MXPA96001659A - Antagonists of the receiver of accession, procedure to prepare them, pharmaceutical compositions that contain them and its employment to prepare medicines, and fight against pharmacy - Google Patents
Antagonists of the receiver of accession, procedure to prepare them, pharmaceutical compositions that contain them and its employment to prepare medicines, and fight against pharmacyInfo
- Publication number
- MXPA96001659A MXPA96001659A MXPA/A/1996/001659A MX9601659A MXPA96001659A MX PA96001659 A MXPA96001659 A MX PA96001659A MX 9601659 A MX9601659 A MX 9601659A MX PA96001659 A MXPA96001659 A MX PA96001659A
- Authority
- MX
- Mexico
- Prior art keywords
- phenyl
- oxazolidin
- piperazinomethyl
- formula
- compound
- Prior art date
Links
- 239000003814 drug Substances 0.000 title claims abstract description 10
- 229940079593 drugs Drugs 0.000 title claims abstract description 6
- 238000000034 method Methods 0.000 title claims description 3
- 230000003042 antagnostic Effects 0.000 title 1
- 239000005557 antagonist Substances 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 110
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 239000011780 sodium chloride Substances 0.000 claims abstract description 19
- 230000000875 corresponding Effects 0.000 claims abstract description 9
- 239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- -1 N-pyridylcarbonylamidino Chemical group 0.000 claims description 285
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 29
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- 150000001408 amides Chemical class 0.000 claims description 8
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 238000003797 solvolysis reaction Methods 0.000 claims description 5
- 230000001131 transforming Effects 0.000 claims description 5
- 241000143392 Oar Species 0.000 claims description 4
- 229910052770 Uranium Inorganic materials 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims description 3
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 3
- XUJNEKJLAYXESH-REOHCLBHSA-N L-cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims description 3
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 3
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims description 3
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 3
- 125000000393 L-methionino group Chemical group [H]OC(=O)[C@@]([H])(N([H])[*])C([H])([H])C(SC([H])([H])[H])([H])[H] 0.000 claims description 3
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 3
- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 claims description 3
- MTCFGRXMJLQNBG-REOHCLBHSA-N L-serine Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 3
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims description 3
- 125000000510 L-tryptophano group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C(C([H])([H])[C@@]([H])(C(O[H])=O)N([H])[*])C2=C1[H] 0.000 claims description 3
- 238000005917 acylation reaction Methods 0.000 claims description 3
- 125000000539 amino acid group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims description 3
- 210000004940 Nucleus Anatomy 0.000 claims description 2
- 230000002152 alkylating Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- 230000003301 hydrolyzing Effects 0.000 claims description 2
- 101700041618 nhr-4 Proteins 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- 101700033614 COR2 Proteins 0.000 claims 3
- 101710008836 UQCRC2 Proteins 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 239000007788 liquid Substances 0.000 claims 2
- YIWFXZNIBQBFHR-LURJTMIESA-N Gly-His Chemical compound [NH3+]CC(=O)N[C@H](C([O-])=O)CC1=CN=CN1 YIWFXZNIBQBFHR-LURJTMIESA-N 0.000 claims 1
- 201000011082 combat disease Diseases 0.000 claims 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 108010020688 glycylhistidine Proteins 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 230000027455 binding Effects 0.000 abstract description 7
- 201000010099 disease Diseases 0.000 abstract description 5
- 229940012952 Fibrinogen Drugs 0.000 abstract description 4
- 102000008946 Fibrinogen Human genes 0.000 abstract description 4
- 108010049003 Fibrinogen Proteins 0.000 abstract description 4
- 229940019698 Fibrinogen containing hemostatics Drugs 0.000 abstract description 4
- 201000009910 diseases by infectious agent Diseases 0.000 abstract description 4
- 206010003210 Arteriosclerosis Diseases 0.000 abstract description 2
- 206010061255 Ischaemia Diseases 0.000 abstract description 2
- 208000010125 Myocardial Infarction Diseases 0.000 abstract description 2
- 208000001132 Osteoporosis Diseases 0.000 abstract description 2
- 208000006011 Stroke Diseases 0.000 abstract description 2
- 208000007536 Thrombosis Diseases 0.000 abstract description 2
- 230000000010 osteolytic Effects 0.000 abstract description 2
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 69
- 239000000126 substance Substances 0.000 description 31
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 17
- 239000002904 solvent Substances 0.000 description 14
- JHUATQWONBPLLJ-UHFFFAOYSA-N C(C)OC(=O)CNC(=O)NC(=N)C1=CC=C(C=C1)N1C(OC(C1C)OS(=O)(=O)C)=O Chemical compound C(C)OC(=O)CNC(=O)NC(=N)C1=CC=C(C=C1)N1C(OC(C1C)OS(=O)(=O)C)=O JHUATQWONBPLLJ-UHFFFAOYSA-N 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- RTRFMODFVFPWRN-UHFFFAOYSA-N C1(=CC=CC=C1)C(C(=O)NC(=N)C1=CC=C(C=C1)N1C(OC(C1C)OS(=O)(=O)C)=O)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)C(C(=O)NC(=N)C1=CC=C(C=C1)N1C(OC(C1C)OS(=O)(=O)C)=O)C1=CC=CC=C1 RTRFMODFVFPWRN-UHFFFAOYSA-N 0.000 description 11
- OQCCNPXLRPWFHH-UHFFFAOYSA-N [2-oxo-3-[4-[N'-(thiophene-3-carbonyl)carbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl methanesulfonate Chemical compound O=C1OC(COS(=O)(=O)C)CN1C1=CC=C(C(N)=NC(=O)C2=CSC=C2)C=C1 OQCCNPXLRPWFHH-UHFFFAOYSA-N 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 125000006239 protecting group Chemical group 0.000 description 11
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- OXRCBTMOGGCQAW-UHFFFAOYSA-N [2-oxo-3-[4-[N'-(pyridine-3-carbonyl)carbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl methanesulfonate Chemical compound O=C1OC(COS(=O)(=O)C)CN1C1=CC=C(C(=N)NC(=O)C=2C=NC=CC=2)C=C1 OXRCBTMOGGCQAW-UHFFFAOYSA-N 0.000 description 9
- QLWLJCOPSYTUKL-UHFFFAOYSA-N [3-[4-[N'-(naphthalene-2-carbonyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate Chemical compound O=C1OC(COS(=O)(=O)C)CN1C1=CC=C(C(N)=NC(=O)C=2C=C3C=CC=CC3=CC=2)C=C1 QLWLJCOPSYTUKL-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000004305 biphenyl Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 230000002401 inhibitory effect Effects 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- NYKGPOPKUKHGSH-UHFFFAOYSA-N [2-oxo-3-[4-[N'-(thiophene-2-carbonyl)carbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl methanesulfonate Chemical compound O=C1OC(COS(=O)(=O)C)CN1C1=CC=C(C(N)=NC(=O)C=2SC=CC=2)C=C1 NYKGPOPKUKHGSH-UHFFFAOYSA-N 0.000 description 7
- 150000002825 nitriles Chemical class 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- KGHXFBVYXDFJGG-UHFFFAOYSA-N (2-carbamoylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1C(N)=O KGHXFBVYXDFJGG-UHFFFAOYSA-N 0.000 description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N Perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 5
- 238000007792 addition Methods 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 5
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- HUSYTLMIRXITQS-UHFFFAOYSA-N 1,3-benzodioxole-5-carboxamide Chemical compound NC(=O)C1=CC=C2OCOC2=C1 HUSYTLMIRXITQS-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- RBGDLYUEXLWQBZ-UHFFFAOYSA-N 2-chlorobenzamide Chemical compound NC(=O)C1=CC=CC=C1Cl RBGDLYUEXLWQBZ-UHFFFAOYSA-N 0.000 description 4
- VKPLPDIMEREJJF-UHFFFAOYSA-N 3-Methoxybenzamide Chemical compound COC1=CC=CC(C(N)=O)=C1 VKPLPDIMEREJJF-UHFFFAOYSA-N 0.000 description 4
- KWAYEPXDGHYGRW-UHFFFAOYSA-N 3-nitrobenzamide Chemical compound NC(=O)C1=CC=CC([N+]([O-])=O)=C1 KWAYEPXDGHYGRW-UHFFFAOYSA-N 0.000 description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 4
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- GUCPYIYFQVTFSI-UHFFFAOYSA-N 4-methoxybenzamide Chemical compound COC1=CC=C(C(N)=O)C=C1 GUCPYIYFQVTFSI-UHFFFAOYSA-N 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- MTFCXMJOGMHYAE-UHFFFAOYSA-N ethyl 2-piperazin-1-ylacetate Chemical compound CCOC(=O)CN1CCNCC1 MTFCXMJOGMHYAE-UHFFFAOYSA-N 0.000 description 4
- XCLNGVSHLDOGFR-UHFFFAOYSA-N ethyl 3-piperazin-1-ylpropanoate Chemical compound CCOC(=O)CCN1CCNCC1 XCLNGVSHLDOGFR-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- MJTGQALMWUUPQM-UHFFFAOYSA-N m-Chlorobenzamide Chemical compound NC(=O)C1=CC=CC(Cl)=C1 MJTGQALMWUUPQM-UHFFFAOYSA-N 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000007127 saponification reaction Methods 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 210000004881 tumor cells Anatomy 0.000 description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 3
- MNWSGMTUGXNYHJ-UHFFFAOYSA-N 2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(N)=O MNWSGMTUGXNYHJ-UHFFFAOYSA-N 0.000 description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 3
- VYZIRLYFWZFTRE-UHFFFAOYSA-N 3-tert-butylbenzamide Chemical compound CC(C)(C)C1=CC=CC(C(N)=O)=C1 VYZIRLYFWZFTRE-UHFFFAOYSA-N 0.000 description 3
- FUKWTMJZHKZKFA-UHFFFAOYSA-N 4-cyanobenzamide Chemical compound NC(=O)C1=CC=C(C#N)C=C1 FUKWTMJZHKZKFA-UHFFFAOYSA-N 0.000 description 3
- VNDHYTGVCGVETQ-UHFFFAOYSA-N 4-fluorobenzamide Chemical compound NC(=O)C1=CC=C(F)C=C1 VNDHYTGVCGVETQ-UHFFFAOYSA-N 0.000 description 3
- VIPMBJSGYWWHAO-UHFFFAOYSA-N 4-tert-butylbenzamide Chemical compound CC(C)(C)C1=CC=C(C(N)=O)C=C1 VIPMBJSGYWWHAO-UHFFFAOYSA-N 0.000 description 3
- QSERSMGSTOWXRP-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)NC(=N)C1=CC=C(C=C1)N1C(OC(C1C)OS(=O)(=O)C)=O Chemical compound C(C1=CC=CC=C1)(=O)NC(=N)C1=CC=C(C=C1)N1C(OC(C1C)OS(=O)(=O)C)=O QSERSMGSTOWXRP-UHFFFAOYSA-N 0.000 description 3
- GBRQGIDFGGMGAJ-SCSAIBSYSA-N CS(=O)(=O)O[C@H]1N(C(OC1)=O)C Chemical compound CS(=O)(=O)O[C@H]1N(C(OC1)=O)C GBRQGIDFGGMGAJ-SCSAIBSYSA-N 0.000 description 3
- 108010012088 Fibrinogen Receptors Proteins 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M Potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 230000000845 anti-microbial Effects 0.000 description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- CTKINSOISVBQLD-UHFFFAOYSA-N glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 235000011007 phosphoric acid Nutrition 0.000 description 3
- 230000002633 protecting Effects 0.000 description 3
- 230000001681 protective Effects 0.000 description 3
- 238000006894 reductive elimination reaction Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- BQQIZPBPWABFMD-UHFFFAOYSA-N (2-acetyloxyphenyl) 2-piperazin-1-ylacetate Chemical compound CC(=O)OC1=CC=CC=C1OC(=O)CN1CCNCC1 BQQIZPBPWABFMD-UHFFFAOYSA-N 0.000 description 2
- RXYGDNDJKRGCPY-UHFFFAOYSA-N (2-acetyloxyphenyl) 3-piperazin-1-ylpropanoate Chemical compound CC(=O)OC1=CC=CC=C1OC(=O)CCN1CCNCC1 RXYGDNDJKRGCPY-UHFFFAOYSA-N 0.000 description 2
- NMHFFQUOUKGBCV-UHFFFAOYSA-N (2-acetyloxyphenyl) piperidine-4-carboxylate Chemical compound CC(=O)OC1=CC=CC=C1OC(=O)C1CCNCC1 NMHFFQUOUKGBCV-UHFFFAOYSA-N 0.000 description 2
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- BCXYJDOYBPPMIU-UHFFFAOYSA-N ethyl 2-[[(E)-[amino-[4-[5-[[4-(2-methoxy-2-oxoethyl)piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]phenyl]methylidene]carbamoyl]amino]acetate Chemical compound C1=CC(C(=N)NC(=O)NCC(=O)OCC)=CC=C1N1C(=O)OC(CN2CCN(CC(=O)OC)CC2)C1 BCXYJDOYBPPMIU-UHFFFAOYSA-N 0.000 description 1
- SPPPGZJRYNPMIB-UHFFFAOYSA-N ethyl 3-(2-oxopiperazin-1-yl)propanoate Chemical compound CCOC(=O)CCN1CCNCC1=O SPPPGZJRYNPMIB-UHFFFAOYSA-N 0.000 description 1
- QFLUAFNPEWPCEO-UHFFFAOYSA-N ethyl 3-[4-[4-[4-(5-phenyl-2,5-dihydro-1,2,4-oxadiazol-3-yl)phenyl]piperazin-1-yl]piperidin-1-yl]propanoate Chemical compound C1CN(CCC(=O)OCC)CCC1N1CCN(C=2C=CC(=CC=2)C=2NC(ON=2)C=2C=CC=CC=2)CC1 QFLUAFNPEWPCEO-UHFFFAOYSA-N 0.000 description 1
- RWRDBYPTGATGQD-UHFFFAOYSA-N ethyl 3-[4-[[2-oxo-3-[4-[N'-(pyridine-3-carbonyl)carbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C1CN(CCC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2C=NC=CC=2)C1 RWRDBYPTGATGQD-UHFFFAOYSA-N 0.000 description 1
- AHOXLNQGJUNVGF-UHFFFAOYSA-N ethyl 3-[4-[[3-[4-[(Z)-N'-methoxycarbonylcarbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C1CN(CCC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)OC)C1 AHOXLNQGJUNVGF-UHFFFAOYSA-N 0.000 description 1
- OTRLBMMYYBMRKS-UHFFFAOYSA-N ethyl 3-[4-[[3-[4-[N'-(2,2-diphenylacetyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]-2-oxopiperazin-1-yl]propanoate Chemical compound C1C(=O)N(CCC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C(C=2C=CC=CC=2)C=2C=CC=CC=2)C1 OTRLBMMYYBMRKS-UHFFFAOYSA-N 0.000 description 1
- JBBGVWZYIGDIQB-UHFFFAOYSA-N ethyl 3-[4-[[3-[4-[N'-(furan-2-carbonyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C1CN(CCC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2OC=CC=2)C1 JBBGVWZYIGDIQB-UHFFFAOYSA-N 0.000 description 1
- LBLDYNJURQURLW-UHFFFAOYSA-N ethyl 3-[4-[[3-[4-[N'-(furan-3-carbonyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C1CN(CCC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)C2=COC=C2)C1 LBLDYNJURQURLW-UHFFFAOYSA-N 0.000 description 1
- JACVLZSXXLWSLB-UHFFFAOYSA-N ethyl 3-[4-[[3-[4-[N'-(naphthalene-2-carbonyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]-2-oxopiperazin-1-yl]propanoate Chemical compound C1C(=O)N(CCC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2C=C3C=CC=CC3=CC=2)C1 JACVLZSXXLWSLB-UHFFFAOYSA-N 0.000 description 1
- JFTKGDYJMNVIGE-UHFFFAOYSA-N ethyl 3-amino-3-[4-[4-(1-benzoylpiperidin-4-yl)butoxy]phenyl]propanoate Chemical compound C1=CC(C(N)CC(=O)OCC)=CC=C1OCCCCC1CCN(C(=O)C=2C=CC=CC=2)CC1 JFTKGDYJMNVIGE-UHFFFAOYSA-N 0.000 description 1
- LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 description 1
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- AVXURJPOCDRRFD-UHFFFAOYSA-N hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
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- UHHVABRWHRKEPJ-UHFFFAOYSA-N methyl 2-piperazin-1-ylacetate Chemical compound COC(=O)CN1CCNCC1 UHHVABRWHRKEPJ-UHFFFAOYSA-N 0.000 description 1
- GGRRUFUYQMNALV-UHFFFAOYSA-N methyl 3-[4-[[2-oxo-3-[4-[N'-(pyridine-3-carbonyl)carbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C1CN(CCC(=O)OC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2C=NC=CC=2)C1 GGRRUFUYQMNALV-UHFFFAOYSA-N 0.000 description 1
- BVNFBHOJDPAZAX-UHFFFAOYSA-N methyl 3-piperazin-1-ylpropanoate Chemical compound COC(=O)CCN1CCNCC1 BVNFBHOJDPAZAX-UHFFFAOYSA-N 0.000 description 1
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
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- MSNZFDLOGHAYJE-UHFFFAOYSA-N pent-1-yn-3-amine Chemical compound CCC(N)C#C MSNZFDLOGHAYJE-UHFFFAOYSA-N 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
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- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 1
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- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical class [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
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- DOMOUWQXQOINLG-UHFFFAOYSA-N propan-2-yl 2-[4-[[2-oxo-3-[4-[N'-(pyridine-3-carbonyl)carbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OC(C)C)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2C=NC=CC=2)C1 DOMOUWQXQOINLG-UHFFFAOYSA-N 0.000 description 1
- ZAKNQUXQBXUUEX-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[4-(N'-methoxycarbonylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1=CC(C(\N)=N/C(=O)OC)=CC=C1N1C(=O)OC(CN2CCN(CC(=O)OC(C)C)CC2)C1 ZAKNQUXQBXUUEX-UHFFFAOYSA-N 0.000 description 1
- DBIFIBMDPBKVAX-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[4-[N'-(2,2-diphenylacetyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OC(C)C)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C(C=2C=CC=CC=2)C=2C=CC=CC=2)C1 DBIFIBMDPBKVAX-UHFFFAOYSA-N 0.000 description 1
- VXYBLWJBEGBJTE-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[4-[N'-(furan-3-carbonyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OC(C)C)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C2=COC=C2)C1 VXYBLWJBEGBJTE-UHFFFAOYSA-N 0.000 description 1
- BNKBSNJRZATVOM-UHFFFAOYSA-N propan-2-yl 2-piperazin-1-ylacetate Chemical compound CC(C)OC(=O)CN1CCNCC1 BNKBSNJRZATVOM-UHFFFAOYSA-N 0.000 description 1
- WWCTWVNCFHPPKJ-UHFFFAOYSA-N propan-2-yl 3-[4-[[2-oxo-3-[4-[N'-(pyridine-3-carbonyl)carbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C1CN(CCC(=O)OC(C)C)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2C=NC=CC=2)C1 WWCTWVNCFHPPKJ-UHFFFAOYSA-N 0.000 description 1
- LTNGKVOTLYKNED-UHFFFAOYSA-N propan-2-yl 3-[4-[[3-[4-[N'-(2,2-diphenylacetyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C1CN(CCC(=O)OC(C)C)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C(C=2C=CC=CC=2)C=2C=CC=CC=2)C1 LTNGKVOTLYKNED-UHFFFAOYSA-N 0.000 description 1
- RGJAFHGYUIPYRT-UHFFFAOYSA-N propan-2-yl 3-piperazin-1-ylpropanoate Chemical compound CC(C)OC(=O)CCN1CCNCC1 RGJAFHGYUIPYRT-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
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- CUGQEEGDFRXWRU-UHFFFAOYSA-N tert-butyl 3-[4-[[3-[4-[N'-(2,2-diphenylacetyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C1CN(CCC(=O)OC(C)(C)C)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C(C=2C=CC=CC=2)C=2C=CC=CC=2)C1 CUGQEEGDFRXWRU-UHFFFAOYSA-N 0.000 description 1
- BWTRHKJAKYHTLL-UHFFFAOYSA-N tert-butyl 3-piperazin-1-ylpropanoate Chemical compound CC(C)(C)OC(=O)CCN1CCNCC1 BWTRHKJAKYHTLL-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Abstract
The invention relates to the compounds of formula I: wherein R1, R2 and R3 have the meanings indicated in claim 1, and to their physiologically acceptable salts. It also relates to a process for preparing said compounds, to a pharmaceutical preparation containing them and to the use thereof for preparing drugs and combating diseases. These compounds inhibit the binding of fibrinogen to its corresponding receptor, and can be used for the treatment of thrombosis, osteoporosis, tumor diseases, strokes, myocardial infarction, ischemia, infections, arteriosclerosis and osteolytic diseases.
Description
-PARING MEDICATIONS, AND COMBATING DISEASES DESCRIPTION OF THE INVENTION The invention relates to the new adhesion receptor antagonists, of formula I
(i) where R represents
wherein B = CH2, CO or CS, R1"= OH or H and m = 0, 1, 2, 3 or 4;
where B - CH2, CO or CS, U = CH1 or CO and R '= H, C02H or C02A? n = 0, 1, 2 or 3;
where n = 1, 2, 3, or 4;
where R4 = H, A-S02, Ar-S02, A-CO, Ar-CO or Het-CO;
wherein R5 = H, A, alkynyl or alkenyl of 2 to 5 carbon atoms or Ar;
where D, E, F and G represent each time, independently of one another, CH or N and y 1 represent each time, independently of one another, 0, 1, 2, 3 or 4, with the exception of k = 0 , when E and F are each N, and of 1 = 0, when G = N;
wherein As is an amino acid residue selected from the group consisting of Ala, Arg, Asn, Asp, Cys, Gln, Glu, Gly, His, Lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr or Val, and which is linked through peptide bonds;
where R6"= - H or A and m independently represents 0, 1, 2, 3, or 4 each time
wherein R7 = OH, OA, OAr, OHet, NHOH, NH2, NHA or NA2, R8 = H or A and n is independently 1, 2, 3 or 4 each time; or
R4 where R4 has the meaning indicated in (d) and p is 2, 3, 4, 5, or 6; R1 represents H, A, Ar-CO, A-CO, OH, OA or AO-CO; R2 represents OH, OA, OAr, OHet, NHOH, NH2, NHA or NA2; R3 represents A-CO, Ar-CO, Het-CO, Het-0-CO, Ar-O-CO, A-O-CO-, Ar-S02 or A-S02; A represents alkyl of 1 to 6 carbon atoms; Ar is diphenyl ethyl, benzyl or aryl of 6 to 10 C atoms unsubstituted or substituted one or two times with A, F, Cl, Br, I, OA, -0-CH2-0, COOA, COOH, CF3, OH, N02, CN. O- CO-A, NH2, NHA or NA2 and Het is a saturated, unsaturated or aromatic heterocycle, of one or two nuclei and containing 1 to 4 N, O and / or N atoms.
S, which may be unsubstituted or monosubstituted with F, Cl, Br, CF3, A, OH, OA, CN or N02, and their salts acceptable from the physiological point of view. In the European document Al-0 0 623 615 (German document 43 14 378) similar compounds are disclosed. The aim of the invention was to develop new compounds with valuable properties, in particular compounds that can be used in the manufacture of medicines. This objective was achieved by the present invention.
It was found that the compounds of formula I and their salts or hydrates possess valuable pharmacological properties and are well tolerated. First of all they act as inhibitors of integrin, in particular, by inhibiting the interaction of the β3 or β5 integrin receptors with the ligands. These compounds have a particular effect in the case of integrins avß3, aß, and apbß3. This effect can be checked, for example, according to the method described by J.W. Smith et al. in J. Biol. Chem. 265. p.12267-12271 (1990). In particular, they inhibit the binding of fibrinogen, fibronectin and Willebrand factor to the platelet fibrinogen receptor (glycoprotein Ilb / IIIa), and also the binding of these and other adhesive proteins such as vitronectin, collagen and laminin, to the corresponding receptors on the surface of different cell types. Thus, the compounds affect intercellular interactions and cell-matrix interactions. In particular, they inhibit the formation of platelet thrombi and, therefore, can be used for the treatment of thrombosis, strokes, myocardial infarction, angina pectoris, osteolytic diseases, in particular osteoporosis and restenosis after angioplasties, ischaemia, infections , arteriosclerosis and acute renal insufficiency. The compounds also inhibit or inhibit vascularization, so they exhibit an anti-angiogenic effect. In addition, they exert an effect on tumor cells by inhibiting their metastasis. Consequently, they can also be used as anti-tumor agents. There are indications that the tumor cells are injected into the vessels by means of microthrombi and thus protect themselves from detection by the cells of the immune system. Likewise, microthrombi contribute to the union of tumor cells to the walls of the vessels. Since the formation of microthrombi is related to the binding of fibrinogen to the fibrinogen receptor (glycoprotein Ilb / IIIa), inhibitors of fibrinogen binding also act as inhibitors of metastasis. Through its anti-angiogenic properties prevent the supply of blood and nutrients to tumor cells. In addition, the compounds are suitable for use as substances with an antimicrobial effect, capable of inhibiting the infections produced, for example, by bacteria, fungi or yeasts. Therefore, the substances can preferably be administered as additional antimicrobial substances when carrying out interventions by which foreign materials are introduced or placed in the body, such as biological materials, implants, a catheter or a pacemaker. These substances act as antiseptic materials. The antimicrobial activities of the compounds can be checked, for example, according to the method of P.Valentin-Weigand et al. described in "Infection and Immunity", p. 2851-2855 (1988). The other properties of the compounds can be checked according to the methods described in European document A1-0 462 960. The inhibition of fibrin binding to the fibrinogen receptor can be checked according to the method described in the European document Al-0 381 033. The inhibitory effect of trobite aggregation can be checked in vitro according to the Born method (Nature 4832, page 927-929, 1962). Another object of the present invention is a process for preparing a compound of formula I and its salts, characterized in that (i) a compound of formula I is released from one of its functional derivatives by solvolysis or hydrogenolysis with a suitable agent, or because (ii) ) a compound of formula II is reacted
wherR, R1 and R2 have the indicated meanings, with a compound of formula III R3-X (III), wherR3 has the indicated meaning and X represents OH, F, Cl, Br, I or another leaving group easily cleavable, or because iü) to prepare a compound of formula I, according to claim 1, wherR = (a), (b), (c) or (d), a compound of formula IV is reacted
wherR * represents R3-CO-NH-C (= NR ') -T__ and -, with R' 10 and R3, as well as B, the meanings indicated in claim 1, and Z represents Cl, Br, I, OH or a reactive group of esterified OH, with a compound of formula Va
> wherY represents -CH- (CH2) m-COR2, -N-CH (C02R9) - (CH2) n-COR or 20 -N- (CH2) n-COR2, and wherU, R2, R, m and n have the meanings indicated in claim 1, or with a compound of formula Vb
WherL represents - (CH2) n-COR2 or -CH2-CH (NHR4) -COR2, and wherR2, R4 and n have the meanings indicated in claim 1, and X 'represents OH or a salt derived from the OH group, or because a compound of formula VI is reacted
in which
and B, L, U and Y, like R 'and R3 have the meanings indicated above, with a reactive derivative of carbonic acid, or because (iv) to prepare a compound of formula I, according to claim 1, in the where R = (e), (f), (g), (h), (i) or (k), a compound of formula VII is reacted
wherR1 and R3 have the meanings indicated above, M is NH2, NH-CO- (CH,) 2-COX, .Q '~~? NH -CO- (AS > -X .co- @ -N ^ -X '.
^ - ^ N ^ -X ', -NR6H or -CONR'H, where
D, E, F, X, X ', AS, R6, R8 and k have the meanings 10 indicated above, with a compound of formula VIII R2-CO-Q (VIII), wherR2 has the indicated meaning and 15 Q is -CH2-CHR5-NHCO- (CH2) 2-COX, -CH2-CHRS-NH2,
wherF, G, X, R5, R7, AS, k, 1, and n have the meanings indicated above, or because (v) to prepare a compound of formula I, according to claim 1, wherR = (1 ), a compound of formula IX is reacted
wherR1, R3, X and p have the indicated meanings, with a compound of formula X
wherR2, R4 and X 'have the indicated meanings, or because to prepare a compound of formula I, according to claim 1, it is transformed, in a compound which corresponds to general formula I, (vi) a radical R1 in another residue R1 by -alkylation or acylation, or (vii) a residue R2 in another residue R2, either by alkylating an amide by hydrolyzing a cyano group totally or partially by esterifying a COOH group or by transforming a COOH or COOA group into a amide, or because (viii) a compound of formula I, according to claim 1, is converted into one of its salts by treatment with an acid or a base. The compounds of formula I have at least one chiral center, whereby they can occur in several enantiomeric forms. All these forams (for example, the forms R and S) and their mixtures (for example, the RS forms) are covered by the formula I. The remains or parameters mentioned in this text have the meanings indicated for the formulas I a X, unless otherwise indicated. If several groups or parameters with the same denomination are found in a molecule, they can independently adopt different de-finitions. In the formulas indicated above, group A has between 1 and 6, preferably 1, 2, 3, or 4 C atoms. In particular, A preferably represents methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or terbuti-lo, then also pentyl, 1-, 2- or 3-methylbutyl, 1,1-, 1,2- or 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1-, 2-, 3- or 4 - ethylpentyl. The rest R represents preferably
with m = 0 or 1, or
with U = CO or CH2 and n = 0, 1 or 2, then also preferably
with R = H, AS02 or Ar-S02;
)
with n = 1 or 2 and R9 = COOH, COOA or H;
with R "= H, A, alkynyl or alkenyl of 2 to 4 C atoms or Ar,
with n = 1 or 2;
R4
with R4 = SO, -A
wherein AS is an amino acid residue selected from the group consisting of Ala, Arg, ASn, Asp, Cys, Gln, Glu, Gly, His, Lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr or Val, which is linked through peptide bonds. R1 preferably represents hydrogen, methyl or ethyl. R2 preferably represents OH or OA, but also preferably phenyl-CH2-0- (benzyloxy), while R3 preferably represents A-CO, Ar-CO, Het-CO, Ar-O-CO, Ar-SO-, or A -S02 Ar preferably represents phenyl, benzyl or di-phenylmethyl, then also preferably 1- or 2-naphthyl, the indicated radicals being preferably unsubstituted, but also substituted one, two or three times with the above-mentioned radicals, in particular A, F , Cl, Br, ethylendioxy, COOH, COOCH3, 0-CO-A, COOC2H5, CF3, OH or OA. Het preferably represents 2- or 3-furyl, 2- or 3-thienyl, 1-, 2- or 3-pyrrolyl, 1-, 2-, 4- or 5-imidazolyl, 1-, 3-, 4- or 5 -pyrazolyl, 2-, 4- or 5-oxazolyl, 3-, 4- or 5-isoxazolyl, 2-, 4- or 5-thiazolyl, 3-, 4- or 5-isothiazolyl, 2-, 3- or 4 -pyridyl, 2-, 4-, 5- or 6-pyrimidinyl, then preferably 1,2,3-triazole-l-, -4- or -5-yl, 1, 2,4-triazole-1-, - 3-or-5-yl, 1- or 5-tetrazolyl, 1, 2, 3-oxadiazol-4- or -5-yl, 1,4-oxadiazol-3 or 5-yl, 1, 3, 4-thiadiazol-2- or -5-yl, l, 2,4-thiadiazol-3- or -5-yl, 1, 2, 3-thiadiazol-4- or -5-yl, 2-, 3-, 4-, 5- or 6-2H-thiopyranyl, 2-, 3- or 4-4H-thiopyranyl, 3-or 4-pyridazinyl, pyrazinyl, 2-, 3-, 4-, 5-, 6- or 7- benzofu-ryl, 2-, 3-, 4-, 5-, 6- or 7-benzothienyl, 1-, 2-, 3-, 4-, 5-, 6- or 7-indolyl, 1-, 2- , 4- or 5-benzimidazolyl, 1-, 3-, 4-, 5-, 6- or 7-benzopyrazolyl, 2-, 4-, 5-, 6- or 7-benzoxazolyl, 3-, 4-, 5 -, 6- or 7-benzoisoxazolyl, 2-, 4-, 5-, 6- or 7-benzothiazolyl, 2-, 4-, 5-, 6- or 7-benzoisothiazolyl, 4- , 5-, 6-or 7-benzo-2, 1, 3-oxadiazolyl, 2-, 3-, 4-, 5-, 6-, 7- or 8-qui-noleinyl, 1-, 3-, 4 -, 5-, 6-, 7- or 8-isoquinolinyl, 1-, 2-, 3-, 4- or 9-carbazolyl, 1-, 2-, 3-, 4-, 5-, 6-, 7 -, 8- or 9-acridinyl, 3-, 4-, 5-, 6-, 7- or 8-cinolinyl, 2-, 4-, 5-, 6-, 7- or 8-quinazolinyl. The heterocyclic moieties may also be partially or totally hydrogenated. Thus, Het can also represent, for example, 2, 3-dihydro-2-, -3-, -4- or -5-furyl, 2,5-dihydro-2-, -3-, -4-or- 5-furyl, tetrahydro-2- or -3-furyl, 1,3-dioxolan-4-yl, tetrahydro-2- or -3-thienyl, 2,3-dihydro-l-, -2-, -3- , -4- or -5-pyrrolyl, 2,5-dihydro-l-, -2-, -3-, -4- or -5-pyrrolyl, 1-, 2- or 3-pyrrolidinyl, tetrahydro-1- , -2- or -4-imidazolyl, 2,3-dihydro-l-, -2-, -3-, -4- or -5-pyrazolyl, tetrahydro-1-, -3- or -4-pyrazolyl, 1,4-dihydro-l-, -2-, -3- or -4-pyridyl, 1,2,3,4-tetrahydro-l-, -2-, -3-, -4-, -5- or -6-pyridyl, 1, 2, 3,6-tetrahydro-l-, -2-, -3-, -4-, -5- or -6-pyridyl. 1-, 2-, 3- or 4-piperidinyl, 2-, 3- or 4-morpholinyl, tetrahydro-2-, -3- or -4-pyranyl, 1,4-dioxanyl, 1,3-dioxan-2 -, -4- or -5-yl, hexahydro-1-, -3- or -4-pyridazinyl, hexahydro-1-, -2-, -4- or -5-pyrimidinyl, 1-, 2- or 3 -piperazinyl, 1, 2, 3, 4-tetra-hydro-1-, -2-, -3-, -4-, -5-, -6-, -7- or -8-quinolinyl, 1,2 , 3,4-tetrahydro-l-, -2-, -3-, -4-, -5-, -6-, -7- or -8-isoquinolinyl. For the whole invention it is worthwhile that all the remains that appear more than once can be the same or different, that is, independent of each other.
Accordingly, it is a particular object of the present invention those compounds of formula I in which at least one of the mentioned moieties has one of the preferred meanings indicated above. Some preferred groups of compounds can be represented by the formulas a to Ih indicated below, which correspond to formula I and in which the moieties which are not explicitly detailed have the meanings indicated for formula I, namely:
n is 1 or 2 and R1 is hydrogen;
R10 is hydrogen or OH, is 0 or 1 and R1 is hydrogen;
and R1 is hydrogen;
in Id R is? C NC_ _J * ~. { C *) (with 1 = 1 0 2, and R1 is hydrogen;
R1 is hydrogen and R2 is OH or OA;
with R 4 = A, alkenyl or alkynyl of 2 to 4 carbon atoms;
with OR4 = A-S02- or Ar-S02-; in Ig R3 is benzoyl, 1- or 2-naphthyl, furoyl, thienoyl or carbobenzoxy and R2 is OH or OA;
benzoyl or 1- or 2-naphthyl. In general, both the compounds of formula I and the starting materials for their preparation are prepared according to known methods, as described in the literature (for example, in certain works such as d Houben-Weyl, "Methoden der Organischen Chemie "(Methods of Organic Chemistry), Georg-Thieme-Verlag, Stuttgart, also e J. Med. Chem. 3_7, pp. 3881-3886 (1994), and in European documents Al-0 381 033 and Al -0462 960) and under reaction conditions that are known and suitable for the reactions mentioned. You can also make use of known variants of these methods that are not detailed in this text. If desired, the starting materials can be prepared in situ, but in such a way that instead of isolating them from the reaction mixture they are reacted directly to form the compounds of formula I. The compounds of formula I can be obtained solvolysis, in particular hydrolysis, or by hydrogenolysis of its functional derivatives. As starting substances for solvolysis or hydrogenolysis, those substances which are formula I-dependent are preferred, but instead of one or more groups of free amino and / or free hydroxyl groups they contain amino groups and / or or hydroxyl correspondingly protected, preferably those which instead of an H atom attached to an N atom carry an amino protecting group, in particular those which instead of a group of NH carry a group of R'-N, R 'an amino protecting group, and / or those which instead of the H atom of the hydroxyl group bear a hydroxyl protecting group, for example, those which respond to formula I, but which instead of a group of - COOH carry a group of -COOR ", where R" is a hydroxyl protecting group. There can also be several groups, the same or different, of protected amino and / or hydroxyl in the starting material molecule. If the protective protecting groups are different from each other, then they can be excised in many cases selectively. The term "amino protecting group" is known and refers to the groups that are adapted to protect (block) an amino group from chemical reactions, but which can easily be cleaved after the desired chemical reaction has been carried out in another place in the molecule. Typical examples of these groups are, in particular, the unsubstituted or substituted groups of acyl, aryl (e.g., 2,4-dinitrophenyl (DNF)), aralkoxymethyl (eg, benzyloxymethyl-lo (BOM)) or aralkyl (e.g., benzyl, 4-nitrobenzyl, tri-phenylmethyl). Since the amino protecting groups are cleaved after the desired reaction (or the sequence of reactions) has elapsed, the type and size thereof is not a critical point; however, those groups from 1 to 20, in particular from 1 to 8, C atoms are preferred. In the context of the process of the present invention, the expression "acyl group" has a very broad interpretation. It encompasses acyl groups deriving from aliphatic, araliphatic, aromatic or heterocyclic carboxylic or sulfonic acids such as, in particular, the alkoxycarbonyl, aryloxycarbonyl and especially aralkoxycarbonyl groups. Examples of acyl groups of this type are alkanoyl groups such as acetyl, propionyl and butyryl; aralkanoyl such as phenylacetyl; aroyl such as benzoyl or toluyl; aryloxyalkanoyl such as phenoxyacetyl; alkoxycarbonyl such as methoxycarbonyl, ethoxycarbonyl, 2,2,2-trichloroethoxycarbonyl, iso-propoxycarbonyl, tert-butoxycarbonyl (BOC), 2-iodoethoxycarbonyl; aralkyloxycarbonyl such as benzyloxycarbonyl (CBZ), 4-methoxybenzyloxycarbonyl, 9-fluorenylmethoxycarbonyl (FMOC). The preferred amino protecting groups are BOC, DNF and BOM, then CBZ, benzyl and acetyl. The expression "hydroxyl protecting group" is also known and refers to the groups that are adapted to protect a hydroxyl group from chemical reactions, but which are easily cleaved once the desired chemical reaction has been carried out. out in a different place on the molecule. Typical examples of these groups are the substituted or unsubstituted groups of aryl, aralkyl or acyl mentioned above, and also the alkyl groups. The nature and size of the hydroxyl protecting groups do not constitute a critical point, as these are re-cleaved once the desired chemical reaction (or chemical reaction sequence) has been completed.; however, the groups from 1 to 20, in particular from 1 to 10, are preferred. Examples of hydroxyl protecting groups are, inter alia, tertbutyl, benzyl, p-nitrobenzoyl, p-toluenesulfonyl and acetyl, with benzyl being and acetyl groups particularly preferred. The functional derivatives of the form-mu Ia compounds which are used as starting substances can be prepared by conventional methods such as are described, for example, in the works and in the patent applications cited therein. this text, for example, by transformation of compounds that respond to formulas II and III, but in which at least one of these compounds has a protective group instead of an H atom. The release of the compounds of formula I to From its functional derivatives, it is carried out according to the protective group used, for example, with strong acids, conveniently with trifluoroacetic or perchloric acid, but also with other strong inorganic acids such as hydrochloric or sulfuric acid, with strong organic carboxylic acids such as trichloroacetic acid, or with sulfonic acids such as benzenesulfonic or p-toluenesulphone. It is possible to carry out the reaction in an additional inert solvent, but the presence thereof is not indispensable in all cases. As inert solvents, organic solvents such as, for example, carboxylic acids such as acetic acid, ethers such as tetrahydrofuran (THF) or dioxane, amides such as dimethylformamide (DMF), halogenated hydrocarbons such as dichloromethane, sulfoxides such as dimethylsulfoxide (DMSO), also alcohols such as methanol, ethanol or isopropanol, and water. Mixtures of these solvents can also be used. The tri-fluoroacetic acid is preferably used in excess and without the additional addition of another solvent; the perchloric acid is used in the form of a mixture composed of acetic acid and 70% perchloric acid in a ratio of 9: 1. The reaction temperatures for the cleavage are suitably comprised between ca. 0 and 50 ° C, preferably between 15 and 30 ° C (room temperature). The BOC group can be cleaved preferably with, for example, 40% trifluoroacetic acid in dichloromethane or with approx. 3N to 5N in dioxane, at a temperature between 15 and 60 ° C; The FMOC group can be cleaved using a 5-20% solution of dimethylamine, diethylamine or piperidine in DMF, at a temperature between 15 and 50 ° C. The cleavage of the DNF group can also be carried out with, for example, a 3-10% solution of 2-mercaptoethanol in DMF / water, at a temperature comprised between 15 and 30 ° C. Protecting groups that are separated by hydrogenolysis (eg, BOM, CBZ or benzyl) can be cleaved, for example, by treatment with hydrogen in the presence of a catalyst (eg, a noble metal catalyst such as palladium, conveniently on a support like coal). Suitable solvents are the same as mentioned above, in particular alcohols such as methanol or ethanol, or amides such as DMF. In general, the hydrogenolysis is carried out at temperatures between 0 and 100 ° C and pressures between 1 and 200 bar, preferably at temperatures between 20 and 30 ° C and pressures between 1 and 10 bar. The hydrogeolysis of the CBZ group proceeds favorably with 5-10% of Pd-C in methanol and at temperatures between 20 and 30 ° C. The compounds of formula I can be prepared preferably by reaction of a compound of formula II with a carboxylic acid derivative of formula III. For this, it is necessary to resort to the known methods for the acylation of amines. The group X of formula III preferably represents Cl, Br, I, alkyl (C, .6) sulfonyloxy such as methanesulfonyloxy or ethanesulfonyloxy, or aryl (C ^) sulfonyloxy such as benzenesulfonyloxy, p-toluenesulfonyloxy or 1- or 2-naphthalenesul-foniloxy. The reaction preferably proceeds in the presence of an additional base, for example, of an alkali metal or alkaline earth metal hydroxide or carbonate such as sodium, potassium or calcium hydroxide, or sodium, potassium or calcium carbonate, in a inert solvent such as, for example, a halogenated hydrocarbon such as dichloromethane, an ether such as THF or dioxane, an amide such as DMF or dimethylacetamide, a nitrile such as acetonitrile, at temperatures ranging from -10 and 200 ° C, preferably between 0 and 120 ° C. If the leaving group is different from Iodine, then it is convenient to add an iodide such as potassium iodide. The starting materials of formula II are generally known and can be prepared, for example, according to the methods described in European patent no.
623. 615 (corresponding to German Patent No. 4,314,378). To prepare an idine of formula II, ammonia can be added to a nitrile of formula II. The addition preferably proceeds in several steps, namely: a) in a known manner, the nitrile is converted to a thioamide with H2S, which is converted into the corresponding S-alkyl-imidothioester by treatment with an alkylating agent, for example CH3I, and then it is reacted with NH3 to form the amidine, b) the nitrile is transformed into the corresponding imidoester by treatment with an alcohol such as, for example, ethanol in the presence of HCL, and then said ester is treated with ammonia, or c) the nitrile is reacted with lithium bis (trimethylsilyl) amide and then the product obtained is hydrolyzed. In an analogous manner, the N-hydroxy amidines of the formula II can be obtained from the corresponding nitriles if working according to a) or b), but using hydroxylamine instead of ammonia. Then, these products can also be modified, for example, by reduction with hydrogen gas. The compounds of formula III are known and most of them are obtained in shops. The reaction of the compounds of formula II with the compounds of formula III proceeds in the manner described above. It is also possible to obtain a compound of formula I, wherein R is (a), (b), (c), or (d), by reacting a compound of formula IV with a compound of formula Va or Vb. The compounds of formula IV are disclosed in part in European patent No. 623,615, or they can be prepared according to the methods described in this patent. For example, they can be prepared by reaction of a substituted aniline of formula R * -NH2 with a compound of formula R5CH2-CHR6-CH2OH (where R5 is Cl, Br or another suitable leaving group and R6 is OH, or R5 and R6, together, also represent 0) to give a compound of formula R * -NH-CH2-CHR8-CH20H (wherein R8 is OH), then by reaction with a carbonic acid derivative such as diethyl carbonate for obtain 3-R * -5-hydroxymethyl-2-oxazolidinones, and optionally by conversion of the hydroxymethyl group to a group of CH2Z '(where Z' represents a leaving group) with, for example, SOClj, S0Br2, methanesulfonyl or p-toluenesulfonyl. In general, the compounds of formula Vb are known, or can be obtained in a manner analogous to that of the known compounds, from phenol or its suitable derivatives. The same can be applied to the compounds of formula Va. These can be prepared according to known methods, from piperidine derivatives or piperazine. The reaction is carried out under conditions similar to those described above for the reaction between compounds II and III. The compounds of formula I can also be obtained by reacting a compound of formula IV (or a reactive derivative thereof) with a reactive derivative of carbonic acid. Suitable derivatives of carbonic acid are, in particular, dialkyl carbonates such as diethyl carbonate, and also alkyl esters of chloroformic acid such as ethyl chloroformate. The carbonic acid derivative, which is conveniently added in excess, also preferably fulfills the function of solvent or suspending agent. You can also work in the presence of one of the solvents mentioned, as long as the latter is inert. In addition, the addition of a base is recommended, in particular an alkali metal alkoxide such as potassium terbutoxide. It is advisable to work at temperatures between 0 and 150 ° C, preferably between 70 and 120 ° C. In general, the starting substances of formula IV are new. They can be obtained, for example, by transforming the aforementioned compounds of the formula R * -NH-CH2-CH (OH) -CH2OH into functional compounds of the formula R * -NH-CH2-CH (OH) -CH2-Z and then making them react with compounds of formula Va or Vb. It is also possible to obtain compounds of formula I, wherein R is (e), (f), (g), (h), (i) or (k), by reaction of a compound of formula VII with a compound of formula VIII. The preparation of compounds VII and VIII can be carried out according to known methods, such as are described, for example, in J. March, "Adv. Org. Chem.", 3rd edition, J. Wiley & amp;; Sons (1985). For example, a compound of form-mule VII can be prepared by transforming a p-CN-aniline, which is eventually derived in the NH2 group, into a p-amidinoa-niline according to the method described above, and then acylating this last with a compound of formula R3-X, wherein X is preferably Cl or Br. To obtain a compound of formula VII a substituted benzoic acid derivative can also be transformed with a residue R3-CO-NH-C (= NR ' ) in another acid derivative, or to bind it to an amino acid or a correspondingly derivatized amino acid. The preparation of the carboxylic acids or of the carboxylic acid derivatives of formula VIII is trivial and can be carried out according to known methods. During the reaction of VII with VIII it is convenient to work in the presence of a base or with an excess of the basic component. Among the suitable bases, for example, the hydroxides, carbonates or alkoxides of alkali or alkaline earth metals or organic bases such as triethylamine or pyridine are preferred, which can also be used in excess and serve at the same time as a solvent. Suitable inert solvents include, in particular, alcohols such as methanol, ethanol or isopropanol, n-butanol or terbutanol; ethers such as diethyl ether, diisopropyl ether, THF or dioxane; glycol ethers such as ethylene glycol onomethyl ether or ethylene glycol monoethyl ether (methyl glycol or ethyl glycol), ethylene glycol dimethyl ether (diglyme); ketones such as acetone or butanone; nitriles such as acetonitrile; nitro compounds such as nitromethane or nitrobenzene; the esters such as ethyl acetate; amides such as hexamethyltriamide of phosphoric acid; sulfoxides such as dimethylsulfoxide (DMSO); chlorinated hydrocarbons such as dichloromethane, chloroform, t-chloroethylene, 1,2-dichloroethane or carbon tetrachloride; hydrocarbons such as benzene, toluene or xylene. Mixtures of these solvents are also suitable. Suitable reaction temperatures are between room temperature and the boiling point of the chosen solvent. The compounds of formula I can also be obtained by reacting a compound of formula IX with a compound of formula X. Both for the preparation of the condensation products IX and X and for the reaction between them, the aforementioned is applied compounds VII and VIII. It is also possible to convert a radical R2 of a compound of formula I into another radical R2 by saponification of an ester of formula I or by esterification of a carboxylic acid of formula I. For the esterification, an acid of formula I can be treated ( R2 = H) with an excess of an alcohol of formula R: -OH 5 (R2 = A or benzyl) conveniently in the presence of a strong acid such as hydrochloric acid or sulfuric acid, at temperatures between 0 and 100 ° C , preferably between 20 and 50 ° C. ) In contrast, an ester of formula I (R2 = A or benzyl) can be converted into the corresponding acid of formula I (R2 = H) conveniently by solvolysis or hydrogenolysis according to one of the methods mentioned above, for example, by treatment with NaOH or KOH in water-dioxane, at temperatures between 0 and 40 ° C, preferably 15 between 10 and 30 ° C. Cyano groups can also be partially or totally hydrolyzed. It is also possible to transform a radical R1 and / or R3 into another radical R1 and / or R3. In particular, the primary or secondary amino groups can be alkylated, acylated, converted to amidines or protected with conventional amino protecting groups or with alkylsulfonyl or arylsulfonyl groups, or, conversely, they can be released by excision of These groups. A base of formula I can be converted into its salt by the addition of an acid. Acids which form acceptable salts from the physiological point of view are suitable for this reaction. Thus, inorganic acids can be used, such as, for example, sulfuric acid, nitric acid, hydrocides such as hydrochloric or hydrobromic acid, phosphoric acids such as orthophosphoric acid, sulphamic acid, and also organic acids, in particular the aliphatic, alicyclic, araliphatic, aromatic or heterocyclic carboxylic, sulfonic or sulfuric monobasic or polybasic acids such as, for example, formic, acetic, trifluoroacetic, propionic, pivalic, diethylactic, malonic, succinic, pimelic, fumaric, maleic, lactic, tartaric, malic, citric, gluconic, ascorbic, ni-cotinic, isonicotinic, methanesulfonic or ethanesulfonic, ethanedisulfonic, 2-hydroxyethanesulfonic, benzenesulfonic, p-toluenesulfonic, naphthalene monosulfonic, naphthalenedisulfonic and lauryl sulfuric. Salts of acids which are not physiologically acceptable, for example picrates, can be used to isolate and / or purify the compounds of formula I. If desired, the bases of formula I can be released from their salts by treatment with strong bases such as sodium or potassium hydroxide, or sodium or potassium carbonate. It is also possible to convert the carboxylic acids of formula I (R2 = H) into their metal or ammonium salts, for example into their sodium, potassium or calcium salts, by reaction with the corresponding bases. The compounds of formula I have one or more chiral centers, whereby they can be obtained as racemates or in their optically active form. The obtained racemates can be separated into their enantiomers by known chemical or mechanical methods. The diastereomers are formed from the racemic mixture, preferably by reaction with an optically active separation agent. Examples of suitable separation agents are optically active acids such as the D and L forms of tartaric, diacetyl tartaric, dibenzoyltartaric, mandelic, malic, lactic acids, or the various optically active camphorsulfonic acids such as β-camphorsulfonic acid. It is also convenient to separate the enantiomers through a column filled with an optically active separation agent (eg dinitrobenzoyl-phenyl-glycine); as the eluent, for example, a hexane / isopropanol / acetonitrile mixture can be used in a volume ratio of, for example, 82: 15: 3. Of course it is also possible to obtain optically active compounds of formula I according to the methods described above, by using optically active starting substances (eg of the type of those of formula II). The compounds of formula I can also have tautomeric forms, which are within the scope of the present invention. The novel compounds of formula I and their physiologically acceptable salts can be used for the preparation of pharmaceutical preparations, by converting them into suitable dosage forms together with at least one excipient or auxiliary product and, optionally, in combination with one or more additional active substances. The preparations thus obtained can be used in medicine and in veterinary medicine as medicines. Among the excipients, mention may be made of organic and inorganic substances which are suitable for enteral (eg oral or rectal) or parenteral administration, or for application in the form of an inhalant aerosol, and which do not react with the new compounds. Examples of these excipients are water, vegetable oils, benzylic alcohols, polyethylene glycols, glycerin triacetate and other glycerides of fatty acids, gelatin, soy lecithin, carbohydrates such as lactose or starch, magnesium stearate. , talc, cellulose. For oral administration, tablets, dragees, capsules, syrups, juices or drops are used in particular; Particularly important are coated tablets and capsules that have a coating or wrap resistant to gastric juices. For the rectal application, the suppositories are used, for the parenteral application the solutions, preferably the oily or aqueous solutions, and also the suspensions, emulsions or implants. For the application in the form of an inhalant aerosol, aerosols containing the active substance either dissolved or suspended in a mixture of the driving gas can be used. It is advisable to use the micron-sized active substance, optionally together with one or more other physiologically acceptable solvents such as, for example, ethanol. Inhalant solutions can be administered with the help of conventional inhalers. The new compounds can also be lyophilised and the resulting lyophilized products can be used, for example, for the preparation of injectable preparations. The preparations mentioned can be sterilized and / or contain auxiliary substances such as preservatives, stabilizers and / or wetting agents, emulsifying agents, salts for influencing the osmotic pressure, pH regulating substances, dyes and / or perfuming substances. If desired, they may also contain one or more additional active substances, such as, for example, one or several vitamins. In general, the substances of the invention are administered in a manner analogous to that of known and commercial medicaments, in particular analogously to the compounds described in the published and examined European Patent Application No. 459,256, preferably in commercially available -dids between approx. 5 mg and 1 g, in particular between 50 and 500 mg per dosage unit. The daily dose is preferably comprised between ca. 0.1 and 20 mg / kg of body weight, in particular between 1 and 10 mg / kg of body weight. However, the particular dose for each patient depends on a wide variety of factors, for example, the activity of the special compound used, age, body weight, general health, sex, the diet, time and method of administration, the rate of excretion, the combination of drugs and the severity of the particular disease to which the therapy is applied. Oral administration is preferred. All temperatures indicated in this text are given in ° C. In the following examples, the expression "is worked (or treated) in the usual way" means the following: if necessary, water is added, the pH is adjusted between 2 and 8 according to the constitution of the final product, it is filtered through an ion exchange column The organic phase is dried over sodium sulphate, concentrated by evaporation, optionally lyophilized and purified by chromatography on silica gel and / or by recrystallization. In the examples that follow, "4-piperidylethyl" always means "2- (4-piperidyl) -ethyl", "4-piperidylpropyl" always means "3- (4-piperidyl) -propyl" and "4-piperidylbutyl" means always "4- (4-piperi-dil) -butyl". In the same way, "4-piperazinylethyl" always means "2- (4-piperazinyl) -ethyl", "4-piperazinylpropyl" always means "3- (4-piperazinyl) -propyl" and "4-piperazinyl-butyl" always means "4- (4-piperazinyl) -butyl". Included in these designations are derivatives provided with protecting groups, for example, compounds protected with BOC. Example 1 To a solution of 1.2 g of 4-ethoxycarbonylmethyl piperazine ("A") in 20 ml of DMF is added 3.0 g of 3- [4- (N-benzoylamino) phenyl] -5-methanesulfonyloxy. -methyl-oxazolidin-2-one [obtained by reaction of 4- (5-oxo-l, 2,4-oxadiazolin-3-yl) -aniline with 2,3-epoxypropan-1-ol to give the N- [ 4- (5-oxo-1,2,4-oxadiazolin-3-yl) -phenyl] -2,3-dihydroxypropylamine, then by reaction with diethyl carbonate in the presence of potassium terbutylate to give 3- [ 4- (5-oxo-l, 2,4-oxadiazolin-3-yl) -phenyl] -5-hydroxymethyl-oxazolidin-2-one, re-ductive removal of the 5-oxo-l, 2,4-oxadiazolino group reaction with benzoyl chloride and finally by esterification with methanesulfonyl chloride], dissolved in 10 ml of DMF, and stirred for 60 minutes at room temperature. After removing the solvent and treating the product in a usual manner, 3- [4- (N-benzoylamino) -phenyl] -5- (4-ethoxycarbonylmethyl-pipera-zinomethyl) -oxazolidin-2-one, m.p. 114 °. Analogously, by reaction of "A" with 3- [4- (N-benzoylamine) -phenyl] -5 (R) -methanesulfonyloxy-methyl-oxazolidin-2-one, the 3- [4- (N -benzoylamino) -phenyl] -5 (R) - (4-ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one, mp 150 °, [a] l \ t, = + 33.4 ° (DMSO); with 3- (4- (N-benzoylamidino) -phenyl] -5 (S) -methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-benzoylamine) -phenyl] -5 (S) - (4-Ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one, mp 149 °, [a] D2u = -32.6 ° (DMSO); with 3- [4- (N-benzyloxycarbonylamido) -phenyl] -5-methanesulfoni - loxi-methyl-oxazolidin-2-one, 3- [4- (N-benzyloxycarbonylamido) -phenyl] -5- (4-ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one, pp. 129 ° with 3- [4- (N-phenoxycarbonylamido) phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-phenoxycarbonylamino) phenyl] -5- (4-ethoxycar- bonylmethyl-piperazinomethyl) -oxazolidin-2-one, p.F. 176 °; con3- [4- (N- (3-pyridylcarbonyl) -amidino) -phenyl] -5-methanesulphonoxymethyl-oxazolidin-2-one, the 3- [4- (N- (3-pyridylcarbonyl) -amidino) -phenyl] -5- (4-ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one, mp 134-135 °; with 3- [4- (N- (L-methyl-piperidyl-4-oxycarbonyl) -amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, the dicl 3- [4- (N- (l-methyl-piperidyl-4-oxycarbonyl) -amidino) -phenyl] -5- (4-ethoxycarbonylmethyl-piperazomethyl) -oxazolidin-2-one, p.f. 91-93 °; 3- [4- (N-naphthoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-naphthylamidino) -phenyl] -5- (4-ethoxycarbonyl methylpiperazinomethyl) -oxazolidin- 2-one, pf 160-161 °; 3- [4- (N-2-naphthoylamidino) -phenyl] -5-methanesulfonyloxymethyl-1-oxazolidin-2-one, 3- [4- (N-2-naphtholamidino) -phenyl] -5- (4-ethoxycarbonyl methylpiperazinomethyl) ) -oxazolidin-2-one; - [4- (N-2-furoylamidino) -phenyl] -5-methanesulfonyloxymethyl-1-oxazolidin-2-one, 3- [4- (N-2-furoylamidino) -phenyl] -5- (4-ethoxycarbonyl methylpiperazinomethyl) -oxazolidin-2-one, mp 172-173 °; - [4- (N-3-furoylamidino) -phenyl] -5-methanesulfonyloxymethyl-1-oxazolidin-2-one, 3- [4- (N-3-furoylamidino) -phenyl] -5- (4-ethoxycarbonyl-ethyl-iperazinomethyl) -oxazolidin-2-one; 3- [4- (N-2-thienoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-thienoylamidino) -phenyl] -5- (4-ethoxycarbonyl methylpiperazinomethyl) ) -oxazolidin-2-one; 3- [4- (N-3-thienoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-3-thienoylamidino) -phenyl] -5- (4-ethoxycarbonyl methylpiperazinomethyl) ) -oxazolidin-2-one; with 3- [4- (N-methoxycarbonyl-amidino) -phenyl] -5-methanesulfonyl ximethyl-oxazolidin-2-one, 3- [4- (N-methoxycarbonyl-amidino) -phenyl] -5- (4- ethoxycarbonyl ethyl-piperazinomethyl) -oxazolidin-2-one, mp 186-187 °. Example 2 Analogously to that of Example 1, the
3- [4- (N-benzoylamino) -phenyl] -5- (4-ethoxycarbonylethyl-piperazinomethyl) -oxazolidin-2-one, m.p. 163-164 °, by reaction of 1.2 g of ethoxycarbonylethyl-piperazine ("B") in 20 ml of DMF with 3.0 g of 3- [4- (N-benzoylamine) -phenyl] -5-methanesulfonate nyloxy-methyl-oxazolidin-2-one [obtained according to example 1], dissolved in 10 ml of DMF, and after removing the solvent and treating the mixture in the usual manner. Analogously, by reaction of "B" with 3- [4- (N-benzoylamine) -phenyl] -5 (S) -methanesulfonyloxy-methyloxazolidin-2-one, 3- [4- (N-benzoylamidine ) -phenyl] -5 (S) - (4-ethoxycarbonyl ethylpiperazinomethyl) -oxazolidin-2-one, mp 149-150 °, [] = -32, 6 ° (DMSO); with 3- [4- (N-benzoylamine) -phenyl] -5 (R) -methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-benzoylamine) -phenyl] -5 (R) - (4) -ethoxycarbonylethyl-piperazinomethyl) -oxazolidin-2-one, pf225-226 °, [a] 0 ^, = + 33.0 ° (DMSO); - [4- (N-Benzyloxycarbonylamidoino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-benzyloxycarbonylamino) -phenyl] -5- (4-ethoxycarbomethyl) -piperazinomethyl) -oxazolidin-2-one, mp 130- 131 °; 3- [4- (N-benzyloxycarbonylamidoino) -phenyl] -5R-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-benzyloxycarbonylamido) -phenyl] -5R- (4-ethoxy-carbonylethyl) -piperazinomethyl) -oxazolidin-2-one, p. f. 133-134 °, [a] D20 = + 29.5 ° (DMSO); 3- [4- (N-Phenoxycarbonylamidoino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-phenoxycarbonylamino) -phenyl] -5- (4-ethoxycarbonylethyl) piperazinomethyl) -oxazolidin-2-one; - [4- (N- (3-pyridylcarbonyl) -amidino) -phenyl] -5-methanesulphonyloxymethyl-oxazolidin-2-one, 3- [4- (N- (3-pyridylcarbonyl) -amidino) -phenyl] -5- (4-ethoxycarbonylethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-methoxycarbonyl-amidino) -phenyl] -5-methanesulfonyl ximethyl-oxazolidin-2-one, 3- [4- (N-methoxycarbonyl-amidino) -phenyl] -5- (4-ethoxy - bonylethyl-piperazinomethyl) -oxazolidin-2-one, mp 168 ° with 3- [4- (N- (1-methyl-piperidyl-4-oxycarbonyl) -amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, the 3- [4- (N- (L-methyl-piperidyl-4-oxycarbonyl) -amidino) -phenyl] -5- (4-ethoxycarbonylethyl-piperazinomethyl) -oxazoli-din-2-one; with 3- [4- (N-ethoxycarbonylmethylcarbamoyl-amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-ethoxycarbonylmethylcarbamoyl-amidino) -phenyl] -5- (4 -ethoxycarbonylethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-methylsulfonylamine) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-methylsulfonylamine) -phenyl] -5- (4-ethoxycarbonylethyl) piperazinomethyl) -oxazolidin-2-one; with 3- [4- (Nl-naphthoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (Nl-naphthoylamidino) -phenyl] -5- (4-ethoxycarbonyl-thi piperazinomethyl) -oxazolidin -2-ona; with 3- [4- (N-2-naphtholamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-naphthoylamido) -phenyl] -5- (4-ethoxycarbonyl) tilpiperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-2-furoylamidino) -phenyl] -5-methanesulfonyloxymethi-oxazolidin-2-one, 3- [4- (N-2-furoylamidino) -phenyl] -5- (4- ethoxycarbonylethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-3-furoylamidino) -phenyl] -5-methanesulfonyloxymethi-1-oxazolidin-2-one, 3- [4- (N-3-furoylamidino) -phenyl] -5- (4- ethoxycarbonylethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-2-thienoylamidoino) -phenyl] -5-methanesulfonyloxymethyl-1-oxazolidin-2-one, 3- [4- (N-2-thienoylamidino) -phenyl] -5- (4-ethoxycarbonyl) tilpiperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-3-thienoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-3-thienoylamidino) -phenyl] -5- (4-ethoxycarbonyl) tilpiperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-diphenylacetyl-amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-diphenylacetyl-amidino) -phenyl] -5- (4 ethoxycarboxylethyl-piperazinomethyl) -oxazolidin-2-one; Example 3 Analogously to that of Example 1, the
3- [4- (N-benzoylamidino) -phenyl] -5- (4-tert-butoxycarbonylethyl-pi-perazinomethyl) -oxazolidin-2-one, m.p. 136-137 °, by reaction of 1.2 g of tert-butoxycarbonylethyl-piperazine ("C") in 20 ml of DMF with 3.0 g of 3- [4- (N-benzoylamidino) -phenyl] -5-methanesulfone nyloxy-methyl-oxazolidin-2-one [obtained according to example 1], after removing the solvent and treating the mixture in the usual manner. Analogously, by reaction of "C" with 3- [4- (N-benzyloxycarbonylamino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, the 3- [4- (N- benzyloxycarbonylamino) -phenyl] -5- (4-terbuto-xicarbonylethyl-piperazinomethyl) -oxazolidin-2-one, mp 133 °; with 3- [4- (N-phenoxycarbonylamidoino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-phenoxycarbonylamino) -phenyl] -5- (4-terbutoxy-carbonylethyl) piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N- (3-pyridylcarbonyl) -amidino) -phenyl] -5-methanesulphonyloxymethyl-oxazolidin-2-one, 3- [4- (N- (3-pyridylcarbonyl) -amidino) - phenyl] -5- (4-terbutoxycarbonylethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N- (l-methyl-piperidyl-4-oxycarbonyl) -amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, the 3- [4- (N- (l methyl-piperidyl-4-oxycarbonyl) -amidino) -phenyl] -5- (4-tert-butoxycarbonylethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-methoxycarbonylamidoino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-methoxycarbonylamidoino) -phenyl] -5- (4-terbutoxy-carbonylethyl-piperazinomethyl) -oxazolidin-2-one, mp 174 °; with 3- [4- (N-ethoxycarbonylmethylcarbamoyl-amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-ethoxycarbonylmethylcarbamoyl-amidino) -phenyl] -5- (4 -terthoxycarbonylethyl-piperazinomethyl) -oxazoli din-2-one, mp 80 °; with 3- [4- (N-methylsulfonylamine) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-methylsulfonylamine) -phenyl] -5- (4-terbutoxycarbomethyl) -piperazinomethyl) -oxazolidin-2-one, mp 205 °; with 3- [4- (Nl-naphthoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [- (N-naphtholamidino) -phenyl] -5- (4-tert-butoxycarbonylethyl-piperazinomethyl) -oxazolidin-2-one, mp 111- 113 °; with 3- [4- (N-2-naphthoylamidino) -phenyl] -5-methanesulfonyloxy-ethyl-oxazolidin-2-one, 3- [4- (N-2-naphthoylamidine) -phenyl] -5- (4- terbutoxicarbo nilethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-diphenylacetyl-amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-diphenylacetyl-amidino) -phenyl] -5- (4 -tert-butoxy-carbonylethyl-piperazinomethyl) -oxazolidin-2-one. Example 4 Analogously to that of Example 1, it is obtained by reacting 4-methoxycarbonylethylpiperazine with 3- [4- (N-benzyloxycarbonylamino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, the 3- [4- (N-benzyloxycarbonylamidoino) -phenyl] -5- (4-methoxy-carbonylethyl-piperazinomethyl) -oxazolidin-2-one; - [4- (N-benzoylamidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-benzoylamine) -phenyl] -5- (4-methoxycarbonylethyl-piperazinomethyl) - oxazolidin-2-one, 3- [4- (N-phenoxycarbonylamidoino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-phenoxycarbonylamido) -phenyl] -5- ( 4-methoxycarbonylethyl-piperazinomethyl) -oxazolidin-2-one; - [4- (N- (3-pyridylcarbonyl) -amidino) -phenyl] -5-methanesulphonyloxymethyl-oxazolidin-2-one, 3- [4- (N- (3-pyridylcarbonyl) -amidino) -phenyl] -5- (4-methoxycarbonylethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N- (l-methyl-piperidyl-4-oxycarbonyl) -amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, the 3- [4- (N- (l- methyl-piperidyl-4-oxycarbonyl) -amidino) -pheneyl] -5- (4-methoxycarbonylethyl-piperazinomethyl) -oxazoli-din-2-one; 3- [4- (N-methoxycarbonylamidoino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-methoxycarbonylamido) -phenyl] -5- (4-methoxycarbonylethyl) piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-ethoxycarbonylmethylcarbamoyl-amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-ethoxycarbonylmethylcarbamoyl-amidino) -phenyl] -5- (4- methoxycarbonylethyl-piperazinomethyl) -oxazolidin-2-one; - [4- (N-methylsulfonylamine) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-methylsulfonylamine) -phenyl] -5- (4-methoxycarbomethyl-piperazinomethyl) - oxazolidin-2-one; 3- [4- (N-naphthoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-naphthoylamidino) -phenyl] -5- (4-methoxycarbonyl-thi piperazinomethyl) -oxazolidin- 2-one; 3- [4- (N-2-naphthoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-naphthoylamidino) -phenyl] -5- (4-methoxycarbonyl) tylpiperazinomethyl ) -oxazolidin-2-one; - [4- (N-2-furoylamidino) -phenyl] -5-methanesulfonyloxymethyl-1-oxazolidin-2-one, 3- [4- (N-2-furoylamidino) -phenyl] -5- (4-methoxycarbonyl-thi piperazinomethyl) -oxazolidin-2-one; - [4- (N-3-furoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-3-furoylamino) -phenyl] -5- (4-methoxycarbonyl ethylpiperazinomethyl) -oxazolidin-2-one; 3- [4- (N-2-thienoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-thienoylamidoino) -phenyl] -5- (4-methoxycarbonyl) thi piperazinomethyl ) -oxazolidin-2-one; with 3- [4- (N-3-thienoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-3-thienoylamidoino) -phenyl] -5- (4-methoxycarbonyl) tilpiperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-diphenylacetyl-amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-diphenylacetyl-amidino) -phenyl] -5- (4 -methoxycarboxylethyl-piperazinomethyl) -oxazolidin-2-one. EXAMPLE 5 Analogously to that of Example 1, it is obtained by reaction of 4-isopropoxycarbonylethylpiperazine with 3- [4- (N-benzyloxycarbonylamidoino) -phenyl] -5-methanesulphonyloxy-methyl-oxazolidin-2-one, - [4- (N-benzyloxycarbonylamino) -phenyl] -5- (4-isopropoxycarbonylethi-piperazinomethyl) -oxazo1idin-2-one; with 3- [4- (N-benzoylamidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-benzoylamidino) -phenyl] -5- (4-isopropoxycarbonyl-ethyl) -piperazinomethyl) -oxazolidin-2-one, with 3- [4- (N-phenoxycarbonylamido) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-phenoxycarbonylamido) -phenyl] ] -5- (4-isopropoxy-carbonylethyl-piperazinomethyl) -oxazolidin-2-one; con3- [4- (N- (3-pyridylcarbonyl) -amidino) -phenyl] -5-methanesulfon or loxymethyl-oxazolidin-2-one, 3- [4- (N- (3-pyridylcarbonyl) -amidino) - phenyl] -5- (4-isopropoxycarbonylethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N- (l-methyl-piperidyl-4-oxycarbonyl) -amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, the 3- [4- (N- (l -methyl-piperidyl-4-oxycarbonyl) -amidino) -pheneyl] -5- (4-isopropoxycarbonylethyl-piperazinomethyl) -oxa-zolidin-2-one; with 3- [4- (N-methoxycarbonylamidoino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-methoxycarbonylamido) phenyl] -5- (4-isopropoxy carbonylethyl) piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-ethoxycarbonylmethylcarbamoyl-amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-ethoxycarbonylmethylcarbamoyl-amidino) -phenyl] -5- (4 isopropoxycarbonyl-1-yl-1-piperazinomethyl) -oxazo1-din-2-one; with 3- [4- (N-methylsulfonylamine) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-methylsulfonylamine) -phenyl] -5- (4-isopropoxy carbonylethyl) piperazinomethyl) -oxazolidin-2-one; with 3- [4- (Nl-naphthoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-naphtholamidino) -phenyl] -5- (4-isopropoxycarbonyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-2-naphthoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-naphthoylamidino) -phenyl] -5- (4-isopropoxycarb) nilethyl-piperazinomethyl) -oxazolidin-2-one; con3- [4- (N-2-furoylamidoino) -phenyl] -5-methanesulfonyloxymethyl-1-oxazolidin-2-one, 3- [4- (N-2-furoylamidino) -phenyl] -5- (4-isopropoxycarbonyl) -piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-3-furoylamidino) -phenyl] -5-methanesulfonyloxymethyl-1-oxazolidin-2-one, 3- [4- (N-3-furoylamido) -phenyl] -5- (4-isopropoxycarb) nilethylpiperazine ethyl) -oxazolidin-2-one; with 3- [4- (N-2-thienoylamidino) -phenyl] -5-methanesulfonyloxy-ethyl-oxazolidin-2-one, 3- [4- (N-2-thienoylamidino) -phenyl] -5- (4- isopropoxycarboxylethylpiperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-3-thienoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-3-thienoylamidino) -phenyl] -5- (4-isopropoxycarb) nilethylpiperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-diphenylacetyl-amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-diphenylacetyl-amidino) -phenyl] -5- (4 isopropoxy-carbonylethyl-piperazinomethyl) -oxazolidin-2-one. EXAMPLE 6 Analogous to that of Example 1, a reaction of 4-n-butoxycarbonylethylpiperazine with 3- [4- (N-benzyloxycarbonylamido) phenyl] -5-methanesulphonyloxymethyl-oxazolidin-2-one is obtained, 3- [4- (N-benzyloxycarbonylamidoino) -phenyl] -5- (4-n-butoxy-carbonylethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-benzoylamidino) -phenyl] -5-methanesulfonyloxy-methy1-oxazolidin-2-one, 3- [4- (N-benzoylamine) -phenyl] -5- (4-n-butoxycarbonyl) - Ethyl-piperazinoethyl) -oxazolidin-2-one, with 3- [4- (N-phenoxycarbonylamido) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-phenoxycarbonylamido ) -phenyl] -5- (4-n-butoxycarbonyl-ethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N- (3-pyridylcarbonyl) -amidino) -phenyl] -5-methanesulphonyloxymethyl-oxazolidin-2-one, 3- [4- (N- (3-pyridylcarbonyl) -amidino) phenyl] -5- (4-n-butoxycarbonylethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N- (l-methyl-piperidyl-4-oxycarbonyl) -amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, la3- [4- (N- (l- methyl-piperidyl-4-oxycarbonyl) -amidino) -pheneyl] -5- (4-n-butoxycarbonylethyl-piperazinomethyl) -oxa-zolidin-2-one; 3- [4- (N-methoxycarbonylamidoino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-methoxycarbonylamido) -phenyl] -5- (4-n-butoxycar- bonylethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-ethoxycarbonylmethylcarbamoyl-amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-ethoxycarbonylmethylcarbamoyl-amidino) -phenyl] -5- (4- n-butoxycarbonylethyl-piperazinomethyl) -oxazolidin-2-one; - [4- (N-methylsulfonylamine) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-methylsulfonylamine) -phenyl] -5- (4-n-butoxycarbomethyl) -piperazinomethyl) -oxazolidin-2-one; 3- [4- (Nl-naphthoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-naphtholamidino) -phenyl] -5- (4-n-butoxycarbonyl-ethyl- piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-2-naphthoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-naphtholamidino) -phenyl] -5- (4-n- butoxycarbonyl-ethi-1-piperazinomethyl) -oxazolidin-2-one; - [4- (N-2-furoylamidino) -phenyl) -5-methanesulfonyloxymethyl-1-oxazolidin-2-one, la3- [4- (N-2-furoylamidino) -phenyl] -5- (4-n-butoxycarbonyl- ethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-3-furoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-3-furoylamido) -phenyl] -5- (4-n) -butoxycarbonyl-ethylpiperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-2-thienoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-thienoylamidino) -phenyl] -5- (4-n) -butoxycarbonyl-ethylpiperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-3-thienoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-3-thienoylamidino) -phenyl] -5- (4-n) -butoxycarbonyl-ethylpiperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-diphenylacetyl-amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-diphenylacetyl-amidino) -phenyl] -5- (4 -n-butoxycarbonylethyl-piperazinomethyl) -oxazolidin-2-one. Example 7 Analogously to that of Example 1, it is obtained by reacting 4-benzyloxycarbonylethylpiperazine with 3- [4- (N-benzyloxycarbonylamido) phenyl] -5-methanesulphonyloxy-methyl-oxazolidin-2-one, - [4- (N-benzyloxycarbonylamino) -phenyl] -5- (4-benzyl-xicarbonylethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [- (N-benzoylamine) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-benzoylamino) -phenyl] -5- (4-benzyloxycarbonyl-ethyl- piperazinomethyl) -oxazolidin-2-one, 3- [4- (N-phenoxycarbonylamine) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-phenoxycarbonylamino) -phenyl] - 5- (4-benzyloxy-carbonylethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N- (3-pyridylcarbonyl) -amidino) -phenyl] -5-methanesulphonyloxymethyl-oxazolidin-2-one, 3- [4- (N- (3-pyridylcarbonyl) -amidino) - phenyl] -5- (4-benzyloxycarbonylethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N- (l-methyl-piperidyl-4-oxycarbonyl) -amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, the 3- [4- (N- (l- methyl-piperidyl-4-oxycarbonyl) -amidino) -pheneyl] -5- (4-benzyloxycarbonylethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-methoxycarbonylamidoino) -phenyl] -5-methanesulfoni loxi-methyl-oxazolidin-2-one, 3- [4- (N-methoxycarbonylamino) -phenyl] -5- (4-benzyloxy-carbonylethyl) piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-ethoxycarbonylmethylcarbamoyl-amidino) -phenyl] -5- ethanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-ethoxycarbonylmethylcarbamoyl-amidino) -phenyl] - 5- (4- benzyloxycarbonylethyl-piperazinomethyl) -oxazoli din-2-one;
- [4- (N-Methylsulfonylamine) -phenyl] -5-methanesulfonyloxymethyl-1-oxazolidin-2-one, 3- [4- (N-methylsulfonylamine) -phenyl] -5- (4-benzyloxycarbonylethyl-piperazinomethyl) - oxazolidin-2-one; 3- [4- (Nl-naphthoylamidino) -phenyl] -5-methanesulfonyloxy-ethyl-oxazolidin-2-one, 3- [4- (N-naphtholamidino) -phenyl] -5- (4-benzyloxycarbo-nilethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-2-naphthoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-naphthoylamidino) -phenyl] -5- (4-benzyloxycarbonyl) -piperazinomethyl) -oxazolidin-2-one; - [- (N-2-furoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-furoylamidino) -phenyl] -5- (4-benzyloxycarbonyl-ethyl- piperazinomethyl) -oxazolidin-2-one; - [4- (N-3-furoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-3-furoylamidino) -phenyl] -5- (4-benzyloxycarbonyl-ethyl-piperazinomethyl) ) -oxazolidin-2-one; 3- [4- (N-2-thienoylamidoino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-thienoylamidoino) -phenyl] -5- (4-benzyloxycarbo- nilethylpiperazinomethyl) -oxazolidin-2-one; 3- [4- (N-3-thienoylamidoino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-3-thienoylamidoino) -phenyl] -5- (4-benzyloxycarbonyl) nylethylpiperazinomethyl ) -oxazolidin-2-one; with 3- [4- (N-diphenylacetyl-amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-diphenylacetyl-amidino) -phenyl] -5- (4 -benzyloxy-carbonylethyl-piperazinomethyl) -oxazolidin-2-one. EXAMPLE 8 Analogously to that of Example 1, it is obtained by reaction of 4-methoxycarbonylmethylpiperazine with 3- [4- (N-benzyloxycarbonylamino) -phenyl] -5-methanesulphonyloxy-methyl-oxazolidin-2-one, - [4- (N-benzyloxycarbonylamido) -phenyl] -5- (4-methoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-benzoylamidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-benzoylamine) -phenyl] -5- (4-methoxycarbonyl-ethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-phenoxycarbonylamidoino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-phenoxycarbonylamino) -phenyl] -5- (4-methoxycarbonylmethyl) -piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N- (3-pyridylcarbonyl) -amidino) -phenyl] -5-methanesulphonyloxymethyl-oxazolidin-2-one, 3- [4- (N- (3-pyridylcarbonyl) -amidino) -phenyl] -5- (4-methoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N- (l-methyl-piperidyl-4-oxycarbonyl) -amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, the 3- [4- (N- (l- methyl-piperidyl-4-oxycarbonyl) -amidino) -pheneyl] -5- (4-methoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-methoxycarbonylamino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-methoxycarbonylamido) phenyl] -5- (4-methoxycarbonylmethyl) piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-ethoxycarbonylmethylcarbamoyl-amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-ethoxycarbonylmethylcarbamoyl-amidino) -phenyl] -5- (4- methoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; - [4- (N-Methylsulfonylamidoino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-methylsulfonylamine) -phenyl] -5- (4-methoxycarbonylmethyl-piperazinomethyl) ) -oxazolidin-2-one; 3- [4- (Nl-naphthoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (Nl-naphthoylamidino) -phenyl] -5- (4-methoxycarbonylmethylpiperazinomethyl) -oxazolidin -2-ona; 3- [4- (N-2-naphthoylamidino) -phenyl] -5-methanesulfonyloxymethyl-1-oxazolidin-2-one, 3- [4- (N-2-naphtholamidino) -phenyl] -5- (4-methoxycarbonylmethyl) tilpiperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-2-furoylamidino) -phenyl] -5-methanesulfonyloxymethyl-1-oxazolidin-2-one, 3- [4- (N-2-furoylamido) -phenyl] -5- (4-methoxycarbonylme tilpiperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-3-furoylamidoino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-3-furoylamido) -phenyl] -5- (4-methoxycarbonyl) ethylpiperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-2-thienoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-thienoylamidoino) -phenyl] -5- (4-methoxycarbonylme - tilpiperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-3-thienoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-3-thienoylamidoino) -phenyl] -5- (4-methoxycarbonylme Tilpiperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-diphenylacetyl-amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-diphenylacetyl-amidino) -phenyl] -5- (4 -methoxycarbonyl-nylmethyl-piperazinomethyl) -oxazolidin-2-one. EXAMPLE 9 Analogously to that of Example 1, by reaction of 4-isopropoxycarbonylmethylpiperazine with 3- [4- (N-benzyloxycarbonylamidoino) -phenyl] -5-methanesulphonyloxy-methyl-oxazolidin-2-one, the reaction is carried out. - [4- (N-benzyloxycarbonylamidoino) -phenyl] -5- (4-isopropoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; con3- [4- (N-benzoylamidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-benzoylamino) -phenyl] -5- (4-isopropoxycarbonylmethyl) piperazinomethyl) -oxazolidin-2-one, with 3- [4- (N-phenoxycarbonylamidoino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-phenoxycarbonylamido) -phenyl] -5- (4-isopropoxy carbonylmethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N- (3-pyridiicarbonyl) -amidino) -phenyl] -5-methanesulphonyloxymethyl-oxazolidin-2-one, 3- [4- (N- (3-pyridylcarbonyl) -amidino) phenyl] -5- (4-iso-propoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; with 3- (4- (N- (l-methyl-piperidyl-4-oxycarbonyl) -amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, the 3- [4- (N- (l -methyl-piperidyl-4-oxycarbonyl) -amidino) -pheneyl] -5- (4-isopropoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-methoxycarbonylamine) -phenyl] -5 -methanesulfonyloxy-methylene-1-oxazoli din-2-one, 3- [4- (N-methoxycarbonylamidino) -phenyl] -5- (4-isopropoxy carbonylmethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- ( N-ethoxycarbonylmethylcarbamoyl-amidino) -phenyl] -5- methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-ethoxycarbonylmethylcarbamoyl-amidino) -phenyl] -5- (4-isopropoxycarbonylmethyl-piperazinomethyl) -oxazoli - din-2-one; - [4- (N-methylsulfonylamine) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-methylsulfonylamine) -phenyl] -5- ( 4-isopropoxy carbonylmethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (Nl-naphthoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-naphtholamidino) - phenyl] -5- ( 4-isopropoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-2-naphthoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-naphthoylamidine) -phenyl] -5- (4-isopropoxycarboxymethyl) -piperazinomethyl) -oxazolidin-2-one; - [4- (N-2-furoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-furoylamidino) -phenyl] -5- (4-isopropoxycarboxymethyl) piperazinomethyl) -oxazolidin-2-one; - [4- (N-3-furoylamidino) -phenyl] -5-methanesulfonyloxymethyl-1-oxazolidin-2-one, 3- [4- (N-3-furoylamidino) -phenyl] -5- (4-isopropoxycarbonylmethylpiperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-2-thienoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-thienoylamidoino) -phenyl] -5- (4-isopropoxycarb) nylmethylpiperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-3-thienoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-3-thienoylamidino) -phenyl] -5- (4-isopropoxycarb) nylmethylpiperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-diphenylacetyl-amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-diphenylacetyl-amidino) -phenyl] -5- (4 -isopropoxy carbonylmethyl-piperazinomethyl) -oxazolidin-2-one. EXAMPLE 10 Analogously to that of Example 1, the reaction is obtained by 4-n-butoxycarbonylmethylpiperazine with 3- [4- (N-benzyloxycarbonylamido) phenyl] -5-methanesulphonyloxymethyl-oxazolidin-2-one, 3- [4- (N-benzyloxycarbonylamidoino) -phenyl] -5- (4-n-butoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-benzoylamidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-benzoylamine) -phenyl] -5- (4-n-butoxycarbonyl) - methyl-piperazinomethyl) -oxazolidin-2-one, with 3- [4- (N-phenoxycarbonylamido) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-phenoxycarbonylamido)) phenyl] -5- (4-n-butoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N- (3-pyridylcarbonyl) -amidino) -phenyl] -5-methanesulphonyloxymethyl-oxazolidin-2-one, 3- [4- (N- (3-pyridylcarbonyl) -amidino) - phenyl] -5- (4-n-butoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N- (l-methyl-piperidyl-4-oxycarbonyl) -amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, the 3- [4- (N- (l- methyl-piperidyl-4-oxycarbonyl) -amidino) -pheneyl] -5- (4-n-butoxycarbonylmethyl-piperazinomethyl) -oxa-zolidin-2-one; with 3- [4- (N-methoxycarbonylamidoino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-methoxycarbonylamidoino) -phenyl] -5- (4-n-butoxycarbonylmethyl) -piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-ethoxycarbonylmethylcarbamoyl-amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-ethoxycarbonylmethylcarbamoyl-amidino) -phenyl] -5- (4- n-butoxycarbonylmethyl-piperazinomethyl) -oxazoli din-2-one; - [4- (N-methylsulfonylamine) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-methylsulfonylamine) -phenyl] -5- (4-n-butoxycarbonylmethyl) -piperazinomethyl) -oxazolidin-2-one; 3- (4- (Nl-naphthoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-naphtholamidino) -phenyl] -5- (4-n-butoxycarbonylmethyl) piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-2-naphtholamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-naphtholamidino) -phenyl] ] -5- (4-n-butoxycarbonyl-methyl-piperazinomethyl) -oxazolidin-2-one; - [4- (N-2-furoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-furoylamidino) -phenyl] -5- (4-n-butoxycarbonyl-methyl-piperazinomethyl) -oxazolidin-2-one; - [4- (N-3-furoylamido) -phenyl] -5 -methanesulphonyloxymethyl-oxazolidin-2-one, 3- (4- (N-3-furoylamino) -phenyl] -5- (4-n-butoxycarbonyl-methyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- ( N-2-thienoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-thienoylamidoino) -phenyl] -5- (4-n-butoxycarbonyl-methyl-piperazinomethyl) -oxazolidin -2-one; 3- [4- (N-3-thienoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2- ona, 3- [4- (N-3-thienoylamidino) -phenyl] -5- (4-n-butoxycarbonyl-methyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-diphenylacetyl-amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-diphenylacetyl-amidino) -phenyl] -5- (4- n-butoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one. EXAMPLE 11 Analogously to that of Example 1, a reaction of 4-benzyloxycarbonylmethylpiperazine with 3- [4- (N-benzyloxycarbonylamidoino) -phenyl] -5-methanesulphonyloxy-methyl-oxazolidin-2-one is obtained. - [4- (N-benzyloxycarbonylamidoino) -phenyl] -5- (4-benzyl-xicarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; con3- [4- (N-benzoylamidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-benzoylamino) -phenyl] -5- (4-benzyloxycarbonylmethyl) piperazinomethyl) -oxazolidin-2-one, with 3- [4- (N-phenoxycarbonylamidoino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-phenoxycarbonylamido) -phenyl] -5- (4-benzyloxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N- (3-pyridylcarbonyl) -amidino) -phenyl] -5-methanesulphonyloxymethyl-oxazolidin-2-one, 3- [4- (N- (3-pyridylcarbonyl) -amidino) phenyl] -5- (4-benzyloxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N- (1-methyl-piperidyl-4-oxycarbonyl) -amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N- ( l-methyl-piperidyl-4-oxycarbonyl) -amidino) -pheneyl] -5- (4-benzyloxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-methoxycarbonylamidoino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-methoxycarbonylamido) phenyl] -5- (4-benzyloxycarbonylmethyl-piperazinomethyl) ) -oxazolidin-2-one; 3- [4- (N-ethoxycarbonylmethylcarbamoyl-amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-ethoxycarbonylmethylcarbamoyl-amidino) -phenyl] -5- (4- benzyloxycarbonylmethyl-piperazinomethyl) -oxazoli din-2-one; - [4- (N-Methylsulfonylamine) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-methylsulfonylamine) -phenyl] -5- (4-benzyloxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (Nl-naphthoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (Nl-naphthoylamidino) -phenyl] -5- (4-benzyloxycarbonylmethyl-piperazinomethyl) - oxazolidin-2-one; 3- [4- (N-2-naphthoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-naphthoylamidino) -phenyl] -5- (4-benzyloxycarbonylmethyl) -piperazinomethyl) -oxazolidin-2-one; - [4- (N-2-furoylamidino) -phenyl] -5-methanesulfonyloxymethyl-1-oxazolidin-2-one, 3- [4- (N-2-furoylamidino) -phenyl] -5- (4-benzyloxycarbonyl-methyl) -piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-3-furoylamidino) -phenyl] -5-methanesulfonyloxymethyl-1-oxazolidin-2-one, 3- [4- (N-3-furoylamido) -phenyl] -5- (4-benzyloxycarbonyl) - methylpiperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-2-thienoylamidoino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-thienoylamidoino) -phenyl] -5- (4-benzyloxycarb nylmethylpiperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-3-thienoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-3-thienoylamidino) -phenyl] -5- (4-benzyloxycarb) nylmethylpiperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-diphenylacetyl-amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-diphenylacetyl-amidino) -phenyl] -5- (4 -benzyloxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one. Example 12 Analogously to that of Example 1, it is obtained by reaction of 3-oxo-4-ethoxycarbonylethylpiperazine with 3- [4- (N-benzyloxycarbonylamino) -phenyl] -5-methanesulphonyloxymethyl-oxazolidin-2- ona, 3- [4- (N-benzyloxycarbonylamidoino) -phenyl] -5- (3-oxo-4-ethoxycarbonylethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-benzoylamidino) -phenyl] -5-methanesulfonyloxy-methy1-oxazolidin-2-one, 3- [4- (N-benzoylamino) -phenyl] -5- (3-oxo-4) -ethoxycarboxylethyl-piperazinomethyl) -oxazolidin-2-one, mp 164 °; with 3- [4- (N-phenoxycarbonylamidoino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-phenoxycarbonylamino) -phenyl] -5- (3-oxo-4) -tetoxycarbonylethyl-piperazinomethyl) -oxazolidin-2-one; con3- [4- (N- (3-pyridylcarbonyl) -amidino) -phenyl] -5-methanesulphonyloxymethyl-oxazolidin-2-one, 3- [4- (N- (3-pyridylcarbonyl) -amidino) -phenyl] ] -5- (3-oxo-4-ethoxycarbonylethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N- (l-methyl-piperidyl-4-oxycarbonyl) -amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, la3- [4- (N- (l- methyl-piperidyl-4-oxycarbonyl) -amidino) -pheneyl] -5- (3-oxo-4-ethoxycarbonylethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-methoxycarbonylamido) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-methoxycarbonylamido) -phenyl] -5- (3-oxo-4) -ethoxy-carbonylethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-ethoxycarbonylmethylcarbamoyl-amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-ethoxycarbonylmethylcarbamoyl-amidino) -phenyl] -5- (3 -oxo-4-ethoxycarbonylethyl-piperazinomethyl) -oxazolidin-2-one;
- [4- (N-methylsulfonylamine) -phenyl] -5-methanesulfonyloxymethyl-1-oxazolidin-2-one, 3- [4- (N-methylsulfonylamine) -phenyl] -5- (3-oxo-4-ethoxy-carbonylethyl) -piperazinomethyl) -oxazolidin-2-one; 3- [4- (Nl-naphthoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-naphtholamidino) -phenyl] -5- (3-oxo-4-ethoxycarbo- nilethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-2-naphthoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-naphthoylamidino) -phenyl] -5- (3-oxo- 4-ethoxycarbonylethyl-piperazinomethyl) -oxazolidin-2-one; - [4- (N-2-furoylamidoino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-furoylamino) -phenyl] -5- (3-oxo-4) ethoxycarboxylethyl-piperazinomethyl) -oxazolidin-2-one; - [4- (N-3-furoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-3-furoylamino) -phenyl] -5- (3-oxo-4) ethoxycarboxylethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-2-thienoylamidoino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-thienoylamidoino) -phenyl] -5- (3-oxo- 4-ethoxycarbonylethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-3-thienoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-3-thienoylamidoino) -phenyl] -5- (3-oxo- 4-ethoxycarbonyl-ethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-diphenylacetyl-amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-diphenylacetyl-amidino) -phenyl] -5- (3 -oxo-4-ethoxy-carbonylethyl-piperazinomethyl) -oxazolidin-2-one. EXAMPLE 13 Analogously to that of Example 1, it is obtained by reacting 3-oxo-4-ethoxycarbonylmethylpiperazine with 3- [4- (N-benzyloxycarbonylamido) phenyl] -5-methanesulphonyloxy-methyl-oxazolidin-2- ona, 3- [4- (N-benzyloxycarbonylamidoino) -phenyl] -5- (3-oxo-4-ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-benzoylamidino) -phenyl] -5-methanesulfonyloxy-methy1-oxazolidin-2-one, 3- [4- (N-benzoylamino) -phenyl] -5- (3-oxo-4) -ethoxycarbonyl-nylmethyl-piperazinomethyl) -oxazolidin-2-one, mp 180-181 °; with 3- [4- (N-phenoxycarbonylamidoino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-phenoxycarbonylamino) -phenyl] -5- (3-oxo-4) -ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N- (3-pyridylcarbonyl) -amidino) -phenyl] -5-methanesulphonyloxymethyl-oxazolidin-2-one, 3- [4- (N- (3-pyridylcarbonyl) -amidino) phenyl] -5- (3-oxo-4-ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N- (l-methyl-piperidyl-4-oxycarbonyl) -amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, the 3- [4- (N- (l- methyl-piperidyl-4-oxycarbonyl) -amidino) -phenyl] -5- (3-oxo-4-ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-methoxycarbonylamido) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-methoxycarbonylamido) -phenyl] -5- (3-oxo-4-) ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-ethoxycarbonylmethylcarbamoyl-amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-ethoxycarbonylmethylcarbamoyl-amidino) -phenyl] -5- (3- oxo-4-ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; - [4- (N-methylsulfonylamine) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-methylsulfonylamine) -phenyl] -5- (3-oxo-4-ethoxy) - carbonylmethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (Nl-naphthoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-naphtholamidino) -phenyl] -5- (3-oxo-4-ethoxycarbo- nylmethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-2-naphthoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-naphthoylamidino) -phenyl] -5- (3-oxo- 4-ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-2-furoylamidoino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-furoylamido) -phenyl] -5- (3-oxo) -4-ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-3-furoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazole-d-n-2-one, 3- [4- (N-3-furoylamidino) -phenyl] -5- (3-oxo-4-ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; with 3- (4- (N-2-thienoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-thienoylamidino) -phenyl] -5- (3-oxo) -4-ethoxycarbonyl-methyl-piperazinomethyl nil) oxazolidin-2-one; with 3- [4- (N-3-tienoilamidino) -phenyl] -5-metanosulfoniloximetil- oxazolidin-2-one, 3- [4 - (N-3-tienoilamidino) -phenyl] -5- (3-oxo-4-ethoxycarbonyl-nilmetil piperazinomethyl) oxazolidin-2-one; with 3- [4- (N-diphenylacetyl-amidino) -phenyl] -5-methyl-oxazolidin metanosulfoniloxi--2-one, 3- [4- (N-diphenylacetyl-amidino) -phenyl] -5- (3-oxo-4-ethoxy- carbonylmethyl-piperazinomethyl) oxazolidin-2- one. example 14 analogously to example 1, reaction of 4-ethoxycarbonylpiperidine with 3- [4- (N-benzyloxycarbonylamidino) -phenyl] -5-methanesulfonic Loxi-methyl-oxazolidin-2-one, 3- [4- (N-benzyloxycarbonylamido) -phenyl] -5- (4-ethoxycarbonylpiperidinomethyl) -oxazolidin-2-one; with 3- [4- (N-benzoylamine) -phenyl] -5-methanesulfonyloxy- meti1- oxazolidin-2-one, 3- [4- (N-be nzoylamidino) -phenyl] -5- (4-ethoxycarbonyl-piperidinomethyl) -oxazolidin-2-one, with 3- [4- (N-phenoxycarbonylamino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-Phenoxycarbonylamino) -phenyl] -5- (4-ethoxycarbonyl-piperidinomethyl) -oxazolidin-2-one; with 3- [4- (N- (3-pyridylcarbonyl) -amidino) -phenyl] -5-methanesulphonyloxymethyl-oxazolidin-2-one, 3- [4- (N- (3-pyridylcarbonyl) -amidino) phenyl] -5- (4-ethoxycarbonyl-piperidinomethyl) -oxazolidin-2-one; with 3- [4- (N- (l-methyl-piperidyl-4-oxycarbonyl) -amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, la3- [4- (N- (l- methyl-piperidyl-4-oxycarbonyl) -amidino) -phenyl] -5- (4-ethoxycarbonyl-piperidinomethyl) -oxazolidin-2-one; with 3- [4- (N-methoxycarbonylamido) phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-methoxycarbonylamino) -phenyl] -5- (4-ethoxycarbonyl) -piperidinomethyl) -oxazolidin-2-one; with 3- [4- (N-ethoxycarbonylmethylcarbamoyl-amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-ethoxycarbonylmethylcarbamoyl-amidino) -phenyl] -5- (4 -ethoxycarbonyl-piperidinomethyl) -oxazolidin-2-one; with 3- [4- (N-methylsulfonylamine) -pheny1] -5-methanesulfonyloxymethyl-1-oxazolidin-2-one, 3- [4- (N-methylsulfonylamine) -phenyl] -5- (4-ethoxycarbonyl-piperidinomethyl) ) -oxazolidin-2-one; with 3- [4- (Nl-naphthoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-naphtholamidino) -phenyl] -5- (4-ethoxycarbonyl-piperidinomethyl) - oxazolidin-2-one; with 3- [4- (N-2-naftoilamidino) -phenyl] -5-metanosulfoniloximetil- oxazolidin-2-one, 3- [4- (N-2-naftoilamidino) -phenyl] -5- (4-ethoxycarbonyl - piperidinomethyl) -oxazolidin-2-one; with 3- [4- (N-2-furoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-furoylamino) -phenyl] -5- (4-ethoxycarbonyl) - piperidinomethyl) -oxazolidin-2-one, mp 158-159 °, [) ü20 = + 32.7 ° (DMSO); con3- [4- (N-3-furoilamidino) -phenyl] -5-metanosulfoniloximetil- oxazolidin-2-one, 3- [4- (N-3-furoilamidino) -phenyl] -5- (4-ethoxycarbonyl piperidino ethyl) -oxazolidin-2-one; with 3- [4- (N-2-thienoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-thienoylamidino) -phenyl] -5- (4-ethoxycarbonyl) - 5-piperidinomethyl) -oxazolidin-2-one; with 3- [4- (N-3-thienoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-3-thienoylamidoino) -phenyl] -5- (4-ethoxycarbonyl) -) piperidinomethyl) -oxazolidin-2-one; 10 with 3- [4- (N-diphenylacetyl-amidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-diphenylacetyl-amidino) -phenyl] -5- ( 4-ethoxycarbonylpiperidinomethyl) -oxazolidin-2-one. Example 15 Analogously to that of Example 1, it is obtained by reaction of 4-ethoxycarbonylmethyl-4-hydroxy-piperidine with 3- [4- (N-benzyloxycarbonylamino) -phenyl] -5-methanesulfonyl-loxi-methyl- oxazolidin-2-one, 3- [4- (N-benzyloxycarbonylamido) -phenyl] -5- (4-ethoxycarbonylmethylmethyl-4-hydroxy-piperidinomethyl) -oxazolidin-2-one; with 3- [4- (N-benzoylamidino) -phenyl] -5-methanesulfonyloxy-methyl-1-oxazolidin-2-one, 3- [4- (N-benzoylamino) -phenyl] -5- (4-ethoxycarbonylmethyl) 4-hydroxy-piperidinomethyl) -oxazolidin-2-one, pf142 °;
with 3- [4- (N-phenoxycarbonylamidoino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-phenoxycarbonylamino) -phenyl] -5- (4-ethoxycarbonylmethyl) -4-hydroxy-piperidinomethyl) -oxazolidin-2- 5 -one; with 3- [4- (N- (3-pyridylcarbonyl) -amidino) -phenyl] -5-methanesulphonyloxymethyl-oxazolidin-2-one, 3- [4- (N- (3-pyridylcarbonyl) -amidino) phenyl] -5- (4-ethoxy-) carbonylmethyl-4-hydroxy-piperidinomethyl) -oxazolidin-2-one-one; with 3- [4- (N- (l-methyl-piperidyl-4-oxycarbonyl) -amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, la3- [4- (N- (l- methyl-piperidyl-4-oxycarbonyl) -amidino) -phenyl] -5- (4-methoxycarbonylmethyl-4-hydroxy-piperidinome-15-yl) -oxazolidin-2-one; with 3- [4- (N-methoxycarbonylamido) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one,? 3- [4- (N-methoxycarbonylamidoino) -phenyl] -5- (4-ethoxycarbonylmethyl-4-hydroxy-piperidinomethyl) -oxazolidin-2-one-one; with 3- [4- (N-ethoxycarbonylmethylcarbamoyl-amidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-ethoxycarbonylmethylcarbamoyl-amidino) -phenyl] -5- (4 -ethoxycarbonylmethyl-4-hydroxy-piperidinomethyl) -25-oxazolidin-2-one;
- [4- (N-methylsulfonylamine) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-methylsulfonylamine) -phenyl] -5- (4-ethoxycarbonylmethyl-4) -hydroxy-piperidinomethyl) -oxazolidin-2-one; 3- [4- (Nl-naphthoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-naphtholamidino) -phenyl] -5- (4-ethoxycarbonylmethyl-4-hydroxy) -piperidinomethyl) -oxazolidin-2-one; 3- [4- (N-2-naphthoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-naphthoylamido) -phenyl] -5- (4-ethoxycarbonylmethyl) -4-hydroxy-piperidinomethyl) -oxazolidin-2-one; - [4- (N-2-furoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-furoylamidino) -phenyl] -5- (4-ethoxycarbonylmethyl) 4-hydroxy-piperidinomethyl) -oxazolidin-2-one; - [4- (N-3-furoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-3-furoylamidino) -phenyl] -5- (4-ethoxycarbonyl) ethyl- 4-hydroxy-piperidinomethyl) -oxazolidin-2-one; 3- [4- (N-2-thienoylamidoino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-thienoylamidino) -phenyl] -5- (4-ethoxycarbonylmethyl) -4-hydroxy-piperidinomethyl) -oxazolidin-2-one;
with 3- [4- (N-3-thienoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-3-thienoylamidino) -phenyl] -5- (4-ethoxycarbonylme til-4-hydroxy-piperidinomethyl) -oxazolidin-2-one; 5 with 3- [4- (N-diphenylacetyl-amidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-diphenylacetyl-amidino) -phenyl] -5- ( 4-ethoxycarbonyl-methyl-4-hydroxy-piperidinomethyl) -oxazolidin-2-one. Example 16 10 0.9 g of 3- [4- (5-phenyl-1,2,4-oxadiazol-3-yl) -phenyl] -5- [4- (2-ethoxycarbonyl-2-N is dissolved. -butylsulfonylaminoethyl) phenoxymethyl] -oxazolidin-2-one [obtained according to example 1 by the reaction of 4- (5-phenyl-1, 2,4-oxadiazolin-3-yl) aniline with 2,3-epoxypropan-1 -ol to give N- [4- (5-phenyl-1,2,4-oxa-15-diazolin-3-yl) phenyl] -2,3-dihydroxy-propyl-amine, then by reaction with diethyl carbonate in the presence of potassium terbutoxide to give 3- [4- (5-phenyl-1,2,4-oxadiazolin-3-yl) -phenyl] -5-hydroxymethyl-oxazolidin-2-one, esterification with methanesulfonyl and reaction with p- (2-ethoxycarbonyl-2-N-butylsulfonylamino-ethyl) -phoxide] in 50 ml of methanol and hydrogenated with Raney-nickel. The reaction mixture is then filtered and the filtrate is concentrated by evaporation in vacuo. The product obtained is treated hot with 20 ml of ethyl acetate and filtered with suction after cooling. 3- [4- (N-benzoylamidino) -phenyl] -5- [4- (2-ethoxycarbonyl-2-N-butylsulfonylamino-ethyl) -phenoxymethyl] -oxazolidin-2-one is obtained. Analogously, it is obtained by reductive elimination of the 5-phenyl-1,2,4-oxadiazolino group and from 3- [4- (5-phenyl-1,2,4-oxadiazolin-3-yl) - phenyl] -5- [4- (2-ethoxycarbonyl-2-N-methylsulfonylamino-ethyl) -phenoxymethyl] -oxazolidin-2-one, 3- [4- (N-benzoylamidine) -phenyl] -5- [4- (2-ethoxycarbonyl-2- N -methylsulfonylamino-ethyl) -phenoxymethyl] -oxazolidin-2-one; 3- [4- (5-phenyl-1,2,4-oxadiazolin-3-yl) -phenyl] -5- [4- (2-ethoxy-carbonyl-2-a-naphthylamino-ethyl) -phenoxymethyl]] -oxazoli din-2-one, 3- [4- (N-benzoylamine) -phenyl] -5- [4- (2-ethoxycarbonyl-2-a-naphthoylamino-ethyl) -phenoxymethyl] -oxazolidin-2-one; of 3- [4- (5-phenyl-1,2,4-oxadiazolin-3-yl) -phenyl] -5- [4- (2-ethoxy-carbonyl-2-b-naphthylamino-ethyl) -phenoxymethyl] -oxazoli din-2-one, 3- [4- (N-benzoylamine) -phenyl] -5- [4- (2-ethoxycarbonyl-2-b-naphthoylamino-ethyl) -phenoxymethyl] -oxazolidin-2-one .
Example 17 0.5 g of l- [4- (5-phenyl-1,2,4-oxadiazo-lin-3-yl) -phenyl] -4- [4- (2-ethoxycarbonyl-ethyl) - is dissolved. piperazino] -piperidine [obtained by reaction of l- (5-phenyl-l, 2,4-oxadiazolin-3-yl) -4-chloro-piperidine with l- (2-ethoxycarbonyl-ethyl) -piperazine] in 50 ml of methanol and hydrogenated with Raney-nickel. The reaction mixture is then filtered and the filtrate is concentrated in vacuo. The product obtained is treated hot with 20 ml of ethyl acetate and filtered by suction after cooling. The l- [4- (N-benzoylamino) -phenyl] -4- [4- (2-ethoxycarbonyl-ethyl) -piperazino] -piperidine is obtained. Analogously, by reducing the 5-phenyl-1,2,4-oxadiazolino group and from 1- [4- (5-pheny1-1,2,4-oxadiazolin-3-yl) - phenyl] -4- (1-ethoxycarbonylmethyl-piperidin-4-yl) -piperazine, 1- [4- (N-benzoylamidino) -phenyl] -4- (1-ethoxycarbonyl-methyl-piperidin-4-yl) ) -piperazine; of l- [4- (5-phenyl-l, 2,4-oxadiazolin-3-yl) -phenyl] -4- [4- (ethoxycarbonyl-methyl) -piperazino] -piperidine, 1- [4- (N-benzoylamino) -phenyl] -4- (4-ethoxycarbonylmethyl) -piperazino] -piperidine; 1- [4- (5-phenyl-1,2,4-oxadiazolin-3-yl) -phenyl] -4- [1- (2-ethoxycarbonyl-ethyl) -piperidin-4-yl] -piperazine , l- [4- (N-benzoylamine) -phenyl] -4- [l- (2-ethoxycarbonyl-ethyl) -piperidin-4-yl] -piperazine. Example 18 Analogously to that of Example 17, the
2-0x0-3 (S) -ethoxycarbonyl-methyl-5 (S) - (4-N-benzoylamino-4'-oxymethyl-biphenyl) -pyrrolidine by hydrogenation of 1.1 g of 2-oxo-3 (S) -ethoxycarbonyl-methyl-5 (S) - [4- (5-phenyl-1,2,4-oxadiazo-3-yl) -4'-oxymethyl-biphenyl] -pyrrolidine [obtained by reaction of the sodium salt of 4- (5-phenyl-1,2,4-oxadiazolin-3-yl) -4'-hydroxy-biphenyl with 2-oxo-3 (S) -ethoxycarbonyl-methyl-5 (S) -methylsulfonyl-pyrrolidine] with Raney nickel in 50 ml of meta-nol and after treating the hydrogenation product in the usual manner. Analogously, it is obtained, by reductive elimination of the 5-phenyl-1,2,4-oxadiazolino group and from 2-oxo-3 (R) -ethoxycarbonyl-methyl-5 (S) - [4- (5 -phenyl-1,2,4-oxadiazolin-3-yl) -4'-oxymethyl-biphenyl] -pyrrolidine 2-0x0-3 (R) -ethoxycarbonyl-methyl-5 (S) - (4-N-benzoylamine) - 4'-oxymethyl-biphenyl] -pyrrolidine, 2-OXO-3 (R) -ethoxycarbonyl-methyl-5 (R) - [4- (5-phenyl-1, 2,4-oxadiazolin-3-yl) -4'-oxymethyl-biphenyl] -pyrrolidine 2-OXO-3 (R) -ethoxycarbonyl-methyl-5 (R) - (4-N-benzoylamino-4'-oxymethyl-biphenyl) -pyrrolidine; 2-OXO -3 (S) -ethoxycarbonyl-methyl-5 (R) - [4- (5-phenyl-1, 2,4-oxadiazolin-3-yl) -4'-oxymethyl-biphenyl] -pyrrolidine 2-OXO- 3 (S) -ethoxycarbonylmethyl-5 (R) - (4-N-benzoylamino-4'-oxymethyl-biphenyl) -pyrrolidine Example 19 0.7 g of [4- (N-benzoylamidino) -phenyl is dissolved. ] -succinamide [obtained by reaction of succinic acid monochloride with p- (N-benzoylamine) -aniline] in 70 ml of buta-nol and mixed with a equivalent of ethyl ester of 3-amino-4-pentyne in the presence of dicylohexylcarbodiimide. After stirring for three hours at room temperature, the reaction mixture is filtered and the filtrate is concentrated in vacuo. The residue obtained is treated in a usual manner. The N- [4- (N-benzoylamidino) -phenyl] -N '(1-ethoxycarbonylmethyl) -prop-2-yn-l-yl-succindyamide is obtained. Analogously, N- [4- (N-benzoylamidino) -phenyl] -succinamide is reacted with N- [4- (N-benzoylamidine) ethyl ester of 3 (S) -amino-4-pentynic acid. ) -phenyl] -N - [l (S) -ethoxycarbonyl methyl] -2-propin-l-yl-succindyamide; with the ethyl ester of 3 (R) -amino-4-pentynic acid the N- [4- (N-benzoylamidino) -phenyl] -N '- [l (R) -ethoxycarbonyl methyl] -2-propin-l- il-succindyamide. EXAMPLE 20 Analogously to Example 16, 1,2,4,5-tetrahydro-2-ethoxycarbonylmethyl-3-oxo-4-N- (2-phenylethyl) -8- [4- (N-benzoylamidine ) -phenyl-N-methylcarbamoyl] -benzodiazepine, from 1, 2,4,5-tetrahydro-2-ethoxy-carbonylmethyl-3-oxo-4-N- (2-phenylethyl) -8 - [4- (5-phenyl-l, 2,4-oxadiazolin-3-yl) -phenyl-N-methylcarbamoyl] -benzodiazepine [obtained by reaction of, 2,4,5-tetrahydro-2-ethoxycarbonylmethyl-3-oxo-4-N- (2-phenylethyl) -8-carboxy-benzodiazepine with 4- (5-phenyl-1,2,4-oxa-diazolin- 3-yl) -N-methylaniline], by reductive removal of the 5-phenyl-1,2,4-oxadiazolino group and subsequent usual treatment of the reaction mixture. EXAMPLE 21 0.6 g of ethyl 3- [4- (4- (N-benzoylpiperidin-4-yl) -butoxy) -phenyl] -3-aminopropionate [obtained by reaction of the sodium salt of 3- (0.6) is dissolved. 4-hydroxyphenyl) -3-N-BOC-ethyl-amine-propionate with l-chloro-4- (N-benzoylpiperidin-4-yl) -butane and subsequent cleavage of the protecting group] in 50 ml of THF, add an equivalent of n-butylsulfonyl chloride and stir for two hours at room temperature. The reaction mixture is then worked up in the usual manner and ethyl 3- [4- (4- (N-benzoylpiperidin-4-yl) -butoxy) -phenyl] -3-N-butylsulfonyl-aminopropionate is obtained. EXAMPLE 22 Analogously to Example 16, 3- [4- (N-benzoylamine) -phenyl] -5- [4- (1,2-di- (ethoxycarbonyl) -ethyl) piperazinomethyl] -oxazolidin- is obtained. 2-one, pf 136 °, by hydrogenation of 1.1 g of 3- [4- (5-phenyl-1,2,4-oxadiazolin-3-yl) -phenyl] -5- [4- (1, 2-diethoxycarbonylethyl) - pioperazinomethyl] -oxa-zolidin-2-one [obtained by the reaction of 4- (5-oxo-l, 2,4-oxa-diazolin-3-yl) -aniline with 2,3-epoxypropan-1-ol to give N- [4- (5-phenyl-1,2,4-oxadiazolin-3-yl) -phenyl] -2,3-dihydroxypropaneamine, then by reaction with diethyl carbonate in the presence of potassium terbutoxide to give 3- [4- (5-phenyl-l, 2,4-oxadiazolin-3-yl) -phenyl] -5-hydroxymethyl-oxazolidin-2-one, esterification with methanesulfonyl chloride and reaction with 1- (1, 2-diethoxycarbonylethyl) -piperazine] with nickel-Raney and subsequent usual treatment of the reaction mixture. In an analogous manner, by reduction of the 5-phenyl-1,2,4-oxadiazolino group and from 3- [4- (5-pheny1-1,2,4-oxadiazolin-3-yl) - phenyl] -5- [4- (1-carboxy-2-ethoxycarbonylethyl) -piperazinomethyl] -oxazolidin-2-one, 3- [4- (N-benzoylamine) -phenyl] -5- [4- ( l-carboxy-2-ethoxycarbonylethyl) -piperazinomethyl] -oxazolidin-2-one; of 3- [4- (5-phenyl-l, 2,4-oxadiazolin-3-yl) -phenyl] -5- [4- (2-carboxy-1-ethoxycarbonylethyl) -piperazinomethyl] -oxazolidin-2 -one, 3- [4- (N-benzoylamino) -phenyl] -5- [4- (2-carboxy-l-ethoxycarbonylethyl) -piperazinomethyl] -oxazolidin-2-one; de 3 - [4- (5-methyl-l, 2,4-oxadiazolin-3-yl) -phenyl] -5- [4- (1, 2-di-ethoxycarbonylethyl) -piperazinomethyl] -oxazolidin-2-one, 3- [4- (N-acetylamidoino) -phenyl] -5- [4- (1, 2-diethoxycarbonylethyl) -piperazinomethyl] -oxazolidin-2-one; of 3- [4- (5-methyl-l, 2,4-oxadiazolin-3-yl) -phenyl] -5- [4- (l-carboxy-2-ethoxycarbonylethyl) -piperazinomethyl] -oxazolidin-2 -one, 3- [4- (N-acetylamidoino) -phenyl] -5- [4- (l-carboxy-2-ethoxycarbonylethyl) -piperazinomethyl] -oxazolidin-2-one; of 3- [4- (5-methyl-l, 2,4-oxadiazolin-3-yl) -phenyl] -5- [4-. { 2-carboxy-1-ethoxycarbonylethyl) -piperazinomethyl] -oxazolidin-2-one, 3- [4- (N-acetylamidoino) -phenyl] -5- [4- (2-carboxy-1-ethoxy-carbonylethyl) -piperazinomethyl] -oxazolidin-2-one; 3- [4- (5-ethyl-l, 2,4-oxadiazolin-3-yl) -phenyl] -5- [4- (1, 2-di-ethoxycarbonylethyl) -piperazinomethyl] -oxazolidin-2-one , 3- [4- (N-propionylamino) -phenyl] -5- (4- (1, 2-diethoxycarbonylethyl) -piperazinomethyl] -oxazolidin-2-one, of 3- [4- (5-ethyl) -l, 2,4-oxadiazolin-3-yl) -phenyl] -5- [4- (1-carboxy-2-ethoxycarbonylethyl) -piperazinomethyl] -oxazolidin-2-one, 3- [4- (N- propionylamino) -phenyl] -5- [4- (l-carboxy-2-ethoxycarbonylethyl) -piperazinomethyl] -oxazolidin-2-one; 3- [4- (5-ethyl-1,2,4-oxadiazolin -3-yl) -phenyl] -5- [4- (2-carboxy-1-ethoxycarbonylethyl) -piperazinomethyl] -oxazolidin-2-one, 3- [4- (N-propionylamino) -phenyl] -5- [4- (2-carboxy-l-ethoxycarbonylethyl) -piperazinomethyl] -oxazolidin-2-one; of 3- [4- (5- (3-pyridyl) -l, 2,4-oxadiazolin-3-yl] ) -phenyl] -5- [4- (1,2-diethoxycarbonylethyl) -piperazinomethyl] -oxazolidin-2-one, 3- [4- (N- (3-pyridyl) -amidino) -phenyl] -5- [4- (1, 2-diethoxy-carbonylethyl) -piperazinomethyl) -oxazolidin-2-one; 3- [4- (5- (3-pyridyl) -l, 2,4-oxadiazolin-3-yl) -phenyl] -5- [4- (l-carboxy-2-ethoxycarbonylethyl) -piperazinomethyl] -oxazoli din-2-one, 3- [4- (N- (3-pyridyl) -amidino) -phenyl] -5- [4- (l-carboxy-2-ethoxycarbonylethyl) -piperazinomethyl] -oxazolidin-2-one; 3- [4- (5- (3-pyridyl) -l, 2,4-oxadiazolin-3-yl) -phenyl] -5- [4- (2-carboxy-1-ethoxycarbonylethyl) -piperazinomethyl] -oxazole i din-2-one, 3- [4- (N- (3-pyridyl) -amidino) -phenyl] -5- [4- (2-carboxy-l-ethoxycarbonylethyl) -piperazinomethyl] -oxazolidin-2- ona EXAMPLE 23 Analogously to that of Example 16, l- [3- (4-hydroxyphenyl) -2-N- (4- (N-benzoylamino) -benzoyl) -aminopropionyl] -4- (ethoxycarbonylmethoxy) is obtained. -piperidine, by hydrogenation of 0.8 g of l- [3- (4-hydroxyphenyl) -2-N- (4- (5-phenyl-1,2,4-oxadiazolin-3-yl) -benzoyl) - aminopropionyl] -4- (ethoxycarbonylmethoxy) -piperidine [obtained by the reaction of 3- (4-hydroxyphenyl) -2-N- (4- (5-phenyl-1,4,4-oxadiazolin-3-yl) - benzoyl) -aminopropionyl with 4- (ethoxycarbonylmethoxy) -piperidine] with nickel-Raney and subsequent usual treatment of the hydrogenated product. In an analogous manner, by reduction of the 5-phenyl-1, 2,4-oxadiazolino group and from 1 - [3-phenyl-2-N- (4- (5-phenyl-1, 2, 4-Oxadiazolin-3-yl) -benzoyl) -aminopropionyl] -4- (ethoxycarbonylmethoxy) -piperi-dine, 1- [3-phenyl-2-N- (4- (N-benzoylamino) -benzoyl) -aminopro pionyl ] -4- (ethoxycarbonylmethoxy) -piperidine;
del- [2-N- (4- (5-phenyl-l, 2,4-oxadiazolin-3-yl) -benzoyl) -aminopropionyl] -4- (ethoxycarbonylmethoxy) -piperidine, the l- [2-N- (4- (N-benzoylamino) -benzoyl) -aminopropionyl] -4- (ethoxycarbonylmethoxy) -piperidine; of l- [2-N- (4- (5-phenyl-1,2,4-oxadiazolin-3-yl) -benzoyl) -amino-acetyl] -4- (ethoxycarbonylmethoxy) -piperidine, 1- [2 -N- (4- (N-benzoylamino) -benzoyl) -aminoacetyl] -4- (ethoxycarbonylmethoxy) -piperidine. EXAMPLES 24 0.8 g of 3- [4- (N-benzoylamidino) -phenyl-5- [4- (1,2-diethoxycarbonylethyl) -piperazinomethyl] -oxazolidin-2-one [obtained according to example 22] is suspended. in 60 ml of methanol, add 10 ml of 2N NaOH solution and stir for 4 hours at room temperature. After removing the solvent, the residue is taken up with water, the pH is adjusted to 3 by the addition of dilute HCl and the reaction mixture is filtered through an ion exchange resin. The filtrate is dried over MgSO4. After removing the solvent and lyophilizing, 3- [4- (N-benzoylamine) -phenyl] -5- [4- (1, 2-dicarbo-xethyl) -piperazinomethyl] -oxazolidin-2-one is obtained. Analogously, by saponification of 3- [4- (N-acetylamidoino) -phenyl] -5- [4- (1, 2-diethoxycarbonylethyl) -piperazinomethyl] -oxazolidin-2-one, the 3- [4 - (N-acetylamidoino) -phenyl] -5- [4- (1, 2-dicarboxyethyl) -piperazinomethyl] -oxazolidin-2-one;
3- [4- (N-propionylamino) -phenyl] -5- [4- (1, 2-diethoxycarbonyl-ethyl) -piperazinomethyl] -oxazolidin-2-one, 3- [4- (N-propionylamidine)] phenyl] -5- [4- (1, 2-dicarboxyethyl) -piperazinomethyl] -oxazolidin-2-one; de 3- [4- (N- (3-pyridyl) -amidino) -phenyl] -5- [4- (1, 2-diethoxycarbonyl-ethyl) -piperazinomethyl] -oxazolidin-2-one, 3- [4 - (N- (3-pyridyl) -amidino) -phenyl] -5- [4-r (1,2-dicarboxylethyl) -piperazinomethyl] -oxazolidin-2-one. Example 25 Analogously to that of Example 1, a reaction of 4-ethoxycarbonylmethyl-piperazine ("A") with 3- [4- (N-4-chlorobenzoylamino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidine is obtained. -2-one, 3- [4- (N-4-chlorobenzoylamine) -phenyl] -5- (4-ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; with3- [4- (N-4-fluorobenzoylamine) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-4-fluorobenzoylamine) -phenyl] -5- (4- ethoxycarbon nylmethyl-piperazinomethyl) -oxazolidin-2-one; con3- [4- (N-4-methoxybenzoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-4-methoxybenzoylamine) -phenyl] -5- (4- ethoxycarbon nylmethyl-piperazinomethyl) -oxazolidin-2-one, mp 115-120 °; with 3- [4- (N -3,4-methylenedioxybenzoylamine) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-3,4-methylenedioxybenzoylamine) -phenyl] -5- (4-ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one, mp 168-169 °; 3- [4- (N-4-trifluoromethylbenzoylamino) -phenyl] -5-methanesulfonyloxy-methy1-oxazolidin-2-one, 3- [4- (N-4-trifluoromethylbenzoylamine) -phenyl] -5- (4 - ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-4-cyanobenzoylamino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-4-cyanobenzoylamine) -phenyl] -5- (4- ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-4-methoxybenzoylamine) -phenyl] -5 (R) -methanesulfonyl-oxoxymethyl-oxazolidin-2-one, 3- [4- (N-4-methoxybenzoylamine) -phenyl] -5 ( R) - (4-ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one, mp 153-154 °, [a] = + 31.2 ° (DMSO); 3- [4- (N-4-nitrobenzoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-4-nitrobenzoylamine) -phenyl] -5- (4- ethoxycarbon nyl-methyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-4-methylbenzoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-4-methylbenzoylamino) -phenyl] -5- (4- ethoxycarbon nyl-methyl-piperazinomethyl) -oxazolidin-2-one;
with 3- [4- (N-4-methoxycarbonylbenzoylamine) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-4-methoxycarbonylbenzoylamine) -phenyl] -5- ( - ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-4-tert-butylbenzoylamine) -phenyl] -5-methanesulphonyloxy-methy1-oxazolidin-2-one, 3- [4- (N-4-tert-butylbenzoylamine) -phenyl] -5- (4-ethoxy-carbonylmethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-3-chlorobenzoylamine) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-3-chlorobenzoylamine) -phenyl] -5- (4 -ethoxycarbonyl-nylmethyl-piperazinomethyl) -oxazolidin-2-one; con3- [4- (N-3-fluorobenzoylamino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-3-fluorobenzoylamine) -phenyl] -5- (4- ethoxycarbonylmethyl-1-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-3-methoxybenzoylamine) -phenyl] -5-methanesulfonyl ximethyl-oxazolidin-2-one, la3- [4- (N-3-methoxybenzoylamine) -phenyl] -5- (4-ethoxycarbon) nilraethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N -3,4-dimethoxybenzoylamidoino) -phenyl] -5-methanesulphonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-3,4-dimethoxybenzoylamine) phenyl] ] -5- (4-ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; con3- [4- (N-3-trifluoromethylbenzoylamino) -phenyl] -5 (R) -methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-3-trifluoromethylbenzoylamine) -phenyl] - 5 (R) - (4-ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one, mp 128-129 °, [a] = + 29.7 ° (DMSO); 3- [4- (N-3-cyanobenzoylamidoino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-3-cyanobenzoylamine) -phenyl] -5- (4- ethoxycarbon nylmethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-3-nitrobenzoylamine) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-3-nitrobenzoylamine) -phenyl] -5- (4- ethoxycarbon nylmethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-3-methylbenzoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-3-methylbenzoylamino) -phenyl] -5- (4- ethoxycarbon nylmethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-3-methoxycarbonylbenzoylamino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-3-methoxycarbonylbenzoylamine) -phenyl] -5- (4 - ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-3-tert-butylbenzoylamine) -phenyl] -5-methanesulphonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-3-tert-butylbenzoylamine) -phenyl] -5- ( 4-ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-2-chlorobenzoylamine) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-chlorobenzoylamine) -phenyl] -5- (4- ethoxycarbon nylmethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-2-fluorobenzoylamino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-fluorobenzoylamine) -phenyl] -5- (4 ethoxycarbon nylmethyl-piperazinomethyl) -oxazolidin-2-one; con3- [4- (N-2-methoxybenzoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-methoxybenzoylamine) -phenyl] -5- (4- ethoxycarbon nylmethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-2, 3, 4-trimethoxybenzoylamidino) -phenyl] -5-methanesul-fonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-2, 3, 4-trimethoxybenzoylamine ) -phenyl] -5- (4-ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-2-trifluoromethylbenzoylamino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-2-trifluoromethylbenzoylamine) -phenyl] -5- (4-ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one, mp 121 °; with 3- [4- (N-2-cyanobenzoylamino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-cyanobenzoylamino) -phenyl] -5- (4 ethoxycarbon nylmethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-2-nitrobenzoylamidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-2-nitrobenzoylamine) -phenyl] -5- (4 ethoxycarbon nylmethyl-piperazinomethyl) -oxazolidin-2-one; on 3- [4- (N-2-methylbenzoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-methylbenzoylamino) -phenyl] -5- (4 ethoxycarbon nylmethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-2-methoxycarbonylbenzoylamine) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-2-methoxycarbonylbenzoylamine) -phenyl] -5- ( 4- ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-2-tert-butylbenzoylamino) -phenyl] -5-methanesulphonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-2-tert-butylbenzoylamine) -phenyl] -5- (4-ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one. EXAMPLE 26 Analogously to that of Example 24, the following acid derivatives are obtained by saponification of the 4-ethoxycarbonylethyl-piperazines of Example 2: 3- [4- (N-benzoylamine) -phenyl] -5- ditrifluoroacetate ( 4- carboxyethyl-piperazinomethyl) -oxazolidin-2-one, mp 172 °; 3- [4- (N-Benzyloxycarbonylamidoino) -phenyl] -5- (4-carboxyethyl-piperazinomethyl) -oxazolidin-2-one ditrifluoroacetate, m.p. 134 °; 3- [4- (N-phenoxycarbonylamido) -phenyl] -5- (4-carboxyethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N- (3-pi idylcarbonyl) -amidino) -phenyl] -5- (4-carbo xethyl-piperazinomethyl) -oxazolidin-2-one; -3- [4- (N- (l-methyl-piperidyl-4-oxycarbonyl)) -amidino) -phenyl] -5- (4-carboxyethyl-piperazinomethyl) -oxazolidin-2-one; - 3- [4- (N-methoxycarbonylamido) phenyl] -5- (4-carboxyethyl-piperazinomethyl) -oxazolidin-2-one ditrifluoroacetate dihydrate, m.p. 99-100 °; 3- [4- (N-ethoxycarbonylmethylcarbamoyl-amidino) -phenyl] -5- (4-carboxyethyl-piperazinomethyl) -oxazolidin-2-one, m.p. 102 °;
- 3- [4- (N-methylsulfonylamine) -phenyl] -5- (4-carboxyethyl-piperazinomethyl) -oxazoli-din-2-one ditrifluoroacetate hydrate, m.p. 174 °; 3- [4- (N-l-naphthoylamidino) -phenyl] -5- (4-carboxyethyl-piperazinomethyl) -oxazolidin-2-one ditrifluoroacetate, p. f.111-113 °;
-3- [4- (N-2-naphthoylamidino) -phenyl] -5- (4-carboxyethyl-piperazomethyl) -oxazolidin-2-one; 3- [4- (N-diphenylacetyl-amidino) -phenyl] -5- (4-carboxyethyl-piperazinomethyl) -oxazolidin-2-one ditrifluoroacetate, m.p. 80- 83 °. Example 27 Analogously to that of Example 1, a reaction of 4-ethoxycarbonylmethyl-piperazine ("A") with 3- [4- (N-2-acetoxybenzoylamidino) -phenyl] -5-methanesulfonyl-ximethyl-oxazolidin is obtained. -2-one, 3- [4- (N-2-acetoxybenzoylamine) -phenyl] -5- (4-ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one. EXAMPLE 28 Analogously to that of Example 1, it is obtained by reacting 4-ethoxycarbonylethyl-piperazine with 3- [4- (N-2-acetoxybenzoylamine) -phenyl] -5-methanesulfonyl-ximethyl-oxazolidin-2-one, 3- [4- (N-2-acetoxybenzoylamine) -phenyl] -5- (4-ethoxycarbonylethyl) -piperazinomethyl) -oxazolidin-2-one. Example 29 Analogously to that of Example 1, it is obtained by reaction of 4- (2-acetoxyphenoxycarbonyl) -piperidine with 3- [4- (N-2-acetoxybenzoylamidoino) -phenyl] -5-methanesulfonyl ximethyl-oxazolidin-2 -one, 3- [4- (N-2-acetoxybenzoylamine) -phenyl] -5- [4- (2-acetoxy-phenoxycarbonyl) -piperidino] -oxazolidin-2-one. Example 30 Analogously to that of Example 1, it is obtained by reacting 4- (2-acetoxyphenoxycarbonyl) -piperidine with 3- [4- (N-benzoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-benzoylamino) -phenyl] -5- [4- (2-acetoxyphenoxycarbonyl) -piperidino] -oxazolidin-2-one. EXAMPLE 31 Analogously to that of Example 1, it is obtained by reaction of 4- (2-acetoxyphenoxycarbonylmethyl) -piperazine with 3- [4- (N-2-acetoxybenzoylamino) -phenyl] -5-methanesulfonyl ximethyl-oxazolidin-2 -one, 3- [4- (N-2-acetoxybenzoylamine) -phenyl] -5- [4- (2-acetoxyphenoxycarbonyl ethyl) -piperazinomethyl] -oxazolidin-2-one. Example 32 Analogously to that of Example 1, it is obtained by reaction of 4- (2-acetoxyphenoxycarbonylethyl) -piperazine with 3- [4- (N-2-acetoxybenzoylamido) -phenyl] -5-methanesulfonyl ximethyl-oxazolidin-2- ona, 3- [4- (N-2-acetoxybenzoylamine) -phenyl] -5- [4- (2-acetoxyphenoxycarbonylethyl) -piperazinomethyl] -oxazolidin-2-one. EXAMPLE 33 Analogously to that of Example 1, it is obtained by reaction of 4- (2-acetoxyphenoxycarbonylmethyl) -piperazine with 3- [4- (N-benzoylamine) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-benzoylamine) -phenyl] -5- [4- (2-acetoxyphenoxycarbonylmethyl) -piperazinomethyl] -oxazolidin-2-one. EXAMPLE 34 Analogously to that of Example 1, it is obtained by reaction of 4- (2-acetoxyphenoxycarbonylethyl) -piperazine with 3- [4- (N-benzoylamino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-benzoylamine) -phenyl] -5- [4- (2-acetoxy-phenoxy-carbonylethyl) -piperazinomethyl] -oxazolidin-2-one. Example 35 Analogously to that of Example 1, a reaction of 4-ethoxycarbonylethylpiperazine with 3- [4- (N-4-chlorobenzoylamine) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one is obtained. 3- [4- (N-4-chlorobenzoylamino) -phenyl] -5- (4-ethoxycarbonyl-n-ethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-4-fluorobenzoylamino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-4-fluorobenzoylamine) -phenyl] -5- (4 ethoxycarboxylethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-4-methoxybenzoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-4-methoxybenzoylamine) -phenyl] -5- (4 -ethoxycarboxylethyl-piperazinomethyl) -oxazolidin-2-one, mp 147-150 °; with 3- [4- (N-3,4-methylenedioxybenzoylamine) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-3,4-methylenedioxybenzoylamine) -phenyl] -5- (4-ethoxycarbonylethyl-piperazino ethyl) -oxazolidin-2-one; with 3- [4- (N-4-trifluoromethylbenzoylamidino) -phenyl] -5-methanesulfonyloxy-methy1-oxazolidin-2-one, 3- [4- (N-4-trifluoromethylbenzoylamine) -phenyl] -5- ( 4- ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one, mp 187 °; 3- [4- (N-4-cyanobenzoylamine) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-4-cyanobenzoylamine) -phenyl] -5- (4- ethoxycarboxylethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-4-nitrobenzoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-4-nitrobenzoylamine) -phenyl] -5- (4- ethoxycarboxylethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-4-methylbenzoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-4-methylbenzoylamino) -phenyl] -5- (4- ethoxycarboxylethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-4-methoxycarbonylbenzoylamino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-4-methoxycarbonylbenzoylamine) -phenyl] -5- (4 - ethoxycarbonylethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-4-tert-butylbenzoylamino) -phenyl] -5-methanesulphonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-4-tert-butylbenzoylamine) -phenyl] -5- ( 4-ethoxy-carbonylethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-3-chlorobenzoylamine) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-3-chlorobenzoylamine) -phenyl] -5- (4- ethoxycarboxylethyl-piperazinomethyl) -oxazolidin-2-one; - [4- (N-3-fluorobenzoylamidino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-3-fluorobenzoylamine) -phenyl] -5- (4-ethoxycarbon) nilethyl-piperazinomethyl) -oxazolidin-2-one; - [4- (N-3-methoxybenzoylamine) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-3-methoxybenzoylamine) -phenyl] -5- (4-ethoxycarbon) nilethyl-piperazinomethyl) -oxazolidin-2-one; - [4- (N -3,4-dimethoxybenzoylamine) -phenyl] -5-methanesulphonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-3,4-dimethoxybenzoylamine) -phenyl] - 5- (4-ethoxy-carbonylethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-3-trifluoromethylbenzoylamino) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-3-trifluoromethylbenzoylamine) -phenyl] -5- ( 4- ethoxycarbonylethyl-piperazinomethyl) -oxazolidin-2-one, mp 130-131 °; 3- [4- (N-3-cyanobenzoylamidoino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-3-cyanobenzoylamine) -phenyl] -5- (4- ethoxycarbon nylmethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-3-nitrobenzoylamine) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-3-nitrobenzoylamine) -phenyl] -5- (4- ethoxycarboxylethyl-piperazinomethyl) -oxazolidin-2-one; on 3- [4- (N-3-methylbenzoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-3-methylbenzoylamino) -phenyl] -5- (4 ethoxycarboxylethyl-piperazinomethyl) -oxazolidin-2-one; on 3- [4- (N-3-methoxycarbonylbenzoylamine) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-3-methoxycarbonylbenzoylamine) -phenyl] -5- ( 4- ethoxycarbonylethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-3-tert-butylbenzoylamino) -phenyl] -5-methanesulphonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-3-tert-butylbenzoylamine) -phenyl] -5- (4-ethoxy-carbonylethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-2-chlorobenzoylamine) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-2-chlorobenzoylamine) -phenyl] -5- (4 ethoxycarboxylethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-2-fluorobenzoylamino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-fluorobenzoylamine) -phenyl] -5- (4 ethoxycarboxylethyl-piperazinomethyl) -oxazolidin-2-one; con3- [4- (N-2-methoxybenzoylamine) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, la3- [4- (N-2-methoxybenzoylamine) -phenyl] -5- (4-ethoxycarbon) nilethyl-piperazinomethyl) -oxazolidin-2-one; - [4- (N-2, 3, 4-trimethoxybenzoylamine) -phenyl] -5-methanesul-fonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2,3,4-trimethoxybenzoylamine) - phenyl] -5- (4-ethoxycarbonylethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-2-trifluoromethylbenzoylamino) -phenyl] -5-methanesulfonyloxy-methy1-oxazolidin-2-one, 3- [4- (N-2-trifluoromethylbenzoylamine) -phenyl] -5- (4- ethoxycarbonylethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-2-cyanobenzoylamine) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-cyanobenzoylamine) -phenyl) -5- (4- ethoxycarboxylethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-2-nitrobenzoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-nitrobenzoylamine) -phenyl] -5- (4- ethoxycarboxylethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-2-methylbenzoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-2-methylbenzoylamino) -phenyl] -5- (4- ethoxycarboxylethyl-piperazinomethyl) -oxazolidin-2-one; 3- [4- (N-2-methoxycarbonylbenzoylamine) -phenyl] -5-methanesulfonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-2-methoxycarbonylbenzoylamine) -phenyl] -5- (4 - ethoxycarbonylethyl-piperazinomethyl) -oxazolidin-2-one;
with 3- [4- (N-2-tert-butylbenzoylamino) -phenyl] -5-methanesulphonyloxy-methyl-oxazolidin-2-one, 3- [4- (N-2-tert-butylbenzoylamine) -phenyl] -5- (4-ethoxy-carbonylethyl-piperazinomethyl) -oxazolidin-2-one. EXAMPLE 36 Analogously to that of Example 1, it is obtained by reaction of 4-tert.-butoxycarbonylmethyl-piperazine with 3- [4- (N-benzoylamino) -phenyl] -5 (R) -methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-benzoylamino) -phenyl] -5 (R) - (4-terbutoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one, mp 160 °, [a] D20 = + 32.7 °; with 3- [4- (N-benzoylamidino) -phenyl] -5-methanesulfonyloxymethyl-oxazolidin-2-one, 3- [4- (N-benzoylamine) -phenyl] -5- (4-tert-butoxycarbonylmethyl-piperazinomethyl) ) -oxazolidin-2-one, pf 182 °. EXAMPLE 37 Analogously to that of Example 1, it is obtained by reacting 4-methoxycarbonylmethyl sodium phenoxide with 3- [4- (N-benzoylamino) phenyl] -5-chloromethyl-oxazolidin-2-one, - [4- (N-benzoylamine) -phenyl] -5- (4-methoxycarbonylmethyl-phenoxymethyl) -oxazolidin-2-one, mp 170 °; analogously to that of Example 1, it is obtained by reacting 4- (l-methoxycarbonylmethyl-lN-butylsulphonylamino-ethyl) -pheno-sodium oxide with 3- [4- (N-benzoylamidino) -phenyl] -5- chloromethyl-oxazolidin-2-one, 3- [4- (N-benzoyiamidino) -phenyl] -5- [4- (1-methoxycarbonyl-1-N-butylsulfonylamino-ethyl) -phenoxymethyl] -oxazolidin-2-one . EXAMPLE 38 Analogously to that of Example 1, it is obtained by reaction of 1-ethoxycarbonylmethyl-piperazine with 3- [4- (N-ethoxycarbonylamino) -phenyl] -5 (R) -chloromethyl-oxazoli-din-2-one , 3- [4- (N-ethoxycarbonylamido) -phenyl] -5 (R) - (4-ethoxycarbonyl ethyl-ethyl-piperazinomethyl) -oxazolidin-2-one, mp 142-143 °; with 3- [4- (N-ethoxycarbonylamino) -phenyl] -5 (S) -chloro-ethyl-oxazolidin-2-one, 3- [4- (N-ethoxycarbonylamido) -phenyl] -5 (S) - (4-ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one, mp 142-143 °; with 3- [4- (N-isopropoxycarbonylamido) -phenyl] -5 (R) -chloromethyl-oxazolidin-2-one, 3- [4- (N-isopropoxycarbonylamido) -phenyl] -5 (R) - (4 -ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one, mp 129-130 °, (a] D20 = + 31.2 ° (DMSO);
with 3- [4- (N-isopropoxycarbonylamido) -phenyl] -5 (S) -chloromethyl-oxazolidin-2-one, 3- [4- (N-isopropoxycarbonylamido) -phenyl] -5 (S) - (4 -tetoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; with 3- [4- (N-methoxycarbonylamido) -phenyl] -5 (R) -chloromethyl-oxa-zolidin-2-one, 3- [4- (N-methoxycarbonylamido) -phenyl] -5 (R) - (4-ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one, mp 175-176 °, [o] D20 = + 51 ° (methanol); with 3- [4- (N-methoxycarbonylamido) -phenyl] -5 (S) -chloromethyl-oxa-zolidin-2-one, 3- [4- (N-methoxycarbonylamido) -phenyl] -5 (S) - (4-ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one; analogously, it is obtained, by reaction of 1-terbutoxicar-bonylmethyl-piperazine with 3- [4- (N-methoxycarbonylamino) -phenyl] -5-chloromethyl-oxaz-olidin-2-one, the 3- [4- (N -methoxycarbonylamine) -phenyl] -5- (4-terbutoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one, mp 181 °; with 3- [4- (N-ethoxycarbonylamidoino) -phenyl] -5-chloromethyl-oxazolidin-2-one, 3- [4- (N-ethoxycarbonylamido) phenyl] -5- (4-tert-butoxycarbonylmethyl-piperazinomethyl) ) -oxazolidin-2-one. Example 39 Analogously to Example 17, 1- [4- (N-benzoylamino) -phenyl] -4- [4- (ethoxycarbonyl) -piperidino] -piperidine, m.p. 118-119 °, from l- [4- (5-phenyl-1,2,4-oxadiazolin-3-yl) -phenyl] -4- [4-ethoxycarbonyl-piperidino] -piperidine [obtained by reaction of 1- (5-phenyl-1,2,4-oxadia-zolin-3-yl) -4-chloropiperidine with 1- (ethoxycarbonyl) -piperazine under the conditions indicated in example 1) and by reductive elimination of group 5 phenyl-1,2,4,4-oxadiazolino. EXAMPLE 40 Analogously to that of Example 24, by saponification of 3- [4- (N-benzoylamino) -phenyl] -5- (4-ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one [p.f. 114 °, Example 1], the 3- [4- (N-benzoylamidoino) -phenyl] -5- (4-carboxymethyl-piperazinomethyl) -oxazolidin-2-one bis-trifluoroacetate, m.p. 91 °; of 3- [4- (N-benzoylamino) -phenyl] -5 (R) - (4-ethoxycarbonylmethyl-piperazinomethyl) -oxazolidin-2-one [p.f. 150 °, Example 1], the 3- [4- (N-benzoylamino-phenyl) -5 (R) - (4-carboxymethyl-piperazinomethyl) -oxazolidin-2-one bis-trifluoroacetate, m.p. 147-150 °, [a] = 27.6 °; of 3- [4- (N-methoxycarbonylamidoino) -phenyl] -5- (4-ethoxycarbonylmethylperazinomethyl) -oxazolidin-2-one [p.f. 181 °, example 39], 3- [4- (N-methoxycarbonylamidoino) -phenyl] -5- (4-carboxymethyl-piperazinomethyl) -oxazolidin-2-one bis-trifluoroacetate, m.p. 92-93 °. The following examples relate to pharmaceutical preparations: Example A: bottles for injections The pH of a solution of 100 g of an active substance of formula I and 5 g of disodium hydrogen phosphate in 3 1 of bidistilled water is adjusted to 6, 5 with 2N hydrochloric acid, then it is filtered under sterile conditions, the bottles are filled with the solution, lyophilized and the bottles are closed under sterile conditions. Each bottle for injection contains 5 mg of the active substance. Example B: suppositories A mixture composed of 20 g of an active substance of formula I, 100 g of soya lecithin and 1400 g of cocoa butter is melted, then the melt is poured into the molds and allowed to cool. Each suppository contains 20 mg of active substance. Example C: solution A solution is prepared with 1 g of an active substance of formula I, 9.38 g of NaH2P04 x 2H20, 28.48 g of Na2HP04 x 12 H20, 0.1 g of benzalkonium chloride and 940 ml of bidistilled water. The pH is adjusted to 6.8, brought to a volume of 1 1 and sterilized by irradiation. This solution can be used in the form of eye drops. Example D: ointment Under aseptic conditions 500 mg of an active substance of formula I are mixed with 99.5 g of Vaseline. Example E: Tablets A mixture composed of 1 kg of an active substance of formula I, 4 kg of lactose, 1.2 kg of starch, 0.2 kg of talc and 0.1 kg of magnesium stearate is compressed in the form of tablets, such that each tablet contains 10 mg of the active substance. Example F: Tablets Tablets are formed analogously to that described in Example E and then coated in a usual manner with a bath of sucrose, starch, talc, tragacanth and dye. Example G: capsules With 2 kg of an active substance of formula I, hard gelatine capsules are filled, so that each capsule contains 20 mg of the active substance. Example H: ampoules A solution of 1 kg of an active substance of formula I in 60 1 of bidistilled water is filtered under sterile conditions. The ampoules are filled with this solution and then lyophilized and closed under sterile conditions. Each ampoule contains 10 mg of the active substance. It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention is that which is clear from the present description of the invention.
Having described the invention as above, property is claimed as contained in the following
Claims (8)
- REVIVALS 1.- Compounds characterized by responding to formula I where R represents where B = CH2, CO or CS, R10 = OH or H and m = 0, 1, 2, 3 0 4; wherein B = CH2, CO or CS, U = CH2 or CO and \ V = H, C02H C02A and n = 0, 1, 2 or 3; where n = 1, 2, 3, or 4; wherein R = H, A-S02, Ar-S02, A-CO, Ar-CO or Het-CO; wherein R5 = H, A, alkynyl or alkenyl of 2 to 5 carbon atoms or Ar; where D, E, F and G represent each time, independently of one another, CH or N and k and 1 represent each time, independently of each other, 0, 1, 2, 3 or 4, with the exception of k = 0, when E and F are each N, and of 1 = 0, when G = N; (g) -V_ / ~ C ° ~ "(5) - _ / ~ ° 'CH2" where As is an amino acid residue selected from the group consisting of Ala, Arg, Asn, Asp, Cys, Gln, Glu, Gly His, Lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Ty or Val, and which is linked through peptide bonds; where R ° = H or A and m independently represents 0, 1, 2, 3, 4 each time where R7 = OH, OA, OAr, OHet, NHOH, NH2, NHA or NA2 R8 = H or A and n is independently 1, 2, 3 or 4 each time where R4 has the meaning indicated in (d) and p is 2, 3, 4, 5, or 6; R1 represents H, A, Ar-CO, A-CO, OH, OA or AO-CO; R2 represents OH, OA, OAr, OHet, NHOH, NH2, NHA or NA2; R3 represents A-CO, Ar-CO, Het-CO, Het-O-CO, Ar-O-CO, A-O-CO, Ar-S02 or A-S02; A represents alkyl of 1 to 6 carbon atoms; Ar is diphenylmethyl, benzyl or aryl of 6 to 10 carbon atoms n substituted or substituted one or two times with A, F, Cl, Br, I, OA, -0-CH2-0, COOA, COOH, CF ,, OH, NO, CN, O-CO-A, NH2, NHA or NA2 and Het is a saturated, unsaturated or aromatic heterocycle, of one or two nuclei and containing 1 to 4 N atoms, and / or S , which may be unsubstituted or monosubstituted with F, Cl, Br, CF3, A, OH, OA, CN or N02, and the salts, physiologically acceptable, of these compounds.
- 2. Compounds of formula I, according to claim 1, characterized by their enantiomers or diastereomers.
- 3. Compounds according to claim 1, characterized by the following designations: (a) 3-p- (N-benzoylamine) -phenyl-5- [4- (ethoxycarbonyl ethyl) -piperazinomethyl] -oxazole idin-2-one; (b) 3-p- (N-pyridylcarbonylamidino) -phenyl-5- [4- (ethocarbonyl ethyl) -piperazinomethyl] -oxazolidin-2-one; (c) 3-p- (N-methyl-4-piperidyloxycarbonylamino) -phenyl-5- [4- (ethoxycarbonyl ethyl) -piperazinomethyl] -oxazoli-2-one; (d) 3-p- (N-methylsulfonylamido) -phenyl-5- (4-carboxyethyl-piperazinoethyl) -oxazole idin-2-one; (e) 3-p- (Nl-naphthoyl idino) -phenyl-1-5- (4-carboxyeti-1-piperazomethyl) -oxazolidin-2-one; (f) 3-p- [N- (ethoxycarbonylmethylcarbamoyl) -amidino] -feni1-5- [4 (terbutoxycarbonylethyl) -piperazinomethyl] -oxazolidin-2-one; (g) 3-p- (N-methylsulfonylamine) -phenyl-5- (4- (terbutoxicanenylethyl) -piperazinomethyl] -oxazole idin-2-one 4.- Process for preparing the compounds of formula I, according to claim 1, characterized in that (i) a compound of formula I is released from one of its functional derivatives by solvolysis or hydrogenolysis with a suitable agent, or because (ii) a compound of formula II is reacted wherein R, R 'and R2 have the indicated meanings with a compound of formula III R3-X (III), wherein R3 has the indicated meaning and X represents OH, F, Cl, Br, I or other leaving group easily cleavable, or because iii) to prepare a compound of formula I, according to claim 1, wherein R = (a), (b), (c) or (d), a compound of formula IV is reacted wherein R * represents R3-C0-NH-C (= NR ') - fi -, R1 and R3 having, like B, the meanings indicated in claim 1, and Z represents Cl, Br, I, OH or an esterified OH reactive group, with a compound of formula Va " { _ (Goes,, wherein Y represents -CH- (CH2) "- COR2, -N-CH (C02R) - (CH2) ,, - COR or -N- (CH2)" - COR2, and wherein U, R2, R, and n have the meanings indicated in claim 1, or with a compound of formula Vb wherein L represents - (CH2) "- COR2 or -CH2-CH (NHR4) -COR2, and wherein R2, R4 and n have the meanings indicated in claim 1, and X 'represents OH or a salt derived from the group OH, or because a compound of formula VI is reacted N-R 'R ».NH ^^ - NIH-CH2-CH (OH) -T (Vi) in which T is -BN ^ Y -CH2-OHTVL, and B, L, U and Y, like R1 and R3 have the meanings indicated above, with a reactive derivative of carbonic acid, or because (iv) to prepare a compound of Formula I, according to claim 1, in which R = (e), (f), (g), (h), (i) or (k), a compound of formula VII is reacted wherein R1 and R3 have the meanings indicated above, / - ^ M is NH2, NH-CO- (CH,) 2-C0X, -D NH. -D E- (CH2 X. -o e- (CH2) k -F NH, -COX, V = / X = J '-NR ° H or -CONRH, where D, E, F, X, X', AS, R °, R8 and k have the meanings indicated above, with a compound of formula VIII R2-CO -Q (VIII), in which R2 has the indicated meaning and Q is -Cfy-CHR'-NHCO- CHjJj-COX, -CH2-CHRS-NH ,, - (CH2), - X, -CH2-O- ^ N-. { AS > -H, wherein F, * G, X, R5, R7, AS, k, 1, and n have the meanings indicated above, or because (v) for preparing a compound of formula I, according to claim 1, wherein R = ( 1), a compound of formula IX is reacted (IX) wherein R1, R3, X and p have the indicated meanings, with a compound of formula X Wherein R 2, R 4 and X 'have the indicated meanings, or because to prepare a compound of formula I, according to claim 1, it is transformed, into a compound corresponding to general formula I, (vi) a R 1 residue in another residue R1 by alkylation or acylation, or (vii) a residue R2 in another residue R2, either by alkylating an amide hydrolyzing all or part of a cyano group by esterifying a COOH group or by transforming a COOH or COOA group into an amide, or because (viii) a compound of formula I, according to claim 1, is converted into one of its salts by treatment with an acid or a base. 5. Process for obtaining a pharmaceutical preparation based on the compounds of claim 1, characterized in that a compound of formula I and / or one of its physiologically acceptable salts is converted into a suitable dosage form, together with at least one excipient or solid, liquid or semi-liquid auxiliary product. 6. Pharmaceutical preparation based on the compounds of claim 1, characterized in that it contains at least one compound of general formula I and / or one of its physiologically acceptable salts. 1 . - Use of a compound of formula I, according to claim 1, and / or one of its physiologically acceptable salts for preparing drugs. 8. Use of a compound of formula I, according to claim 1, and / or one of its physiologically acceptable salts to combat diseases. 10 fifteen ) twenty 25
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE19516483.0 | 1995-05-05 | ||
DE19516483A DE19516483A1 (en) | 1995-05-05 | 1995-05-05 | Adhesion receptor antagonists |
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MX9601659A MX9601659A (en) | 1997-07-31 |
MXPA96001659A true MXPA96001659A (en) | 1997-12-01 |
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