DE10159453A1 - Use of 1-phenyl-oxazolidin-2-one compounds as a protease - Google Patents

Abstract

The invention relates to the use of the 1-phenyl-oxazolidine-2-one compounds of formula (I), wherein R and R<1> are defined as in patent claim 1, the stereoisomers and physiologically acceptable salts or solvates thereof as protease M inhibitors and to novel 1-phenyl-oxazolidine-2-one compounds and the use thereof.

Description

The invention relates to the use of 1-phenyl-oxazolidin-2-one Compounds of formula I as protease M inhibitors and new 1- Phenyl-oxazolidin-2-one compounds and their use.

Compounds of formula I are:


wherein
R unsubstituted or single, double or triple by A, Ar, (CH ₂ ) _n Ar, OR ² , OAr, OCF ₃ , OCOR ³ , CF ₃ , N (R ² ) ₂ , NHAr, Hal, NO ₂ , CN, (CH ₂ ) _n COOR ² , (CH ₂ ) _n COOAr, (CH ₂ ) _n CONHA, (CH ₂ ) _n CONH cycloalkyl, (CH ₂ ) _n CONA ₂ , (CH ₂ ) _n CONH (CH ₂ ) _m Ar, COR ² , COAr, SA, S (= O) A, SO ₂ A, SAr, S (= O) Ar, SO ₂ Ar, NHCOA, NHCOAr, NHSO ₂ A, NHSO ₂ Ar NHSO ₂ Ar and / or


is substituted phenyl, naphthyl, or Het ¹ ,
R ¹ H ₂ NC (= NH) - is
R ² H, A phenyl or benzyl
Ar unsubstituted or single, double or triple by A, OR ² , OCF ₃ , CF ₃ , N (R ² ) ₂ , Hal, NO ₂ , CN, (CH ₂ ) _n COOR ² , CON (R ² ) ₂ , COR ² , SA, S (= O) A, SO ₂ A, NHCOA, substituted cycloalkyl, phenyl, naphthyl, indanyl or Het ² ,
Het ^{1 is} an aromatic mono- or dinuclear heterocycle with 1 to 4 N, O and / or S atoms,
Het ^{2 is} an aromatic mono- or dinuclear heterocycle with 1 to 4 N, O and / or S atoms,
A alkyl having 1 to 8 carbon atoms,
Hal F, Cl, Br, I,
m is 0, 1, 2, or 3
n is 0, 1, 2, 3 or 4
their stereoisomers and / or their physiologically acceptable salts or solvates.

Compounds of the formula I are known in part from EP 0 741 133 A1, EP 0 710 657 B1 and EP 0 645 376 B1. According to the documents mentioned, the compounds act as integrin inhibitors, in particular inhibiting interactions of the β ₃ and β ₅ integrin receptors, and here in particular α _V β ₃ , α _V β ₅ and α _IIb β ₃ receptors, with their ligands. In particular, they inhibit the binding of fibrinogen, fibronectin and von Willebrand factor to the fibrinogen receptor of platelets (glycoprotein IIb / IIIa) as well as the binding of the same and other adhesive proteins, such as vitronectin, collagen and laminin, to the corresponding receptors on the Surface of different cell types and thus influence cell-cell and cell-matrix interactions, inhibit or prevent vascular formation and thus show an antiangiogenic effect. It has therefore been proposed to use the compounds for the treatment of thromboses, apoplexy, myocardial infarction, angina pectoris, osteolytic diseases, in particular osteoporosis and restenosis after angioplasty, ischemia, inflammation, arteriosclerosis, acute kidney failure and as an anti-tumor agent. The use of the compounds as antiseptics is also described.

Surprisingly, it has now been found that the above Compounds also inhibit protease M. Protease M is one Serine protease found in various tumor tissues and cell lines is expressed (primary breast, ovary, and pancreatic tumors, as well as breast and intestinal tract tumor cell lines; Anisowicz A. et al., Molecular Medicine, 624 ff. (1996), Yamashiro, K. et al. Biochim. Biophys. Acta, 1350, 11 ff. (1997)). Overexpression of, in particular, was found in ovarian tumors Protease M shown and with the invasive nature and their ability to Growth associated (Tanimoto H. et al., Tumour-Biol., 22, 11 ff. (2001)). Protease M is also considered a biomarker for ovarian tumors (Diamandis E.P. et al. Clin. Biochem. 33, 579 ff. (2000)). Protease M has also been demonstrated in the human brain and could be due to neurogenerative diseases such as Alzheimer's and Parkinson's disease may be involved (Little, S.P. et al. JBC 272, 2513 ff. (1997)). In Alzheimer's disease, proteinase M was found in elevated concentrations proven and proposed as a biomarker for this disease (Diamandis E.P. et al., Clin. Biochem. 33, 663 ff. (2000)).

The compounds can inhibit the enzymatic activity for example, according to that of Yamashiro K. et al. described method be carried out (Yamashiro K. et al., Biochimica et Biophysica Acta, 1350, 11 ff. (1997).

The invention relates to the use of the compounds of Formula I for inhibiting protease M.

Another object of the invention is the use of the compounds of formula I for the manufacture of a medicament for therapy and / or Prophylaxis of diseases with an increased expression of the Protease M go hand in hand.

Examples of diseases associated with increased expression of protease M go hand in hand and in which the compounds of formula I can be used according to the invention are certain Tumor diseases such as primary breast, ovary, and pancreatic tumors and neurodegenerative diseases such as Alzheimer's and Morbus Parkinson.

The compounds of formula I have at least one chiral center and can therefore occur in several stereoisomeric forms. All these forms (e.g. D and L forms) and their mixtures (e.g. the DL- Shapes) are included in the formula.

In the compounds according to claim 1, so-called prodrug Derivatives included, i.e. H. with z. B. alkyl or acyl groups, sugars or oligopeptides modified compounds of formula I, which in Organism quickly to the active compounds of the invention be split.

Furthermore, free amino groups or free hydroxyl groups can be used as Substituents of compounds of formula I with corresponding Protecting groups.

Solvates of the compounds of the formula I include additions of inert solvent molecules to the compounds of formula I. understood that due to their mutual attraction form. Solvates are e.g. B. mono- or dihydrates or Addition compounds with alcohols, such as. B. with methanol or ethanol.

For the entire invention applies that all residues, the multiple occur, such as B. A, may be the same or different, d. H. are independent of each other.

In the above formulas, A means alkyl, is linear or branched, and has 1 to 8, preferably 1, 2, 3, 4, 5 or 6 carbon atoms. A is preferably methyl, furthermore ethyl, n-propyl, isopropyl, n-butyl, sec-butyl or tert-butyl, furthermore also pentyl, 1-, 2- or 3-methylbutyl, 1,1-, 1,2 - or 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1-, 2-, 3- or 4-methylpentyl, 1,1-, 1,2-, 1,3-, 2,2-, 2,3 - or 3,3-dimethylbutyl, 1- or 2-ethylbutyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, 1,1,2- or 1,2,2-trimethylpropyl, heptyl or octyl. Further preferred embodiments of A are the alkyl groups mentioned, which, however, can be substituted one or more times by Hal or NO ₂ , preferably trifluoromethyl, 2,2,2-trifluoroethyl or 2-nitroethyl, or alkyl groups whose carbon chain is interrupted by -O- can be, preferably -CH ₂ -O-CH ₃ , -CH ₂ -O-CH ₂ -CH ₃ or -CH ₂ -CH ₂ -O-CH ₃ .

A is particularly preferably methyl or ethyl.

Ar is unsubstituted or single, double or triple by A, OR ² , OCF ₃ , CF ₃ , N (R ² ) ₂ , Hal, NO ₂ , CN, (CH ₂ ) _n COOR ² , CON (R ² ) ₂ , COR ² , SA, S (= O) A, SO ₂ A, NHCOA, substituted cycloalkyl, phenyl, naphthyl, indanyl or Het ² . Unsubstituted, preferably - as indicated - monosubstituted phenyl, naphthy, indanyl or Het ^{2 is} preferred. Naphthyl, phenyl, o-, m- or p-tolyl, o-, m- or p- ethylphenyl, o-, m- or p-propylphenyl, o-, m- or p-isopropylphenyl, o- , m- or p-tert-butylphenyl, o-, m- or p-cyanophenyl, o-, m- or p-methoxyphenyl, o-, m- or p-ethoxyphenyl, o-, m- or p-fluorophenyl , o-, m- or p-bromophenyl, o-, m- or p-chlorophenyl, o-, m- or p-methylthiophenyl, o-, m- or p-methylsulfinylphenyl, o-, m- or p-methylsulfonylphenyl , o-, m- or p-aminophenyl, o-, m- or p-methylaminophenyl, o-, m- or p-dimethylaminophenyl, o-, m- or p-nitrophenyl, o-, m- or p-acetylphenyl , o-, m- or p-methoxycarbonylphenyl, o-, m- or p-aminocarbonylphenyl, more preferably 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3, 5-difluorophenyl, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-dichlorophenyl, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-dibromophenyl, 2-chloro-3-methyl, 2-chloro-4-methyl, 2-chloro-5-methyl, 2-chloro-6-methyl -, 2-methyl-3-chloro, 2-methyl-4-chloro, 2-methyl-5-chloro, 2-methyl -6-chloro, 3-chloro-4-methyl-, 3-chloro-5-methyl- or 3-methyl-4-chlorophenyl, 2-bromo-3-methyl-, 2-bromo-4-methyl-, 2-bromo-5-methyl, 2-bromo-6-methyl, 2-methyl-3-bromo, 2-methyl-4-bromo, 2-methyl-5-bromo, 2-methyl-6 -bromo-, 3-bromo-4-methyl-, 3-bromo-5-methyl- or 3-methyl-4-bromophenyl, 2,4- or 2,5-dinitrophenyl, 2,5- or 3,4- Dimethoxyphenyl, 2,3,4-, 2,3,5-, 2,3,6-, 2,4,6- or 3,4,5-trichlorophenyl, 2,4,6-tri-tert-butylphenyl , 2,5-dimethylphenyl, p-iodophenyl, 4-fluoro-3-chlorophenyl, 4-fluoro-3,5-dimethylphenyl, 2-fluoro-4-bromophenyl, 2,5-difluoro-4-bromophenyl, 2,4 - Dichloro-5-methylphenyl, 3-bromo-6-methoxyphenyl, 3-chloro-6-methoxyphenyl, 2-methoxy-5-methylphenyl, 2,4,6-triisopropylphenyl.

Cycloalkyl has 3 to 15 carbon atoms and is preferably cyclopropyl, Cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl, particularly preferably cyclohexyl. Cycloalkyl also means mono- or bicyclic terpenes, preferably p-menthan, menthol, pinan, bornan or camphor, including any known stereoisomeric form is or adamantyl. For camphor this means both L-camphor and also D-camphor.

Hal is preferably F, Cl, Br or I. Hal F is particularly preferred or Cl.

Het ¹ is a heterocycle having 1, 2, 3 and / or 4 N, O and / or S atoms, preferably 1-, 2- or 3-pyrrolyl, 1-, 2-, 4- or 5-imidazolyl , 1-, 3-, 4- or 5-pyrazolyl, 2-, 3- or 4-pyridyl, 2-, 4-, 5- or 6-pyrimidinyl, further preferably 1,2,3-triazol-1-, -4- or -5-yl, 1,2,4-triazol-1-, -3- or 5-yl, 1- or 5-tetrazolyl, 3- or 4-pyridazinyl, pyrazinyl, 1-, 2-, 3-, 4-, 5-, 6- or 7-indolyl, indan-1- or -2-yl, 1-, 2-, 4- or 5-benzimidazolyl, 1-, 3-, 4-, 5- , 6- or 7-benzopyrazolyl, 2-, 3-, 4-, 5-, 6-, 7- or 8-quinolinyl, 1-, 3- 4-, 5-, 6-, 7- or 8-isoquinolinyl , 3-, 4-, 5-, 6-, 7- or 8-cinnolinyl, 2-, 4-, 5-, 6-, 7- or 8-quinazolinyl, 1H-imidazo [4,5-b] pyridine -2-yl or 1,8-naphthyridin-7-yl. 4-Pyridyl is particularly preferred.

The heterocyclic radicals can also be partially or completely hydrogenated. Het ¹ can, for. B. also mean 2,3-dihydro-1-, -2-, -3-, -4- or - 5-pyrrolyl, 2,5-dihydro-1-, -2-, -3-, -4- or -5-pyrrolyl, 1-, 2- or 3-pyrrolidinyl, tetrahydro-1-, -2- or -4-imidazolyl, 4,5-dihydro-imidazol-2-yl, 2,3-dihydro-1- , -2-, -3-, -4- or -5-pyrazolyl, tetrahydro-1-, -3- or -4- pyrazolyl, 1,4-dihydro-1-, -2-, -3- or - 4-pyridyl, 1,2,3,4-tetrahydro-1-, -2-, -3-, -4-, -5- or -6-pyridyl, 1-, 2-, 3- or 4-piperidinyl , Morpholinyl, benzo [1,3] dioxol-4- or -5-yl, 5-, 6-, 7-, 8-chromanyl, hexahydro-1-, -3- or -4-pyridazinyl, hexahydro-1- , -2-, -4- or -5-pyrimidinyl, 1-, 2- or 3-piperazinyl, 1,2,3,4-tetrahydro-1-, -2-, -3-, -4-, - 5-, -6-, -7- or -8-quinolyl, 1,2,3,4-tetrahydro-1-, -2-, -3-, -4-, -5-, -6-, - 7- or -8-isoquinolyl or 1,2,3,4-tetrahydro-1,8-naphthyridin-7-yl.

Hydrogenated or partially hydrogenated Het residues can additionally by = NH or Carbonyl oxygen may be substituted.

Het ² is a heterocycle having 1, 2, 3 and / or 4 N, O and / or S atoms, preferably thiazol-2-, -3-, -4- or 5-yl, isothiazol-2-, -3-, -4- or 5-yl, 1-, 2- or 3-pyrrolyl, 1-, 2, 4- or 5-imidazolyl, 1-, 3-, 4- or 5-pyrazolyl, 2-, 3- or 4-pyridinyl, 2-, 4-, 5- or 6-pyrimidinyl, further preferably 1,2,3-triazol-1-, -4- or -5-yl, 1,2,4-triazol- 1-, -3- or 5-yl, 1- or 5-tetrazolyl, 3- or 4-pyridazinyl, pyrazinyl, 1-, 2-, 3-, 4-, 5-, 6- or 7- indolyl, 1 -, 2-, 4- or 5-benzimidazolyl, 1-, 3-, 4-, 5-, 6- or 7- benzopyrazolyl, 2-, 3-, 4-, 5-, 6-, 7- or 8 -Quinolinyl, 1-, 3-, 4-, 5-, 6-, 7- or 8-isoquinolinyl, 3-, 4-, 5-, 6-, 7- or 8-cinnolinyl, 2-, 4-, 5-, 6-, 7- or 8-quinazolinyl, 1H-imidazo [4,5-b] pyridin-2-yl or 1,8-naphthyridin-7-yl.

4-Pyridyl is particularly preferred.

The heterocyclic radicals can also be partially or completely hydrogenated. Het ² can, for. B. also mean 2,3-dihydro-1-, -2-, -3-, -4- or - 5-pyrrolyl, 2,5-dihydro-1-, -2-, -3-, -4- or -5-pyrrolyl, tetrahydro-1-, -2-, or -3-pyrrolyl, 1-, 2- or 3-pyrrolidinyl, tetrahydro-1-, -2- or -4- imidazolyl, 4,5-dihydro -imidazol-2-yl, 2,3-dihydro-1-, -2-, -3-, -4- or -5- pyrazolyl, tetrahydro-1-, -3- or -4-pyrazolyl, 1,4 -Dihydro-1-, -2-, -3- or - 4-pyridyl, 1,2,3,4-tetrahydro-1-, -2-, -3-, -4-, -5- or -6 -pyridyl, 1-, 2-, 3- or 4-piperidinyl, morpholinyl, benzo [1,3] dioxolyl, chromanyl, hexahydro- 1-, -3- or -4-pyridazinyl, hexahydro-1-, -2- , -4- or -5-pyrimidinyl, 1-, 2-, 3- or 4-piperazinyl, 1,2,3,4-tetrahydro-1-, -2-, -3-, -4-, -5 -, -6-, -7- or - 8-quinolyl, 1,2,3,4-tetrahydro-1-, -2-, -3-, -4-, -5-, -6-, -7 - or -8-isoquinolyl or 1,2,3,4-tetrahydro-1,8-naphthyridin-7-yl.

Hydrogenated or partially hydrogenated Het residues can additionally by = NH or Carbonyl oxygen may be substituted. 3H-Quinazolin-4-one-yl is preferred.

n is preferably 0, 1, 2, 3 or 4, very particularly preferably n means 0, 1 or 2.

m is preferably 0, 1, 2 or 3, very particularly preferably m means 0, 1 or 2.

As far as the compounds of formula I contain biphenyl, the second is Phenyl radical preferably in the 3- or 4-position on the first phenyl radical coupled, particularly preferably to the 4-position of the first phenyl ring.

Accordingly, the invention relates in particular to the use of those compounds of the formula I as proteinase M inhibitors in which at least one of the radicals mentioned has one of the preferred meanings indicated above. Some of the groups of compounds preferred for use as porteinase M inhibitors can be expressed by the following sub-formulas Ia to Ii, which correspond to the formula I and in which the radicals not specified have the meaning given for the formula I, but in which
in Ia) R ² denotes A;
in Ib) R unsubstituted or single, double or triple by A, Ar, (CH ₂ ) _n Ar, OR ² , OAr, OCF ₃ , OCOR ³ , CF ₃ , N (R ² ) ₂ , NHAr, Hal, NO ₂ , CN, (CH ₂ ) _n COOR ² , (CH ₂ ) _n COOAr, (CH ₂ ) _n CONHA, (CH ₂ ) _n CONH cycloalkyl, (CH ₂ ) _n CONA ₂ , (CH ₂ ) _n CONH (CH ₂ ) _m Ar, COR ² , COAr, NHCOA, NHCOAr, and / or


is substituted phenyl, naphthyl, or Het ¹ ,
in Ic) R ² denotes A;
R unsubstituted or single, double or triple by A, Ar, (CH ₂ ) _n Ar, OR ² , OAr, OCF ₃ , OCOR ³ , CF ₃ , N (R ² ) ₂ , NHAr, Hal, NO ₂ , CN, (CH ₂ ) _n COOR ² , (CH ₂ ) _n COOAr, (CH ₂ ) _n CONHA, (CH ₂ ) _n CONH cycloalkyl, (CH ₂ ) _n CONA ₂ , (CH ₂ ) _n CONH (CH ₂ ) _m Ar, COR ² , COAr, NHCOA, NHCOAr, and / or


is substituted phenyl, naphthyl, or Het ¹ ,
in Id) Ar unsubstituted or single, double or triple by A, OR ² , OCF ₃ , CF ₃ , N (R ² ) ₂ , Hal, NO ₂ , CN, (CH ₂ ) _n COOR ² , CON (R ² ) ₂ , COR ² , NHCOA, substituted cycloalkyl, phenyl, naphthyl, indanyl or Het ² ,
in Ie) R ² denotes A;
Ar unsubstituted or single, double or triple by A, OR ² , OCF ₃ , CF ₃ , N (R ² ) ₂ , Hal, NO ₂ , CN, (CH ₂ ) _n COOR ² , CON (R ² ) ₂ , COR ² , NHCOA, substituted cycloalkyl, phenyl, naphthyl, indanyl or Het ² ,
in If) Het ^{1 is} an aromatic mono- or dinuclear heterocycle with 1 or 2 N and / or O atoms
in Ig) Het ^{2 is} an aromatic mono- or dinuclear heterocycle with 1, 2 or 3 N, S and / or O atoms
in ih) R unsubstituted or single, double or triple by A, Ar, (CH ₂ ) _n Ar, OR ² , OAr, OCF ₃ , OCOR ³ , CF ₃ , N (R ² ) ₂ , NHAr, Hal, NO ₂ , CN, (CH ₂ ) _n COOR ² , (CH ₂ ) _n COOAr, (CH ₂ ) _n CONHA, (CH ₂ ) _n CONH cycloalkyl, (CH ₂ ) _n CONA ₂ , (CH ₂ ) _n CONH (CH ₂ ) _m Ar, COR ² , COAr, NHCOA, NHCOAr, and / or


is substituted phenyl, naphthyl, or Het ¹ ,
R ¹ H ₂ NC (= NH) - is
R ^{2 represents} A;
Ar unsubstituted or single, double or triple by A, OR ² , OCF ₃ , CF ₃ , N (R ² ) ₂ , Hal, NO ₂ , CN, (CH ₂ ) _n COOR ² , CON (R ² ) ₂ , COR ² , NHCOA, substituted cycloalkyl, phenyl, naphthyl, indanyl or Het ² ,
Het ^{1 is} an aromatic mono- or dinuclear heterocycle with 1 or 2 N and / or O atoms
Het ^{2 is} an aromatic mono- or dinuclear heterocycle with 1, 2 or 3 N, S and / or O atoms
A alkyl of 1 to 8 carbon atoms
Hal F, Cl, Br, I,
m 0, 1, 2, or 3
n is 0, 1, 2, 3 or 4
in ii) R unsubstituted or mono-, di- or triple by (CH ₂ ) _n Ar, OR ² , OAr, OCOR ² , (CH ₂ ) _n COOR ² , (CH ₂ ) _n CONHA, (CH ₂ ) _n CONHCycloalkyl , (CH ₂ ) _n CONA ₂ , (CH ₂ ) _n CONH (CH ₂ ) _m Ar, COR ² , COHet ² and / or NHCOA substituted phenyl, naphthyl, or Het ¹ ,
R ¹ H ₂ NC (= NH) - is
R ^{2 represents} A;
Ar is unsubstituted or monosubstituted or trisubstituted by A, OR ² , OCF ₃ , CF ₃ , Hal, (CH ₂ ) _n COOR ² , COR ² , NHCOA, cycloalkyl, phenyl or het,
Het ¹ 1-, 2-, 3-, 4-, 5-, 6- or 7-indolyl, indan-1- or -2-yl, 2-, 3-, 4-, 5-, 6-, 7 - or 8-quinolinyl, 1-, 3-, 4-, 5-, 6-, 7- or 8-isoquinolinyl, benzo [1,3] dioxol-4- or-5-yl or 5-, 6-, 7-, 8-Chromanyl means
Het ² thiazol-2-, -3-, -4- or 5-yl, 1-, 2, 4- or 5-imidazolyl, 1-, 3-, 4- or 5-pyrazolyl, 2-, 3- or 4-pyridinyl, 1,2,4-triazol-1-, -3- or 5-yl, 1-, 2-, 3-, 4-, 5-, 6- or 7-indolyl, tetrahydro-1-, -2-, or -3-pyrrolyl, 1-, 2- or 3- pyrrolidinyl, 1-, 2-, 3- or 4-piperidinyl, morpholinyl, 1-, 2-, 3- or 4-piperazinyl or 3H- Quinazolin-4-one-yl;
A alkyl of 1, 2, 3, 4, 5 or 6 carbon atoms
Hal F, Cl, Br, I,
m 0, 1, 2, or 3
n is 0, 1, 2, 3 or 4

It was a further object of the invention to provide further compounds which are suitable for inhibiting protease M. The invention therefore furthermore relates to the following compounds:
3- [3- (4-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N-phenylbenzamide;
N-butyl-3- [3- (4-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] benzamide;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N, N-diethyl-benzamide;
3- [3- (4-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N, N-dipropylbenzamide;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N, N-dibutyl-benzamide;
4- {2-oxo-5- [3- (pyrrolidin-1-carbonyl) phenoxymethyl] oxazolidin-3-yl} benzamidine;
4- {2-oxo-5- [3- (piperidin-1-carbonyl) phenoxymethyl] oxazolidin-3-yl} benzamidine;
4- {5- [3- (morpholine-1-carbonyl) phenoxymethyl] -2-oxo-oxazolidin-3-yl} benzamidine;
3- [3- (4-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N-cyclohexylbenzamide;
N-benzyl-3- [3- (4-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] benzamide;
3- [3- (4-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N-ethylbenzamide;
3- [3- (4-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N-propylbenzamide;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (3-fluorobenzyl) benzamide;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (4-fluorobenzyl) benzamide;
3- [3- (4-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (4-methylbenzyl) benzamide;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (3-methoxy-benzyl) benzamide;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (4-methoxy-benzyl) benzamide;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (4-triflouromethoxy-benzyl) benzamide;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N-phenethylbenzamide;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (3-methoxy-phenethyl) benzamide;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (3,4-dimethoxy-phenethyl) benzamide;
3- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (4-methoxyphenethyl) benzamide
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (4-fluorophenyl) benzamide;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (4-methylphenyl) benzamide;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (3-methoxy-phenyl) benzamide;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N, N-dimethyl-benzamide;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (3,4,5-trimethoxy-phenyl) benzamide;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N-thiazol-2-yl-benzamide;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (4-methoxy-phenyl) benzamide;
4- {5- [4- (5-methyl-pyridin-2-yl) phenoxymethyl] -2-oxo-oxazolidin-3-yl} benzamidine;
2- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N, N-dimethyl-benzamide;
4- {5- [3-methyl-4- (2-methyl-4-oxo-4H-quinazolin-3-yl) phenoxymethyl] -2-oxo-oxazolidin-3-yl} benzamidine;
5- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolide in-5-ylmethoxy] -2-methyl-1-propyl-1H-indole-3-carboxylic acid ethyl ester;
4- {5- [4- (4-acetyl-piperazin-1-yl) phenoxymethyl] -2-oxo-oxazolidin-3-yl} - benzamidine;
4- {2-oxo-5- [4- (1,3,5-trimethyl-1H-pyrazol-4-ylmethyl) phenoxymethyl] oxazolidin-3-yl} benzamidine;
4- [2-oxo-5- (2-piperidin-1-yl-phenoxymethyl) oxazolidin-3-yl] -benzamidine;
4- [5- (2-morpholin-4-yl-phenoxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
4- [2-oxo-5- (3-piperidin-1-yl-phenoxymethyl) oxazolidin-3-yl] -benzamidine;
4- [5- (4-imidazol-1-yl-phenoxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
4- [5- (3-Acetyl-phenoxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
{4- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] phenyl} ethyl acetate;
N- {4- [3- (4-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] phenyl} acetamide;
2- [3- (4-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N-phenylbenzamide;
4- {2-oxo-5- [4- (2-p-tolyl-ethyl) phenoxymethyl] oxazolidin-3-yl} -benzamidine;
Methyl 2- [3- (4-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] -4-methoxybenzoate;
4- [2-oxo-5- (4-propoxy-phenoxymethyl) oxazolidin-3-yl] -benzamidine;
4- {2-oxo-5- [4- (4-propylcyclohexyl) phenoxymethyl] oxazolidin-3-yl} benzamidine;
4- [5- (naphthalene-1-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
4- [5- (naphthalene-2-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
4- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] ethyl benzoate;
Methyl 2- [3- (4-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] benzoate;
2- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] ethyl benzoate;
4- [2-oxo-5- (3-trifluoromethyl-phenoxymethyl) oxazolidin-3-yl] -benzamidine;
4- [5- (4-cyclohexyl-phenoxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
4- [5- (2,4-dichloro-6-piperidin-1-ylmethylphenoxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine;
4- [5- (2-Benzyl-4-chloro-phenoxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
4- [5- (chroman-6-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
4- [5- (4-indan-1-yl-phenoxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidim
3- {4- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] phenyl} propionic acid methyl ester;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] methyl benzoate;
4- [5- (6-methoxy-naphthalene-2-yloxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine;
4- [2-oxo-5- (4-trifluoromethoxyphenoxymethyl) oxazolidin-3-yl] benzamidine;
4- [5- (1H-indol-5-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
4- [2-oxo-5- (4-phenoxy-phenoxymethyl) oxazolidin-3-yl] -benzamidine;
4- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] dimethyl phthalate;
4- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -3-propyl-benzoic acid methyl ester;
4- [2-oxo-5- (4-propionyl-phenoxymethyl) oxazolidin-3-yl] -benzamidine;
4- [5- (4-acetyl-2-methoxyphenoxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine;
4- [5- (4-propionyl-2-methoxy-phenoxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine;
2- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N, N-bis (3-methyl-butyl) benzamide;
N- {4- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -3-methyl-naphthalene-1-yl} acetamide;
4- [2-oxo-5- (2-trifluoromethyl-phenoxymethyl) oxazolidin-3-yl] -benzamidine;
4- [5- (Biphenyl-3-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
4- [2-oxo-5- (3-phenoxy-phenoxymethyl) oxazolidin-3-yl] -benzamidine;
4- [5- (biphenyl-4-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
N- {2- [3- (4-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] phenyl} acetamide;
Methyl 2- [3- (3-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] -4-methoxybenzoate;
3- [2-oxo-5- (4-propoxy-phenoxymethyl) oxazolidin-3-yl] -benzamidine;
3- {2-Oxo-5- [4- (4-propylcyclohexyl) phenoxymethyl] oxazolidin-3-yl} benzamidine;
3- [5- (naphthalene-1-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
3- [5- (naphthalene-2-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
2- [3- (3-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] ethyl benzoate;
3- [5- (4-cyclohexyl-phenoxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
3- [5- (2,4-dichloro-6-piperidin-1-ylmethylphenoxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine;
3- [5- (2-Benzyl-4-chloro-phenoxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
3- {5- [5-methyl-2- (3-phenyl-propyl) phenoxymethyl] -2-oxo-oxazolidin-3-yl} benzamidine;
4- [5- (2-Acetyl-phenoxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
4- [5- (4-tert-Butyl-phenoxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
3- {2-oxo-5- [4- (2-p-tolyl-ethyl) phenoxymethyl] oxazolidin-3-yl} -benzamidine;
2- [3- (3-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N-phenyl-benzamide;
3- [5- (4-indan-1-yl-phenoxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
Methyl 3- {4- [3- (3-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] phenyl} propionate;
3- [5- (7-methoxy-naphthalene-2-yloxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine;
3- [5- (6-methoxy-naphthalene-2-yloxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine;
3- [3- (3-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] methyl benzoate;
4- [5- (3-Acetyl-phenoxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
3- [5- (2-methyl-1H-indol-4-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
N- {4- [3- (3-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] phenyl} acetamide;
Methyl 2- [3- (3-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] benzoate;
4- [3- (3-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] ethyl benzoate;
3- [2-oxo-5- (3-trifluoromethyl-phenoxymethyl) oxazolidin-3-yl] -benzamidine;
3- [2-oxo-5- (4-phenoxy-phenoxymethyl) oxazolidin-3-yl] -benzamidine;
N- {2- [3- (3-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] phenyl} acetamide;
4- [5- (Benzo [1,3] dioxol-5-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
3- [2-oxo-5- (quinolin-6-yloxymethyl) oxazolidin-3-yl] -benzamidine;
4- [3- (3-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] dimethyl phthalate;
4- [3- (3-Carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] -3-propylbenzoic acid methyl ester;
3- [2-oxo-5- (4-propionyl-phenoxymethyl) oxazolidin-3-yl] -benzamidine;
3- [5- (4-acetyl-2-methoxy-phenoxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine;
3- [2-oxo-5- (3-phenoxy-phenoxymethyl) oxazolidin-3-yl] -benzamidine;
3- [5- (Biphenyl-3-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
3- [2-oxo-5- (2-trifluoromethyl-phenoxymethyl) oxazolidin-3-yl] -benzamidine;
N- {4- [3- (3-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -3-methyl-naphthalene-1-yl} acetamide;
2- [3- (3-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N, N-bis (3-methyl-butyl) benzamide;
3- [5- (2-methoxy-4-propionylphenoxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine;
4- [5- (2-acetyl-4-bromo-phenoxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
3- [5- (isoquinoline-5-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] phenyl acetic acid ester;
4- [2-oxo-5- (quinolin-8-yloxymethyl) oxazolidin-3-yl] -benzamidine;
4- [2-oxo-5- (quinolin-5-yloxymethyl) oxazolidin-3-yl] -benzamidine;
4- [5- (2-methoxy-4-morpholin-4-ylmethylphenoxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine;
3- [2-oxo-5- (quinolin-8-yloxymethyl) oxazolidin-3-yl] -benzamidine;
4- [5- (1H-indol-6-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
4- {5- [4- (4-Methyl-4H- [1,2,4] triazol-3-yl) phenoxymethyl] -2-oxo-oxazolidin-3-yl} benzamidine;
3- [5- (1H-indol-5-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
3- [5- (Benzo [1,3] dioxol-5-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
3- [5- (4-tert-Butyl-phenoxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
3- [5- (biphenyl-4-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
4- [2-oxo-5- (isoquinolin-5-yloxymethyl) oxazolidin-3-yl] -benzamidine;
3- [5- (chroman-6-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
3- [3- (3-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N-phenyl-benzamide;
3- {2-Oxo-5- [3- (1-pyrrolidin-1-yl-methanoyl) phenoxymethyl] oxazolidin-3-yl} benzamidine;
3- {5- [3- (1-morpholin-4-yl-methanoyl) phenoxymethyl] -2-oxo-oxazolidin-3-yl} benzamidine;
3- [3- (3-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N, N-dimethyl-benzamide;
3- [3- (3-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (4-methoxy-phenyl) benzamide;
3- {2-Oxo-5- [4- (1-pyrrolidin-1-ylmethanoyl) phenoxymethyl] oxazolidin-3-yl} benzamidine;
3- {2-Oxo-5- [4- (1-piperidin-1-yl-methanoyl) phenoxymethyl] oxazolidin-3-yl} benzamidine;
3- {2-oxo-5- [3- (1-piperidin-1-yl-methanoyl) phenoxymethyl] oxazolidin-3-yl} benzamidine;
3- [3- (3-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (3-methoxy-benzyl) benzamide;
N, N-dibutyl-3- [3- (3-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] benzamide;
4- {2-oxo-5- [4- (1-pyrrolidin-1-yl-methanoyl) phenoxymethyl] oxazolidin-3-yl} benzamidine;
4- [3- (3-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N, N-dipropylbenzamide;
4- [3- (3-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N-phenyl-benzamide,
their stereoisomers and / or their physiologically acceptable salts or solvates

• a) 5.71 g 1 (32 mmol) und 14.6 g Cäsiumfluorid (96.14 mmol) wurden in 40 ml DMF unter Argon-Atmosphäre gelöst und 30 min gerührt. Anschließend wurden 14.63 g Glycidyltosylat (64.09 mmol), gelöst in 17 ml DMF, zugetropft. Nach 96 h Rühren bei Raumtemperatur wurde das Reaktionsgemisch mit 300 ml Dichlormethan verdünnt, mit 75 ml 1 N NaOH-Lösung extrahiert, mit Wasser (3 ×) gewaschen, über Na₂SO₄ getrocknet, filtriert und eingedampft. Nach Reinigung mittels Vakuumflashchromatographie (215 g Kieselgel, Eluens: Petrolether (40-60°C)/Diethylether (4 : 1)) wurden 7.28 g (97%) 2, farbloses Öl, erhalten.
• b) 218.3 mg Tri-n-butylphosphinoxid und 86.8 mg Lithiumbromid wurden in 1 ml Xylol gelöst und 1 h bei 140°C gerührt. 1.31 g 3 (6.52 mmol) wurden unter Argon-Atmosphäre in 6.5 ml Xylol suspendiert und bei Raumtemperatur mit 2.29 g 2 (9.78 mmol), gelöst in 6.5 ml Xylol versetzt und auf 60°C erwärmt. Nun wurden 650 µl (0.65 mmol) der vorbereiteten Katalysatorlösung zugetropft und das Reaktionsgemisch 4 h bei 95°C gerührt. Das Reaktionsgemisch wurde eingeengt und der Rückstand mit 20 ml Diethylether versetzt. Der ausgefallene Niederschlag wurde abgesaugt, mit Diethylether/Petrolether (40-60°C) (7 : 3) nachgewaschen und über Nacht im Vakuum getrocknet. Die Mutterlauge wurde eingedampft und aus dem Rückstand wurde weiteres Produkt durch Kristallisation mit Diethylether/Petrolether gewonnen.
  Ausbeute: 2.46 g (87%) 4, farblose Kristalle
• c) 7.43 g 4 (17.06 mmol), 268.5 mg Triphenylphosphin (1.02 mmol) und 591.5 mg Tetrakis(triphenylphosphin)palladium (0.51 mmol) wurden unter Argon-Atmosphäre in 100 ml Dichlormethan suspendiert und auf auf 0°C abgekühlt. Anschließend wurden 2.82 ml Pyrrolidin (34.12 mmol) zugegeben, das Reaktionsgemisch 1.5 h bei 0°C und 1 h bei Raumtemperatur gerührt. Das Reaktionsgemisch wurde mit 300 ml Dichlormethan verdünnt und 150 ml 1 N HCl gewaschen. Die organische Phase wurde abgetrennt und der entstandene Niederschlag in der wässrigen Phase abgesaugt, mit Wasser gewaschen im Vakuum getrocknet. Das Filtrat wurde mehrmals mit Dichlormethan extrahiert. Die organischen Phasen wurden vereinigt, mit Wasser (2 × 50 ml) gewaschen, über Na₂SO₄ getrocknet, filtriert und eingedampft. Der Rückstand wurde mit 30 ml Ethylacetat/Diethylether (8 : 2) digeriert, abgesaugt, mit Diethylether gewaschen und im Vakuum getrocknet.
  Ausbeute: 6.28 g (93%) 5, farbloser Feststoff
• d) 84 mg (0.25 mmol) polymergebundenes Triphenylphosphin wurden unter Argon-Atmosphäre nacheinander mit einer Lösung von 50 mg 5 (0.126 mmol) in 2 ml DMF und 51 µl Trichloracetonitril (0.5 mmol) versetzt und 3 h bei Raumtemperatur gerührt. Anschließend wurden 5 Äquivalente (0.63 mmol) des entsprechenden Amins und 264 µl (1.89 mmol) Triethylamin zugegeben und weitere 20 h bei Raumtemperatur gerührt. Das Reaktionsgemisch wurde abgesaugt und der Rückstand mit warmen DMF (2 ml) und Dichlormethan (2 ml) nachgewaschen. Die vereinigten Filtrate wurden eingedampft. Der Rückstand wurde in 3 ml Chloroform aufgenommen und mit Wasser gewaschen. Die wäßrige Phase wurde mit Chloroform (2 × 2 ml) extrahiert und die vereinigten organischen Phasen zur Trockene eingedampft. Der Rückstand wurde mit Aceton (1 ml) digeriert, abgesaugt, mit Aceton/Diethylether (1 : 1) nachgewaschen und im Vakuum getrocknet. Die erhaltenen Verbindungen wurden abschließend mit Raney- Nickel in MeOH/THF - 1/3 unter Zusatz von Eisessig hydriert. Die Reaktionslösung wurde über Kieselgur abfiltriert, mit 1 ml MeOH nachgewaschen und anschließend eingeengt. Der Rückstand wurde in 3 ml Acetonitril/Wasser (1 : 1) aufgenommen, eingefroren und gefriergetrocknet.

Syntheseschema 2

• a) 50 mg (0.142 mmol) Mesylat 1 wurden zusammen mit 60.3 mg (0.185 mmol) Cäsiumcarbonat und 4.3 mg (0.028 mmol) Cäsiumfluorid in 1.5 ml Dimethylformamid gelöst, mit 1.1 Äquivalenten (0.156 mmol) des entsprechenden Phenols 2 versetzt und 18 h bei 50°C gerührt. Das Reaktionsgemisch wurde mit 2 ml Wasser und 0.5 ml 1 N NaOH versetzt und 5 min gerührt. Der ausgefallene Niederschlag wurde abgesaugt, mit 2 ml VE-Wasser und etwas Aceton gewaschen und im Vakuum bei 40°C über Nacht getrocknet.
• b) Verbindungen 3 wurden abschließend mit Raney-Nickel in MeOH/THF - 1/3 unter Zusatz von Eisessig hydriert. Die Reaktionslösung wurde über Kieselgur abfiltriert, mit 1 ml MeOH nachgewaschen und anschließend eingeengt. Der Rückstand wurde in 3 ml Acetonitril/Wasser (1 : 1) aufgenommen, eingefroren und gefriergetrocknet.

The above compounds can be prepared as follows. Synthesis scheme 1

• a) 5.71 g 1 (32 mmol) and 14.6 g cesium fluoride (96.14 mmol) were dissolved in 40 ml DMF under an argon atmosphere and stirred for 30 min. 14.63 g of glycidyl tosylate (64.09 mmol), dissolved in 17 ml of DMF, were then added dropwise. After stirring at room temperature for 96 h, the reaction mixture was diluted with 300 ml of dichloromethane, extracted with 75 ml of 1N NaOH solution, washed with water (3 ×), dried over Na ₂ SO ₄ , filtered and evaporated. After purification by means of vacuum flash chromatography (215 g of silica gel, eluent: petroleum ether (40-60 ° C.) / diethyl ether (4: 1)), 7.28 g (97%) 2, colorless oil, were obtained.
• b) 218.3 mg of tri-n-butylphosphine oxide and 86.8 mg of lithium bromide were dissolved in 1 ml of xylene and stirred at 140 ° C. for 1 h. 1.31 g 3 (6.52 mmol) were suspended in 6.5 ml xylene under an argon atmosphere, and 2.29 g 2 (9.78 mmol), dissolved in 6.5 ml xylene, were added at room temperature and the mixture was heated to 60.degree. 650 μl (0.65 mmol) of the prepared catalyst solution were then added dropwise and the reaction mixture was stirred at 95 ° C. for 4 h. The reaction mixture was concentrated and 20 ml of diethyl ether were added to the residue. The precipitate was filtered off, washed with diethyl ether / petroleum ether (40-60 ° C) (7: 3) and dried in vacuo overnight. The mother liquor was evaporated and further product was obtained from the residue by crystallization with diethyl ether / petroleum ether.
  Yield: 2.46 g (87%) 4, colorless crystals
• c) 7.43 g 4 (17.06 mmol), 268.5 mg triphenylphosphine (1.02 mmol) and 591.5 mg tetrakis (triphenylphosphine) palladium (0.51 mmol) were suspended in 100 ml dichloromethane under an argon atmosphere and cooled to 0 ° C. 2.82 ml of pyrrolidine (34.12 mmol) were then added, and the reaction mixture was stirred at 0 ° C. for 1.5 h and at room temperature for 1 h. The reaction mixture was diluted with 300 ml dichloromethane and washed 150 ml 1N HCl. The organic phase was separated off and the precipitate formed was suction filtered in the aqueous phase, washed with water and dried in vacuo. The filtrate was extracted several times with dichloromethane. The organic phases were combined, washed with water (2 × 50 ml), dried over Na ₂ SO ₄ , filtered and evaporated. The residue was digested with 30 ml of ethyl acetate / diethyl ether (8: 2), suction filtered, washed with diethyl ether and dried in vacuo.
  Yield: 6.28 g (93%) 5, colorless solid
• d) 84 mg (0.25 mmol) of polymer-bound triphenylphosphine were successively mixed with a solution of 50 mg of 5 (0.126 mmol) in 2 ml of DMF and 51 μl of trichloroacetonitrile (0.5 mmol) under an argon atmosphere, and the mixture was stirred at room temperature for 3 h. 5 equivalents (0.63 mmol) of the corresponding amine and 264 μl (1.89 mmol) of triethylamine were then added and the mixture was stirred at room temperature for a further 20 h. The reaction mixture was filtered off with suction and the residue was washed with warm DMF (2 ml) and dichloromethane (2 ml). The combined filtrates were evaporated. The residue was taken up in 3 ml of chloroform and washed with water. The aqueous phase was extracted with chloroform (2 × 2 ml) and the combined organic phases were evaporated to dryness. The residue was digested with acetone (1 ml), suction filtered, washed with acetone / diethyl ether (1: 1) and dried in vacuo. The compounds obtained were finally hydrogenated with Raney nickel in MeOH / THF - 1/3 with the addition of glacial acetic acid. The reaction solution was filtered off over kieselguhr, washed with 1 ml of MeOH and then concentrated. The residue was taken up in 3 ml of acetonitrile / water (1: 1), frozen and freeze-dried.

Synthesis scheme 2

• a) 50 mg (0.142 mmol) of mesylate 1 together with 60.3 mg (0.185 mmol) of cesium carbonate and 4.3 mg (0.028 mmol) of cesium fluoride were dissolved in 1.5 ml of dimethylformamide, 1.1 equivalents (0.156 mmol) of the corresponding phenol 2 were added and the mixture was stirred for 18 h 50 ° C stirred. The reaction mixture was mixed with 2 ml of water and 0.5 ml of 1N NaOH and stirred for 5 min. The precipitate was filtered off, washed with 2 ml of deionized water and a little acetone and dried in vacuo at 40 ° C overnight.
• b) Compounds 3 were finally hydrogenated with Raney nickel in MeOH / THF - 1/3 with the addition of glacial acetic acid. The reaction solution was filtered off over kieselguhr, washed with 1 ml of MeOH and then concentrated. The residue was taken up in 3 ml of acetonitrile / water (1: 1), frozen and freeze-dried.

The bases of the above-mentioned, detailed compounds can be converted into the associated acid addition salt with an acid be, for example by reacting equivalent amounts of the base and the acid in an inert solvent such as ethanol and subsequent evaporation. In particular come for this implementation Acids in question that provide physiologically acceptable salts. So can inorganic acids are used, e.g. B. sulfuric acid, sulphurous Acid, dithionic acid, nitric acid, hydrohalic acids such as Hydrochloric acid or hydrobromic acid, phosphoric acids such as z. B. orthophosphoric acid, sulfamic acid, also organic acids, in particular aliphatic, alicyclic, araliphatic, aromatic or heterocyclic mono- or poly-based carbon, sulfonic or Sulfuric acids, e.g. B. formic acid, acetic acid, propionic acid, Hexanoic acid, octanoic acid, decanoic acid, hexadecanoic acid, octadecanoic acid, Pivalic acid, diethyl acetic acid, malonic acid, succinic acid, Pimelic acid, fumaric acid, maleic acid, lactic acid, tartaric acid, Malic acid, citric acid, gluconic acid, ascorbic acid, nicotinic acid, Isonicotinic acid, methane or ethanesulfonic acid, benzenesulfonic acid, Trimethoxybenzoic acid, adamantane carboxylic acid, p-toluenesulfonic acid, Glycolic acid, embonic acid, chlorophenoxyacetic acid, aspartic acid, Glutamic acid, proline, glyoxylic acid, palmitic acid, Parachlorophenoxyisobutyric acid, cyclohexane carboxylic acid, glucose-1 phosphate, naphthalene mono- and disulfonic acids or lauryl sulfuric acid. Salts with physiologically unacceptable acids, e.g. B. picrates for the isolation and / or purification of the compounds of formula I. be used.

On the other hand, compounds of the formula I with bases (e.g. sodium or potassium hydroxide or carbonate) in the corresponding metal, especially alkali metal or alkaline earth metal or in the corresponding ammonium salts are converted.

The invention also relates to the aforementioned, in detail listed compounds, their stereoisomers and / or their physiologically acceptable salts or solvates as drugs.

The invention furthermore relates to the aforementioned, in detail listed compounds, their stereoisomers and / or their physiologically acceptable salts or solvates as integrins and / or Proteinase M inhibitors.

The invention also relates to the aforementioned, in detail listed compounds, their stereoisomers and / or their physiologically acceptable salts or solvates for prophylaxis and / or therapy of tumor diseases and / or neurodegenerative Diseases.

The invention further relates to at least one preparation containing one of the aforementioned, listed in detail Compounds, their stereoisomers and / or one of their physiological harmless salts or solvates. Here, the aforementioned, in Individual listed compounds together with at least one solid, liquid and / or semi-liquid carrier or auxiliary and optionally in combination with one or more others Active ingredients are brought into a suitable dosage form.

These preparations can be used as medicinal products in human or Veterinary medicine can be used. Organic come as carriers or inorganic substances that are suitable for enteral (e.g. oral), parenteral or topical application and with the new Compounds do not react, e.g. water, vegetable oils, Benzyl alcohols, alkylene glycols, polyethylene glycols, glycerol triacetate, Gelatin, carbohydrates such as lactose or starch, magnesium stearate, talc, Vaseline. Tablets, pills, Dragees, capsules, powders, granules, syrups, juices or drops, for rectal use suppositories, for parenteral use Solutions, preferably oily or aqueous solutions, further Suspensions, emulsions or implants, for topical use Ointments, creams or powder. The new connections can too lyophilized and the resulting lyophilizates z. B. for the production of Injectables are used. The specified preparations can be sterilized and / or auxiliary substances such as lubricants, preservatives, Stabilizing and / or wetting agents, emulsifiers, salts for influencing of osmotic pressure, buffer substances, color, taste and / or contain several other active ingredients, e.g. B. one or more Vitamins.

For the application as an inhalation spray, sprays can be used which contain the active ingredient either dissolved or suspended in a propellant gas or propellant gas mixture (e.g. CO ₂ or chlorofluorocarbons). The active ingredient is expediently used in micronized form, it being possible for one or more additional physiologically acceptable solvents to be present, for. B. ethanol. Inhalation solutions can be administered using standard inhalers.

The above-mentioned, detailed connections are in the Usually administered in doses between about 0.05 and 500 mg, preferably between 0.5 and 100 mg per dosage unit. The daily Dosage is preferably between about 0.01 and 2 mg / kg Body weight. However, the specific dose for each patient depends on various factors, such as the effectiveness of used special connection, by age, body weight, general State of health, sex, of food, of Time and route of administration from which Elimination rate, drug combination and severity of respective disease to which the therapy applies.

Furthermore, the above-mentioned, listed compounds as integrin ligands for the production of columns for the Affinity chromatography used for the purification of integrins become.

The ligand, i.e. H. one of the aforementioned, listed in detail Connections is done via an anchor function, e.g. B. the Carboxy group, covalently coupled to a polymeric support.

As polymeric carrier materials, they are suitable per se in peptide chemistry known polymeric solid phases with preferably hydrophilic Properties, for example cross-linked poly sugars such as cellulose, Sepharose or Sephadex®, acrylamides, polymer Polyethylene glycol base or tentacle polymer®.

The manufacture of materials for affinity chromatography Integrin cleaning takes place under conditions such as those for condensation of amino acids are common and known per se.

The abovementioned compounds listed in detail contain one or more chiral centers and can therefore be racemic or in optically active form. Racemates obtained can by themselves known methods mechanically or chemically in the enantiomers be separated. Preferably, the racemic mixture by reaction with an optically active release agent diastereomers educated. As a release agent z. B. optically active acids, such as the D- and L-forms of tartaric acid, diacetyltartaric acid, dibenzoyltartaric acid, Mandelic acid, malic acid, lactic acid or the various optically active camphorsulfonic acids such as β-camphorsulfonic acid. It is advantageous also enantiomer separation using one with an optically active Separating agent (e.g. dinitrobenzoyl-phenylglycine) filled column; as an eluent is suitable for. B. a mixture of hexane / isopropanol / acetonitrile, e.g. B. in Volume ratio 82: 15: 3.

Of course, it is also possible to use optically active connections aforementioned compounds listed in detail according to the above methods described by using starting materials used that are already optically active.

All temperatures above and below are given in ° C. In the The following examples mean "customary work-up": if required to add water, if necessary, depending on the constitution of the End product to pH values between 2 and 10, extracted with Ethyl acetate or dichloromethane, separates, dries the organic phase over sodium sulfate, evaporated and purified by chromatography Silica gel, by preparative HPLC and / or by crystallization. The purified compounds are optionally freeze-dried.

Gradients from acetonitrile (B) with 0.01% TFA are used as eluents (Trifluoroacetic acid) and water (A) with 0.01% TFA. The Gradient is given in percent by volume of acetonitrile.

The HPLC analyzes (retention time RT) were carried out in the following systems:
Column: Lichrospher RP-select-B (5 µm / 125 mm) with a 9 minute gradient from 20 to 100% water / acetonitrile / 0.01% trifluoroacetic acid, at 1.5 ml / min flow and detection at 220 nm.

Mass spectrometry (MS) using ESI (Electro Spray Ionization): MS-ESI (M + H) ⁺ .

The examples illustrate, but are not limited to, the invention. As far as the compounds described as examples as different Stereoisomers can be present and no information on stereochemistry there are mixtures of the stereoisomers.

The compounds can be administered to humans or animals locally or systemically, orally, intravenous, intraperitoneal, intramuscular, subcutaneous, transdermal, nasal, can be administered buccally or iontophoretically.

Examples

According to reaction scheme 1 (d), compound 5 is reacted with phenylamine and then hydrogenated. 3- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N-phenyl-benzamide acetate is obtained, RT 3.93 min, ESI-MS (M + H) ⁺ 430, 47th

According to reaction scheme 1 (d), compound 5 is reacted with n-butylamine and then hydrogenated. This gives N-butyl-3- [3- (4-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] benzamide acetate, RT 3.48 min, ESI-MS (M + H) ⁺ 410, 48th

According to reaction scheme 1 (d), compound 5 is reacted with N, N-diethylamine and then hydrogenated. 3- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N, N-diethyl-benzamide acetate, RT 3.17 min, ESI-MS (M + H) ^{+ are obtained} 410.48.

According to reaction scheme 1 (d), compound 5 is reacted with N, N-dipropylamine and then hydrogenated. This gives 3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N, N-dipropyl-benzamide acetate, RT 3.79 min, ESI-MS (M + H) ⁺ 438.53.

According to reaction scheme 1 (d), compound 5 is reacted with N, N-di-n-butylamine and then hydrogenated. 3- [3- (4- Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N, N-dibutyl-benzamide acetate, RT 4.45 min, ESI-MS (M + H) ^{+ is obtained} 466.59.

According to reaction scheme 1 (d), compound 5 is reacted with pyrrolidine and then hydrogenated. 4- {2-Oxo-5- [3- (pyrrolidin-1-carbonyl) phenoxymethyl] oxazolidin-3-yl} benzamidine acetate, RT 2.79 min, ESI-MS (M + H) ^{+ is obtained} 408.46.

According to reaction scheme 1 (d), compound 5 is reacted with piperidine and then hydrogenated. 4- {2-Oxo-5- [3- (piperidin-1-carbonyl) phenoxymethyl] oxazolidin-3-yl} benzamidine acetate, RT 3.27 min, ESI-MS (M + H) ⁺ 422.49.

According to reaction scheme 1 (d), compound 5 is reacted with morpholine and then hydrogenated. 4- {5- (3- (Morpholin-1-carbonyl) -phenoxymethyl] -2-oxo-oxazolidin-3-yl} -benzamidine acetate, RT 2.26 min, ESI-MS (M + H) ^{+ are obtained} 424.46.

According to reaction scheme 1 (d), compound 5 is reacted with cyclohexylamine and then hydrogenated. 3- [3- (4- Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N-cyclohexyl-benzamide acetate is obtained, RT 3.83 min, ESI-MS (M + H) ⁺ 436, 52nd

According to reaction scheme 1 (d), compound 5 is reacted with benzylamine and then hydrogenated. This gives N-benzyl-3- [3- (4-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] benzamide acetate, RT 3.71 min, ESI-MS (M + H) ⁺ 444, 49th

According to reaction scheme 1 (d), compound 5 is reacted with ethylamine and then hydrogenated. 3- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N-ethyl-benzamide acetate is obtained, RT 2.75 min, ESI-MS (M + H) ⁺ 382, 42nd

According to reaction scheme 1 (d), compound 5 is reacted with propylamine and then hydrogenated. 3- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N-propyl-benzamide acetate is obtained, RT 3.21 min, ESI-MS (M + H) ⁺ 396, 45th

According to reaction scheme 1 (d), compound 5 is reacted with 3-fluorobenzylamine and then hydrogenated. 3- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (3-flouro-benzyl) benzamide acetate, RT 3.97 min, ESI-MS (M. + H) ⁺ 462.49.

According to reaction scheme 1 (d), compound 5 is reacted with 4-fluorobenzylamine and then hydrogenated. 3- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (4-flouro-benzyl) benzamide acetate, RT 3.76 min, ESI-MS (M. + H) ⁺ 462.49.

According to reaction scheme 1 (d), compound 5 is reacted with 4-methylbenzylamine and then hydrogenated. This gives 3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (4-methyl-benzyl) benzamide acetate, RT 4.11 min, ESI-MS (M + H) ⁺ 458.52.

According to reaction scheme 1 (d), compound 5 is reacted with 3-methoxybenzylamine and then hydrogenated. 3- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (3-methoxy-benzyl) -benzamide acetate is obtained, RT 3.81 min, ESI-MS (M + H) ⁺ 474.52.

According to reaction scheme 1 (d), compound 5 is reacted with 4-methoxybenzylamine and then hydrogenated. 3- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (4-methoxy-benzyl) -benzamide acetate is obtained, RT 3.88 min, ESI-MS (M. + H) ⁺ 474.52.

According to reaction scheme 1 (d), compound 5 is reacted with triflouromethoxy-benzylamine and then hydrogenated. 3- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (4-triflouromethoxy-benzyl) -benzamide acetate, RT 4.62 min, ESI-MS (M. + H) ⁺ 528.49.

According to reaction scheme 1 (d), compound 5 is reacted with phenethylamine and then hydrogenated. This gives 3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N-phenethylbenzamide acetate, RT 3.99 min, ESI-MS (M + H) ⁺ 458, 52nd

According to reaction scheme 1 (d), compound 5 is reacted with 3-methoxyphenethylamine and then hydrogenated. This gives 3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (3-methoxy-phenethyl) -benzamide acetate, RT 4.01 min, ESI-MS (M + H) ⁺ 488.55.

According to reaction scheme 1 (d), compound 5 is reacted with 3,4-dimethoxy-phenethylamine and then hydrogenated. 3- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (3,4-dimethoxy-phenethyl) -benzamide acetate is obtained, RT 3.43 min, ESI-MS (M + H) ⁺ 504.55.

According to reaction scheme 1 (d), compound 5 is reacted with 4-methoxyphenethylamine and then hydrogenated. 3- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (4-methoxy-phenethyl) -benzamide acetate is obtained, RT 3.75 min, ESI-MS (M + H) ⁺ 488.55.

According to reaction scheme 1 (d), compound 5 is reacted with 4-fluorophenylamine and then hydrogenated. 3- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (4-flourophenyl) benzamide acetate, RT 3.97 min, ESI-MS (M. + H) ⁺ 448.46.

According to reaction scheme 1 (d), compound 5 is reacted with 4-methylphenylamine and then hydrogenated. 3- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (4-methyl-phenyl) -benzamide acetate is obtained, RT 4.01 min, ESI-MS (M. + H) ⁺ 444.49.

According to reaction scheme 1 (d), compound 5 is reacted with 3-methoxyphenylamine and then hydrogenated. Preparative HPLC gives 3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] - N- (3-methoxy-phenyl) -benzamide formate, RT 4.06 min, ESI- MS (M + H) ⁺ 460.49.

According to reaction scheme 1 (d), compound 5 is reacted with dimethylamine and then hydrogenated. After preparative HPLC, 3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N, N-dimethyl-benzamide formate, RT 2.56 min, ESI-MS (M + H) ⁺ 382.42.

According to reaction scheme 1 (d), compound 5 is reacted with 3,4,5-trimethoxyphenylamine and then hydrogenated. Preparative HPLC gives 3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (3,4,5-trimethoxy-phenyl) benzamide formate, RT 3.77 min, ESI MS (M + H) ⁺ 520.55.

According to reaction scheme 1 (d), compound 5 is reacted with thiazol-2-ylamine and then hydrogenated. After preparative HPLC, 3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] - N-thiazol-2-yl-benzamide formate, RT 3.51 min, ESI-MS ( M + H) ⁺ 437.48.

According to reaction scheme 1 (d), compound 5 is reacted with 4-methoxyphenylamine and then hydrogenated. After preparative HPLC, 3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] - N- (4-methoxy-phenyl) -benzamide formate, RT 3.91 min, ESI- MS (M + H) ⁺ 460.49.

According to Reaction Scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3-yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) is mixed with 4- (methyl-pyridine) 2-yl) phenol (compound 2) reacted and then catalytically hydrogenated. 4- {5- [4- (5-Methyl-pyridin-2-yl) -phenoxymethyl] -2-oxo-oxazolidin-3-yl} -benzamidine diacetate, RT 2.61 min, ESI-MS (M. + H) ⁺ 402.46.

According to Reaction Scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3-yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 2-hydroxy-N, N - Dimethyl-benzamide (compound 2) reacted and then catalytically hydrogenated. 2- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N, N-dimethyl-benzamide acetate, RT 2.07 min, ESI-MS (M + H) ^{+ are obtained} 382.42.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidin-5yl mesylate (Compound 1) with 3- (4-hydroxy-2- methyl-phenyl) -2-methyl-3H-quinazolinon-4-one (compound 2) implemented and then catalytically hydrogenated.

4- {5- (3-Methyl-4- (2-methyl-4-oxo-4H-quinazolin-3-yl) phenoxymethyl] -2-oxo-oxazolidin-3-yl} benzamidine diacetate, RT is obtained 3.69 min, ESI-MS (M + H) ⁺ 483.53.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 5-hydroxy-2- ethyl methyl-1-propyl-1H-indole-3-carboxylate (compound 2) implemented and then catalytically hydrogenated.

5- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -2-methyl-1-propyl-1H-indole-3-carboxylic acid ethyl acetate, RT 4.73 min, ESI is obtained -MS (M + H) ⁺ 478.55.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidin-5yl mesylate (Compound 1) with 1- [4- (4-hydroxy- phenyl) -piperazin-1-yl-] ethanone (compound 2) implemented and then catalytically hydrogenated.

4- {5- [4- (4-Acetyl-piperazin-1-yl) phenoxymethyl] -2-oxoxazolidin-3-yl} benzamidine acetate, RT 2.40 min, ESI-MS (M. + H) ⁺ 437.50.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) -phenyl] -2-oxo-oxazolidin-5yl mesylate (Compound 1) with 4- (1,3,5- Trimethyl-1H-pyrazol-4-ylmethyl) phenol (compound 2) implemented and then catalytically hydrogenated.

4- {2-Oxo-5- [4- (1,3,5-trimethyl-1H-pyrazol-4-ylmethyl) phenoxymethyl] oxazolidin-3-yl} benzamidine diacetate is obtained, RT 3.52 min , ESI-MS (M + H) ⁺ 433.51.

According to Reaction Scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3-yl) phenyl] -2-oxo-oxazolidin-5yl mesylate (Compound 1) with 2-piperidin-1-yl - phenol (compound 2) reacted and then catalytically hydrogenated. 4- [2-Oxo-5- (2-piperidin-1-yl-phenoxymethyl) oxazolidin-3-yl] benzamidine acetate, RT 1.43 min, ESI-MS (M + H) ⁺ 394, 48th

According to Reaction Scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3-yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 2-morpholin-4-yl -phenol (compound 2) and then catalytically hydrogenated. 4- [5- (2-Morpholin-4-yl-phenoxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine acetate, RT 2.92 min, ESI-MS (M + H) ⁺ 396, 45th

According to Reaction Scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3-yl) phenyl] -2-oxo-oxazolidin-5yl mesylate (Compound 1) with 3-piperidin-1-yl - phenol (compound 2) reacted and then catalytically hydrogenated. 4- [2-Oxo-5- (3-piperidin-1-yl-phenoxymethyl) oxazolidin-3-yl] benzamidine acetate, RT 1.71 min, ESI-MS (M + H) ⁺ 394, 48th

According to Reaction Scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3-yl) phenyl] -2-oxo-oxazolidin-5yl mesylate (compound 1) with 4-imidazol-1-yl - phenol (compound 2) reacted and then catalytically hydrogenated. 4- [5- (4-Imidazol-1-yl-phenoxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine diacetate, RT 1.11 min, ESI-MS (M + H) ⁺ 394, 48th

According to Reaction Scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3-yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) is combined with 3-acetyl-phenol (Compound 2) implemented and then catalytically hydrogenated. 4- [5- (3-Acetylphenoxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine acetate is obtained, RT 3.25 min, ESI-MS (M + H) ⁺ 353.38.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 4- (hydroxy- phenyl) -acetic acid ethyl ester (compound 2) and then catalytically hydrogenated.

This gives ethyl {4- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] phenyl} acetate, RT 3.93 min, ESI-MS (M + H) ⁺ 397, 44th

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidin-5yl mesylate (Compound 1) with N-4- (hydroxy- phenyl) acetamide (compound 2) and then catalytically hydrogenated.

N- {4- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -phenyl} -acetamide acetate is obtained, RT 2.09 min, ESI-MS (M + H) ⁺ 368.40.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) -phenyl] -2-oxo-oxazolidine-5yl mesylate (compound 1) with 2-hydroxy-N- phenyl-benzamide (compound 2) and then catalytically hydrogenated.

2- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] - N-phenyl-benzamide acetate, RT 3.71 min, ESI-MS (M + H) ⁺ 430, 47th

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidin-5yl mesylate (Compound 1) with 4- (2-p-tolyl- ethyl) phenol (compound 2) and then catalytically hydrogenated.

4- {2-Oxo-5- [4- (2-p-tolyl-ethyl) -phenoxymethyl] -oxazolidin-3-yl} - benzamidine acetate, RT 5.52 min, ESI-MS (M + H ) ⁺ 429.52.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 2-hydroxy-4- methyl methoxy-benzoate (Compound 2) implemented and then catalytically hydrogenated.

This gives 2- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -4-methoxy-benzoic acid methyl acetate, RT 3.43 min, ESI-MS (M + H) ⁺ 399, 41st

According to Reaction Scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3-yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (compound 1) is combined with 4-propoxyphenol (compound 2) implemented and then catalytically hydrogenated. 4- [2-Oxo-5- (4-propoxyphenoxymethyl) oxazolidin-3-yl] benzamidine acetate is obtained, RT 4.18 min, ESI-MS (M + H) ⁺ 369.42.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) -phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 4- (4-propyl- cyclohexyl) phenol (compound 2) and then catalytically hydrogenated.

4- {2-Oxo-5- [4- (4-propylcyclohexyl) phenoxymethyl] oxazolidin-3-yl} benzamidine acetate, RT 5.83 min, ESI-MS (M + H) ^{+ are obtained} 435.57.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidin-5yl mesylate (Compound 1) with naphthalene-1-ol (Compound 2) reacted and then catalytically hydrogenated.

4- [5- (Naphthalene-1-yloxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine acetate is obtained, RT 4.10 min, ESI-MS (M + H) ⁺ 361.40.

According to Reaction Scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3-yl) phenyl] -2-oxo-oxazolidin-5yl mesylate (Compound 1) is combined with naphthalene-2-ol (Compound 2) implemented and then catalytically hydrogenated. 4- [5- (Naphthalen-2-yloxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine acetate is obtained, RT 4.37 min, ESI-MS (M + H) ⁺ 361.40.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 4-hydroxy- implemented ethyl benzoate (compound 2) and then catalytically hydrogenated.

4- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] ethyl acetate acetate is obtained, RT 3.84 min, ESI-MS (M + H) ⁺ 383.41.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) -phenyl] -2-oxo-oxazolidine-5yl mesylate (compound 1) with 2-hydroxy- methyl benzoate (compound 2) and then reacted catalytically hydrogenated.

2- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] - methyl benzoate acetate is obtained, RT 3.19 min, ESI-MS (M + H) ⁺ 369.38.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) -phenyl] -2-oxo-oxazolidine-5yl mesylate (compound 1) with 2-hydroxy- implemented ethyl benzoate (compound 2) and then catalytically hydrogenated.

2- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] ethyl benzoate acetate, RT 3.49 min, ESI-MS (M + H) ⁺ 383.41 is obtained.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) -phenyl] -2-oxo-oxazolidine-5yl mesylate (compound 1) with 3- Triflouromethyl-phenol (compound 2) implemented and then catalytically hydrogenated.

4- [2-Oxo-5- (3-trifluoromethyl-phenoxymethyl) oxazolidin-3-yl] benzamidine acetate is obtained, RT 4.33 min, ESI-MS (M + H) ⁺ 379.34.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) -phenyl] -2-oxo-oxazolidine-5yl mesylate (compound 1) with 4-cyclohexyl phenol (compound 2) reacted and then catalytically hydrogenated.

4- [5- (4-Cyclohexyl-phenoxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine acetate, RT 5.17 min, ESI-MS (M + H) ⁺ 393.49 are obtained.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 2,4-dichloro-6- implemented piperidin-1-ylmethyl-phenol (compound 2) and then catalytically hydrogenated.

4- [5- (2,4-Dichloro-6-piperidin-1-ylmethyl-phenoxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine acetate, RT 2.84 min, ESI-MS (M. + H) ⁺ 477.40.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) -phenyl] -2-oxo-oxazolidine-5yl mesylate (compound 1) with 2-benzyl-4- chloro-phenol (compound 2) and then catalytically hydrogenated.

4- [5- (2-Benzyl-4-chlorophenoxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine acetate, RT 4.78 min, ESI-MS (M + H) ⁺ 435, 91st

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidin-5yl mesylate (Compound 1) with chroman-6-ol (Compound 2) reacted and then catalytically hydrogenated.

4- [5- (Chroman-6-yloxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine acetate is obtained, RT 3.67 min, ESI-MS (M + H) ⁺ 367.41.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidin-5yl mesylate (Compound 1) with 4-indan-1-yl- phenol (compound 2) reacted and then catalytically hydrogenated.

4- [5- (4-Indan-1-yl-phenoxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine acetate is obtained, RT 5.03 min, ESI-MS (M + H) ⁺ 427, 51st

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 3- (4-hydroxy- phenyl) propionic acid methyl ester (compound 2) and then catalytically hydrogenated.

3- {4- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -phenyl} -propionic acid methyl acetate, RT, 3.78 min, ESI-MS (M + H) ^{+ is obtained} 397.44.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) -phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 3-hydroxy- methyl benzoate (compound 2) and then reacted catalytically hydrogenated.

3- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] methyl benzoate acetate, RT 3.49 min, ESI-MS (M + H) ⁺ 369.38 is obtained.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 6-methoxy- naphthalen-2-ol (compound 2) and then catalytically hydrogenated.

4- [5- (6-Methoxy-naphthalen-2-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine acetate, RT 4.21 min, ESI-MS (M + H) ⁺ 391, 43rd

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 4- Trifluoromethoxy-phenol (compound 2) implemented and then catalytically hydrogenated.

4- [2-Oxo-5- (4-trifluoromethoxyphenoxymethyl) oxazolidin-3-yl] benzamidine acetate is obtained, RT 4.34 min, ESI-MS (M + H) ⁺ 395.34.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidin-5yl mesylate (Compound 1) with 1H-indol-5-ol (Compound 2) reacted and then catalytically hydrogenated.

4- [5- (1H-Indol-5-yloxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine acetate is obtained, RT 3.30 min, ESI-MS (M + H) ⁺ 350.38.

According to Reaction Scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3-yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (compound 1) is combined with 4-phenoxyphenol (compound 2) implemented and then catalytically hydrogenated. 4- [2-Oxo-5- (4-phenoxyphenoxymethyl) oxazolidin-3-yl] benzamidine acetate is obtained, RT 4.52 min, ESI-MS (M + H) ⁺ 403.44.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 4-hydroxy- implemented phthalic acid dimethyl ester (compound 2) and then catalytically hydrogenated.

4- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] dimethyl acetate is obtained, RT 3.31 min, ESI-MS (M + H) ⁺ 427.42.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) -phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 4-hydroxy-3- methyl propyl benzoate (Compound 2) implemented and then catalytically hydrogenated.

4- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -3-propyl-benzoic acid methyl acetate is obtained, RT 4.03 min, ESI-MS (M + H) ⁺ 411, 46th

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidin-5yl mesylate (Compound 1) with 1- (4-hydroxy- phenyl) propan-1-one (compound 2) and then catalytically hydrogenated.

4- [2-Oxo-5- (4-propionylphenoxymethyl) oxazolidin-3-yl] benzamidine acetate is obtained, RT 3.23 min, ESI-MS (M + H) ⁺ 367.41.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 1- (4-hydroxy-3- implemented methoxy-phenyl) -ethanone (compound 2) and then catalytically hydrogenated.

4- [5- (4-Acetyl-2-methoxy-phenoxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine acetate is obtained, RT 2.79 min, ESI-MS (M + H) ⁺ 383, 41st

According to reaction scheme 2, 3- [4- (5-methyl- (1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 1- (4-hydroxy-3- implemented methoxy-phenyl) propane-1-an (compound 2) and then catalytically hydrogenated.

4- [5- (4-propionyl-2-methoxy-phenoxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine acetate is obtained, RT 3.29 min, ESI-MS (M + H) ⁺ 397, 44th

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 2- [bis- (3-methyl- butyl) amino] -1- (2-hydroxyphenyl) ethanone (Compound 2) implemented and then catalytically hydrogenated.

2- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] - N, N-bis- (3-methyl-butyl) -benzamide acetate, RT 4.71 min, ESI is obtained -MS (M + H) ⁺ 494.64.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with N- (4-hydroxy-3- methyl-naphthalene-1-yl) acetamide (compound 2) implemented and then catalytically hydrogenated.

N- {4- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -3-methyl-naphthalen-1-yl} -acetamide acetate is obtained, RT 2.93 min, ESI - MS (M + H) ⁺ 494.64.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 2- Triflouromethyl-phenol (compound 2) implemented and then catalytically hydrogenated.

4- [2-Oxo-5- (2-trifluoromethylphenoxymethyl) oxazolidin-3-yl] benzamidine acetate is obtained, RT 3.6 min, ESI-MS (M + H) ⁺ 379.34.

According to Reaction Scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3-yl) phenyl] -2-oxo-oxazolidin-5yl mesylate (Compound 1) with biphenyl-3-ol (Compound 2) implemented and then catalytically hydrogenated. 4- [5- (Biphenyl-3-yloxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine acetate is obtained, RT 4.43 min, ESI-MS (M + H) ⁺ 378.44.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3-yl) -phenyl] -2-oxo-oxazolidine-5yl mesylate (compound 1) is combined with 3-phenoxyphenol (compound 2) implemented and then catalytically hydrogenated. 4- [2-Oxo-5- (3-phenoxyphenoxymethyl) oxazolidin-3-yl] benzamidine acetate is obtained, RT 4.41 min, ESI-MS (M + H) ⁺ 403.44.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidin-5yl mesylate (Compound 1) with biphenyl-4-ol (Compound 2) reacted and then catalytically hydrogenated.

4- [5- (Biphenyl-4-yloxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine acetate is obtained, RT 4.41 min, ESI-MS (M + H) ⁺ 378.44.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) -phenyl] -2-oxo-oxazolidine-5yl mesylate (compound 1) with 2-hydroxy-N- acetylbenzamide (compound 2) and then catalytically hydrogenated.

N- {2- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -phenyl} -acetamide acetate is obtained, RT 1.86 min, ESI-MS (M + H) ⁺ 368.40.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 2-hydroxy-4- methyl methoxy-benzoate (Compound 2) implemented and then catalytically hydrogenated.

2- [3- (3-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -4-methoxy-benzoic acid methyl acetate is obtained, RT 3.27 min, ESI-MS (M + H) ⁺ 399, 41st

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 4-propoxy- phenol (compound 2) reacted and then catalytically hydrogenated.

3- [2-Oxo-5- (4-propoxyphenoxymethyl) oxazolidin-3-yl] benzamidine acetate is obtained, RT 4.11 min, ESI-MS (M + H) ⁺ 369.42.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) -phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 4- (4-propyl- cyclohexyl) phenol (compound 2) and then catalytically hydrogenated.

3- {2-Oxo-5- [4- (4-propylcyclohexyl) phenoxymethyl] oxazolidin-3-yl} benzamidine acetate, RT 5.77 min, ESI-MS (M + H) ^{+ is obtained} 369.42.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidin-5yl mesylate (Compound 1) with naphthalene-1-ol implemented and then catalytically hydrogenated.

This gives 3- [5- (naphthalene-1-yloxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine acetate, RT 4.15 min, ESI-MS (M + H) ⁺ 361.40.

According to Reaction Scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3-yl) phenyl] -2-oxo-oxazolidin-5yl mesylate (Compound 1) with naphthalen-2-ol (Compound 2) implemented and then catalytically hydrogenated. 3- [5- (Naphthalen-2-yloxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine acetate is obtained, RT 4.32 min, ESI-MS (M + H) ⁺ 361.40.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine 5yl mesylate (Compound 1) with (Compound 2) 2-Hydroxy-benzoic acid and then catalytically hydrogenated.

2- [3- (3-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] ethyl acetate is obtained, RT 3.55 min, ESI-MS (M + H) ⁺ 383.41.

According to Reaction Scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3-yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with (Compound 2) 4-cyclohexylphenol implemented and then catalytically hydrogenated. 3- [5- (4-Cyclohexylphenoxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine acetate is obtained, RT 3.46 min, ESI-MS (M + H) ⁺ 393.49.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 2,4-dichloro-6- implemented piperidin-1-ylmethyl-phenol (compound 2) and then catalytically hydrogenated.

This gives 3- [5- (2,4-dichloro-6-piperidin-1-ylmethyl-phenoxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine acetate, RT 2.69 min, ESI-MS (M. + H) ⁺ 477.40.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- chloro-phenol (compound 2) and then catalytically hydrogenated.

This gives 3- [5- (2-benzyl-4-chlorophenoxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine acetate, RT 4.65 min, ESI-MS (M + H) ⁺ 435, 91st

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 5-methyl-2- (3- phenyl-propyl) -phenol (compound 2) implemented and then catalytically hydrogenated.

3- {5- [5-Methyl-2- (3-phenyl-propyl) -phenoxymethyl] -2-oxo-oxazolidin-3-yl} -benzamidine acetate is obtained, RT 5.05 min, ESI-MS (M. + H) ⁺ 443.55.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 1- (2-hydroxy- phenyl) -ethanone (compound 2) and then catalytically hydrogenated.

4- [5- (2-Acetylphenoxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine acetate is obtained, RT 3.12 min, ESI-MS (M + H) ⁺ 353.38.

According to Reaction Scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3-yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) is mixed with 4-tert-butyl phenol (compound 2) reacted and then catalytically hydrogenated. 4- [5- (4-tert-Butyl-phenoxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine acetate is obtained, RT 4.71 min, ESI-MS (M + H) ⁺ 367.45 ,

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) -phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 4- [2- (4-methyl- phenyl) ethyl phenol (compound 2) and then catalytically hydrogenated.

3- {2-Oxo-5- [4- (2-p-tolyl-ethyl) -phenoxymethyl] -oxazolidin-3-yl} - benzamidine acetate, RT 5.17 min, ESI-MS (M + H ) ⁺ 429.52.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) -phenyl] -2-oxo-oxazolidine-5yl mesylate (compound 1) with 2-hydroxy-N- phenyl-benzamide (compound 2) and then catalytically hydrogenated.

2- [3- (3-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] - N-phenyl-benzamide acetate, RT 3.6 min, ESI-MS (M + H) ⁺ 430, 47th

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine 5yl mesylate (Compound 1) with 4-indan-1yl phenol (compound 2) reacted and then catalytically hydrogenated.

This gives 3- [5- (4-indan-1-yl-phenoxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine acetate, RT 5.03 min, ESI-MS (M + H) ⁺ 427, 51st

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 3- (4-hydroxy- phenyl) propionic acid methyl ester (compound 2) and then catalytically hydrogenated.

This gives methyl 3- {4- [3- (3-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] phenyl} propionate acetate, RT 3.73 min, ESI-MS (M + H) ⁺ 397.43.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 7-methoxy- naphthalen-2-ol (compound 2) and then catalytically hydrogenated.

3- [5- (7-Methoxy-naphthalene-2-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine acetate is obtained, RT 4.31 min, ESI-MS (M + H) ⁺ 391, 43rd

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 6-methoxy- naphthalen-2-ol (compound 2) and then catalytically hydrogenated.

3- [5- (6-Methoxy-naphthalen-2-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine acetate is obtained, RT 4.25 min, ESI-MS (M + H) ⁺ 391, 43rd

According to reaction scheme 2, 3- [3- (5-methyl- (1,2,4] oxadiazol-3- yl) -phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 3-hydroxy- methyl benzoate (compound 2) and then reacted catalytically hydrogenated.

This gives 3- [3- (3-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] methyl benzoate acetate, RT 3.61 min, ESI-MS (M + H) ⁺ 369.38.

According to reaction scheme 2, 3- [3- (5-methyl- (1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 1- (3-hydroxy- phenyl) -ethanone (compound 2) and then catalytically hydrogenated.

4- [5- (3-Acetyl-phenoxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine acetate is obtained, RT 3.31 min, ESI-MS (M + H) ⁺ 353.38.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) -phenyl] -2-oxo-oxazolidine-5yl mesylate (compound 1) with 2-methyl-1H- reacted indol-4-ol (compound 2) and then catalytically hydrogenated.

3- [5- (2-Methyl-1H-indol-4-yloxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine acetate is obtained, RT 3.62 min, ESI-MS (M + H) ⁺ 353.38.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidin-5yl mesylate (Compound 1) with N- (4-hydroxy- phenyl) acetamide (compound 2) and then catalytically hydrogenated.

N- {4- [3- (3-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -phenyl} -acetamide acetate is obtained, RT 2.12 min, ESI-MS (M + H) ⁺ 368.40.

According to reaction scheme 2, 3- [3- (5-methyl- (1,2,4] oxadiazol-3- yl) -phenyl] -2-oxo-oxazolidine-5yl mesylate (compound 1) with 2-hydroxy- methyl benzoate (compound 2) and then reacted catalytically hydrogenated.

2- [3- (3-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] - methyl benzoate acetate is obtained, RT 3.21 min, ESI-MS (M + H) ⁺ 369.38.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 4-hydroxy- implemented ethyl benzoate (compound 2) and then catalytically hydrogenated.

4- [3- (3-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] ethyl acetate acetate is obtained, RT 3.86 min, ESI-MS (M + H) ⁺ 383.41.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) -phenyl] -2-oxo-oxazolidine-5yl mesylate (compound 1) with 3- Triflouromethyl-phenol (compound 2) implemented and then catalytically hydrogenated.

3- [2-Oxo-5- (3-trifluoromethylphenoxymethyl) oxazolidin-3-yl] benzamidine acetate is obtained, RT 4.29 min, ESI-MS (M + H) ⁺ 379.34.

According to reaction scheme 2, 3- [3- (5-methyl- (1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 4-phenoxy- phenol (compound 2) reacted and then catalytically hydrogenated.

3- [2-Oxo-5- (4-phenoxyphenoxymethyl) oxazolidin-3-yl] benzamidine acetate is obtained, RT 4.61 min, ESI-MS (M + H) ⁺ 403.44.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidin-5yl mesylate (Compound 1) with N- (2-hydroxy- phenyl) acetamide (compound 2) and then catalytically hydrogenated.

N- {2- [3- (3-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -phenyl} -acetamide acetate is obtained, RT 2.28 min, ESI-MS (M + H) ⁺ 368.40.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with Benzo [1,3] dioxol-5-ol (compound 2) reacted and then catalytically hydrogenated.

4- [5- (Benzo [1,3] dioxol-5-yloxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine acetate are obtained, RT 3.51 min, ESI-MS (M + H) ⁺ 355.35.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidin-5yl mesylate (Compound 1) with quinolin-6-ol (Compound 2) reacted and then catalytically hydrogenated.

3- [2-Oxo-5- (quinolin-6-yloxymethyl) oxazolidin-3-yl] benzamidine acetate is obtained, RT 1.31 min, ESI-MS (M + H) ⁺ 362.39.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 4-hydroxy- implemented phthalic acid dimethyl ester (compound 2) and then catalytically hydrogenated.

4- (3- (3-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] dimethyl acetate is obtained, RT 3.43 min, ESI-MS (M + H) ⁺ 427.42.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) -phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 4-hydroxy-3- methyl propyl benzoate (Compound 2) implemented and then catalytically hydrogenated.

4- [3- (3-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -3-propyl-benzoic acid methyl acetate is obtained, RT 4.05 min, ESI-MS (M + H) ⁺ 411, 46th

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidin-5yl mesylate (Compound 1) with 1- (4-hydroxy- phenyl) propane-1-an (compound 2) and then catalytically hydrogenated.

3- [2-Oxo-5- (4-propionylphenoxymethyl) oxazolidin-3-yl] benzamidine acetate is obtained, RT 3.47 min, ESI-MS (M + H) ⁺ 367.41.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 1- (4-hydroxy-3- implemented methoxy-phenyl) -ethanone (compound 2) and then catalytically hydrogenated.

3- [5- (4-Acetyl-2-methoxy-phenoxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine acetate, RT 2.90 min, ESI-MS (M + H) ⁺ 383, 41st

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (compound 1) with 3-phenoxy- phenol (compound 2) reacted and then catalytically hydrogenated.

3- [2-Oxo-5- (3-phenoxyphenoxymethyl) oxazolidin-3-yl] benzamidine acetate is obtained, RT 4.46 min, ESI-MS (M + H) ⁺ 403.44.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidin-5yl mesylate (Compound 1) with biphenyl-2-ol (Compound 2) reacted and then catalytically hydrogenated.

3- [5- (Biphenyl-3-yloxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine acetate is obtained, RT 4.37 min, ESI-MS (M + H) ⁺ 387.44.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 2- Triflouromethyl-phenol (compound 2) implemented and then catalytically hydrogenated.

3- [2-Oxo-5- (2-trifluoromethylphenoxymethyl) oxazolidin-3-yl] benzamidine acetate is obtained, RT 3.71 min, ESI-MS (M + H) ⁺ 379.34.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with N- (4-hydroxy-3- methyl-naphthalene-1 yl) acetamide (compound 2) implemented and then catalytically hydrogenated.

N- {4- [3- (3-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -3-methyl-naphthalen-1-yl} -acetamide acetate, RT 2.94 min, ESI is obtained - MS (M + H) ⁺ 432.48.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) N, N-bis- (3-methyl- butyl) benzamide (compound 2) and then catalytically hydrogenated.

2- [3- (3-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] - N, N-bis- (3-methyl-butyl) -benzamide acetate, RT 4.75 min, ESI is obtained -MS (M + H) ⁺ 494.64.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 1- (4-hydroxy-3- implemented methoxy-phenyl) propan-1-one (compound 2) and then catalytically hydrogenated.

This gives 3- [5- (2-methoxy-4-propionylphenoxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine acetate, RT 3.27 min, ESI-MS (M + H) ⁺ 397, 43rd

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 1- (5-bromo-2- hydroxy-phenyl) -ethanone (compound 2) implemented and then catalytically hydrogenated.

4- [5- (2-Acetyl-4-bromo-phenoxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine acetate, RT 3.73 min, ESI-MS (M + H) ⁺ 432, 28th

According to Reaction Scheme 2, 343- (5-methyl- [1,2,4] oxadiazol-3-yl) phenyl] -2-oxo-oxazolidin-5yl mesylate (compound 1) is reacted with isoquinolin-5-ol (compound 2) and then catalytically hydrogenated. 3- [5- (Isoquinolin-5-yloxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine acetate is obtained, RT 1.17 min, ESI-MS (M + H) ⁺ 362.39.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with (3-hydroxy- phenyl) acetic acid ester (compound 2) and then catalytically hydrogenated.

This gives 3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] phenylacetic acid acetate, RT 3.32 min, ESI-MS (M + H) ⁺ 369.38.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidin-5yl mesylate (Compound 1) with quinolin-8-ol (Compound 2) reacted and then catalytically hydrogenated.

4- [2-Oxo-5- (quinolin-8-yloxymethyl) oxazolidin-3-yl] benzamidine acetate is obtained, RT 1.30 min, ESI-MS (M + H) ⁺ 362.39.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidin-5yl mesylate (Compound 1) with quinolin-5-ol (Compound 2) reacted and then catalytically hydrogenated.

4- [2-Oxo-5- (quinolin-5-yloxymethyl) oxazolidin-3-yl] benzamidine acetate is obtained, RT 1.35 min, ESI-MS (M + H) ⁺ 362.39.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 2-methoxy-4- morpholin-4-ylmethyl-phenol (compound 2) and then reacted catalytically hydrogenated.

4- [5- (2-Methoxy-4-morpholin-4-ylmethyl-phenoxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine formate, RT 1.15 min, ESI-MS (M + H ) ⁺ 440.50.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidin-5yl mesylate (Compound 1) with quinolin-8-ol (Compound 2) reacted and then catalytically hydrogenated.

3- [2-Oxo-5- (quinolin-8-yloxymethyl) oxazolidin-3-yl] benzamidine diformate is obtained, RT 1.17 min, ESI-MS (M + H) ⁺ 362.39.

According to reaction scheme 2, 3- [4- (5-methyl- (1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidin-5yl mesylate (Compound 1) with 1-H-indol-6-ol (Compound 2) reacted and then catalytically hydrogenated.

4- [5- (1H-Indol-6-yloxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine diformate is obtained, RT 3.59 min, ESI-MS (M + H) ⁺ 350.38.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 4- (4-methyl-4-H- [1,2,4] triazol-3-yl) phenol (compound 2) and then reacted catalytically hydrogenated.

4- {5- [4- (4-Methyl-4H- [1,2,4] triazol-3-yl) phenoxymethyl] -2-oxoxazolidin-3-yl} benzamidine diformate, RT 1 is obtained , 08 min, ESI-MS (M + H) ⁺ 392.42.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidin-5yl mesylate (Compound 1) with 1-H-indol-5-ol (Compound 2) reacted and then catalytically hydrogenated.

3- [5- (1H-Indol-5-yloxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine diformate is obtained, RT 3.39 min, ESI-MS (M + H) ⁺ 350.38.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with Benzo [1,3] dioxol-5-ol (compound 2) reacted and then catalytically hydrogenated.

3- [5- (Benzo [1,3] dioxol-5-yloxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine acetate is obtained, RT 3.29 min, ESI-MS (M + H) ⁺ 355.35.

According to Reaction Scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3-yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) is treated with 4-tert-butyl phenol (compound 2) reacted and then catalytically hydrogenated. 3- [5- (4-tert-Butylphenoxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine acetate is obtained, RT 4.57 min, ESI-MS (M + H) ⁺ 367.45.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidin-5yl mesylate (Compound 1) with biphenyl-4-ol (Compound 2) reacted and then catalytically hydrogenated.

3- [5- (Biphenyl-4-yloxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine acetate is obtained, RT 4.55 min, ESI-MS (M + H) ⁺ 387.44.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidin-5yl mesylate (Compound 1) with isoquinolin-5-ol (Compound 2) reacted and then catalytically hydrogenated.

4- [2-Oxo-5- (isoquinolin-5-yloxymethyl) oxazolidin-3-yl] benzamidine diacetate, RT 1.35 min, ESI-MS (M + H) ⁺ 362.39 are obtained.

According to Reaction Scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3-yl) phenyl] -2-oxo-oxazolidin-5yl mesylate (compound 1) is combined with chroman-6-ol (compound 2) implemented and then catalytically hydrogenated. 3- [5- (Chroman-6-yloxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine acetate is obtained, RT 3.53 min, ESI-MS (M + H) ⁺ 367.41.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) -phenyl] -2-oxo-oxazolidin-5yl mesylate (compound 1) with 3-hydroxy-N- phenyl-benzamide (compound 2) and then catalytically hydrogenated.

3- [3- (3-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] - N-phenyl-benzamide acetate, RT 3.91 min, ESI-MS (M + H) ⁺ 430, 47th

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with (3-hydroxy- phenyl) pyrrolidin-1-yl-methanone (compound 2) implemented and then catalytically hydrogenated.

3- {2-Oxo-5- [3- (1-pyrrolidin-1-yl-methanoyl) phenoxymethyl] oxazolidin-3-yl} benzamidine acetate, RT 2.91 min, ESI-MS (M. + H) ⁺ 408.46.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with (3-hydroxy- phenyl) -morpholin-4-yl-methanone (compound 2) implemented and then catalytically hydrogenated.

3- {5- [3- (1-Morpholin-4-yl-methanoyl) -phenoxymethyl] -2-oxo-oxazolidin-3-yl} -benzamidine acetate, RT 2.37 min, ESI-MS (M. + H) ⁺ 424.46.

According to reaction scheme 2, 343- (5-methyl- [1,2,4] oxadiazol-3- yl) -phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 3-hydroxy-N, N- implemented dimethyl-benzamide (compound 2) and then catalytically hydrogenated.

3- [3- (3-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] - N, N-dimethyl-benzamide acetate, RT 2.19 min, ESI-MS (M + H) ^{+ is obtained} 382.42.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidin-5yl mesylate (Compound 1) with 3-hydroxy-N- (4- implemented methoxy-phenyl) -benzamid (compound 2) and then catalytically hydrogenated.

3- [3- (3-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] - N- (4-methoxy-phenyl) -benzamide acetate, RT 3.92 min, ESI-MS (M. + H) ⁺ 460.49.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with (4-hydroxy- phenyl) pyrrolidin-1-yl-methanone (compound 2) implemented and then catalytically hydrogenated.

3- {2-Oxo-5- [4- (1-pyrrolidin-1-yl-methanoyl) phenoxymethyl] oxazolidin-3-yl} benzamidine acetate, RT 3.03 min, ESI-MS (M. + H) ⁺ 408.46.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with (4-hydroxy- phenyl) -piperidin-1-yl-methanone (compound 2) implemented and then catalytically hydrogenated.

3- {2-Oxo-5- [4- (1-piperidin-1-yl-methanoyl) phenoxymethyl] oxazolidin-3-yl} benzamidine acetate, RT 3.45 min, ESI-MS (M. + H) ⁺ 422.49.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with (4-hydroxy- phenyl) -morpholin-4-yl-methanone (compound 2) implemented and then catalytically hydrogenated.

3- {5- [4- (1-Morpholin-4-yl-methanoyl) -phenoxymethyl] -2-oxo-oxazolidin-3-yl} -benzamidine acetate, RT 2.33 min, ESI-MS (M. + H) ⁺ 424.46.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with (3-hydroxy- phenyl) -piperidin-1-yl-methanone (compound 2) implemented and then catalytically hydrogenated.

3- {2-Oxo-5- [3- (1-piperidin-1-yl-methanoyl) phenoxymethyl] oxazolidin-3-yl} benzamidine acetate, RT 3.31 min, ESI-MS (M. + H) ⁺ 422.49.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) -phenyl] -2-oxo-oxazolidin-5yl mesylate (Compound 1) with 3-hydroxy-N- (3- implemented methoxy-benzyl) -benzamide (compound 2) and then catalytically hydrogenated.

3- [3- (3-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] - N- (3-methoxy-benzyl) -benzamide acetate, RT 3.87 min, ESI-MS (M. + H) ⁺ 474.52.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) -phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 3-hydroxy-N, N- dibutyl-benzamide (compound 2) and then catalytically hydrogenated.

N, N-Dibutyl-3- [3- (3-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] benzamide acetate is obtained, RT 4.81 min, ESI-MS (M + H) ⁺ 466.59.

According to reaction scheme 2, 3- [4- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with (4-hydroxy- phenyl) pyrrolidin-1-yl-methanone (compound 2) implemented and then catalytically hydrogenated.

4- {2-Oxo-5- [4- (1-pyrrolidin-1-yl-methanoyl) phenoxymethyl] oxazolidin-3-yl} benzamidine acetate, RT 3.12 min, ESI-MS (M. + H) ⁺ 408.46.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) -phenyl] -2-oxo-oxazolidine-5yl mesylate (compound 1) with 4-hydroxy-N, N- implemented dipropyl-benzamide (compound 2) and then catalytically hydrogenated.

4- [3- (3-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] - N, N-dipropyl-benzamide acetate, RT 4.11 min, ESI-MS (M + H) ^{+ are obtained} 438.53.

According to reaction scheme 2, 3- [3- (5-methyl- [1,2,4] oxadiazol-3- yl) phenyl] -2-oxo-oxazolidine-5yl mesylate (Compound 1) with 4-hydroxy-N- phenyl-benzamide (compound 2) and then catalytically hydrogenated.

4- [3- (3-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] - N-phenyl-benzamide acetate are obtained, RT 4.06 min, ESI-MS (M + H) ⁺ 430, 47 (.

Claims (9)

1. Use of the compounds of formula I.


wherein
R unsubstituted or single, double or triple by A, Ar, (CH₂)_nAr, OR², OAr, OCF₃, OCOR³, CF₃, NO²)₂, NHAr, Hal, NO₂. CN, (CH₂)_nCOOR², (CH₂)_nCOOAr, (CH₂)_nCONHA, (CH₂)_nCONH cycloalkyl, (CH₂)_nCONA₂, (CH₂)_nCONH (CH₂)_mAr, COR², COAr, SA, S (= O) A, SO₂A, SAr, S (= O) Ar, SO₂Ar, NHCOA, NHCOAr, NHSO₂A, NHSO₂Ar NHSO₂Ar and / or


substituted phenyl, naphthyl, or het¹ is
R¹ H₂N-C (= NH) - is
R² H, A phenyl or benzyl
Ar unsubstituted or single, double or triple by A, OR², OCF₃, CF₃, NO²)₂, Hal, NO₂, CN, (CH₂)_nCOOR². CON (R²)₂, COR², SA, S (= O) A, SO₂A, NHCOA, substituted Cycloalkyl, phenyl, naphthyl, indanyl or het² is
Het¹ an aromatic mono- or dinuclear heterocycle with 1 is up to 4 N, O and / or S atoms,
Het² an aromatic mono- or dinuclear heterocycle with 1 is up to 4 N, O and / or S atoms,
A alkyl having 1 to 8 carbon atoms,
Hal F, Cl, Br, I,
m is 0, 1, 2, or 3
n is 0, 1, 2, 3 or 4,
their stereoisomers and / or their physiologically acceptable salts or Solvate for the manufacture of a medicament for therapy and / or Prophylaxis of diseases with increased expression of the Protease M go hand in hand 2. Use according to claim 1, characterized in that with increased expression of the protease M associated disease Is a tumor or a neurodegenerative disease 3. Use according to claim 2, characterized in that the Tumor disease is a breast, ovary or pancreatic tumor 4. Use according to claim 2, characterized in that the neurogenerative disease Alzheimer's disease or Parkinson's disease is 5. Compounds with the following chemical names:
3- [3- (4-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N-phenylbenzamide;
N-butyl-3- [3- (4-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] benzamide;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N, N-diethyl-benzamide;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N, N-dipropyl-benzamide;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N, N-dibutyl-benzamide;
4- {2-oxo-5- [3- (pyrrolidin-1-carbonyl) phenoxymethyl] oxazolidin-3-yl} benzamidine;
4- {2-oxo-5- [3- (piperidin-1-carbonyl) phenoxymethyl] oxazolidin-3-yl} benzamidine;
4- {5- [3- (morpholine-1-carbonyl) phenoxymethyl] -2-oxo-oxazolidin-3-yl} benzamidine;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N-cyclohexyl-benzamide;
N-benzyl-3- [3- (4-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] benzamide;
3- [3- (4-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N-ethylbenzamide;
3- [3- (4-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N-propylbenzamide;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (3-flouro-benzyl) benzamide;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (4-flouro-benzyl) benzamide;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (4-methyl-benzyl) benzamide;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (3-methoxy-benzyl) benzamide;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (4-methoxy-benzyl) benzamide;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (4-triflouromethoxy-benzyl) benzamide;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N-phenethyl-benzamide;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (3-methoxy-phenethyl) benzamide;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (3,4-dimethoxy-phenethyl) benzamide;
3- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (4-methoxyphenethyl) benzamide
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (4-fluorophenyl) benzamide;
3- [3- (4-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (4-methylphenyl) benzamide;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (3-methoxy-phenyl) benzamide;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N, N-dimethyl-benzamide;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (3,4,5-trimethoxy-phenyl) benzamide;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N-thiazol-2-yl-benzamide;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (4-methoxy-phenyl) benzamide;
4- {5- [4- (5-methyl-pyridin-2-yl) phenoxymethyl] -2-oxo-oxazolidin-3-yl} benzamidine;
2- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N, N-dimethyl-benzamide;
4- {5- [3-methyl-4- (2-methyl-4-oxo-4H-quinazolin-3-yl) phenoxymethyl] -2-oxo-oxazolidin-3-yl} benzamidine;
5- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -2-methyl-1-propyl-1H-indole-3-carboxylic acid ethyl ester;
4- {5- [4- (4-acetyl-piperazin-1-yl) phenoxymethyl] -2-oxo-oxazolidin-3-yl} - benzamidine;
4- {2-oxo-5- [4- (1,3,5-trimethyl-1H-pyrazol-4-ylmethyl) phenoxymethyl] oxazolidin-3-yl} benzamidine;
4- [2-oxo-5- (2-piperidin-1-yl-phenoxymethyl) oxazolidin-3-yl] -benzamidine;
4- [5- (2-morpholin-4-yl-phenoxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine;
4- [2-oxo-5- (3-piperidin-1-yl-phenoxymethyl) oxazolidin-3-yl] -benzamidine;
4- [5- (4-imidazol-1-yl-phenoxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
4- [5- (3-Acetyl-phenoxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
{4- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] phenyl} ethyl acetate;
N- {4- [3- (4-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] phenyl} acetamide;
2- [3- (4-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N-phenylbenzamide;
4- {2-oxo-5- [4- (2-p-tolyl-ethyl) phenoxymethyl] oxazolidin-3-yl} benzamidine;
2- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -4-methoxy-benzoic acid methyl ester;
4- [2-oxo-5- (4-propoxy-phenoxymethyl) oxazolidin-3-yl] -benzamidine;
4- {2-oxo-5- [4- (4-propylcyclohexyl) phenoxymethyl] oxazolidin-3-yl} benzamidine;
4- [5- (naphthalene-1-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
4- [5- (naphthalene-2-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
4- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] ethyl benzoate;
Methyl 2- [3- (4-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] benzoate;
2- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] ethyl benzoate;
4- [2-oxo-5- (3-trifluoromethylphenoxymethyl) oxazolidin-3-yl] benzamidine;
4- [5- (4-cyclohexyl-phenoxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
4- [5- (2,4-dichloro-6-piperidin-1-ylmethylphenoxymethyl) -2-oxooxazolidin-3-yl] benzamidine;
4- [5- (2-benzyl-4-chlorophenoxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine;
4- [5- (chroman-6-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
4- [5- (4-indan-1-yl-phenoxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
3- {4- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] phenyl} propionic acid methyl ester;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] methyl benzoate;
4- [5- (6-methoxy-naphthalene-2-yloxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine;
4- [2-oxo-5- (4-trifluoromethoxyphenoxymethyl) oxazolidin-3-yl] benzamidine;
4- [5- (1H-indol-5-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
4- [2-oxo-5- (4-phenoxy-phenoxymethyl) oxazolidin-3-yl] -benzamidine;
4- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] dimethyl phthalate;
4- [3- (4-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -3-propyl-benzoic acid methyl ester;
4- [2-oxo-5- (4-propionyl-phenoxymethyl) oxazolidin-3-yl] -benzamidine;
4- [5- (4-acetyl-2-methoxyphenoxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine;
4- [5- (4-propionyl-2-methoxy-phenoxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine;
2- [3- (4-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N, N-bis (3-methylbutyl) benzamide;
N- {4- [3- (4-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] -3-methyl-naphthalene-1-yl} acetamide;
4- [2-oxo-5- (2-trifluoromethylphenoxymethyl) oxazolidin-3-yl] benzamidine;
4- [5- (Biphenyl-3-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
4- [2-oxo-5- (3-phenoxy-phenoxymethyl) oxazolidin-3-yl] -benzamidine;
4- [5- (biphenyl-4-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
N- {2- [3- (4-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] phenyl} acetamide;
2- [3- (3-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -4-methoxy-benzoic acid methyl ester;
3- [2-oxo-5- (4-propoxy-phenoxymethyl) oxazolidin-3-yl] -benzamidine;
3- {2-Oxo-5- [4- (4-propylcyclohexyl) phenoxymethyl] oxazolidin-3-yl} benzamidine;
3- [5- (naphthalene-1-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
3- [5- (naphthalene-2-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
2- [3- (3-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] ethyl benzoate;
3- [5- (4-cyclohexyl-phenoxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
3- [5- (2,4-dichloro-6-piperidin-1-ylmethylphenoxymethyl) -2-oxooxazolidin-3-yl] benzamidine;
3- [5- (2-benzyl-4-chlorophenoxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine;
3- {5- (5-methyl-2- (3-phenyl-propyl) phenoxymethyl] -2-oxo-oxazolidin-3-yl} benzamidine;
4- [5- (2-Acetyl-phenoxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
4- [5- (4-tert-Butyl-phenoxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
3- {2-Oxo-5- [4- (2-p-tolyl-ethyl) phenoxymethyl] oxazolidin-3-yl} benzamidine;
2- [3- (3-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N-phenyl-benzamide;
3- [5- (4-indan-1-yl-phenoxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
Methyl 3- {4- [3- (3-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] phenyl} propionate;
3- [5- (7-methoxy-naphthalene-2-yloxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine;
3- [5- (6-methoxy-naphthalene-2-yloxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine;
3- [3- (3-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] methyl benzoate;
4- [5- (3-Acetyl-phenoxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
3- [5- (2-methyl-1H-indol-4-yloxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine;
N- {4- [3- (3-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] phenyl} acetamide;
Methyl 2- [3- (3-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] benzoate;
4- [3- (3-Carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] ethyl benzoate;
3- [2-oxo-5- (3-trifluoromethylphenoxymethyl) oxazolidin-3-yl] benzamidine;
3- [2-oxo-5- (4-phenoxy-phenoxymethyl) oxazolidin-3-yl] -benzamidine;
N- {2- [3- (3-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] phenyl} acetamide;
4- [5- (Benzo [1,3] dioxol-5-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
3- [2-oxo-5- (quinolin-6-yloxymethyl) oxazolidin-3-yl] -benzamidine;
4- [3- (3-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] dimethyl phthalate;
4- [3- (3-Carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] -3-propylbenzoic acid methyl ester;
3- [2-oxo-5- (4-propionyl-phenoxymethyl) oxazolidin-3-yl] -benzamidine;
3- [5- (4-acetyl-2-methoxy-phenoxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine;
3- [2-oxo-5- (3-phenoxy-phenoxymethyl) oxazolidin-3-yl] -benzamidine;
3- [5- (Biphenyl-3-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
3- [2-oxo-5- (2-trifluoromethylphenoxymethyl) oxazolidin-3-yl] benzamidine;
N- {4- [3- (3-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -3-methyl-naphthalene-1-yl} acetamide;
2- [3- (3-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N, N-bis (3-methylbutyl) benzamide;
3- [5- (2-methoxy-4-propionylphenoxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine;
4- [5- (2-acetyl-4-bromo-phenoxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine;
3- [5- (isoquinoline-5-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
3- [3- (4-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] phenyl acetic acid ester;
4- [2-oxo-5- (quinolin-8-yloxymethyl) oxazolidin-3-yl] -benzamidine;
4- [2-oxo-5- (quinolin-5-yloxymethyl) oxazolidin-3-yl] -benzamidine;
4- [5- (2-methoxy-4-morpholin-4-ylmethylphenoxymethyl) -2-oxooxazolidin-3-yl] benzamidine;
3- [2-oxo-5- (quinolin-8-yloxymethyl) oxazolidin-3-yl] -benzamidine;
4- [5- (1H-indol-6-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
4- {5- [4- (4-Methyl-4H- [1, 2, 4] triazol-3-yl) phenoxymethyl] -2-oxo-oxazolidin-3-yl} benzamidine;
3- [5- (1H-indol-5-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
3- [5- (Benzo [1, 3] dioxol-5-yloxymethyl) -2-oxo-oxazolidin-3-yl] benzamidine;
3- [5- (4-tert-Butyl-phenoxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
3- [5- (biphenyl-4-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
4- [2-oxo-5- (isoquinolin-5-yloxymethyl) oxazolidin-3-yl] -benzamidine;
3- [5- (chroman-6-yloxymethyl) -2-oxo-oxazolidin-3-yl] -benzamidine;
3- [3- (3-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N-phenyl-benzamide;
3- {2-Oxo-5- [3- (1-pyrrolidin-1-yl-methanoyl) phenoxymethyl] oxazolidin-3-yl} benzamidine;
3- {5- [3- (1-morpholin-4-yl-methanoyl) phenoxymethyl] -2-oxo-oxazolidin-3-yl} benzamidine;
3- [3- (3-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N, N-dimethyl-benzamide;
3- [3- (3-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (4-methoxy-phenyl) benzamide;
3- {2-oxo-5- [4- (1-pyrrolid in-1-yl-methanoyl) phenoxymethyl] oxazolidin-3-yl} benzamidine;
3- {2-oxo-5- [4- (1-piperidin-1-yl-methanoyl) phenoxymethyl] oxazolidin-3-yl} benzamidine;
3- {2-oxo-5- [3- (1-piperidin-1-yl-methanoyl) phenoxymethyl] oxazolidin-3-yl} benzamidine;
3- [3- (3-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N- (3-methoxy-benzyl) benzamide;
N, N -dibutyl-3- [3- (3-carbamimidoylphenyl) -2-oxo-oxazolidin-5-ylmethoxy] benzamide;
4- {2-oxo-5- [4- (1-pyrrolidin-1-yl-methanoyl) phenoxymethyl] oxazolidin-3-yl} benzamidine;
4- [3- (3-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N, N-dipropyl-benzamide;
4- [3- (3-carbamimidoyl-phenyl) -2-oxo-oxazolidin-5-ylmethoxy] -N-phenyl-benzamide
their stereoisomers and / or their physiologically acceptable salts or solvates 6. Compounds according to claim 5, their stereoisomers and / or their physiologically acceptable salts or solvates as medicinal substances 7. Use of the compounds according to claim 5, the Stereoisomers and / or their physiologically acceptable salts or Solvates as integrin and / or protease M inhibitors 8. Use of the compounds according to claim 5, the Stereoisomers and / or their physiologically acceptable salts or Solvate for the manufacture of a medicament for prophylaxis and / or Therapy of tumor diseases and / or neurodegerative diseases 9. Preparation containing at least one of the compounds according to Claim 5, their stereoisomers and / or one of their physiological harmless salts or solvates