SK281815B6 - 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
- SK281815B6 SK281815B6 SK1368-95A SK136895A SK281815B6 SK 281815 B6 SK281815 B6 SK 281815B6 SK 136895 A SK136895 A SK 136895A SK 281815 B6 SK281815 B6 SK 281815B6
- Authority
- SK
- Slovakia
- Prior art keywords
- piperazino
- methyloxazolidin
- piperidyl
- amidino
- piperazinyl
- Prior art date
Links
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 7
- 239000000825 pharmaceutical preparation Substances 0.000 title 1
- -1 NH or NA Inorganic materials 0.000 claims abstract description 277
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 13
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 3
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 62
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 53
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 239000012442 inert solvent Substances 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 238000010306 acid treatment Methods 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- PGWBLVNRAXJCNF-UHFFFAOYSA-N 3-[4-[[3-(1-carbamimidoylpiperidin-4-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoic acid Chemical compound C1CN(C(=N)N)CCC1N1C(=O)OC(CN2CCN(CCC(O)=O)CC2)C1 PGWBLVNRAXJCNF-UHFFFAOYSA-N 0.000 claims 1
- KUNXCZMKRPUITO-UHFFFAOYSA-N methyl 3-[4-[[3-(1-benzylpiperidin-4-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]propanoate Chemical compound C1CN(CCC(=O)OC)CCN1CC1OC(=O)N(C2CCN(CC=3C=CC=CC=3)CC2)C1 KUNXCZMKRPUITO-UHFFFAOYSA-N 0.000 claims 1
- 229940012952 fibrinogen Drugs 0.000 abstract description 12
- 108010049003 Fibrinogen Proteins 0.000 abstract description 11
- 102000008946 Fibrinogen Human genes 0.000 abstract description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 9
- 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
- 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
- 201000010099 disease Diseases 0.000 abstract description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 3
- 230000004054 inflammatory process Effects 0.000 abstract description 3
- 208000010125 myocardial infarction Diseases 0.000 abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 abstract description 3
- 206010028980 Neoplasm Diseases 0.000 abstract description 2
- 208000001132 Osteoporosis Diseases 0.000 abstract description 2
- 201000011510 cancer Diseases 0.000 abstract description 2
- 230000000010 osteolytic effect Effects 0.000 abstract description 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 49
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 43
- 238000006243 chemical reaction Methods 0.000 description 29
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 24
- VWIIJDNADIEEDB-UHFFFAOYSA-N 3-methyl-1,3-oxazolidin-2-one Chemical compound CN1CCOC1=O VWIIJDNADIEEDB-UHFFFAOYSA-N 0.000 description 19
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 125000006239 protecting group Chemical group 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 239000002585 base Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000003826 tablet Substances 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
- 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
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 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
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 5
- 238000007327 hydrogenolysis reaction Methods 0.000 description 5
- 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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 102100037362 Fibronectin Human genes 0.000 description 4
- 108010067306 Fibronectins Proteins 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
- 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
- 125000004432 carbon atom Chemical group C* 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
- 108020003175 receptors Proteins 0.000 description 4
- 102000005962 receptors Human genes 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 108010047303 von Willebrand Factor Proteins 0.000 description 4
- GEUZBVKRIHXPDT-UHFFFAOYSA-N C(N)(=N)N1CCN(CC1)CCN1C(OC(C1C)N1CCN(CC1)CCC(=O)O)=O Chemical compound C(N)(=N)N1CCN(CC1)CCN1C(OC(C1C)N1CCN(CC1)CCC(=O)O)=O GEUZBVKRIHXPDT-UHFFFAOYSA-N 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- RKNJSSPPMAHYLB-UHFFFAOYSA-N [2-oxo-3-[2-(1-propan-2-ylpiperidin-4-yl)ethyl]-1,3-oxazolidin-5-yl]methyl methanesulfonate Chemical compound C1CN(C(C)C)CCC1CCN1C(=O)OC(COS(C)(=O)=O)C1 RKNJSSPPMAHYLB-UHFFFAOYSA-N 0.000 description 3
- MMXCASNBXSKXJF-UHFFFAOYSA-N [3-[(1-ethylpiperidin-4-yl)methyl]-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate Chemical compound C1CN(CC)CCC1CN1C(=O)OC(COS(C)(=O)=O)C1 MMXCASNBXSKXJF-UHFFFAOYSA-N 0.000 description 3
- KTVFFBSECNZJLV-UHFFFAOYSA-N [3-[(1-tert-butylpiperidin-4-yl)methyl]-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate Chemical compound C1CN(C(C)(C)C)CCC1CN1C(=O)OC(COS(C)(=O)=O)C1 KTVFFBSECNZJLV-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 230000002862 amidating effect Effects 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 239000012154 double-distilled water Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000005764 inhibitory process Effects 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
- 125000004193 piperazinyl group Chemical group 0.000 description 3
- 125000003386 piperidinyl group Chemical group 0.000 description 3
- 125000005936 piperidyl group Chemical group 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 238000003797 solvolysis reaction Methods 0.000 description 3
- 208000010110 spontaneous platelet aggregation Diseases 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 210000004881 tumor cell Anatomy 0.000 description 3
- 102100036537 von Willebrand factor Human genes 0.000 description 3
- 229960001134 von willebrand factor Drugs 0.000 description 3
- RJMWHMNYGUZOEU-UHFFFAOYSA-N 2-[4-[3-[2-(1-carbamimidoylpiperidin-4-yl)ethyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]acetic acid Chemical compound C(N)(=N)N1CCC(CC1)CCN1C(OC(C1C)N1CCN(CC1)CC(=O)O)=O RJMWHMNYGUZOEU-UHFFFAOYSA-N 0.000 description 2
- KAMIFQXNHVMUBE-UHFFFAOYSA-N 2-[4-[3-[4-(1-carbamimidoylpiperidin-4-yl)butyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]acetic acid Chemical compound C(N)(=N)N1CCC(CC1)CCCCN1C(OC(C1C)N1CCN(CC1)CC(=O)O)=O KAMIFQXNHVMUBE-UHFFFAOYSA-N 0.000 description 2
- LYLNDCPDPBIZKP-UHFFFAOYSA-N 3-[4-[3-(1-carbamimidoylpiperidin-4-yl)-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoic acid Chemical compound C(N)(=N)N1CCC(CC1)N1C(OC(C1C)N1CCN(CC1)CCC(=O)O)=O LYLNDCPDPBIZKP-UHFFFAOYSA-N 0.000 description 2
- OJADXLLKVRNBBS-UHFFFAOYSA-N 3-[4-[3-[(1-benzylpiperidin-4-yl)methyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoic acid Chemical compound CC1C(N2CCN(CCC(O)=O)CC2)OC(=O)N1CC(CC1)CCN1CC1=CC=CC=C1 OJADXLLKVRNBBS-UHFFFAOYSA-N 0.000 description 2
- HHTPNOLMPSYKDU-UHFFFAOYSA-N 3-[4-[3-[2-(1-carbamimidoylpiperidin-4-yl)ethyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoic acid Chemical compound C(N)(=N)N1CCC(CC1)CCN1C(OC(C1C)N1CCN(CC1)CCC(=O)O)=O HHTPNOLMPSYKDU-UHFFFAOYSA-N 0.000 description 2
- HDKOTUIXGOELOO-UHFFFAOYSA-N 3-[4-[3-[4-(1-carbamimidoylpiperidin-4-yl)butyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoic acid Chemical compound C(N)(=N)N1CCC(CC1)CCCCN1C(OC(C1C)N1CCN(CC1)CCC(=O)O)=O HDKOTUIXGOELOO-UHFFFAOYSA-N 0.000 description 2
- UVWANKJCCRBKOC-UHFFFAOYSA-N 4-[4-[3-[2-(1-carbamimidoylpiperidin-4-yl)ethyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]butanoic acid Chemical compound C(N)(=N)N1CCC(CC1)CCN1C(OC(C1C)N1CCN(CC1)CCCC(=O)O)=O UVWANKJCCRBKOC-UHFFFAOYSA-N 0.000 description 2
- WFAVLPODQWWIHQ-UHFFFAOYSA-N 4-[4-[3-[3-(1-carbamimidoylpiperidin-4-yl)propyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]butanoic acid Chemical compound C(N)(=N)N1CCC(CC1)CCCN1C(OC(C1C)N1CCN(CC1)CCCC(=O)O)=O WFAVLPODQWWIHQ-UHFFFAOYSA-N 0.000 description 2
- DYFBXJKDOZDLQV-UHFFFAOYSA-N 4-[4-[3-[4-(4-carbamimidoylpiperazin-1-yl)butyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]butanoic acid Chemical compound C(N)(=N)N1CCN(CC1)CCCCN1C(OC(C1C)N1CCN(CC1)CCCC(=O)O)=O DYFBXJKDOZDLQV-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 125000006847 BOC protecting group Chemical group 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 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
- 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
- 206010027476 Metastases Diseases 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-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
- WEKYZXPDNNSDBS-UHFFFAOYSA-N [2-oxo-3-(1-propan-2-ylpiperidin-4-yl)-1,3-oxazolidin-5-yl]methyl methanesulfonate Chemical compound C1CN(C(C)C)CCC1N1C(=O)OC(COS(C)(=O)=O)C1 WEKYZXPDNNSDBS-UHFFFAOYSA-N 0.000 description 2
- FUHFHRIHHLOQHH-UHFFFAOYSA-N [3-(1-benzylpiperidin-4-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate Chemical compound O=C1OC(COS(=O)(=O)C)CN1C1CCN(CC=2C=CC=CC=2)CC1 FUHFHRIHHLOQHH-UHFFFAOYSA-N 0.000 description 2
- IBDVBGRFTHIBFS-UHFFFAOYSA-N [3-(1-methylpiperidin-4-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate Chemical compound C1CN(C)CCC1N1C(=O)OC(COS(C)(=O)=O)C1 IBDVBGRFTHIBFS-UHFFFAOYSA-N 0.000 description 2
- BGTRQDVKLZGMIV-UHFFFAOYSA-N [3-[(1-benzylpiperidin-4-yl)methyl]-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate Chemical compound O=C1OC(COS(=O)(=O)C)CN1CC1CCN(CC=2C=CC=CC=2)CC1 BGTRQDVKLZGMIV-UHFFFAOYSA-N 0.000 description 2
- YTNDJWXNZRHQBV-UHFFFAOYSA-N [3-[4-(1-tert-butylpiperidin-4-yl)butyl]-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate Chemical compound C1CN(C(C)(C)C)CCC1CCCCN1C(=O)OC(COS(C)(=O)=O)C1 YTNDJWXNZRHQBV-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
- 239000003513 alkali Substances 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 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
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 210000004211 gastric acid Anatomy 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 239000007943 implant Substances 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 230000009401 metastasis Effects 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- UHHVABRWHRKEPJ-UHFFFAOYSA-N methyl 2-piperazin-1-ylacetate Chemical compound COC(=O)CN1CCNCC1 UHHVABRWHRKEPJ-UHFFFAOYSA-N 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
- 239000001301 oxygen Substances 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
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 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
- 238000006894 reductive elimination reaction Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000012453 solvate Substances 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
- ZCPFOMNUPUPWFK-UHFFFAOYSA-N tert-butyl 2-carbamimidoyl-4-[5-(methylsulfonyloxymethyl)-2-oxo-1,3-oxazolidin-3-yl]piperidine-1-carboxylate Chemical compound C1C(C(N)=N)N(C(=O)OC(C)(C)C)CCC1N1C(=O)OC(COS(C)(=O)=O)C1 ZCPFOMNUPUPWFK-UHFFFAOYSA-N 0.000 description 2
- JNHNIPWQUGWFEF-UHFFFAOYSA-N tert-butyl 4-[5-(methylsulfonyloxymethyl)-2-oxo-1,3-oxazolidin-3-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1N1C(=O)OC(COS(C)(=O)=O)C1 JNHNIPWQUGWFEF-UHFFFAOYSA-N 0.000 description 2
- BESSCNABRVRYTM-UHFFFAOYSA-N tert-butyl 4-[5-[4-(3-methoxy-3-oxopropyl)piperazin-1-yl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl]piperidine-1-carboxylate Chemical compound C1CN(CCC(=O)OC)CCN1C1C(C)N(C2CCN(CC2)C(=O)OC(C)(C)C)C(=O)O1 BESSCNABRVRYTM-UHFFFAOYSA-N 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
- 238000010626 work up procedure Methods 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- DNISEZBAYYIQFB-PHDIDXHHSA-N (2r,3r)-2,3-diacetyloxybutanedioic acid Chemical compound CC(=O)O[C@@H](C(O)=O)[C@H](C(O)=O)OC(C)=O DNISEZBAYYIQFB-PHDIDXHHSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- 125000003088 (fluoren-9-ylmethoxy)carbonyl 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
- PZNPLUBHRSSFHT-RRHRGVEJSA-N 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCCCC PZNPLUBHRSSFHT-RRHRGVEJSA-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
- MBLLGIRLDKWFQG-UHFFFAOYSA-N 2-[4-(4-methyl-2-oxo-3-piperidin-4-yl-1,3-oxazolidin-5-yl)piperazin-1-yl]acetic acid Chemical compound CC1C(N2CCN(CC(O)=O)CC2)OC(=O)N1C1CCNCC1 MBLLGIRLDKWFQG-UHFFFAOYSA-N 0.000 description 1
- XPIVYDXYJSXKAE-UHFFFAOYSA-N 2-[4-[3-(1-carbamimidoylpiperidin-4-yl)-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]acetic acid Chemical compound C(N)(=N)N1CCC(CC1)N1C(OC(C1C)N1CCN(CC1)CC(=O)O)=O XPIVYDXYJSXKAE-UHFFFAOYSA-N 0.000 description 1
- MWKUQCKKSNZSCL-UHFFFAOYSA-N 2-[4-[3-[(1-benzylpiperidin-4-yl)methyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]acetic acid Chemical compound CC1C(N2CCN(CC(O)=O)CC2)OC(=O)N1CC(CC1)CCN1CC1=CC=CC=C1 MWKUQCKKSNZSCL-UHFFFAOYSA-N 0.000 description 1
- ZEXGVLFSCMAYPC-UHFFFAOYSA-N 2-[4-[3-[2-(4-carbamimidoylpiperazin-1-yl)ethyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]acetic acid Chemical compound C(N)(=N)N1CCN(CC1)CCN1C(OC(C1C)N1CCN(CC1)CC(=O)O)=O ZEXGVLFSCMAYPC-UHFFFAOYSA-N 0.000 description 1
- UDWBDPKBNVJFMW-UHFFFAOYSA-N 2-[4-[3-[3-(1-carbamimidoylpiperidin-4-yl)propyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]acetic acid Chemical compound C(N)(=N)N1CCC(CC1)CCCN1C(OC(C1C)N1CCN(CC1)CC(=O)O)=O UDWBDPKBNVJFMW-UHFFFAOYSA-N 0.000 description 1
- QDBIRAANKNWGAC-UHFFFAOYSA-N 2-[4-[3-[3-(4-carbamimidoylpiperazin-1-yl)propyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]acetic acid Chemical compound C(N)(=N)N1CCN(CC1)CCCN1C(OC(C1C)N1CCN(CC1)CC(=O)O)=O QDBIRAANKNWGAC-UHFFFAOYSA-N 0.000 description 1
- GHXUKCWSMZUXOY-UHFFFAOYSA-N 2-[4-[3-[4-(1-cyclopropylpiperidin-4-yl)butyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]acetic acid Chemical compound CC1C(N2CCN(CC(O)=O)CC2)OC(=O)N1CCCCC(CC1)CCN1C1CC1 GHXUKCWSMZUXOY-UHFFFAOYSA-N 0.000 description 1
- RCPJGVJPGDGXJU-UHFFFAOYSA-N 2-[4-[3-[4-(4-benzylpiperazin-1-yl)butyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]acetic acid Chemical compound CC1C(N2CCN(CC(O)=O)CC2)OC(=O)N1CCCCN(CC1)CCN1CC1=CC=CC=C1 RCPJGVJPGDGXJU-UHFFFAOYSA-N 0.000 description 1
- AXLPCGWOYOKZLZ-UHFFFAOYSA-N 2-[4-[3-[4-(4-cyclohexylpiperazin-1-yl)butyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]acetic acid Chemical compound CC1C(N2CCN(CC(O)=O)CC2)OC(=O)N1CCCCN(CC1)CCN1C1CCCCC1 AXLPCGWOYOKZLZ-UHFFFAOYSA-N 0.000 description 1
- VQLOHWMMJRPNDK-UHFFFAOYSA-N 2-[4-[4-methyl-2-oxo-3-(1-propan-2-ylpiperidin-4-yl)-1,3-oxazolidin-5-yl]piperazin-1-yl]acetic acid Chemical compound C1CN(C(C)C)CCC1N1C(=O)OC(N2CCN(CC(O)=O)CC2)C1C VQLOHWMMJRPNDK-UHFFFAOYSA-N 0.000 description 1
- WNHRUUBHQOWQDP-UHFFFAOYSA-N 2-[4-[4-methyl-2-oxo-3-[4-(4-propylpiperazin-1-yl)butyl]-1,3-oxazolidin-5-yl]piperazin-1-yl]acetic acid Chemical compound C1CN(CCC)CCN1CCCCN1C(=O)OC(N2CCN(CC(O)=O)CC2)C1C WNHRUUBHQOWQDP-UHFFFAOYSA-N 0.000 description 1
- PVATVQSRXQYABV-UHFFFAOYSA-N 2-[4-[4-methyl-2-oxo-3-[4-[1-(5-oxo-2h-1,2,4-oxadiazol-3-yl)piperidin-4-yl]butyl]-1,3-oxazolidin-5-yl]piperazin-1-yl]acetic acid Chemical compound CC1C(N2CCN(CC(O)=O)CC2)OC(=O)N1CCCCC(CC1)CCN1C1=NC(=O)ON1 PVATVQSRXQYABV-UHFFFAOYSA-N 0.000 description 1
- COEBRHQCBAVAHE-UHFFFAOYSA-N 2-[4-[4-methyl-3-(1-methylpiperidin-4-yl)-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]acetic acid Chemical compound CC1C(N2CCN(CC(O)=O)CC2)OC(=O)N1C1CCN(C)CC1 COEBRHQCBAVAHE-UHFFFAOYSA-N 0.000 description 1
- KMGUEILFFWDGFV-UHFFFAOYSA-N 2-benzoyl-2-benzoyloxy-3-hydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)C(C(C(O)=O)O)(C(O)=O)OC(=O)C1=CC=CC=C1 KMGUEILFFWDGFV-UHFFFAOYSA-N 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
- PCJFEVUKVKQSSL-UHFFFAOYSA-N 2h-1,2,4-oxadiazol-5-one Chemical compound O=C1N=CNO1 PCJFEVUKVKQSSL-UHFFFAOYSA-N 0.000 description 1
- GAZRNXIMWKZADY-UHFFFAOYSA-N 3,5-dimethylpyrazole-1-carboximidamide Chemical compound CC=1C=C(C)N(C(N)=N)N=1 GAZRNXIMWKZADY-UHFFFAOYSA-N 0.000 description 1
- CJWLVBVPPMAECY-UHFFFAOYSA-N 3-(piperidin-4-ylamino)propane-1,2-diol Chemical compound OCC(O)CNC1CCNCC1 CJWLVBVPPMAECY-UHFFFAOYSA-N 0.000 description 1
- HMEWGLOYKGDWIK-UHFFFAOYSA-N 3-[4-(4-methyl-2-oxo-3-piperidin-4-yl-1,3-oxazolidin-5-yl)piperazin-1-yl]propanoic acid Chemical compound CC1C(N2CCN(CCC(O)=O)CC2)OC(=O)N1C1CCNCC1 HMEWGLOYKGDWIK-UHFFFAOYSA-N 0.000 description 1
- ASJQIXLPADWYIG-UHFFFAOYSA-N 3-[4-[2-[5-(methylsulfonylmethyl)-2-oxo-1,3-oxazolidin-3-yl]ethyl]piperazin-1-yl]-2h-1,2,4-oxadiazol-5-one Chemical compound O=C1OC(CS(=O)(=O)C)CN1CCN1CCN(C=2NC(=O)ON=2)CC1 ASJQIXLPADWYIG-UHFFFAOYSA-N 0.000 description 1
- HSRNWPWBIZOZED-UHFFFAOYSA-N 3-[4-[3-(1-benzylpiperidin-4-yl)-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoic acid Chemical compound CC1C(N2CCN(CCC(O)=O)CC2)OC(=O)N1C(CC1)CCN1CC1=CC=CC=C1 HSRNWPWBIZOZED-UHFFFAOYSA-N 0.000 description 1
- NEHDBXAUFAVZBS-UHFFFAOYSA-N 3-[4-[3-[(1-carbamimidoylpiperidin-4-yl)methyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoic acid Chemical compound C(N)(=N)N1CCC(CC1)CN1C(OC(C1C)N1CCN(CC1)CCC(=O)O)=O NEHDBXAUFAVZBS-UHFFFAOYSA-N 0.000 description 1
- TUQYNYKDDBBBBG-UHFFFAOYSA-N 3-[4-[3-[(1-ethylpiperidin-4-yl)methyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoic acid Chemical compound C1CN(CC)CCC1CN1C(=O)OC(N2CCN(CCC(O)=O)CC2)C1C TUQYNYKDDBBBBG-UHFFFAOYSA-N 0.000 description 1
- DVZVZDPQPRJLEG-UHFFFAOYSA-N 3-[4-[3-[2-(1-benzylpiperidin-4-yl)ethyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoic acid Chemical compound CC1C(N2CCN(CCC(O)=O)CC2)OC(=O)N1CCC(CC1)CCN1CC1=CC=CC=C1 DVZVZDPQPRJLEG-UHFFFAOYSA-N 0.000 description 1
- WXILVKQRBRRDGQ-UHFFFAOYSA-N 3-[4-[3-[2-(4-benzylpiperazin-1-yl)ethyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoic acid Chemical compound CC1C(N2CCN(CCC(O)=O)CC2)OC(=O)N1CCN(CC1)CCN1CC1=CC=CC=C1 WXILVKQRBRRDGQ-UHFFFAOYSA-N 0.000 description 1
- XVVYXPAUHSHFDM-UHFFFAOYSA-N 3-[4-[3-[2-amino-2-imino-1-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]ethyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoic acid Chemical compound C(=O)(OC(C)(C)C)N1CCC(CC1)C(N1C(OC(C1C)N1CCN(CC1)CCC(=O)O)=O)C(N)=N XVVYXPAUHSHFDM-UHFFFAOYSA-N 0.000 description 1
- OEGGULMYGIEIAP-UHFFFAOYSA-N 3-[4-[3-[3-(1-benzylpiperidin-4-yl)propyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoic acid Chemical compound CC1C(N2CCN(CCC(O)=O)CC2)OC(=O)N1CCCC(CC1)CCN1CC1=CC=CC=C1 OEGGULMYGIEIAP-UHFFFAOYSA-N 0.000 description 1
- OLZORFPBQWZHPS-UHFFFAOYSA-N 3-[4-[3-[3-(4-ethylpiperazin-1-yl)propyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoic acid Chemical compound C1CN(CC)CCN1CCCN1C(=O)OC(N2CCN(CCC(O)=O)CC2)C1C OLZORFPBQWZHPS-UHFFFAOYSA-N 0.000 description 1
- GMHGVYUUODMIDQ-UHFFFAOYSA-N 3-[4-[3-[3-[3-carbamimidoyl-4-[(2-methylpropan-2-yl)oxycarbonyl]piperazin-1-yl]propyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoic acid Chemical compound C(=O)(OC(C)(C)C)N1C(CN(CC1)CCCN1C(OC(C1C)N1CCN(CC1)CCC(=O)O)=O)C(N)=N GMHGVYUUODMIDQ-UHFFFAOYSA-N 0.000 description 1
- KHFYRCHJVTYWGC-UHFFFAOYSA-N 3-[4-[3-[4-(1-benzylpiperidin-4-yl)butyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoic acid Chemical compound CC1C(N2CCN(CCC(O)=O)CC2)OC(=O)N1CCCCC(CC1)CCN1CC1=CC=CC=C1 KHFYRCHJVTYWGC-UHFFFAOYSA-N 0.000 description 1
- BYONVEKVENWUSG-UHFFFAOYSA-N 3-[4-[3-[4-(1-cyclopropylpiperidin-4-yl)butyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoic acid Chemical compound CC1C(N2CCN(CCC(O)=O)CC2)OC(=O)N1CCCCC(CC1)CCN1C1CC1 BYONVEKVENWUSG-UHFFFAOYSA-N 0.000 description 1
- OBSXCUHWYYJTRG-UHFFFAOYSA-N 3-[4-[3-[4-(1-tert-butylpiperidin-4-yl)butyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoic acid Chemical compound C(C)(C)(C)N1CCC(CC1)CCCCN1C(OC(C1C)N1CCN(CC1)CCC(=O)O)=O OBSXCUHWYYJTRG-UHFFFAOYSA-N 0.000 description 1
- DQDPVDSNEZCXTJ-UHFFFAOYSA-N 3-[4-[3-[4-(4-carbamimidoylpiperazin-1-yl)butyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoic acid Chemical compound C(N)(=N)N1CCN(CC1)CCCCN1C(OC(C1C)N1CCN(CC1)CCC(=O)O)=O DQDPVDSNEZCXTJ-UHFFFAOYSA-N 0.000 description 1
- GNGRDDDKTPXESR-UHFFFAOYSA-N 3-[4-[3-[4-(4-cyclohexylpiperazin-1-yl)butyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoic acid Chemical compound CC1C(N2CCN(CCC(O)=O)CC2)OC(=O)N1CCCCN(CC1)CCN1C1CCCCC1 GNGRDDDKTPXESR-UHFFFAOYSA-N 0.000 description 1
- QWYBFMSJKPLQGO-UHFFFAOYSA-N 3-[4-[4-methyl-2-oxo-3-(1-propan-2-ylpiperidin-4-yl)-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoic acid Chemical compound C1CN(C(C)C)CCC1N1C(=O)OC(N2CCN(CCC(O)=O)CC2)C1C QWYBFMSJKPLQGO-UHFFFAOYSA-N 0.000 description 1
- OXLNQKBPHLBIFI-UHFFFAOYSA-N 3-[4-[4-methyl-2-oxo-3-(3-piperidin-4-ylpropyl)-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoic acid Chemical compound N1CCC(CC1)CCCN1C(OC(C1C)N1CCN(CC1)CCC(=O)O)=O OXLNQKBPHLBIFI-UHFFFAOYSA-N 0.000 description 1
- NGODXMDIFTZUEJ-UHFFFAOYSA-N 3-[4-[4-methyl-2-oxo-3-[4-(4-propylpiperazin-1-yl)butyl]-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoic acid Chemical compound C1CN(CCC)CCN1CCCCN1C(=O)OC(N2CCN(CCC(O)=O)CC2)C1C NGODXMDIFTZUEJ-UHFFFAOYSA-N 0.000 description 1
- YMUKDRLQTPTJOG-UHFFFAOYSA-N 3-[4-[4-methyl-2-oxo-3-[4-[1-(5-oxo-2h-1,2,4-oxadiazol-3-yl)piperidin-4-yl]butyl]-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoic acid Chemical compound CC1C(N2CCN(CCC(O)=O)CC2)OC(=O)N1CCCCC(CC1)CCN1C1=NC(=O)ON1 YMUKDRLQTPTJOG-UHFFFAOYSA-N 0.000 description 1
- BLDOUHKRTODHAH-UHFFFAOYSA-N 3-[4-[4-methyl-3-(1-methylpiperidin-4-yl)-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoic acid Chemical compound CC1C(N2CCN(CCC(O)=O)CC2)OC(=O)N1C1CCN(C)CC1 BLDOUHKRTODHAH-UHFFFAOYSA-N 0.000 description 1
- NNXRBVIAIIJBJO-UHFFFAOYSA-N 3-[4-[4-methyl-3-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoic acid Chemical compound CC1C(N2CCN(CCC(O)=O)CC2)OC(=O)N1C1CCN(C(=O)OC(C)(C)C)CC1 NNXRBVIAIIJBJO-UHFFFAOYSA-N 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- RSEHHYMPNZWTGQ-UHFFFAOYSA-N 3-piperazin-4-ium-1-ylpropanoate Chemical compound OC(=O)CCN1CCNCC1 RSEHHYMPNZWTGQ-UHFFFAOYSA-N 0.000 description 1
- YSWPAJWYBQUKNK-UHFFFAOYSA-N 4-[4-[3-(1-benzylpiperidin-4-yl)-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]butanoic acid Chemical compound CC1C(N2CCN(CCCC(O)=O)CC2)OC(=O)N1C(CC1)CCN1CC1=CC=CC=C1 YSWPAJWYBQUKNK-UHFFFAOYSA-N 0.000 description 1
- LWUZBSBCXKADCA-UHFFFAOYSA-N 4-[4-[3-[(1-benzylpiperidin-4-yl)methyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]butanoic acid Chemical compound CC1C(N2CCN(CCCC(O)=O)CC2)OC(=O)N1CC(CC1)CCN1CC1=CC=CC=C1 LWUZBSBCXKADCA-UHFFFAOYSA-N 0.000 description 1
- ZMRAIHPTBMVWFI-UHFFFAOYSA-N 4-[4-[3-[2-(1-cyclohexylpiperidin-4-yl)ethyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]butanoic acid Chemical compound CC1C(N2CCN(CCCC(O)=O)CC2)OC(=O)N1CCC(CC1)CCN1C1CCCCC1 ZMRAIHPTBMVWFI-UHFFFAOYSA-N 0.000 description 1
- ONUGKPCLGFVXFC-UHFFFAOYSA-N 4-[4-[3-[2-(4-benzylpiperazin-1-yl)ethyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]butanoic acid Chemical compound CC1C(N2CCN(CCCC(O)=O)CC2)OC(=O)N1CCN(CC1)CCN1CC1=CC=CC=C1 ONUGKPCLGFVXFC-UHFFFAOYSA-N 0.000 description 1
- IYHXOEKCYVXQAJ-UHFFFAOYSA-N 4-[4-[3-[2-(4-cyclopropylpiperazin-1-yl)ethyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]butanoic acid Chemical compound CC1C(N2CCN(CCCC(O)=O)CC2)OC(=O)N1CCN(CC1)CCN1C1CC1 IYHXOEKCYVXQAJ-UHFFFAOYSA-N 0.000 description 1
- QRFHGJDDLYBFBU-UHFFFAOYSA-N 4-[4-[3-[2-carbamimidoyl-1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]butanoic acid Chemical compound C(=O)(OC(C)(C)C)N1C(CC(CC1)N1C(OC(C1C)N1CCN(CC1)CCCC(=O)O)=O)C(N)=N QRFHGJDDLYBFBU-UHFFFAOYSA-N 0.000 description 1
- NGQFSFPVDUDAGX-UHFFFAOYSA-N 4-[4-[3-[3-(4-carbamimidoylpiperazin-1-yl)propyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]butanoic acid Chemical compound C(N)(=N)N1CCN(CC1)CCCN1C(OC(C1C)N1CCN(CC1)CCCC(=O)O)=O NGQFSFPVDUDAGX-UHFFFAOYSA-N 0.000 description 1
- XVEMISHUSQABJC-UHFFFAOYSA-N 4-[4-[3-[3-(4-ethylpiperazin-1-yl)propyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]butanoic acid Chemical compound C1CN(CC)CCN1CCCN1C(=O)OC(N2CCN(CCCC(O)=O)CC2)C1C XVEMISHUSQABJC-UHFFFAOYSA-N 0.000 description 1
- ZUXRWIQDIQZZAX-UHFFFAOYSA-N 4-[4-[3-[4-(1-benzylpiperidin-4-yl)butyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]butanoic acid Chemical compound CC1C(N2CCN(CCCC(O)=O)CC2)OC(=O)N1CCCCC(CC1)CCN1CC1=CC=CC=C1 ZUXRWIQDIQZZAX-UHFFFAOYSA-N 0.000 description 1
- UNNGXRFRCIEZHF-UHFFFAOYSA-N 4-[4-[3-[4-(1-cyclopropylpiperidin-4-yl)butyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]butanoic acid Chemical compound CC1C(N2CCN(CCCC(O)=O)CC2)OC(=O)N1CCCCC(CC1)CCN1C1CC1 UNNGXRFRCIEZHF-UHFFFAOYSA-N 0.000 description 1
- MNKIYWBFRBCBJL-UHFFFAOYSA-N 4-[4-[3-[4-(4-cyclohexylpiperazin-1-yl)butyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]butanoic acid Chemical compound CC1C(N2CCN(CCCC(O)=O)CC2)OC(=O)N1CCCCN(CC1)CCN1C1CCCCC1 MNKIYWBFRBCBJL-UHFFFAOYSA-N 0.000 description 1
- UODHVLMGEGQNRW-UHFFFAOYSA-N 4-[4-[4-methyl-2-oxo-3-[2-(1-propan-2-ylpiperidin-4-yl)ethyl]-1,3-oxazolidin-5-yl]piperazin-1-yl]butanoic acid Chemical compound C1CN(C(C)C)CCC1CCN1C(=O)OC(N2CCN(CCCC(O)=O)CC2)C1C UODHVLMGEGQNRW-UHFFFAOYSA-N 0.000 description 1
- GWGMLSHLLIEBNW-UHFFFAOYSA-N 4-[4-[4-methyl-2-oxo-3-[2-[1-(5-oxo-2h-1,2,4-oxadiazol-3-yl)piperidin-4-yl]ethyl]-1,3-oxazolidin-5-yl]piperazin-1-yl]butanoic acid Chemical compound CC1C(N2CCN(CCCC(O)=O)CC2)OC(=O)N1CCC(CC1)CCN1C1=NC(=O)ON1 GWGMLSHLLIEBNW-UHFFFAOYSA-N 0.000 description 1
- FMFKECPJAHNUGO-UHFFFAOYSA-N 4-[4-[4-methyl-2-oxo-3-[3-(4-propan-2-ylpiperazin-1-yl)propyl]-1,3-oxazolidin-5-yl]piperazin-1-yl]butanoic acid Chemical compound C1CN(C(C)C)CCN1CCCN1C(=O)OC(N2CCN(CCCC(O)=O)CC2)C1C FMFKECPJAHNUGO-UHFFFAOYSA-N 0.000 description 1
- AGIPGJXSZBCGSI-UHFFFAOYSA-N 4-[4-[4-methyl-2-oxo-3-[3-[1-(5-oxo-2h-1,2,4-oxadiazol-3-yl)piperidin-4-yl]propyl]-1,3-oxazolidin-5-yl]piperazin-1-yl]butanoic acid Chemical compound CC1C(N2CCN(CCCC(O)=O)CC2)OC(=O)N1CCCC(CC1)CCN1C1=NC(=O)ON1 AGIPGJXSZBCGSI-UHFFFAOYSA-N 0.000 description 1
- YQBLODFMNCYPPS-UHFFFAOYSA-N 4-[4-[4-methyl-2-oxo-3-[4-(4-propylpiperazin-1-yl)butyl]-1,3-oxazolidin-5-yl]piperazin-1-yl]butanoic acid Chemical compound C1CN(CCC)CCN1CCCCN1C(=O)OC(N2CCN(CCCC(O)=O)CC2)C1C YQBLODFMNCYPPS-UHFFFAOYSA-N 0.000 description 1
- ABBQVJVLIQOPDS-UHFFFAOYSA-N 4-[4-[4-methyl-3-[2-(4-methylpiperazin-1-yl)ethyl]-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]butanoic acid Chemical compound CC1C(N2CCN(CCCC(O)=O)CC2)OC(=O)N1CCN1CCN(C)CC1 ABBQVJVLIQOPDS-UHFFFAOYSA-N 0.000 description 1
- 208000009304 Acute Kidney Injury Diseases 0.000 description 1
- LBCCPKFTHIBIKU-UHFFFAOYSA-N Aethyl-propyl-glyoxal Natural products CCCC(=O)C(=O)CC LBCCPKFTHIBIKU-UHFFFAOYSA-N 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
- ZSOBAEUZPNDARR-UHFFFAOYSA-N C(=O)(O)CCN1CCN(CC1)C1CN(C(O1)=O)C Chemical compound C(=O)(O)CCN1CCN(CC1)C1CN(C(O1)=O)C ZSOBAEUZPNDARR-UHFFFAOYSA-N 0.000 description 1
- UQERICJBHKUYJT-UHFFFAOYSA-N C(=O)(OC(C)(C)C)N1CCC(CC1)C(N1C(OC(C1C)N1CCN(CC1)CCCC(=O)OC)=O)C(N)=N.C(=O)(OC(C)(C)C)N1CCC(CC1)C(N1C(OC(C1)COS(=O)(=O)C)=O)C(N)=N Chemical compound C(=O)(OC(C)(C)C)N1CCC(CC1)C(N1C(OC(C1C)N1CCN(CC1)CCCC(=O)OC)=O)C(N)=N.C(=O)(OC(C)(C)C)N1CCC(CC1)C(N1C(OC(C1)COS(=O)(=O)C)=O)C(N)=N UQERICJBHKUYJT-UHFFFAOYSA-N 0.000 description 1
- JDDZTCKBJXZNNX-UHFFFAOYSA-N C(=O)(OC(C)(C)C)NC(=N)N1CCC(CC1)CN1C(OC(C1)COS(=O)(=O)C)=O Chemical compound C(=O)(OC(C)(C)C)NC(=N)N1CCC(CC1)CN1C(OC(C1)COS(=O)(=O)C)=O JDDZTCKBJXZNNX-UHFFFAOYSA-N 0.000 description 1
- JHURUJVLSKVVBH-UHFFFAOYSA-N C(C)(C)N1CCC(CC1)CCCN1C(OC(C1C)N1CCN(CC1)CCC(=O)O)=O Chemical compound C(C)(C)N1CCC(CC1)CCCN1C(OC(C1C)N1CCN(CC1)CCC(=O)O)=O JHURUJVLSKVVBH-UHFFFAOYSA-N 0.000 description 1
- JTMJMQKFAGKVFW-UHFFFAOYSA-N C(C1=CC=CC=C1)N1CCC(CC1)N1C(OC(C1C)N1CCN(CC1)CC(=O)OC)=O.C(C1=CC=CC=C1)N1CCC(CC1)N1C(OC(C1)COS(=O)(=O)C)=O Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)N1C(OC(C1C)N1CCN(CC1)CC(=O)OC)=O.C(C1=CC=CC=C1)N1CCC(CC1)N1C(OC(C1)COS(=O)(=O)C)=O JTMJMQKFAGKVFW-UHFFFAOYSA-N 0.000 description 1
- VSTSJRXAZANPLG-UHFFFAOYSA-N C1CN(C(=O)OC(C)(C)C)CCC1C(C(N)=N)N1C(=O)OC(COS(C)(=O)=O)C1 Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C(C(N)=N)N1C(=O)OC(COS(C)(=O)=O)C1 VSTSJRXAZANPLG-UHFFFAOYSA-N 0.000 description 1
- KHOQAKZPCDURPR-UHFFFAOYSA-N CN1CCN(CC1)CCN1C(OC(C1C)N1CCN(CC1)CC(=O)OC)=O.CN1CCN(CC1)CCN1C(OC(C1C)OS(=O)(=O)C)=O Chemical compound CN1CCN(CC1)CCN1C(OC(C1C)N1CCN(CC1)CC(=O)OC)=O.CN1CCN(CC1)CCN1C(OC(C1C)OS(=O)(=O)C)=O KHOQAKZPCDURPR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VXMSASRRTVZGPQ-UHFFFAOYSA-N Cl.N1CCC(CC1)N1C(OC(C1C)N1CCN(CC1)CCC(=O)OC)=O Chemical compound Cl.N1CCC(CC1)N1C(OC(C1C)N1CCN(CC1)CCC(=O)OC)=O VXMSASRRTVZGPQ-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 102100022337 Integrin alpha-V Human genes 0.000 description 1
- 102000007547 Laminin Human genes 0.000 description 1
- 108010085895 Laminin Proteins 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 238000007126 N-alkylation reaction Methods 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 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
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 108010031318 Vitronectin Proteins 0.000 description 1
- 102100035140 Vitronectin Human genes 0.000 description 1
- 108010048673 Vitronectin Receptors Proteins 0.000 description 1
- UUFYEWRMNKWDHW-UHFFFAOYSA-N [2-oxo-3-[3-(4-propan-2-ylpiperazin-1-yl)propyl]-1,3-oxazolidin-5-yl]methyl methanesulfonate Chemical compound C1CN(C(C)C)CCN1CCCN1C(=O)OC(COS(C)(=O)=O)C1 UUFYEWRMNKWDHW-UHFFFAOYSA-N 0.000 description 1
- BRQIINRSOOIFJP-UHFFFAOYSA-N [3-[2-(1-benzylpiperidin-4-yl)ethyl]-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate Chemical compound O=C1OC(COS(=O)(=O)C)CN1CCC1CCN(CC=2C=CC=CC=2)CC1 BRQIINRSOOIFJP-UHFFFAOYSA-N 0.000 description 1
- LWUJSZYILGLIJE-UHFFFAOYSA-N [3-[2-(1-cyclohexylpiperidin-4-yl)ethyl]-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate Chemical compound O=C1OC(COS(=O)(=O)C)CN1CCC1CCN(C2CCCCC2)CC1 LWUJSZYILGLIJE-UHFFFAOYSA-N 0.000 description 1
- OLPFBHNSSCPRRL-UHFFFAOYSA-N [3-[2-(4-cyclopropylpiperazin-1-yl)ethyl]-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate Chemical compound O=C1OC(COS(=O)(=O)C)CN1CCN1CCN(C2CC2)CC1 OLPFBHNSSCPRRL-UHFFFAOYSA-N 0.000 description 1
- IWDVQJJQXDATMB-UHFFFAOYSA-N [3-[3-(4-benzylpiperazin-1-yl)propyl]-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate Chemical compound O=C1OC(COS(=O)(=O)C)CN1CCCN1CCN(CC=2C=CC=CC=2)CC1 IWDVQJJQXDATMB-UHFFFAOYSA-N 0.000 description 1
- XOBJAGLKHGBHQE-UHFFFAOYSA-N [3-[3-(4-ethylpiperazin-1-yl)propyl]-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate Chemical compound C1CN(CC)CCN1CCCN1C(=O)OC(COS(C)(=O)=O)C1 XOBJAGLKHGBHQE-UHFFFAOYSA-N 0.000 description 1
- TTWKNLARLWWXAM-UHFFFAOYSA-N [3-[4-(1-benzylpiperidin-4-yl)butyl]-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate Chemical compound O=C1OC(COS(=O)(=O)C)CN1CCCCC1CCN(CC=2C=CC=CC=2)CC1 TTWKNLARLWWXAM-UHFFFAOYSA-N 0.000 description 1
- NALPCIOPEUMZLK-UHFFFAOYSA-N [3-[4-(4-cyclohexylpiperazin-1-yl)butyl]-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate Chemical compound O=C1OC(COS(=O)(=O)C)CN1CCCCN1CCN(C2CCCCC2)CC1 NALPCIOPEUMZLK-UHFFFAOYSA-N 0.000 description 1
- SSBPTTUXOXKMAT-UHFFFAOYSA-M [Na+].C(N)(=N)N1CCC(CC1)N1C(OC(C1C)N1CCN(CC1)CCC(=O)[O-])=O Chemical compound [Na+].C(N)(=N)N1CCC(CC1)N1C(OC(C1C)N1CCN(CC1)CCC(=O)[O-])=O SSBPTTUXOXKMAT-UHFFFAOYSA-M 0.000 description 1
- 201000011040 acute kidney failure Diseases 0.000 description 1
- 208000012998 acute renal failure Diseases 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 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
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 125000004429 atom 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
- NAFHEOXWMJWUCD-UHFFFAOYSA-N benzyl 3-[4-[3-[3-(1-benzylpiperidin-4-yl)propyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoate Chemical compound CC1C(N2CCN(CCC(=O)OCC=3C=CC=CC=3)CC2)OC(=O)N1CCCC(CC1)CCN1CC1=CC=CC=C1 NAFHEOXWMJWUCD-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
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 239000000872 buffer Substances 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
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 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
- 239000007795 chemical reaction product Substances 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
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000001816 cooling Methods 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
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 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
- 238000001035 drying Methods 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
- 125000004185 ester group Chemical group 0.000 description 1
- 125000005949 ethanesulfonyloxy group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 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
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 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
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 239000008273 gelatin Substances 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
- 125000000623 heterocyclic group Chemical group 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
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 208000028867 ischemia Diseases 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
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 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
- GIDBCRLFECRVQK-UHFFFAOYSA-N methyl 2-[4-(4-methyl-2-oxo-3-piperidin-4-yl-1,3-oxazolidin-5-yl)piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OC)CCN1C1C(C)N(C2CCNCC2)C(=O)O1 GIDBCRLFECRVQK-UHFFFAOYSA-N 0.000 description 1
- LYESVDCRTYSJJB-UHFFFAOYSA-N methyl 2-[4-[3-[(1-carbamimidoylpiperidin-4-yl)methyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]acetate Chemical compound C(N)(=N)N1CCC(CC1)CN1C(OC(C1C)N1CCN(CC1)CC(=O)OC)=O LYESVDCRTYSJJB-UHFFFAOYSA-N 0.000 description 1
- PDVNEVJIJUICGQ-UHFFFAOYSA-N methyl 2-[4-[3-[(1-ethylpiperidin-4-yl)methyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]acetate Chemical compound C1CN(CC)CCC1CN1C(=O)OC(N2CCN(CC(=O)OC)CC2)C1C PDVNEVJIJUICGQ-UHFFFAOYSA-N 0.000 description 1
- ZAQYWFLJDUPENF-UHFFFAOYSA-N methyl 2-[4-[3-[3-(1-benzylpiperidin-4-yl)propyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OC)CCN1C1C(C)N(CCCC2CCN(CC=3C=CC=CC=3)CC2)C(=O)O1 ZAQYWFLJDUPENF-UHFFFAOYSA-N 0.000 description 1
- HESFSGGFDQRVCS-UHFFFAOYSA-N methyl 2-[4-[3-[4-(1-benzylpiperidin-4-yl)butyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OC)CCN1C1C(C)N(CCCCC2CCN(CC=3C=CC=CC=3)CC2)C(=O)O1 HESFSGGFDQRVCS-UHFFFAOYSA-N 0.000 description 1
- SSWPFGKFNLVOBK-UHFFFAOYSA-N methyl 2-[4-[3-[4-(1-cyclopropylpiperidin-4-yl)butyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OC)CCN1C1C(C)N(CCCCC2CCN(CC2)C2CC2)C(=O)O1 SSWPFGKFNLVOBK-UHFFFAOYSA-N 0.000 description 1
- RIUWHFCMYBQFGZ-UHFFFAOYSA-N methyl 2-[4-[3-[4-(4-carbamimidoylpiperazin-1-yl)butyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]acetate Chemical compound C(N)(=N)N1CCN(CC1)CCCCN1C(OC(C1C)N1CCN(CC1)CC(=O)OC)=O RIUWHFCMYBQFGZ-UHFFFAOYSA-N 0.000 description 1
- NDRKXBWZZRDQKL-UHFFFAOYSA-N methyl 2-[4-[4-methyl-2-oxo-3-[2-(1-propan-2-ylpiperidin-4-yl)ethyl]-1,3-oxazolidin-5-yl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OC)CCN1C1C(C)N(CCC2CCN(CC2)C(C)C)C(=O)O1 NDRKXBWZZRDQKL-UHFFFAOYSA-N 0.000 description 1
- FVZHUTWYRSLYSA-UHFFFAOYSA-N methyl 2-[4-[4-methyl-2-oxo-3-[4-(4-propylpiperazin-1-yl)butyl]-1,3-oxazolidin-5-yl]piperazin-1-yl]acetate Chemical compound C1CN(CCC)CCN1CCCCN1C(=O)OC(N2CCN(CC(=O)OC)CC2)C1C FVZHUTWYRSLYSA-UHFFFAOYSA-N 0.000 description 1
- QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 1
- UEBNDKDMFDTZGP-UHFFFAOYSA-N methyl 3-[4-[3-[(1-ethylpiperidin-4-yl)methyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoate Chemical compound C1CN(CC)CCC1CN1C(=O)OC(N2CCN(CCC(=O)OC)CC2)C1C UEBNDKDMFDTZGP-UHFFFAOYSA-N 0.000 description 1
- LZCIWMRWOKFXOR-UHFFFAOYSA-N methyl 3-[4-[3-[2-(1-carbamimidoylpiperidin-4-yl)ethyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoate Chemical compound C(N)(=N)N1CCC(CC1)CCN1C(OC(C1C)N1CCN(CC1)CCC(=O)OC)=O LZCIWMRWOKFXOR-UHFFFAOYSA-N 0.000 description 1
- YJXKOYCRYWPMNE-UHFFFAOYSA-N methyl 3-[4-[3-[2-(4-cyclopropylpiperazin-1-yl)ethyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoate Chemical compound C1CN(CCC(=O)OC)CCN1C1C(C)N(CCN2CCN(CC2)C2CC2)C(=O)O1 YJXKOYCRYWPMNE-UHFFFAOYSA-N 0.000 description 1
- MTRYJYSWONNPBH-UHFFFAOYSA-N methyl 3-[4-[3-[3-(4-benzylpiperazin-1-yl)propyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoate Chemical compound C1CN(CCC(=O)OC)CCN1C1C(C)N(CCCN2CCN(CC=3C=CC=CC=3)CC2)C(=O)O1 MTRYJYSWONNPBH-UHFFFAOYSA-N 0.000 description 1
- HRRFPWMOCMNBFA-UHFFFAOYSA-N methyl 3-[4-[3-[4-(1-benzylpiperidin-4-yl)butyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoate Chemical compound C1CN(CCC(=O)OC)CCN1C1C(C)N(CCCCC2CCN(CC=3C=CC=CC=3)CC2)C(=O)O1 HRRFPWMOCMNBFA-UHFFFAOYSA-N 0.000 description 1
- YQCQHNVAVDECJO-UHFFFAOYSA-N methyl 3-[4-[3-[4-(4-benzylpiperazin-1-yl)butyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoate Chemical compound C1CN(CCC(=O)OC)CCN1C1C(C)N(CCCCN2CCN(CC=3C=CC=CC=3)CC2)C(=O)O1 YQCQHNVAVDECJO-UHFFFAOYSA-N 0.000 description 1
- QDPIQBUYYIMXHC-UHFFFAOYSA-N methyl 3-[4-[3-[4-(4-cyclohexylpiperazin-1-yl)butyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoate Chemical compound C1CN(CCC(=O)OC)CCN1C1C(C)N(CCCCN2CCN(CC2)C2CCCCC2)C(=O)O1 QDPIQBUYYIMXHC-UHFFFAOYSA-N 0.000 description 1
- JANQJOVSVGLFHZ-UHFFFAOYSA-N methyl 3-[4-[4-methyl-2-oxo-3-(1-propan-2-ylpiperidin-4-yl)-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoate Chemical compound C1CN(CCC(=O)OC)CCN1C1C(C)N(C2CCN(CC2)C(C)C)C(=O)O1 JANQJOVSVGLFHZ-UHFFFAOYSA-N 0.000 description 1
- DYPLXIKLCYWBHH-UHFFFAOYSA-N methyl 3-[4-[4-methyl-3-(1-methylpiperidin-4-yl)-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoate Chemical compound C1CN(CCC(=O)OC)CCN1C1C(C)N(C2CCN(C)CC2)C(=O)O1 DYPLXIKLCYWBHH-UHFFFAOYSA-N 0.000 description 1
- IMVONEHPSYJZPK-UHFFFAOYSA-N methyl 3-[4-[4-methyl-3-[2-(4-methylpiperazin-1-yl)ethyl]-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]propanoate Chemical compound C1CN(CCC(=O)OC)CCN1C1C(C)N(CCN2CCN(C)CC2)C(=O)O1 IMVONEHPSYJZPK-UHFFFAOYSA-N 0.000 description 1
- GZGJIACHBCQSPC-UHFFFAOYSA-N methyl 3-chloropropanoate Chemical compound COC(=O)CCCl GZGJIACHBCQSPC-UHFFFAOYSA-N 0.000 description 1
- USGKZPDBGYZADJ-UHFFFAOYSA-N methyl 4-[4-[3-(1-carbamimidoylpiperidin-4-yl)-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]butanoate Chemical compound C(N)(=N)N1CCC(CC1)N1C(OC(C1C)N1CCN(CC1)CCCC(=O)OC)=O USGKZPDBGYZADJ-UHFFFAOYSA-N 0.000 description 1
- QIVBVDXOZRETCY-UHFFFAOYSA-N methyl 4-[4-[3-[(1-benzylpiperidin-4-yl)methyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]butanoate Chemical compound C1CN(CCCC(=O)OC)CCN1C1C(C)N(CC2CCN(CC=3C=CC=CC=3)CC2)C(=O)O1 QIVBVDXOZRETCY-UHFFFAOYSA-N 0.000 description 1
- HEIBYECAGOKMGK-UHFFFAOYSA-N methyl 4-[4-[3-[(1-carbamimidoylpiperidin-4-yl)methyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]butanoate Chemical compound C(N)(=N)N1CCC(CC1)CN1C(OC(C1C)N1CCN(CC1)CCCC(=O)OC)=O HEIBYECAGOKMGK-UHFFFAOYSA-N 0.000 description 1
- SDZOXQVALZXYFV-UHFFFAOYSA-N methyl 4-[4-[3-[(1-ethylpiperidin-4-yl)methyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]butanoate Chemical compound C1CN(CC)CCC1CN1C(=O)OC(N2CCN(CCCC(=O)OC)CC2)C1C SDZOXQVALZXYFV-UHFFFAOYSA-N 0.000 description 1
- AOEMVSNJUAHWSO-UHFFFAOYSA-N methyl 4-[4-[3-[2-(1-carbamimidoylpiperidin-4-yl)ethyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]butanoate Chemical compound C(N)(=N)N1CCC(CC1)CCN1C(OC(C1C)N1CCN(CC1)CCCC(=O)OC)=O AOEMVSNJUAHWSO-UHFFFAOYSA-N 0.000 description 1
- LALCZAOUFQMSCM-UHFFFAOYSA-N methyl 4-[4-[3-[2-(1-cyclohexylpiperidin-4-yl)ethyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]butanoate Chemical compound C1CN(CCCC(=O)OC)CCN1C1C(C)N(CCC2CCN(CC2)C2CCCCC2)C(=O)O1 LALCZAOUFQMSCM-UHFFFAOYSA-N 0.000 description 1
- CDJBMKMHVOSHDA-UHFFFAOYSA-N methyl 4-[4-[3-[2-(4-carbamimidoylpiperazin-1-yl)ethyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]butanoate Chemical compound C(N)(=N)N1CCN(CC1)CCN1C(OC(C1C)N1CCN(CC1)CCCC(=O)OC)=O CDJBMKMHVOSHDA-UHFFFAOYSA-N 0.000 description 1
- PFHUDICUZVWUMI-UHFFFAOYSA-N methyl 4-[4-[3-[3-(4-carbamimidoylpiperazin-1-yl)propyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]butanoate Chemical compound C(N)(=N)N1CCN(CC1)CCCN1C(OC(C1C)N1CCN(CC1)CCCC(=O)OC)=O PFHUDICUZVWUMI-UHFFFAOYSA-N 0.000 description 1
- CBBRVBIZVGTZST-UHFFFAOYSA-N methyl 4-[4-[3-[4-(1-carbamimidoylpiperidin-4-yl)butyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]butanoate Chemical compound C(N)(=N)N1CCC(CC1)CCCCN1C(OC(C1C)N1CCN(CC1)CCCC(=O)OC)=O CBBRVBIZVGTZST-UHFFFAOYSA-N 0.000 description 1
- OCBPGAKKGQRIPB-UHFFFAOYSA-N methyl 4-[4-[3-[4-(4-carbamimidoylpiperazin-1-yl)butyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]butanoate Chemical compound C(N)(=N)N1CCN(CC1)CCCCN1C(OC(C1C)N1CCN(CC1)CCCC(=O)OC)=O OCBPGAKKGQRIPB-UHFFFAOYSA-N 0.000 description 1
- SWOJIOLLYMMSFV-UHFFFAOYSA-N methyl 4-[4-[3-[4-(4-cyclohexylpiperazin-1-yl)butyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]butanoate Chemical compound C1CN(CCCC(=O)OC)CCN1C1C(C)N(CCCCN2CCN(CC2)C2CCCCC2)C(=O)O1 SWOJIOLLYMMSFV-UHFFFAOYSA-N 0.000 description 1
- QULATZBKUJHXIB-UHFFFAOYSA-N methyl 4-[4-[4-methyl-2-oxo-3-(1-propan-2-ylpiperidin-4-yl)-1,3-oxazolidin-5-yl]piperazin-1-yl]butanoate Chemical compound C1CN(CCCC(=O)OC)CCN1C1C(C)N(C2CCN(CC2)C(C)C)C(=O)O1 QULATZBKUJHXIB-UHFFFAOYSA-N 0.000 description 1
- UJDGEBUZYHEIGV-UHFFFAOYSA-N methyl 4-[4-[4-methyl-2-oxo-3-[2-(1-propan-2-ylpiperidin-4-yl)ethyl]-1,3-oxazolidin-5-yl]piperazin-1-yl]butanoate Chemical compound C1CN(CCCC(=O)OC)CCN1C1C(C)N(CCC2CCN(CC2)C(C)C)C(=O)O1 UJDGEBUZYHEIGV-UHFFFAOYSA-N 0.000 description 1
- PISXTTDVCJXPGR-UHFFFAOYSA-N methyl 4-[4-[4-methyl-3-(1-methylpiperidin-4-yl)-2-oxo-1,3-oxazolidin-5-yl]piperazin-1-yl]butanoate Chemical compound C1CN(CCCC(=O)OC)CCN1C1C(C)N(C2CCN(C)CC2)C(=O)O1 PISXTTDVCJXPGR-UHFFFAOYSA-N 0.000 description 1
- KARQMLCFZRMBSP-UHFFFAOYSA-N methyl 4-piperazin-1-ylbutanoate Chemical compound COC(=O)CCCN1CCNCC1 KARQMLCFZRMBSP-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 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
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910000510 noble metal Inorganic materials 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
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000008196 pharmacological composition Substances 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
- 150000003053 piperidines Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 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
- 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
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 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
- 239000000375 suspending agent Substances 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
- GLVRFPAWDPTART-UHFFFAOYSA-N tert-butyl 2-carbamimidoyl-4-[2-[5-(methylsulfonyloxymethyl)-2-oxo-1,3-oxazolidin-3-yl]ethyl]piperazine-1-carboxylate Chemical compound C(=O)(OC(C)(C)C)N1C(CN(CC1)CCN1C(OC(C1)COS(=O)(=O)C)=O)C(N)=N GLVRFPAWDPTART-UHFFFAOYSA-N 0.000 description 1
- ILXZTXBNHGGRPG-UHFFFAOYSA-N tert-butyl 2-carbamimidoyl-4-[3-[5-(methylsulfonyloxymethyl)-2-oxo-1,3-oxazolidin-3-yl]propyl]piperazine-1-carboxylate Chemical compound C(=O)(OC(C)(C)C)N1C(CN(CC1)CCCN1C(OC(C1)COS(=O)(=O)C)=O)C(N)=N ILXZTXBNHGGRPG-UHFFFAOYSA-N 0.000 description 1
- NSJZTHMUUMEPCJ-UHFFFAOYSA-N tert-butyl 2-carbamimidoyl-4-[3-[5-(methylsulfonyloxymethyl)-2-oxo-1,3-oxazolidin-3-yl]propyl]piperidine-1-carboxylate Chemical compound C(=O)(OC(C)(C)C)N1C(CC(CC1)CCCN1C(OC(C1)COS(=O)(=O)C)=O)C(N)=N NSJZTHMUUMEPCJ-UHFFFAOYSA-N 0.000 description 1
- CUOVGCYVRMVJMT-UHFFFAOYSA-N tert-butyl 2-carbamimidoyl-4-[3-[5-[4-(2-methoxy-2-oxoethyl)piperazin-1-yl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl]propyl]piperidine-1-carboxylate Chemical compound C(=O)(OC(C)(C)C)N1C(CC(CC1)CCCN1C(OC(C1C)N1CCN(CC1)CC(=O)OC)=O)C(N)=N CUOVGCYVRMVJMT-UHFFFAOYSA-N 0.000 description 1
- CZXHESSBLIOILK-UHFFFAOYSA-N tert-butyl 2-carbamimidoyl-4-[4-[5-(methylsulfonyloxymethyl)-2-oxo-1,3-oxazolidin-3-yl]butyl]piperazine-1-carboxylate Chemical compound C(=O)(OC(C)(C)C)N1C(CN(CC1)CCCCN1C(OC(C1)COS(=O)(=O)C)=O)C(N)=N CZXHESSBLIOILK-UHFFFAOYSA-N 0.000 description 1
- UBSWQGWXZAPWHM-UHFFFAOYSA-N tert-butyl 2-carbamimidoyl-4-[4-[5-(methylsulfonyloxymethyl)-2-oxo-1,3-oxazolidin-3-yl]butyl]piperidine-1-carboxylate Chemical compound C1C(C(N)=N)N(C(=O)OC(C)(C)C)CCC1CCCCN1C(=O)OC(COS(C)(=O)=O)C1 UBSWQGWXZAPWHM-UHFFFAOYSA-N 0.000 description 1
- RMFFJASAKUNZHW-UHFFFAOYSA-N tert-butyl 2-carbamimidoyl-4-[4-[5-[4-(2-methoxy-2-oxoethyl)piperazin-1-yl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl]butyl]piperazine-1-carboxylate Chemical compound C(=O)(OC(C)(C)C)N1C(CN(CC1)CCCCN1C(OC(C1C)N1CCN(CC1)CC(=O)OC)=O)C(N)=N RMFFJASAKUNZHW-UHFFFAOYSA-N 0.000 description 1
- UPBAHNBHZDCDSR-UHFFFAOYSA-N tert-butyl 2-carbamimidoyl-4-[5-[4-(2-methoxy-2-oxoethyl)piperazin-1-yl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl]piperidine-1-carboxylate Chemical compound C(=O)(OC(C)(C)C)N1C(CC(CC1)N1C(OC(C1C)N1CCN(CC1)CC(=O)OC)=O)C(N)=N UPBAHNBHZDCDSR-UHFFFAOYSA-N 0.000 description 1
- WUXVSQVXDUGEOM-UHFFFAOYSA-N tert-butyl 4-[2-amino-2-imino-1-[5-[4-(3-methoxy-3-oxopropyl)piperazin-1-yl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl]ethyl]piperidine-1-carboxylate Chemical compound C(=O)(OC(C)(C)C)N1CCC(CC1)C(N1C(OC(C1C)N1CCN(CC1)CCC(=O)OC)=O)C(N)=N WUXVSQVXDUGEOM-UHFFFAOYSA-N 0.000 description 1
- DKPAJZKGQLWDLH-UHFFFAOYSA-N tert-butyl 4-[5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1N1C(=O)OC(CO)C1 DKPAJZKGQLWDLH-UHFFFAOYSA-N 0.000 description 1
- OTNFZMWXGFZGPZ-UHFFFAOYSA-N tert-butyl 4-[5-[4-(2-methoxy-2-oxoethyl)piperazin-1-yl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl]piperidine-1-carboxylate Chemical compound C1CN(CC(=O)OC)CCN1C1C(C)N(C2CCN(CC2)C(=O)OC(C)(C)C)C(=O)O1 OTNFZMWXGFZGPZ-UHFFFAOYSA-N 0.000 description 1
- LZRDHSFPLUWYAX-UHFFFAOYSA-N tert-butyl 4-aminopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(N)CC1 LZRDHSFPLUWYAX-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 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
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (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)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4439846A DE4439846A1 (de) | 1994-11-08 | 1994-11-08 | Adhäsionsrezeptor-Antagonisten |
Publications (2)
Publication Number | Publication Date |
---|---|
SK136895A3 SK136895A3 (en) | 1996-06-05 |
SK281815B6 true SK281815B6 (sk) | 2001-08-06 |
Family
ID=6532768
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SK1368-95A SK281815B6 (sk) | 1994-11-08 | 1995-11-02 | Derivát oxazolidinónu, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje |
Country Status (22)
Country | Link |
---|---|
US (1) | US5776937A (sv) |
EP (1) | EP0711770A1 (sv) |
JP (1) | JPH08208629A (sv) |
KR (1) | KR100384978B1 (sv) |
CN (1) | CN1069640C (sv) |
AR (1) | AR002245A1 (sv) |
AU (1) | AU704184B2 (sv) |
BR (1) | BR9505109A (sv) |
CA (1) | CA2162223A1 (sv) |
CO (1) | CO4520229A1 (sv) |
CZ (1) | CZ291049B6 (sv) |
DE (1) | DE4439846A1 (sv) |
FI (1) | FI955351A (sv) |
HU (1) | HU217085B (sv) |
NO (1) | NO306113B1 (sv) |
PL (1) | PL183595B1 (sv) |
RU (1) | RU2155762C2 (sv) |
SK (1) | SK281815B6 (sv) |
TR (1) | TR199501389A2 (sv) |
TW (1) | TW316903B (sv) |
UA (1) | UA41928C2 (sv) |
ZA (1) | ZA959434B (sv) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2123889T3 (es) * | 1994-11-02 | 1999-01-16 | Merck Patent Gmbh | Antagonistas de receptores de adhesion. |
US6046331A (en) * | 1998-12-17 | 2000-04-04 | Synaptic Pharmaceutical Corporation | Imidazolones and their use in treating benign prostatic hyperplasia and other disorders |
AU2593600A (en) | 1998-12-23 | 2000-07-12 | G.D. Searle & Co. | Method of using a cyclooxygenase-2 inhibitor and a matrix metalloproteinase inhibitor as a combination therapy in the treatment of neoplasia |
WO2000045177A1 (en) | 1999-01-27 | 2000-08-03 | Pharmacia & Upjohn Company | Assays for modulators of elongation factor p activity |
WO2004032856A2 (en) * | 2002-10-07 | 2004-04-22 | Smithkline Beecham Corporation | Compounds |
CN102796091A (zh) * | 2011-05-24 | 2012-11-28 | 北大方正集团有限公司 | 取代的噁唑烷酮化合物及其制备方法和应用 |
MX2015002399A (es) * | 2012-10-29 | 2015-06-10 | Hoffmann La Roche | Derivados de oxazolidinona 3,4-disustituidos y su uso como inhibidores del canal de potasio activado con calcio. |
CN104230915B (zh) * | 2014-08-29 | 2016-08-17 | 南京大学 | 含噻唑烷二酮的苯基哌嗪衍生物及其制备方法与用途 |
IL283725B2 (en) | 2017-06-20 | 2024-04-01 | Imbria Pharmaceuticals Inc | Preparations and methods for increasing the efficiency of heart metabolism |
US11780811B2 (en) | 2020-06-30 | 2023-10-10 | Imbria Pharmaceuticals, Inc. | Methods of synthesizing 2-[4-[(2,3,4-trimethoxyphenyl)methyl]piperazin-1-yl]ethyl pyridine-3-carboxylate |
US11530184B2 (en) | 2020-06-30 | 2022-12-20 | Imbria Pharmaceuticals, Inc. | Crystal forms of 2-[4-[(2,3,4-trimethoxyphenyl)methyl]piperazin-1-yl]ethyl pyridine-3-carboxylate |
US11883396B2 (en) | 2021-05-03 | 2024-01-30 | Imbria Pharmaceuticals, Inc. | Methods of treating kidney conditions using modified forms of trimetazidine |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3723797A1 (de) * | 1987-07-18 | 1989-01-26 | Merck Patent Gmbh | Oxazolidinone |
US5053393A (en) * | 1988-07-20 | 1991-10-01 | Monsanto Company | Novel platelet-aggregation inhibitor |
US5084466A (en) * | 1989-01-31 | 1992-01-28 | Hoffmann-La Roche Inc. | Novel carboxamide pyridine compounds which have useful pharmaceutical utility |
DE4005371A1 (de) * | 1990-02-21 | 1991-08-22 | Merck Patent Gmbh | Oxazolidinone |
DE4017211A1 (de) * | 1990-05-29 | 1991-12-05 | Merck Patent Gmbh | Oxazolidinone |
DE4405633A1 (de) * | 1993-05-01 | 1994-11-03 | Merck Patent Gmbh | Adhäsionsrezeptor-Antagonisten |
DE4332384A1 (de) * | 1993-09-23 | 1995-03-30 | Merck Patent Gmbh | Adhäsionsrezeptor-Antagonisten III |
-
1994
- 1994-11-08 DE DE4439846A patent/DE4439846A1/de not_active Withdrawn
-
1995
- 1995-10-26 EP EP95116889A patent/EP0711770A1/de not_active Withdrawn
- 1995-11-01 UA UA95114761A patent/UA41928C2/uk unknown
- 1995-11-02 SK SK1368-95A patent/SK281815B6/sk unknown
- 1995-11-02 AU AU36618/95A patent/AU704184B2/en not_active Ceased
- 1995-11-06 CA CA002162223A patent/CA2162223A1/en not_active Abandoned
- 1995-11-06 CZ CZ19952888A patent/CZ291049B6/cs not_active IP Right Cessation
- 1995-11-06 TW TW084111748A patent/TW316903B/zh active
- 1995-11-07 NO NO954458A patent/NO306113B1/no not_active IP Right Cessation
- 1995-11-07 KR KR1019950040017A patent/KR100384978B1/ko not_active IP Right Cessation
- 1995-11-07 ZA ZA959434A patent/ZA959434B/xx unknown
- 1995-11-07 US US08/551,743 patent/US5776937A/en not_active Expired - Fee Related
- 1995-11-07 CN CN95118753A patent/CN1069640C/zh not_active Expired - Fee Related
- 1995-11-07 FI FI955351A patent/FI955351A/sv not_active IP Right Cessation
- 1995-11-07 BR BR9505109A patent/BR9505109A/pt not_active IP Right Cessation
- 1995-11-07 HU HU9503191A patent/HU217085B/hu not_active IP Right Cessation
- 1995-11-07 PL PL95311257A patent/PL183595B1/pl not_active IP Right Cessation
- 1995-11-08 CO CO95052761A patent/CO4520229A1/es unknown
- 1995-11-08 RU RU95119427/04A patent/RU2155762C2/ru not_active IP Right Cessation
- 1995-11-08 AR ARP950100091A patent/AR002245A1/es unknown
- 1995-11-08 TR TR95/01389A patent/TR199501389A2/xx unknown
- 1995-11-08 JP JP7313684A patent/JPH08208629A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
HU9503191D0 (en) | 1996-01-29 |
CN1132201A (zh) | 1996-10-02 |
EP0711770A1 (de) | 1996-05-15 |
CZ291049B6 (cs) | 2002-12-11 |
JPH08208629A (ja) | 1996-08-13 |
CZ288895A3 (en) | 1996-06-12 |
UA41928C2 (uk) | 2001-10-15 |
TR199501389A2 (tr) | 1996-07-21 |
SK136895A3 (en) | 1996-06-05 |
NO954458D0 (no) | 1995-11-07 |
NO954458L (no) | 1996-05-09 |
ZA959434B (en) | 1996-05-15 |
PL183595B1 (pl) | 2002-06-28 |
PL311257A1 (en) | 1996-05-13 |
TW316903B (sv) | 1997-10-01 |
KR100384978B1 (ko) | 2003-09-02 |
NO306113B1 (no) | 1999-09-20 |
AU3661895A (en) | 1996-05-23 |
HU217085B (hu) | 1999-11-29 |
US5776937A (en) | 1998-07-07 |
CN1069640C (zh) | 2001-08-15 |
DE4439846A1 (de) | 1996-05-09 |
AU704184B2 (en) | 1999-04-15 |
FI955351A0 (sv) | 1995-11-07 |
HUT76052A (en) | 1997-06-30 |
CO4520229A1 (es) | 1997-10-15 |
FI955351A (sv) | 1996-05-09 |
AR002245A1 (es) | 1998-03-11 |
KR960017663A (ko) | 1996-06-17 |
BR9505109A (pt) | 1997-09-09 |
CA2162223A1 (en) | 1996-05-09 |
RU2155762C2 (ru) | 2000-09-10 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP3810837B2 (ja) | 接着受容体拮抗物質 | |
JP3570744B2 (ja) | 接着レセプター拮抗物質 | |
US5561148A (en) | Adhesion receptor antagonists III | |
KR100462176B1 (ko) | 점착성수용체길항제 | |
SK281815B6 (sk) | Derivát oxazolidinónu, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje | |
HU223844B1 (hu) | 2-Oxazolidinon-származékok, eljárás előállításukra és az ezeket tartalmazó gyógyszerkészítmények | |
SK281449B6 (sk) | Derivát oxazolidinónu, spôsob jeho prípravy, farmaceutický prostriedok, ktorý ho obsahuje a použitie | |
KR100379996B1 (ko) | 점착성수용체길항제 | |
KR100349209B1 (ko) | 점착성수용체길항제 |