Tetrahydropyrido compounds

Details Tetrahydropyrido compounds Tetrahydropyrido compounds

1999-09-24

2001-03-06

Huang, Evelyn Mei (Department: 1612)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C546S082000

Reexamination Certificate

active

06197783

ABSTRACT:

RELATED APPLICATION
The subject matter disclosed and claimed herein is related to subject matter disclosed and claimed in copending application Ser. No. 09/582,212, filed Jul. 19, 2000.
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.
DESCRIPTION OF THE INVENTION
The Invention relates to compounds of the formula I
in which
R1 is 1-4C-alkyl,
R2 is 1-4C-alkyl or hydroxy-1-4C-alkyl,
R3 is hydrogen or halogen, one of the substituents R4a and R4b is hydrogen and the other is hydrogen, hydroxyl, 1-4C-alkoxy, 1-4C-alkoxy-1-4C-alkoxy or 1-4C-alkylcarbonyloxy, or in which R4a and R4b together are O (oxygen),
one of the substituents R5a and R5b is hydrogen and the other is hydrogen, hydroxyl, 1-4C-alkoxy, 1-4C-alkoxy-1-4C-alkoxy or 1-4C-alkylcarbonyloxy, or in which R5a and R5b together are O (oxygen),
or in which
one of the substituents R4a and R4b on the one hand and one of the substituents R5a and R5b on the other hand is in each case hydrogen, and the other substituents in each case together form a methylenedioxy radical (—O—CH
2
—O—) or an ethylenedioxy radical (—O—CH
2
—CH
2
—O—),
where R4a, R4b, R5a and R5b are not simultaneously hydrogen,
R6 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, 1-4C-alkoxycarbonylamino, 1-4C-alkoxy-1-4C-alkoxycarbonylamino or trifluoromethyl and
R7 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
3
—O—CH
2
—CH
2
—O—) and 2-(ethoxy)ethoxy (CH
3
—CH
2
—O—CH
2
—CH
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
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
3
O—C(O)—) and the ethoxycarbonyl radical (CH
3
CH
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 methoxycarbonylamino radical.
1-4C-alkoxy-1-4C-alkoxycarbonyl represents a carbonyl group to which is bonded one of the abovementioned 1-4C-alkoxy-1-4C-alkoxy radicals. Examples which may be mentioned are the 2-(methoxy)ethoxycarbonyl radical (CH
3
—O—CH
2
CH
2
—O—CO—) and the 2-(ethoxy)ethoxycarbonyl radical (CH
3
CH
2
—O—CH
2
CH
2
—O—CO—).
1-4C-alkoxy-1-4C-alkoxycarbonylamino represents an amino radical which is substituted by one of the abovementioned 1-4C-alkoxy-1-4C-alkoxycarbonyl radicals. Examples which may be mentioned are the 2-(methoxy)ethoxycarbonylamino radical and the 2-(ethoxy)ethoxy-carbonylamino radical.
Suitable salts of compounds of the formula I—depending on substitution—are especially all acid addition salts. Particular mention may be made of the pharmacologically tolerable salts of the inorganic and organic acids customarily used in pharmacy. Those suitable are water-soluble and water-insoluble acid addition salts with acids such as, for example, hydrochloric acid, hydrobromic acid, phosphoric acid, nitric acid, sulfuric acid, acetic acid, citric acid, D-gluconic acid, benzoic acid, 2-(4-hydroxybenzoyl)benzoic acid, butyric acid, sulfosalicylic acid, maleic acid, lauric acid, malic acid, fumaric acid, succinic acid, oxalic acid, tartaric acid, embonic acid, stearic acid, toluenesulfonic acid, methanesulfonic acid or 3-hydroxy-2-naphthoic acid, where the acids are employed in salt preparation—depending on whether a mono- or polybasic acid is concerned and depending on which salt is desired—in an equimolar quantitative ratio or one differing therefrom.
Pharmacologically intolerable salts which can be initially obtained as process products, for example in the preparation of the compounds according to the invention on an industrial scale, are converted into pharmacologically tolerable salts by processes known to the person skilled in the art.
According to expert's knowledge the compounds of the invention as well as their salts may contain, e.g. when isolated in crystalline form, varying amounts of solvents. Included within the scope of the invention are therefore all solvates and in particular all hydrates of the compounds of formula I as well as all solvates and in particular all hydrates of the salts of the compounds of formula I.
The compounds of the formula I have three chiral centers. The invention relates to all eight conceivable stereoisomer in any desired mixing ratio with one another, including the pure enantiomers, which are a preferred subject of the invention.
If one of the substituents R4a and R4b on the one hand and one of the substituents R5a and R5b on the other hand together form a methylenedioxy radical or ethylenedioxy radical, the two substituents which form the methylenedioxy radical or ethylenedioxy radical are preferably cis to one another.
Compounds to be emphasized are those of the formula I, in which
R1 is 1-4C-alkyl,
R2 is 1-4C-alkyl or hydroxy-1-4C-alkyl,
R3 is hydrogen,
one of the substituents R4a and R4b is hydrogen and the other is hydrogen, hydroxyl or 1-4C-alkoxy, or in which R4a and R4b together are O (oxygen),
one of the substituents R5a and R5b is hydrogen and the other is hydrogen, hydroxyl or 1-4C-alkoxy, or in which R5a and R5b together are O (oxygen),
where R4a, R4b, R5a and R5b are not simultaneously hydrogen,
R6 is hydrogen, halogen or trifluoromethyl and
R7 is hydrogen or halogen,
and their salts.
An embodiment of the invention to be emphasized are compounds of the formula I*
in which
R1 is 1-4C-alkyl,
R2 is 1-4C-alkyl or hydroxy-1-4C-alkyl,
R3 is hydrogen,
one of the substituents R4a and R4b is hydrogen and the other is hydrogen, hydroxyl or 1-4C-alkoxy,
one of the substituents R5a and R5b is hydrogen and the other is hydrogen, hydroxyl or 1-4C-alkoxy,
where R4a, R4b, R5a and R5b are not simultaneously hydrogen,
R6 is hydrogen, halogen or trifluoromethyl and
R7 is hydrogen or halogen,
and their salts.
An embodiment of the invention particularly to be emphasized are compounds of the formula I*, in which
R1 is 1-4C-alkyl,
R2 is 1-4C-alkyl or hydroxymethyl,
R3 is hydrogen,
R4a is hydrogen,
R4b is hydroxyl or 1-4C-alkoxy,
R5a is hydrogen, hydroxyl or 1-4C-alkoxy,
R5b is hydrogen,
R6 is hydrogen, halogen or trifluoromethyl and
R7 is hydrogen or halogen,
and their salts.
A preferred embodiment of the invention are compounds of the formula I*, in which
R1 is 1-4C-alkyl,
R2 is 1-4C-alkyl,
R3 is hydrogen,
R4a

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