represent a bond, with the exception of compounds of the formula I in which
  • R 5 is a heterocycle A where R 7 is hydrogen, and R 3 is hydroxy and R 4 is hydrogen and R 6
  • Salts are valuable for making the compounds, even if the special salt is only for the purpose of
  • Purification or identification is formed, or when used as an intermediate in the manufacture of a pharmaceutically acceptable salt, for example by ion exchange processes.
  • R configuration are particularly preferred.
  • the invention also relates to the new compounds of the formulas II, III, IV, V and VI:
  • R 1 , R 2 and R 6 serve as intermediate or intermediate products
  • alkylene parts of groups are straight-chain or branched, and they each preferably have 1-6 carbon atoms, preferably 1-4
  • Carbon atoms particularly preferably 1 or 2
  • the branched alkyl groups have at least 3 carbon atoms.
  • Preferred alkyl or alkylene parts are methyl, ethyl, n-propyl, isopropyl, Butyl or correspondingly methylene, ethylene, n-propylene, isopropylene and butylene.
  • C 1-8 alkylcarbonyloxy C 1-8 alkyl-CO-O-
  • C 1-8 alkoxycarbonyloxy C 1-8 alkyl-O-CO-O-
  • C 1-8 monoalkylaminocarbonyloxy C 1- 8- alkyl-NH-CO-0-
  • C 1-8 -dialkylaminocarbonyloxy (C 1 _ 8 -alkyl) 2 N-CO-0-
  • Halogen fluorine, chlorine, bromine, iodine
  • trifluoroethyl group or trifluoroethyl as part of other radicals according to the invention such as trifluoroethylthio is preferably 2,2,2-trifluoroethyl.
  • R 1 is preferably hydrogen, methyl or ethyl, particularly preferably methyl.
  • R 2 is preferably hydrogen, methyl or ethyl, particularly preferably methyl.
  • R 1 and R 2 are particularly preferably both at the same time
  • R 1 and R 2 are preferred branched alkyl or cycloalkyl, isopropyl or cyclopropyl are particularly preferred.
  • R 3 preferably represents hydroxyl or particularly preferably forms a bond with R. so that there is a between the C 3 and C 4 positions of the benzopyran skeleton
  • R 3 is alkoxy, ethoxy and especially methoxy are preferred.
  • R 3 is alkylcarbonyloxy, propionyloxy and especially acetoxy and formyloxy are preferred.
  • R 5 is preferably a heterocycle of the formula A.
  • R 6 is preferably difluoromethoxy, difluoromethylthio, difluoromethylsulfonyl, difluoromethylsulfinyl,
  • Trifluoromethylsulfinyl and trifluoromethylsulfonyl especially difluoromethoxy, trifluoromethylthio and trifluoromethylsulfonyl.
  • R 7 is preferably hydrogen, methyl, ethyl, methoxy, ethoxy or halogen, is particularly preferred
  • Chlorine is preferred among the halogens.
  • R 2 is selected from the group hydrogen, methyl, ethyl,
  • R 3 either symbolizes a bond together with R 4 or is selected from the group hydroxy, methoxy, ethoxy,
  • R 6 is selected from the group difluoromethoxy
  • R 7 is selected from the group consisting of hydrogen, methyl, ethyl, methoxy, ethoxy and chlorine.
  • R 6 is difluoromethoxy, trifluoromethylthio
  • Trifluoromethylsulfinyl or trifluoromethylsulfonyl means and R 7 represents hydrogen.
  • Acid addition products and their tautomeric and optical isomers are therapeutic agents, have high pharmacological activity and are
  • vasodilating, vasospasmolytic, especially broncholytic effect The can
  • vasospasmolytic effect in the entire vascular system or more or less isolated in circumscribed vascular areas such as brain, coronary or
  • antihypertensive agents can be used.
  • the substances according to the invention are distinguished by a considerable reduction in arterial blood pressure. Doses of 0.01-10 mg / kg s.c. lead to a reduction in blood pressure of at least 20%
  • the substances according to the invention are distinguished by a particular influence on the flow of potassium ions in the cells. In particular, they are
  • Potassium channel activators are suitable for the prophylaxis and treatment of the following diseases
  • Airway disorders including bronchial asthma,
  • the compounds according to the invention promote blood circulation to the scalp and hair growth. They are also tocolytically effective.
  • the compounds according to the invention have a long duration of action with only low toxicity. Therefore, they are particularly suitable for the treatment of acute and chronic heart diseases, for the treatment of high blood pressure, heart failure and for the treatment of asthma and cerebral and peripheral circulatory disorders.
  • the compounds of the present invention can be found in
  • Example two to four times a day are advantageous for the treatment of the diseases mentioned above, in particular of
  • the dosage is about 0.05 to 30 mg, preferably 0.1 to 10 mg, per day.
  • the above dosages are particularly preferred for the treatment of hypertension.
  • the invention also relates to
  • Contain diluents or carriers Contain diluents or carriers.
  • the usual pharmaceutical additives can be used here.
  • the compounds according to the invention can with
  • Oral preparations can contain one or more additives such as sweeteners,
  • Tablets can contain the active ingredient mixed with customary pharmaceutically acceptable auxiliaries, for example inert diluents such as calcium carbonate,
  • Sodium carbonate, lactose and talc, granulating agents and agents which promote the disintegration of the tablets when administered orally such as starch or alginic acid, Binders such as starch or gelatin, lubricants such as
  • Magnesium stearate, stearic acid and talc Magnesium stearate, stearic acid and talc.
  • Suitable carriers are, for example, milk sugar (lactose), gelatin, corn starch, stearic acid, ethanol, propylene glycol, ether of tetrahydrofuryl alcohol and water.
  • auxiliary substances are:
  • Non-toxic organic solvents such as paraffins (e.g. petroleum fractions), vegetable oils (e.g. peanut or sesame oil), alcohols (e.g. ethyl alcohol, glycerin), glycols (e.g. propylene glycol,
  • paraffins e.g. petroleum fractions
  • vegetable oils e.g. peanut or sesame oil
  • alcohols e.g. ethyl alcohol, glycerin
  • glycols e.g. propylene glycol
  • Polyethylene glycol polyethylene glycol
  • solid carriers such as e.g.
  • natural stone flours e.g. kaolins, clays,
  • finely divided silica, silicates), sugar e.g.
  • emulsifiers e.g. polyoxyethylene fatty acid esters
  • the formulations are prepared, for example, by stretching the active ingredients with solvents and / or carriers, optionally using emulsifiers and / or dispersants, for example: if water is used as
  • Solvents can be used as auxiliary solvents.
  • the application is carried out in the usual way, preferably orally or parenterally, in particular perlingually or intravenously.
  • oral use preferably orally or parenterally, in particular perlingually or intravenously.
  • Carriers also additives such as sodium citrate,
  • Lubricants such as magnesium stearate,
  • Sodium lauryl sulfate and talc can also be used for tableting.
  • the active compounds can be used in addition to those mentioned above
  • solutions of the active ingredients can be used using suitable liquid carrier materials.
  • the tablets can be coated according to known procedures to delay the breakdown and absorption in the gastrointestinal tract, whereby the activity of the active ingredient can extend over a longer period of time.
  • the active ingredient can be mixed in the suspensions with auxiliaries which are customary for the preparation of such compositions, for example suspending agents such as methyl cellulose, tragacanth or sodium alginate, wetting agents such as lecithin,
  • Preservatives such as ethyl parahydroxybenzoate.
  • Capsules can contain the active ingredient as a single ingredient or mixed with a solid diluent such as calcium carbonate, calcium phosphate or kaolin.
  • the injectable preparations are also formulated in a manner known per se.
  • the pharmaceutical preparations can contain the active ingredient in an amount of 0.1 to 90 percent by weight,
  • Carrier or additive is. In terms of
  • Solid preparations such as tablets and capsules are preferred for preparation and administration.
  • the preparations preferably contain the active ingredient in an amount of 0.05 to 10 mg.
  • the invention also relates to a process for the preparation of pharmaceutical preparations, characterized in that one or more compounds according to claim 1 or their physiologically tolerable salts and, if appropriate, customary carriers and / or diluents are mixed.
  • the anions of the formulas A 'or B' and ammonia are preferably used as nucleophiles.
  • the resulting compounds of the formulas I and IV are obtained as trans isomers and are practically free from cis isomers.
  • the anions A 'and B' are from the compounds of
  • R 7 has the meaning given above.
  • Base is preferably sodium hydride.
  • Nitro aromatics for example with hydrogen and
  • Raney nickel as a catalyst or by nascent hydrogen to the corresponding 4-substituted anilines and diazotization and boiling to the
  • R 6 is difluoromethylthio, difluoromethylsulfinyl, difluoromethylsulfonyl
  • 2,2,2-trifluoroethyl has, to 2H-benzo (b) pyrans, in which R 6 is difluoromethylthio,
  • Trifluoromethylthio and 2,2,2-trifluoroethylthio has to implement.
  • Examples of possible oxidizing agents are: potassium permanganate, sodium periodate,
  • Chlorine trioxide or preferably oxone (potassium persulfate) and hydrogen peroxide / glacial acetic acid preferably oxone (potassium persulfate) and hydrogen peroxide / glacial acetic acid.
  • 6-Fluoroalkylthio-2H-benzo (b) pyrans V in which R 1 and R 2 have the meaning given above, and then the desired oxidation to the respective 6-fluoroalkylsulfinyl-2H-benzo (b) pyrans of the general formula V to make, in which R 6 has the meaning given above.
  • the selectivity is this
  • the starting materials used are known or can be prepared by processes known per se or analogously to the processes described here or analogously to processes known per se.
  • bromohydrins of the formula III accessible from the bromohydrins according to formula III. If it is desired to isolate the oxiranes, it is advantageous to bromohydrins of the formula III in an ether, for example diethyl ether, dioxane or THF with a base, for example
  • Potassium hydroxide but preferably sodium hydride in THF to implement.
  • Chloroform methylene chloride or lower alcohols, for example methanol, ethanol, propanol or
  • isopropanol Ethanol or aqueous solutions of such alcohols are preferred. Are advantageous
  • Reaction temperatures between 0o C and the boiling point of the respective solvent, preferably
  • the compounds of general formula VI can by reacting oxiranes of formula II with
  • Alkali metal azides such as sodium azide.
  • trans-4-azido-2H-benzo (b) pyran-3-ols of the formula VI the corresponding compounds IV can be prepared by reduction, preferably by hydrogen over 10% palladium / carbon.
  • R 8 is one C 1-6 alkyl radical, preferably methyl or ethyl,
  • Preferred solvents are, for example, lower alcohols such as methanol and ethanol, or nitromethane or acetonitrile.
  • the alkylation is carried out in the presence of organic or inorganic bases, for example tertiary amines such as triethylamine or alkali metal carbonates such as K 2 CO 3 .
  • reaction temperatures between 0 ° C and the boiling point of the respective
  • the reaction mixture was initially kept at room temperature until the alkylation reaction had ended.
  • m is 0 or 1
  • R 8 is a C 1-6 -alkyl radical, preferably methyl or ethyl.
  • a suitable reducing agent is in particular
  • Toluene is particularly suitable as a solvent for these reactions. It is favorable to choose the reaction temperature between 10 ° C and the boiling point of the respective solvent.
  • the reaction mixture is preferably first kept at room temperature until the reductive alkylation has ended, and then the cyclization is carried out in situ at a higher temperature, preferably the boiling point of the particular solvent.
  • the compounds of the formula Ia obtainable by the processes described above contain the free hydroxyl group R 3 . They can be converted by O-alkylation or O-acylation into other compounds of the formula Ia in which R 3 is C 1-8 alkoxy or C 1-8 alkylcarbonyloxy, C 1-8 alkoxycarbonyloxy, formyloxy, C 1 -8 -monoalkylaminocarbonyloxy or
  • R 1 , R 2 , R 6 and R 6 have the have the meaning given and R 4 represents hydrogen.
  • Alkylation can e.g. by using a
  • C 1-8 alkyl iodide can be carried out in an inert solvent such as toluene or dimethylformamide in the presence of a base such as potassium hydroxide or barium hydroxide.
  • a base such as potassium hydroxide or barium hydroxide.
  • Esterification can be accomplished by using a
  • C 1-8 acyl chloride or acyl anhydride or another activated derivative of the alkanoic acid in question optionally in the presence of an organic base such as pyridine or triethylamine or an inorganic base such as potassium carbonate, optionally under
  • Condensation reagents such as dicyclohexylcarbodiimide are carried out in an inert solvent, if appropriate at elevated temperature.
  • a conversion to carbonates is carried out analogously
  • Formyloxy can be introduced by reaction with formic acid in the presence of pyridine.
  • the dehydration is caused by reagents such as
  • the compounds of the formula Ib can be used under the conditions described in 5.1
  • Main products are obtained when the reaction of the oxiranes II with the heterocycles H-A or H-B at elevated temperature, preferably 40 ° C, longer
  • Any resulting mixtures of compounds of types Ia and Ib can be separated by conventional methods such as chromatography or fractional crystallization.
  • Difluoromethylthio, trifluoromethylthio or 2,2,2-trifluoroethylthio can have meaning by suitable oxidizing agents such as e.g. Hydrogen peroxide in
  • Sulfonyl compounds can be separated into the pure components by conventional methods such as chromatography or fractional crystallization.
  • the compounds of formula I can be basic
  • acids that provide physiologically acceptable salts are suitable for this implementation.
  • So inorganic acids can be used, e.g.
  • heterocyclic mono- or polybasic carboxylic, sulfonic or sulfuric acids e.g. Formic acid, acetic acid, propionic acid, pivalic acid, diethyl acetic acid,
  • Ascorbic acid Ascorbic acid, nicotinic acid, sonic acid, methane or ethanesulfonic acid, ethanedisulfonic acid,
  • the hot alcoholic solution of the base is mixed with the alcoholic solution of a suitable acid, and the salt is obtained, if appropriate after adding ether.
  • Salts with physiologically unacceptable acids e.g. Picrates can be used to purify the compounds.
  • Compounds of formula I can have one or more chiral centers due to asymmetric sulfur or carbon atoms. They can therefore be prepared as racemates, diastereomeric mixtures of racemates, or, if optically active starting materials are used, also in optically active form as enantiomers or mixtures of
  • connections e.g. two or more chiral centers, then they can be synthesized as
  • racemates can be separated mechanically or chemically into their enantiomers by methods known per se.
  • diastereomers can be formed by reaction with a chiral separating agent.
  • a release agent for basic compounds of Formula I are suitable, for example, chiral acids such as D- and
  • Carbinols i.e.
  • R- or S-1- (1-naphthyl) ethyl isocyanate are esterified and then separated (cf. EP-A2-0 314 446).
  • the various forms of the enantiomers of the formula I can be obtained in a manner known per se from the
  • the invention also relates to a process for the preparation of pharmaceutical preparations, characterized in that a compound of the formula I and / or one of its physiologically acceptable salts is combined with at least one solid, liquid or semi-liquid carrier or auxiliary and
  • the compound is accessible analogously to Example 1 from trans-2- (2,3-dihydro-2,2-dimethyl-3-hydroxy-6- (difluoromethoxy) -2H-1-benzopyran-4-amine and 2- ( Bromomethyl) benzoic acid ethyl ester.
  • Crystals of the compound are obtained (melting point 198-201 ° C.).
  • connection is accessible analogously to the process described under 1 ', A' or 1 ', B'.
  • the compound is available analogously to method V, A 'or 1', B '.
  • the residue is filtered through silica gel.
  • 1,2-dichlorobenzo heated to 180 ° C. for 4 hours.
  • Sodium hydride (3.5 g, 80%, in paraffin ⁇ l) was added in portions. After stirring for one hour at room temperature, another 1 g of sodium hydride is added. After a further hour, the mixture is filtered through silica gel and the solution is evaporated.
  • 6-Trifluoromethylsulfiny1-2,2-dimethyl-2H-benzo (b) pyran in 45 ml DMSO and 0.7 ml water are at 20 - 25 ° C 51 g (28.6 mmol) of N-bromosuccinimide were added. After a
  • Tet rahydrof uran is de-oiled under nitrogen
  • R 6 CF 3 S-trans-2,3-dimethyl-3-hydroxy-6- (trifluoromethylthio) -2H-1-benzopyran-4-amine
  • Ampoules containing the components mentioned below can be produced in a known manner.
  • the active ingredient is dissolved in water and 1,2-propanediol and filled into glass ampoules under nitrogen.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Dérivés du benzopyranne de formule générale (I) dont les substituants ont les significations données dans la description, ainsi que les formes tautomères et isomères de (I) et les sels et/ou les produits d'addition acides de ces composés.
PCT/DE1992/000357 1991-05-11 1992-05-06 Derives du benzopyranne portant des substituants isoindolyle et isoquinolyle, produits intermediaires et leur procede de fabrication Ceased WO1992020672A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4115521.1 1991-05-11
DE19914115521 DE4115521A1 (de) 1991-05-11 1991-05-11 Isoindolyl- und isochinolylsubstituierte benzopyran-derivate, zwischenprodukte, sowie verfahren zu ihrer herstellung

Publications (1)

Publication Number Publication Date
WO1992020672A1 true WO1992020672A1 (fr) 1992-11-26

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Application Number Title Priority Date Filing Date
PCT/DE1992/000357 Ceased WO1992020672A1 (fr) 1991-05-11 1992-05-06 Derives du benzopyranne portant des substituants isoindolyle et isoquinolyle, produits intermediaires et leur procede de fabrication

Country Status (4)

Country Link
AU (1) AU1692192A (fr)
DE (1) DE4115521A1 (fr)
PL (1) PL297369A1 (fr)
WO (1) WO1992020672A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7576094B2 (en) 2004-12-13 2009-08-18 Eli Lilly And Company Spiro derivatives as lipoxygenase inhibitors

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9225859D0 (en) * 1992-12-11 1993-02-03 Smithkline Beecham Plc Novel treatment

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0158923A2 (fr) * 1984-04-14 1985-10-23 Beecham Group Plc Dérivés de chromane
EP0350805A1 (fr) * 1988-07-12 1990-01-17 Beiersdorf-Lilly GmbH Dérivés benzopyraniques, procédé pour leur préparation et leur application, aussi bien que les préparations les contenant
WO1990012011A1 (fr) * 1989-04-12 1990-10-18 American Home Products Corporation Nouveaux derives de benzopyrans anti-hypertensifs
EP0482931A1 (fr) * 1990-10-24 1992-04-29 Sankyo Company Limited Dérivés de benzopyranne ayant une activité antihypertensive et vasodilatoire, leur préparation et leur utilisation

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL88035A0 (en) * 1987-10-27 1989-06-30 American Home Prod Benzopyran derivatives,their preparation and pharmaceutical compositions containing them
DE3923839A1 (de) * 1989-07-19 1991-01-31 Beiersdorf Ag Benzopyran-derivate, verfahren zu ihrer herstellung und ihre verwendung sowie die verbindungen enthaltende zubereitungen

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0158923A2 (fr) * 1984-04-14 1985-10-23 Beecham Group Plc Dérivés de chromane
EP0350805A1 (fr) * 1988-07-12 1990-01-17 Beiersdorf-Lilly GmbH Dérivés benzopyraniques, procédé pour leur préparation et leur application, aussi bien que les préparations les contenant
WO1990012011A1 (fr) * 1989-04-12 1990-10-18 American Home Products Corporation Nouveaux derives de benzopyrans anti-hypertensifs
EP0482931A1 (fr) * 1990-10-24 1992-04-29 Sankyo Company Limited Dérivés de benzopyranne ayant une activité antihypertensive et vasodilatoire, leur préparation et leur utilisation

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7576094B2 (en) 2004-12-13 2009-08-18 Eli Lilly And Company Spiro derivatives as lipoxygenase inhibitors

Also Published As

Publication number Publication date
AU1692192A (en) 1992-12-30
DE4115521A1 (de) 1992-11-12
PL297369A1 (en) 1993-09-20

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