Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-11-17
2002-11-12
Raymond, Richard L. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S314000, C514S256000, C514S269000, C514S323000, C544S242000, C544S333000, C544S335000, C546S001000, C546S135000, C546S159000, C546S229000, C548S225000, C548S226000, C548S300100, C548S311100, C549S029000, C549S054000, C549S078000, C549S083000
Reexamination Certificate
active
06479514
ABSTRACT:
FIELD OF APPLICATION OF THE INVENTION
The invention relates to compounds which are intended to be used in the pharmaceutical industry as active compounds for the production of medicaments.
1. Prior Art
International Patent Applications WO 94/13290, 94/19346, 95/01351, 95/15324, 96/00224, 95/34554, 95/34553, 96/02534 and 96/02505 describe benzimidazole and imidazopyridine derivatives which are said to be suitable for the control of Helicobacter bacteria.
2. Description of the Invention
The invention relates to compounds of the formula I
in which
R1, R2 and R3 are identical to or different from one another and are hydrogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxyl, halogen, carboxyl or 1-4C-alkylthio,
R4 is hydrogen or 1-4C-alkyl,
R5 is hydrogen or 1-4C-alkyl,
R6 is hydrogen or 1-4C-alkyl,
R7 is hydrogen, 1-4C-alkyl, 1-4C-alkoxy or halogen,
R8 is hydrogen, 1-4C-alkyl, 1-4C-alkoxy or halogen,
R9 is hydrogen or 14C-alkyl,
A is 1-7C-alkylene, 2-7C-alkenylene, 3-7C-cycloalkylene or phenylene,
G is hydrogen, 1-7C-alkyl, 1-4C-alkyl which is completely or mainly substituted by fluorine, 2-7C-alkenyl, 3-7C-cycloalkyl, a mono- or di-1-4C-alkylcarbamoyl or -thiocarbamoyl radical, an N-1-4C-alkyl-N′-cyanoamidino radical, a 1-N-1-4C-alkylamino-2-nitroethylene radical, an N-2-propynyl-N′-cyanoamidino radical, an aminosulfonylamidino radical, the radical —N(R10)R11, the part of the compound of the above formula I bonded to A (including X and via X) or a cyclic system or bicyclic system which is unsubstituted or substituted by R12 and R13 and which is selected from the group consisting of benzene, naphthalene, furan, thiophene, pyrrole, oxazole, oxazoline, oxazolidinone, isoxazole, thiazole, thiazoline, isothiazole, imidazole, imidazoline, pyrazole, triazole, tetrazole, thiadiazole, thiadiazole 1-oxide, oxadiazole, pyridine, pyridine N-oxide, pyrimidine, halopyrimidine, piperidine, triazine, pyridone, benzimidazole, imidazopyridine, benzothiazole, benzoxazole, quinoline and imidazopyridazine,
in which
R10 is 1-7C-alkyl, 3-7C-cycloalkyl or Ar-1-4C-alkyl and
R11 is 1-7C-alkyl, 3-7C-cycloalkyl or Ar-1-4C-alkyl,
where
Ar is phenyl, furyl, naphthyl, tetrahydronaphthyl or phenyl which is substituted by R14, R15 and R16,
or in which
R10 and R 11, together and including the nitrogen atom to which both are bonded, are an unsubstituted or substituted 5- or 6-membered ring hetero(bi)cyclic system which is selected from the group consisting of pyrrolidine, piperidine, piperazine, morpholine, thiomorpholine, indoline, 1,2,3,4-tetrahydroquinoline and 1,2,3,4-tetrahydroisoquinoline,
where
a substituted pyrrolidino radical is substituted by one or two identical or different substituents selected from the group consisting of 1-4C-alkyl, 1-4C-alkoxy, 1-4C-alkoxy-1-4C-alkyl, 1-4C-alkoxycarbonyl, 1-4C-alkylcarbonyloxy, hydroxy-1-4C-alkyl, hydroxyl and carboxyl,
a substituted piperidino radical is substituted by one, two or three identical or different substituents selected from the group consisting of 1-4C-alkyl, 1-4C-alkoxycarbonyl, hydroxy-1-4C-alkyl, phenyl or phenyl-1-4C-alkyl, which is substituted by R14, R15 and R16, benzoyl, benzoyl substituted by halogen and carboxyl,
a substituted piperazino radical can be substituted in the 2-, 3-, 5- or 6-position by a 1-4C-alkyl radical, and is substituted in the 4-position by a substituent selected from the group consisting of 1-4C-alkyl, 3-7C-cycloalkyl, 3-7C-cycloalkyl-1-4C-alkyl, 1-4C-alkoxycarbonyl-1-4C-alkyl and carbamoyl,
a substituted morpholino radical is substituted by one or two identical or different 1-4C-alkyl radicals,
a substituted thiomorpholino radical is substituted by one or two identical or different 1-4C-alkyl radicals or a carboxyl group,
a substituted indolin-1-yl radical can be substituted in the 2- and/or 3-position by a carboxyl group or by one or two identical or different 1-4C-alkyl radicals, and can be substituted in the benzo moiety by one or two identical or different substituents selected from the group consisting of 1-4C-alkyl, halogen and nitro,
a substituted 1,2,3,4-tetrahydroquinoline radical is substituted by one or two identical or different substituents selected from the group consisting of 1-4C-alkyl, 1-4C-alkoxycarbonyl and halogen,
a substituted 1,2,3,4-tetrahydroisoquinoline radical is substituted by one or two identical or different substituents selected from the group consisting of 1-4C-alkyl, carboxyl and phenyl,
R12 is hydrogen, 1-4C-alkyl, hydroxyl, 1-4C-alkoxy, halogen, nitro, guanidino, carboxyl, 1-4C-alkoxycarbonyl, 1-4C-alkyl substituted by R17, phenyl substituted by R14, R15 and R16 or —N(R18)R19,
R13 is hydrogen, 1-4C-alkyl, hydroxyl, 1-4C-alkoxy, halogen or trifluoromethyl,
R14 is hydrogen, 1-4C-alkyl, hydroxyl, 1-4C-alkoxy, 1-4C-alkylcarbonyl, halogen, trifluoromethyl, 1-4C-alkylamino or nitro,
R15 is hydrogen, 1-4C-alkyl, hydroxyl, 1-4C-alkoxy, halogen or nitro, and
R16 is hydrogen or trifluoromethyl,
R17 is hydroxyl, 3-7C-cycloalkyl, 1-4C-alkoxy, carboxyl, 1-4C-alkoxycarbonyl, pyridinyl or —N(R18)R19,
where
R18 is hydrogen, 1-4C-alkyl or —CO—R20 and
R19 is hydrogen or 1-4C-alkyl,
or where
R18 and R19, together and including the nitrogen atom to which both are bonded, are a piperidino or morpholino radical,
R20 is hydrogen, 1-4C-alkyl or 1-4C-alkoxy,
X is O (oxygen), N-1-4C-alkyl, NH or S,
Y is O (oxygen), N-1-4C-alkyl, NH, S, 1,4-piperazinylene or 1,4-piperidinylene,
Z is O (oxygen), N-1-4C-alkyl, NH or S or CO,
m is a number from 1 to 7,
n is a number from 0 to 4,
t is the number 0 or 1 and
u is the number 0 or 1,
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, isobutyl, sec-butyl, tert-butyl, propyl, isopropyl, ethyl and methyl radicals.
1-4C-Alkoxy represents a radical which, in addition to the oxygen atom, contains one of the abovementioned 1-4C-alkyl radicals. Examples which may be mentioned are the methoxy and the ethoxy radicals.
Halogen within the meaning of the present invention is bromine, chlorine or fluorine.
1-4C-Alkylthio represents a radical which, in addition to the sulfur atom, contains one of the abovementioned 1-4C-alkyl radicals. Examples which may be mentioned are the methylthio and the ethylthio radicals.
1-7C-Alkylene represents straight-chain or branched 1-7C-alkylene radicals, for example the methylene (—CH
2
—), ethylene (—CH
2
—CH
2
—), trimethylene (—CH
2
—CH
2
—CH
2
—), tetra-methylene (—CH
2
—CH
2
—CH
2
—), 1,2-dimethylethylene [—CH(CH
3
)—CH(CH
3
)—], 1,1-dimethylethylene [—C(CH
3
)
2
—CH
2
—], 2,2-dimethylethylene [—CH
2
—C(CH
3
)
2
—], isopropylidene [—C(CH
3
)
2
—], 1-methylethylene [—CH(CH
3
)—CH
2
—], pentamethylene (—CH
2
—CH
2
—CH
2
—CH
2
—CH
2
—), hexamethylene (—CH
2
—CH
2
—CH
2
—CH
2
—CH
2
—CH
2
—) and the heptamethylene (—CH
2
—CH
2
—CH
2
—CH
2
—CH
2
—CH
2
—CH
2
—) radicals. When t is the number 1 or t is the number 0 and at the same time u is the number 1, A preferably has the meaning 2-7C-alkylene. Of the alkylene radicals A, the ethylene, the propylene and the butylene radicals are preferred.
2-7C-Alkenylene represents straight-chain or branched 2-7C-alkenylene radicals, under which is understood a mono- or polyunsaturated divalent hydrocarbon radical. Examples which may be mentioned are the vinylene (—CH═CH—), 1-propenylene (—CH═CH—CH
2
—), 2-butenylene (—CH
2
—CH═CH—CH
2
—) and the 1,3-butadienylene (—CH═CH—CH═CH—) radicals.
3-7C-Cycloalkyl represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl.
3-7C-Cycloalkylene represents one of the abovementioned 3-7C-cycloalkyl radicals having two bonds. An example which may be mentioned is the 1,4-cyclohexylene radical.
Phenylene represents the 1,2-, 1,3- and 1,4-phenylene radicals, of which the 1,4-phenylene radical is preferred.
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 (
Grundler Gerhard
Zimmerman Peter
Altana Pharma AG
Juneau Todd L.
Nath Gary M.
Nath & Associates PLLC
Patel Sudhaker B.
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