Imidazonaphthyridines

Details Imidazonaphthyridines Imidazonaphthyridines

2001-04-27

2002-05-07

Aulakh, Charanjit S. (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

06384048

ABSTRACT:

FIELD OF APPLICATION OF THE INVENTION
The invention relates to novel compounds which are used in the pharmaceuticals industry as active compounds for preparing medicaments.
KNOWN TECHNICAL BACKGROUND
U.S. Pat. No. 4,468,400 describes tricyclic imidazo[1,2-a]pyridines having different ring systems fused to the imidazopyridine skeleton, which compounds are said to be suitable for treating peptic ulcer disorders. The International Patent Application WO98/42707 discloses tetrahydroimidazonaphthyridines having a very particular substitution pattern, which compounds are likewise said to be suitable for treating gastrointestinal disorders.
DESCRIPTION OF THE INVENTION
The invention provides 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, 1-4C-alkylcarbonyloxy or the radical R4′, or R4a and R4b together are O (oxygen),
where
R4′ is
—O—(CH
2
)
m
S(O)
n
—R9,
—S(O),—(CH
2
)
m
—OH,
—S(O)
n
—(CH
2
)
m
—O—R9,
—S(O)
n
—(CH
2
)
m
—S(O)
p
—R9,
—O-alk1-S(O)
n
—R9,
—S(O)
n
—R9,
—S(O)
n
-alk1-OH,
—S(O),-alk1-O—R9 or
—S(O),-alk1-S(O)
p
—R9,
in which
R9 is 1-7C-alkyl, halo-1-4C-alkyl, hydroxy-1-4C-alkyl, 1-4C-alkoxy-1-4C-alkyl, carboxy-1-4C-alkyl, 1-4C-alkoxycarbonyl-1-4C-alkyl or di-1-4C-alkylamino-1-4C-alkyl, Ar or Ar-1-4C-alkyl, where Ar is phenyl or substituted phenyl having one, two or three identical or different substituents selected from the group consisting of 1-4C-alkyl, 1-4C-alkoxy, 1-4C-alkylcarbonyl, 1-4C-alkoxycarbonyl, halogen, trifluoromethyl, difluoromethoxy, trifluoromethoxy, amino, 1-4C-alkoxycarbonylamino, 1-4C-alkoxy-1-4C-alkoxycarbonylamino and nitro,
alk1 is 1-4C-alkyl-, hydroxyl-, oxo-, carboxyl-, halogen-, amino-, 1-4C-alkoxycarbonylamino- or phenyl-substituted 2-7C-alkylene or 3-4C-alkenylene,
m is an integer from 2 to 7,
n is the number 0, 1 or 2 and
p is the number 0, 1 or 2,
one of the substituents R5a and R5b is hydrogen and the other is hydrogen, hydroxyl, 1-4C-alkoxy, 1-4C-alkoxy-1-4C-alkoxy, 1-4C-alkylcarbonyloxy or the radical R5′, or R5a and R5b together are O (oxygen),
where
R5′ is
—O—(CH
2
)
q
—S(O)
r
—R10,
—S(O)
r
(CH
2
)
q
—OH,
—S(O)
r
(CH
2
)
q
—O—R10,
—S(O)
r
(CH
2
)
q
—S(O)
t
—R10,
—O-alk2-S(O)
r
—R10,
—S(O)
r
—R10,
—S(O)
r
-alk2-OH,
—S(O)
r
-alk2-O—R10 or
—S(O)
r
-alk2-S(O)
t
—R10,
in which
R10 is 1-7C-alkyl, halo-1-4C-alkyl, hydroxy-1-4C-alkyl, 1-4C-alkoxy-1-4C-alkyl, carboxy-1-4C-alkyl, 1-4C-alkoxycarbonyl-1-4C-alkyl or di-1-4C-alkylamino-1-4C-alkyl, Ar or Ar-1-4C-alkyl, where Ar is phenyl or substituted phenyl having one, two or three identical or different substituents selected from the group consisting of 1-4C-alkyl, 1-4C-alkoxy, 1-4C-alkylcarbonyl, 1-4C-alkoxycarbonyl, halogen, trifluoromethyl, difluoromethoxy, trifluoromethoxy, amino, 1-4C-alkoxycarbonylamino, 1-4C-alkoxy-1-4C-alkoxycarbonylamino and nitro,
alk2 is 1-4C-alkyl-, hydroxyl-, oxo-, carboxyl-, halogen-, amino-, 1-4C-alkoxycarbonylamino- or phenyl-substituted 2-7C-alkylene or 3-4C-alkenylene,
q is an integer from 2 to 7,
r is the number 0, 1 or 2 and
t is the number 0, 1 or 2,
R6 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, 1-4C-alkoxycarbonylamino, 1-4C-alkoxy-1-4C-alkoxycarbonylamino or trifluoromethyl,
R7 is hydrogen, halogen, 1-4C-alkyl or 1-4C-alkoxy and
R8 is hydrogen or 1-4C-alkyl,
and their salts,
where one of the substituents R4a and R4b has to be R4′and/or one of the substituents R5a and R5b has to be R5′.
1-4C-Alkyl represents straight-chain or branched alkyl radicals having 1 to 4 carbon atoms. Examples which may be mentioned are the butyl, isobutyl, sec-butyl, tert-butyl, propyl, isopropyl, ethyl and methyl radicals.
Hydroxy-1-4C-alkyl represents the abovementioned 1-4C-alkyl radicals, substituted by a hydroxyl group. Examples which may be mentioned are the hydroxymethyl, the 2-hydroxyethyl and the 3-hydroxypropyl radicals.
For the purpose of the invention, halogen is bromine, chlorine and 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, isobutoxy, sec-butoxy, tert-butoxy, propoxy, isopropoxy and preferably the ethoxy and methoxy radicals.
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
2
—CH
2
—O—CH
2
—CH
2
—O—).
1-4C-Alkylcarbonyl represents a radical which, in addition to the carbonyl group, contains one of the abovementioned 1-4C-alkyl radicals. An example which may be mentioned is the acetyl radical.
1—4C-Alkylcarbonyloxy represents a carbonyloxy group to which is attached one of the abovementioned 1-4C-alkyl radicals. An example which may be mentioned is the acetoxy radical (CH
3
CO—O—).
1-7C-Alkyl represents straight-chain or branched alkyl radicals having 1 to 7 carbon atoms. Examples which may be mentioned are the heptyl, isoheptyl (5-methylhexyl), hexyl, isohexyl(4-methylpentyl), neohexyl(3,3-dimethylbutyl), pentyl, isopentyl(3-methylbutyl), neopentyl(2,2-dimethylpropyl), butyl, iso-butyl, sec-butyl, tert-butyl, propyl, isopropyl, ethyl and methyl radicals.
Halo-1-4C-alkyl represents one of the abovementioned 1-4C-alkyl radicals which is substituted by one of the abovementioned halogen atoms. An example which may be mentioned is the 3-chloropropyl radical.
1-4C-Alkoxy-1-4C-alkyl represents one of the above-mentioned 1-4C-alkyl radicals which is substituted by one of the abovementioned 1-4C-alkoxy radicals. Examples which may be mentioned are the methoxymethyl, the methoxyethyl and the butoxyethyl radicals.
Carboxy-1-4alkyl represents, for example, the carboxy-methyl (—CH
2
COOH) or the carboxyethyl (—CH
2
CH
2
COOH) radicals.
1-4C-Alkoxycarbonyl represents a carbonyl group to which is attached one of the abovementioned 1-4C-alkoxy radicals. Examples which may be mentioned are the methoxycarbonyl (CH
3
O—C(O)—) and the ethoxycarbonyl (CH
3
CH
2
O—C(O)—) radicals.
1-4C-Alkoxycarbonyl-1-4C-alkyl represents one of the abovementioned 1-4C-alkyl radicals which is substituted by one of the abovementioned 1-4C-alkoxycarbonyl radicals. An example which may be mentioned is the ethoxycarbonylmethyl radical (CH
3
CH
2
OC(O)CH
2
—).
Di-1-4C-alkylamino represents an amino radical which is substituted by two of the abovementioned 1-4C-alkyl radicals, which may be identical or different. Examples which may be mentioned are the dimethylamino, the diethylamino and the diisopropylamino radicals.
Di-1-4C-alkylamino-1-4C-alkyl represents one of the abovementioned 1-4C-alkyl radicals which is substituted by one of the abovementioned di-1-4C-alkylamino radicals. Examples which may be mentioned are the dimethylaminomethyl, the dimethylaminoethyl and the diethylaminoethyl radicals.
Ar-1-4C-alkyl represents one of the abovementioned 1-4C-alkyl radicals which is substituted by Ar, where Ar is as defined above. Examples which may be mentioned are the phenethyl and the benzyl radicals.
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 and the methoxycarbonylamino radicals.
1-4C-Alkoxy-1-4C-alkoxycarbonyl represents a carbonyl group to which is attached one of the abovementioned 1-4C-alkoxy-1-4C-alkoxy radicals. Examples which may be mentioned are the 2-(methoxy)ethoxycarbonyl (CH
3
—O—CH
2
CH
2
—CO—) and the 2-(ethoxy)ethoxycarbonyl (CH
3
CH
2
—O—CH
2
CH
2
—O—CO—) radicals.
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 and the 2-(ethoxy)ethoxycarbonylamino radicals.
1-7C-Alkyl

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