JP2009511513A - 微小血管障害の処置および予防 - Google Patents

Info

Publication number

JP2009511513A

JP2009511513A JP2008534890A JP2008534890A JP2009511513A JP 2009511513 A JP2009511513 A JP 2009511513A JP 2008534890 A JP2008534890 A JP 2008534890A JP 2008534890 A JP2008534890 A JP 2008534890A JP 2009511513 A JP2009511513 A JP 2009511513A

Authority

JP

Japan

Prior art keywords

oxo

chloro

methyl

phenyl

thiophenecarboxamide

Prior art date

2005-10-10

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Pending

Links

• Espacenet
• Global Dossier
• Discuss

• 230000002265 prevention Effects 0.000 title abstract description 6
• 239000003814 drug Substances 0.000 claims abstract description 34
• 238000004519 manufacturing process Methods 0.000 claims abstract description 22
• IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims abstract description 15
• 238000000034 method Methods 0.000 claims description 188
• 150000001875 compounds Chemical class 0.000 claims description 88
• -1 nitro, amino Chemical group 0.000 claims description 56
• 239000000460 chlorine Substances 0.000 claims description 38
• 150000003839 salts Chemical class 0.000 claims description 36
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 33
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 33
• 239000012453 solvate Substances 0.000 claims description 33
• 229910052757 nitrogen Inorganic materials 0.000 claims description 27
• 208000035475 disorder Diseases 0.000 claims description 26
• 125000005842 heteroatom Chemical group 0.000 claims description 24
• 229940079593 drug Drugs 0.000 claims description 21
• 229910052739 hydrogen Inorganic materials 0.000 claims description 20
• 125000004432 carbon atom Chemical group C* 0.000 claims description 19
• 239000001257 hydrogen Substances 0.000 claims description 19
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
• 208000034841 Thrombotic Microangiopathies Diseases 0.000 claims description 16
• 125000000623 heterocyclic group Chemical group 0.000 claims description 14
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
• 229920006395 saturated elastomer Polymers 0.000 claims description 13
• 229910052717 sulfur Inorganic materials 0.000 claims description 13
• 229910052801 chlorine Inorganic materials 0.000 claims description 12
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
• 208000011580 syndromic disease Diseases 0.000 claims description 10
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
• 208000032759 Hemolytic-Uremic Syndrome Diseases 0.000 claims description 9
• 241001465754 Metazoa Species 0.000 claims description 9
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
• 231100000252 nontoxic Toxicity 0.000 claims description 8
• 230000003000 nontoxic effect Effects 0.000 claims description 8
• 230000000414 obstructive effect Effects 0.000 claims description 8
• 201000010099 disease Diseases 0.000 claims description 7
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
• 229910052794 bromium Inorganic materials 0.000 claims description 6
• 239000011737 fluorine Substances 0.000 claims description 6
• 229910052731 fluorine Inorganic materials 0.000 claims description 6
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
• 206010043561 Thrombocytopenic purpura Diseases 0.000 claims description 5
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
• 210000000056 organ Anatomy 0.000 claims description 5
• 206010012665 Diabetic gangrene Diseases 0.000 claims description 4
• 206010012689 Diabetic retinopathy Diseases 0.000 claims description 4
• 201000007023 Thrombotic Thrombocytopenic Purpura Diseases 0.000 claims description 4
• 201000011510 cancer Diseases 0.000 claims description 4
• 206010014665 endocarditis Diseases 0.000 claims description 4
• 208000019180 nutritional disease Diseases 0.000 claims description 4
• 230000003169 placental effect Effects 0.000 claims description 4
• 230000035935 pregnancy Effects 0.000 claims description 4
• 238000002054 transplantation Methods 0.000 claims description 4
• 208000010353 central nervous system vasculitis Diseases 0.000 claims description 3
• 239000003795 chemical substances by application Substances 0.000 claims description 3
• 206010012601 diabetes mellitus Diseases 0.000 claims description 3
• 208000015181 infectious disease Diseases 0.000 claims description 3
• 208000008899 Habitual abortion Diseases 0.000 claims description 2
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
• 208000034213 recurrent susceptibility to 1 pregnancy loss Diseases 0.000 claims description 2
• 208000027932 Collagen disease Diseases 0.000 claims 1
• 230000002440 hepatic effect Effects 0.000 claims 1
• 229940123583 Factor Xa inhibitor Drugs 0.000 abstract description 17
• 239000000126 substance Substances 0.000 abstract description 2
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 172
• 238000004128 high performance liquid chromatography Methods 0.000 description 143
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 107
• 239000000203 mixture Substances 0.000 description 80
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 63
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 58
• 239000000243 solution Substances 0.000 description 58
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 56
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 42
• 235000019439 ethyl acetate Nutrition 0.000 description 36
• 150000003254 radicals Chemical class 0.000 description 32
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 29
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 26
• 239000000047 product Substances 0.000 description 26
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 24
• 238000006243 chemical reaction Methods 0.000 description 24
• 238000002360 preparation method Methods 0.000 description 24
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 22
• 238000002844 melting Methods 0.000 description 21
• 230000008018 melting Effects 0.000 description 21
• 108010074860 Factor Xa Proteins 0.000 description 20
• 150000001204 N-oxides Chemical class 0.000 description 20
• 239000012043 crude product Substances 0.000 description 20
• 239000011347 resin Substances 0.000 description 20
• 229920005989 resin Polymers 0.000 description 20
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 19
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 19
• 239000012074 organic phase Substances 0.000 description 19
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
• 238000012360 testing method Methods 0.000 description 18
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 16
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 16
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• 150000001412 amines Chemical class 0.000 description 15
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
• 239000011541 reaction mixture Substances 0.000 description 14
• 239000000741 silica gel Substances 0.000 description 14
• 229910002027 silica gel Inorganic materials 0.000 description 14
• 229930192474 thiophene Natural products 0.000 description 14
• 238000005160 1H NMR spectroscopy Methods 0.000 description 13
• 230000015572 biosynthetic process Effects 0.000 description 13
• 238000004007 reversed phase HPLC Methods 0.000 description 13
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
• 229910004298 SiO 2 Inorganic materials 0.000 description 12
• 208000007536 Thrombosis Diseases 0.000 description 12
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
• 238000010898 silica gel chromatography Methods 0.000 description 12
• 239000002904 solvent Substances 0.000 description 12
• 239000000725 suspension Substances 0.000 description 12
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
• 239000003480 eluent Substances 0.000 description 11
• 229910052736 halogen Inorganic materials 0.000 description 11
• 150000002367 halogens Chemical class 0.000 description 11
• 239000002244 precipitate Substances 0.000 description 11
• 239000011734 sodium Substances 0.000 description 11
• 239000007858 starting material Substances 0.000 description 11
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 10
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 10
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 10
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 10
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 9
• 239000004698 Polyethylene Substances 0.000 description 9
• 239000000706 filtrate Substances 0.000 description 9
• 239000003826 tablet Substances 0.000 description 9
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 8
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
• 235000019253 formic acid Nutrition 0.000 description 8
• 230000005764 inhibitory process Effects 0.000 description 8
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
• 238000003756 stirring Methods 0.000 description 8
• 238000003786 synthesis reaction Methods 0.000 description 8
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 7
• QZLSBOVWPHXCLT-UHFFFAOYSA-N 5-chlorothiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(Cl)S1 QZLSBOVWPHXCLT-UHFFFAOYSA-N 0.000 description 7
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 7
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 7
• YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 7
• 239000002253 acid Substances 0.000 description 7
• 229910052786 argon Inorganic materials 0.000 description 7
• 239000008280 blood Substances 0.000 description 7
• 210000004369 blood Anatomy 0.000 description 7
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 7
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
• 238000001816 cooling Methods 0.000 description 7
• 229910052760 oxygen Inorganic materials 0.000 description 7
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
• 229920000573 polyethylene Polymers 0.000 description 7
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
• 230000008569 process Effects 0.000 description 7
• 125000004076 pyridyl group Chemical group 0.000 description 7
• 239000007787 solid Substances 0.000 description 7
• 239000007790 solid phase Substances 0.000 description 7
• 125000001424 substituent group Chemical group 0.000 description 7
• 125000001544 thienyl group Chemical group 0.000 description 7
• BMPDCQVRKDNUAP-UHFFFAOYSA-N 5-chlorothiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)S1 BMPDCQVRKDNUAP-UHFFFAOYSA-N 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• 239000004677 Nylon Substances 0.000 description 6
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
• 238000003818 flash chromatography Methods 0.000 description 6
• 230000008570 general process Effects 0.000 description 6
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
• 235000019341 magnesium sulphate Nutrition 0.000 description 6
• 229920001778 nylon Polymers 0.000 description 6
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 5
• WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 5
• HQZBFUCRRYMCAS-UHFFFAOYSA-N 5-(aminomethyl)-3-[4-(2-oxopyrrolidin-1-yl)phenyl]-1,3-oxazolidin-2-one Chemical compound O=C1OC(CN)CN1C1=CC=C(N2C(CCC2)=O)C=C1 HQZBFUCRRYMCAS-UHFFFAOYSA-N 0.000 description 5
• LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 description 5
• 108090000631 Trypsin Proteins 0.000 description 5
• 102000004142 Trypsin Human genes 0.000 description 5
• 150000001408 amides Chemical class 0.000 description 5
• 230000002785 anti-thrombosis Effects 0.000 description 5
• 239000002585 base Substances 0.000 description 5
• 229910052799 carbon Inorganic materials 0.000 description 5
• WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 5
• 238000007429 general method Methods 0.000 description 5
• 239000003112 inhibitor Substances 0.000 description 5
• 125000001624 naphthyl group Chemical group 0.000 description 5
• 230000003647 oxidation Effects 0.000 description 5
• 238000007254 oxidation reaction Methods 0.000 description 5
• 229940012957 plasmin Drugs 0.000 description 5
• 230000009467 reduction Effects 0.000 description 5
• 239000012588 trypsin Substances 0.000 description 5
• PGOHTUIFYSHAQG-LJSDBVFPSA-N (2S)-6-amino-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-1-[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-4-methylsulfanylbutanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-carbamimidamidopentanoyl]amino]propanoyl]pyrrolidine-2-carbonyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]acetyl]amino]-3-hydroxypropanoyl]amino]-4-methylpentanoyl]amino]-3-sulfanylpropanoyl]amino]-4-methylsulfanylbutanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-hydroxybutanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-hydroxypropanoyl]amino]-3-hydroxypropanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxybutanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-carbamimidamidopentanoyl]amino]-5-oxopentanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxypropanoyl]amino]-3-carboxypropanoyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]-5-oxopentanoyl]amino]-3-phenylpropanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-4-oxobutanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-4-carboxybutanoyl]amino]-5-oxopentanoyl]amino]hexanoic acid Chemical compound CSCC[C@H](N)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H](Cc1cnc[nH]1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCCN)C(O)=O PGOHTUIFYSHAQG-LJSDBVFPSA-N 0.000 description 4
• GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 4
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
• 125000000041 C6-C10 aryl group Chemical group 0.000 description 4
• 125000005915 C6-C14 aryl group Chemical group 0.000 description 4
• 101150065749 Churc1 gene Proteins 0.000 description 4
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
• 102100038239 Protein Churchill Human genes 0.000 description 4
• 108010000499 Thromboplastin Proteins 0.000 description 4
• 102000002262 Thromboplastin Human genes 0.000 description 4
• 238000002835 absorbance Methods 0.000 description 4
• 230000004913 activation Effects 0.000 description 4
• 150000001409 amidines Chemical class 0.000 description 4
• 239000008346 aqueous phase Substances 0.000 description 4
• 230000004087 circulation Effects 0.000 description 4
• 239000000470 constituent Substances 0.000 description 4
• 239000013078 crystal Substances 0.000 description 4
• 238000002425 crystallisation Methods 0.000 description 4
• 230000008025 crystallization Effects 0.000 description 4
• 125000000753 cycloalkyl group Chemical group 0.000 description 4
• UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 4
• 230000006378 damage Effects 0.000 description 4
• 230000003511 endothelial effect Effects 0.000 description 4
• 238000005516 engineering process Methods 0.000 description 4
• 239000012442 inert solvent Substances 0.000 description 4
• 239000007788 liquid 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
• 125000002950 monocyclic group Chemical group 0.000 description 4
• TXOLUCZGHYRKIK-UHFFFAOYSA-N n-[[3-(4-aminophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound C1=CC(N)=CC=C1N1C(=O)OC(CNC(=O)C=2SC(Cl)=CC=2)C1 TXOLUCZGHYRKIK-UHFFFAOYSA-N 0.000 description 4
• 150000002828 nitro derivatives Chemical class 0.000 description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
• 150000002924 oxiranes Chemical class 0.000 description 4
• 238000007911 parenteral administration Methods 0.000 description 4
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 4
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 4
• 239000000843 powder Substances 0.000 description 4
• 238000000746 purification Methods 0.000 description 4
• JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
• 210000003462 vein Anatomy 0.000 description 4
• 238000005406 washing Methods 0.000 description 4
• 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 description 3
• 125000005862 (C1-C6)alkanoyl group Chemical group 0.000 description 3
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 3
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
• CWYUNIAGLBIPIP-AWEZNQCLSA-N 5-chloro-n-[[(5s)-2-oxo-3-[4-(2-oxopyrrolidin-1-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NC[C@@H]1OC(=O)N(C=2C=CC(=CC=2)N2C(CCC2)=O)C1 CWYUNIAGLBIPIP-AWEZNQCLSA-N 0.000 description 3
• KGFYHTZWPPHNLQ-UHFFFAOYSA-N 5-chloro-n-[[2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1OC(=O)N(C=2C=CC(=CC=2)N2C(COCC2)=O)C1 KGFYHTZWPPHNLQ-UHFFFAOYSA-N 0.000 description 3
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• 125000005974 C6-C14 arylcarbonyl group Chemical group 0.000 description 3
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 3
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
• 208000022461 Glomerular disease Diseases 0.000 description 3
• 101001098529 Homo sapiens Proteinase-activated receptor 1 Proteins 0.000 description 3
• 101000713169 Homo sapiens Solute carrier family 52, riboflavin transporter, member 2 Proteins 0.000 description 3
• 238000005684 Liebig rearrangement reaction Methods 0.000 description 3
• 238000005481 NMR spectroscopy Methods 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• 241000700159 Rattus Species 0.000 description 3
• 108010022999 Serine Proteases Proteins 0.000 description 3
• 102000012479 Serine Proteases Human genes 0.000 description 3
• 102100036862 Solute carrier family 52, riboflavin transporter, member 2 Human genes 0.000 description 3
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
• 108090000190 Thrombin Proteins 0.000 description 3
• PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 3
• 125000002252 acyl group Chemical group 0.000 description 3
• 230000010933 acylation Effects 0.000 description 3
• 238000005917 acylation reaction Methods 0.000 description 3
• 125000000217 alkyl group Chemical group 0.000 description 3
• 125000003277 amino group Chemical group 0.000 description 3
• 125000002619 bicyclic group Chemical group 0.000 description 3
• 210000004204 blood vessel Anatomy 0.000 description 3
• 230000037396 body weight Effects 0.000 description 3
• 239000002775 capsule Substances 0.000 description 3
• 239000003054 catalyst Substances 0.000 description 3
• 239000003153 chemical reaction reagent Substances 0.000 description 3
• 239000003593 chromogenic compound Substances 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• 238000003776 cleavage reaction Methods 0.000 description 3
• 238000007796 conventional method Methods 0.000 description 3
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
• 239000002552 dosage form Substances 0.000 description 3
• IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 3
• 239000000284 extract Substances 0.000 description 3
• 238000001914 filtration Methods 0.000 description 3
• 125000002541 furyl group Chemical group 0.000 description 3
• 238000001990 intravenous administration Methods 0.000 description 3
• 238000005259 measurement Methods 0.000 description 3
• VSEAAEQOQBMPQF-UHFFFAOYSA-N morpholin-3-one Chemical compound O=C1COCCN1 VSEAAEQOQBMPQF-UHFFFAOYSA-N 0.000 description 3
• 239000012452 mother liquor Substances 0.000 description 3
• PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 3
• 239000007800 oxidant agent Substances 0.000 description 3
• 239000008194 pharmaceutical composition Substances 0.000 description 3
• 239000001267 polyvinylpyrrolidone Substances 0.000 description 3
• 229910000027 potassium carbonate Inorganic materials 0.000 description 3
• 239000002243 precursor Substances 0.000 description 3
• 150000003141 primary amines Chemical class 0.000 description 3
• 238000010992 reflux Methods 0.000 description 3
• KGFYHTZWPPHNLQ-AWEZNQCLSA-N rivaroxaban Chemical compound S1C(Cl)=CC=C1C(=O)NC[C@@H]1OC(=O)N(C=2C=CC(=CC=2)N2C(COCC2)=O)C1 KGFYHTZWPPHNLQ-AWEZNQCLSA-N 0.000 description 3
• 230000007017 scission Effects 0.000 description 3
• 150000003335 secondary amines Chemical class 0.000 description 3
• 239000011780 sodium chloride Substances 0.000 description 3
• 229910000104 sodium hydride Inorganic materials 0.000 description 3
• 150000003457 sulfones Chemical class 0.000 description 3
• 150000003462 sulfoxides Chemical class 0.000 description 3
• 238000010998 test method Methods 0.000 description 3
• 229960004072 thrombin Drugs 0.000 description 3
• 229960000281 trometamol Drugs 0.000 description 3
• XUUZBGPHLFARMT-GFCCVEGCSA-N (5r)-5-(hydroxymethyl)-3-[4-(2-oxopyrrolidin-1-yl)phenyl]-1,3-oxazolidin-2-one Chemical compound O=C1O[C@@H](CO)CN1C1=CC=C(N2C(CCC2)=O)C=C1 XUUZBGPHLFARMT-GFCCVEGCSA-N 0.000 description 2
• HQZBFUCRRYMCAS-LBPRGKRZSA-N (5s)-5-(aminomethyl)-3-[4-(2-oxopyrrolidin-1-yl)phenyl]-1,3-oxazolidin-2-one Chemical compound O=C1O[C@@H](CN)CN1C1=CC=C(N2C(CCC2)=O)C=C1 HQZBFUCRRYMCAS-LBPRGKRZSA-N 0.000 description 2
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 2
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 2
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 2
• ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 2
• QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
• IOMOVAPYJQVJDK-UHFFFAOYSA-N 1-(4-aminophenyl)pyrrolidin-2-one Chemical compound C1=CC(N)=CC=C1N1C(=O)CCC1 IOMOVAPYJQVJDK-UHFFFAOYSA-N 0.000 description 2
• GQIRIWDEZSKOCN-UHFFFAOYSA-N 1-chloro-n,n,2-trimethylprop-1-en-1-amine Chemical compound CN(C)C(Cl)=C(C)C GQIRIWDEZSKOCN-UHFFFAOYSA-N 0.000 description 2
• PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
• DUILGEYLVHGSEE-ZETCQYMHSA-N 2-[[(2s)-oxiran-2-yl]methyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C[C@H]1CO1 DUILGEYLVHGSEE-ZETCQYMHSA-N 0.000 description 2
• YNSCKPCDFIDINW-UHFFFAOYSA-N 3-[[2-[[1-[2-(dimethylamino)acetyl]-6-methoxy-4,4-dimethyl-2,3-dihydroquinolin-7-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]thiophene-2-carboxamide Chemical compound COC1=CC(C(CCN2C(=O)CN(C)C)(C)C)=C2C=C1NC(N=C1NC=CC1=1)=NC=1NC=1C=CSC=1C(N)=O YNSCKPCDFIDINW-UHFFFAOYSA-N 0.000 description 2
• MHCRLDZZHOVFEE-UHFFFAOYSA-N 4-(4-aminophenyl)morpholin-3-one Chemical compound C1=CC(N)=CC=C1N1C(=O)COCC1 MHCRLDZZHOVFEE-UHFFFAOYSA-N 0.000 description 2
• OWMGEFWSGOTGAU-UHFFFAOYSA-N 4-(4-nitrophenyl)morpholin-3-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1N1C(=O)COCC1 OWMGEFWSGOTGAU-UHFFFAOYSA-N 0.000 description 2
• YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
• CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 2
• IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 2
• LLRCNCXTSFGOGG-UHFFFAOYSA-N 5-chloro-n-(oxiran-2-ylmethyl)thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1OC1 LLRCNCXTSFGOGG-UHFFFAOYSA-N 0.000 description 2
• ZSCSRVHAIFYVEH-UHFFFAOYSA-N 5-chloro-n-[(2-oxo-1,3-oxazolidin-5-yl)methyl]thiophene-2-carboxamide Chemical class S1C(Cl)=CC=C1C(=O)NCC1OC(=O)NC1 ZSCSRVHAIFYVEH-UHFFFAOYSA-N 0.000 description 2
• WNBKYNIODVTCON-LBPRGKRZSA-N 5-chloro-n-[[(5s)-2-oxo-3-(2-oxo-3-propan-2-yl-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound C([C@H]1CN(C(O1)=O)C1=CC=C2N(C(OC2=C1)=O)C(C)C)NC(=O)C1=CC=C(Cl)S1 WNBKYNIODVTCON-LBPRGKRZSA-N 0.000 description 2
• IQOWGQZZKKHHOD-HNNXBMFYSA-N 5-chloro-n-[[(5s)-2-oxo-3-(4-pyrrolidin-1-ylphenyl)-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NC[C@@H]1OC(=O)N(C=2C=CC(=CC=2)N2CCCC2)C1 IQOWGQZZKKHHOD-HNNXBMFYSA-N 0.000 description 2
• QHHSMTMRHRZXPG-HNNXBMFYSA-N 5-chloro-n-[[(5s)-2-oxo-3-[4-(2-oxopiperidin-1-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NC[C@@H]1OC(=O)N(C=2C=CC(=CC=2)N2C(CCCC2)=O)C1 QHHSMTMRHRZXPG-HNNXBMFYSA-N 0.000 description 2
• UTGGEGWCQFMLAP-HNNXBMFYSA-N 5-chloro-n-[[(5s)-3-[4-(diethylamino)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(N(CC)CC)=CC=C1N1C(=O)O[C@@H](CNC(=O)C=2SC(Cl)=CC=2)C1 UTGGEGWCQFMLAP-HNNXBMFYSA-N 0.000 description 2
• SACOFAMTBDMJNN-UHFFFAOYSA-N 5-chloro-n-prop-2-enylthiophene-2-carboxamide Chemical compound ClC1=CC=C(C(=O)NCC=C)S1 SACOFAMTBDMJNN-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
• VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
• 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 2
• 206010053567 Coagulopathies Diseases 0.000 description 2
• NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 2
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
• 108010049003 Fibrinogen Proteins 0.000 description 2
• 102000008946 Fibrinogen Human genes 0.000 description 2
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
• 206010018910 Haemolysis Diseases 0.000 description 2
• 241000282412 Homo Species 0.000 description 2
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
• UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 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
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
• JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
• FIHMYTZODDAHKP-VIFPVBQESA-N NC[C@@H](CN1c(cc2)cc(F)c2NCCO)OC1=O Chemical compound NC[C@@H](CN1c(cc2)cc(F)c2NCCO)OC1=O FIHMYTZODDAHKP-VIFPVBQESA-N 0.000 description 2
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
• 241000283973 Oryctolagus cuniculus Species 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• 239000002202 Polyethylene glycol Substances 0.000 description 2
• 108010094028 Prothrombin Proteins 0.000 description 2
• 102100027378 Prothrombin Human genes 0.000 description 2
• 229940124639 Selective inhibitor Drugs 0.000 description 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• 239000007983 Tris buffer Substances 0.000 description 2
• 238000010521 absorption reaction Methods 0.000 description 2
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
• 239000012190 activator Substances 0.000 description 2
• 239000013543 active substance Substances 0.000 description 2
• 125000003342 alkenyl group Chemical group 0.000 description 2
• 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
• 125000003545 alkoxy group Chemical group 0.000 description 2
• 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 2
• 230000009435 amidation Effects 0.000 description 2
• 238000007112 amidation reaction Methods 0.000 description 2
• 230000033115 angiogenesis Effects 0.000 description 2
• 150000001448 anilines Chemical class 0.000 description 2
• 239000005557 antagonist Substances 0.000 description 2
• 230000002429 anti-coagulating effect Effects 0.000 description 2
• 239000003146 anticoagulant agent Substances 0.000 description 2
• 125000005605 benzo group Chemical group 0.000 description 2
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
• HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 2
• KHKPKIOFQNTCEV-UHFFFAOYSA-N benzyl n-[4-(2-oxopyrrolidin-1-yl)phenyl]carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC(C=C1)=CC=C1N1CCCC1=O KHKPKIOFQNTCEV-UHFFFAOYSA-N 0.000 description 2
• 229940098773 bovine serum albumin Drugs 0.000 description 2
• 150000001718 carbodiimides Chemical class 0.000 description 2
• 150000001721 carbon Chemical group 0.000 description 2
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
• 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 2
• 210000001715 carotid artery Anatomy 0.000 description 2
• 239000003638 chemical reducing agent Substances 0.000 description 2
• 229960001701 chloroform Drugs 0.000 description 2
• 238000004587 chromatography analysis Methods 0.000 description 2
• 230000035602 clotting Effects 0.000 description 2
• 230000015271 coagulation Effects 0.000 description 2
• 238000005345 coagulation Methods 0.000 description 2
• 238000000576 coating method Methods 0.000 description 2
• 238000007906 compression Methods 0.000 description 2
• 230000006835 compression Effects 0.000 description 2
• 239000012141 concentrate Substances 0.000 description 2
• 239000007822 coupling agent Substances 0.000 description 2
• 238000000354 decomposition reaction Methods 0.000 description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
• 238000001035 drying Methods 0.000 description 2
• 239000000839 emulsion Substances 0.000 description 2
• 230000002255 enzymatic effect Effects 0.000 description 2
• DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 2
• 238000002474 experimental method Methods 0.000 description 2
• 238000000605 extraction Methods 0.000 description 2
• 229940012952 fibrinogen Drugs 0.000 description 2
• 230000002496 gastric effect Effects 0.000 description 2
• 239000008187 granular material Substances 0.000 description 2
• 230000008588 hemolysis Effects 0.000 description 2
• 210000002989 hepatic vein Anatomy 0.000 description 2
• 125000001072 heteroaryl group Chemical group 0.000 description 2
• 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
• QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 2
• 239000007943 implant Substances 0.000 description 2
• 238000000338 in vitro Methods 0.000 description 2
• 238000002347 injection Methods 0.000 description 2
• 239000007924 injection Substances 0.000 description 2
• 238000007918 intramuscular administration Methods 0.000 description 2
• PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
• 210000004731 jugular vein Anatomy 0.000 description 2
• VCMGMSHEPQENPE-UHFFFAOYSA-N ketamine hydrochloride Chemical compound [Cl-].C=1C=CC=C(Cl)C=1C1([NH2+]C)CCCCC1=O VCMGMSHEPQENPE-UHFFFAOYSA-N 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
• AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
• 235000019359 magnesium stearate Nutrition 0.000 description 2
• 230000014759 maintenance of location Effects 0.000 description 2
• 238000002483 medication Methods 0.000 description 2
• 238000003328 mesylation reaction Methods 0.000 description 2
• 125000002757 morpholinyl group Chemical group 0.000 description 2
• JNZQZWXLEQBGDK-UHFFFAOYSA-N n-(3-amino-2-hydroxypropyl)-5-chlorothiophene-2-carboxamide Chemical class NCC(O)CNC(=O)C1=CC=C(Cl)S1 JNZQZWXLEQBGDK-UHFFFAOYSA-N 0.000 description 2
• TXOLUCZGHYRKIK-NSHDSACASA-N n-[[(5s)-3-(4-aminophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound C1=CC(N)=CC=C1N1C(=O)O[C@@H](CNC(=O)C=2SC(Cl)=CC=2)C1 TXOLUCZGHYRKIK-NSHDSACASA-N 0.000 description 2
• LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
• 239000012285 osmium tetroxide Substances 0.000 description 2
• 229910000489 osmium tetroxide Inorganic materials 0.000 description 2
• 125000003386 piperidinyl group Chemical group 0.000 description 2
• 229920001223 polyethylene glycol Polymers 0.000 description 2
• 229920000136 polysorbate Polymers 0.000 description 2
• 229950008882 polysorbate Drugs 0.000 description 2
• FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 2
• 239000000651 prodrug Substances 0.000 description 2
• 229940002612 prodrug Drugs 0.000 description 2
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
• 125000006239 protecting group Chemical group 0.000 description 2
• 229940039716 prothrombin Drugs 0.000 description 2
• 125000002098 pyridazinyl group Chemical group 0.000 description 2
• 125000000714 pyrimidinyl group Chemical group 0.000 description 2
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
• 108020003175 receptors Proteins 0.000 description 2
• 102000005962 receptors Human genes 0.000 description 2
• 210000001525 retina Anatomy 0.000 description 2
• 239000000523 sample Substances 0.000 description 2
• XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 2
• 229910052708 sodium Inorganic materials 0.000 description 2
• 239000001509 sodium citrate Substances 0.000 description 2
• NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 2
• 229910052938 sodium sulfate Inorganic materials 0.000 description 2
• 235000011152 sodium sulphate Nutrition 0.000 description 2
• 208000000995 spontaneous abortion Diseases 0.000 description 2
• 229940124530 sulfonamide Drugs 0.000 description 2
• 150000003456 sulfonamides Chemical class 0.000 description 2
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 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
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 2
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
• 239000008096 xylene Substances 0.000 description 2
• VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
• HUTMQVPRHVKKGL-UHFFFAOYSA-N (2-morpholin-4-ylphenyl) carbamate Chemical compound NC(=O)OC1=CC=CC=C1N1CCOCC1 HUTMQVPRHVKKGL-UHFFFAOYSA-N 0.000 description 1
• NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
• MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
• VXIWZOWWQMRVRF-NSHDSACASA-N (5s)-5-(aminomethyl)-3-(3-fluoro-4-morpholin-4-ylphenyl)-1,3-oxazolidin-2-one Chemical compound O=C1O[C@@H](CN)CN1C(C=C1F)=CC=C1N1CCOCC1 VXIWZOWWQMRVRF-NSHDSACASA-N 0.000 description 1
• KGWSQTFKWUBMOC-NSHDSACASA-N (5s)-5-(aminomethyl)-3-(3-fluoro-4-thiomorpholin-4-ylphenyl)-1,3-oxazolidin-2-one Chemical compound O=C1O[C@@H](CN)CN1C(C=C1F)=CC=C1N1CCSCC1 KGWSQTFKWUBMOC-NSHDSACASA-N 0.000 description 1
• OPUMRROEUCLJBB-QMMMGPOBSA-N (5s)-5-(aminomethyl)-3-(3-methyl-2-oxo-1,3-benzothiazol-6-yl)-1,3-oxazolidin-2-one Chemical compound C1=C2SC(=O)N(C)C2=CC=C1N1C[C@H](CN)OC1=O OPUMRROEUCLJBB-QMMMGPOBSA-N 0.000 description 1
• ZDSNUSXJVVDEEW-VIFPVBQESA-N (5s)-5-(aminomethyl)-3-(6-methylthieno[2,3-b]pyridin-2-yl)-1,3-oxazolidin-2-one Chemical compound S1C2=NC(C)=CC=C2C=C1N1C[C@H](CN)OC1=O ZDSNUSXJVVDEEW-VIFPVBQESA-N 0.000 description 1
• HZEFJZMFCZYHBZ-LBPRGKRZSA-N (5s)-5-(aminomethyl)-3-[3-fluoro-4-(4-methylpiperazin-1-yl)phenyl]-1,3-oxazolidin-2-one Chemical compound C1CN(C)CCN1C1=CC=C(N2C(O[C@@H](CN)C2)=O)C=C1F HZEFJZMFCZYHBZ-LBPRGKRZSA-N 0.000 description 1
• HKSRGKXIAYYSDO-INIZCTEOSA-N (5s)-5-(aminomethyl)-3-[3-fluoro-4-(4-pyridin-4-ylpiperazin-1-yl)phenyl]-1,3-oxazolidin-2-one Chemical compound O=C1O[C@@H](CN)CN1C(C=C1F)=CC=C1N1CCN(C=2C=CN=CC=2)CC1 HKSRGKXIAYYSDO-INIZCTEOSA-N 0.000 description 1
• 125000005859 (C1-C6)alkanoyloxymethyl group Chemical group 0.000 description 1
• 125000006555 (C3-C5) cycloalkyl group Chemical group 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
• UKDOTCFNLHHKOF-FGRDZWBJSA-N (z)-1-chloroprop-1-ene;(z)-1,2-dichloroethene Chemical group C\C=C/Cl.Cl\C=C/Cl UKDOTCFNLHHKOF-FGRDZWBJSA-N 0.000 description 1
• KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
• UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
• KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
• 125000004161 1,4-diazepinyl group Chemical group 0.000 description 1
• RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
• APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 description 1
• HFOLSRFQZMMEAA-UHFFFAOYSA-N 1-(4-amino-2-chlorophenyl)pyrrolidin-2-one Chemical compound ClC1=CC(N)=CC=C1N1C(=O)CCC1 HFOLSRFQZMMEAA-UHFFFAOYSA-N 0.000 description 1
• MBVAZGKHRAOOJA-UHFFFAOYSA-N 1-(4-aminophenyl)piperidin-4-one Chemical compound C1=CC(N)=CC=C1N1CCC(=O)CC1 MBVAZGKHRAOOJA-UHFFFAOYSA-N 0.000 description 1
• OJERYNQVBAYNLX-UHFFFAOYSA-N 1-(4-aminophenyl)piperidine-3-carboxamide Chemical compound C1C(C(=O)N)CCCN1C1=CC=C(N)C=C1 OJERYNQVBAYNLX-UHFFFAOYSA-N 0.000 description 1
• SXFSOZCNRLOVFG-UHFFFAOYSA-N 1-(4-aminophenyl)piperidine-4-carboxamide Chemical compound C1CC(C(=O)N)CCN1C1=CC=C(N)C=C1 SXFSOZCNRLOVFG-UHFFFAOYSA-N 0.000 description 1
• RBMVXWHTQSNQOJ-UHFFFAOYSA-N 1-(5-amino-2-morpholin-4-ylphenyl)ethanone Chemical compound CC(=O)C1=CC(N)=CC=C1N1CCOCC1 RBMVXWHTQSNQOJ-UHFFFAOYSA-N 0.000 description 1
• RSCLMSOLYFHRJJ-UHFFFAOYSA-N 1-[4-[5-[[(5-chlorothiophene-2-carbonyl)amino]methyl]-2-oxo-1,3-oxazolidin-3-yl]phenyl]piperidine-3-carboxamide Chemical compound C1C(C(=O)N)CCCN1C1=CC=C(N2C(OC(CNC(=O)C=3SC(Cl)=CC=3)C2)=O)C=C1 RSCLMSOLYFHRJJ-UHFFFAOYSA-N 0.000 description 1
• APBGRKATFAPRFH-UHFFFAOYSA-N 1-[4-[5-[[(5-chlorothiophene-2-carbonyl)amino]methyl]-2-oxo-1,3-oxazolidin-3-yl]phenyl]piperidine-4-carboxamide Chemical compound C1CC(C(=O)N)CCN1C1=CC=C(N2C(OC(CNC(=O)C=3SC(Cl)=CC=3)C2)=O)C=C1 APBGRKATFAPRFH-UHFFFAOYSA-N 0.000 description 1
• NFZPILKNAHMNSE-UHFFFAOYSA-N 1-[4-[[3-[(5-chlorothiophene-2-carbonyl)amino]-2-hydroxypropyl]amino]phenyl]piperidine-3-carboxamide Chemical compound C1C(C(=O)N)CCCN1C(C=C1)=CC=C1NCC(O)CNC(=O)C1=CC=C(Cl)S1 NFZPILKNAHMNSE-UHFFFAOYSA-N 0.000 description 1
• BYOWTBYZRQSJIY-UHFFFAOYSA-N 1-[4-[[3-[(5-chlorothiophene-2-carbonyl)amino]-2-hydroxypropyl]amino]phenyl]piperidine-4-carboxamide Chemical compound C1CC(C(=O)N)CCN1C(C=C1)=CC=C1NCC(O)CNC(=O)C1=CC=C(Cl)S1 BYOWTBYZRQSJIY-UHFFFAOYSA-N 0.000 description 1
• QIUZDTXQLZXAJD-UHFFFAOYSA-N 1-[4-amino-2-(trifluoromethyl)phenyl]pyrrolidin-2-one Chemical compound FC(F)(F)C1=CC(N)=CC=C1N1C(=O)CCC1 QIUZDTXQLZXAJD-UHFFFAOYSA-N 0.000 description 1
• BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
• PWKNBLFSJAVFAB-UHFFFAOYSA-N 1-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1F PWKNBLFSJAVFAB-UHFFFAOYSA-N 0.000 description 1
• YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
• RJXOVESYJFXCGI-UHFFFAOYSA-N 2,4-difluoro-1-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1F RJXOVESYJFXCGI-UHFFFAOYSA-N 0.000 description 1
• YCWRFIYBUQBHJI-UHFFFAOYSA-N 2-(4-aminophenyl)acetonitrile Chemical group NC1=CC=C(CC#N)C=C1 YCWRFIYBUQBHJI-UHFFFAOYSA-N 0.000 description 1
• DUILGEYLVHGSEE-UHFFFAOYSA-N 2-(oxiran-2-ylmethyl)isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CC1CO1 DUILGEYLVHGSEE-UHFFFAOYSA-N 0.000 description 1
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
• LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
• VRPJIFMKZZEXLR-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid Chemical compound CC(C)(C)OC(=O)NCC(O)=O VRPJIFMKZZEXLR-UHFFFAOYSA-N 0.000 description 1
• CKFVSMPWXAASIQ-MRXNPFEDSA-N 2-[(2r)-2-hydroxy-3-[4-(3-oxomorpholin-4-yl)anilino]propyl]isoindole-1,3-dione Chemical compound C([C@@H](O)CN1C(C2=CC=CC=C2C1=O)=O)NC(C=C1)=CC=C1N1CCOCC1=O CKFVSMPWXAASIQ-MRXNPFEDSA-N 0.000 description 1
• KUQNYAUTIWQAKY-MRXNPFEDSA-N 2-[[(5s)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]isoindole-1,3-dione Chemical compound C([C@H](CN1C(C2=CC=CC=C2C1=O)=O)OC1=O)N1C(C=C1)=CC=C1N1CCOCC1=O KUQNYAUTIWQAKY-MRXNPFEDSA-N 0.000 description 1
• QPGIJQUTGABQLQ-UHFFFAOYSA-N 2-[carboxymethyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]acetic acid Chemical compound CC(C)(C)OC(=O)N(CC(O)=O)CC(O)=O QPGIJQUTGABQLQ-UHFFFAOYSA-N 0.000 description 1
• GUWXWPWKFMLCPW-UHFFFAOYSA-N 2-amino-n,n-dimethylbenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=CC=C1N GUWXWPWKFMLCPW-UHFFFAOYSA-N 0.000 description 1
• GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
• VJEBIHTVWPSCEM-UHFFFAOYSA-N 2-fluoro-1,3-dimethyl-5-nitrobenzene Chemical compound CC1=CC([N+]([O-])=O)=CC(C)=C1F VJEBIHTVWPSCEM-UHFFFAOYSA-N 0.000 description 1
• ZGJUJDQANIYVAL-UHFFFAOYSA-N 2-methyl-4-morpholin-4-ylaniline Chemical compound C1=C(N)C(C)=CC(N2CCOCC2)=C1 ZGJUJDQANIYVAL-UHFFFAOYSA-N 0.000 description 1
• LEGKNUIZNFTVBI-UHFFFAOYSA-N 2-methylmorpholin-3-one Chemical compound CC1OCCNC1=O LEGKNUIZNFTVBI-UHFFFAOYSA-N 0.000 description 1
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
• BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 1
• LINBWYYLPWJQHE-UHFFFAOYSA-N 3-(9h-fluoren-9-ylmethoxycarbonylamino)propanoic acid Chemical compound C1=CC=C2C(COC(=O)NCCC(=O)O)C3=CC=CC=C3C2=C1 LINBWYYLPWJQHE-UHFFFAOYSA-N 0.000 description 1
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
• SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 description 1
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
• FAJSLXVGFFLZMR-UHFFFAOYSA-N 3-chloro-4-pyrrolidin-1-ylaniline Chemical compound ClC1=CC(N)=CC=C1N1CCCC1 FAJSLXVGFFLZMR-UHFFFAOYSA-N 0.000 description 1
• GPKDGVXBXQTHRY-UHFFFAOYSA-N 3-chloropropane-1-sulfonyl chloride Chemical compound ClCCCS(Cl)(=O)=O GPKDGVXBXQTHRY-UHFFFAOYSA-N 0.000 description 1
• BRTDKJDVVFXVQK-UHFFFAOYSA-N 3-methoxy-4-morpholin-4-ylaniline Chemical compound COC1=CC(N)=CC=C1N1CCOCC1 BRTDKJDVVFXVQK-UHFFFAOYSA-N 0.000 description 1
• IFZPXYKJYRUOFL-UHFFFAOYSA-N 4-(2-fluoro-4-nitrophenyl)morpholin-3-one Chemical compound FC1=CC([N+](=O)[O-])=CC=C1N1C(=O)COCC1 IFZPXYKJYRUOFL-UHFFFAOYSA-N 0.000 description 1
• KPPNUQUMJMBCKB-UHFFFAOYSA-N 4-(4-amino-2,6-dimethylphenyl)morpholin-3-one Chemical compound CC1=CC(N)=CC(C)=C1N1C(=O)COCC1 KPPNUQUMJMBCKB-UHFFFAOYSA-N 0.000 description 1
• JAYUBKIVPJXUON-UHFFFAOYSA-N 4-(4-amino-2-chlorophenyl)-2-methylmorpholin-3-one Chemical compound O=C1C(C)OCCN1C1=CC=C(N)C=C1Cl JAYUBKIVPJXUON-UHFFFAOYSA-N 0.000 description 1
• GCQFJYMKCROIPH-UHFFFAOYSA-N 4-(4-amino-2-chlorophenyl)morpholin-3-one Chemical compound ClC1=CC(N)=CC=C1N1C(=O)COCC1 GCQFJYMKCROIPH-UHFFFAOYSA-N 0.000 description 1
• OYBFNNGXWGVIIT-UHFFFAOYSA-N 4-(4-amino-2-fluorophenyl)morpholin-3-one Chemical compound FC1=CC(N)=CC=C1N1C(=O)COCC1 OYBFNNGXWGVIIT-UHFFFAOYSA-N 0.000 description 1
• KGPAZBJHRVLNJU-UHFFFAOYSA-N 4-(4-amino-2-methylphenyl)morpholin-3-one Chemical compound CC1=CC(N)=CC=C1N1C(=O)COCC1 KGPAZBJHRVLNJU-UHFFFAOYSA-N 0.000 description 1
• BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
• VSBLPKFRZOWFSZ-UHFFFAOYSA-N 4-[4-amino-2-(trifluoromethyl)phenyl]morpholin-3-one Chemical compound FC(F)(F)C1=CC(N)=CC=C1N1C(=O)COCC1 VSBLPKFRZOWFSZ-UHFFFAOYSA-N 0.000 description 1
• KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
• PHNDZBFLOPIMSM-UHFFFAOYSA-N 4-morpholin-4-ylaniline Chemical compound C1=CC(N)=CC=C1N1CCOCC1 PHNDZBFLOPIMSM-UHFFFAOYSA-N 0.000 description 1
• TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
• VAAASCUUHAHDMZ-UHFFFAOYSA-N 4-pyrrolidin-1-yl-3-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC(N)=CC=C1N1CCCC1 VAAASCUUHAHDMZ-UHFFFAOYSA-N 0.000 description 1
• HUHZAMBLEKHDBP-UHFFFAOYSA-N 5-(aminomethyl)-1,3-oxazolidin-2-one Chemical compound NCC1CNC(=O)O1 HUHZAMBLEKHDBP-UHFFFAOYSA-N 0.000 description 1
• MYQOFWXLYPTHJO-UHFFFAOYSA-N 5-(bromomethyl)-3-(4-fluoro-3-nitrophenyl)-1,3-oxazolidin-2-one Chemical compound C1=C(F)C([N+](=O)[O-])=CC(N2C(OC(CBr)C2)=O)=C1 MYQOFWXLYPTHJO-UHFFFAOYSA-N 0.000 description 1
• UWVQVSGACKTALD-UHFFFAOYSA-N 5-amino-2-(3-oxomorpholin-4-yl)benzonitrile Chemical compound N#CC1=CC(N)=CC=C1N1C(=O)COCC1 UWVQVSGACKTALD-UHFFFAOYSA-N 0.000 description 1
• RPXYGWOWNPRMRE-AWEZNQCLSA-N 5-bromo-n-[[(5s)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Br)=CC=C1C(=O)NC[C@@H]1OC(=O)N(C=2C=CC(=CC=2)N2C(COCC2)=O)C1 RPXYGWOWNPRMRE-AWEZNQCLSA-N 0.000 description 1
• OZNBZSGVGPEVAB-ZDUSSCGKSA-N 5-bromo-n-[[(5s)-3-(3-fluoro-4-thiomorpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound FC1=CC(N2C(O[C@@H](CNC(=O)C=3SC(Br)=CC=3)C2)=O)=CC=C1N1CCSCC1 OZNBZSGVGPEVAB-ZDUSSCGKSA-N 0.000 description 1
• ODBNMTFTNNWNCT-UHFFFAOYSA-N 5-bromo-n-[[2-oxo-3-[4-(2-oxopyrrolidin-1-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Br)=CC=C1C(=O)NCC1OC(=O)N(C=2C=CC(=CC=2)N2C(CCC2)=O)C1 ODBNMTFTNNWNCT-UHFFFAOYSA-N 0.000 description 1
• COWZPSUDTMGBAT-UHFFFAOYSA-N 5-bromothiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(Br)S1 COWZPSUDTMGBAT-UHFFFAOYSA-N 0.000 description 1
• DDJSHNILPXODQL-ZDUSSCGKSA-N 5-chloro-N-[[(5S)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]-N-hydroxythiophene-2-carboxamide Chemical compound C([C@H](OC1=O)CN(O)C(=O)C=2SC(Cl)=CC=2)N1C(C=C1F)=CC=C1N1CCOCC1 DDJSHNILPXODQL-ZDUSSCGKSA-N 0.000 description 1
• DEMJYVDXDRTKPZ-UHFFFAOYSA-N 5-chloro-n-[(2-oxo-3-phenyl-1,3-oxazolidin-5-yl)methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1OC(=O)N(C=2C=CC=CC=2)C1 DEMJYVDXDRTKPZ-UHFFFAOYSA-N 0.000 description 1
• ZXPXUWAFLGCBEW-UHFFFAOYSA-N 5-chloro-n-[2-hydroxy-3-(3-methoxy-4-morpholin-4-ylanilino)propyl]thiophene-2-carboxamide Chemical compound C=1C=C(N2CCOCC2)C(OC)=CC=1NCC(O)CNC(=O)C1=CC=C(Cl)S1 ZXPXUWAFLGCBEW-UHFFFAOYSA-N 0.000 description 1
• CVXRTGZTLBFDER-UHFFFAOYSA-N 5-chloro-n-[2-hydroxy-3-[3-methyl-4-(3-oxomorpholin-4-yl)anilino]propyl]thiophene-2-carboxamide Chemical compound C=1C=C(N2C(COCC2)=O)C(C)=CC=1NCC(O)CNC(=O)C1=CC=C(Cl)S1 CVXRTGZTLBFDER-UHFFFAOYSA-N 0.000 description 1
• OXEJMKXHLJUMGM-UHFFFAOYSA-N 5-chloro-n-[2-hydroxy-3-[4-(2-methyl-3a,4,6,6a-tetrahydro-3h-pyrrolo[3,4-d][1,2]oxazol-5-yl)anilino]propyl]thiophene-2-carboxamide Chemical compound C1C2ON(C)CC2CN1C(C=C1)=CC=C1NCC(O)CNC(=O)C1=CC=C(Cl)S1 OXEJMKXHLJUMGM-UHFFFAOYSA-N 0.000 description 1
• VHZZFYZLUNMFMB-UHFFFAOYSA-N 5-chloro-n-[2-hydroxy-3-[4-(2-oxopyrrolidin-1-yl)-3-(trifluoromethyl)anilino]propyl]thiophene-2-carboxamide Chemical compound C=1C=C(N2C(CCC2)=O)C(C(F)(F)F)=CC=1NCC(O)CNC(=O)C1=CC=C(Cl)S1 VHZZFYZLUNMFMB-UHFFFAOYSA-N 0.000 description 1
• LLUVTGIXIULQSJ-UHFFFAOYSA-N 5-chloro-n-[2-hydroxy-3-[4-(3-oxomorpholin-4-yl)-3-(trifluoromethyl)anilino]propyl]thiophene-2-carboxamide Chemical compound C=1C=C(N2C(COCC2)=O)C(C(F)(F)F)=CC=1NCC(O)CNC(=O)C1=CC=C(Cl)S1 LLUVTGIXIULQSJ-UHFFFAOYSA-N 0.000 description 1
• WJVSLEYKVOVXPZ-UHFFFAOYSA-N 5-chloro-n-[2-hydroxy-3-[4-(4-oxopiperidin-1-yl)anilino]propyl]thiophene-2-carboxamide Chemical compound C=1C=C(N2CCC(=O)CC2)C=CC=1NCC(O)CNC(=O)C1=CC=C(Cl)S1 WJVSLEYKVOVXPZ-UHFFFAOYSA-N 0.000 description 1
• AKQILUJPNJCWCF-UHFFFAOYSA-N 5-chloro-n-[2-hydroxy-3-[4-(triazol-1-yl)anilino]propyl]thiophene-2-carboxamide Chemical compound C=1C=C(N2N=NC=C2)C=CC=1NCC(O)CNC(=O)C1=CC=C(Cl)S1 AKQILUJPNJCWCF-UHFFFAOYSA-N 0.000 description 1
• VLDMSRDJAOCFFD-UHFFFAOYSA-N 5-chloro-n-[2-hydroxy-3-[4-[(3-oxomorpholin-4-yl)methyl]anilino]propyl]thiophene-2-carboxamide Chemical compound C=1C=C(CN2C(COCC2)=O)C=CC=1NCC(O)CNC(=O)C1=CC=C(Cl)S1 VLDMSRDJAOCFFD-UHFFFAOYSA-N 0.000 description 1
• WCIZPSQROUIWBM-UHFFFAOYSA-N 5-chloro-n-[2-hydroxy-3-[4-[2-(hydroxymethyl)piperidin-1-yl]anilino]propyl]thiophene-2-carboxamide Chemical compound OCC1CCCCN1C(C=C1)=CC=C1NCC(O)CNC(=O)C1=CC=C(Cl)S1 WCIZPSQROUIWBM-UHFFFAOYSA-N 0.000 description 1
• NMTXAWHWQFQXIK-UHFFFAOYSA-N 5-chloro-n-[2-hydroxy-3-[4-[2-(hydroxymethyl)pyrrolidin-1-yl]anilino]propyl]thiophene-2-carboxamide Chemical compound OCC1CCCN1C(C=C1)=CC=C1NCC(O)CNC(=O)C1=CC=C(Cl)S1 NMTXAWHWQFQXIK-UHFFFAOYSA-N 0.000 description 1
• LNPNAWHNWCPPKU-UHFFFAOYSA-N 5-chloro-n-[2-hydroxy-3-[4-[3-(hydroxymethyl)piperidin-1-yl]anilino]propyl]thiophene-2-carboxamide Chemical compound C1C(CO)CCCN1C(C=C1)=CC=C1NCC(O)CNC(=O)C1=CC=C(Cl)S1 LNPNAWHNWCPPKU-UHFFFAOYSA-N 0.000 description 1
• COJTZJWUYAKXTA-UHFFFAOYSA-N 5-chloro-n-[2-hydroxy-3-[4-pyrrolidin-1-yl-3-(trifluoromethyl)anilino]propyl]thiophene-2-carboxamide Chemical compound C=1C=C(N2CCCC2)C(C(F)(F)F)=CC=1NCC(O)CNC(=O)C1=CC=C(Cl)S1 COJTZJWUYAKXTA-UHFFFAOYSA-N 0.000 description 1
• YWPNDIFDXSQAHS-UHFFFAOYSA-N 5-chloro-n-[3-(3-chloro-4-pyrrolidin-1-ylanilino)-2-hydroxypropyl]thiophene-2-carboxamide Chemical compound C=1C=C(N2CCCC2)C(Cl)=CC=1NCC(O)CNC(=O)C1=CC=C(Cl)S1 YWPNDIFDXSQAHS-UHFFFAOYSA-N 0.000 description 1
• IAXDGLYXUGKZGN-UHFFFAOYSA-N 5-chloro-n-[3-(3-cyanoanilino)-2-hydroxypropyl]thiophene-2-carboxamide Chemical compound C=1C=CC(C#N)=CC=1NCC(O)CNC(=O)C1=CC=C(Cl)S1 IAXDGLYXUGKZGN-UHFFFAOYSA-N 0.000 description 1
• WFYMXRXBBHPDNH-UHFFFAOYSA-N 5-chloro-n-[3-(4-cyanoanilino)-2-hydroxypropyl]thiophene-2-carboxamide Chemical compound C=1C=C(C#N)C=CC=1NCC(O)CNC(=O)C1=CC=C(Cl)S1 WFYMXRXBBHPDNH-UHFFFAOYSA-N 0.000 description 1
• USBPTPDPYDHXRE-UHFFFAOYSA-N 5-chloro-n-[3-[3,5-dimethyl-4-(3-oxomorpholin-4-yl)anilino]-2-hydroxypropyl]thiophene-2-carboxamide Chemical compound C=1C(C)=C(N2C(COCC2)=O)C(C)=CC=1NCC(O)CNC(=O)C1=CC=C(Cl)S1 USBPTPDPYDHXRE-UHFFFAOYSA-N 0.000 description 1
• WGUBAMOOAYOSSK-UHFFFAOYSA-N 5-chloro-n-[3-[3-(cyanomethyl)anilino]-2-hydroxypropyl]thiophene-2-carboxamide Chemical compound C=1C=CC(CC#N)=CC=1NCC(O)CNC(=O)C1=CC=C(Cl)S1 WGUBAMOOAYOSSK-UHFFFAOYSA-N 0.000 description 1
• JIACIOIAFWMNNY-UHFFFAOYSA-N 5-chloro-n-[3-[3-chloro-4-(2-methyl-3-oxomorpholin-4-yl)anilino]-2-hydroxypropyl]thiophene-2-carboxamide Chemical compound O=C1C(C)OCCN1C(C(=C1)Cl)=CC=C1NCC(O)CNC(=O)C1=CC=C(Cl)S1 JIACIOIAFWMNNY-UHFFFAOYSA-N 0.000 description 1
• ULHDORIDVIGANT-UHFFFAOYSA-N 5-chloro-n-[3-[3-chloro-4-(2-methyl-5-oxomorpholin-4-yl)anilino]-2-hydroxypropyl]thiophene-2-carboxamide Chemical compound O=C1COC(C)CN1C(C(=C1)Cl)=CC=C1NCC(O)CNC(=O)C1=CC=C(Cl)S1 ULHDORIDVIGANT-UHFFFAOYSA-N 0.000 description 1
• HZBUNXZHKHYFGK-UHFFFAOYSA-N 5-chloro-n-[3-[3-chloro-4-(2-oxopyrrolidin-1-yl)anilino]-2-hydroxypropyl]thiophene-2-carboxamide Chemical compound C=1C=C(N2C(CCC2)=O)C(Cl)=CC=1NCC(O)CNC(=O)C1=CC=C(Cl)S1 HZBUNXZHKHYFGK-UHFFFAOYSA-N 0.000 description 1
• BAAJBRUUAQCMLC-UHFFFAOYSA-N 5-chloro-n-[3-[3-chloro-4-(3-oxomorpholin-4-yl)anilino]-2-hydroxypropyl]thiophene-2-carboxamide Chemical compound C=1C=C(N2C(COCC2)=O)C(Cl)=CC=1NCC(O)CNC(=O)C1=CC=C(Cl)S1 BAAJBRUUAQCMLC-UHFFFAOYSA-N 0.000 description 1
• YSUPIIJSHZYYHO-UHFFFAOYSA-N 5-chloro-n-[3-[3-cyano-4-(3-oxomorpholin-4-yl)anilino]-2-hydroxypropyl]thiophene-2-carboxamide Chemical compound C=1C=C(N2C(COCC2)=O)C(C#N)=CC=1NCC(O)CNC(=O)C1=CC=C(Cl)S1 YSUPIIJSHZYYHO-UHFFFAOYSA-N 0.000 description 1
• IRZZJNIBNHRPSA-UHFFFAOYSA-N 5-chloro-n-[3-[3-fluoro-4-(3-oxomorpholin-4-yl)anilino]-2-hydroxypropyl]thiophene-2-carboxamide Chemical compound C=1C=C(N2C(COCC2)=O)C(F)=CC=1NCC(O)CNC(=O)C1=CC=C(Cl)S1 IRZZJNIBNHRPSA-UHFFFAOYSA-N 0.000 description 1
• XQRRKWGVJZRXIJ-UHFFFAOYSA-N 5-chloro-n-[3-[4-(cyanomethyl)anilino]-2-hydroxypropyl]thiophene-2-carboxamide Chemical compound C=1C=C(CC#N)C=CC=1NCC(O)CNC(=O)C1=CC=C(Cl)S1 XQRRKWGVJZRXIJ-UHFFFAOYSA-N 0.000 description 1
• WVHCHEJRXNKQJP-INIZCTEOSA-N 5-chloro-n-[[(5s)-2-oxo-3-(4-piperidin-1-ylphenyl)-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NC[C@@H]1OC(=O)N(C=2C=CC(=CC=2)N2CCCCC2)C1 WVHCHEJRXNKQJP-INIZCTEOSA-N 0.000 description 1
• VWZJPRSLXFXBIU-AWEZNQCLSA-N 5-chloro-n-[[(5s)-2-oxo-3-(6-pyridin-4-ylpyridin-3-yl)-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NC[C@@H]1OC(=O)N(C=2C=NC(=CC=2)C=2C=CN=CC=2)C1 VWZJPRSLXFXBIU-AWEZNQCLSA-N 0.000 description 1
• NWNJMGFPKUJZAK-ZDUSSCGKSA-N 5-chloro-n-[[(5s)-2-oxo-3-[4-(2-oxoazetidin-1-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NC[C@@H]1OC(=O)N(C=2C=CC(=CC=2)N2C(CC2)=O)C1 NWNJMGFPKUJZAK-ZDUSSCGKSA-N 0.000 description 1
• OYFFEZUIIXCYJD-HNNXBMFYSA-N 5-chloro-n-[[(5s)-3-(2-methyl-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound C([C@H]1CN(C(O1)=O)C1=CC=C(C=C1C)N1CCOCC1)NC(=O)C1=CC=C(Cl)S1 OYFFEZUIIXCYJD-HNNXBMFYSA-N 0.000 description 1
• VRACWCMNTPKTQF-ZDUSSCGKSA-N 5-chloro-n-[[(5s)-3-(3-chloro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NC[C@@H]1OC(=O)N(C=2C=C(Cl)C(N3CCOCC3)=CC=2)C1 VRACWCMNTPKTQF-ZDUSSCGKSA-N 0.000 description 1
• MAOZUYDDGGFCKF-ZDUSSCGKSA-N 5-chloro-n-[[(5s)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound FC1=CC(N2C(O[C@@H](CNC(=O)C=3SC(Cl)=CC=3)C2)=O)=CC=C1N1CCOCC1 MAOZUYDDGGFCKF-ZDUSSCGKSA-N 0.000 description 1
• RCVMZVZBCGIKNQ-ZDUSSCGKSA-N 5-chloro-n-[[(5s)-3-(3-fluoro-4-piperazin-1-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound FC1=CC(N2C(O[C@@H](CNC(=O)C=3SC(Cl)=CC=3)C2)=O)=CC=C1N1CCNCC1 RCVMZVZBCGIKNQ-ZDUSSCGKSA-N 0.000 description 1
• UDUYCVOUOVCOFL-ZDUSSCGKSA-N 5-chloro-n-[[(5s)-3-(3-fluoro-4-thiomorpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound FC1=CC(N2C(O[C@@H](CNC(=O)C=3SC(Cl)=CC=3)C2)=O)=CC=C1N1CCSCC1 UDUYCVOUOVCOFL-ZDUSSCGKSA-N 0.000 description 1
• VWGHMVAUEQPGJV-JTQLQIEISA-N 5-chloro-n-[[(5s)-3-(3-methyl-2-oxo-1,3-benzothiazol-6-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound C([C@H]1CN(C(O1)=O)C1=CC=C2N(C(SC2=C1)=O)C)NC(=O)C1=CC=C(Cl)S1 VWGHMVAUEQPGJV-JTQLQIEISA-N 0.000 description 1
• KLGDIFUIQLJAAR-HNNXBMFYSA-N 5-chloro-n-[[(5s)-3-(4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NC[C@@H]1OC(=O)N(C=2C=CC(=CC=2)N2CCOCC2)C1 KLGDIFUIQLJAAR-HNNXBMFYSA-N 0.000 description 1
• FAKWSAHEBQZTOC-AWEZNQCLSA-N 5-chloro-n-[[(5s)-3-(4-morpholin-4-ylsulfonylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NC[C@@H]1OC(=O)N(C=2C=CC(=CC=2)S(=O)(=O)N2CCOCC2)C1 FAKWSAHEBQZTOC-AWEZNQCLSA-N 0.000 description 1
• CCFJTXMTRJOQLK-NSHDSACASA-N 5-chloro-n-[[(5s)-3-(6-methylthieno[2,3-b]pyridin-2-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound C([C@H]1CN(C(O1)=O)C1=CC2=CC=C(N=C2S1)C)NC(=O)C1=CC=C(Cl)S1 CCFJTXMTRJOQLK-NSHDSACASA-N 0.000 description 1
• ARZBFCUVAXIONR-AWEZNQCLSA-N 5-chloro-n-[[(5s)-3-[3-fluoro-4-(4-methylpiperazin-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1CN(C)CCN1C1=CC=C(N2C(O[C@@H](CNC(=O)C=3SC(Cl)=CC=3)C2)=O)C=C1F ARZBFCUVAXIONR-AWEZNQCLSA-N 0.000 description 1
• LSARTDMQGYOGME-SFHVURJKSA-N 5-chloro-n-[[(5s)-3-[3-fluoro-4-(4-pyridin-4-ylpiperazin-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound FC1=CC(N2C(O[C@@H](CNC(=O)C=3SC(Cl)=CC=3)C2)=O)=CC=C1N(CC1)CCN1C1=CC=NC=C1 LSARTDMQGYOGME-SFHVURJKSA-N 0.000 description 1
• PKEZUVZCWCPZHR-HNNXBMFYSA-N 5-chloro-n-[[(5s)-3-[4-(5-chloropentanoylamino)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(NC(=O)CCCCCl)=CC=C1N1C(=O)O[C@@H](CNC(=O)C=2SC(Cl)=CC=2)C1 PKEZUVZCWCPZHR-HNNXBMFYSA-N 0.000 description 1
• AGHXCYDCAOWVPM-LBPRGKRZSA-N 5-chloro-n-[[(5s)-3-[4-(dimethylsulfamoyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1N1C(=O)O[C@@H](CNC(=O)C=2SC(Cl)=CC=2)C1 AGHXCYDCAOWVPM-LBPRGKRZSA-N 0.000 description 1
• OUVWLQSDEQSQIB-UHFFFAOYSA-N 5-chloro-n-[[2-oxo-3-(4-piperidin-1-ylsulfonylphenyl)-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1OC(=O)N(C=2C=CC(=CC=2)S(=O)(=O)N2CCCCC2)C1 OUVWLQSDEQSQIB-UHFFFAOYSA-N 0.000 description 1
• IQOWGQZZKKHHOD-UHFFFAOYSA-N 5-chloro-n-[[2-oxo-3-(4-pyrrolidin-1-ylphenyl)-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1OC(=O)N(C=2C=CC(=CC=2)N2CCCC2)C1 IQOWGQZZKKHHOD-UHFFFAOYSA-N 0.000 description 1
• OAJGJVSOQZSABH-UHFFFAOYSA-N 5-chloro-n-[[2-oxo-3-(4-pyrrolidin-1-ylsulfonylphenyl)-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1OC(=O)N(C=2C=CC(=CC=2)S(=O)(=O)N2CCCC2)C1 OAJGJVSOQZSABH-UHFFFAOYSA-N 0.000 description 1
• AYQBPPBBKPKAMR-UHFFFAOYSA-N 5-chloro-n-[[2-oxo-3-[4-(2-oxopyrrolidin-1-yl)-3-(trifluoromethyl)phenyl]-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound FC(F)(F)C1=CC(N2C(OC(CNC(=O)C=3SC(Cl)=CC=3)C2)=O)=CC=C1N1CCCC1=O AYQBPPBBKPKAMR-UHFFFAOYSA-N 0.000 description 1
• DRBHMPWPYAXXIX-UHFFFAOYSA-N 5-chloro-n-[[2-oxo-3-[4-(3-oxomorpholin-4-yl)-3-(trifluoromethyl)phenyl]-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound FC(F)(F)C1=CC(N2C(OC(CNC(=O)C=3SC(Cl)=CC=3)C2)=O)=CC=C1N1CCOCC1=O DRBHMPWPYAXXIX-UHFFFAOYSA-N 0.000 description 1
• SMHIEDRXKJQDCC-UHFFFAOYSA-N 5-chloro-n-[[2-oxo-3-[4-(4-oxopiperidin-1-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1OC(=O)N(C=2C=CC(=CC=2)N2CCC(=O)CC2)C1 SMHIEDRXKJQDCC-UHFFFAOYSA-N 0.000 description 1
• HUZANKQWACRXDD-UHFFFAOYSA-N 5-chloro-n-[[2-oxo-3-[4-(thiophene-2-carbonylamino)phenyl]-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1OC(=O)N(C=2C=CC(NC(=O)C=3SC=CC=3)=CC=2)C1 HUZANKQWACRXDD-UHFFFAOYSA-N 0.000 description 1
• OFCMULVNWOFNAW-UHFFFAOYSA-N 5-chloro-n-[[2-oxo-3-[4-(triazol-1-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1OC(=O)N(C=2C=CC(=CC=2)N2N=NC=C2)C1 OFCMULVNWOFNAW-UHFFFAOYSA-N 0.000 description 1
• RLRUZWZNFFRWKA-UHFFFAOYSA-N 5-chloro-n-[[2-oxo-3-[4-[(3-oxomorpholin-4-yl)methyl]phenyl]-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1OC(=O)N(C=2C=CC(CN3C(COCC3)=O)=CC=2)C1 RLRUZWZNFFRWKA-UHFFFAOYSA-N 0.000 description 1
• ABRDSYPPMWQMEH-UHFFFAOYSA-N 5-chloro-n-[[2-oxo-3-[4-pyrrolidin-1-yl-3-(trifluoromethyl)phenyl]-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound FC(F)(F)C1=CC(N2C(OC(CNC(=O)C=3SC(Cl)=CC=3)C2)=O)=CC=C1N1CCCC1 ABRDSYPPMWQMEH-UHFFFAOYSA-N 0.000 description 1
• JOAAAXOTFLYFEQ-UHFFFAOYSA-N 5-chloro-n-[[3-(3-chloro-4-pyrrolidin-1-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1OC(=O)N(C=2C=C(Cl)C(N3CCCC3)=CC=2)C1 JOAAAXOTFLYFEQ-UHFFFAOYSA-N 0.000 description 1
• FYGSIFGKVCKYPY-UHFFFAOYSA-N 5-chloro-n-[[3-(3-cyanophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1OC(=O)N(C=2C=C(C=CC=2)C#N)C1 FYGSIFGKVCKYPY-UHFFFAOYSA-N 0.000 description 1
• JADWRZXMZVQXHY-UHFFFAOYSA-N 5-chloro-n-[[3-(3-methoxy-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound COC1=CC(N2C(OC(CNC(=O)C=3SC(Cl)=CC=3)C2)=O)=CC=C1N1CCOCC1 JADWRZXMZVQXHY-UHFFFAOYSA-N 0.000 description 1
• VDZQAMJMAPJQLF-UHFFFAOYSA-N 5-chloro-n-[[3-[3,5-dimethyl-4-(3-oxomorpholin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound CC1=CC(N2C(OC(CNC(=O)C=3SC(Cl)=CC=3)C2)=O)=CC(C)=C1N1CCOCC1=O VDZQAMJMAPJQLF-UHFFFAOYSA-N 0.000 description 1
• SZALQORQGIDWDU-UHFFFAOYSA-N 5-chloro-n-[[3-[3-(2-imino-2-morpholin-4-ylethyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1OC(=O)N(C=2C=C(CC(=N)N3CCOCC3)C=CC=2)C1 SZALQORQGIDWDU-UHFFFAOYSA-N 0.000 description 1
• RJHJLKLYFFZILW-UHFFFAOYSA-N 5-chloro-n-[[3-[3-(2-imino-2-pyrrolidin-1-ylethyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1OC(=O)N(C=2C=C(CC(=N)N3CCCC3)C=CC=2)C1 RJHJLKLYFFZILW-UHFFFAOYSA-N 0.000 description 1
• HEZTWVFYCJXNHI-UHFFFAOYSA-N 5-chloro-n-[[3-[3-(4,5-dihydro-1h-imidazol-2-ylmethyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1OC(=O)N(C=2C=C(CC=3NCCN=3)C=CC=2)C1 HEZTWVFYCJXNHI-UHFFFAOYSA-N 0.000 description 1
• DPFDUSLNEIQQSS-UHFFFAOYSA-N 5-chloro-n-[[3-[3-(cyanomethyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1OC(=O)N(C=2C=C(CC#N)C=CC=2)C1 DPFDUSLNEIQQSS-UHFFFAOYSA-N 0.000 description 1
• LLDIRJZVTWAVJA-UHFFFAOYSA-N 5-chloro-n-[[3-[3-chloro-4-(2-methyl-3-oxomorpholin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound O=C1C(C)OCCN1C1=CC=C(N2C(OC(CNC(=O)C=3SC(Cl)=CC=3)C2)=O)C=C1Cl LLDIRJZVTWAVJA-UHFFFAOYSA-N 0.000 description 1
• CINLGKARBZRUHA-UHFFFAOYSA-N 5-chloro-n-[[3-[3-chloro-4-(2-methyl-5-oxomorpholin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound O=C1COC(C)CN1C1=CC=C(N2C(OC(CNC(=O)C=3SC(Cl)=CC=3)C2)=O)C=C1Cl CINLGKARBZRUHA-UHFFFAOYSA-N 0.000 description 1
• CCXMKHCTYBPHGE-UHFFFAOYSA-N 5-chloro-n-[[3-[3-chloro-4-(2-oxopyrrolidin-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1OC(=O)N(C=2C=C(Cl)C(N3C(CCC3)=O)=CC=2)C1 CCXMKHCTYBPHGE-UHFFFAOYSA-N 0.000 description 1
• PTEATNHBXYPOGI-UHFFFAOYSA-N 5-chloro-n-[[3-[3-chloro-4-(3-oxomorpholin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1OC(=O)N(C=2C=C(Cl)C(N3C(COCC3)=O)=CC=2)C1 PTEATNHBXYPOGI-UHFFFAOYSA-N 0.000 description 1
• DCPACTHLXVKWPS-UHFFFAOYSA-N 5-chloro-n-[[3-[3-cyano-4-(3-oxomorpholin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1OC(=O)N(C=2C=C(C(N3C(COCC3)=O)=CC=2)C#N)C1 DCPACTHLXVKWPS-UHFFFAOYSA-N 0.000 description 1
• XVBPEQFOAPLQGK-UHFFFAOYSA-N 5-chloro-n-[[3-[3-fluoro-4-(3-oxomorpholin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound FC1=CC(N2C(OC(CNC(=O)C=3SC(Cl)=CC=3)C2)=O)=CC=C1N1CCOCC1=O XVBPEQFOAPLQGK-UHFFFAOYSA-N 0.000 description 1
• BKYWCRZWJHOAJZ-UHFFFAOYSA-N 5-chloro-n-[[3-[3-methyl-4-(3-oxomorpholin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound CC1=CC(N2C(OC(CNC(=O)C=3SC(Cl)=CC=3)C2)=O)=CC=C1N1CCOCC1=O BKYWCRZWJHOAJZ-UHFFFAOYSA-N 0.000 description 1
• JRRSRJDAQWOVLK-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(2-imino-2-morpholin-4-ylethyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1OC(=O)N(C=2C=CC(CC(=N)N3CCOCC3)=CC=2)C1 JRRSRJDAQWOVLK-UHFFFAOYSA-N 0.000 description 1
• AHLFWIUFZAENMH-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(2-imino-2-piperidin-1-ylethyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1OC(=O)N(C=2C=CC(CC(=N)N3CCCCC3)=CC=2)C1 AHLFWIUFZAENMH-UHFFFAOYSA-N 0.000 description 1
• FQXFNTKLRHWYDM-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(2-imino-2-pyrrolidin-1-ylethyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1OC(=O)N(C=2C=CC(CC(=N)N3CCCC3)=CC=2)C1 FQXFNTKLRHWYDM-UHFFFAOYSA-N 0.000 description 1
• MBXZCPGGTOYKOP-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(2-methyl-3a,4,6,6a-tetrahydro-3h-pyrrolo[3,4-d][1,2]oxazol-5-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1C2ON(C)CC2CN1C(C=C1)=CC=C1N(C(O1)=O)CC1CNC(=O)C1=CC=C(Cl)S1 MBXZCPGGTOYKOP-UHFFFAOYSA-N 0.000 description 1
• KGQZMGDQAHIPQC-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(3-chloropropylsulfonylamino)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(NS(=O)(=O)CCCCl)=CC=C1N1C(=O)OC(CNC(=O)C=2SC(Cl)=CC=2)C1 KGQZMGDQAHIPQC-UHFFFAOYSA-N 0.000 description 1
• FXUJJSFAWMGGCC-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(4,5-dihydro-1h-imidazol-2-ylmethyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1OC(=O)N(C=2C=CC(CC=3NCCN=3)=CC=2)C1 FXUJJSFAWMGGCC-UHFFFAOYSA-N 0.000 description 1
• QMOWUHGZUGFSQC-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(4-hydroxypiperidin-1-yl)sulfonylphenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1CC(O)CCN1S(=O)(=O)C1=CC=C(N2C(OC(CNC(=O)C=3SC(Cl)=CC=3)C2)=O)C=C1 QMOWUHGZUGFSQC-UHFFFAOYSA-N 0.000 description 1
• CXUZIZRHDJTNRW-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC=C(N2C(OC(CNC(=O)C=3SC(Cl)=CC=3)C2)=O)C=C1 CXUZIZRHDJTNRW-UHFFFAOYSA-N 0.000 description 1
• SDHRSUBLVNEWLU-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(cyanomethyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1OC(=O)N(C=2C=CC(CC#N)=CC=2)C1 SDHRSUBLVNEWLU-UHFFFAOYSA-N 0.000 description 1
• BKDSZEWNGUNWLC-UHFFFAOYSA-N 5-chloro-n-[[3-[4-[(2-methoxyacetyl)amino]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(NC(=O)COC)=CC=C1N1C(=O)OC(CNC(=O)C=2SC(Cl)=CC=2)C1 BKDSZEWNGUNWLC-UHFFFAOYSA-N 0.000 description 1
• IGQFQVUKWORHKK-UHFFFAOYSA-N 5-chloro-n-[[3-[4-[2-(hydroxymethyl)piperidin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound OCC1CCCCN1C1=CC=C(N2C(OC(CNC(=O)C=3SC(Cl)=CC=3)C2)=O)C=C1 IGQFQVUKWORHKK-UHFFFAOYSA-N 0.000 description 1
• BPMNNLBKERMQPF-UHFFFAOYSA-N 5-chloro-n-[[3-[4-[2-(hydroxymethyl)pyrrolidin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound OCC1CCCN1C1=CC=C(N2C(OC(CNC(=O)C=3SC(Cl)=CC=3)C2)=O)C=C1 BPMNNLBKERMQPF-UHFFFAOYSA-N 0.000 description 1
• MECXHZOXSJQQQM-UHFFFAOYSA-N 5-chloro-n-[[3-[4-[3-(hydroxymethyl)piperidin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1C(CO)CCCN1C1=CC=C(N2C(OC(CNC(=O)C=3SC(Cl)=CC=3)C2)=O)C=C1 MECXHZOXSJQQQM-UHFFFAOYSA-N 0.000 description 1
• SVNNWKWHLOJLOK-UHFFFAOYSA-N 5-chloropentanoyl chloride Chemical compound ClCCCCC(Cl)=O SVNNWKWHLOJLOK-UHFFFAOYSA-N 0.000 description 1
• 125000000290 5-chloropentanoyl group Chemical group ClCCCCC(=O)* 0.000 description 1
• YWRVKEHHSZEJNV-INIZCTEOSA-N 5-methyl-n-[[(5s)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(C)=CC=C1C(=O)NC[C@@H]1OC(=O)N(C=2C=CC(=CC=2)N2C(COCC2)=O)C1 YWRVKEHHSZEJNV-INIZCTEOSA-N 0.000 description 1
• JDZMFDDYWDYSSV-UHFFFAOYSA-N 5-methyl-n-[[2-oxo-3-[4-(2-oxopyrrolidin-1-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(C)=CC=C1C(=O)NCC1OC(=O)N(C=2C=CC(=CC=2)N2C(CCC2)=O)C1 JDZMFDDYWDYSSV-UHFFFAOYSA-N 0.000 description 1
• VCNGNQLPFHVODE-UHFFFAOYSA-N 5-methylthiophene-2-carboxylic acid Chemical compound CC1=CC=C(C(O)=O)S1 VCNGNQLPFHVODE-UHFFFAOYSA-N 0.000 description 1
• KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 description 1
• XGXUFECUXBGUTE-PPHPATTJSA-N 6-[(5s)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]-3-propan-2-yl-1,3-benzoxazol-2-one;hydrochloride Chemical compound Cl.C1=C2OC(=O)N(C(C)C)C2=CC=C1N1C[C@H](CN)OC1=O XGXUFECUXBGUTE-PPHPATTJSA-N 0.000 description 1
• 125000003341 7 membered heterocyclic group Chemical group 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
• 206010000234 Abortion spontaneous Diseases 0.000 description 1
• 108010088751 Albumins Proteins 0.000 description 1
• 102000009027 Albumins Human genes 0.000 description 1
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
• WSVLPVUVIUVCRA-KPKNDVKVSA-N Alpha-lactose monohydrate Chemical compound O.O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O WSVLPVUVIUVCRA-KPKNDVKVSA-N 0.000 description 1
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
• 239000005695 Ammonium acetate Substances 0.000 description 1
• 239000004475 Arginine Substances 0.000 description 1
• 239000005711 Benzoic acid Substances 0.000 description 1
• PBMUJOYMXDGUNM-MARWXBMYSA-N C(=O)(OC(C)(C)C)N[C@H](CCSC)C(=O)O.C(C)(C)(C)OC(=O)N[C@H](CCSC)C(=O)NC1=CC=C(C=C1)N1C(O[C@H](C1)CNC(=O)C=1SC(=CC1)Cl)=O Chemical compound C(=O)(OC(C)(C)C)N[C@H](CCSC)C(=O)O.C(C)(C)(C)OC(=O)N[C@H](CCSC)C(=O)NC1=CC=C(C=C1)N1C(O[C@H](C1)CNC(=O)C=1SC(=CC1)Cl)=O PBMUJOYMXDGUNM-MARWXBMYSA-N 0.000 description 1
• YDFCPXDVMCCRCR-UHFFFAOYSA-N C1(C=2C(C(N1NN)=O)=CC=CC2)=O.[K] Chemical compound C1(C=2C(C(N1NN)=O)=CC=CC2)=O.[K] YDFCPXDVMCCRCR-UHFFFAOYSA-N 0.000 description 1
• GCUAMQAQLVUXMU-JTQLQIEISA-N CC(C)N(c(c(O1)c2)ccc2N(C[C@H](CN)O2)C2=O)C1=O Chemical compound CC(C)N(c(c(O1)c2)ccc2N(C[C@H](CN)O2)C2=O)C1=O GCUAMQAQLVUXMU-JTQLQIEISA-N 0.000 description 1
• KZQVXBBMCFRHNA-UHFFFAOYSA-N CC1OCC(NC1)=O.NC1=CC(=C(C=C1)N1C(COC(C1)C)=O)Cl Chemical compound CC1OCC(NC1)=O.NC1=CC(=C(C=C1)N1C(COC(C1)C)=O)Cl KZQVXBBMCFRHNA-UHFFFAOYSA-N 0.000 description 1
• CPBLERXNSUUHOT-UHFFFAOYSA-N CN1OC2C(C1)CNC2.CN2OC1C(C2)CN(C1)C1=CC=C(C=C1)N Chemical compound CN1OC2C(C1)CNC2.CN2OC1C(C2)CN(C1)C1=CC=C(C=C1)N CPBLERXNSUUHOT-UHFFFAOYSA-N 0.000 description 1
• DKVAPTHJGIYLTB-LBPRGKRZSA-N COCCNc(ccc(N(C[C@H](CNC(c([s]1)ccc1Cl)=O)O1)C1=O)c1)c1F Chemical compound COCCNc(ccc(N(C[C@H](CNC(c([s]1)ccc1Cl)=O)O1)C1=O)c1)c1F DKVAPTHJGIYLTB-LBPRGKRZSA-N 0.000 description 1
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
• 208000035473 Communicable disease Diseases 0.000 description 1
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
• 229920002261 Corn starch Polymers 0.000 description 1
• PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 1
• 108010036949 Cyclosporine Proteins 0.000 description 1
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
• 206010054044 Diabetic microangiopathy Diseases 0.000 description 1
• BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
• XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
• RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
• 208000005189 Embolism Diseases 0.000 description 1
• 102000004190 Enzymes Human genes 0.000 description 1
• 108090000790 Enzymes Proteins 0.000 description 1
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
• ALTQZYXZBDGQGN-UHFFFAOYSA-N FC1=C(C=C(C=C1)[N+](=O)[O-])[N+](=O)[O-].NC1=C(C=CC(=C1)N)N1C(COCC1)=O Chemical compound FC1=C(C=C(C=C1)[N+](=O)[O-])[N+](=O)[O-].NC1=C(C=CC(=C1)N)N1C(COCC1)=O ALTQZYXZBDGQGN-UHFFFAOYSA-N 0.000 description 1
• XKVVCLYSRRZJOA-UHFFFAOYSA-N FC=1C=C(C=CC1N1C(CCC1)=O)[N+](=O)[O-].N1(C(CCC1)=O)C1=CC=C(C=C1)[N+](=O)[O-].[N+](=O)([O-])C1=CC=CC=C1 Chemical compound FC=1C=C(C=CC1N1C(CCC1)=O)[N+](=O)[O-].N1(C(CCC1)=O)C1=CC=C(C=C1)[N+](=O)[O-].[N+](=O)([O-])C1=CC=CC=C1 XKVVCLYSRRZJOA-UHFFFAOYSA-N 0.000 description 1
• FLOOUSOXMVURRI-UHFFFAOYSA-N FC=1C=C(N)C=CC1N1C(CCC1)=O.N1(C(CCC1)=O)C1=CC=C(N)C=C1.NC1=CC=CC=C1 Chemical compound FC=1C=C(N)C=CC1N1C(CCC1)=O.N1(C(CCC1)=O)C1=CC=C(N)C=C1.NC1=CC=CC=C1 FLOOUSOXMVURRI-UHFFFAOYSA-N 0.000 description 1
• 108010054265 Factor VIIa Proteins 0.000 description 1
• 229940122564 Factor X inhibitor Drugs 0.000 description 1
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
• 208000032843 Hemorrhage Diseases 0.000 description 1
• 206010021143 Hypoxia Diseases 0.000 description 1
• 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 1
• ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
• 239000004472 Lysine Substances 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• 229930195725 Mannitol Natural products 0.000 description 1
• 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 1
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
• 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
• 229930192392 Mitomycin Natural products 0.000 description 1
• NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 1
• AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
• UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
• WCDUJQXGPHZLKG-UHFFFAOYSA-N NC1=CC(=C(C=C1)N1C(COCC1)=O)F.ClC1=CC=C(S1)C(=O)NCC(CNC1=CC(=C(C=C1)N1C(COCC1)=O)F)O Chemical compound NC1=CC(=C(C=C1)N1C(COCC1)=O)F.ClC1=CC=C(S1)C(=O)NCC(CNC1=CC(=C(C=C1)N1C(COCC1)=O)F)O WCDUJQXGPHZLKG-UHFFFAOYSA-N 0.000 description 1
• DGHKPQPBPHHUHL-UHFFFAOYSA-N NC1=CC=C(C=C1)N(C(C)=O)C1CC1.C(C)(=O)N(C1=CC=C(C=C1)NCC(CNC(=O)C=1SC(=CC1)Cl)O)C1CC1 Chemical compound NC1=CC=C(C=C1)N(C(C)=O)C1CC1.C(C)(=O)N(C1=CC=C(C=C1)NCC(CNC(=O)C=1SC(=CC1)Cl)O)C1CC1 DGHKPQPBPHHUHL-UHFFFAOYSA-N 0.000 description 1
• XVIDFYSLCZKCJJ-UHFFFAOYSA-N NC1=CC=C(C=C1)N1C(COCC1)=O.ClC1=CC=C(S1)C(=O)NCC(CNC1=CC=C(C=C1)N1C(COCC1)=O)O Chemical compound NC1=CC=C(C=C1)N1C(COCC1)=O.ClC1=CC=C(S1)C(=O)NCC(CNC1=CC=C(C=C1)N1C(COCC1)=O)O XVIDFYSLCZKCJJ-UHFFFAOYSA-N 0.000 description 1
• VOFMNTQHEZOENN-UHFFFAOYSA-N NC1=CC=C(CNC(OC(C)(C)C)=O)C=C1.ClC1=CC=C(S1)C(=O)NCC(CNC1=CC=C(CNC(OC(C)(C)C)=O)C=C1)O Chemical compound NC1=CC=C(CNC(OC(C)(C)C)=O)C=C1.ClC1=CC=C(S1)C(=O)NCC(CNC1=CC=C(CNC(OC(C)(C)C)=O)C=C1)O VOFMNTQHEZOENN-UHFFFAOYSA-N 0.000 description 1
• 206010029113 Neovascularisation Diseases 0.000 description 1
• IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 1
• KZCXFADDWNNLRM-NSHDSACASA-N OCCNc(ccc(N(C[C@H](CNC(c([s]1)ccc1Cl)=O)O1)C1=O)c1)c1F Chemical compound OCCNc(ccc(N(C[C@H](CNC(c([s]1)ccc1Cl)=O)O1)C1=O)c1)c1F KZCXFADDWNNLRM-NSHDSACASA-N 0.000 description 1
• 208000031481 Pathologic Constriction Diseases 0.000 description 1
• 108091005804 Peptidases Proteins 0.000 description 1
• 102000035195 Peptidases Human genes 0.000 description 1
• 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
• 239000004365 Protease Substances 0.000 description 1
• 206010038848 Retinal detachment Diseases 0.000 description 1
• 208000017442 Retinal disease Diseases 0.000 description 1
• 206010038923 Retinopathy Diseases 0.000 description 1
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
• DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
• 229920002472 Starch Polymers 0.000 description 1
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
• 229940122388 Thrombin inhibitor Drugs 0.000 description 1
• 208000001435 Thromboembolism Diseases 0.000 description 1
• GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
• 208000034698 Vitreous haemorrhage Diseases 0.000 description 1
• 208000027418 Wounds and injury Diseases 0.000 description 1
• VVLRASGCTQMFFU-UHFFFAOYSA-N [1-(4-aminophenyl)piperidin-2-yl]methanol Chemical compound C1=CC(N)=CC=C1N1C(CO)CCCC1 VVLRASGCTQMFFU-UHFFFAOYSA-N 0.000 description 1
• ZPGVLDQXMSGLHG-UHFFFAOYSA-N [1-(4-aminophenyl)piperidin-3-yl]methanol Chemical compound C1=CC(N)=CC=C1N1CC(CO)CCC1 ZPGVLDQXMSGLHG-UHFFFAOYSA-N 0.000 description 1
• JKNODKXGKFKOCM-UHFFFAOYSA-N [1-(4-aminophenyl)pyrrolidin-2-yl]methanol Chemical compound C1=CC(N)=CC=C1N1C(CO)CCC1 JKNODKXGKFKOCM-UHFFFAOYSA-N 0.000 description 1
• CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 1
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
• 239000012346 acetyl chloride Substances 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 230000001154 acute effect Effects 0.000 description 1
• 239000000443 aerosol Substances 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• 229910052783 alkali metal Inorganic materials 0.000 description 1
• 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
• 150000008041 alkali metal carbonates Chemical class 0.000 description 1
• 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
• 125000000278 alkyl amino alkyl group Chemical group 0.000 description 1
• 150000001350 alkyl halides Chemical class 0.000 description 1
• 125000004390 alkyl sulfonyl 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
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 238000011938 amidation process Methods 0.000 description 1
• 150000001413 amino acids Chemical class 0.000 description 1
• 150000001414 amino alcohols Chemical class 0.000 description 1
• 125000004103 aminoalkyl group Chemical group 0.000 description 1
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
• 229910021529 ammonia Inorganic materials 0.000 description 1
• 235000019257 ammonium acetate Nutrition 0.000 description 1
• 229940043376 ammonium acetate Drugs 0.000 description 1
• 235000019270 ammonium chloride Nutrition 0.000 description 1
• 150000003863 ammonium salts Chemical class 0.000 description 1
• 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
• 239000003242 anti bacterial agent Substances 0.000 description 1
• 230000000844 anti-bacterial effect Effects 0.000 description 1
• 230000000845 anti-microbial effect Effects 0.000 description 1
• 229940088710 antibiotic agent Drugs 0.000 description 1
• 229940127219 anticoagulant drug Drugs 0.000 description 1
• 230000010100 anticoagulation Effects 0.000 description 1
• 229940082992 antihypertensives mao inhibitors Drugs 0.000 description 1
• 239000003963 antioxidant agent Substances 0.000 description 1
• 235000006708 antioxidants Nutrition 0.000 description 1
• 229940127217 antithrombotic drug Drugs 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
• 125000005129 aryl carbonyl group Chemical group 0.000 description 1
• 125000003118 aryl group Chemical group 0.000 description 1
• 235000010323 ascorbic acid Nutrition 0.000 description 1
• 229960005070 ascorbic acid Drugs 0.000 description 1
• 239000011668 ascorbic acid Substances 0.000 description 1
• 238000003149 assay kit Methods 0.000 description 1
• 125000002785 azepinyl group Chemical group 0.000 description 1
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
• PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 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
• 235000010233 benzoic acid Nutrition 0.000 description 1
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical group NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 1
• 239000011230 binding agent Substances 0.000 description 1
• 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 1
• 230000000740 bleeding effect Effects 0.000 description 1
• 230000023555 blood coagulation Effects 0.000 description 1
• 239000003114 blood coagulation factor Substances 0.000 description 1
• 229930188620 butyrolactone Natural products 0.000 description 1
• 239000011575 calcium Substances 0.000 description 1
• 229910052791 calcium Inorganic materials 0.000 description 1
• GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 1
• 229950005499 carbon tetrachloride Drugs 0.000 description 1
• 150000001735 carboxylic acids Chemical class 0.000 description 1
• 239000000969 carrier Substances 0.000 description 1
• 230000003197 catalytic effect Effects 0.000 description 1
• XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
• 229960001265 ciclosporin Drugs 0.000 description 1
• 235000015165 citric acid Nutrition 0.000 description 1
• 239000003086 colorant Substances 0.000 description 1
• 238000004440 column chromatography Methods 0.000 description 1
• 239000013068 control sample Substances 0.000 description 1
• 229910052802 copper Inorganic materials 0.000 description 1
• 239000010949 copper Substances 0.000 description 1
• 239000008120 corn starch Substances 0.000 description 1
• 239000006071 cream Substances 0.000 description 1
• 125000006165 cyclic alkyl group Chemical group 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 229930182912 cyclosporin Natural products 0.000 description 1
• 229960002887 deanol Drugs 0.000 description 1
• 230000003111 delayed effect Effects 0.000 description 1
• 238000001212 derivatisation Methods 0.000 description 1
• 238000001514 detection method Methods 0.000 description 1
• 238000011161 development Methods 0.000 description 1
• 201000009101 diabetic angiopathy Diseases 0.000 description 1
• LZPVNFLWFSSMJC-UHFFFAOYSA-N dichloromethane;n,n-diethylethanamine;methanol Chemical compound OC.ClCCl.CCN(CC)CC LZPVNFLWFSSMJC-UHFFFAOYSA-N 0.000 description 1
• ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
• SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
• 229940043279 diisopropylamine Drugs 0.000 description 1
• 238000010790 dilution Methods 0.000 description 1
• 239000012895 dilution Substances 0.000 description 1
• 239000002270 dispersing agent Substances 0.000 description 1
• 238000004090 dissolution Methods 0.000 description 1
• 239000008298 dragée Substances 0.000 description 1
• 238000007876 drug discovery Methods 0.000 description 1
• 238000010410 dusting Methods 0.000 description 1
• 230000000694 effects Effects 0.000 description 1
• 238000010828 elution Methods 0.000 description 1
• 230000010102 embolization Effects 0.000 description 1
• 239000003995 emulsifying agent Substances 0.000 description 1
• 239000002702 enteric coating Substances 0.000 description 1
• 238000009505 enteric coating Methods 0.000 description 1
• 238000006911 enzymatic reaction Methods 0.000 description 1
• 229940088598 enzyme Drugs 0.000 description 1
• GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
• SYKSWMRKMBTSMG-UHFFFAOYSA-N ethyl 1-(4-aminophenyl)piperidine-2-carboxylate Chemical compound CCOC(=O)C1CCCCN1C1=CC=C(N)C=C1 SYKSWMRKMBTSMG-UHFFFAOYSA-N 0.000 description 1
• NMCRRSVXBVKKFL-UHFFFAOYSA-N ethyl 1-[4-[5-[[(5-chlorothiophene-2-carbonyl)amino]methyl]-2-oxo-1,3-oxazolidin-3-yl]phenyl]piperidine-2-carboxylate Chemical compound CCOC(=O)C1CCCCN1C1=CC=C(N2C(OC(CNC(=O)C=3SC(Cl)=CC=3)C2)=O)C=C1 NMCRRSVXBVKKFL-UHFFFAOYSA-N 0.000 description 1
• NTDSBWRJJRHKKH-UHFFFAOYSA-N ethyl 1-[4-[[3-[(5-chlorothiophene-2-carbonyl)amino]-2-hydroxypropyl]amino]phenyl]piperidine-2-carboxylate Chemical compound CCOC(=O)C1CCCCN1C(C=C1)=CC=C1NCC(O)CNC(=O)C1=CC=C(Cl)S1 NTDSBWRJJRHKKH-UHFFFAOYSA-N 0.000 description 1
• OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 1
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 229940012414 factor viia Drugs 0.000 description 1
• 239000000796 flavoring agent Substances 0.000 description 1
• 125000001153 fluoro group Chemical group F* 0.000 description 1
• 239000006260 foam Substances 0.000 description 1
• 235000013355 food flavoring agent Nutrition 0.000 description 1
• 238000009472 formulation Methods 0.000 description 1
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
• 239000001530 fumaric acid Substances 0.000 description 1
• 235000011087 fumaric acid Nutrition 0.000 description 1
• 125000000524 functional group Chemical group 0.000 description 1
• 239000007789 gas Substances 0.000 description 1
• 239000007903 gelatin capsule Substances 0.000 description 1
• 229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 1
• 239000008103 glucose Substances 0.000 description 1
• 150000008282 halocarbons Chemical class 0.000 description 1
• 230000002439 hemostatic effect Effects 0.000 description 1
• GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
• 150000004677 hydrates Chemical class 0.000 description 1
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
• 229930195733 hydrocarbon Natural products 0.000 description 1
• 150000002430 hydrocarbons Chemical class 0.000 description 1
• 150000002431 hydrogen Chemical class 0.000 description 1
• 229910000041 hydrogen chloride Inorganic materials 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
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
• 230000001146 hypoxic effect Effects 0.000 description 1
• 239000005457 ice water Substances 0.000 description 1
• LFKYBJLFJOOKAE-UHFFFAOYSA-N imidazol-2-ylidenemethanone Chemical compound O=C=C1N=CC=N1 LFKYBJLFJOOKAE-UHFFFAOYSA-N 0.000 description 1
• 125000002636 imidazolinyl group Chemical group 0.000 description 1
• 125000002883 imidazolyl group Chemical group 0.000 description 1
• 238000001727 in vivo Methods 0.000 description 1
• 238000011534 incubation Methods 0.000 description 1
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
• 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
• 125000001041 indolyl group Chemical group 0.000 description 1
• 238000001802 infusion Methods 0.000 description 1
• 230000002401 inhibitory effect Effects 0.000 description 1
• 230000000977 initiatory effect Effects 0.000 description 1
• 208000014674 injury Diseases 0.000 description 1
• 150000007529 inorganic bases Chemical class 0.000 description 1
• 229910052500 inorganic mineral Inorganic materials 0.000 description 1
• 239000001023 inorganic pigment Substances 0.000 description 1
• 239000000543 intermediate Substances 0.000 description 1
• 238000001361 intraarterial administration Methods 0.000 description 1
• 238000007913 intrathecal administration Methods 0.000 description 1
• 229910052740 iodine Chemical group 0.000 description 1
• 239000011630 iodine Chemical group 0.000 description 1
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 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
• 239000012948 isocyanate Substances 0.000 description 1
• 150000002513 isocyanates Chemical class 0.000 description 1
• NIZHERJWXFHGGU-UHFFFAOYSA-N isocyanato(trimethyl)silane Chemical compound C[Si](C)(C)N=C=O NIZHERJWXFHGGU-UHFFFAOYSA-N 0.000 description 1
• 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([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
• 125000005956 isoquinolyl group Chemical group 0.000 description 1
• 125000000842 isoxazolyl group Chemical group 0.000 description 1
• 239000004310 lactic acid Substances 0.000 description 1
• 235000014655 lactic acid Nutrition 0.000 description 1
• 229940057995 liquid paraffin Drugs 0.000 description 1
• 239000006193 liquid solution 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
• DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
• 210000004185 liver Anatomy 0.000 description 1
• 239000006210 lotion Substances 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• 159000000003 magnesium salts Chemical class 0.000 description 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• 239000011976 maleic acid Substances 0.000 description 1
• 239000001630 malic acid Substances 0.000 description 1
• 235000011090 malic acid Nutrition 0.000 description 1
• 239000000594 mannitol Substances 0.000 description 1
• 235000010355 mannitol Nutrition 0.000 description 1
• 239000000463 material Substances 0.000 description 1
• 230000001404 mediated effect Effects 0.000 description 1
• 230000002503 metabolic effect Effects 0.000 description 1
• LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
• 229940098779 methanesulfonic acid Drugs 0.000 description 1
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
• 230000004089 microcirculation Effects 0.000 description 1
• 239000008108 microcrystalline cellulose Substances 0.000 description 1
• 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
• 229940016286 microcrystalline cellulose Drugs 0.000 description 1
• 210000004088 microvessel Anatomy 0.000 description 1
• 235000013336 milk Nutrition 0.000 description 1
• 239000008267 milk Substances 0.000 description 1
• 210000004080 milk Anatomy 0.000 description 1
• 235000010755 mineral Nutrition 0.000 description 1
• 239000011707 mineral Substances 0.000 description 1
• 208000015994 miscarriage Diseases 0.000 description 1
• 229960004857 mitomycin Drugs 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• 239000002899 monoamine oxidase inhibitor Substances 0.000 description 1
• NALMPLUMOWIVJC-UHFFFAOYSA-N n,n,4-trimethylbenzeneamine oxide Chemical compound CC1=CC=C([N+](C)(C)[O-])C=C1 NALMPLUMOWIVJC-UHFFFAOYSA-N 0.000 description 1
• LSEBNNVPNHIBJL-UHFFFAOYSA-N n-(3-anilino-2-hydroxypropyl)-5-chlorothiophene-2-carboxamide Chemical compound C=1C=CC=CC=1NCC(O)CNC(=O)C1=CC=C(Cl)S1 LSEBNNVPNHIBJL-UHFFFAOYSA-N 0.000 description 1
• QFELUFGHFLYZEZ-UHFFFAOYSA-N n-(4-aminophenyl)-n-methylacetamide Chemical compound CC(=O)N(C)C1=CC=C(N)C=C1 QFELUFGHFLYZEZ-UHFFFAOYSA-N 0.000 description 1
• GPLWJZMYONSNHQ-UHFFFAOYSA-N n-[(3-benzyl-2-oxo-1,3-oxazolidin-5-yl)methyl]-5-chlorothiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1OC(=O)N(CC=2C=CC=CC=2)C1 GPLWJZMYONSNHQ-UHFFFAOYSA-N 0.000 description 1
• MPPGNRZLQFQBSG-UHFFFAOYSA-N n-[3-(3-acetyl-4-morpholin-4-ylanilino)-2-hydroxypropyl]-5-chlorothiophene-2-carboxamide Chemical compound C=1C=C(N2CCOCC2)C(C(=O)C)=CC=1NCC(O)CNC(=O)C1=CC=C(Cl)S1 MPPGNRZLQFQBSG-UHFFFAOYSA-N 0.000 description 1
• TYRCYIDQBNIZIZ-UHFFFAOYSA-N n-[3-(3-carbamoyl-4-morpholin-4-ylanilino)-2-hydroxypropyl]-5-chlorothiophene-2-carboxamide Chemical compound C=1C=C(N2CCOCC2)C(C(=O)N)=CC=1NCC(O)CNC(=O)C1=CC=C(Cl)S1 TYRCYIDQBNIZIZ-UHFFFAOYSA-N 0.000 description 1
• MORAMQXLQFKNTC-UHFFFAOYSA-N n-[3-[3-amino-4-(3-oxomorpholin-4-yl)anilino]-2-hydroxypropyl]-5-chlorothiophene-2-carboxamide Chemical compound C=1C=C(N2C(COCC2)=O)C(N)=CC=1NCC(O)CNC(=O)C1=CC=C(Cl)S1 MORAMQXLQFKNTC-UHFFFAOYSA-N 0.000 description 1
• BJUNVMRXLXFTHE-UHFFFAOYSA-N n-[3-[4-[acetyl(methyl)amino]anilino]-2-hydroxypropyl]-5-chlorothiophene-2-carboxamide Chemical compound C1=CC(N(C(C)=O)C)=CC=C1NCC(O)CNC(=O)C1=CC=C(Cl)S1 BJUNVMRXLXFTHE-UHFFFAOYSA-N 0.000 description 1
• YBADWWMMZZTPMY-UHFFFAOYSA-N n-[4-[5-[[(5-chlorothiophene-2-carbonyl)amino]methyl]-2-oxo-1,3-oxazolidin-3-yl]phenyl]-3,5-dimethyl-1,2-oxazole-4-carboxamide Chemical compound CC1=NOC(C)=C1C(=O)NC1=CC=C(N2C(OC(CNC(=O)C=3SC(Cl)=CC=3)C2)=O)C=C1 YBADWWMMZZTPMY-UHFFFAOYSA-N 0.000 description 1
• QOWLKZRBOPUDMF-HNNXBMFYSA-N n-[[(5s)-3-(3-fluoro-4-thiomorpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]-5-methylthiophene-2-carboxamide Chemical compound S1C(C)=CC=C1C(=O)NC[C@@H]1OC(=O)N(C=2C=C(F)C(N3CCSCC3)=CC=2)C1 QOWLKZRBOPUDMF-HNNXBMFYSA-N 0.000 description 1
• GIXLIWAEQBSWQF-ZDUSSCGKSA-N n-[[(5s)-3-[4-(3-bromopropanoylamino)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NC[C@@H]1OC(=O)N(C=2C=CC(NC(=O)CCBr)=CC=2)C1 GIXLIWAEQBSWQF-ZDUSSCGKSA-N 0.000 description 1
• UBRFEYZOFGCGPG-ZDUSSCGKSA-N n-[[(5s)-3-[4-(azetidin-1-ylsulfonyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NC[C@@H]1OC(=O)N(C=2C=CC(=CC=2)S(=O)(=O)N2CCC2)C1 UBRFEYZOFGCGPG-ZDUSSCGKSA-N 0.000 description 1
• QGAHLMALZJUCBJ-LMRHVHIWSA-N n-[[(5s)-3-[4-[(3r)-3-amino-2-oxopyrrolidin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]-5-chlorothiophene-2-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.O=C1[C@H](N)CCN1C1=CC=C(N2C(O[C@@H](CNC(=O)C=3SC(Cl)=CC=3)C2)=O)C=C1 QGAHLMALZJUCBJ-LMRHVHIWSA-N 0.000 description 1
• XVEMBZCTWXFDEQ-UHFFFAOYSA-N n-[[2-oxo-3-[4-(2-oxopyrrolidin-1-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound C=1C=CSC=1C(=O)NCC(OC1=O)CN1C(C=C1)=CC=C1N1CCCC1=O XVEMBZCTWXFDEQ-UHFFFAOYSA-N 0.000 description 1
• JWDAIONOPSCCPT-UHFFFAOYSA-N n-[[3-(3-acetamido-4-pyrrolidin-1-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound CC(=O)NC1=CC(N2C(OC(CNC(=O)C=3SC(Cl)=CC=3)C2)=O)=CC=C1N1CCCC1 JWDAIONOPSCCPT-UHFFFAOYSA-N 0.000 description 1
• LXYHSFHUIZPJCD-UHFFFAOYSA-N n-[[3-(3-acetyl-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound CC(=O)C1=CC(N2C(OC(CNC(=O)C=3SC(Cl)=CC=3)C2)=O)=CC=C1N1CCOCC1 LXYHSFHUIZPJCD-UHFFFAOYSA-N 0.000 description 1
• MNEJYVBQMDHDJW-UHFFFAOYSA-N n-[[3-(3-amino-4-piperidin-1-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound NC1=CC(N2C(OC(CNC(=O)C=3SC(Cl)=CC=3)C2)=O)=CC=C1N1CCCCC1 MNEJYVBQMDHDJW-UHFFFAOYSA-N 0.000 description 1
• XEVPKKMPKZYKRM-UHFFFAOYSA-N n-[[3-(3-amino-4-pyrrolidin-1-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound NC1=CC(N2C(OC(CNC(=O)C=3SC(Cl)=CC=3)C2)=O)=CC=C1N1CCCC1 XEVPKKMPKZYKRM-UHFFFAOYSA-N 0.000 description 1
• YHWFFKBTUDKTHG-UHFFFAOYSA-N n-[[3-(3-carbamoyl-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound NC(=O)C1=CC(N2C(OC(CNC(=O)C=3SC(Cl)=CC=3)C2)=O)=CC=C1N1CCOCC1 YHWFFKBTUDKTHG-UHFFFAOYSA-N 0.000 description 1
• BXMKQFJSSNEYSN-UHFFFAOYSA-N n-[[3-(4-acetamidophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound C1=CC(NC(=O)C)=CC=C1N1C(=O)OC(CNC(=O)C=2SC(Cl)=CC=2)C1 BXMKQFJSSNEYSN-UHFFFAOYSA-N 0.000 description 1
• YNJCAKBMZXWXFW-UHFFFAOYSA-N n-[[3-[3-(2-amino-2-iminoethyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound NC(=N)CC1=CC=CC(N2C(OC(CNC(=O)C=3SC(Cl)=CC=3)C2)=O)=C1 YNJCAKBMZXWXFW-UHFFFAOYSA-N 0.000 description 1
• IDYPOYBBRVGBAW-UHFFFAOYSA-N n-[[3-[3-(3-aminopropanoylamino)-4-(3-hydroxypropylamino)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound C1=C(NCCCO)C(NC(=O)CCN)=CC(N2C(OC(CNC(=O)C=3SC(Cl)=CC=3)C2)=O)=C1 IDYPOYBBRVGBAW-UHFFFAOYSA-N 0.000 description 1
• INLXEGDYWOAZAA-UHFFFAOYSA-N n-[[3-[3-amino-4-(3-oxomorpholin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound NC1=CC(N2C(OC(CNC(=O)C=3SC(Cl)=CC=3)C2)=O)=CC=C1N1CCOCC1=O INLXEGDYWOAZAA-UHFFFAOYSA-N 0.000 description 1
• SJSHNMCDQUNQDA-UHFFFAOYSA-N n-[[3-[4-(2-amino-2-cyclopentyliminoethyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1OC(=O)N(C=2C=CC(CC(=N)NC3CCCC3)=CC=2)C1 SJSHNMCDQUNQDA-UHFFFAOYSA-N 0.000 description 1
• NCGZANAEJURZIR-UHFFFAOYSA-N n-[[3-[4-(2-amino-2-iminoethyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound C1=CC(CC(=N)N)=CC=C1N1C(=O)OC(CNC(=O)C=2SC(Cl)=CC=2)C1 NCGZANAEJURZIR-UHFFFAOYSA-N 0.000 description 1
• UJKUWPIUQWPJAJ-UHFFFAOYSA-N n-[[3-[4-(2-amino-2-phenyliminoethyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1OC(=O)N(C=2C=CC(CC(=N)NC=3C=CC=CC=3)=CC=2)C1 UJKUWPIUQWPJAJ-UHFFFAOYSA-N 0.000 description 1
• NKXFERSMJVXBHV-UHFFFAOYSA-N n-[[3-[4-(2-amino-2-pyridin-2-yliminoethyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1OC(=O)N(C=2C=CC(CC(=N)NC=3N=CC=CC=3)=CC=2)C1 NKXFERSMJVXBHV-UHFFFAOYSA-N 0.000 description 1
• UXJNFKXJLUIZHS-UHFFFAOYSA-N n-[[3-[4-(3-aminopyrrolidin-1-yl)-3-nitrophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound C1C(N)CCN1C1=CC=C(N2C(OC(CNC(=O)C=3SC(Cl)=CC=3)C2)=O)C=C1[N+]([O-])=O UXJNFKXJLUIZHS-UHFFFAOYSA-N 0.000 description 1
• OSQBVNRIDCZDCS-UHFFFAOYSA-N n-[[3-[4-(acetamidomethyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound C1=CC(CNC(=O)C)=CC=C1N1C(=O)OC(CNC(=O)C=2SC(Cl)=CC=2)C1 OSQBVNRIDCZDCS-UHFFFAOYSA-N 0.000 description 1
• BTTMEOJYEMXTOD-UHFFFAOYSA-N n-[[3-[4-(aminomethyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound C1=CC(CN)=CC=C1N1C(=O)OC(CNC(=O)C=2SC(Cl)=CC=2)C1 BTTMEOJYEMXTOD-UHFFFAOYSA-N 0.000 description 1
• SQPPEVRCRPVSFD-UHFFFAOYSA-N n-[[3-[4-[(2-aminoacetyl)amino]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound C1=CC(NC(=O)CN)=CC=C1N1C(=O)OC(CNC(=O)C=2SC(Cl)=CC=2)C1 SQPPEVRCRPVSFD-UHFFFAOYSA-N 0.000 description 1
• VEDPEZVHGAYYBV-UHFFFAOYSA-N n-[[3-[4-[(carbamoylamino)methyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound C1=CC(CNC(=O)N)=CC=C1N1C(=O)OC(CNC(=O)C=2SC(Cl)=CC=2)C1 VEDPEZVHGAYYBV-UHFFFAOYSA-N 0.000 description 1
• CCSYXCMSRWYLDO-UHFFFAOYSA-N n-[[3-[4-[2-amino-2-(2,2,2-trifluoroethylimino)ethyl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound C1=CC(CC(=N)NCC(F)(F)F)=CC=C1N1C(=O)OC(CNC(=O)C=2SC(Cl)=CC=2)C1 CCSYXCMSRWYLDO-UHFFFAOYSA-N 0.000 description 1
• XCYOXLDFXWCASJ-UHFFFAOYSA-N n-[[3-[4-[acetyl(cyclopropyl)amino]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound C=1C=C(N2C(OC(CNC(=O)C=3SC(Cl)=CC=3)C2)=O)C=CC=1N(C(=O)C)C1CC1 XCYOXLDFXWCASJ-UHFFFAOYSA-N 0.000 description 1
• QGJUIIVNTVDABG-UHFFFAOYSA-N n-[[3-[4-[acetyl(methyl)amino]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]-5-chlorothiophene-2-carboxamide Chemical compound C1=CC(N(C(C)=O)C)=CC=C1N1C(=O)OC(CNC(=O)C=2SC(Cl)=CC=2)C1 QGJUIIVNTVDABG-UHFFFAOYSA-N 0.000 description 1
• MIYKHJXFICMPOJ-UHFFFAOYSA-N n-benzyl-1-phenylmethanimine Chemical compound C=1C=CC=CC=1CN=CC1=CC=CC=C1 MIYKHJXFICMPOJ-UHFFFAOYSA-N 0.000 description 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
• JNUIOYAYNFFHTC-UHFFFAOYSA-N n-methylthiophene-2-carboxamide Chemical group CNC(=O)C1=CC=CS1 JNUIOYAYNFFHTC-UHFFFAOYSA-N 0.000 description 1
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
• 239000007923 nasal drop Substances 0.000 description 1
• 229940100662 nasal drops Drugs 0.000 description 1
• 229920005615 natural polymer Polymers 0.000 description 1
• 150000005181 nitrobenzenes Chemical class 0.000 description 1
• 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
• 230000001453 nonthrombogenic effect Effects 0.000 description 1
• 239000002674 ointment Substances 0.000 description 1
• 229940049964 oleate Drugs 0.000 description 1
• ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
• 229940100688 oral solution Drugs 0.000 description 1
• 229940100692 oral suspension Drugs 0.000 description 1
• 150000007530 organic bases Chemical class 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• 125000002971 oxazolyl group Chemical group 0.000 description 1
• 125000004430 oxygen atom Chemical group O* 0.000 description 1
• 239000012188 paraffin wax Substances 0.000 description 1
• 239000006072 paste Substances 0.000 description 1
• 230000008506 pathogenesis Effects 0.000 description 1
• 230000001991 pathophysiological effect Effects 0.000 description 1
• 239000008188 pellet Substances 0.000 description 1
• 230000000144 pharmacologic effect Effects 0.000 description 1
• 238000005191 phase separation Methods 0.000 description 1
• 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
• BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 1
• XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
• 230000001766 physiological effect Effects 0.000 description 1
• 125000004193 piperazinyl group Chemical group 0.000 description 1
• 230000010118 platelet activation Effects 0.000 description 1
• 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
• BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
• 159000000001 potassium salts Chemical class 0.000 description 1
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
• 238000012746 preparative thin layer chromatography Methods 0.000 description 1
• MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
• 229960004919 procaine Drugs 0.000 description 1
• 230000000750 progressive effect Effects 0.000 description 1
• 230000002035 prolonged effect Effects 0.000 description 1
• 235000019260 propionic acid Nutrition 0.000 description 1
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
• 230000002685 pulmonary effect Effects 0.000 description 1
• 125000003373 pyrazinyl group Chemical group 0.000 description 1
• 125000003226 pyrazolyl group Chemical group 0.000 description 1
• 125000001422 pyrrolinyl group Chemical group 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
• 125000005493 quinolyl group Chemical group 0.000 description 1
• 230000002829 reductive effect Effects 0.000 description 1
• 238000011160 research Methods 0.000 description 1
• 230000004044 response Effects 0.000 description 1
• 230000004264 retinal detachment Effects 0.000 description 1
• 238000012552 review Methods 0.000 description 1
• 238000007363 ring formation reaction Methods 0.000 description 1
• 229940069575 rompun Drugs 0.000 description 1
• 239000012047 saturated solution Substances 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
• ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
• 235000017557 sodium bicarbonate Nutrition 0.000 description 1
• WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
• 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
• 239000012312 sodium hydride Substances 0.000 description 1
• 239000011697 sodium iodate Substances 0.000 description 1
• 235000015281 sodium iodate Nutrition 0.000 description 1
• 229940032753 sodium iodate Drugs 0.000 description 1
• MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
• 239000011877 solvent mixture Substances 0.000 description 1
• 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
• 239000007921 spray Substances 0.000 description 1
• 239000003381 stabilizer Substances 0.000 description 1
• 239000008107 starch Substances 0.000 description 1
• 235000019698 starch Nutrition 0.000 description 1
• 230000036262 stenosis Effects 0.000 description 1
• 208000037804 stenosis Diseases 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• 125000003107 substituted aryl group Chemical group 0.000 description 1
• 125000000565 sulfonamide group Chemical group 0.000 description 1
• 150000003460 sulfonic acids Chemical class 0.000 description 1
• 239000006228 supernatant Substances 0.000 description 1
• 239000000829 suppository Substances 0.000 description 1
• 229920001059 synthetic polymer Polymers 0.000 description 1
• 239000011975 tartaric acid Substances 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• PCEMTBKNDSHYGA-AWEZNQCLSA-N tert-butyl 4-[4-[(5s)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=C(N2C(O[C@@H](CN)C2)=O)C=C1F PCEMTBKNDSHYGA-AWEZNQCLSA-N 0.000 description 1
• LLTHQDWVWAPJQT-INIZCTEOSA-N tert-butyl 4-[4-[(5s)-5-[[(5-chlorothiophene-2-carbonyl)amino]methyl]-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=C(N2C(O[C@@H](CNC(=O)C=3SC(Cl)=CC=3)C2)=O)C=C1F LLTHQDWVWAPJQT-INIZCTEOSA-N 0.000 description 1
• WTHJFJGQTBGBRJ-UHFFFAOYSA-N tert-butyl 4-[4-[5-[[(5-chlorothiophene-2-carbonyl)amino]methyl]-2-oxo-1,3-oxazolidin-3-yl]phenyl]-3,5-dioxopiperazine-1-carboxylate Chemical compound O=C1CN(C(=O)OC(C)(C)C)CC(=O)N1C1=CC=C(N2C(OC(CNC(=O)C=3SC(Cl)=CC=3)C2)=O)C=C1 WTHJFJGQTBGBRJ-UHFFFAOYSA-N 0.000 description 1
• WIVYTYZCVWHWSH-UHFFFAOYSA-N tert-butyl n-(4-aminophenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(N)C=C1 WIVYTYZCVWHWSH-UHFFFAOYSA-N 0.000 description 1
• RITLKULOFFEIBW-DLBZAZTESA-N tert-butyl n-[(3r)-1-[4-[(5s)-5-[[(5-chlorothiophene-2-carbonyl)amino]methyl]-2-oxo-1,3-oxazolidin-3-yl]phenyl]-2-oxopyrrolidin-3-yl]carbamate Chemical compound O=C1[C@H](NC(=O)OC(C)(C)C)CCN1C1=CC=C(N2C(O[C@@H](CNC(=O)C=3SC(Cl)=CC=3)C2)=O)C=C1 RITLKULOFFEIBW-DLBZAZTESA-N 0.000 description 1
• DQQJBEAXSOOCPG-ZETCQYMHSA-N tert-butyl n-[(3s)-pyrrolidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H]1CCNC1 DQQJBEAXSOOCPG-ZETCQYMHSA-N 0.000 description 1
• DOXDHYXNJADXDZ-UHFFFAOYSA-N tert-butyl n-[2-[4-[5-[[(5-chlorothiophene-2-carbonyl)amino]methyl]-2-oxo-1,3-oxazolidin-3-yl]anilino]-2-oxoethyl]carbamate Chemical compound C1=CC(NC(=O)CNC(=O)OC(C)(C)C)=CC=C1N1C(=O)OC(CNC(=O)C=2SC(Cl)=CC=2)C1 DOXDHYXNJADXDZ-UHFFFAOYSA-N 0.000 description 1
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
• WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
• 230000001225 therapeutic effect Effects 0.000 description 1
• 125000000335 thiazolyl group Chemical group 0.000 description 1
• 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
• DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 description 1
• 239000003868 thrombin inhibitor Substances 0.000 description 1
• 230000002885 thrombogenetic effect Effects 0.000 description 1
• 230000001732 thrombotic effect Effects 0.000 description 1
• 210000002105 tongue Anatomy 0.000 description 1
• CMMXCVYESRODNH-UHFFFAOYSA-N trichloroepoxyethane Chemical class ClC1OC1(Cl)Cl CMMXCVYESRODNH-UHFFFAOYSA-N 0.000 description 1
• VFJYIHQDILEQNR-UHFFFAOYSA-M trimethylsulfanium;iodide Chemical compound [I-].C[S+](C)C VFJYIHQDILEQNR-UHFFFAOYSA-M 0.000 description 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
• 229920002554 vinyl polymer Polymers 0.000 description 1
• 239000003643 water by type Substances 0.000 description 1
• 238000005303 weighing Methods 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1
• 239000000230 xanthan gum Substances 0.000 description 1
• 229920001285 xanthan gum Polymers 0.000 description 1
• 235000010493 xanthan gum Nutrition 0.000 description 1
• 229940082509 xanthan gum Drugs 0.000 description 1
• QYEFBJRXKKSABU-UHFFFAOYSA-N xylazine hydrochloride Chemical compound Cl.CC1=CC=CC(C)=C1NC1=NCCCS1 QYEFBJRXKKSABU-UHFFFAOYSA-N 0.000 description 1