Bicyclic heterocycles, pharmaceutical compositions containing them, their use, and processes for preparing them

• US 20060063752A1
• Filed: 11/04/2005
• Published: 03/23/2006
• Est. Priority Date: 03/14/2000
• Status: Abandoned Application

• Current Assignee: Boehringer Ingelheim Pharma GmbH & Company Kg (C.H. Boehringer Sohn AG & Co. KG)
• Original Assignee: Boehringer Ingelheim Pharma GmbH & Company Kg (C.H. Boehringer Sohn AG & Co. KG)
• Inventors: Himmelsbach, Frank, Langkopf, Elke, Metz, Thomas, Jung, Birgit, Blech, Stefan, Solca, Flavio
• Application Number:
  US11/266,920
• Publication Number:
  US 20060063752A1
• Time in Patent Office: Days
• US Class Current: 514/211.50
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: C07D 221/00 Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
• CPC Class Codes: C07D 401/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 403/12 linked by a chain containing hetero atoms as chain links

Abstract

A compound of formula (I)
wherein R_a, R_b, R_c, A, B, C, D, and X are as defined herein, or a tautomer, stereoisomer, or salt thereof, particularly a physiologically acceptable salt thereof. In addition, pharmaceutical compositions comprising an effective amount of a compound of formula (I), methods for the treatment or prophylaxis of benign or malignant tumors, diseases of the airways and lungs, polyps, diseases of the gastrointestinal tract, bile duct, gall bladder, kidneys, and skin, and methods for making compounds of formula (I) are disclosed.

Claims

1. A compound of formula (I)

wherein:

R_a is a hydrogen atom or a C_1-4-alkyl group;

R_b is a phenyl, benzyl, or 1-phenylethyl group wherein the phenyl nucleus is substituted in each case by R₁, R₂, and R₃, wherein;

R₁ and R₂, which are identical or different, each are;

(i) a hydrogen, fluorine, chlorine, bromine, or iodine atom,

(ii) a C_1-4-alkyl, hydroxy, C_1-4-alkoxy, C_3-6-cycloalkyl, C_4-6-cycloalkoxy, C_2-5-alkenyl, or C_2-5-alkynyl group,

(iii) an aryl, aryloxy, arylmethyl, or arylmethoxy group,

(iv) a C_3-5-alkenyloxy or C_3-5-alkynyloxy group, wherein the unsaturated moiety thereof is not linked to the oxygen atom,

(v) a C_1-4-alkylsulfenyl, C_1-4-alkylsulfinyl, C_1-4-alkylsulfonyl, C_1-4-alkylsulfonyloxy, trifluoromethylsulfenyl, trifluoromethylsulfinyl, or trifluoromethylsulfonyl group,

(vi) a methyl or methoxy group substituted by 1 to 3 fluorine atoms,

(vii) an ethyl or ethoxy group substituted by 1 to 5 fluorine atoms, or

(viii) a cyano or nitro group or an amino group optionally substituted by one or two C_1-4-alkyl groups, wherein the substituents are identical or different, or

R₁ together with R₂, if they are bound to adjacent carbon atoms, are a —

CH═

CH—

CH═

CH, —

CH═

CH—

NH, or —

CH═

N—

NH group, and

R₃ is a hydrogen, fluorine, chlorine, or bromine atom, or a C_1-4-alkyl, trifluoromethyl, or C_1-4-alkoxy group;

X is a methine group substituted by a cyano group or a nitrogen atom;

A is a group consisting of;

(a) —

O—

C_1-6-alkylene, —

O—

C_4-7-cycloalkylene, —

O—

C_1-3-alkylene-C_3-7-cycloalkylene, —

O—

C_4-7-cycloalkylene-C_1-3-alkylene, or —

O—

C_1-3-alkylene-C_3-7-cycloalkylene-C_1-3-alkylene group, wherein the oxygen atom thereof in each case is linked to the bicyclic heteroaromatic moiety of formula (I),

(b) an —

O—

C_1-6-alkylene group substituted by an R₆O—

CO or R₆O—

CO—

C_1-4-alkyl group, wherein the oxygen atom of the —

O—

C_1-6-alkylene group is linked to the bicyclic heteroaromatic moiety of formula (I),

(c) an —

O—

C_2-6-alkylene group substituted at a position other than position 1 by a hydroxy, C_1-4-alkoxy, amino, C_1-4-alkylamino, di-(C_1-4-alkyl)-amino, pyrrolidino, piperidino, morpholino, piperazino, or 4-(C_1-4-alkyl)-piperazino group, wherein the oxygen atom of the —

O—

C_2-6-alkylene group is linked to the bicyclic heteroaromatic moiety of formula (I),

(d) a —

C_1-6-alkylene group,

(e) an —

NR₄—

C_1-6-alkylene, —

NR—

C_3-7-cycloalkylene, —

N—

C_1-3-alkylene-C_3-7-cycloalkylene, —

NR₄—

C_3-7-cycloalkylene-C_1-3-alkylene, or —

NR₄—

C_1-3-alkylene-C_3-7-cycloalkylene-C_1-3-alkylene group, wherein the —

NR₄—

moiety thereof in each case is linked to the bicyclic heteroaromatic moiety of formula (I),

(f) an oxygen atom linked to a carbon atom of the group B, or

(g) a NR₄ group linked to a carbon atom of the group B,

B is a group consisting of;

(a) an R₆O—

CO-alkylene-NR₅, (R₇O—

PO—

OR₈)-alkylene-NR₅, or (R₇O—

PO—

R₉)-alkylene-NR₅ group, wherein in each case the alkylene moiety, which is straight-chained and contains 1 to 6 carbon atoms, is additionally optionally substituted by one or two C_1-2-alkyl groups or by an R₆O—

CO or R₆O—

CO—

C_1-2-alkyl group,

(b) a 4- to 7-membered alkyleneimino group substituted by an R₆O—

CO, (R₇O—

PO—

OR₈), (R₇O—

PO—

R₉), R₆O—

CO—

C_1-4-alkyl, bis-(R₆O—

CO)—

C_1-4-alkyl, (R₇O—

PO—

OR₈)—

C_1-4-alkyl, or (R₇O—

PO—

R₉)—

C_1-4-alkyl group,

(c) a 4- to 7-membered alkyleneimino group substituted by two R₆O—

CO or R₆O—

CO—

C_1-4-alkyl groups or by an R₆OCO group and an R₆O—

CO—

C_1-4-alkyl group,

(d) a piperazino or homopiperazino group substituted in each case at the 4 position by R₁₀ and additionally substituted at a cyclic carbon atom thereof by an R₆O—

CO, (R₇O—

PO—

OR₈), (R₇O—

PO—

R₉), R₆O—

CO—

C_1-4-alkyl, bis-(R₆O—

CO)—

C_1-4-alkyl, (R₇O—

PO—

OR₈)—

C_1-4-alkyl, or (R₇O—

PO—

R₉)—

C_1-4-alkyl group,

(e) a piperazino or homopiperazino group substituted in each case at the 4 position by R₁₀ and additionally substituted at cyclic carbon atoms thereof by two R₆O—

CO or R₆O—

CO—

C_1-4-alkyl groups or by an R₆O—

CO group and an R₆O—

CO—

C_1-4-alkyl group,

(f) a piperazino or homopiperazino group substituted in each case at the 4 position by an R₆O—

CO—

C_1-4-alkyl, bis-(R₆O—

CO)—

C_1-4-alkyl, (R₇O—

PO—

OR₈)—

C_1-4-alkyl, or (R₇O—

PO—

R₉)—

C_1-4-alkyl group,

(g) a piperazino or homopiperazino group substituted in each case at the 4 position by an R₆O—

CO—

C_1-4-alkyl, bis-(R₆O—

CO)—

C_1-4-alkyl, (R₇O—

PO—

OR₈)—

C_1-4-alkyl, or (R₇O—

PO—

R₉)—

C_1-4-alkyl group and additionally substituted at cyclic carbon atoms thereof by one or two R₆O—

CO or R₆O—

CO—

C_1-4-alkyl groups or by an R₆O—

CO group and an R₆O—

CO—

C_1-4-alkyl group,

(h) a morpholino or homomorpholino group substituted in each case by an R₆O—

CO, (R₇O—

PO—

OR₈), (R₇O—

PO—

R₉), R₆O—

CO—

C_1-4-alkyl, bis-(R₆O—

CO)—

C_1-4-alkyl, (R₇O—

PO—

OR₈)—

C_1-4-alkyl, or (R₇O—

PO—

R₉)—

C_1-4-alkyl group,

(i) a morpholino or homomorpholino group substituted in each case by two R₆O—

CO or R₆O—

CO—

C_1-4-alkyl groups or by an R₆O—

CO group and an R₆O—

CO—

C_1-4-alkyl group,

(j) a pyrrolidinyl, piperidinyl, or hexahydroazepinyl group substituted in each case at the 1 position by R₁₀, wherein the 5 to 7-membered rings thereof in each case are additionally substituted at a carbon atom thereof by an R₆O—

CO, (R₇O—

PO—

OR₈), (R₇O—

PO—

R₉), R₆O—

CO—

C_1-4-alkyl, bis-(R₆O—

CO)—

C_1-4-alkyl, (R₇O—

PO—

OR₈)—

C_1-4-alkyl, or (R₇O—

PO—

R₉)—

C_1-4-alkyl group,

(k) a pyrrolidinyl, piperidinyl, or hexahydroazepinyl group substituted in each case at the 1 position by R₁₀, wherein the 5 to 7-membered rings thereof in each case are additionally substituted at carbon atoms thereof by two R₆O—

CO or R₆O—

CO—

C_1-4-alkyl groups or by an R₆O—

CO group and an R₆O—

CO—

C_1-4-alkyl group,

(l) a pyrrolidinyl, piperidinyl, or hexahydroazepinyl group substituted in each case at the 1 position by an R₆O—

CO—

C_1-4-alkyl, bis-(R₆O—

CO)—

C_1-4-alkyl, (R₇O—

PO—

OR₈)—

C_1-4-alkyl, or (R₇O—

PO—

R₉)—

C_1-4-alkyl group,

(m) a pyrrolidinyl, piperidinyl, or hexahydroazepinyl group substituted in each case at the 1 position by an R₆O—

CO—

C_1-4-alkyl, bis-(R₆O—

CO)—

C_1-4-alkyl, (R₇O—

PO—

OR₈)—

C_1-4-alkyl, or (R₇O—

PO—

R₉)—

C_1-4-alkyl group, wherein the 5- to 7-membered rings thereof in each case are additionally substituted at carbon atoms thereof by one or two R₆O—

CO or R₆O—

CO—

C_1-4-alkyl groups or by an R₆O—

CO group and an R₆O—

CO—

C_1-4-alkyl group,

(n) a 2-oxomorpholino group substituted by 1 to 4 C_1-2-alkyl groups,

(o) a 2-oxomorpholinyl group substituted at the 4 position by a hydrogen atom, or by a C_1-4-alkyl, R₆O—

CO—

C_1-4-alkyl, (R₇O—

PO—

OR₈)—

C_1-4-alkyl, or (R₇O—

PO—

R₉)—

C_1-4-alkyl group, wherein the 2-oxomorpholinyl group thereof is linked to a carbon atom of the group A, and

(p) an R₁₁NR₅ group, or

A together with B are a group consisting of;

(a) a hydrogen, fluorine, or chlorine atom,

(b) a C_1-6-alkoxy group,

(c) a C_2-6-alkoxy group substituted at a position other than position 1 by a hydroxy, C_1-4-alkoxy, amino, C_1-4-alkylamino, di-(C_1-4-alkyl)-amino, pyrrolidino, piperidino, hexahydroazepino, morpholino, homomorpholino, piperazino, 4-(C_1-4-alkyl)-piperazino, homopiperazino, 4-(C_1-4-alkyl)-homopiperazino, or 1-imidazolyl group,

(d) a C_1-4-alkoxy group substituted by a pyrrolidinyl, piperidinyl, or hexahydroazepinyl group substituted at the 1 position by R₁₀,

(e) a C_1-6-alkoxy group substituted by an R₆O—

CO, (R₇O—

PO—

OR₈), or (R₇O—

PO—

R₉) group,

(f) a C_3-7-cycloalkoxy or C_3-7-cycloalkyl-C_1-4-alkoxy group,

(g) an amino, C_1-4-alkylamino, di-(C_1-4-alkyl)-amino, pyrrolidino, piperidino, hexahydroazepino, morpholino, homomorpholino, piperazino, 4-(C_1-4-alkyl)-piperazino, homopiperazino, or 4-(C_1-4-alkyl)-homopiperazino group, and

(h) a 2-oxomorpholino group optionally substituted by 1 or 2 methyl groups;

C is a group consisting of;

(a) an —

O—

C_1-6-alkylene, —

O—

C_4-7-cycloalkylene, —

O—

C_1-3-alkylene-C_3-7-cycloalkylene, —

O—

C_4-7-cycloalkylene-C_1-3-alkylene, or —

O—

C_1-3-alkylene-C_3-7-cycloalkylene-C_1-3-alkylene group, wherein the oxygen atom thereof in each case is linked to the bicyclic heteroaromatic moiety of formula (I),

(b) an —

O—

C_1-6-alkylene group substituted by an R₆O—

CO or R₆O—

CO—

C_1-4-alkyl group, wherein the oxygen atom of the —

O—

C_1-6-alkylene group is linked to the bicyclic heteroaromatic moiety of formula (I),

(c) an —

O—

C_2-6-alkylene group substituted at a position other than position 1 by a hydroxy, C_1-4-alkoxy, amino, C_1-4-alkylamino, di-(C_1-4-alkyl)-amino, pyrrolidino, piperidino, morpholino, piperazino, or 4-(C_1-4-alkyl)-piperazino group and the oxygen atom of the —

O—

C_2-6-alkylene group is linked to the bicyclic heteroaromatic moiety of formula (I),

(d) a —

C_1-6-alkylene group,

(e) an —

NR₄—

C_1-6-alkylene, —

NR₄—

C_3-7-cycloalkylene, —

NR₄—

C_1-3-alkylene-C_3-7-cycloalkylene, —

NR₄—

C_3-7-cycloalkylene-C_1-3-alkylene, or —

NR₄—

C_1-3-alkylene-C_3-7-cycloalkylene-C_1-3-alkylene group, wherein the —

NR₄—

moiety thereof in each case is linked to the bicyclic heteroaromatic moiety of formula (I),

(f) an oxygen atom linked to a carbon atom of the group D, and

(g) a NR₄ group linked to a carbon atom of the group D,

D is a group consisting of;

(a) an R₆O—

CO-alkylene-NR₅, (R₇O—

PO—

OR₈)-alkylene-NR₅, or (R₇O—

PO—

R₉)-alkylene-NR₅ group wherein in each case the alkylene moiety thereof, which is straight-chained and contains 1 to 6 carbon atoms, is additionally optionally substituted by one or two C_1-2-alkyl groups or by an R₆O—

CO or R₆O—

CO—

C_1-2-alkyl group,

(b) a 4- to 7-membered alkyleneimino group substituted by an R₆O—

CO, (R₇O—

PO—

OR₈), (R₇O—

PO—

R₉), R₆O—

CO—

C_1-4-alkyl, bis-(R₆O—

CO)—

C_1-4-alkyl, (R₇O—

PO—

OR₈)—

C_1-4-alkyl, or (R₇O—

PO—

R₉)—

C_1-4-alkyl group,

(c) a 4- to 7-membered alkyleneimino group substituted by two R₆O—

CO or R₆O—

CO—

C_1-4-alkyl groups or by an R₆OCO group and an R₆O—

CO—

C_1-4-alkyl group,

(d) a piperazino or homopiperazino group in each case substituted at the 4 position by R₁₀ and additionally substituted at a cyclic carbon atom thereof by an R₆O—

CO, (R₇O—

PO—

OR₈), (R₇O—

PO—

R₉), R₆O—

CO—

C_1-4-alkyl, bis-(R₆O—

CO)—

C_1-4-alkyl, (R₇O—

PO—

OR₈)—

C_1-4-alkyl, or (R₇O—

PO—

R₉)—

C_1-4-alkyl group,

(e) a piperazino or homopiperazino group in each case substituted at the 4 position by R₁₀ and additionally substituted at cyclic carbon atoms thereof by two R₆O—

CO or R₆O—

CO—

C_1-4-alkyl groups or by an R₆O—

CO group and an R₆O—

CO—

C_1-4-alkyl group,

(f) a piperazino or homopiperazino group substituted in each case at the 4 position by an R₆O—

CO—

C_1-4-alkyl, bis-(R₆—

CO)—

C_1-4-alkyl, (R₇O—

PO—

OR₈)—

C_1-4-alkyl, or (R₇O—

PO—

R₉)—

C_1-4-alkyl group,

(g) a piperazino or homopiperazino group substituted in each case at the 4 position by an R₆O—

CO—

C_1-4-alkyl, bis-(R₆O—

CO)—

C_1-4-alkyl, (R₇O—

PO—

OR₈)—

C_1-4-alkyl, or (R₇O—

PO—

R₉)—

C_1-4-alkyl group and additionally substituted at cyclic carbon atoms thereof by one or two R₆O—

CO or R₆O—

CO—

C_1-4-alkyl groups or by an R₆O—

CO group and an R₆O—

CO—

C_1-4-alkyl group,

(h) a morpholino or homomorpholino group substituted in each case by an R₆O—

CO, (R₇O—

PO—

OR₈), (R₇O—

PO—

R₉), R₆O—

CO—

C_1-4-alkyl, bis-(R₆O—

CO)—

C_1-4-alkyl, (R₇O—

PO—

OR₈)—

C_1-4-alkyl, or (R₇O—

PO—

R₉)—

C_1-4-alkyl group,

(i) a morpholino or homomorpholino group substituted in each case by two R₆O—

CO or R₆O—

CO—

C_1-4-alkyl groups or by an R₆O—

CO group and an R₆O—

CO—

C_1-4-alkyl group,

(j) a pyrrolidinyl, piperidinyl, or hexahydroazepinyl group substituted in each case at the 1 position by R₁₀, wherein the 5- to 7-membered rings thereof in each case are additionally substituted at a carbon atom by an R₆O—

CO, (R₇O—

PO—

OR₈), (R₇O—

PO—

R₉), R₆O—

CO—

C_1-4-alkyl, bis-(R₆O—

CO)—

C_1-4-alkyl, (R₇O—

PO—

OR₈)—

C_1-4-alkyl, or (R₇O—

PO—

R₉)—

C_1-4-alkyl group,

(k) a pyrrolidinyl, piperidinyl, or hexahydroazepinyl group substituted in each case at the 1 position by R₁₀, wherein the 5- to 7-membered rings thereof in each case are additionally substituted at carbon atoms thereof by two R₆O—

CO or R₆O—

CO—

C_1-4-alkyl groups or by an R₆O—

CO group and an R₆O—

CO—

C_1-4-alkyl group,

(l) a pyrrolidinyl, piperidinyl, or hexahydroazepinyl group substituted in each case at the 1 position by an R₆O—

CO—

C_1-4-alkyl, bis-(R₆O—

CO)—

C_1-4-alkyl, (R₇O—

PO—

OR₈)—

C_1-4-alkyl, or (R₇O—

PO—

R₉)—

C_1-4-alkyl group,

(m) a pyrrolidinyl, piperidinyl, or hexahydroazepinyl group substituted in each case at the 1 position by an R₇O—

CO—

C_1-4-alkyl, bis-(R₆O—

CO)—

C_1-4-alkyl, (R₇O—

PO—

OR₈)—

C_1-4-alkyl, or (R₇O—

PO—

R₉)—

C_1-4-alkyl group, wherein the 5- to 7-membered rings thereof in each case are additionally substituted at carbon atoms thereof by one or two R₆O—

CO or R₆O—

CO—

C_1-4-alkyl groups or by an R₆O—

CO group and an R₆O—

CO—

C_1-4-alkyl group,

(n) a 2-oxomorpholino group optionally substituted by 1 to 4 C_1-2-alkyl groups,

(o) a 2-oxomorpholinyl group substituted at the 4 position by a hydrogen atom, or by a C_1-4-alkyl, R₆O—

CO—

C_1-4-alkyl, (R₇O—

PO—

OR₈)—

C_1-4-alkyl, or (R₇O—

PO—

R₉)—

C_1-4-alkyl group, wherein the 2-oxomorpholinyl group is linked to a carbon atom of the group C, and

(p) an R₁₁NR₅ group, or

C and D together are a group consisting of;

(a) a hydrogen, fluorine, or chlorine atom;

(b) a C_1-6-alkoxy group,

(c) a C_2-6-alkoxy group substituted at a position other than position 1 by a hydroxy, C_1-4-alkoxy, amino, C_1-4-alkylamino, di-(C_1-4-alkyl)-amino, pyrrolidino, piperidino, hexahydroazepino, morpholino, homomorpholino, piperazino, 4-(C_1-4-alkyl)-piperazino, homopiperazino, 4-(C_1-4-alkyl)-homopiperazino, or 1-imidazolyl group,

(d) a C_1-4-alkoxy group substituted by a pyrrolidinyl, piperidinyl, or hexahydroazepinyl group substituted at the 1 position by R₁₀,

(e) a C_1-6-alkoxy group substituted by an R₆O—

CO, (R₇O—

PO—

OR₈), or (R₇O—

PO—

R₉) group,

(f) a C_3-7-cycloalkoxy or C_3-7-cycloalkyl-C_1-4-alkoxy group,

(g) an amino, C_1-4-alkylamino, di-(C_1-4-alkyl)-amino, pyrrolidino, piperidino, hexahydroazepino, morpholino, homomorpholino, piperazino, 4-(C_1-4-alkyl)-piperazino, homopiperazino, or 4-(C_1-4-alkyl)-homopiperazino group, and

(h) a 2-oxomorpholino group optionally substituted by 1 or 2 methyl groups,

with the proviso that;

(i) at least one of the groups B or D, or A together with B, or C together with D contains an optionally substituted 2-oxomorpholinyl group, an (R₇O—

PO—

OR₈) or (R₇O—

PO—

R₉) group, or

(ii) that at least one of the groups B or D contains an optionally substituted 2-oxotetrahydrofuran-3-yl, 2-oxotetrahydrofuran-4-yl, 2-oxotetrahydropyran-3-yl, 2-oxotetrahydropyran-4-yl, or 2-oxotetrahydropyran-5-yl group, or

(iii) that at least one of the groups A, B, C, or D, or A together with B, or C together with D contains an R₆O—

CO group and additionally one of the groups A, B, C, or D, or A together with B, or C together with D contains a primary, secondary, or tertiary amino function, wherein the nitrogen atom of this amino function is not linked to a carbon atom of an aromatic group,

R_c and R_d, which are identical or different, each are a hydrogen, fluorine, or chlorine atom, or a methoxy group or a methyl group optionally substituted by a methoxy, dimethylamino, diethylamino, pyrrolidino, piperidino, or morpholino group;

R_e and R_f, which are identical or different, in each case are a hydrogen atom or a C_1-4-alkyl group;

R_g is a C_1-4-alkyl, C_3-7-cycloalkyl, C_1-4-alkoxy, or C_5-7-cycloalkoxy group;

R₄ is a hydrogen atom or a C_1-4-alkyl group;

R₅ is a hydrogen atom,

a C_1-4-alkyl group optionally substituted by an R₆O—

CO, (R₇O—

PO—

OR₈), or (R₇O—

PO—

R₆) group,

a C_2-4-alkyl group substituted at a position other than position 1 by a hydroxy, C_1-4-alkoxy, amino, C_1-4-alkylamino, or di-(C_1-4-alkyl)-amino group, or by a 4- to 7-membered alkyleneimino group, wherein a methylene group at the 4 position of the 6- to 7-membered alkyleneimino group is optionally replaced by an oxygen or sulfur atom, or by a sulfinyl, sulfonyl, imino, or N—

(C_1-4-alkyl)-imino group, or

a C_3-7-cycloalkyl or C_3-7-cycloalkyl-C_1-3-alkyl group;

R₆, R₇, and R₈, which are identical or different, in each case are a hydrogen atom,

a C_1-8-alkyl group optionally substituted at a position other than position 1 by a hydroxy, C_1-4-alkoxy, amino, C_1-4-alkylamino, or di-(C_1-4-alkyl)-amino group or by a 4- to 7-membered alkyleneimino group, wherein a methylene group at the 4 position of the 6- to 7-membered alkyleneimino group is optionally replaced by an oxygen or sulfur atom, or by a sulfinyl, sulfonyl, imino, or N—

(C_1-4-alkyl)-imino group,

a C_4-7-cycloalkyl group optionally substituted by 1 or 2 methyl groups,

a C_3-5-alkenyl or C_3-5-alkynyl group, wherein the unsaturated moiety thereof is not linked to the oxygen atom, or

a C_3-7-cycloalkyl-C_1-4-alkyl, aryl, aryl-C_1-4-alkyl, or R₆CO—

O—

(R_eCR_f) group;

R₉ is a C_1-4-alkyl, aryl, or aryl-C_1-4-alkyl group;

R₁₀ is a hydrogen atom, or a C_1-4-alkyl, formyl, C_1-4-alkylcarbonyl, or C_1-4-alkylsulfonyl group;

R₁₁ is a 2-oxotetrahydrofuran-3-yl, 2-oxotetrahydrofuran-4-yl, 2-oxotetrahydropyran-3-yl, 2-oxotetrahydropyran-4-yl, or 2-oxotetrahydropyran-5-yl group each optionally substituted by one or two methyl groups;

R₁₂ is a cyano, carboxy, C_1-4-alkoxycarbonyl, aminocarbonyl, C_1-4-alkylaminocarbonyl, di-(C_1-4-alkyl)-aminocarbonyl, C_1-4-alkylsulfenyl, C_1-4-alkylsulfinyl, C_1-4-alkylsulfonyl, hydroxy, C_1-4-alkylsulfonyloxy, trifluoromethyloxy, nitro, amino, C_1-4-alkylamino, di-(C_1-4-alkyl)-amino, C_1-4-alkylcarbonylamino, N—

(C_1-4-alkyl)-C_1-4-alkylcarbonylamino, C_1-4-alkylsulfonylamino, N—

(C_1-4-alkyl)-C_1-4-alkylsulfonylamino, aminosulfonyl, C_1-4-alkylaminosulfonyl, or di-(C_1-4-alkyl)-aminosulfonyl group or a carbonyl group substituted by a 5- to 7-membered alkyleneimino group, wherein a methylene group at the 4 position of the 6- to 7-membered alkyleneimino group is optionally replaced by an oxygen or sulfur atom, or by a sulfinyl, sulfonyl, imino, or N—

(C_1-4-alkyl)-imino group; and

R₁₃ is a fluorine, chlorine, bromine, or iodine atom, or a C_1-4-alkyl, trifluoromethyl, or C_1-4-alkoxy group, or two groups R₁₃, if they are bound to adjacent carbon atoms, together are a C_3-5-alkylene, methylenedioxy, or 1,3-butadien-1,4-ylene group,

wherein the aryl moieties of the abovementioned groups are identical or different phenyl groups optionally monosubstituted by R₁₂, mono-, di-, or trisubstituted by R₁₃, or monosubstituted by R₁₂ and additionally mono- or disubstituted by R₁₃, wherein the substituents are identical or different,

or a tautomer, stereoisomer, or salt thereof.

2. The compound of formula (I) according to claim 1, wherein R_a is a hydrogen atom.

3. The compound of formula (I) according to claim 1, wherein:

R_a is a hydrogen atom;

R_b is a phenyl, benzyl, or 1-phenylethyl group wherein the phenyl nucleus is substituted in each case by R₁, R₂, and R₃, wherein;

R₁ and R₂, which are identical or different, each are;

(i) a hydrogen, fluorine, chlorine, bromine, or iodine atom;

(ii) a methyl, ethyl, hydroxy, methoxy, ethoxy, amino, cyano, vinyl, or ethynyl group,

(iii) an aryl, aryloxy, arylmethyl, or arylmethoxy group, or

(iv) a methyl or methoxy group substituted by 1 to 3 fluorine atoms, or R₁ together with R₂, if they are bound to adjacent carbon atoms, are a —

CH═

CH—

CH═

CH, —

CH═

CH—

NH, or —

CH═

N—

NH group, and

R₃ is a hydrogen, fluorine, chlorine, or bromine atom;

X is a nitrogen atom;

A is group consisting of;

(a) an —

O—

C_1-4-alkylene, —

O—

C_4-7-cycloalkylene, —

O—

C_1-3-alkylene-C_3-7-cycloalkylene, —

O—

C_4-7-cycloalkylene-C_1-3-alkylene, or —

O—

C_1-3-alkylene-C_3-7-cycloalkylene-C_1-3-alkylene group, wherein the oxygen atom thereof in each case is linked to the bicyclic heteroaromatic moiety of formula (I),

(b) an —

O—

C_2-4-alkylene group substituted at a position other than position 1 by a hydroxy group, wherein the oxygen atom of the —

O—

C_2-4-alkylene group is linked to the bicyclic heteroaromatic moiety of formula (I), or

(c) an oxygen atom linked to a carbon atom of the group B,

B is a group consisting of;

(a) an R₆O—

CO-alkylene-NR₅, (R₇O—

PO—

OR₈)-alkylene-NR₅, or (R₇O—

PO—

R₉)-alkylene-NR₅ group wherein in each case the alkylene moiety, which is straight-chained and contains 1 to 4 carbon atoms, is additionally optionally substituted by one or two C_1-2-alkyl groups or by an R₆O—

CO or R₆O—

CO—

C_1-2-alkyl group,

(b) a 4- to 7-membered alkyleneimino group substituted by an R₆O—

CO, R₆O—

CO—

C_1-4-alkyl, or bis-(R₆O—

CO)—

C_1-4-alkyl group,

(c) a 4- to 7-membered alkyleneimino group substituted by two R₆O—

CO or R₆O—

CO—

C_1-4-alkyl groups,

(d) a piperazino or homopiperazino group substituted at the 4 position by R₁₀ and additionally substituted at a cyclic carbon atom thereof by an R₆O—

CO, R₆O—

CO—

C_1-4-alkyl, or bis-(R₆O—

CO)—

C_1-4-alkyl group,

(e) a piperazino or homopiperazino group substituted at the 4 position by R₁₀ and additionally substituted at cyclic carbon atoms thereof by two R₆O—

CO or R₆O—

CO—

C_1-4-alkyl groups,

(f) a piperazino or homopiperazino group which in each case is substituted at the 4 position by an R₆O—

CO—

C_1-4-alkyl, bis-(R₆O—

CO)—

C_1-4-alkyl, (R₇O—

PO—

OR₈)—

C_1-4-alkyl, or (R₇O—

PO—

R₉)—

C_1-4-alkyl group,

(g) a piperazino or homopiperazino group substituted in each case at the 4 position by an R₆O—

CO—

C_1-4-alkyl or bis-(R₆O—

CO)—

C_1-4-alkyl group and additionally substituted at cyclic carbon atoms thereof by one or two R₆O—

CO or R₆O—

CO—

C_1-4-alkyl groups,

(h) a morpholino or homomorpholino group substituted in each case by an R₆O—

CO, R₆O—

CO—

C_1-4-alkyl, or bis-(R₆O—

CO)—

C_1-4-alkyl group,

(i) a morpholino or homomorpholino group substituted in each case by two R₆O—

CO or R₆O—

CO—

C_1-4-alkyl groups,

(j) a pyrrolidinyl, piperidinyl, or hexahydroazepinyl group substituted in each case at the 1 position by R₁₀, wherein the 5- to 7-membered rings thereof in each case are additionally substituted at a carbon atom thereof by an R₆O—

CO, R₆O—

CO—

C_1-4-alkyl, or bis-(R₆O—

CO)—

C_1-4-alkyl group,

(k) a pyrrolidinyl, piperidinyl, or hexahydroazepinyl group substituted in each case at the 1 position by R₁₀, wherein the 5- to 7-membered rings thereof in each case are additionally substituted at carbon atoms thereof by two R₆O—

CO or R₆O—

CO—

C_1-4-alkyl groups,

(l) a pyrrolidinyl, piperidinyl, or hexahydroazepinyl group substituted in each case at the 1 position by an R₆O—

CO—

C_1-4-alkyl, bis-(R₆O—

CO)—

C_1-4-alkyl, (R₇O—

PO—

OR₈)—

C_1-4-alkyl, or (R₇O—

PO—

R₉)—

C_1-4-alkyl group,

(m) a pyrrolidinyl, piperidinyl, or hexahydroazepinyl group substituted in each case at the 1 position by an R₆O—

CO—

C_1-4-alkyl or bis-(R₆O—

CO)—

C_1-4-alkyl group, wherein the 5- to 7-membered rings thereof in each case are additionally substituted at carbon atoms thereof by one or two R₆O—

CO or R₆O—

CO—

C_1-4-alkyl groups,

(n) a 2-oxomorpholino group optionally substituted by 1 to 4 C_1-2-alkyl groups,

(o) a 2-oxomorpholinyl group substituted at the 4 position by a hydrogen atom, or by a C_1-4-alkyl or R₆O—

CO—

C_1-4-alkyl group, wherein the 2-oxomorpholinyl group is linked to a carbon atom of the group A, and

(p) an R₁₁NR₅ group, or

A together with B are a group consisting of;

(a) a hydrogen atom,

(b) a C_1-4-alkoxy group,

(c) a C_2-4-alkoxy group substituted at a position other than position 1 by a hydroxy, C_1-4-alkoxy, amino, C_1-4-alkylamino, di-(C_1-4-alkyl)-amino, pyrrolidino, piperidino, morpholino, piperazino, or 4-(C_1-4-alkyl)-piperazino group,

(d) a C_1-4-alkoxy group substituted by a pyrrolidinyl or piperidinyl group substituted at the 1 position by R₁₀,

(e) a C_1-4-alkoxy group substituted by an R₆O—

CO group, and

(f) a C_4-7-cycloalkoxy or C_3-7-cycloalkyl-C_1-4-alkoxy group;

C is a group consisting of;

(a) an —

O—

C_1-4-alkylene, —

O—

C_4-7-cycloalkylene, —

O—

C_1-3-alkylene-C_3-7-cycloalkylene, —

O—

C_4-7-cycloalkylene-C_1-3-alkylene, or —

O—

C_1-3-alkylene-C_3-7-cycloalkylene-C_1-3-alkylene group, wherein the oxygen atom thereof in each case is linked to the bicyclic heteroaromatic moiety of formula (I),

(b) an —

O—

C_2-4-alkylene group substituted at a position other than position 1 by a hydroxy group, wherein the oxygen atom of the —

O—

C_2-4-alkylene group is linked to the bicyclic heteroaromatic moiety of formula (I), and

(c) an oxygen atom linked to a carbon atom of the group D,

D is a group consisting of;

(a) an R₆O—

CO-alkylene-NR₅, (R₇O—

PO—

OR₈)-alkylene-NR₅, or (R₇O—

PO—

R₉)-alkylene-NR₅ group wherein in each case the alkylene moiety, which is straight-chained and contains 1 to 4 carbon atoms, is additionally optionally substituted by one or two C_1-2-alkyl groups or by an R₆O—

CO or R₆O—

CO—

C_1-2-alkyl group,

(b) a 4- to 7-membered alkyleneimino group substituted by an R₆O—

CO, R₆O—

CO—

C_1-4-alkyl, or bis-(R₆O—

CO)—

C_1-4-alkyl group,

(c) a 4- to 7-membered alkyleneimino group substituted by two R₆O—

CO or R₆O—

CO—

C_1-4-alkyl groups,

(d) a piperazino or homopiperazino group substituted at the 4 position by R₁₀ and additionally at a cyclic carbon atom thereof by an R₆O—

CO, R₆O—

CO—

C_1-4-alkyl, or bis-(R₆O—

CO)—

C_1-4-alkyl group,

(e) a piperazino or homopiperazino group substituted at the 4 position by R₁₀ and additionally substituted at cyclic carbon atoms thereof by two R₆O—

CO or R₆O—

CO—

C_1-4-alkyl groups,

(f) a piperazino or homopiperazino group substituted in each case at the 4 position by an R₆O—

CO—

C_1-4-alkyl, bis-(R₆O—

CO)—

C_1-4-alkyl, (R₇O—

PO—

OR₈)—

C_1-4-alkyl, or (R₇O—

PO—

R₉)—

C_1-4-alkyl group,

(g) a piperazino or homopiperazino group substituted at the 4 position by an R₆O—

CO—

C_1-4-alkyl or bis-(R₆O—

CO)—

C_1-4-alkyl group and additionally substituted at cyclic carbon atoms thereof by one or two R₆O—

CO or R₆O—

CO—

C_1-4-alkyl groups,

(h) a morpholino or homomorpholino group substituted in each case by an R₆O—

CO, R₆O—

CO—

C_1-4-alkyl, or bis-(R₆O—

CO)—

C_1-4-alkyl group,

(i) a morpholino or homomorpholino group substituted by two R₆O—

CO or R₆O—

CO—

C_1-4-alkyl groups,

(l) a pyrrolidinyl, piperidinyl, or hexahydroazepinyl group substituted at the 1 position by R₁₀, wherein the 5- to 7-membered rings thereof in each case are additionally substituted at a carbon atom thereof by an R₆O—

CO, R₆O—

CO—

C_1-4-alkyl, or bis-(R₆O—

CO)—

C_1-4-alkyl group,

(k) a pyrrolidinyl, piperidinyl, or hexahydroazepinyl group substituted at the 1 position by R₁₀, wherein the 5- to 7-membered rings thereof in each case are additionally substituted at carbon atoms thereof by two R₆O—

CO or R₆O—

CO—

C_1-4-alkyl groups,

(l) a pyrrolidinyl, piperidinyl, or hexahydroazepinyl group substituted at the 1 position by an R₆O—

CO—

C_1-4-alkyl, bis-(R₆O—

CO)—

C_1-4-alkyl, (R₇O—

PO—

OR₈)—

C_1-4-alkyl, or (R₇O—

PO—

R₉)—

C_1-4-alkyl group,

(m) a pyrrolidinyl, piperidinyl, or hexahydroazepinyl group substituted at the 1 position by an R₆O—

CO—

C_1-4-alkyl or bis-(R₆O—

CO)—

C_1-4-alkyl group, wherein the 5- to 7-membered rings thereof in each case are additionally substituted at carbon atoms thereof by one or two R₆O—

CO or R₆O—

CO—

C_1-4-alkyl groups,

(n) a 2-oxomorpholino group optionally substituted by 1 to 4 C_1-2-alkyl groups,

(o) a 2-oxomorpholinyl group substituted at the 4 position by a hydrogen atom, or by a C_1-4-alkyl or R₆O—

CO—

C_1-4-alkyl group, wherein the 2-oxomorpholinyl group is linked to a carbon atom of the group C, and

(p) an R₁₁NR₅ group, or

C together with D are a group consisting of;

(a) a hydrogen atom,

(b) a C_1-4-alkoxy group,

(c) a C_2-4-alkoxy group substituted at a position other than position 1 by a hydroxy, C_1-4-alkoxy, amino, C_1-4-alkylamino, di-(C_1-4-alkyl)-amino, pyrrolidino, piperidino, morpholino, piperazino, or 4-(C_1-4-alkyl)-piperazino group,

(d) a C_1-4-alkoxy group substituted by a pyrrolidinyl or piperidinyl group substituted at the 1 position by R₁₀,

(e) a C_1-4-alkoxy group substituted by an R₆O—

CO group, and

(f) a C_4-7-cycloalkoxy or C_3-7-cycloalkyl-C_1-4-alkoxy group;

R_c and R_d in each case are a hydrogen atom;

R_e and R_f, which are identical or different, in each case are a hydrogen atom or a C_1-4-alkyl group;

R_g is a C_1-4-alkyl, C_3-6-cycloalkyl, C_1-4-alkoxy, or C_5-6-cycloalkoxy group;

R₅ is a hydrogen atom,

a C_1-4-alkyl group optionally substituted by an R₆O—

CO group,

a C_2-4-alkyl group substituted at a position other than position 1 by a hydroxy or C_1-4-alkoxy group, or

a C_3-6-cycloalkyl or C_3-6-cycloalkyl-C_1-3-alkyl group;

R₆, R₇, and R₈, which are identical or different, in each case are a hydrogen atom,

a C_1-8-alkyl group optionally substituted at a position other than position 1 by a hydroxy, C_1-4-alkoxy, or di-(C_1-4-alkyl)-amino group or by a 4- to 7-membered alkyleneimino group, wherein a methylene group at the 4 position of the 6- to 7-membered alkyleneimino group is optionally replaced by an oxygen atom or by an N—

(C_1-2-alkyl)-imino group,

a C_4-6-cycloalkyl group,

a C_3-5-alkenyl or C_3-5-alkynyl group, wherein the unsaturated moiety is not linked to the oxygen atom,

a C_3-6-cycloalkyl-C_1-4-alkyl, aryl, aryl-C_1-4-alkyl, or R_gCO—

O—

(R_eCR_f) group, wherein

R₉ is a C_1-4-alkyl group;

R₁₀ is a hydrogen atom, or a methyl or ethyl group;

R₁₁ is a 2-oxotetrahydrofuran-3-yl, 2-oxotetrahydrofuran-4-yl, 2-oxotetrahydropyran-3-yl, 2-oxotetrahydropyran-4-yl, or 2-oxotetrahydropyran-5-yl group optionally substituted by one or two methyl groups;

R₁₂ is a cyano, C_1-2-alkoxycarbonyl, aminocarbonyl, C_1-2-alkylaminocarbonyl, di-(C_1-2-alkyl)-aminocarbonyl, C_1-2-alkylsulfenyl, C_1-2-alkylsulfinyl, C_1-2-alkylsulfonyl, hydroxy, nitro, amino, C_1-4-alkylamino, or di-(C_1-4-alkyl)-amino group; and

R₁₃ is a fluorine, chlorine, bromine, or iodine atom, or a C_1-2-alkyl, trifluoromethyl, or C_1-2-alkoxy group, or two groups R₁₃, if they are bound to adjacent carbon atoms, together are a C_3-5-alkylene, methylenedioxy, or 1,3-butadien-1,4-ylene group,

or a tautomer, stereoisomer, or salt thereof.

4. The compound of formula (I) according to claim 1, wherein:

R_a is a hydrogen atom,

R_b is a phenyl, benzyl, or 1-phenylethyl group wherein the phenyl nucleus is substituted in each case by R₁, R₂, and R₃, wherein;

R₁ and R₂, which are identical or different, each are;

(i) a hydrogen, fluorine, chlorine, or bromine atom, or

(ii) a methyl, trifluoromethyl, methoxy, ethynyl, or cyano group, and

R₃ is a hydrogen atom;

X is a nitrogen atom;

A is an —

O—

C_1-4-alkylene or —

O—

CH₂—

CH(OH)—

CH₂ group, wherein the oxygen atom thereof in each case is linked to the bicyclic heteroaromatic moiety of formula (I);

B is a group consisting of;

(a) an R₆O—

CO-alkylene-NR₅ group wherein the alkylene moiety, which is straight-chained and contains 1 or 2 carbon atoms, is additionally optionally substituted by an R₆O—

CO or R₆O—

CO-methyl group;

(b) a pyrrolidino or piperidino group substituted by an R₆O—

CO or R₆O—

CO—

C_1-2-alkyl group,

(c) a pyrrolidino or piperidino group substituted by two R₆O—

CO or R₆O—

CO—

C_1-2-alkyl groups,

(d) a piperazino group substituted at the 4 position by R₁₀ and additionally at a cyclic carbon atom thereof by an R₆O—

CO or R₆O—

CO—

C_1-2-alkyl group,

(e) a piperazino group substituted at the 4 position by an R₆O—

CO—

C_1-4-alkyl, bis-(R₆O—

CO)—

C_1-4-alkyl, (R₇O—

PO—

OR₈)-methyl, or (R₇O—

PO—

R₉)-methyl group,

(f) a piperazino group substituted at the 4 position by an R₆O—

CO—

C_1-2-alkyl group and additionally at a cyclic carbon atom thereof by an R₆O—

CO or R₆O—

CO—

C_1-2-alkyl group,

(g) a morpholino group substituted by an R₆O—

CO or R₆O—

CO—

C_1-2-alkyl group,

(h) a pyrrolidinyl or piperidinyl group substituted at the 1 position by an R₆O—

CO—

C_1-4-alkyl, bis-(R₆O—

CO)—

C_1-4-alkyl, (R₇O—

PO—

OR₈)-methyl, or (R₇O—

PO—

R₉)-methyl group,

(i) a 2-oxomorpholino group optionally substituted by 1 or 2 methyl groups,

(j) a 2-oxomorpholinyl group substituted at the 4 position by a methyl, ethyl, or R₆O—

CO—

C_1-2-alkyl group, wherein the 2-oxomorpholinyl group is linked to a carbon atom of the group A, and

(k) a R₁₁N(C_1-2-alkyl) group, or

A and together with B are a group consisting of;

(a) a hydrogen atom, or a methoxy, ethoxy, or 2-methoxyethoxy group,

(b) a C_1-2-alkoxy group substituted by an R₆O—

CO group, and

(c) a C_4-6-cycloalkoxy or C_3-6-cycloalkyl-C_1-3-alkoxy group;

C is an —

O—

C_1-4-alkylene or —

O—

CH₂—

CH(OH)—

CH₂ group, wherein the oxygen atom thereof in each case is linked to the bicyclic heteroaromatic moiety of formula (I),

D is a group consisting of;

(a) an R₆O—

CO-alkylene-NR₅ group wherein the alkylene moiety, which is straight-chained and contains 1 or 2 carbon atoms, is additionally optionally substituted by an R₆O—

CO or R₆O—

CO-methyl group,

(b) a pyrrolidino or piperidino group substituted by an R₆O—

CO or R₆O—

CO—

C_1-2-alkyl group,

(c) a pyrrolidino or piperidino group substituted by two R₆O—

CO or R₆O—

CO—

C_1-2-alkyl groups,

(d) a piperazino group substituted at the 4 position by R₁₀ and additionally substituted at a cyclic carbon atom thereof by an R₆O—

CO or R₆O—

CO—

C_1-2-alkyl group,

(e) a piperazino group substituted at the 4 position by an R₆O—

CO—

C_1-4-alkyl, bis-(R₆O—

CO)—

C_1-4-alkyl, (R₇O—

PO—

OR₈)-methyl, or (R₇O—

PO—

R₉)-methyl group,

(f) a piperazino group substituted at the 4 position by an R₆O—

CO—

C_1-2-alkyl group and additionally substituted at a cyclic carbon atom thereof by an R₆O—

CO or R₆O—

CO—

C_1-2-alkyl group,

(g) a morpholino group substituted by an R₆O—

CO or R₆O—

CO—

C_1-2-alkyl group,

(h) a pyrrolidinyl or piperidinyl group substituted at the 1 position by an R₆O—

CO—

C_1-4-alkyl, bis-(R₆O—

CO)—

C_1-4-alkyl, (R₇O—

PO—

OR₈)-methyl, or (R₇O—

PO—

R₉)-methyl group,

(i) a 2-oxomorpholino group optionally substituted by 1 or 2 methyl groups,

a 2-oxomorpholinyl group substituted at the 4 position by a methyl, ethyl, or R₆O—

CO—

C_1-2-alkyl group, wherein the 2-oxomorpholinyl group is linked to a carbon atom of the group C, and

(k) a R₁₁N(C_1-2-alkyl) group, or

C together with D are a group consisting of;

(a) a hydrogen atom, or a methoxy, ethoxy, or 2-methoxyethoxy group,

(b) a C_1-2-alkoxy group substituted by an R₆O—

CO group, and

(c) a C_4-6-cycloalkoxy or C_3-6-cycloalkyl-C_1-3-alkoxy group;

R_c and R_d in each case are a hydrogen atom;

R_e is a hydrogen atom or a C_1-4-alkyl group;

R_f is a hydrogen atom;

R_g is a C_1-4-alkyl, cyclopentyl, cyclohexyl, C_1-4-alkoxy, cyclopentyloxy, or cyclohexyloxy group;

R₅ is a hydrogen atom,

a C_1-2-alkyl group optionally substituted by an R₆O—

CO group,

a C_2-4-alkyl group substituted at a position other than position 1 by a hydroxy group, or

a C_3-6-cycloalkyl or C_3-6-cycloalkylmethyl group;

R₆ is a hydrogen atom, or a C_1-6-alkyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, cyclohexylmethyl, phenyl, benzyl, 5-indanyl, or R_gCO—

O—

(R_eCR_f) group;

R₇ and R₈, which are identical or different, in each case are a hydrogen atom, or a methyl, ethyl, phenyl, benzyl, 5-indanyl, or R_gCO—

O—

(R_eCR_f) group;

R₉ is a methyl or ethyl group;

R₁₀ is a hydrogen atom, or a methyl or ethyl group; and

R₁₁ is a 2-oxotetrahydrofuran-3-yl or 2-oxotetrahydrofuran-4-yl group,

or a tautomer, stereoisomer, or salt thereof.

5. The compound of formula (I) according to claim 1, wherein:

R_a is a hydrogen atom;

R_b is a phenyl, benzyl, or 1-phenylethyl group wherein the phenyl nucleus is substituted in each case by R₁, R₂, and R₃, wherein;

R₁ and R₂, which are identical or different, each are a hydrogen, fluorine, chlorine, or bromine atom, or a methyl, trifluoromethyl, methoxy, ethynyl, or cyano group, and R₃ is a hydrogen atom;

X is a nitrogen atom;

A is an —

O—

C_1-4-alkylene or —

O—

CH₂—

CH(OH)—

CH₂ group, wherein the oxygen atom thereof in each case is linked to the bicyclic heteroaromatic moiety of formula (I);

B is a group consisting of;

(a) a R₆O—

CO-alkylene-NR₅ group wherein the alkylene moiety, which is straight-chained and contains 1 or 2 carbon atoms, is additionally optionally substituted by an R₆O—

CO or R₆O—

CO-methyl group,

(b) a pyrrolidino or piperidino group substituted by an R₆O—

CO or R₆O—

CO—

C_1-2-alkyl group,

(c) a pyrrolidino or piperidino group substituted by two R₆O—

CO or R₆O—

CO—

C_1-2-alkyl groups,

(d) a piperazino group substituted at the 4 position by R₁₀ and additionally substituted at a cyclic carbon atom thereof by an R₆O—

CO or R₆O—

CO—

C_1-2-alkyl group,

(e) a piperazino group substituted at the 4 position by an R₆O—

CO—

C_1-4-alkyl, bis-(R₆O—

CO)—

C_1-4-alkyl, (R₇O—

PO—

OR₈)-methyl, or (R₇O—

PO—

R₉)-methyl group,

(f) a piperazino group substituted at the 4 position by an R₆O—

CO—

C_1-2-alkyl group and additionally substituted at a cyclic carbon atom thereof by an R₆O—

CO or R₆O—

CO—

C_1-2-alkyl group,

(g) a morpholino group substituted by an R₆O—

CO or R₆O—

CO—

C_1-2-alkyl group,

(h) a pyrrolidinyl or piperidinyl group substituted at the 1 position by an R₆O—

CO—

C_1-4-alkyl, bis-(R₆O—

CO)—

C_1-4-alkyl, (R₇O—

PO—

OR₈)-methyl, or (R₇O—

PO—

R₉)-methyl group,

(i) a 2-oxomorpholino group optionally substituted by 1 or 2 methyl groups,

a 2-oxomorpholinyl group substituted at the 4 position by a methyl, ethyl, or R₆O—

CO—

C_1-2-alkyl group, wherein the 2-oxomorpholinyl group is linked to a carbon atom of the group A, and

(k) a R₁₁N(C_1-2-alkyl) group, or

C together with D are a group consisting of a hydrogen atom, and a methoxy, ethoxy, 2-methoxyethoxy, C_4-6-cycloalkoxy, and C_3-6-cycloalkyl-C_1-3-alkoxy group;

R_c and R_d in each case are a hydrogen atom;

R_e is a hydrogen atom or a C_1-4-alkyl group;

R_f is a hydrogen atom;

R_g is a C_1-4-alkyl, cyclopentyl, cyclohexyl, C_1-4-alkoxy, cyclopentyloxy, or cyclohexyloxy group;

R₅ is a hydrogen atom,

a C_1-2-alkyl group optionally substituted by an R₆O—

CO group,

a C_2-4-alkyl group substituted at a position other than position 1 by a hydroxy group, or

a C_3-6-cycloalkyl or C_3-6-cycloalkylmethyl group;

R₆ is a hydrogen atom, or a C_1-6-alkyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, cyclohexylmethyl, phenyl, benzyl, 5-indanyl, or R_gCO—

O—

(R_eCR_f) group;

R₇ and R₈, which are identical or different, in each case are a hydrogen atom, or a methyl, ethyl, phenyl, benzyl, 5-indanyl, or R_gCO—

O—

(R_eCR_f) group;

R₉ is a methyl or ethyl group;

R₁₀ is a hydrogen atom, or a methyl or ethyl group; and

R₁₁ is a 2-oxotetrahydrofuran-3-yl or 2-oxotetrahydrofuran-4-yl group,

or a tautomer, stereoisomer, or salt thereof.

6. The compound of formula (I) according to claim 1, wherein:

R_a is a hydrogen atom;

R_b is a phenyl, benzyl, or 1-phenylethyl group wherein the phenyl nucleus is substituted in each case by R₁, R₂, and R₃, wherein;

R₁ and R₂, which are identical or different, each are;

(i) a hydrogen, fluorine, chlorine, or bromine atom, or

(ii) a methyl, trifluoromethyl, methoxy, ethynyl, or cyano group, and

R₃ is a hydrogen atom;

X is a nitrogen atom;

A together with B are a group consisting of;

a hydrogen atom, or a methoxy, ethoxy, 2-methoxyethoxy, C_4-6-cycloalkoxy, or C_3-6-cycloalkyl-C_1-3-alkoxy group;

C is an —

O—

C_1-4-alkylene or —

O—

CH₂—

CH(OH)—

CH₂ group, wherein the oxygen atom thereof in each case is linked to the bicyclic heteroaromatic moiety of formula (I);

D is a group consisting of;

(a) R₆O—

CO-alkylene-NR₅ group wherein the alkylene moiety, which is straight-chained and contains 1 or 2 carbon atoms, is additionally optionally substituted by an R₆O—

CO or R₆O—

CO-methyl group,

(b) a pyrrolidino or piperidino group substituted by an R₆O—

CO or R₆O—

CO—

C_1-2-alkyl group,

(c) a pyrrolidino or piperidino group substituted by two R₆O—

CO or R₆O—

CO—

C_1-2-alkyl groups,

(d) a piperazino group substituted at the 4 position by R₁₀ and additionally at a cyclic carbon atom thereof by an R₆O—

CO or R₆O—

CO—

C_1-2-alkyl group,

(e) a piperazino group substituted at the 4 position by an R₆O—

CO—

C_1-4-alkyl, bis-(R₆O—

CO)—

C_1-4-alkyl, (R₇O—

PO—

OR₈)-methyl, or (R₇O—

PO—

R₉)-methyl group,

(f) a piperazino group substituted at the 4 position by an R₆O—

CO—

C_1-2-alkyl group and additionally substituted at a cyclic carbon atom thereof by an R₆O—

CO or R₆O—

CO—

C_1-2-alkyl group,

(g) a morpholino group substituted by an R₆O—

CO or R₆O—

CO—

C_1-2-alkyl group,

(h) a pyrrolidinyl or piperidinyl group substituted at the 1 position by an R₆O—

CO—

C_1-4-alkyl, bis-(R₆O—

CO)—

C_1-4-alkyl, (R₇O—

PO—

OR₈)-methyl, or (R₇O—

PO—

R₉)-methyl group,

(i) a 2-oxomorpholino group optionally substituted by 1 or 2 methyl groups,

(j) a 2-oxomorpholinyl group substituted at the 4 position by a methyl, ethyl, or R₆O—

CO—

C_1-2-alkyl group, wherein the 2-oxomorpholinyl group is linked to a carbon atom of the group C, and

(k) a R₁₁N(C_1-2-alkyl) group;

R_c and R_d in each case are a hydrogen atom;

R_e is a hydrogen atom or a C_1-4-alkyl group;

R_f is a hydrogen atom;

R_g is a C_1-4-alkyl, cyclopentyl, cyclohexyl, C_1-4-alkoxy, cyclopentyloxy, or cyclohexyloxy group;

R₅ is a hydrogen atom,

a C_1-2-alkyl group optionally substituted by an R₆O—

CO group,

a C_2-4-alkyl group substituted at position 2 by a hydroxy group, or

a C_3-6-cycloalkyl or C_3-6-cycloalkylmethyl group;

R₆ is a hydrogen atom, or

a C_1-6-alkyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, cyclohexylmethyl, phenyl, benzyl, 5-indanyl, or R_gCO—

O—

(R_eCR_f) group;

R₇ and R₈, which are identical or different, in each case are a hydrogen atom, or a methyl, ethyl, phenyl, benzyl, 5-indanyl, or R_gCO—

O—

(R_eCR_f) group;

R₉ is a methyl or ethyl group;

R₁₀ is a hydrogen atom, or a methyl or ethyl group;

R₁₁ is a 2-oxotetrahydrofuran-3-yl or 2-oxotetrahydrofuran-4-yl group,

or a tautomer, stereoisomer, or salt thereof.

7. The compound of formula (I) according to claim 1, wherein:

R_a is a hydrogen atom;

R_b is a phenyl group wherein the phenyl nucleus is substituted in each case by R₁, R₂, and R₃, wherein;

R₁ and R₂, which are identical or different, each are a hydrogen, fluorine, chlorine, or bromine atom, and

R₃ is a hydrogen atom;

X is a nitrogen atom;

A is an —

O—

C_1-4-alkylene or —

O—

CH₂—

CH(OH)—

CH₂ group, wherein the oxygen atom thereof in each case is linked to the bicyclic heteroaromatic moiety of formula (I);

B is a group consisting of;

(a) an R₆—

CO—

CH₂—

NR₅ group;

(b) a pyrrolidino or piperidino group substituted by an R₆O—

CO group,

(c) a piperazino group substituted at the 4 position by an R₆O—

CO—

CH₂ or bis-(R₆O—

CO)—

C_1-3-alkyl group,

(d) a pyrrolidinyl or piperidinyl group substituted at the 1 position by an R₆O—

CO—

CH₂ group,

(e) a 2-oxomorpholino group optionally substituted by one or two methyl groups, or

(f) a R₁₁N(C_1-2-alkyl) group, or

C together with D is a group consisting of a methoxy, C_4-6-cycloalkoxy, or C_3-6-cycloalkylmethoxy group;

R_c and R_d in each case are a hydrogen atom;

R₅ is a hydrogen atom or a methyl group optionally substituted by an R₆O—

CO group, or

a C_2-4-alkyl group substituted at a position other than position 1 by a hydroxy group;

R₆ is a hydrogen atom, or a methyl or ethyl group;

R₁₁ is a 2-oxotetrahydrofuran-3-yl or 2-oxotetrahydrofuran-4-yl group, and

or a tautomer, stereoisomer, or salt thereof.

9. The compound according to one of claims 1 to 8, wherein the compound is a physiologically acceptable salt.

10. A pharmaceutical composition comprising an effective amount of a compound of formula (I) according to one of claims 1 to 8 and an inert carrier or diluent.

11. A pharmaceutical composition comprising an effective amount of a compound of formula (I) according to claim 9 and an inert carrier or diluent.

12. A method for treatment or prophylaxis of benign or malignant tumors, diseases of the airways and lungs, polyps, diseases of the gastrointestinal tract, bile duct, gall bladder, kidneys, and skin, in a host in need of such treatment or prophylaxis, which method comprises administering the host an effective amount of a compound according to one of claims 1 to 8.

13. A method for treatment or prophylaxis of benign or malignant tumors, diseases of the airways and lungs, polyps, diseases of the gastrointestinal tract, bile duct, gall bladder, kidneys, and skin, in a host in need of such treatment or prophylaxis, which method comprises administering the host an effective amount of a compound according to claim 9.

8. A compound selected from the group consisting of:

(1) 4-(3-chloro-4-fluorophenylamino)-6-{3-[4-(methoxycarbonylmethyl)-1-piperazinyl]propyloxy}-7-methoxyquinazoline;

(2) 4-[(3-bromophenyl)amino]-6-(2-{4-[(ethoxycarbonyl)methyl]piperazin-1-yl}ethoxy)-7-methoxyquinazoline;

(3) (S)-4-[(3-bromophenyl)amino]-6-[3-(2-methoxycarbonylpyrrolidin-1-yl)propyloxy]-7-methoxyquinazoline;

(4) 4-[(3-bromophenyl)amino]-6-(3-{4-[(ethoxycarbonyl)methyl]piperazin-1-yl}-2-hydroxypropyloxy)-7-methoxyquinazoline;

(5) (S)-4-[(3-bromophenyl)amino]-6-({1-[(ethoxycarbonyl)methyl]pyrrolidine-2-yl}methoxy)-7-methoxyquinazoline; and

(6) 4-[(3-bromophenyl)amino]-6-(2-{4-[1,2-bis(methoxycarbonyl)ethyl]piperazin-1-yl}ethoxy)-7-methoxyquinazoline,

and the salts thereof.