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CA2508233A1 - New substituted imidazo-pyridinones and imidazo-pyridazinones, the preparation thereof and their use as pharmaceutical compositions - Google Patents

New substituted imidazo-pyridinones and imidazo-pyridazinones, the preparation thereof and their use as pharmaceutical compositions Download PDF

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CA2508233A1
CA2508233A1 CA002508233A CA2508233A CA2508233A1 CA 2508233 A1 CA2508233 A1 CA 2508233A1 CA 002508233 A CA002508233 A CA 002508233A CA 2508233 A CA2508233 A CA 2508233A CA 2508233 A1 CA2508233 A1 CA 2508233A1
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amino
alkyl
methyl
imidazo
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CA2508233C (en
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Norbert Hauel
Frank Himmelsbach
Elke Langkopf
Matthias Eckhardt
Roland Maier
Michael Mark
Mohammad Tadayyon
Iris Kauffmann-Hefner
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Boehringer Ingelheim Pharma GmbH and Co KG
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Priority claimed from DE2003109927 external-priority patent/DE10309927A1/en
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Abstract

The present invention relates to substituted imidazo-pyridinones and imidazo--pyridazinones of general formula (see formula I) wherein R1 to R4 are defined as in claim 1, the tautomers, the stereoisomers, the mixtures thereof and the salts thereof, which have valuable pharmacological properties, particularly an inhibitory effect on the activity of the enzyme dipeptidylpeptidase-IV (DPP-IV).

Claims (10)

1. Compounds of general formula wherein X denotes a nitrogen atom or a group of formula C-R5, while R5 denotes a hydrogen atom or a methyl group, R1 denotes a 5- to 7-membered cycloalkyleneimino group which is substituted by an amino group in the carbon skeleton and may be substituted by a C1-3-alkyl group, a 6- to 7-membered cycloalkyleneimino group wherein the methylene group is replaced by a -NH- group in the 4 position, or an amino group substituted by a C5-7-cycloalkyl group, while the C5-7-cycloalkyl group is substituted by an amino group or a carbon atom in the 3 position of the C5-7-cycloalkyl group is replaced by an -NH- group, R2 denotes a benzyl group wherein the phenyl group may be substituted by one or two fluorine, chlorine or bromine atoms or by a cyano group, a straight-chain or branched C3-5-alkenyl group, a C3-5-alkynyl group, a C3-7-cycloalkylmethyl group, a C5-7-cycloalkenylmethyl group, or a furylmethyl, thienylmethyl, pyrrolylmethyl, thiazolylmethyl, imidazolyl-methyl, pyridinylmethyl, pyrimidinylmethyl, pyridazinylmethyl or pyrazinyl-methyl group, R3 denotes a straight-chain or branched C1-6-alkyl group, a phenyl-C1-3-alkyl or naphthyl-C1-3-alkyl group optionally substituted in the aryl moiety by a halogen atom, a cyano, a C1-3-alkyl or a methoxy group, a 2-phenyl-2-hydroxy-ethyl group, a phenylcarbonylmethyl group, wherein the phenyl group may be substituted by a hydroxy, C1-3-alkyloxy, aminocarbonyl-C1-3-alkoxy, (C1-3-alkylamino)-carbonyl-C1-3-alkoxy, [di-(C1-3-alkyl)-amino]-carbonyl-C1-3-alkoxy, amino, C1-3-alkyl-carbonylamino, C3-6-cycloalkyl-carbonylamino, C1-3-alkoxy-carbonylamino, C1-3-alkylsulphonylamino or aminocarbonyl group, a (3-methyl-2-oxo-2,3-dihydro-benzoxazolyl)-carbonylmethyl group, a thienylcarbonylmethyl group, a heteroaryl-C1-3-alkyl group, while by the phrase "heteroaryl group" is meant a monocyclic 5- or 6-membered heteroaryl group optionally substituted by one or two C1-3-alkyl groups or by a morpholin-4-yl, pyridyl or phenyl group, while the 6-membered heteroaryl group contains one, two or three nitrogen atoms and the 5-membered heteroaryl group contains an imino group optionally substituted by a C1-3-alkyl or phenyl-C1-3-alkyl group, or an oxygen or sulphur atom or an imino group optionally substituted by a C1-3-alkyl or phenyl-C1-3-alkyl group or an oxygen or sulphur atom and additionally contains a nitrogen atom or an imino group optionally substituted by a C1-3-alkyl or phenyl-C1-3-alkyl group or an oxygen or sulphur atom and additionally contains two or three nitrogen atoms, and additionally a phenyl ring, which may optionally be substituted by a halogen atom, by one or two C1-3-alkyl groups or by a trifluoromethyl or methoxy group, may be fused to the above-mentioned monocyclic heteroaryl groups via two adjacent carbon atoms and the bond may be formed via an atom of the heterocyclic moiety or of the fused-on phenyl ring, a bicyclic heteroarylmethyl group according to one of the formulae or a group of formula or a group of formulae or wherein R6 in each case denotes a hydrogen atom or a methyl group, and R4 denotes a hydrogen atom or a C1-3-alkyl group, while unless otherwise stated the alkyl and alkoxy groups listed in the definitions which have more than two carbon atoms may be straight-chain or branched, and the hydrogen atoms of the methyl or ethyl groups listed in the definitions may be wholly or partly replaced by fluorine atoms, the tautomers, the enantiomers, the diastereomers, the mixtures thereof and the salts thereof.
2. Compounds of general formula I according to claim 1, wherein X denotes a nitrogen atom or a methyne group, R1 denotes a piperazin-1-yl, 3-amino-piperidin-1-yl, 3-amino-3-methyl-piperidin-1-yl, 3-amino-pyrrolidin-1-yl, 1,4-diazepan-1-yl, (2-amino-cyclohexyl)-amino or piperidin-3-yl-amino group, R2 denotes a benzyl group wherein the phenyl group may be substituted by one or two fluorine atoms, by a chlorine or bromine atom or by a cyano group, a straight-chain or branched C3-8-alkenyl group, a propyn-3-yl or but-2-yn-4-yl group, a cyclopropylmethyl group, a C5-7-cycloalkenylmethyl group, or a furylmethyl or thienylmethyl group, R3 denotes a straight-chain or branched C1-6-alkyl group, a phenyl-C1-2-alkyl or naphthyl-C1-2-alkyl group optionally substituted in the aryl moiety by a fluorine, chlorine or bromine atom or by a cyano, C1-3-alkyl or methoxy group, a 2-phenyl-2-hydroxy-ethyl group, a phenylcarbonylmethyl group, wherein the phenyl group may be substituted by a hydroxy, C1-3-alkyloxy, aminocarbonyl-C1-3-alkoxy, (C1-3-alkylamino)-carbonyl-C1-3-alkoxy, [di-(C1-3-alkyl)-amino)-carbonyl-C1-3-alkoxy, amino, C1-3-alkyl-carbonylamino, C3-6-cycloalkyl-carbonylamino, C1-3-alkoxy-carbonylamino, C1-3-alkylsulphonylamino or aminocarbonyl group, a (3-methyl-2-oxo-2,3-dihydro-benzoxazolyl)-carbonylmethyl group, a thienylcarbonylmethyl group, a heteroaryl-methyl group, while by the phrase a "heteroaryl group" is meant a pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, thiazolyl, oxazolyl, isothiazolyl, isoxazolyl, pyrazolyl, imidazolyl, oxadiazolyl, thiadiazolyl or thienyl group optionally substituted by one or two methyl groups or by a pyridyl or phenyl group, and while additionally a phenyl ring, which may optionally be substituted by a chlorine atom, by one or two methyl groups or by a trifluoromethyl or methoxy group, may be fused to the above-mentioned monocyclic heteroaryl groups via two adjacent carbon atoms and the bond may be formed via an atom of the heterocyclic moiety or of the fused-on phenyl ring, an imidazo[1,2-a)pyridin-2-yl-methyl group of formulae or a 1,2,4-triazolo[4,3-a]pyridin-3-yl group of formula or a group of formulae or wherein R6 in each case denotes a hydrogen atom or a methyl group, and R4 denotes a hydrogen atom or a methyl group, while unless otherwise stated the alkyl and alkoxy groups listed in the definitions which have more than two carbon atoms may be straight-chain or branched, and the hydrogen atoms of the methyl or ethyl groups listed in the definitions may be wholly or partly replaced by fluorine atoms, the tautomers, the enantiomers, the diastereomers, the mixtures thereof and the salts thereof.
3. Compounds of general formula I according to claim 1, wherein X, R2, R3 and R4 are defined as in claim 2 and R1 denotes a 3-amino-piperidin-1-yl group, the tautomers, the enantiomers, the diastereomers, the mixtures thereof and the salts thereof.
4. Compounds of general formula I according to claim 1, wherein X, R1, R3 and R4 are defined as in claim 2 or 3 and R2 denotes a 3-methylallyl, a 3,3-dimethylallyl or a but-2-yn-4-yl group, the tautomers, the enantiomers, the diastereomers, the mixtures thereof and the salts thereof.
5. The following compounds of general formula I according to claim 1:

(1) 2-(3-amino-piperidin-1-yl)-3-(but-2-ynyl)-5-(naphthalen-1-ylmethyl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one (2) 2-(3-amino-piperidin-1-yl)-3-but-2-ynyl-5-(3-methyl-isoquinolin-1-yl-methyl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one, (3) 2-(3-amino-piperidin-1-yl)-3-(but-2-ynyl)-5-(quinazolin-2-ylmethyl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one (4) 2-((R)-3-amino-piperidin-1-yl)-3-(but-2-ynyl)-5-(4-methyl-quinazolin-2-ylmethyl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one (5) 2-((R)-3-amino-piperidin-1-yl)-3-(but-2-ynyl)-5-(4-cyano-naphthalen-1-ylmethyl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one (6) 2-((R)-3-amino-piperidin-1-yl)-3-(but-2-ynyl)-5-(4-bromonaphth-1-ylmethyl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one (7) 2-((R)-3-amino-piperidin-1-yl)-3-(but-2-ynyl)-5-(benzo[1,2,5]thiadiazol-5-ylmethyl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one (8) 2-((R)-3-amino-piperidin-1-yl)-3-(2-chlorobenzyl)-5-(3-methyl-isoquinolin-1-ylmethyl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one (9) 2-(3-amino-piperidin-1-yl)-3-(but-2-ynyl)-5-(quinoxalin-6-ylmethyl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one (10) 2-((R)-3-amino-piperidin-1-yl)-3-(but-2-ynyl)-5-(2,3-dimethyl-quinoxalin-
6-ylmethyl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one (11) 2-((R)-3-amino-piperidin-1-yl)-3-(but-2-ynyl)-5-(5-methyl-imidazo[1,2-a]pyridin-2-ylmethyl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one (12) 2-((R)-3-amino-piperidin-1-yl)-3-(but-2-ynyl)-5-(1-methyl-1H-quinolin-2-on-6-ylmethyl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one (13) 2-((R)-3-amino-piperidin-1-yl)-3-(but-2-ynyl)-5-(4-methyl-phthalazin-1-ylmethyl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one (14) 2-((R)-3-amino-piperidin-1-yl)-3-(but-2-ynyl)-5-([1,5]naphthyridin-2-ylmethyl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one (15) 2-((R)-3-amino-piperidin-1-yl)-3-(but-2-ynyl)-5-(2,3,8-trimethyl-quinoxalin-6-ylmethyl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one and the enantiomers and the salts thereof.

6. Physiologically acceptable salts of the compounds according to at least one of claims 1 to 5 with inorganic or organic acids.
7. Pharmaceutical compositions containing a compound according to at least one of claims 1 to 5 or a salt according to claim 6 optionally together with one or more inert carriers and/or diluents.
8. Use of a compound according to at least one of claims 1 to 5 or a salt according to claim 6 for preparing a pharmaceutical composition which is suitable for the treatment of type I and type II diabetes mellitus, arthritis, obesity, allograft transplantation and osteoporosis caused by calcitonin.
9. Process for preparing a pharmaceutical composition according to claim 7, characterised in that a compound according to at least one of claims 1 to 5 or a salt according to claim 6 is incorporated in one or more inert carriers and/or diluents by a non-chemical method.
10. Process for preparing the compounds of general formula I according to claims 1 to 6, characterised in that a) a compound of general formula wherein X, R2, R3 and R4 are defined as in claims 1 to 5 and Z1 denotes a nucleofugic leaving group such as for example a chlorine or bromine atom or a C1-3-alkylsulphanyl, C1-3-alkylsulphinyl or C1-3-alkylsulphonyl group, is reacted with an amine of general formula H-R1 (III), wherein R1 is defined as in claims 1 to 5, or b) a compound of general formula wherein R2, R3 and R4 are defined as in claims 1 to 5 and R1 denotes one of the groups mentioned for R1 hereinbefore, wherein the imino, amino or alkylamino group is substituted by a protective group, is deprotected and subsequently if desired any protecting group used to protect reactive groups during the reactions is cleaved and/or a compound of general formula I thus obtained is resolved into its stereoisomers and/or a compound of general formula I thus obtained is converted into the salts thereof, particularly for pharmaceutical use into the physiologically acceptable salts thereof with an inorganic or organic acid.
CA2508233A 2002-12-03 2003-12-03 New substituted imidazo-pyridinones and imidazo-pyridazinones, the preparation thereof and their use as pharmaceutical compositions Expired - Lifetime CA2508233C (en)

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DE2003109927 DE10309927A1 (en) 2003-03-07 2003-03-07 New trisubstituted dihydro-imidazo-pyridazinone or imidazo-pyridinone derivatives, useful as dipeptidylpeptidase-IV inhibitors for e.g. treating diabetes mellitus type I or II, arthritis or obesity
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