Tetrahydropyridoethers

Details Tetrahydropyridoethers Tetrahydropyridoethers

2000-07-19

2002-08-20

Rotman, Alan L. (Department: 1625)

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

06436953

ABSTRACT:

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 are said to be suitable for the treatment of peptic ulcer disorders.
DESCRIPTION OF THE INVENTION
The invention relates to compounds of the formula 1
in which
R1 is methyl or hydroxymethyl,
one of the substituents R2a and R2b is hydrogen and the other is hydroxy, methoxy, ethoxy, isopropoxy, methoxyethoxy or methoxypropoxy,
one of the substituents R3a and R3b is hydrogen and the other is hydroxy, methoxy, ethoxy, isopropoxy, methoxyethoxy or methoxypropoxy,
where R2a or R2b on the one hand and R3a or R3b on the other hand are not simulataneously hydroxy, and their seats.
Suitable salts of compounds of the formula 1 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, acelic acid, citric acid, D-gluconic acid, benzoic acid, 2-(4-hydroxybenzoyl)benzoic acid, butyric acid, sulfosalicyclic acid, maleic acid, lauric acid, malic acid, fumaric acid, succinic acid, oxalic acid, tartaric acid, embonic acid, stearic acid, toluenesulfonic acid, methanesulfonci acid or 3-hydroxy-2-naphtholc 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 1 as well as all solvates and in particular all hydrates of the salts of the compounds of formula 1.
The compounds of the formula 1 have three chiral centers. The invention relates to all eight conceivable stereoisomers in any desired mixing ratio with one another, including the pure enantiomers, which are a preferred subject of the invention.
A preferred embodiment of the invention are compounds of the formula 1*
in which
R1 is methyl or hydroxymethyl,
one of the substituents R2a and R2b is hydrogen and the other is hydroxy, methoxy, ethoxy, isopropoxy, methoxyethoxy or methoxypropoxy,
one of the substituents R3a and R3b is hydrogen and the other is hydroxy, methoxy, ethoxy, isopropoxy, methoxyethoxy or methoxypropoxy,
where R2a or R2b on the one hand and R3a and R3b on the other hand are not simultaneously hydroxy, and their salts.
An embodiment (embodiment a) of the invention are compounds of the formula 1*,
in which
R1 is methyl,
one of the substituents R2a and R2b is hydrogen and the other is methoxy, ethoxy, isopropoxy, methoxyethoxy or methoxypropoxy,
one of the substituents R3a and R3b is hydrogen and the other is hydroxy, and their salts.
A further embodiment (embodiment b) of the invention are compounds of the formula 1,
in which
R1 is methyl,
one of the substituents R2a and R2b is hydrogen and the other is hydroxy,
one of the substituents R3a and R3b is hydrogen and the other is methoxy, ethoxy, isopropoxy, methoxyethoxy or methoxypropoxy,
and their salts.
A further embodiment (embodiment c) of the invention are compounds of the formula 1*,
in which
R1 methyl,
one of the substituents R2a and R2b is hydrogen and the other is methoxy, ethoxy, isopropoxy, methoxyethoxy or methoxypyropoxy,
one of the substituents R3a and R3b is hydrogen and the other is methoxy, ethoxy, isopropoxy, methoxyethoxy or methoxypyropoxy,
and their salts.
A further embodiment (embodiment d) of the invention are compounds of the formula 1*,
in which
R1 is hydroxymethyl,
one of the substituents R2a and R2b is hydrogen and the other is methoxy, ethoxy, isopropoxy, methoxyethoxy or methoxypropoxy,
one of the substituents R3a and R3b is hydrogen and the other is hydroxy,
and their salts.
A further embodiment (embodiment e) of the invention are compounds of the formula 1*,
in which
R1 is hydroxymethyl,
one of the substituents R2a and R2b is hydrogen and the other is hydroxy.
one of the substituents R3a and R3b is hydrogen and the other is methoxy, ethoxy, isopropoxy, methoxyethoxy or methoxypropoxy,
and their salts.
A further embodiment (embodiment f) of the invention are compounds of the formula 1*,
in which
R1 is hydroxymethyl,
one of the substituents R2a and R2b is hydrogen and the other is methoxy, ethoxy, isopropoxy, methoxyethoxy or methoxypropoxy, one of the substituents R3a and R3b is hydrogen and the other is methoxy, ethoxy, isopropoxy, methoxyethoxy or methoxypropoxy,
and their salts.
Preferred compounds of the embodiments a to f are those, in which R3b is hydrogen.
Particularly preferred compounds of the embodiments a to f are those, in which R2a and R3b are hydrogen.
Preferred compounds within the scope of the invention are those of embodiment a, which can be characterized by the formula 1**
in which
one of the substituents Ra and Rb is hydrogen and the other is methoxy, ethoxy, isopropoxy, methoxyethoxy or methoxypropoxy
and their salts.
Particularly preferred compounds of embodiment a are those of formula 1**,
in which
Ra is hydrogen and
Rb is methoxy, ethoxy, isopropoxy, methoxyethoxy or methoxypropoxy,
and their salts.
With the aid of the general formula 1*, the following exemplary preferred compounds according to the invention may actually be mentioned by means of the substituent meanings for R1, R2a, R2b, R3a and R3b in the following Table 1 (Tab. 1):
TABLE 1
R1
R2a
R2b
R3a
R3b
CH
3
H
OCH
3
OH
H
CH
3
H
OC
2
H
5
OH
H
CH
3
H
OCH(CH
3
)
2
OH
H
CH
3
H
OCH
2
CH
2
OCH
3
OH
H
CH
3
H
OCH
2
CH
2
CH
2
OCH
3
OH
H
CH
3
H
OH
OCH
3
H
CH
3
H
OH
OC
2
H
5
H
CH
3
H
OH
OCH(CH
3
)
2
H
CH
3
H
OH
OCH
2
CH
2
OCH
3
H
CH
3
H
OH
OCH
2
CH
2
CH
2
OCH
3
H
CH
3
H
OCH
3
OCH
3
H
CH
3
H
OC
2
H
5
OC
2
H
5
H
CH
3
H
OCH(CH
3
)
2
OCH(CH
3
)
2
H
CH
3
H
OCH
2
CH
2
OCH
3
OCH
2
CH
2
OCH
3
H
CH
3
H
OCH
2
CH
2
CH
2
OCH
3
OCH
2
CH
2
CH
2
OCH
3
H
CH
2
OH
H
OCH
3
OH
H
CH
2
OH
H
OC
2
H
5
OH
H
CH
2
OH
H
OCH(CH
3
)
2
OH
H
CH
2
OH
H
OCH
2
CH
2
OCH
3
OH
H
CH
2
OH
H
OCH
2
CH
2
CH
2
OCH
3
OH
H
CH
2
OH
H
OH
OCH
3
H
CH
2
OH
H
OH
OC
2
H
5
H
CH
2
OH
H
OH
OCH(CH
3
)
2
H
CH
2
OH
H
OH
OCH
2
CH
2
OCH
3
H
CH
2
OH
H
OH
OCH
2
CH
2
CH
2
OCH
3
H
CH
2
OH
H
OCH
3
OCH
3
H
CH
2
OH
H
OC
2
H
5
OC
2
H
5
H
CH
2
OH
H
OCH(CH
3
)
2
OCH(CH
3
)
2
H
CH
2
OH
H
OCH
2
CH
2
OCH
3
OCH
2
CH
2
OCH
3
H
CH
2
OH
H
OCH
2
CH
2
CH
2
OCH
3
OCH
2
CH
2
CH
2
OCH
3
H
CH
3
OCH
3
H
OH
H
CH
3
OC
2
H
5
H
OH
H
CH
3
OCH(CH
3
)
2
H
OH
H
CH
3
OCH
2
CH
2
CH
3
H
OH
H
CH
3
OCH
2
CH
2
CH
2
OCH
3
H
OH
H
CH
3
OH
H
OCH
3
H
CH
3
OH
H
OC
2
H
5
H
CH
3
OH
H
OCH(CH
3
)
2
H
CH
3
OH
H
OCH
2
CH
2
OCH
3
H
CH
3
OH
H
OCH
2
CH
2
CH
2
OCH
3
H
CH
3
OCH
3
H
OCH
3
H
CH
3
OC
3
H
5
H
OC
2
H
5
CH
3
OCH(CH
3
)
2
H
OCH(CH
3
)
2
H
CH
3
OCH
2
CH
2
OCH
3
H
OCH
2
CH
2
OCH
3
H
CH
3
OCH
2
CH
2
CH
2
OCH
3
H
OCH
2
CH
2
CH
2
OCH
3
H
CH
2
OH
OCH
3
H
OH
H
CH
2
OH
OC
2
H
5
H
OH
H
CH
2
OH
OCH(CH
3
)
2
H
OH
H
CH
2
OH
OCH
2
CH
2
OCH
3
H
OH
H
CH
2
OH
OCH
2
CH
2
CH
2
OCH
3
H
OH
H
CH
2
OH
OH
H
OCH
3
H
CH
2
OH
OH
H
OC
2
H
5
H
CH
2
OH
OH
H
OCH(CH
3
)
2
H
CH
2
OH
OH
H
OCH
2
CH
2
OCH
3
H
CH
2
OH
OH
H
OCH
2
CH
2
CH
2
OCH
3
H
CH
2
OH
OCH
3
H
OCH
3
H
CH
2
OH
OC
2
H
3
H
OC
2
H
5
H
CH
2
OH
OCH(CH
3
)
2
H
OCH(CH
3
)
2
H
CH
2
OH
OCH
2
CH
2
OCH
3
H
OCH
2
CH
2
OCH
3
H
CH
2
OH
OCH
2
CH
2
CH
2
OCH
3
H

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