SK282563B6 - Derivát oxazolidinónu, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje - Google Patents
Derivát oxazolidinónu, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje Download PDFInfo
- Publication number
- SK282563B6 SK282563B6 SK573-96A SK57396A SK282563B6 SK 282563 B6 SK282563 B6 SK 282563B6 SK 57396 A SK57396 A SK 57396A SK 282563 B6 SK282563 B6 SK 282563B6
- Authority
- SK
- Slovakia
- Prior art keywords
- phenyl
- oxazolidin
- methanesulfonyloxymethyloxazolidin
- formula
- group
- Prior art date
Links
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 title claims abstract description 77
- 238000002360 preparation method Methods 0.000 title claims description 7
- 239000000825 pharmaceutical preparation Substances 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 12
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 10
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 9
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 5
- 125000001424 substituent group Chemical group 0.000 claims abstract description 5
- 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 abstract description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 3
- 125000002619 bicyclic group Chemical group 0.000 claims abstract description 3
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 3
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 3
- -1 N-methylsulfonylamidino Chemical group 0.000 claims description 273
- 150000001875 compounds Chemical class 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 150000001408 amides Chemical class 0.000 claims description 6
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 238000003797 solvolysis reaction Methods 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims 2
- 108010049003 Fibrinogen Proteins 0.000 abstract description 8
- 102000008946 Fibrinogen Human genes 0.000 abstract description 8
- 229940012952 fibrinogen Drugs 0.000 abstract description 8
- 201000010099 disease Diseases 0.000 abstract description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 5
- 206010003210 Arteriosclerosis Diseases 0.000 abstract description 3
- 206010008190 Cerebrovascular accident Diseases 0.000 abstract description 3
- 206010061218 Inflammation Diseases 0.000 abstract description 3
- 208000001132 Osteoporosis Diseases 0.000 abstract description 3
- 208000006011 Stroke Diseases 0.000 abstract description 3
- 208000007536 Thrombosis Diseases 0.000 abstract description 3
- 208000011775 arteriosclerosis disease Diseases 0.000 abstract description 3
- 230000004054 inflammatory process Effects 0.000 abstract description 3
- 208000028867 ischemia Diseases 0.000 abstract description 3
- 208000010125 myocardial infarction Diseases 0.000 abstract description 3
- 230000000010 osteolytic effect Effects 0.000 abstract description 3
- 125000000041 C6-C10 aryl group Chemical group 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 252
- 238000006243 chemical reaction Methods 0.000 description 47
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 24
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 22
- WMSDOZUBILXRSY-UHFFFAOYSA-N [3-[4-(n'-benzoylcarbamimidoyl)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=CC=CC=2)C=C1 WMSDOZUBILXRSY-UHFFFAOYSA-N 0.000 description 16
- OHTFCTUQSFTCIO-UHFFFAOYSA-N [2-oxo-3-[4-(n'-phenylmethoxycarbonylcarbamimidoyl)phenyl]-1,3-oxazolidin-5-yl]methyl methanesulfonate Chemical compound O=C1OC(COS(=O)(=O)C)CN1C1=CC=C(C(=N)NC(=O)OCC=2C=CC=CC=2)C=C1 OHTFCTUQSFTCIO-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- OEEPIWZXDXYQPH-UHFFFAOYSA-N [2-oxo-3-[4-(n'-phenoxycarbonylcarbamimidoyl)phenyl]-1,3-oxazolidin-5-yl]methyl methanesulfonate Chemical compound O=C1OC(COS(=O)(=O)C)CN1C1=CC=C(C(=N)NC(=O)OC=2C=CC=CC=2)C=C1 OEEPIWZXDXYQPH-UHFFFAOYSA-N 0.000 description 11
- DKQYQXZPJPMCFF-UHFFFAOYSA-N [3-[4-[(e)-n'-methylsulfonylcarbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate Chemical compound C1=CC(C(=N)NS(=O)(=O)C)=CC=C1N1C(=O)OC(COS(C)(=O)=O)C1 DKQYQXZPJPMCFF-UHFFFAOYSA-N 0.000 description 11
- HCZFUAUIZSJPRZ-UHFFFAOYSA-N ethyl 2-[[(e)-[amino-[4-[5-(methylsulfonyloxymethyl)-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(COS(C)(=O)=O)C1 HCZFUAUIZSJPRZ-UHFFFAOYSA-N 0.000 description 11
- 125000006239 protecting group Chemical group 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- JYIYJUGNIXKYFW-UHFFFAOYSA-N [3-[4-[n'-(2,2-diphenylacetyl)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(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 JYIYJUGNIXKYFW-UHFFFAOYSA-N 0.000 description 9
- PMIQBANJPGQQRD-UHFFFAOYSA-N [3-[4-[n'-(naphthalene-1-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=2C3=CC=CC=C3C=CC=2)C=C1 PMIQBANJPGQQRD-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
- 239000004480 active ingredient Substances 0.000 description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-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
- 238000006894 reductive elimination reaction Methods 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- 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 7
- ZABBALBVJIQHRV-UHFFFAOYSA-N [3-[4-[(e)-n'-methoxycarbonylcarbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate Chemical compound C1=CC(C(=N)NC(=O)OC)=CC=C1N1C(=O)OC(COS(C)(=O)=O)C1 ZABBALBVJIQHRV-UHFFFAOYSA-N 0.000 description 7
- 125000002252 acyl group Chemical group 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- JPSKIVXPJPRREK-UHFFFAOYSA-N 5-phenyl-2,5-dihydro-1,2,4-oxadiazole Chemical group N1C=NOC1C1=CC=CC=C1 JPSKIVXPJPRREK-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
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-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
- 239000002585 base Substances 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 239000007868 Raney catalyst Substances 0.000 description 5
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 5
- 229910000564 Raney nickel Inorganic materials 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- 108020003175 receptors Proteins 0.000 description 5
- 102000005962 receptors Human genes 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 4
- MTFCXMJOGMHYAE-UHFFFAOYSA-N Ethyl piperazinoacetate Chemical compound CCOC(=O)CN1CCNCC1 MTFCXMJOGMHYAE-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 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
- 239000000047 product Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 210000004881 tumor cell Anatomy 0.000 description 4
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 3
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 3
- 108010012088 Fibrinogen Receptors Proteins 0.000 description 3
- 102100037362 Fibronectin Human genes 0.000 description 3
- 108010067306 Fibronectins Proteins 0.000 description 3
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 3
- 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 3
- 239000013543 active substance Substances 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000012154 double-distilled water Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- XCLNGVSHLDOGFR-UHFFFAOYSA-N ethyl 3-piperazin-1-ylpropanoate Chemical compound CCOC(=O)CCN1CCNCC1 XCLNGVSHLDOGFR-UHFFFAOYSA-N 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 150000003460 sulfonic acids Chemical class 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
- 108010047303 von Willebrand Factor Proteins 0.000 description 3
- 102100036537 von Willebrand factor Human genes 0.000 description 3
- 229960001134 von willebrand factor Drugs 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
- DCTSCCYMGLMYKY-UHFFFAOYSA-N 3-(4-aminophenyl)-2h-1,2,4-oxadiazol-5-one Chemical compound C1=CC(N)=CC=C1C1=NOC(=O)N1 DCTSCCYMGLMYKY-UHFFFAOYSA-N 0.000 description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- JMRRJBJGXNGGOO-UHFFFAOYSA-N 4-[4-(n'-benzoylcarbamimidoyl)anilino]-4-oxobutanoic acid Chemical compound C1=CC(NC(=O)CCC(=O)O)=CC=C1C(=N)NC(=O)C1=CC=CC=C1 JMRRJBJGXNGGOO-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 241000282693 Cercopithecidae Species 0.000 description 2
- 108010035532 Collagen Proteins 0.000 description 2
- 102000008186 Collagen Human genes 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 2
- 108090000288 Glycoproteins Proteins 0.000 description 2
- 102000003886 Glycoproteins Human genes 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 206010027476 Metastases Diseases 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- WDPSYQUEXBDCRN-UHFFFAOYSA-N O=C1OC(COS(=O)(=O)C)CN1C1=CC=C(C(N)=NC(=O)C=2C=CC(=CC=2)[N+]([O-])=O)C=C1 Chemical compound O=C1OC(COS(=O)(=O)C)CN1C1=CC=C(C(N)=NC(=O)C=2C=CC(=CC=2)[N+]([O-])=O)C=C1 WDPSYQUEXBDCRN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 108010031318 Vitronectin Proteins 0.000 description 2
- 102100035140 Vitronectin Human genes 0.000 description 2
- VCAWEKFZMSLIIY-UHFFFAOYSA-N [2-[[amino-[4-[5-(methylsulfonyloxymethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]methylidene]carbamoyl]phenyl] acetate Chemical compound CC(=O)OC1=CC=CC=C1C(=O)N=C(N)C1=CC=C(N2C(OC(COS(C)(=O)=O)C2)=O)C=C1 VCAWEKFZMSLIIY-UHFFFAOYSA-N 0.000 description 2
- AMXDVQDUMKGJHJ-UHFFFAOYSA-N [3-[4-[n'-(1,3-benzodioxole-5-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=C3OCOC3=CC=2)C=C1 AMXDVQDUMKGJHJ-UHFFFAOYSA-N 0.000 description 2
- HHZFGHRTZYSQNC-UHFFFAOYSA-N [3-[4-[n'-(2-chlorobenzoyl)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(=CC=CC=2)Cl)C=C1 HHZFGHRTZYSQNC-UHFFFAOYSA-N 0.000 description 2
- RUYIBKUFRXBFLY-UHFFFAOYSA-N [3-[4-[n'-(3-chlorobenzoyl)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=C(Cl)C=CC=2)C=C1 RUYIBKUFRXBFLY-UHFFFAOYSA-N 0.000 description 2
- UIOVKUSKPDCOSV-UHFFFAOYSA-N [3-[4-[n'-(4-tert-butylbenzoyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)N=C(N)C1=CC=C(N2C(OC(COS(C)(=O)=O)C2)=O)C=C1 UIOVKUSKPDCOSV-UHFFFAOYSA-N 0.000 description 2
- RAWQRBSONNUHAS-UHFFFAOYSA-N [3-[4-[n'-(furan-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=2OC=CC=2)C=C1 RAWQRBSONNUHAS-UHFFFAOYSA-N 0.000 description 2
- MXTKSGRDHFMORP-UHFFFAOYSA-N [3-[4-[n'-(furan-3-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)C2=COC=C2)C=C1 MXTKSGRDHFMORP-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 230000001772 anti-angiogenic effect Effects 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229920001436 collagen Polymers 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- DORYZKWDSPBKKM-UHFFFAOYSA-N diethyl 2-[4-[[3-[4-(n'-benzoylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]butanedioate Chemical compound C1CN(C(CC(=O)OCC)C(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)C=2C=CC=CC=2)C1 DORYZKWDSPBKKM-UHFFFAOYSA-N 0.000 description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
- IQHUNRUDSIXLEE-JOCHJYFZSA-N ethyl 2-[4-[[(5r)-3-[4-(n'-benzoylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCN1C[C@H]1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)C=2C=CC=CC=2)C1 IQHUNRUDSIXLEE-JOCHJYFZSA-N 0.000 description 2
- IQHUNRUDSIXLEE-UHFFFAOYSA-N ethyl 2-[4-[[3-[4-(n'-benzoylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)C=2C=CC=CC=2)C1 IQHUNRUDSIXLEE-UHFFFAOYSA-N 0.000 description 2
- VDKVPBCMAIZLLR-UHFFFAOYSA-N ethyl 2-piperidin-4-yloxyacetate Chemical compound CCOC(=O)COC1CCNCC1 VDKVPBCMAIZLLR-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 210000004211 gastric acid Anatomy 0.000 description 2
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000007943 implant Substances 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 108010044426 integrins Proteins 0.000 description 2
- 102000006495 integrins Human genes 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000009401 metastasis Effects 0.000 description 2
- BVNFBHOJDPAZAX-UHFFFAOYSA-N methyl 3-piperazin-1-ylpropanoate Chemical compound COC(=O)CCN1CCNCC1 BVNFBHOJDPAZAX-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229920001592 potato starch Polymers 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 239000008347 soybean phospholipid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- JOJBGPBSHQZRDA-UHFFFAOYSA-N tert-butyl 2-piperazin-1-ylacetate Chemical compound CC(C)(C)OC(=O)CN1CCNCC1 JOJBGPBSHQZRDA-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 1
- 125000005940 1,4-dioxanyl group Chemical group 0.000 description 1
- OOSZCNKVJAVHJI-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]piperazine Chemical compound C1=CC(F)=CC=C1CN1CCNCC1 OOSZCNKVJAVHJI-UHFFFAOYSA-N 0.000 description 1
- 125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 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 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- JODXKZAUFHEYGO-UHFFFAOYSA-N 2,3-dihydroxybutanedioyl dichloride Chemical compound ClC(=O)C(O)C(O)C(Cl)=O JODXKZAUFHEYGO-UHFFFAOYSA-N 0.000 description 1
- UZYQSNQJLWTICD-UHFFFAOYSA-N 2-(n-benzoylanilino)-2,2-dinitroacetic acid Chemical compound C=1C=CC=CC=1N(C(C(=O)O)([N+]([O-])=O)[N+]([O-])=O)C(=O)C1=CC=CC=C1 UZYQSNQJLWTICD-UHFFFAOYSA-N 0.000 description 1
- CHOVOSNYINSVEC-HXUWFJFHSA-N 2-[4-[[(5r)-3-[4-(n'-benzoylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCN1C[C@H]1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)C=2C=CC=CC=2)C1 CHOVOSNYINSVEC-HXUWFJFHSA-N 0.000 description 1
- SGWISPNVNDVIER-UHFFFAOYSA-N 2-[4-[[3-[4-(n'-benzoylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]-4-ethoxy-4-oxobutanoic acid Chemical compound C1CN(C(CC(=O)OCC)C(O)=O)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)C=2C=CC=CC=2)C1 SGWISPNVNDVIER-UHFFFAOYSA-N 0.000 description 1
- NCLDBBBBJGEGQG-UHFFFAOYSA-N 2-[4-[[3-[4-(n'-benzoylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]butanedioic acid Chemical compound C1CN(C(CC(=O)O)C(O)=O)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)C=2C=CC=CC=2)C1 NCLDBBBBJGEGQG-UHFFFAOYSA-N 0.000 description 1
- WHAHIZSSWLJJKW-UHFFFAOYSA-N 2-[4-[[3-[4-[(e)-n'-methoxycarbonylcarbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetic acid Chemical compound C1=CC(C(=N)NC(=O)OC)=CC=C1N1C(=O)OC(CN2CCN(CC(O)=O)CC2)C1 WHAHIZSSWLJJKW-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 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 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- PCJFEVUKVKQSSL-UHFFFAOYSA-N 2h-1,2,4-oxadiazol-5-one Chemical group O=C1N=CNO1 PCJFEVUKVKQSSL-UHFFFAOYSA-N 0.000 description 1
- CRBWGQGSZPAPFM-UHFFFAOYSA-N 3-(2-phenylethyl)-1H-1,2-benzodiazepine-8-carboxylic acid Chemical compound C1(=CC=CC=C1)CCC1=NNC2=C(C=C1)C=CC(=C2)C(=O)O CRBWGQGSZPAPFM-UHFFFAOYSA-N 0.000 description 1
- WLDYTMATFBTXBJ-UHFFFAOYSA-N 3-(4-chloropiperidin-1-yl)-5-phenyl-2,5-dihydro-1,2,4-oxadiazole Chemical compound C1CC(Cl)CCN1C1=NOC(C=2C=CC=CC=2)N1 WLDYTMATFBTXBJ-UHFFFAOYSA-N 0.000 description 1
- VLOZFUCTUDOGPK-UHFFFAOYSA-N 3-(piperazin-1-ylmethyl)-1,3-oxazolidin-2-one Chemical compound N1(CCNCC1)CN1C(OCC1)=O VLOZFUCTUDOGPK-UHFFFAOYSA-N 0.000 description 1
- FYIBDDHKBYHCRZ-UHFFFAOYSA-N 3-[4-(2,3-dihydroxypropylamino)phenyl]-2h-1,2,4-oxadiazol-5-one Chemical compound C1=CC(NCC(O)CO)=CC=C1C1=NOC(=O)N1 FYIBDDHKBYHCRZ-UHFFFAOYSA-N 0.000 description 1
- RTOZRTJRRHOPOI-UHFFFAOYSA-N 3-[4-[5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]-2h-1,2,4-oxadiazol-5-one Chemical compound O=C1OC(CO)CN1C1=CC=C(C=2NC(=O)ON=2)C=C1 RTOZRTJRRHOPOI-UHFFFAOYSA-N 0.000 description 1
- AYIBLONMGAOHGT-UHFFFAOYSA-N 3-[4-[[2-oxo-3-[4-[(z)-n'-phenylmethoxycarbonylcarbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoic acid Chemical compound C1CN(CCC(=O)O)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)OCC=2C=CC=CC=2)C1 AYIBLONMGAOHGT-UHFFFAOYSA-N 0.000 description 1
- SKMSCAAUKZGAEX-UHFFFAOYSA-N 3-[4-[[3-[4-(n'-benzoylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]-4-ethoxy-4-oxobutanoic acid Chemical compound C1CN(C(CC(O)=O)C(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2C=CC=CC=2)C1 SKMSCAAUKZGAEX-UHFFFAOYSA-N 0.000 description 1
- BWXOCMORGCTYEK-UHFFFAOYSA-N 3-[4-[[3-[4-(n'-benzoylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoic acid Chemical class C1CN(CCC(=O)O)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)C=2C=CC=CC=2)C1 BWXOCMORGCTYEK-UHFFFAOYSA-N 0.000 description 1
- ZTFZMOYUDNTZAL-UHFFFAOYSA-N 3-[4-[[3-[4-[N-[(2-ethoxy-2-oxoethyl)carbamoyl]carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoic acid Chemical compound C1=CC(C(=N)NC(=O)NCC(=O)OCC)=CC=C1N1C(=O)OC(CN2CCN(CCC(O)=O)CC2)C1 ZTFZMOYUDNTZAL-UHFFFAOYSA-N 0.000 description 1
- ASRAXZHFGZXZAJ-UHFFFAOYSA-N 3-[4-[[3-[4-[n'-(naphthalene-1-carbonyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoic acid Chemical compound C1CN(CCC(=O)O)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)C=2C3=CC=CC=C3C=CC=2)C1 ASRAXZHFGZXZAJ-UHFFFAOYSA-N 0.000 description 1
- TWGQHCAZYFFMMD-UHFFFAOYSA-N 3-[4-[[3-[4-[n'-(naphthalene-2-carbonyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoic acid Chemical compound C1CN(CCC(=O)O)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)C=2C=C3C=CC=CC3=CC=2)C1 TWGQHCAZYFFMMD-UHFFFAOYSA-N 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- QGWCYYDJPGZGOF-UHFFFAOYSA-N 4-(5-phenyl-2,5-dihydro-1,2,4-oxadiazol-3-yl)aniline Chemical compound C1=CC(N)=CC=C1C1=NOC(C=2C=CC=CC=2)N1 QGWCYYDJPGZGOF-UHFFFAOYSA-N 0.000 description 1
- VMPUZKDPSWRKBE-UHFFFAOYSA-N 4-ethoxy-2-[4-[[3-[4-(5-ethyl-2,5-dihydro-1,2,4-oxadiazol-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]-4-oxobutanoic acid Chemical compound C1CN(C(CC(=O)OCC)C(O)=O)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C=2NC(CC)ON=2)C1 VMPUZKDPSWRKBE-UHFFFAOYSA-N 0.000 description 1
- SRFMJXXWHNCKDX-UHFFFAOYSA-N 4-ethoxy-2-[4-[[3-[4-(5-methyl-2,5-dihydro-1,2,4-oxadiazol-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]-4-oxobutanoic acid Chemical compound C1CN(C(CC(=O)OCC)C(O)=O)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C=2NOC(C)N=2)C1 SRFMJXXWHNCKDX-UHFFFAOYSA-N 0.000 description 1
- PPANQFZCHKYZRF-UHFFFAOYSA-N 4-ethoxy-3-[4-[[3-[4-(5-ethyl-2,5-dihydro-1,2,4-oxadiazol-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]-4-oxobutanoic acid Chemical compound C1CN(C(CC(O)=O)C(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C=2NC(CC)ON=2)C1 PPANQFZCHKYZRF-UHFFFAOYSA-N 0.000 description 1
- FHAARLGXPBNVNQ-UHFFFAOYSA-N 4-ethoxy-3-[4-[[3-[4-(5-methyl-2,5-dihydro-1,2,4-oxadiazol-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]-4-oxobutanoic acid Chemical compound C1CN(C(CC(O)=O)C(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C=2NOC(C)N=2)C1 FHAARLGXPBNVNQ-UHFFFAOYSA-N 0.000 description 1
- GSKBDOFUJSINLG-UHFFFAOYSA-N 4-ethoxy-4-oxo-2-[4-[[2-oxo-3-[4-(n'-pyridin-3-ylcarbamimidoyl)phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]butanoic acid Chemical compound C1CN(C(CC(=O)OCC)C(O)=O)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC=2C=NC=CC=2)C1 GSKBDOFUJSINLG-UHFFFAOYSA-N 0.000 description 1
- DMPMSNQJKHGGMM-UHFFFAOYSA-N 4-ethoxy-4-oxo-3-[4-[[2-oxo-3-[4-(5-phenyl-2,5-dihydro-1,2,4-oxadiazol-3-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]butanoic acid Chemical compound C1CN(C(CC(O)=O)C(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C=2NC(ON=2)C=2C=CC=CC=2)C1 DMPMSNQJKHGGMM-UHFFFAOYSA-N 0.000 description 1
- XSWZNBWQMHCENV-UHFFFAOYSA-N 4-ethoxy-4-oxo-3-[4-[[2-oxo-3-[4-(5-pyridin-3-yl-2,5-dihydro-1,2,4-oxadiazol-3-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]butanoic acid Chemical compound C1CN(C(CC(O)=O)C(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C=2NC(ON=2)C=2C=NC=CC=2)C1 XSWZNBWQMHCENV-UHFFFAOYSA-N 0.000 description 1
- CJFBEOPRPLOYRU-UHFFFAOYSA-N 4-ethoxy-4-oxo-3-[4-[[2-oxo-3-[4-(n'-propanoylcarbamimidoyl)phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]butanoic acid Chemical compound C1CN(C(CC(O)=O)C(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)CC)C1 CJFBEOPRPLOYRU-UHFFFAOYSA-N 0.000 description 1
- YVZCOQQLLSXZRQ-UHFFFAOYSA-N 4-ethoxy-4-oxo-3-[4-[[2-oxo-3-[4-(n'-pyridin-3-ylcarbamimidoyl)phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]butanoic acid Chemical compound C1CN(C(CC(O)=O)C(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC=2C=NC=CC=2)C1 YVZCOQQLLSXZRQ-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
- YORRNWWTUREMMW-UHFFFAOYSA-N 5-(hydroxymethyl)-3-[4-(5-phenyl-2,5-dihydro-1,2,4-oxadiazol-3-yl)phenyl]-1,3-oxazolidin-2-one Chemical compound O=C1OC(CO)CN1C1=CC=C(C=2NC(ON=2)C=2C=CC=CC=2)C=C1 YORRNWWTUREMMW-UHFFFAOYSA-N 0.000 description 1
- 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 description 1
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 208000009304 Acute Kidney Injury Diseases 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- OVQASIIRFGOFSF-UHFFFAOYSA-N C(C)(=O)OC1=C(C(=O)NC(=N)C2=CC=C(C=C2)N2C(OC(C2C2=CC=C(C=C2)C(NC(C2=C(C=CC=C2)OC(C)=O)=O)=N)COS(=O)(=O)C)=O)C=CC=C1 Chemical compound C(C)(=O)OC1=C(C(=O)NC(=N)C2=CC=C(C=C2)N2C(OC(C2C2=CC=C(C=C2)C(NC(C2=C(C=CC=C2)OC(C)=O)=O)=N)COS(=O)(=O)C)=O)C=CC=C1 OVQASIIRFGOFSF-UHFFFAOYSA-N 0.000 description 1
- VPHXFSHJQOZTGD-UHFFFAOYSA-N C1(=CC=CC2=CC=CC=C12)NC(=N)C1=CC=C(C=C1)N1C(OC(C1)COS(=O)(=O)C)=O Chemical compound C1(=CC=CC2=CC=CC=C12)NC(=N)C1=CC=C(C=C1)N1C(OC(C1)COS(=O)(=O)C)=O VPHXFSHJQOZTGD-UHFFFAOYSA-N 0.000 description 1
- SAMKGWGWSUHZJL-UHFFFAOYSA-N C1(=CC=CC=C1)C1NC(=NO1)C1=CC=C(C=C1)N1C(OC(C1)COC1=CC=C(C=C1)CC(NC(=O)C1=CC=CC2=CC=CC=C12)C(=O)OCC)=O Chemical compound C1(=CC=CC=C1)C1NC(=NO1)C1=CC=C(C=C1)N1C(OC(C1)COC1=CC=C(C=C1)CC(NC(=O)C1=CC=CC2=CC=CC=C12)C(=O)OCC)=O SAMKGWGWSUHZJL-UHFFFAOYSA-N 0.000 description 1
- ZLVWWPUFFJTLKH-UHFFFAOYSA-N C1(=CC=CC=C1)CCC1=NNC2=C(C=C1)C=CC(=C2)C(N(C)C2=CC=C(C=C2)C(NC(C2=CC=CC=C2)=O)=N)=O Chemical compound C1(=CC=CC=C1)CCC1=NNC2=C(C=C1)C=CC(=C2)C(N(C)C2=CC=C(C=C2)C(NC(C2=CC=CC=C2)=O)=N)=O ZLVWWPUFFJTLKH-UHFFFAOYSA-N 0.000 description 1
- KFFLRWVZULFCRC-UHFFFAOYSA-N C1=CC(C(=N)NC(=O)NCC(=O)OCC)=CC=C1N1C(=O)OC(CN2CCN(CCC(=O)OC(C)(C)C)CC2)C1 Chemical compound C1=CC(C(=N)NC(=O)NCC(=O)OCC)=CC=C1N1C(=O)OC(CN2CCN(CCC(=O)OC(C)(C)C)CC2)C1 KFFLRWVZULFCRC-UHFFFAOYSA-N 0.000 description 1
- BDACEACYDKITPO-UHFFFAOYSA-N C1=CC(C(=N)NC(=O)NCC(=O)OCC)=CC=C1N1C(=O)OC(CN2CCN(CCC(=O)OC(C)C)CC2)C1 Chemical compound C1=CC(C(=N)NC(=O)NCC(=O)OCC)=CC=C1N1C(=O)OC(CN2CCN(CCC(=O)OC(C)C)CC2)C1 BDACEACYDKITPO-UHFFFAOYSA-N 0.000 description 1
- WJVZRXIRKCINCH-UHFFFAOYSA-N C1=CC(C(=N)NC(=O)NCC(=O)OCC)=CC=C1N1C(=O)OC(CN2CCN(CCC(=O)OC)CC2)C1 Chemical compound C1=CC(C(=N)NC(=O)NCC(=O)OCC)=CC=C1N1C(=O)OC(CN2CCN(CCC(=O)OC)CC2)C1 WJVZRXIRKCINCH-UHFFFAOYSA-N 0.000 description 1
- PURAJBZQTZOFJG-ZSIJNCSSSA-N C1=CC(C(=N)NC(=O)OC)=CC=C1N1C(=O)O[C@@H](CCl)C1.C1CN(CC(=O)OCC)CCN1C[C@H]1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)OC)C1 Chemical compound C1=CC(C(=N)NC(=O)OC)=CC=C1N1C(=O)O[C@@H](CCl)C1.C1CN(CC(=O)OCC)CCN1C[C@H]1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)OC)C1 PURAJBZQTZOFJG-ZSIJNCSSSA-N 0.000 description 1
- YHFLTFHLCGKNJO-WZYASKPUSA-N C1=CC(C(=N)NC(=O)OCC)=CC=C1N1C(=O)O[C@@H](CCl)C1.C1CN(CC(=O)OCC)CCN1C[C@H]1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)OCC)C1 Chemical compound C1=CC(C(=N)NC(=O)OCC)=CC=C1N1C(=O)O[C@@H](CCl)C1.C1CN(CC(=O)OCC)CCN1C[C@H]1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)OCC)C1 YHFLTFHLCGKNJO-WZYASKPUSA-N 0.000 description 1
- YHFLTFHLCGKNJO-ROIBDPJQSA-N C1=CC(C(=N)NC(=O)OCC)=CC=C1N1C(=O)O[C@H](CCl)C1.C1CN(CC(=O)OCC)CCN1C[C@@H]1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)OCC)C1 Chemical compound C1=CC(C(=N)NC(=O)OCC)=CC=C1N1C(=O)O[C@H](CCl)C1.C1CN(CC(=O)OCC)CCN1C[C@@H]1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)OCC)C1 YHFLTFHLCGKNJO-ROIBDPJQSA-N 0.000 description 1
- ODWFLAONCUJUHX-UHFFFAOYSA-N C1=CC(C(=N)NS(=O)(=O)C)=CC=C1N1C(=O)OC(COS(C)(=O)=O)C1.C1CN(CCC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NS(C)(=O)=O)C1 Chemical compound C1=CC(C(=N)NS(=O)(=O)C)=CC=C1N1C(=O)OC(COS(C)(=O)=O)C1.C1CN(CCC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NS(C)(=O)=O)C1 ODWFLAONCUJUHX-UHFFFAOYSA-N 0.000 description 1
- UUUIHMISZAJGSB-UHFFFAOYSA-N C1CN(CC(=O)OCCCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)NCC(=O)OCC)C1 Chemical compound C1CN(CC(=O)OCCCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)NCC(=O)OCC)C1 UUUIHMISZAJGSB-UHFFFAOYSA-N 0.000 description 1
- ARAUZHOLBVPUCP-UHFFFAOYSA-N CCOC(=O)CNC(=O)NC1=CC=C(C=C1)N2CC(OC2=O)COS(=O)(=O)C Chemical compound CCOC(=O)CNC(=O)NC1=CC=C(C=C1)N2CC(OC2=O)COS(=O)(=O)C ARAUZHOLBVPUCP-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZFSTVDHUSJAQII-UHFFFAOYSA-N ClN(C(=N)C1=CC=C(C=C1)N1C(OC(C1)CN1CCN(CC1)C(CC(=O)O)C(=O)OCC)=O)C(C1=CC=CC=C1)=O Chemical compound ClN(C(=N)C1=CC=C(C=C1)N1C(OC(C1)CN1CCN(CC1)C(CC(=O)O)C(=O)OCC)=O)C(C1=CC=CC=C1)=O ZFSTVDHUSJAQII-UHFFFAOYSA-N 0.000 description 1
- LUTLZXGBWHKGMR-UHFFFAOYSA-N ClN(C(=N)C1=CC=C(C=C1)N1C(OC(C1)CN1CCN(CC1)C(CC(=O)OCC)C(=O)OCC)=O)C(C1=CC=CC=C1)=O Chemical compound ClN(C(=N)C1=CC=C(C=C1)N1C(OC(C1)CN1CCN(CC1)C(CC(=O)OCC)C(=O)OCC)=O)C(C1=CC=CC=C1)=O LUTLZXGBWHKGMR-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 102000007547 Laminin Human genes 0.000 description 1
- 108010085895 Laminin Proteins 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- GEFUERUCKMQXLI-UHFFFAOYSA-N O=C1OC(COS(=O)(=O)C)CN1C1=CC=C(C(=N)NC(=O)C=2C=C3C=CC=CC3=CC=2)C=C1.C1CN(CCC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)C=2C=C3C=CC=CC3=CC=2)C1 Chemical compound O=C1OC(COS(=O)(=O)C)CN1C1=CC=C(C(=N)NC(=O)C=2C=C3C=CC=CC3=CC=2)C=C1.C1CN(CCC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)C=2C=C3C=CC=CC3=CC=2)C1 GEFUERUCKMQXLI-UHFFFAOYSA-N 0.000 description 1
- FVNWLRKDLAXSSZ-UHFFFAOYSA-N O=C1OC(COS(=O)(=O)C)CN1C1=CC=C(C(=N)NC(=O)C=2C=CC(Cl)=CC=2)C=C1.C1CN(CC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)C=2C=CC(Cl)=CC=2)C1 Chemical compound O=C1OC(COS(=O)(=O)C)CN1C1=CC=C(C(=N)NC(=O)C=2C=CC(Cl)=CC=2)C=C1.C1CN(CC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)C=2C=CC(Cl)=CC=2)C1 FVNWLRKDLAXSSZ-UHFFFAOYSA-N 0.000 description 1
- SDMMRBTZINJVRW-UHFFFAOYSA-N O=C1OC(COS(=O)(=O)C)CN1C1=CC=C(C(=N)NC(=O)C=2C=NC=CC=2)C=C1.C1CN(CCC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)C=2C=NC=CC=2)C1 Chemical compound O=C1OC(COS(=O)(=O)C)CN1C1=CC=C(C(=N)NC(=O)C=2C=NC=CC=2)C=C1.C1CN(CCC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)C=2C=NC=CC=2)C1 SDMMRBTZINJVRW-UHFFFAOYSA-N 0.000 description 1
- FMTXUJOWMHXTAV-UHFFFAOYSA-N O=C1OC(COS(=O)(=O)C)CN1C1=CC=C(C(=N)NC(=O)C=2OC=CC=2)C=C1.C1CN(CCC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)C=2OC=CC=2)C1 Chemical compound O=C1OC(COS(=O)(=O)C)CN1C1=CC=C(C(=N)NC(=O)C=2OC=CC=2)C=C1.C1CN(CCC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)C=2OC=CC=2)C1 FMTXUJOWMHXTAV-UHFFFAOYSA-N 0.000 description 1
- RKTASVBRJRGPBA-UHFFFAOYSA-N O=C1OC(COS(=O)(=O)C)CN1C1=CC=C(C(=N)NC(=O)OC=2C=CC=CC=2)C=C1.C1CN(CCC(=O)OC(C)(C)C)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)OC=2C=CC=CC=2)C1 Chemical compound O=C1OC(COS(=O)(=O)C)CN1C1=CC=C(C(=N)NC(=O)OC=2C=CC=CC=2)C=C1.C1CN(CCC(=O)OC(C)(C)C)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)OC=2C=CC=CC=2)C1 RKTASVBRJRGPBA-UHFFFAOYSA-N 0.000 description 1
- DXMMYCOBDVDTQQ-UHFFFAOYSA-N O=C1OC(COS(=O)(=O)C)CN1C1=CC=C(C(=N)NC(=O)OC=2C=CC=CC=2)C=C1.C1CN(CCC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)OC=2C=CC=CC=2)C1 Chemical compound O=C1OC(COS(=O)(=O)C)CN1C1=CC=C(C(=N)NC(=O)OC=2C=CC=CC=2)C=C1.C1CN(CCC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)OC=2C=CC=CC=2)C1 DXMMYCOBDVDTQQ-UHFFFAOYSA-N 0.000 description 1
- 229920002230 Pectic acid Polymers 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 208000033626 Renal failure acute Diseases 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- AJMWPNYCWKQNFY-MQPQYVOESA-N [(5S)-3-[4-(N-benzoylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate ethyl 3-[4-[[(5S)-3-[4-(N-benzoylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound O=C1O[C@H](COS(=O)(=O)C)CN1C1=CC=C(C(=N)NC(=O)C=2C=CC=CC=2)C=C1.C1CN(CCC(=O)OCC)CCN1C[C@@H]1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)C=2C=CC=CC=2)C1 AJMWPNYCWKQNFY-MQPQYVOESA-N 0.000 description 1
- WMSDOZUBILXRSY-MRXNPFEDSA-N [(5r)-3-[4-(n'-benzoylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate Chemical compound O=C1O[C@@H](COS(=O)(=O)C)CN1C1=CC=C(C(=N)NC(=O)C=2C=CC=CC=2)C=C1 WMSDOZUBILXRSY-MRXNPFEDSA-N 0.000 description 1
- AMTRNGAMYMRHSH-QGZVFWFLSA-N [(5r)-3-[4-[n'-(4-methoxybenzoyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate Chemical compound C1=CC(OC)=CC=C1C(=O)NC(=N)C1=CC=C(N2C(O[C@@H](COS(C)(=O)=O)C2)=O)C=C1 AMTRNGAMYMRHSH-QGZVFWFLSA-N 0.000 description 1
- WMSDOZUBILXRSY-INIZCTEOSA-N [(5s)-3-[4-(n'-benzoylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate Chemical compound O=C1O[C@H](COS(=O)(=O)C)CN1C1=CC=C(C(=N)NC(=O)C=2C=CC=CC=2)C=C1 WMSDOZUBILXRSY-INIZCTEOSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- XAQMUNOLWHQDEY-UHFFFAOYSA-N [3-[4-[n'-(3-cyanobenzoyl)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=C(C=CC=2)C#N)C=C1 XAQMUNOLWHQDEY-UHFFFAOYSA-N 0.000 description 1
- BRWOHUOZTWDGNN-UHFFFAOYSA-N [3-[4-[n'-(3-nitrobenzoyl)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=C(C=CC=2)[N+]([O-])=O)C=C1 BRWOHUOZTWDGNN-UHFFFAOYSA-N 0.000 description 1
- BBCGYHQUWUFFMA-UHFFFAOYSA-N [3-[4-[n'-(3-tert-butylbenzoyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate Chemical compound CC(C)(C)C1=CC=CC(C(=O)N=C(N)C=2C=CC(=CC=2)N2C(OC(COS(C)(=O)=O)C2)=O)=C1 BBCGYHQUWUFFMA-UHFFFAOYSA-N 0.000 description 1
- MWLCPBZLOBUMCC-UHFFFAOYSA-N [3-[4-[n'-(4-chlorobenzoyl)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=CC(Cl)=CC=2)C=C1 MWLCPBZLOBUMCC-UHFFFAOYSA-N 0.000 description 1
- MCBLRIDYGLCDGZ-UHFFFAOYSA-N [3-[4-[n'-(4-fluorobenzoyl)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=CC(F)=CC=2)C=C1 MCBLRIDYGLCDGZ-UHFFFAOYSA-N 0.000 description 1
- JUCRCEMVHOUWFJ-UHFFFAOYSA-N [4-(4-chlorobutyl)piperidin-1-yl]-phenylmethanone Chemical compound C1CC(CCCCCl)CCN1C(=O)C1=CC=CC=C1 JUCRCEMVHOUWFJ-UHFFFAOYSA-N 0.000 description 1
- YSGFYDSDPVXNQA-UHFFFAOYSA-N [Na].C(C)OC(CC(N)C1=CC=C(C=C1)OCCCCC1CCN(CC1)C(C1=CC=CC=C1)=O)=O Chemical compound [Na].C(C)OC(CC(N)C1=CC=C(C=C1)OCCCCC1CCN(CC1)C(C1=CC=CC=C1)=O)=O YSGFYDSDPVXNQA-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 201000011040 acute kidney failure Diseases 0.000 description 1
- 208000012998 acute renal failure Diseases 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 108010013985 adhesion receptor Proteins 0.000 description 1
- 102000019997 adhesion receptor Human genes 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000002399 angioplasty Methods 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940064004 antiseptic throat preparations Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 229960000686 benzalkonium chloride Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- CXDXHADNERDKLT-UHFFFAOYSA-N benzyl 2-[4-[[2-oxo-3-[4-(n'-phenoxycarbonylcarbamimidoyl)phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C=1C=C(N2C(OC(CN3CCN(CC(=O)OCC=4C=CC=CC=4)CC3)C2)=O)C=CC=1C(/N)=N\C(=O)OC1=CC=CC=C1 CXDXHADNERDKLT-UHFFFAOYSA-N 0.000 description 1
- ZWZVYBFWMURBLJ-UHFFFAOYSA-N benzyl 2-[4-[[2-oxo-3-[4-(n'-phenylmethoxycarbonylcarbamimidoyl)phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C=1C=C(N2C(OC(CN3CCN(CC(=O)OCC=4C=CC=CC=4)CC3)C2)=O)C=CC=1C(/N)=N\C(=O)OCC1=CC=CC=C1 ZWZVYBFWMURBLJ-UHFFFAOYSA-N 0.000 description 1
- JGBLUXSPIAMJME-UHFFFAOYSA-N benzyl 2-[4-[[2-oxo-3-[4-[n'-(thiophene-2-carbonyl)carbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C=1C=C(N2C(OC(CN3CCN(CC(=O)OCC=4C=CC=CC=4)CC3)C2)=O)C=CC=1C(N)=NC(=O)C1=CC=CS1 JGBLUXSPIAMJME-UHFFFAOYSA-N 0.000 description 1
- VPVHFWWZOFTWJG-UHFFFAOYSA-N benzyl 2-[4-[[2-oxo-3-[4-[n'-(thiophene-3-carbonyl)carbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C=1C=C(N2C(OC(CN3CCN(CC(=O)OCC=4C=CC=CC=4)CC3)C2)=O)C=CC=1C(N)=NC(=O)C=1C=CSC=1 VPVHFWWZOFTWJG-UHFFFAOYSA-N 0.000 description 1
- LGBIESZNUOOALB-UHFFFAOYSA-N benzyl 2-[4-[[3-[4-(n'-benzoylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C=1C=C(N2C(OC(CN3CCN(CC(=O)OCC=4C=CC=CC=4)CC3)C2)=O)C=CC=1C(N)=NC(=O)C1=CC=CC=C1 LGBIESZNUOOALB-UHFFFAOYSA-N 0.000 description 1
- LUFWXGJDXPQVKO-UHFFFAOYSA-N benzyl 2-[4-[[3-[4-[(e)-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)OCC=3C=CC=CC=3)CC2)C1 LUFWXGJDXPQVKO-UHFFFAOYSA-N 0.000 description 1
- XUHQSZWDAOFILT-UHFFFAOYSA-N benzyl 2-[4-[[3-[4-[(e)-n'-methylsulfonylcarbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1=CC(C(/N)=N/S(=O)(=O)C)=CC=C1N1C(=O)OC(CN2CCN(CC(=O)OCC=3C=CC=CC=3)CC2)C1 XUHQSZWDAOFILT-UHFFFAOYSA-N 0.000 description 1
- WYCAMWWSTMZAMB-UHFFFAOYSA-N benzyl 2-[4-[[3-[4-[n'-(furan-2-carbonyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C=1C=C(N2C(OC(CN3CCN(CC(=O)OCC=4C=CC=CC=4)CC3)C2)=O)C=CC=1C(N)=NC(=O)C1=CC=CO1 WYCAMWWSTMZAMB-UHFFFAOYSA-N 0.000 description 1
- RHRBSOVESSVPNK-UHFFFAOYSA-N benzyl 2-[4-[[3-[4-[n'-(furan-3-carbonyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C=1C=C(N2C(OC(CN3CCN(CC(=O)OCC=4C=CC=CC=4)CC3)C2)=O)C=CC=1C(N)=NC(=O)C=1C=COC=1 RHRBSOVESSVPNK-UHFFFAOYSA-N 0.000 description 1
- FBLBQVFULKJZRD-UHFFFAOYSA-N benzyl 2-[4-[[3-[4-[n'-(naphthalene-1-carbonyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C=1C=CC2=CC=CC=C2C=1C(=O)N=C(N)C(C=C1)=CC=C1N(C(O1)=O)CC1CN(CC1)CCN1CC(=O)OCC1=CC=CC=C1 FBLBQVFULKJZRD-UHFFFAOYSA-N 0.000 description 1
- LFUOHBIGOYCWJD-UHFFFAOYSA-N benzyl 2-[4-[[3-[4-[n'-(naphthalene-2-carbonyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C=1C=C2C=CC=CC2=CC=1C(=O)N=C(N)C(C=C1)=CC=C1N(C(O1)=O)CC1CN(CC1)CCN1CC(=O)OCC1=CC=CC=C1 LFUOHBIGOYCWJD-UHFFFAOYSA-N 0.000 description 1
- FDTQLXHLYYPMEG-UHFFFAOYSA-N benzyl 2-piperazin-1-ylacetate Chemical compound C=1C=CC=CC=1COC(=O)CN1CCNCC1 FDTQLXHLYYPMEG-UHFFFAOYSA-N 0.000 description 1
- MGOSDJWEBUIAQH-UHFFFAOYSA-N benzyl 3-[4-[[2-oxo-3-[4-[(z)-n'-phenoxycarbonylcarbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C=1C=C(N2C(OC(CN3CCN(CCC(=O)OCC=4C=CC=CC=4)CC3)C2)=O)C=CC=1C(N)=NC(=O)OC1=CC=CC=C1 MGOSDJWEBUIAQH-UHFFFAOYSA-N 0.000 description 1
- UXNXCAPNBCUARJ-UHFFFAOYSA-N benzyl 3-[4-[[2-oxo-3-[4-[(z)-n'-phenylmethoxycarbonylcarbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C=1C=C(N2C(OC(CN3CCN(CCC(=O)OCC=4C=CC=CC=4)CC3)C2)=O)C=CC=1C(N)=NC(=O)OCC1=CC=CC=C1 UXNXCAPNBCUARJ-UHFFFAOYSA-N 0.000 description 1
- WADNZFJFIUVPHF-UHFFFAOYSA-N benzyl 3-[4-[[2-oxo-3-[4-[n'-(pyridine-3-carbonyl)carbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C=1C=C(N2C(OC(CN3CCN(CCC(=O)OCC=4C=CC=CC=4)CC3)C2)=O)C=CC=1C(N)=NC(=O)C1=CC=CN=C1 WADNZFJFIUVPHF-UHFFFAOYSA-N 0.000 description 1
- FPXAZYNVRLVBKG-UHFFFAOYSA-N benzyl 3-[4-[[2-oxo-3-[4-[n'-(thiophene-2-carbonyl)carbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C=1C=C(N2C(OC(CN3CCN(CCC(=O)OCC=4C=CC=CC=4)CC3)C2)=O)C=CC=1C(N)=NC(=O)C1=CC=CS1 FPXAZYNVRLVBKG-UHFFFAOYSA-N 0.000 description 1
- NVKBABXTJFMGHW-UHFFFAOYSA-N benzyl 3-[4-[[2-oxo-3-[4-[n'-(thiophene-3-carbonyl)carbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C=1C=C(N2C(OC(CN3CCN(CCC(=O)OCC=4C=CC=CC=4)CC3)C2)=O)C=CC=1C(N)=NC(=O)C=1C=CSC=1 NVKBABXTJFMGHW-UHFFFAOYSA-N 0.000 description 1
- PEYBOPBZCGIQAN-UHFFFAOYSA-N benzyl 3-[4-[[3-[4-(n'-benzoylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C=1C=C(N2C(OC(CN3CCN(CCC(=O)OCC=4C=CC=CC=4)CC3)C2)=O)C=CC=1C(N)=NC(=O)C1=CC=CC=C1 PEYBOPBZCGIQAN-UHFFFAOYSA-N 0.000 description 1
- KYNWBCXKDHUSBG-UHFFFAOYSA-N benzyl 3-[4-[[3-[4-(n'-methoxycarbonylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C1=CC(C(/N)=N/C(=O)OC)=CC=C1N1C(=O)OC(CN2CCN(CCC(=O)OCC=3C=CC=CC=3)CC2)C1 KYNWBCXKDHUSBG-UHFFFAOYSA-N 0.000 description 1
- QBHAQOCHLBMXOZ-UHFFFAOYSA-N benzyl 3-[4-[[3-[4-(n'-methylsulfonylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C1=CC(C(/N)=N/S(=O)(=O)C)=CC=C1N1C(=O)OC(CN2CCN(CCC(=O)OCC=3C=CC=CC=3)CC2)C1 QBHAQOCHLBMXOZ-UHFFFAOYSA-N 0.000 description 1
- BHPXLWSEEMLCEZ-UHFFFAOYSA-N benzyl 3-[4-[[3-[4-[n'-(furan-2-carbonyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C=1C=C(N2C(OC(CN3CCN(CCC(=O)OCC=4C=CC=CC=4)CC3)C2)=O)C=CC=1C(N)=NC(=O)C1=CC=CO1 BHPXLWSEEMLCEZ-UHFFFAOYSA-N 0.000 description 1
- GVCYWLJOTMBOEL-UHFFFAOYSA-N benzyl 3-[4-[[3-[4-[n'-(furan-3-carbonyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C=1C=C(N2C(OC(CN3CCN(CCC(=O)OCC=4C=CC=CC=4)CC3)C2)=O)C=CC=1C(N)=NC(=O)C=1C=COC=1 GVCYWLJOTMBOEL-UHFFFAOYSA-N 0.000 description 1
- LXAMXJRCKRMKGL-UHFFFAOYSA-N benzyl 3-[4-[[3-[4-[n'-(naphthalene-2-carbonyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C=1C=C2C=CC=CC2=CC=1C(=O)N=C(N)C(C=C1)=CC=C1N(C(O1)=O)CC1CN(CC1)CCN1CCC(=O)OCC1=CC=CC=C1 LXAMXJRCKRMKGL-UHFFFAOYSA-N 0.000 description 1
- QEXYDSARFDWBPV-UHFFFAOYSA-N benzyl 3-piperazin-1-ylpropanoate Chemical compound C=1C=CC=CC=1COC(=O)CCN1CCNCC1 QEXYDSARFDWBPV-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 150000003938 benzyl alcohols Chemical class 0.000 description 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- WEDIIKBPDQQQJU-UHFFFAOYSA-N butane-1-sulfonyl chloride Chemical compound CCCCS(Cl)(=O)=O WEDIIKBPDQQQJU-UHFFFAOYSA-N 0.000 description 1
- LCJCYMGLDPAAKD-UHFFFAOYSA-N butyl 2-[4-[[2-oxo-3-[4-[(z)-n'-phenoxycarbonylcarbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCCCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)OC=2C=CC=CC=2)C1 LCJCYMGLDPAAKD-UHFFFAOYSA-N 0.000 description 1
- FETNWECUOIIZGR-UHFFFAOYSA-N butyl 2-[4-[[2-oxo-3-[4-[(z)-n'-phenylmethoxycarbonylcarbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCCCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)OCC=2C=CC=CC=2)C1 FETNWECUOIIZGR-UHFFFAOYSA-N 0.000 description 1
- AYHOZUCUXJLDTH-UHFFFAOYSA-N butyl 2-[4-[[2-oxo-3-[4-[n'-(thiophene-2-carbonyl)carbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCCCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2SC=CC=2)C1 AYHOZUCUXJLDTH-UHFFFAOYSA-N 0.000 description 1
- CNAKRZFFTHTHHS-UHFFFAOYSA-N butyl 2-[4-[[2-oxo-3-[4-[n'-(thiophene-3-carbonyl)carbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCCCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C2=CSC=C2)C1 CNAKRZFFTHTHHS-UHFFFAOYSA-N 0.000 description 1
- ZKCZMYMIMPDDID-UHFFFAOYSA-N butyl 2-[4-[[3-[4-(N-methoxycarbonylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate [3-[4-(N-methoxycarbonylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate Chemical compound C1=CC(C(=N)NC(=O)OC)=CC=C1N1C(=O)OC(COS(C)(=O)=O)C1.C1CN(CC(=O)OCCCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)OC)C1 ZKCZMYMIMPDDID-UHFFFAOYSA-N 0.000 description 1
- XUULDBIUHDHYFD-UHFFFAOYSA-N butyl 2-[4-[[3-[4-(n'-benzoylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCCCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2C=CC=CC=2)C1 XUULDBIUHDHYFD-UHFFFAOYSA-N 0.000 description 1
- PUOVTLTUZQZMIY-UHFFFAOYSA-N butyl 2-[4-[[3-[4-[(z)-n'-methylsulfonylcarbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCCCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NS(C)(=O)=O)C1 PUOVTLTUZQZMIY-UHFFFAOYSA-N 0.000 description 1
- AUZJIOXMPYMINZ-UHFFFAOYSA-N butyl 2-[4-[[3-[4-[n'-(furan-2-carbonyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCCCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2OC=CC=2)C1 AUZJIOXMPYMINZ-UHFFFAOYSA-N 0.000 description 1
- FHLZOKHEZSBRDS-UHFFFAOYSA-N butyl 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)OCCCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C2=COC=C2)C1 FHLZOKHEZSBRDS-UHFFFAOYSA-N 0.000 description 1
- GYCKMWXJBZTKLD-UHFFFAOYSA-N butyl 2-[4-[[3-[4-[n'-(naphthalene-1-carbonyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCCCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2C3=CC=CC=C3C=CC=2)C1 GYCKMWXJBZTKLD-UHFFFAOYSA-N 0.000 description 1
- MFNKJEGQWRBDFD-UHFFFAOYSA-N butyl 2-[4-[[3-[4-[n'-(naphthalene-2-carbonyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCCCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2C=C3C=CC=CC3=CC=2)C1 MFNKJEGQWRBDFD-UHFFFAOYSA-N 0.000 description 1
- VOADUIVUHIYVOR-UHFFFAOYSA-N butyl 2-piperazin-1-ylacetate Chemical compound CCCCOC(=O)CN1CCNCC1 VOADUIVUHIYVOR-UHFFFAOYSA-N 0.000 description 1
- PHTHSQDSPXBHHI-UHFFFAOYSA-N butyl 3-[4-[[2-oxo-3-[4-[(z)-n'-phenoxycarbonylcarbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C1CN(CCC(=O)OCCCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)OC=2C=CC=CC=2)C1 PHTHSQDSPXBHHI-UHFFFAOYSA-N 0.000 description 1
- XGHXZYSFHXKJIE-UHFFFAOYSA-N butyl 3-[4-[[2-oxo-3-[4-[(z)-n'-phenylmethoxycarbonylcarbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C1CN(CCC(=O)OCCCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)OCC=2C=CC=CC=2)C1 XGHXZYSFHXKJIE-UHFFFAOYSA-N 0.000 description 1
- YKVZPBAKBCOZDM-UHFFFAOYSA-N butyl 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)OCCCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)C=2C=NC=CC=2)C1 YKVZPBAKBCOZDM-UHFFFAOYSA-N 0.000 description 1
- HCBHFWZZFYQHHS-UHFFFAOYSA-N butyl 3-[4-[[2-oxo-3-[4-[n'-(thiophene-2-carbonyl)carbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C1CN(CCC(=O)OCCCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2SC=CC=2)C1 HCBHFWZZFYQHHS-UHFFFAOYSA-N 0.000 description 1
- BRPYKOTYTHXENG-UHFFFAOYSA-N butyl 3-[4-[[2-oxo-3-[4-[n'-(thiophene-3-carbonyl)carbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C1CN(CCC(=O)OCCCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C2=CSC=C2)C1 BRPYKOTYTHXENG-UHFFFAOYSA-N 0.000 description 1
- FAFLKAWGRMRLPR-UHFFFAOYSA-N butyl 3-[4-[[3-[4-(n'-benzoylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C1CN(CCC(=O)OCCCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2C=CC=CC=2)C1 FAFLKAWGRMRLPR-UHFFFAOYSA-N 0.000 description 1
- IUDUDGXIZHNDNA-UHFFFAOYSA-N butyl 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)OCCCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)OC)C1 IUDUDGXIZHNDNA-UHFFFAOYSA-N 0.000 description 1
- QGTNONVPWPZGSB-UHFFFAOYSA-N butyl 3-[4-[[3-[4-[(z)-n'-methylsulfonylcarbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C1CN(CCC(=O)OCCCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NS(C)(=O)=O)C1 QGTNONVPWPZGSB-UHFFFAOYSA-N 0.000 description 1
- BCVBNTMSHADTHV-UHFFFAOYSA-N butyl 3-[4-[[3-[4-[N-[(2-ethoxy-2-oxoethyl)carbamoyl]carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C(C)OC(=O)CNC(=O)NC(=N)C1=CC=C(C=C1)N1C(OC(C1)CN1CCN(CC1)CCC(=O)OCCCC)=O BCVBNTMSHADTHV-UHFFFAOYSA-N 0.000 description 1
- BWFIEDXPTDIPTP-UHFFFAOYSA-N butyl 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)OCCCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2OC=CC=2)C1 BWFIEDXPTDIPTP-UHFFFAOYSA-N 0.000 description 1
- MTSZRFIQRLMBQT-UHFFFAOYSA-N butyl 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)OCCCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C2=COC=C2)C1 MTSZRFIQRLMBQT-UHFFFAOYSA-N 0.000 description 1
- RDZRKJONRMEXIR-UHFFFAOYSA-N butyl 3-[4-[[3-[4-[n'-(naphthalene-1-carbonyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C1CN(CCC(=O)OCCCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2C3=CC=CC=C3C=CC=2)C1 RDZRKJONRMEXIR-UHFFFAOYSA-N 0.000 description 1
- JRCTVMPLSCUOOU-UHFFFAOYSA-N butyl 3-[4-[[3-[4-[n'-(naphthalene-2-carbonyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C1CN(CCC(=O)OCCCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2C=C3C=CC=CC3=CC=2)C1 JRCTVMPLSCUOOU-UHFFFAOYSA-N 0.000 description 1
- CXAHABITOXEGFU-UHFFFAOYSA-N butyl 3-piperazin-1-ylpropanoate Chemical compound CCCCOC(=O)CCN1CCNCC1 CXAHABITOXEGFU-UHFFFAOYSA-N 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical class C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- RLOVQEPDZNAOHO-UHFFFAOYSA-N diethyl 2-[4-[[2-oxo-3-[4-(n'-propanoylcarbamimidoyl)phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]butanedioate Chemical compound C1CN(C(CC(=O)OCC)C(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)CC)C1 RLOVQEPDZNAOHO-UHFFFAOYSA-N 0.000 description 1
- KBXSMBOOWMUCOB-UHFFFAOYSA-N diethyl 2-[4-[[3-[4-(5-methyl-2,5-dihydro-1,2,4-oxadiazol-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]butanedioate Chemical compound C1CN(C(CC(=O)OCC)C(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C=2NC(C)ON=2)C1 KBXSMBOOWMUCOB-UHFFFAOYSA-N 0.000 description 1
- KYQPSGVKIBHDAQ-UHFFFAOYSA-N diethyl 2-[4-[[3-[4-(n'-acetylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]butanedioate Chemical compound C1CN(C(CC(=O)OCC)C(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(C)=O)C1 KYQPSGVKIBHDAQ-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical class CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 239000000890 drug combination Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000005949 ethanesulfonyloxy group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- KUSJUSFXKUCOFD-UHFFFAOYSA-N ethyl (ne)-n-[amino-[4-[5-(chloromethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]methylidene]carbamate Chemical compound C1=CC(C(=N)NC(=O)OCC)=CC=C1N1C(=O)OC(CCl)C1 KUSJUSFXKUCOFD-UHFFFAOYSA-N 0.000 description 1
- FNDYVVOTDHKKOR-UHFFFAOYSA-N ethyl 1-[(2-oxo-1,3-oxazolidin-3-yl)methyl]piperidine-4-carboxylate Chemical compound C(C)OC(=O)C1CCN(CC1)CN1C(OCC1)=O FNDYVVOTDHKKOR-UHFFFAOYSA-N 0.000 description 1
- URHDSBVFRURKAM-UHFFFAOYSA-N ethyl 1-[1-[4-(n'-benzoylcarbamimidoyl)phenyl]piperidin-4-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1CCN(C=2C=CC(=CC=2)C(=N)NC(=O)C=2C=CC=CC=2)CC1 URHDSBVFRURKAM-UHFFFAOYSA-N 0.000 description 1
- RISSRIKEANCOSO-UHFFFAOYSA-N ethyl 1-[[2-oxo-3-[4-(n'-phenoxycarbonylcarbamimidoyl)phenyl]-1,3-oxazolidin-5-yl]methyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(\N)=N/C(=O)OC=2C=CC=CC=2)C1 RISSRIKEANCOSO-UHFFFAOYSA-N 0.000 description 1
- LVWDEWIMLPFQCS-UHFFFAOYSA-N ethyl 1-[[2-oxo-3-[4-(n'-phenylmethoxycarbonylcarbamimidoyl)phenyl]-1,3-oxazolidin-5-yl]methyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(\N)=N/C(=O)OCC=2C=CC=CC=2)C1 LVWDEWIMLPFQCS-UHFFFAOYSA-N 0.000 description 1
- DJOALIJMOSPGPN-UHFFFAOYSA-N ethyl 1-[[2-oxo-3-[4-[n'-(thiophene-2-carbonyl)carbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2SC=CC=2)C1 DJOALIJMOSPGPN-UHFFFAOYSA-N 0.000 description 1
- SASRHKIGLKFLSU-UHFFFAOYSA-N ethyl 1-[[3-[4-(n'-benzoylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)C=2C=CC=CC=2)C1 SASRHKIGLKFLSU-UHFFFAOYSA-N 0.000 description 1
- IALXJDFJQGPUAW-UHFFFAOYSA-N ethyl 1-[[3-[4-(n'-methoxycarbonylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(\N)=N/C(=O)OC)C1 IALXJDFJQGPUAW-UHFFFAOYSA-N 0.000 description 1
- DNFZEYOQOGBUMY-UHFFFAOYSA-N ethyl 1-[[3-[4-(n'-methylsulfonylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(\N)=N/S(C)(=O)=O)C1 DNFZEYOQOGBUMY-UHFFFAOYSA-N 0.000 description 1
- BEDWZJZTHYGFTP-UHFFFAOYSA-N ethyl 1-[[3-[4-[(e)-n'-[(2-ethoxy-2-oxoethyl)carbamoyl]carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperidine-4-carboxylate Chemical compound C1=CC(C(=N)NC(=O)NCC(=O)OCC)=CC=C1N1C(=O)OC(CN2CCC(CC2)C(=O)OCC)C1 BEDWZJZTHYGFTP-UHFFFAOYSA-N 0.000 description 1
- USPRYMATYXRQJI-UHFFFAOYSA-N ethyl 1-[[3-[4-[n'-(furan-2-carbonyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2OC=CC=2)C1 USPRYMATYXRQJI-UHFFFAOYSA-N 0.000 description 1
- IPFLXQVABOOIRH-UHFFFAOYSA-N ethyl 1-[[3-[4-[n'-(furan-3-carbonyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C2=COC=C2)C1 IPFLXQVABOOIRH-UHFFFAOYSA-N 0.000 description 1
- NGIWYXPEYLRFBM-UHFFFAOYSA-N ethyl 1-[[3-[4-[n'-(naphthalene-1-carbonyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2C3=CC=CC=C3C=CC=2)C1 NGIWYXPEYLRFBM-UHFFFAOYSA-N 0.000 description 1
- ZHJOSYWNXXCZHC-UHFFFAOYSA-N ethyl 1-[[3-[4-[n'-(naphthalene-2-carbonyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2C=C3C=CC=CC3=CC=2)C1 ZHJOSYWNXXCZHC-UHFFFAOYSA-N 0.000 description 1
- GGTJQJVNFTWWRS-UHFFFAOYSA-N ethyl 2-(2-oxopiperazin-1-yl)acetate Chemical compound CCOC(=O)CN1CCNCC1=O GGTJQJVNFTWWRS-UHFFFAOYSA-N 0.000 description 1
- UJFVBUOKRXMEOV-UHFFFAOYSA-N ethyl 2-(4-hydroxypiperidin-4-yl)acetate Chemical compound CCOC(=O)CC1(O)CCNCC1 UJFVBUOKRXMEOV-UHFFFAOYSA-N 0.000 description 1
- VIAWPTWUFGRPFE-UHFFFAOYSA-N ethyl 2-(naphthalene-2-carbonylamino)-3-[4-[[2-oxo-3-[4-(5-phenyl-2,5-dihydro-1,2,4-oxadiazol-3-yl)phenyl]-1,3-oxazolidin-5-yl]methoxy]phenyl]propanoate Chemical compound C=1C=C2C=CC=CC2=CC=1C(=O)NC(C(=O)OCC)CC(C=C1)=CC=C1OCC(OC1=O)CN1C(C=C1)=CC=C1C(NO1)=NC1C1=CC=CC=C1 VIAWPTWUFGRPFE-UHFFFAOYSA-N 0.000 description 1
- MJDGYLOTVVZGMJ-UHFFFAOYSA-N ethyl 2-[1-[[3-[4-(n'-benzoylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]-4-hydroxypiperidin-4-yl]acetate Chemical compound C1CC(CC(=O)OCC)(O)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)C=2C=CC=CC=2)C1 MJDGYLOTVVZGMJ-UHFFFAOYSA-N 0.000 description 1
- IBJZHAUBWFWIKV-UHFFFAOYSA-N ethyl 2-[1-[[3-[4-[n'-(2,2-diphenylacetyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]-4-hydroxypiperidin-4-yl]acetate Chemical compound C1CC(CC(=O)OCC)(O)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C(C=2C=CC=CC=2)C=2C=CC=CC=2)C1 IBJZHAUBWFWIKV-UHFFFAOYSA-N 0.000 description 1
- LQNNEJYCFOTHCM-UHFFFAOYSA-N ethyl 2-[1-[[3-[4-[n'-(furan-2-carbonyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]-4-hydroxypiperidin-4-yl]acetate Chemical compound C1CC(CC(=O)OCC)(O)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2OC=CC=2)C1 LQNNEJYCFOTHCM-UHFFFAOYSA-N 0.000 description 1
- CVHJSHGVMDIOTO-UHFFFAOYSA-N ethyl 2-[2-oxo-4-[[2-oxo-3-[4-(n'-phenoxycarbonylcarbamimidoyl)phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1C(=O)N(CC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(\N)=N/C(=O)OC=2C=CC=CC=2)C1 CVHJSHGVMDIOTO-UHFFFAOYSA-N 0.000 description 1
- LBDYWDGGKCZEOF-UHFFFAOYSA-N ethyl 2-[2-oxo-4-[[2-oxo-3-[4-(n'-phenylmethoxycarbonylcarbamimidoyl)phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1C(=O)N(CC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(\N)=N/C(=O)OCC=2C=CC=CC=2)C1 LBDYWDGGKCZEOF-UHFFFAOYSA-N 0.000 description 1
- SXUYTSXOOPBFMO-UHFFFAOYSA-N ethyl 2-[2-oxo-4-[[2-oxo-3-[4-[n'-(thiophene-2-carbonyl)carbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1C(=O)N(CC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2SC=CC=2)C1 SXUYTSXOOPBFMO-UHFFFAOYSA-N 0.000 description 1
- SBRNJEDEBHCHGP-UHFFFAOYSA-N ethyl 2-[2-oxo-4-[[2-oxo-3-[4-[n'-(thiophene-3-carbonyl)carbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1C(=O)N(CC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C2=CSC=C2)C1 SBRNJEDEBHCHGP-UHFFFAOYSA-N 0.000 description 1
- HURAVVPVBSTUGQ-NLTBZMROSA-N ethyl 2-[4-[[(5R)-2-oxo-3-[4-(N-propan-2-yloxycarbonylcarbamimidoyl)phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate propan-2-yl N-[4-[(5R)-5-(chloromethyl)-2-oxo-1,3-oxazolidin-3-yl]benzenecarboximidoyl]carbamate Chemical compound C(C)(C)OC(=O)NC(=N)C1=CC=C(C=C1)N1C(O[C@@H](C1)CN1CCN(CC1)CC(=O)OCC)=O.C(C)(C)OC(=O)NC(=N)C1=CC=C(C=C1)N1C(O[C@H](C1)CCl)=O HURAVVPVBSTUGQ-NLTBZMROSA-N 0.000 description 1
- HURAVVPVBSTUGQ-DJKKGWPCSA-N ethyl 2-[4-[[(5S)-2-oxo-3-[4-(N-propan-2-yloxycarbonylcarbamimidoyl)phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate propan-2-yl N-[4-[(5S)-5-(chloromethyl)-2-oxo-1,3-oxazolidin-3-yl]benzenecarboximidoyl]carbamate Chemical compound C1=CC(C(=N)NC(=O)OC(C)C)=CC=C1N1C(=O)O[C@H](CCl)C1.C1CN(CC(=O)OCC)CCN1C[C@@H]1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)OC(C)C)C1 HURAVVPVBSTUGQ-DJKKGWPCSA-N 0.000 description 1
- WQHBPTPTWDFAKK-HSZRJFAPSA-N ethyl 2-[4-[[(5r)-3-[4-[n'-(4-methoxybenzoyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCN1C[C@H]1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)C=2C=CC(OC)=CC=2)C1 WQHBPTPTWDFAKK-HSZRJFAPSA-N 0.000 description 1
- IQHUNRUDSIXLEE-QFIPXVFZSA-N ethyl 2-[4-[[(5s)-3-[4-(n'-benzoylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCN1C[C@@H]1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)C=2C=CC=CC=2)C1 IQHUNRUDSIXLEE-QFIPXVFZSA-N 0.000 description 1
- YNBHAPKHWDNTMZ-KRWDZBQOSA-N ethyl 2-[4-[[(5s)-3-[4-[(z)-n'-methoxycarbonylcarbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCN1C[C@@H]1OC(=O)N(C=2C=CC(=CC=2)C(\N)=N\C(=O)OC)C1 YNBHAPKHWDNTMZ-KRWDZBQOSA-N 0.000 description 1
- WKCBXCRSGVOBIR-UHFFFAOYSA-N ethyl 2-[4-[[2-oxo-3-[4-(n'-phenoxycarbonylcarbamimidoyl)phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)OC=2C=CC=CC=2)C1 WKCBXCRSGVOBIR-UHFFFAOYSA-N 0.000 description 1
- NYDNJQZAPVYJCC-UHFFFAOYSA-N ethyl 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)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)C=2C=NC=CC=2)C1 NYDNJQZAPVYJCC-UHFFFAOYSA-N 0.000 description 1
- SGOGDIZFMNEFOT-UHFFFAOYSA-N ethyl 2-[4-[[2-oxo-3-[4-[n'-(thiophene-2-carbonyl)carbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2SC=CC=2)C1 SGOGDIZFMNEFOT-UHFFFAOYSA-N 0.000 description 1
- KNLDDVGGXDXRMI-UHFFFAOYSA-N ethyl 2-[4-[[2-oxo-3-[4-[n'-(thiophene-3-carbonyl)carbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C2=CSC=C2)C1 KNLDDVGGXDXRMI-UHFFFAOYSA-N 0.000 description 1
- FIAAHLPRNAJOMG-UHFFFAOYSA-N ethyl 2-[4-[[3-[4-(n'-benzoylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]-2-oxopiperazin-1-yl]acetate Chemical compound C1C(=O)N(CC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2C=CC=CC=2)C1 FIAAHLPRNAJOMG-UHFFFAOYSA-N 0.000 description 1
- IQRAIEHWSPSMFJ-UHFFFAOYSA-N ethyl 2-[4-[[3-[4-(n'-methoxycarbonylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]-2-oxopiperazin-1-yl]acetate Chemical compound C1C(=O)N(CC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(\N)=N/C(=O)OC)C1 IQRAIEHWSPSMFJ-UHFFFAOYSA-N 0.000 description 1
- CQGBAZOXOXCWLW-UHFFFAOYSA-N ethyl 2-[4-[[3-[4-(n'-methylsulfonylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]-2-oxopiperazin-1-yl]acetate Chemical compound C1C(=O)N(CC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(\N)=N/S(C)(=O)=O)C1 CQGBAZOXOXCWLW-UHFFFAOYSA-N 0.000 description 1
- YNBHAPKHWDNTMZ-UHFFFAOYSA-N ethyl 2-[4-[[3-[4-[(e)-n'-methoxycarbonylcarbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)OC)C1 YNBHAPKHWDNTMZ-UHFFFAOYSA-N 0.000 description 1
- XKDQOXPAPKDNMK-UHFFFAOYSA-N ethyl 2-[4-[[3-[4-[N'-(3-cyanobenzoyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound CCOC(=O)CN1CCN(CC2CN(C(=O)O2)C2=CC=C(C=C2)C(=N)NC(=O)C2=CC(=CC=C2)C#N)CC1 XKDQOXPAPKDNMK-UHFFFAOYSA-N 0.000 description 1
- QGSINYQESGTYPJ-UHFFFAOYSA-N ethyl 2-[4-[[3-[4-[n'-(1,3-benzodioxole-5-carbonyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)C=2C=C3OCOC3=CC=2)C1 QGSINYQESGTYPJ-UHFFFAOYSA-N 0.000 description 1
- STUBGRYTKMCCIN-UHFFFAOYSA-N ethyl 2-[4-[[3-[4-[n'-(2-fluorobenzoyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2C(=CC=CC=2)F)C1 STUBGRYTKMCCIN-UHFFFAOYSA-N 0.000 description 1
- QKRNOSQZUCHSCV-UHFFFAOYSA-N ethyl 2-[4-[[3-[4-[n'-(2-methoxybenzoyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2C(=CC=CC=2)OC)C1 QKRNOSQZUCHSCV-UHFFFAOYSA-N 0.000 description 1
- DVABXTBPGIZFAA-UHFFFAOYSA-N ethyl 2-[4-[[3-[4-[n'-(3-fluorobenzoyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2C=C(F)C=CC=2)C1 DVABXTBPGIZFAA-UHFFFAOYSA-N 0.000 description 1
- NGHSNNGLLOTWAA-UHFFFAOYSA-N ethyl 2-[4-[[3-[4-[n'-(3-methoxybenzoyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2C=C(OC)C=CC=2)C1 NGHSNNGLLOTWAA-UHFFFAOYSA-N 0.000 description 1
- UCHIYLDKMAPLDE-UHFFFAOYSA-N ethyl 2-[4-[[3-[4-[n'-(3-methylbenzoyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2C=C(C)C=CC=2)C1 UCHIYLDKMAPLDE-UHFFFAOYSA-N 0.000 description 1
- IUAUWOQCLJAOMR-UHFFFAOYSA-N ethyl 2-[4-[[3-[4-[n'-(3-nitrobenzoyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2C=C(C=CC=2)[N+]([O-])=O)C1 IUAUWOQCLJAOMR-UHFFFAOYSA-N 0.000 description 1
- QVWVCESGCOSIIM-UHFFFAOYSA-N ethyl 2-[4-[[3-[4-[n'-(3-tert-butylbenzoyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2C=C(C=CC=2)C(C)(C)C)C1 QVWVCESGCOSIIM-UHFFFAOYSA-N 0.000 description 1
- GYBLHMPNJBFOMU-UHFFFAOYSA-N ethyl 2-[4-[[3-[4-[n'-(4-fluorobenzoyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2C=CC(F)=CC=2)C1 GYBLHMPNJBFOMU-UHFFFAOYSA-N 0.000 description 1
- OSRAQPUVPLYPFL-UHFFFAOYSA-N ethyl 2-[4-[[3-[4-[n'-(4-nitrobenzoyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2C=CC(=CC=2)[N+]([O-])=O)C1 OSRAQPUVPLYPFL-UHFFFAOYSA-N 0.000 description 1
- INGJKQWHZMJYHU-UHFFFAOYSA-N ethyl 2-[4-[[3-[4-[n'-(furan-2-carbonyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)C=2OC=CC=2)C1 INGJKQWHZMJYHU-UHFFFAOYSA-N 0.000 description 1
- CXRRNNGWQSRQRQ-UHFFFAOYSA-N ethyl 2-[4-[[3-[4-[n'-(furan-3-carbonyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]-2-oxopiperazin-1-yl]acetate Chemical compound C1C(=O)N(CC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C2=COC=C2)C1 CXRRNNGWQSRQRQ-UHFFFAOYSA-N 0.000 description 1
- XWLPRRUFAHTSDO-UHFFFAOYSA-N ethyl 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)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C2=COC=C2)C1 XWLPRRUFAHTSDO-UHFFFAOYSA-N 0.000 description 1
- FJPTVAWFXRJLIM-UHFFFAOYSA-N ethyl 2-[4-[[3-[4-[n'-(naphthalene-1-carbonyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]-2-oxopiperazin-1-yl]acetate Chemical compound C1C(=O)N(CC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2C3=CC=CC=C3C=CC=2)C1 FJPTVAWFXRJLIM-UHFFFAOYSA-N 0.000 description 1
- YBAINCDRZURGHZ-UHFFFAOYSA-N ethyl 2-[4-[[3-[4-[n'-(naphthalene-2-carbonyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]-2-oxopiperazin-1-yl]acetate Chemical compound C1C(=O)N(CC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2C=C3C=CC=CC3=CC=2)C1 YBAINCDRZURGHZ-UHFFFAOYSA-N 0.000 description 1
- GFRMUYLXTKSULA-UHFFFAOYSA-N ethyl 2-[4-[[3-[4-[n'-(naphthalene-2-carbonyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2C=C3C=CC=CC3=CC=2)C1 GFRMUYLXTKSULA-UHFFFAOYSA-N 0.000 description 1
- UDHPKTUNTMHUCJ-UHFFFAOYSA-N ethyl 2-[4-hydroxy-1-[[2-oxo-3-[4-(n'-phenoxycarbonylcarbamimidoyl)phenyl]-1,3-oxazolidin-5-yl]methyl]piperidin-4-yl]acetate Chemical compound C1CC(CC(=O)OCC)(O)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(\N)=N/C(=O)OC=2C=CC=CC=2)C1 UDHPKTUNTMHUCJ-UHFFFAOYSA-N 0.000 description 1
- PYVRCOUTRULJLU-UHFFFAOYSA-N ethyl 2-[4-hydroxy-1-[[2-oxo-3-[4-[n'-(pyridine-3-carbonyl)carbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperidin-4-yl]acetate Chemical compound C1CC(CC(=O)OCC)(O)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2C=NC=CC=2)C1 PYVRCOUTRULJLU-UHFFFAOYSA-N 0.000 description 1
- ORUGPLCUXIJKKH-UHFFFAOYSA-N ethyl 2-[4-hydroxy-1-[[3-[4-[(e)-n'-methylsulfonylcarbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperidin-4-yl]acetate;[3-[4-[(e)-n'-methylsulfonylcarbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate Chemical compound C1=CC(C(=N)NS(=O)(=O)C)=CC=C1N1C(=O)OC(COS(C)(=O)=O)C1.C1CC(CC(=O)OCC)(O)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NS(C)(=O)=O)C1 ORUGPLCUXIJKKH-UHFFFAOYSA-N 0.000 description 1
- FIZBCQJIXOCAAO-UHFFFAOYSA-N ethyl 2-[4-hydroxy-1-[[3-[4-[n'-(naphthalene-2-carbonyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperidin-4-yl]acetate Chemical compound C1CC(CC(=O)OCC)(O)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2C=C3C=CC=CC3=CC=2)C1 FIZBCQJIXOCAAO-UHFFFAOYSA-N 0.000 description 1
- IFXZZZOVEXUANQ-UHFFFAOYSA-N ethyl 2-[[(e)-[amino-[4-[2-oxo-5-[[4-(2-oxo-2-phenylmethoxyethyl)piperazin-1-yl]methyl]-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)OCC=3C=CC=CC=3)CC2)C1 IFXZZZOVEXUANQ-UHFFFAOYSA-N 0.000 description 1
- VYHODCWYWGBUJS-UHFFFAOYSA-N ethyl 2-[[(e)-[amino-[4-[2-oxo-5-[[4-(2-oxo-2-propan-2-yloxyethyl)piperazin-1-yl]methyl]-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(C)C)CC2)C1 VYHODCWYWGBUJS-UHFFFAOYSA-N 0.000 description 1
- 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
- XIMLFPHRUXIAAN-UHFFFAOYSA-N ethyl 3-[2-oxo-4-[[2-oxo-3-[4-[(z)-n'-phenoxycarbonylcarbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C1C(=O)N(CCC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)OC=2C=CC=CC=2)C1 XIMLFPHRUXIAAN-UHFFFAOYSA-N 0.000 description 1
- NBWLPKGANLDAAQ-UHFFFAOYSA-N ethyl 3-[2-oxo-4-[[2-oxo-3-[4-[(z)-n'-phenylmethoxycarbonylcarbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C1C(=O)N(CCC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)OCC=2C=CC=CC=2)C1 NBWLPKGANLDAAQ-UHFFFAOYSA-N 0.000 description 1
- UFKCUDYNAUZEOE-UHFFFAOYSA-N ethyl 3-[2-oxo-4-[[2-oxo-3-[4-[n'-(pyridine-3-carbonyl)carbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-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=NC=CC=2)C1 UFKCUDYNAUZEOE-UHFFFAOYSA-N 0.000 description 1
- RARCPYZPFFDSBD-UHFFFAOYSA-N ethyl 3-[2-oxo-4-[[2-oxo-3-[4-[n'-(thiophene-2-carbonyl)carbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C1C(=O)N(CCC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2SC=CC=2)C1 RARCPYZPFFDSBD-UHFFFAOYSA-N 0.000 description 1
- QFASYEJDMIKKIO-UHFFFAOYSA-N ethyl 3-[2-oxo-4-[[2-oxo-3-[4-[n'-(thiophene-3-carbonyl)carbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C1C(=O)N(CCC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C2=CSC=C2)C1 QFASYEJDMIKKIO-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
- MRLMJRDPOKFXPO-UHFFFAOYSA-N ethyl 3-[4-[4-[4-(n'-benzoylcarbamimidoyl)phenyl]piperazin-1-yl]piperidin-1-yl]propanoate Chemical compound C1CN(CCC(=O)OCC)CCC1N1CCN(C=2C=CC(=CC=2)C(=N)NC(=O)C=2C=CC=CC=2)CC1 MRLMJRDPOKFXPO-UHFFFAOYSA-N 0.000 description 1
- NFGVXGYBYYCRTR-HSZRJFAPSA-N ethyl 3-[4-[[(5r)-3-[4-(n'-benzoylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C1CN(CCC(=O)OCC)CCN1C[C@H]1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)C=2C=CC=CC=2)C1 NFGVXGYBYYCRTR-HSZRJFAPSA-N 0.000 description 1
- OIKLZHZWGYXOGA-UHFFFAOYSA-N ethyl 3-[4-[[2-oxo-3-[4-(N-phenylmethoxycarbonylcarbamimidoyl)phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate [2-oxo-3-[4-(N-phenylmethoxycarbonylcarbamimidoyl)phenyl]-1,3-oxazolidin-5-yl]methyl methanesulfonate Chemical compound O=C1OC(COS(=O)(=O)C)CN1C1=CC=C(C(=N)NC(=O)OCC=2C=CC=CC=2)C=C1.C1CN(CCC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)OCC=2C=CC=CC=2)C1 OIKLZHZWGYXOGA-UHFFFAOYSA-N 0.000 description 1
- MJMRGHLDHHGLJZ-UHFFFAOYSA-N ethyl 3-[4-[[2-oxo-3-[4-[(z)-n'-phenylmethoxycarbonylcarbamimidoyl]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)OCC=2C=CC=CC=2)C1 MJMRGHLDHHGLJZ-UHFFFAOYSA-N 0.000 description 1
- LPOQEJWAXJIIFJ-UHFFFAOYSA-N ethyl 3-[4-[[2-oxo-3-[4-[N-(thiophene-2-carbonyl)carbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate [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.C1CN(CCC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)C=2SC=CC=2)C1 LPOQEJWAXJIIFJ-UHFFFAOYSA-N 0.000 description 1
- LINOOWQJGWQXHF-UHFFFAOYSA-N ethyl 3-[4-[[2-oxo-3-[4-[N-(thiophene-3-carbonyl)carbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate [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.C1CN(CCC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)C2=CSC=C2)C1 LINOOWQJGWQXHF-UHFFFAOYSA-N 0.000 description 1
- WAFNBKSCIKNVGP-UHFFFAOYSA-N ethyl 3-[4-[[3-[4-(N-methoxycarbonylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]-2-oxopiperazin-1-yl]propanoate [3-[4-(N-methoxycarbonylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate Chemical compound C1=CC(C(=N)NC(=O)OC)=CC=C1N1C(=O)OC(COS(C)(=O)=O)C1.C1C(=O)N(CCC(=O)OCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)OC)C1 WAFNBKSCIKNVGP-UHFFFAOYSA-N 0.000 description 1
- WQBPOLHRLVUBHQ-UHFFFAOYSA-N ethyl 3-[4-[[3-[4-(n'-benzoylcarbamimidoyl)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=CC=CC=2)C1 WQBPOLHRLVUBHQ-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
- NSYJVNPHDKWGEZ-UHFFFAOYSA-N ethyl 3-[4-[[3-[4-[(z)-n'-methylsulfonylcarbamimidoyl]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)=NS(C)(=O)=O)C1 NSYJVNPHDKWGEZ-UHFFFAOYSA-N 0.000 description 1
- WJAOCQUTLBKBAZ-UHFFFAOYSA-N ethyl 3-[4-[[3-[4-[n'-(1,3-benzodioxole-5-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=2C=C3OCOC3=CC=2)C1 WJAOCQUTLBKBAZ-UHFFFAOYSA-N 0.000 description 1
- DJVFETSNBFNOJZ-UHFFFAOYSA-N ethyl 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)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 DJVFETSNBFNOJZ-UHFFFAOYSA-N 0.000 description 1
- FXDSICMPQFDRMQ-UHFFFAOYSA-N ethyl 3-[4-[[3-[4-[n'-(2-chlorobenzoyl)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=2C(=CC=CC=2)Cl)C1 FXDSICMPQFDRMQ-UHFFFAOYSA-N 0.000 description 1
- RJNIMWLWLWGTDW-UHFFFAOYSA-N ethyl 3-[4-[[3-[4-[n'-(2-methylbenzoyl)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=2C(=CC=CC=2)C)C1 RJNIMWLWLWGTDW-UHFFFAOYSA-N 0.000 description 1
- QWMOEAARHJLDND-UHFFFAOYSA-N ethyl 3-[4-[[3-[4-[n'-(2-nitrobenzoyl)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=2C(=CC=CC=2)[N+]([O-])=O)C1 QWMOEAARHJLDND-UHFFFAOYSA-N 0.000 description 1
- PGPIOYVMPMKLRW-UHFFFAOYSA-N ethyl 3-[4-[[3-[4-[n'-(3-chlorobenzoyl)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=2C=C(Cl)C=CC=2)C1 PGPIOYVMPMKLRW-UHFFFAOYSA-N 0.000 description 1
- BATNVYOPKOBWDH-UHFFFAOYSA-N ethyl 3-[4-[[3-[4-[n'-(3-fluorobenzoyl)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=2C=C(F)C=CC=2)C1 BATNVYOPKOBWDH-UHFFFAOYSA-N 0.000 description 1
- LLKCPBBCORWCKZ-UHFFFAOYSA-N ethyl 3-[4-[[3-[4-[n'-(3-methylbenzoyl)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=2C=C(C)C=CC=2)C1 LLKCPBBCORWCKZ-UHFFFAOYSA-N 0.000 description 1
- DHJWSVVBMFRJOX-UHFFFAOYSA-N ethyl 3-[4-[[3-[4-[n'-(3-nitrobenzoyl)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=2C=C(C=CC=2)[N+]([O-])=O)C1 DHJWSVVBMFRJOX-UHFFFAOYSA-N 0.000 description 1
- LUDVXIOAGBNMBX-UHFFFAOYSA-N ethyl 3-[4-[[3-[4-[n'-(3-tert-butylbenzoyl)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=2C=C(C=CC=2)C(C)(C)C)C1 LUDVXIOAGBNMBX-UHFFFAOYSA-N 0.000 description 1
- QFWBLVOGFSIJDM-UHFFFAOYSA-N ethyl 3-[4-[[3-[4-[n'-(4-chlorobenzoyl)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=2C=CC(Cl)=CC=2)C1 QFWBLVOGFSIJDM-UHFFFAOYSA-N 0.000 description 1
- OMTFWZBNYQLFLL-UHFFFAOYSA-N ethyl 3-[4-[[3-[4-[n'-(4-fluorobenzoyl)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=2C=CC(F)=CC=2)C1 OMTFWZBNYQLFLL-UHFFFAOYSA-N 0.000 description 1
- VOHLHICAYKNBMS-UHFFFAOYSA-N ethyl 3-[4-[[3-[4-[n'-(4-methylbenzoyl)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=2C=CC(C)=CC=2)C1 VOHLHICAYKNBMS-UHFFFAOYSA-N 0.000 description 1
- ADBVNDKWBPSZDU-UHFFFAOYSA-N ethyl 3-[4-[[3-[4-[n'-(4-nitrobenzoyl)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=2C=CC(=CC=2)[N+]([O-])=O)C1 ADBVNDKWBPSZDU-UHFFFAOYSA-N 0.000 description 1
- KCFWGGPLKHWFLM-UHFFFAOYSA-N ethyl 3-[4-[[3-[4-[n'-(4-tert-butylbenzoyl)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=2C=CC(=CC=2)C(C)(C)C)C1 KCFWGGPLKHWFLM-UHFFFAOYSA-N 0.000 description 1
- ZYAXSCWUKWNGJM-UHFFFAOYSA-N ethyl 3-[4-[[3-[4-[n'-(furan-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=2OC=CC=2)C1 ZYAXSCWUKWNGJM-UHFFFAOYSA-N 0.000 description 1
- VMBUVJJYKIPCPL-UHFFFAOYSA-N ethyl 3-[4-[[3-[4-[n'-(furan-3-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)C2=COC=C2)C1 VMBUVJJYKIPCPL-UHFFFAOYSA-N 0.000 description 1
- LGZLCYHBPCIASK-UHFFFAOYSA-N ethyl 3-[4-[[3-[4-[n'-(naphthalene-1-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=2C3=CC=CC=C3C=CC=2)C1 LGZLCYHBPCIASK-UHFFFAOYSA-N 0.000 description 1
- LXPGZAICFHIXBP-UHFFFAOYSA-N ethyl 3-[4-[[3-[4-[n'-(naphthalene-1-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=2C3=CC=CC=C3C=CC=2)C1 LXPGZAICFHIXBP-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
- LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 description 1
- RUJPPJYDHHAEEK-UHFFFAOYSA-N ethyl piperidine-4-carboxylate Chemical compound CCOC(=O)C1CCNCC1 RUJPPJYDHHAEEK-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002463 imidates Chemical class 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- UZJCZGKLFRQEPW-UHFFFAOYSA-N methyl 2-[4-[[2-oxo-3-[4-(n'-phenoxycarbonylcarbamimidoyl)phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(\N)=N/C(=O)OC=2C=CC=CC=2)C1 UZJCZGKLFRQEPW-UHFFFAOYSA-N 0.000 description 1
- KCCRZRRFDDWPJY-UHFFFAOYSA-N methyl 2-[4-[[2-oxo-3-[4-(n'-phenylmethoxycarbonylcarbamimidoyl)phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(\N)=N/C(=O)OCC=2C=CC=CC=2)C1 KCCRZRRFDDWPJY-UHFFFAOYSA-N 0.000 description 1
- PZYBJRLVTKJKMA-UHFFFAOYSA-N methyl 2-[4-[[2-oxo-3-[4-[n'-(thiophene-2-carbonyl)carbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2SC=CC=2)C1 PZYBJRLVTKJKMA-UHFFFAOYSA-N 0.000 description 1
- ZYSGEFCNZSZVDJ-UHFFFAOYSA-N methyl 2-[4-[[2-oxo-3-[4-[n'-(thiophene-3-carbonyl)carbamimidoyl]phenyl]-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C2=CSC=C2)C1 ZYSGEFCNZSZVDJ-UHFFFAOYSA-N 0.000 description 1
- PLJFGZFSSYGZNJ-UHFFFAOYSA-N methyl 2-[4-[[3-[4-(n'-benzoylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2C=CC=CC=2)C1 PLJFGZFSSYGZNJ-UHFFFAOYSA-N 0.000 description 1
- OXTYBCWKWCFIMQ-UHFFFAOYSA-N methyl 2-[4-[[3-[4-(n'-methoxycarbonylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(\N)=N/C(=O)OC)C1 OXTYBCWKWCFIMQ-UHFFFAOYSA-N 0.000 description 1
- NNNHKAWUUWNXRK-UHFFFAOYSA-N methyl 2-[4-[[3-[4-(n'-methylsulfonylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(\N)=N/S(C)(=O)=O)C1 NNNHKAWUUWNXRK-UHFFFAOYSA-N 0.000 description 1
- RBYNXNKHWOFFEO-UHFFFAOYSA-N methyl 2-[4-[[3-[4-[n'-(furan-2-carbonyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2OC=CC=2)C1 RBYNXNKHWOFFEO-UHFFFAOYSA-N 0.000 description 1
- TZGQWIWTJIZTOT-UHFFFAOYSA-N methyl 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)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C2=COC=C2)C1 TZGQWIWTJIZTOT-UHFFFAOYSA-N 0.000 description 1
- QTWPVHXSTZCMLD-UHFFFAOYSA-N methyl 2-[4-[[3-[4-[n'-(naphthalene-1-carbonyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2C3=CC=CC=C3C=CC=2)C1 QTWPVHXSTZCMLD-UHFFFAOYSA-N 0.000 description 1
- XCXCKQJLOOPLAU-UHFFFAOYSA-N methyl 2-[4-[[3-[4-[n'-(naphthalene-2-carbonyl)carbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2C=C3C=CC=CC3=CC=2)C1 XCXCKQJLOOPLAU-UHFFFAOYSA-N 0.000 description 1
- UHHVABRWHRKEPJ-UHFFFAOYSA-N methyl 2-piperazin-1-ylacetate Chemical compound COC(=O)CN1CCNCC1 UHHVABRWHRKEPJ-UHFFFAOYSA-N 0.000 description 1
- XBEMKYKBSKPVRA-UHFFFAOYSA-N methyl 3-[4-[[2-oxo-3-[4-[(z)-n'-phenoxycarbonylcarbamimidoyl]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)OC=2C=CC=CC=2)C1 XBEMKYKBSKPVRA-UHFFFAOYSA-N 0.000 description 1
- WYMBTGOMAOHGRF-UHFFFAOYSA-N methyl 3-[4-[[2-oxo-3-[4-[(z)-n'-phenylmethoxycarbonylcarbamimidoyl]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)OCC=2C=CC=CC=2)C1 WYMBTGOMAOHGRF-UHFFFAOYSA-N 0.000 description 1
- DRURLRSTQZVXJS-UHFFFAOYSA-N methyl 3-[4-[[2-oxo-3-[4-[n'-(thiophene-2-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=2SC=CC=2)C1 DRURLRSTQZVXJS-UHFFFAOYSA-N 0.000 description 1
- HJZCFARZINDINB-UHFFFAOYSA-N methyl 3-[4-[[2-oxo-3-[4-[n'-(thiophene-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)C2=CSC=C2)C1 HJZCFARZINDINB-UHFFFAOYSA-N 0.000 description 1
- VBWQCWSZFBJMPL-UHFFFAOYSA-N methyl 3-[4-[[3-[4-(n'-benzoylcarbamimidoyl)phenyl]-2-oxo-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=CC=CC=2)C1 VBWQCWSZFBJMPL-UHFFFAOYSA-N 0.000 description 1
- DVWYCTZQJRDITP-UHFFFAOYSA-N methyl 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)OC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)OC)C1 DVWYCTZQJRDITP-UHFFFAOYSA-N 0.000 description 1
- BICMUCAHEMDHKT-UHFFFAOYSA-N methyl 3-[4-[[3-[4-[(z)-n'-methylsulfonylcarbamimidoyl]phenyl]-2-oxo-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)NS(C)(=O)=O)C1 BICMUCAHEMDHKT-UHFFFAOYSA-N 0.000 description 1
- WJVRORXCOYWLIO-UHFFFAOYSA-N methyl 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)OC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)C=2OC=CC=2)C1 WJVRORXCOYWLIO-UHFFFAOYSA-N 0.000 description 1
- SWHISGWULISCDZ-UHFFFAOYSA-N methyl 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)OC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)C2=COC=C2)C1 SWHISGWULISCDZ-UHFFFAOYSA-N 0.000 description 1
- OMPAAEQAKNATNL-UHFFFAOYSA-N methyl 3-[4-[[3-[4-[n'-(naphthalene-1-carbonyl)carbamimidoyl]phenyl]-2-oxo-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=2C3=CC=CC=C3C=CC=2)C1 OMPAAEQAKNATNL-UHFFFAOYSA-N 0.000 description 1
- LJCDGQFQCQLUKU-UHFFFAOYSA-N methyl 3-[4-[[3-[4-[n'-(naphthalene-2-carbonyl)carbamimidoyl]phenyl]-2-oxo-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=C3C=CC=CC3=CC=2)C1 LJCDGQFQCQLUKU-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 description 1
- 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- AAZQKMDDOJFZGA-UHFFFAOYSA-N n-[amino-[4-[5-(chloromethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]methylidene]benzamide Chemical compound O=C1OC(CCl)CN1C1=CC=C(C(=N)NC(=O)C=2C=CC=CC=2)C=C1 AAZQKMDDOJFZGA-UHFFFAOYSA-N 0.000 description 1
- WEKVLXOSXPMTNG-UHFFFAOYSA-N n-[amino-[4-[5-(chloromethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]methylidene]benzamide;methyl 2-[4-[[3-[4-(n'-benzoylcarbamimidoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methoxy]phenyl]acetate Chemical compound C=1C=C(N2C(OC(CCl)C2)=O)C=CC=1C(N)=NC(=O)C1=CC=CC=C1.C1=CC(CC(=O)OC)=CC=C1OCC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2C=CC=CC=2)C1 WEKVLXOSXPMTNG-UHFFFAOYSA-N 0.000 description 1
- 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
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 125000000109 phenylethoxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])O* 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000010318 polygalacturonic acid Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- SESPITJTZNBARS-UHFFFAOYSA-N propan-2-yl 2-[4-[[2-oxo-3-[4-(n'-phenoxycarbonylcarbamimidoyl)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)=N/C(=O)OC=2C=CC=CC=2)C1 SESPITJTZNBARS-UHFFFAOYSA-N 0.000 description 1
- LYHKKCZCXPDSNZ-UHFFFAOYSA-N propan-2-yl 2-[4-[[2-oxo-3-[4-(n'-phenylmethoxycarbonylcarbamimidoyl)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)=N/C(=O)OCC=2C=CC=CC=2)C1 LYHKKCZCXPDSNZ-UHFFFAOYSA-N 0.000 description 1
- CHRAZNRCEAXZLN-UHFFFAOYSA-N propan-2-yl 2-[4-[[2-oxo-3-[4-[n'-(thiophene-2-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=2SC=CC=2)C1 CHRAZNRCEAXZLN-UHFFFAOYSA-N 0.000 description 1
- XRXFMSLNSSKNPF-UHFFFAOYSA-N propan-2-yl 2-[4-[[2-oxo-3-[4-[n'-(thiophene-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)C2=CSC=C2)C1 XRXFMSLNSSKNPF-UHFFFAOYSA-N 0.000 description 1
- VPLLSBIUEZJKSM-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[4-(n'-benzoylcarbamimidoyl)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=2C=CC=CC=2)C1 VPLLSBIUEZJKSM-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
- CEAGCBZXHPVOJV-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[4-(n'-methylsulfonylcarbamimidoyl)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)=N/S(C)(=O)=O)C1 CEAGCBZXHPVOJV-UHFFFAOYSA-N 0.000 description 1
- ZETALPFIGWEECF-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[4-[n'-(furan-2-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)C=2OC=CC=2)C1 ZETALPFIGWEECF-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
- JTNPLBOXZDARLK-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[4-[n'-(naphthalene-1-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)C=2C3=CC=CC=C3C=CC=2)C1 JTNPLBOXZDARLK-UHFFFAOYSA-N 0.000 description 1
- FDXPLYUVHSFKSL-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[4-[n'-(naphthalene-2-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)C=2C=C3C=CC=CC3=CC=2)C1 FDXPLYUVHSFKSL-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
- LHYAYWSEWNYOCW-UHFFFAOYSA-N propan-2-yl 3-[4-[[2-oxo-3-[4-[(z)-n'-phenoxycarbonylcarbamimidoyl]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)OC=2C=CC=CC=2)C1 LHYAYWSEWNYOCW-UHFFFAOYSA-N 0.000 description 1
- YKLISYFGKGMLOL-UHFFFAOYSA-N propan-2-yl 3-[4-[[2-oxo-3-[4-[(z)-n'-phenylmethoxycarbonylcarbamimidoyl]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)OCC=2C=CC=CC=2)C1 YKLISYFGKGMLOL-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
- JCQAXMBCABVODQ-UHFFFAOYSA-N propan-2-yl 3-[4-[[2-oxo-3-[4-[n'-(thiophene-2-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=2SC=CC=2)C1 JCQAXMBCABVODQ-UHFFFAOYSA-N 0.000 description 1
- FAIJOCTYGSTESW-UHFFFAOYSA-N propan-2-yl 3-[4-[[2-oxo-3-[4-[n'-(thiophene-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)C2=CSC=C2)C1 FAIJOCTYGSTESW-UHFFFAOYSA-N 0.000 description 1
- LUCRMRXZEVIYRN-UHFFFAOYSA-N propan-2-yl 3-[4-[[3-[4-(n'-benzoylcarbamimidoyl)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=2C=CC=CC=2)C1 LUCRMRXZEVIYRN-UHFFFAOYSA-N 0.000 description 1
- RRLRHGLXZCUIJF-UHFFFAOYSA-N propan-2-yl 3-[4-[[3-[4-[(z)-n'-methoxycarbonylcarbamimidoyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C1=CC(C(N)=NC(=O)OC)=CC=C1N1C(=O)OC(CN2CCN(CCC(=O)OC(C)C)CC2)C1 RRLRHGLXZCUIJF-UHFFFAOYSA-N 0.000 description 1
- RLBFAOBETLEPSN-UHFFFAOYSA-N propan-2-yl 3-[4-[[3-[4-[(z)-n'-methylsulfonylcarbamimidoyl]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)=NS(C)(=O)=O)C1 RLBFAOBETLEPSN-UHFFFAOYSA-N 0.000 description 1
- PHWLVLFCZXUXFL-UHFFFAOYSA-N propan-2-yl 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)OC(C)C)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2OC=CC=2)C1 PHWLVLFCZXUXFL-UHFFFAOYSA-N 0.000 description 1
- JGBXKVHSFQTQFX-UHFFFAOYSA-N propan-2-yl 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)OC(C)C)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C2=COC=C2)C1 JGBXKVHSFQTQFX-UHFFFAOYSA-N 0.000 description 1
- MBORKRYRJNHBJK-UHFFFAOYSA-N propan-2-yl 3-[4-[[3-[4-[n'-(naphthalene-1-carbonyl)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=2C3=CC=CC=C3C=CC=2)C1 MBORKRYRJNHBJK-UHFFFAOYSA-N 0.000 description 1
- DGGYTKHHSPJYRB-UHFFFAOYSA-N propan-2-yl 3-[4-[[3-[4-[n'-(naphthalene-2-carbonyl)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=2C=C3C=CC=CC3=CC=2)C1 DGGYTKHHSPJYRB-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
- 239000003380 propellant Substances 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
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940074545 sodium dihydrogen phosphate dihydrate Drugs 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- JGKIXQVVHVHVHG-UHFFFAOYSA-M sodium;4-(2-methoxy-2-oxoethyl)phenolate Chemical compound [Na+].COC(=O)CC1=CC=C([O-])C=C1 JGKIXQVVHVHVHG-UHFFFAOYSA-M 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- OQFKAOSDYYOXCA-UHFFFAOYSA-N tert-butyl 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)C)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)C=2C=NC=CC=2)C1 OQFKAOSDYYOXCA-UHFFFAOYSA-N 0.000 description 1
- YJSLABJYIOQSLO-UHFFFAOYSA-N tert-butyl 3-[4-[[3-[4-(n'-benzoylcarbamimidoyl)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=2C=CC=CC=2)C1 YJSLABJYIOQSLO-UHFFFAOYSA-N 0.000 description 1
- GPIWOUDOPKRHLP-UHFFFAOYSA-N tert-butyl 3-[4-[[3-[4-[(z)-n'-methylsulfonylcarbamimidoyl]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)NS(C)(=O)=O)C1 GPIWOUDOPKRHLP-UHFFFAOYSA-N 0.000 description 1
- MDMDPZVOOSKTPF-UHFFFAOYSA-N tert-butyl 3-[4-[[3-[4-[n'-(naphthalene-2-carbonyl)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=2C=C3C=CC=CC3=CC=2)C1 MDMDPZVOOSKTPF-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
- 125000005425 toluyl group Chemical group 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/04—Drugs for skeletal disorders for non-specific disorders of the connective tissue
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/02—Local antiseptics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/08—Plasma substitutes; Perfusion solutions; Dialytics or haemodialytics; Drugs for electrolytic or acid-base disorders, e.g. hypovolemic shock
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
- C07C257/20—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having nitrogen atoms of amidino groups acylated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/14—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Physical Education & Sports Medicine (AREA)
- Immunology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Oncology (AREA)
- Rheumatology (AREA)
- Communicable Diseases (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Transplantation (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Biomedical Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19516483A DE19516483A1 (de) | 1995-05-05 | 1995-05-05 | Adhäsionsrezeptor-Antagonisten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK57396A3 SK57396A3 (en) | 1996-11-06 |
| SK282563B6 true SK282563B6 (sk) | 2002-10-08 |
Family
ID=7761137
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK573-96A SK282563B6 (sk) | 1995-05-05 | 1996-05-06 | Derivát oxazolidinónu, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US6455529B1 (cs) |
| EP (1) | EP0741133B1 (cs) |
| JP (1) | JP4202438B2 (cs) |
| KR (1) | KR100462176B1 (cs) |
| CN (1) | CN1134423C (cs) |
| AR (1) | AR003121A1 (cs) |
| AT (1) | ATE258548T1 (cs) |
| AU (1) | AU708813B2 (cs) |
| BR (1) | BR9602150A (cs) |
| CA (1) | CA2175767C (cs) |
| CO (1) | CO4950623A1 (cs) |
| CZ (1) | CZ291621B6 (cs) |
| DE (2) | DE19516483A1 (cs) |
| DK (1) | DK0741133T3 (cs) |
| ES (1) | ES2213758T3 (cs) |
| HU (1) | HUP9601176A3 (cs) |
| NO (1) | NO305906B1 (cs) |
| PL (1) | PL187000B1 (cs) |
| PT (1) | PT741133E (cs) |
| RU (1) | RU2162086C2 (cs) |
| SK (1) | SK282563B6 (cs) |
| TR (1) | TR199600359A2 (cs) |
| TW (1) | TW378205B (cs) |
| UA (1) | UA53608C2 (cs) |
| ZA (1) | ZA963535B (cs) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6218387B1 (en) | 1996-12-20 | 2001-04-17 | Hoechst Aktiengesellschaft | Vitronectin receptor anatagonists, their preparation and their use |
| US6482821B2 (en) | 1996-12-20 | 2002-11-19 | Hoechst Aktiengellschaft | Vitronectin receptor antagonists, their preparation and their use |
| DE19653647A1 (de) | 1996-12-20 | 1998-06-25 | Hoechst Ag | Vitronectin - Rezeptorantagonisten, deren Herstellung sowie deren Verwendung |
| DE19653645A1 (de) * | 1996-12-20 | 1998-06-25 | Hoechst Ag | Vitronectin - Rezeptorantagonisten, deren Herstellung sowie deren Verwendung |
| DE19755268A1 (de) * | 1997-12-12 | 1999-06-17 | Merck Patent Gmbh | Benzamidinderivate |
| AU1687699A (en) * | 1997-12-25 | 1999-07-19 | Yamanouchi Pharmaceutical Co., Ltd. | Nitrogenous heterocyclic derivatives |
| TR200003595T2 (tr) | 1998-06-05 | 2001-07-23 | Astrazeneca Ab | Kimyasal bileşikler |
| EP1140183A1 (en) | 1998-12-23 | 2001-10-10 | G.D. Searle & Co. | Use of a matrix metalloproteinase inhibitor and an integrin antagonist in the treatment of neoplasia |
| KR20010108499A (ko) | 1999-04-13 | 2001-12-07 | 스타르크, 카르크 | 인테그린 수용체 리간드 |
| EP1188440A4 (en) * | 1999-06-18 | 2004-04-14 | Yamanouchi Pharma Co Ltd | MEDICINAL COMPOSITION FOR ORAL ADMINISTRATION |
| GB9928568D0 (en) | 1999-12-03 | 2000-02-02 | Zeneca Ltd | Chemical compounds |
| AU2001253113B2 (en) * | 2000-04-20 | 2005-02-03 | Pharmacia & Upjohn Company | Use of thioamide oxazolidinones for the treatment of bone resorption and osteoporosis |
| GB0009803D0 (en) * | 2000-04-25 | 2000-06-07 | Astrazeneca Ab | Chemical compounds |
| DE10108995A1 (de) * | 2001-02-23 | 2002-09-05 | Abbott Gmbh & Co Kg | Substituierte Pyrimidinon-Derivate als Liganden von Integrinrezeptoren |
| DE10159453A1 (de) * | 2001-12-04 | 2003-06-18 | Merck Patent Gmbh | Verwendung von 1-Phenyl-oxazolidin-2-on-Verbindungen als Protease |
| PT1539739E (pt) * | 2002-08-16 | 2011-01-05 | Janssen Pharmaceutica Nv | Compostos de piperidinilo que ligam selectivamente integrinas |
| TWI344955B (en) * | 2003-03-14 | 2011-07-11 | Ono Pharmaceutical Co | Heterocyclic rinf having nitrogen atom derivatives and medicament containing the derivatives as active ingredient |
| US7405210B2 (en) * | 2003-05-21 | 2008-07-29 | Osi Pharmaceuticals, Inc. | Pyrrolopyridine-2-carboxylic acid amide inhibitors of glycogen phosphorylase |
| JP2007527904A (ja) | 2004-03-08 | 2007-10-04 | プロシディオン・リミテッド | グリコーゲンホスホリラーゼ阻害剤としてのピロロピリジン−2−カルボン酸ヒドラジド化合物 |
| PT2484365E (pt) | 2004-06-04 | 2013-12-12 | Scripps Research Inst | Composições e métodos para o tratamento de doenças neovasculares |
| EP1609784A1 (de) * | 2004-06-25 | 2005-12-28 | Boehringer Ingelheim Pharma GmbH & Co.KG | Verfahren zur Herstellung von 4-(Benzimidazolylmethylamino)-Benzamidinen |
| WO2006052962A2 (en) | 2004-11-10 | 2006-05-18 | Janssen Pharmaceutica, N.V. | Bicyclic triazole a4 integrin inhibitors |
| JP2008521873A (ja) | 2004-12-02 | 2008-06-26 | プロシディオン・リミテッド | ピロロピリジン−2−カルボン酸アミド類 |
| EP2146722A4 (en) * | 2007-05-10 | 2011-08-03 | Amr Technology Inc | ARYL AND HETEROARYL SUBSTITUTED TETRAHYDROBENZO-1,4-DIAZEPINES AND THEIR USE FOR BLOCKING THE RECOVERY OF NOREPINEPHRIN, DOPAMINE AND SEROTONINE |
| US9802954B2 (en) | 2011-08-24 | 2017-10-31 | Boehringer Ingelheim International Gmbh | Piperidino-dihydrothienopyrimidine sulfoxides and their use for treating COPD and asthma |
| DE102015011861B4 (de) | 2015-09-10 | 2018-03-01 | Rudolf Schindler | Neue cyclische Carboxamide als NMDA NR2B Rezeptor Inhibitoren |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6183170A (ja) * | 1984-09-28 | 1986-04-26 | Nippon Chemiphar Co Ltd | 新規な1,3−オキサゾリジン−2−オン誘導体およびその製造法 |
| US5053393A (en) * | 1988-07-20 | 1991-10-01 | Monsanto Company | Novel platelet-aggregation inhibitor |
| US5256812A (en) | 1989-01-31 | 1993-10-26 | Hoffmann-La Roche Inc. | Carboxamides and sulfonamides |
| US5084466A (en) | 1989-01-31 | 1992-01-28 | Hoffmann-La Roche Inc. | Novel carboxamide pyridine compounds which have useful pharmaceutical utility |
| DE4017211A1 (de) | 1990-05-29 | 1991-12-05 | Merck Patent Gmbh | Oxazolidinone |
| AU666318B2 (en) * | 1991-06-28 | 1996-02-08 | Smithkline Beecham Corporation | Bicyclic fibrinogen antagonists |
| US5239113A (en) * | 1991-10-15 | 1993-08-24 | Monsanto Company | Substituted β-amino acid derivatives useful as platelet aggregation inhibitors and intermediates thereof |
| TW221996B (cs) * | 1991-11-14 | 1994-04-01 | Glaxo Group Ltd | |
| DE4234295A1 (de) * | 1992-10-12 | 1994-04-14 | Thomae Gmbh Dr K | Carbonsäurederivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| CN1041921C (zh) * | 1992-12-21 | 1999-02-03 | 史密丝克莱恩比彻姆公司 | 双环血纤维蛋白原拮抗剂 |
| DK0623615T3 (da) * | 1993-05-01 | 1999-12-13 | Merck Patent Gmbh | Adhæsionsreceptor-antagonister |
| DE4324393A1 (de) * | 1993-07-21 | 1995-01-26 | Merck Patent Gmbh | 4-Aryloxy- und 4-Arylthiopiperidinderivate |
| DE4332384A1 (de) | 1993-09-23 | 1995-03-30 | Merck Patent Gmbh | Adhäsionsrezeptor-Antagonisten III |
| US5563158A (en) * | 1993-12-28 | 1996-10-08 | The Dupont Merck Pharmaceutical Company | Aromatic compounds containing basic and acidic termini useful as fibrinogen receptor antagonists |
| MA23420A1 (fr) * | 1994-01-07 | 1995-10-01 | Smithkline Beecham Corp | Antagonistes bicycliques de fibrinogene. |
| DE4429461A1 (de) * | 1994-08-19 | 1996-02-22 | Merck Patent Gmbh | Adhäsionsrezeptor-Antagonisten |
| EP0710657B1 (de) * | 1994-11-02 | 1998-08-26 | MERCK PATENT GmbH | Adhäsionsrezeptor-Antagonisten |
| DE19504954A1 (de) * | 1995-02-15 | 1996-08-22 | Merck Patent Gmbh | Adhäsionsrezeptor-Antagonisten |
-
1995
- 1995-05-05 DE DE19516483A patent/DE19516483A1/de not_active Withdrawn
-
1996
- 1996-03-26 TW TW085103612A patent/TW378205B/zh not_active IP Right Cessation
- 1996-04-24 DK DK96106423T patent/DK0741133T3/da active
- 1996-04-24 PT PT96106423T patent/PT741133E/pt unknown
- 1996-04-24 ES ES96106423T patent/ES2213758T3/es not_active Expired - Lifetime
- 1996-04-24 DE DE59610900T patent/DE59610900D1/de not_active Expired - Fee Related
- 1996-04-24 EP EP96106423A patent/EP0741133B1/de not_active Expired - Lifetime
- 1996-04-24 AT AT96106423T patent/ATE258548T1/de not_active IP Right Cessation
- 1996-04-26 UA UA96041680A patent/UA53608C2/uk unknown
- 1996-04-29 RU RU96108122/04A patent/RU2162086C2/ru not_active IP Right Cessation
- 1996-04-30 AU AU51969/96A patent/AU708813B2/en not_active Ceased
- 1996-04-30 PL PL96314044A patent/PL187000B1/pl not_active IP Right Cessation
- 1996-05-02 JP JP13413796A patent/JP4202438B2/ja not_active Expired - Fee Related
- 1996-05-03 US US08/642,268 patent/US6455529B1/en not_active Expired - Fee Related
- 1996-05-03 NO NO961813A patent/NO305906B1/no not_active IP Right Cessation
- 1996-05-03 BR BR9602150A patent/BR9602150A/pt not_active Application Discontinuation
- 1996-05-03 AR ARP960102444A patent/AR003121A1/es not_active Application Discontinuation
- 1996-05-03 CZ CZ19961295A patent/CZ291621B6/cs not_active IP Right Cessation
- 1996-05-03 TR TR96/00359A patent/TR199600359A2/xx unknown
- 1996-05-03 HU HU9601176A patent/HUP9601176A3/hu unknown
- 1996-05-03 CN CNB961062258A patent/CN1134423C/zh not_active Expired - Fee Related
- 1996-05-03 CA CA002175767A patent/CA2175767C/en not_active Expired - Fee Related
- 1996-05-03 ZA ZA963535A patent/ZA963535B/xx unknown
- 1996-05-06 KR KR1019960014643A patent/KR100462176B1/ko not_active Expired - Fee Related
- 1996-05-06 SK SK573-96A patent/SK282563B6/sk unknown
- 1996-05-06 CO CO96022358A patent/CO4950623A1/es unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SK282563B6 (sk) | Derivát oxazolidinónu, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje | |
| JP3810837B2 (ja) | 接着受容体拮抗物質 | |
| SK112194A3 (en) | Oxazolidine derivative, method of its preparation and pharmaceutical agent which containt its | |
| SK281469B6 (sk) | Deriváty oxazolidínu, spôsob ich výroby, ich použitie a farmaceutický prípravok | |
| RU2155762C2 (ru) | Производные оксазолидина, способ их получения, фармацевтическая композиция | |
| CZ290984B6 (cs) | Deriváty oxazolidinonkarboxylové kyseliny, způsob jejich výroby a pouľití a farmaceutické přípravky na jejich bázi | |
| RU2163602C2 (ru) | Производные оксазолидин-2-она, способ их получения и фармацевтическая композиция на их основе | |
| MXPA96001659A (en) | 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 | |
| SK1402002A3 (en) | Fluorene derivative, process for the preparation thereof and pharmaceutical composition comprising same |