Fused dihydropyrans

Details Fused dihydropyrans Fused dihydropyrans

1999-11-16

2000-12-12

Dentz, Bernard

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

514293, 546 65, 546 83, A61K 31435, C07D491147, C07D49122

Patent

active

061601195

DESCRIPTION:

BRIEF SUMMARY
This is a 371 of PCT/EP99/03057 filed May 23, 1998.


FIELD OF APPLICATION OF THE INVENTION

The invention relates to novel compounds which are used in the pharmaceutical industry as active compounds for the production of medicaments.


KNOWN TECHNICAL BACKGROUND

U.S. Pat. No. 4,468,400 describes tricyclic imidazo[1,2-a]pyridines having various ring systems fused onto the imidazopyridine parent structure, which should be suitable for the treatment of peptic ulcer disorders. The International Patent Application WO 95/27714 describes 8,9-dihydropyrano[2,3-c]imidazo[1,2-a]pyridines having gastric acid secretion-inhibiting properties.


DESCRIPTION OF THE INVENTION

It has now been found that the compounds described below in greater detail, which differ from the compounds of the prior art, in particular by the substitution in the 7- and/or 8-position of the 8,9-dihydropyrano[2,3-c]imidazo[2-a]pyridine, have particularly advantageous properties.
The invention relates to compounds of the formula I ##STR2## in which R.sub.1 is 1-4C-alkyl, R.sub.4 b is hydrogen and the other is hydrogen, hydroxyl, 1-4C-alkoxy, 1-4C-alkoxy-1-4C-alkoxy or 1-4C-alkylcarbonyloxy, or in which R.sub.4 a and R.sub.4 b together are O (oxygen), one of the substituents R.sub.5 a and R.sub.5 b is hydrogen and the other is hydrogen, hydroxyl, 1-4C-alkoxy, 1-4C-alkoxy-1-4C-alkoxy or 1-4C-alkylcarbonyloxy, or in which R.sub.5 a and R.sub.5 b together are O (oxygen), where R.sub.4 a, R.sub.4 b, R.sub.5 a and R.sub.5 b are not simultaneously hydrogen, or in which one of the substituents R.sub.4 a and R.sub.4 b on the one hand and one of the substituents R.sub.5 a and R.sub.5 b on the other hand is in each case hydrogen, and the other substituents in each case together form a methylenedioxy radical (--O--CH2--O--) or an ethylenedioxy radical (--O--CH.sub.2 --CH.sub.2 --O--), R.sub.6 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, 1-4C-alkoxycarbonylamino, 1-4C-alkoxy-1-4C-alkoxycarbonylamino or trifluoromethyl and R.sub.7 is hydrogen, halogen, 1-4C-alkyl or 1-4C-alkoxy, 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 radical, isobutyl radical, sec-butyl radical, tert-butyl radical, propyl radical, isopropyl radical, ethyl radical and the methyl radical. The methyl radical is preferred.
Hydroxy-1-4C-alkyl represents abovementioned 1-4C-alkyl radicals which are substituted by a hydroxyl group. Examples which may be mentioned are the hydroxymethyl radical, the 2-hydroxyethyl radical and the 3-hydroxypropyl radical. The hydroxymethyl radical is preferred.
Halogen in the sense of the invention is bromine, chlorine or fluorine.
1-4C-alkoxy represents radicals which, in addition to the oxygen atom, contain a straight-chain or branched alkyl radical having 1 to 4 carbon atoms. Examples which may be mentioned are the butoxy radical, isobutoxy radical, sec-butoxy radical, tert-butoxy radical, propoxy radical, isopropoxy radical and preferably the ethoxy radical and methoxy radical.
1-4C-alkoxy-1-4C-alkoxy represents one of the abovementioned 1-4C-alkoxy radicals which is substituted by a further 1-4C-alkoxy radical. Examples which may be mentioned are the radicals 2-(methoxy)ethoxy (CH.sub.3 --O--CH.sub.2 --CH.sub.2 --O--) and 2-(ethoxy)ethoxy (CH.sub.3 --CH.sub.2 --O--CH.sub.2 --CH.sub.2 --O--).
1-4C-alkylcarbonyloxy represents a carbonyloxy group to which is bonded one of the abovementioned 1-4C-alkyl radicals. An example which may be mentioned is the acetoxy radical (CH.sub.3 CO--O--).
1-4C-alkoxycarbonyl represents a carbonyl group to which is bonded one of the abovementioned 1-4C-alkoxy radicals. Examples which may be mentioned are the methoxycarbonyl radical (CH.sub.3 O--C(O)--) and the ethoxycarbonyl radical (CH.sub.3 CH.sub.2 O--C(O)--).
1-4C-alkoxycarbonylamino represents an amino radical which is substituted by one of the abovementioned 1-4C-alkoxycarbonyl radicals. Examples which may be mentioned are the ethoxycarbonylamino radical and the m

REFERENCES:
patent: 4468400 (1984-08-01), Gold et al.

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