Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2001-10-03
2003-01-07
Huang, Evelyn Mei (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
06503923
ABSTRACT:
This is a nationalization of PCT/EP00/03388 filed Apr. 14, 2000 and published in English.
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 to the imidazopyridine parent structure, which are intended to be suitable for the treatment of peptic ulcers.—International Patent Application WO98/42707 discloses tetrahydroimidazonaphthyridines having a very specific substitution pattern, which are likewise intended to be suitable for the treatment of gastric and intestinal disorders.
DESCRIPTION OF THE INVENTION
The invention relates to compounds of the formula I
in which
R1 is hydrogen, 1-4C-alkyl or hydroxy-1-4C-alkyl,
R2 is hydrogen, 1-4C-alkyl, hydroxy-1-4C-alkyl, halogen, 2-4C-alkenyl or 2-4C-alkynyl,
R3 is hydrogen, halogen, trifluoromethyl, 1-4C-alkyl, 2-4C-alkenyl or 2-4C-alkynyl,
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 in which R4a and R4b together are O (oxygen),
where R4′ is 1-4C-alkoxy which is completely or mainly substituted by halogen,
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 in which R5a and R5b together are O (oxygen),
where R5′ is 1-4C-alkoxy which is completely or mainly substituted by halogen,
where one of the substituents R4a and R4b must have the meaning R4′ and/or one of the substituents R5a and R5b must have the meaning R5′,
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 in each case is hydrogen, and the other substituents in each case together form a 1-2C-alkylenedioxy radical which is completely or partially substituted by halogen,
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 strain-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 radical.
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, the 2-hydroxyethyl and the 3-hydroxypropyl radical.
Halogen within the meaning of the invention is bromine, chlorine or fluorine.
2-4C-alkenyl represents straight-chain or branched alkenyl radicals having 2 to 4 carbon atoms. Examples which may be mentioned are the 2-butenyl, 3-butenyl, 1-propenyl and the 2-propenyl radical (allyl radical).
2-4C-alkynyl represents straight-chain or branched alkynyl radicals having 2 to 4 carbon atoms. Examples which may be mentioned are the 2-butynyl, 3-butynyl and preferably the 2-propynyl radical (propargyl radical).
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 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-methoxyethoxy (CH
3
—O—CH
2
—CH
2
—O—) and 2-ethoxyethoxy (CH
3
—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 1-4C-alkylcarbonyl group which is bonded to an oxygen atom. An example which may be mentioned is the acetoxy radical (CH
3
CO—O—).
Completely or mainly halogen-substituted 1-4C-alkoxy which may be primarily mentioned are chlorine and/or, in particular, fluorine-substituted 1-4C-alkoxy radicals. Examples of halogen-substituted 1-4C-alkoxy which may be mentioned are the 2,2,2-trichloroethoxy, the hexachloroisopropoxy, the pentachloroisopropoxy, the 1,1,1-trichloro-3,3,3-trifluoro-2-propoxy, the 1,1,1-trichloro-2-methyl-2-propoxy, the 1,1,1-trichloro-2-propoxy, the 3-bromo-1,1,1-trifluoro-2-propoxy, the 3-bromo-1,1,1-trifluoro-2-butoxy, the 4-bromo-3,3,4,4-tetrafluoro-1-butoxy, the chlorodifluoromethoxy, the 1,1,1,3,3,3-hexafluoro-2-propoxy, the 2-trifluoromethyl-2-propoxy, the 1,1,1-trifluoro-2-propoxy, the perfluoro-tert-butoxy, the 2,2,3,3,4,4,4-heptafluoro-1-butoxy, the 4,4,4-trifluoro-1-butoxy, the 2,2,3,3,3-pentafluoropropoxy, the perfluoroethoxy, the 1,2,2-trifluoroethoxy, in particular the 1,1,2,2-tetrafluoroethoxy, the 2,2,2-trifluoroethoxy, the trifluoromethoxy and preferably the difluoromethoxy radical.
Completely or partially halogen-substituted 1-2C-alkylenedioxy which may be mentioned in particular are fluorine-substituted 1-2C-alkylenedioxy, for example the difluoroethylenedioxy (—O—CF
2
—CH
2
—O—), the tetrafluoroethylenedioxy (—O—CF
2
—CF
2
—O—) and in particular the difluoromethylenedioxy (—O—CF
2
—O—), and the 1,1,2-trifluoroethylenedioxy radical (—O—CF
2
CHF—O—) and also the chlorotrifluoroethylenedioxy radical.
1-4C-alkoxycarbonyl represents a carbonyl group to which one of the abovementioned 1-4C-alkoxy radicals is bonded. Examples which may be mentioned are the methoxycarbonyl (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 and the methoxycarbonylamino radical.
1-4C-alkoxy-1-4C-alkoxycarbonyl represents a carbonyl group to which one of the abovementioned 1-4C-alkoxy-1-4C-alkoxy radicals is bonded. Examples which may be mentioned are the 2-methoxyethoxycarbonyl(CH
3
—O—CH
2
CH
2
—O—CO—) and the 2-ethoxyethoxycarbonyl 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-methoxyethoxycarbonylamino and der 2-ethoxyethoxycarbonylamino radical.
Possible 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 which are 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 it is a mono- or polybasic acid and depending on which salt is desired—in an equimolar quantitative ratio or one differing therefrom.
Pharmacologically intolerable salts, which can be initially obtained, for example, as process products in the preparation of the compounds according to the invention on the industrial scale, are converted into pharmacologically tolerable salts by processes known to the person skilled in the art.
It is known to the person skilled in the art that the compounds according to the invention and their salts can contain various amounts of solvents if they are isolated, for example, in crystal
ALTANA Pharma AG
Huang Evelyn Mei
Jacobson & Holman PLLC
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