Heterocyclic derivatives
View Patent ↗The invention relates to novel heterocyclic derivatives of the general formula (I), processes for their preparation, and their use in medicaments, especially for the treatment of chronic obstructive pulmonary diseases, acute coronary syndrome, acute myocardial infarction, and heart failure development.
1. A compound of formula (I)
wherein
A represents heteroaryl ring,
R 1 , R 2 and R 3 independently from each other represent hydrogen, halogen, nitro, cyano, C 1 -C 6 -alkyl, hydroxy or C 1 -C 6 -alkoxy, wherein C 1 -C 6 -alkyl and C 1 -C 6 -alkoxy can be further substituted with one to three identical or different radicals selected from the group consisting of halogen, hydroxy and C 1 -C 4 -alkoxy,
R 4 represents trifluoromethylcarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenoxycarbonyl, hydroxycaxbonyl, aminocarbonyl, mono- or di-C 1 -C 4 -alkylamino-carbonyl, C 6 -C 10 -arylaminocaxbonyl, arylcarbonyl, heteroarylcarbonyl, heterocyclylcarbonyl, heteroaryl, heterocyclyl or cyano, wherein C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxy-carbonyl, mono- and di-C 1 -C 4 -alkylaminocarbonyl can be further substituted with one to three identical or different radicals selected from the group consisting of C 3 -C 8 -cycloalkyl, hydroxy, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl, hydroxycarbonyl, aminocarbonyl, mono- and di-C 1 -C 4 -alkylaminocarbonyl, C 1 -C 4 -alkylcarbonylamino, N—(C 1 -C 4 -alkylcarbonyl)-N—(C 1 -C 4 -alkyl)amino, cyano, amino, mono- and di-C 1 -C 4 -alkylamino, heteroaryl, heterocyclyl and tri-(C 1 -C 6 -alkyl)-silyl, and wherein heteroarylcarbonyl, heterocyclylcarbonyl, heteroaryl and heterocyclyl can be further substituted with C 1 -C 4 -alkyl,
R 5 represents C 1 -C 4 -alkyl, which can be substituted with one to three identical or different radicals selected from the group consisting of halogen, hydroxy, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenoxy, C 1 -C 6 -alkylthio, amino, mono- and di-C 1 -C 6 -alkylamino, arylamino, hydroxycarbonyl, C 1 -C 6 -alkoxycarbonyl and the radical —O—C 1 -C 4 -alkyl-O—C 1 -C 4 -alkyl,
or
R 5 represents amino,
R 6 represents
a group of the formula -T-U wherein
T represents a C 1 -C 6 -alkanediyl or C 2 -C 6 -alkenediyl group
and
U represents
C 6 -C 10 -aryl or 5- or 6-membered heteroaryl each of which is substituted by one, two or three radicals independently selected from the group consisting of halogen, C 1 -C 6 -alkyl, 5- or 6-membered heteroaryl and a group of the formula —V—W wherein V represents a bond or a C 1 -C 6 -alkanediyl or C 2 -C 6 -alkenediyl group both of which can be further substituted by C 3 -C 8 -cycloalkyl, and W represents C 1 -C 6 -alkoxycarbonyl or hydroxycarbonyl,
a group of the formula —C(═O)—NR a —SO 2 —R b wherein R a represents hydrogen or C 1 -C 6 -alkyl, and R b represents C 1 -C 6 -alkyl which can be substituted by trifluoromethyl, or R b represents C 6 -C 10 -aryl which can be substituted by C 1 -C 6 -alkyl, halogen, cyano, nitro or trifluoromethyl,
a group of the formula —C(═O)—NR c R d wherein R c represents hydrogen or C 1 -C 6 -alkyl, and R d represents C 6 -C 10 -aryl which can be substituted by C 1 -C 6 -alkoxycarbonyl or hydroxycarbonyl,
a group of the formula —C(═O)—NR e —OR f wherein R e and R f independently from each other represent hydrogen or C 1 -C 6 -alkyl,
or
C 6 -C 10 -arylalkoxy which, in the aryl part, can be substituted by halogen,
C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl or hydroxycarbonyl,
or
R 6 represents
C 3 -C 8 -cycloalkyl which can be substituted by up to three radicals independently selected from the group consisting of C 1 -C 6 -alkyl, hydroxy, oxo, C 1 -C 6 -alkoxycarbonyl and hydroxycarbonyl,
C 2 -C 6 -alkenyl which can be substituted by C 1 -C 6 -alkoxycarbonyl or hydroxycarbonyl,
C 1 -C 6 -alkyl or C 1 -C 6 -alkylcarbonyl which are substituted by C 1 -C 6 -alkoxycarbonylamino,
C 1 -C 6 -alkoxycarbonyl which is substituted by phenyl-C 1 -C 6 -alkoxycarbonyl which for its part, in the phenyl moiety, can be further substituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl or hydroxycarbonyl,
or
a group of the formula —SO 2 —R g wherein R g represents C 1 -C 6 -alkyl which can be substituted by trifluoromethyl, or R g represents C 6 -C 10 -aryl which can be substituted by C 1 -C 6 -alkyl, halogen, cyano, nitro, trifluoromethyl, C 1 -C 6 -alkoxycarbonyl or hydroxycarbonyl,
R 7 represents halogen, nitro, cyano, C 1 -C 6 -alkyl, hydroxy or C 1 -C 6 -alkoxy, wherein C 1 -C 6 -alkyl and C 1 -C 6 -alkoxy can be further substituted with one to three identical or different radicals selected from the group consisting of halogen, hydroxy and C 1 -C 4 -alkoxy,
and
Y 1 , Y 2 , Y 3 , Y 4 and Y 5 independently from each other represent CH or N, wherein the ring contains either 0, 1 or 2 nitrogen atoms,
and salts thereof.
2. The compound of formula (I) according to claim 1 , wherein
A represents heteroaryl ring,
R 1 , R 2 and R 3 independently from each other represent hydrogen, halogen, nitro, cyano, C 1 -C 6 -alkyl, hydroxy or C 1 -C 6 -alkoxy, wherein C 1 -C 6 -alkyl and C 1 -C 6 -alkoxy can be further substituted with one to three identical or different radicals selected from the group consisting of halogen, hydroxy and C 1 -C 4 -alkoxy,
R 4 represents C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenoxycarbonyl, hydroxy-carbonyl, aminocarbonyl, mono- or di-C 1 -C 4 -alkylaminocarbonyl, C 6 -C 10 -arylaminocarbonyl, heteroarylcarbonyl, heterocyclylcarbonyl, heteroaryl, heterocyclyl or cyano, wherein C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, mono- and di-C 1 -C 4 -alkylaminocarbonyl can be further substituted with one to three identical or different radicals selected from the group consisting of C 3 -C 8 -cycloalkyl, hydroxy, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl, hydroxycarbonyl, aminocarbonyl, mono- and di-C 1 -C 4 -alkylaminocarbonyl, C 1 -C 4 -alkylcarbonylamino, amino, mono- and di-C 1 -C 4 -alkylamino, heteroaryl, heterocyclyl and tri-(C 1 -C 6 -alkyl)-silyl,
R 5 represents C 1 -C 4 -alkyl, which can be substituted with one to three identical or different radicals selected from the group consisting of halogen, hydroxy, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenoxy, C 1 -C 6 -alkylthio, amino, mono- and di-C 1 -C 6 -alkylamino, arylamino, hydroxycarbonyl, C 1 -C 6 -alkoxycarbonyl and the radical —O—C 1 -C 4 -alkyl-O—C 1 -C 4 -alkyl,
R 6 represents
a group of the formula -T-U wherein
T represents a C 1 -C 4 -alkanediyl or C 2 -C 4 -alkenediyl group
and
U represents
C 6 -C 10 -aryl or 5- or 6-membered heteroaryl each of which is substituted by one, two or three radicals independently selected from the group consisting of halogen, C 1 -C 6 -alkyl, 5- or 6-membered heteroaryl and a group of the formula —V—W wherein V represents a bond, a C 2 -C 6 -alkenediyl group or a C 1 -C 6 -alkanediyl group the latter of which can be further substituted by C 3 -C 8 -cycloalkyl, and W represents C 1 -C 6 -alkoxy-carbonyl or hydroxycarbonyl,
a group of the formula —C(═O)—NH—SO 2 —R b wherein R b represents C 1 -C 6 -alkyl which can be substituted by trifluoromethyl, or R b represents C 6 -C 10 -aryl which can be substituted by C 1 -C 6 -alkyl, halogen, cyano, nitro or trifluoromethyl,
or
a group of the formula —C(═O)NHR d wherein R d represents C 6 -C 10 -aryl which can be substituted by C 1 -C 6 -alkoxycarbonyl or hydroxycarbonyl,
or
R 6 represents
C 3 -C 8 -cycloalkyl which can be substituted by up to three radicals independently selected from the group consisting of C 1 -C 6 -alkyl, hydroxy, oxo, C 1 -C 6 -alkoxycarbonyl and hydroxycarbonyl,
or
C 2 -C 6 -alkenyl which can be substituted by C 1 -C 6 -alkoxycarbonyl or hydroxyl-carbonyl,
R 7 represents halogen, nitro, cyano, C 1 -C 6 -alkyl, hydroxy or C 1 -C 6 -alkoxy, wherein C 1 -C 6 -alkyl and C 1 -C 6 -alkoxy can be further substituted with one to three identical or different radicals selected from the group consisting of halogen, hydroxy and C 1 -C 4 -alkoxy,
and
Y 1 , Y 2 , Y 3 , Y 4 and Y 5 independently from each other represent CH or N, wherein the ring contains either 0, 1 or 2 nitrogen atoms.
3. The compound of formula (I) according to claim 1 , wherein
A represents a pyridyl ring,
R 1 , R 2 and R 3 independently from each other represent hydrogen, fluoro, chloro, bromo, nitro, cyano, methyl, ethyl, trifluoromethyl or trifluoromethoxy,
R 4 represents C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, allyloxycarbonyl, hydroxycarbonyl, aminocarbonyl, mono-C 1 -C 4 -alkylaminocarbonyl, furylcarbonyl, pyridylcarbonyl or cyano, wherein C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl and mono-C 1 -C 4 -alkylaminocarbonyl can be substituted with one to three identical or different radicals selected from the group consisting of C 3 -C 6 -cycloalkyl, hydroxy, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl, hydroxy-carbonyl, amino, mono- and di-C 1 -C 4 -alkylamino,
R 5 represents methyl or ethyl,
R 6 represents
a group of the formula -T-U wherein
T represents a C 1 -C 4 -alkanediyl group
and
U represents
phenyl, furyl, thienyl, oxazolyl, thiazolyl or pyridyl each of which is substituted by one or two radicals independently selected from the group consisting of fluoro, chloro, bromo, C 1 -C 4 -alkyl, thienyl, pyridyl and a group of the formula —V—W wherein V represents a bond or a C 1 -C 4 -alkanediyl or C 2 -C 4 -alkenediyl group, and W represents C 1 -C 4 -alkoxy-carbonyl or hydroxycarbonyl,
a group of the formula —C(═O)—NH—SO 2 —R b wherein R b represents C 1 -C 4 -alkyl which can be substituted by trifluoromethyl, or R b represents phenyl which can be substituted by C 1 -C 4 -alkyl, fluoro, chloro, bromo, cyano, nitro or trifluoromethyl,
or
a group of the formula —C(═O)—NHR d wherein R d represents phenyl which can be substituted by C 1 -C 4 -alkoxycarbonyl or hydroxycarbonyl,
or
R 6 represents
C 3 -C 6 -cycloalkyl which can be substituted by up to two radicals independently selected from the group consisting of C 1 -C 4 -alkyl; hydroxy, oxo, C 1 -C 4 -alkoxycarbonyl and hydroxycarbonyl,
or
C 2 -C 4 -alkenyl which is substituted by C 1 -C 4 -alkoxycarbonyl or hydroxycarbonyl,
R 7 represents halogen, nitro, cyano, trifluoromethyl, trifluoromethoxy, methyl or ethyl,
and
Y 1 , Y 2 , Y 3 , Y 4 and Y 1 each represent CH.
4. The compound of formula (I) according to claim 1 , wherein
A represents a pyridyl ring,
R 1 and R 3 each represent hydrogen,
R 2 represents fluoro, chloro, bromo, nitro or cyano,
R 4 represents cyano, hydroxycarbonyl, furylcarbonyl, pyridylcarbonyl, C 1 -C 4 -alkylcarbonyl or C 1 -C 4 -alkoxycarbonyl, wherein C 1 -C 4 -alkylcarbonyl and C 1 -C 4 -alkoxycarbonyl can be substituted with a radical selected from the group consisting of hydroxy, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl, hydroxycarbonyl, mono- and di-C 1 -C 4 -alkylamino,
R 5 represents methyl,
R 6 represents
a group of the formula -T-U wherein
T represents a —CH 2 — group
and
U represents
phenyl, furyl or oxazolyl each of which is substituted by one or two radicals independently selected from the group consisting of fluoro, chloro, bromo, C 1 -C 4 -alkyl and a group of the formula —V—W wherein V represents a bond, a —CH 2 — group or a —CH═CH— group, and W represents C 1 -C 4 -alkoxycarbonyl or hydroxy-carbonyl,
a group of the formula —C(═O)—NH—SO 2 —R b wherein R b represents C 1 -C 4 -alkyl which can be substituted by trifluoromethyl, or R b represents phenyl which can be substituted by C 1 -C 4 -alkyl, fluoro, chloro, bromo, cyano, nitro or trifluoromethyl,
or
a group of the formula —C(═O)—NHR d wherein R d represents phenyl which can be substituted by C 1 -C 4 -alkoxycarbonyl or hydroxycarbonyl,
or
R 6 represents
C 3 -C 6 -cycloalkyl which can be substituted by up to two radicals independently selected from the group consisting of C 1 -C 4 -alkyl, hydroxy, oxo, C 1 -C 4 -alkoxycarbonyl and hydroxycarbonyl,
or
a —CH═CH— group which is substituted by C 1 -C 4 -alkoxycarbonyl or hydroxycarbonyl,
R 7 represents trifluoromethyl or nitro,
and
Y 1 , Y 2 , Y 3 , Y 4 and Y 1 each represent CH.
5. The compound of formula (I) according to claim 1 , wherein A is pyridyl.
6. The compound of formula (I) according to claim 1 , wherein R 1 is hydrogen.
7. The compound of formula (I) according to claim 1 , wherein R 2 is cyano.
8. The compound of formula (I) according to claim 1 , wherein R 3 is hydrogen.
9. The compound of formula (I) according to claim 1 , wherein R 4 is C 1 -C 4 -alkoxycarbonyl optionally substituted by hydroxy, or wherein R 4 is C 1 -C 4 -alkylcarbonyl, hydroxycarbonyl or cyano.
10. The compound of formula (I) according to claim 1 , wherein R 5 is methyl.
11. The compound of formula (I) according to claim 1 , wherein R 7 is trifluoromethyl or nitro.
12. A compound of formula (IA)
wherein
Z represents N, and
R 1 and R 3 independently from each other represent hydrogen, halogen, nitro, cyano, C 1 -C 6 -alkyl, hydroxy or C 1 -C 6 -alkoxy, wherein C 1 -C 6 -alkyl and C 1 -C 6 -alkoxy can be further substituted with one to three identical or different radicals selected from the group consisting of halogen hydroxy and C 1 -C 4 -alkoxy,
R 4 represents trifluoromethylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenoxycarbonyl, hydroxycaxbonyl aminocarbonyl, mono- or di-C 1 -C 4 -alkylaminocarbonyl C 6 -C 10 -arylaminocaxbonyl, arylcarbonyl, heteroarylcarbonyl, heterocyclylcarbonyl, heteroaryl, heterocyclyl or cyano, wherein C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxy-carbonyl, mono- and di-C 1 -C 4 -alkylaminocarbonyl can be further substituted with one to three identical or different radicals selected from the group consisting of C 3 -C 8 -cycloalkyl, hydroxy, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl, hydroxycarbonyl, aminocarbonyl, mono- and di-C 1 -C 4 -alkylaminocarbonyl, C 1 -C 4 -alkylcarbonylamino, N—(C 1 -C 4 -alkylcarbonyl)-N—(C 1 -C 4 -alkyl)amino, cyano amino, mono- and di-C 1 -C 4 -alkylamino heteroaryl, heterocyclyl and tri-(C 1 -C 6 -alkyl)-silyl, and wherein heteroarylcarbonyl, heterocyclylcarbonyl, heteroaryl and heterocyclyl can be further substituted with C 1 -C 4 -alkyl,
R 6 represents
a group of the formula -T-U wherein
T represents a C 1 -C 6 -alkanediyl or C 2 -C 6 -alkenediyl group
and
U represents
C 6 -C 10 -aryl or 5- or 6-membered heteroaryl each of which is substituted by one, two or three radicals independently selected from the group consisting of halogen C 1 -C 6 -alkyl, 5- or 6-membered heteroaryl and a group of the formula —V—W wherein V represents a bond or a C 1 -C 6 -alkanediyl or C 2 -C 6 -alkenediyl group both of which can be further substituted by C 3 -C 8 -cycloalkyl, and W represents C 1 -C 6 -alkoxycarbonyl or hydroxycarbonyl,
a group of the formula —C(═O)—NR a —SO 2 —R b wherein R a represents hydrogen or C 1 -C 6 -alkyl, and R b represents C 1 -C 6 -alkyl which can be substituted b trifluoromethyl, or R b represents C 6 -C 10 -aryl which can be substituted b C 1 -C 6 -alkyl, halogen, cyano, nitro or trifluoromethyl,
a group of the formula —C(═O)—NR c R d wherein R c represents hydrogen or C 1 -C 6 -alkyl, and R d represents C 6 -C 10 -aryl which can be substituted by C 1 -C 6 -alkoxycarbonyl or hydroxycarbonyl,
a group of the formula —C(═O)—NR e —OR f wherein R e and R f independently from each other represent hydrogen or C 1 -C 6 -alkyl,
or
C 6 -C 10 -arylalkoxy which, in the aryl part can be substituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl or hydroxycarbonyl,
or
R 6 represents
C 3 -C 8 -cycloalkyl which can be substituted by up to three radicals independently selected from the group consisting of C 1 -C 6 -alkyl, hydroxy, oxo, C 1 -C 6 -alkoxycarbonyl and hydroxycarbonyl,
C 2 -C 6 -alkenyl which can be substituted b C 1 -C 6 -alkoxycarbonyl or hydroxycarbonyl,
C 1 -C 6 -alkyl or C 1 -C 6 -alkylcarbonyl which are substituted by C 1 -C 6 alkoxycarbonylamino,
C 1 -C 6 -alkoxycarbonyl which is substituted by phenyl-C 1 -C 6 -alkoxycarbonyl which for its part in the phenyl moiety, can be further substituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl or hydroxycarbonyl,
or
a group of the formula —SO 2 —R g wherein R g represents C 1 -C 6 -alkyl which can be substituted b trifluoromethyl or R g represents C 6 -C 10 -aryl which can be substituted by C 1 -C 6 -alkyl, halogen, cyano, nitro, trifluoromethyl, C 1 -C 6 -alkoxycarbonyl or hydroxycarbonyl.
13. A process for synthesizing a compound of formula (I)
wherein
A represents an aryl or heteroaryl ring,
R 1 , R 2 and R 3 independently from each other represent hydrogen, halogen, nitro, cyano, C 1 -C 6 -alkyl, hydroxy or C 1 -C 6 -alkoxy, wherein C 1 -C 6 -alkyl and C 1 -C 6 -alkoxy can be further substituted with one to three identical or different radicals selected from the group consisting of halogen, hydroxy and C 1 -C 4 -alkoxy,
R 4 represents trifluoromethylcarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -aralkoxycarbonyl, C 2 -C 6 -alkenoxycarbonyl, hydroxycaxbonyl, aminocarbonyl, mono- or di-C 1 -C 4 -alkylaminocarbonyl, C 6 -C 10 -arylaminocaxbonyl, arylcarbonyl, heteroarylcarbonyl, heterocyclylcarbonyl, heteroaryl, heterocyclyl or cyano, wherein C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbon mono- and di-C 1 -C 4 -alkylaminocarbonyl can be further substituted with one to three identical or different radicals selected from the group consisting of C 3 -C 8 -cycloalkyl, hydroxy, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl, hydroxycarbonyl, aminocarbonyl, mono- and di-C 1 -C 4 -alkylaminocarbonyl, C 1 -C 4 -alkylcarbonylamino, N—(C 1 -C 4 -alkylcarbonyl)-N—(C 1 -C 4 -alkyl)amino cyano, amino, mono- and di-C 1 -C 4 -alkylamino heteroaryl, heterocyclyl and tri-(C 1 -C 6 -alkyl)-silyl and wherein heteroarylcarbonyl, heterocyclylcarbonyl, heteroaryl and heterocyclyl can be further substituted with C 1 -C 4 -alkyl,
R 5 represents C 1 -C 4 -alkyl, which can be substituted with one to three identical or different radicals selected from the group consisting of halogen, hydroxy, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenoxy, C 1 -C 6 -alkylthio, amino, mono- and di-C 1 -C 6 -alkylamino, arylamino hydroxycarbonyl, C 1 -C 6 -alkoxycarbonyl and the radical —O—C 1 -C 4 -alkyl-O—C 1 -C 4 -alkyl,
or
R 5 represents amino,
R 6 represents
a group of the formula -T-U wherein
T represents a C 1 -C 6 -alkanediyl or C 2 -C 6 -alkenediyl group
and
U represents
C 6 -C 10 -aryl or 5- or 6-membered heteroaryl each of which is substituted by one, two or three radicals independently selected from the group consisting of halogen C 1 -C 6 -alkyl, 5- or 6-membered heteroaryl and a group of the formula —V—W wherein V represents a bond or a C 1 -C 6 -alkanediyl or C 2 -C 6 -alkenediyl group both of which can be further substituted b C 3 -C 8 -cycloalkyl, and W represents C 1 -C 6 -alkoxycarbonyl or hydroxycarbonyl,
a group of the formula —C(═O)—NR a —SO 2 —R b wherein R a represents hydrogen or C 1 -C 6 -alkyl, and R b represents C 1 -C 6 -alkyl which can be substituted by trifluoromethyl or R b represents C 6 -C 10 -aryl which can be substituted b C 1 -C 6 -alkyl, halogen, cyano, nitro or trifluoromethyl,
a group of the formula —C(═O)—NR c R d wherein R c represents hydrogen or C 1 -C 6 -alkyl, and R d represents C 6 -C 10 -aryl which can be substituted by C 1 -C 6 -alkoxycarbonyl or hydroxycarbonyl,
a group of the formula —C(═O)—NR e —OR f wherein R e and R f independently from each other represent hydrogen or C 1 -C 6 -alkyl,
or
C 6 -C 10 -arylalkoxy which, in the aryl part, can be substituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl or hydroxycarbonyl,
or
R 6 represents
C 3 -C 8 -cycloalkyl which can be substituted by up to three radicals independently selected from the group consisting of C 1 -C 6 -alkyl, hydroxy, oxo, C 1 -C 6 -alkoxycarbonyl and hydroxycarbonyl,
C 2 -C 6 -alkenyl which can be substituted by C 1 -C 6 -alkoxycarbonyl or hydroxycarbonyl,
C 1 -C 6 -alkyl or C 1 -C 6 -alkylcarbonyl which are substituted by C 1 -C 6 -alkoxycarbonylamino,
C 1 -C 6 -alkoxycarbonyl which is substituted by phenyl-C 1 -C 6 -alkoxycarbonyl which for its part, in the phenyl moiety, can be further substituted by halogen C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl or hydroxycarbonyl,
or
a group of the formula —SO 2 —R g wherein R g represents C 1 -C 6 -alkyl which can be substituted b trifluoromethyl, or R g represents C 6 -C 10 -aryl which can be substituted by C 1 -C 6 -alkyl, halogen, cyano, nitro, trifluoromethyl, C 1 -C 6 -alkoxycarbonyl or hydroxycarbonyl,
R 7 represent halogen, nitro, cyano, C 1 -C 6 -alkyl, hydroxy or C 1 -C 6 -alkoxy, wherein C 1 -C 6 -alkyl and C 1 -C 6 -alkoxy can be further substituted with one to three identical or different radicals selected from the group consisting of halogen hydroxy and C 1 -C 4 -alkoxy,
and
Y 1 , Y 2 , Y 3 , Y 4 and Y 5 independently from each other represent CH or N, wherein the ring contains either 0, 1 or 2 nitrogen atoms,
the process comprising the step of condensing a compound of formula (II)
wherein A, R 1 and R 2 have the meaning indicated in this claim,
with a compound of formula (III)
wherein R 4 and R 5 have the meaning indicated in this claim,
and a compound of formula (IV)
wherein R 3 , R 7 , and Y 1 to Y 5 have the meaning indicated in this claim, to give a compound of formula (IB)
wherein A, R 1 to R 5 , R 7 , and Y 1 to Y 5 have the meaning indicated in this claim, and reactomg the compound of general (IB) with a compound of formula (V)
R 6 —X (V),
wherein
R 6 has the meaning indicated in this claim, and
X represents a leaving group,
in the presence of a base.
14. The composition containing at least one compound of general formula (I) according to claim 1 and a pharmacologically acceptable diluent.
15. A method for treating chronic obstructive pulmonary disease, acute myocardial syndrome, or acute myocardial infarction by administering to a human in need thereof a neutrophil elastase inhibitory amount of a compound of formula (I) according to claim 1 .