EP0000128A1 - Sulfamoylarylcétones et procédé pour leur préparation ainsi que leur application comme médicament - Google Patents

Sulfamoylarylcétones et procédé pour leur préparation ainsi que leur application comme médicament Download PDF

Info

Publication number
EP0000128A1
EP0000128A1 EP78100118A EP78100118A EP0000128A1 EP 0000128 A1 EP0000128 A1 EP 0000128A1 EP 78100118 A EP78100118 A EP 78100118A EP 78100118 A EP78100118 A EP 78100118A EP 0000128 A1 EP0000128 A1 EP 0000128A1
Authority
EP
European Patent Office
Prior art keywords
chloro
sulfamoylbenzoyl
compounds
furan
benzo
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.)
Withdrawn
Application number
EP78100118A
Other languages
German (de)
English (en)
Inventor
Hans Jochen Dr. Lang
Josef Dr. Musil
Roman Dr. Muschaweck
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.)
Hoechst AG
Original Assignee
Hoechst AG
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 Hoechst AG filed Critical Hoechst AG
Publication of EP0000128A1 publication Critical patent/EP0000128A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/80—Radicals substituted by oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/10—Antioedematous agents; Diuretics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/12—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D333/56—Radicals substituted by oxygen atoms

Definitions

  • the invention relates to compounds of general formula I. in which R 1 is hydrogen, halogen, alkyl having 1 to 3 C atoms, methoxy or ethoxy, R 2 and R 3 can be identical or different and is hydrogen or alkyl having 1 to 4 C atoms, X is a halogen atom, methyl or trifluoromethyl and Y is oxygen, sulfur or NR 4 , where R 4 is hydrogen or alkyl having 1 to 4 carbon atoms.
  • the alkyl radicals for R 1 to R 4 can be straight-chain or branched.
  • halogen-substituted benzene derivatives such as fluoro-, difluoro-, chloro- or dichlorobenzene, among others, have proven to be particularly suitable.
  • Aluminum chloride, tin and titanium tetrachloride are preferably used as Friedel-Krafts catalysts, which include both Lewis acids and protonic acids, although other catalysts, such as HF, BF 3 , ZnCl 2 , GaCl 3 , J 2 , are also used can.
  • HF, HClO 4 or polyphosphoric acid are suitable as protonic acids.
  • A is hydroxy, aluminum chloride, zinc chloride, boron trifluoride, but also hydrogen fluoride and perchloric acid, and also polyphosphoric acid or phosphorus oxychloride are preferably used as catalysts, while POCl 3 is used as a catalyzing Lewis acid, especially when reacting III with the acid amide derivatives of the formula II , both-.
  • NEN Y stands for -NR 2 , advantageously used.
  • Polar solvents such as water, lower alcohols with 1 to 5 carbon atoms, dioxane, tetrahydrofuran, dimethylacetamide, mono-, di- or triethylene glycol dimethyl ether have proven to be particularly suitable as reaction media, the reaction being between 0 and 100 ° C. , preferably between 10 and 50 ° C.
  • the reaction time is between 1/2 and 70 hours, preferably 4 to 14 hours.
  • the sulfochlorides of the formula IV can be obtained in various ways in a manner known per se. They are preferably obtained from the amino derivatives of the formula X by the Meerwein reaction (Chem. Ber. 90, 841 (1957)) wherein the substituents have the meaning given.
  • the compounds of formula X are, for example, compounds XI in which X and A have the meaning given, by a reaction analogous to procedure a) with compounds III and subsequent reduction of the nitro compound XII shown.
  • compounds of the general formula VI are converted into the compounds of the formula I using an oxidizing agent.
  • organic and inorganic oxidizing agents such as salts and complex compounds of Fe +3 , nickel peroxide, potassium permanganate, chromium-VI compounds, copper-II salts, halogen, nitrogen oxides such as N 2 0 3 in situ or N0 2 , ENT are suitable 3 , oxygen, inorganic and organic peroxo compounds such as H 2 0 2 , Behzoper- and m-chlorobenzoperic acid, N-chloro- and N-bromosuccinimide, dimethyl sulfoxide, aliphatic nitro compounds, ketones in the presence of an aluminum alcoholate in the sinus of an Oppenauer oxidation.
  • active manganese IV oxide has proven to be a mild and particularly suitable oxidizing agent (cf., for example, AJ Fatiadi, Synthesis 1976 , 65; DE-OS 2 436 263), the solvent used preferably being acetonitrile or halogenated hydrocarbons, such as methylene chloride, chloroform, tetrachloroethane, and the reaction at temperatures between 0 ° and 40 ° C., preferably between 20 ° and 30 ° C. , over a period of 6 to 60 hours.
  • oxidizing agent cf., for example, AJ Fatiadi, Synthesis 1976 , 65; DE-OS 2 436 263
  • the solvent used preferably being acetonitrile or halogenated hydrocarbons, such as methylene chloride, chloroform, tetrachloroethane, and the reaction at temperatures between 0 ° and 40 ° C., preferably between 20 ° and 30 ° C. , over a
  • ketimines of the formula VII which can also be present in the form of their acid addition salts, are hydrolyzed.
  • the nitriles of the formula XIV are brought with the compounds of formula III in the sense of a Houben-Hoesch reaction for the reaction, cf. Organic Reactions 5, 387 (1949).
  • the two reactants are preferably reacted in a molar ratio of 1: 1 in an inert polar and, as far as possible, water-free organic solvent, such as diethyl ether, diisopropyl ether, tetrahydrofuran, glacial acetic acid, dioxane, a halogenobenzene, preferably chlorobenzene, advantageously using mono- , Dier triethylene glycol dimethyl or diethyl ether as a solvent.
  • the reaction mixture is passed over a period of 2 to 20 hours a dry stream of HCI gas until saturation, at temperatures between -30 ° and + 40 ° C, advantageously between -5 ° and + 15 ° C. Subsequently, the mixture is advantageously left at -5 ° to + for 1 to 3 days Stand at 15 ° C. It is also possible to work in the presence of an additional Lewis acid, such as, in particular, anhydrous zinc or aluminum chloride.
  • ketimine hydrochlorides of the formula VII are obtained by adding a less polar solvent by precipitation, in particular by means of diisopropyl ether, ether, but also lower alkyl acetate, acetone and mixtures of the stated solvents with petroleum ether or cyclohexane.
  • the hydrolysis of the ketimine hydrochloride can be carried out either in an alkaline or acidic medium, the compounds VII being heated in water or ethanol / water mixtures, if appropriate in the presence of small amounts of ammonia, sodium hydroxide solution, calcium carbonate, dilute hydrochloric acid or sulfuric acid, and the resulting mixture Filtered ketone or isolated after extraction with an organic solvent, preferably with ethyl acetate.
  • the ketimines of the formula VII can also be obtained by reacting compounds of the formula VIII with the nitriles of the formula XIV by the method of Blaise, cf. Houben-Weyl, 4th edition, volume 7/2 a, page 603 (1973) become.
  • the solvents used are the inert and anhydrous solvents customary for organometallic reactions, preferably ethers such as diethyl ether, dibutyl ether, but particularly advantageously tetrahydrofuran or mono-, di-, tri- ethylene glycol dimethyl or diethyl ether.
  • Inert aromatic hydrocarbons such as toluene or xylene can be used.
  • the process is preferably carried out between 30 ° and 130 ° C., between 3 and 50 hours; the reaction mixture is usually worked up by stirring with water for 10 to 24 hours.
  • the imines obtained are converted into the compounds of formula I by hydrolysis in an acidic or basic medium.
  • reaction is carried out in an inert and anhydrous solvent customary for organometallic reactions, preferably in ether, tetrahydrofuran, dioxane or in a mono-, di- or triethylene glycol dimethyl or -diethyl ether, preferably at temperatures between -0100 ° and + 100 ° C.
  • the reaction products are hydrolyzed in a customary manner, for example by introducing the reaction mixture into an aqueous saturated ammonium chloride solution at temperatures between -5 ° and + 20 ° C. while maintaining a pH range from 6 to 11.
  • the starting materials of the formula IX are obtained by reacting a halogen ketone of the formula XV where Hal is preferably bromine or iodine, with compounds of the formula XVI known from the literature wherein Z is preferably S or O.
  • the process is carried out using the bases described in the cyclocondensation in the solvents mentioned there, advantageously under milder temperature conditions between -10 ° and + 60 ° C, but preferably between + 10 ° and + 40 ° C.
  • the preparation of IX and whose cyclocondensation to I can proceed without isolation of the compounds IX in a one-pot reaction.
  • R 3 denotes lower alkyl
  • R 3 -X conventional alkylating agents of the formula R 3 -X are used, in which X is, for example, bromine, iodine, chlorine, -O-SO 2 CH 3 , -O-SO 2 OR 3 or stands..
  • the alkylation is carried out in water, but preferably in polar organic solvents such as a lower alcohol having 1 to 4 carbon atoms, in dioxane, tetrahydrofuran, dimethylformamide, dimethylacetamide or a mono-, di-, triethylene glycol mono- or dimethyl- or -ethyl ether at temperatures. between -20 ° and + 50 ° C, preferably between + 15 ° and + 35 ° C, being left to regress for a period of 5 to 72 hours.
  • a base for Acid binding is preferably carried out using carbonates, alcoholates or hydroxides of sodium or potassium.
  • the most important compounds according to the invention are those of the general formula I in which the substituent X is bromine or chlorine, preferably chlorine, R 3 is hydrogen, methyl or ethyl, preferably hydrogen, R 2 is hydrogen, methyl or ethyl, R1 is hydrogen , Chlorine, methyl or methoxy in position 4 or 5 of the heterocycle, but is preferably hydrogen and Y is oxygen or sulfur.
  • the process products are valuable medicinal products and cause a very good effect, which lowers the uric acid level of the blood, which is caused in particular by a uricosuric effect.
  • the compounds according to the invention are distinguished by a desired good diuretic and saluretic activity, and are therefore superior to the previously known uricosuric agents.
  • the uricosuric effect of the new process products was determined on the oxonate-treated rat in a unit dose of 50 mg / kg per os. They show the antiuricopathic efficacy of known commercial preparations of the probencid type and the benzbromarone type.
  • the salidiuretic activity of the compounds according to the invention was determined on the rat in a unit dose of 50 mg / kg per os. You will achieve the salidiuretic activity of well-known commercial products like that of chlorothalidone.
  • the new process products are characterized by a long-lasting effect, which means that the preparations are also suitable for the treatment of hypertensive conditions in humans. You can combine them with an antihypertensive.
  • Tablets, dragees, capsules, suppositories and ampoules for parenteral administration are particularly suitable as therapeutic preparations for the new compounds.
  • the therapeutic unit dose is between 5 and 1000 mg, preferably 10 to 500 mg per tablet.
  • these preparations can also contain an antihypertensive, such as, for example, reserpine, hydralazine, guanethidine, ⁇ -methyldopa, a ⁇ -sympathicolytic or chloridine.
  • an antihypertensive such as, for example, reserpine, hydralazine, guanethidine, ⁇ -methyldopa, a ⁇ -sympathicolytic or chloridine.
  • potassium-retaining compounds such as aldosterone antagonists, for example spironolactone, or pseudoaldosterol antagonists, such as triamterene or amiloride
  • aldosterone antagonists for example spironolactone
  • pseudoaldosterol antagonists such as triamterene or amiloride
  • K + substitution can also be used in various forms of application, for example coated tablets, tablets, effervescent tablets, juices and others.
  • Combinations of the compounds according to the invention with another antihyperuricemic active agent can also be of therapeutic interest, which agent leads to an increase in the antiuricopathic effects, particularly by inhibiting xanthine oxidase.
  • Any desired desired enhancement of the salidiuretic activity can be achieved by combining the compounds according to the invention with a salidiuretic.
  • Example 10 a is obtained analogously to the procedure given in Example 10 a) from 2.68 g of 4-chloro-3-methylsulfamoylbenzoyl chloride and 1.3 g of 2-methylindole in the presence of 2.7 g of aluminum chloride in dichloroethane. Colorless crystals, mp 246 ° C.
  • Example 10 a is obtained analogously to the procedure given in Example 10 a) from 10 g of 4-chloro-3-sulfamoylbenzoyl chloride and 7.8 g of 2,5-dimethylindole in dichloroethane in the presence of 12 g of aluminum chloride. Mp 248 ° - 250 ° C.
  • Example 10 a is obtained analogously to the procedure given in Example 10 a) from 10 g of 4-chloro-3-sulfamoylbenzoyl chloride and 6.53 g of 1,2-dimethylindole in dichloroethane in the presence of 12 g of aluminum chloride. After treatment with isopropanol, crystals with a melting point of 247 ° -249 ° C. are obtained.
  • Example 2 is obtained analogously to the procedure given in Example 1 from 2.5 g of 4-chloro-3-sulfamoylbenzoyl chloride, 1.6 g of 3-methyl-benzo [b] thiophene and 3 g of aluminum chloride in 50 ml of chlorobenzene. Colorless crystals, mp 210 ° C.
  • Example 10 a is obtained analogously to the procedure given in Example 10 a) from 10.0 g of 4-chloro-3-sulfamoylbenzoyl chloride, 5.1 g of 3-methylindole in the presence of 10.4 g of aluminum chloride. Colorless crystals of isopropanol, mp. 205 ° C.
  • Example 10 a is obtained analogously to the procedure given in Example 10 a) from 4-chloro-3-sulfamoylbenzoyl chloride and 2-methylbenzo [b] thiophene in dichloroethane in the presence of aluminum chloride.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Rheumatology (AREA)
  • Pain & Pain Management (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Furan Compounds (AREA)
  • Indole Compounds (AREA)
EP78100118A 1977-06-21 1978-06-08 Sulfamoylarylcétones et procédé pour leur préparation ainsi que leur application comme médicament Withdrawn EP0000128A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19772727802 DE2727802A1 (de) 1977-06-21 1977-06-21 Sulfamoyl-arylketone und verfahren zu ihrer herstellung
DE2727802 1977-06-21

Publications (1)

Publication Number Publication Date
EP0000128A1 true EP0000128A1 (fr) 1979-01-10

Family

ID=6011950

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100118A Withdrawn EP0000128A1 (fr) 1977-06-21 1978-06-08 Sulfamoylarylcétones et procédé pour leur préparation ainsi que leur application comme médicament

Country Status (9)

Country Link
US (1) US4156732A (fr)
EP (1) EP0000128A1 (fr)
JP (1) JPS549259A (fr)
AU (1) AU3728978A (fr)
DE (1) DE2727802A1 (fr)
DK (1) DK278178A (fr)
IL (1) IL54945A0 (fr)
IT (1) IT1096492B (fr)
ZA (1) ZA783511B (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002000210A3 (fr) * 2000-06-28 2002-10-24 Merck & Co Inc Traitement de maladie cardio-vasculaire
US8841333B2 (en) 2005-05-09 2014-09-23 Takeda Pharmaceuticals U.S.A., Inc. Methods for treating nephrolithiasis
US9107912B2 (en) 2010-09-10 2015-08-18 Takeda Pharmaceuticals U.S.A., Inc. Methods for concomitant treatment of theophylline and febuxostat

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5835653U (ja) * 1981-09-03 1983-03-08 三國工業株式会社 始動装置のワツクス加熱調整回路
JPS5848963U (ja) * 1981-09-28 1983-04-02 本田技研工業株式会社 電熱式オ−トチヨ−ク付気化器
JPS58186152U (ja) * 1982-06-07 1983-12-10 本田技研工業株式会社 多連式気化器におけるア−ス装置
DE3317884A1 (de) * 1983-05-17 1984-11-22 Hoechst Ag, 6230 Frankfurt 5-(4-chlor-3-sulfamoylbenzoyl)-2,3-dihydro-2-benzofurancarbonsaeuren und verfahren zu ihrer herstellung
US4745222A (en) * 1983-05-25 1988-05-17 Merrell Dow Pharmaceuticals Inc. Novel aryloxycycloalkanolaminoalkylene aryl ketones
JP3157882B2 (ja) * 1991-11-15 2001-04-16 帝国臓器製薬株式会社 新規なベンゾチオフエン誘導体
JP5242393B2 (ja) * 2005-08-03 2013-07-24 タケダ ファーマシューティカルズ ユー．エス．エー． インコーポレイティド 高血圧症の治療方法
US20090124623A1 (en) * 2006-11-13 2009-05-14 Christopher Lademacher Methods for preserving and/or increasing renal function using xanthine oxidoreductase inhibitors
EP2101761A4 (fr) * 2006-11-13 2010-01-27 Takeda Pharmaceuticals North A Procédés pour préserver la fonction rénale au moyen d'inhibiteurs de xanthine oxydoréductase
AU2008206231A1 (en) * 2007-01-19 2008-07-24 Takeda Pharmaceuticals U.S.A., Inc. Methods for preventing or reducing the number of gout flares using xanthine oxidoreductase inhibitors and anti-inflammatory agents
AU2009228765B2 (en) * 2008-03-24 2012-05-31 Novartis Ag Arylsulfonamide-based matrix metalloprotease inhibitors
US20100311756A1 (en) * 2009-01-22 2010-12-09 Takeda Pharmaceuticals North America, Inc. Methods for delaying the progression of at least one of cardiac hypertrophy, cardiac remodeling or left ventricular function or the onset of heart failure in subjects in need of treatment thereof
CN106008421A (zh) * 2016-06-12 2016-10-12 南方医科大学 一种能促进尿酸排泄的人体尿酸盐转运体-1抑制剂及其制备方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL108331C (fr) *

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1521932A (en) * 1976-03-08 1978-08-16 Labaz Sulphonamide derivatives and process for preparing the same

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL108331C (fr) *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002000210A3 (fr) * 2000-06-28 2002-10-24 Merck & Co Inc Traitement de maladie cardio-vasculaire
US7799794B2 (en) 2000-06-28 2010-09-21 Merck Sharp & Dohme Corp. Treatment for cardiovascular disease
US8841333B2 (en) 2005-05-09 2014-09-23 Takeda Pharmaceuticals U.S.A., Inc. Methods for treating nephrolithiasis
US9107912B2 (en) 2010-09-10 2015-08-18 Takeda Pharmaceuticals U.S.A., Inc. Methods for concomitant treatment of theophylline and febuxostat

Also Published As

Publication number Publication date
JPS549259A (en) 1979-01-24
IL54945A0 (en) 1978-08-31
IT7824695A0 (it) 1978-06-19
AU3728978A (en) 1980-01-03
US4156732A (en) 1979-05-29
DE2727802A1 (de) 1979-04-19
ZA783511B (en) 1979-06-27
IT1096492B (it) 1985-08-26
DK278178A (da) 1978-12-22

Similar Documents

Publication Publication Date Title
CA1254216A (fr) Derives de benzothiazole et de benzothiophene
DE2727802A1 (de) Sulfamoyl-arylketone und verfahren zu ihrer herstellung
CH650782A5 (de) Carbostyrilverbindungen, verfahren zu deren herstellung und arzneimittel, welche diese enthalten.
DE1939809C3 (fr)
DE3419009A1 (de) Neue substituierte bis(4-aminophenyl)sulfone, ihre herstellung und ihre verwendung als arzneimittel
EP0071935B1 (fr) Composés du 1-phényl-2-aminocarbonylindole, procédé de préparation et intermédiaires et médicaments contenant ces composés
US4196292A (en) 6-Substituted amiloride derivatives
EP0064027B1 (fr) Dérivés de benzodioxolanes, procédé pour leur préparation et compositions pharmaceutiques les contenant
DE2351411C2 (de) (1-Oxo-2,3-hydrocarbylen-6,7-dichlor-5- indanyloxy)-essigsäuren, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Mittel
DE3784835T2 (de) Chinoxalinon-derivate.
US4134900A (en) 5,6-Dihydro-4-oxo-4H-thieno[2,3-b]thiopyran-5-carboxamides, and process for the preparation thereof
DE2436263C2 (de) Thiazolidinderivate und Verfahren zu ihrer Herstellung
DE2740836A1 (de) Anellierte indolderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
EP0107622B1 (fr) Dérivés de benzodioxole, leur procédé de préparation et compositions pharmaceutiques les contenant
DE2737407A1 (de) Verfahren zur herstellung neuer benzopyranderivate
US4154734A (en) Amides of 4-hydroxy-6H-thieno[2,3-b]thiopyran-5-carboxylic acid-7,7-dioxide
EP0072961B1 (fr) Composés 1-phénylindazol-3-one ainsi qu'un procédé et produits intermédiaires pour leur fabrication et médicaments contenant ces composés
Catsoulacos et al. Thiazo compounds. Derivatives of 4, 5-dihydro-7, 8-dimethoxybenzothiazepin-3-one 1, 1-dioxides
DE2106038C3 (de) 2-Imidazolin-2-ylamino-benzo [b] thiophene und diese enthaltende pharmazeutische Präparate
CH625217A5 (fr)
DE2804894A1 (de) Halogen-benzofuranon-carbonsaeuren
EP0064026B1 (fr) Dérivés dioxahétérocycliques, procédé pour leur préparation et compositions pharmaceutiques les contenant
US3697517A (en) 1,3-benzoxazines
AT330201B (de) Verfahren zur herstellung von neuen 7-(gamma- (n-methylphenathylamino) -propyl)-theophyllinen
US4185020A (en) 5-(4-Nitrophenyl)-2-furanmethanamines derivatives

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): BE CH DE FR GB NL SE

17P Request for examination filed
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn
RIN1 Information on inventor provided before grant (corrected)

Inventor name: MUSCHAWECK, ROMAN, DR.

Inventor name: MUSIL, JOSEF, DR.

Inventor name: LANG, HANS JOCHEN, DR.