MXPA01013004A - Antagonistas del receptor de interleucina-8. - Google Patents
Antagonistas del receptor de interleucina-8.Info
- Publication number
- MXPA01013004A MXPA01013004A MXPA01013004A MXPA01013004A MXPA01013004A MX PA01013004 A MXPA01013004 A MX PA01013004A MX PA01013004 A MXPA01013004 A MX PA01013004A MX PA01013004 A MXPA01013004 A MX PA01013004A MX PA01013004 A MXPA01013004 A MX PA01013004A
- Authority
- MX
- Mexico
- Prior art keywords
- urea
- hydroxy
- bromophenyl
- alkyl
- phenyl
- Prior art date
Links
- 102000010681 interleukin-8 receptors Human genes 0.000 title description 6
- 108010038415 interleukin-8 receptors Proteins 0.000 title description 5
- 239000002464 receptor antagonist Substances 0.000 title 1
- 229940044551 receptor antagonist Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 189
- 102000019034 Chemokines Human genes 0.000 claims abstract description 36
- 108010012236 Chemokines Proteins 0.000 claims abstract description 36
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 35
- 201000010099 disease Diseases 0.000 claims abstract description 34
- 150000003839 salts Chemical class 0.000 claims abstract description 26
- 230000001404 mediated effect Effects 0.000 claims abstract description 18
- 102000012740 beta Adrenergic Receptors Human genes 0.000 claims abstract description 11
- 108010079452 beta Adrenergic Receptors Proteins 0.000 claims abstract description 11
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 208
- -1 C1-10 alkyl halogen Chemical class 0.000 claims description 146
- 239000004202 carbamide Substances 0.000 claims description 111
- 125000000217 alkyl group Chemical group 0.000 claims description 108
- 229910052739 hydrogen Inorganic materials 0.000 claims description 106
- 239000001257 hydrogen Substances 0.000 claims description 94
- 125000000623 heterocyclic group Chemical group 0.000 claims description 81
- 229910052736 halogen Inorganic materials 0.000 claims description 71
- 125000001072 heteroaryl group Chemical group 0.000 claims description 60
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 54
- 150000002367 halogens Chemical class 0.000 claims description 54
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 46
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 45
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 39
- 125000003545 alkoxy group Chemical group 0.000 claims description 37
- 125000003118 aryl group Chemical group 0.000 claims description 33
- 125000003107 substituted aryl group Chemical group 0.000 claims description 29
- 125000003342 alkenyl group Chemical group 0.000 claims description 25
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
- 125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 23
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 150000001540 azides Chemical class 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 125000004104 aryloxy group Chemical group 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- 229910052717 sulfur Chemical group 0.000 claims description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 14
- 239000011593 sulfur Chemical group 0.000 claims description 14
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 13
- 241000124008 Mammalia Species 0.000 claims description 12
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 11
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
- 229940124530 sulfonamide Drugs 0.000 claims description 8
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 150000003456 sulfonamides Chemical class 0.000 claims description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- UUDFKBXAWIEQJG-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(2-hydroxy-3-nitrophenyl)urea Chemical compound C1=CC=C([N+]([O-])=O)C(O)=C1NC(=O)NC1=CC=CC=C1Br UUDFKBXAWIEQJG-UHFFFAOYSA-N 0.000 claims description 6
- XJGIXEVHERZBQV-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(3-cyano-2-hydroxyphenyl)urea Chemical compound C1=CC=C(C#N)C(O)=C1NC(=O)NC1=CC=CC=C1Br XJGIXEVHERZBQV-UHFFFAOYSA-N 0.000 claims description 6
- 108010018976 Interleukin-8A Receptors Proteins 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000002950 monocyclic group Chemical group 0.000 claims description 5
- GZOMTDYQJHIAGF-UHFFFAOYSA-N 1-(2,3-dichlorophenyl)-3-(2-hydroxy-5-nitrophenyl)urea Chemical compound OC1=CC=C([N+]([O-])=O)C=C1NC(=O)NC1=CC=CC(Cl)=C1Cl GZOMTDYQJHIAGF-UHFFFAOYSA-N 0.000 claims description 4
- PEBCQTKZVQCXJP-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(3,4-dichloro-2-hydroxyphenyl)urea Chemical compound OC1=C(Cl)C(Cl)=CC=C1NC(=O)NC1=CC=CC=C1Br PEBCQTKZVQCXJP-UHFFFAOYSA-N 0.000 claims description 4
- VIKJECVSALYBJB-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(4-cyano-2-hydroxyphenyl)urea Chemical compound OC1=CC(C#N)=CC=C1NC(=O)NC1=CC=CC=C1Br VIKJECVSALYBJB-UHFFFAOYSA-N 0.000 claims description 4
- JFLMWUAMXJXUAG-UHFFFAOYSA-N 1-(2-chlorophenyl)-3-(2-hydroxy-4-nitrophenyl)urea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=CC=CC=C1Cl JFLMWUAMXJXUAG-UHFFFAOYSA-N 0.000 claims description 4
- KNPLCJZGNRGZAN-UHFFFAOYSA-N 1-(2-hydroxy-4-nitrophenyl)-3-(2-methoxyphenyl)urea Chemical compound COC1=CC=CC=C1NC(=O)NC1=CC=C([N+]([O-])=O)C=C1O KNPLCJZGNRGZAN-UHFFFAOYSA-N 0.000 claims description 4
- UZWXETXUKFOJFK-UHFFFAOYSA-N 1-(2-hydroxy-4-nitrophenyl)-3-(2-methylsulfanylphenyl)urea Chemical compound CSC1=CC=CC=C1NC(=O)NC1=CC=C([N+]([O-])=O)C=C1O UZWXETXUKFOJFK-UHFFFAOYSA-N 0.000 claims description 4
- MHEWCJHSRKVNIF-UHFFFAOYSA-N 1-(2-hydroxy-4-nitrophenyl)-3-(2-phenoxyphenyl)urea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=CC=CC=C1OC1=CC=CC=C1 MHEWCJHSRKVNIF-UHFFFAOYSA-N 0.000 claims description 4
- PXEWTGQJHBTLOG-UHFFFAOYSA-N 1-(3,4-dichloro-2-hydroxyphenyl)-3-(2-methoxyphenyl)urea Chemical compound COC1=CC=CC=C1NC(=O)NC1=CC=C(Cl)C(Cl)=C1O PXEWTGQJHBTLOG-UHFFFAOYSA-N 0.000 claims description 4
- UROHGCKFAXVYKN-UHFFFAOYSA-N 1-(3,4-dichloro-2-hydroxyphenyl)-3-(2-phenylphenyl)urea Chemical compound OC1=C(Cl)C(Cl)=CC=C1NC(=O)NC1=CC=CC=C1C1=CC=CC=C1 UROHGCKFAXVYKN-UHFFFAOYSA-N 0.000 claims description 4
- GTJXCKKJNGSTCK-UHFFFAOYSA-N 1-(3-chloro-2-methoxyphenyl)-3-(2-hydroxy-4-nitrophenyl)urea Chemical compound COC1=C(Cl)C=CC=C1NC(=O)NC1=CC=C([N+]([O-])=O)C=C1O GTJXCKKJNGSTCK-UHFFFAOYSA-N 0.000 claims description 4
- IAIFWAOFGOIHNN-UHFFFAOYSA-N 1-(3-cyano-2-hydroxyphenyl)-3-(2,3-dichlorophenyl)urea Chemical compound C1=CC=C(C#N)C(O)=C1NC(=O)NC1=CC=CC(Cl)=C1Cl IAIFWAOFGOIHNN-UHFFFAOYSA-N 0.000 claims description 4
- DQRKQLTUZBFHPB-UHFFFAOYSA-N 1-(4-cyano-2-hydroxyphenyl)-3-(2,3-dichlorophenyl)urea Chemical compound OC1=CC(C#N)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1Cl DQRKQLTUZBFHPB-UHFFFAOYSA-N 0.000 claims description 4
- ZHFMJOHHDQGOTA-UHFFFAOYSA-N 1-(4-cyano-2-hydroxyphenyl)-3-(2-methoxyphenyl)urea Chemical compound COC1=CC=CC=C1NC(=O)NC1=CC=C(C#N)C=C1O ZHFMJOHHDQGOTA-UHFFFAOYSA-N 0.000 claims description 4
- WXLBSLQDYGMCGF-UHFFFAOYSA-N 1-(4-cyano-2-hydroxyphenyl)-3-(2-methylphenyl)urea Chemical compound CC1=CC=CC=C1NC(=O)NC1=CC=C(C#N)C=C1O WXLBSLQDYGMCGF-UHFFFAOYSA-N 0.000 claims description 4
- YZAZGBOPFBFDAC-UHFFFAOYSA-N 1-(4-cyano-2-hydroxyphenyl)-3-(2-phenylphenyl)urea Chemical compound OC1=CC(C#N)=CC=C1NC(=O)NC1=CC=CC=C1C1=CC=CC=C1 YZAZGBOPFBFDAC-UHFFFAOYSA-N 0.000 claims description 4
- 241000700605 Viruses Species 0.000 claims description 4
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 claims description 3
- CBPGTUOXTFTWTE-UHFFFAOYSA-N 1-(1,3-benzodioxol-4-yl)-3-(2-hydroxy-4-nitrophenyl)urea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=CC=CC2=C1OCO2 CBPGTUOXTFTWTE-UHFFFAOYSA-N 0.000 claims description 3
- WTBSKJMUSCALAE-UHFFFAOYSA-N 1-(2,3-dichlorophenyl)-3-(2-hydroxy-4-nitrophenyl)urea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1Cl WTBSKJMUSCALAE-UHFFFAOYSA-N 0.000 claims description 3
- DNYOWRQDSNGAQQ-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(3-cyano-2-hydroxy-4-methylphenyl)urea Chemical compound OC1=C(C#N)C(C)=CC=C1NC(=O)NC1=CC=CC=C1Br DNYOWRQDSNGAQQ-UHFFFAOYSA-N 0.000 claims description 3
- MPSVIJAQCVNHHQ-UHFFFAOYSA-N 1-(2-hydroxy-4-nitrophenyl)-3-(2-phenylphenyl)urea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=CC=CC=C1C1=CC=CC=C1 MPSVIJAQCVNHHQ-UHFFFAOYSA-N 0.000 claims description 3
- BNWWISXBCWURFH-UHFFFAOYSA-N 3-[(2-bromophenyl)carbamoylamino]-2-hydroxy-n-phenylbenzamide Chemical compound C1=CC=C(C(=O)NC=2C=CC=CC=2)C(O)=C1NC(=O)NC1=CC=CC=C1Br BNWWISXBCWURFH-UHFFFAOYSA-N 0.000 claims description 3
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- 241000723346 Cinnamomum camphora Species 0.000 claims description 3
- 208000001132 Osteoporosis Diseases 0.000 claims description 3
- 230000033115 angiogenesis Effects 0.000 claims description 3
- 229960000846 camphor Drugs 0.000 claims description 3
- 229930008380 camphor Natural products 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical group OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 208000007565 gingivitis Diseases 0.000 claims description 3
- 210000003958 hematopoietic stem cell Anatomy 0.000 claims description 3
- 201000004792 malaria Diseases 0.000 claims description 3
- 230000000241 respiratory effect Effects 0.000 claims description 3
- 150000003573 thiols Chemical group 0.000 claims description 3
- MQBZVUNNWUIPMK-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(2-hydroxy-4-nitrophenyl)urea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=CC=CC=C1Br MQBZVUNNWUIPMK-UHFFFAOYSA-N 0.000 claims description 2
- 241000711557 Hepacivirus Species 0.000 claims description 2
- 241000700721 Hepatitis B virus Species 0.000 claims description 2
- SBDNCFMDGBKCIR-UHFFFAOYSA-N OC1=C(C=CC(=C1)[N+](=O)[O-])N(C(=O)N)C1=C(C=CC=C1)I Chemical compound OC1=C(C=CC(=C1)[N+](=O)[O-])N(C(=O)N)C1=C(C=CC=C1)I SBDNCFMDGBKCIR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 208000006454 hepatitis Diseases 0.000 claims description 2
- 231100000283 hepatitis Toxicity 0.000 claims description 2
- 208000002672 hepatitis B Diseases 0.000 claims description 2
- 125000004001 thioalkyl group Chemical group 0.000 claims description 2
- 125000005000 thioaryl group Chemical group 0.000 claims description 2
- 241001529453 unidentified herpesvirus Species 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 4
- QIGMVYSPXPXCPN-UHFFFAOYSA-N (2-bromophenyl)thiourea Chemical compound NC(=S)NC1=CC=CC=C1Br QIGMVYSPXPXCPN-UHFFFAOYSA-N 0.000 claims 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 136
- 108090001007 Interleukin-8 Proteins 0.000 abstract description 64
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 553
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 399
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 258
- 238000002360 preparation method Methods 0.000 description 238
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 237
- 239000000047 product Substances 0.000 description 164
- 238000007429 general method Methods 0.000 description 140
- 238000005481 NMR spectroscopy Methods 0.000 description 131
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 118
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 113
- 238000001556 precipitation Methods 0.000 description 111
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 100
- 239000007787 solid Substances 0.000 description 96
- 239000011541 reaction mixture Substances 0.000 description 91
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 88
- 239000000741 silica gel Substances 0.000 description 85
- 229910002027 silica gel Inorganic materials 0.000 description 85
- 235000019439 ethyl acetate Nutrition 0.000 description 82
- 230000015572 biosynthetic process Effects 0.000 description 79
- 238000003786 synthesis reaction Methods 0.000 description 79
- 239000000243 solution Substances 0.000 description 76
- 238000004587 chromatography analysis Methods 0.000 description 71
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 66
- 239000002904 solvent Substances 0.000 description 63
- 102000004890 Interleukin-8 Human genes 0.000 description 62
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 61
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 61
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 60
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 60
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 60
- XKTZWUACRZHVAN-VADRZIEHSA-N interleukin-8 Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@@H](NC(C)=O)CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CCSC)C(=O)N1[C@H](CCC1)C(=O)N1[C@H](CCC1)C(=O)N[C@@H](C)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC(O)=CC=1)C(=O)N[C@H](CO)C(=O)N1[C@H](CCC1)C(N)=O)C1=CC=CC=C1 XKTZWUACRZHVAN-VADRZIEHSA-N 0.000 description 57
- 229940096397 interleukin-8 Drugs 0.000 description 57
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 56
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 55
- 239000000203 mixture Substances 0.000 description 54
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 52
- 238000010790 dilution Methods 0.000 description 47
- 239000012895 dilution Substances 0.000 description 47
- 239000000706 filtrate Substances 0.000 description 44
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 44
- 235000019341 magnesium sulphate Nutrition 0.000 description 44
- 102100034221 Growth-regulated alpha protein Human genes 0.000 description 42
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 42
- 229910001868 water Inorganic materials 0.000 description 42
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 40
- 239000000460 chlorine Substances 0.000 description 38
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 38
- DOPJTDJKZNWLRB-UHFFFAOYSA-N 2-Amino-5-nitrophenol Chemical compound NC1=CC=C([N+]([O-])=O)C=C1O DOPJTDJKZNWLRB-UHFFFAOYSA-N 0.000 description 33
- 229910052786 argon Inorganic materials 0.000 description 30
- 239000012044 organic layer Substances 0.000 description 30
- 239000012074 organic phase Substances 0.000 description 30
- 238000003756 stirring Methods 0.000 description 30
- 239000000463 material Substances 0.000 description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- QXEDXIJDCOADGG-UHFFFAOYSA-N (2-bromophenyl)urea Chemical compound NC(=O)NC1=CC=CC=C1Br QXEDXIJDCOADGG-UHFFFAOYSA-N 0.000 description 23
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 23
- 239000012267 brine Substances 0.000 description 23
- 230000003197 catalytic effect Effects 0.000 description 23
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 23
- 101001069921 Homo sapiens Growth-regulated alpha protein Proteins 0.000 description 22
- 230000002829 reductive effect Effects 0.000 description 21
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 20
- 101000973997 Homo sapiens Nucleosome assembly protein 1-like 4 Proteins 0.000 description 20
- 101000947178 Homo sapiens Platelet basic protein Proteins 0.000 description 20
- 102100036154 Platelet basic protein Human genes 0.000 description 20
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 20
- 239000004317 sodium nitrate Substances 0.000 description 20
- 235000010344 sodium nitrate Nutrition 0.000 description 20
- 235000011150 stannous chloride Nutrition 0.000 description 20
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 20
- 238000003818 flash chromatography Methods 0.000 description 19
- 235000010288 sodium nitrite Nutrition 0.000 description 19
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
- 229940086542 triethylamine Drugs 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- 210000000440 neutrophil Anatomy 0.000 description 17
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 17
- GOOVAYJIVMBWPP-UHFFFAOYSA-N 1-bromo-2-isocyanatobenzene Chemical compound BrC1=CC=CC=C1N=C=O GOOVAYJIVMBWPP-UHFFFAOYSA-N 0.000 description 16
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 16
- 210000004027 cell Anatomy 0.000 description 14
- 102000005962 receptors Human genes 0.000 description 13
- 108020003175 receptors Proteins 0.000 description 13
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 12
- HKZPOGZBKIWMPO-UHFFFAOYSA-N 4-amino-3-hydroxybenzonitrile Chemical compound NC1=CC=C(C#N)C=C1O HKZPOGZBKIWMPO-UHFFFAOYSA-N 0.000 description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- 125000001188 haloalkyl group Chemical group 0.000 description 12
- 229910052763 palladium Inorganic materials 0.000 description 12
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 11
- 239000000284 extract Substances 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 238000001953 recrystallisation Methods 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 9
- 238000004364 calculation method Methods 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 239000008194 pharmaceutical composition Substances 0.000 description 9
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 8
- FUZKSCLFHRBHJG-UHFFFAOYSA-N BrC1=C(C=CC=C1)NC(N)=O.NC(=O)N Chemical compound BrC1=C(C=CC=C1)NC(N)=O.NC(=O)N FUZKSCLFHRBHJG-UHFFFAOYSA-N 0.000 description 8
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
- 239000003085 diluting agent Substances 0.000 description 8
- 125000005114 heteroarylalkoxy group Chemical group 0.000 description 8
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 8
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical class NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 7
- LBKNLCXXJZQFHU-UHFFFAOYSA-N 6-amino-2,3-dichlorophenol Chemical compound NC1=CC=C(Cl)C(Cl)=C1O LBKNLCXXJZQFHU-UHFFFAOYSA-N 0.000 description 7
- 102000000589 Interleukin-1 Human genes 0.000 description 7
- 108010002352 Interleukin-1 Proteins 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 7
- 235000011054 acetic acid Nutrition 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- UFYKIHANBCVMKW-UHFFFAOYSA-N 1-(4-azido-2-hydroxyphenyl)-3-(2-methoxyphenyl)urea Chemical compound COC1=CC=CC=C1NC(=O)NC1=CC=C(N=[N+]=[N-])C=C1O UFYKIHANBCVMKW-UHFFFAOYSA-N 0.000 description 6
- VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 description 6
- FMQVUWGTHZPXQU-UHFFFAOYSA-N 3-amino-2-hydroxybenzonitrile Chemical compound NC1=CC=CC(C#N)=C1O FMQVUWGTHZPXQU-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- 102000004127 Cytokines Human genes 0.000 description 6
- 108090000695 Cytokines Proteins 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 230000004913 activation Effects 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 125000005504 styryl group Chemical group 0.000 description 6
- 206010040070 Septic Shock Diseases 0.000 description 5
- 210000001744 T-lymphocyte Anatomy 0.000 description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 230000035605 chemotaxis Effects 0.000 description 5
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 5
- 210000002889 endothelial cell Anatomy 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- DEVUYWTZRXOMSI-UHFFFAOYSA-N (sulfamoylamino)benzene Chemical compound NS(=O)(=O)NC1=CC=CC=C1 DEVUYWTZRXOMSI-UHFFFAOYSA-N 0.000 description 4
- JYYRLQNSIZPUPF-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(2-hydroxy-4-nitrophenyl)thiourea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=S)NC1=CC=CC=C1Br JYYRLQNSIZPUPF-UHFFFAOYSA-N 0.000 description 4
- PQAXIHNOJWBTGN-UHFFFAOYSA-N 1-(2-hydroxy-5-nitrophenyl)-3-(3-methoxythiophen-2-yl)urea Chemical compound C1=CSC(NC(=O)NC=2C(=CC=C(C=2)[N+]([O-])=O)O)=C1OC PQAXIHNOJWBTGN-UHFFFAOYSA-N 0.000 description 4
- IVTNMVXSFFOHJN-UHFFFAOYSA-N 1-(3-azido-2-hydroxyphenyl)-3-(2-bromophenyl)urea Chemical compound C1=CC=C(N=[N+]=[N-])C(O)=C1NC(=O)NC1=CC=CC=C1Br IVTNMVXSFFOHJN-UHFFFAOYSA-N 0.000 description 4
- IIDUNAVOCYMUFB-UHFFFAOYSA-N 2-amino-5-fluorophenol Chemical compound NC1=CC=C(F)C=C1O IIDUNAVOCYMUFB-UHFFFAOYSA-N 0.000 description 4
- IFCGVNYNIRTWNU-UHFFFAOYSA-N 2-amino-5-propan-2-ylphenol Chemical compound CC(C)C1=CC=C(N)C(O)=C1 IFCGVNYNIRTWNU-UHFFFAOYSA-N 0.000 description 4
- MPLDLWHRQIVKLC-UHFFFAOYSA-N 2-bromo-3-methyl-6-nitrophenol Chemical compound CC1=CC=C([N+]([O-])=O)C(O)=C1Br MPLDLWHRQIVKLC-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 101000611183 Homo sapiens Tumor necrosis factor Proteins 0.000 description 4
- 102000004889 Interleukin-6 Human genes 0.000 description 4
- 108090001005 Interleukin-6 Proteins 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 102100040247 Tumor necrosis factor Human genes 0.000 description 4
- 150000001448 anilines Chemical class 0.000 description 4
- 210000003651 basophil Anatomy 0.000 description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 4
- 235000015165 citric acid Nutrition 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 4
- 239000003937 drug carrier Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 230000006870 function Effects 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 230000008595 infiltration Effects 0.000 description 4
- 238000001764 infiltration Methods 0.000 description 4
- 230000002757 inflammatory effect Effects 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 229940100601 interleukin-6 Drugs 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000006210 lotion Substances 0.000 description 4
- 210000002540 macrophage Anatomy 0.000 description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
- 210000001616 monocyte Anatomy 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 210000003491 skin Anatomy 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 4
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 4
- IDEIMXJJLMVTNN-UHFFFAOYSA-N 1,3-bis(2-hydroxy-4-nitrophenyl)urea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=CC=C([N+]([O-])=O)C=C1O IDEIMXJJLMVTNN-UHFFFAOYSA-N 0.000 description 3
- MHNCVYSYIFOKDX-UHFFFAOYSA-N 1-(2,3-dichlorophenyl)-3-(2-hydroxy-3-phenylphenyl)urea Chemical compound C1=CC=C(C=2C=CC=CC=2)C(O)=C1NC(=O)NC1=CC=CC(Cl)=C1Cl MHNCVYSYIFOKDX-UHFFFAOYSA-N 0.000 description 3
- XCUDXBBFNPKYKN-UHFFFAOYSA-N 1-(2,3-dichlorophenyl)-3-(3-hydroxynaphthalen-2-yl)urea Chemical compound OC1=CC2=CC=CC=C2C=C1NC(=O)NC1=CC=CC(Cl)=C1Cl XCUDXBBFNPKYKN-UHFFFAOYSA-N 0.000 description 3
- SEBYEVXUHHITRG-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(2-hydroxy-3-propylphenyl)urea Chemical compound CCCC1=CC=CC(NC(=O)NC=2C(=CC=CC=2)Br)=C1O SEBYEVXUHHITRG-UHFFFAOYSA-N 0.000 description 3
- SWZSLTLBOSGOGA-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(2-hydroxy-4-phenylphenyl)urea Chemical compound OC1=CC(C=2C=CC=CC=2)=CC=C1NC(=O)NC1=CC=CC=C1Br SWZSLTLBOSGOGA-UHFFFAOYSA-N 0.000 description 3
- IFOKUNVJYFFYQT-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(3,4-difluoro-2-hydroxyphenyl)urea Chemical compound OC1=C(F)C(F)=CC=C1NC(=O)NC1=CC=CC=C1Br IFOKUNVJYFFYQT-UHFFFAOYSA-N 0.000 description 3
- DHXOJNFEHNIGMB-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(4-fluoro-2-hydroxyphenyl)urea Chemical compound OC1=CC(F)=CC=C1NC(=O)NC1=CC=CC=C1Br DHXOJNFEHNIGMB-UHFFFAOYSA-N 0.000 description 3
- JGLOHKYHPQNEJY-UHFFFAOYSA-N 1-(2-bromophenyl)-3-[2-hydroxy-4-(trifluoromethyl)phenyl]urea Chemical compound OC1=CC(C(F)(F)F)=CC=C1NC(=O)NC1=CC=CC=C1Br JGLOHKYHPQNEJY-UHFFFAOYSA-N 0.000 description 3
- PMMYTIINRJXKSU-UHFFFAOYSA-N 1-(2-hydroxy-4-nitrophenyl)-3-(2-iodophenyl)urea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=CC=CC=C1I PMMYTIINRJXKSU-UHFFFAOYSA-N 0.000 description 3
- USGOTVZCMDLNGF-UHFFFAOYSA-N 1-(2-hydroxy-4-nitrophenyl)-3-(3-methoxythiophen-2-yl)urea Chemical compound C1=CSC(NC(=O)NC=2C(=CC(=CC=2)[N+]([O-])=O)O)=C1OC USGOTVZCMDLNGF-UHFFFAOYSA-N 0.000 description 3
- KACUYPOBOHDUPW-UHFFFAOYSA-N 1-(2-hydroxy-4-nitrophenyl)-3-phenylthiourea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=S)NC1=CC=CC=C1 KACUYPOBOHDUPW-UHFFFAOYSA-N 0.000 description 3
- MHNNUSRLYWTBJF-UHFFFAOYSA-N 1-(2-hydroxy-5-nitrophenyl)-3-phenylurea Chemical compound OC1=CC=C([N+]([O-])=O)C=C1NC(=O)NC1=CC=CC=C1 MHNNUSRLYWTBJF-UHFFFAOYSA-N 0.000 description 3
- WJGRUAQVAFBYOC-UHFFFAOYSA-N 1-(3,4-dichloro-2-hydroxyphenyl)-3-(2,3-dichlorophenyl)urea Chemical compound OC1=C(Cl)C(Cl)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1Cl WJGRUAQVAFBYOC-UHFFFAOYSA-N 0.000 description 3
- SCVQAOCTYSFKTL-UHFFFAOYSA-N 1-(3-cyano-2-hydroxyphenyl)-3-(2-methoxyphenyl)urea Chemical compound COC1=CC=CC=C1NC(=O)NC1=CC=CC(C#N)=C1O SCVQAOCTYSFKTL-UHFFFAOYSA-N 0.000 description 3
- QOMIBRVYULIIPL-UHFFFAOYSA-N 1-(4-azido-2-hydroxyphenyl)-3-(2-iodophenyl)urea Chemical compound OC1=CC(N=[N+]=[N-])=CC=C1NC(=O)NC1=CC=CC=C1I QOMIBRVYULIIPL-UHFFFAOYSA-N 0.000 description 3
- DUMLBLQIHLMJQY-UHFFFAOYSA-N 1-(4-cyano-2-hydroxyphenyl)-3-(4-methoxyphenyl)urea Chemical compound C1=CC(OC)=CC=C1NC(=O)NC1=CC=C(C#N)C=C1O DUMLBLQIHLMJQY-UHFFFAOYSA-N 0.000 description 3
- PSODDICKDGEFJX-UHFFFAOYSA-N 1-(4-cyano-2-hydroxyphenyl)-3-[2-(trifluoromethyl)phenyl]urea Chemical compound OC1=CC(C#N)=CC=C1NC(=O)NC1=CC=CC=C1C(F)(F)F PSODDICKDGEFJX-UHFFFAOYSA-N 0.000 description 3
- PICNBCJMPWKROU-UHFFFAOYSA-N 1-[2-(benzenesulfonamido)-4-nitrophenyl]-3-phenylurea Chemical compound C=1C=CC=CC=1S(=O)(=O)NC1=CC([N+](=O)[O-])=CC=C1NC(=O)NC1=CC=CC=C1 PICNBCJMPWKROU-UHFFFAOYSA-N 0.000 description 3
- FLLYDYSIHJCMKD-UHFFFAOYSA-N 1-[2-[[3,5-bis(trifluoromethyl)phenyl]sulfonylamino]phenyl]-3-(2-bromophenyl)urea Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(S(=O)(=O)NC=2C(=CC=CC=2)NC(=O)NC=2C(=CC=CC=2)Br)=C1 FLLYDYSIHJCMKD-UHFFFAOYSA-N 0.000 description 3
- SWIRMXTXRCDCJK-UHFFFAOYSA-N 1-[2-hydroxy-4-(trifluoromethyl)phenyl]-3-(2-phenylphenyl)urea Chemical compound OC1=CC(C(F)(F)F)=CC=C1NC(=O)NC1=CC=CC=C1C1=CC=CC=C1 SWIRMXTXRCDCJK-UHFFFAOYSA-N 0.000 description 3
- VSCVMMZCYHQJQD-UHFFFAOYSA-N 2-[(2,4-dichlorophenyl)carbamoylamino]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC(=O)NC1=CC=C(Cl)C=C1Cl VSCVMMZCYHQJQD-UHFFFAOYSA-N 0.000 description 3
- ILZRAAUVZAXXKZ-UHFFFAOYSA-N 2-amino-5-(trifluoromethyl)phenol Chemical compound NC1=CC=C(C(F)(F)F)C=C1O ILZRAAUVZAXXKZ-UHFFFAOYSA-N 0.000 description 3
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 description 3
- LSSMRBBQCHSDNS-UHFFFAOYSA-N 3-methoxythiophene-2-carboxylic acid Chemical compound COC=1C=CSC=1C(O)=O LSSMRBBQCHSDNS-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 201000004681 Psoriasis Diseases 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 229940061631 citric acid acetate Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- MOMPWLMXIZNJGK-UHFFFAOYSA-N methyl 3-hydroxy-4-(phenylcarbamoylamino)benzoate Chemical compound OC1=CC(C(=O)OC)=CC=C1NC(=O)NC1=CC=CC=C1 MOMPWLMXIZNJGK-UHFFFAOYSA-N 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 230000035939 shock Effects 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- ZJHHPAUQMCHPRB-UHFFFAOYSA-N urea urea Chemical compound NC(N)=O.NC(N)=O ZJHHPAUQMCHPRB-UHFFFAOYSA-N 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- PLONVGBGMNBYSF-RRABGKBLSA-N (2-bromophenyl)urea;methyl (e)-3-[3-[(2-bromophenyl)carbamoylamino]-2-hydroxyphenyl]prop-2-enoate Chemical compound NC(=O)NC1=CC=CC=C1Br.COC(=O)\C=C\C1=CC=CC(NC(=O)NC=2C(=CC=CC=2)Br)=C1O PLONVGBGMNBYSF-RRABGKBLSA-N 0.000 description 2
- DRAKOGLGKMMYMG-UHFFFAOYSA-N (3-amino-2-hydroxyphenyl)-phenylmethanone Chemical compound NC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1O DRAKOGLGKMMYMG-UHFFFAOYSA-N 0.000 description 2
- GTIBQOVZWUVLOF-UHFFFAOYSA-N (4-amino-3-hydroxyphenyl)-phenylmethanone Chemical compound C1=C(O)C(N)=CC=C1C(=O)C1=CC=CC=C1 GTIBQOVZWUVLOF-UHFFFAOYSA-N 0.000 description 2
- WTRTYLZMKRSHMF-CMDGGOBGSA-N (e)-3-[3-[(2-bromophenyl)carbamoylamino]-2-hydroxyphenyl]prop-2-enamide Chemical compound NC(=O)\C=C\C1=CC=CC(NC(=O)NC=2C(=CC=CC=2)Br)=C1O WTRTYLZMKRSHMF-CMDGGOBGSA-N 0.000 description 2
- HAXYXBBIILZWIZ-HRNDJLQDSA-N (e)-3-[3-[(2-bromophenyl)carbamoylamino]-2-hydroxyphenyl]prop-2-enamide;(2-bromophenyl)urea Chemical compound NC(=O)NC1=CC=CC=C1Br.NC(=O)\C=C\C1=CC=CC(NC(=O)NC=2C(=CC=CC=2)Br)=C1O HAXYXBBIILZWIZ-HRNDJLQDSA-N 0.000 description 2
- ZSVYFOVBIDQOMP-WVLIHFOGSA-N (e)-3-[4-[(2-bromophenyl)carbamoylamino]-3-hydroxyphenyl]prop-2-enamide;(2-bromophenyl)urea Chemical compound NC(=O)NC1=CC=CC=C1Br.OC1=CC(/C=C/C(=O)N)=CC=C1NC(=O)NC1=CC=CC=C1Br ZSVYFOVBIDQOMP-WVLIHFOGSA-N 0.000 description 2
- DBUAYOWCIUQXQW-UHFFFAOYSA-N 1,3-benzodioxole-4-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=C1OCO2 DBUAYOWCIUQXQW-UHFFFAOYSA-N 0.000 description 2
- GANKNIPTHRSOST-UHFFFAOYSA-N 1-(2,3-dichlorophenyl)-3-(2-hydroxy-4-propan-2-ylphenyl)urea Chemical compound OC1=CC(C(C)C)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1Cl GANKNIPTHRSOST-UHFFFAOYSA-N 0.000 description 2
- NNURDMPNQHPAIX-UHFFFAOYSA-N 1-(2,3-dichlorophenyl)-3-(5-ethylsulfonyl-2-hydroxyphenyl)urea Chemical compound CCS(=O)(=O)C1=CC=C(O)C(NC(=O)NC=2C(=C(Cl)C=CC=2)Cl)=C1 NNURDMPNQHPAIX-UHFFFAOYSA-N 0.000 description 2
- MGOABCWEOZZCDP-UHFFFAOYSA-N 1-(2,4-dibromophenyl)-3-(2-hydroxy-4-nitrophenyl)urea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=CC=C(Br)C=C1Br MGOABCWEOZZCDP-UHFFFAOYSA-N 0.000 description 2
- CWCZXUGASXHLMK-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-3-(2-hydroxy-4-nitrophenyl)urea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1Cl CWCZXUGASXHLMK-UHFFFAOYSA-N 0.000 description 2
- MIUZBQLHNFEROV-UHFFFAOYSA-N 1-(2,6-difluorophenyl)-3-(2-hydroxy-4-nitrophenyl)urea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=C(F)C=CC=C1F MIUZBQLHNFEROV-UHFFFAOYSA-N 0.000 description 2
- UHOSHUNGLMWKCU-UHFFFAOYSA-N 1-(2-anilinophenyl)-3-(2-hydroxy-4-nitrophenyl)urea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=CC=CC=C1NC1=CC=CC=C1 UHOSHUNGLMWKCU-UHFFFAOYSA-N 0.000 description 2
- OQVARPSTLHEQDV-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(2-hydroxy-3-iodophenyl)urea Chemical compound OC1=C(I)C=CC=C1NC(=O)NC1=CC=CC=C1Br OQVARPSTLHEQDV-UHFFFAOYSA-N 0.000 description 2
- YPUIHNGFAQOMLY-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(2-hydroxy-3-phenylmethoxyphenyl)urea Chemical compound C1=CC=C(OCC=2C=CC=CC=2)C(O)=C1NC(=O)NC1=CC=CC=C1Br YPUIHNGFAQOMLY-UHFFFAOYSA-N 0.000 description 2
- ZDQFTSZMJHUTNA-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(2-hydroxy-4-methylphenyl)urea Chemical compound OC1=CC(C)=CC=C1NC(=O)NC1=CC=CC=C1Br ZDQFTSZMJHUTNA-UHFFFAOYSA-N 0.000 description 2
- FWFSLMHCHRDAMD-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(2-hydroxynaphthalen-1-yl)urea Chemical compound OC1=CC=C2C=CC=CC2=C1NC(=O)NC1=CC=CC=C1Br FWFSLMHCHRDAMD-UHFFFAOYSA-N 0.000 description 2
- XDJSETLIIYOAOI-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(2-hydroxyphenyl)urea Chemical compound OC1=CC=CC=C1NC(=O)NC1=CC=CC=C1Br XDJSETLIIYOAOI-UHFFFAOYSA-N 0.000 description 2
- XCDHYNNOCDUAGE-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(3,5-dichloro-2-hydroxyphenyl)urea Chemical compound OC1=C(Cl)C=C(Cl)C=C1NC(=O)NC1=CC=CC=C1Br XCDHYNNOCDUAGE-UHFFFAOYSA-N 0.000 description 2
- MPBMQOWOKKDSFC-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(3-chloro-2-hydroxyphenyl)urea Chemical compound OC1=C(Cl)C=CC=C1NC(=O)NC1=CC=CC=C1Br MPBMQOWOKKDSFC-UHFFFAOYSA-N 0.000 description 2
- KYMGMLIJGMOCOG-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(3-fluoro-2-hydroxyphenyl)urea Chemical compound OC1=C(F)C=CC=C1NC(=O)NC1=CC=CC=C1Br KYMGMLIJGMOCOG-UHFFFAOYSA-N 0.000 description 2
- ANTFJOTVFCVVAW-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(3-hydroxynaphthalen-2-yl)urea Chemical compound OC1=CC2=CC=CC=C2C=C1NC(=O)NC1=CC=CC=C1Br ANTFJOTVFCVVAW-UHFFFAOYSA-N 0.000 description 2
- QWLSUPKOFQHSRW-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(4-bromo-2-sulfanylphenyl)urea Chemical compound SC1=CC(Br)=CC=C1NC(=O)NC1=CC=CC=C1Br QWLSUPKOFQHSRW-UHFFFAOYSA-N 0.000 description 2
- ZILKNQHGVMDEEV-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(5-cyano-2-hydroxyphenyl)urea Chemical compound OC1=CC=C(C#N)C=C1NC(=O)NC1=CC=CC=C1Br ZILKNQHGVMDEEV-UHFFFAOYSA-N 0.000 description 2
- KPJZGZQNCRHCPT-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(5-fluoro-2-hydroxyphenyl)urea Chemical compound OC1=CC=C(F)C=C1NC(=O)NC1=CC=CC=C1Br KPJZGZQNCRHCPT-UHFFFAOYSA-N 0.000 description 2
- KHTGUBPZTDJRNE-UHFFFAOYSA-N 1-(2-bromophenyl)-3-[2-(2-phenyl-1-sulfamoylethenyl)phenyl]urea Chemical compound C=1C=CC=C(NC(=O)NC=2C(=CC=CC=2)Br)C=1C(S(=O)(=O)N)=CC1=CC=CC=C1 KHTGUBPZTDJRNE-UHFFFAOYSA-N 0.000 description 2
- YIQZPEHGQARGRD-UHFFFAOYSA-N 1-(2-bromophenyl)-3-[2-[2-(sulfamoylamino)phenyl]phenyl]urea Chemical compound NS(=O)(=O)NC1=CC=CC=C1C1=CC=CC=C1NC(=O)NC1=CC=CC=C1Br YIQZPEHGQARGRD-UHFFFAOYSA-N 0.000 description 2
- YWKGOEOCYBFILN-UHFFFAOYSA-N 1-(2-bromophenyl)-3-[2-[[2-(trifluoromethyl)phenyl]sulfonylamino]phenyl]urea Chemical compound FC(F)(F)C1=CC=CC=C1S(=O)(=O)NC1=CC=CC=C1NC(=O)NC1=CC=CC=C1Br YWKGOEOCYBFILN-UHFFFAOYSA-N 0.000 description 2
- IGNKQJCDASZUBP-UHFFFAOYSA-N 1-(2-bromophenyl)-3-[2-hydroxy-3-(trifluoromethyl)phenyl]urea Chemical compound C1=CC=C(C(F)(F)F)C(O)=C1NC(=O)NC1=CC=CC=C1Br IGNKQJCDASZUBP-UHFFFAOYSA-N 0.000 description 2
- IHPOVFSDJQPNOC-BUHFOSPRSA-N 1-(2-bromophenyl)-3-[2-hydroxy-3-[(E)-2-phenylethenyl]phenyl]urea Chemical compound C1=CC=C(\C=C\C=2C=CC=CC=2)C(O)=C1NC(=O)NC1=CC=CC=C1Br IHPOVFSDJQPNOC-BUHFOSPRSA-N 0.000 description 2
- MZFHJQMUHUVVLD-UHFFFAOYSA-N 1-(2-bromophenyl)-3-[2-hydroxy-5-(trifluoromethyl)phenyl]urea Chemical compound OC1=CC=C(C(F)(F)F)C=C1NC(=O)NC1=CC=CC=C1Br MZFHJQMUHUVVLD-UHFFFAOYSA-N 0.000 description 2
- MWODCLJTSRCRGB-UHFFFAOYSA-N 1-(2-bromophenyl)-3-[3-fluoro-2-hydroxy-4-(trifluoromethyl)phenyl]urea Chemical compound OC1=C(F)C(C(F)(F)F)=CC=C1NC(=O)NC1=CC=CC=C1Br MWODCLJTSRCRGB-UHFFFAOYSA-N 0.000 description 2
- LCOWZPIPSUYVOG-UHFFFAOYSA-N 1-(2-bromophenyl)-3-phenylurea Chemical compound BrC1=CC=CC=C1NC(=O)NC1=CC=CC=C1 LCOWZPIPSUYVOG-UHFFFAOYSA-N 0.000 description 2
- PPCPBEOXHRRPRQ-UHFFFAOYSA-N 1-(2-fluorophenyl)-3-(2-hydroxy-4-nitrophenyl)urea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=CC=CC=C1F PPCPBEOXHRRPRQ-UHFFFAOYSA-N 0.000 description 2
- QZOTURNBPCCOPX-UHFFFAOYSA-N 1-(2-hydroxy-4-nitrophenyl)-3-(3-methoxyphenyl)urea Chemical compound COC1=CC=CC(NC(=O)NC=2C(=CC(=CC=2)[N+]([O-])=O)O)=C1 QZOTURNBPCCOPX-UHFFFAOYSA-N 0.000 description 2
- SAUHQYBXEGARCC-UHFFFAOYSA-N 1-(2-hydroxy-4-nitrophenyl)-3-phenylurea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=CC=CC=C1 SAUHQYBXEGARCC-UHFFFAOYSA-N 0.000 description 2
- ZZQDGDJCUKXXBC-UHFFFAOYSA-N 1-(2-hydroxy-4-propan-2-ylphenyl)-3-[3-(trifluoromethyl)phenyl]urea Chemical compound OC1=CC(C(C)C)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 ZZQDGDJCUKXXBC-UHFFFAOYSA-N 0.000 description 2
- RTLALTGENBGFDX-UHFFFAOYSA-N 1-(2-hydroxy-5-nitrophenyl)-3-(2-methoxyphenyl)urea Chemical compound COC1=CC=CC=C1NC(=O)NC1=CC([N+]([O-])=O)=CC=C1O RTLALTGENBGFDX-UHFFFAOYSA-N 0.000 description 2
- SUVXETMUHQVVFC-UHFFFAOYSA-N 1-(2-hydroxy-5-nitrophenyl)-3-(2-phenylphenyl)urea Chemical compound OC1=CC=C([N+]([O-])=O)C=C1NC(=O)NC1=CC=CC=C1C1=CC=CC=C1 SUVXETMUHQVVFC-UHFFFAOYSA-N 0.000 description 2
- MPHQBIQHINWCQF-UHFFFAOYSA-N 1-(3,4-dichloro-2-hydroxyphenyl)-3-(2,4-dimethoxyphenyl)urea Chemical compound COC1=CC(OC)=CC=C1NC(=O)NC1=CC=C(Cl)C(Cl)=C1O MPHQBIQHINWCQF-UHFFFAOYSA-N 0.000 description 2
- SXDDKYMVNSTNIY-UHFFFAOYSA-N 1-(3,4-dichloro-2-hydroxyphenyl)-3-(4-phenylphenyl)urea Chemical compound OC1=C(Cl)C(Cl)=CC=C1NC(=O)NC1=CC=C(C=2C=CC=CC=2)C=C1 SXDDKYMVNSTNIY-UHFFFAOYSA-N 0.000 description 2
- UAXAGWYQMOAGGL-UHFFFAOYSA-N 1-(3,4-dichloro-2-hydroxyphenyl)-3-[3-(trifluoromethyl)phenyl]urea Chemical compound OC1=C(Cl)C(Cl)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 UAXAGWYQMOAGGL-UHFFFAOYSA-N 0.000 description 2
- YDCPBZQRMMLIFE-UHFFFAOYSA-N 1-(3-amino-2-hydroxyphenyl)-3-(2-bromophenyl)urea Chemical compound NC1=CC=CC(NC(=O)NC=2C(=CC=CC=2)Br)=C1O YDCPBZQRMMLIFE-UHFFFAOYSA-N 0.000 description 2
- YENXEPKNDWFMOD-UHFFFAOYSA-N 1-(3-cyano-2-hydroxyphenyl)-3-(2-phenylphenyl)urea Chemical compound C1=CC=C(C#N)C(O)=C1NC(=O)NC1=CC=CC=C1C1=CC=CC=C1 YENXEPKNDWFMOD-UHFFFAOYSA-N 0.000 description 2
- ANAOKSOOHCYGTR-UHFFFAOYSA-N 1-(3-cyano-2-hydroxyphenyl)-3-[3-(trifluoromethyl)phenyl]urea Chemical compound C1=CC=C(C#N)C(O)=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 ANAOKSOOHCYGTR-UHFFFAOYSA-N 0.000 description 2
- OGRVRTFZEUPTGZ-UHFFFAOYSA-N 1-(4-cyano-2-hydroxyphenyl)-3-(3-methoxyphenyl)urea Chemical compound COC1=CC=CC(NC(=O)NC=2C(=CC(=CC=2)C#N)O)=C1 OGRVRTFZEUPTGZ-UHFFFAOYSA-N 0.000 description 2
- QIYGBMTTYPAFGZ-UHFFFAOYSA-N 1-(4-cyano-2-hydroxyphenyl)-3-(4-phenylphenyl)urea Chemical compound OC1=CC(C#N)=CC=C1NC(=O)NC1=CC=C(C=2C=CC=CC=2)C=C1 QIYGBMTTYPAFGZ-UHFFFAOYSA-N 0.000 description 2
- HGRXXAGRIICSQS-UHFFFAOYSA-N 1-(4-cyano-2-hydroxyphenyl)-3-[3-(trifluoromethyl)phenyl]urea Chemical compound OC1=CC(C#N)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 HGRXXAGRIICSQS-UHFFFAOYSA-N 0.000 description 2
- YGAGRJGVAXCRFI-UHFFFAOYSA-N 1-(4-fluoro-2-hydroxyphenyl)-3-phenylurea Chemical compound OC1=CC(F)=CC=C1NC(=O)NC1=CC=CC=C1 YGAGRJGVAXCRFI-UHFFFAOYSA-N 0.000 description 2
- CENOMWDZGNQIGT-UHFFFAOYSA-N 1-(5-bromo-3-fluoro-2-hydroxyphenyl)-3-(2-bromophenyl)urea Chemical compound OC1=C(F)C=C(Br)C=C1NC(=O)NC1=CC=CC=C1Br CENOMWDZGNQIGT-UHFFFAOYSA-N 0.000 description 2
- ASMCVDDUQQZBFK-UHFFFAOYSA-N 1-(5-chloro-2-hydroxy-4-nitrophenyl)-3-phenylurea Chemical compound OC1=CC([N+]([O-])=O)=C(Cl)C=C1NC(=O)NC1=CC=CC=C1 ASMCVDDUQQZBFK-UHFFFAOYSA-N 0.000 description 2
- ROVKFKQMANVQJQ-UHFFFAOYSA-N 1-[2-chloro-5-(trifluoromethyl)phenyl]-3-(2-hydroxy-4-propan-2-ylphenyl)urea Chemical compound OC1=CC(C(C)C)=CC=C1NC(=O)NC1=CC(C(F)(F)F)=CC=C1Cl ROVKFKQMANVQJQ-UHFFFAOYSA-N 0.000 description 2
- QCPKCLJVLUZRHH-UHFFFAOYSA-N 1-[2-chloro-5-(trifluoromethyl)phenyl]-3-(3,4-dichloro-2-hydroxyphenyl)urea Chemical compound OC1=C(Cl)C(Cl)=CC=C1NC(=O)NC1=CC(C(F)(F)F)=CC=C1Cl QCPKCLJVLUZRHH-UHFFFAOYSA-N 0.000 description 2
- JOUCNJAIDGFKOE-UHFFFAOYSA-N 1-[3-amino-2-(2-sulfamoylphenyl)phenyl]-3-(2-bromophenyl)urea Chemical compound C=1C=CC=C(S(N)(=O)=O)C=1C=1C(N)=CC=CC=1NC(=O)NC1=CC=CC=C1Br JOUCNJAIDGFKOE-UHFFFAOYSA-N 0.000 description 2
- PAFORXDSYWMYGP-UHFFFAOYSA-N 1-bromo-2-isothiocyanatobenzene Chemical compound BrC1=CC=CC=C1N=C=S PAFORXDSYWMYGP-UHFFFAOYSA-N 0.000 description 2
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 2
- IHHUGFJSEJSCGE-UHFFFAOYSA-N 1-isocyanato-2-phenylbenzene Chemical compound O=C=NC1=CC=CC=C1C1=CC=CC=C1 IHHUGFJSEJSCGE-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- QAUYDNWQNRMCIU-UHFFFAOYSA-N 1-phenyl-3-(2-sulfanylphenyl)urea Chemical compound SC1=CC=CC=C1NC(=O)NC1=CC=CC=C1 QAUYDNWQNRMCIU-UHFFFAOYSA-N 0.000 description 2
- 125000006017 1-propenyl group Chemical group 0.000 description 2
- HYNQTSZBTIOFKH-UHFFFAOYSA-N 2-Amino-5-hydroxybenzoic acid Chemical compound NC1=CC=C(O)C=C1C(O)=O HYNQTSZBTIOFKH-UHFFFAOYSA-N 0.000 description 2
- PJIQDIIKISUDNK-UHFFFAOYSA-N 2-[(2-amino-5-bromophenyl)disulfanyl]-4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1SSC1=CC(Br)=CC=C1N PJIQDIIKISUDNK-UHFFFAOYSA-N 0.000 description 2
- HPIWUVVNMOAVQD-UHFFFAOYSA-N 2-[(2-methoxyphenyl)methylcarbamoylamino]benzoic acid Chemical compound COC1=CC=CC=C1CNC(=O)NC1=CC=CC=C1C(O)=O HPIWUVVNMOAVQD-UHFFFAOYSA-N 0.000 description 2
- WDEWMHZCLLLPCQ-UHFFFAOYSA-N 2-[(3-methoxyphenyl)methylcarbamoylamino]benzoic acid Chemical compound COC1=CC=CC(CNC(=O)NC=2C(=CC=CC=2)C(O)=O)=C1 WDEWMHZCLLLPCQ-UHFFFAOYSA-N 0.000 description 2
- JSHJJLQJRLNBBA-UHFFFAOYSA-N 2-amino-3-chlorophenol Chemical compound NC1=C(O)C=CC=C1Cl JSHJJLQJRLNBBA-UHFFFAOYSA-N 0.000 description 2
- WASQBNCGNUTVNI-UHFFFAOYSA-N 2-amino-4,6-dichlorophenol Chemical compound NC1=CC(Cl)=CC(Cl)=C1O WASQBNCGNUTVNI-UHFFFAOYSA-N 0.000 description 2
- BHTKIYIEMXRHGL-UHFFFAOYSA-N 2-amino-4-(trifluoromethyl)phenol Chemical compound NC1=CC(C(F)(F)F)=CC=C1O BHTKIYIEMXRHGL-UHFFFAOYSA-N 0.000 description 2
- ULDFRPKVIZMKJG-UHFFFAOYSA-N 2-amino-4-fluorophenol Chemical compound NC1=CC(F)=CC=C1O ULDFRPKVIZMKJG-UHFFFAOYSA-N 0.000 description 2
- VBCFPAKCBOGUBW-UHFFFAOYSA-N 2-amino-5-ethylphenol Chemical compound CCC1=CC=C(N)C(O)=C1 VBCFPAKCBOGUBW-UHFFFAOYSA-N 0.000 description 2
- ILGJVPVZCNNBKI-UHFFFAOYSA-N 2-amino-5-phenylphenol Chemical compound C1=C(O)C(N)=CC=C1C1=CC=CC=C1 ILGJVPVZCNNBKI-UHFFFAOYSA-N 0.000 description 2
- XOXAZFFGKMIJKE-UHFFFAOYSA-N 2-amino-6-(trifluoromethyl)phenol Chemical compound NC1=CC=CC(C(F)(F)F)=C1O XOXAZFFGKMIJKE-UHFFFAOYSA-N 0.000 description 2
- APMAGJYKMMAXBU-MDZDMXLPSA-N 2-amino-6-[(E)-2-phenylethenyl]phenol Chemical compound NC1=CC=CC(\C=C\C=2C=CC=CC=2)=C1O APMAGJYKMMAXBU-MDZDMXLPSA-N 0.000 description 2
- UDVRKKAWBVVSAM-UHFFFAOYSA-N 2-amino-6-phenylphenol Chemical compound NC1=CC=CC(C=2C=CC=CC=2)=C1O UDVRKKAWBVVSAM-UHFFFAOYSA-N 0.000 description 2
- ABKAJPLOOIISSW-UHFFFAOYSA-N 2-amino-6-propylphenol Chemical compound CCCC1=CC=CC(N)=C1O ABKAJPLOOIISSW-UHFFFAOYSA-N 0.000 description 2
- UTYJWCLETJNCCW-UHFFFAOYSA-N 2-amino-9h-fluoren-1-ol Chemical compound C1=CC=C2C3=CC=C(N)C(O)=C3CC2=C1 UTYJWCLETJNCCW-UHFFFAOYSA-N 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
- IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
- CHZCERSEMVWNHL-UHFFFAOYSA-N 2-hydroxybenzonitrile Chemical compound OC1=CC=CC=C1C#N CHZCERSEMVWNHL-UHFFFAOYSA-N 0.000 description 2
- 125000006020 2-methyl-1-propenyl group Chemical group 0.000 description 2
- HYPKGPVDQYUOSV-UHFFFAOYSA-N 2-nitro-5-phenylphenol Chemical compound C1=C([N+]([O-])=O)C(O)=CC(C=2C=CC=CC=2)=C1 HYPKGPVDQYUOSV-UHFFFAOYSA-N 0.000 description 2
- OSIJREAKAWRMJQ-UHFFFAOYSA-N 2-nitro-6-phenylmethoxyphenol Chemical compound C1=CC=C([N+]([O-])=O)C(O)=C1OCC1=CC=CC=C1 OSIJREAKAWRMJQ-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- CAHLKWGNFWVZRJ-UHFFFAOYSA-N 3-[(2-bromophenyl)carbamoylamino]-2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(NC(=O)NC=2C(=CC=CC=2)Br)=C1O CAHLKWGNFWVZRJ-UHFFFAOYSA-N 0.000 description 2
- JJIHEKRAOZPTLG-UHFFFAOYSA-N 3-[3-(hydroxymethyl)-4-nitrophenyl]prop-2-enoic acid Chemical compound OCC1=CC(C=CC(O)=O)=CC=C1[N+]([O-])=O JJIHEKRAOZPTLG-UHFFFAOYSA-N 0.000 description 2
- JPPJUPXPQUNYOH-UHFFFAOYSA-N 3-amino-2-hydroxy-1,2,3,4-tetrahydroinden-5-one Chemical compound C1C(=O)C=CC2=C1C(N)C(O)C2 JPPJUPXPQUNYOH-UHFFFAOYSA-N 0.000 description 2
- NTUMBWHJAMGXFO-UHFFFAOYSA-N 3-amino-2-hydroxy-6-methylbenzonitrile Chemical compound CC1=CC=C(N)C(O)=C1C#N NTUMBWHJAMGXFO-UHFFFAOYSA-N 0.000 description 2
- PTGSDRFHFSNCIP-UHFFFAOYSA-N 3-amino-2-hydroxy-n-phenylbenzamide Chemical compound NC1=CC=CC(C(=O)NC=2C=CC=CC=2)=C1O PTGSDRFHFSNCIP-UHFFFAOYSA-N 0.000 description 2
- ZEWCASRNRWXXSO-UHFFFAOYSA-N 3-amino-4-hydroxybenzonitrile Chemical compound NC1=CC(C#N)=CC=C1O ZEWCASRNRWXXSO-UHFFFAOYSA-N 0.000 description 2
- ZHVPTERSBUMMHK-UHFFFAOYSA-N 3-aminonaphthalen-2-ol Chemical compound C1=CC=C2C=C(O)C(N)=CC2=C1 ZHVPTERSBUMMHK-UHFFFAOYSA-N 0.000 description 2
- JHNIFYUIFUWEFO-UHFFFAOYSA-N 3-hydroxy-4-nitrobenzonitrile Chemical compound OC1=CC(C#N)=CC=C1[N+]([O-])=O JHNIFYUIFUWEFO-UHFFFAOYSA-N 0.000 description 2
- YBAZINRZQSAIAY-UHFFFAOYSA-N 4-aminobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1 YBAZINRZQSAIAY-UHFFFAOYSA-N 0.000 description 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 2
- NKJIFDNZPGLLSH-UHFFFAOYSA-N 4-nitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC=C(C#N)C=C1 NKJIFDNZPGLLSH-UHFFFAOYSA-N 0.000 description 2
- QQURWFRNETXFTN-UHFFFAOYSA-N 5-fluoro-2-nitrophenol Chemical compound OC1=CC(F)=CC=C1[N+]([O-])=O QQURWFRNETXFTN-UHFFFAOYSA-N 0.000 description 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 2
- 206010009900 Colitis ulcerative Diseases 0.000 description 2
- 208000011231 Crohn disease Diseases 0.000 description 2
- 206010012438 Dermatitis atopic Diseases 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 206010018364 Glomerulonephritis Diseases 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 2
- 102000008072 Lymphokines Human genes 0.000 description 2
- 108010074338 Lymphokines Proteins 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 206010063837 Reperfusion injury Diseases 0.000 description 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 description 2
- 206010040047 Sepsis Diseases 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 2
- 208000007536 Thrombosis Diseases 0.000 description 2
- 206010044248 Toxic shock syndrome Diseases 0.000 description 2
- 231100000650 Toxic shock syndrome Toxicity 0.000 description 2
- 206010054094 Tumour necrosis Diseases 0.000 description 2
- 201000006704 Ulcerative Colitis Diseases 0.000 description 2
- ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 description 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- 206010003246 arthritis Diseases 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 201000008937 atopic dermatitis Diseases 0.000 description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 2
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- HQCVEGNPQFRFPC-UHFFFAOYSA-N carboxy acetate Chemical compound CC(=O)OC(O)=O HQCVEGNPQFRFPC-UHFFFAOYSA-N 0.000 description 2
- 230000000747 cardiac effect Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000002975 chemoattractant Substances 0.000 description 2
- 230000003399 chemotactic effect Effects 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- NHADDZMCASKINP-HTRCEHHLSA-N decarboxydihydrocitrinin Natural products C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OCC2=C1O NHADDZMCASKINP-HTRCEHHLSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 210000002950 fibroblast Anatomy 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 208000024908 graft versus host disease Diseases 0.000 description 2
- 230000003394 haemopoietic effect Effects 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-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
- 239000000865 liniment Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- HVSWRCHXFZIJMA-UHFFFAOYSA-N methyl 3-hydroxy-4-[(2-phenylphenyl)carbamoylamino]benzoate Chemical compound OC1=CC(C(=O)OC)=CC=C1NC(=O)NC1=CC=CC=C1C1=CC=CC=C1 HVSWRCHXFZIJMA-UHFFFAOYSA-N 0.000 description 2
- OCZXDVNSNDITBS-UHFFFAOYSA-N methyl 4-amino-3-hydroxybenzoate Chemical compound COC(=O)C1=CC=C(N)C(O)=C1 OCZXDVNSNDITBS-UHFFFAOYSA-N 0.000 description 2
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 2
- KUJANOFPCPKYLF-UHFFFAOYSA-N n-(2-amino-5-nitrophenyl)benzenesulfonamide Chemical compound NC1=CC=C([N+]([O-])=O)C=C1NS(=O)(=O)C1=CC=CC=C1 KUJANOFPCPKYLF-UHFFFAOYSA-N 0.000 description 2
- WMWPOLBAWLJWPR-UHFFFAOYSA-N n-(2-aminophenyl)-1-phenylmethanesulfonamide Chemical compound NC1=CC=CC=C1NS(=O)(=O)CC1=CC=CC=C1 WMWPOLBAWLJWPR-UHFFFAOYSA-N 0.000 description 2
- NFPKLXASODMBIP-UHFFFAOYSA-N n-(2-aminophenyl)quinoline-8-sulfonamide Chemical compound NC1=CC=CC=C1NS(=O)(=O)C1=CC=CC2=CC=CN=C12 NFPKLXASODMBIP-UHFFFAOYSA-N 0.000 description 2
- OTFMOOMWUNLLKQ-UHFFFAOYSA-N n-[4-[[2-[(2-bromophenyl)carbamoylamino]phenyl]sulfamoyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC1=CC=CC=C1NC(=O)NC1=CC=CC=C1Br OTFMOOMWUNLLKQ-UHFFFAOYSA-N 0.000 description 2
- AEURYAULWMMTBR-UHFFFAOYSA-N n-[5-[[2-[(2-bromophenyl)carbamoylamino]phenyl]sulfamoyl]-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC(C)=C1S(=O)(=O)NC1=CC=CC=C1NC(=O)NC1=CC=CC=C1Br AEURYAULWMMTBR-UHFFFAOYSA-N 0.000 description 2
- NHDUIVOKCKQWEF-UHFFFAOYSA-N n-benzyl-4-[(2-bromophenyl)carbamoylamino]-3-hydroxybenzamide Chemical compound OC1=CC(C(=O)NCC=2C=CC=CC=2)=CC=C1NC(=O)NC1=CC=CC=C1Br NHDUIVOKCKQWEF-UHFFFAOYSA-N 0.000 description 2
- 125000004957 naphthylene group Chemical group 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 229920001184 polypeptide Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 102000004196 processed proteins & peptides Human genes 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 230000036303 septic shock Effects 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 238000007910 systemic administration Methods 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 150000003557 thiazoles Chemical class 0.000 description 2
- 238000011200 topical administration Methods 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
- NTJBWZHVSJNKAD-UHFFFAOYSA-N triethylazanium;fluoride Chemical compound [F-].CC[NH+](CC)CC NTJBWZHVSJNKAD-UHFFFAOYSA-N 0.000 description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 2
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 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
- AKCUGQGKWDRTGL-UHFFFAOYSA-N (2-hydroxy-3-nitrophenyl)-phenylmethanone Chemical compound C1=CC=C([N+]([O-])=O)C(O)=C1C(=O)C1=CC=CC=C1 AKCUGQGKWDRTGL-UHFFFAOYSA-N 0.000 description 1
- OEBDKVHFNVETAN-UHFFFAOYSA-N (2-hydroxy-3-nitrophenyl)-phenylmethanone;(2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1.C1=CC=C([N+]([O-])=O)C(O)=C1C(=O)C1=CC=CC=C1 OEBDKVHFNVETAN-UHFFFAOYSA-N 0.000 description 1
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- UIVHJEKZRQNSEB-UHFFFAOYSA-N (3-hydroxy-4-nitrophenyl)-phenylmethanone Chemical compound C1=C([N+]([O-])=O)C(O)=CC(C(=O)C=2C=CC=CC=2)=C1 UIVHJEKZRQNSEB-UHFFFAOYSA-N 0.000 description 1
- WJEYKGGOHNCWTL-UHFFFAOYSA-N (3-hydroxy-4-nitrophenyl)-phenylmethanone;(3-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1.C1=C([N+]([O-])=O)C(O)=CC(C(=O)C=2C=CC=CC=2)=C1 WJEYKGGOHNCWTL-UHFFFAOYSA-N 0.000 description 1
- 125000000229 (C1-C4)alkoxy 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
- ONWRSBMOCIQLRK-VOTSOKGWSA-N (e)-2-phenylethenesulfonyl chloride Chemical compound ClS(=O)(=O)\C=C\C1=CC=CC=C1 ONWRSBMOCIQLRK-VOTSOKGWSA-N 0.000 description 1
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
- FYWJWWMKCARWQG-UHFFFAOYSA-N 1,2-dichloro-3-isocyanatobenzene Chemical compound ClC1=CC=CC(N=C=O)=C1Cl FYWJWWMKCARWQG-UHFFFAOYSA-N 0.000 description 1
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 1
- ZFMWVFOQAAUFDD-UHFFFAOYSA-N 1,3-bis(3-methylphenyl)thiourea Chemical compound CC1=CC=CC(NC(=S)NC=2C=C(C)C=CC=2)=C1 ZFMWVFOQAAUFDD-UHFFFAOYSA-N 0.000 description 1
- CFFRUCPLXOUIGF-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(2,3,5-trifluoro-6-hydroxyphenyl)urea Chemical compound OC1=C(F)C=C(F)C(F)=C1NC(=O)NC1=CC=CC=C1Br CFFRUCPLXOUIGF-UHFFFAOYSA-N 0.000 description 1
- BWFIEDHJOPRIMJ-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(2-hydroxy-3,4-diphenylphenyl)urea Chemical compound C1=CC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(O)=C1NC(=O)NC1=CC=CC=C1Br BWFIEDHJOPRIMJ-UHFFFAOYSA-N 0.000 description 1
- HFRRBYZUABIDFD-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(2-hydroxy-3,4-diphenylphenyl)urea;1-(2-bromophenyl)-3-[2-hydroxy-3-(trifluoromethyl)phenyl]urea Chemical compound C1=CC=C(C(F)(F)F)C(O)=C1NC(=O)NC1=CC=CC=C1Br.C1=CC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(O)=C1NC(=O)NC1=CC=CC=C1Br HFRRBYZUABIDFD-UHFFFAOYSA-N 0.000 description 1
- MGACCYGHGSFOQC-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(3-hydroxy-9,10-dioxoanthracen-2-yl)urea Chemical compound OC1=CC=2C(=O)C3=CC=CC=C3C(=O)C=2C=C1NC(=O)NC1=CC=CC=C1Br MGACCYGHGSFOQC-UHFFFAOYSA-N 0.000 description 1
- ZXNGXQUBIUOUHQ-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(4-cyanophenyl)urea Chemical compound BrC1=CC=CC=C1NC(=O)NC1=CC=C(C#N)C=C1 ZXNGXQUBIUOUHQ-UHFFFAOYSA-N 0.000 description 1
- RPEYJVQVLVKTBY-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(4-ethyl-2-hydroxyphenyl)urea Chemical compound OC1=CC(CC)=CC=C1NC(=O)NC1=CC=CC=C1Br RPEYJVQVLVKTBY-UHFFFAOYSA-N 0.000 description 1
- JGHIGXYVAWUVLN-UHFFFAOYSA-N 1-(2-bromophenyl)-3-[2-(2-phenylethylsulfonylamino)phenyl]urea Chemical compound BrC1=CC=CC=C1NC(=O)NC1=CC=CC=C1NS(=O)(=O)CCC1=CC=CC=C1 JGHIGXYVAWUVLN-UHFFFAOYSA-N 0.000 description 1
- GLAXMZMFLGMTKJ-UHFFFAOYSA-N 1-(2-bromophenyl)-3-[2-(quinolin-8-ylsulfonylamino)phenyl]urea Chemical compound BrC1=CC=CC=C1NC(=O)NC1=CC=CC=C1NS(=O)(=O)C1=CC=CC2=CC=CN=C12 GLAXMZMFLGMTKJ-UHFFFAOYSA-N 0.000 description 1
- KKBLAUFCLVADNC-UHFFFAOYSA-N 1-(2-bromophenyl)-3-[2-[phenyl(sulfamoyl)methyl]phenyl]urea Chemical compound C=1C=CC=C(NC(=O)NC=2C(=CC=CC=2)Br)C=1C(S(=O)(=O)N)C1=CC=CC=C1 KKBLAUFCLVADNC-UHFFFAOYSA-N 0.000 description 1
- ZGBWDCCQBAHGGC-UHFFFAOYSA-N 1-(2-chloro-6-methylphenyl)-3-(2-hydroxy-4-nitrophenyl)urea Chemical compound CC1=CC=CC(Cl)=C1NC(=O)NC1=CC=C([N+]([O-])=O)C=C1O ZGBWDCCQBAHGGC-UHFFFAOYSA-N 0.000 description 1
- XXMZFIZXCJRLQC-UHFFFAOYSA-N 1-(2-ethoxyphenyl)-3-(2-hydroxy-4-nitrophenyl)urea Chemical compound CCOC1=CC=CC=C1NC(=O)NC1=CC=C([N+]([O-])=O)C=C1O XXMZFIZXCJRLQC-UHFFFAOYSA-N 0.000 description 1
- PZBLZIXURGLVNI-UHFFFAOYSA-N 1-(2-ethylphenyl)-3-(2-hydroxy-4-nitrophenyl)urea Chemical compound CCC1=CC=CC=C1NC(=O)NC1=CC=C([N+]([O-])=O)C=C1O PZBLZIXURGLVNI-UHFFFAOYSA-N 0.000 description 1
- RUBDEDUAMQGILI-UHFFFAOYSA-N 1-(2-ethylphenyl)-3-(2-hydroxy-4-nitrophenyl)urea Chemical compound CCC1=CC=CC=C1NC(=O)NC1=CC=C([N+]([O-])=O)C=C1O.CCC1=CC=CC=C1NC(=O)NC1=CC=C([N+]([O-])=O)C=C1O RUBDEDUAMQGILI-UHFFFAOYSA-N 0.000 description 1
- VJKCGAIAKWBLEZ-UHFFFAOYSA-N 1-(2-hydroxy-4-nitrophenyl)-3-(2-methoxyphenyl)urea Chemical compound COC1=CC=CC=C1NC(=O)NC1=CC=C([N+]([O-])=O)C=C1O.COC1=CC=CC=C1NC(=O)NC1=CC=C([N+]([O-])=O)C=C1O VJKCGAIAKWBLEZ-UHFFFAOYSA-N 0.000 description 1
- JDKDJPABXADLJT-UHFFFAOYSA-N 1-(2-hydroxy-4-nitrophenyl)-3-(2-methylphenyl)urea Chemical compound CC1=CC=CC=C1NC(=O)NC1=CC=C([N+]([O-])=O)C=C1O JDKDJPABXADLJT-UHFFFAOYSA-N 0.000 description 1
- LFOBOPSOPJKTMG-UHFFFAOYSA-N 1-(2-hydroxy-4-nitrophenyl)-3-(2-nitrophenyl)urea Chemical compound OC1=C(C=CC(=C1)[N+](=O)[O-])NC(=O)NC1=C(C=CC=C1)[N+](=O)[O-].OC1=C(C=CC(=C1)[N+](=O)[O-])NC(=O)NC1=C(C=CC=C1)[N+](=O)[O-] LFOBOPSOPJKTMG-UHFFFAOYSA-N 0.000 description 1
- TVHIIIDDOHJFQT-UHFFFAOYSA-N 1-(2-hydroxy-4-nitrophenyl)-3-(2-nitrophenyl)urea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=CC=CC=C1[N+]([O-])=O TVHIIIDDOHJFQT-UHFFFAOYSA-N 0.000 description 1
- NHCNZPFYEHIAAT-UHFFFAOYSA-N 1-(2-hydroxy-4-nitrophenyl)-3-(3-methoxyphenyl)urea;1-(2-hydroxy-4-nitrophenyl)-3-[3-(trifluoromethyl)phenyl]urea Chemical compound COC1=CC=CC(NC(=O)NC=2C(=CC(=CC=2)[N+]([O-])=O)O)=C1.OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 NHCNZPFYEHIAAT-UHFFFAOYSA-N 0.000 description 1
- CLRDVEMJNUPVTM-UHFFFAOYSA-N 1-(2-hydroxy-4-nitrophenyl)-3-(4-nitrophenyl)urea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=CC=C([N+]([O-])=O)C=C1 CLRDVEMJNUPVTM-UHFFFAOYSA-N 0.000 description 1
- HJGCROGLAWQCDZ-UHFFFAOYSA-N 1-(2-hydroxy-4-nitrophenyl)-3-[2-(trifluoromethoxy)phenyl]urea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=CC=CC=C1OC(F)(F)F HJGCROGLAWQCDZ-UHFFFAOYSA-N 0.000 description 1
- OGTOIQDAKFXVIH-UHFFFAOYSA-N 1-(2-hydroxy-4-nitrophenyl)-3-[3-(trifluoromethyl)phenyl]urea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 OGTOIQDAKFXVIH-UHFFFAOYSA-N 0.000 description 1
- DAJJRPMUKJGYSD-UHFFFAOYSA-N 1-(2-hydroxy-4-nitrophenyl)-3-[4-(trifluoromethyl)phenyl]urea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=CC=C(C(F)(F)F)C=C1 DAJJRPMUKJGYSD-UHFFFAOYSA-N 0.000 description 1
- SBPFCKQEIYYHBN-UHFFFAOYSA-N 1-(2-hydroxy-4-nitrophenyl)-3-naphthalen-1-ylurea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=CC=CC2=CC=CC=C12 SBPFCKQEIYYHBN-UHFFFAOYSA-N 0.000 description 1
- ZSLIIGIYWQZBOQ-UHFFFAOYSA-N 1-(2-hydroxy-5-nitrophenyl)-3-[3-(trifluoromethyl)phenyl]urea Chemical compound OC1=CC=C([N+]([O-])=O)C=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 ZSLIIGIYWQZBOQ-UHFFFAOYSA-N 0.000 description 1
- KSPGSKWILGYAFB-UHFFFAOYSA-N 1-(3,4-dichloro-2-hydroxyphenyl)-3-(4-methoxyphenyl)urea Chemical compound C1=CC(OC)=CC=C1NC(=O)NC1=CC=C(Cl)C(Cl)=C1O KSPGSKWILGYAFB-UHFFFAOYSA-N 0.000 description 1
- LMDCBZBTIQBAGN-UHFFFAOYSA-N 1-(3,4-dichloro-2-hydroxyphenyl)-3-(4-methoxyphenyl)urea urea Chemical compound OC1=C(C=CC(=C1Cl)Cl)NC(=O)NC1=CC=C(C=C1)OC.NC(=O)N LMDCBZBTIQBAGN-UHFFFAOYSA-N 0.000 description 1
- WBNBOYLRUMMMIM-UHFFFAOYSA-N 1-(3,4-dichloro-2-hydroxyphenyl)-3-[3-(trifluoromethyl)phenyl]urea urea Chemical compound OC1=C(C=CC(=C1Cl)Cl)NC(=O)NC1=CC(=CC=C1)C(F)(F)F.NC(=O)N WBNBOYLRUMMMIM-UHFFFAOYSA-N 0.000 description 1
- LYGPWVRHLXLGNP-UHFFFAOYSA-N 1-(3-bromophenyl)-3-(2-hydroxy-4-nitrophenyl)urea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=CC=CC(Br)=C1 LYGPWVRHLXLGNP-UHFFFAOYSA-N 0.000 description 1
- YRQTZTMQVYXFLH-UHFFFAOYSA-N 1-(4-amino-2-hydroxyphenyl)-3-(2-iodophenyl)urea Chemical compound OC1=CC(N)=CC=C1NC(=O)NC1=CC=CC=C1I YRQTZTMQVYXFLH-UHFFFAOYSA-N 0.000 description 1
- WRABKWBTESAPEL-UHFFFAOYSA-N 1-(4-bromophenyl)-3-(2-hydroxy-4-nitrophenyl)urea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=CC=C(Br)C=C1 WRABKWBTESAPEL-UHFFFAOYSA-N 0.000 description 1
- BIMKTPJMZSGZJT-UHFFFAOYSA-N 1-(4-cyano-2-hydroxyphenyl)-3-[4-(trifluoromethyl)phenyl]urea Chemical compound OC1=CC(C#N)=CC=C1NC(=O)NC1=CC=C(C(F)(F)F)C=C1 BIMKTPJMZSGZJT-UHFFFAOYSA-N 0.000 description 1
- HZWWPMXKFYNCEK-UHFFFAOYSA-N 1-(4-fluoro-2-hydroxyphenyl)-3-phenylurea Chemical compound OC1=CC(F)=CC=C1NC(=O)NC1=CC=CC=C1.OC1=CC(F)=CC=C1NC(=O)NC1=CC=CC=C1 HZWWPMXKFYNCEK-UHFFFAOYSA-N 0.000 description 1
- HTCRMPSYJMYZAP-UHFFFAOYSA-N 1-[2-(benzenesulfonamido)-4-nitrophenyl]-3-phenylurea Chemical compound [N+](=O)([O-])C1=CC(=C(C=C1)NC(=O)NC1=CC=CC=C1)NS(=O)(=O)C1=CC=CC=C1.[N+](=O)([O-])C1=CC(=C(C=C1)NC(=O)NC1=CC=CC=C1)NS(=O)(=O)C1=CC=CC=C1 HTCRMPSYJMYZAP-UHFFFAOYSA-N 0.000 description 1
- WDUQWXBGIVITRM-UHFFFAOYSA-N 1-[2-(benzylsulfonylamino)phenyl]-3-(2-bromophenyl)urea Chemical compound BrC1=CC=CC=C1NC(=O)NC1=CC=CC=C1NS(=O)(=O)CC1=CC=CC=C1 WDUQWXBGIVITRM-UHFFFAOYSA-N 0.000 description 1
- FHMMQQXRSYSWCM-UHFFFAOYSA-N 1-aminonaphthalen-2-ol Chemical compound C1=CC=C2C(N)=C(O)C=CC2=C1 FHMMQQXRSYSWCM-UHFFFAOYSA-N 0.000 description 1
- VQVBCZQTXSHJGF-UHFFFAOYSA-N 1-bromo-3-isocyanatobenzene Chemical compound BrC1=CC=CC(N=C=O)=C1 VQVBCZQTXSHJGF-UHFFFAOYSA-N 0.000 description 1
- CZQIJQFTRGDODI-UHFFFAOYSA-N 1-bromo-4-isocyanatobenzene Chemical compound BrC1=CC=C(N=C=O)C=C1 CZQIJQFTRGDODI-UHFFFAOYSA-N 0.000 description 1
- FBTQQNYGMICJQZ-UHFFFAOYSA-N 1-chloro-2-isocyanato-3-methylbenzene Chemical compound CC1=CC=CC(Cl)=C1N=C=O FBTQQNYGMICJQZ-UHFFFAOYSA-N 0.000 description 1
- NOHQUGRVHSJYMR-UHFFFAOYSA-N 1-chloro-2-isocyanatobenzene Chemical compound ClC1=CC=CC=C1N=C=O NOHQUGRVHSJYMR-UHFFFAOYSA-N 0.000 description 1
- BUIQXUQLYZPMLS-UHFFFAOYSA-N 1-ethoxy-2-isocyanatobenzene Chemical compound CCOC1=CC=CC=C1N=C=O BUIQXUQLYZPMLS-UHFFFAOYSA-N 0.000 description 1
- ZVFNUQWYLXXSJM-UHFFFAOYSA-N 1-ethyl-2-isocyanatobenzene Chemical compound CCC1=CC=CC=C1N=C=O ZVFNUQWYLXXSJM-UHFFFAOYSA-N 0.000 description 1
- VZNCSZQPNIEEMN-UHFFFAOYSA-N 1-fluoro-2-isocyanatobenzene Chemical compound FC1=CC=CC=C1N=C=O VZNCSZQPNIEEMN-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- CTMGYQHKKIEXKF-UHFFFAOYSA-N 1-isocyanato-2-(trifluoromethoxy)benzene Chemical compound FC(F)(F)OC1=CC=CC=C1N=C=O CTMGYQHKKIEXKF-UHFFFAOYSA-N 0.000 description 1
- GZWGTVZRRFPVAS-UHFFFAOYSA-N 1-isocyanato-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1N=C=O GZWGTVZRRFPVAS-UHFFFAOYSA-N 0.000 description 1
- SUVCZZADQDCIEQ-UHFFFAOYSA-N 1-isocyanato-2-methoxybenzene Chemical compound COC1=CC=CC=C1N=C=O SUVCZZADQDCIEQ-UHFFFAOYSA-N 0.000 description 1
- WQXASSKJZYKJSI-UHFFFAOYSA-N 1-isocyanato-2-methylsulfanylbenzene Chemical compound CSC1=CC=CC=C1N=C=O WQXASSKJZYKJSI-UHFFFAOYSA-N 0.000 description 1
- JRVZITODZAQRQM-UHFFFAOYSA-N 1-isocyanato-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1N=C=O JRVZITODZAQRQM-UHFFFAOYSA-N 0.000 description 1
- QZTWVDCKDWZCLV-UHFFFAOYSA-N 1-isocyanato-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(N=C=O)C=C1 QZTWVDCKDWZCLV-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- SJWMPHKDBJQBBJ-UHFFFAOYSA-N 2,3-dichloro-6-nitrophenol Chemical compound OC1=C(Cl)C(Cl)=CC=C1[N+]([O-])=O SJWMPHKDBJQBBJ-UHFFFAOYSA-N 0.000 description 1
- UMPSXRYVXUPCOS-UHFFFAOYSA-N 2,3-dichlorophenol Chemical compound OC1=CC=CC(Cl)=C1Cl UMPSXRYVXUPCOS-UHFFFAOYSA-N 0.000 description 1
- CGEZHWIPFKRZBF-UHFFFAOYSA-N 2,4-dibromo-1-isocyanatobenzene Chemical compound BrC1=CC=C(N=C=O)C(Br)=C1 CGEZHWIPFKRZBF-UHFFFAOYSA-N 0.000 description 1
- OLBJNSPBWLCTOT-UHFFFAOYSA-N 2,4-dichloro-1-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C(Cl)=C1 OLBJNSPBWLCTOT-UHFFFAOYSA-N 0.000 description 1
- RQPVXOUSZLDZFI-UHFFFAOYSA-N 2-(phenylcarbamoylamino)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC(=O)NC1=CC=CC=C1 RQPVXOUSZLDZFI-UHFFFAOYSA-N 0.000 description 1
- ZIZGWNOAHUCACM-UHFFFAOYSA-N 2-(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC(F)(F)C1=CC=CC=C1S(Cl)(=O)=O ZIZGWNOAHUCACM-UHFFFAOYSA-N 0.000 description 1
- MROIECGIYKVCQE-UHFFFAOYSA-N 2-[(3,4-dichlorophenyl)carbamoylamino]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC(=O)NC1=CC=C(Cl)C(Cl)=C1 MROIECGIYKVCQE-UHFFFAOYSA-N 0.000 description 1
- LCZQWCSGKIRNIT-UHFFFAOYSA-N 2-[(3-chlorophenyl)carbamoylamino]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 LCZQWCSGKIRNIT-UHFFFAOYSA-N 0.000 description 1
- CSGHSMMERAWFTP-UHFFFAOYSA-N 2-[(3-chlorophenyl)carbamoylamino]benzoic acid;2-[(3-fluorophenyl)carbamoylamino]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC(=O)NC1=CC=CC(F)=C1.OC(=O)C1=CC=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 CSGHSMMERAWFTP-UHFFFAOYSA-N 0.000 description 1
- IARYNIDODMTYSE-UHFFFAOYSA-N 2-[(3-fluorophenyl)carbamoylamino]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC(=O)NC1=CC=CC(F)=C1 IARYNIDODMTYSE-UHFFFAOYSA-N 0.000 description 1
- GFSBFEFJWQVKFS-UHFFFAOYSA-N 2-[(4-chlorophenyl)carbamoylamino]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC(=O)NC1=CC=C(Cl)C=C1 GFSBFEFJWQVKFS-UHFFFAOYSA-N 0.000 description 1
- VQJMBIKSZASZRM-UHFFFAOYSA-N 2-[(4-chlorophenyl)carbamoylamino]benzoic acid 2-[(4-methoxyphenyl)methylcarbamoylamino]benzoic acid Chemical compound C(C1=CC=C(C=C1)OC)NC(=O)NC1=C(C=CC=C1)C(=O)O.C(=O)(O)C1=C(C=CC=C1)NC(=O)NC1=CC=C(C=C1)Cl VQJMBIKSZASZRM-UHFFFAOYSA-N 0.000 description 1
- ZFHPJWWTGIZRLR-UHFFFAOYSA-N 2-[(4-methoxyphenyl)carbamoylamino]benzoic acid Chemical compound C1=CC(OC)=CC=C1NC(=O)NC1=CC=CC=C1C(O)=O ZFHPJWWTGIZRLR-UHFFFAOYSA-N 0.000 description 1
- WAFUAYGNTDBHDS-UHFFFAOYSA-N 2-[tert-butyl(dimethyl)silyl]oxy-4-nitroaniline Chemical compound CC(C)(C)[Si](C)(C)OC1=CC([N+]([O-])=O)=CC=C1N WAFUAYGNTDBHDS-UHFFFAOYSA-N 0.000 description 1
- NXGKPRKPUCSEIL-UHFFFAOYSA-N 2-acetamido-4-methyl-1,3-thiazole-5-sulfonyl chloride Chemical compound CC(=O)NC1=NC(C)=C(S(Cl)(=O)=O)S1 NXGKPRKPUCSEIL-UHFFFAOYSA-N 0.000 description 1
- BOBATFKNMFWLFG-UHFFFAOYSA-N 2-amino-2-cyano-n-methylacetamide Chemical compound CNC(=O)C(N)C#N BOBATFKNMFWLFG-UHFFFAOYSA-N 0.000 description 1
- NNJHZWICFMKUOE-UHFFFAOYSA-N 2-amino-3,4,6-trifluorophenol Chemical compound NC1=C(O)C(F)=CC(F)=C1F NNJHZWICFMKUOE-UHFFFAOYSA-N 0.000 description 1
- QOZLOYKAFDTQNU-UHFFFAOYSA-N 2-amino-3-fluorophenol Chemical compound NC1=C(O)C=CC=C1F QOZLOYKAFDTQNU-UHFFFAOYSA-N 0.000 description 1
- BXNQDUMAPNIZAG-UHFFFAOYSA-N 2-amino-4-bromo-6-fluorophenol Chemical compound NC1=CC(Br)=CC(F)=C1O BXNQDUMAPNIZAG-UHFFFAOYSA-N 0.000 description 1
- UPJVUFCLBYQKFH-UHFFFAOYSA-N 2-amino-4-ethylsulfonylphenol Chemical compound CCS(=O)(=O)C1=CC=C(O)C(N)=C1 UPJVUFCLBYQKFH-UHFFFAOYSA-N 0.000 description 1
- FZENJANBQJQMMF-UHFFFAOYSA-N 2-amino-5-(trifluoromethyl)phenol Chemical compound NC1=CC=C(C(F)(F)F)C=C1O.NC1=CC=C(C(F)(F)F)C=C1O FZENJANBQJQMMF-UHFFFAOYSA-N 0.000 description 1
- HCPJEHJGFKWRFM-UHFFFAOYSA-N 2-amino-5-methylphenol Chemical compound CC1=CC=C(N)C(O)=C1 HCPJEHJGFKWRFM-UHFFFAOYSA-N 0.000 description 1
- MDIAVSZFIQWYST-UHFFFAOYSA-N 2-amino-6-fluorophenol Chemical compound NC1=CC=CC(F)=C1O MDIAVSZFIQWYST-UHFFFAOYSA-N 0.000 description 1
- WKOJOGYKEWTXHX-UHFFFAOYSA-N 2-amino-6-iodophenol Chemical compound NC1=CC=CC(I)=C1O WKOJOGYKEWTXHX-UHFFFAOYSA-N 0.000 description 1
- AACMNEWXGKOJJK-UHFFFAOYSA-N 2-amino-6-nitrophenol Chemical compound NC1=CC=CC([N+]([O-])=O)=C1O AACMNEWXGKOJJK-UHFFFAOYSA-N 0.000 description 1
- OOHJKDQCYDJZJX-UHFFFAOYSA-N 2-amino-6-phenylmethoxyphenol Chemical compound NC1=CC=CC(OCC=2C=CC=CC=2)=C1O OOHJKDQCYDJZJX-UHFFFAOYSA-N 0.000 description 1
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 1
- RMNCOQJSXAJRRL-UHFFFAOYSA-N 2-bromo-3-methyl-6-nitrophenol;2-hydroxy-6-methyl-3-nitrobenzonitrile Chemical compound CC1=CC=C([N+]([O-])=O)C(O)=C1Br.CC1=CC=C([N+]([O-])=O)C(O)=C1C#N RMNCOQJSXAJRRL-UHFFFAOYSA-N 0.000 description 1
- AOPBDRUWRLBSDB-UHFFFAOYSA-N 2-bromoaniline Chemical compound NC1=CC=CC=C1Br AOPBDRUWRLBSDB-UHFFFAOYSA-N 0.000 description 1
- JWILHLGCYCOTNG-UHFFFAOYSA-N 2-bromophenol;urea Chemical compound NC(N)=O.OC1=CC=CC=C1Br JWILHLGCYCOTNG-UHFFFAOYSA-N 0.000 description 1
- JWHPQBAWKJSXAL-UHFFFAOYSA-N 2-chloro-1-isocyanato-3-methoxybenzene Chemical compound COC1=CC=CC(N=C=O)=C1Cl JWHPQBAWKJSXAL-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- LFAHYSRYSVNIET-UHFFFAOYSA-N 2-hydroxy-3-nitro-1,2,3,4-tetrahydroinden-5-one Chemical compound [O-][N+](=O)C1C(O)CC2=C1CC(=O)C=C2 LFAHYSRYSVNIET-UHFFFAOYSA-N 0.000 description 1
- ZWZZWLBNEPKBAR-UHFFFAOYSA-N 2-hydroxy-3-nitro-n-phenylbenzamide Chemical compound C1=CC=C([N+]([O-])=O)C(O)=C1C(=O)NC1=CC=CC=C1 ZWZZWLBNEPKBAR-UHFFFAOYSA-N 0.000 description 1
- ZUOCMGGILLTISV-UHFFFAOYSA-N 2-hydroxy-3-nitrobenzonitrile Chemical compound OC1=C(C#N)C=CC=C1[N+]([O-])=O ZUOCMGGILLTISV-UHFFFAOYSA-N 0.000 description 1
- ZMBBNCSYNZSXHB-UHFFFAOYSA-N 2-hydroxybenzonitrile;2-hydroxy-3-nitrobenzonitrile Chemical compound OC1=CC=CC=C1C#N.OC1=C(C#N)C=CC=C1[N+]([O-])=O ZMBBNCSYNZSXHB-UHFFFAOYSA-N 0.000 description 1
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 1
- CJNZAXGUTKBIHP-UHFFFAOYSA-N 2-iodobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1I CJNZAXGUTKBIHP-UHFFFAOYSA-N 0.000 description 1
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
- NFCPRRWCTNLGSN-UHFFFAOYSA-N 2-n-phenylbenzene-1,2-diamine Chemical compound NC1=CC=CC=C1NC1=CC=CC=C1 NFCPRRWCTNLGSN-UHFFFAOYSA-N 0.000 description 1
- ATXBGHLILIABGX-UHFFFAOYSA-N 2-nitro-4-(trifluoromethyl)aniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O ATXBGHLILIABGX-UHFFFAOYSA-N 0.000 description 1
- KXEMVGQZZLRLBE-UHFFFAOYSA-N 2-nitro-4-(trifluoromethyl)benzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1S(Cl)(=O)=O KXEMVGQZZLRLBE-UHFFFAOYSA-N 0.000 description 1
- XZEDEVRSUANQEM-UHFFFAOYSA-N 2-nitro-4-(trifluoromethyl)phenol Chemical compound OC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O XZEDEVRSUANQEM-UHFFFAOYSA-N 0.000 description 1
- QJJGPZTVVISLNI-UHFFFAOYSA-N 2-nitro-5-propan-2-ylphenol Chemical compound CC(C)C1=CC=C([N+]([O-])=O)C(O)=C1 QJJGPZTVVISLNI-UHFFFAOYSA-N 0.000 description 1
- YNRCTIUUZWJXKQ-UHFFFAOYSA-N 2-nitro-5-propan-2-ylphenol;3-propan-2-ylphenol Chemical compound CC(C)C1=CC=CC(O)=C1.CC(C)C1=CC=C([N+]([O-])=O)C(O)=C1 YNRCTIUUZWJXKQ-UHFFFAOYSA-N 0.000 description 1
- FMPKXGYPBUWNNG-UHFFFAOYSA-N 2-nitro-6-(trifluoromethyl)phenol Chemical compound OC1=C([N+]([O-])=O)C=CC=C1C(F)(F)F FMPKXGYPBUWNNG-UHFFFAOYSA-N 0.000 description 1
- UZXYRUOSHRFKND-MDZDMXLPSA-N 2-nitro-6-[(E)-2-phenylethenyl]phenol Chemical compound C1=CC=C([N+]([O-])=O)C(O)=C1\C=C\C1=CC=CC=C1 UZXYRUOSHRFKND-MDZDMXLPSA-N 0.000 description 1
- QMBIPOMGUFPDHY-UHFFFAOYSA-N 2-nitro-6-phenylmethoxyphenol;2-phenylmethoxyphenol Chemical compound OC1=CC=CC=C1OCC1=CC=CC=C1.C1=CC=C([N+]([O-])=O)C(O)=C1OCC1=CC=CC=C1 QMBIPOMGUFPDHY-UHFFFAOYSA-N 0.000 description 1
- IIBOYMCHHLZIKC-UHFFFAOYSA-N 2-nitro-6-phenylphenol Chemical compound C1=CC=C([N+]([O-])=O)C(O)=C1C1=CC=CC=C1 IIBOYMCHHLZIKC-UHFFFAOYSA-N 0.000 description 1
- SNIBPLNVBYUZKZ-UHFFFAOYSA-N 2-nitro-6-propylphenol Chemical compound CCCC1=CC=CC([N+]([O-])=O)=C1O SNIBPLNVBYUZKZ-UHFFFAOYSA-N 0.000 description 1
- NKAYMSAPNXUYBD-UHFFFAOYSA-N 2-nitro-9h-fluoren-1-ol Chemical compound C1=CC=C2C3=CC=C([N+]([O-])=O)C(O)=C3CC2=C1 NKAYMSAPNXUYBD-UHFFFAOYSA-N 0.000 description 1
- PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- VAYMIYBJLRRIFR-UHFFFAOYSA-N 2-tolyl isocyanate Chemical compound CC1=CC=CC=C1N=C=O VAYMIYBJLRRIFR-UHFFFAOYSA-N 0.000 description 1
- RSJSYCZYQNJQPY-UHFFFAOYSA-N 3,4-dimethoxybenzenesulfonyl chloride Chemical compound COC1=CC=C(S(Cl)(=O)=O)C=C1OC RSJSYCZYQNJQPY-UHFFFAOYSA-N 0.000 description 1
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
- NBECSRZXAMQLLS-UHFFFAOYSA-N 3-(2-hydroxy-3-nitrophenyl)prop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=CC([N+]([O-])=O)=C1O NBECSRZXAMQLLS-UHFFFAOYSA-N 0.000 description 1
- GMLPYACMPUSEGC-UHFFFAOYSA-N 3-(2-hydroxy-3-nitrophenyl)prop-2-enoic acid;3-(2-hydroxyphenyl)prop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=CC=C1O.OC(=O)C=CC1=CC=CC([N+]([O-])=O)=C1O GMLPYACMPUSEGC-UHFFFAOYSA-N 0.000 description 1
- UCDHERSZARNKOB-UHFFFAOYSA-N 3-(3-hydroxy-4-nitrophenyl)prop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=C([N+]([O-])=O)C(O)=C1 UCDHERSZARNKOB-UHFFFAOYSA-N 0.000 description 1
- RKMOQMFLVWHPHK-UHFFFAOYSA-N 3-(3-hydroxy-4-nitrophenyl)prop-2-enoic acid;3-(3-hydroxyphenyl)prop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=CC(O)=C1.OC(=O)C=CC1=CC=C([N+]([O-])=O)C(O)=C1 RKMOQMFLVWHPHK-UHFFFAOYSA-N 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
- CGZWSGLCVUWYAT-UHFFFAOYSA-N 3-(benzoylcarbamoylamino)-2-hydroxy-n-phenylbenzamide Chemical compound C1=CC=C(C(=O)NC=2C=CC=CC=2)C(O)=C1NC(=O)NC(=O)C1=CC=CC=C1 CGZWSGLCVUWYAT-UHFFFAOYSA-N 0.000 description 1
- IQGMRVWUTCYCST-UHFFFAOYSA-N 3-Aminosalicylic acid Chemical compound NC1=CC=CC(C(O)=O)=C1O IQGMRVWUTCYCST-UHFFFAOYSA-N 0.000 description 1
- CQFHTGIXWOGKOR-UHFFFAOYSA-N 3-[2-(hydroxymethyl)-3-nitrophenyl]prop-2-enoic acid Chemical compound OCC1=C(C=CC(O)=O)C=CC=C1[N+]([O-])=O CQFHTGIXWOGKOR-UHFFFAOYSA-N 0.000 description 1
- IUUXZDXFVTWINA-UHFFFAOYSA-N 3-[2-[(2-bromophenyl)carbamoylamino]phenyl]-2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(C=2C(=CC=CC=2)NC(=O)NC=2C(=CC=CC=2)Br)=C1O IUUXZDXFVTWINA-UHFFFAOYSA-N 0.000 description 1
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
- NGJXVRLGYMLJIW-UHFFFAOYSA-N 3-[3-amino-2-(hydroxymethyl)phenyl]prop-2-enoic acid Chemical compound NC1=CC=CC(C=CC(O)=O)=C1CO NGJXVRLGYMLJIW-UHFFFAOYSA-N 0.000 description 1
- CQXVCXOOWZJYNA-UHFFFAOYSA-N 3-[4-amino-3-(hydroxymethyl)phenyl]prop-2-enoic acid Chemical compound NC1=CC=C(C=CC(O)=O)C=C1CO CQXVCXOOWZJYNA-UHFFFAOYSA-N 0.000 description 1
- NJXPYZHXZZCTNI-UHFFFAOYSA-N 3-aminobenzonitrile Chemical compound NC1=CC=CC(C#N)=C1 NJXPYZHXZZCTNI-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
- DFMDAJMTLJGKFW-UHFFFAOYSA-N 3-chloro-2-nitrophenol Chemical compound OC1=CC=CC(Cl)=C1[N+]([O-])=O DFMDAJMTLJGKFW-UHFFFAOYSA-N 0.000 description 1
- GAWNBKUTBVLIPL-UHFFFAOYSA-N 3-fluoro-2-nitrophenol Chemical compound OC1=CC=CC(F)=C1[N+]([O-])=O GAWNBKUTBVLIPL-UHFFFAOYSA-N 0.000 description 1
- JELNXWUZFOQXGZ-UHFFFAOYSA-N 3-hydroxy-2-nitrobenzonitrile Chemical compound OC1=CC=CC(C#N)=C1[N+]([O-])=O JELNXWUZFOQXGZ-UHFFFAOYSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- YMIKCZUFAPAVLQ-UHFFFAOYSA-N 3-hydroxybenzonitrile;3-hydroxy-4-nitrobenzonitrile Chemical compound OC1=CC=CC(C#N)=C1.OC1=CC(C#N)=CC=C1[N+]([O-])=O YMIKCZUFAPAVLQ-UHFFFAOYSA-N 0.000 description 1
- RFSKGCVUDQRZSD-UHFFFAOYSA-N 3-methoxythiophene Chemical compound COC=1C=CSC=1 RFSKGCVUDQRZSD-UHFFFAOYSA-N 0.000 description 1
- KFPMLWUKHQMEBU-UHFFFAOYSA-N 3-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC(S(Cl)(=O)=O)=C1 KFPMLWUKHQMEBU-UHFFFAOYSA-N 0.000 description 1
- MWWNNNAOGWPTQY-UHFFFAOYSA-N 3-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(S(Cl)(=O)=O)=C1 MWWNNNAOGWPTQY-UHFFFAOYSA-N 0.000 description 1
- IVTWLTRKVRJPNG-UHFFFAOYSA-N 4,5-dichlorothiophene-2-sulfonyl chloride Chemical compound ClC=1C=C(S(Cl)(=O)=O)SC=1Cl IVTWLTRKVRJPNG-UHFFFAOYSA-N 0.000 description 1
- SIPAGAIYBSRGJB-UHFFFAOYSA-N 4-[(2-bromophenyl)carbamoylamino]-3-hydroxybenzamide Chemical compound OC1=CC(C(=O)N)=CC=C1NC(=O)NC1=CC=CC=C1Br SIPAGAIYBSRGJB-UHFFFAOYSA-N 0.000 description 1
- MDQZQLIOAULXOM-UHFFFAOYSA-N 4-[(2-bromophenyl)carbamoylamino]-3-hydroxybenzamide;1-(2-bromophenyl)-3-(2,3,5-trifluoro-6-hydroxyphenyl)urea Chemical compound OC1=CC(C(=O)N)=CC=C1NC(=O)NC1=CC=CC=C1Br.OC1=C(F)C=C(F)C(F)=C1NC(=O)NC1=CC=CC=C1Br MDQZQLIOAULXOM-UHFFFAOYSA-N 0.000 description 1
- GRDXCFKBQWDAJH-UHFFFAOYSA-N 4-acetamidobenzenesulfonyl chloride Chemical compound CC(=O)NC1=CC=C(S(Cl)(=O)=O)C=C1 GRDXCFKBQWDAJH-UHFFFAOYSA-N 0.000 description 1
- GLJFZIKVMDSXMY-UHFFFAOYSA-N 4-amino-3-hydroxybenzamide Chemical compound NC(=O)C1=CC=C(N)C(O)=C1 GLJFZIKVMDSXMY-UHFFFAOYSA-N 0.000 description 1
- NFPYJDZQOKCYIE-UHFFFAOYSA-N 4-amino-3-hydroxybenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1O NFPYJDZQOKCYIE-UHFFFAOYSA-N 0.000 description 1
- RXCMFQDTWCCLBL-UHFFFAOYSA-N 4-amino-3-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(N)=C(O)C=C(S(O)(=O)=O)C2=C1 RXCMFQDTWCCLBL-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
- ACQVEWFMUBXEMR-UHFFFAOYSA-N 4-bromo-2-fluoro-6-nitrophenol Chemical compound OC1=C(F)C=C(Br)C=C1[N+]([O-])=O ACQVEWFMUBXEMR-UHFFFAOYSA-N 0.000 description 1
- DNYRLBZBDGVLHF-UHFFFAOYSA-N 4-bromo-5-methyl-2-nitrophenol Chemical compound CC1=CC(O)=C([N+]([O-])=O)C=C1Br DNYRLBZBDGVLHF-UHFFFAOYSA-N 0.000 description 1
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
- ZHRLVDHMIJDWSS-UHFFFAOYSA-N 4-fluoro-2-nitrophenol Chemical compound OC1=CC=C(F)C=C1[N+]([O-])=O ZHRLVDHMIJDWSS-UHFFFAOYSA-N 0.000 description 1
- INBLGVOPOSGVTA-UHFFFAOYSA-N 4-hydroxy-3-nitrobenzonitrile Chemical compound OC1=CC=C(C#N)C=C1[N+]([O-])=O INBLGVOPOSGVTA-UHFFFAOYSA-N 0.000 description 1
- RAUWPNXIALNKQM-UHFFFAOYSA-N 4-nitro-1,2-phenylenediamine Chemical compound NC1=CC=C([N+]([O-])=O)C=C1N RAUWPNXIALNKQM-UHFFFAOYSA-N 0.000 description 1
- XJNPNXSISMKQEX-UHFFFAOYSA-N 4-nitrocatechol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1O XJNPNXSISMKQEX-UHFFFAOYSA-N 0.000 description 1
- QIZPONOMFWAPRR-UHFFFAOYSA-N 4-phenoxybenzenesulfonyl chloride Chemical compound C1=CC(S(=O)(=O)Cl)=CC=C1OC1=CC=CC=C1 QIZPONOMFWAPRR-UHFFFAOYSA-N 0.000 description 1
- FVKYLHATVWKUMW-UHFFFAOYSA-N 402-17-5 Chemical compound OC1=CC(C(F)(F)F)=CC=C1[N+]([O-])=O FVKYLHATVWKUMW-UHFFFAOYSA-N 0.000 description 1
- YJIUQVPMLSGDMP-UHFFFAOYSA-N 5-ethyl-2-nitrophenol Chemical compound CCC1=CC=C([N+]([O-])=O)C(O)=C1 YJIUQVPMLSGDMP-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
- KRURHZHJEDNBCM-UHFFFAOYSA-N 6-amino-2,3-difluorophenol Chemical compound NC1=CC=C(F)C(F)=C1O KRURHZHJEDNBCM-UHFFFAOYSA-N 0.000 description 1
- JBMHSKGUMDJIIU-UHFFFAOYSA-N 6-amino-2,3-diphenylphenol Chemical compound C=1C=CC=CC=1C1=C(O)C(N)=CC=C1C1=CC=CC=C1 JBMHSKGUMDJIIU-UHFFFAOYSA-N 0.000 description 1
- MVGYYGCFVPMJAQ-UHFFFAOYSA-N 6-amino-7-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(O)C(N)=CC2=C1 MVGYYGCFVPMJAQ-UHFFFAOYSA-N 0.000 description 1
- LYPMXMBQPXPNIQ-UHFFFAOYSA-N 609-89-2 Chemical compound OC1=C(Cl)C=C(Cl)C=C1[N+]([O-])=O LYPMXMBQPXPNIQ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [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
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920001817 Agar Polymers 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
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical class N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 235000003911 Arachis Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 206010003645 Atopy Diseases 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- NNCCLVVUBLJCIM-UHFFFAOYSA-N C(C)C=1C=C(C=CC1)O.[N+](=O)([O-])C1=C(C=C(C=C1)CC)O Chemical compound C(C)C=1C=C(C=CC1)O.[N+](=O)([O-])C1=C(C=C(C=C1)CC)O NNCCLVVUBLJCIM-UHFFFAOYSA-N 0.000 description 1
- BRVONJGWHOVUHW-UHFFFAOYSA-N C(CC)C1=C(C=CC=C1)O.[N+](=O)([O-])C1=C(C(=CC=C1)CCC)O Chemical compound C(CC)C1=C(C=CC=C1)O.[N+](=O)([O-])C1=C(C(=CC=C1)CCC)O BRVONJGWHOVUHW-UHFFFAOYSA-N 0.000 description 1
- IVECOXMQRZSGIX-UHFFFAOYSA-N C1(=CC=CC=C1)C1=C(C=CC=C1)O.[N+](=O)([O-])C1=C(C(=CC=C1)C1=CC=CC=C1)O Chemical compound C1(=CC=CC=C1)C1=C(C=CC=C1)O.[N+](=O)([O-])C1=C(C(=CC=C1)C1=CC=CC=C1)O IVECOXMQRZSGIX-UHFFFAOYSA-N 0.000 description 1
- BTGRZTQDYYLQDN-UHFFFAOYSA-N C1(=CC=CC=C1)NC(=O)C1=C(C=CC=C1)O.[N+](=O)([O-])C1=C(C(=CC=C1)C(=O)NC1=CC=CC=C1)O Chemical compound C1(=CC=CC=C1)NC(=O)C1=C(C=CC=C1)O.[N+](=O)([O-])C1=C(C(=CC=C1)C(=O)NC1=CC=CC=C1)O BTGRZTQDYYLQDN-UHFFFAOYSA-N 0.000 description 1
- JOWLORANCVLMOD-UHFFFAOYSA-N CN(S(=O)(=O)NC1(N)CC=CC=C1)C Chemical compound CN(S(=O)(=O)NC1(N)CC=CC=C1)C JOWLORANCVLMOD-UHFFFAOYSA-N 0.000 description 1
- 101100289995 Caenorhabditis elegans mac-1 gene Proteins 0.000 description 1
- 101100504320 Caenorhabditis elegans mcp-1 gene Proteins 0.000 description 1
- XINPVAWOMDJLMT-UHFFFAOYSA-N ClC1=C(C=CC=C1Cl)O.[N+](=O)([O-])C1=C(C(=C(C=C1)Cl)Cl)O Chemical compound ClC1=C(C=CC=C1Cl)O.[N+](=O)([O-])C1=C(C(=C(C=C1)Cl)Cl)O XINPVAWOMDJLMT-UHFFFAOYSA-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
- 206010014824 Endotoxic shock Diseases 0.000 description 1
- 241000709661 Enterovirus Species 0.000 description 1
- GNHKKOQXPZEAHK-UHFFFAOYSA-N FC(C1=C(C=CC=C1)O)(F)F.[N+](=O)([O-])C1=C(C(=CC=C1)C(F)(F)F)O Chemical compound FC(C1=C(C=CC=C1)O)(F)F.[N+](=O)([O-])C1=C(C(=CC=C1)C(F)(F)F)O GNHKKOQXPZEAHK-UHFFFAOYSA-N 0.000 description 1
- NPQQQNHVSXEKJN-UHFFFAOYSA-N FC1=C(C(=CC=C1F)[N+](=O)[O-])O.OC1=C(N)C=CC(=C1F)F Chemical compound FC1=C(C(=CC=C1F)[N+](=O)[O-])O.OC1=C(N)C=CC(=C1F)F NPQQQNHVSXEKJN-UHFFFAOYSA-N 0.000 description 1
- GFLCJGXRRDSRFT-UHFFFAOYSA-N FC=1C=C(C(=CC1)[N+](=O)[O-])O.OC1=C(N)C=CC(=C1)F Chemical compound FC=1C=C(C(=CC1)[N+](=O)[O-])O.OC1=C(N)C=CC(=C1)F GFLCJGXRRDSRFT-UHFFFAOYSA-N 0.000 description 1
- 108091006027 G proteins Proteins 0.000 description 1
- 102000030782 GTP binding Human genes 0.000 description 1
- 108091000058 GTP-Binding Proteins 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 208000009889 Herpes Simplex Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 101001046686 Homo sapiens Integrin alpha-M Proteins 0.000 description 1
- 101000935040 Homo sapiens Integrin beta-2 Proteins 0.000 description 1
- 101001055222 Homo sapiens Interleukin-8 Proteins 0.000 description 1
- 101000818522 Homo sapiens fMet-Leu-Phe receptor Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- 101000668058 Infectious salmon anemia virus (isolate Atlantic salmon/Norway/810/9/99) RNA-directed RNA polymerase catalytic subunit Proteins 0.000 description 1
- 102100022338 Integrin alpha-M Human genes 0.000 description 1
- 102100025390 Integrin beta-2 Human genes 0.000 description 1
- 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 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 102000004083 Lymphotoxin-alpha Human genes 0.000 description 1
- 108090000542 Lymphotoxin-alpha Proteins 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-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
- IHDWBCYPAYQMCW-UHFFFAOYSA-N NC(N(C1=C(C(C2=CC=CC=C2)S(N)(=O)=O)C=CC=C1)C(C=CC=C1)=C1Br)=O Chemical compound NC(N(C1=C(C(C2=CC=CC=C2)S(N)(=O)=O)C=CC=C1)C(C=CC=C1)=C1Br)=O IHDWBCYPAYQMCW-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 206010029113 Neovascularisation Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- QNCLNCQKWKPAHZ-UHFFFAOYSA-N OC1=C(C=CC(=C1)C#N)NC(=O)NC1=CC(=CC=C1)C(F)(F)F.NC(=O)N Chemical compound OC1=C(C=CC(=C1)C#N)NC(=O)NC1=CC(=CC=C1)C(F)(F)F.NC(=O)N QNCLNCQKWKPAHZ-UHFFFAOYSA-N 0.000 description 1
- QQASHPOWEWGVHT-UHFFFAOYSA-N OC1=C(C=CC(=C1)C#N)NC(=O)NC1=CC=C(C=C1)C1=CC=CC=C1.NC(=O)N Chemical compound OC1=C(C=CC(=C1)C#N)NC(=O)NC1=CC=C(C=C1)C1=CC=CC=C1.NC(=O)N QQASHPOWEWGVHT-UHFFFAOYSA-N 0.000 description 1
- RKVCUXXMFJSCBQ-UHFFFAOYSA-N OC1=C(C=CC(=C1)C)NC(=O)NC1=C(C=CC=C1)Br.NC(=O)N Chemical compound OC1=C(C=CC(=C1)C)NC(=O)NC1=C(C=CC=C1)Br.NC(=O)N RKVCUXXMFJSCBQ-UHFFFAOYSA-N 0.000 description 1
- JBZAVRFVWOEFNF-UHFFFAOYSA-N OC1=C(C=CC(=C1)[N+](=O)[O-])NC(=O)NC1=C(C=CC=C1)OCC.OC1=C(C=CC(=C1)[N+](=O)[O-])NC(=O)NC1=C(C=CC=C1)OCC Chemical compound OC1=C(C=CC(=C1)[N+](=O)[O-])NC(=O)NC1=C(C=CC=C1)OCC.OC1=C(C=CC(=C1)[N+](=O)[O-])NC(=O)NC1=C(C=CC=C1)OCC JBZAVRFVWOEFNF-UHFFFAOYSA-N 0.000 description 1
- NKEDKJVJQCTWAR-UHFFFAOYSA-N OC1=C(C=CC(=C1)[N+](=O)[O-])NC(=O)NC1=CC=CC2=CC=CC=C12.OC1=C(C=CC(=C1)[N+](=O)[O-])NC(=O)NC1=CC=CC2=CC=CC=C12 Chemical compound OC1=C(C=CC(=C1)[N+](=O)[O-])NC(=O)NC1=CC=CC2=CC=CC=C12.OC1=C(C=CC(=C1)[N+](=O)[O-])NC(=O)NC1=CC=CC2=CC=CC=C12 NKEDKJVJQCTWAR-UHFFFAOYSA-N 0.000 description 1
- HBXDGTXUHWLULR-UHFFFAOYSA-N OC1=C(C=CC(=C1Cl)Cl)NC(=O)NC1=C(C=CC=C1)Br.NC(=O)N Chemical compound OC1=C(C=CC(=C1Cl)Cl)NC(=O)NC1=C(C=CC=C1)Br.NC(=O)N HBXDGTXUHWLULR-UHFFFAOYSA-N 0.000 description 1
- FCYCSRITRRDGIN-UHFFFAOYSA-N OC1=C(C=CC=C1C#N)NC(=O)NC1=CC(=CC=C1)C(F)(F)F.NC(=O)N Chemical compound OC1=C(C=CC=C1C#N)NC(=O)NC1=CC(=CC=C1)C(F)(F)F.NC(=O)N FCYCSRITRRDGIN-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-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
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- 102000000479 TCF Transcription Factors Human genes 0.000 description 1
- 108010016283 TCF Transcription Factors Proteins 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
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- IXKSXJFAGXLQOQ-XISFHERQSA-N WHWLQLKPGQPMY Chemical compound C([C@@H](C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(O)=O)NC(=O)[C@@H](N)CC=1C2=CC=CC=C2NC=1)C1=CNC=N1 IXKSXJFAGXLQOQ-XISFHERQSA-N 0.000 description 1
- LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- SLVJLNZLOZPQID-UHFFFAOYSA-N [2-[(2-hydroxy-4-nitrophenyl)carbamoylamino]phenyl]methyl hydrogen sulfate Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=CC=CC=C1COS(O)(=O)=O SLVJLNZLOZPQID-UHFFFAOYSA-N 0.000 description 1
- JPCWPWWDILCKCA-UHFFFAOYSA-N [Si](C)(C)(C(C)(C)C)OC1=C(C=CC(=C1)[N+](=O)[O-])SN=C=O Chemical compound [Si](C)(C)(C(C)(C)C)OC1=C(C=CC(=C1)[N+](=O)[O-])SN=C=O JPCWPWWDILCKCA-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000004450 alkenylene 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
- 150000001408 amides Chemical class 0.000 description 1
- 150000001413 amino acids Chemical group 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- WUVCQOUWKXAJHS-UHFFFAOYSA-N anilino 4-amino-3-hydroxybenzoate Chemical compound C1=C(O)C(N)=CC=C1C(=O)ONC1=CC=CC=C1 WUVCQOUWKXAJHS-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- 210000001130 astrocyte Anatomy 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 210000003719 b-lymphocyte Anatomy 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- UBXYXCRCOKCZIT-UHFFFAOYSA-N biphenyl-3-ol Chemical compound OC1=CC=CC(C=2C=CC=CC=2)=C1 UBXYXCRCOKCZIT-UHFFFAOYSA-N 0.000 description 1
- 210000004271 bone marrow stromal cell Anatomy 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 230000009172 bursting Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000005482 chemotactic factor Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 208000037976 chronic inflammation Diseases 0.000 description 1
- 208000037893 chronic inflammatory disorder Diseases 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000002944 cyanoaryl group Chemical group 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- ZJULYDCRWUEPTK-UHFFFAOYSA-N dichloromethyl Chemical compound Cl[CH]Cl ZJULYDCRWUEPTK-UHFFFAOYSA-N 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000003511 endothelial effect Effects 0.000 description 1
- 231100000284 endotoxic Toxicity 0.000 description 1
- 230000002346 endotoxic effect Effects 0.000 description 1
- 210000005175 epidermal keratinocyte Anatomy 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 210000002919 epithelial cell Anatomy 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005713 exacerbation Effects 0.000 description 1
- 102100021145 fMet-Leu-Phe receptor Human genes 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229960002598 fumaric acid Drugs 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 229940074045 glyceryl distearate Drugs 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 125000005553 heteroaryloxy group Chemical group 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000021995 interleukin-8 production Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- 150000002513 isocyanates Chemical class 0.000 description 1
- NONOKGVFTBWRLD-UHFFFAOYSA-N isocyanatosulfanylimino(oxo)methane Chemical compound O=C=NSN=C=O NONOKGVFTBWRLD-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229960000448 lactic acid Drugs 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 230000000527 lymphocytic effect Effects 0.000 description 1
- KKSDGJDHHZEWEP-UHFFFAOYSA-N m-hydroxycinnamic acid Natural products OC(=O)C=CC1=CC=CC(O)=C1 KKSDGJDHHZEWEP-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 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
- 229940098895 maleic acid Drugs 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 229940099690 malic acid Drugs 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 210000004962 mammalian cell Anatomy 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- DDUNMNVFNVRLFB-VQHVLOKHSA-N methyl (e)-3-[4-[(2-bromophenyl)carbamoylamino]-3-hydroxyphenyl]prop-2-enoate Chemical compound OC1=CC(/C=C/C(=O)OC)=CC=C1NC(=O)NC1=CC=CC=C1Br DDUNMNVFNVRLFB-VQHVLOKHSA-N 0.000 description 1
- FGMISCVVYSYIAQ-UHFFFAOYSA-N methyl 4-[(2-bromophenyl)carbamoylamino]-3-hydroxybenzoate Chemical compound OC1=CC(C(=O)OC)=CC=C1NC(=O)NC1=CC=CC=C1Br FGMISCVVYSYIAQ-UHFFFAOYSA-N 0.000 description 1
- DYBDOVKHIAJFQP-UHFFFAOYSA-N methyl 4-anilino-3-nitrobenzoate Chemical compound [O-][N+](=O)C1=CC(C(=O)OC)=CC=C1NC1=CC=CC=C1 DYBDOVKHIAJFQP-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000005087 mononuclear cell Anatomy 0.000 description 1
- JFCHSQDLLFJHOA-UHFFFAOYSA-N n,n-dimethylsulfamoyl chloride Chemical compound CN(C)S(Cl)(=O)=O JFCHSQDLLFJHOA-UHFFFAOYSA-N 0.000 description 1
- GOYLVLYWQRBVRD-UHFFFAOYSA-N n-(2-aminophenyl)-3-methylbenzenesulfonamide Chemical compound CC1=CC=CC(S(=O)(=O)NC=2C(=CC=CC=2)N)=C1 GOYLVLYWQRBVRD-UHFFFAOYSA-N 0.000 description 1
- KKBCMONERKOXFP-UHFFFAOYSA-N n-(2-aminophenyl)thiophene-2-sulfonamide Chemical compound NC1=CC=CC=C1NS(=O)(=O)C1=CC=CS1 KKBCMONERKOXFP-UHFFFAOYSA-N 0.000 description 1
- JGOAZQAXRONCCI-UHFFFAOYSA-N n-(benzylideneamino)aniline Chemical compound C=1C=CC=CC=1NN=CC1=CC=CC=C1 JGOAZQAXRONCCI-UHFFFAOYSA-N 0.000 description 1
- OIVLDUXIJRSENC-UHFFFAOYSA-N n-(sulfonylamino)aniline Chemical compound O=S(=O)=NNC1=CC=CC=C1 OIVLDUXIJRSENC-UHFFFAOYSA-N 0.000 description 1
- RPCJBRNNUZKOEW-UHFFFAOYSA-N n-[(4-cyano-2-hydroxyphenyl)carbamoyl]benzamide Chemical compound OC1=CC(C#N)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1 RPCJBRNNUZKOEW-UHFFFAOYSA-N 0.000 description 1
- WLHJKINWCGVNEU-UHFFFAOYSA-N n-[4-[(2-anilinophenyl)sulfamoyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC1=CC=CC=C1NC1=CC=CC=C1 WLHJKINWCGVNEU-UHFFFAOYSA-N 0.000 description 1
- HJPVUCISGFMYLB-UHFFFAOYSA-N n-[[2-hydroxy-3-(trifluoromethyl)phenyl]carbamoyl]benzamide Chemical compound C1=CC=C(C(F)(F)F)C(O)=C1NC(=O)NC(=O)C1=CC=CC=C1 HJPVUCISGFMYLB-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
- 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
- 230000030505 negative regulation of chemotaxis Effects 0.000 description 1
- 230000011242 neutrophil chemotaxis Effects 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- PMOWTIHVNWZYFI-UHFFFAOYSA-N o-Coumaric acid Natural products OC(=O)C=CC1=CC=CC=C1O PMOWTIHVNWZYFI-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229940116315 oxalic acid Drugs 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- OAHKWDDSKCRNFE-UHFFFAOYSA-N phenylmethanesulfonyl chloride Chemical compound ClS(=O)(=O)CC1=CC=CC=C1 OAHKWDDSKCRNFE-UHFFFAOYSA-N 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001243 protein synthesis Methods 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001525 receptor binding assay Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000019254 respiratory burst Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 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
- 150000003384 small molecules Chemical class 0.000 description 1
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- OVYTZAASVAZITK-UHFFFAOYSA-M sodium;ethanol;hydroxide Chemical compound [OH-].[Na+].CCO OVYTZAASVAZITK-UHFFFAOYSA-M 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 210000002325 somatostatin-secreting cell Anatomy 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- QCZNZEFAVZZKPE-UHFFFAOYSA-N tert-butyl-(2-isocyanato-5-nitrophenoxy)-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OC1=CC([N+]([O-])=O)=CC=C1N=C=O QCZNZEFAVZZKPE-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YJBKVPRVZAQTPY-UHFFFAOYSA-J tetrachlorostannane;dihydrate Chemical compound O.O.Cl[Sn](Cl)(Cl)Cl YJBKVPRVZAQTPY-UHFFFAOYSA-J 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
- VNNLHYZDXIBHKZ-UHFFFAOYSA-N thiophene-2-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CS1 VNNLHYZDXIBHKZ-UHFFFAOYSA-N 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- KKSDGJDHHZEWEP-SNAWJCMRSA-N trans-3-coumaric acid Chemical compound OC(=O)\C=C\C1=CC=CC(O)=C1 KKSDGJDHHZEWEP-SNAWJCMRSA-N 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 241000712461 unidentified influenza virus Species 0.000 description 1
- 210000003556 vascular endothelial cell Anatomy 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/17—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Virology (AREA)
- Physical Education & Sports Medicine (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Epidemiology (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Molecular Biology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Vascular Medicine (AREA)
- Diabetes (AREA)
- Pulmonology (AREA)
- Urology & Nephrology (AREA)
- Biotechnology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13967599P | 1999-06-16 | 1999-06-16 | |
PCT/US2000/016499 WO2000076495A1 (en) | 1999-06-16 | 2000-06-15 | Il-8 receptor antagonists |
Publications (1)
Publication Number | Publication Date |
---|---|
MXPA01013004A true MXPA01013004A (es) | 2002-07-30 |
Family
ID=22487790
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
MXPA01013004A MXPA01013004A (es) | 1999-06-16 | 2000-06-15 | Antagonistas del receptor de interleucina-8. |
Country Status (20)
Country | Link |
---|---|
EP (1) | EP1185261A4 (xx) |
JP (1) | JP2003501459A (xx) |
KR (1) | KR20020010709A (xx) |
CN (1) | CN1355697A (xx) |
AR (1) | AR030391A1 (xx) |
AU (1) | AU766083B2 (xx) |
BR (1) | BR0010802A (xx) |
CA (1) | CA2377341A1 (xx) |
CO (1) | CO5200760A1 (xx) |
CZ (1) | CZ20014471A3 (xx) |
HK (1) | HK1044483A1 (xx) |
HU (1) | HUP0201571A3 (xx) |
IL (1) | IL145761A0 (xx) |
MX (1) | MXPA01013004A (xx) |
NO (1) | NO20016053L (xx) |
NZ (1) | NZ514695A (xx) |
PL (1) | PL352232A1 (xx) |
TR (1) | TR200103680T2 (xx) |
WO (1) | WO2000076495A1 (xx) |
ZA (1) | ZA200109479B (xx) |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7521479B2 (en) * | 2001-04-16 | 2009-04-21 | Panacea Pharmaceuticals, Inc. | Methods of treating prion disease in mammals |
GB0201882D0 (en) * | 2002-01-28 | 2002-03-13 | Novartis Ag | Organic compounds |
IL166040A0 (en) * | 2002-08-01 | 2006-01-15 | Neurosearch As | Compounds useful for the treatment of diseases responsive to antiangiogenetic therapy |
CA2565519A1 (en) * | 2004-05-12 | 2005-12-01 | Schering Corporation | Cxcr1 and cxcr2 chemokine antagonists |
US7550499B2 (en) | 2004-05-12 | 2009-06-23 | Bristol-Myers Squibb Company | Urea antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions |
TW200600492A (en) | 2004-05-18 | 2006-01-01 | Achillion Pharmaceuticals Inc | Substituted aryl acylthioureas and related compounds; inhibitors of viral replication |
JP2008517930A (ja) | 2004-10-21 | 2008-05-29 | トランス テック ファーマ,インコーポレイテッド | GalR1のアゴニストとしてのビススルホンアミド化合物、組成物、及び使用法 |
MX2007008434A (es) | 2005-01-19 | 2007-07-25 | Squibb Bristol Myers Co | Derivados de 2-fenoxi-n-(1,3,4-tiadizol-2il)piridin-3-amina y compuestos relacionados como inhibidores del receptor p2y1 para el tratamiento de trastornos tromboembolicos. |
WO2006089871A2 (en) * | 2005-02-23 | 2006-08-31 | Neurosearch A/S | Diphenylurea derivatives useful as erg channel openers for the treatment of cardiac arrhythmias |
ES2360818T3 (es) | 2005-06-27 | 2011-06-09 | Bristol-Myers Squibb Company | Miméticos de urea lineal antagonistas del receptor p2y, útiles en el tratamiento de afecciones trombóticas. |
WO2007002635A2 (en) | 2005-06-27 | 2007-01-04 | Bristol-Myers Squibb Company | C-linked cyclic antagonists of p2y1 receptor useful in the treatment of thrombotic conditions |
US7728008B2 (en) | 2005-06-27 | 2010-06-01 | Bristol-Myers Squibb Company | N-linked heterocyclic antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions |
WO2007002634A1 (en) | 2005-06-27 | 2007-01-04 | Bristol-Myers Squibb Company | Carbocycle and heterocycle antagonists of p2y1 receptor useful in the treatment of thrombotic conditions |
US7960569B2 (en) | 2006-10-17 | 2011-06-14 | Bristol-Myers Squibb Company | Indole antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions |
JP2008184403A (ja) * | 2007-01-29 | 2008-08-14 | Japan Health Science Foundation | 新規c型肝炎ウイルス阻害剤 |
KR100982661B1 (ko) * | 2008-04-22 | 2010-09-17 | 전남대학교산학협력단 | 플라스멥신 ⅱ 활성을 저해하는 화합물을 유효성분으로함유하는 말라리아 예방 및 치료를 위한 약학 조성물 및이를 이용한 말라리아 치료방법 |
KR100970940B1 (ko) * | 2010-05-03 | 2010-07-20 | 전남대학교산학협력단 | 플라스멥신 ⅱ 활성을 저해하는 화합물을 유효성분으로 함유하는 말라리아 예방 및 치료를 위한 약학 조성물 및 이를 이용한 말라리아 치료방법 |
US10093617B1 (en) * | 2015-10-30 | 2018-10-09 | Sumitomo Chemical Company, Limited | Method for producing 2-amino-4-substituted phenol |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ZA921120B (en) * | 1991-02-19 | 1993-01-27 | Smithkline Beecham Corp | Cytokine inhibitors |
JPH11503110A (ja) * | 1995-02-17 | 1999-03-23 | スミスクライン・ビーチャム・コーポレイション | Il−8受容体拮抗剤 |
WO2000016768A1 (en) * | 1998-09-18 | 2000-03-30 | Smithkline Beecham Corporation | Cxcr2 inhibitors and pmn adhesion and t-cell chemotaxis |
-
2000
- 2000-06-13 CO CO00043844A patent/CO5200760A1/es not_active Application Discontinuation
- 2000-06-14 AR ARP000102923A patent/AR030391A1/es not_active Application Discontinuation
- 2000-06-15 NZ NZ514695A patent/NZ514695A/en unknown
- 2000-06-15 HU HU0201571A patent/HUP0201571A3/hu unknown
- 2000-06-15 CN CN00809045A patent/CN1355697A/zh active Pending
- 2000-06-15 KR KR1020017016142A patent/KR20020010709A/ko not_active Application Discontinuation
- 2000-06-15 MX MXPA01013004A patent/MXPA01013004A/es unknown
- 2000-06-15 EP EP00942843A patent/EP1185261A4/en not_active Withdrawn
- 2000-06-15 CZ CZ20014471A patent/CZ20014471A3/cs unknown
- 2000-06-15 CA CA002377341A patent/CA2377341A1/en not_active Abandoned
- 2000-06-15 TR TR2001/03680T patent/TR200103680T2/xx unknown
- 2000-06-15 WO PCT/US2000/016499 patent/WO2000076495A1/en not_active Application Discontinuation
- 2000-06-15 PL PL00352232A patent/PL352232A1/xx not_active Application Discontinuation
- 2000-06-15 IL IL14576100A patent/IL145761A0/xx unknown
- 2000-06-15 AU AU57413/00A patent/AU766083B2/en not_active Ceased
- 2000-06-15 JP JP2001502828A patent/JP2003501459A/ja not_active Withdrawn
- 2000-06-15 BR BR0010802-2A patent/BR0010802A/pt not_active IP Right Cessation
-
2001
- 2001-11-16 ZA ZA200109479A patent/ZA200109479B/en unknown
- 2001-12-11 NO NO20016053A patent/NO20016053L/no not_active Application Discontinuation
-
2002
- 2002-08-22 HK HK02106188.7A patent/HK1044483A1/zh unknown
Also Published As
Publication number | Publication date |
---|---|
CZ20014471A3 (cs) | 2002-08-14 |
HUP0201571A2 (en) | 2002-08-28 |
CO5200760A1 (es) | 2002-09-27 |
EP1185261A1 (en) | 2002-03-13 |
NZ514695A (en) | 2004-05-28 |
PL352232A1 (en) | 2003-08-11 |
AU5741300A (en) | 2001-01-02 |
JP2003501459A (ja) | 2003-01-14 |
KR20020010709A (ko) | 2002-02-04 |
NO20016053D0 (no) | 2001-12-11 |
CN1355697A (zh) | 2002-06-26 |
TR200103680T2 (tr) | 2002-07-22 |
HUP0201571A3 (en) | 2002-11-28 |
CA2377341A1 (en) | 2000-12-21 |
NO20016053L (no) | 2001-12-11 |
AR030391A1 (es) | 2003-08-20 |
ZA200109479B (en) | 2002-11-18 |
HK1044483A1 (zh) | 2002-10-25 |
WO2000076495A1 (en) | 2000-12-21 |
EP1185261A4 (en) | 2004-02-25 |
IL145761A0 (en) | 2002-07-25 |
AU766083B2 (en) | 2003-10-09 |
BR0010802A (pt) | 2002-02-19 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US6180675B1 (en) | IL-8 receptor antagonists | |
US6262113B1 (en) | IL-8 receptor antagonists | |
US6005008A (en) | IL-8 receptor antagonists | |
US5780483A (en) | IL-8 receptor antagonists | |
US6211373B1 (en) | Phenyl urea antagonists of the IL-8 receptor | |
US6271261B1 (en) | IL-8 receptor antagonists | |
AU726858B2 (en) | IL-8 receptor antagonists | |
MXPA01013004A (es) | Antagonistas del receptor de interleucina-8. | |
AU3409197A (en) | Il-8 receptor antagonists | |
WO1997049399A1 (en) | Il-8 receptor antagonists | |
AU729893B2 (en) | IL-8 receptor antagonists | |
MXPA01013005A (es) | Antagonistas de receptor de interleucina-8. | |
CA2375683A1 (en) | Il-8 receptor antagonists | |
WO1997049287A1 (en) | Il-8 receptor antagonists | |
IL141121A (en) | Process for preparing cyano-phenol derivatives | |
CA2432662A1 (en) | Il-8 receptor antagonists | |
CZ256998A3 (cs) | Antagonista IL-8 receptoru | |
CA2377397A1 (en) | Il-8 receptor antagonists | |
WO2000076508A1 (en) | Il-8 receptor antagonists | |
NZ500441A (en) | Preparation of benzo-2-triazole substituted compounds for use in treating chemokine mediated diseases |