Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1999-05-12
2000-03-28
Gerstl, Robert
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514337, 546269, 548203, 548204, C07D41704, A61K 31425
Patent
active
060432632
DESCRIPTION:
BRIEF SUMMARY
FIELD OF APPLICATION OF THE INVENTION
The invention relates to novel thiazole derivatives which are used in the pharmaceutical industry for the production of medicaments.
KNOWN TECHNICAL BACKGROUND
Japanese patent specification JP 46-15935 describes substituted 4-(carboxyphenyl)thiazoles and their use for the treatment of thrombosis, arteriosclerosis, gastric ulcers and hypersecretion. European patent applications EP 0 513 387 and EP 0 600 092 describe, inter alia, 4-(substituted phenyl)thiazole derivatives, 4-(substituted 2,3-dihydrobenzofuran)thiazole derivatives and their use as inhibitors of oxygen radical release by neutrophils. The compounds are therefore described as suitable for the treatment of acute inflammatory processes such as ischemia and reperfusion damage.
International patent application WO94/12461 describes 4-substituted catechol diethers, which are substituted in the 4-position, inter alia, with thiazole derivatives, and their use as inhibitors of phosphodiesterase IV.
DESCRIPTION OF THE INVENTION
It has now surprisingly been found that the novel thiazole derivatives described below in greater detail, which differ from the previously published thiazoles, in particular, by the substituents on the 4-(2,3-dihydrobenzofuran ring), are selective inhibitors of phosphodiesterase IV.
The invention thus relates to compounds of the formula I (see attached formula sheet I), in which benzyloxy or 1-4C-alkoxy which is completely or mainly substituted by fluorine, bonded, are a 5-, 6- or 7-membered hydrocarbon ring which, if desired, is interrupted by an oxygen atom, mono- or bicyclic heterocycle which is substituted by R44, R45 and R46 and which is selected from the group consisting of pyridine, pyrrole, quinoline, isoquinoline, indole, isoindole, indolizine, pyrimidine, pyrazine, pyridazine, quinoxaline, quinazoline, cinnoline, benzimidazole, thiophene and furan or a mono- or bicyclic heterocycle which is substituted by R44 and R45 and which is selected from the group consisting of pyrazole, imidazole, purine, oxazole, isoxazole, thiazole and isothiazole, where sulfamoyl, mono- or di-1-4C-alkylaminocarbonyl, mono- or di-1-4C-alkylami-nosulfonyl, amino, mono- or di-1-4C-alkylamino, 1-4C-alkylcarbonylamino, 1-4C-alkylsulfonyl, 1-4C-alkoxysulfonyl, hydroxy-1-4C-alkyl, hydroxyl, 1-4C-alkoxy, 1-4C-alkyl, 1-4C-alkylcarbonyl, 1-4C-alkylcarbonyloxy, halogen, cyano or nitro, fluorine, hydroxyl, amino, nitro, halogen, 1-4C-alkoxycarbonyl, 1-4C-alkyl-carbonyloxy, 1-4C-alkylcarbonyl, carboxyl, 1-4C-alkyl or 1-4C-alkoxy, sulfamoyl, mono- or di-1-4C-alkylaminocarbonyl, mono- or di-1-4C-alkylaminosulfonyl, amino, mono- or di-1-4C-alkylamino, 1-4C-alkylcarbonylamino, hydroxy-1-4C-alkyl, hydroxyl, 1-4C-alkoxy, 1-4C-alkyl, 1-4C-alkylcarbonyl, 1-4C-alkylcarbonyloxy, halogen, cyano or nitro, 1-4C-alkylcarbonyl, 1-4C-alkoxycarbonyl or 1-4C-alkoxy and isoquinolines, pyrimidines, pyrazines, imidazoles, quinoxalines, quinazolines and benzimidazoles and their salts.
1-4C-alkyl represents straight-chain or branched alkyl radicals having 1 to 4 carbon atoms. Examples which may be mentioned are the butyl, the isobutyl, the secbutyl, the tert-butyl, the propyl, the isopropyl, the ethyl and the methyl radical.
1-4C-alkoxy represents a radical which, in addition to the oxygen atom, contains one of the abovementioned straight-chain or branched alkyl radicals having 1 to 4 carbon atoms. Alkoxy radicals having 1 to 4 carbon atoms which may be mentioned here are, for example, the butoxy, isobutoxy, sec-butoxy, tert-butoxy, propoxy, isopropoxy, ethoxy and the methoxy radical.
3-7C-cycloalkoxy represents the cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy and cycloheptyloxy radical. The 3-5C-cycloalkoxy radicals cyclopropyloxy, cyclobutyloxy and cyclopentyloxy may preferably be mentioned.
3-7C-cycloalkylmethoxy represents cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy and cycloheptylmethoxy. The 3-5C-cycloalkylmethoxy radicals cyclopropylmethoxy, cyclobutylmethoxy and cyclopentylmethoxy
REFERENCES:
patent: 5639770 (1997-06-01), Chihiro
patent: 5677319 (1997-10-01), Chihiro
patent: 5814651 (1998-09-01), Duplantier
Bar Thomas
Ulrich Wolf-Rudiger
ByK Gulden Lomberg Chemische Fabrik GmbH
Gerstl Robert
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