EP1575925A1 - Nouveaux amides d'acide carboxylique, leur production et leur utilisation en tant que medicaments - Google Patents

Nouveaux amides d'acide carboxylique, leur production et leur utilisation en tant que medicaments

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Publication number
EP1575925A1
EP1575925A1 EP03767800A EP03767800A EP1575925A1 EP 1575925 A1 EP1575925 A1 EP 1575925A1 EP 03767800 A EP03767800 A EP 03767800A EP 03767800 A EP03767800 A EP 03767800A EP 1575925 A1 EP1575925 A1 EP 1575925A1
Authority
EP
European Patent Office
Prior art keywords
chloro
benzimidazol
benzamide
carbonyl
methyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP03767800A
Other languages
German (de)
English (en)
Inventor
Henning Priepke
Roland Pfau
Kai Gerlach
James Gillard
Eckhart Bauer
Wolfgang Wienen
Sandra Handschuh
Herbert Nar
Annette Schuler-Metz
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Boehringer Ingelheim International GmbH
Original Assignee
Boehringer Ingelheim International GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DE2002159407 external-priority patent/DE10259407A1/de
Priority claimed from DE10335545A external-priority patent/DE10335545A1/de
Application filed by Boehringer Ingelheim International GmbH filed Critical Boehringer Ingelheim International GmbH
Publication of EP1575925A1 publication Critical patent/EP1575925A1/fr
Withdrawn legal-status Critical Current

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    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
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    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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    • C07D513/04—Ortho-condensed systems

Definitions

  • New carboxylic acid amides their preparation and their use as pharmaceuticals
  • the present invention relates to novel substituted carboxylic acid amides of the general formula
  • the compounds of the above general formula I and their tautomers, their enantiomers, their diastereomers, their mixtures and their salts, in particular their physiologically acceptable salts with inorganic or organic acids or bases, and their stereoisomers have valuable pharmacological properties, in particular an antithrombotic activity and a factor Xa-inhibiting effect.
  • the present application thus provides the novel compounds of the above general formula I, their preparation, the medicaments containing the pharmacologically active compounds, their preparation and use.
  • R 1 is an amino, C ⁇ -5 alkylamino, C 3-7 cycloalkylamino or (phenyl-C ⁇ -3 alkyl) amino group, each on the amine nitrogen atom additionally by a phenylcarbonyl or phenylsulphonyl group or by an in alkyl moiety is optionally substituted by a hydroxy, C ⁇ -3 alkyloxy or carboxyl group, can be converted in vivo into a carboxy group, an amino, C ⁇ -3 alkylamino, di- (C ⁇ -3 alkyl) amino or a 4- to 7-gliedri- ge cycloalkyleneimino group substituted C ⁇ -5 alkyl or C 1-5 alkylcarbonyl in the above-mentioned substituted C 1-8 -alkyl group, two heteroatoms are separated from one another by at least two carbon atoms,
  • C- ⁇ - 3 alkyl amino-C ⁇ - 3 alkyl, C 3 - 6 cycloalkylamino C ⁇ .3-alkyl, phenylamino-C 1-3 alkyl- -AL-, Ci-s-alkylamino- Ci-s-alkyl, di (C ⁇ -5- alkyl) -amino-C- ⁇ -3 -alkyl, / V- (C 3-6 -cycloalkyl) -C ⁇ .
  • a methylene group in the 3-position of a 5-membered cycloalkyleneimino group may be replaced by a sulfur atom, a sulfinyl or sulfonyl group, or a methylene group in the 4-position of a 6- or 7-membered cycloalkyleneimino group by an oxygen or sulfur atom, a carbonyl, sulfinyl or sulfonyl group or by an optionally by a C- ⁇ - 3 alkyl, hydroxy, formyl - or C ⁇ -3 alkylcarbonyl group substituted -NH group may be replaced, and in addition a methylene group adjacent to the above-mentioned optionally substituted -NH group by a carbonyl, sulphinyl or sulphonyl group may be replaced, with the proviso that
  • C ⁇ -3 alkyl amino-C ⁇ . 3 alkyl, C ⁇ -3 alkyl amino-3 C ⁇ - -alkyl, di- (3 C ⁇ - alkyl) -ami ⁇ o ⁇ alkyl--C-, a 4- to 7-membered cycloalkylene imino-C- ⁇ - 3 -alkyl, C 3-6 -cycloalkylamino-C ⁇ -3 alkyl, phenyl, phenyl-C ⁇ -3 alkyl, aryl Hefero-, heteroaryl-C ⁇ -3 alkyl, aminocarbonyl, C ⁇ -3 alkylaminocarbonyl, di- (C ⁇ -3 alkyl) - aminocarbonyl or 4- to 7-membered Cycloalkyleniminocarbonyl deficit substituted 5- to 7-membered Cycloalkenyleniminocarbonyl- or Cycloalkenyleniminosulfonyl- group, wherein the double
  • the methylene group in the 2-, 3- or 4-position in a C 3-7 cycloalkylcarbonyl group may be replaced by an oxygen or sulfur atom, a carbonyl, sulfinyl, sulfonyl or -NH group in which
  • the hydrogen atom of the -NH group can be replaced by a C 1-3 -alkyl or d-3-alkylcarbonyl group,
  • the phenyl moiety by a fluorine, chlorine or bromine atom, by a trifluoromethyl, d- 3- alkyl, amino-d.3-alkyl, ds-alkylamino-C ⁇ s-alkyl, di (d -3 alkyl) amino
  • C ⁇ - 3 alkyl a 4- to 7-membered CycIoalkylenimino-C ⁇ .3-alkyl or d- 3 alkoxy group may be substituted and / or
  • a methylene group which is adjacent to the nitrogen atom may be replaced by a carbonyl group in a 5- to 7-membered cycloalkyleneimino group, or a group of the formula
  • heterocyclic portion represents a hydrogen atom by a C 1-3 alkyl, d-3 alkyloxy, C ⁇ -3 alkyloxycarbonyl-, C ⁇ -5 -Alkyloxycarbonylamino-
  • C 3 -alkyl-, methylsulfonylmethyl-, amino-C 3 -3 -alkyl-, d-3-alkylamino-C 3 -3 -alkyl-, di- (C 3 -alkyl) -amino-d- 3- alkyl- group, a 4- to 7-membered Cycloalkylenimino-C ⁇ -3-alkyl, morpholin-4-yl-C ⁇ -3 alkyl, piperazinyl-d-3-alkyl, a / - (C 1-3 alkyl) -piperazin-4-yl-C 1-3 -alkyl, aminocarbonyl, d- 3- alkylaminocarbonyl or di- (C 3 -3 -alkyl) -aminocarbonyl group may be replaced and
  • n 1 or 2
  • R 2 is a hydrogen, fluorine, chlorine or bromine atom, a C 3 alkyl group in which the hydrogen atoms may be wholly or partly replaced by fluorine atoms, a C 2 -3-alkenyl, C 2 - 3 alkynyl , d-3-alkoxy, a mono-, di- or trifluoromethoxy group, R 3 is a hydrogen atom or a d -3 -alkyl group,
  • R 4 is a hydrogen atom, a C 2 - 3 -alkenyl or C 2-3 -alkynyl group or a straight-chain or branched d-5-alkyl group, optionally substituted by a fluorine atom, a mono-, di- or trifluoromethyl, a Nitrile, hydroxy, a C ⁇ - 5 alkyloxy group in which the hydrogen atoms may be wholly or partially replaced by fluorine atoms, an allyloxy, Propargyloxy-, benzyloxy, -C -5 -alkylcarbonyloxy-, -C -5 -alkyloxycarbonyloxy-, Carboxy-d- 3 -alkyloxy, C ⁇ .
  • R 1 is a hydrogen atom or a C 3 alkyl group
  • A is a heteroaryl group or a C 5-7 cycloalkyl group, in the the methine group may be replaced in position 1 by a nitrogen atom and / or
  • -N (OH) -, -N (-C 3 -alkyl) -, -N (C 3 -alkylcarbonyl) - or -N (heteroaryl) group can be replaced and / or
  • Carbonyl, sulfinyl or sulfonyl group may be replaced,
  • (D- 3- alkyl) amino group may be substituted and / or
  • -NH-group can be replaced, and in addition a methylene group adjacent to an above-mentioned -NH- or -N (C ⁇ -3 alkyl) group by a carbonyl group may be substituted, or
  • a methylene group in the 2-position of a 5-membered cycloalkyleneimino group may be replaced by a carbonyl, sulphinyl or sulphonyl group,
  • R 8 is a hydrogen atom, a 3 C ⁇ - -alkyl or C 1-3 -alkylcarbonyl group is substituted,
  • a 3- to 7-membered cycloalkyl-d-3-alkyl or C ⁇ - Cycloalkylenimino-3 alkyl group a methylene group optionally substituted in the in the cyclic moiety by one by a C ⁇ -3 alkyl or C ⁇ -3 alkylcarbonyl group - NH group can be replaced and in addition one of a -NH-, -N (C ⁇ - 3 alkylcarbonyl) - or -N (C ⁇ _ 3 alkyl) - group adjacent methylene group may be replaced by a carbonyl or sulfonyl group with the proviso that a cycloalkyleneimino group as defined above, in which two nitrogen atoms are separated by exactly one -CH 2 group, is excluded, R 5 is a hydrogen atom or an alkyl group or C ⁇ -3
  • R 4 and R 5 together with the carbon atom to which they are attached, a C 3 - 7 cycloalkyl group wherein
  • one of the methylene groups of the C 3 -7-cycloalkyl group may be replaced by an imino, d -3- alkyl-imino, acylimino or sulfonylimino group,
  • A is a carbonylamino or aminocarbonyl group, wherein the hydrogen atom of the amino function may optionally be substituted by a C 1-3 alkyl group, and
  • n is the number 1 or 2
  • R 6 is a hydrogen atom or a d -3 alkyl, hydroxy, C ⁇ - 5 -alkyloxycarbonyl, carboxy-d-3-alkyl, d-3-alkoxycarbonyl-3 C ⁇ - alkyl, amino or C ⁇ - 3-Alkylamino- group and
  • R 7 is a hydrogen, fluorine, chlorine or bromine atom, a d -3 alkyl group in which the Hydrogen atoms may be replaced by fluorine atoms totally or partially, a C 2-3 alkenyl or C 2- 3-alkynyl, hydroxy, C ⁇ -3-alkoxy, trifluoromethoxy, amino, nitro or cyano group,
  • heteroaryl group in the carbon skeleton optionally by a fluorine, chlorine, bromine or iodine atom, a C 3-alkyl, amino, d- 3 alkyl amino, di- (C ⁇ -3 alkyl) -amino, d-3-alkyloxy, carboxy, C ⁇ -3 -alkoxy-carbonyl or C ⁇ - 3 alkoxycarbonylamino substituted monocyclic 5- or 6- is to understand the heteroaryl group, wherein
  • the 6-membered heteroaryl group contains one, two or three nitrogen atoms and
  • the 5-membered heteroaryl group is an imino group optionally substituted by a C 1-3 -alkyl or phenyl-C 1-3 -alkyl group, an oxygen or sulfur atom or
  • a -C 3 alkyl amino C 2-3 alkyl, C 3 -alkylamino C 2 -3 -alkyl, di- (C 3 -alkyl) amino C 2 . 3 -alkyl-, a 4- to 7-membered cycloalkylene-imino-d- 3 -alkyl or phenyl-C ⁇ - 3 -alkyl group substituted imino group or a
  • the bond is via a nitrogen atom or via a carbon atom of the heterocyclic part or a fused-on phenyl ring, wherein the alkyl and alkoxy groups having more than two carbon atoms contained in the above-mentioned definitions, unless otherwise mentioned, may be straight-chain or branched, and the alkyl groups in the above-mentioned dialkylated groups, for example, the dialkylamino groups, the same or different could be,
  • Examples of monocyclic heteroaryl groups are the pyridyl, ⁇ / -oxypyridyl, pyrazolyl, pyridazinyl, pyrimidinyl, pyrazinyl, [1,2,3] triazinyl, f1, 3,5] triazinyl, [1 , 2,4] triazinyl, pyrrolyl, imidazolyl, [1, 2,4] triazolyl, [1, 2,3] trazazolyl, tetrazolyl, furanyl, isoxazolyl, oxazolyl, [1, 2 , 3] oxadiazolyl, [1, 2,4] oxadiazolyl, furazanyl, thiophenyl, thiazolyl, isothiazolyl, [1, 2,3] thiadiazolyl, [1, 2,4] thiadiazolyl or [1 , 2,5] thiadiazolyl group.
  • bicyclic heteroaryl groups are the benzimidazolyl, benzofuranyl, benzo [c] furanyl, benzothiophenyl, benzo [c] thiophenyl, benzothiazolyl, benzo [c] isothiazolyl, benzo [c /] isothiazolyl, benzooxazolyl , Benzo [c] isoxazolyl, benzo [c /] isoxazolyl, benzo [1, 2,5] oxadiazolyl, benzo [1, 2,5] thiadiazolyl, benzo [1,2,3] thiadiazolyl , Benzo [cj [1, 2,3] triazinyl, benzo [1,2,4] triazinyl, benzotriazolyl, cinnolinyl, quinolinyl, ⁇ / oxyquinolinyl, isoquinolinyl, quinazolinyl, ⁇ / Oxyquina
  • Examples of the d -B- alkyl groups mentioned above in the definitions are the methyl, ethyl, 1-propyl, 2-propyl, ⁇ -butyl, sec-butyl, terf-butyl, 1-pentyl , 2-pentyl, 3-pentyl, 1-hexyl, 2-hexyl, 3-hexyl, 1-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, 1-octyl , 2-octyl, 3-octyl or 4-octyl group.
  • Examples of the d -8- alkyloxy groups mentioned above in the definitions are the methyloxy, ethyloxy, 1-propyloxy, 2-propyloxy, ⁇ -butyloxy, sec-butyloxy, tert-butyloxy, 1-pentyloxy , 2-pentyloxy, 3-pentyloxy, 1-hexyloxy, 2-hexyloxy, 3-hexyloxy, 1-heptyloxy, 2-heptyloxy, 3-heptyloxy, 4-heptyloxy, 1-octyloxy, 2-octyloxy, 3-octyloxy or 4-octyloxy.
  • a converted in vivo into a carboxy group is, for example, an esterified carboxy group with an alcohol in which the alcoholic moiety is preferably a Ci-e-alkanol, a phenyl-d -3 -alkanol, a C 3- 9-cycloalkanol, C 5-7 -CycloaIkenol, a C 3-5 alkenol, a phenyl-C 3- 5-alkenol, a C3 -5-alkynol or Phenvl-ds-alkynol with the proviso that no bond to the oxygen atom by a carbon atom originates, which carries a double or triple bond, a C 3-8 cycloalkyl d- 3 alkanol or an alcohol of the formula
  • R 9 is -CO-O- (R 10 CR 11 ) -OH
  • R 9 is a d -8 alkyl, C 5 - 7 -Cycioa ⁇ kyl, phenyl or phenyl-d -3 -aIkyl distr,
  • R 10 is a hydrogen atom, a d -3 alkyl, Cs 7 cycloalkyl or phenyl group and
  • R 11 represents a hydrogen atom or a C 1-3 -alkyl group
  • Preferred radicals which can be split off from a carboxy group in vivo are a C 1-4 -alkoxy group such as the methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, ⁇ -pentyloxy, n-hexyloxy or cyclohexyloxy group or a Phenyl-d- 3- alkoxy group such as the benzyloxy group into consideration.
  • a second embodiment of the present invention includes those compounds of general formula I, in which
  • R, R, R, R, A and B are defined as described in the 1st embodiment, and
  • R is the hydrogen atom
  • R 1 , R 2 , R 4 , R 5 and B are defined as described in the first embodiment, wherein R 4 is not the hydrogen atom, and
  • R 6 is the hydrogen atom
  • R 1 to R 5 and A are defined as described in the first embodiment, wherein R 2 is not the hydrogen atom, and B is a group of. formula
  • n, R 6 and R 7 are defined as described in the first embodiment
  • R 1 , R 2 , R 4 , R 5 , A and B are defined as described in the 4th embodiment, and
  • R 3 is the hydrogen atom
  • R 1 , R 2 , R 4 and R 5 are as defined in the 4th embodiment, wherein R 4 is not the hydrogen atom, and
  • R 7 is a fluorine, chlorine or bromine atom, a -C 3 alkyl group in which the hydrogen atoms may be wholly or partially replaced by fluorine atoms, a C 2-3 alkenyl or C 2 - 3 alkynyl, a -C 3- alkyloxy, trifluoromethoxy or cyano group,
  • R 1 is an amino, d -5 alkylamino, C 3-7 cycloalkylamino or (phenyl-C ⁇ -3 alkyl) amino group, each on the amine nitrogen atom additionally by a in the alkyl portion optionally substituted by a carboxy group, a in vivo into a carboxy group convertible group, an amino, C-3-alkylamino, di (d -3 -alkyl) -amino or a 4- to 7-membered cycloalkyleneimino group substituted C 1-5 alkyl or d -5 alkylcarbonyl group may be substituted, wherein, in the above-mentioned substituted alkyl group C ⁇ - 5 two heteroatoms by at least two carbon atoms from each other, are separated,
  • 3 -alkyl a 4- to 7-membered cycloalkyleneimino-C 1 .
  • a methylene group in the 3-position of a 5-g-membered cycloalkyleneimino group may be replaced by a sulfur atom, a sulfinyl or sulfonyl group, or
  • a methylene group in the 4-position of a 6- or 7-membered cycloalkyleneimino group may be replaced by an oxygen or sulfur atom, a carbonyl or by an optionally substituted by a methyl or hydroxy group -NH group, wherein additionally a methylene group adjacent to the above said -NH group may be replaced by a carbonyl group,
  • alkyl optionally substituted by one or two C ⁇ -3-alkyl, amino-d -3 alkyl, C ⁇ -3-alkyl amino-C- ⁇ - 3, di (C ⁇ -3 alkyl) amino -C ⁇ -3-alkyl, a 4- to 7-membered cycloalkylene imino-C ⁇ .
  • substituents may be the same or different and each one of C ⁇ -5 alkyl groups, alkyl interrupted by one or two hydroxy-d- 3, C ⁇ - 3 alkoxy-3 C ⁇ - alkyl, amino-3 C ⁇ - alkyl, C ⁇ -3 alkylamino-C 1-3 alkyl, di (d -3 alkyl) amino d 3 alkyl, 4- to 7-membered cycloalkyleneimino-d, 3- alkyl or C 3 . 6 -cycloalkylamino-C ⁇ - 3- alkyl group may be substituted,
  • a methylene group which is adjacent to the nitrogen atom may be replaced by a carbonyl group in a 5- to 7-membered cycloalkyleneimino group
  • a hydrogen atom by a d- 3 -AlkyI- oxycarbonyl, C ⁇ -5 -AIkyloxycarbonylamino-C ⁇ - 3 -alkyl, amino-d -3 -alkyl, d -3 -alkylamino-d - 3- alkyl, di- (C ⁇ -3 alkyl) amino-C ⁇ -3 alkyl or aminocarbonyl can be replaced and
  • n 1 or 2
  • R 2 is a fluorine, chlorine or bromine atom, a d-3-alkyl group in which the hydrogen atoms may be wholly or partially replaced by fluorine atoms, a C 2 - 3 alkenyl, C 2-3 alkynyl or -C. 3- alkyloxy group in which the hydrogen atoms may be wholly or partly replaced by fluorine atoms,
  • R 3 is a hydrogen atom
  • R 4 is a hydrogen atom, a C 2-3 -alkenyl or C 2-3 -alkynyl group or a straight or branched C ⁇ -5 alkyl group optionally substituted by a hydroxy, C ⁇ - 3 alkyloxy group in which the hydrogen atoms atoms may be replaced entirely or partly replaced by fluorine, an allyloxy, propargyloxy, benzyloxy, carboxy-C ⁇ -3 -AL- kyloxy-, C ⁇ -5 -A!
  • a methylene group of the Cycloalkyleniminoteils by an optionally substituted by a hydroxy, amino, C ⁇ -3 alkylamino, di- (C ⁇ -3 alkyl) amino, a 4- to 7-membered cycloalkyleneimino or -C -5 alkyloxycarbonylamino group substituted d -3 -alkenyl group and a non-imino group adjacent the methylene group of the cycloalkylenimine by a hydroxy, amino, C 3 -alkylamino, di (d -3 -alkyl) - amino, aminocarbonyl, C 1-3 alkylaminocarbonyl or di- (C ⁇ - 3 alkyl) -aminocarbo- nyl distr may be substituted and / or a methylene group in the 4-position of a 6- or 7-membered cycloalkyleneimino group by an oxygen or sulfur atom, by a carbonyl,
  • R 8 is a hydrogen atom, a C ⁇ -3 alkyl or C ⁇ means -3 alkylcarbonyl group is substituted,
  • R 5 is a hydrogen atom
  • A is a carbonylamino or aminocarbonyl group
  • R 7 represents a fluorine, chlorine or bromine atom
  • heteroaryl group one in the carbon skeleton optionally substituted by a C 1-3 -alkyl, d -3- alkylamino, di (d -3 -alkyl) - amino, carboxy, d- 3- alkoxycarbonyl or d- 3- alkoxycarbonylamino group is to be understood monocyclic substituted 5- or 6-membered heteroaryl group, wherein
  • the 6-membered heteroaryl group contains one, two or three nitrogen atoms and
  • the 5-membered heteroaryl group optionally substituted by a C ⁇ -3 alkyl or
  • C ⁇ -3 alkyl optionally substituted by a C ⁇ -3 alkyl, amino-C 2 - 3 alkyl, d- 3 alkylamino C 2 -3-alkyl-, di- (C ⁇ -3 alkyl) amino-C 2- 3-alkyl, a 4- to 7-membered cycloalkylene-imino-C ⁇ - 3 -alkyl-, or phenyl-C 3 -alkyl group-substituted imino group or an oxygen or sulfur atom and additionally a nitrogen atom or
  • a phenyl ring optionally substituted by a chlorine or bromine atom may be fused and the bond is via a nitrogen atom or via a carbon atom of the heterocyclic part or a fused-on phenyl ring,
  • alkyl and alkoxy groups having more than two carbon atoms contained in the above-mentioned definitions, unless otherwise mentioned, may be straight-chain or branched, and the alkyl groups in the above-mentioned dialkylated groups, for example, the dialkylamino groups, the same or different could be,
  • D R2, D R4 4 and R ö are defined as described in the 7th embodiment, wherein R 4 is not the hydrogen atom, and
  • R 7 represents a chlorine or bromine atom
  • R is a group of the formula
  • R 13 represents a hydrogen atom, a methyl or aminomethyl group
  • R 2 is a fluorine, chlorine or bromine atom, a methyl, ethyl, trifluoromethyl or methoxy group,
  • R 4 is a d -4- alkyl group which is represented by a fluorine atom, a hydroxy, C 1-3 -alkyloxy, trifluoromethoxy, 2,2,2-trifluoroethyloxy, allyloxy, propargyloxy, mercapto, C ⁇ - alkyl sulfanyl, C ⁇ - alkylsulfinyl, C ⁇ -4 alkylsulfonyl, amino, C ⁇ -3 alkylcarbonylamino, d- 3 alkylsulfonylamino, carboxy, aminocarbonyl, d- 3 alkylaminocarbonyl, di (d 3- alkyl) -aminocarbonyl or a 4- to 7-membered cycloalkyleniminocarbonyl group may be substituted,
  • R 7 is a chlorine or bromine atom
  • R 1 is a group of the formula
  • R 12 is the hydrogen atom, a methyl, aminomethyl, C 3 -3 -alkylamino-d 2 -alkyl, di (C 3 -alkyl) amino-C 2 -alkyl, pyrrolidin-1-yl methyl- or 2- (pyrrolidin-1-yl) -ethyl- group and
  • R 1 represents a hydrogen atom, a methyl or aminomethyl group
  • R is a fluorine, chlorine or bromine atom, a methyl, ethyl, trifluoromethyl or methoxy group
  • R 4 is a C ⁇ -4 alkyl group by fluorine atom, a hydroxy, d- 3 alkyloxy, trifluoromethoxy, 2,2,2-Trifluorethyloxy-, allyloxy, propargyloxy, mercapto, d- 4 - alkyl sulfanyl, C 1- -AIkylsulfinyl-, d- alkylsulfonyl, amino, C ⁇ -3 -alkylcarbonylamino-, C ⁇ -3 alkylsulfonylamino, carboxy, aminocarbonyl, C ⁇ -3 alkylaminocarbonyl, di- (C ⁇ -3 alkyl) aminocarbonyl or a 4- to 7-membered Cycloalkyleniminocarbonyl- group is substituted,
  • R 7 is a chlorine or bromine atom
  • An 11th embodiment of the present invention comprises the compounds of the above general formula I in which
  • R 1 is a 2,5-dihydro-1H-pyrro-1-yl-carbonyl, pyrrolidin-1-yl-carbonyl, ⁇ / -acetyl-N-cyclobutylamino, 2- ( ⁇ / -fet. Butoxycarbonylaminomethyl ) -pyrrolidin-1-yl-carbonyl, 2- (aminomethyl) -pyrrolidin-1-yl-carbonyl, 3-oxo-piperazin-1-yl-carbonyl, 4-methyl-3-oxo-piperazine-1 - yl-carbonyl, 2,3-dihydro-imidazo [2,1-b] -thiazo!
  • R 2 is a fluorine, chlorine or bromine atom, a C ⁇ -3 alkyl group in which the hydrogen atoms may be wholly or partly replaced by fluorine atoms, a C ⁇ -3 alkyloxy- or C 2-3 alkynyl group,
  • R 3 is a hydrogen atom
  • R 4 is a hydrogen atom or a methyl, ethyl, propyl, isopropyl, isobutyl, tert-butyl, hydroxymethyl, 1-hydroxyethyl, methoxymethyl, 2-methoxyethyl, phenyl, 2-chlorophenyl , 3-chlorophenyl, 4-chlorophenyl, benzyl, 4-hydroxybenzyl, 4-methoxycarbonylmethoxy-phenyl-methyl, pyridin-4-yl-methyl, pyridin-2-yl-methyl, piperidine 1-yl-methyl, piperidin-3-yl-methyl, 1-himidazol-4-yl-methyl, aminocarbonylmethyl, 4-benzyloxycarbonylaminobutyl, 2-methylsulfanyl-ethyl, 2-methylsulfinyl-ethyl, 2- Methylsulfonylethyl, ethylsulfanylmethyl
  • R is a hydrogen atom
  • A is an aminocarbonyl or carbonylamino group
  • R 7 represents a fluorine, chlorine or bromine atom or a methyl group
  • R 1 is an amino, C ⁇ - 5 alkylamino, C 3-7 cycloalkylamino or (phenyl-C ⁇ -3 alkyl) - amino group, respectively, on the amine nitrogen atom additionally by a phenylcarbonyl or phenylsulphonyl group or by a in the alkyl moiety optionally substituted by a hydroxy, C ⁇ -3 alkyloxy or carboxyl group, can be converted in vivo into a carboxy group, an amino, C ⁇ -3 alkylamino, di- (C ⁇ -3 alkyl) amino group or a 4 - to 7-membered cycloalkyleneimino group substituted d- 5 alkyl or d -5 alkylcarbonyl group may be substituted, said substituted in the above-mentioned d-5-alkyl group two heteroatoms are separated by at least two carbon atoms,
  • the cycloalkyleneimine part in the carbon skeleton is replaced by one or two C 1-3 -alkyl
  • a methylene group in the 3-position of a 5-membered cycloalkyleneimino group may be replaced by a sulfur atom, a sulfinyl or sulfonyl group, or
  • Formyl or C 1-3 -alkylcarbonyl substituted -NH group may be replaced, wherein additionally a methylene group adjacent to the above -NH group may be replaced by a carbonyl group, with the proviso that
  • the methylene group in the 2-, 3- or 4-position in a C 3-7 cycloalkylcarbonyl group may be replaced by an oxygen or sulfur atom, a carbonyl, sulfinyl, sulfonyl or -NH group in which
  • the hydrogen atom of the -NH group can be replaced by a C 1-3 -alkyl or d -3- alkylcarbonyl group, phenylcarbonyl or heteroarylcarbonyl group, the alkyl in the phenyl or heteroaryl moiety by a fluorine, chlorine or bromine atom, by a trifluoromethyl, C ⁇ -3 alkyl, amino-C ⁇ - 3, C ⁇ -3-alkylamino-C ⁇ - 3- alkyl, di- (C 3 -alkyl) amino-d. 3 -alkyl-, C 3 - 6 -cycloalkylenimino-C ⁇ . 3- alkyl or C 1-3 alkoxy group may be substituted,
  • the phenyl moiety by a fluorine, chlorine or bromine atom, by a trifluoromethyl, d- C3 alkyl, amino-C ⁇ .3 alkyl, C ⁇ -3 alkylamino-C ⁇ .3-alkyl, di- (C 1-3 -alkyl) -amino-C ⁇ -3 -alkyl-, C 3-6 -cycloalkylenimino-C ⁇ . 3 alkyl or C ⁇ -3 alkoxy group may be substituted and / or
  • the hydrogen atom of the -NH group may be replaced by a d -3 -alkyl or d- 3- alkylcarbonyl group, and / or
  • a methylene group which is adjacent to the nitrogen atom may be replaced by a carbonyl group in a 5- to 7-membered cycloalkyleneimino group
  • a hydrogen atom by a C- ⁇ - 3 -alkyloxycarbonyl, d.5-alkyloxycarbonylamino-d -3 alkyl, methylsulfonyl, methyl, amino-C ⁇ - 3 alkyl in the heterocyclic part, -3 C ⁇ - alkylamino-C ⁇ -3 alkyl, di- (d -3 alkyl) amino C ⁇ -3 alkyl, aminocarbonyl, C ⁇ -3 alkylaminocarbonyl or di- (C ⁇ -3 alkyl) amino carbonyl group can be replaced and
  • n 1 or 2
  • R is a hydrogen, fluorine, chlorine or bromine atom, a C 1-3 -alkyl group in which the hydrogen atoms may be wholly or partly replaced by fluorine atoms, a C 2-3 alkenyl, C 2-3 alkynyl, d -3 -alkoxy, a mono-, di- or trifluoromethoxy group,
  • R 3 is a hydrogen atom or a C ⁇ -3 alkyl group
  • R 4 is a hydrogen atom or a straight-chain or branched C. 5 alkyl group optionally substituted by a fluorine atom, a mono-, di- or trifluoromethyl, a hydroxy, a C 3 alkyloxy group in which the hydrogen atoms may be wholly or partly replaced by fluorine atoms, an allyloxy, propargyloxy , benzyloxy, C ⁇ -5-alkylcarbonyloxy, C 1-5 -Alkyloxycarbonyloxy-, carboxy-d -3 alkyloxy, C 1-5 alkyloxy- carbonyl-C ⁇ -3 alkyloxy, d-8 alkyloxycarbonylamino , Chloro-C 1-3 -alkylaminocarbonylamino, mercapto, C 1-3 -alkylsulfanyl, d- 3 -alkylsulfinyl, d.
  • a 4- to 7-membered cycloalkyleneiminocarbonyl-d- 3- alkyl group wherein a methylene group of the Cycloalkyleniminoteils by an optionally substituted by a hydroxy, amino, C ⁇ - 3 alkylamino, di (d -3 alkyl) amino, a 4- to 7-membered cycloalkyleneimino or C -5 alkyloxycarbonylamino group substituted C ⁇ . 3- alkyl group and a non-imino group adjacent methylene group of
  • Cycloalkyleniminoteils by a hydroxy, amino, C ⁇ -3 alkylamino, di (C 3 -3 alkyl) amino, aminocarbonyl, C ⁇ -3 alkylaminocarbonyl or di (d -3 alkyl) - aminocarbonyl distr may be substituted and / or
  • a methylene group in the 4-position of a 6- or 7-membered cycloalkyleneimino group may be replaced by an oxygen or sulfur atom, by a carbonyl, sulfinyl, sulfonyl or -NH group optionally substituted by a d -3 -alkyl group and additionally a methylene group may be replaced group adjacent to an above-mentioned -NH- or -N (C ⁇ -3 alkyl) by a carbonyl group,
  • R 8 is a hydrogen atom, a C 1-3 alkyl or d. 3- alkylcarbonyl group, is substituted,
  • R 5 is a hydrogen atom or a d -3 -alkyl group or
  • one of the methylene groups of the C 3-7 -cycloalkyl group may be replaced by an imino, d -3- alkyl-imino, acylimino or sulfonylimino group,
  • A is a carbonylamino or aminocarbonyl group, wherein the hydrogen atom of the amino function may optionally be substituted by a C 1-3 alkyl group, and
  • n is the number 1 or 2
  • R 6 is a hydrogen atom or a d -3 alkyl, hydroxy, carboxy-C 1-3 alkyl, C- ⁇ . 3- alkyloxycarbonyl-C 1-3 -alkyl, amino or d -3 -alkylamino group and
  • R 7 is a hydrogen, fluorine, chlorine or bromine atom, a C ⁇ -3 alkyl group in which the hydrogen atoms may be wholly or partly replaced by fluorine atoms, a C 2 - kenyl- 3 -A 3 or C 2 alkynyl! -, hydroxy, C ⁇ constitute -3 alkoxy, trifluoromethoxy, amino, nitro or cyano group,
  • heteroaryl group in the carbon skeleton optionally by a fluorine, chlorine, bromine or iodine atom, a d- 3 alkyl, d -3 alkyloxy, carboxy, d 3- alkoxy-carbonyl or - d -3 -alkoxycarbonylamino-substituted monocyclic 5- or 6-membered heteroaryl group, where
  • the 6-membered heteroaryl group contains one, two or three nitrogen atoms and
  • the 5-membered heteroaryl group optionally substituted by a C ⁇ -3 alkyl or phenyl-d-3-alkyl imino group, an oxygen or sulfur atom or an optionally substituted by a d -3 alkyl, amino d -3 alkyl, d. 3 alkylamino d-3-alkyl, di- (C ⁇ -3-alkyl) -amino-C ⁇ -3 alkyl, C 3 - 6 -Cycloalkylenimino-C ⁇ - 3 alkyl or phenyl-C ⁇ -3- alkyl group substituted imino group or an oxygen or sulfur atom and additionally a nitrogen atom or
  • an imino group which is optionally substituted by a C 1-3 -alkyl or phenyl-C 1-3 -alkyl group and contains two or three nitrogen atoms,
  • a phenyl ring may be fused to the above-mentioned monocyclic heteroaryl groups through two adjacent carbon atoms
  • the bond is via a nitrogen atom or via a carbon atom of the heterocyclic part or a fused-on phenyl ring,
  • alkyl and AI koxy groups contained in the definitions which have more than two carbon atoms, unless otherwise mentioned, may be straight-chain or branched,
  • R 1 , R 2 , R 4 , R 5 , A and B are defined as described in the 12th embodiment and
  • R 3 is the hydrogen atom
  • a 14th embodiment of the present invention comprises the compounds of the above general formula (la), in the
  • R 1 , R 2 , R 4 , R 5 and B are defined as described in the 12th embodiment, wherein R 4 is not the hydrogen atom, and
  • R ⁇ is the hydrogen atom
  • a 15th embodiment of the present invention comprises the compounds of the above general formula I in which
  • R 1 to R 5 and A are defined as described in the 12th embodiment, wherein R 2 is not the hydrogen atom, and
  • n, R 6 and R 7 are defined as described in the first embodiment
  • a 16th embodiment comprises those compounds of the above general formula I in which _
  • R 1 , R 2 , R 4 , R 5 , A and B are defined as described in the 15th embodiment, and
  • R 3 is the hydrogen atom
  • a 17th embodiment of the present invention comprises the compounds of the above general formula (Ib) in which
  • R 1 , R 2 , R 4 and R 5 are defined as in the 15th embodiment, wherein R 4 is not the hydrogen atom, and
  • R 7 is a hydrogen, fluorine, chlorine or bromine atom, a C 3 alkyl group in which the hydrogen atoms may be wholly or partly replaced by fluorine atoms, a C 2 - 3 alkenyl or C 2-3 alkynyl , hydroxy, C ⁇ means -3 alkyloxy, trifluoromethoxy, amino, nitro or cyano group,
  • An 18th embodiment of the present invention comprises the compounds of the above general formula I in which
  • R 1 is an amino, C ⁇ -5-alkylamino, C 3-7 cycloalkylamino or (phenyl-C ⁇ -3 alkyl) - amino group, each on the amine nitrogen atom additionally by a in the alkyl portion optionally substituted by a carboxy group, a in vivo into a carboxy group convertible group, an amino, C 1-3 alkylamino, di- (C ⁇ - 3 -alkyl) -amino or a 4- to 7-membered cycloalkylene imino substituted C 1-5 alkyl or d -5- alkylcarbonyl group may be substituted, wherein in the above-mentioned substituted d-5-alkyl group two heteroatoms are separated from each other by at least two carbon atoms, a 4- to 7-membered cycloalkyleneiminocarbonyl or cycloalkyleneiminosulfonyl group, wherein
  • (C 3 -alkyl) amino, an aryl or a 5-. to 6-membered heteroaryl group may be substituted with the proviso that in the substitution of one of the imino group adjacent methylene group two heteroatoms are separated by at least two carbon atoms, and / or
  • a methylene group in the 3-position of a 5-membered cycloalkyleneimino group may be replaced by a sulfur atom, a sulfinyl or sulfonyl group, or
  • a methylene group in the 4-position of a 6- or 7-membered cycloalkyleneimino group may be replaced by an oxygen or sulfur atom, a carbonyl or by an optionally substituted by a methyl or hydroxy group -NH group, additionally adjacent a methylene group to the above mentioned -NH group may be replaced by a carbonyl group,
  • alkyl d- C3 alkyl amino-C 1-3, C 1-3 alkyl amino-C ⁇ -3-alkyl, di- (C ⁇ -3-alkyl) amino -C ⁇ - 3 -alkyl-, a 4- to 7-membered cycloalkyleneimino-C 3 -alkyl or C 3 .6-Cycloalkylamino-C ⁇ .
  • 3- alkyl groups substituted 5- to 7-membered cycloalkenyleneiminocarbonyl group, wherein the double bond is not bonded to a nitrogen atom and may be condensed with a 5- or 6-membered heteroaryl group,
  • a methylene group which is adjacent to the nitrogen atom may be replaced by a carbonyl group in a 5- to 7-membered cycloalkyleneimino group
  • heterocyclic part methyl- each represents a hydrogen atom by a C 3 alkyloxycarbonyl-, C- ⁇ - 5 alkyloxycarbonylamino-C ⁇ -3-alkyl, methylsulfonyl, amino-C ⁇ .
  • 3- alkyl or aminocarbonyl group may be replaced and
  • n 1 or 2
  • R 2 is a fluorine, chlorine or bromine atom, a d-3-alkyl group in which the hydrogen atoms may be wholly or partly replaced by fluorine atoms, a C 2-3 alkenyl, C 2 - 3 -alkynyl or d 3- alkyloxy group in which the hydrogen atoms may be wholly or partly replaced by fluorine atoms,
  • R 3 is a hydrogen atom
  • R 4 is a hydrogen atom or a straight-chain or branched ds-alkyl group which is optionally substituted by a hydroxyl, a C 1-3 -alkyloxy group in which the hydrogen atoms may be wholly or partly replaced by fluorine atoms, a carboxy-d- 3 -alkyloxy-, d- 5 alkyloxycarbonyl-C ⁇ - 3 alkyloxy, C ⁇ - amino- 5 alkyloxycarbonyl-, chlorine-C ⁇ -3 -alkylaminocarbonylamino-, mercapto, C 1-3 alkylsulphanyl, C ⁇ - alkyl sulfinyl 3 , d -3 alkylsulfonyl, carboxy, aminocarbonyl, C ⁇ -3 alkylaminocarbonyl, di- (C ⁇ -3 alkyl) aminocarbonyl, amino, C -3 alkylamino, di- (C 1- -alkyl) -amin
  • a methylene group of the Cycloalkyleniminoteils by an optionally substituted by a hydroxy, amino, d-3-alkylamino, di- (C ⁇ - 3 -alkyl) -amino, a 4- to 7-membered cycloalkyleneimino or d- 5- alkyloxycarbonylamino group substituted D 3 -alkyl group and a non-imino group adjacent the methylene group of the Cycloalkyleniminoteils by a hydroxy, amino, C 3 -alkylamino, di- (C 3 -3 -alkyl) amino, aminocarbonyl, C 3 -alkylaminocarbonyl - or di- (C ⁇ -3 alkyl) - aminocarbonyl group may be substituted and / or
  • R 8 represents a hydrogen atom, a d -3 -alkyl or d-3-alkyicarbonyl group
  • a phenyl or heteroaryl phenyl-C 3 -3 alkyl or heteroaryl-C. 3 -alkyl group which is optionally substituted by a chlorine atom, a hydroxy, C ⁇ -4 -alkyloxy, trifluoromethoxy, carboxy or d -3 -alkyloxycarbonyl group,
  • R 5 is a hydrogen atom
  • A is a carbonylamino or aminocarbonyl group
  • R 7 represents a fluorine, chlorine or bromine atom
  • heteroaryl is a in the carbon skeleton are optionally substituted by a C 3 alkyl, carboxy, C ⁇ -3 alkoxy carbonyl or C 3 alkoxy-carbonylamino group substituted monocyclic 5- or 6-membered heteroaryl group is understood, wherein
  • the 6-membered heteroaryl group contains one, two or three nitrogen atoms and
  • the 5-membered heteroaryl group optionally substituted by a C ⁇ -Alky -3 - substituted or phenyl-d-3-alkyl imino group, an oxygen or sulfur atom or an optionally substituted by a -3 C ⁇ -alkyl, amino-C ⁇ -3 -alkyl, d- 3- Alkylamino- C ⁇ .3-alkyl, di- (C 3 -alkyl) -amino-C ⁇ -3 alkyl -, Cse-Cycloalkylenimino-ds-alkyl-, or phenyl-C ⁇ - 3 -alkyl group substituted imino group or an oxygen or sulfur atom and additionally a nitrogen atom or
  • a phenyl ring may be fused to the above-mentioned monocyclic heteroaryl groups through two adjacent carbon atoms
  • the bond is via a nitrogen atom or via a carbon atom of the heterocyclic part or a fused-on phenyl ring,
  • alkyl and alkoxy groups having more than two carbon atoms contained in the definitions, unless otherwise mentioned, may be straight-chain or branched,
  • a 19th embodiment of the present invention comprises the compounds of the above general formula (Ib) in which
  • R 1 , R 2 , R 4 and R 5 are defined as described in the 18th embodiment, wherein R 4 is not the hydrogen atom, and
  • R 7 represents a chlorine or bromine atom, their tautomers, their diastereomers, their enantiomers, their genes and their salts.
  • a 20th embodiment of the present invention comprises the compounds of the above general formula (Ic), in which
  • R 1 is a group of the formula
  • R 12 is the hydrogen atom, a methyl, aminomethyl, C 3 -alkylamino-d- 2- alkyl, di (d_ 3 -alkyl) -amino-C 2 -2 -alkyl, pyrrolidin-1-yl-methyl or 2- (pyrrolidin-1-yl) -ethyl group and
  • R 13 represents a hydrogen atom, a methyl or aminomethyl group
  • R 2 is a fluorine, chlorine or bromine atom, a methyl, trifluoromethyl or methoxy group
  • R 4 is a C ⁇ - -Alkyinosti, by a fluorine atom, a hydroxy, C ⁇ -3 alkyloxy, trifluoromethoxy, 2,2,2-Trifluorethyloxy-, mercapto, d -4 alkylsulphanyl, C ⁇ - 4 - alkyl sulfinyl, d-4-alkylsulfonyl, amino, C 1-3 alkylcarbonylamino, d -3 alkylsulfonylamino, carboxy, aminocarbonyl, C ⁇ -3 alkylaminocarbonyl, di- (C ⁇ -3- alkyl) -aminocarbonyl or a 4- to 7-membered cycloalkyleneimino group may be substituted and
  • R 7 is a chlorine or bromine atom
  • a 21st embodiment of the present invention comprises the compounds of the above general formula (Ic) in which
  • R 12 is the hydrogen atom, a methyl, aminomethyl, C 3 -alkylamino-C 2 -alkyl, di- (C 3 -alkyl) -amino-C 2 -alkyl, pyrrolidin-1-yl methyl- or 2- (pyrrolidin-1-yl) -ethyl group and
  • R 13 represents a hydrogen atom, a methyl or aminomethyl group
  • R 2 is a fluorine, chlorine or bromine atom, a methyl, trifluoromethyl or methoxy group
  • R 4 is a d -4 alkyl group by fluorine atom, a hydroxy, C ⁇ - 3 alkyloxy, trifluoromethoxy, 2,2,2-Trifluorethyloxy-, mercapto, C ⁇ -4 alkylsulphanyl, C -4 alkyl sulfinyl, d -4 alkylsulfonyl, amino, C ⁇ -3 alkylcarbonylamino, C 1-3 alkylsulfonylamino, carboxy, aminocarbonyl, C ⁇ -3 alkylaminocarbonyl, di- (C ⁇ - 3 -alkyl) -aminocarbonyl or a 4- to 7-membered cycloalkyleneimino group is substituted and
  • R 7 is a chlorine or bromine atom
  • a 22nd embodiment of the present invention comprises the compounds of the above general formula (Ic), in which
  • R 1 is a 2,5-dihydro-1H-pyrrole-1-ylcarbonyl, pyrrolidine-1-ylcarbonyl, / V-acetyl-N-cyclobutylamino, 2- ( ⁇ / -terf-butoxycarbonylaminomethyl ) -pyrrolidine-1-yl-carbonyl-, 2- (aminomethyl) -pyrrolidin-1-yl-carbonyl, 3-oxo-piperazine-1-yl-carbonyl, 4-methyl-3-oxo-piperazine-1 - yl-carbonyl, 2,3-dihydro-imidazo [2,1-b] -thiazo!
  • R 2 is a fluorine, chlorine or bromine atom, a C ⁇ - -Alkylgru ⁇ pe 3, in which the hydrogen atoms may be wholly or partly replaced by fluorine atoms, a C 3 alkyloxy or dxrAlkinyl distr,
  • R 3 is a hydrogen atom
  • R 5 is a hydrogen atom
  • A is an aminocarbonyl or carbonylamino group
  • R 7 represents a fluorine, chlorine or bromine atom or a methyl group
  • a 23rd embodiment of the present invention comprises the compounds of the above general formula I in which
  • R 1 is an amino, C ⁇ -5 alkylamino, C 3-7 cycloalkyl amino or (phenyl-C 1-3 -alkyl) - amino group, each on the amine nitrogen atom by a phenylcarbonyl or phenylsulphonyl group or by a in the alkyl moiety optionally substituted by a carboxy group, a in vivo into a carboxy group, an amino, C ⁇ - 3 -Alkylamino-, di- (C ⁇ -3 -alkyl) -amino or C 3 -6-Cycloalkylenimino substituted C ⁇ - 5 alkyl - or C ⁇ - 5 alkylcarbonyl group may be substituted, wherein two nitrogen atoms are separated by at least two carbon atoms,
  • a non-adjacent imino group of the methyl group by a hydroxy, benzyloxy, C ⁇ -3 alkoxy, amino, C ⁇ -3 alkylamino, di- (C 1-3 -alkyl) -amino or C 3-6 - Cycloalkylenimino distr may be substituted and / or
  • a methylene group in the 3-position of a 5-membered cycloalkyleneimino group may be replaced by a sulfur atom, a sulfinyl or sulfonyl group, or a methylene group in the 4-position of a 6- or 7-membered cycloalkyleneimino group by an oxygen or sulfur atom or by an -NH-, -N-C ⁇ - 3 -alkyl-, -N (C 2 -3-alkanoyl) -, sulfinyl - or sulfonyl group may be replaced and / or
  • a -CH 2 -CH 2 - group in a 5- to 7-membered cycloalkyleneimino group by a -NH-CO-, -CO-NH-, -CO-N (CH 3 ) - or a -N (CH 3 ) - CO group can be replaced,
  • a non-adjacent imino group of the methyl group by a hydroxy, benzyloxy, d- 3 alkoxy, amino, d -3 alkylamino, di- (C ⁇ -3 alkyl) amino or C 3-6 -Cycloa ) kylenimino group may be substituted, a -7 d alkylcarbonyl or C 3- 7 ⁇ cycloalkylcarbonyl group, wherein
  • the methyl group in the 2-, 3- or 4-position in a C 3 - 7 cycloalkylcarbonyl group may be replaced by an oxygen or sulfur atom, a carbonyl, sulphinyl, sulphonyl or -NH group, in the
  • the hydrogen atom of the -NH group may be replaced by a C ⁇ -3 alkyl or C ⁇ -3 alkyl carbonyl group,
  • a phenylcarbonyl or heteroarylcarbonyl group which in the phenyl or heteroaryl part by a fluorine, chlorine or bromine atom, by a trifluoromethyl, d -3 alkyl, amino-C 3 -alkyl, C 3 -alkylamino-C ⁇ -3-alkyl, di- (3 C ⁇ - alkyl) amino-C ⁇ -3 alkyl,
  • 6 may be -Cycloalkylenimino-d- 3 alkyl or C ⁇ -3-alkoxy group, - C 3
  • the phenyl part by a fluorine, chlorine or bromine atom, by a trifluoromethyl, d- 3- alkyl, amino-d- 3- alkyl, ds-alkylamino-ds-alkyl, di (C ⁇ -3 alkyl ) -amino-d-3 alkyl, C 3- 6-Cycloalkylenimino-C ⁇ -3-alkyl or C ⁇ -3 alkoxy group may be substituted and / or
  • a methylene group which is adjacent to the nitrogen atom may be replaced by a carbonyl group in a 5- to 7-membered cycloalkyleneimino group
  • n 1 or 2
  • R is a hydrogen, fluorine, chlorine or bromine atom, a C 3 alkyl group in which the hydrogen atoms may be replaced by fluorine atoms totally or partially, a C 2 - 3 alkenyl, C 2-3 alkynyl, d 3 -alkoxy or trifluoromethoxy group,
  • R 3 is a hydrogen atom or a C 1-3 -alkyl group
  • R 4 is a hydrogen atom or a straight-chain or branched d -5- alkyl group which is optionally substituted by a hydroxy, C 1-3 -alkyloxy, mercapto, d -3 -alkylsulfanyl, d- 3 -alkylsulfinyl-, C- 3- alkylsulfonyl, carboxy, aminocarbonyl, d- 3- alkylaminocarbonyl, di (C 1-3 -alkyl) aminocarbonyl, C 3-6 -cycloalkyleniminocarbonyl, amino, C 1-3 -alkylamino di- (C ⁇ -3-alkyl) -amino, C 3 - 6 -Cycloalkylenimino-, d- amino-3 alkylcarbonyl, C 3 - 6 -Cycloalkylcarbonylamino-, benzyloxycarbonylamino or guanidino group is substituted,
  • a phenyl or heteroaryl, phenyl-C ⁇ -3 -alkyl or heteroaryl-C ⁇ - 3- alkyl group optionally substituted by a hydroxy, C ⁇ -4 -alkyloxy, benzyloxy, hydroxycarbonyl-C 3-alkoxy, -C 3- alkyloxycarbonyl-C 1-3 -alkyloxy, aminocarbonyl-C 1-3 -alkyloxy, C 1-5 -alkylaminocarbonyl-C 1-5 -alkyloxy-, di- (C 3-3 -alkyl) -aminocarbonyl-C 3 - alkyloxy, C 3-6 CycloalkyleniminocarbonyI-C -3 alkoxy, carboxy, alkyloxycarbonyl C ⁇ -3 is substituted,
  • a 4- to 7-membered cycloalkyl-C ⁇ - 3 -alkyl group in which one or two methylene groups may be replaced by a -NH- or -N (C ⁇ - 3- alkyl) - group and in which one or two of the -NH or -N (C 1-3 -alkyl) -group adjacent methylene groups may each be replaced by a carbonyl group, with the proviso that a cycloalkyl group as defined above in which two -NH- or -N (C 1-3 -) Alkyl) groups are separated by exactly one -CH 2 group, are excluded,
  • R 5 is a hydrogen atom or a d -3 -alkyl group or
  • one of the methylene groups of the C 3-7 cycloalkyl group, by an imino, d-3 alkyl imino, Acylimino- or Sulfonyiimino distr may be replaced,
  • A is a carbonylamino or aminocarbonyl group, wherein the hydrogen atom of the amino function may optionally be substituted by a d -3 alkyl group, and
  • n is the number 1 or 2
  • R 6 is a hydrogen atom or a C 3-alkyl, hydroxy, amino, Ci. 3 - alkyl amino group and
  • R 7 is a hydrogen, fluorine, chlorine or bromine atom, a C ⁇ -3 alkyl group in which the hydrogen atoms may be wholly or partly replaced by fluorine atoms, a dw-alkenyl or C 2-3 alkynyl, a hydroxy represent -, d- 3 -alkoxy, trifluoromethoxy or cyano group,
  • heteroaryl is a in the carbon skeleton are optionally substituted by a d -3 alkyl, carboxy, d -3 alkoxy carbonyl or C 3 alkoxy-carbonylamino group substituted monocyclic 5- or 6-membered heteroaryl group is understood, wherein
  • the 6-membered heteroaryl group contains one, two or three nitrogen atoms and
  • the 5-membered heteroaryl group contains an alkyl group optionally by a C 1-3 alkyl or phenyl-C ⁇ - 3 substituted imino group, an oxygen or sulfur atom or
  • a phenyl ring may be fused to the above-mentioned monocyclic heteroaryl groups through two adjacent carbon atoms
  • alkyl and alkoxy groups having more than two carbon atoms contained in the definitions, unless otherwise mentioned, may be straight-chain or branched,
  • a twenty-fourth embodiment of the present invention comprises the compounds of the above general formula I, in which :
  • R is an amino, C 1-5 -alkylamino, C 3J 7 -cycloalkylamino or (Phehyl-C ⁇ - 3 -alkyl) - amino group, each at the amine nitrogen atom by a phenylcarbonyl or phenylsulfonyl group or by a in the alkyl moiety optionally by a carb 20 oxy group, a group in vivo in a carboxy group, an amino, d- 3 alkylamino, di (C 3 -3 alkyl) amino or C 3-6 cycloalkylene imino substituted C ⁇ - 5 alkyl or C ⁇ - 5 alkylcarbonyl group may be substituted, wherein two nitrogen atoms are separated from each other by at least two carbon atoms,
  • 25 is a di- (C ⁇ -5 alkyl) amino or N- (C 3- 7 cycloalkyl) -d -5 alkylamino group, wherein the Ci .5- alkyl part with the exception of the 1-position in each case by a hydroxy, d -3 alkoxy, amino, C ⁇ -3 alkylamino, di - (. C ⁇ -3 alkyl) -amino or C 3 - 6 -Cycloalkylenimino distr may be substituted,
  • 5- alkyl-aminocarbonyl, di- (d -3 -alkyl) -aminocarbonyl or C 3-6 -cycloalkylenimino- carbonyl group may be substituted or
  • C 3-6 cycloalkyleneimino group may be substituted and / or
  • a methylene group in the 3-position of a 5-membered cycloalkyleneimino group may be replaced by a sulfur atom, a sulfinyl or sulfonyl group, or
  • a methylene group in the 4-position of a 6- or 7-membered cycloalkyleneimino group by an oxygen or sulfur atom or by an -NH-, -Nd- 3- alkyl, -N (C 2-3 alkanoyl) -, sulfinyl or Sulfonyl group may be replaced and / or
  • a -CH 2 -CH 2 - group in a 5- to 7-membered cycloalkyleneimino group by a -NH-CO-, -CO-NH-, -CO-N (CH 3 ) - or a -N (CH 3 ) - CO group can be replaced,
  • each one of C ⁇ -5 alkyl groups by one or two d-3 alkyl d, -3 alkoxy d-3 alkyl, amino-C ⁇ -3 alkyl, C ⁇ -3 alkylamino-C ⁇ - 3 alkyl, di (C ⁇ -3 alkyl) -amino-d-3 alkyl, C3-6-Cycloa!
  • kylenimino-d-3-alkyl C ⁇ - 5 -Alkyloxycarbonylamino- C 1-3 alkyl -, C 3-6 -cycloalkylamino-C ⁇ -3-alkyl, aminocarbonyl, C 1-3 alkylamino carbonyl, N- (C3-7-cycloalkyl) -d -5 alkylaminocarbonyl, / V- ( phenyl-C ⁇ -3-alky ⁇ ) -C ⁇ -5 - alkylaminocarbonyl, di- (C ⁇ -3 alkyl) aminocarbonyl or C 3 -6-Cycloalkylenimino- carbonyl group may be substituted or
  • a non-adjacent imino group of the methyl group by a hydroxy, benzyloxy, C ⁇ - 3 alkoxy, amino, C ⁇ -3 -AlkyIamino-, di- (d -3 alkyl) amino or C 3-6 -Cycloalkylenimino distr may be substituted
  • the methyl group in the 2-, 3- or 4-position in a C 3 - 7 cycloalkylcarbonyl group may be replaced by an oxygen or sulfur atom, a carbonyl, sulphinyl, sulphonyl or -NH group, in the
  • the hydrogen atom of the -NH-group by a carbonyl group d -3 alkyl or C ⁇ - 3 alkyl may be replaced,
  • phenylcarbonyl or heteroarylcarbonyl group in the phenyl or heteroaryl moiety by a fluorine, chlorine or bromine atom, by a trifluoromethyl, d -3 alkyl, amino-C ⁇ alkyl -3, -3 alkylamino C ⁇ -C ⁇ -3-alkyI-, di- (C 1-3 -alkyl) -amino-C ⁇ -3 alkyl,
  • a methylene group which is adjacent to the nitrogen atom may be replaced by a carbonyl group in a 5- to 7-membered cycloalkyleneimino group
  • n 1 or 2
  • R 2 is a chlorine or bromine atom, a C 1-3 -alkyl group in which the hydrogen atoms may be wholly or partly replaced by fluorine atoms, or a C 2 - 3 alkenyl group,
  • R 3 is a hydrogen atom or a C ⁇ -3 alkyl group
  • R 4 is a hydrogen atom or a straight-chain or branched C ⁇ - 5 alkyl group, the optionally by a hydroxy, d -3 -alkyloxy, mercapto, C 3 -alkylsulfanyl-, -C.
  • alkylsulfinyl C 1-3 AI kylsulf onyl-, carboxy, aminocarbonyl, C ⁇ -3-alkylamino- carbonyl, di- (C ⁇ -3 alkyl) aminocarbonyl, C 3-6 -Cycloalkyleniminocarbonyl-, Amino, C 1-3 -alkylamino, di- (C 3-3 -alkyl) -amino, C 3-6 -cycloalkylenimino, C ⁇ . Substituted by 3- alkylcarbonylamino, C 3-6 -cycloalkylcarbonylamino, benzyloxycarbonylamino or guanidino group,
  • 3 alkyl-, or heteroaryl-C ⁇ -3 alkyl group optionally substituted by a hydroxy d- d -4 alkyloxy, benzyloxy, hydroxycarbonyl 3 alkoxy, C ⁇ -3 alkyloxycarbonyl-C ⁇ - 3 alkyloxy, aminocarbonyl-C ⁇ -3 alkyloxy, C ⁇ - 3 alkylaminocarbonyl-C ⁇ -3 alkyloxy, di (C -3 alkyl) aminocarbonyl-C ⁇ - 3 alkyloxy,
  • a 4- to 7-membered cycloalkyl C ⁇ _ 3 alkyl group in which one or two methylene groups by a -NH- or -N (C 1-3 -alkyl) - group may be replaced and in which one or two of the -NH - or -N (d -3 alkyl) group adjacent methylene groups may each be replaced by a carbonyl group, with the proviso that a cycloalkyl group as defined above, in the two -NH- or -N (C ⁇ - 3 -A! kyl) groups are separated by exactly one -CH 2 group, are excluded,
  • R 5 is a hydrogen atom or a d -3 alkyl group or
  • R 4 and R 5 together with the carbon atom to which they are attached, a C 3 - 7 cycloalkyl group wherein
  • one of the methylene groups of the C 3-7 -cycloalkyl group may be replaced by an imino, d- 3- alkyl-imino, acylimino or sulfonylimino group,
  • A is a carbonylamino or aminocarbonyl group, wherein the hydrogen atom of the amino function may optionally be substituted by a d -3 alkyl group, and B is a group of the formula
  • n is the number 1
  • R 6 is a hydrogen atom or a C ⁇ -3 alkyl, hydroxy, amino, C ⁇ - group 3 and -Alkyiamino-
  • R 7 is a hydrogen, fluorine, chlorine or bromine atom, a C ⁇ -3 alkyl group in which the hydrogen atoms may be wholly or partly replaced by fluorine atoms, a C 2 - 3 alkenyl or C 2 alkynyl -3- , a hydroxy, C ⁇ -3 alkoxy, trifluoromethoxy or
  • heteroaryl carbonyl- a in the carbon skeleton are optionally substituted by a C ⁇ -3 alkyl, carboxy, d-3 alkoxy or C ⁇ - alkoxy-carbonylamino group substituted monocyclic 5- or 6-membered heteroaryl group is understood, wherein
  • the 6-membered heteroaryl group contains one, two or three nitrogen atoms and
  • the 5-membered heteroaryl group is optionally substituted by a d -3 -alkyl or
  • a phenyl ring may be fused
  • the bond is via a nitrogen atom or via a carbon atom of the heterocyclic part or a fused-on phenyl ring,
  • alkyl and alkoxy groups having more than two carbon atoms contained in the definitions, unless otherwise mentioned, may be straight-chain or branched,
  • a 25th embodiment of the present invention comprises the compounds of the above general formula I in which
  • R 1 is an amino, alkylamino C ⁇ .5, C 3-7 cycloalkylamino or (phenyl-C -3 alkyl) - amino group, each on the amine nitrogen atom by a phenylcarbonyl or phenylsulphonyl group or by a in the alkyl moiety is optionally substituted by a carboxy group, a group convertible in vivo into a carboxy group, an amino, C ⁇ .
  • a di- (C ⁇ -5 alkyl) amino or ⁇ / V- (C 3-7 cycloalkyl) -5 -C ⁇ alkylamino group wherein the alkyl portion C ⁇ - 5 with the exception of the 1-position in each case by a hydroxy, C ⁇ -3 alkoxy, amino, d -3 alkylamino, di- (C ⁇ -3 alkyl) -amino or C 3 -6-cycloalkyleneimino group may be substituted,
  • C 3-6 -cycloalkylamino-d- 3- alkyl, aminocarbonyl, d- 3- alkylaminocarbonyl, ⁇ / - (C 3-7 -cycloalkyl) -G ⁇ -5- alkylaminocarbonyl, ⁇ / - (phenyl-d 3- alkyl) -C ⁇ -5- alkyl-aminocarbonyl, di- (C ⁇ -3 -alkyl) -aminocarbonyl or C 3 -6-Cycloalkylenimino- carbonyl group may be substituted or
  • a non-adjacent imino group of the methyl group by a hydroxy, benzyloxy, d- 3 alkoxy, amino, C ⁇ -3 alkylamino, di- (d. 3 -alkyl) -amino or C ⁇ 3-6 -Cycloalkylenimino distr may be substituted and / or
  • a methylene group in the 3-position of a 5-membered cycloalkyleneimino group may be replaced by a sulfur atom, a sulfinyl or sulfonyl group, or
  • a methylene group in the 4-position of a 6- or 7-membered cycloalkyleneimino group by an oxygen or sulfur atom or by an -NH-, -Nd- 3 -alkyl-, -N (C 2-3 -alkanoyl) -, sulfinyl- or Sulfonyl group may be replaced and / or a -CH 2 -CH 2 - group in a 5- to 7-membered cycloalkyleneimino group by a -NH-CO-, -CO-NH-, -CO-N (CH 3 ) - or a -N (CH 3 ) - CO group can be replaced,
  • each one of C ⁇ -5 alkyl groups by one or two C ⁇ -3 alkyl, d -3 alkoxy C ⁇ alkyl- -3, amino-d -3 alkyl, C ⁇ . 3- alkylamino-d- 3- alkyl] -, di- (d -3 -alkyl) amino-C ⁇ - 3 -alkyl-, Cs- ⁇ -cycloalkylenimino-ds-alkyl, C ⁇ - 5 -alkyloxycarbonylamino- d- 3-alkyl, C 3- 6-cycloalkylamino C ⁇ .3 alkyl, aminocarbonyl, d -3 alkylamino carbonyl, / V- (C 3-7 cycloalkyl) -C ⁇ -5-alkylaminocarbonyl, ⁇ / - (phenyl-C ⁇ -3 -alkyl) -d -5 - alkylaminocarbonyl, di- (C ⁇ -3 -alkyI)
  • a methylene group which is adjacent to the nitrogen atom may be replaced by a carbonyl group in a 5- to 7-membered cycloalkyleneimino group
  • n 1 or 2
  • R represents a chlorine or bromine atom, a C ⁇ -3 alkyl group in which the hydrogen atoms may be wholly or partly replaced by fluorine atoms, or a C 2-3 alkenyl group,
  • R 3 is a hydrogen atom
  • R 4 is a hydrogen atom or a linear or branched C 5 alkyl group optionally substituted by a hydroxy -3 d alkyloxy, mercapto, C ⁇ -3 alkylsulphanyl, d- 3 alkylsulfinyl, C ⁇ -3 alkylsulfonyl, carboxy, aminocarbonyl, d -3 alkylamino- carbonyl, di- (C ⁇ -3 alkyl) aminocarbonyl, C 3-6 -Cycloalkyleniminocarbonyl-, amino, d- 3 alkylamino, di- (d -3 alkyl) amino, C 3 -6-Cycloalkylenimino-, C ⁇ - amino-3 alkylcarbonyl, C 3-6 -Cycloalkylcarbonylamino-, benzyloxycarbonylamino or guanidino group is substituted,
  • a phenyl- or heteroaryl, phenyl-C ⁇ -3 -alkyl- or heteroaryl-d- 3- alkyl group optionally substituted by a hydroxy, d- 4 -alkyloxy, benzyloxy, hydroxycarbonyl-C ⁇ -3 -alkoxy-, d - 3 alkyloxycarbonyl-C ⁇ -3-alkyloxy, aminocarbonyl-C ⁇ -3 alkyloxy, C ⁇ - 3 alkylaminocarbonyl-C 1- 3-alkyloxy, di- (C ⁇ -3 alkyl) aminocarbonyl-C ⁇ - 3 -alkyloxy, C 3 - 6 -cycloalkyleniminocarbonyl-C 3 -alkyloxy, carboxy, C 1-3 -alkyloxycarbonyl is substituted,
  • a 4- to 7-membered cycloalkyl-d -3 alkyl group in which one or two methylene groups by a -NH- or -N (C ⁇ -3 alkyl) - group may be replaced and in which one or two of the -NH - or -N (d-C3 alkyl.) group adjacent methylene groups may each be replaced by a carbonyl group, with the proviso that a cycloalkyl group as defined above, in the two -NH- or -N (C ⁇ -3 -Alky! ) Groups are separated by exactly one -CH 2 group, are excluded,
  • R 5 is a hydrogen atom
  • one of the methylene groups of the C 3-7 -cycloalkyl group may be replaced by an imino, C 1-3 -alkyl-imino, acylimino or sulfonylimino group,
  • A is a carbonylamino or aminocarbonyl group, wherein the hydrogen atom of the amino function may optionally be substituted by a C 1-3 alkyl group, and B is a group of the formula
  • n is the number 1
  • R 6 is a hydrogen atom or a C ⁇ - 3 alkyl, hydroxy, amino, C 1-3 alkylamino group and
  • R 7 is a fluorine, chlorine or bromine atom, a C ⁇ -3 -AlkyI distr in which the hydrogen atoms may be wholly or partly replaced by fluorine atoms, a C 2-3 alkenyl, C 2-3 alkynyl or a hydroxy represent

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Abstract

La présente invention concerne de nouveaux amides d'acide carboxylique substitués de formule générale (I), dans laquelle A, B et R1 à R5 sont tels que définis dans la revendication 1, leurs tautomères, leurs énantiomères, leurs diastéréomères, leurs mélanges et leurs sels, en particulier leurs sels physiologiquement acceptables à acides ou bases inorganiques ou organiques, qui présentent de précieuses caractéristiques. Les composés de la formule générale I susmentionnée ainsi que leurs tautomères, leurs énantiomères, leurs diastéréomères, leurs mélanges et leurs sels, en particulier leurs sels physiologiquement acceptables à acides ou bases inorganiques ou organiques, et leurs stéréoisomères présentent de précieuses caractéristiques pharmacologiques, en particulier un effet antithrombotique et un effet inhibiteur de facteur Xa.
EP03767800A 2002-12-19 2003-12-13 Nouveaux amides d'acide carboxylique, leur production et leur utilisation en tant que medicaments Withdrawn EP1575925A1 (fr)

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DE2002159407 DE10259407A1 (de) 2002-12-19 2002-12-19 Neue Carbonsäureamide, deren Herstellung und deren Verwendung als Arzneimittel
DE10259407 2002-12-19
DE10335545A DE10335545A1 (de) 2003-08-02 2003-08-02 Neue Carbonsäureamide, deren Herstellung und deren Verwendung als Arzneimittel
DE10335545 2003-08-02
PCT/EP2003/014195 WO2004056784A1 (fr) 2002-12-19 2003-12-13 Nouveaux amides d'acide carboxylique, leur production et leur utilisation en tant que medicaments

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CL2003002665A1 (es) 2005-01-14
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US20080132496A1 (en) 2008-06-05
US7326791B2 (en) 2008-02-05
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