MX2008004780A - Antibacterial active 5-chinolin derivative - Google Patents

Abstract

The invention relates to novel antibacterial compounds of formula (I) which, in particular, are embodied in the form of DNA gyrase and topoisomerase inhibitors ( for example topoisomerase II and IV) of interest

Description

ACTIVE DERIVATIVE ANTIBACTERIAL 5-QUINOLINE DESCRIPTION OF THE INVENTION Resistance to antibiotics currently used has increased appreciably in many countries of the world in recent years and in some cases has reached alarming proportions. The main problem is that pathogens show not only a single resistance but, as a rule, multiple resistance. This is especially true for some groups of gram-positive pathogens such as staphylococci, pneumococci and enterococci (S. Ewig et al., Anti-biotika-Resistenz bei Erregern ambulant erworbener Atemwegsinfektionen (Antibiotic resistance in pathogens of outpatient-acquired respiratory tract infections), Chemother, J. 2002, 11, 12-26; F, Tenover, Development and Spread of Bacterial Resistance to Antimicrobial Agents: an overview, Clin. Infect. Dis. 2001 Sep 15, 33 Suppl 3, 108-115). Recently, a long-standing development has been presented: The first strain of Staphylococcus aureus has been described in the United States, which is not only resistant to methicillin but is highly resistant to vancomycin (Centers for Disease Control and Prevention, Staphylococcus aureus). resistant to vancomycin -United States, 2002, MMR 2002, 51, 565-567). In addition to hygienic measures in hospitals, therefore, increasing efforts are also required to find new antibiotics that, as far as possible, have a novel structure and a novel mechanism of action in order to be effective against these problematic pathogens. The present invention describes novel classes of compounds having antibacterial activity. These compounds are, among others, of interest as inhibitors of DNA gyrase and topoisomerase (for example topoisomerase II and IV). The present invention relates to compounds of the general formula (I): wherein the residue R1 is a hydrogen atom, a halogen atom, a hydroxy, an amino, a cyano, a nitro, a thiol, an alkyl of 1 to 6 carbon atoms, an alkenyl of 2 to 6 carbon atoms , an alkynyl of 2 to 6 carbon atoms, a heteroalkyl, an alkyloxy, a heteroalkyloxy, a cycloalkyloxy, an alkylcycloalkyloxy, a heterocycloalkyloxy or a heteroalkylcycloalkyloxy group; the residue R2 is a hydrogen atom, a halogen atom, a hydroxy, an amino, a cyano, an alkyl of 1 to 6 carbon atoms, an alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms carbon or a heteroalkyl group; the residue R3 is a group of the following formula: wherein U and V independently from each other are nitrogen atoms or groups of the formula CH or CR6; the R4 residues independently of one another are a halogen atom, a hydroxy, an amino, a cyano, a nitro or a thiol group, an alkyl, alkenyl, alkynyl or heteroalkyl group; n is equal to 0, 1 or 2; the residue Rs is an alkyl, alkenyl, alkynyl, heteroalkyl, aryl, heteroaryl, cycloalkyl, alkylcycloalkyl, heteroalkylcycloalkyl, heterocycloalkyl, aralkyl or heteroaralkyl group, the R6 residues independently of each other being a halogen atom, a hydroxy group, alkyl, alkenyl, alkynyl or heteroalkyl; A is selected from the following groups: -CR10 (OR11) CR12R13-, -CR8R9CR10 (OR11) -, -OCR8R9CR12R13-, -CR8R9CR12R130-, -CR8R9S02-, -S02CR8R9-, -CR8R9NR7-, -NR7CR8R9-, -CR8R90- , -OCR8R9-, -CR8R9S-, -SCR8R9-, -NRC (= 0) -, -C (= 0) NR7- and -CR8R9CR1R13-; the residue R7 is a hydrogen atom, a trifluoromethyl, an alkyl group of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkoxycarbonyl of 1 to 6 carbon atoms, alkylcarbonyl of 1 to 6 carbon atoms or carbonylamino, wherein the amino group of the carbonylamino group, if applicable, may be substituted by an alkoxycarbonyl group of 1 to 6 carbon atoms, alkylcarbonyl of 1 to 6 carbon atoms, alkenyloxycarbonyl of 2 to 6 carbon atoms, alkenylcarbonyl of 2 to 6 carbon atoms, an alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms and, if applicable, may be further substituted by an alkyl group of 1 to 6 carbon atoms or alkenyl of 2 to 6 carbon atoms. to 6 carbon atoms; the residues R8, R9, R10, R12 and R13 independently of each other are a hydrogen atom, a halogen atom, an azide, a trifluoromethyl, hydroxy, amino, alkyloxy of 1 to 6 carbon atoms, alkylthio of 1 to 6 atoms of carbon, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkoxycarbonyl of 1 to 6 carbon atoms, alkenyloxycarbonyl of 2 to 6 carbon atoms, alkylsulfonyl of 1 to 6 carbon atoms, alkenylsulfonyl of 2 to 6 carbon atoms or a sulfonylamino group, wherein the amino group of the sulfonylaraine group, if applicable, may be substituted by an alkyl group of 1 to 6 carbon atoms or phenyl; the residue R11 is a hydrogen atom, a trifluoromethyl group, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkoxycarbonyl of 1 to 6 carbon atoms, alkylcarbonyl of 1 to 6 carbon atoms or carbonylamino , wherein the amino group of the carbonylamino group, if applicable, may be substituted by an alkoxycarbonyl group of 1 to 6 carbon atoms, alkylcarbonyl of 1 to 6 carbon atoms, alkenyloxycarbonyl of 2 to 6 carbon atoms, alkenylcarbonyl of 2 to 6 carbon atoms, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms and, if applicable, may be further substituted by an alkyl group of 1 to 6 carbon atoms or alkenyl of 2 to 6 carbon atoms; or a pharmaceutically acceptable salt, solvate, hydrate or a pharmacologically acceptable formulation thereof. The term "alkyl" refers to a saturated straight or branched chain hydrocarbon group containing from 1 to 20 carbon atoms, preferably from 1 to 12 carbon atoms, particularly preferably from 1 to 6 carbon atoms, for example a group methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tertbutyl, n-pentyl, n-hexyl, 2,2-dimethylbutyl or n-octyl. The terms alkenyl and alkynyl refer to at least partially unsaturated straight or branched chain hydrocarbon groups containing from 2 to 20 carbon atoms, preferably from 2 to 12 carbon atoms, particularly preferably from 2 to 6 carbon atoms , for example the group ethenyl, allyl, acetylenyl, propargyl, isoprenyl or hex-2-enyl. Preferably, the alkenyl groups have one or two (preferably especially one) double bonds and the alkynyl groups have one or two (preferably especially one) triple bond. In addition, the terms alkyl, alkenyl and alkynyl refer to groups in which one or more hydrogen atoms have been replaced by a halogen atom (preferably F or Cl) such as, for example, a group 2, 2, 2- trichloroethyl or a trifluoromethyl group. The term "heteroalkyl" refers to an alkyl, alkenyl or alkynyl group in which one or more carbon atoms (preferably 1, 2 or 3) have been replaced by an oxygen, nitrogen, phosphorus, boron, selenium, silicon or sulfur atom (preferably by an oxygen, sulfur or nitrogen atom). The term "heteroalkyl" further refers to a carboxylic acid or a group derived from a carboxylic acid such as, for example, acyl, acyloalkyl, alkoxycarbonyl, acyloxy, acyloxyalkyl, carboxyalkylamide or alkoxycarbonyloxy. Examples of heteroalkyl groups are groups of the formulas: Ra-0-Ya. Ra-S-Ya, RaN (Rb) -Ya-, Ra-CO-Ya-, Ra-0-CO-O-Y3-, Ra-CO-N (RD) -Ya-, Ra-N (Rb) -CO-Ya-, Ra-0-CO-N (R) -Ya-, Ra-N (Rb) -CO-0-Y3, Ra-N (Rb) -CO-N (Rc) -Ya-, Ra-0-CO-0-Ya-, Ra ~ N (Rb) -C (= NRd) -N (RC) -Ya-, Ra-CS-Ya-, Ra-0-CS-Ya-, Ra- CS-0-Ya-, Ra-CS-0-Ya-, Ra-CS-N (Rb) -Ya-, RaN (Rb) -CS-Ya-, Ra-0-CS-N (Rb) -Ya -, Ra-N (Rb) -CS-N (RC) -Ya-, Ra-0-CS-0-Ya-, Ra-S-CO-Ya-, Ra-CO-SN (Rb) -Ya- , Ra-CS-S-Ya-, Ra-S-CS-N (Rb) -Ya-, Ra-N (Rb) -CS-S-Y3-, Ra-S-CS-0-Ya-, Ra -0-CS-S-Ya-, wherein Ra is a hydrogen atom, an alkyl group of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms or alkynyl of 2 to 6 carbon atoms; Rb is a hydrogen atom, an alkyl group of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms or alkynyl of 2 to 6 carbon atoms; Rc is a hydrogen atom, an alkyl group of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms or alkynyl of 2 to 6 carbon atoms; Rd is a hydrogen atom, an alkyl group of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms or alkynyl of 2 to 6 carbon atoms and Y is a direct bond, an alkylene group of 1 to 6 atoms of carbon, alkenylene of 2 to 6 carbon atoms or alkynylene of 2 to 6 carbon atoms, in each of each heteroalkyl group contains at least one carbon atom and one or more hydrogen atoms which may be substituted by fluorine atoms or chlorine. Specific examples of heteroalkyl groups are methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropyloxy, tert-butyloxy, methoxymethyl, ethoxymethyl, -CH2CH20H, -CH20H, methoxyethyl, methylamino, ethylamino, dimethylamino, diethylamino, isopropylethylamino, methylaminomethyl, ethylaminomethyl, diisopropylaminoethyl, enol ether , dimethylaminomethyl, dimethylaminoethyl, acetyl, propionyl, butyryloxy, acetyloxy, methoxycarbonyl, ethoxycarbonyl, N-ethyl-N-methylcarbamoyl or N-methylcarbamoyl. Additional examples of heteroalkyl groups are nitrile, isonitrile, cyanate, thiocyanate, isocyanate, isothiocyanate and alkyl nitrile groups. An example of a heteroalkylene group is a group of formula -CH2CH (0H) -. The term "cycloalkyl" refers to a saturated or partially saturated cyclic group (for example a cycloalkenyl group) that contains one or more rings (preferably 1 or 2) and contains from 3 to 14 carbon atoms in the ring, preferably from 3 to 10. carbon atoms in the ring (especially 3, 4, 5, 6 or 7). The term cycloalkyl further refers to groups in which one or more hydrogen atoms have been replaced by fluorine, chlorine, bromine or iodine atoms, or by OH groups, = 0, SH, = S, NH2 or N02, thus, for example, cyclic ketones such as, for example, cyclohexanone, 2-cyclohexanone or cyclopentanone. Additional specific examples of cycloalkyl groups are cyclopropyl, cyclobutyl, cyclopentyl, spiro [4,5] decanyl, norbornyl, cyclohexyl, cyclopentenyl, cyclohexadienyl, decalinyl, bicyclo [4.3.0] nonyl, tetralin, cyclopentacyclohexyl, fluorocyclohexyl or cyclohexyl- 2-enyl. The term "heterocycloalkyl" refers to a cycloalkyl group as defined above in which one or more carbon atoms in the ring (preferably 1, 2 or 3) have been replaced by an oxygen, nitrogen, silicon, selenium, phosphorus or sulfur atom (preferably by an oxygen, sulfur or nitrogen atom). A heterocycloalkyl group preferably has one or two rings containing from 3 to 10 ring atoms (especially 3, 4, 5, 6 or 7). The term "heterocycloalkyl" further refers to groups in which one or more hydrogen atoms have been replaced by fluorine, chlorine, bromine or iodine atoms, or by OH groups, = 0, SH, = S, NH2 or N02. Examples are piperidyl, piperazinyl, morpholinyl, urotropinyl, pyrrolidinyl, tetrahydrothiophenyl, tetrahydropyranyl, tetrahydrofuryl or a 2-pyrazolinyl group and also lactams, lactones, cyclic imides and cyclic anhydrides. The term "alkylcycloalkyl" refers to groups containing both cycloalkyl and alkyl, alkenyl or alkynyl groups according to the above definitions, for example alkylcycloalkyl, cycloalkylalkyl, alkylcycloalkenyl, alkenylcycloalkyl and alkynylcycloalkyl groups. An alkylcycloalkyl group preferably contains a cycloalkyl group containing one or two ring systems having from 3 to 10 (especially 3, 4, 5, 6 or 7) carbon atoms in the ring and one or two alkyl, alkenyl or alkynyl groups that have 1 or 2 to 6 carbon atoms. The term "heteroalkylcycloalkyl" refers to alkylcycloalkyl groups as defined above in which one or more (preferably 1, 2 or 3) carbon atoms have been replaced by an oxygen, nitrogen, silicon, selenium, phosphorus or sulfur atom (preferably by an oxygen, sulfur or nitrogen atom). Preferably, a heteroalkylcycloalkyl group contains one or two ring systems having from 3 to 10 (especially 3, 4, 5, 6 or 7) ring atoms and one or two alkyl, alkenyl, alkynyl or heteroalkyl groups having 1 or 2 to 6 carbon atoms. Examples of such groups are alkylheterocycloalkyl, alkylheterocycloalkenyl, alkenylheterocycloalkyl, alkynylheterocycloalkyl, heteroalkylcycloalkyl, heteroalkylheterocycloalkyl and heteroalkylheterocycloalkenyl, the cyclic groups are saturated or monounsaturated, diunsaturated or triunsaturated. The term "aryl" or "Ar" refers to an aromatic group containing one or more rings containing from 6 to 14 carbon atoms in the ring, preferably from 6 to 10 (especially 6) carbon atoms in the ring. The expression aryl (or Ar respectively) also refers to groups in which one or more hydrogen atoms have been replaced by fluorine, chlorine, bromine or iodine atoms or by OH, SH, NH2 or N02 groups. Examples are phenyl, naphthyl, biphenyl, 2-fluorophenyl, anilinyl, 3-nitrophenyl or 4-hydroxyphenyl groups. The term "heteroaryl" refers to an aromatic group containing one or more rings containing from 5 to 14 ring atoms, preferably from 5 to 10 (especially 5 or 6) atoms in the ring and containing one or more (preferably 1) , 2, 3 or 4) atoms in the oxygen, nitrogen, phosphorus or sulfur ring (preferably 0, S or N). The term "heteroaryl" further refers to groups in which one or more hydrogen atoms have been replaced by fluorine, chlorine, bromine or iodine atoms or by OH, SH, NH2 or N02 groups. Examples are 4-pyridyl, 2-imidazolyl, 3-phenylpyrrolyl, thiazolyl, oxazolyl, triazolyl, tetrazolyl, isoxazolyl, indazolyl, indolyl, benzimidazolyl, pyridazinyl, quinolinyl, purinyl, carbazolyl, acridinyl, pyrimidyl, 2,3 '- bifuryl, 3-pyrazolyl and isoquinolyl. The term "aralkyl" refers to groups containing aryl groups and also alkyl, alkenyl, alkynyl or cycloalkyl, according to the above definitions, such as, for example, arylalkyl, arylalkenyl, arylalkynyl, arylcycloalkyl, arylcycloalkenyl, alkylarylcycloalkyl and alkylarylcycloalkenyl groups. The specific examples of aralkyl are toluene, xylene, mesitylene, styrene, benzyl chloride, o-fluorotoluene, lH-indene, tetralin, dihydronaphthalene, indanone, phenylcyclopentyl, eumeno, cyclohexylphenyl, fluorene and indane. An aralkyl group preferably contains one or two aromatic ring systems (1 or 2 rings) containing from 6 to 10 carbon atoms and 1 or 2 alkyl, alkenyl or alkynyl groups containing from 1 or 2 to 6 carbon atoms or a cycloalkyl group containing 5 or 6 carbon atoms in the ring.

The term "heteroalkyl" refers to an aralkyl group as defined above in which one or more carbon atoms (preferably 1, 2, 3 or 4) have been replaced by an oxygen, nitrogen, silicon, selenium, phosphorus atom , boron or sulfur (preferably oxygen, sulfur or nitrogen) ie groups containing both aryl or heteroaryl, respectively as well as alkyl, alkenyl, alkynyl or heteroalkyl or cycloalkyl or heterocycloalkyl groups, according to the above definitions. A heteroaralkyl group preferably contains one or two aromatic ring systems (1 or 2 rings) containing from 5 or 6 to 10 carbon atoms in the ring and one or two alkyl, alkenyl or alkynyl groups containing 1 or 2 to 6 atoms carbon or a cycloalkyl group containing 5 or 6 carbon atoms in the ring, wherein 1, 2, 3 or 4 of these carbon atoms have been replaced by oxygen, sulfur or nitrogen atoms. Examples are arylheteroalkyl groups, arylheterocycloalkyl, arylheterocycloalkenyl, arilalquilheterocicloalquilo, arilalquenilheterocicio-alkyl, arilalquinilheterocicloalquilo, arylalkyl heterocic? Oalquenilo, heteroarylalkyl, heteroarylalkenyl, heteroarylalkynyl, heteroaryl-heteroalkyl, heteroarylcycloalkyl, heteroarylcycloalkenyl, heteroarylheterocycloalkyl, heteroarylheterocycloalkenyl, heteroarilalquilciclo-alkyl, heteroarilalquilheterocicloalquenilo, heteroaryl- heteroalkylcycloalkyl, heteroarylheteroalkyl-cycloalkenyl and heteroarylheteroalkylhetero-cycloalkyl, the cyclic groups are saturated or monounsaturated, diunsaturated or tri-unsaturated. Specific examples are tetrahydroisoquinolinyl, benzoyl, 2- or 3-ethylindolyl, 4-methylpyridino, 2-, 3- or 4-methoxyphenyl, 4-ethoxyphenyl or a 2-, 3- or 4-carboxyphenylalkyl group. The terms cycloalkyl, heterocycloalkyl, alkylcycloalkyl, heteroalkylcycloalkyl, aryl, heteroaryl, aralkyl and heteroaralkyl refer to groups in which one or more hydrogen atoms of such groups have been replaced by fluorine, chlorine, bromine or iodine atoms or by OH groups , = 0, SH. = S, NH2, = NH or N02. The term "optionally substituted" refers to groups in which one or more hydrogen atoms have been replaced by fluorine, chlorine, bromine or iodine atoms or by OH groups, = 0, SH, = S, NH2, = NH or N02 This term also refers to groups which are substituted by the unsubstituted forms of the alkyl groups of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, heteroalkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 10 carbon atoms, heterocycloalkyl of 2 to 9 carbon atoms, aryl of 6 to 10 carbon atoms, heteroaryl of 1 to 9 carbon atoms, aralkyl of 7 to 12 carbon atoms or heteroaralkyl from 2 to 11 carbon atoms. Preferred are the compounds of the formula (I), wherein A is selected from the following groups: -CH (0H) CH2-, -CH2CH (0H) -, -0CH2CH2-, -CH2CH20-, -CH2S02-, -S02CH2 -, -CH2N (alkyl of 1 to 4 carbon atoms) -, -C (alkyl of 1 to 4 carbon atoms) CH2-, -CH2NH-, -NHCH2-, -CH20-, -0CH2-, -CH2S- , -SCH2-, -N (alkyl of 1 to 4 carbon atoms) C (= 0) -, -C (= 0) N (alkyl of 1 to 4 carbon atoms) -, -NHC (= 0) - , -C (= 0) NH- or -CH2CH2-. Especially preferred are compounds of formula (I) wherein A is a group of the formula -CH (OH) CH2- or -OCH2CH2-. Again, preferably, the residue R1 is a cyano group, an alkoxy group of 1 to 4 carbon atoms or a heteroalkyloxy group of 1 to 4 carbon atoms wherein one or more -atoms of hydrogen in these groups may be substituted by fluorine atoms. Especially preferably, the residue R1 is a methoxy group. Preferably, the residue R2 is a hydrogen atom or a halogen atom, particularly preferably the residue R2 is a hydrogen or chlorine or fluorine atom. Again and preferably, the residue R3 is selected from the following groups: Especially preferably, the residue R3 is selected from the following groups: Again preferably, the residues R4 are independently of each other a halogen atom, a hydroxy group, a cyano, an alkyl of 1 to 4 carbon atoms or a heteroalkyl of 1 to 4 carbon atoms (for example a hydroxymethyl group) . Particularly preferably, the radicals R4 are independently of one another a fluorine or chlorine atom or a heteroalkyl group of 1 to 4 carbon atoms (for example a hydroxymethyl group). Preferably, n is equal to 0 or 1, particularly preferably n is equal to 0. Preferably, the residue R5 is a heteroalkylcycloalkyl or heteroaralkyl group. Especially preferably, the residue R5 is a group of formula -BY, wherein B is a bond, an alkylene (especially an alkylene group having 1 to 4 carbon atoms), an alkenylene, an alkynylene, a group -NH- , -NHS02-, -S02-, -C (= 0), a heteroalkylene (especially a heteroalkylene group of 1 to 4 carbon atoms) or a heterocycloalkylene group and Y is an aryl, heteroaryl, aralkyl, heteroaralkyl, cycloalkyl group, heterocycloalkyl, alkylcycloalkyl, heteroalkylcycloalkyl, heteroarylheterocycloalkyl or an arylheterocycloalkyl (especially a heterocycloalkyl, heteroaryl, aralkyl, heteroaralkyl, heteroarylheterocycloalkyl or arylheterocycloalkyl group). Preferably, B is a bond or a group of the formula -NH-, -NHCH2-, -CH2NH-, -NHCH2CH2-, -CH2CH2NH-, -NHCH2CH2CH2-, -CH2CH2CH2NH-, -CH2-, -CH2CH2-, -CH2CH2CH2-, -NHC (= 0) -, -C (= 0) NH-, -CH (OH) -, -CH2CH (0H) -, -CH (0H) CH2-, -NHS02-, -S02NH- , -S02-, -C (= S) NH-, -NHC (= S) -, -C (= N0H) -, -CH2C (= NOH) -, -C (= N0H) CH2-, -C ( = 0) -, -C (= 0) -C (= 0) -, -CH2C (= 0) -, -C (= 0) CH2-, -N (alkyl of 1 to 4 carbon atoms) CH2- , -CH2N (alkyl of 1 to 4 carbon atoms) - or a piperazine group. Especially preferably, B is a bond or a group of the formula -NHCH2-, -CH2NH-, -CH2-, -CH2CH2-, -CH2CH2CH2-, -NHC (= 0) -, -C (= 0) NH -, -CH2CH (0H) -, -CH (0H) CH2-, -NHS02-, -S02NH-, -S02-, -C (= 0) - or a piperazine group. Preferably, Y is a bicyclic system wherein the two rings independently of each other are a cycloalkyl, a heterocycloalkyl, an aryl (especially a phenyl ring) or a heteroaryl ring, and each has from 3 to 8 ring atoms (preferably 5). , 6 or 7 atoms in the ring) (especially preferably the heteroaryl ring has 5 or 6 ring atoms), and if applicable, the system can be substituted (for example by F, = O, methyl, trifluoromethyl, methoxy, -C (= 0) OH, cyclopropyl). Again preferably, Y is a group of the formula -Y1-Y2, wherein Y1 is a bond, an alkylene (especially an alkylene group of 1 to 4 carbon atoms), an alkenylene (especially an alkenylene group of 2 to 4 carbon atoms), an alkynylene, -NH-, -S-, -O-, -NHC (= 0 ) -, -C (= 0) NH-, or a heteroalkylene group (especially a heteroalkylene group of 1 to 4 carbon atoms) and Y2 is an aryl, heteroaryl, aralkyl, heteroaralkyl, cycloalkyl, heterocycloalkyl, alkylcycloalkyl, heteroalkylcycloalkyl group, heteroarylheterocycloalkyl or an arylheterocycloalkyl (especially a heterocycloalkyl, aryl, heteroaryl, aralkyl, heteroaralkyl, heteroarylheterocycloalkyl or arylheterocycloalkyl group). Especially preferably Y1 is a bond or a group of the formula -CH = CH-, -CH2CH2-, -S-, -CH20-, -C (= 0) NH-, -NH- or -CH2C (= 0) -e Y2 is an optionally substituted phenyl group or a heteroaryl group having 5 or 6 ring atoms. Especially preferably, Y has one of the following structures: wherein X1, X2 and X3, independently of each other, are nitrogen atoms or groups of the formula CR20, X4 and X5, independently of each other are oxygen or sulfur atoms or groups of the formula NR21, or is equal to 0, 1 or 2, R14, R15, R16, R17, R19 and R20 independently of each other are hydrogen atoms, halogen atoms, hydroxy, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms or heteroalkyl groups of 1 to 6 carbon atoms and R18 and R21 independently of each other are hydrogen atoms, alkyl groups of 1 to 6 carbon atoms, alkenyl of 2 to 6 atoms of carbon, alkynyl of 2 to 6 carbon atoms or heteroalkyl of 1 to 6 carbon atoms. Especially preferably, Y has one of the following structures: Especially preferably, Y has one of the following structures Preferably, the R6 residues independently of each other are a halogen atom, a hydroxy group, alkyl of 1 to 4 carbon atoms or heteroalkyl of 1 to 4 carbon atoms (for example a hydroxyethyl group). Again, preferably further, the R6 residues independently of one another are a fluorine or chlorine atom or a hydroxy group, alkyloxy of 1 to 4 carbon atoms, heteroalkyl of 1 to 4 carbon atoms (for example a hydroxyethyl group) or dialkylaminomethyl of 3 to 6 carbon atoms, wherein one or more hydrogen atoms of these groups may be substituted by fluorine atoms. Particularly preferably, the R6 residues independently of one another are a heteroalkyl group having 1 to 4 carbon atoms (for example a hydroxyethyl group). Particularly preferred are the compounds of formula (II): (II) wherein the residues R2, R4a and R6a independently of each other are a hydrogen atom or a halogen atom or a heteroalkyl group of 1 to 4 carbon atoms (for example a hydroxymethyl or hydroxyethyl group) (especially R2 is a hydrogen atom and R4 and RSa are a hydrogen or fluorine atom or a heteroalkyl group of 1 to 4 carbon atoms). B and Y are as defined in the above.

Especially, B is a bond or a group of the formula -NHCH2, -NHC (= 0) - or -NHS02-. Especially preferred are the compounds of the formula (III): (III) wherein the residue R2 is a hydrogen atom or a halogen atom (especially R2 is a hydrogen atom). B and Y are as defined in the above. Especially, B is a bond or a group of the formula -CH2CH2-, -CH2CH2CH2- or -CH2CH (0H) -. Especially preferred are the compounds of the formula (IV): (IV) wherein the residue R2 is a hydrogen atom or a halogen atom (especially R2 is a hydrogen atom). B and Y are as defined in the above. Especially, B is a bond or a group of the formula -CH2-, -CH2CH2-, -S02- or -C (= 0) -. It is especially preferred to combine the preferred embodiments for each generic group in formulas (I), (II), (III) and (IV) in any possible way. Due to their substitution, the compounds of formulas (I) to (IV) may contain one or more centers of chirality. In this manner, the present invention comprises both pure enantiomers and pure diastereomers and also mixtures thereof in any mixing ratio. In addition, the present invention also comprises all cis / trans isomers of the compounds of the general formulas (I) to (IV) as well as mixtures thereof. Additionally, the present invention comprises all tautomeric forms of the compounds according to formulas (I) to (IV). The therapeutic use of compounds according to formulas (I) to (IV), their pharmacologically acceptable salts, solvates and hydrates, respectively as well as formulations and pharmaceutical compositions are also within the scope of the present invention. The pharmaceutical compositions according to the present invention comprise at least one compound of the formulas (I) to (IV) as an active ingredient and, optionally, carrier substances and / or adjuvants.

Examples of pharmacologically acceptable salts of the compounds of formulas (I) to (IV) are salts of physiologically acceptable mineral acids such as hydrochloric acid, sulfuric acid and phosphoric acid or salts of organic acids such as methanesulfonic acid, p-toluenesulfonic acid , lactic acid, acetic acid, trifluoroacetic acid, citric acid, succinic acid, fumaric acid, maleic acid and salicylic acid. Additional examples of pharmacologically acceptable salts of the compounds of the formulas (I) to (IV) are alkali metal and alkaline earth metal salts such as, for example, sodium salts, potassium, lithium, calcium or magnesium, ammonium salts or salts of organic bases such as, for example, methylamine, dimethylamine, triethylamine, piperidine, ethylenediamine, lysine, choline hydroxide, meglumine, morpholine or arginine salts. The compounds of the formulas (I) to (IV) can be solvated, especially hydrated. The hydration can be carried out, for example, during the preparation process or as a consequence of the hygroscopic nature of the initially anhydrous compounds of the formulas (I) to (IV). When the compounds of formulas (I) to (IV) comprise asymmetric carbon atoms, they may be present in the form of achiral compounds, diastereomeric mixtures, mixtures of enantiomers or in the form of optical-pure compounds. The precursors (eg, RB Silverman, Medizinische Chemie, VCH einheim, 1995, chapter 8, p.3611 ff) with which the present invention also relates consist of a compound of formulas (I) to (IV) and at least one pharmacologically acceptable protecting group which will be removed under physiological conditions such as, for example, an alkoxy, aralkyloxy, acyl or acyloxy group such as, for example, a methoxy, ethoxy, benzyloxy, acetyl or acetyloxy group. The present invention also relates to the use of those active ingredients in the preparation of medicaments. In general, the compounds of formulas (I) to (IV) are administered individually or in combination with any other desired therapeutic agent, using known and acceptable methods. Said therapeutically useful agents can be administered, for example, by one of the following routes: oral, for example in the form of dragees, coated tablets, pills, semi-solid substances, soft or hard capsules, solutions, emulsions or suspensions.; parenterally, for example in the form of an injectable solution; rectally in the form of suppositories; by inhalation, for example in the form of a powder formulation or a spray; transdermally or intranasally. For the preparation of compressed dices, pills, semi-solid substances, coated tablets, dragees and hard gelatine capsules, the therapeutically usable product can be mixed with pharmacologically inert, inorganic or organic pharmaceutical carrier substances, for example with lactose, sucrose, glucose , gelatin, malt, silica gel, starch or derivatives thereof, talc, stearic acid or salts thereof, delayed milk powder and the like. For the preparation of soft capsules, pharmaceutical carrier substances such as, for example, vegetable oils, petroleum oils, animal or synthetic origin, wax, fat and polyols can be used. For the preparation of liquid solutions and syrups, pharmaceutical carrier substances such as, for example, water, alcohols, aqueous saline, aqueous dextrose, polyols, glycerol, vegetable oils, petroleum oils and of animal or synthetic origin can be used. For suppositories, pharmaceutical carrier substances such as, for example, vegetable oils, petroleum oils of animal or synthetic origin, wax, fat and polyols can be used. For aerosol formulations, compressed gases suitable for this purpose can be used, such as, for example, oxygen, nitrogen and carbon dioxide. The pharmaceutically acceptable agents may also comprise additives for preservation and stabilization, emulsifiers, sweeteners, flavors, salts for altering the osmotic pressure, buffers, encapsulating additives and antioxidants. The compounds of the formulas (I), (II), (III) and (IV) have improved properties when compared with antibacterial compounds known in the state of the art. Especially in this context, improved antibacterial activity, improved solubility or improved PK properties have been mentioned. Combinations with other therapeutic agents may comprise other antimicrobial or antifungal active ingredients. For the prevention and / or treatment of the diseases described in the foregoing, the dose of the biologically active compound according to the invention can vary within wide limits and can be adjusted to individual requirements. A dose of 10 mg to 4000 mg per day is generally adequate, with a dose of 50 to 3000 mg per day being preferred. In appropriate cases, the dose may also be below or above the established values. The daily dose can be administered as a single dose or in a plurality of doses. A typical single dose contains approximately 50 mg, 100 mg, 250 mg, 500 mg, 1 g or 2 g of the active ingredient.

EXAMPLES Example 1: 6- ( { L- [2-hydroxy-2- (3-methoxy-quinolin-5-yl) -ethyl] -piperidin-4-ylamino} -methyl) -4H-benzo [1, 4] oxazin-3-one (enantiomer 2) Enantiomer 2 la) 3, 5-dibromoquinoline 250 g of 3-bromoquinoline are added dropwise to 625 ml of concentrated sulfuric acid cooled with ice so that the temperature does not increase above 15 ° C. Subsequently, 240 g of N-bromosuccinimide are added slowly and in portions so that the temperature does not increase above 20 ° C and the reaction mixture is stirred at room temperature overnight. The reaction mixture is poured into 10 kg of ice and, during cooling, mixed with solid sodium hydroxide. The suspension that is produced is filtered, the solid is washed with water and dried at 40 ° C under vacuum. The solid is resuspended in 1.5 l of methanol and then heated to reflux. After cooling, the solid is filtered, rinsed again with 500 ml of cold methanol and the filtrate is concentrated. The crude product is purified by flash chromatography (silica gel, ethyl acetate: heptane: 1:29, 1:19, 1: 9) and results in 151 g of the desired product. X H NMR (300 MHz, CDC13): d: 8.85 (d, HH), 8.65-8.64 (m, HH), 7.99 (d, HH), 7.78 (d, HH), 7.56-7.49 (m, HH) Ib ) 5-bromo-3-methoxyquinoline 150 g of 3,5-dibromoquinoline (la) are added to a stirred suspension of 35.78 g of sodium methylate in 1.5 1 of dry DMPU at 100 ° C and then heated to 125 ° C. for 90 minutes. After cooling, the reaction mixture is poured into 7.5 kg of ice and stirred overnight. The solid that is produced is separated by filtration, washed with water and dried at 40 ° C under vacuum. The crude product is purified by flash chromatography (silica gel, ethyl acetate: heptane: 1:19, 1: 4) and results in 65.2 g of the desired product. XH NMR (300 MHz, CDC13): d: 8.60 (d, HH), 7.95 (d, HH), 7.72 (d, HH), 7.65 (d, HH), 7.37-7.31 (m, HH), 3.93 ( s, 3H) le) 3-methoxy-5-vinylquinoline Under a gaseous nitrogen atmosphere, 1155 g of tetrakis (triphenylphosphine) palladium (0) are added to a solution of 9.52 h of methoxyquinoline (Ib) in 450 ml of 1: 2. -dimethoxyethane dried at room temperature and stirred for 20 minutes. Subsequently, 5.57 g of potassium carbonate, 120 ml of water and 2,4,6-trivinylcyclobonoxane pyridine complex (3.85 g - O'Sheas reagent, see J. Org. Chem., Volume 67 (2002), are added). 4968-4971) and heated at 100 ° C for 4 hours. After cooling to room temperature 200 ml of water are added and the reaction mixture is extracted with acetic acid ethyl ester (150 ml, 4 times). The combined organic phases are dried over sodium sulfate, filtered and concentrated. The crude product is purified by flash chromatography (silica gel, heptane: ethyl ester of acetic acid: 9: 1, 3: 2) and results in 7.41 g of the desired product. NMR XH (300 MHz, CDC13): d: 8.60 (d, ÍH), 7.91 (d, ÍH), 7.57-7.41 (m, 3H), 7.28-7.22 (m, ÍH), 5.72 (dd, ÍH), 5.43 (dd, ÍH), 3.87 (s, 3H) Id) 1- (3-methoxyquinoline- 5-yl) -ethan-1,2-diol (enantiomer 2) 90.2 g of mixture AD and 7.6 g of methanesulfonic acid amide are dissolved in 280 ml of water and 280 ml of terbutanol at room temperature. The orange solution is cooled to 0 ° C, 14.4 g of vinylquinoline (le) are added and the mixture is stirred at 0-4 ° C for 2 days. Then add 108 g of sodium pyrosulfite at 0 ° C and stir for 30 minutes at this temperature. After warming to room temperature the reaction mixture is extracted with ethyl acetate (150 ml, 5 times). The combined organic phases are dried over sodium sulfate, filtered and concentrated. The crude product is purified by flash chromatography (silica gel, dichloromethane: methanol: 29: 1, 4: 1) and 14.91 g of the desired product are obtained. NMR * H (300 MHz, d6-DMSO): d: 8.65 (d, ÍH), 7.88-7.85 (m, 2H), 7.66 (d, ÍH), 7.58-7.53 (m, ÍH), 5.51 (d, ÍH), 5.31-5.26 (m, HH), 4.87-4.84 (m, HH), 3.96 (s, 3H), 3.67-3.57 (m, 2H) le) 2-hydroxy-2- (3-methoxyquinoline-5-) ester il) ethyl toluene-4-sulfonic acid (enantiomer 2) Under an atmosphere of nitrogen gas, 0.33 g of dibutyltin oxide, 12.78 g of p-toluenesulfonic acid and 9.33 ml of triethylamine are added to a suspension of 14.4 g of the diol (Id) in 150 ml of dry dichloromethane at room temperature under stirring. The reaction mixture is stirred for 14 hours and then suspended with 150 ml of water and the organic phase is separated. The aqueous phase is extracted again twice with 150 ml of dichloromethane each. The combined organic phases are washed with 150 ml of water and 150 ml of a saturated solution of sodium chloride, dried over sodium sulfate, filtered and concentrated. The crude product is purified by flash chromatography (silica gel, dichloromethane: methanol: 9: 1) and 16.12 g of the desired product is obtained as a result. X H NMR (300 MHz, d6-DMSO): d: 8.63 (d, ÍH), 7.89 (d, ÍH), 7.67-7.62 (m, 2H), 7.58-7.47 (m, 3H), 7.27 (d, 2H), 6.05 (s broad, ÍH), 5.56 (s broad, ÍH), 4.25 (dd) , ÍH), 4.14 (dd, ÍH), 3.89 (s, 3H), 2.34 (s, 3H) lf) 3-methoxy-5-oxiranylquinoline (enantiomer 2) A solution of 15.97 g of tosylate (le) in 300 ml of diethyl ether is mixed under stirring with a 2 N solution of 110 ml of sodium hydroxide at room temperature. The two phase mixture is stirred at room temperature for 3 hours and then the organic phase is separated. The aqueous phase is extracted again three times with 150 ml of diethyl ether. The combined organic phases are dried over sodium sulfate, filtered and concentrated. The crude product is purified by flash chromatography (silica gel, ethyl acetate: heptane: 1: 1) and 5.8 g of the desired product are obtained.

XH NMR (300 MHz, CDC13): d: 8.64 (d, HH), 7.94 (dd, HH), 7.59 (d, HH), 7.48-7.39 (m, 2H), 4.30 (m, HH), 3.91 ( s, 3H), 3.22 (dd, ÍH), 2.81 (dd, ÍH) lg) terbutyl ester of the acid. { l- [2-Hydroxy-2- (3-methoxyquinolin-5-yl) -ethyl] -piperidin-4-yl} -carbamic (enantiomer 2) Dissolve 689 mg of the epoxide (lf) and 686 mg of 4- (terbutoxycarbonylamino) piperidine in 11 ml of DMF, mix with 497 mg of potassium carbonate and 364 mg of lithium perchlorate and stir at 80 ° C for 2 days. The solution is concentrated, the residue is dissolved in dichloromethane and extracted with water and a saturated solution of sodium chloride. The organic phase is dried over magnesium sulfate, filtered and concentrated. The residue is purified by flash chromatography (silica gel, dichloromethane: methanol: 97: 3) and 1.22 g of the desired product is obtained. NMR * H (300 MHz, CDC13): d: 8.56 (d, ÍH), 7.92 (m, ÍH), 7.64 (m, ÍH), 7.48-7.43 (m, ÍH), 5.72 (s broad, ÍH), 4.51 (m, ÍH), 3.85 (s, 3H), 3.60-3.46 (m, ÍH), 3.29-3.26 (m, 2H), 2.84-2.73 (m, 2H), 2.67-2.40 (m, 2H), 2.09-1.95 (m, 2H), 1.84-1.64 (m, 2H), 1.38 (s, 9H) lh) 2- (4-aminopiperidin-1-yl) -1- (3-methoxyquinolin-5-yl) -ethanol (enantiomer 2) 1.22 g of Boc-amine (lg) are dissolved in 23 ml of dichloromethane, and treated with 2.3 ml of trifluoroacetic acid at 0-5 ° C and stirred overnight at room temperature. The solution is adjusted to an alkaline pH value with a 2 N sodium hydroxide solution and the phases are separated. The aqueous phase is extracted with dichloromethane. The combined organic phases are washed with a saturated solution of sodium chloride, dried over magnesium sulfate, filtered and concentrated. The residue is purified by flash chromatography (silica gel, dichloromethane, methanol: 9: 1 + 1% ammonia) and 557 mg of the desired product are obtained. 1 H-NMR (300 MHz, d6-DMSO): d: 8.66-8.63 (m, HH), 7.87-7.82 (m, 2H), 7.67 (m, HH), 7.58-7.51 (m, HH), 5.43-5.39 (m, ÍH), 5.26-5.23 (m, 1H), 3.95 (s, 3H), 2.99-2.85 (m, 2H), 2.62-2.55 (m, ÍH), 2.19-1.99 (m, 2H), 1.72 -1.57 (m, 2H). li) Ethyl ester of (4-formyl-2-nor rofenoxy) acetic acid 25 g of 4-hydroxy-3-nitrobenzaldehyde are dissolved in 250 ml of DMF. Subsequently 22.7 g of potassium carbonate are added and 23.2 ml of chloroacetic acid ethyl ester are added dropwise. The solution is stirred at 50 ° C for 2 days and at room temperature for a further 2 days, then it is partitioned with water and extracted with ethyl acetate. The combined organic phases are washed with water, dried over magnesium sulfate, dried and concentrated and 37.8 g of the desired product are obtained. 1 H NMR (300 MHz, d6-DMSO): d: 9.96 (s, HH), 8.44 (s, HH), 8.15 (dd, HH), 7.52 (d, HH), 5.17 (s, 2H), 4.18 ( c, 2H), 1.21 (t, 3H) 1j) 3-OXO-3, 4-dihydro-2H-benzo [1,4] oxazin-6-carbaldehyde 37.7 g of the phenoxyacetic acid ethyl ester (Li) is dissolved in 1000 ml of acetic acid.

Subsequently, 83 g of iron powder are added and the mixture is stirred at 80 ° C for 1.5 hours. The reaction mixture is filtered through Decalit and concentrated. The residue is resuspended or redissolved, respectively, in a saturated solution of sodium hydrogen carbonate and extracted with ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered and concentrated. The residue is mixed with ether, the precipitate is filtered, whereby 20 g of the desired product are obtained. X H NMR (300 MHz, d 6 -DMSO): d: 11.00 (s broad, ÍH), 9.84 (s, ÍH), 7.54 (dd, ÍH), 7.39 (d, ÍH), 7.14 (d, ÍH), 4.72 (s, 2H) lk) T compound 100 mg of the amine (lh) are dissolved in 6 ml of 1,2-dichloroethane and 2 ml of methanol and mixed with 1.00 g of 3A molecular sieve and 71 mg of the aldehyde ( lj). The mixture is stirred overnight at room temperature. Then 13 mg of sodium borohydride are added thereto and the mixture is stirred for 4 hours at room temperature. The molecular sieve is filtered off and the filtrate is washed with a saturated solution of sodium hydrogen carbonate and a saturated solution of sodium chloride. The organic phase is dried over magnesium sulfate, filtered and concentrated. The residue is purified by flash chromatography (silica gel, dichloromethane: methanol: 9.1 + 1% ammonia), whereby 70 mg of the desired product is obtained. 1 H-NMR (300 MHz, d6-DMSO): d: 10.78 (s, HH), 8.66 (d, HH), 7.96 (s, HH), 7.88-7.84 (m, 2H), 7.70-7.68 (m, HH) ), 7.59-7.54 (m, ÍH), 7.00-6.91 (m, 3H), 5.75 (s, ÍH), 5.49-5.46 (m, ÍH), 4.56 (s, 2H), 3.96 (s, 3H), 2.82 (s, 2H), 3.12-3.03 (m, 2H), 2.72-2.60 (m, 2H), 2.30-2.10 (m, 2H), 2.00-1.85 (m, 2H), 1.58-1.36 (m, 3H) ) Example 2: 6- ( { 1- [2-hydroxy-2- (3-methoxy-quinolin-5-yl) -ethyl] -piperidin-4-ylamino} -methyl) -4H-pyrido [3.2 -b] [1, 4] iazin-3-one (enantiomer 2) Enantiomer 2 2a) N- (6-methylpyridin-2-yl) -acetamide A solution of 39 g of 3-amino-6-picoline in 200 ml of acetic anhydride is heated at 70 ° C for 90 minutes and then concentrated. The residue is resuspended or redissolved, respectively, in 500 ml of water, adjusted to a pH value of 8 with solid sodium acid carbonate and extracted with ethyl acetate (200 ml, 2 times). The combined organic phases are washed with a saturated solution of sodium chloride, dried over magnesium sulfate, filtered and concentrated to obtain 53.3 g of the desired product. NMR XH (300 MHz, CDC13): d: 8.43 (broad s, ÍH), 8. 00 (d, ÍH), 7.62-7.57 (m, ÍH), 6.89 (d, ÍH), 2.45 (s, 3H), 2.18 (s, 3H) 2b) 6-Acetylaminopyridine-2-carboxylic acid A suspension of 53.3 g of acetamide (2a) in 530 ml of water is heated to 75 ° C until a homogeneous solution has been formed. 133 g of potassium permanganate are added in small portions in the following 1.25 hours (the reaction temperature in the reaction flask is monitored with caution). After stirring for 3 hours at 75 ° C the reaction solution is filtered through Celite in the hot state and rinsed again with hot water. The filtrate is concentrated to approximately 100 ml and concentrated hydrochloric acid is added until a white precipitate has formed. The white solid is prepared by filtration, dried, whereby 32 g of the desired product are obtained. NMR * H (300 MHz, d6-DMS0): d: 10.85 (s, HH), 8.26 (d, HH), 7.97-7.72 (m, HH), 7.73 (dd, HH), 2.11 (s, 3H) 2c 6-aminopyridine-2-carboxylic acid methyl ester 18 g of the acid (2b) are suspended in methanol, saturated with gaseous HCl and heated overnight under reflux. After cooling the reaction mixture is concentrated and the residue is resuspended or redissolved, respectively in water and dichloromethane. Solid sodium hydrogen carbonate is added and the phases are separated. The aqueous phase is extracted with dichloromethane. The combined organic phases are washed with a saturated solution of sodium chloride, dried over magnesium sulfate, filtered and concentrated. The residue is purified by flash chromatography (silica gel, dichloromethane: ethyl acetate: 1: 1) to obtain 9.64 g of the desired product. 1 H NMR (300 MHz, CDC13): d: 7.52-7.1 (m, 2H), 6.66 (dd, 1H), 5.12 (broad s, 2H), 3.91 (s, 3H) 2d) 6-amino acid methyl ester -5-Bromopyridine-2-carboxylic acid To a solution of 9.64 g of the ester (2c) in 408 ml of chloroform, a solution of 3.35 ml of bromine in 70 ml of chloroform is added dropwise over the next 60 minutes. After the reaction mixture has been stirred at room temperature for 40 hours they are added 150 ml of a saturated solution of sodium thiosulfate and the phases are separated. The aqueous phase is extracted with dichloromethane. The combined organic phases are washed with a saturated solution of sodium chloride, dried over magnesium sulfate, filtered and concentrated. The residue is purified by flash chromatography (silica gel, hexane: acetic acid ethyl ester: 2: 1) to obtain 1.8 g of the desired product. X H NMR (300 MHz, CDC13): d: 7.73 (d, 1H), 7.29 (d, 1H), 5.39 (broad s, 2H), 3.90 (s, 3H) 2e) 3-Oxo-3 methyl ester , 4-dihydro-2H-pyrido [3,2-b] [1,4] thiazine-6-carboxylic acid To a solution of 2.4 ml of methyl thioglycolate in 75 ml of DMF is added 1.1 g of sodium hydride. After one hour, 5 g of bromopyridine are added (2d) and stirred for 12 hours at room temperature. The reaction solution is diluted with 150 ml of water. The solid is filtered off, washed with a small amount of acetic acid ethyl ester and acetonitrile and 1.65 g of the desired product is obtained as a result. i NMR * H (300 MHz, d6-DMS0): d: 11.29 (s, ÍH), 7.97 (d, ÍH), 7.66 (d, ÍH), 3.86 (s, 3H), 3.64 (s, 2H), 3.33 (s, 3H) 2f) 3-Oxo-3,4-dihydro-2H-pyrido acid [ 3,2-b] [1,4] thiazine-6-carboxylic acid To a solution of 2.33 g of the ester (2e) in 354 ml of dioxane and 90 ml of water are added dropwise in the next 2 hours 24 ml of a 2 N solution of sodium hydroxide and then stirred at room temperature overnight. The solution is concentrated and the pH value is adjusted to 4 with a 2 N solution of hydrochloric acid. The solid that is produced is separated by filtration, washed with a small amount of water and dried overnight under vacuum, which provides 1.72 g of the desired product. MS (El): m / z: 211 [M + H] + 2g) 6-hydroxymethyl-4H-pyrido [3,2-b] [1,4] thiazin-3-one To a solution of 1.72 g of the acid (2f) in 82 ml of THF are added at -10 ° C 1.4 ml of triethylamine and 1.2 ml of isobutyl chloroformate. After 25 minutes the solution is filtered through Celite in an ice-cooled solution of 1.1 g of sodium borohydride in 28 ml of water, stirred at this temperature for 30 minutes and the pH value is adjusted to 7 with a 0.2 N solution of hydrochloric acid. After the concentration step, the produced solid is filtered off, washed with water and dried, which generates 1.1 g of the desired product. MS (El) m / z: 197 [M + H] + 2h) 3-oxo-3,4-dihydro-2H-pyrido [3,2-b] [1,4] thiazine-6-carbaldehyde to a solution from 1.1 g of the alcohol (2 g) in 100 ml of dichloromethane and 100 ml of THF are added 2.5 g of manganese dioxide. After stirring at room temperature for 90 minutes, add an additional 3 g of manganese dioxide, stir for an additional 2 hours at room temperature and then the reaction mixture is filtered through Celite. The filtrate is concentrated, whereby 598 mg of the desired product are obtained. 1 H-NMR (300 MHz, CDC13): d: 9.85 (s, ÍH), 8.40 (broad s, ÍH), 7.74 (d, ÍH), 7.55 (d, ÍH), 3.50 (s, 2H) 2i) Compound title This compound is prepared as in Example Ik from the aldehyde (2H) in 96% yield. NMR * H (300 MHz, d6-DMSO): d: 10.85 (s, 1H), 8.65 (d, 1H), 7.87-7.82 (m, 2H), 7.74-7.67 (m, 2H), 7.58-7.51 ( m, ÍH), 7.11-7.05 (m, ÍH), 5.50-5.36 (m, ÍH), 5.30-5.19 (m, ÍH), 3.95 (m, 1H), 3.72 (s, 2H), 3.53 (s, 2H), 3.02-2.87 (m, 2H), 2.65-2.54 (m, 2H), 2.44-2.32 (m, ÍH), 2.21-2.02 (m, 2H), 1.86-1.70 (m, 3H), 1.42- 1.13 (m, 3H) Example 3: 7-Fluoro-6- ( { 1- [2-hydroxy-2- (3-methoxy-quinolin-5-yl) -ethyl] -piperidin-4-ylamino} -methyl) -4H-benzo [1,4] thiazin-3-one (enantiomer 2) Enantiomer 2 3a) Ethyl 2-4-difluorobenzoic acid 5.00 g of 2,4-difluorobenzoic acid are dissolved in 50 ml of ethanol and gaseous HCl is passed through the solution for 20 minutes. Subsequently the solution is heated under reflux for 5 hours, the solution is concentrated and the residue is dissolved in ether. The organic phase is washed with a 1 N solution of sodium hydroxide and a saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to obtain 3.8 g of the desired product. NMR XH (300 MHz, CDC13): d: 08.05-7.95 (m, ÍH), 6. 99-6.82 (m, 2H), 4.40 (c, 2H), 1.22 (t, 3H) 3b) 2, 4-difluoro-5-nitrobenzoic acid ethyl ester 3.8 g of the ethyl ester (3a) are dissolved in 3 ml of fuming nitric acid and 3 ml of concentrated sulfuric acid at 0 ° C and stirred for 2.5 hours. Subsequently, the reaction mixture is diluted with 10 ml of water and extracted with 200 ml of dichloromethane. The organic phase is washed with a saturated solution of sodium chloride, dried over magnesium sulfate, filtered and concentrated. The residue is purified by flash chromatography (silica gel, hexane: ethyl acetate: 6: 1) to obtain 3.96 g of the desired product. NMR XH (300 MHz, CDC13): d: 8.70 (m, HH), 7.05 (m, ÍH), 4.36 (c, 2H), 1.35 (t, 3H) 3c) 2-Fluoro-4-methoxycarbonylmethylsulfanyl-5-nitrobenzoic acid ethyl ester 3.96 g of nitrobenzoic acid (3b) are dissolved in 75 ml of dichloromethane, it is mixed with 2.8 ml of triethylamine and cooled to 0 ° C. After the addition of 1.5 ml of methyl thioglycolate, the reaction mixture is stirred at 0-5 ° C for 3.5 hours and the solution is stored overnight in the refrigerator. The solution is concentrated and the residue is purified by flash chromatography (silica gel, hexane: acetic acid ethyl ester: 6: 1), whereby 3.86 g of the desired product are obtained. X H NMR (300 MHz, CDC13): d: 8.82 (d, ÍH), 7.19 (d, ÍH), 4.35 (c, 2H), 3.72 (s, 3H), 3.70 (s, 2H), 1.35 (t, 3H) 3d) 7-Fluoro-3-oxo-3,4-dihydro-2H-benzo [1,4] thiazine-6-carboxylic acid ethyl ester 3.86 of the compound (3c) are dissolved in 142 ml of acetic acid, it is mixed with 6.8 g of iron powder and stirred at 60 ° C for 4 hours. The reaction mixture is filtered through silica gel, rinsed again with methanol and the filtrate is partially concentrated. Water and ethyl acetate are added and the phases are separated. The aqueous phase is extracted once more with ethyl acetate. The combined organic phases are washed four times with water, dried over magnesium sulfate, filtered and concentrated, whereby 3.11 g of the desired product are obtained. X H NMR (300 MHz, d6-DMSO): d: 10.71 (s, ÍH), 7.50-7.39 (m, 2H), 4.30 (c, 2H), 3.56 (s, 2H), 1.30 (t, 3H) 3e ) 7-Fluoro-3-oxo-3,4-dihydro-2H-benzo [1,4] thiazine-6-carboxylic acid 3.11 g of thiazine (3d) are suspended in 37 ml of THF, mixed with a solution 1 N of 37 ml of sodium hydroxide and stir at room temperature overnight. The solution is acidified to a pH value of 3 with a 1 N solution of hydrochloric acid and partially concentrated. The precipitate that is produced is separated by filtration and washed with water. The solids are dried under reduced pressure (100 mbar, 40 ° C), whereby 2.49 g of the desired product are obtained. 1 H-NMR (300 MHz, d6-DMSO): d: 13.26 (broad s, HI), 10.72 (s, ÍH), 7.48 (d, ÍH), 7.38 (d, ÍH), 3.57 (s, 2H) 3f) 7-fluoro-6-hydroxymethyl-4H-benzo [1,4] thiazin-3-one 2.49 g of thiazinecarboxylic acid (3e) are suspended in 80 ml of dry THF, cooled to 0 ° C, mixed with 1.8 ml of triethylamine and 1.6 ml of isobutyl chloroformate and the reaction mixture is stirred for 30 minutes. The suspension is filtered rapidly through Celite in an ice-cooled solution of 1.24 g of sodium borohydride in 24 ml of water. After 45 minutes, the solution is adjusted to a pH value of 1 with a 1 N hydrochloric acid solution and extracted with ethyl acetate. The organic phase is washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated giving 2.29 g of the desired product. 1N-NMR (300 MHz, d6-DMSO): d: 10.61 (s, ÍH), 7.19 (d, HH), 7.10 (d, HH), 5.33 (m, HH), 4.47 (d, 2H), 3.26 (s, 2H) 3g) 7-fl-3-oxo-3, 4-dihydro- 2H-benzo [1,4] thiazine-6-carbaldehyde 1.63 g of thiazinone (3f) are dissolved in 138 ml of dichloromethane: THF 1: 1, mixed with 6.63 g of manganese dioxide and stirred for 2 days at room temperature. ambient. 3.32 g of additional manganese dioxide are added and stirred for an additional 3 days. The suspension is filtered through Celite and rinsed again with THF. The filtrate is concentrated and the residue is purified by flash chromatography (silica gel, hexane: acetic acid ethyl ester: 7: 3), whereby 765 mg of the desired product are obtained. X H NMR (300 MHz, d 6 -DMSO): d: 10.80 (s, 1 H), 10.14 (s, ÍH), 7.51 (d, ÍH), 7.35 (d, ÍH), 3.60 (s, 2H) 3h) Compound of the title The compound is prepared as in example lk from the aldehyde (3g) in a yield 93% X H NMR (300 MHz, d6-DMSO): d: 10.53 (s, 1H), 8.65 (d, 1H), 7.87-7.82 (m, 2H), 7.68 (d, 1H), 7.58-7.53 (m, 1H) ), 7.18 (d, ÍH), 7.09 (d, ÍH), 5.49-5.38 (m, ÍH), 5.33-5.21 (m, ÍH), 3.95 (s, 3H), 3.69 (s, 2H), 3.45 ( s, 2H), 3.05-2.90 (m, 2H), 2.65-2.55 (m, 2H), 2.45-2.29 (m, ÍH), 2.23-2.03 (m, 2H), 1.88-1.74 (m, 2H), 1.42-1.16 (m, 3H) Example 4: 6- ( { 1- [2-idroxy-2- (3-methoxy-quinolin-5-yl) -ethyl] -piperidin-4-ylamino} -methyl) -4H-benzo [1.4 ] thiazin-3-one (enantiomer 2) Enantiomer 2 4a) (4-formyl-2-nitrophenylsulfanyl) acetic acid methyl ester 10 g of 4-chloro-3-nitrobenzaldehyde are dissolved in 100 ml of DMF, 2.35 g of sodium hydride are added thereto and stirred for 15 minutes at room temperature. Subsequently, 3.45 ml of methyl thioglycolate is added in drops and stirred for 5 hours at room temperature. The reaction mixture is diluted with water and extracted with ethyl acetate. The combined organic phases are washed twice with water, dried over sodium sulfate, filtered and concentrated. The crude product is purified by flash chromatography (silica gel, hexane: acetic acid ethyl ester: 2: 1) whereby 5.5 g of the desired product are obtained. XH NMR (300 MHz, CDC13): d: 10.05 (s, ÍH), 8.75 (d, ÍH), 8.09 (dd, ÍH), 7.68 (d, ÍH), 3.84 (s, 2H), 3.81 (s, 3H). 4b) 3-oxo-3,4-dihydro-2H-benzo [1,4] thiazine-6-carbaldehyde 5.5 g of compound (4a) are dissolved in 115 ml of acetic acid and 8.42 g of amber powder are added thereto. iron. The reaction mixture is stirred first for 15 minutes at room temperature and then for 3 hours at 50 ° C and subsequently filtered through Decalit. The filter cake is washed with methanol and the filtrate is concentrated. The residue is dissolved in a saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate, filtered and concentrated. The crude product is purified by flash chromatography (silica gel, hexane: acetic acid ethyl ester: 2: 1) which produces 1 g of the desired product. NMR * H (300 MHz, CDC13): d: 10.18 (broad s, HI), 9.85 (s, 1H), 7.45-7.34 (m, 3H), 3.39 (s, 2H) 4c) Title Compound The compound is prepare as in example lk from the aldehyde (4b) with a yield of 80%. X H NMR (300 MHz, d6-DMSO): d: 10.49 (s, 1H), 8.65 (d, 1H), 7.87-7.82 (m, 2H), 7.68 (d, 1H), 7.58-7.53 (m, 1H) ), 7.23 (d, ÍH), 6.97-6.91 (m, 2H), 5.46-5.36 (m, ÍH), 5.28-5.20 (m, ÍH), 3.95 (s, 3H), 3.62 (s, 2H), 3.43 (s, 2H), 3.04-2.98 (m, 2H), 2.65-2.55 (m, 2H), 2.43-2.28 (m, ÍH), 2.20-2.00 (m, 2H), 1.85-1.71 (m, 2H) ), 1.40-1.16 (m, 3H).

Example 5: 2- { 4- [(2,3-dihydro- [1,4] dioxino [2, 3-c] pyridin-7-ylmethyl) amino] -piperidin-1-yl} -l- (3-methoxyquinolin-5-yl) -ethanol (enantiomer 2) Enantiomer 2 5a) 5-benzyloxy-2-hydroxymethylpyran-4 -one To a solution of 10.36 g of kojic acid in 135 ml of hot methanol 4.3 g of sodium methylate are added in portions and then 9.6 ml of benzyl chloride are added dropwise. . The reaction mixture is heated overnight at 70 ° C, cooled and poured into ice water. The solid is separated by filtration and dried which yields 6.43 g of the desired product. X H NMR (300 MHz, d6-DMS0): d: 8.18 (s, ÍH), 7.44-7.32 (m, 5H), 6.33 (s, ÍH), 5.71-5.66 (m, ÍH), 4.95 (s, 2H) ), 4.30 (d, 2H). 5b) 5-benzyloxy-2-hydroxymethyl-1H-pyridin-4 -one A suspension of 6.43 g of the pyranone (5a) in 67 ml of concentrated ammonia and 14 ml of ethanol are heated at reflux overnight. The solution is cooled, the solid is filtered off and dried, yielding 5.1 g of the desired product. NMR XH (300 MHz, ds-DMS0): d: 11.17 (broad s, HI), 7.48-7.29 (m, 5H), 6.14 (broad s, ÍH), 5.59 (s broad, ÍH), 5.02 (s, 2H), 4.34 (s, 2H). 5c) (2,3-dihydro- [1,4] dioxino [2, 3-c] pyridin-7-yl) -methanol To a solution of 12.6 g of the pyridinone (5b) in 1. 4 1 of water are added 4.36 g of sodium hydroxide and 6.7 g of palladium 10% in charcoal and hydrogenated during 2 days. The catalyst is separated by filtration and the solution is lyophilized. The residue is dissolved in 106 ml of DMF, 18.3 g of potassium carbonate and 3.84 ml of 1,2-dibromoethane is added thereto and heated at 100 ° C overnight. After cooling the solution is concentrated, the residue is resuspended or redissolved, respectively in water and extracted several times with acetic acid ethyl ester. The combined organic phases are dried over sodium sulfate, filtered and concentrated. The crude product is purified by flash chromatography (silica gel, dichloromethane: methanol: 9: 1) to obtain 1.49 g of the desired product. X H NMR (300 MHz, d 6 -DMS0): d: 8.00 (s, ÍH), 6.91 (s, ÍH), 5.31-5.26 (m, ÍH), 4.41 (d, 2H), 4.36-4.33 (m, 2H) ), 4.29-4.26 (m, 2H). 5d) 2,3-dihydro- [1,4] dioxino [2, 3-c] pyridine-7-carbaldehyde To a solution of 2.2 ml of oxalyl chloride in 22 ml of dichloromethane is added thereto dropwise to - 78 ° C a solution of 2.2 ml of dimethyl sulfoxide (DMSO) in 22 ml of dichloromethane for 15 minutes. Subsequently, a solution of 1.49 g of the alcohol (5c) in dichloromethane (16 ml) is added, stirred for 1 hour and then a solution of 8.7 ml of triethylamine in 11 ml of dichloromethane is added thereto. After 20 minutes the reaction mixture is heated to 0 ° C and stirred for 30 minutes. Subsequently, water is added and the phases are separated and the aqueous phase is extracted twice with dichloromethane. The combined organic phases are dried over sodium sulfate, filtered and concentrated. The crude product is purified by flash chromatography (silica gel, dichloromethane: methanol: 19: 1) resulting in 1.36 g of the desired product. X H NMR (300 MHz, CDC13): d: 9.91 (s, ÍH), 8.24 (s, ÍH), 7.45 (s, ÍH), 4.33 (s, 4H). 5e) Title compound The compound is prepared as in example lk from the aldehyde (5d) in a yield of 78%. NMR 'H (300 MHz, d6-DMS0): d: 8.65 (d, HH), 8.03 (s, HH), 7.87-7.81 (m, 2H), 7.68 (d, HH), 7.58-7.51 (m, ÍH), 6.96 (s, ÍH), 5.48-5.38 (m, ÍH), 5.36-5.19 (m, ÍH), 4.36-4.33 (m, 2H), 4.29-4.27 (m, 2H), 3.95 (s, 3H), 3.73 (s, 2H), 3.04-2.90 (m, ÍH), 2.78-2.55 (m, 2H), 2.46-2.34 (m, ÍH), 2.21-2.03 (m, 2H), 1.89-1.74 ( m, 2H), 1.43-1.11 (m, 4H).

Example 6: 2-. { 4- [(2,3-dihydrobenzo [1,4] dioxin-6-ylmethyl) amino] -piperidin-1-yl} -l- (3-methoxyquinolin-5-yl) -ethanol (enantiomer 2) Enantiomer 2 The compound is prepared as in Example 1k from (2,3-dihydrobenzo [1,4] dioxin-6-carbaldehyde MS (El): m / z: 450 [M + H] + Example 7: 6- ( { L- [2-hydroxy-2- (3-methoxy-quinolin-5-yl) -ethyl] -piperidin-4-ylamino} -methyl) -4H-benzo [1, 4 ] oxazin-3-one (enantiomer 1) Enantiomer 1 7a) 3-methoxy-5-oxiranylquinoline (enantiomer 1) The compound is synthesized as described in the examples Id a lf. Instead of the mixture AD a, the mixture AD ß is used for the preparation of the diol (Id) 7b) Terbutyl ester of the acid. { l- [2-Hydroxy-2- (3-methoxyquinolin-5-yl) -ethyl] -piperidin-4-yl} -4-Carbamic (enantiomer 1) The title compound is prepared as in the example lg from the epoxide (7a) in a yield of 56%. XH NMR (300 MHz, CDC13): d: 8.56 (d, ÍH), 7.92 (m, ÍH), 7.64 (m, ÍH), 7.48-7.43 (m, ÍH), 5.72 (s broad, ÍH), 4.51 (m, ÍH), 3.85 (s, 3H), 3.60-3.46 (m, ÍH), 3.29-3.27 (m, 2H), 2.84-2.73 (m, 2H), 2.67-2.40 (m, 2H), 2.09-1.95 (m, 2H), 1.84-1.64 (m, 2H), 1.38 (s, 9H). 7c) 2- (4-aminopiperidin-1-yl) -1- (3-methoxyquinolin-5-yl) -ethanol (enantiomer 1) The title compound is prepared as in example lh from Boc-amine (7b) ) with a yield of 63%. NMR * H (300 MHz, d6-DMS0): d: 8.66-8.63 (m, ÍH), 7. 87-7.82 (m, 2H), 7.67 (m, ÍH), 7.58-7.51 (m, ÍH), 5.43-5.39 (m, ÍH), 5.26-5.23 (m, ÍH), 3.95 (s, 3H), 2.99-2.85 (m, 2H), 2.62-2.55 (m, ÍH), 2.19-1.99 (m, 2H), 1.72-1.57 (m, 2H). 7d) Title compound The title compound is prepared as in Example Ik from the amine (7c) and the aldehyde (Ij) in a yield of 86%. NMR * H (300 MHz, d6-DMS0): d: 10.78 (s, ÍH), 8.66 (d, ÍH), 7.96 (s, ÍH), 7.88-7.84 (m, 2H), 7.70-7.68 (m, ÍH), 7.59-7.54 (m, ÍH), 7.00-6.91 (m, 3H), 5.75 (s, ÍH), 5.49-5.46 (m, ÍH), 4.56 (s, 2H), 3.96 (s, 3H) , 2.82 (s, 2H), 3.12-3.03 (m, 2H), 2.72-2.60 (m, 2H), 2.30-2.10 (m, 2H), 2.00-1.85 (m, 2H), 1.58-1.36 (m, 3H).

Example 8: 7-fluoro-6- (. {1 l- [2-hydroxy-2- (3-methoxyquinolin-5-yl) -ethyl] piperidin-4-ylamino} -methyl) -4H-benzo [ 1,4] thiazin-3-one (enantiomer 1) Enantiomer 1 The title compound is prepared as in Example 7d from the aldehyde (3g) in a yield of 78%. X H NMR (300 MHz, d6-DMS0): d: 10.53 (s, 1H), 8.65 (d, 1H), 7.87-7.82 (m, 2H), 7.68 (d, 1H), 7.58-7.53 (m, 1H) ), 7.18 (d, ÍH), 7.09 (d, ÍH), 5.49-5.38 (m, ÍH), 5.33-5.21 (m, ÍH), 3.95 (s, 3H), 3.69 (s, 2H), 3.45 ( s, 2H), 3.05-2.90 (m, 2H), 2.65-2.55 (m, 2H), 2.45-2.29 (m, ÍH), 2.23-2.03 (m, 2H), 1.88-1.74 (m, 2H), 1.42-1.16 (m, 3H).

Example 9: 6- ( { L- [2-hydroxy-2- (3-methoxyquinolin-5-yl) ethyl] -piperidin-4-ylamino.} - methyl) -4 H -benzo [1,4] thiazin-3-one (enantiomer 1) Enantiomer 1 The title compound is prepared as in Example 7d from the aldehyde (4b) in 73% yield. X H NMR (300 MHz, d6-DMSO): d: 10.49 (s, ÍH), 8.65 (d, ÍH), 7.87-7.82 (m, 2H), 7.68 (d, ÍH), 7.58-7.53 (m, ÍH), 7.23 (d, ÍH), 6.97-6.91 (m, 2H), 5.46-5.36 (m, ÍH), 5.28-5.20 (m, ÍH), 3.95 (s, 3H), 3.62 (s, 2H), 3.43 (s, 2H), 3.04-2.98 (m, 2H), 2.65-2.55 (m , 2H), 2.43-2.28 (m, ÍH), 2.20-2.00 (m, 2H), 1.85-1.71 (m, 2H), 1.40-1.16 (m, 3H) Example 10: 6- ( { L- [2-hydroxy-2- (3-methoxy-quinolin-5-yl) -ethyl] -piperidin-4-ylamino} -methyl) -4H-pyrido [3.2 -b] thiazin-3 -one (enantiomer 1) Enantiomer 1 The title compound is prepared as in Example 7d from the aldehyde (2h) in a yield of 83%. X H NMR (300 MHz, d6-DMSO): d: 10.85 (s, ÍH), 7.87-7.82 (m, 2H), 7.74-7.67 (m, 2H), 7.58-7.51 (m, ÍH), 7.11-7.05 (m, ÍH), 5.50-5.36 (m, ÍH), 5.30-5.19 (m, ÍH), 3.95 (m, ÍH), 3.72 (s, 2H), 3.53 (s, 2H), 3.02-2.87 (m , 2H), 2.65-2.54 (m, 2H), 2.44-2.32 (m, ÍH), 2.21-2.02 (m, 2H), 1.86-1.70 (m, 3H), 1.42-1.13 (m, 3H).

Example 11: 2- { 4- [(2,3-dihydro- [1,4] dioxino [2, 3 c] pyridin-7-ylmethyl) amino] -piperidin-1-yl} -l- (3-methoxyquinolin-5-yl) -ethanol (enantiomer 1) Enantiomer 1 The title compound is prepared as in Example 7d from the aldehyde (5d) in a yield of 78%. H NMR (300 MHz, d6-DMS0): d: 8.65 (d, ÍH), 8.03 (s, ÍH), 7.87-7.81 (m, 2H), 7.68 (d, ÍH), 7.58-7.51 (m, ÍH), 6.96 (s, ÍH), 5.48-5.38 (m, ÍH), 5.36-5.19 (m, ÍH), 4.36-4.33 (m, 2H), 4.29-4.27 (m, 2H), 3.95 (s, 3H), 3.04-2.90 (m, ÍH), 2.78-2.55 (m, 2H), 2.46 -2.34 (m, ÍH), 2.21-2.03 (m, 2H), 1.89-1.74 (m, 2H), 1.43-1.11 (m, 4H).

Example 12: 2- { 4- [(2,3-dihydrobenzo [1,4] dioxin-6-ylmethyl) -amino] -piperidin-1-yl} -l- (3-methoxyquinolin-5-yl) ethanol (enantiomer 1) Enantiomer 1 The title compound is prepared as in Example 7d from 2,3-dihydrobenzo [1,4] dione-6-carbaldehyde MS (El): m / z 450 [M + H] + Example 13: 2-. { l- [2-Hydroxy-2- (3-methoxyquinolin-5-yl) -ethyl] -piperidin-4-ylamino} -N-pyridin-2-acetamide Enantiomer 1 13a) 2-chloro-N-pyridin-2-ylacetamide 1.8 ml of chloroacetyl chloride are added dropwise to an ice-cooled solution of 1.88 g of 2-aminopyridine in THF: pyridine (20 ml, 1: 1). After stirring for 3 hours at room temperature, the solution is poured into water and extracted with ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered and concentrated. The residue is recrystallized from ethyl acetate: ether, resulting in 3.4 g of the desired product.

MS (El): m / z: 171 [M + H] \ 13b) Title compound A To a solution of 0.05 g of the amine (7c) in 1 ml of DMF are added 0.034 g of the chloride (13a) and 0.05 g of sodium carbonate and stirred for 2 hours at 60 ° C. After concentrating the reaction mixture the crude product is purified by flash chromatography (silica gel, dichloromethane: methanol: 9: 1) resulting in the desired product EM (El): m / z: 436 [M + H] \ Example 14: 2- { 4- [(2,3-dihydrobenzo [1,4] dioxin-6-ylmethyl) amino] -piperidin-1-yl} -l- (3-methoxyquinolin-5-l) -ethanol (racemate) Racemate 14a) 3-methoxyquinoline-5-carbaldehyde To a solution of 2.68 g of the bromide (Ib) in 37 ml of ether and 37 ml of THF are added at -78 ° C n-butyllithium (9.3 ml, 2.5 M in hexane), stirred for 30 minutes and suspended with 5 ml of DMF. After 15 minutes add 8 ml of ethanol and a 50 ml solution of ammonium chloride and heat to room temperature. The aqueous phase is extracted with ethyl acetate. The combined organic phases are washed with a saturated solution of sodium chloride, dried over magnesium sulfate, filtered and concentrated. The residue is purified by flash chromatography (silica gel, hexane: acetic acid ethyl ester: 2: 1, 1: 2) resulting in 1.06 g of the desired product. MS (El): m / z: 188 [M + H] + 14b) 3-methoxy-5-oxiranylquinoline To a solution of 1.06 g of the aldehyde (14a) in 17.6 ml of acetonitrile are added 9 drops of water, 1.19 g of trimethylsulfonium iodide and 2.25 g of potassium hydroxide and heated at 60 ° C for 20 minutes. After cooling the solution is filtered, the filtrate is diluted with 10 ml of water and concentrated. The residue is extracted with ethyl acetate and the combined organic phases are concentrated. The residue is purified by flash chromatography (silica gel, hexane: acetic acid methyl ester: 2: 1, 1: 1) resulting in 1 g of the desired product. 1N-NMR (300 MHz, CDC13): d: 8.64 (d, HH), 7.94 (dd, HH), 7.59 (d, HH), 7.48-7.39 (m, 2H), 4.30 (m, HH), 3.91 ( s, 3H), 3.22 (dd, ÍH), 2.81 (dd, ÍH) 14c) terbutyl ester of the acid. { 1- [2-hydroxy-2- (3-methoxyquinolin-5-yl) -ethyl] -piperidin-4-yl} -carbamic (racemate) The compound is prepared as in example lg from the epoxide (14b) in a 65% yield. XH NMR (300 MHz, CDC13): d: 8.56 (d, ÍH), 7.92 (m, ÍH), 7.64 (m, ÍH), 7.48-7.43 (m, ÍH), 5.72 (s broad, ÍH), 4.51 (m, ÍH), 3.85 (s, 3H), 3.60-3.46 (m, 1H), 3.29-3.26 (m, 2H), 2.84-2.73 (m, 2H), 2.67-2.40 (m, 2H), 2.09-1.95 (m, 2H), 1.84-1.64 (m, 2H), 1.38 (s, 9H) 14d) 2- (2-aminopiperidin-1-yl) -l- (3-methoxyquinolin-5-yl) -ethanol (racemate) The compound is prepared as in Example 1h from Boc-amine (14c) with a yield of 78%. MS (El): m / z: 302 [M + H] + 14e) Title compound The title compound is prepared as in example lk from the amine (14d) and 2,3-dihydrobenzo [1, 4]. ] dioxin-6-carbaldehyde with a yield of 50%. MS (El): m / z: 450 [M + H] + Example 15: 2- { 4- [(benzo [1, 2, 5] thiadiazol-5-ylmethyl) -amino] -piperidin-1-yl} -1- (3-methoxyquinolin-5-yl) -ethanol (racemate) Racemate The compound is prepared as in example 14e from benzo [1, 2, 5] thiadiazole-5-carbaldehyde. MS (El): m / z: 450 [M + H] + Example 16: 1- (3-methoxyquinolin-5-yl) -2-. { 4- [(2-methylbenzofuran-5-ylmethyl) -amino] -piperidin-1-yl} -ethanol (racemate) Racemate 16a) 4-prop-2-ynyloxybenzaldehyde To a suspension of 5.91 g of 4-hydroxybenzaldehyde in 80 ml of toluene are added 87.4 g of potassium carbonate and propargyl bromide (8 ml, 80% solution in toluene) and heated at 100 ° C for 7 hours. The suspension is then filtered and the filtrate is concentrated. The residue is purified by flash chromatography (silica gel, hexane: acetic acid ethyl ester: 3: 1), whereby 5 g of the desired product are obtained. MS (El): m / z: 161 [M + H] + 16b) 2-methyl-benzofuran-5-carbaldehyde 40 ml of PEG 300 is heated at 220 ° C. A solution of 5 g of propylaldehyde (16a) in 10 ml of PEG 300 is added and stirred at 220 ° C for 90 minutes. After cooling the reaction mixture was poured into 200 g of ice and extracted with dichloromethane: ether (1: 1, 2 x 300 ml). The combined organic phases are concentrated. The residue is purified by flash chromatography (silica gel, hexane: acetic acid ethyl ester 9: 1), whereby 2 g of the desired product are obtained. 1 H NMR (300 MHz, CDC13): d: 9.93 (s, ÍH), 7.91 (s, ÍH), 7.67 (dd, ÍH), 7.40 (d, ÍH), 6.38 (s, ÍH), 2.39 (s, 3H) 16c) Compound of the title The compound is prepared as in example 14e from the aldehyde (16b) ) MS (El): m / z: 446 [M + H] + Example 17: 1- (3-methoxyquinolin-5-yl) -2-. { 4- [(quinoxalin-2-ylmethyl) -amino] -piperidin-1-yl} Ethanol (racemate) Racemate 17a) Quinoxaline-2-carbaldehyde To a solution of 12 g of selenium dioxide in 120 ml of dioxane and 5 ml of boiling water under reflux, a solution of 10 g of 2- methylquinoxaline in 20 ml of dioxane and then heated to reflux for 4 hours. After cooling the suspension is filtered through silica gel and the filtrate is concentrated. The residue is purified by flash chromatography (silica gel, hexane: acetic acid ethyl ester: 2: 1) resulting in 8 g of the desired product. MS (El): m / z: 159 [M + H] + 17 b) Title compound The compound is prepared as in example 14e from the aldehyde (17a). MS (El): m / z: 445 [M + H] + Example 18: 2- [4- ((E) -3-furan-2-yl-allylamino) -piperidin-1-yl] -1- (3-methoxyquinolin-5-yl) -ethanol (racemate) Racemate Prepared the compound as in Example 14e from (E) -3-furan-2-yl-propenal. MS (El): m / z: 408 [M + H] + Example 19: 2 -. { 4 - [(benzofuran-2-ylmethyl) -amino] -piperidin-1-yl} -l- (3-methoxyquinolin-5-yl) -ethanol (racemate) Racemate The compound is prepared as in example 14e from benzofuran-2-carbaldehyde. MS (El): m / z: 432 [M + H] + Example 20: 1- (3-methoxyquinolin-5-yl) -2- [4- (2-phenoxyethylamino) -piperidin-1-yl] -ethanol (racemate) Racemate The compound is prepared as in example 14e from phenoxyacetaldehyde (according to Syn. Lett., vol 11, 2004, P. 2010). MS (El): m / z: 422 [M + H] + Example 21: 5- ( { 1 - [2-Hydroxy-2- (3-methoxyquinolin-5-yl) -ethyl] -piperidin-4-ylamino.} - methyl) -3H-benzoxazol-2-one (racemate) Racemate 21a) 4- [1,3] dioxan-2-yl-2-nitrophenol To a solution of 5.54 g of 4-hydroxy-3-nitrobenzaldehyde in 110 ml of toluene are added 3.80 g of 1,3-propanediol and 0.11 g. g of p-toluenesulfonic acid and heated at reflux for 3 hours. After cooling, the solution is washed with a saturated solution of sodium hydrogen carbonate and the aqueous phase is extracted again with ether. The combined organic phases are washed with a saturated solution of sodium chloride, dried over magnesium sulfate, filtered and concentrated, resulting in 3.5 g of the desired product. XH NMR (300 MHz, CDC13): d: 10.63 (s, ÍH), 8.26 (s, ÍH), 7.73 (d, ÍH), 7.17 (d, ÍH), 5.49 (s, ÍH), 4.32-4.26 (m, 2H), 4.04-3.96 (m, 2H), 1.51-1.46 (m , 2H) 21b) 2-amino-4- [1,3-dioxan-2-ylphenol To a solution of 2 g of nitrophenol (21a) in THF add Raney nickel and stir for 5 hours under an atmosphere of hydrogen gas . The reaction mixture is filtered and the filter cake is washed with ethyl acetate. The filtrate is concentrated resulting in 1.66 g of the desired product. MS (El): m / z: 196 [M + H] + 21c) 5- [1,3] dioxan-2-yl-3H-benzoxazol-2-one To a solution of 1.66 g of aminophenol (21b) in 40 ml of dichloromethane are added at 0 ° C 1.72 ml of triethylamine and 3.33 g of triphosgene and stirred for 1.5 hours. The solution is concentrated and the residue is purified by flash chromatography (silica gel, ethyl acetate: hexane: 1: 1) resulting in 1.5 g of the desired product. MS (El): m / z: 222 [M + H] + 21d) 2-OXO-2, 3-dihydrobenzoxazole-5-carbaldehyde To a solution of 1.5 g of benzoxazole (21c) in 20 ml of methanol is added a 3 M solution of 2.5 ml hydrochloric acid and stir for 2 hours. Subsequently, the solution is partially concentrated and extracted with ethyl acetate. The combined organic phases are washed with a saturated sodium hydrogen carbonate solution, dried over magnesium sulfate, filtered and concentrated resulting in 0.84 g of the desired product. 1 H NMR (300 MHz, d6-DMSO): d: 12.00 (broad s, HI), 9.96 (s, HI), 7.73 (d, ÍH), 7.54-7.50 (m, 2H) 21e) Title compound Prepared the title compound as in Example 14e from the aldehyde (21d) MS (El): m / z: 449 [M + H] + Example 22: 2-. { 4- [(2,3-dihydro- [1,4] dioxino [2, 3-c] pyridin-7-ylmethyl) -amino] -piperidin-1-yl} -l- (3-methoxyquinolin-5-yl) -ethanol (racemate) Racemate The compound is prepared as in example 14e from the aldehyde (5d). MS (El): m / z: 451 [M + H] + Example 23: 2-. { 4- [(3, -dihydro-2H-benzo [b] [1,4] dioxepin-7-ylmethyl) -amino] -piperidin-1-yl} -1- (3-methoxyquinolin-5-yl) -ethanol (racemate) Racemate 23a) 3,4-dihydro-2H-benzo [b] [1,4] dioxepin-7-carbaldehyde To a solution of 1.67 g of 3,4-dihydroxybenzaldehyde and 3.34 g of potassium carbonate in 15 ml of acetonitrile add 1.36 ml of 1,3-dibromopropane and heat to reflux. Subsequently, the reaction mixture is filtered and rinsed again with ether. The filtrate is concentrated and the residue is purified by flash chromatography (silica gel, hexane: ethyl acetate: 4: 1) and resulting in 1.5 g of the desired product. X H NMR (300 MHz, CDC13): d: 9.86 (s, ÍH), 7.50-7.43 (m, 2H), 7.08-7.04 (m, ÍH), 4.39-4.21 (m, 4H), 2.31-2.23 (m , 2H) 23b) Title compound The compound is prepared as in example 14e from the aldehyde (23a). MS (El): m / z: 464 [M + H] + Example 24: 1- (3-methoxyquinolin-5-yl) -2- [4- ((E) -3-phenylamino) -piperidin-1-yl] -ethanol (racemate) Racemate The compound is prepared as in example 14e from the cinnamic aldehyde. MS (El): m / z: 418 [M + H] + Example 25: 1- (3-methoxyquinolin-5-yl) -2-. { 4 - [(1-methyl-lH-indol-2-ylmethyl) -amino] -piperidin-1-yl} -ethanol (racemate) Racemate The compound is prepared as in example 14e from l-methyl-lH-indole-2-carbaldehyde. MS (El): m / z: 445 [M + H] + Example 26: 1- (3-methoxyquinolin-5-yl) -2- [4- (3-phenylpropylamino) -piperidin-1-yl] -ethanol (racemate) Racemate The compound is prepared as in example 14e from 3-phenylpropionaldehyde. MS (El): m / z: 420 [M + H] * Example 27: 7- ( { L- [2-hydroxy-2- (3-methoxy-quinolin-5-yl) -ethyl] -piperidin-4-ylamino} -methyl) -4H-benzo [1.4 ] oxazin-3-one (racemate 27a) (5-formyl-2-nitrophenoxy) acetic acid ethyl ester To a solution of 3-hydroxy-4-nitrobenzaldehyde in 100 ml of DMF is added 7 ml of chloroacetic acid ethyl ester and 10 g of potassium carbonate and heated for 2 hours at 50 ° C. Water is added to the reaction mixture and the reaction mixture is extracted with ethyl acetate: ether. The organic phase is concentrated and the residue is purified by flash chromatography (silica gel, hexane: acetic acid ethyl ester: 4: 1, 3: 1, 2: 1, 1: 1) resulting in 14.2 g of the product wanted. XH NMR (300 MHz, CDC13): d: 10.04 (s, HH), 7.98 (d, HH), 7.62 (d, HH), 7.50 (s, HH), 4.87 (s, 2H), 4.29 (c, 2H), 1.31 (t, 3H) 27b) 7-hydroxymethyl-4H-benzo [1,4] oxazin-3-one A suspension of 7 g of nitrobenzaldehyde (27a) in 200 ml of acetic acid is mixed with 15.4 g of Iron powder and heat to reflux. Then the reaction mixture is filtered through Celite and rinsed again with acetic acid. The filtrate is concentrated and the residue is resuspended or redissolved, respectively, in acetic acid ethyl ester and washed with a saturated sodium hydrogen carbonate solution. The organic phase is dried over sodium sulfate, filtered and concentrated. The crude product is purified by flash chromatography (silica gel, hexane: ethyl acetate: 1: 1) resulting in 1.5 g of the desired product. X H NMR (300 MHz, d6-DMSO): d: 10.64 (s, ÍH), 6.88-6.81 (m, 3H), 5.13-5.09 (m, ÍH), 4.54 (s, 2H), 4.38 (d, 2H) ) 27c) 3-oxo-3,4-dihydro-2H-benzo [1,4] oxazin-7-carbaldehyde A solution of 1.5 g of alcohol (27b) in THF: dichloromethane (150 ml, 1: 1) is mixed with 7.3 g of manganese dioxide and stir for 1.5 hours. Then the reaction mixture is filtered through Celite, rinsed again with THF and the filtrate is concentrated. The residue is treated with ether, the solid that is produced is filtered off which results in 1 g of the desired product. X H NMR (300 MHz, d6-DMS0): d: 9.83 (s, 1H), 7.54 (d, 1H), 7.43 (s, 1H), 7.06 (d, 1H), 4.68 (s, 2H) 27d) Compound of the title The compound is prepared as in example 14e from the aldehyde (27c).

MS (El): m / z: 464 [M + H] + Example 28: 6- ( { 1- [2-hydroxy-2- (3-methoxy-quinolin-5-yl) -ethyl] -piperidin-4-ylamino} -methyl) -4H-benzo [1.4] ] oxazin-3-one (racemate) Racemate The title compound is prepared as in example 14e from the aldehyde (lj). X H NMR (300 MHz, d6-DMSO): d: 10.78 (s, 1H), 8.66 (d, 1H), 7.96 (s, 1H), 7.88-7.84 (m, 2H), 7.70-7.68 (m, 1H) ), 7.59-7.54 (m, ÍH), 7.00-6.91 (m, 3H), 5.75 (s, ÍH), 5.49-5.46 (m, ÍH), 4.56 (s, 2H), 3.96 (s, 3H), 2.82 (s, 2H), 3.12-3.03 (m, 2H), 2.72-2.60 (m, 2H), 2.30-2.10 (m, 2H), 2.00-1.85 (m, 2H), 1.58-1.36 (m, 3H) ) Example 29: 6- ( { 1- [2-hydroxy-2- (3-methoxy-quinolin-5-yl) -ethyl] -piperidin-4-ylamino} -methyl) -4H-pyrido [3.2 -b] [1,] oxazin-3-one (racemate) Racemate The title compound is prepared as in example 14e from 3-oxo-3,4-dihydro-2H-pyrido [3,2-b] [1,] oxazin-6-carbaldehyde (this compound is prepared from according to what is described in WO 2006/021 448). MS (El): m / z: 464 [M + H] + Example 30: 1- (3-methoxyquinolin-5-yl) -2- [4- ((E) -3-pyridin-2-yl-allylamino) -piperidin-1-yl] -ethanol (racemate) Racemate The title compound is prepared as in example 14e from (E) -3-pyridin-2-yl-propenal (this compound is prepared according to that described in WO 2006/021 448). MS (El): m / z: 419 [M + H] + Example 31: 2-. { 4- [(E) -3- (2,5-difluorophenyl) -arylamino] -piperidin-1-yl} -l- (3-methoxyquinolin-5-yl) -ethanol (racemate) Racemate The title compound is prepared as in example 14e from (E) -3- (2,5-difluorophenyl) propenal (this compound is prepared according to that described in WO 2004/087 647). MS (El): m / z: 454 [M + H] + Example 32: 1 (3-methoxyquinolin-5-yl) -2-. { 4- [(naphthalen-2-ylmethyl) amino] -piperidin-1-yl} -ethanol Racemate The title compound is prepared as in example 14e from naphthalene-2-carbaldehyde MS (El): m / z: 442 [M + H] +.

Example 33: { l- [2-Hydroxy-2- (3-methoxyquinolin-5-yl) -ethyl] -piperidin-4-yl} 3-oxo-3,4-dihydro-2H-benzo [1,4-oxazine-6-carboxylic acid amide (racemate) Racemate To a solution of 180 mg of the amine (14d) in a mixture of 6 ml of dichloromethane and 1 ral of DMF is added 116 mg of 3-oxo-3,4-dihydro-2H-benzo [1, 4] oxazin-6-carboxylic acid, 112 mg of EDC and 98 mg of HOBT at room temperature. After stirring for 12 hours at room temperature, the solution is concentrated. The residue is purified by flash chromatography (silica gel, 2-3% methanol in dichloromethane + 1% ammonium hydroxide) resulting in 111 mg of the desired product. MS (ESI): m / z: 477 [M + H] *.

Example 34:. { l- [2-Hydroxy-2- (3-methoxyquinolin-5-yl) -ethyl] -piperidin-4-yl} 3-oxo-3,4-dihydro-2H-benzo [1,4] thiazine-6-carboxylic acid amide (racemate) Racemate The title compound is prepared as in Example 33 from 3-oxo-3,4-dihydro-2H-benzo [1,4] thiazine-6-carboxylic acid MS (El): m / z: 493 [ M + H] +.

Example 35: { l- [2-Hydroxy-2- (3-methoxyquinolin-5-yl) -ethyl] -piperidin-4-yl} 3-oxo-3,4-dihydro-2H-pyrido [3,2-b] thiazine-6-carboxylic acid amide (racemate) Racemate The title compound is prepared as in Example 33 from 3-oxo-3,4-dihydro-2H-pyrido [3,2-1] [1,4] thiazine-6-carboxylic acid (2f) MS (El): m / z: 494 [M + H] +.

Example 36:. { l- [2-Hydroxy-2- (3-methoxyquinolin-5-yl) -ethyl] -piperidin-4-yl} 2,3-dihydro-benzo [1,4] dioxin-6-carboxylic acid amide (racemate) Racemate The title compound is prepared as in Example 33 from 2,3-dihydro-benzo [1,4] dioxin-6-carboxylic acid MS (El): m / z: 464 [M + H] +.

Example 37: { l- [2-Hydroxy-2- (3-methoxyquinolin-5-yl) -ethyl] -piperidin-4-yl} 3-oxo-3,4-dihydro-2H-benzo [1,4] oxazine-6-sulfonic acid amide (racemate) Racemate To a solution of 0.3 g of the amine (14d) in 15 ml of dry dichloromethane 0.21 ml of triethylamine and 0.27 g of 3-oxo-3,4-dihydro-2H-benzo [1] chloride are added at room temperature. 4] oxazin-6-sulfonyl. After stirring for 24 hours at room temperature the reaction mixture is concentrated. The residue is purified by flash chromatography (silica gel, chloroform: methanol: 9: 1 + 5% ammonium hydroxide) resulting in 0.15 g of the desired product. MS (El): m / z: 513 [M + H] +.

Example 38: { l- [2-Hydroxy-2- (3-methoxyquinolin-5-yl) -ethyl] -piperidin-4-yl} 3-Oxo-3,4-dihydro-2H-benzo [1,4] -thiazine-6-sulfonic acid (racemate) amide Racemate The title compound is prepared as in example 37 from 3-oxo-3,4-dihydro-2H-benzo [1,4] thiazine-6-sulfonyl chloride MS (El): m / z: 529 [M + H] \ Example 39:. { l- [2-Hydroxy-2- (3-methoxyquinolin-5-yl) -ethyl] -piperidin-4-yl} 2,3-dihydrobenzo [1,4] dioxin-6-sulfonic acid amide (racemate) Racemate The title compound is prepared as in example 37 from 2,3-dihydro-2H-benzo [1,4] dioxin-6-sulfonyl EM (El): m / z: 500 [M + H] chloride. ] Example 40: 2- { 4- [(2,3-dihydrobenzo [1,4] dioxin-6-ylmethyl) -amino] -3-fluoropiperidin-1-yl} -l- (3-methoxyquinolin-5-yl) -ethanol (enantiomer 1) Enantiomer 1 40a) 4-Oxopiperidine-1-carboxylic acid terbutyl ester 15.00 g of 4-piperidone hydrochloride hydrate are dissolved in a 1 N solution of 102 ml of sodium hydroxide, 102 ml of water and 102 ml of dioxane. A solution of 23.44 g of Boc anhydride in 102 ml of dioxane is added dropwise at room temperature and the reaction mixture is stirred overnight at room temperature. The solution is partially concentrated and extracted several times with ethyl acetate. The combined organic phases are washed with a saturated solution of sodium chloride, dried over magnesium sulfate, concentrated resulting in 19.27 g of the desired product. MS (El): m / z: 200 [M + H] +. 40b) 4-Trimethylsilanyloxy-3,6-dihydro-2H-pyridine-l-carboxylic acid terbutyl ester To a solution of 10.12 g of the ketone (40a) in ml of DMF is added 7.8 ml of trimethylsilyl chloride and 17 ml of triethylamine and heated at 80 ° C overnight. After cooling, DMF is removed under reduced pressure, and the residue is resuspended or redissolved, respectively, in a saturated solution of sodium hydrogencarbonate and extracted with hexane. The organic phase is dried over magnesium sulfate, filtered and concentrated. The residue is purified by flash chromatography (silica gel, hexane: acetic acid ethyl ester: 9: 1) resulting in 10.5 g of the desired product. MS (El): m / z: 272 [M + H] +. 40c) 3-Fluoro-4-oxopiperidine-1-carboxylic acid terbutyl ester To a solution of 10.5 g of silylenyl ether (40b) in 420 ml of acetonitrile add 15.1 g of Selectfluor and stir for 75 minutes at room temperature. A saturated solution of sodium chloride is added and acetonitrile is removed under reduced pressure. The residue is extracted with ethyl acetate, and the organic phase is dried over sodium sulfate, filtered and concentrated. The residue is purified by flash chromatography (aluminum oxide III, acetic acid ethyl ester, ethyl acetate: methanol: 9: 1) resulting in 8.5 g of the desired product. MS (El): m / z: 218 [M + H] +. 40d) 4-Benzylamino-3-fluoropiperidine-1-carboxylic acid terbutyl ester To a solution of 7.12 g of fluoride (40c) in 150 ml of 1,2-dichloroethane are added 4 ml of benzylamine and then 8.5 g of triacetoxy of Sodium borohydride and stir overnight at room temperature. Subsequently, 100 ml of a saturated solution of sodium hydrogen carbonate is added and the pH value is adjusted to 8 with solid sodium hydrogen carbonate. The phases are separated and the aqueous phase is extracted with dichloromethane. The combined organic phases are washed with a saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The residue is purified by flash chromatography (silica gel, hexane: acetic acid ethyl ester: 1: 1) resulting in the desired product. MS (El): m / z: 309 [M + H] +. 40e) 4-Amino-3-fluoropiperidine-1-carboxylic acid terbutyl ester To a solution of 4 g of benzylamine (40d) in 100 ml of methanol, 2.7 g of 20% palladium hydroxide are added and the reaction mixture is added. stir under an atmosphere of hydrogen gas for 4 hours. The solution is filtered, it is concentrated under vacuum resulting in 2.84 g of the desired product. MS (El): m / z: 219 [M + H] \ 40f) 4-Benzyloxycarbonylamino-3-fluoropiperidine-1-carboxylic acid terbutyl ester To a solution of 2.84 g of the amine (40e) in 50 ml of ester Ethyl acetic acid and a saturated solution of 50 ml of sodium hydrogen carbonate add 2 ml of Z-chloride and stir for 1 hour at room temperature. The two phases are separated and the aqueous phase is extracted with ethyl acetate. The combined organic phases are washed with a saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The residue is purified by flash chromatography (silica gel, hexane: acetic acid ethyl ester: 2: 1) resulting in the desired product. MS (El): m / z: 353 [M + H] +. 40g) (3-fluoropiperidin-4-yl) -carbamic acid benzyl ester A solution of the protected amine (40f) in 10 ml of TFA is stirred at room temperature for 30 minutes.

The solvent is removed under reduced pressure and the residue is resuspended or redissolved, respectively, in a 3N sodium hydroxide solution and extracted several times with 9: 1 dichloromethane: methanol. The combined organic phases are washed with a saturated solution of sodium chloride, dried over sodium sulfate, filtered, concentrated resulting in 2.9 g of the desired product. MS (El): m / z: 253 [M + H] +. 40h) Benzyl acid ester. { 3-Fluoro-l- [2-hydroxy-2- (3-methoxyquinolin-5-yl) -ethyl] -piperidin-4-yl} -carbamic (enantiomer 1) To a solution of 0.8 g of 3-methoxy-5-oxiranylquinoline (7a) and 1.01 g of piperidine (40 g) in 10 ml of DMF is added 0.425 g of lithium perchlorate and heated to 80 °. C during the night. The solvent is removed under reduced pressure and the residue is purified by flash chromatography (silica gel, acetic acid ethyl ester) resulting in 1.7 g of the desired product. MS (El): m / z: 454 [M + H] +. 40i) 2- (4-amino-3-fluorpyridin-1-yl) -1- (3-methoxyquinolin-5-yl) -ethanol (enantiomer 1 To a solution of 1.7 g of the compound (40 h) in 50 ml of ester ethyl acetate and 10 ml of ethanol are added 0.7 g of 10% palladium in charcoal and stirred for 6 hours under an atmosphere of hydrogen gas.The solution is filtered, concentrated resulting in a desired product. El): m / z: 320 [M + H] +. 40j) Title compound The compound is prepared as in example 7d from the amine (40i) and 2,3-dihydrobenzo [1,4] dioxin- 6-carbaldehyde. MS (El): m / z: 468 [M + H] \ Example 41: 6- (3-Fluoro-1- [2-hydroxy-2- (3-methoxy-quinolin-5-yl) -ethyl] -piperidin-4-ylamino} -methyl) -4H-benzo [1, 4] oxazin-3-one (enantiomer 1) Enantiomer 1 The compound is prepared as in example 40j from the aldehyde (lj) MS (El): m / z: 481 [M + H] \ Example 42: 2- (3-Fluoro-4- ((E) -3-phenylallylamino-piperidin-1-yl] -1- (3-methoxyquinolin-5-yl) -ethanol (enantiomer 1) Enantiomer 1 The compound is prepared as in Example 40j from the cinnamic aldehyde. MS (El): m / z: 436 [M + H] +.

Example 43: 6- ( { 3-Fluoro-1- [2-hydroxy-2- (3-methoxy-quinolin-5-yl) -ethyl] -piperidin-4-ylamino} -methyl) -4H-pyrido [3, 2-b] [1,4] thiazin-3-one (enantiomer 1) Enantiomer 1 The compound is prepared as in Example 40j from the aldehyde. MS (El): m / z: 498 [M + H] \ Example 44: 2-. { 4- [(3,4-Dihydro-2H-benzo [1,4] oxazin-6-ylmethyl) -amino] -3-fluoropiperidin-1-yl} -l- (3-methoxyquinolin-5-yl) -ethanol (enantiomer 1) Enantiomer 1 44a) (3,4-dihydro-2H-benzo [1,4] oxazin-6-yl) -methanol To an ice-cooled solution of 1.77 g of the aldehyde (lj) in 100 ml of THF, 1 is added. g of lithium aluminum hydride, stirred for 30 minutes at 0 ° C and then heated to reflux for 90 minutes. After cooling with 1 ml of water, 1 ml of a 15% solution of sodium hydroxide and 3 ml of water are subsequently added. The reaction mixture is diluted with 100 ml of THF and the precipitate is separated by filtration. The filtrate is concentrated and the residue is purified by flash chromatography (silica gel, acetic acid ethyl ester) resulting in 1.5 g of the desired product. MS (El): m / z: 166 [M + H] +. 44b) 3,4-dihydro-2H-benzo [1,4] oxazin-6-carbaldehyde To a solution of 1.5 g of the alcohol (44a) in 100 ml of dichloromethane and 100 ml of THF are added 3 g of manganese dioxide . After stirring for 2 hours at room temperature, 3 g of additional manganese dioxide are added thereto and stirred for an additional 3 hours. Subsequently, the reaction mixture is filtered through Celite and rinsed again with THF. The filtrate is concentrated resulting in 1 g of the desired product. MS (El): m / z: 164 [M + H] +. 44c) Title compound The compound is prepared as in example 40j from the aldehyde (44b). MS (El): m / z: 467 [M + H] +.

Example 45: 2- { 4- [(2,3-dihydro- [1,4] dioxino [2, 3-c] pyridin-7-ylmethyl) amino] -3-fluoropiperidin-1-yl} -l- (3-methoxyquinolin-5-yl) -ethanol (enantiomer 1) Enantiomer 1 The compound is prepared as in Example 40j from the aldehyde (5d). MS (El): m / z: 470 [M + H] +.

Example 46: 2- { 4- [(benzo [1, 2, 5] thiadiazol-5-ylmethyl) -amino] -3-fluoropiperidin-1-yl} -l- (3-methoxyquinolin-5-yl) ethanol (enantiomer 1) Enantiomer 1 The compound is prepared as in Example 40j from benzo [1, 2, 5] thiadiazole-5-carbaldehyde. MS (El): m / z: 468 [M + H] +.

Example 47: 6- ( { 3-Fluoro-1- [2-hydroxy-2- (3-methoxy-quinolin-5-yl) -ethyl] -piperidin-4-ylamino} -methyl) -4H -benzo [1,4] thiazin-3-one (enantiomer 1) Enantiomer 1 The compound is prepared as in example 40 from aldehyde (4b). MS (El): m / z: 497 [M + H] + Example 48: 2 { [4- [(2,3-dihydro-benzo [1,4] dioxin-6-ylmethyl) -amino] -4- (2-hydroxy-ethyl) -piperidin-1-yl] -1- (3-methoxyquinoline) -5-yl) -ethanol (racemate) Racemato 48a) 4-amino-4-carboxymethyl-piperidine-1-carboxylic acid benzyl ester To a solution of 10 g of the 4-oxo-piperidin-1-carboxylic acid benzyl ester and 4-93 g of ammonium formate in 20 ml of methanol, 4.5 g of malonic acid are added and the mixture is refluxed for 3 days. After concentrating, 12 g of the crude product is further processed without further purification. 48b) 4-Amino-4-methoxycarbonylmethyl-piperidine-1-carboxylic acid benzyl ester To a solution of 5 g of the ester (48a) in 25 ml of methanol and 25 ml of hexane is added the same TMS-diazomethane (2 M) in hexane, 9 ml) and stirred for 3 hours at room temperature. After concentrating, the residue is resuspended or redissolved, respectively, in 100 ml of acetic acid ethyl ester and 30 ml of a 1 N sodium hydroxide solution. The organic phase is washed with 30 ml of a solution of 1N sodium hydroxide and 30 ml of a saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated, yielding 4.9 g of the desired product. MS (El): m / z: 307 [M + H] + 48c) 4- [(2,3-Dihydro-benzo [1,4] dioxin-6-ylmethyl) -amino] -4- benzyl ester methoxy-carbonylmethyl-piperidine-1-carboxylic acid To a solution of 0.86 g of aminopiperidine (48b) and 0.5 g of 2,3-dihydro-benzo [1,4] -dioxin-6-carbaldehyde in 15 ml of 1, 2 - dichloroethane 0.72 g of sodium triacetoxy borohydride are added and stirred for 16 hours at room temperature. Subsequently, a saturated solution of 20 ml of sodium bicarbonate and 50 ml of dichloromethane is added, the phases are separated and the aqueous phase is extracted with 50 ml of dichloromethane. The combined organic phases are washed with a saturated solution of sodium chloride, dried over sodium sulfate, filtered and concentrated. The residue is purified by flash chromatography (silica gel, acetic acid ethyl ester) resulting in 0.75 g of the desired product. MS (El): m / z 455 [M + H] + 48d) 4- [(2,3-Dihydro-benzo [1,4] dioxin-6-ylmethyl) -amino] -4- benzyl ester ( 2-hydroxy-ethyl) -piperidine-1-carboxylic acid To a solution of 0.75 g of the ester (48c) in 20 ml of THF, add 0.3 g of lithium borohydride and stir for 2 hours at room temperature. 5 ml of water, 2 ml of methanol and a saturated solution of 50 ml of sodium potassium tartrate are added. After stirring for 20 minutes, 100 ml of dichloromethane are added, the phases are separated and the aqueous phase is extracted with dichloromethane (50 ml, 3 times). The combined organic phases are concentrated and the residue is purified by flash chromatography (silica gel, ethyl acetate) which results in 0.5 g of the desired product. MS (ESI: m / z: 427 [M + H] + 48e) 2-. { 4- [(2,3-dihydro-benzo [1,4] dioxin-6-ylmethyl) -amino] -piperidin-4-yl} -ethanol To a solution of 0.5 g of protected piperidine (48d) in 8 ml of THF and 2 ml of methanol is added 0.5 g of 20% palladium hydroxide and stirred for 4 hours at room temperature under an atmosphere of hydrogen gas. The solution is filtered, concentrated, which generates 340 mg of the desired product. MS (El): m / z: 293 [M + H] + 48f) Title compound The title compound is prepared as in example lg from the epoxide (14b) and the piperidine (48e). MS (El): m / z: 494 [M + H] + Example 49: 2- [4- [(benzo [1,3] dixol-5-ylmethyl) -amino] -4- (2-hydroxy-ethyl) -piperidin-1-yl] -1- (3-methoxy) quinolin-5-yl) -ethanol (racemate) Racemate Piperidine (2- {4- [(benzo [1,3] dioxol-5-ylmethyl) -amino] -piperidin-4-yl} -ethanol is prepared analogously to steps 48c to 48e from benzo [1, 3] dioxol-5-carbaldehyde The title compound is prepared as in example 48f from epoxide (14b) and 2-. {4- [(benzo [1,3] dioxol] -5-ylmethyl) -amino] -piperidin-4-yl.} - ethanol, MS (El): m / z: 480 [M + H] + Example 50: 6- (. {4- (2-Hydroxy-ethyl) -1- [2-hydroxy-2- (3-methoxy-quinolin-5-yl) -ethyl] -piperidin-4-ylamino} .methyl) -4 H -benzo [1,4] oxazin-3-one (racemate) Racemate Piperidine (6 { [4- (2-hydroxy-ethyl) -piperidin-4-ylamino] -methyl} -4 H -benzo [1,4] oxazin-3-one) is prepared analogously to steps 48c to 48e from the aldehyde (lj). The title compound is prepared as in example 48f from epoxide (14b) and 6-. { [4- (2-hydroxy-ethyl) -piperidin-4-ylamino] -methyl} -4H-benzo [1,4] oxazin-3-one. In the); m / z: 507 (M + H] + Example 51: 2- { 4- [(2,3-dihydro-benzo [1,4] dioxin-6-ylmethyl) -amino] -3-hydroxymethyl-piperidin-1-yl} -l- (3-methoxy-quinolin-5-yl) -ethanol (racemate) 51a) l-benzyl-3-hydroxymethyl-piperidin-4-ol To a mixture of 1344 g of sodium hydroxide and 10 g of l-benzyl-3-carbethoxy-4-piperidone hydrochloride in 160 ml of methanol are added 2.543 g of sodium borohydride at 0 ° C and stirred for 30 minutes. Then 150 ml of water are added dropwise and the solution is partially concentrated. The aqueous phase is extracted with dichloromethane (150 ml, 3 times). The combined organic phases are washed with a saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The residue is resuspended or redissolved, respectively in 140 ml of ether and 2.55 g of lithium aluminum hydride are added at 0 ° C and stirred for 1 hour. Subsequently, 2 ml of water, 4 ral of a 3 N sodium hydroxide solution and 9 ml of water are added, the mixture is heated to room temperature and 150 ml of ether are added. The solid is filtered off, the filtrate is concentrated resulting in 5.33 g of the desired product.

MS (El): m / z: 222 [M + H] + 51b) l-benzyl-3- (tert-butyl-dimethylsilanyloxymethyl) -piperidin-4-ol To a solution of 5.33 g of the diol (51a) in 47 ml of dichloromethane are added at 0 ° C 3.9 g of tert-butyldimethylsilyl chloride, 6.6 ml of triethylamine and 0.287 mg of DMAP, and stirred for 4 days at 0 ° C. After concentrating, the residue is resuspended or redissolved, respectively, in water and acetic acid ethyl ester, the phases are separated and the aqueous phase is extracted with ethyl ether of acetic acid (100 ml, 3 times).

The combined organic phases are washed with a saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The residue is purified by flash chromatography (silica gel, acetic acid ethyl ester: hexane: 1: 2) resulting in 5.6 g of the desired product. MS (El): m / z: 336 [M + H] + 51c) 3- (tert-butyl-dimethylsilanyloxyethyl) -piperidin-4-ol To a solution of 5.6 g of benzylpiperidine (51b) in 90 ml of THF: methanol 1: 1 3.6 g of 10% palladium hydroxide are added and stirred overnight under an atmosphere of gaseous hydrogen. Subsequently the reaction mixture is filtered and the filtrate is concentrated resulting in 4. 1 g of the desired product. MS (El): m / z: 246 [M + H] + 51d) 3- (tert-Butyl-dimethylsilyloxymethyl) -4-hydroxy-piperidine-1-carboxylic acid benzyl ester To a solution of 4.1 g of piperidinyl ( 51c) in 87 ml of acetone: water: 2: 1, 2,803 g of sodium bicarbonate and 2.35 ml of Z-chloride are added. After stirring for 1 hour at room temperature the solution is partially concentrated and the aqueous phase is extracted with ethyl ether of acetic acid. The combined organic phases are washed with a saturated solution of sodium chloride, dried over magnesium sulfate, filtered and concentrated. The residue is purified by flash chromatography (silica gel, ethyl acetate: hexane: 1: 4, 1: 1) resulting in 6.1 g of the desired product. MS (El): m / z: 380 [M + H] + 51e) 3- (tert-Butyl-ethyl-silayloxymethyl) -4-oxo-piperidine-1-carboxylic acid benzyl ester To a solution of 3 g of alcohol (51d) in 1. 857 g of N-methylmorpholine N-oxide and 3.95 g of pulverized molecular sieves 4A in 15 ml of dichloromethane are added 0.139 g of TPAP at room temperature. After 1 hour the solution is filtered through silica gel and the filtrate is concentrated. The residue is purified by flash chromatography (silica gel, ethyl acetate: hexane 1: 4) resulting in 2 g of the desired product. MS (El): m / z: 378 [M + H] + 51f) 4-amino-3- (tert-butyl-dimethyl-silanyloxymethyl) -piperidine-1-carboxylic acid benzyl ester To a solution of 2 g of the ketone (51e) in 50 ml of methanol is added 6.13 g of ammonium acetate and 1.69 g of sodium triacetoxyborohydride and stirred overnight at room temperature. After concentrating the reaction mixture the residue is resuspended or redissolved, respectively, in water and dichloromethane, the phases are separated and the aqueous phase is extracted with dichloromethane (70 ml, 3 times). The combined organic phases are washed with a saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. 1 g of the crude product is used additionally without further purification. 51g) 3- (Tertbutyl-dimethyl-silanyloxymethyl) -4- [(2,3-dihydro-benzo [1,4] -dioxin-6-ylmethyl) -amino] -piperidine-1-carboxylic acid benzyl ester To a solution of 1 g of the amine (51f) in 7 ml of methanol and 2 ml of dichloromethane is added 7 g of molecular sieve 3A and 0.434 g of 2,3-dihydro-benzo [1,4] dioxan-5-carbaldehyde and it is stirred for 20 hours at room temperature. Then add 0.120 g of sodium borohydride and stir for an additional 2 hours. The molecular sieve is filtered off and the filtrate is washed with saturated sodium bicarbonate solution and saturated sodium chloride solution. The organic phase is dried over magnesium sulfate, filtered and concentrated. The residue is purified by flash chromatography (silica gel, dichloromethane: methanol: 9: 1 + 1% ammonia) resulting in 500 mg of the desired product. MS (El): m / z: 527 [M + H] + 51h) [3- (tert-butyl-dimethylsilanyloxymethyl) -piperidin-4-yl] - (2,3-dihydro-benzo [1,4] dioxin] -6-ylmethyl) -amine To a solution of 500 mg of the Z-protected piperidine (51 g) in 15 ml of acetic acid ethyl ester is added 0.4 g of 10% palladium in charcoal and stirred for 2 hours under a gaseous hydrogen atmosphere. The solution is filtered and concentrated resulting in 0.37 g of the desired product. MS (El): m / z: 393 [M + H] + 51i) 2-. { 3- (tert-butyl-dimethyl-silanyloxymethyl) -4- [(2,3-dihydro-benzo- [1,4] dioxin-6-ylmethyl) -amino] -piperidin-1-yl} -l- (3-methoxy-quinolin-5-yl) -ethanol To a solution of 150 mg of the epoxide (14b) and 293 mg of protected piperidine (51h) in 3 ml of DMF is added 0.150 g of potassium carbonate and 0.083 g of lithium perchlorate and stir overnight at 80 ° C. After cooling, the solution is filtered and concentrated. The residue is purified by flash chromatography (silica gel, dichloromethane: methanol: 9: 1) resulting in 304 mg of the desired product. MS (El): m / z: 594 [M + H] + 51j) Title compound To a solution of 304 mg of the silyl ether (51i) in 1 ml of acetonitrile 0.62 ml of an aqueous solution is added at 0 ° C. N of hydrofluoric acid and stirred for 1 hour. Subsequently, the reaction mixture becomes alkaline with 1 ml of a 3 N sodium hydroxide solution and the solution is concentrated. The residue is purified by flash chromatography (silica gel, dichloromethane: methanol: 9: 1 + 1% ammonia) resulting in 112 mg of the desired product. MS (El): m / z: 480 [M + H] + Example 52: 6- ( { L- [2-Hydroxy-2- (3-methoxy-quinolin-5-yl) -ethyl] -3-hydroxymethyl-piperidin-4-ylamino} -methyl) -4H -benzo [1,4] oxazin-3 -one (racemate) Racemate The piperidine (6- { [3- (tert-butyl-dimethyl-silanyloxy-methyl) -piperidin-4-ylamido] -methyl} -4 H -benzo [1,4] oxazin-3-one) is prepared from analogously to steps 51g to 51h from the aldehyde (lj). The title compote is prepared as in example 51i to 51j from epoxide (14b) and 6-. { [3- (tert-butyl-dimethyl-silanyloxy-methyl) -piperidin-4-ylamino] -methyl} -4H-benzo [1,4] oxazin-3-one. MS (El): m / z: 493 [M + H] + Example 53: 1- (3-methoxy-quinolin-5-yl) -2-. { 4- [3- (thiophen-2-ylsulfanyl) -propyl] -piperazin-1-yl} -ethanol Racemate 53a) 2- (3-bromo-propylsulfane) -thiophene To a solution of 2.5 g of thiophene thiol and 2 g of sodium hydroxide in 10 ml of water is added 6.59 ml of 1,3-dibromopropane and heated during the night at 80 ° C. After cooling, the reaction mixture is diluted with ether, the phases are separated and the aqueous phase is extracted with ether. The combined organic phases are washed with a saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The residue is purified by flash chromatography (silica gel, hexane) resulting in 2.37 g of the desired product. MS (El): m / z: 238 [M + H] + 53b) 4- [3- (Thiophen-2-ylsulfanyl) -propyl] -piperazine-1-carboxylic acid terbutyl ester To a solution of 0.43 g of The terbutyl ester of piperazine-1-carboxylic acid and 0.5 g of the bromide (53a) in 5 ml of DMF are added 0.4 g of potassium carbonate and heated for 14 hours at 60 ° C. The solution is then concentrated and the residue is purified by flash chromatography (silica gel, dichloromethane: methanol: 9: 1) resulting in 500 mg of the desired product. MS (El): m / z: 343 [M + H] + 53c) 1- [3- (thiophen-2-ylsufanyl) -propyl] -piperazine A solution of 0.5 g of the protected piperazine (53b) in 5 ml of TFA is stirred for 20 minutes at room temperature. After concentrating the reaction mixture the residue is resuspended or redissolved, respectively, in a 1 N solution of 30 ml of sodium hydroxide and extracted with dichloromethane (30 ml, 3 times). The combined organic phases are dried over sodium sulfate, filtered and concentrated resulting in 346 mg of the desired product. i MS (El): m / z: 243 [M + H] + 53d) Title compound A a solution of 0.1 g of the epoxide (14b) and 0. 130 g of the piperazine (53c) in 5 ml of DMF are added 0.06 g of lithium perchlorate and 0.1 g of potassium carbonate and heated for 2 hours at 40 ° C. The solution is then concentrated and the residue is purified by flash chromatography (silica gel, dichloromethane: methanol: 19: 1) resulting in the desired product. MS (El): m / z: 444 [M + H] + Example 54: 6- (l-hydroxy-2 { 4- [2-hydroxy-2- (3-methoxy-quinolin-5-yl) -ethyl] -piperazin-1-yl}.-Ethyl) - 4H-benzo [1,4] oxazin-3-one (racemate) Racemato 54a) 4- [2-Hydroxy-2- (3-oxo-3,4-dihydro-2H-benzo [1,4] oxazin-6-yl) -ethyl] -piperazine-1-carboxylic acid benzyl ester a solution of 2.2 g of the benzyl ester of piperazine-1-carboxylic acid in 20 ml of ethanol and 10 ml of acetonitrile is added 2.25 g of 6- (2-chloro-acetyl) -4H-benzo [1,4] oxazin- 3-one and 1.67 ml of triethylamine and heated for 3 hours at 65 ° C. The solution is then concentrated and the residue is resuspended and redissolved, respectively, in 30 ml of methanol. After cooling to 0 ° C, 2 g of sodium borohydride are added in portions and stirred for 30 minutes. Then 20 ml of water are added and the solution is partially concentrated. The residue is extracted with ethyl acetate (100 ml, 3 times). The combined organic phases are washed with a saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The residue is purified by flash chromatography (silica gel, dichloromethane: methanol: 19: 1) resulting in 2 g of the desired product. MS (El): m / z: 412 [M + H] + 54b) 6- (1-hydroxy-2-piperazin-1-ylethyl) -4 H -benzo [1,4] oxazin-3-one To one solution of 3 g of the protected piperazine (54a) in 100 ml of acetic acid ethyl ester, 1.5 g of 10% palladium in charcoal are added. The reaction mixture is stirred overnight under an atmosphere of hydrogen gas and then filtered and concentrated resulting in 2 g of the desired product. MS (El): m / z: 278 [M + H] + 54c) Title compound The title compound is prepared as in Example 53d from the epoxide (14b) and the piperazine (54b). MS (El): m / z: 479 [M + H] + Example 55: 6- (l-hydroxy-2- { 4- [2-hydroxy-2- (3-methoxyquinolin-5-yl) -ethyl] -piperazin-1-yl} -ethyl) -4H -benzo [1,4] thiazin-3-one (racemate) racemate Piperazine (6- (l-hydroxy-2-piperazin-1-ylethyl) -4H-benzo [1,4] thiazin-3-one) is prepared analogously to steps 54a to 54b from 6- (2-chloroacetyl) -4H-benzo [1,4] thiazin-3-one. The title compound is prepared as in Example 54c from epoxide (14b) and 6- (1-hydroxy-2-piperazin-1-ylethyl) -4H-benzo [1,4] thiazin-3-one. MS (El): m / z: 495 [M + H] + Example 56: 2- { 4- [2- (2,3-dihydro-benzo [1,4] dioxin-6-yl) -2-hydroxyethyl] -piperazin-1-yl} -l- (3-methoxyquinolin-5-yl) -ethanol (enantiomer 1) racemate Piperazine (1- (2,3-dihydro-benzo [1,4] dioxin-6-yl) -2-piperazin-1-ylethanol) is prepared in a manner analogous to steps 54a and 54b from 2- chloro-l- (2,3-dihydro-benzo [1,4] dioxin-6-yl) -ethanone. The title compound is prepared as in Example 54c from epoxide (14b) and 1- (2,3-dihydro-benzo [1,4] dioxin-6-yl) -2-piperazin-1-ylethanol. MS (El): m / z: 466 [M + H] + Example 57: 5-. { 2- [4- (2,3-dihydro-benzo [1,4] dioxin-6-ylmethyl) -piperazin-1-yl] -ethoxy} -3-methoxyquinoline 57a) 3-methoxy-5- (4, 4, 5, 5-tetramethyl [1,3,2] -dioxaborolan-2-yl) -quinoline To a mixture of 6.14 g of bis (pinacolato) diborone, 1475 are added g of 1,1-bis (diphenylphosphino) ferrocene palladium (II) dichloride dichloromethane complex and 5.93 g of potassium acetate, a solution of 4.8 g of Ib in 145 ml of DMSO is added. The reaction mixture is stirred overnight at 80 ° C. After cooling to room temperature the reaction mixture is diluted with 300 ml of water and 300 ml of acetic acid ethyl ester. The phases are separated and the aqueous phase is extracted with ethyl acetate (300 ml, 2 times). The combined organic phases are washed with a saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The brown residue is purified by flash chromatography (silica gel, ethyl acetate: hexane: 1: 4) resulting in 4.65 g of the desired product. MS (El): m / z: 286 [M + H] + 57b) 3-methoxyquinolin-5-ol To an ice-cooled solution of 4.6 g of 57a in 110 ml of THF is added dropwise 13 ml of a solution of 3N sodium hydroxide. Subsequently, 5.6 ml of an aqueous solution of 30% hydrogen peroxide are added dropwise and the reaction mixture is stirred for 1 hour at 0 ° C. The reaction mixture is resuspended or redissolved, respectively in 100 ml of water and extracted once with 200 ml of acetic acid ethyl ester. The pH value of the aqueous phase is adjusted to 4 with a 1N solution of hydrochloric acid and subsequently the reaction mixture is extracted with ethyl acetate (100 ml, 3 times). The organic phases are combined, dried over sodium sulfate, filtered and concentrated. The residue is purified by flash chromatography (silica gel, dichloromethane-methanol: 29: 1) resulting in 2.82 g of the desired product. MS (El): m / z: 176 [M + H] + 57c) 4- (2-Hydroxyethyl) -piperazine-1-carboxylic acid benzyl ester To a solution of 13 ml of hydroxyethylpiperazine in 200 ml of acetone are added under vigorous stirring 254 ml of a 10% sodium hydrogen carbonate solution. Subsequently, the reaction mixture is cooled to 0 ° C and 17.92 ml of benzyl chloroformate are added dropwise. The reaction mixture is stirred for 4 hours at room temperature. After separating the acetone under vacuum, the aqueous phase is extracted with ethyl acetate (250 ml, 3 times). The combined organic phases are washed once with a saturated sodium chloride solution, dried over sodium sulfate, filtered, concentrated, resulting in 28.2 g of the desired product. MS (El): m / z: 265 [M + H] + 57d) 4- (2-methanesulfonyloxyethyl) -piperazine-1-carboxylic acid benzyl ester A 2.0 g solution of 57c in 10 ml of dichloromethane is cooled to 0 ° C and mixed with 1.27 ml of triethylamine and 706 μl of methanesulfonyl chloride. The solution is warmed to room temperature and then stirred for 30 minutes. The reaction mixture is diluted with dichloromethane and then subsequently washed with a saturated solution of sodium hydrogen carbonate., water and a saturated solution of sodium chloride. By concentrating the desired product, 2.57 g are obtained. MS (El): m / z: 343 [M + H] + 57e) 4- [2- (3-Methoxyquinolin-5-yloxy) -ethyl] -piperazine-1-carboxylic acid benzyl ester. 350 mg of the Compound (57b) in 2 ml of DMF and mix at room temperature with 87 mg of sodium hydride. After stirring for 10 minutes, a solution of 684 mg of the compound (57b) in 2 ml of DMF is slowly added dropwise. The reaction mixture is stirred overnight at room temperature, and then resuspended or redissolved, respectively, in water and extracted with ethyl acetate (5 ml, 3 times). The combined organic phases are washed several times with water, dried over sodium sulfate, filtered, concentrated, whereby 320 mg of the desired product are obtained. MS (El): m / z: 422 [M + H] + 57f) 3-methoxy-5- (2-piperazin-1-ylethoxy) -quinoline To a solution of 250 mg of the compound (57e) in 25 ml of acetic acid ethyl ester and 25 ml of methanol, 50 mg of palladium 10% are added in charcoal and stirred for 4 hours under an atmosphere of hydrogen gas. The solution is filtered, concentrated and the desired product is obtained as a result. MS (El): m / z: 288 [M + H] + 57g) Title compound The title compound is prepared as in the example lk from 3-methoxy-5- (2-piperazin-1-ylethoxy) -quinoline (57f) and 2,3-dihydro-benzo [1,4] dioxin-6-carbaldehyde with a yield of 66%. MS (El): m / z: 436 [M + H] + Example 58: 6- { 4- [2- (3-methoxyquinolin-5-yloxy) -ethyl] -piperazin-1-ylmethyl} -4H-benzo [1,4] oxazin-3-one The title compound is prepared as in Example 57g from the aldehyde (Ij) in a yield of 71%. MS (El): m / z: 449 [M + H] + Example 59: 6- { 4- [2- (3-methoxyquinolin-5-yloxy) -ethyl] -piperazin-1-ylmethyl} -4H-benzo [1,4] thiazin-3-one The title compound is prepared as in Example 57g from aldehyde (4b) in 56% yield. MS (El): m / z: 465 [M + H] + Example 60: 6- { 4- [2- (3-methoxyquinolin-5-yloxy) -ethyl] piperazin-1-ylmethyl} -4H-pir gone [3, 2-b] [1,4] thiazin-3-one The title compound is prepared as in Example 57g from the aldehyde (2h) in 80% yield. MS (El): m / z: 466 [M + H] + Example 61: 5- (2- { 4- [(E) -3- (2,5-difluorophenyl) -allyl] piperazine-1- il.}. ethoxy) -3-methoxyquinoline The title compound is prepared as in Example 57g from (E) -3- (2,5-difluorophenyl) -propenal (this compound is prepared according to WO 2004/087 647). MS (El): m / z: 440 [M + H] + Example 62: 3-methoxy-5- [2- (4-naphthalen-2-ylmethylpiperazin-1-yl) -ethoxy] -quinoline The title compound is prepared as in Example 57g from 2-carbaldehyde naphthalene.

MS (El): m / z: 428 [M + H] Example 63: 3-methoxy-5- (2- { 4- [2- (thiophen-2-ylsulphanyl) ethyl] -piperazin-1-yl} -ethoxy) -quinoline 63a) 2- (2-bromoethylsulfanyl) -thiophene The compound is prepared as in example 53a from 1,2-dibromoethane. MS (El): m / z: 224 [M + H] + 63 b) Title compound The compound is prepared as in Example 53b from 3-methoxy-5- (2-piperazin-1-ylethoxy) -quinoline. (57f) and 2- (2-bromoethylsulfanyl) -thiophene (63a) with a yield of 86%. MS (El): m / z: 430 [M + H] + Example 64: 6- { 4 - [2 - (3-methoxyquinolin-5-yloxy) -ethyl] -piperazin-1-carbonyl} -4H-benzo [1, 4] .thiazin-3 -one The title compound is prepared as in Example 33 from 3-methoxy-5- (2-piperazin-1-ylethoxy) -quinoline (57f) and 3-oxo-3, 4-dihydro-2H-benzo [ 1,4] thiazine-6-carboxylic acid MS (El): m / z: 479 [M + H] +.

Example 65: 6- { 4- [2- (3-methoxyquinolin-5-yloxy) -ethyl] -piperazine-1-carbonyl} -4H-benzo [1,4] oxazin-3-one The title compound is prepared as in Example 33 from 3-methoxy-5- (2-piperazin-1-ylethoxy) -quinoline (57f) and 3-oxo-3, 4-dihydro-2H-benzo [ 1,4] oxazine-6-carboxylic acid MS (El): m / z: 463 [M + H] \ Example 66: 6- { 4- [2- (3-methoxyquinolin-5-yloxy) -ethyl] piperazin-1-sulphonyl} -4H-benzo [1,4] thiazin-3-one The title compound is prepared as in example 37 from 3-methoxy-5- (2-piperazin-1-ylethoxy) -quinoline (57f) and 3-oxo-3,4-dihydro-2H-benzoyl chloride [1,4] thiazine-6-sulfonyl EM (El): m / z: 515 [M + H] \ Example 67: 6- { 4- [2- (3-methoxyquinolin-5-yloxo) -ethyl] -piperazin-1-sulfonyl} -4H-benzo [1,4] oxazin-3-one The title compound is prepared as in example 37 from 3-methoxy-5- (2-piperazin-1-ylethoxy) -quinoline (57f) and 3 -oxo-3,4-dihydro-2H-benzoyl chloride [1,4] oxazin-6-sulfonyl EM (El): m / z: 499 [M + H] +.

Example 68: 2- { 4- [2- (2,3-dihydrobenzene [1,4] dioxin-6-yl) -ethyl] -piperazin-1-yl} -l- (3-methoxyquinolin-5-yl) -ethanol (enantiomer 1) Enantiomer 1 68a) 6-vinyl-2,3-dihydrobenzo [1,4] dioxin A solution of 13.2 g of methyltriphenylphosphonium bromide in 120 ml of THF is cooled to -78 ° C and then butyllithium (15 ml) is added. , 2.5M solution in hexane) and subsequently stirred for 15 minutes at -78 ° C and then further stirred for 45 minutes at 0 ° C. After cooling to -78 ° C, a solution of 5 g of 2,3-dihydrobenzo [1,4] dioxin-6-carbaldehyde in 20 ml of THF is added, warming to room temperature and stirring for 2 hours. The reaction mixture is washed with ethyl acetate (100 ml, 3 times) and the combined organic phases are washed with a saturated solution of sodium chloride, dried over sodium sulfate., they filter and concentrate. The residue is purified by flash chromatography (silica gel, ethyl acetate: hexane: 1: 6) to obtain 3.9 g of the desired product. MS (El): m / z: 163 [M + H] +. 68b) 2- (2,3-dihydrobenzo [1,4] dioxin-6-yl) -ethanol To a solution of 5 g of the vinyl compound (68a) in 100 ml of THF 2.2 g of 9-BBN are added and Stir for 16 hours at room temperature. Subsequently the reaction mixture is cooled to 0 ° C and 20 ml of ethanol, 110 ml of a 3 N sodium hydroxide solution and 110 ml of a 30% hydrogen peroxide solution are added. The reaction mixture is stirred for 1 hour at room temperature and then mixed with 120 ml of a 10% sodium sulfite solution and stirred for an additional 30 minutes. The phases are separated and the aqueous phase is extracted with ethyl acetate (100 ml, 2 times). The combined organic phases are washed with a saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The residue is purified by flash chromatography (silica gel, acetic acid ethyl ester: hexane: 2: 1) to obtain 3.75 g of the desired product. MS (El): m / z: 181 [M + H] +. 68c) 2- (2, 3-Dihydrobenzo [1,4] dioxin-6-yl) -ethyl ester of toluene-4-sulfonic acid To a solution of 3.55 g of the alcohol (68 g) in 70 ml of dichloromethane are added at 0 ° C 4.2 g of DMAP and 4.13 g of tosyl chloride. The solution is stirred for 20 minutes at 0 ° C and then warmed to room temperature. After 2 hours the solution is concentrated and the residue is purified by flash chromatography (silica gel, ethyl acetate: hexane 1: 3), whereby 3.23 g of the desired product are obtained. MS (El): m / z: 335 [M + H] +. 68d) 4- [2- (2,3-Dihydrobenzo [1,4] dioxin-6-yl) -ethyl] -piperazine-1-carboxylic acid benzyl ester To a solution of 0.7 g of tosylate (68c) in 10 ml of DMF are added 0.49 g of piperazine-1-carboxylic acid benzyl ester and 1 ml of triethylamine. The reaction mixture is heated for 16 hours at 60 ° C and then concentrated. The residue is purified by flash chromatography (silica gel, acetic acid ethyl ester: hexane: 2: 1) resulting in 0.6 g of the desired product. MS (El): m / z: 383 [M + H] J 68e) 1- [2- (2,3-dihydrobenzo [1,4] dioxin-6-yl) -ethyl] -piperazine To a solution of 0.180 g of piperazine protected (68d) in 5 ml of acetic acid ethyl ester, 0.18 g of 10% palladium in charcoal is added and hydrogenated at room temperature for 1 hour under an atmosphere of hydrogen gas. The reaction mixture is filtered, the filtrate is concentrated resulting in 0.13 g of the desired product. MS- (El): m / z: 249 [M + H] + 68f) Title compound A a solution of 0.1 g of the epoxide (7a, enantiomer 1) and 0.13 g of the piperazine (68e) in 2 ml of DMF , 0.06 g of lithium perchlorate are added and the reaction mixture is heated for 4 hours at 60 ° C. The solution is then concentrated and the residue is purified by flash chromatography (silica gel, dichloromethane: methanol: 19: 1) resulting in the desired product. MS (El): m / z: 450 [M + H] +.

Example 69: 6- (2- { 4- [2-hydroxy-2- (3-methoxyquinolin-5-yl) -ethyl] -piperazin-1-yl}.-Ethyl) -4H-benzo [l , 4] oxazin-3-one (enantiomer 1) The piperazine (6- (2-piperazin-1-ylethyl) -4H-benzo [1,4] oxazin-3-one) is prepared analogously to the reaction steps 68a to 68e from the aldehyde (lj). The title compound is prepared as in Example 68f from epoxide (7a) and 1- (2,3-dihydrobenzo [1,4] dioxin-6-yl) -2-piperazin-1-ylethanol. MS (El): m / z: 463 [M + H] +.

Example 70: 2- [4- (2-Benzo [1,3] dioxol-5-yl-ethyl) -piperazin-1-yl] -1- (3-methoxyquinolin-5-yl) -ethanol (enantiomer 1) Enantiomer 1 Piperazine (1- (2-benzo [1,3] dioxol-5-yl-ethyl) -piperazine) is prepared analogously to reaction steps 68a to 68e from benzo [1, 3] dioxol -5-carbaldehyde. The title compound is prepared as in Example 68f from the epoxide (7a) and l- (2-benzo [1,3] dioxol-5-yl) -piperazine. MS (El): m / z: 436 [M + H] + Example 71: L-cyclopropyl-6-fluoro-7 - acid. { 4- [2-hydroxy-2- (3-methoxyquinolin-5-yl) -ethyl] -piperazin-1-yl} -4-oxo-l, 4-dihydroquinolin-3-carboxylic acid Racemate 50 mg of the epoxide (14a) and 91.4 mg of ciprofloxacin are suspended in 0.2 ml of DMF and 34.3 mg of potassium carbonate is added thereto. The reaction mixture is stirred overnight at 100 ° C. After cooling to room temperature, the reaction mixture is concentrated. The residue is purified by flash chromatography (silica gel, dichloromethane: methanol: 9: 1). The concentrated fractions are recrystallized from ether: dichloromethane. MS (El): m / z: 533 [M + H] + Example 72: L-cyclopropyl-6-fluoro-7 - (4. {1 - l - [2-hydroxy-2- (3-methoxy-quinolin-5-yl) -ethyl] -piperidin-4-yl} - acid. piperazin-1-yl) -4 -oxo-1,4-dihydroquinoline-3-carboxylic acid (racemate) Racemate 72a) 4- (4-Benzylpiperazin-1-yl) -piperidin-1-carboxylic acid terbutyl ester 5.0 g of N-ter-Boc-4-piperidinone and 4.43 g of 1-benzylpiperazine in 60 ml of methanol are dissolved. and mixed with 1.58 g of acetic acid. Mix . it is stirred for 7 hours at room temperature. Subsequently, 1.89 g of sodium cyanoborohydride and 20 ml of methanol are added. The mixture is stirred overnight at room temperature. After the addition of 250 ml of water, the mixture is extracted with ethyl ether of acetic acid (250 ml, 4 times). The combined organic phases are dried over sodium sulfate, filtered and concentrated. The residue is purified by HPLC resulting in 4.52 g of the desired product. MS (El): m / z: 360 [M + H] + 72b) 4-Piperazin-1-yl-piperidine-1-carboxylic acid terbutyl ester To a solution of 2.0 g of protected piperazine (72a) in 20 ml of methanol is added 0.5 g of 10% palladium hydroxide and stirred at room temperature for 48 hours under an atmosphere of gaseous hydrogen. The reaction mixture is filtered, the filtrate is concentrated and the residue is purified by flash chromatography (silica gel, dichloromethane: methanol: ammonia: 19: 0.9: 0.1, then 9: 0.9: 0.1, then 4: 0.9: 0.1, then 3: 1.8: 0.2) which generates 1.0 mg of the desired product. MS (El): m / z: 270 [M + H] + 72c) Terbutyl ester of 4 - acid. { 4- [2-hydroxy-2- (3-methoxyquinolin-5-yl) -ethyl] -piperazin-1-yl} -piperidine-1-carboxylic acid 0.39 g of the epoxide (14b) are dissolved, 0.29 g of piperazine (72b), 0.29 g of potassium carbonate and 0.12 g of lithium perchlorate in 4 ml of dry DMF and stirred under an atmosphere of nitrogen gas for 24 hours at 100 ° C. The mixture is cooled to room temperature and concentrated. The residue is purified by flash chromatography (silica gel, first of all, dichloromethane and then dichloromethane: methanol: ammonia: 19: 0.9: 0.1, then 9: 09: 0.1) resulting in 472 mg of the desired product. MS (El): m / z: 471 [M + H] + 72d) 1- (3-methoxyquinolin-5-yl) -2- (4-piperidin-4-yl-piperazin-1-yl) -ethanol A an ice-cooled solution of 317 mg of the Boc-piperidine (72c) in 10 ml of dichloromethane is added dropwise 1.5 ml of TFA. The mixture is then stirred for 15 minutes at 0 ° C and then warmed to room temperature within the next 45 minutes. The mixture is concentrated, adjusted to an alkaline pH value with ammonia and subsequently extracted with dichloromethane: methanol (9: 1) (25 ml, 5 times). The combined organic phases are concentrated, resulting in 93 mg of the desired product. MS (El): m / z: 371 [M + H] + 72e) Title compound 80 mg of the amine (72d) and 101 mg of a 7-chloro-l-cyclopropyl-6-fluoro acid complex are dissolved -1,4-dihydro-4-oxo-3-quinolinecarboxylic acid and boron diacetate in 5 ml of NMP and 0.3 ml of N-ethyl-diisopropylamine are added dropwise. The mixture is stirred for 24 hours at 80 ° C. After cooling to room temperature the reaction mixture is concentrated. The residue is stirred for 30 minutes at 0 ° C in a 4 N solution of hydrochloric acid in 10 ml of methanol and then once more for 1 hour at room temperature. The reaction mixture is combined with 50 ml of acetic acid ethyl ester. The precipitate is filtered, washed and dried. 50 mg of the desired product are obtained. MS (El): m / z: 616 [M + H] + The maximum inhibitory concentration (maximale Hemm-Konzentration; MHK) (μg / ml) of the substances according to the examples against different organisms was determined: A. ba umannii ATCC 19606, E. cloacae ATCC 23355, E. coli ATCC 25922, K. pneumoniae ATCC 27736, P. mirabilis ATCC 29906, P. aeruginosa ATCC 27853, S. mal tophilia ATCC 13637, S. a ureus ATCC 43300, S. epidermidis ATCC 14990, S. haemolyticus ATCC 29970, E. faecalis ATCC 29212 and E. faecium ATCC 19434. Substances according to Examples 1-12, 14-15, 17-20, 22-26, 28-53 and 56-71 have a maximum inhibitory concentration (MHK) of less than or equal to 4 μg / ml against at least two of the organisms mentioned above.

Claims (13)

2. Compounds of the formula (I): wherein the residue R1 is a hydrogen atom, a halogen atom, a hydroxy, an amino, a cyano, a nitro, a thiol, an alkyl of 1 to 6 carbon atoms, an alkenyl of 2 to 6 carbon atoms , an alkynyl of 2 to 6 carbon atoms, a heteroalkyl, an alkyloxy, a heteroalkyloxy, a cycloalkyloxy, an alkylcycloalkyloxy, a heterocycloalkyloxy or a heteroalkylcycloalkyloxy group; the residue R2 is a hydrogen atom, a halogen atom, a hydroxy, an amino, a cyano, an alkyl of 1 to 6 carbon atoms, an alkenyl of 2 to 6 carbon atoms, an alkynyl of 2 to 6 atoms of carbon or a heteroalkyl group; the residue R3 is a group of the following formula: wherein U and V independently from each other are nitrogen atoms or groups of the formula CH or CR6; the R4 residues independently of one another are a halogen atom, a hydroxy group, an amino, a cyano, a nitro or a thiol group, an alkyl, alkenyl, alkynyl or a heteroalkyl group; n is equal to 0, 1 or 2; the residue Rs is an alkyl, alkenyl, alkynyl, heteroalkyl, aryl, heteroaryl, cycloalkyl, alkylcycloalkyl, heteroalkylcycloalkyl, heterocycloalkyl, aralkyl or heteroaralkyl group; the residues Rd independently of each other are a halogen atom, a hydroxy, alkyl, alkenyl, alkynyl or heteroalkyl group; A is selected from the following groups: -CR10 (OR11) CR12R13-, -CR8R9CR10 (OR11) -, -OCR8R9CR12R13-, -CR8R9CR12R130-, -CR8R9S02-, -S02CR8R9-, -CR8R9NR7-, -NR7CR8R9-, -CR8R90- , -0CR8R9-, -CR8R9S-, -SCR8R9-, -NR7C (= 0) -, -C (= 0) NR7- and -CR8R9CR12R13-; the residue R7 is a hydrogen atom, a trifluoromethyl group, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkoxycarbonyl of 1 to 6 carbon atoms, alkylcarbonyl of 1 to 6 carbon atoms or carbonylamino , wherein the amino group of the carbonylamino group, if applicable, may be substituted by an alkoxycarbonyl group of 1 to 6 carbon atoms, alkylcarbonyl of 1 to 6 carbon atoms, alkenyloxycarbonyl of 2 to 6 carbon atoms, alkenylcarbonyl of 2 to 6 carbon atoms, an alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms and, if applicable, may be further substituted by an alkyl group of 1 to 6 carbon atoms or alkenyl of 2 to 6 carbon atoms; the residues R8, R9, R10, R12 and R13 independently of each other are a hydrogen atom, a halogen atom, an azide, a trifluoromethyl, hydroxy, amino, alkyloxy of 1 to 6 carbon atoms, alkylthio of 1 to 6 atoms of carbon, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkoxycarbonyl of 1 to 6 carbon atoms, alkenyloxycarbonyl of 2 to 6 carbon atoms, alkylsulfonyl of 1 to 6 carbon atoms, alkenylsulfonyl of 2 to 6 carbon atoms or a sulfonylamino group, wherein the amino group of the sulfonylamino group, if applicable, may be substituted by an alkyl group of 1 to 6 carbon atoms or phenyl; the residue R11 is a hydrogen atom, a trifluoromethyl group, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkoxycarbonyl of 1 to 6 carbon atoms, alkylcarbonyl of 1 to 6 carbon atoms or carbonylamino, wherein the amino group of the carbonylamino group, if applicable, may be substituted by an alkoxycarbonyl group of 1 to 6 carbon atoms, alkylcarbonyl of 1 to 6 carbon atoms, alkenyloxycarbonyl of 2 to 6 carbon atoms, alkenylcarbonyl of 2 to 6 carbon atoms, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms and, if applicable, may be further substituted by an alkyl group of 1 to 6 carbon atoms or alkenyl of 2 to 6 carbon atoms. to 6 carbon atoms; or a pharmaceutically acceptable salt, solvate, hydrate or a pharmacologically acceptable formulation thereof. 2. Compounds as described in claim 1, wherein A is selected from the following groups: -CH (OH) CH2-, -CH2CH (OH) -, -OCH2CH2-, -CH2CH20-, -CH2S02-, -S02CH2 -, -CH2N (alkyl of 1 to 4 carbon atoms) -, -N (alkyl of 1 to 4 carbon atoms) CH2-, -CH2NH-, -NHCH2-, -CH20-, -0CH2-, -CH2S- , -SCH2-, -N (C 1 -C 4 alkyl) C (= 0) -, -C (= 0) N (C 1 -C 4 alkyl) -, -NHC (= 0) - , -C (= 0) NH- or -CH2CH2-.
3. 3. Compounds as described in claim 1 or 2, wherein A is a group of the formula-CH (0H) CH2- or -0CH2CH2-.
4. 4. Compounds as described in claim 1, 2 or 3, wherein the residue R1 is a methoxy group.
5. 5. Compounds as described in claim 1, 2, 3 or 4, wherein the residue R2 is a hydrogen atom or a halogen atom.
6. 6. Compounds as described in claim 1, 2, 3, 4 or 5, wherein the residue R5 is a group of formula -BY, wherein B is a bond, an alkylene group, an alkenylene, an alkynylene, a group -NH-, -NHS02-, -S02-, -C (= 0), a heteroalkylene group or a heterocycloalkylene group and Y is an aryl, heteroaryl, aralkyl, heteroaralkyl, cycloalkyl, heterocycloalkyl, alkylcycloalkyl, heteroalkylcycloalkyl, heteroarylheterocycloalkyl or an arylheterocycloalkyl.
7. 7. Compounds as described in claim 6, wherein B is a group of the formula -NH -NHCH, CH2NH- -NHCH, CH, -CH2CH2NH- -NHCH2CH2CH2- -CH2CH2CH2NH- -CH, -CH2CH2- -CH2CH2CH2-, -NHC (= 0) -C (= 0) NH- • CH (OH) -CH2CH (OH) -CH (0H) CH, -NHSO, -S02NH-, -SO. -C (= S) NH-, -NHC (= S) -C (= NOH) - -CH2C (= NOH) -, -C (= N0H) CH2-, -C (= 0) -, -C ( = 0) -C (= 0) -CH2C (= 0) -, -C (= 0) CH2-, -N (alkyl of 1 to 4 carbon atoms) CH2-, -CH2N (alkyl of 1 to 4 atoms carbon) - or a piperazine group.
8. 8. Compounds as described in claim 6 or 7, wherein Y has one of the following structures:
9. 9. Compounds as described in claims 1, 2, 3, 4, 5, 6, 7 or 8, wherein the residue R3 is selected from the following groups:
10. 10. Compounds as described in claim 9, wherein the residues R4, independently of each other, are a halogen atom, a hydroxy group, cyano, alkyl of 1 to 4 carbon atoms or heteroalkyl of 1 to 4 carbon atoms.
11. 11. Compounds as described in claim 9, wherein the R6 residues, independently of each other, are a halogen atom, a hydroxy group, alkyl of 1 to 4 carbon atoms or heteroalkyl of 1 to 4 carbon atoms.
12. 12. Pharmaceutical compositions containing a compound as described in claims 1 to 11 as an active ingredient and optionally carriers or adjuvants.
13. 13. Use of a compound or a pharmaceutical composition as described in claims 1 to 12, for the treatment of bacterial infections.