CA2351690A1 - Heterocyclic carboxamide-containing thiourea inhibitors of herpes viruses containing a substituted phenylenediamine group - Google Patents
Heterocyclic carboxamide-containing thiourea inhibitors of herpes viruses containing a substituted phenylenediamine group Download PDFInfo
- Publication number
- CA2351690A1 CA2351690A1 CA002351690A CA2351690A CA2351690A1 CA 2351690 A1 CA2351690 A1 CA 2351690A1 CA 002351690 A CA002351690 A CA 002351690A CA 2351690 A CA2351690 A CA 2351690A CA 2351690 A1 CA2351690 A1 CA 2351690A1
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- thioureido
- chloro
- carbon atoms
- amide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 241001529453 unidentified herpesvirus Species 0.000 title claims abstract description 18
- -1 Heterocyclic carboxamide Chemical class 0.000 title description 156
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title description 12
- 239000003112 inhibitor Substances 0.000 title description 12
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 title description 4
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical group NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 title description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 131
- 150000001875 compounds Chemical class 0.000 claims abstract description 113
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 45
- 239000001257 hydrogen Substances 0.000 claims abstract description 45
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 35
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 15
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 13
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
- 125000004001 thioalkyl group Chemical group 0.000 claims abstract description 6
- 241000701024 Human betaherpesvirus 5 Species 0.000 claims abstract description 5
- 241000700584 Simplexvirus Species 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 223
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 22
- 150000002431 hydrogen Chemical group 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 241000701085 Human alphaherpesvirus 3 Species 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 230000010076 replication Effects 0.000 claims description 3
- RTHGALAUXSQETR-UHFFFAOYSA-N 5-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-2-(furan-2-carbonylamino)benzoic acid Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1C(O)=O)=CC=C1NC(=O)C1=CC=CO1 RTHGALAUXSQETR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- IVZPBGXWYFFTRA-UHFFFAOYSA-N n-[2-chloro-4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]phenyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1Cl)=CC=C1NC(=O)C1=CC=CO1 IVZPBGXWYFFTRA-UHFFFAOYSA-N 0.000 claims description 2
- IVWGGGIKOICPHX-UHFFFAOYSA-N n-[3-chloro-4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]phenyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C(=C1)Cl)=CC=C1NC(=O)C1=CC=CO1 IVWGGGIKOICPHX-UHFFFAOYSA-N 0.000 claims description 2
- VVCYTMKINNBCAU-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-2-(phenylcarbamoyl)phenyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1C(=O)NC=2C=CC=CC=2)=CC=C1NC(=O)C1=CC=CO1 VVCYTMKINNBCAU-UHFFFAOYSA-N 0.000 claims description 2
- BALIPFKCBQPMKC-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-2-(trifluoromethyl)phenyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1C(F)(F)F)=CC=C1NC(=O)C1=CC=CO1 BALIPFKCBQPMKC-UHFFFAOYSA-N 0.000 claims description 2
- MVDDTRTYCQAJNC-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-2-methoxy-5-methylphenyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C(=C1)C)=CC(OC)=C1NC(=O)C1=CC=CO1 MVDDTRTYCQAJNC-UHFFFAOYSA-N 0.000 claims description 2
- HHPFMXDSJANDMY-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-2-methoxyphenyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1OC)=CC=C1NC(=O)C1=CC=CO1 HHPFMXDSJANDMY-UHFFFAOYSA-N 0.000 claims description 2
- YMWKSEPIFCEVMT-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-2-methylphenyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1C)=CC=C1NC(=O)C1=CC=CO1 YMWKSEPIFCEVMT-UHFFFAOYSA-N 0.000 claims description 2
- BXFNYZZUCCFYSD-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-3-cyanophenyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C(=C1)C#N)=CC=C1NC(=O)C1=CC=CO1 BXFNYZZUCCFYSD-UHFFFAOYSA-N 0.000 claims description 2
- MVPZQPMABBRKST-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-3-methoxyphenyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C(=C1)OC)=CC=C1NC(=O)C1=CC=CO1 MVPZQPMABBRKST-UHFFFAOYSA-N 0.000 claims description 2
- HQSLZZTYRDVJIX-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]naphthalen-1-yl]furan-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C1=CC=CC=C11)=CC=C1NC(=O)C1=CC=CO1 HQSLZZTYRDVJIX-UHFFFAOYSA-N 0.000 claims description 2
- 101100134925 Gallus gallus COR6 gene Proteins 0.000 claims 4
- 208000029433 Herpesviridae infectious disease Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- QXBSQMBUEFIUPQ-UHFFFAOYSA-N n-[2-benzoyl-4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]phenyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1C(=O)C=2C=CC=CC=2)=CC=C1NC(=O)C1=CC=CO1 QXBSQMBUEFIUPQ-UHFFFAOYSA-N 0.000 claims 1
- JPZGNXJCBOMBMR-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-2,5-dimethoxyphenyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C(=C1)OC)=CC(OC)=C1NC(=O)C1=CC=CO1 JPZGNXJCBOMBMR-UHFFFAOYSA-N 0.000 claims 1
- IMKYKPMGBIAZML-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-2-cyanophenyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1C#N)=CC=C1NC(=O)C1=CC=CO1 IMKYKPMGBIAZML-UHFFFAOYSA-N 0.000 claims 1
- UWEFSTBGDNYWES-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-3-(trifluoromethyl)phenyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C(=C1)C(F)(F)F)=CC=C1NC(=O)C1=CC=CO1 UWEFSTBGDNYWES-UHFFFAOYSA-N 0.000 claims 1
- GDUBTFSXSUOPTA-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-3-methylphenyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C(=C1)C)=CC=C1NC(=O)C1=CC=CO1 GDUBTFSXSUOPTA-UHFFFAOYSA-N 0.000 claims 1
- NSOSRWUCBJXURG-UHFFFAOYSA-N n-[5-chloro-4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-2-hydroxyphenyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C(=C1)Cl)=CC(O)=C1NC(=O)C1=CC=CO1 NSOSRWUCBJXURG-UHFFFAOYSA-N 0.000 claims 1
- UDAPAWGOOPLTNL-UHFFFAOYSA-N n-[5-chloro-4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-2-methylphenyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C(=C1)Cl)=CC(C)=C1NC(=O)C1=CC=CO1 UDAPAWGOOPLTNL-UHFFFAOYSA-N 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 abstract description 18
- 241000700605 Viruses Species 0.000 abstract description 15
- 241000282414 Homo sapiens Species 0.000 abstract description 13
- 238000011282 treatment Methods 0.000 abstract description 13
- 201000010099 disease Diseases 0.000 abstract description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 12
- 241000701044 Human gammaherpesvirus 4 Species 0.000 abstract description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 234
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 220
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 166
- 239000002904 solvent Substances 0.000 description 154
- 239000000243 solution Substances 0.000 description 147
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 138
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 111
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 107
- 239000000203 mixture Substances 0.000 description 104
- HJZYBDPHAHGHAZ-UHFFFAOYSA-N thiadiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSN=N1 HJZYBDPHAHGHAZ-UHFFFAOYSA-N 0.000 description 100
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 99
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 91
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 88
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 82
- 239000000047 product Substances 0.000 description 79
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 71
- 238000006243 chemical reaction Methods 0.000 description 66
- 239000007787 solid Substances 0.000 description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 66
- 239000007858 starting material Substances 0.000 description 63
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 60
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 56
- 229920006395 saturated elastomer Polymers 0.000 description 53
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 48
- 239000002253 acid Substances 0.000 description 46
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 43
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 42
- 150000001412 amines Chemical class 0.000 description 42
- 238000010992 reflux Methods 0.000 description 40
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 39
- 239000003921 oil Substances 0.000 description 39
- 235000019198 oils Nutrition 0.000 description 39
- 239000011780 sodium chloride Substances 0.000 description 39
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 38
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 37
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 35
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 31
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 30
- 239000000741 silica gel Substances 0.000 description 29
- 229910002027 silica gel Inorganic materials 0.000 description 29
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 22
- 238000001704 evaporation Methods 0.000 description 22
- 230000008020 evaporation Effects 0.000 description 22
- 239000000284 extract Substances 0.000 description 22
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 20
- 239000002585 base Substances 0.000 description 20
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 20
- 229960000583 acetic acid Drugs 0.000 description 19
- 229910000027 potassium carbonate Inorganic materials 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 14
- 238000003756 stirring Methods 0.000 description 13
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- 208000015181 infectious disease Diseases 0.000 description 12
- 239000000543 intermediate Substances 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 12
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 12
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 11
- OFFSPAZVIVZPHU-UHFFFAOYSA-N 1-benzofuran-2-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)=CC2=C1 OFFSPAZVIVZPHU-UHFFFAOYSA-N 0.000 description 10
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 10
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 10
- 229910052786 argon Inorganic materials 0.000 description 10
- 238000003556 assay Methods 0.000 description 10
- 239000012298 atmosphere Substances 0.000 description 10
- 239000011877 solvent mixture Substances 0.000 description 10
- 150000003512 tertiary amines Chemical class 0.000 description 10
- 150000003585 thioureas Chemical class 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 9
- 150000001448 anilines Chemical class 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 229910052763 palladium Inorganic materials 0.000 description 9
- 230000009467 reduction Effects 0.000 description 9
- 238000006722 reduction reaction Methods 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 8
- 239000012230 colorless oil Substances 0.000 description 8
- 239000012362 glacial acetic acid Substances 0.000 description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 239000005909 Kieselgur Substances 0.000 description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 150000008359 benzonitriles Chemical class 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 150000005181 nitrobenzenes Chemical class 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 230000011514 reflex Effects 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- XXWIYOBCHKCWNT-UHFFFAOYSA-N 2,4-dimethoxy-1-nitrobenzene Chemical compound COC1=CC=C([N+]([O-])=O)C(OC)=C1 XXWIYOBCHKCWNT-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 235000019270 ammonium chloride Nutrition 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 6
- 239000012279 sodium borohydride Substances 0.000 description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 description 6
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- NRTULWPODYLFOJ-UHFFFAOYSA-N 5-methoxy-2-nitrophenol Chemical group COC1=CC=C([N+]([O-])=O)C(O)=C1 NRTULWPODYLFOJ-UHFFFAOYSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- 108010060309 Glucuronidase Proteins 0.000 description 5
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 230000000840 anti-viral effect Effects 0.000 description 5
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 5
- PPDJNZTUDFPAHX-UHFFFAOYSA-N benzyltrimethylammonium dichloroiodate Chemical compound Cl[I-]Cl.C[N+](C)(C)CC1=CC=CC=C1 PPDJNZTUDFPAHX-UHFFFAOYSA-N 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical class CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 5
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 5
- 239000000499 gel Substances 0.000 description 5
- 201000006747 infectious mononucleosis Diseases 0.000 description 5
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 5
- 239000000391 magnesium silicate Substances 0.000 description 5
- 229910052919 magnesium silicate Inorganic materials 0.000 description 5
- 235000019792 magnesium silicate Nutrition 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- DPHCXXYPSYMICK-UHFFFAOYSA-N 2-chloro-1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C(Cl)=C1 DPHCXXYPSYMICK-UHFFFAOYSA-N 0.000 description 4
- HSHNITRMYYLLCV-UHFFFAOYSA-N 4-methylumbelliferone Chemical compound C1=C(O)C=CC2=C1OC(=O)C=C2C HSHNITRMYYLLCV-UHFFFAOYSA-N 0.000 description 4
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 4
- 239000005708 Sodium hypochlorite Substances 0.000 description 4
- 150000001733 carboxylic acid esters Chemical class 0.000 description 4
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 description 4
- 125000004663 dialkyl amino group Chemical group 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- 210000003953 foreskin Anatomy 0.000 description 4
- IRSCQMHQWWYFCW-UHFFFAOYSA-N ganciclovir Chemical compound O=C1NC(N)=NC2=C1N=CN2COC(CO)CO IRSCQMHQWWYFCW-UHFFFAOYSA-N 0.000 description 4
- 229960002963 ganciclovir Drugs 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229940098779 methanesulfonic acid Drugs 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- ZJAOAACCNHFJAH-UHFFFAOYSA-N phosphonoformic acid Chemical compound OC(=O)P(O)(O)=O ZJAOAACCNHFJAH-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 230000007420 reactivation Effects 0.000 description 4
- 150000003335 secondary amines Chemical class 0.000 description 4
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 4
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 4
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 150000003871 sulfonates Chemical class 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 4
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 4
- 230000003612 virological effect Effects 0.000 description 4
- NDMFETHQFUOIQX-UHFFFAOYSA-N 1-(3-chloropropyl)imidazolidin-2-one Chemical compound ClCCCN1CCNC1=O NDMFETHQFUOIQX-UHFFFAOYSA-N 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- REXUYBKPWIPONM-UHFFFAOYSA-N 2-bromoacetonitrile Chemical compound BrCC#N REXUYBKPWIPONM-UHFFFAOYSA-N 0.000 description 3
- ONZHMGRKWJMTDE-UHFFFAOYSA-N 3-chloro-4-iodoaniline Chemical compound NC1=CC=C(I)C(Cl)=C1 ONZHMGRKWJMTDE-UHFFFAOYSA-N 0.000 description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 3
- 208000030507 AIDS Diseases 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 241000701022 Cytomegalovirus Species 0.000 description 3
- 206010011831 Cytomegalovirus infection Diseases 0.000 description 3
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 3
- GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 description 3
- 102000053187 Glucuronidase Human genes 0.000 description 3
- 241000701041 Human betaherpesvirus 7 Species 0.000 description 3
- 241000701027 Human herpesvirus 6 Species 0.000 description 3
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001350 alkyl halides Chemical class 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000003443 antiviral agent Substances 0.000 description 3
- 150000003935 benzaldehydes Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- UISAVXQFGRNLNT-UHFFFAOYSA-N ethyl 3-(dimethylamino)-2-isocyanoprop-2-enoate Chemical compound CCOC(=O)C([N+]#[C-])=CN(C)C UISAVXQFGRNLNT-UHFFFAOYSA-N 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 239000012091 fetal bovine serum Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- XAAKCCMYRKZRAK-UHFFFAOYSA-N isoquinoline-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=NC=CC2=C1 XAAKCCMYRKZRAK-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- ZZJMXELPMGQPDD-UHFFFAOYSA-N n-(4-aminophenyl)thiadiazole-4-carboxamide Chemical compound C1=CC(N)=CC=C1NC(=O)C1=CSN=N1 ZZJMXELPMGQPDD-UHFFFAOYSA-N 0.000 description 3
- RRHNGIRRWDWWQQ-UHFFFAOYSA-N n-iodoaniline Chemical compound INC1=CC=CC=C1 RRHNGIRRWDWWQQ-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000002916 oxazoles Chemical class 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
- 239000011698 potassium fluoride Substances 0.000 description 3
- 235000003270 potassium fluoride Nutrition 0.000 description 3
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 3
- 229910000105 potassium hydride Inorganic materials 0.000 description 3
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- MKMREWXKJLJHMK-UHFFFAOYSA-N tert-butyl n-[3-chloro-4-[3-(dimethylamino)prop-2-enoyl]phenyl]carbamate Chemical compound CN(C)C=CC(=O)C1=CC=C(NC(=O)OC(C)(C)C)C=C1Cl MKMREWXKJLJHMK-UHFFFAOYSA-N 0.000 description 3
- BXCZJWHJYRELHY-UHFFFAOYSA-N thiadiazole-5-carboxylic acid Chemical class OC(=O)C1=CN=NS1 BXCZJWHJYRELHY-UHFFFAOYSA-N 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 238000001665 trituration Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 230000029812 viral genome replication Effects 0.000 description 3
- 239000011592 zinc chloride Substances 0.000 description 3
- 235000005074 zinc chloride Nutrition 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- ZZLPSWPBRZRREN-UHFFFAOYSA-N (4-ethenylphenyl)urea Chemical compound NC(=O)NC1=CC=C(C=C)C=C1 ZZLPSWPBRZRREN-UHFFFAOYSA-N 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- HMVYYTRDXNKRBQ-UHFFFAOYSA-N 1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSC=N1 HMVYYTRDXNKRBQ-UHFFFAOYSA-N 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- RLGAJHHDRHLPQW-UHFFFAOYSA-N 1-(4-aminophenyl)-3-(2-phenoxyethyl)thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NCCOC1=CC=CC=C1 RLGAJHHDRHLPQW-UHFFFAOYSA-N 0.000 description 2
- CXPZIOZLMSUMJO-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[1-(4-fluorophenyl)ethyl]thiourea Chemical compound C=1C=C(F)C=CC=1C(C)NC(=S)NC1=CC=C(N)C=C1 CXPZIOZLMSUMJO-UHFFFAOYSA-N 0.000 description 2
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
- MWUCSURZWUDISB-UHFFFAOYSA-N 2-(4-aminophenyl)isoindole-1,3-dione Chemical compound C1=CC(N)=CC=C1N1C(=O)C2=CC=CC=C2C1=O MWUCSURZWUDISB-UHFFFAOYSA-N 0.000 description 2
- MFQYCZUGKJGRBX-UHFFFAOYSA-N 2-[4-[(4-acetamidophenyl)carbamothioylamino]-2,6-dichlorophenoxy]acetic acid Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC1=CC(Cl)=C(OCC(O)=O)C(Cl)=C1 MFQYCZUGKJGRBX-UHFFFAOYSA-N 0.000 description 2
- AVMHSPJDWZHUPG-UHFFFAOYSA-N 2-[4-[(4-acetamidophenyl)carbamothioylamino]-2,6-dichlorophenoxy]ethyl acetate Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC1=CC(Cl)=C(OCCOC(C)=O)C(Cl)=C1 AVMHSPJDWZHUPG-UHFFFAOYSA-N 0.000 description 2
- CXXQTSWVWIDQEF-UHFFFAOYSA-N 2-[4-[(4-acetamidophenyl)carbamothioylamino]-2,6-dichlorophenoxy]ethyl benzoate Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC(C=C1Cl)=CC(Cl)=C1OCCOC(=O)C1=CC=CC=C1 CXXQTSWVWIDQEF-UHFFFAOYSA-N 0.000 description 2
- HRCOEVSFYVJQMT-UHFFFAOYSA-N 2-butyl-1,3-thiazole-4-carboxylic acid Chemical compound CCCCC1=NC(C(O)=O)=CS1 HRCOEVSFYVJQMT-UHFFFAOYSA-N 0.000 description 2
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 2
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 2
- IBUSLNJQKLZPNR-UHFFFAOYSA-N 2-phenyl-1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSC(C=2C=CC=CC=2)=N1 IBUSLNJQKLZPNR-UHFFFAOYSA-N 0.000 description 2
- XHYVJUUPYNCLHY-UHFFFAOYSA-N 2-propan-2-yl-1,3-thiazole-4-carboxylic acid Chemical compound CC(C)C1=NC(C(O)=O)=CS1 XHYVJUUPYNCLHY-UHFFFAOYSA-N 0.000 description 2
- CNYVFIKUIUSPCD-UHFFFAOYSA-N 2-trimethylsilylethyl n-(3-chloro-4-ethenylphenyl)carbamate Chemical compound C[Si](C)(C)CCOC(=O)NC1=CC=C(C=C)C(Cl)=C1 CNYVFIKUIUSPCD-UHFFFAOYSA-N 0.000 description 2
- ZSTJMYZXBGCMIG-UHFFFAOYSA-M 3,5-dichloro-1-fluoropyridin-1-ium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.F[N+]1=CC(Cl)=CC(Cl)=C1 ZSTJMYZXBGCMIG-UHFFFAOYSA-M 0.000 description 2
- DHYHYLGCQVVLOQ-UHFFFAOYSA-N 3-bromoaniline Chemical compound NC1=CC=CC(Br)=C1 DHYHYLGCQVVLOQ-UHFFFAOYSA-N 0.000 description 2
- IHCCAYCGZOLTEU-UHFFFAOYSA-N 3-furoic acid Chemical compound OC(=O)C=1C=COC=1 IHCCAYCGZOLTEU-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
- FEJUGLKDZJDVFY-UHFFFAOYSA-N 9-borabicyclo(3.3.1)nonane Chemical compound C1CCC2CCCC1B2 FEJUGLKDZJDVFY-UHFFFAOYSA-N 0.000 description 2
- UJTTUOLQLCQZEA-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-(4-hydroxybutyl)carbamate Chemical compound C1=CC=C2C(COC(=O)NCCCCO)C3=CC=CC=C3C2=C1 UJTTUOLQLCQZEA-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- 241000283707 Capra Species 0.000 description 2
- VWFCHDSQECPREK-LURJTMIESA-N Cidofovir Chemical compound NC=1C=CN(C[C@@H](CO)OCP(O)(O)=O)C(=O)N=1 VWFCHDSQECPREK-LURJTMIESA-N 0.000 description 2
- 102000016928 DNA-directed DNA polymerase Human genes 0.000 description 2
- 108010014303 DNA-directed DNA polymerase Proteins 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- 238000002965 ELISA Methods 0.000 description 2
- 238000012286 ELISA Assay Methods 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 2
- 208000007514 Herpes zoster Diseases 0.000 description 2
- 241000700586 Herpesviridae Species 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 241000701074 Human alphaherpesvirus 2 Species 0.000 description 2
- 241001502974 Human gammaherpesvirus 8 Species 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- 239000003810 Jones reagent Substances 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 239000012448 Lithium borohydride Substances 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 241001529936 Murinae Species 0.000 description 2
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- 150000001204 N-oxides Chemical class 0.000 description 2
- 206010029155 Nephropathy toxic Diseases 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- 206010035664 Pneumonia Diseases 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 206010038910 Retinitis Diseases 0.000 description 2
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 description 2
- 206010039491 Sarcoma Diseases 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 2
- 125000004647 alkyl sulfenyl group Chemical group 0.000 description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 2
- 235000019257 ammonium acetate Nutrition 0.000 description 2
- 229940043376 ammonium acetate Drugs 0.000 description 2
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 230000007969 cellular immunity Effects 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 2
- 229940047583 cetamide Drugs 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229960000724 cidofovir Drugs 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- XXTZHYXQVWRADW-UHFFFAOYSA-N diazomethanone Chemical compound [N]N=C=O XXTZHYXQVWRADW-UHFFFAOYSA-N 0.000 description 2
- 125000005805 dimethoxy phenyl group Chemical group 0.000 description 2
- FFHWGQQFANVOHV-UHFFFAOYSA-N dimethyldioxirane Chemical compound CC1(C)OO1 FFHWGQQFANVOHV-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- FPULFENIJDPZBX-UHFFFAOYSA-N ethyl 2-isocyanoacetate Chemical compound CCOC(=O)C[N+]#[C-] FPULFENIJDPZBX-UHFFFAOYSA-N 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 210000002950 fibroblast Anatomy 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 229960005102 foscarnet Drugs 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical class CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- UAKUACVJZBWEFO-UHFFFAOYSA-N n-(1-naphthalen-2-ylethyl)formamide Chemical compound C1=CC=CC2=CC(C(NC=O)C)=CC=C21 UAKUACVJZBWEFO-UHFFFAOYSA-N 0.000 description 2
- CWVDLMKNLHAFHL-UHFFFAOYSA-N n-[4-[[3,5-dichloro-4-(2-hydroxyethoxy)phenyl]carbamothioylamino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC1=CC(Cl)=C(OCCO)C(Cl)=C1 CWVDLMKNLHAFHL-UHFFFAOYSA-N 0.000 description 2
- 230000007694 nephrotoxicity Effects 0.000 description 2
- 231100000417 nephrotoxicity Toxicity 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- 239000002777 nucleoside Substances 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical class N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical class [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 2
- VQMSRUREDGBWKT-UHFFFAOYSA-N quinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=NC2=C1 VQMSRUREDGBWKT-UHFFFAOYSA-N 0.000 description 2
- QRDZFPUVLYEQTA-UHFFFAOYSA-N quinoline-8-carboxylic acid Chemical compound C1=CN=C2C(C(=O)O)=CC=CC2=C1 QRDZFPUVLYEQTA-UHFFFAOYSA-N 0.000 description 2
- 150000007659 semicarbazones Chemical class 0.000 description 2
- KZJPVUDYAMEDRM-UHFFFAOYSA-M silver;2,2,2-trifluoroacetate Chemical compound [Ag+].[O-]C(=O)C(F)(F)F KZJPVUDYAMEDRM-UHFFFAOYSA-M 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 229910052979 sodium sulfide Inorganic materials 0.000 description 2
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 2
- 235000011150 stannous chloride Nutrition 0.000 description 2
- 239000008174 sterile solution Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- GUEFWIPNCZYUAR-UHFFFAOYSA-N tert-butyl n-(3,5-dichloro-4-hydroxyphenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(Cl)=C(O)C(Cl)=C1 GUEFWIPNCZYUAR-UHFFFAOYSA-N 0.000 description 2
- BEPCEEDBEMSIIB-UHFFFAOYSA-N tert-butyl n-(3-amino-5-chlorophenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(N)=CC(Cl)=C1 BEPCEEDBEMSIIB-UHFFFAOYSA-N 0.000 description 2
- XRORQEWOPJOBMY-UHFFFAOYSA-N tert-butyl n-[3-chloro-4-[3-(dimethylamino)prop-1-ynyl]phenyl]carbamate Chemical compound CN(C)CC#CC1=CC=C(NC(=O)OC(C)(C)C)C=C1Cl XRORQEWOPJOBMY-UHFFFAOYSA-N 0.000 description 2
- YTEZNKLIOIQXIV-UHFFFAOYSA-N tert-butyl n-[4-[[3-(dimethylamino)benzoyl]amino]phenyl]carbamate Chemical compound CN(C)C1=CC=CC(C(=O)NC=2C=CC(NC(=O)OC(C)(C)C)=CC=2)=C1 YTEZNKLIOIQXIV-UHFFFAOYSA-N 0.000 description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 2
- 150000003557 thiazoles Chemical class 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- NDLIRBZKZSDGSO-UHFFFAOYSA-N tosyl azide Chemical compound CC1=CC=C(S(=O)(=O)[N-][N+]#N)C=C1 NDLIRBZKZSDGSO-UHFFFAOYSA-N 0.000 description 2
- QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 2
- BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 2
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 1
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- PFVWEAYXWZFSSK-YFKPBYRVSA-N (1s)-1-[3,5-bis(trifluoromethyl)phenyl]ethanamine Chemical compound C[C@H](N)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 PFVWEAYXWZFSSK-YFKPBYRVSA-N 0.000 description 1
- WHKVGIDSQKDXEE-UHFFFAOYSA-N (4-amino-2-chlorophenyl)carbamic acid Chemical compound NC1=CC=C(NC(O)=O)C(Cl)=C1 WHKVGIDSQKDXEE-UHFFFAOYSA-N 0.000 description 1
- IQFUADQPSYSDIP-UHFFFAOYSA-N (4-aminophenyl)carbamic acid Chemical compound NC1=CC=C(NC(O)=O)C=C1 IQFUADQPSYSDIP-UHFFFAOYSA-N 0.000 description 1
- 101150084750 1 gene Proteins 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- MIIQJAUWHSUTIT-UHFFFAOYSA-N 1,2-oxazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=NO1 MIIQJAUWHSUTIT-UHFFFAOYSA-N 0.000 description 1
- HYGVAYCCFMGZCN-UHFFFAOYSA-N 1,3-dichloro-5-nitro-2-phenoxybenzene Chemical compound ClC1=CC([N+](=O)[O-])=CC(Cl)=C1OC1=CC=CC=C1 HYGVAYCCFMGZCN-UHFFFAOYSA-N 0.000 description 1
- JBCFJMYPJJWIRG-UHFFFAOYSA-N 1,3-oxazole-4-carboxylic acid Chemical compound OC(=O)C1=COC=N1 JBCFJMYPJJWIRG-UHFFFAOYSA-N 0.000 description 1
- HZFCTMZSKIDZPA-UHFFFAOYSA-N 1-(2,4-dimethoxyphenyl)-3-(4-methoxyphenyl)thiourea Chemical compound C1=CC(OC)=CC=C1NC(=S)NC1=CC=C(OC)C=C1OC HZFCTMZSKIDZPA-UHFFFAOYSA-N 0.000 description 1
- IBJFQYOXVOUXBY-UHFFFAOYSA-N 1-(2-bromo-4-fluorophenyl)-N-methoxyethanimine 1-(3,4-dibromophenyl)-N-methoxyethanimine Chemical compound CON=C(C)C1=CC(=C(C=C1)Br)Br.CON=C(C)C1=C(C=C(C=C1)F)Br IBJFQYOXVOUXBY-UHFFFAOYSA-N 0.000 description 1
- DSAXBVQQKYZELF-UHFFFAOYSA-N 1-(2-bromophenyl)ethanamine Chemical compound CC(N)C1=CC=CC=C1Br DSAXBVQQKYZELF-UHFFFAOYSA-N 0.000 description 1
- VENQOHAPVLVQKV-UHFFFAOYSA-N 1-(2-methoxyphenyl)ethanamine Chemical compound COC1=CC=CC=C1C(C)N VENQOHAPVLVQKV-UHFFFAOYSA-N 0.000 description 1
- ZCDYTNZJBGSKFI-UHFFFAOYSA-N 1-(2-methylphenyl)ethanamine Chemical compound CC(N)C1=CC=CC=C1C ZCDYTNZJBGSKFI-UHFFFAOYSA-N 0.000 description 1
- JPEWBAUSNPWVEW-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-n-methoxyethanimine Chemical compound CON=C(C)C1=CC=C(Cl)C(Cl)=C1 JPEWBAUSNPWVEW-UHFFFAOYSA-N 0.000 description 1
- PHYDEVHOQGLZQC-UHFFFAOYSA-N 1-(3,4-difluorophenyl)-N-methoxyethanimine Chemical compound CON=C(C)C1=CC=C(F)C(F)=C1 PHYDEVHOQGLZQC-UHFFFAOYSA-N 0.000 description 1
- LIBZHYLTOAGURM-UHFFFAOYSA-N 1-(3-bromophenyl)ethanamine Chemical compound CC(N)C1=CC=CC(Br)=C1 LIBZHYLTOAGURM-UHFFFAOYSA-N 0.000 description 1
- DQEYVZASLGNODG-UHFFFAOYSA-N 1-(3-chlorophenyl)ethanamine Chemical compound CC(N)C1=CC=CC(Cl)=C1 DQEYVZASLGNODG-UHFFFAOYSA-N 0.000 description 1
- HQQVIKFUKBTOLA-UHFFFAOYSA-N 1-(4-amino-2-chlorophenyl)ethanol Chemical compound CC(O)C1=CC=C(N)C=C1Cl HQQVIKFUKBTOLA-UHFFFAOYSA-N 0.000 description 1
- BNUWFVUYOMMJQV-UHFFFAOYSA-N 1-(4-amino-3,5-dibromophenyl)-3-(4-aminophenyl)thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NC1=CC(Br)=C(N)C(Br)=C1 BNUWFVUYOMMJQV-UHFFFAOYSA-N 0.000 description 1
- HITMASHYZRMWKE-UHFFFAOYSA-N 1-(4-amino-3-cyanophenyl)-3-[1-(4-fluorophenyl)ethyl]thiourea Chemical compound C=1C=C(F)C=CC=1C(C)NC(=S)NC1=CC=C(N)C(C#N)=C1 HITMASHYZRMWKE-UHFFFAOYSA-N 0.000 description 1
- LLJFZNNKKTWWIL-UHFFFAOYSA-N 1-(4-amino-3-methylphenyl)-3-[1-(4-fluorophenyl)ethyl]thiourea Chemical compound C=1C=C(F)C=CC=1C(C)NC(=S)NC1=CC=C(N)C(C)=C1 LLJFZNNKKTWWIL-UHFFFAOYSA-N 0.000 description 1
- NCUCMRRVSDPCSQ-UHFFFAOYSA-N 1-(4-aminophenyl)-3-(1-phenylpropan-2-yl)thiourea Chemical compound C=1C=C(N)C=CC=1NC(=S)NC(C)CC1=CC=CC=C1 NCUCMRRVSDPCSQ-UHFFFAOYSA-N 0.000 description 1
- SKMLBIUZLMTWBJ-UHFFFAOYSA-N 1-(4-aminophenyl)-3-(2,3-dichlorophenyl)thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NC1=CC=CC(Cl)=C1Cl SKMLBIUZLMTWBJ-UHFFFAOYSA-N 0.000 description 1
- KJXRYNXFXIDWLR-UHFFFAOYSA-N 1-(4-aminophenyl)-3-(2,3-dihydro-1H-inden-1-yl)thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NC1C2=CC=CC=C2CC1 KJXRYNXFXIDWLR-UHFFFAOYSA-N 0.000 description 1
- HGRYLKJMQBUZTG-UHFFFAOYSA-N 1-(4-aminophenyl)-3-(2-phenylsulfanylethyl)thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NCCSC1=CC=CC=C1 HGRYLKJMQBUZTG-UHFFFAOYSA-N 0.000 description 1
- YJJQMCYEYXQPOQ-UHFFFAOYSA-N 1-(4-aminophenyl)-3-(3,4-dichlorophenyl)thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NC1=CC=C(Cl)C(Cl)=C1 YJJQMCYEYXQPOQ-UHFFFAOYSA-N 0.000 description 1
- ZMPCHKHSWBSJPL-UHFFFAOYSA-N 1-(4-aminophenyl)-3-(3,5-dimethoxyphenyl)thiourea Chemical compound COC1=CC(OC)=CC(NC(=S)NC=2C=CC(N)=CC=2)=C1 ZMPCHKHSWBSJPL-UHFFFAOYSA-N 0.000 description 1
- FVJWFPNKRSUMFC-UHFFFAOYSA-N 1-(4-aminophenyl)-3-(3-bromophenyl)thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NC1=CC=CC(Br)=C1 FVJWFPNKRSUMFC-UHFFFAOYSA-N 0.000 description 1
- PHVMADJNFKAABM-UHFFFAOYSA-N 1-(4-aminophenyl)-3-(3-chloro-4-iodophenyl)thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NC1=CC=C(I)C(Cl)=C1 PHVMADJNFKAABM-UHFFFAOYSA-N 0.000 description 1
- BZWDEQVYVAYYFZ-UHFFFAOYSA-N 1-(4-aminophenyl)-3-(4-bromophenyl)thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NC1=CC=C(Br)C=C1 BZWDEQVYVAYYFZ-UHFFFAOYSA-N 0.000 description 1
- QXFDAVXWFYKNTD-UHFFFAOYSA-N 1-(4-aminophenyl)-3-(4-phenylbutan-2-yl)thiourea Chemical compound C=1C=C(N)C=CC=1NC(=S)NC(C)CCC1=CC=CC=C1 QXFDAVXWFYKNTD-UHFFFAOYSA-N 0.000 description 1
- DKNFRAHVZWVDRB-UHFFFAOYSA-N 1-(4-aminophenyl)-3-(4-phenylbutyl)thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NCCCCC1=CC=CC=C1 DKNFRAHVZWVDRB-UHFFFAOYSA-N 0.000 description 1
- BXNCGUXWPPOXDI-UHFFFAOYSA-N 1-(4-aminophenyl)-3-(5-chloro-2-methoxy-4-methylphenyl)thiourea Chemical compound COC1=CC(C)=C(Cl)C=C1NC(=S)NC1=CC=C(N)C=C1 BXNCGUXWPPOXDI-UHFFFAOYSA-N 0.000 description 1
- JZEHHFNUCORORN-UHFFFAOYSA-N 1-(4-aminophenyl)-3-(pyridin-4-ylmethyl)thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NCC1=CC=NC=C1 JZEHHFNUCORORN-UHFFFAOYSA-N 0.000 description 1
- WJCCVWSFGLETSE-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[(3,4-difluorophenyl)methyl]thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NCC1=CC=C(F)C(F)=C1 WJCCVWSFGLETSE-UHFFFAOYSA-N 0.000 description 1
- NKYSUCOJIVRLPN-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[(3,5-difluorophenyl)methyl]thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NCC1=CC(F)=CC(F)=C1 NKYSUCOJIVRLPN-UHFFFAOYSA-N 0.000 description 1
- UIOKCEVJKGIFHO-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[(3-chloro-4-fluorophenyl)methyl]thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NCC1=CC=C(F)C(Cl)=C1 UIOKCEVJKGIFHO-UHFFFAOYSA-N 0.000 description 1
- FTGPGFAKGWDATB-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[(3-chlorophenyl)methyl]thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NCC1=CC=CC(Cl)=C1 FTGPGFAKGWDATB-UHFFFAOYSA-N 0.000 description 1
- YBVMFJJGGRHJDW-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[(3-iodophenyl)methyl]thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NCC1=CC=CC(I)=C1 YBVMFJJGGRHJDW-UHFFFAOYSA-N 0.000 description 1
- ARNWYFXPNVQBHE-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[(4-chlorophenyl)methyl]thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NCC1=CC=C(Cl)C=C1 ARNWYFXPNVQBHE-UHFFFAOYSA-N 0.000 description 1
- CSCXAMBVSNQHKJ-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[2-(2,6-dichlorophenyl)ethyl]thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NCCC1=C(Cl)C=CC=C1Cl CSCXAMBVSNQHKJ-UHFFFAOYSA-N 0.000 description 1
- JFGFYHBFISJTEM-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[2-(2-methoxyphenyl)ethyl]thiourea Chemical compound COC1=CC=CC=C1CCNC(=S)NC1=CC=C(N)C=C1 JFGFYHBFISJTEM-UHFFFAOYSA-N 0.000 description 1
- LCBWMXOLSZTRRE-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[2-(3,4-dichlorophenoxy)ethyl]thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NCCOC1=CC=C(Cl)C(Cl)=C1 LCBWMXOLSZTRRE-UHFFFAOYSA-N 0.000 description 1
- QJWFVQRVYVQJPK-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[2-(3,4-dichlorophenyl)ethyl]thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NCCC1=CC=C(Cl)C(Cl)=C1 QJWFVQRVYVQJPK-UHFFFAOYSA-N 0.000 description 1
- RXCZHMJEEWWTBY-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[2-(3,4-dichlorophenyl)sulfanylethyl]thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NCCSC1=CC=C(Cl)C(Cl)=C1 RXCZHMJEEWWTBY-UHFFFAOYSA-N 0.000 description 1
- UXFDWXKWPUJZEZ-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[2-(3,5-difluorophenyl)ethyl]thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NCCC1=CC(F)=CC(F)=C1 UXFDWXKWPUJZEZ-UHFFFAOYSA-N 0.000 description 1
- PTYCEEQGFSOJFW-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[2-(3-bromophenyl)sulfanylethyl]thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NCCSC1=CC=CC(Br)=C1 PTYCEEQGFSOJFW-UHFFFAOYSA-N 0.000 description 1
- XKNAXAKEJIVXQU-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[2-(3-chlorophenoxy)ethyl]thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NCCOC1=CC=CC(Cl)=C1 XKNAXAKEJIVXQU-UHFFFAOYSA-N 0.000 description 1
- PHXDCDNRZXOQOB-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[2-(3-fluorophenyl)ethyl]thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NCCC1=CC=CC(F)=C1 PHXDCDNRZXOQOB-UHFFFAOYSA-N 0.000 description 1
- HNNBDBUSAHULOE-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[2-(3-iodophenoxy)ethyl]thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NCCOC1=CC=CC(I)=C1 HNNBDBUSAHULOE-UHFFFAOYSA-N 0.000 description 1
- RUSVOBMUCSKOMF-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[2-(3-methoxyphenyl)ethyl]thiourea Chemical compound COC1=CC=CC(CCNC(=S)NC=2C=CC(N)=CC=2)=C1 RUSVOBMUCSKOMF-UHFFFAOYSA-N 0.000 description 1
- WFXCLEVKCSCQJD-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[2-(4-methoxyphenyl)ethyl]thiourea Chemical compound C1=CC(OC)=CC=C1CCNC(=S)NC1=CC=C(N)C=C1 WFXCLEVKCSCQJD-UHFFFAOYSA-N 0.000 description 1
- UFENEOGVFCSDEU-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[2-(4-nitrophenyl)ethyl]thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NCCC1=CC=C([N+]([O-])=O)C=C1 UFENEOGVFCSDEU-UHFFFAOYSA-N 0.000 description 1
- QFHYSVIUCWZSFJ-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[2-[3,5-bis(trifluoromethyl)phenyl]ethyl]thiourea Chemical compound C1=CC(=CC=C1N)NC(=S)NCCC2=CC(=CC(=C2)C(F)(F)F)C(F)(F)F QFHYSVIUCWZSFJ-UHFFFAOYSA-N 0.000 description 1
- VUCZVKDPEMPLKE-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[2-[3-(trifluoromethyl)phenyl]ethyl]thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NCCC1=CC=CC(C(F)(F)F)=C1 VUCZVKDPEMPLKE-UHFFFAOYSA-N 0.000 description 1
- RIIPOCYZVYXVIP-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[3-(1-hydroxyethyl)phenyl]thiourea Chemical compound CC(O)C1=CC=CC(NC(=S)NC=2C=CC(N)=CC=2)=C1 RIIPOCYZVYXVIP-UHFFFAOYSA-N 0.000 description 1
- IIEKLMQACHMETA-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[3-(hydrazinecarbonyl)phenyl]thiourea Chemical compound NNC(=O)C1=CC=CC(NC(=S)NC=2C=CC(N)=CC=2)=C1 IIEKLMQACHMETA-UHFFFAOYSA-N 0.000 description 1
- WCTBRYWGUILJPN-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[3-bromo-4-(trifluoromethoxy)phenyl]thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NC1=CC=C(OC(F)(F)F)C(Br)=C1 WCTBRYWGUILJPN-UHFFFAOYSA-N 0.000 description 1
- SOZPMAQRQCOPGM-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[3-chloro-4-[cyclohexyl(methyl)amino]phenyl]thiourea Chemical compound C=1C=C(NC(=S)NC=2C=CC(N)=CC=2)C=C(Cl)C=1N(C)C1CCCCC1 SOZPMAQRQCOPGM-UHFFFAOYSA-N 0.000 description 1
- LSPXEHGKKGSBJK-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[3-chloro-4-[methyl-(1-methylpiperidin-4-yl)amino]phenyl]thiourea Chemical compound C=1C=C(NC(=S)NC=2C=CC(N)=CC=2)C=C(Cl)C=1N(C)C1CCN(C)CC1 LSPXEHGKKGSBJK-UHFFFAOYSA-N 0.000 description 1
- HPEKONJDHQXNGK-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[4-[(1-benzylpyrrolidin-3-yl)-methylamino]-3-chlorophenyl]thiourea Chemical compound C=1C=C(NC(=S)NC=2C=CC(N)=CC=2)C=C(Cl)C=1N(C)C(C1)CCN1CC1=CC=CC=C1 HPEKONJDHQXNGK-UHFFFAOYSA-N 0.000 description 1
- MPXRHZRWKLUCCI-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[4-fluoro-3-(trifluoromethyl)phenyl]thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NC1=CC=C(F)C(C(F)(F)F)=C1 MPXRHZRWKLUCCI-UHFFFAOYSA-N 0.000 description 1
- VHVFXNZHRHCVTP-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[[2-fluoro-5-(trifluoromethyl)phenyl]methyl]thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NCC1=CC(C(F)(F)F)=CC=C1F VHVFXNZHRHCVTP-UHFFFAOYSA-N 0.000 description 1
- GJMCIVIVOFURCE-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[[3-(dimethylamino)-5-(trifluoromethyl)phenyl]methyl]thiourea Chemical compound FC(F)(F)C1=CC(N(C)C)=CC(CNC(=S)NC=2C=CC(N)=CC=2)=C1 GJMCIVIVOFURCE-UHFFFAOYSA-N 0.000 description 1
- ATFXLWOBFIRTEF-UHFFFAOYSA-N 1-(4-aminophenyl)-3-benzylthiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NCC1=CC=CC=C1 ATFXLWOBFIRTEF-UHFFFAOYSA-N 0.000 description 1
- NOJDRBIFAPHSEA-UHFFFAOYSA-N 1-(4-chloro-3-fluorophenyl)-n-methoxyethanimine Chemical compound CON=C(C)C1=CC=C(Cl)C(F)=C1 NOJDRBIFAPHSEA-UHFFFAOYSA-N 0.000 description 1
- JISSZMBAZDURRH-UHFFFAOYSA-N 1-(4-fluorophenyl)-n-methoxy-1-phenylmethanimine Chemical compound C=1C=C(F)C=CC=1C(=NOC)C1=CC=CC=C1 JISSZMBAZDURRH-UHFFFAOYSA-N 0.000 description 1
- HCJGKNUUHOOUJS-UHFFFAOYSA-N 1-(4-fluorophenyl)pentan-1-amine Chemical compound CCCCC(N)C1=CC=C(F)C=C1 HCJGKNUUHOOUJS-UHFFFAOYSA-N 0.000 description 1
- JTDGKQNNPKXKII-UHFFFAOYSA-N 1-(4-methoxyphenyl)ethanamine Chemical compound COC1=CC=C(C(C)N)C=C1 JTDGKQNNPKXKII-UHFFFAOYSA-N 0.000 description 1
- UZDDXUMOXKDXNE-UHFFFAOYSA-N 1-(4-methylphenyl)ethanamine Chemical compound CC(N)C1=CC=C(C)C=C1 UZDDXUMOXKDXNE-UHFFFAOYSA-N 0.000 description 1
- QCZZSANNLWPGEA-UHFFFAOYSA-N 1-(4-phenylphenyl)ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C1=CC=CC=C1 QCZZSANNLWPGEA-UHFFFAOYSA-N 0.000 description 1
- YCLUFWACGHXZLX-UHFFFAOYSA-N 1-(4-piperidin-1-ylsulfonylphenyl)ethanamine Chemical compound C1=CC(C(N)C)=CC=C1S(=O)(=O)N1CCCCC1 YCLUFWACGHXZLX-UHFFFAOYSA-N 0.000 description 1
- LMDQIQIHHVIYKA-UHFFFAOYSA-N 1-(5-aminopyridin-2-yl)-3-(5-chloro-2,4-dimethoxyphenyl)thiourea Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC1=CC=C(N)C=N1 LMDQIQIHHVIYKA-UHFFFAOYSA-N 0.000 description 1
- CRJHADGHPNYTBA-UHFFFAOYSA-N 1-(5-chloro-2,4-dimethoxyphenyl)-3-(2-nitrophenyl)thiourea Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC1=CC=CC=C1[N+]([O-])=O CRJHADGHPNYTBA-UHFFFAOYSA-N 0.000 description 1
- HUWOYDZBTGTXJX-UHFFFAOYSA-N 1-(5-chloro-2,4-dimethoxyphenyl)-3-(4-morpholin-4-ylphenyl)thiourea Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC1=CC=C(N2CCOCC2)C=C1 HUWOYDZBTGTXJX-UHFFFAOYSA-N 0.000 description 1
- JYXGCMLOKDKUAX-UHFFFAOYSA-N 1-(furan-2-yl)ethanamine Chemical compound CC(N)C1=CC=CO1 JYXGCMLOKDKUAX-UHFFFAOYSA-N 0.000 description 1
- XOLPBNUWTYBPRT-UHFFFAOYSA-N 1-[(4-aminophenyl)methyl]-3-(3,5-dichlorophenyl)thiourea Chemical compound C1=CC(N)=CC=C1CNC(=S)NC1=CC(Cl)=CC(Cl)=C1 XOLPBNUWTYBPRT-UHFFFAOYSA-N 0.000 description 1
- WDSCRLMZHHPIMU-UHFFFAOYSA-N 1-[(4-aminophenyl)methyl]-3-[4-chloro-3-(trifluoromethyl)phenyl]thiourea Chemical compound C1=CC(N)=CC=C1CNC(=S)NC1=CC=C(Cl)C(C(F)(F)F)=C1 WDSCRLMZHHPIMU-UHFFFAOYSA-N 0.000 description 1
- URNDNLYYRIAMSX-UHFFFAOYSA-N 1-[2,4-bis(trifluoromethyl)phenyl]ethanamine 1-(2,4-dimethylphenyl)ethanamine Chemical compound FC(C1=C(C=CC(=C1)C(F)(F)F)C(C)N)(F)F.CC1=C(C=CC(=C1)C)C(C)N URNDNLYYRIAMSX-UHFFFAOYSA-N 0.000 description 1
- DPLIMKBGTYIUCB-UHFFFAOYSA-N 1-[2-(trifluoromethyl)phenyl]ethanamine Chemical compound CC(N)C1=CC=CC=C1C(F)(F)F DPLIMKBGTYIUCB-UHFFFAOYSA-N 0.000 description 1
- FYDUUODXZQITBF-UHFFFAOYSA-N 1-[2-(trifluoromethyl)phenyl]ethanone Chemical compound CC(=O)C1=CC=CC=C1C(F)(F)F FYDUUODXZQITBF-UHFFFAOYSA-N 0.000 description 1
- UQYFFQLBPVBKOF-UHFFFAOYSA-N 1-[2-fluoro-5-(trifluoromethyl)phenyl]ethanamine Chemical compound CC(N)C1=CC(C(F)(F)F)=CC=C1F UQYFFQLBPVBKOF-UHFFFAOYSA-N 0.000 description 1
- MCYCSIKSZLARBD-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)phenyl]ethanone Chemical compound CC(=O)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 MCYCSIKSZLARBD-UHFFFAOYSA-N 0.000 description 1
- JDBPNFXZESJTAH-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)phenyl]propan-1-amine Chemical compound CCC(N)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 JDBPNFXZESJTAH-UHFFFAOYSA-N 0.000 description 1
- ODZXRBRYQGYVJY-UHFFFAOYSA-N 1-[3-(trifluoromethyl)phenyl]ethanamine Chemical compound CC(N)C1=CC=CC(C(F)(F)F)=C1 ODZXRBRYQGYVJY-UHFFFAOYSA-N 0.000 description 1
- HHAISVSEJFEWBZ-UHFFFAOYSA-N 1-[4-(trifluoromethyl)phenyl]ethanone Chemical compound CC(=O)C1=CC=C(C(F)(F)F)C=C1 HHAISVSEJFEWBZ-UHFFFAOYSA-N 0.000 description 1
- UYNMUXTXDHJBEN-UHFFFAOYSA-N 1-[4-chloro-3-(trifluoromethyl)phenyl]ethanone Chemical compound CC(=O)C1=CC=C(Cl)C(C(F)(F)F)=C1 UYNMUXTXDHJBEN-UHFFFAOYSA-N 0.000 description 1
- RMDLJKUKXHHAKP-UHFFFAOYSA-N 1-benzyl-n-(2-chloro-4-nitrophenyl)piperidin-4-amine Chemical compound ClC1=CC([N+](=O)[O-])=CC=C1NC1CCN(CC=2C=CC=CC=2)CC1 RMDLJKUKXHHAKP-UHFFFAOYSA-N 0.000 description 1
- XJAUKWKZKRKWBD-UHFFFAOYSA-N 1-bromo-2,4-dimethoxy-5-nitrobenzene Chemical compound COC1=CC(OC)=C([N+]([O-])=O)C=C1Br XJAUKWKZKRKWBD-UHFFFAOYSA-N 0.000 description 1
- MCDOADUSEVWUIQ-UHFFFAOYSA-N 1-butylsulfanyl-2-chloro-4-nitrobenzene Chemical compound CCCCSC1=CC=C([N+]([O-])=O)C=C1Cl MCDOADUSEVWUIQ-UHFFFAOYSA-N 0.000 description 1
- COSVEXSXJCUYOT-UHFFFAOYSA-N 1-chloro-5-isocyanato-2,4-dimethoxybenzene Chemical compound COC1=CC(OC)=C(N=C=O)C=C1Cl COSVEXSXJCUYOT-UHFFFAOYSA-N 0.000 description 1
- KADJLLXINJRFKF-UHFFFAOYSA-N 1-fluoro-2,4-dimethoxy-5-nitrobenzene Chemical compound COC1=CC(OC)=C([N+]([O-])=O)C=C1F KADJLLXINJRFKF-UHFFFAOYSA-N 0.000 description 1
- SJJCQDRGABAVBB-UHFFFAOYSA-N 1-hydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC=C21 SJJCQDRGABAVBB-UHFFFAOYSA-N 0.000 description 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
- SCCCFNJTCDSLCY-UHFFFAOYSA-N 1-iodo-4-nitrobenzene Chemical class [O-][N+](=O)C1=CC=C(I)C=C1 SCCCFNJTCDSLCY-UHFFFAOYSA-N 0.000 description 1
- KGFADEJSZXEVMC-UHFFFAOYSA-N 1-methoxy-4-nitro-2-(trifluoromethyl)benzene Chemical compound COC1=CC=C([N+]([O-])=O)C=C1C(F)(F)F KGFADEJSZXEVMC-UHFFFAOYSA-N 0.000 description 1
- FLVFPAIGVBQGET-UHFFFAOYSA-N 1-methylpyrrolidin-3-ol Chemical compound CN1CCC(O)C1 FLVFPAIGVBQGET-UHFFFAOYSA-N 0.000 description 1
- KOFZWWMCDUHEEM-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound [CH2]N1CCCC1 KOFZWWMCDUHEEM-UHFFFAOYSA-N 0.000 description 1
- KHSYYLCXQKCYQX-UHFFFAOYSA-N 1-naphthalen-2-ylethanamine Chemical compound C1=CC=CC2=CC(C(N)C)=CC=C21 KHSYYLCXQKCYQX-UHFFFAOYSA-N 0.000 description 1
- IUGUPWHFLZEPHN-UHFFFAOYSA-N 1-prop-2-ynylpyrrolidine Chemical compound C#CCN1CCCC1 IUGUPWHFLZEPHN-UHFFFAOYSA-N 0.000 description 1
- AIHHJLBGHZOVRZ-UHFFFAOYSA-N 1-quinolin-6-ylethanamine Chemical compound N1=CC=CC2=CC(C(N)C)=CC=C21 AIHHJLBGHZOVRZ-UHFFFAOYSA-N 0.000 description 1
- PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 1
- KTXFXDMDYZIXSJ-UHFFFAOYSA-N 2,4-difluorobenzamide Chemical compound NC(=O)C1=CC=C(F)C=C1F KTXFXDMDYZIXSJ-UHFFFAOYSA-N 0.000 description 1
- AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 description 1
- CYZKZWUUVPAPEJ-UHFFFAOYSA-N 2-(3,5-dichlorophenyl)sulfanylacetonitrile Chemical compound ClC1=CC(Cl)=CC(SCC#N)=C1 CYZKZWUUVPAPEJ-UHFFFAOYSA-N 0.000 description 1
- WRPAZHKOVLYSCH-UHFFFAOYSA-N 2-(3,5-difluorophenyl)ethanamine Chemical compound NCCC1=CC(F)=CC(F)=C1 WRPAZHKOVLYSCH-UHFFFAOYSA-N 0.000 description 1
- VZSSMGVYOSLFQZ-UHFFFAOYSA-N 2-(3-bromophenyl)sulfanylacetonitrile 2-(3-chlorophenyl)sulfanylacetonitrile 2-(4-iodophenoxy)acetonitrile 2-[3-(trifluoromethyl)phenyl]sulfanylacetonitrile Chemical compound FC(C=1C=C(C=CC1)SCC#N)(F)F.IC1=CC=C(OCC#N)C=C1.ClC=1C=C(C=CC1)SCC#N.BrC=1C=C(C=CC1)SCC#N VZSSMGVYOSLFQZ-UHFFFAOYSA-N 0.000 description 1
- RNTREYCXKDDKIR-UHFFFAOYSA-N 2-(4-amino-2,6-dichlorophenoxy)acetic acid Chemical compound NC1=CC(Cl)=C(OCC(O)=O)C(Cl)=C1 RNTREYCXKDDKIR-UHFFFAOYSA-N 0.000 description 1
- LPLDAFPYOIWSDP-UHFFFAOYSA-N 2-(4-amino-2-chlorophenyl)ethanol Chemical compound NC1=CC=C(CCO)C(Cl)=C1 LPLDAFPYOIWSDP-UHFFFAOYSA-N 0.000 description 1
- PMDDXFGYBKIPKR-UHFFFAOYSA-N 2-(4-bromophenoxy)acetonitrile Chemical compound BrC1=CC=C(OCC#N)C=C1 PMDDXFGYBKIPKR-UHFFFAOYSA-N 0.000 description 1
- PMOSJSPFNDUAFY-UHFFFAOYSA-N 2-(4-bromophenyl)ethanol Chemical compound OCCC1=CC=C(Br)C=C1 PMOSJSPFNDUAFY-UHFFFAOYSA-N 0.000 description 1
- KZTWONRVIPPDKH-UHFFFAOYSA-N 2-(piperidin-1-yl)ethanol Chemical compound OCCN1CCCCC1 KZTWONRVIPPDKH-UHFFFAOYSA-N 0.000 description 1
- SRAQMSPJVHGYHT-UHFFFAOYSA-N 2-[2,4-bis(trifluoromethyl)phenyl]ethanamine Chemical compound NCCC1=CC=C(C(F)(F)F)C=C1C(F)(F)F SRAQMSPJVHGYHT-UHFFFAOYSA-N 0.000 description 1
- UKTRSEPUPYOFQY-UHFFFAOYSA-N 2-[2-[(4-acetamidophenyl)carbamothioylamino]-4-chloro-5-methoxyphenoxy]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(OCC(O)=O)=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 UKTRSEPUPYOFQY-UHFFFAOYSA-N 0.000 description 1
- UBSMVJITILEVAX-UHFFFAOYSA-N 2-[2-fluoro-5-(trifluoromethyl)phenoxy]acetonitrile Chemical compound FC1=CC=C(C(F)(F)F)C=C1OCC#N UBSMVJITILEVAX-UHFFFAOYSA-N 0.000 description 1
- GTJVLFSLUFRLKN-UHFFFAOYSA-N 2-[3-[[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]phenyl]carbamoyl]phenoxy]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC(OCC(O)=O)=C1 GTJVLFSLUFRLKN-UHFFFAOYSA-N 0.000 description 1
- HKCQBEWZJZKBQM-UHFFFAOYSA-N 2-[3-fluoro-5-(trifluoromethyl)phenyl]acetonitrile Chemical compound FC1=CC(CC#N)=CC(C(F)(F)F)=C1 HKCQBEWZJZKBQM-UHFFFAOYSA-N 0.000 description 1
- HNTMJWMRAYELRY-UHFFFAOYSA-N 2-[3-fluoro-5-(trifluoromethyl)phenyl]ethanamine;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.NCCC1=CC(F)=CC(C(F)(F)F)=C1 HNTMJWMRAYELRY-UHFFFAOYSA-N 0.000 description 1
- VYZRSFZGFBXKHJ-UHFFFAOYSA-N 2-[4-[(4-acetamidophenyl)carbamothioylamino]-2,6-dichlorophenoxy]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC1=CC(Cl)=C(OCC(N)=O)C(Cl)=C1 VYZRSFZGFBXKHJ-UHFFFAOYSA-N 0.000 description 1
- VPRBGMOXLAAYLL-UHFFFAOYSA-N 2-[4-[(4-acetamidophenyl)carbamothioylamino]-2,6-dichlorophenoxy]ethyl methanesulfonate Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC1=CC(Cl)=C(OCCOS(C)(=O)=O)C(Cl)=C1 VPRBGMOXLAAYLL-UHFFFAOYSA-N 0.000 description 1
- OMDPDDUNMGJQOY-UHFFFAOYSA-N 2-[4-[(4-acetamidophenyl)carbamothioylamino]-2-chloro-5-methoxyphenoxy]acetamide Chemical compound COC1=CC(OCC(N)=O)=C(Cl)C=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 OMDPDDUNMGJQOY-UHFFFAOYSA-N 0.000 description 1
- WPWSWMMLFPSRSF-UHFFFAOYSA-N 2-[4-[(4-acetamidophenyl)carbamothioylamino]-2-chlorophenoxy]-4,5-dichlorobenzenesulfonic acid Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC(C=C1Cl)=CC=C1OC1=CC(Cl)=C(Cl)C=C1S(O)(=O)=O WPWSWMMLFPSRSF-UHFFFAOYSA-N 0.000 description 1
- AQUZPBABSUBRLS-UHFFFAOYSA-N 2-[4-amino-2-chloro-n-(2-hydroxyethyl)anilino]ethanol Chemical compound NC1=CC=C(N(CCO)CCO)C(Cl)=C1 AQUZPBABSUBRLS-UHFFFAOYSA-N 0.000 description 1
- HJRYAGVNRREVDZ-UHFFFAOYSA-N 2-acetamido-5-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]benzoic acid Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC1=CC=C(NC(C)=O)C(C(O)=O)=C1 HJRYAGVNRREVDZ-UHFFFAOYSA-N 0.000 description 1
- BPCYWJYTOHXEHM-UHFFFAOYSA-N 2-acetamido-n-(4-aminophenyl)benzamide Chemical compound CC(=O)NC1=CC=CC=C1C(=O)NC1=CC=C(N)C=C1 BPCYWJYTOHXEHM-UHFFFAOYSA-N 0.000 description 1
- MHELKOQSSJCBHZ-UHFFFAOYSA-N 2-amino-4-chloro-5-methoxyphenol 4-amino-2-chloro-5-methoxyphenol Chemical compound NC1=C(C=C(C(=C1)Cl)OC)O.NC1=CC(=C(C=C1OC)O)Cl MHELKOQSSJCBHZ-UHFFFAOYSA-N 0.000 description 1
- ZUFQMRDGVYDVAF-UHFFFAOYSA-N 2-amino-5-iodobenzamide Chemical compound NC(=O)C1=CC(I)=CC=C1N ZUFQMRDGVYDVAF-UHFFFAOYSA-N 0.000 description 1
- CCMQBFUTGYIKCY-UHFFFAOYSA-N 2-bromo-n-[4-[1-(4-fluorophenyl)ethylcarbamothioylamino]phenyl]benzamide Chemical compound C=1C=C(F)C=CC=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1Br CCMQBFUTGYIKCY-UHFFFAOYSA-N 0.000 description 1
- DXWGZZDXYVQOLW-UHFFFAOYSA-N 2-chloro-1,3-dimethoxy-4-nitrobenzene Chemical compound COC1=CC=C([N+]([O-])=O)C(OC)=C1Cl DXWGZZDXYVQOLW-UHFFFAOYSA-N 0.000 description 1
- FQXFHRSYMORXKN-UHFFFAOYSA-N 2-chloro-1-iodo-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(I)C(Cl)=C1 FQXFHRSYMORXKN-UHFFFAOYSA-N 0.000 description 1
- RNBSXWJOVLUYPI-UHFFFAOYSA-N 2-chloro-1-n-methyl-1-n-phenylbenzene-1,4-diamine Chemical compound C=1C=C(N)C=C(Cl)C=1N(C)C1=CC=CC=C1 RNBSXWJOVLUYPI-UHFFFAOYSA-N 0.000 description 1
- NNEQEZPLIXXULJ-UHFFFAOYSA-N 2-chloro-3-methoxy-6-nitrophenol;2,4-dichloro-3-methoxy-6-nitrophenol Chemical compound COC1=CC=C([N+]([O-])=O)C(O)=C1Cl.COC1=C(Cl)C=C([N+]([O-])=O)C(O)=C1Cl NNEQEZPLIXXULJ-UHFFFAOYSA-N 0.000 description 1
- MOTWHSMEZCFDOD-UHFFFAOYSA-N 2-chloro-4-nitro-1-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC=C(C(F)(F)F)C(Cl)=C1 MOTWHSMEZCFDOD-UHFFFAOYSA-N 0.000 description 1
- LOCWBQIWHWIRGN-UHFFFAOYSA-N 2-chloro-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Cl LOCWBQIWHWIRGN-UHFFFAOYSA-N 0.000 description 1
- CRRPJMGQJLYCIU-UHFFFAOYSA-N 2-chloro-n-(2-methoxyethyl)-n-methyl-4-nitroaniline Chemical compound COCCN(C)C1=CC=C([N+]([O-])=O)C=C1Cl CRRPJMGQJLYCIU-UHFFFAOYSA-N 0.000 description 1
- ORAHOABYCNJMSD-UHFFFAOYSA-N 2-chloro-n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]phenyl]benzamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1Cl ORAHOABYCNJMSD-UHFFFAOYSA-N 0.000 description 1
- BTUPOKNGPMPSJN-UHFFFAOYSA-N 2-chloro-n-cyclopentyl-n-methyl-4-nitroaniline Chemical compound C=1C=C([N+]([O-])=O)C=C(Cl)C=1N(C)C1CCCC1 BTUPOKNGPMPSJN-UHFFFAOYSA-N 0.000 description 1
- BYXQHIOMCSYHNV-UHFFFAOYSA-N 2-chloro-n-methyl-4-nitro-n-phenylaniline Chemical compound C=1C=C([N+]([O-])=O)C=C(Cl)C=1N(C)C1=CC=CC=C1 BYXQHIOMCSYHNV-UHFFFAOYSA-N 0.000 description 1
- 125000000872 2-diethylaminoethoxy group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- IQFJMIYFBRMRMF-UHFFFAOYSA-N 2-fluoro-N-(4-isothiocyanatophenyl)benzamide N-(4-isothiocyanatophenyl)furan-2-carboxamide Chemical compound N(=C=S)C1=CC=C(C=C1)NC(=O)C=1OC=CC1.FC1=C(C(=O)NC2=CC=C(C=C2)N=C=S)C=CC=C1 IQFJMIYFBRMRMF-UHFFFAOYSA-N 0.000 description 1
- DKEQQAIVWBYFBO-UHFFFAOYSA-N 2-fluoro-n-(2-methyl-4-nitrophenyl)benzamide Chemical compound CC1=CC([N+]([O-])=O)=CC=C1NC(=O)C1=CC=CC=C1F DKEQQAIVWBYFBO-UHFFFAOYSA-N 0.000 description 1
- LNCOLGQYPPALEM-UHFFFAOYSA-N 2-fluoro-n-[4-(1-isoquinolin-1-ylethylcarbamothioylamino)phenyl]benzamide Chemical compound N=1C=CC2=CC=CC=C2C=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F LNCOLGQYPPALEM-UHFFFAOYSA-N 0.000 description 1
- AHORKAMLDYDROX-UHFFFAOYSA-N 2-fluoro-n-[4-(1-isoquinolin-3-ylethylcarbamothioylamino)phenyl]benzamide Chemical compound C=1C2=CC=CC=C2C=NC=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F AHORKAMLDYDROX-UHFFFAOYSA-N 0.000 description 1
- CJHCDXCWGMOBKJ-UHFFFAOYSA-N 2-fluoro-n-[4-(1-phenylethylcarbamothioylamino)phenyl]benzamide Chemical compound C=1C=CC=CC=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F CJHCDXCWGMOBKJ-UHFFFAOYSA-N 0.000 description 1
- NXQYDRDCCHELPZ-UHFFFAOYSA-N 2-fluoro-n-[4-(1-pyridin-4-ylethylcarbamothioylamino)phenyl]benzamide Chemical compound C=1C=NC=CC=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F NXQYDRDCCHELPZ-UHFFFAOYSA-N 0.000 description 1
- PLRKIMRBRNZPLQ-UHFFFAOYSA-N 2-fluoro-n-[4-(1-quinolin-3-ylethylcarbamothioylamino)phenyl]benzamide Chemical compound C=1N=C2C=CC=CC2=CC=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F PLRKIMRBRNZPLQ-UHFFFAOYSA-N 0.000 description 1
- JRQTYQXLIHTOJO-UHFFFAOYSA-N 2-fluoro-n-[4-(1-thiophen-3-ylethylcarbamothioylamino)phenyl]benzamide Chemical compound C1=CSC=C1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F JRQTYQXLIHTOJO-UHFFFAOYSA-N 0.000 description 1
- UCMWVHFKPQDSNT-UHFFFAOYSA-N 2-fluoro-n-[4-(1h-indazol-5-ylcarbamothioylamino)phenyl]benzamide Chemical compound FC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NC1=CC=C(NN=C2)C2=C1 UCMWVHFKPQDSNT-UHFFFAOYSA-N 0.000 description 1
- NEAXFBDKRUMUKN-UHFFFAOYSA-N 2-fluoro-n-[4-(2-phenylethylcarbamothioylamino)phenyl]benzamide Chemical compound FC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NCCC1=CC=CC=C1 NEAXFBDKRUMUKN-UHFFFAOYSA-N 0.000 description 1
- VXXFWBOJMFSSRR-UHFFFAOYSA-N 2-fluoro-n-[4-(2-phenylsulfanylethylcarbamothioylamino)phenyl]benzamide Chemical compound FC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NCCSC1=CC=CC=C1 VXXFWBOJMFSSRR-UHFFFAOYSA-N 0.000 description 1
- OXRVUFVSKGWCRE-UHFFFAOYSA-N 2-fluoro-n-[4-(phenylcarbamothioylamino)phenyl]benzamide Chemical compound FC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NC1=CC=CC=C1 OXRVUFVSKGWCRE-UHFFFAOYSA-N 0.000 description 1
- PRXMCWWVOAKXGH-UHFFFAOYSA-N 2-fluoro-n-[4-(pyridin-2-ylcarbamothioylamino)phenyl]benzamide Chemical compound FC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NC1=CC=CC=N1 PRXMCWWVOAKXGH-UHFFFAOYSA-N 0.000 description 1
- JETZYHJPWPNFLL-UHFFFAOYSA-N 2-fluoro-n-[4-(pyridin-3-ylmethylcarbamothioylamino)phenyl]benzamide Chemical compound FC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NCC1=CC=CN=C1 JETZYHJPWPNFLL-UHFFFAOYSA-N 0.000 description 1
- XYNBCQKLNWNSJS-UHFFFAOYSA-N 2-fluoro-n-[4-(pyridin-4-ylmethylcarbamothioylamino)phenyl]benzamide Chemical compound FC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NCC1=CC=NC=C1 XYNBCQKLNWNSJS-UHFFFAOYSA-N 0.000 description 1
- BKJWSTYYRNWKAC-UHFFFAOYSA-N 2-fluoro-n-[4-[(3-fluoro-4-methylphenyl)carbamothioylamino]phenyl]benzamide Chemical compound C1=C(F)C(C)=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F BKJWSTYYRNWKAC-UHFFFAOYSA-N 0.000 description 1
- XAZVWWUMJFKGHO-UHFFFAOYSA-N 2-fluoro-n-[4-[(3-fluorophenyl)carbamothioylamino]phenyl]benzamide Chemical compound FC1=CC=CC(NC(=S)NC=2C=CC(NC(=O)C=3C(=CC=CC=3)F)=CC=2)=C1 XAZVWWUMJFKGHO-UHFFFAOYSA-N 0.000 description 1
- JSNUDWAEDMKQFV-UHFFFAOYSA-N 2-fluoro-n-[4-[(3-iodo-4-methoxyphenyl)carbamothioylamino]phenyl]benzamide Chemical compound C1=C(I)C(OC)=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F JSNUDWAEDMKQFV-UHFFFAOYSA-N 0.000 description 1
- JDSXJNVEUVIDCB-UHFFFAOYSA-N 2-fluoro-n-[4-[(3-methylphenyl)carbamothioylamino]phenyl]benzamide Chemical compound CC1=CC=CC(NC(=S)NC=2C=CC(NC(=O)C=3C(=CC=CC=3)F)=CC=2)=C1 JDSXJNVEUVIDCB-UHFFFAOYSA-N 0.000 description 1
- NFWRSJIBUKAHPB-UHFFFAOYSA-N 2-fluoro-n-[4-[(3-propan-2-ylphenyl)carbamothioylamino]phenyl]benzamide Chemical compound CC(C)C1=CC=CC(NC(=S)NC=2C=CC(NC(=O)C=3C(=CC=CC=3)F)=CC=2)=C1 NFWRSJIBUKAHPB-UHFFFAOYSA-N 0.000 description 1
- HHFJNIYKTRCGSG-UHFFFAOYSA-N 2-fluoro-n-[4-[1-(1,3-thiazol-2-yl)ethylcarbamothioylamino]phenyl]benzamide Chemical compound N=1C=CSC=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F HHFJNIYKTRCGSG-UHFFFAOYSA-N 0.000 description 1
- OJRURTRRAYQONT-UHFFFAOYSA-N 2-fluoro-n-[4-[1-(2-fluorophenyl)ethylcarbamothioylamino]phenyl]benzamide Chemical compound C=1C=CC=C(F)C=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F OJRURTRRAYQONT-UHFFFAOYSA-N 0.000 description 1
- KIYOLSYEMCSBFQ-UHFFFAOYSA-N 2-fluoro-n-[4-[1-(2-methoxyphenyl)ethylcarbamothioylamino]phenyl]benzamide Chemical compound COC1=CC=CC=C1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F KIYOLSYEMCSBFQ-UHFFFAOYSA-N 0.000 description 1
- LUACNYLGVFZBPQ-UHFFFAOYSA-N 2-fluoro-n-[4-[1-(2-methylphenyl)ethylcarbamothioylamino]phenyl]benzamide Chemical compound C=1C=CC=C(C)C=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F LUACNYLGVFZBPQ-UHFFFAOYSA-N 0.000 description 1
- GPQKIFXDZGCODD-UHFFFAOYSA-N 2-fluoro-n-[4-[1-(3-methylphenyl)ethylcarbamothioylamino]phenyl]benzamide Chemical compound C=1C=CC(C)=CC=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F GPQKIFXDZGCODD-UHFFFAOYSA-N 0.000 description 1
- FUIGVZHIPMTNHN-UHFFFAOYSA-N 2-fluoro-n-[4-[1-(4-fluorophenyl)pentylcarbamothioylamino]phenyl]benzamide Chemical compound C=1C=C(F)C=CC=1C(CCCC)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F FUIGVZHIPMTNHN-UHFFFAOYSA-N 0.000 description 1
- NQSAVUKDGXHDDK-UHFFFAOYSA-N 2-fluoro-n-[4-[1-(4-methoxyphenyl)ethylcarbamothioylamino]phenyl]benzamide Chemical compound C1=CC(OC)=CC=C1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F NQSAVUKDGXHDDK-UHFFFAOYSA-N 0.000 description 1
- JBAVFKKQNLPAOH-UHFFFAOYSA-N 2-fluoro-n-[4-[1-(4-methylphenyl)ethylcarbamothioylamino]phenyl]benzamide Chemical compound C=1C=C(C)C=CC=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F JBAVFKKQNLPAOH-UHFFFAOYSA-N 0.000 description 1
- NFHXKERZNANDJF-UHFFFAOYSA-N 2-fluoro-n-[4-[1-(furan-2-yl)ethylcarbamothioylamino]phenyl]benzamide Chemical compound C=1C=COC=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F NFHXKERZNANDJF-UHFFFAOYSA-N 0.000 description 1
- URIVRPICAKEUJT-UHFFFAOYSA-N 2-fluoro-n-[4-[1-[2-(trifluoromethyl)phenyl]ethylcarbamothioylamino]phenyl]benzamide Chemical compound C=1C=CC=C(C(F)(F)F)C=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F URIVRPICAKEUJT-UHFFFAOYSA-N 0.000 description 1
- QDQNTSLGFZNXCF-UHFFFAOYSA-N 2-fluoro-n-[4-[1-[4-(trifluoromethyl)phenyl]ethylcarbamothioylamino]phenyl]benzamide Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F QDQNTSLGFZNXCF-UHFFFAOYSA-N 0.000 description 1
- GMIHCFZCKGLGCM-UHFFFAOYSA-N 2-fluoro-n-[4-[2-(2-fluorophenyl)ethylcarbamothioylamino]phenyl]benzamide Chemical compound FC1=CC=CC=C1CCNC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F GMIHCFZCKGLGCM-UHFFFAOYSA-N 0.000 description 1
- JTHLGMLZIIEEBQ-UHFFFAOYSA-N 2-fluoro-n-[4-[2-(4-fluorophenyl)ethylcarbamothioylamino]phenyl]benzamide Chemical compound C1=CC(F)=CC=C1CCNC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F JTHLGMLZIIEEBQ-UHFFFAOYSA-N 0.000 description 1
- JBAVFKKQNLPAOH-MRXNPFEDSA-N 2-fluoro-n-[4-[[(1r)-1-(4-methylphenyl)ethyl]carbamothioylamino]phenyl]benzamide Chemical compound N([C@H](C)C=1C=CC(C)=CC=1)C(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F JBAVFKKQNLPAOH-MRXNPFEDSA-N 0.000 description 1
- CJHCDXCWGMOBKJ-OAHLLOKOSA-N 2-fluoro-n-[4-[[(1r)-1-phenylethyl]carbamothioylamino]phenyl]benzamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F CJHCDXCWGMOBKJ-OAHLLOKOSA-N 0.000 description 1
- JBAVFKKQNLPAOH-INIZCTEOSA-N 2-fluoro-n-[4-[[(1s)-1-(4-methylphenyl)ethyl]carbamothioylamino]phenyl]benzamide Chemical compound N([C@@H](C)C=1C=CC(C)=CC=1)C(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F JBAVFKKQNLPAOH-INIZCTEOSA-N 0.000 description 1
- CJHCDXCWGMOBKJ-HNNXBMFYSA-N 2-fluoro-n-[4-[[(1s)-1-phenylethyl]carbamothioylamino]phenyl]benzamide Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F CJHCDXCWGMOBKJ-HNNXBMFYSA-N 0.000 description 1
- KVPDWPONYGLREP-UHFFFAOYSA-N 2-fluoro-n-[4-[[1-(4-fluorophenyl)-2-phenylethyl]carbamothioylamino]phenyl]benzamide Chemical compound C1=CC(F)=CC=C1C(NC(=S)NC=1C=CC(NC(=O)C=2C(=CC=CC=2)F)=CC=1)CC1=CC=CC=C1 KVPDWPONYGLREP-UHFFFAOYSA-N 0.000 description 1
- OFORWHPUXKLTEF-UHFFFAOYSA-N 2-fluoro-n-[4-[[2-fluoro-5-(trifluoromethyl)phenyl]methylcarbamothioylamino]phenyl]benzamide Chemical compound FC1=CC=C(C(F)(F)F)C=C1CNC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F OFORWHPUXKLTEF-UHFFFAOYSA-N 0.000 description 1
- QDZIRMLZFBIPAY-UHFFFAOYSA-N 2-fluoro-n-[4-[[2-methoxy-4-(2,2,2-trifluoroethoxy)phenyl]carbamothioylamino]phenyl]benzamide Chemical compound COC1=CC(OCC(F)(F)F)=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F QDZIRMLZFBIPAY-UHFFFAOYSA-N 0.000 description 1
- PZNYIPCHDRIJKP-UHFFFAOYSA-N 2-fluoro-n-[4-[[3-(2-methylpropyl)-5-(trifluoromethyl)phenyl]carbamothioylamino]phenyl]benzamide Chemical compound FC(F)(F)C1=CC(CC(C)C)=CC(NC(=S)NC=2C=CC(NC(=O)C=3C(=CC=CC=3)F)=CC=2)=C1 PZNYIPCHDRIJKP-UHFFFAOYSA-N 0.000 description 1
- ATBJGJWHERJTST-UHFFFAOYSA-N 2-fluoro-n-[4-[[3-(hydrazinecarbonyl)phenyl]carbamothioylamino]phenyl]benzamide Chemical compound NNC(=O)C1=CC=CC(NC(=S)NC=2C=CC(NC(=O)C=3C(=CC=CC=3)F)=CC=2)=C1 ATBJGJWHERJTST-UHFFFAOYSA-N 0.000 description 1
- NHKPKVBHWVECST-UHFFFAOYSA-N 2-fluoro-n-[4-[[3-(trifluoromethoxy)phenyl]carbamothioylamino]phenyl]benzamide Chemical compound FC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NC1=CC=CC(OC(F)(F)F)=C1 NHKPKVBHWVECST-UHFFFAOYSA-N 0.000 description 1
- GOAYILFNFRXTCN-UHFFFAOYSA-N 2-fluoro-n-[4-[[3-(trifluoromethyl)phenyl]carbamothioylamino]phenyl]benzamide Chemical compound FC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NC1=CC=CC(C(F)(F)F)=C1 GOAYILFNFRXTCN-UHFFFAOYSA-N 0.000 description 1
- JYTBXQUVDYWJOE-UHFFFAOYSA-N 2-fluoro-n-[4-[[3-[methyl(2-methylpropyl)amino]-5-(trifluoromethyl)phenyl]carbamothioylamino]phenyl]benzamide Chemical compound FC(F)(F)C1=CC(N(C)CC(C)C)=CC(NC(=S)NC=2C=CC(NC(=O)C=3C(=CC=CC=3)F)=CC=2)=C1 JYTBXQUVDYWJOE-UHFFFAOYSA-N 0.000 description 1
- NLPXBOBMIPWVRG-UHFFFAOYSA-N 2-fluoro-n-[4-[[3-fluoro-5-(trifluoromethyl)phenyl]methylcarbamothioylamino]phenyl]benzamide Chemical compound FC(F)(F)C1=CC(F)=CC(CNC(=S)NC=2C=CC(NC(=O)C=3C(=CC=CC=3)F)=CC=2)=C1 NLPXBOBMIPWVRG-UHFFFAOYSA-N 0.000 description 1
- AVNWHPITOLCPML-UHFFFAOYSA-N 2-fluoro-n-[4-[[4-(4-methylpiperazin-1-yl)-3-(trifluoromethyl)phenyl]methylcarbamothioylamino]phenyl]benzamide Chemical compound C1CN(C)CCN1C(C(=C1)C(F)(F)F)=CC=C1CNC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F AVNWHPITOLCPML-UHFFFAOYSA-N 0.000 description 1
- ZJAQLFXJDGNPLK-UHFFFAOYSA-N 2-fluoro-n-[4-[[4-methyl-3-(trifluoromethyl)phenyl]carbamothioylamino]phenyl]benzamide Chemical compound C1=C(C(F)(F)F)C(C)=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F ZJAQLFXJDGNPLK-UHFFFAOYSA-N 0.000 description 1
- OWQFFWBZZNAZFD-UHFFFAOYSA-N 2-fluoro-n-[4-[[4-piperidin-1-yl-3-(trifluoromethyl)phenyl]methylcarbamothioylamino]phenyl]benzamide Chemical compound FC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NCC(C=C1C(F)(F)F)=CC=C1N1CCCCC1 OWQFFWBZZNAZFD-UHFFFAOYSA-N 0.000 description 1
- KGGHWIKBOIQEAJ-UHFFFAOYSA-N 2-fluorobenzamide Chemical compound NC(=O)C1=CC=CC=C1F KGGHWIKBOIQEAJ-UHFFFAOYSA-N 0.000 description 1
- RAAGZOYMEQDCTD-UHFFFAOYSA-N 2-fluorobenzoyl chloride Chemical compound FC1=CC=CC=C1C(Cl)=O RAAGZOYMEQDCTD-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- WTUYBONQHDGSSN-UHFFFAOYSA-N 2-methoxy-n-(4-nitrophenyl)acetamide Chemical compound COCC(=O)NC1=CC=C([N+]([O-])=O)C=C1 WTUYBONQHDGSSN-UHFFFAOYSA-N 0.000 description 1
- DJVXQOSLQBMQBY-UHFFFAOYSA-N 2-methoxy-n-[4-(1-thiophen-3-ylethylcarbamothioylamino)phenyl]benzamide Chemical compound COC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NC(C)C1=CSC=C1 DJVXQOSLQBMQBY-UHFFFAOYSA-N 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- ZHDRDZMTEOIWSX-UHFFFAOYSA-N 2-methyl-1,3-thiazole-4-carboxylic acid Chemical compound CC1=NC(C(O)=O)=CS1 ZHDRDZMTEOIWSX-UHFFFAOYSA-N 0.000 description 1
- XEPVIJLDANFVIX-UHFFFAOYSA-N 2-methylpropyl n-(4-aminophenyl)carbamate Chemical compound CC(C)COC(=O)NC1=CC=C(N)C=C1 XEPVIJLDANFVIX-UHFFFAOYSA-N 0.000 description 1
- UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 description 1
- ILYSAKHOYBPSPC-UHFFFAOYSA-N 2-phenylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC=C1 ILYSAKHOYBPSPC-UHFFFAOYSA-N 0.000 description 1
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical class OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 1
- OFBDXJMVPKCKBB-UHFFFAOYSA-N 2-piperidin-1-ylethyl n-[2-chloro-4-[[4-[(2-fluorobenzoyl)amino]phenyl]carbamothioylamino]phenyl]carbamate Chemical compound FC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NC(C=C1Cl)=CC=C1NC(=O)OCCN1CCCCC1 OFBDXJMVPKCKBB-UHFFFAOYSA-N 0.000 description 1
- MXONPYVPZLUMER-UHFFFAOYSA-N 2-trimethylsilylethyl n-[3-chloro-4-(1-hydroxyethyl)phenyl]carbamate Chemical compound CC(O)C1=CC=C(NC(=O)OCC[Si](C)(C)C)C=C1Cl MXONPYVPZLUMER-UHFFFAOYSA-N 0.000 description 1
- GTODOEDLCNTSLG-UHFFFAOYSA-N 2h-triazole-4-carboxylic acid Chemical compound OC(=O)C1=CNN=N1 GTODOEDLCNTSLG-UHFFFAOYSA-N 0.000 description 1
- MKWFYXWVSGCEAK-UHFFFAOYSA-N 3,5-dichloro-1-fluoro-2h-pyridine;trifluoromethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)F.FN1CC(Cl)=CC(Cl)=C1 MKWFYXWVSGCEAK-UHFFFAOYSA-N 0.000 description 1
- CITXWPNOZYUNNO-UHFFFAOYSA-N 3,5-dichloro-4-methoxy-2-methylaniline Chemical compound COC1=C(Cl)C=C(N)C(C)=C1Cl CITXWPNOZYUNNO-UHFFFAOYSA-N 0.000 description 1
- KFAAKHZTICEVTO-UHFFFAOYSA-N 3,5-dichloro-4-phenoxyaniline Chemical compound ClC1=CC(N)=CC(Cl)=C1OC1=CC=CC=C1 KFAAKHZTICEVTO-UHFFFAOYSA-N 0.000 description 1
- UQRLKWGPEVNVHT-UHFFFAOYSA-N 3,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC(Cl)=C1 UQRLKWGPEVNVHT-UHFFFAOYSA-N 0.000 description 1
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 1
- OXNZCDDYBDTVBS-UHFFFAOYSA-N 3-(2-aminoethyl)-N,N-dimethyl-5-(trifluoromethyl)aniline 4-(2-aminoethyl)-N,N,2-trimethylaniline 3-(aminomethyl)-N,N-dimethyl-5-(trifluoromethyl)aniline Chemical compound NCCC1=CC(=C(C=C1)N(C)C)C.NCCC=1C=C(C=C(C1)C(F)(F)F)N(C)C.NCC=1C=C(C=C(C1)C(F)(F)F)N(C)C OXNZCDDYBDTVBS-UHFFFAOYSA-N 0.000 description 1
- BLHCNHQMHNNBDT-UHFFFAOYSA-N 3-(2-chloro-4-nitrophenoxy)-1-methylpyrrolidine Chemical compound C1N(C)CCC1OC1=CC=C([N+]([O-])=O)C=C1Cl BLHCNHQMHNNBDT-UHFFFAOYSA-N 0.000 description 1
- MMOFOGZKRRPULJ-UHFFFAOYSA-N 3-(2-ethoxy-2-oxoethoxy)benzoic acid Chemical compound CCOC(=O)COC1=CC=CC(C(O)=O)=C1 MMOFOGZKRRPULJ-UHFFFAOYSA-N 0.000 description 1
- NYAAGBAMENVXCE-UHFFFAOYSA-N 3-(dimethylamino)-5-(trifluoromethyl)benzonitrile Chemical compound CN(C)C1=CC(C#N)=CC(C(F)(F)F)=C1 NYAAGBAMENVXCE-UHFFFAOYSA-N 0.000 description 1
- SWVVDMMMEQUMDR-UHFFFAOYSA-N 3-[[4-(furan-2-carbonylamino)phenyl]carbamothioylamino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NC(=S)NC=2C=CC(NC(=O)C=3OC=CC=3)=CC=2)=C1 SWVVDMMMEQUMDR-UHFFFAOYSA-N 0.000 description 1
- MATTXHSAGGJGDG-UHFFFAOYSA-N 3-[[4-[(2-fluorobenzoyl)amino]phenyl]carbamothioylamino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NC(=S)NC=2C=CC(NC(=O)C=3C(=CC=CC=3)F)=CC=2)=C1 MATTXHSAGGJGDG-UHFFFAOYSA-N 0.000 description 1
- OSLFKRUDXPALFD-UHFFFAOYSA-N 3-[[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]phenyl]carbamoyl]benzoic acid Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC(C(O)=O)=C1 OSLFKRUDXPALFD-UHFFFAOYSA-N 0.000 description 1
- VNIHAHRMFJVBGJ-UHFFFAOYSA-N 3-bromo-4-methoxyaniline 3-chloro-2,4-dimethoxyaniline 3-chloro-1-N,1-N-dimethylbenzene-1,2-diamine 3-chloro-4-ethoxyaniline 3-chloro-4-propoxyaniline 3-iodo-4-methoxyaniline Chemical compound ClC=1C=C(C=CC1OCC)N.BrC=1C=C(C=CC1OC)N.ClC=1C(=C(N)C=CC1OC)OC.IC=1C=C(C=CC1OC)N.ClC=1C=C(C=CC1OCCC)N.ClC1=C(C(=CC=C1)N(C)C)N VNIHAHRMFJVBGJ-UHFFFAOYSA-N 0.000 description 1
- HJTLKVYOWNTDPF-UHFFFAOYSA-N 3-bromo-5-(trifluoromethyl)aniline Chemical compound NC1=CC(Br)=CC(C(F)(F)F)=C1 HJTLKVYOWNTDPF-UHFFFAOYSA-N 0.000 description 1
- AYRFQLRYTJYNPA-UHFFFAOYSA-N 3-bromo-n,n-dimethyl-5-(trifluoromethyl)aniline Chemical compound CN(C)C1=CC(Br)=CC(C(F)(F)F)=C1 AYRFQLRYTJYNPA-UHFFFAOYSA-N 0.000 description 1
- VQQLWBUTTMNMFT-UHFFFAOYSA-N 3-bromothiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC=CC=1Br VQQLWBUTTMNMFT-UHFFFAOYSA-N 0.000 description 1
- OOZHTWCSBRHXNG-UHFFFAOYSA-N 3-butoxy-n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]phenyl]benzamide Chemical compound CCCCOC1=CC=CC(C(=O)NC=2C=CC(NC(=S)NC=3C(=CC(OC)=C(Cl)C=3)OC)=CC=2)=C1 OOZHTWCSBRHXNG-UHFFFAOYSA-N 0.000 description 1
- DPFOXMVFJHIWGQ-UHFFFAOYSA-N 3-chloro-4-cyclohexyloxyaniline Chemical compound ClC1=CC(N)=CC=C1OC1CCCCC1 DPFOXMVFJHIWGQ-UHFFFAOYSA-N 0.000 description 1
- JSHWVUGYYWWQCV-UHFFFAOYSA-N 3-chloro-4-ethenylaniline Chemical compound NC1=CC=C(C=C)C(Cl)=C1 JSHWVUGYYWWQCV-UHFFFAOYSA-N 0.000 description 1
- RCJMWDBAXQQCPC-UHFFFAOYSA-N 3-chloro-4-methylsulfanylaniline;2,6-dichlorobenzene-1,4-diamine Chemical compound CSC1=CC=C(N)C=C1Cl.NC1=CC(Cl)=C(N)C(Cl)=C1 RCJMWDBAXQQCPC-UHFFFAOYSA-N 0.000 description 1
- YXBDJALKYPUAFT-UHFFFAOYSA-N 3-chloro-4-propan-2-yloxyaniline Chemical compound CC(C)OC1=CC=C(N)C=C1Cl YXBDJALKYPUAFT-UHFFFAOYSA-N 0.000 description 1
- BNPSPBWNZBGVDT-UHFFFAOYSA-N 3-chloro-n-[4-[1-(4-fluorophenyl)ethylcarbamothioylamino]phenyl]benzamide Chemical compound C=1C=C(F)C=CC=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC(Cl)=C1 BNPSPBWNZBGVDT-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- KYENQJICITXEGJ-UHFFFAOYSA-N 3-cyano-n-[4-[1-(4-fluorophenyl)ethylcarbamothioylamino]phenyl]benzamide Chemical compound C=1C=C(F)C=CC=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC(C#N)=C1 KYENQJICITXEGJ-UHFFFAOYSA-N 0.000 description 1
- KLIRZBPSXYYRIN-UHFFFAOYSA-N 3-fluoro-n-[4-[1-(4-fluorophenyl)ethylcarbamothioylamino]phenyl]benzamide Chemical compound C=1C=C(F)C=CC=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC(F)=C1 KLIRZBPSXYYRIN-UHFFFAOYSA-N 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- BNYIQEFWGSXIKQ-UHFFFAOYSA-N 3-methylfuran-2-carboxylic acid Chemical compound CC=1C=COC=1C(O)=O BNYIQEFWGSXIKQ-UHFFFAOYSA-N 0.000 description 1
- IVQIGNIDIKGVHH-UHFFFAOYSA-N 3-morpholin-4-yl-5-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC(N)=CC(N2CCOCC2)=C1 IVQIGNIDIKGVHH-UHFFFAOYSA-N 0.000 description 1
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 1
- VNGPHYFVHGSJRA-UHFFFAOYSA-N 4-(2-chloro-4-nitrophenoxy)-1-methylpiperidine Chemical compound C1CN(C)CCC1OC1=CC=C([N+]([O-])=O)C=C1Cl VNGPHYFVHGSJRA-UHFFFAOYSA-N 0.000 description 1
- NFIAPDCCKPTYJB-UHFFFAOYSA-N 4-(3,4,4a,5,6,7,8,8a-octahydro-2h-quinolin-1-yl)-3-chloroaniline Chemical compound ClC1=CC(N)=CC=C1N1C2CCCCC2CCC1 NFIAPDCCKPTYJB-UHFFFAOYSA-N 0.000 description 1
- OAMILPMFQFIAPO-UHFFFAOYSA-N 4-(aminomethyl)-n,n-dimethyl-2-(trifluoromethyl)aniline Chemical compound CN(C)C1=CC=C(CN)C=C1C(F)(F)F OAMILPMFQFIAPO-UHFFFAOYSA-N 0.000 description 1
- BFWYZZPDZZGSLJ-UHFFFAOYSA-N 4-(aminomethyl)aniline Chemical compound NCC1=CC=C(N)C=C1 BFWYZZPDZZGSLJ-UHFFFAOYSA-N 0.000 description 1
- UUKQLJHJAVCMSX-UHFFFAOYSA-N 4-(dimethylamino)-3-(trifluoromethyl)benzonitrile Chemical compound CN(C)C1=CC=C(C#N)C=C1C(F)(F)F UUKQLJHJAVCMSX-UHFFFAOYSA-N 0.000 description 1
- KUBZDRHYLATWGV-UHFFFAOYSA-N 4-(dimethylamino)-3-methylbenzaldehyde;3-(dimethylamino)-5-(trifluoromethyl)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1C.CN(C)C1=CC(C=O)=CC(C(F)(F)F)=C1 KUBZDRHYLATWGV-UHFFFAOYSA-N 0.000 description 1
- FVRVFRZKHOOQBD-UHFFFAOYSA-N 4-(dimethylamino)-n-[4-[1-(4-fluorophenyl)ethylcarbamothioylamino]phenyl]benzamide Chemical compound C=1C=C(F)C=CC=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=C(N(C)C)C=C1 FVRVFRZKHOOQBD-UHFFFAOYSA-N 0.000 description 1
- CANLULJYEHSQFU-ZETCQYMHSA-N 4-[(1s)-1-aminoethyl]benzonitrile Chemical compound C[C@H](N)C1=CC=C(C#N)C=C1 CANLULJYEHSQFU-ZETCQYMHSA-N 0.000 description 1
- HFOFVIVGYAEWAV-UHFFFAOYSA-N 4-[(4-acetamidophenyl)carbamothioylamino]-2-chlorobenzoic acid Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC1=CC=C(C(O)=O)C(Cl)=C1 HFOFVIVGYAEWAV-UHFFFAOYSA-N 0.000 description 1
- KYRHYXQTWMRXQU-UHFFFAOYSA-N 4-amino-n-[3-(dimethylamino)prop-1-ynyl]benzamide Chemical compound CN(C)CC#CNC(=O)C1=CC=C(N)C=C1 KYRHYXQTWMRXQU-UHFFFAOYSA-N 0.000 description 1
- SRTSTGXCDFPQNW-UHFFFAOYSA-N 4-amino-n-[3-(dimethylamino)prop-2-enoyl]benzamide Chemical compound CN(C)C=CC(=O)NC(=O)C1=CC=C(N)C=C1 SRTSTGXCDFPQNW-UHFFFAOYSA-N 0.000 description 1
- WPBZMCGPFHZRHJ-UHFFFAOYSA-N 4-aminobenzohydrazide Chemical compound NNC(=O)C1=CC=C(N)C=C1 WPBZMCGPFHZRHJ-UHFFFAOYSA-N 0.000 description 1
- KGEXISHTCZHGFT-UHFFFAOYSA-N 4-azaniumyl-2,6-dichlorophenolate Chemical compound NC1=CC(Cl)=C(O)C(Cl)=C1 KGEXISHTCZHGFT-UHFFFAOYSA-N 0.000 description 1
- IVWSVUAULSWZNB-UHFFFAOYSA-N 4-bromo-2,4-dimethoxycyclohexa-1,5-dien-1-amine Chemical compound COC1=C(N)C=CC(Br)(OC)C1 IVWSVUAULSWZNB-UHFFFAOYSA-N 0.000 description 1
- QALYBHRYGIXHOF-UHFFFAOYSA-N 4-bromofuran-2-carboxylic acid Chemical compound OC(=O)C1=CC(Br)=CO1 QALYBHRYGIXHOF-UHFFFAOYSA-N 0.000 description 1
- NBXIUZZKRDDNRX-UHFFFAOYSA-N 4-chloro-n-[4-[1-(4-fluorophenyl)ethylcarbamothioylamino]phenyl]benzamide Chemical compound C=1C=C(F)C=CC=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C=C1 NBXIUZZKRDDNRX-UHFFFAOYSA-N 0.000 description 1
- RNOVGJWJVRESAA-UHFFFAOYSA-N 4-fluoro-2-(trifluoromethyl)phenol Chemical group OC1=CC=C(F)C=C1C(F)(F)F RNOVGJWJVRESAA-UHFFFAOYSA-N 0.000 description 1
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- PIIZYNQECPTVEO-UHFFFAOYSA-N 4-nitro-m-cresol Chemical compound CC1=CC(O)=CC=C1[N+]([O-])=O PIIZYNQECPTVEO-UHFFFAOYSA-N 0.000 description 1
- ODVBBZFQPGORMJ-UHFFFAOYSA-N 4-nitrobenzylamine Chemical compound NCC1=CC=C([N+]([O-])=O)C=C1 ODVBBZFQPGORMJ-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- QSUILVWOWLUOEU-GOVZDWNOSA-N 4-nitrophenyl beta-D-glucuronide Chemical compound O1[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1OC1=CC=C([N+]([O-])=O)C=C1 QSUILVWOWLUOEU-GOVZDWNOSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- LWXSNJGJZZXDAN-UHFFFAOYSA-N 5-(furan-3-yl)thiadiazole-4-carboxylic acid Chemical compound N1=NSC(C2=COC=C2)=C1C(=O)O LWXSNJGJZZXDAN-UHFFFAOYSA-N 0.000 description 1
- FCNMSVZMRSGGGE-UHFFFAOYSA-N 5-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-2-[(2-fluorobenzoyl)amino]-n-phenylbenzamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1C(=O)NC=2C=CC=CC=2)=CC=C1NC(=O)C1=CC=CC=C1F FCNMSVZMRSGGGE-UHFFFAOYSA-N 0.000 description 1
- LWALGMOXWQYQTG-UHFFFAOYSA-N 5-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-2-[(2-fluorobenzoyl)amino]benzoic acid Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1C(O)=O)=CC=C1NC(=O)C1=CC=CC=C1F LWALGMOXWQYQTG-UHFFFAOYSA-N 0.000 description 1
- JDTWONPNHDXHEZ-UHFFFAOYSA-N 5-bromo-1,5-dimethoxy-2-nitrocyclohexa-1,3-diene Chemical compound COC1=C([N+]([O-])=O)C=CC(Br)(OC)C1 JDTWONPNHDXHEZ-UHFFFAOYSA-N 0.000 description 1
- KXTIRUXWVONFBK-UHFFFAOYSA-N 5-chloro-2-ethoxy-4-methoxyaniline 5-chloro-4-ethoxy-2-methoxyaniline 3,5-diiodo-2,4-dimethoxyaniline 5-iodo-2,4-dimethoxyaniline Chemical compound IC=1C(=C(C=C(C1OC)I)N)OC.IC=1C(=CC(=C(C1)N)OC)OC.ClC=1C(=CC(=C(C1)N)OC)OCC.ClC=1C(=CC(=C(C1)N)OCC)OC KXTIRUXWVONFBK-UHFFFAOYSA-N 0.000 description 1
- ZLJIFINJKVSIRN-UHFFFAOYSA-N 5-methylthiadiazole-4-carboxylic acid Chemical compound CC=1SN=NC=1C(O)=O ZLJIFINJKVSIRN-UHFFFAOYSA-N 0.000 description 1
- XPQVOJPPGWAQKB-UHFFFAOYSA-N 5-phenylthiadiazole-4-carboxylic acid Chemical compound N1=NSC(C=2C=CC=CC=2)=C1C(=O)O XPQVOJPPGWAQKB-UHFFFAOYSA-N 0.000 description 1
- PXSGFTWBZNPNIC-UHFFFAOYSA-N 618-80-4 Chemical compound OC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl PXSGFTWBZNPNIC-UHFFFAOYSA-N 0.000 description 1
- BOFRXDMCQRTGII-UHFFFAOYSA-N 619-08-9 Chemical compound OC1=CC=C([N+]([O-])=O)C=C1Cl BOFRXDMCQRTGII-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 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
- 235000003911 Arachis Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 102100022717 Atypical chemokine receptor 1 Human genes 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- DBTUQENLPAQSJX-UHFFFAOYSA-N C(C(C)C)N(C1=CC(=CC(=C1)C(F)(F)F)N)C.CN(C1=CC(=CC(=C1)C(F)(F)F)N)C.N1(CCCC1)C=1C=C(C=C(C1)C(F)(F)F)N Chemical compound C(C(C)C)N(C1=CC(=CC(=C1)C(F)(F)F)N)C.CN(C1=CC(=CC(=C1)C(F)(F)F)N)C.N1(CCCC1)C=1C=C(C=C(C1)C(F)(F)F)N DBTUQENLPAQSJX-UHFFFAOYSA-N 0.000 description 1
- KXGNRFJTIBJACH-UHFFFAOYSA-N C(C(C)C)[AlH]CC(C)C.CN(C=1C=C(C=O)C=C(C1)C(F)(F)F)C Chemical compound C(C(C)C)[AlH]CC(C)C.CN(C=1C=C(C=O)C=C(C1)C(F)(F)F)C KXGNRFJTIBJACH-UHFFFAOYSA-N 0.000 description 1
- REQPTKPZSZHZHS-UHFFFAOYSA-N C(C)(=O)O.NC1=CC=C(C=C1)NC(C1=C(C=CC=C1)C)=O.ClC=1C=C(C=CC1S(=O)(=O)C)N.BrC=1C=C(C=NC1)N Chemical compound C(C)(=O)O.NC1=CC=C(C=C1)NC(C1=C(C=CC=C1)C)=O.ClC=1C=C(C=CC1S(=O)(=O)C)N.BrC=1C=C(C=NC1)N REQPTKPZSZHZHS-UHFFFAOYSA-N 0.000 description 1
- VBFFTNLOIAJWRJ-UHFFFAOYSA-N C(C)(C)(C)OC(NC1=CC(=C(C=C1)Br)Cl)=O.C(C)(C)(C)OC(NC1=CC(=C(C=C1)I)Cl)=O.C(C)(C)(C)OC(=O)NNC(C1=CC=C(C=C1)[N+](=O)[O-])=O Chemical compound C(C)(C)(C)OC(NC1=CC(=C(C=C1)Br)Cl)=O.C(C)(C)(C)OC(NC1=CC(=C(C=C1)I)Cl)=O.C(C)(C)(C)OC(=O)NNC(C1=CC=C(C=C1)[N+](=O)[O-])=O VBFFTNLOIAJWRJ-UHFFFAOYSA-N 0.000 description 1
- MXNWCTPMKOBLBR-UHFFFAOYSA-N C(C)(C)(C)OC(NC1=CC=C(C=C1)NC(=O)C1=C(N=NS1)C)=O.C(C)(C)(C)OC(NC1=CC=C(C=C1)NC(=O)C1=CC=NC2=CC=CC=C12)=O Chemical compound C(C)(C)(C)OC(NC1=CC=C(C=C1)NC(=O)C1=C(N=NS1)C)=O.C(C)(C)(C)OC(NC1=CC=C(C=C1)NC(=O)C1=CC=NC2=CC=CC=C12)=O MXNWCTPMKOBLBR-UHFFFAOYSA-N 0.000 description 1
- DTOVHEFQRITHRU-UHFFFAOYSA-N C(C)(C)(C)OC(NC1=CC=C(C=C1)NC(=O)C1=CC2=CC=CC=C2C=C1)=O.C(C)(C)(C)OC(NC1=CC=C(C=C1)NC(=O)C1=CC=NC=C1)=O Chemical compound C(C)(C)(C)OC(NC1=CC=C(C=C1)NC(=O)C1=CC2=CC=CC=C2C=C1)=O.C(C)(C)(C)OC(NC1=CC=C(C=C1)NC(=O)C1=CC=NC=C1)=O DTOVHEFQRITHRU-UHFFFAOYSA-N 0.000 description 1
- KKIHZSKUQOXXPT-UHFFFAOYSA-N C(C)(C)(C)OC(NC1=CC=C(C=C1)NC(=O)C=1N(C=CC1)C)=O.C(C)(C)(C)OC(NC1=CC=C(C=C1)NC(=O)C=1SC(=CC1)C)=O Chemical compound C(C)(C)(C)OC(NC1=CC=C(C=C1)NC(=O)C=1N(C=CC1)C)=O.C(C)(C)(C)OC(NC1=CC=C(C=C1)NC(=O)C=1SC(=CC1)C)=O KKIHZSKUQOXXPT-UHFFFAOYSA-N 0.000 description 1
- FTKYIHNNFKBRMV-UHFFFAOYSA-N C(C)(C)(C)OC(NC1=CC=C(C=C1)NC(=O)C=1NC2=CC=CC=C2C1)=O.C(C)(C)(C)OC(NC1=CC=C(C=C1)NC(=O)C1=C(N=NS1)C1=CC=CC=C1)=O Chemical compound C(C)(C)(C)OC(NC1=CC=C(C=C1)NC(=O)C=1NC2=CC=CC=C2C1)=O.C(C)(C)(C)OC(NC1=CC=C(C=C1)NC(=O)C1=C(N=NS1)C1=CC=CC=C1)=O FTKYIHNNFKBRMV-UHFFFAOYSA-N 0.000 description 1
- RAZLGBVHSBIDIL-UHFFFAOYSA-N C(C)(C)(C)OC(NC1=CC=C(C=C1)NC(=O)C=1OC2=C(C1)C=CC=C2)=O.C(C)(C)(C)OC(NC2=CC=C(C=C2)NC(=O)C=2C=CC=C1C=CC=NC21)=O Chemical compound C(C)(C)(C)OC(NC1=CC=C(C=C1)NC(=O)C=1OC2=C(C1)C=CC=C2)=O.C(C)(C)(C)OC(NC2=CC=C(C=C2)NC(=O)C=2C=CC=C1C=CC=NC21)=O RAZLGBVHSBIDIL-UHFFFAOYSA-N 0.000 description 1
- PECVBQGPONNYOF-UHFFFAOYSA-N C(C)(C)(C)OC(NC1=CC=C(C=C1)NC(C1=C(C=CC=C1)SC)=O)=O.C(C)(C)(C)OC(NC1=CC=C(C=C1)NC(=O)C=1N=NNC1)=O Chemical compound C(C)(C)(C)OC(NC1=CC=C(C=C1)NC(C1=C(C=CC=C1)SC)=O)=O.C(C)(C)(C)OC(NC1=CC=C(C=C1)NC(=O)C=1N=NNC1)=O PECVBQGPONNYOF-UHFFFAOYSA-N 0.000 description 1
- CDBAWZFDPYERLM-UHFFFAOYSA-N C(C)(C)(C)OC(NC1=CC=C(C=C1)NC(C1=CC(=CC=C1)OCCCl)=O)=O.C(C)(C)(C)OC(NC1=CC=C(C=C1)NC(C1=CC(=CC=C1)OCC(N)=O)=O)=O Chemical compound C(C)(C)(C)OC(NC1=CC=C(C=C1)NC(C1=CC(=CC=C1)OCCCl)=O)=O.C(C)(C)(C)OC(NC1=CC=C(C=C1)NC(C1=CC(=CC=C1)OCC(N)=O)=O)=O CDBAWZFDPYERLM-UHFFFAOYSA-N 0.000 description 1
- JBTZBMNYUSBEHP-UHFFFAOYSA-N C(N)(=O)COC=1C=C(C(=O)O)C=CC1.COC(C1=CC(=CC=C1)OCC(=O)OC(C)(C)C)=O.COC(C1=CC(=CC=C1)OCCCC)=O.COC(COC1=C(C=C(C=C1Cl)NC(=O)OC(C)(C)C)Cl)=O Chemical compound C(N)(=O)COC=1C=C(C(=O)O)C=CC1.COC(C1=CC(=CC=C1)OCC(=O)OC(C)(C)C)=O.COC(C1=CC(=CC=C1)OCCCC)=O.COC(COC1=C(C=C(C=C1Cl)NC(=O)OC(C)(C)C)Cl)=O JBTZBMNYUSBEHP-UHFFFAOYSA-N 0.000 description 1
- KRSVPFDGKXHKGD-UHFFFAOYSA-L C([O-])([O-])=O.[K+].NC1=C(C=C(C=C1)NC(C1=C(C=CC=C1)F)=O)C#N.[K+] Chemical compound C([O-])([O-])=O.[K+].NC1=C(C=C(C=C1)NC(C1=C(C=CC=C1)F)=O)C#N.[K+] KRSVPFDGKXHKGD-UHFFFAOYSA-L 0.000 description 1
- OXXGMQKXVXICOA-UHFFFAOYSA-N C=1C=C(NC(=S)NC=2C=CC(NC(=O)C=3N=CC=CC=3)=CC=2)C=C(Cl)C=1N(C)C1CCCCC1 Chemical compound C=1C=C(NC(=S)NC=2C=CC(NC(=O)C=3N=CC=CC=3)=CC=2)C=C(Cl)C=1N(C)C1CCCCC1 OXXGMQKXVXICOA-UHFFFAOYSA-N 0.000 description 1
- OEDNTECCQYLELK-UHFFFAOYSA-N CN1CCN(CC1)C1=C(C=C(C#N)C=C1)C(F)(F)F.CN(C1=C(C=C(C#N)C=C1)C(F)(F)F)C.N1(CCCCC1)C1=C(C=C(C#N)C=C1)C(F)(F)F Chemical compound CN1CCN(CC1)C1=C(C=C(C#N)C=C1)C(F)(F)F.CN(C1=C(C=C(C#N)C=C1)C(F)(F)F)C.N1(CCCCC1)C1=C(C=C(C#N)C=C1)C(F)(F)F OEDNTECCQYLELK-UHFFFAOYSA-N 0.000 description 1
- RCSKZHHONYEASE-UHFFFAOYSA-N CN1CCN(CC1)C1=C(C=C(CN)C=C1)C(F)(F)F.NCC1=CC(=C(C=C1)N(C)C)C(F)(F)F.N1(CCCCC1)C1=C(C=C(CN)C=C1)C(F)(F)F Chemical compound CN1CCN(CC1)C1=C(C=C(CN)C=C1)C(F)(F)F.NCC1=CC(=C(C=C1)N(C)C)C(F)(F)F.N1(CCCCC1)C1=C(C=C(CN)C=C1)C(F)(F)F RCSKZHHONYEASE-UHFFFAOYSA-N 0.000 description 1
- PXKAJLFYSDFGJK-UHFFFAOYSA-N CON=C(C)C1=C(C=C(C=C1)F)Cl.CON=C(C)C1=CC=C(C=C1)N1CCOCC1 Chemical compound CON=C(C)C1=C(C=C(C=C1)F)Cl.CON=C(C)C1=CC=C(C=C1)N1CCOCC1 PXKAJLFYSDFGJK-UHFFFAOYSA-N 0.000 description 1
- JNYWMGXZCOOVTN-UHFFFAOYSA-N CON=C(C)C=1OC=CC1.CON=C(C)C1=CC=C(C=C1)C(F)(F)F.CON=C(C)C1=CC(=CC=C1)C(F)(F)F.CON=C(C)C1=CC(=CC=C1)OC Chemical compound CON=C(C)C=1OC=CC1.CON=C(C)C1=CC=C(C=C1)C(F)(F)F.CON=C(C)C1=CC(=CC=C1)C(F)(F)F.CON=C(C)C1=CC(=CC=C1)OC JNYWMGXZCOOVTN-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 208000014912 Central Nervous System Infections Diseases 0.000 description 1
- 102000019034 Chemokines Human genes 0.000 description 1
- 108010012236 Chemokines Proteins 0.000 description 1
- 201000006082 Chickenpox Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- BCXMHXWHCRXUKO-UHFFFAOYSA-N ClC1=C(C=CC(=C1)[N+](=O)[O-])N(C)CCCCCC.ClC1=C(C=CC(=C1)[N+](=O)[O-])N(C)CC(C)C.ClC1=C(C=CC(=C1)[N+](=O)[O-])N(CCO)CCO Chemical compound ClC1=C(C=CC(=C1)[N+](=O)[O-])N(C)CCCCCC.ClC1=C(C=CC(=C1)[N+](=O)[O-])N(C)CC(C)C.ClC1=C(C=CC(=C1)[N+](=O)[O-])N(CCO)CCO BCXMHXWHCRXUKO-UHFFFAOYSA-N 0.000 description 1
- WJQJOVSUPPYDKU-UHFFFAOYSA-N ClC1=C(C=CC=C1)C(C)N.C1(=CC=CC=C1)SCCN.ClC=1C=C(C=C(C1)Cl)SCCN.IC=1C=C(OCCN)C=CC1 Chemical compound ClC1=C(C=CC=C1)C(C)N.C1(=CC=CC=C1)SCCN.ClC=1C=C(C=C(C1)Cl)SCCN.IC=1C=C(OCCN)C=CC1 WJQJOVSUPPYDKU-UHFFFAOYSA-N 0.000 description 1
- IBHNGMFNHRIKSF-UHFFFAOYSA-N ClC1=C(OCC#N)C=CC=C1.FC=1C=C(OCC#N)C=CC1.FC1=C(OCC#N)C=CC=C1.ClC=1C=C(OCC#N)C=CC1Cl.ClC=1C=C(C=CC1Cl)SCC#N Chemical compound ClC1=C(OCC#N)C=CC=C1.FC=1C=C(OCC#N)C=CC1.FC1=C(OCC#N)C=CC=C1.ClC=1C=C(OCC#N)C=CC1Cl.ClC=1C=C(C=CC1Cl)SCC#N IBHNGMFNHRIKSF-UHFFFAOYSA-N 0.000 description 1
- JBJWAMQVYLLMQF-UHFFFAOYSA-N ClC=1C(=CC(=C(C1)N)OC)C.BrC=1C(=C(C=C(C1OC)Br)N)OC Chemical compound ClC=1C(=CC(=C(C1)N)OC)C.BrC=1C(=C(C=C(C1OC)Br)N)OC JBJWAMQVYLLMQF-UHFFFAOYSA-N 0.000 description 1
- HXTUOVIIMFQZCW-UHFFFAOYSA-N ClC=1C=C(C=C(C1Cl)Cl)[N+](=O)[O-].ClC1=C(C(=CC(=C1)[N+](=O)[O-])Cl)O Chemical compound ClC=1C=C(C=C(C1Cl)Cl)[N+](=O)[O-].ClC1=C(C(=CC(=C1)[N+](=O)[O-])Cl)O HXTUOVIIMFQZCW-UHFFFAOYSA-N 0.000 description 1
- AMLDGODTYFUSMV-UHFFFAOYSA-N ClC=1C=C(C=CC1)SCCN.ClC=1C=C(OCCN)C=CC1Cl.IC1=CC=C(OCCN)C=C1.BrC1=CC=C(OCCN)C=C1.BrC=1C=C(C=CC1)SCCN Chemical compound ClC=1C=C(C=CC1)SCCN.ClC=1C=C(OCCN)C=CC1Cl.IC1=CC=C(OCCN)C=C1.BrC1=CC=C(OCCN)C=C1.BrC=1C=C(C=CC1)SCCN AMLDGODTYFUSMV-UHFFFAOYSA-N 0.000 description 1
- 206010062343 Congenital infection Diseases 0.000 description 1
- 108020004414 DNA Proteins 0.000 description 1
- 102000053602 DNA Human genes 0.000 description 1
- 101710088194 Dehydrogenase Proteins 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 description 1
- 241001340534 Eido Species 0.000 description 1
- 241000353621 Eilat virus Species 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 201000005866 Exanthema Subitum Diseases 0.000 description 1
- 208000001860 Eye Infections Diseases 0.000 description 1
- FMRSUNBIQHPCBZ-UHFFFAOYSA-N FC=1C=C(C=CC1C(F)(F)F)C(C)N.FC1=C(C=CC(=C1)F)C(C)N.FC=1C=C(C=CC1)C(C)N.BrC1=CC(=C(C=C1)C(C)N)F.FC=1C=C(C=CC1F)C(C)N Chemical compound FC=1C=C(C=CC1C(F)(F)F)C(C)N.FC1=C(C=CC(=C1)F)C(C)N.FC=1C=C(C=CC1)C(C)N.BrC1=CC(=C(C=C1)C(C)N)F.FC=1C=C(C=CC1F)C(C)N FMRSUNBIQHPCBZ-UHFFFAOYSA-N 0.000 description 1
- ITDYPBNAWYKQHA-UHFFFAOYSA-N FC=1C=C(OCCN)C=CC1.BrC=1C=C(OCCN)C=CC1.ClC1=C(OCCN)C=CC=C1.FC1=C(OCCN)C=CC=C1.BrC1=CC=C(C=C1)CCCN.ClC=1C=C(C=CC1Cl)SCCN Chemical compound FC=1C=C(OCCN)C=CC1.BrC=1C=C(OCCN)C=CC1.ClC1=C(OCCN)C=CC=C1.FC1=C(OCCN)C=CC=C1.BrC1=CC=C(C=C1)CCCN.ClC=1C=C(C=CC1Cl)SCCN ITDYPBNAWYKQHA-UHFFFAOYSA-N 0.000 description 1
- 239000009484 FIBS Substances 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229940126656 GS-4224 Drugs 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 102000003886 Glycoproteins Human genes 0.000 description 1
- 108090000288 Glycoproteins Proteins 0.000 description 1
- 238000001321 HNCO Methods 0.000 description 1
- 208000001688 Herpes Genitalis Diseases 0.000 description 1
- 208000004898 Herpes Labialis Diseases 0.000 description 1
- 101000678879 Homo sapiens Atypical chemokine receptor 1 Proteins 0.000 description 1
- 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- GRSZFWQUAKGDAV-KQYNXXCUSA-N IMP Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(O)=O)O[C@H]1N1C(NC=NC2=O)=C2N=C1 GRSZFWQUAKGDAV-KQYNXXCUSA-N 0.000 description 1
- 206010061598 Immunodeficiency Diseases 0.000 description 1
- 102000004890 Interleukin-8 Human genes 0.000 description 1
- 108090001007 Interleukin-8 Proteins 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
- 208000032420 Latent Infection Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 208000036626 Mental retardation Diseases 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- KWFFPPOBIZXFEK-UHFFFAOYSA-N N-(2-chloro-4-nitrophenyl)methanesulfonamide N-[3-methoxy-4-[(2,2,2-trifluoroacetyl)amino]phenyl]furan-2-carboxamide Chemical compound COC=1C=C(C=CC1NC(C(F)(F)F)=O)NC(=O)C=1OC=CC1.ClC1=C(C=CC(=C1)[N+](=O)[O-])NS(=O)(=O)C KWFFPPOBIZXFEK-UHFFFAOYSA-N 0.000 description 1
- UPSPCUNZCLFUKC-UHFFFAOYSA-N N-(4-amino-2-methoxy-5-methylphenyl)-2-fluorobenzamide N-(4-amino-2-methoxy-5-methylphenyl)furan-2-carboxamide Chemical compound COC1=CC(N)=C(C)C=C1NC(=O)C1=CC=CO1.COC1=CC(N)=C(C)C=C1NC(=O)C1=CC=CC=C1F UPSPCUNZCLFUKC-UHFFFAOYSA-N 0.000 description 1
- IJYVJYWTAQEYSQ-UHFFFAOYSA-N N-(4-aminophenyl)-2,2-dimethylpropanamide N-(4-aminophenyl)-4-methoxybenzamide N-(4-aminophenyl)-2-phenylacetamide N-(4-aminophenyl)-2,2,2-trifluoroacetamide thiophene-2-carboxylic acid Chemical compound S1C(=CC=C1)C(=O)O.NC1=CC=C(C=C1)NC(C(F)(F)F)=O.NC1=CC=C(C=C1)NC(C(C)(C)C)=O.NC1=CC=C(C=C1)NC(CC1=CC=CC=C1)=O.NC1=CC=C(C=C1)NC(C1=CC=C(C=C1)OC)=O IJYVJYWTAQEYSQ-UHFFFAOYSA-N 0.000 description 1
- UXNHDEKERZPOFY-UHFFFAOYSA-N N-(4-aminophenyl)isoquinoline-4-carboxamide 4-butoxy-3,5-dichloroaniline 3,5-dichloro-4-ethoxyaniline Chemical compound NC1=CC=C(C=C1)NC(=O)C1=CN=CC2=CC=CC=C12.C(CCC)OC1=C(C=C(C=C1Cl)N)Cl.ClC=1C=C(C=C(C1OCC)Cl)N UXNHDEKERZPOFY-UHFFFAOYSA-N 0.000 description 1
- AGTMUTUNPGDWIJ-UHFFFAOYSA-N N-[3-cyano-4-[(2,2,2-trifluoroacetyl)amino]phenyl]-2-fluorobenzamide N-[3-cyano-4-[(2,2,2-trifluoroacetyl)amino]phenyl]furan-2-carboxamide Chemical compound C(#N)C=1C=C(C=CC1NC(C(F)(F)F)=O)NC(=O)C=1OC=CC1.C(#N)C=1C=C(C=CC1NC(C(F)(F)F)=O)NC(C1=C(C=CC=C1)F)=O AGTMUTUNPGDWIJ-UHFFFAOYSA-N 0.000 description 1
- HHQVGXJOFJKPSE-UHFFFAOYSA-N N-[4-[(4-aminophenyl)carbamothioylamino]-2-chlorophenyl]-2-(dipropylamino)acetamide Chemical compound C1=C(Cl)C(NC(=O)CN(CCC)CCC)=CC=C1NC(=S)NC1=CC=C(N)C=C1 HHQVGXJOFJKPSE-UHFFFAOYSA-N 0.000 description 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
- FULZLIGZKMKICU-UHFFFAOYSA-N N-phenylthiourea Chemical class NC(=S)NC1=CC=CC=C1 FULZLIGZKMKICU-UHFFFAOYSA-N 0.000 description 1
- IFFIJLKQGIOOAC-UHFFFAOYSA-N NC(=O)NN=C(OCC)CC(=O)C1=CC=CC=C1 Chemical compound NC(=O)NN=C(OCC)CC(=O)C1=CC=CC=C1 IFFIJLKQGIOOAC-UHFFFAOYSA-N 0.000 description 1
- BKGZAPAVMULQPV-UHFFFAOYSA-N NC(C)C=1C=C(C#N)C=CC1.NC(C)C=1C=C(C=CC1)N(C)C.FC1=CC=C(C=C1)C(C(C)C)N Chemical compound NC(C)C=1C=C(C#N)C=CC1.NC(C)C=1C=C(C=CC1)N(C)C.FC1=CC=C(C=C1)C(C(C)C)N BKGZAPAVMULQPV-UHFFFAOYSA-N 0.000 description 1
- OGPGXBVXEKITLV-UHFFFAOYSA-N NC1=C(C=C(C=C1)NC(C)=O)C.NC1=CC(=C(C=C1)NC(=O)C=1OC=CC1)C(C1=CC=CC=C1)=O Chemical compound NC1=C(C=C(C=C1)NC(C)=O)C.NC1=CC(=C(C=C1)NC(=O)C=1OC=CC1)C(C1=CC=CC=C1)=O OGPGXBVXEKITLV-UHFFFAOYSA-N 0.000 description 1
- ROOZVAUEGLSIOQ-UHFFFAOYSA-N NC1=CC(=C(C=C1)NC(=O)C=1OC=CC1)C(NC1=CC=CC=C1)=O.NC=1C=CC(=C(C(=O)NC2=CC=CC=C2)C1)NC(C1=C(C=CC=C1)F)=O.NC1=C(C=C(C=C1)NC(=O)C=1OC=CC1)C Chemical compound NC1=CC(=C(C=C1)NC(=O)C=1OC=CC1)C(NC1=CC=CC=C1)=O.NC=1C=CC(=C(C(=O)NC2=CC=CC=C2)C1)NC(C1=C(C=CC=C1)F)=O.NC1=C(C=C(C=C1)NC(=O)C=1OC=CC1)C ROOZVAUEGLSIOQ-UHFFFAOYSA-N 0.000 description 1
- QXMYZHITRKQWTJ-UHFFFAOYSA-N NC1=CC(=C(OCC(=O)N)C(=C1)Cl)Cl.C(C1=CC=CC=C1)OC1=C(C=C(C=C1Cl)N)Cl.NC1=CC=C(C=C1)NC(=O)C=1SC=CC1Br.NC1=CC=C(C=C1)NC(=O)C=1N=NNC1 Chemical compound NC1=CC(=C(OCC(=O)N)C(=C1)Cl)Cl.C(C1=CC=CC=C1)OC1=C(C=C(C=C1Cl)N)Cl.NC1=CC=C(C=C1)NC(=O)C=1SC=CC1Br.NC1=CC=C(C=C1)NC(=O)C=1N=NNC1 QXMYZHITRKQWTJ-UHFFFAOYSA-N 0.000 description 1
- POWAIDUTNCDOCK-UHFFFAOYSA-N NC1=CC=C(C=C1)NC(=O)C1=NC=CC2=CC=CC=C12.NC1=CC=C(C=C1)NC(=O)C1=CC=CC2=CC=CC=C12.NC1=CC=C(C=C1)NC(=O)C1=CC2=CC=CC=C2C=C1.NC1=CC=C(C=C1)NC(C1=CC=NC=C1)=O Chemical compound NC1=CC=C(C=C1)NC(=O)C1=NC=CC2=CC=CC=C12.NC1=CC=C(C=C1)NC(=O)C1=CC=CC2=CC=CC=C12.NC1=CC=C(C=C1)NC(=O)C1=CC2=CC=CC=C2C=C1.NC1=CC=C(C=C1)NC(C1=CC=NC=C1)=O POWAIDUTNCDOCK-UHFFFAOYSA-N 0.000 description 1
- FEGVNBCYJQNJBA-UHFFFAOYSA-N NC1=CC=C(C=C1)NC(=O)C1=NC=CC=C1.C(C)OC(COC1=CC(=CC=C1)C(NC1=CC=C(C=C1)N)=O)=O.NC1=CC=C(C=C1)NC(C1=CC(=CC=C1)OCCCC)=O.NC1=CC=C(C=C1)NC(C1=CC(=CC=C1)OCC1=CC=CC=C1)=O Chemical compound NC1=CC=C(C=C1)NC(=O)C1=NC=CC=C1.C(C)OC(COC1=CC(=CC=C1)C(NC1=CC=C(C=C1)N)=O)=O.NC1=CC=C(C=C1)NC(C1=CC(=CC=C1)OCCCC)=O.NC1=CC=C(C=C1)NC(C1=CC(=CC=C1)OCC1=CC=CC=C1)=O FEGVNBCYJQNJBA-UHFFFAOYSA-N 0.000 description 1
- YTMYEFIMYYHQBZ-UHFFFAOYSA-N NC1=CC=C(C=C1)NC(C1=CC(=CC=C1)OC)=O.NC1=CC=C(C=C1)NC(C1=C(C=CC=C1)OC)=O.NC1=CC=C(C=C1)NC(C1=C(C=CC=C1)F)=O.NC1=CC=C(C=C1)NC(C1=CC(=CC=C1)F)=O.NC1=CC=C(C=C1)NC(C1=CC=C(C=C1)F)=O Chemical compound NC1=CC=C(C=C1)NC(C1=CC(=CC=C1)OC)=O.NC1=CC=C(C=C1)NC(C1=C(C=CC=C1)OC)=O.NC1=CC=C(C=C1)NC(C1=C(C=CC=C1)F)=O.NC1=CC=C(C=C1)NC(C1=CC(=CC=C1)F)=O.NC1=CC=C(C=C1)NC(C1=CC=C(C=C1)F)=O YTMYEFIMYYHQBZ-UHFFFAOYSA-N 0.000 description 1
- RDTUOFKEQAACCR-UHFFFAOYSA-N O1C(=CC=C1)C(=O)O.C(CCCCC)OC(NC1=CC=C(C=C1)N)=O.NC1=CC=C(C=C1)NC(C1=CC(=CC=C1)OCCN1CCOCC1)=O Chemical compound O1C(=CC=C1)C(=O)O.C(CCCCC)OC(NC1=CC=C(C=C1)N)=O.NC1=CC=C(C=C1)NC(C1=CC(=CC=C1)OCCN1CCOCC1)=O RDTUOFKEQAACCR-UHFFFAOYSA-N 0.000 description 1
- XWJQJLVQCVWDAA-UHFFFAOYSA-N OC(=O)c1cscn1.Cc1nnsc1C(O)=O.Cc1snnc1C(O)=O Chemical compound OC(=O)c1cscn1.Cc1nnsc1C(O)=O.Cc1snnc1C(O)=O XWJQJLVQCVWDAA-UHFFFAOYSA-N 0.000 description 1
- 206010067152 Oral herpes Diseases 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- QPFYXYFORQJZEC-FOCLMDBBSA-N Phenazopyridine Chemical compound NC1=NC(N)=CC=C1\N=N\C1=CC=CC=C1 QPFYXYFORQJZEC-FOCLMDBBSA-N 0.000 description 1
- 208000035415 Reinfection Diseases 0.000 description 1
- 241000701037 Rhadinovirus Species 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 230000024932 T cell mediated immunity Effects 0.000 description 1
- 206010052779 Transplant rejections Diseases 0.000 description 1
- 206010046980 Varicella Diseases 0.000 description 1
- UDGVIWPWWKEVEN-UHFFFAOYSA-N [2-[(4-aminophenyl)carbamoyl]phenyl] acetate Chemical compound CC(=O)OC1=CC=CC=C1C(=O)NC1=CC=C(N)C=C1 UDGVIWPWWKEVEN-UHFFFAOYSA-N 0.000 description 1
- FHTCIZUOUOZCNH-UHFFFAOYSA-N [3,5-dichloro-4-(2-hydroxyethoxy)phenyl]carbamic acid Chemical compound OCCOC1=C(Cl)C=C(NC(O)=O)C=C1Cl FHTCIZUOUOZCNH-UHFFFAOYSA-N 0.000 description 1
- MTKKUSMYUNSWNA-UHFFFAOYSA-N [3-(2-methylpropyl)-5-(trifluoromethyl)phenyl]carbamic acid Chemical compound CC(C)CC1=CC(NC(O)=O)=CC(C(F)(F)F)=C1 MTKKUSMYUNSWNA-UHFFFAOYSA-N 0.000 description 1
- HTGWBBDKGLZVSJ-UHFFFAOYSA-N [3-chloro-4-(1-hydroxyethyl)phenyl]carbamic acid Chemical compound CC(O)C1=CC=C(NC(O)=O)C=C1Cl HTGWBBDKGLZVSJ-UHFFFAOYSA-N 0.000 description 1
- RDXMMWKXBYRMRU-UHFFFAOYSA-N [3-chloro-4-(2-hydroxyethyl)phenyl]carbamic acid Chemical compound OCCC1=CC=C(NC(O)=O)C=C1Cl RDXMMWKXBYRMRU-UHFFFAOYSA-N 0.000 description 1
- GMPMBOPZHAFGEO-UHFFFAOYSA-N [4-(1-hydroxyethyl)phenyl]urea Chemical compound CC(O)C1=CC=C(NC(N)=O)C=C1 GMPMBOPZHAFGEO-UHFFFAOYSA-N 0.000 description 1
- LBROXRHAHMXBLZ-UHFFFAOYSA-N [4-(1h-pyrrole-2-carbonylamino)phenyl]carbamic acid Chemical compound C1=CC(NC(=O)O)=CC=C1NC(=O)C1=CC=CN1 LBROXRHAHMXBLZ-UHFFFAOYSA-N 0.000 description 1
- VWYCWXVWWJURNT-UHFFFAOYSA-N [4-(furan-2-carbonylamino)phenyl]carbamic acid Chemical compound C1=CC(NC(=O)O)=CC=C1NC(=O)C1=CC=CO1 VWYCWXVWWJURNT-UHFFFAOYSA-N 0.000 description 1
- JTKYUAMFBDGZBG-UHFFFAOYSA-N [4-(naphthalene-1-carbonylamino)phenyl]carbamic acid Chemical compound C1=CC(NC(=O)O)=CC=C1NC(=O)C1=CC=CC2=CC=CC=C12 JTKYUAMFBDGZBG-UHFFFAOYSA-N 0.000 description 1
- ZQXPWJDBBAUSPC-UHFFFAOYSA-N [4-(phenoxycarbonylamino)phenyl]carbamic acid Chemical compound C1=CC(NC(=O)O)=CC=C1NC(=O)OC1=CC=CC=C1 ZQXPWJDBBAUSPC-UHFFFAOYSA-N 0.000 description 1
- ZQNWFEVUCCBGCY-UHFFFAOYSA-N [4-[(2-bromobenzoyl)amino]phenyl]carbamic acid Chemical compound C1=CC(NC(=O)O)=CC=C1NC(=O)C1=CC=CC=C1Br ZQNWFEVUCCBGCY-UHFFFAOYSA-N 0.000 description 1
- IGPHKYXTGDUMIR-UHFFFAOYSA-N [4-[(2-methoxyacetyl)amino]phenyl]carbamic acid Chemical compound COCC(=O)NC1=CC=C(C=C1)NC(O)=O IGPHKYXTGDUMIR-UHFFFAOYSA-N 0.000 description 1
- VZWJLWCJMOGQRN-UHFFFAOYSA-N [4-[(2-methoxybenzoyl)amino]phenyl]carbamic acid Chemical compound COC1=CC=CC=C1C(=O)NC1=CC=C(NC(O)=O)C=C1 VZWJLWCJMOGQRN-UHFFFAOYSA-N 0.000 description 1
- FAPZAYKSNIMUMV-UHFFFAOYSA-N [4-[(2-methylsulfinylbenzoyl)amino]phenyl]carbamic acid Chemical compound CS(=O)C1=CC=CC=C1C(=O)NC1=CC=C(NC(O)=O)C=C1 FAPZAYKSNIMUMV-UHFFFAOYSA-N 0.000 description 1
- PJLYAKPZOKGEAT-UHFFFAOYSA-N [4-[(2-phenoxyacetyl)amino]phenyl]carbamic acid Chemical compound C1=CC(NC(=O)O)=CC=C1NC(=O)COC1=CC=CC=C1 PJLYAKPZOKGEAT-UHFFFAOYSA-N 0.000 description 1
- KYUBNGYSGDSWHJ-UHFFFAOYSA-N [4-[(2-thiophen-2-ylacetyl)amino]phenyl]carbamic acid Chemical compound C1=CC(NC(=O)O)=CC=C1NC(=O)CC1=CC=CS1 KYUBNGYSGDSWHJ-UHFFFAOYSA-N 0.000 description 1
- QPBSJPXUEASCKI-UHFFFAOYSA-N [4-[(3-butoxybenzoyl)amino]phenyl]carbamic acid Chemical compound CCCCOC1=CC=CC(C(=O)NC=2C=CC(NC(O)=O)=CC=2)=C1 QPBSJPXUEASCKI-UHFFFAOYSA-N 0.000 description 1
- AVBBIJMVLMAATM-UHFFFAOYSA-N [4-[(4-acetamidophenyl)carbamothioylamino]-3-hydroxyphenyl] benzoate Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC(C(=C1)O)=CC=C1OC(=O)C1=CC=CC=C1 AVBBIJMVLMAATM-UHFFFAOYSA-N 0.000 description 1
- ILJLAZQUJZLIMB-UHFFFAOYSA-N [4-[(5-chlorofuran-2-carbonyl)amino]phenyl]carbamic acid Chemical compound C1=CC(NC(=O)O)=CC=C1NC(=O)C1=CC=C(Cl)O1 ILJLAZQUJZLIMB-UHFFFAOYSA-N 0.000 description 1
- MINPJJFYWWBKEG-UHFFFAOYSA-N [4-[[3-(trifluoromethoxy)benzoyl]amino]phenyl]carbamic acid Chemical compound C1=CC(NC(=O)O)=CC=C1NC(=O)C1=CC=CC(OC(F)(F)F)=C1 MINPJJFYWWBKEG-UHFFFAOYSA-N 0.000 description 1
- UUSUGWLYJLRWBS-UHFFFAOYSA-N [4-[[4-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]carbamoyl]phenyl] acetate Chemical compound C1=CC(OC(=O)C)=CC=C1C(=O)NC1=CC=C(NC(=O)OC(C)(C)C)C=C1 UUSUGWLYJLRWBS-UHFFFAOYSA-N 0.000 description 1
- HUDKUXIKKJOFLT-UHFFFAOYSA-N [4-[[4-[1-(4-fluorophenyl)ethylcarbamothioylamino]phenyl]carbamoyl]phenyl] acetate Chemical compound C=1C=C(F)C=CC=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=C(OC(C)=O)C=C1 HUDKUXIKKJOFLT-UHFFFAOYSA-N 0.000 description 1
- JTFKFMXJQDECPF-UHFFFAOYSA-N [O-]C([S+]1N=NC=C1)=O Chemical compound [O-]C([S+]1N=NC=C1)=O JTFKFMXJQDECPF-UHFFFAOYSA-N 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
- MOQOOKGPCBQMCY-UHFFFAOYSA-N acetic acid;hexane Chemical class CC(O)=O.CCCCCC MOQOOKGPCBQMCY-UHFFFAOYSA-N 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 229960004150 aciclovir Drugs 0.000 description 1
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 125000002252 acyl group Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 210000004100 adrenal gland Anatomy 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 230000000735 allogeneic effect Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003622 anti-hsv Effects 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- HRDJIMDVNVUCFH-UHFFFAOYSA-N argon;oxolane Chemical compound [Ar].C1CCOC1 HRDJIMDVNVUCFH-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000001499 aryl bromides Chemical class 0.000 description 1
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 description 1
- 125000002393 azetidinyl group Chemical group 0.000 description 1
- 125000004069 aziridinyl group Chemical group 0.000 description 1
- 125000005604 azodicarboxylate group Chemical group 0.000 description 1
- 238000010945 base-catalyzed hydrolysis reactiony Methods 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- UIFNOQFFGAJPIQ-UHFFFAOYSA-N benzamide furan-2-carboxylic acid Chemical compound O1C(=CC=C1)C(=O)O.C(C1=CC=CC=C1)(=O)N UIFNOQFFGAJPIQ-UHFFFAOYSA-N 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- BJUJSLXVBATBSB-UHFFFAOYSA-N benzotriazol-1-yl 2-trimethylsilylethyl carbonate Chemical compound C1=CC=C2N(OC(=O)OCC[Si](C)(C)C)N=NC2=C1 BJUJSLXVBATBSB-UHFFFAOYSA-N 0.000 description 1
- BJFLSHMHTPAZHO-UHFFFAOYSA-N benzotriazole Chemical compound [CH]1C=CC=C2N=NN=C21 BJFLSHMHTPAZHO-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- ZJRCIQAMTAINCB-UHFFFAOYSA-N benzoylacetonitrile Chemical class N#CCC(=O)C1=CC=CC=C1 ZJRCIQAMTAINCB-UHFFFAOYSA-N 0.000 description 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- VRAVWQUXPCWGSU-UHFFFAOYSA-N bis(1h-1,2,4-triazol-5-yl)methanone Chemical compound N1=CNN=C1C(=O)C=1N=CNN=1 VRAVWQUXPCWGSU-UHFFFAOYSA-N 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 1
- 210000001185 bone marrow Anatomy 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000007541 cellular toxicity Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 229940117975 chromium trioxide Drugs 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012059 conventional drug carrier Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- SNRCKKQHDUIRIY-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloromethane;dichloropalladium;iron(2+) Chemical compound [Fe+2].ClCCl.Cl[Pd]Cl.C1=C[CH-]C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.C1=C[CH-]C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 SNRCKKQHDUIRIY-UHFFFAOYSA-L 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 1
- 239000002037 dichloromethane fraction Substances 0.000 description 1
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical class ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical class [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- SBNKFTQSBPKMBZ-UHFFFAOYSA-N ethenzamide Chemical compound CCOC1=CC=CC=C1C(N)=O SBNKFTQSBPKMBZ-UHFFFAOYSA-N 0.000 description 1
- HSVBDIVPVPWHKD-UHFFFAOYSA-N ethyl 2-[4-[(4-acetamidophenyl)carbamothioylamino]-2,6-dichlorophenoxy]acetate Chemical compound C1=C(Cl)C(OCC(=O)OCC)=C(Cl)C=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 HSVBDIVPVPWHKD-UHFFFAOYSA-N 0.000 description 1
- ZIEJMPGRHLTTOX-UHFFFAOYSA-N ethyl 4-(furan-3-yl)thiadiazole-5-carboxylate;ethyl 4-phenylthiadiazole-5-carboxylate;methyl 4-methylthiadiazole-5-carboxylate Chemical compound COC(=O)C=1SN=NC=1C.S1N=NC(C2=COC=C2)=C1C(=O)OCC.S1N=NC(C=2C=CC=CC=2)=C1C(=O)OCC ZIEJMPGRHLTTOX-UHFFFAOYSA-N 0.000 description 1
- NCLKBCSIANMYJL-UHFFFAOYSA-N ethyl 5-phenyl-2h-thiadiazole-5-carboxylate Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)SNN=C1 NCLKBCSIANMYJL-UHFFFAOYSA-N 0.000 description 1
- KVIAEOXZBFTCMZ-UHFFFAOYSA-N ethyl n-[2-chloro-4-[[4-(furan-2-carbonylamino)phenyl]carbamothioylamino]phenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCC)=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CO1 KVIAEOXZBFTCMZ-UHFFFAOYSA-N 0.000 description 1
- KEKHPJQJWXDBSK-UHFFFAOYSA-N ethyl n-[2-chloro-4-[[4-[(2-fluorobenzoyl)amino]phenyl]carbamothioylamino]phenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCC)=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F KEKHPJQJWXDBSK-UHFFFAOYSA-N 0.000 description 1
- XXILPAMPLXWBQS-UHFFFAOYSA-N ethyl n-[4-[(4-acetamidophenyl)carbamothioylamino]-2-chlorophenyl]carbamate Chemical compound C1=C(Cl)C(NC(=O)OCC)=CC=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 XXILPAMPLXWBQS-UHFFFAOYSA-N 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 208000011323 eye infectious disease Diseases 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 210000003754 fetus Anatomy 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 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
- 201000004946 genital herpes Diseases 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 210000004524 haematopoietic cell Anatomy 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 210000002216 heart Anatomy 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000020256 human milk Nutrition 0.000 description 1
- 210000004251 human milk Anatomy 0.000 description 1
- 125000005638 hydrazono group Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 230000008629 immune suppression Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 235000013902 inosinic acid Nutrition 0.000 description 1
- 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 1
- 229940096397 interleukin-8 Drugs 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- MCVMLYSLPCECGO-UHFFFAOYSA-N isoquinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CN=CC2=C1 MCVMLYSLPCECGO-UHFFFAOYSA-N 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 150000003854 isothiazoles Chemical class 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 150000002545 isoxazoles Chemical class 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- FYYHWMGAXLPEAU-OUBTZVSYSA-N magnesium-25 atom Chemical compound [25Mg] FYYHWMGAXLPEAU-OUBTZVSYSA-N 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- LVKCSZQWLOVUGB-UHFFFAOYSA-M magnesium;propane;bromide Chemical compound [Mg+2].[Br-].C[CH-]C LVKCSZQWLOVUGB-UHFFFAOYSA-M 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- NRVFDGZJTPCULU-UHFFFAOYSA-N meda Chemical compound Cl.CN(C)CCS NRVFDGZJTPCULU-UHFFFAOYSA-N 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- QERAEVIIGFQGIL-UHFFFAOYSA-N methyl 2-[4-[(4-acetamidophenyl)carbamothioylamino]-2-chloro-5-methoxyphenoxy]acetate Chemical compound C1=C(Cl)C(OCC(=O)OC)=CC(OC)=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 QERAEVIIGFQGIL-UHFFFAOYSA-N 0.000 description 1
- UTDSGIAZQKHFLL-UHFFFAOYSA-N methyl 3-[[4-(furan-2-carbonylamino)phenyl]carbamothioylamino]benzoate Chemical compound COC(=O)C1=CC=CC(NC(=S)NC=2C=CC(NC(=O)C=3OC=CC=3)=CC=2)=C1 UTDSGIAZQKHFLL-UHFFFAOYSA-N 0.000 description 1
- DHWHVXWZHNDIDB-UHFFFAOYSA-N methyl 4-methylthiadiazole-5-carboxylate Chemical compound COC(=O)C=1SN=NC=1C DHWHVXWZHNDIDB-UHFFFAOYSA-N 0.000 description 1
- FJNHAAAKQDMAHK-UHFFFAOYSA-N methyl 5-phenylthiadiazole-4-carboxylate Chemical compound N1=NSC(C=2C=CC=CC=2)=C1C(=O)OC FJNHAAAKQDMAHK-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- LKKTYMNXCFDLCX-UHFFFAOYSA-N methyl n-(4-acetamidophenyl)-n'-(5-chloro-2,4-dimethoxyphenyl)carbamimidothioate Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1N=C(SC)NC1=CC=C(NC(C)=O)C=C1 LKKTYMNXCFDLCX-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 238000004264 monolayer culture Methods 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 238000002703 mutagenesis Methods 0.000 description 1
- 231100000350 mutagenesis Toxicity 0.000 description 1
- CZGIEJXGCLWRPY-UHFFFAOYSA-N n,1-dimethylpyrrolidin-3-amine Chemical compound CNC1CCN(C)C1 CZGIEJXGCLWRPY-UHFFFAOYSA-N 0.000 description 1
- ILBIXZPOMJFOJP-UHFFFAOYSA-N n,n-dimethylprop-2-yn-1-amine Chemical compound CN(C)CC#C ILBIXZPOMJFOJP-UHFFFAOYSA-N 0.000 description 1
- PXFVMCWKLVIEBZ-UHFFFAOYSA-N n-(2-chloro-4-nitrophenyl)-2-[2-(dimethylamino)ethylsulfanyl]acetamide Chemical compound CN(C)CCSCC(=O)NC1=CC=C([N+]([O-])=O)C=C1Cl PXFVMCWKLVIEBZ-UHFFFAOYSA-N 0.000 description 1
- BCTFYSXVHAFEGT-UHFFFAOYSA-N n-(2-chloro-4-nitrophenyl)benzamide Chemical compound ClC1=CC([N+](=O)[O-])=CC=C1NC(=O)C1=CC=CC=C1 BCTFYSXVHAFEGT-UHFFFAOYSA-N 0.000 description 1
- ROIFYZDOQOPGNG-UHFFFAOYSA-N n-(3-methoxy-4-nitrophenyl)acetamide Chemical compound COC1=CC(NC(C)=O)=CC=C1[N+]([O-])=O ROIFYZDOQOPGNG-UHFFFAOYSA-N 0.000 description 1
- URSIBCBOBKGZJB-UHFFFAOYSA-N n-(4-acetamido-2-cyanophenyl)-2,2,2-trifluoroacetamide Chemical compound CC(=O)NC1=CC=C(NC(=O)C(F)(F)F)C(C#N)=C1 URSIBCBOBKGZJB-UHFFFAOYSA-N 0.000 description 1
- WXSJNSOLMGVNAB-UHFFFAOYSA-N n-(4-acetamido-2-methoxyphenyl)-2,2,2-trifluoroacetamide Chemical compound COC1=CC(NC(C)=O)=CC=C1NC(=O)C(F)(F)F WXSJNSOLMGVNAB-UHFFFAOYSA-N 0.000 description 1
- JFIICRGSBZIZGC-UHFFFAOYSA-N n-(4-amino-2-benzoylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1C(=O)C1=CC=CC=C1 JFIICRGSBZIZGC-UHFFFAOYSA-N 0.000 description 1
- YMBWSFWVMBXXCI-UHFFFAOYSA-N n-(4-amino-2-chlorophenyl)-2-(3-methylpiperidin-1-yl)acetamide Chemical compound C1C(C)CCCN1CC(=O)NC1=CC=C(N)C=C1Cl YMBWSFWVMBXXCI-UHFFFAOYSA-N 0.000 description 1
- UUPBQZMEYUFRQW-UHFFFAOYSA-N n-(4-amino-2-chlorophenyl)-2-(dipropylamino)acetamide;n-(4-amino-2-chlorophenyl)-2-thiomorpholin-4-ylacetamide Chemical compound ClC1=CC(N)=CC=C1NC(=O)CN1CCSCC1.CCCN(CCC)CC(=O)NC1=CC=C(N)C=C1Cl UUPBQZMEYUFRQW-UHFFFAOYSA-N 0.000 description 1
- DUHPYDJTWXYDHN-UHFFFAOYSA-N n-(4-amino-2-chlorophenyl)-2-fluorobenzamide Chemical compound ClC1=CC(N)=CC=C1NC(=O)C1=CC=CC=C1F DUHPYDJTWXYDHN-UHFFFAOYSA-N 0.000 description 1
- WQGWKZGGLARDCS-UHFFFAOYSA-N n-(4-amino-2-cyanophenyl)-2,2,2-trifluoroacetamide Chemical compound NC1=CC=C(NC(=O)C(F)(F)F)C(C#N)=C1 WQGWKZGGLARDCS-UHFFFAOYSA-N 0.000 description 1
- CMHQZTVPXAZJJR-UHFFFAOYSA-N n-(4-amino-2-methoxyphenyl)furan-2-carboxamide Chemical compound COC1=CC(N)=CC=C1NC(=O)C1=CC=CO1 CMHQZTVPXAZJJR-UHFFFAOYSA-N 0.000 description 1
- GWFPMSIIVJMYRZ-UHFFFAOYSA-N n-(4-amino-2-methylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1C GWFPMSIIVJMYRZ-UHFFFAOYSA-N 0.000 description 1
- KYIFBTMTQXRRCU-UHFFFAOYSA-N n-(4-amino-2-methylphenyl)furan-2-carboxamide Chemical compound CC1=CC(N)=CC=C1NC(=O)C1=CC=CO1 KYIFBTMTQXRRCU-UHFFFAOYSA-N 0.000 description 1
- QQMYMLJHLLHUJU-UHFFFAOYSA-N n-(4-amino-3-chlorophenyl)-2-fluorobenzamide Chemical compound C1=C(Cl)C(N)=CC=C1NC(=O)C1=CC=CC=C1F QQMYMLJHLLHUJU-UHFFFAOYSA-N 0.000 description 1
- KOVUPRZXMQZXCC-UHFFFAOYSA-N n-(4-amino-3-chlorophenyl)furan-2-carboxamide Chemical compound C1=C(Cl)C(N)=CC=C1NC(=O)C1=CC=CO1 KOVUPRZXMQZXCC-UHFFFAOYSA-N 0.000 description 1
- UFZGWYKCLSCGHV-UHFFFAOYSA-N n-(4-amino-3-methoxyphenyl)acetamide Chemical compound COC1=CC(NC(C)=O)=CC=C1N UFZGWYKCLSCGHV-UHFFFAOYSA-N 0.000 description 1
- UOLVMIUXQSLXDM-UHFFFAOYSA-N n-(4-amino-3-methoxyphenyl)furan-2-carboxamide Chemical compound C1=C(N)C(OC)=CC(NC(=O)C=2OC=CC=2)=C1 UOLVMIUXQSLXDM-UHFFFAOYSA-N 0.000 description 1
- TURNHGUNFSXRJC-UHFFFAOYSA-N n-(4-aminophenyl)-1h-pyrrole-2-carboxamide Chemical compound C1=CC(N)=CC=C1NC(=O)C1=CC=CN1 TURNHGUNFSXRJC-UHFFFAOYSA-N 0.000 description 1
- CNVDXCAKXRSFSJ-UHFFFAOYSA-N n-(4-aminophenyl)-2,3,4-trifluorobenzamide Chemical compound C1=CC(N)=CC=C1NC(=O)C1=CC=C(F)C(F)=C1F CNVDXCAKXRSFSJ-UHFFFAOYSA-N 0.000 description 1
- DRQLMGGEDKYWTF-UHFFFAOYSA-N n-(4-aminophenyl)-2-fluorobenzamide Chemical compound C1=CC(N)=CC=C1NC(=O)C1=CC=CC=C1F DRQLMGGEDKYWTF-UHFFFAOYSA-N 0.000 description 1
- ACVACKIEZDGXND-UHFFFAOYSA-N n-(4-aminophenyl)-2-hydroxybenzamide Chemical compound C1=CC(N)=CC=C1NC(=O)C1=CC=CC=C1O ACVACKIEZDGXND-UHFFFAOYSA-N 0.000 description 1
- FTWXILTVCJYFEW-UHFFFAOYSA-N n-(4-aminophenyl)-3-methylfuran-2-carboxamide Chemical compound C1=COC(C(=O)NC=2C=CC(N)=CC=2)=C1C FTWXILTVCJYFEW-UHFFFAOYSA-N 0.000 description 1
- CKLIFWGHVLSLGH-UHFFFAOYSA-N n-(4-fluorophenyl)-4-[1-(4-fluorophenyl)ethylcarbamothioylamino]benzamide Chemical compound C=1C=C(F)C=CC=1C(C)NC(=S)NC(C=C1)=CC=C1C(=O)NC1=CC=C(F)C=C1 CKLIFWGHVLSLGH-UHFFFAOYSA-N 0.000 description 1
- CMFYEBBLFRJKTF-UHFFFAOYSA-N n-(4-isothiocyanatophenyl)-1,3-thiazole-4-carboxamide Chemical compound C=1SC=NC=1C(=O)NC1=CC=C(N=C=S)C=C1 CMFYEBBLFRJKTF-UHFFFAOYSA-N 0.000 description 1
- AHCKZUHLDVQMDY-UHFFFAOYSA-N n-(4-isothiocyanatophenyl)thiadiazole-4-carboxamide Chemical compound C=1SN=NC=1C(=O)NC1=CC=C(N=C=S)C=C1 AHCKZUHLDVQMDY-UHFFFAOYSA-N 0.000 description 1
- DFKKBOJXPCXEGX-UHFFFAOYSA-N n-(4-nitrophenyl)prop-2-enamide Chemical compound [O-][N+](=O)C1=CC=C(NC(=O)C=C)C=C1 DFKKBOJXPCXEGX-UHFFFAOYSA-N 0.000 description 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
- SIINNNXUPNEKBK-UHFFFAOYSA-N n-(5-nitropyridin-2-yl)furan-2-carboxamide Chemical compound N1=CC([N+](=O)[O-])=CC=C1NC(=O)C1=CC=CO1 SIINNNXUPNEKBK-UHFFFAOYSA-N 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- QITODMPCSILJIK-UHFFFAOYSA-N n-[1-(4-fluorophenyl)-2-methylpropyl]formamide Chemical compound O=CNC(C(C)C)C1=CC=C(F)C=C1 QITODMPCSILJIK-UHFFFAOYSA-N 0.000 description 1
- LBBVCHPZOXWXDY-UHFFFAOYSA-N n-[2-benzoyl-4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]phenyl]acetamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC1=CC=C(NC(C)=O)C(C(=O)C=2C=CC=CC=2)=C1 LBBVCHPZOXWXDY-UHFFFAOYSA-N 0.000 description 1
- KHEXVDMWIAFDOU-UHFFFAOYSA-N n-[2-chloro-4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]phenyl]acetamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC1=CC=C(NC(C)=O)C(Cl)=C1 KHEXVDMWIAFDOU-UHFFFAOYSA-N 0.000 description 1
- MXCWBWVHMUGQAA-UHFFFAOYSA-N n-[2-chloro-4-[1-(4-fluorophenyl)ethylcarbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound C=1C=C(F)C=CC=1C(C)NC(=S)NC(C=C1Cl)=CC=C1NC(=O)C1=CC=CC=C1F MXCWBWVHMUGQAA-UHFFFAOYSA-N 0.000 description 1
- ZVJDULDRODKUIJ-UHFFFAOYSA-N n-[3-chloro-4-[(3-chloro-4-methylphenyl)carbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound C1=C(Cl)C(C)=CC=C1NC(=S)NC(C(=C1)Cl)=CC=C1NC(=O)C1=CC=CC=C1F ZVJDULDRODKUIJ-UHFFFAOYSA-N 0.000 description 1
- MCCBSHTWLVJVAO-UHFFFAOYSA-N n-[3-chloro-4-[(3-chloro-4-methylsulfanylphenyl)carbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound C1=C(Cl)C(SC)=CC=C1NC(=S)NC(C(=C1)Cl)=CC=C1NC(=O)C1=CC=CC=C1F MCCBSHTWLVJVAO-UHFFFAOYSA-N 0.000 description 1
- YDOAEKQCEWFTFB-UHFFFAOYSA-N n-[3-chloro-5-(dimethylamino)phenyl]acetamide Chemical compound CN(C)C1=CC(Cl)=CC(NC(C)=O)=C1 YDOAEKQCEWFTFB-UHFFFAOYSA-N 0.000 description 1
- ZVJOZHWICZLBJM-UHFFFAOYSA-N n-[3-chloro-5-[(2,2,2-trifluoroacetyl)amino]phenyl]-2,2,2-trifluoroacetamide Chemical compound FC(F)(F)C(=O)NC1=CC(Cl)=CC(NC(=O)C(F)(F)F)=C1 ZVJOZHWICZLBJM-UHFFFAOYSA-N 0.000 description 1
- ZZYHJDUJBQWSRK-UHFFFAOYSA-N n-[4-(1,3-benzothiazol-5-ylcarbamothioylamino)phenyl]-2-fluorobenzamide Chemical compound FC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NC1=CC=C(SC=N2)C2=C1 ZZYHJDUJBQWSRK-UHFFFAOYSA-N 0.000 description 1
- CMVYTILRLRMAFA-UHFFFAOYSA-N n-[4-(1,3-benzothiazol-5-ylcarbamothioylamino)phenyl]furan-2-carboxamide Chemical compound C=1C=C(NC(=S)NC=2C=C3N=CSC3=CC=2)C=CC=1NC(=O)C1=CC=CO1 CMVYTILRLRMAFA-UHFFFAOYSA-N 0.000 description 1
- GVTKPZGXZHFDNO-UHFFFAOYSA-N n-[4-(1h-indazol-5-ylcarbamothioylamino)phenyl]furan-2-carboxamide Chemical compound C=1C=C(NC(=S)NC=2C=C3C=NNC3=CC=2)C=CC=1NC(=O)C1=CC=CO1 GVTKPZGXZHFDNO-UHFFFAOYSA-N 0.000 description 1
- OLOIVXSKQLGKSH-UHFFFAOYSA-N n-[4-(2-anilinoethylcarbamothioylamino)phenyl]thiadiazole-4-carboxamide Chemical compound C=1SN=NC=1C(=O)NC(C=C1)=CC=C1NC(=S)NCCNC1=CC=CC=C1 OLOIVXSKQLGKSH-UHFFFAOYSA-N 0.000 description 1
- CCCMTJNYNXRWAU-UHFFFAOYSA-N n-[4-(2-phenylethylcarbamothioylamino)phenyl]furan-2-carboxamide Chemical compound C=1C=COC=1C(=O)NC(C=C1)=CC=C1NC(=S)NCCC1=CC=CC=C1 CCCMTJNYNXRWAU-UHFFFAOYSA-N 0.000 description 1
- IXBDRRPRZAOYFV-UHFFFAOYSA-N n-[4-(2-phenylsulfanylethylcarbamothioylamino)phenyl]furan-2-carboxamide Chemical compound C=1C=COC=1C(=O)NC(C=C1)=CC=C1NC(=S)NCCSC1=CC=CC=C1 IXBDRRPRZAOYFV-UHFFFAOYSA-N 0.000 description 1
- SKLZXESXHRTPRV-UHFFFAOYSA-N n-[4-(3-phenylpropylcarbamothioylamino)phenyl]furan-2-carboxamide Chemical compound C=1C=COC=1C(=O)NC(C=C1)=CC=C1NC(=S)NCCCC1=CC=CC=C1 SKLZXESXHRTPRV-UHFFFAOYSA-N 0.000 description 1
- SPMDRDHGKJONDG-UHFFFAOYSA-N n-[4-(3-phenylpropylcarbamothioylamino)phenyl]thiadiazole-4-carboxamide Chemical compound C=1SN=NC=1C(=O)NC(C=C1)=CC=C1NC(=S)NCCCC1=CC=CC=C1 SPMDRDHGKJONDG-UHFFFAOYSA-N 0.000 description 1
- JDECKVWWJLSUNR-UHFFFAOYSA-N n-[4-([1,3]thiazolo[5,4-b]pyridin-2-ylamino)phenyl]furan-2-carboxamide Chemical compound C=1C=C(N=C2SC3=NC=CC=C3N2)C=CC=1NC(=O)C1=CC=CO1 JDECKVWWJLSUNR-UHFFFAOYSA-N 0.000 description 1
- CREVGCYXCRCFJW-UHFFFAOYSA-N n-[4-(benzylcarbamothioylamino)phenyl]-2-fluorobenzamide Chemical compound FC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NCC1=CC=CC=C1 CREVGCYXCRCFJW-UHFFFAOYSA-N 0.000 description 1
- BHHCZUMCEGEZIU-UHFFFAOYSA-N n-[4-(phenylcarbamothioylamino)phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC1=CC=CC=C1 BHHCZUMCEGEZIU-UHFFFAOYSA-N 0.000 description 1
- WBBGZIDRERLKGM-UHFFFAOYSA-N n-[4-(phenylcarbamothioylamino)phenyl]furan-2-carboxamide Chemical compound C=1C=COC=1C(=O)NC(C=C1)=CC=C1NC(=S)NC1=CC=CC=C1 WBBGZIDRERLKGM-UHFFFAOYSA-N 0.000 description 1
- LYNYBHMEYAAYRM-UHFFFAOYSA-N n-[4-(pyridin-2-ylcarbamothioylamino)phenyl]furan-2-carboxamide Chemical compound C=1C=COC=1C(=O)NC(C=C1)=CC=C1NC(=S)NC1=CC=CC=N1 LYNYBHMEYAAYRM-UHFFFAOYSA-N 0.000 description 1
- HCODTFCPTNJKLW-UHFFFAOYSA-N n-[4-(pyridin-3-ylcarbamothioylamino)phenyl]furan-2-carboxamide Chemical compound C=1C=COC=1C(=O)NC(C=C1)=CC=C1NC(=S)NC1=CC=CN=C1 HCODTFCPTNJKLW-UHFFFAOYSA-N 0.000 description 1
- SHVAQVWIBIFSDJ-UHFFFAOYSA-N n-[4-(pyridin-3-ylmethylcarbamothioylamino)phenyl]thiadiazole-4-carboxamide Chemical compound C=1SN=NC=1C(=O)NC(C=C1)=CC=C1NC(=S)NCC1=CC=CN=C1 SHVAQVWIBIFSDJ-UHFFFAOYSA-N 0.000 description 1
- LLBUGQSIMOHQNG-UHFFFAOYSA-N n-[4-(pyridin-4-ylcarbamothioylamino)phenyl]furan-2-carboxamide Chemical compound C=1C=COC=1C(=O)NC(C=C1)=CC=C1NC(=S)NC1=CC=NC=C1 LLBUGQSIMOHQNG-UHFFFAOYSA-N 0.000 description 1
- OTEWLZBULJSJMK-UHFFFAOYSA-N n-[4-(pyrimidin-4-ylcarbamothioylamino)phenyl]furan-2-carboxamide Chemical compound C=1C=COC=1C(=O)NC(C=C1)=CC=C1NC(=S)NC1=CC=NC=N1 OTEWLZBULJSJMK-UHFFFAOYSA-N 0.000 description 1
- LZXKVGMRDDSLQC-SSDOTTSWSA-N n-[4-[(1r)-1-aminoethyl]phenyl]thiadiazole-4-carboxamide Chemical compound C1=CC([C@H](N)C)=CC=C1NC(=O)C1=CSN=N1 LZXKVGMRDDSLQC-SSDOTTSWSA-N 0.000 description 1
- AQWGSIKUHIEVQG-UHFFFAOYSA-N n-[4-[(2,3-dichlorophenyl)carbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound FC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NC1=CC=CC(Cl)=C1Cl AQWGSIKUHIEVQG-UHFFFAOYSA-N 0.000 description 1
- SQCCZEHVEFOQNM-UHFFFAOYSA-N n-[4-[(2,3-dichlorophenyl)carbamothioylamino]phenyl]furan-2-carboxamide Chemical compound ClC1=CC=CC(NC(=S)NC=2C=CC(NC(=O)C=3OC=CC=3)=CC=2)=C1Cl SQCCZEHVEFOQNM-UHFFFAOYSA-N 0.000 description 1
- KOTCUYOPZWWQLD-UHFFFAOYSA-N n-[4-[(2,4-dimethoxyphenyl)carbamothioylamino]phenyl]acetamide Chemical compound COC1=CC(OC)=CC=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 KOTCUYOPZWWQLD-UHFFFAOYSA-N 0.000 description 1
- XLLWMPXCZQSJQK-UHFFFAOYSA-N n-[4-[(2,5-dichlorophenyl)carbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound ClC1=CC=C(Cl)C(NC(=S)NC=2C=CC(NC(=O)C=3N=NSC=3)=CC=2)=C1 XLLWMPXCZQSJQK-UHFFFAOYSA-N 0.000 description 1
- PFQSWLSSDSYKLR-UHFFFAOYSA-N n-[4-[(2-amino-3-chlorophenyl)carbamothioylamino]phenyl]-2,6-difluorobenzamide Chemical compound NC1=C(Cl)C=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F PFQSWLSSDSYKLR-UHFFFAOYSA-N 0.000 description 1
- JXCZIFHXSXVBIJ-UHFFFAOYSA-N n-[4-[(2-amino-5-chlorophenyl)carbamothioylamino]phenyl]furan-2-carboxamide Chemical compound NC1=CC=C(Cl)C=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CO1 JXCZIFHXSXVBIJ-UHFFFAOYSA-N 0.000 description 1
- DUXPIIWERTUJBF-UHFFFAOYSA-N n-[4-[(2-hydroxy-4-methoxyphenyl)carbamothioylamino]phenyl]acetamide Chemical compound OC1=CC(OC)=CC=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 DUXPIIWERTUJBF-UHFFFAOYSA-N 0.000 description 1
- OCTJNHPMUPJXPA-UHFFFAOYSA-N n-[4-[(2-methoxyphenyl)methylcarbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound COC1=CC=CC=C1CNC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSN=N1 OCTJNHPMUPJXPA-UHFFFAOYSA-N 0.000 description 1
- MBWCWENAJWPYOQ-UHFFFAOYSA-N n-[4-[(2-nitrophenyl)carbamothioylamino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC1=CC=CC=C1[N+]([O-])=O MBWCWENAJWPYOQ-UHFFFAOYSA-N 0.000 description 1
- UTFZNELXHKXLDB-UHFFFAOYSA-N n-[4-[(3,4,5-trimethoxyphenyl)carbamothioylamino]phenyl]acetamide Chemical compound COC1=C(OC)C(OC)=CC(NC(=S)NC=2C=CC(NC(C)=O)=CC=2)=C1 UTFZNELXHKXLDB-UHFFFAOYSA-N 0.000 description 1
- HEDKVZYHBICADW-UHFFFAOYSA-N n-[4-[(3,4-dichlorophenyl)carbamothioylamino]phenyl]-1,3-thiazole-4-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSC=N1 HEDKVZYHBICADW-UHFFFAOYSA-N 0.000 description 1
- TVTXIIAKIYEQJL-UHFFFAOYSA-N n-[4-[(3,4-dichlorophenyl)carbamothioylamino]phenyl]-2-phenyl-1,3-thiazole-4-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSC(C=2C=CC=CC=2)=N1 TVTXIIAKIYEQJL-UHFFFAOYSA-N 0.000 description 1
- XEOLKZSEUITENJ-UHFFFAOYSA-N n-[4-[(3,4-dichlorophenyl)carbamothioylamino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC1=CC=C(Cl)C(Cl)=C1 XEOLKZSEUITENJ-UHFFFAOYSA-N 0.000 description 1
- WSUBPBYNVPQKTP-UHFFFAOYSA-N n-[4-[(3,4-dichlorophenyl)methylcarbamothioylamino]phenyl]-1,3-thiazole-4-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1CNC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSC=N1 WSUBPBYNVPQKTP-UHFFFAOYSA-N 0.000 description 1
- WGQAWBNXIFFFSN-UHFFFAOYSA-N n-[4-[(3,4-dichlorophenyl)methylcarbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound FC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NCC1=CC=C(Cl)C(Cl)=C1 WGQAWBNXIFFFSN-UHFFFAOYSA-N 0.000 description 1
- IKIQZZFHUBHYCQ-UHFFFAOYSA-N n-[4-[(3,4-dichlorophenyl)methylcarbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1CNC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSN=N1 IKIQZZFHUBHYCQ-UHFFFAOYSA-N 0.000 description 1
- DWUCGXJXYPKJBR-UHFFFAOYSA-N n-[4-[(3,4-dichlorophenyl)methylcarbamoylamino]phenyl]thiadiazole-4-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1CNC(=O)NC(C=C1)=CC=C1NC(=O)C1=CSN=N1 DWUCGXJXYPKJBR-UHFFFAOYSA-N 0.000 description 1
- RGRKKEDVFYLVRK-UHFFFAOYSA-N n-[4-[(3,4-difluorophenyl)methylcarbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound C1=C(F)C(F)=CC=C1CNC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F RGRKKEDVFYLVRK-UHFFFAOYSA-N 0.000 description 1
- XRADSYIIHIDOOW-UHFFFAOYSA-N n-[4-[(3,4-difluorophenyl)methylcarbamothioylamino]phenyl]furan-2-carboxamide Chemical compound C1=C(F)C(F)=CC=C1CNC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CO1 XRADSYIIHIDOOW-UHFFFAOYSA-N 0.000 description 1
- VKRIDLBUERBZTO-UHFFFAOYSA-N n-[4-[(3,5-dichloro-2-methoxy-4-methylphenyl)carbamothioylamino]phenyl]acetamide Chemical compound COC1=C(Cl)C(C)=C(Cl)C=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 VKRIDLBUERBZTO-UHFFFAOYSA-N 0.000 description 1
- QZCTVLLJPJMUNQ-UHFFFAOYSA-N n-[4-[(3,5-dichloro-4-methoxyphenyl)carbamothioylamino]phenyl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NC=2C=CC(NC(=S)NC=3C=C(Cl)C(OC)=C(Cl)C=3)=CC=2)=C1 QZCTVLLJPJMUNQ-UHFFFAOYSA-N 0.000 description 1
- DJFMQMXPVYQTKO-UHFFFAOYSA-N n-[4-[(3,5-dichloro-4-phenoxyphenyl)carbamothioylamino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC(C=C1Cl)=CC(Cl)=C1OC1=CC=CC=C1 DJFMQMXPVYQTKO-UHFFFAOYSA-N 0.000 description 1
- WPYKPJZCXQXTSH-UHFFFAOYSA-N n-[4-[(3,5-dichlorophenyl)carbamothioylamino]phenyl]-1,3-oxazole-4-carboxamide Chemical compound ClC1=CC(Cl)=CC(NC(=S)NC=2C=CC(NC(=O)C=3N=COC=3)=CC=2)=C1 WPYKPJZCXQXTSH-UHFFFAOYSA-N 0.000 description 1
- IKORUKNULFGMGE-UHFFFAOYSA-N n-[4-[(3,5-dichlorophenyl)carbamothioylamino]phenyl]-1,3-thiazole-4-carboxamide Chemical compound ClC1=CC(Cl)=CC(NC(=S)NC=2C=CC(NC(=O)C=3N=CSC=3)=CC=2)=C1 IKORUKNULFGMGE-UHFFFAOYSA-N 0.000 description 1
- JBACKOUYBLBJHU-UHFFFAOYSA-N n-[4-[(3,5-dichlorophenyl)methylcarbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound FC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NCC1=CC(Cl)=CC(Cl)=C1 JBACKOUYBLBJHU-UHFFFAOYSA-N 0.000 description 1
- HFHUTXMUHDYHTJ-UHFFFAOYSA-N n-[4-[(3,5-dichlorophenyl)methylcarbamothioylamino]phenyl]furan-2-carboxamide Chemical compound ClC1=CC(Cl)=CC(CNC(=S)NC=2C=CC(NC(=O)C=3OC=CC=3)=CC=2)=C1 HFHUTXMUHDYHTJ-UHFFFAOYSA-N 0.000 description 1
- GRBFDRJZBPMTJV-UHFFFAOYSA-N n-[4-[(3,5-difluorophenyl)methylcarbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound FC1=CC(F)=CC(CNC(=S)NC=2C=CC(NC(=O)C=3C(=CC=CC=3)F)=CC=2)=C1 GRBFDRJZBPMTJV-UHFFFAOYSA-N 0.000 description 1
- WOXDVXOYMFMFIJ-UHFFFAOYSA-N n-[4-[(3,5-dimethylphenyl)methylcarbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound CC1=CC(C)=CC(CNC(=S)NC=2C=CC(NC(=O)C=3N=NSC=3)=CC=2)=C1 WOXDVXOYMFMFIJ-UHFFFAOYSA-N 0.000 description 1
- PAGNWPPWZVKTLS-UHFFFAOYSA-N n-[4-[(3-acetamidophenyl)carbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound CC(=O)NC1=CC=CC(NC(=S)NC=2C=CC(NC(=O)C=3C(=CC=CC=3)F)=CC=2)=C1 PAGNWPPWZVKTLS-UHFFFAOYSA-N 0.000 description 1
- XPAIHJFKFNGQCD-UHFFFAOYSA-N n-[4-[(3-acetamidophenyl)carbamothioylamino]phenyl]furan-2-carboxamide Chemical compound CC(=O)NC1=CC=CC(NC(=S)NC=2C=CC(NC(=O)C=3OC=CC=3)=CC=2)=C1 XPAIHJFKFNGQCD-UHFFFAOYSA-N 0.000 description 1
- SDYQOVUAEGRODH-UHFFFAOYSA-N n-[4-[(3-amino-5-chlorophenyl)carbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound NC1=CC(Cl)=CC(NC(=S)NC=2C=CC(NC(=O)C=3C(=CC=CC=3)F)=CC=2)=C1 SDYQOVUAEGRODH-UHFFFAOYSA-N 0.000 description 1
- MXDFQVKHONLKLY-UHFFFAOYSA-N n-[4-[(3-aminophenyl)carbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound NC1=CC=CC(NC(=S)NC=2C=CC(NC(=O)C=3C(=CC=CC=3)F)=CC=2)=C1 MXDFQVKHONLKLY-UHFFFAOYSA-N 0.000 description 1
- BMWUNMMRRLWLSA-UHFFFAOYSA-N n-[4-[(3-aminophenyl)carbamothioylamino]phenyl]furan-2-carboxamide Chemical compound NC1=CC=CC(NC(=S)NC=2C=CC(NC(=O)C=3OC=CC=3)=CC=2)=C1 BMWUNMMRRLWLSA-UHFFFAOYSA-N 0.000 description 1
- NEQSJXNFGMVFRD-UHFFFAOYSA-N n-[4-[(3-carbamoylphenyl)carbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound NC(=O)C1=CC=CC(NC(=S)NC=2C=CC(NC(=O)C=3C(=CC=CC=3)F)=CC=2)=C1 NEQSJXNFGMVFRD-UHFFFAOYSA-N 0.000 description 1
- PFLHXPDSCRBVEC-UHFFFAOYSA-N n-[4-[(3-chloro-4-cyclohexylsulfanylphenyl)carbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound FC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NC(C=C1Cl)=CC=C1SC1CCCCC1 PFLHXPDSCRBVEC-UHFFFAOYSA-N 0.000 description 1
- VSDYXOSAMMYMII-UHFFFAOYSA-N n-[4-[(3-chloro-4-ethenylphenyl)carbamothioylamino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC1=CC=C(C=C)C(Cl)=C1 VSDYXOSAMMYMII-UHFFFAOYSA-N 0.000 description 1
- TYPWYVOJLXJYFC-UHFFFAOYSA-N n-[4-[(3-chloro-4-ethoxyphenyl)carbamothioylamino]phenyl]acetamide Chemical compound C1=C(Cl)C(OCC)=CC=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 TYPWYVOJLXJYFC-UHFFFAOYSA-N 0.000 description 1
- QXCHHEYPJWZLTI-UHFFFAOYSA-N n-[4-[(3-chloro-4-ethylsulfanylphenyl)carbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound C1=C(Cl)C(SCC)=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F QXCHHEYPJWZLTI-UHFFFAOYSA-N 0.000 description 1
- VVCCWEPCXCOWRG-UHFFFAOYSA-N n-[4-[(3-chloro-4-iodophenyl)carbamothioylamino]phenyl]furan-2-carboxamide Chemical compound C1=C(I)C(Cl)=CC(NC(=S)NC=2C=CC(NC(=O)C=3OC=CC=3)=CC=2)=C1 VVCCWEPCXCOWRG-UHFFFAOYSA-N 0.000 description 1
- ZEKUBFNVVXAVJX-UHFFFAOYSA-N n-[4-[(3-chloro-4-methoxyphenyl)carbamothioylamino]phenyl]-3-fluorobenzamide Chemical compound C1=C(Cl)C(OC)=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC(F)=C1 ZEKUBFNVVXAVJX-UHFFFAOYSA-N 0.000 description 1
- VNOIBPGQPRMMPE-UHFFFAOYSA-N n-[4-[(3-chloro-4-methoxyphenyl)carbamothioylamino]phenyl]-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NC1=CC=C(OC)C(Cl)=C1 VNOIBPGQPRMMPE-UHFFFAOYSA-N 0.000 description 1
- TWYCXOOIVLDZOZ-UHFFFAOYSA-N n-[4-[(3-chloro-4-methylphenyl)carbamothioylamino]-2-methylphenyl]-2-fluorobenzamide Chemical compound C1=C(Cl)C(C)=CC=C1NC(=S)NC(C=C1C)=CC=C1NC(=O)C1=CC=CC=C1F TWYCXOOIVLDZOZ-UHFFFAOYSA-N 0.000 description 1
- KDORCFHEBHHIML-UHFFFAOYSA-N n-[4-[(3-chloro-4-methylphenyl)carbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound C1=C(Cl)C(C)=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F KDORCFHEBHHIML-UHFFFAOYSA-N 0.000 description 1
- OVEZYAVCJYOATK-UHFFFAOYSA-N n-[4-[(3-chloro-4-methylphenyl)carbamothioylamino]phenyl]-2-methylbenzamide Chemical compound C1=C(Cl)C(C)=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C OVEZYAVCJYOATK-UHFFFAOYSA-N 0.000 description 1
- GZLNHXTXALDNBU-UHFFFAOYSA-N n-[4-[(3-chloro-4-methylphenyl)carbamothioylamino]phenyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(C)=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CO1 GZLNHXTXALDNBU-UHFFFAOYSA-N 0.000 description 1
- FZRHHJMSAPLRGW-UHFFFAOYSA-N n-[4-[(3-chloro-4-methylphenyl)carbamothioylamino]phenyl]pyridine-2-carboxamide Chemical compound C1=C(Cl)C(C)=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=N1 FZRHHJMSAPLRGW-UHFFFAOYSA-N 0.000 description 1
- FQVZBXNCAKUOGQ-UHFFFAOYSA-N n-[4-[(3-chloro-4-methylsulfanylphenyl)carbamothioylamino]-2-methylphenyl]-2-fluorobenzamide Chemical compound C1=C(Cl)C(SC)=CC=C1NC(=S)NC(C=C1C)=CC=C1NC(=O)C1=CC=CC=C1F FQVZBXNCAKUOGQ-UHFFFAOYSA-N 0.000 description 1
- UFQGZMRTGWTGDI-UHFFFAOYSA-N n-[4-[(3-chloro-4-methylsulfanylphenyl)carbamothioylamino]phenyl]-2,6-difluorobenzamide Chemical compound C1=C(Cl)C(SC)=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F UFQGZMRTGWTGDI-UHFFFAOYSA-N 0.000 description 1
- ONBOIEWSNZSDMM-UHFFFAOYSA-N n-[4-[(3-chloro-4-methylsulfanylphenyl)carbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound C1=C(Cl)C(SC)=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F ONBOIEWSNZSDMM-UHFFFAOYSA-N 0.000 description 1
- RFPIBPURKDGAIS-UHFFFAOYSA-N n-[4-[(3-chloro-4-methylsulfanylphenyl)carbamothioylamino]phenyl]acetamide Chemical compound C1=C(Cl)C(SC)=CC=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 RFPIBPURKDGAIS-UHFFFAOYSA-N 0.000 description 1
- SROPMZYBIMUKBX-UHFFFAOYSA-N n-[4-[(3-chloro-4-methylsulfanylphenyl)carbamothioylamino]phenyl]pyridine-2-carboxamide Chemical compound C1=C(Cl)C(SC)=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=N1 SROPMZYBIMUKBX-UHFFFAOYSA-N 0.000 description 1
- LXTQNRUZXAYOQR-UHFFFAOYSA-N n-[4-[(3-chloro-4-methylsulfinylphenyl)carbamothioylamino]phenyl]-2,6-difluorobenzamide Chemical compound C1=C(Cl)C(S(=O)C)=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F LXTQNRUZXAYOQR-UHFFFAOYSA-N 0.000 description 1
- PJJYMGAVXRANDX-UHFFFAOYSA-N n-[4-[(3-chloro-4-methylsulfonylphenyl)carbamothioylamino]phenyl]-2,6-difluorobenzamide Chemical compound C1=C(Cl)C(S(=O)(=O)C)=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F PJJYMGAVXRANDX-UHFFFAOYSA-N 0.000 description 1
- YAELWEDKNWTUBI-UHFFFAOYSA-N n-[4-[(3-chloro-4-morpholin-4-ylphenyl)carbamothioylamino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC(C=C1Cl)=CC=C1N1CCOCC1 YAELWEDKNWTUBI-UHFFFAOYSA-N 0.000 description 1
- FWIJFVJYQKXCEA-UHFFFAOYSA-N n-[4-[(3-chloro-4-phenylmethoxyphenyl)carbamothioylamino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC(C=C1Cl)=CC=C1OCC1=CC=CC=C1 FWIJFVJYQKXCEA-UHFFFAOYSA-N 0.000 description 1
- BMAZXHFRMIBTQW-UHFFFAOYSA-N n-[4-[(3-chloro-4-piperidin-1-ylphenyl)carbamothioylamino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC(C=C1Cl)=CC=C1N1CCCCC1 BMAZXHFRMIBTQW-UHFFFAOYSA-N 0.000 description 1
- NFVKCYLHMKKVGM-UHFFFAOYSA-N n-[4-[(3-chloroanilino)carbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound FC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NNC1=CC=CC(Cl)=C1 NFVKCYLHMKKVGM-UHFFFAOYSA-N 0.000 description 1
- YXEFGHZTDICUDO-UHFFFAOYSA-N n-[4-[(3-chloroanilino)carbamothioylamino]phenyl]furan-2-carboxamide Chemical compound ClC1=CC=CC(NNC(=S)NC=2C=CC(NC(=O)C=3OC=CC=3)=CC=2)=C1 YXEFGHZTDICUDO-UHFFFAOYSA-N 0.000 description 1
- ZRBCZPPODWRKBV-UHFFFAOYSA-N n-[4-[(3-chlorophenyl)carbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound FC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NC1=CC=CC(Cl)=C1 ZRBCZPPODWRKBV-UHFFFAOYSA-N 0.000 description 1
- ZTYVECSYNJQCKI-UHFFFAOYSA-N n-[4-[(3-chlorophenyl)carbamothioylamino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC1=CC=CC(Cl)=C1 ZTYVECSYNJQCKI-UHFFFAOYSA-N 0.000 description 1
- AXYWLWKGMDNWKP-UHFFFAOYSA-N n-[4-[(3-chlorophenyl)carbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound ClC1=CC=CC(NC(=S)NC=2C=CC(NC(=O)C=3N=NSC=3)=CC=2)=C1 AXYWLWKGMDNWKP-UHFFFAOYSA-N 0.000 description 1
- RAEFYYFFJDZYEY-UHFFFAOYSA-N n-[4-[(3-chlorophenyl)methylcarbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound FC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NCC1=CC=CC(Cl)=C1 RAEFYYFFJDZYEY-UHFFFAOYSA-N 0.000 description 1
- AITSATANWXVVGN-UHFFFAOYSA-N n-[4-[(3-chlorophenyl)methylcarbamothioylamino]phenyl]furan-2-carboxamide Chemical compound ClC1=CC=CC(CNC(=S)NC=2C=CC(NC(=O)C=3OC=CC=3)=CC=2)=C1 AITSATANWXVVGN-UHFFFAOYSA-N 0.000 description 1
- GUBWQQZHHFGXAJ-UHFFFAOYSA-N n-[4-[(3-cyanophenyl)carbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound FC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NC1=CC=CC(C#N)=C1 GUBWQQZHHFGXAJ-UHFFFAOYSA-N 0.000 description 1
- ABQWODUQZTYNBZ-UHFFFAOYSA-N n-[4-[(3-cyanophenyl)carbamothioylamino]phenyl]furan-2-carboxamide Chemical compound C=1C=COC=1C(=O)NC(C=C1)=CC=C1NC(=S)NC1=CC=CC(C#N)=C1 ABQWODUQZTYNBZ-UHFFFAOYSA-N 0.000 description 1
- FVYZCLBOTGGUTQ-UHFFFAOYSA-N n-[4-[(3-fluorophenyl)carbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound FC1=CC=CC(NC(=S)NC=2C=CC(NC(=O)C=3N=NSC=3)=CC=2)=C1 FVYZCLBOTGGUTQ-UHFFFAOYSA-N 0.000 description 1
- WDVSABRKPOIKKA-UHFFFAOYSA-N n-[4-[(3-iodophenyl)carbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound IC1=CC=CC(NC(=S)NC=2C=CC(NC(=O)C=3N=NSC=3)=CC=2)=C1 WDVSABRKPOIKKA-UHFFFAOYSA-N 0.000 description 1
- IFSGLUTZVHXDEZ-UHFFFAOYSA-N n-[4-[(3-iodophenyl)methylcarbamothioylamino]phenyl]furan-2-carboxamide Chemical compound IC1=CC=CC(CNC(=S)NC=2C=CC(NC(=O)C=3OC=CC=3)=CC=2)=C1 IFSGLUTZVHXDEZ-UHFFFAOYSA-N 0.000 description 1
- SKGBGDPWJGZPGA-UHFFFAOYSA-N n-[4-[(3-methoxyphenyl)carbamothioylamino]phenyl]furan-2-carboxamide Chemical compound COC1=CC=CC(NC(=S)NC=2C=CC(NC(=O)C=3OC=CC=3)=CC=2)=C1 SKGBGDPWJGZPGA-UHFFFAOYSA-N 0.000 description 1
- QKBOPUWYSUCOCO-UHFFFAOYSA-N n-[4-[(3-nitrophenyl)carbamothioylamino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC1=CC=CC([N+]([O-])=O)=C1 QKBOPUWYSUCOCO-UHFFFAOYSA-N 0.000 description 1
- XMTGVZPXMSQTET-UHFFFAOYSA-N n-[4-[(3-propan-2-ylphenyl)carbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound CC(C)C1=CC=CC(NC(=S)NC=2C=CC(NC(=O)C=3N=NSC=3)=CC=2)=C1 XMTGVZPXMSQTET-UHFFFAOYSA-N 0.000 description 1
- FFLRXUWYNBQNJE-UHFFFAOYSA-N n-[4-[(3-tert-butylphenyl)carbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound CC(C)(C)C1=CC=CC(NC(=S)NC=2C=CC(NC(=O)C=3N=NSC=3)=CC=2)=C1 FFLRXUWYNBQNJE-UHFFFAOYSA-N 0.000 description 1
- JVMFXNLWELAOIC-UHFFFAOYSA-N n-[4-[(4-acetamidophenyl)carbamothioylamino]-2-chlorophenyl]-2-(dipropylamino)acetamide Chemical compound C1=C(Cl)C(NC(=O)CN(CCC)CCC)=CC=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 JVMFXNLWELAOIC-UHFFFAOYSA-N 0.000 description 1
- KRKRPNJMSQVVHV-UHFFFAOYSA-N n-[4-[(4-acetamidophenyl)carbamothioylamino]-2-chlorophenyl]-2-piperidin-1-ylacetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC(C=C1Cl)=CC=C1NC(=O)CN1CCCCC1 KRKRPNJMSQVVHV-UHFFFAOYSA-N 0.000 description 1
- CQPMRYFXTYFJER-UHFFFAOYSA-N n-[4-[(4-amino-3,5-dibromophenyl)carbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound C1=C(Br)C(N)=C(Br)C=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F CQPMRYFXTYFJER-UHFFFAOYSA-N 0.000 description 1
- LYOQPUXQMQXSAS-UHFFFAOYSA-N n-[4-[(4-amino-3,5-dichlorophenyl)carbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound C1=C(Cl)C(N)=C(Cl)C=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F LYOQPUXQMQXSAS-UHFFFAOYSA-N 0.000 description 1
- CEANFLSCWSWVRA-UHFFFAOYSA-N n-[4-[(4-benzamido-3-chlorophenyl)carbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound FC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NC(C=C1Cl)=CC=C1NC(=O)C1=CC=CC=C1 CEANFLSCWSWVRA-UHFFFAOYSA-N 0.000 description 1
- NIUDMQWWCRWWMQ-UHFFFAOYSA-N n-[4-[(4-benzamido-3-chlorophenyl)carbamothioylamino]phenyl]furan-2-carboxamide Chemical compound C=1C=C(NC(=O)C=2C=CC=CC=2)C(Cl)=CC=1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CO1 NIUDMQWWCRWWMQ-UHFFFAOYSA-N 0.000 description 1
- OLPNFAUIYXFRTK-UHFFFAOYSA-N n-[4-[(4-bromo-3-chlorophenyl)carbamothioylamino]phenyl]furan-2-carboxamide Chemical compound C1=C(Br)C(Cl)=CC(NC(=S)NC=2C=CC(NC(=O)C=3OC=CC=3)=CC=2)=C1 OLPNFAUIYXFRTK-UHFFFAOYSA-N 0.000 description 1
- KXRPODARNOZDIC-UHFFFAOYSA-N n-[4-[(4-butan-2-yloxy-3-chlorophenyl)carbamothioylamino]phenyl]acetamide Chemical compound C1=C(Cl)C(OC(C)CC)=CC=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 KXRPODARNOZDIC-UHFFFAOYSA-N 0.000 description 1
- FCCZKNCSWYOTBH-UHFFFAOYSA-N n-[4-[(4-butoxy-3-chlorophenyl)carbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound C1=C(Cl)C(OCCCC)=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F FCCZKNCSWYOTBH-UHFFFAOYSA-N 0.000 description 1
- YXOUMPBNNPLLLD-UHFFFAOYSA-N n-[4-[(4-butoxy-3-chlorophenyl)carbamothioylamino]phenyl]acetamide Chemical compound C1=C(Cl)C(OCCCC)=CC=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 YXOUMPBNNPLLLD-UHFFFAOYSA-N 0.000 description 1
- NXZYRFJUGVKZPP-UHFFFAOYSA-N n-[4-[(4-butylsulfanyl-3-chlorophenyl)carbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound C1=C(Cl)C(SCCCC)=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F NXZYRFJUGVKZPP-UHFFFAOYSA-N 0.000 description 1
- XFKVTRSTGCCNAD-UHFFFAOYSA-N n-[4-[(4-chlorophenyl)carbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSN=N1 XFKVTRSTGCCNAD-UHFFFAOYSA-N 0.000 description 1
- VOIFYAVEMNIQOH-UHFFFAOYSA-N n-[4-[(4-fluorophenyl)methylcarbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound C1=CC(F)=CC=C1CNC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSN=N1 VOIFYAVEMNIQOH-UHFFFAOYSA-N 0.000 description 1
- BOISRWYWGUXGRG-UHFFFAOYSA-N n-[4-[(4-methoxyphenyl)carbamothioylamino]phenyl]acetamide Chemical compound C1=CC(OC)=CC=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 BOISRWYWGUXGRG-UHFFFAOYSA-N 0.000 description 1
- UFUWRBZVRMUAEQ-UHFFFAOYSA-N n-[4-[(5-bromo-2,4-dimethoxyphenyl)carbamothioylamino]phenyl]acetamide Chemical compound C1=C(Br)C(OC)=CC(OC)=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 UFUWRBZVRMUAEQ-UHFFFAOYSA-N 0.000 description 1
- VEFPZVDGZQDEKV-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-2,5-dimethoxyphenyl]-2-fluorobenzamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C(=C1)OC)=CC(OC)=C1NC(=O)C1=CC=CC=C1F VEFPZVDGZQDEKV-UHFFFAOYSA-N 0.000 description 1
- RGITYOKYWDJAOG-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-2,5-dimethoxyphenyl]acetamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC1=CC(OC)=C(NC(C)=O)C=C1OC RGITYOKYWDJAOG-UHFFFAOYSA-N 0.000 description 1
- MFTXFWFSHUNARL-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-2-cyanophenyl]-2-fluorobenzamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1C#N)=CC=C1NC(=O)C1=CC=CC=C1F MFTXFWFSHUNARL-UHFFFAOYSA-N 0.000 description 1
- RYZXMFCLUKJUTK-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-2-cyanophenyl]acetamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC1=CC=C(NC(C)=O)C(C#N)=C1 RYZXMFCLUKJUTK-UHFFFAOYSA-N 0.000 description 1
- OZLGQXCNURDBKQ-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-2-methoxyphenyl]-2-fluorobenzamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1OC)=CC=C1NC(=O)C1=CC=CC=C1F OZLGQXCNURDBKQ-UHFFFAOYSA-N 0.000 description 1
- JXSCBJYCNOLNDN-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-2-methylphenyl]-2-fluorobenzamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1C)=CC=C1NC(=O)C1=CC=CC=C1F JXSCBJYCNOLNDN-UHFFFAOYSA-N 0.000 description 1
- GFBPVDJAUSCCJH-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-2-methylphenyl]acetamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC1=CC=C(NC(C)=O)C(C)=C1 GFBPVDJAUSCCJH-UHFFFAOYSA-N 0.000 description 1
- KIMDZSMWMIFCHG-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-3-(trifluoromethyl)phenyl]acetamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1C(F)(F)F KIMDZSMWMIFCHG-UHFFFAOYSA-N 0.000 description 1
- AWCDXSJRQKVAKF-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-3-cyanophenyl]-2-fluorobenzamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C(=C1)C#N)=CC=C1NC(=O)C1=CC=CC=C1F AWCDXSJRQKVAKF-UHFFFAOYSA-N 0.000 description 1
- PYMFFWXUOGNIOY-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-3-cyanophenyl]acetamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1C#N PYMFFWXUOGNIOY-UHFFFAOYSA-N 0.000 description 1
- XHPMPKSGMYGLIM-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-3-methylphenyl]-2,6-difluorobenzamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C(=C1)C)=CC=C1NC(=O)C1=C(F)C=CC=C1F XHPMPKSGMYGLIM-UHFFFAOYSA-N 0.000 description 1
- DQEDPEUMWANTNQ-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-3-methylphenyl]acetamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1C DQEDPEUMWANTNQ-UHFFFAOYSA-N 0.000 description 1
- SMSBXMKSTSOVRJ-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]naphthalen-1-yl]acetamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC1=CC=C(NC(C)=O)C2=CC=CC=C12 SMSBXMKSTSOVRJ-UHFFFAOYSA-N 0.000 description 1
- JDEOXVMKPYNKBM-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]phenyl]-1,3-benzodioxole-4-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC2=C1OCO2 JDEOXVMKPYNKBM-UHFFFAOYSA-N 0.000 description 1
- BJXCYOJTHNPMDI-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]phenyl]-1-benzofuran-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC2=CC=CC=C2O1 BJXCYOJTHNPMDI-UHFFFAOYSA-N 0.000 description 1
- RCEOEJHBCXPDGP-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]phenyl]-1-benzothiophene-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC2=CC=CC=C2S1 RCEOEJHBCXPDGP-UHFFFAOYSA-N 0.000 description 1
- XFENDSWRHPKDIT-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]phenyl]-2-(trifluoromethyl)benzamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C(F)(F)F XFENDSWRHPKDIT-UHFFFAOYSA-N 0.000 description 1
- KKIBDJYZVDPZDR-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]phenyl]-2-hydroxybenzamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1O KKIBDJYZVDPZDR-UHFFFAOYSA-N 0.000 description 1
- JORUHCIDYDBPDA-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]phenyl]-2-methoxybenzamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1OC JORUHCIDYDBPDA-UHFFFAOYSA-N 0.000 description 1
- JDUZJLKXSFRGHY-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]phenyl]-2-nitrobenzamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1[N+]([O-])=O JDUZJLKXSFRGHY-UHFFFAOYSA-N 0.000 description 1
- GUFPKTJEOVYWQR-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]phenyl]-3-(methanesulfonamido)benzamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC(NS(C)(=O)=O)=C1 GUFPKTJEOVYWQR-UHFFFAOYSA-N 0.000 description 1
- KVERYTKDHRWPSM-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]phenyl]-3-(trifluoromethoxy)benzamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC(OC(F)(F)F)=C1 KVERYTKDHRWPSM-UHFFFAOYSA-N 0.000 description 1
- SMICJXSJCJUHCM-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]phenyl]-3-[2-(dimethylamino)ethoxy]benzamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC(OCCN(C)C)=C1 SMICJXSJCJUHCM-UHFFFAOYSA-N 0.000 description 1
- IBGCSGJHYCRMKX-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]phenyl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NC=2C=CC(NC(=S)NC=3C(=CC(OC)=C(Cl)C=3)OC)=CC=2)=C1 IBGCSGJHYCRMKX-UHFFFAOYSA-N 0.000 description 1
- ASFIRALEXLLPGP-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]phenyl]-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NC1=CC(Cl)=C(OC)C=C1OC ASFIRALEXLLPGP-UHFFFAOYSA-N 0.000 description 1
- QKMDDLJQZUXSCG-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]phenyl]benzamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1 QKMDDLJQZUXSCG-UHFFFAOYSA-N 0.000 description 1
- FAGIUUMOOOYDKJ-UHFFFAOYSA-N n-[4-[(5-chloro-2-hydroxy-4-methoxyphenyl)carbamothioylamino]phenyl]acetamide Chemical compound C1=C(Cl)C(OC)=CC(O)=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 FAGIUUMOOOYDKJ-UHFFFAOYSA-N 0.000 description 1
- AVXMQRHKZSQDFG-UHFFFAOYSA-N n-[4-[(5-chloro-2-hydroxyphenyl)carbamothioylamino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC1=CC(Cl)=CC=C1O AVXMQRHKZSQDFG-UHFFFAOYSA-N 0.000 description 1
- FJIGHNLIEIJPIO-UHFFFAOYSA-N n-[4-[(5-chloro-2-methoxy-4-methylphenyl)carbamothioylamino]phenyl]-2-methylbenzamide Chemical compound COC1=CC(C)=C(Cl)C=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C FJIGHNLIEIJPIO-UHFFFAOYSA-N 0.000 description 1
- XPVABVFSBQYVBH-UHFFFAOYSA-N n-[4-[(5-chloro-4-methoxy-2-morpholin-4-ylphenyl)carbamothioylamino]phenyl]acetamide Chemical compound C=1C=C(NC(C)=O)C=CC=1NC(=S)NC=1C=C(Cl)C(OC)=CC=1N1CCOCC1 XPVABVFSBQYVBH-UHFFFAOYSA-N 0.000 description 1
- ZIWOVRWAZDVWFM-UHFFFAOYSA-N n-[4-[(5-chloro-4-methoxy-2-pyrrolidin-1-ylphenyl)carbamothioylamino]phenyl]acetamide Chemical compound C=1C=C(NC(C)=O)C=CC=1NC(=S)NC=1C=C(Cl)C(OC)=CC=1N1CCCC1 ZIWOVRWAZDVWFM-UHFFFAOYSA-N 0.000 description 1
- CHOAFNBZWWGXLN-UHFFFAOYSA-N n-[4-[(5-fluoro-2,4-dimethoxyphenyl)carbamothioylamino]phenyl]acetamide Chemical compound C1=C(F)C(OC)=CC(OC)=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 CHOAFNBZWWGXLN-UHFFFAOYSA-N 0.000 description 1
- HJNOVKXEQJNJIA-UHFFFAOYSA-N n-[4-[(6-chloropyridin-3-yl)carbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound C1=NC(Cl)=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSN=N1 HJNOVKXEQJNJIA-UHFFFAOYSA-N 0.000 description 1
- RQBTYCUGENXNOG-UHFFFAOYSA-N n-[4-[1-(1-benzofuran-2-yl)ethylcarbamothioylamino]-2-methylphenyl]-2-fluorobenzamide Chemical compound C=1C2=CC=CC=C2OC=1C(C)NC(=S)NC(C=C1C)=CC=C1NC(=O)C1=CC=CC=C1F RQBTYCUGENXNOG-UHFFFAOYSA-N 0.000 description 1
- SJBUNTRROQMRCF-UHFFFAOYSA-N n-[4-[1-(1-benzofuran-2-yl)ethylcarbamothioylamino]phenyl]-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NC(C)C1=CC2=CC=CC=C2O1 SJBUNTRROQMRCF-UHFFFAOYSA-N 0.000 description 1
- CKUDUAKETAJLBX-UHFFFAOYSA-N n-[4-[1-(2-bromophenyl)ethylcarbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound C=1C=CC=C(Br)C=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F CKUDUAKETAJLBX-UHFFFAOYSA-N 0.000 description 1
- JDPIWHGWTZUGBW-UHFFFAOYSA-N n-[4-[1-(3-chlorophenyl)ethylcarbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound C=1C=CC(Cl)=CC=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F JDPIWHGWTZUGBW-UHFFFAOYSA-N 0.000 description 1
- PPXUPLTWZAIFJF-UHFFFAOYSA-N n-[4-[1-(4-bromophenyl)ethylcarbamothioylamino]-2-(2-morpholin-4-ylethoxy)phenyl]-2-fluorobenzamide Chemical compound C=1C=C(Br)C=CC=1C(C)NC(=S)NC(C=C1OCCN2CCOCC2)=CC=C1NC(=O)C1=CC=CC=C1F PPXUPLTWZAIFJF-UHFFFAOYSA-N 0.000 description 1
- IOABVAYQZBFYFU-UHFFFAOYSA-N n-[4-[1-(4-bromophenyl)ethylcarbamothioylamino]phenyl]-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NC(C)C1=CC=C(Br)C=C1 IOABVAYQZBFYFU-UHFFFAOYSA-N 0.000 description 1
- MZNGRRVYCARXOA-UHFFFAOYSA-N n-[4-[1-(4-bromophenyl)ethylcarbamothioylamino]phenyl]isoquinoline-1-carboxamide Chemical compound C=1C=C(NC(=O)C=2C3=CC=CC=C3C=CN=2)C=CC=1NC(=S)NC(C)C1=CC=C(Br)C=C1 MZNGRRVYCARXOA-UHFFFAOYSA-N 0.000 description 1
- SUWGJAQKGMMPAP-UHFFFAOYSA-N n-[4-[1-(4-chlorophenyl)ethylcarbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound C=1C=C(Cl)C=CC=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F SUWGJAQKGMMPAP-UHFFFAOYSA-N 0.000 description 1
- ATMJGGXWNSUDPI-UHFFFAOYSA-N n-[4-[1-(4-cyanophenyl)ethylcarbamothioylamino]-2,5-dimethoxyphenyl]-2-fluorobenzamide Chemical compound COC=1C=C(NC(=S)NC(C)C=2C=CC(=CC=2)C#N)C(OC)=CC=1NC(=O)C1=CC=CC=C1F ATMJGGXWNSUDPI-UHFFFAOYSA-N 0.000 description 1
- MNWXBRGNWXIYIH-UHFFFAOYSA-N n-[4-[1-(4-cyanophenyl)ethylcarbamothioylamino]-2-ethoxyphenyl]-2-fluorobenzamide Chemical compound C=1C=C(NC(=O)C=2C(=CC=CC=2)F)C(OCC)=CC=1NC(=S)NC(C)C1=CC=C(C#N)C=C1 MNWXBRGNWXIYIH-UHFFFAOYSA-N 0.000 description 1
- QHEYRSYAQFNEQH-UHFFFAOYSA-N n-[4-[1-(4-cyanophenyl)ethylcarbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound C=1C=C(C#N)C=CC=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F QHEYRSYAQFNEQH-UHFFFAOYSA-N 0.000 description 1
- TVATXXIZGDVIGL-UHFFFAOYSA-N n-[4-[1-(4-cyanophenyl)ethylcarbamothioylamino]phenyl]-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NC(C)C1=CC=C(C#N)C=C1 TVATXXIZGDVIGL-UHFFFAOYSA-N 0.000 description 1
- KQJUBGBULPYQRX-UHFFFAOYSA-N n-[4-[1-(4-fluorophenyl)ethylcarbamothioylamino]-2-(trifluoromethyl)phenyl]-1-benzofuran-2-carboxamide Chemical compound C=1C=C(NC(=O)C=2OC3=CC=CC=C3C=2)C(C(F)(F)F)=CC=1NC(=S)NC(C)C1=CC=C(F)C=C1 KQJUBGBULPYQRX-UHFFFAOYSA-N 0.000 description 1
- FZRWUNBPJGKTHD-UHFFFAOYSA-N n-[4-[1-(4-fluorophenyl)ethylcarbamothioylamino]-2-methylphenyl]isoquinoline-1-carboxamide Chemical compound C=1C=C(NC(=O)C=2C3=CC=CC=C3C=CN=2)C(C)=CC=1NC(=S)NC(C)C1=CC=C(F)C=C1 FZRWUNBPJGKTHD-UHFFFAOYSA-N 0.000 description 1
- LDSWYNOVUGAEFH-UHFFFAOYSA-N n-[4-[1-(4-fluorophenyl)ethylcarbamothioylamino]phenyl]-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NC(C)C1=CC=C(F)C=C1 LDSWYNOVUGAEFH-UHFFFAOYSA-N 0.000 description 1
- AAPKUPYEJSKOEO-UHFFFAOYSA-N n-[4-[1-(4-fluorophenyl)ethylcarbamothioylamino]phenyl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NC=2C=CC(NC(=S)NC(C)C=3C=CC(F)=CC=3)=CC=2)=C1 AAPKUPYEJSKOEO-UHFFFAOYSA-N 0.000 description 1
- HNWMYUNXUZWIFV-UHFFFAOYSA-N n-[4-[1-(4-fluorophenyl)ethylcarbamothioylamino]phenyl]-4-(trifluoromethyl)benzamide Chemical compound C=1C=C(F)C=CC=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1 HNWMYUNXUZWIFV-UHFFFAOYSA-N 0.000 description 1
- IEZAHSYLYAEHSK-UHFFFAOYSA-N n-[4-[1-(4-fluorophenyl)ethylcarbamothioylamino]phenyl]benzamide Chemical compound C=1C=C(F)C=CC=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1 IEZAHSYLYAEHSK-UHFFFAOYSA-N 0.000 description 1
- YJSUVOYUNHXRHO-UHFFFAOYSA-N n-[4-[1-(4-fluorophenyl)ethylcarbamothioylamino]phenyl]pyridine-4-carboxamide Chemical compound C=1C=C(F)C=CC=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=NC=C1 YJSUVOYUNHXRHO-UHFFFAOYSA-N 0.000 description 1
- AXSHDVBYRZOMLM-UHFFFAOYSA-N n-[4-[1-(4-fluorophenyl)ethylcarbamothioylamino]phenyl]quinoline-4-carboxamide Chemical compound C=1C=C(NC(=O)C=2C3=CC=CC=C3N=CC=2)C=CC=1NC(=S)NC(C)C1=CC=C(F)C=C1 AXSHDVBYRZOMLM-UHFFFAOYSA-N 0.000 description 1
- KEFLYAXBYLYEMC-UHFFFAOYSA-N n-[4-[1-[3-(dimethylamino)phenyl]ethylcarbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound C=1C=CC(N(C)C)=CC=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F KEFLYAXBYLYEMC-UHFFFAOYSA-N 0.000 description 1
- SMDGODVCAWMWEY-UHFFFAOYSA-N n-[4-[1-[4-(dimethylamino)phenyl]ethylcarbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound C=1C=C(N(C)C)C=CC=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F SMDGODVCAWMWEY-UHFFFAOYSA-N 0.000 description 1
- KOOVZLLETLDOIE-UHFFFAOYSA-N n-[4-[1-[4-(dimethylsulfamoyl)phenyl]ethylcarbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound C=1C=C(S(=O)(=O)N(C)C)C=CC=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F KOOVZLLETLDOIE-UHFFFAOYSA-N 0.000 description 1
- PLXUJLKMMBELPB-UHFFFAOYSA-N n-[4-[2-(2,4-dichlorophenyl)ethylcarbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound ClC1=CC(Cl)=CC=C1CCNC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSN=N1 PLXUJLKMMBELPB-UHFFFAOYSA-N 0.000 description 1
- ACSJVXCEXCPWND-UHFFFAOYSA-N n-[4-[2-(2-chlorophenyl)ethylcarbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound ClC1=CC=CC=C1CCNC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSN=N1 ACSJVXCEXCPWND-UHFFFAOYSA-N 0.000 description 1
- LVYNYELTCAJRLQ-UHFFFAOYSA-N n-[4-[2-(3,4-dichlorophenyl)ethylcarbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound FC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NCCC1=CC=C(Cl)C(Cl)=C1 LVYNYELTCAJRLQ-UHFFFAOYSA-N 0.000 description 1
- MVTRSKODOGPSBM-UHFFFAOYSA-N n-[4-[2-(3,4-dichlorophenyl)ethylcarbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1CCNC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSN=N1 MVTRSKODOGPSBM-UHFFFAOYSA-N 0.000 description 1
- NNOUHZRJCZZECG-UHFFFAOYSA-N n-[4-[2-(3,4-difluorophenyl)ethylcarbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound C1=C(F)C(F)=CC=C1CCNC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSN=N1 NNOUHZRJCZZECG-UHFFFAOYSA-N 0.000 description 1
- HPNDFYKFMBSLMH-UHFFFAOYSA-N n-[4-[2-(3,4-dimethoxyphenyl)ethylcarbamothioylamino]phenyl]furan-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1CCNC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CO1 HPNDFYKFMBSLMH-UHFFFAOYSA-N 0.000 description 1
- PQXKEPGPGUCDOJ-UHFFFAOYSA-N n-[4-[2-(3,4-dimethoxyphenyl)ethylcarbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1CCNC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSN=N1 PQXKEPGPGUCDOJ-UHFFFAOYSA-N 0.000 description 1
- ZFGYSBPLKDVLKC-UHFFFAOYSA-N n-[4-[2-(3,5-dichlorophenoxy)ethylcarbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound FC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NCCOC1=CC(Cl)=CC(Cl)=C1 ZFGYSBPLKDVLKC-UHFFFAOYSA-N 0.000 description 1
- ZJPYVQDMJSDTLP-UHFFFAOYSA-N n-[4-[2-(3,5-dichlorophenoxy)ethylcarbamothioylamino]phenyl]furan-2-carboxamide Chemical compound ClC1=CC(Cl)=CC(OCCNC(=S)NC=2C=CC(NC(=O)C=3OC=CC=3)=CC=2)=C1 ZJPYVQDMJSDTLP-UHFFFAOYSA-N 0.000 description 1
- YXRRQNIPUUOPGV-UHFFFAOYSA-N n-[4-[2-(3-bromo-4-methoxyphenyl)ethylcarbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound C1=C(Br)C(OC)=CC=C1CCNC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSN=N1 YXRRQNIPUUOPGV-UHFFFAOYSA-N 0.000 description 1
- KDQXTLJABZXURL-UHFFFAOYSA-N n-[4-[2-(3-bromophenyl)ethylcarbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound BrC1=CC=CC(CCNC(=S)NC=2C=CC(NC(=O)C=3N=NSC=3)=CC=2)=C1 KDQXTLJABZXURL-UHFFFAOYSA-N 0.000 description 1
- UFWIBMLEMQAFAM-UHFFFAOYSA-N n-[4-[2-(3-bromophenyl)sulfanylethylcarbamothioylamino]phenyl]furan-2-carboxamide Chemical compound BrC1=CC=CC(SCCNC(=S)NC=2C=CC(NC(=O)C=3OC=CC=3)=CC=2)=C1 UFWIBMLEMQAFAM-UHFFFAOYSA-N 0.000 description 1
- NIWGSTIYBRDSPX-UHFFFAOYSA-N n-[4-[2-(3-chlorophenoxy)ethylcarbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound FC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NCCOC1=CC=CC(Cl)=C1 NIWGSTIYBRDSPX-UHFFFAOYSA-N 0.000 description 1
- KMOALIQIXMVFNO-UHFFFAOYSA-N n-[4-[2-(3-chlorophenoxy)ethylcarbamothioylamino]phenyl]furan-2-carboxamide Chemical compound ClC1=CC=CC(OCCNC(=S)NC=2C=CC(NC(=O)C=3OC=CC=3)=CC=2)=C1 KMOALIQIXMVFNO-UHFFFAOYSA-N 0.000 description 1
- KSYYUWWWUKUBHC-UHFFFAOYSA-N n-[4-[2-(3-iodophenyl)ethylcarbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound IC1=CC=CC(CCNC(=S)NC=2C=CC(NC(=O)C=3N=NSC=3)=CC=2)=C1 KSYYUWWWUKUBHC-UHFFFAOYSA-N 0.000 description 1
- DJLMFEWHKYWWIV-UHFFFAOYSA-N n-[4-[2-(3-methoxyphenyl)ethylcarbamothioylamino]phenyl]furan-2-carboxamide Chemical compound COC1=CC=CC(CCNC(=S)NC=2C=CC(NC(=O)C=3OC=CC=3)=CC=2)=C1 DJLMFEWHKYWWIV-UHFFFAOYSA-N 0.000 description 1
- RRMFXFHDBSPONP-UHFFFAOYSA-N n-[4-[2-(4-bromophenyl)ethylcarbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound C1=CC(Br)=CC=C1CCNC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSN=N1 RRMFXFHDBSPONP-UHFFFAOYSA-N 0.000 description 1
- SYMKZGUUAOZKQI-UHFFFAOYSA-N n-[4-[2-(4-chlorophenyl)ethylcarbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound C1=CC(Cl)=CC=C1CCNC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSN=N1 SYMKZGUUAOZKQI-UHFFFAOYSA-N 0.000 description 1
- BRLAUQYLWMNXHR-UHFFFAOYSA-N n-[4-[2-(4-fluorophenyl)ethylcarbamothioylamino]phenyl]furan-2-carboxamide Chemical compound C1=CC(F)=CC=C1CCNC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CO1 BRLAUQYLWMNXHR-UHFFFAOYSA-N 0.000 description 1
- ACQCBINZEQZVFI-UHFFFAOYSA-N n-[4-[2-(4-methylphenyl)ethylcarbamothioylamino]phenyl]furan-2-carboxamide Chemical compound C1=CC(C)=CC=C1CCNC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CO1 ACQCBINZEQZVFI-UHFFFAOYSA-N 0.000 description 1
- WEBGHZQARPYDPF-UHFFFAOYSA-N n-[4-[2-(4-methylphenyl)ethylcarbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound C1=CC(C)=CC=C1CCNC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSN=N1 WEBGHZQARPYDPF-UHFFFAOYSA-N 0.000 description 1
- ZFRBKFKEQJQPMZ-UHFFFAOYSA-N n-[4-[2-(5-bromo-2-methoxyphenyl)ethylcarbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound COC1=CC=C(Br)C=C1CCNC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSN=N1 ZFRBKFKEQJQPMZ-UHFFFAOYSA-N 0.000 description 1
- ROOSMUIARLRNIS-UHFFFAOYSA-N n-[4-[2-[2-fluoro-5-(trifluoromethyl)phenyl]ethylcarbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound FC1=CC=C(C(F)(F)F)C=C1CCNC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSN=N1 ROOSMUIARLRNIS-UHFFFAOYSA-N 0.000 description 1
- YNHGIETXKFUDTP-UHFFFAOYSA-N n-[4-[2-[3,5-bis(trifluoromethyl)phenyl]ethylcarbamothioylamino]phenyl]furan-2-carboxamide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(CCNC(=S)NC=2C=CC(NC(=O)C=3OC=CC=3)=CC=2)=C1 YNHGIETXKFUDTP-UHFFFAOYSA-N 0.000 description 1
- BXEBTQZOVOISNT-UHFFFAOYSA-N n-[4-[2-[4-fluoro-3-(trifluoromethyl)phenyl]ethylcarbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1CCNC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSN=N1 BXEBTQZOVOISNT-UHFFFAOYSA-N 0.000 description 1
- SUWGJAQKGMMPAP-AWEZNQCLSA-N n-[4-[[(1s)-1-(4-chlorophenyl)ethyl]carbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound N([C@@H](C)C=1C=CC(Cl)=CC=1)C(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F SUWGJAQKGMMPAP-AWEZNQCLSA-N 0.000 description 1
- TXAUXQJSBQEKMA-UHFFFAOYSA-N n-[4-[[(3,4-dichlorophenyl)carbamothioylamino]methyl]phenyl]-2-fluorobenzamide Chemical compound FC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1CNC(=S)NC1=CC=C(Cl)C(Cl)=C1 TXAUXQJSBQEKMA-UHFFFAOYSA-N 0.000 description 1
- BWLSHSAXVIWFKM-UHFFFAOYSA-N n-[4-[[(3,5-dichlorophenyl)carbamothioylamino]methyl]phenyl]furan-2-carboxamide Chemical compound ClC1=CC(Cl)=CC(NC(=S)NCC=2C=CC(NC(=O)C=3OC=CC=3)=CC=2)=C1 BWLSHSAXVIWFKM-UHFFFAOYSA-N 0.000 description 1
- MDHLIHMVUCLFRA-UHFFFAOYSA-N n-[4-[[2,4-bis(2,2,2-trifluoroethoxy)phenyl]carbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound FC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NC1=CC=C(OCC(F)(F)F)C=C1OCC(F)(F)F MDHLIHMVUCLFRA-UHFFFAOYSA-N 0.000 description 1
- HFJBAUQMZVLTTR-UHFFFAOYSA-N n-[4-[[2,4-dimethoxy-5-(trifluoromethyl)phenyl]carbamothioylamino]phenyl]acetamide Chemical compound COC1=CC(OC)=C(C(F)(F)F)C=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 HFJBAUQMZVLTTR-UHFFFAOYSA-N 0.000 description 1
- YAZCPQJGXRBHQJ-UHFFFAOYSA-N n-[4-[[2-(benzylamino)-4-methoxyphenyl]carbamothioylamino]phenyl]acetamide Chemical compound C=1C=CC=CC=1CNC1=CC(OC)=CC=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 YAZCPQJGXRBHQJ-UHFFFAOYSA-N 0.000 description 1
- CWMKRERJLLFOBU-UHFFFAOYSA-N n-[4-[[2-amino-3-chloro-5-(trifluoromethyl)phenyl]carbamothioylamino]phenyl]furan-2-carboxamide Chemical compound NC1=C(Cl)C=C(C(F)(F)F)C=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CO1 CWMKRERJLLFOBU-UHFFFAOYSA-N 0.000 description 1
- YONZHEHVTCKMPJ-UHFFFAOYSA-N n-[4-[[3,5-bis(trifluoromethyl)phenyl]carbamothioylamino]phenyl]-1,3-oxazole-4-carboxamide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(NC(=S)NC=2C=CC(NC(=O)C=3N=COC=3)=CC=2)=C1 YONZHEHVTCKMPJ-UHFFFAOYSA-N 0.000 description 1
- RFXFEMFEQYCDOL-UHFFFAOYSA-N n-[4-[[3,5-bis(trifluoromethyl)phenyl]carbamothioylamino]phenyl]-1,3-thiazole-4-carboxamide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(NC(=S)NC=2C=CC(NC(=O)C=3N=CSC=3)=CC=2)=C1 RFXFEMFEQYCDOL-UHFFFAOYSA-N 0.000 description 1
- FJFOACNNYIIPDJ-UHFFFAOYSA-N n-[4-[[3,5-bis(trifluoromethyl)phenyl]carbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound FC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 FJFOACNNYIIPDJ-UHFFFAOYSA-N 0.000 description 1
- DFHFPGDHFBONRO-UHFFFAOYSA-N n-[4-[[3,5-bis(trifluoromethyl)phenyl]carbamothioylamino]phenyl]-2-methyl-1,3-thiazole-4-carboxamide Chemical compound S1C(C)=NC(C(=O)NC=2C=CC(NC(=S)NC=3C=C(C=C(C=3)C(F)(F)F)C(F)(F)F)=CC=2)=C1 DFHFPGDHFBONRO-UHFFFAOYSA-N 0.000 description 1
- IGXRYXHEOOPPEN-UHFFFAOYSA-N n-[4-[[3,5-bis(trifluoromethyl)phenyl]carbamothioylamino]phenyl]-2-phenyl-1,3-thiazole-4-carboxamide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(NC(=S)NC=2C=CC(NC(=O)C=3N=C(SC=3)C=3C=CC=CC=3)=CC=2)=C1 IGXRYXHEOOPPEN-UHFFFAOYSA-N 0.000 description 1
- DDGXWVKXUNNNAQ-UHFFFAOYSA-N n-[4-[[3,5-bis(trifluoromethyl)phenyl]carbamothioylamino]phenyl]-2-propan-2-yl-1,3-thiazole-4-carboxamide Chemical compound S1C(C(C)C)=NC(C(=O)NC=2C=CC(NC(=S)NC=3C=C(C=C(C=3)C(F)(F)F)C(F)(F)F)=CC=2)=C1 DDGXWVKXUNNNAQ-UHFFFAOYSA-N 0.000 description 1
- FVEJUWCKIKESSP-UHFFFAOYSA-N n-[4-[[3,5-bis(trifluoromethyl)phenyl]carbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(NC(=S)NC=2C=CC(NC(=O)C=3N=NSC=3)=CC=2)=C1 FVEJUWCKIKESSP-UHFFFAOYSA-N 0.000 description 1
- QCRBYLUURQEWKB-UHFFFAOYSA-N n-[4-[[3,5-bis(trifluoromethyl)phenyl]carbamoylamino]phenyl]thiadiazole-4-carboxamide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(NC(=O)NC=2C=CC(NC(=O)C=3N=NSC=3)=CC=2)=C1 QCRBYLUURQEWKB-UHFFFAOYSA-N 0.000 description 1
- CHYVJTHXYGYFBF-UHFFFAOYSA-N n-[4-[[3,5-bis(trifluoromethyl)phenyl]methylcarbamothioylamino]phenyl]furan-2-carboxamide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(CNC(=S)NC=2C=CC(NC(=O)C=3OC=CC=3)=CC=2)=C1 CHYVJTHXYGYFBF-UHFFFAOYSA-N 0.000 description 1
- DNIRDEFJLNOEJA-UHFFFAOYSA-N n-[4-[[3,5-dichloro-4-(cyanomethoxy)phenyl]carbamothioylamino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC1=CC(Cl)=C(OCC#N)C(Cl)=C1 DNIRDEFJLNOEJA-UHFFFAOYSA-N 0.000 description 1
- QGYNRENOPHEELJ-UHFFFAOYSA-N n-[4-[[3,5-dichloro-4-[2-(dimethylamino)ethoxy]phenyl]carbamothioylamino]phenyl]acetamide Chemical compound C1=C(Cl)C(OCCN(C)C)=C(Cl)C=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 QGYNRENOPHEELJ-UHFFFAOYSA-N 0.000 description 1
- NIQFUJFNJCNMIX-UHFFFAOYSA-N n-[4-[[3-(1-hydroxyethyl)phenyl]carbamothioylamino]phenyl]furan-2-carboxamide Chemical compound CC(O)C1=CC=CC(NC(=S)NC=2C=CC(NC(=O)C=3OC=CC=3)=CC=2)=C1 NIQFUJFNJCNMIX-UHFFFAOYSA-N 0.000 description 1
- ONLPXJZOZWISIF-UHFFFAOYSA-N n-[4-[[3-(2-hydroxyethylsulfonyl)phenyl]carbamothioylamino]phenyl]furan-2-carboxamide Chemical compound OCCS(=O)(=O)C1=CC=CC(NC(=S)NC=2C=CC(NC(=O)C=3OC=CC=3)=CC=2)=C1 ONLPXJZOZWISIF-UHFFFAOYSA-N 0.000 description 1
- HMUXDIKVZVLSQP-UHFFFAOYSA-N n-[4-[[3-(3-hydroxypyrrolidin-1-yl)-5-(trifluoromethyl)phenyl]carbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound C1C(O)CCN1C1=CC(NC(=S)NC=2C=CC(NC(=O)C=3N=NSC=3)=CC=2)=CC(C(F)(F)F)=C1 HMUXDIKVZVLSQP-UHFFFAOYSA-N 0.000 description 1
- ASEHSSHDTQMKIJ-UHFFFAOYSA-N n-[4-[[3-(butylsulfamoyl)phenyl]carbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound CCCCNS(=O)(=O)C1=CC=CC(NC(=S)NC=2C=CC(NC(=O)C=3C(=CC=CC=3)F)=CC=2)=C1 ASEHSSHDTQMKIJ-UHFFFAOYSA-N 0.000 description 1
- ITLYKGIJFLNRSK-UHFFFAOYSA-N n-[4-[[3-(hydrazinecarbonyl)phenyl]carbamothioylamino]phenyl]furan-2-carboxamide Chemical compound NNC(=O)C1=CC=CC(NC(=S)NC=2C=CC(NC(=O)C=3OC=CC=3)=CC=2)=C1 ITLYKGIJFLNRSK-UHFFFAOYSA-N 0.000 description 1
- VRHVRMNUCONYCR-UHFFFAOYSA-N n-[4-[[3-(trifluoromethyl)phenyl]carbamothioylamino]phenyl]furan-2-carboxamide Chemical compound FC(F)(F)C1=CC=CC(NC(=S)NC=2C=CC(NC(=O)C=3OC=CC=3)=CC=2)=C1 VRHVRMNUCONYCR-UHFFFAOYSA-N 0.000 description 1
- KJOFLPMJQXPCOA-UHFFFAOYSA-N n-[4-[[3-bromo-5-(trifluoromethyl)phenyl]carbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound FC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NC1=CC(Br)=CC(C(F)(F)F)=C1 KJOFLPMJQXPCOA-UHFFFAOYSA-N 0.000 description 1
- GQFPPTDVHZMIMB-UHFFFAOYSA-N n-[4-[[3-bromo-5-(trifluoromethyl)phenyl]carbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound FC(F)(F)C1=CC(Br)=CC(NC(=S)NC=2C=CC(NC(=O)C=3N=NSC=3)=CC=2)=C1 GQFPPTDVHZMIMB-UHFFFAOYSA-N 0.000 description 1
- OCQHGIQVXLDNKE-UHFFFAOYSA-N n-[4-[[3-chloro-2-(dimethylamino)phenyl]carbamothioylamino]phenyl]-2,6-difluorobenzamide Chemical compound CN(C)C1=C(Cl)C=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=C(F)C=CC=C1F OCQHGIQVXLDNKE-UHFFFAOYSA-N 0.000 description 1
- IDWGAUMZDCHLHX-UHFFFAOYSA-N n-[4-[[3-chloro-2-(dimethylamino)phenyl]carbamothioylamino]phenyl]furan-2-carboxamide Chemical compound CN(C)C1=C(Cl)C=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CO1 IDWGAUMZDCHLHX-UHFFFAOYSA-N 0.000 description 1
- KEXPKVDCQWXNIK-UHFFFAOYSA-N n-[4-[[3-chloro-4-(1,2-oxazol-5-yl)phenyl]carbamothioylamino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC(C=C1Cl)=CC=C1C1=CC=NO1 KEXPKVDCQWXNIK-UHFFFAOYSA-N 0.000 description 1
- OAQQILOKEKFXDS-UHFFFAOYSA-N n-[4-[[3-chloro-4-(1,2-oxazol-5-yl)phenyl]carbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound C=1C=C(C=2ON=CC=2)C(Cl)=CC=1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSN=N1 OAQQILOKEKFXDS-UHFFFAOYSA-N 0.000 description 1
- JRUUBDQAEFJKPD-UHFFFAOYSA-N n-[4-[[3-chloro-4-(1-hydroxyethyl)phenyl]carbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound C1=C(Cl)C(C(O)C)=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F JRUUBDQAEFJKPD-UHFFFAOYSA-N 0.000 description 1
- SXPLSYRTGBXNSW-UHFFFAOYSA-N n-[4-[[3-chloro-4-(1-methylpyrrolidin-3-yl)oxyphenyl]carbamothioylamino]phenyl]acetamide Chemical compound C1N(C)CCC1OC(C(=C1)Cl)=CC=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 SXPLSYRTGBXNSW-UHFFFAOYSA-N 0.000 description 1
- MDZCAGYLVWARNM-UHFFFAOYSA-N n-[4-[[3-chloro-4-(2-hydroxyethyl)phenyl]carbamothioylamino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC1=CC=C(CCO)C(Cl)=C1 MDZCAGYLVWARNM-UHFFFAOYSA-N 0.000 description 1
- NDZYDNIBLOBBOI-UHFFFAOYSA-N n-[4-[[3-chloro-4-(cyanomethoxy)phenyl]carbamothioylamino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC1=CC=C(OCC#N)C(Cl)=C1 NDZYDNIBLOBBOI-UHFFFAOYSA-N 0.000 description 1
- VRAIMOGNYDZQGZ-UHFFFAOYSA-N n-[4-[[3-chloro-4-(diethylamino)phenyl]carbamothioylamino]phenyl]acetamide Chemical compound C1=C(Cl)C(N(CC)CC)=CC=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 VRAIMOGNYDZQGZ-UHFFFAOYSA-N 0.000 description 1
- AYDFYRGKYARHIJ-UHFFFAOYSA-N n-[4-[[3-chloro-4-(dimethylamino)phenyl]carbamothioylamino]phenyl]-2-methylbenzamide Chemical compound C1=C(Cl)C(N(C)C)=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C AYDFYRGKYARHIJ-UHFFFAOYSA-N 0.000 description 1
- DIIVMKYDRTUBBU-UHFFFAOYSA-N n-[4-[[3-chloro-4-(dimethylamino)phenyl]carbamothioylamino]phenyl]acetamide Chemical compound C1=C(Cl)C(N(C)C)=CC=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 DIIVMKYDRTUBBU-UHFFFAOYSA-N 0.000 description 1
- LZAQKUNWKGNVOE-UHFFFAOYSA-N n-[4-[[3-chloro-4-(dipropylamino)phenyl]carbamothioylamino]phenyl]acetamide Chemical compound C1=C(Cl)C(N(CCC)CCC)=CC=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 LZAQKUNWKGNVOE-UHFFFAOYSA-N 0.000 description 1
- ABLXTILENPDUHD-UHFFFAOYSA-N n-[4-[[3-chloro-4-(methanesulfonamido)phenyl]carbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound C1=C(Cl)C(NS(=O)(=O)C)=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F ABLXTILENPDUHD-UHFFFAOYSA-N 0.000 description 1
- MWRVGBVWOCDENO-UHFFFAOYSA-N n-[4-[[3-chloro-4-(methanesulfonamido)phenyl]carbamothioylamino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC1=CC=C(NS(C)(=O)=O)C(Cl)=C1 MWRVGBVWOCDENO-UHFFFAOYSA-N 0.000 description 1
- ZTGCIXGPDGCGRD-UHFFFAOYSA-N n-[4-[[3-chloro-4-(methanesulfonamido)phenyl]carbamothioylamino]phenyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(NS(=O)(=O)C)=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CO1 ZTGCIXGPDGCGRD-UHFFFAOYSA-N 0.000 description 1
- HWJQWSYHRJKZAG-UHFFFAOYSA-N n-[4-[[3-chloro-4-(n-methylanilino)phenyl]carbamothioylamino]phenyl]acetamide Chemical compound C=1C=C(NC(=S)NC=2C=CC(NC(C)=O)=CC=2)C=C(Cl)C=1N(C)C1=CC=CC=C1 HWJQWSYHRJKZAG-UHFFFAOYSA-N 0.000 description 1
- JSOKLUOMYSMRHK-UHFFFAOYSA-N n-[4-[[3-chloro-4-[(2-piperidin-1-ylacetyl)amino]phenyl]carbamothioylamino]phenyl]furan-2-carboxamide Chemical compound C=1C=C(NC(=O)CN2CCCCC2)C(Cl)=CC=1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CO1 JSOKLUOMYSMRHK-UHFFFAOYSA-N 0.000 description 1
- LNLHJZPWAHNFCD-UHFFFAOYSA-N n-[4-[[3-chloro-4-[2-(dimethylamino)ethoxy]phenyl]carbamothioylamino]phenyl]acetamide Chemical compound C1=C(Cl)C(OCCN(C)C)=CC=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 LNLHJZPWAHNFCD-UHFFFAOYSA-N 0.000 description 1
- FIHKXDPQXUEFBO-UHFFFAOYSA-N n-[4-[[3-chloro-4-[2-(dimethylamino)ethylamino]phenyl]carbamothioylamino]phenyl]acetamide Chemical compound C1=C(Cl)C(NCCN(C)C)=CC=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 FIHKXDPQXUEFBO-UHFFFAOYSA-N 0.000 description 1
- UDAZHDLQBZAAHP-UHFFFAOYSA-N n-[4-[[3-chloro-4-[2-methoxyethyl(methyl)amino]phenyl]carbamothioylamino]phenyl]acetamide Chemical compound C1=C(Cl)C(N(C)CCOC)=CC=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 UDAZHDLQBZAAHP-UHFFFAOYSA-N 0.000 description 1
- MOOSEYBMWJUQSV-UHFFFAOYSA-N n-[4-[[3-chloro-4-[3-(dimethylamino)propoxy]phenyl]carbamothioylamino]phenyl]acetamide Chemical compound C1=C(Cl)C(OCCCN(C)C)=CC=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 MOOSEYBMWJUQSV-UHFFFAOYSA-N 0.000 description 1
- OQCOINWPTIGWMO-UHFFFAOYSA-N n-[4-[[3-chloro-4-[cyclohexyl(methyl)amino]phenyl]carbamothioylamino]phenyl]-2,6-difluorobenzamide Chemical compound C=1C=C(NC(=S)NC=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)C=C(Cl)C=1N(C)C1CCCCC1 OQCOINWPTIGWMO-UHFFFAOYSA-N 0.000 description 1
- JLTGXKKEIIPOLX-UHFFFAOYSA-N n-[4-[[3-chloro-4-[cyclohexyl(methyl)amino]phenyl]carbamothioylamino]phenyl]-2-methylbenzamide Chemical compound C=1C=C(NC(=S)NC=2C=CC(NC(=O)C=3C(=CC=CC=3)C)=CC=2)C=C(Cl)C=1N(C)C1CCCCC1 JLTGXKKEIIPOLX-UHFFFAOYSA-N 0.000 description 1
- IKJKDVJFMKFRHR-UHFFFAOYSA-N n-[4-[[3-chloro-4-[cyclohexyl(methyl)amino]phenyl]carbamothioylamino]phenyl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NC=2C=CC(NC(=S)NC=3C=C(Cl)C(N(C)C4CCCCC4)=CC=3)=CC=2)=C1 IKJKDVJFMKFRHR-UHFFFAOYSA-N 0.000 description 1
- XNBUSZVHSRETFI-UHFFFAOYSA-N n-[4-[[3-chloro-4-[cyclohexyl(methyl)amino]phenyl]carbamothioylamino]phenyl]acetamide Chemical compound C=1C=C(NC(=S)NC=2C=CC(NC(C)=O)=CC=2)C=C(Cl)C=1N(C)C1CCCCC1 XNBUSZVHSRETFI-UHFFFAOYSA-N 0.000 description 1
- TXZBFXJOYGVEGC-UHFFFAOYSA-N n-[4-[[3-chloro-4-[cyclopentyl(methyl)amino]phenyl]carbamothioylamino]phenyl]acetamide Chemical compound C=1C=C(NC(=S)NC=2C=CC(NC(C)=O)=CC=2)C=C(Cl)C=1N(C)C1CCCC1 TXZBFXJOYGVEGC-UHFFFAOYSA-N 0.000 description 1
- HMHKITLXMBFXEG-UHFFFAOYSA-N n-[4-[[3-chloro-4-[methyl-(1-methylpiperidin-4-yl)amino]phenyl]carbamothioylamino]phenyl]-2,6-difluorobenzamide Chemical compound C=1C=C(NC(=S)NC=2C=CC(NC(=O)C=3C(=CC=CC=3F)F)=CC=2)C=C(Cl)C=1N(C)C1CCN(C)CC1 HMHKITLXMBFXEG-UHFFFAOYSA-N 0.000 description 1
- XUYGKPABAXLTML-UHFFFAOYSA-N n-[4-[[3-chloro-4-[methyl-(1-methylpiperidin-4-yl)amino]phenyl]carbamothioylamino]phenyl]-2-methylbenzamide Chemical compound C=1C=C(NC(=S)NC=2C=CC(NC(=O)C=3C(=CC=CC=3)C)=CC=2)C=C(Cl)C=1N(C)C1CCN(C)CC1 XUYGKPABAXLTML-UHFFFAOYSA-N 0.000 description 1
- RSVQHLYCQRUUSU-UHFFFAOYSA-N n-[4-[[3-chloro-4-[methyl-(1-methylpyrrolidin-3-yl)amino]phenyl]carbamothioylamino]phenyl]acetamide Chemical compound C=1C=C(NC(=S)NC=2C=CC(NC(C)=O)=CC=2)C=C(Cl)C=1N(C)C1CCN(C)C1 RSVQHLYCQRUUSU-UHFFFAOYSA-N 0.000 description 1
- AEJDQFFFJWYGQS-UHFFFAOYSA-N n-[4-[[3-chloro-4-[methyl-(1-methylpyrrolidin-3-yl)amino]phenyl]carbamothioylamino]phenyl]pyridine-2-carboxamide Chemical compound C=1C=C(NC(=S)NC=2C=CC(NC(=O)C=3N=CC=CC=3)=CC=2)C=C(Cl)C=1N(C)C1CCN(C)C1 AEJDQFFFJWYGQS-UHFFFAOYSA-N 0.000 description 1
- QZHCRVZKZKLNDB-UHFFFAOYSA-N n-[4-[[3-chloro-5-(dimethylamino)phenyl]carbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound CN(C)C1=CC(Cl)=CC(NC(=S)NC=2C=CC(NC(=O)C=3C(=CC=CC=3)F)=CC=2)=C1 QZHCRVZKZKLNDB-UHFFFAOYSA-N 0.000 description 1
- TWSPQWDIFAUADA-UHFFFAOYSA-N n-[4-[[3-chloro-5-(dimethylamino)phenyl]carbamothioylamino]phenyl]furan-2-carboxamide Chemical compound CN(C)C1=CC(Cl)=CC(NC(=S)NC=2C=CC(NC(=O)C=3OC=CC=3)=CC=2)=C1 TWSPQWDIFAUADA-UHFFFAOYSA-N 0.000 description 1
- STFSWEWVUJNWJF-UHFFFAOYSA-N n-[4-[[3-chloro-5-[[4-(thiadiazole-4-carbonylamino)phenyl]carbamothioylamino]phenyl]carbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound C=1C(NC(=S)NC=2C=CC(NC(=O)C=3N=NSC=3)=CC=2)=CC(Cl)=CC=1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSN=N1 STFSWEWVUJNWJF-UHFFFAOYSA-N 0.000 description 1
- BYOFCDYVDBOHGM-UHFFFAOYSA-N n-[4-[[3-fluoro-5-(trifluoromethyl)phenyl]methylcarbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound FC(F)(F)C1=CC(F)=CC(CNC(=S)NC=2C=CC(NC(=O)C=3N=NSC=3)=CC=2)=C1 BYOFCDYVDBOHGM-UHFFFAOYSA-N 0.000 description 1
- PJKZXPGUYFYLJM-UHFFFAOYSA-N n-[4-[[4-(1-azidoethyl)-3-chlorophenyl]carbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound C1=C(Cl)C(C(N=[N+]=[N-])C)=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F PJKZXPGUYFYLJM-UHFFFAOYSA-N 0.000 description 1
- HVYHZVXYPGONHA-UHFFFAOYSA-N n-[4-[[4-(2-aminopyrimidin-4-yl)-3-chlorophenyl]carbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound NC1=NC=CC(C=2C(=CC(NC(=S)NC=3C=CC(NC(=O)C=4N=NSC=4)=CC=3)=CC=2)Cl)=N1 HVYHZVXYPGONHA-UHFFFAOYSA-N 0.000 description 1
- DJZFRFOAILHKJU-UHFFFAOYSA-N n-[4-[[4-(3,4,4a,5,6,7,8,8a-octahydro-2h-quinolin-1-yl)-3-chlorophenyl]carbamothioylamino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC(C=C1Cl)=CC=C1N1C2CCCCC2CCC1 DJZFRFOAILHKJU-UHFFFAOYSA-N 0.000 description 1
- ILGQVFKSSGWQGW-UHFFFAOYSA-N n-[4-[[4-(4-methylpiperazin-1-yl)-3-(trifluoromethyl)phenyl]methylcarbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound C1CN(C)CCN1C(C(=C1)C(F)(F)F)=CC=C1CNC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSN=N1 ILGQVFKSSGWQGW-UHFFFAOYSA-N 0.000 description 1
- NMHGDMRLSRPXDU-UHFFFAOYSA-N n-[4-[[4-(benzylamino)-3-chlorophenyl]carbamothioylamino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC(C=C1Cl)=CC=C1NCC1=CC=CC=C1 NMHGDMRLSRPXDU-UHFFFAOYSA-N 0.000 description 1
- IFMOCIVVVOZCBR-UHFFFAOYSA-N n-[4-[[4-(dimethylamino)-3-(trifluoromethyl)phenyl]methylcarbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound C1=C(C(F)(F)F)C(N(C)C)=CC=C1CNC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSN=N1 IFMOCIVVVOZCBR-UHFFFAOYSA-N 0.000 description 1
- SNYDYVQBHDSDKM-UHFFFAOYSA-N n-[4-[[4-[(1-benzylpyrrolidin-3-yl)-methylamino]-3-chlorophenyl]carbamothioylamino]phenyl]acetamide Chemical compound C=1C=C(NC(=S)NC=2C=CC(NC(C)=O)=CC=2)C=C(Cl)C=1N(C)C(C1)CCN1CC1=CC=CC=C1 SNYDYVQBHDSDKM-UHFFFAOYSA-N 0.000 description 1
- XMLXGQBBDZWZMN-UHFFFAOYSA-N n-[4-[[4-[[2-(azepan-1-yl)acetyl]amino]-3-chlorophenyl]carbamothioylamino]phenyl]furan-2-carboxamide Chemical compound C=1C=C(NC(=O)CN2CCCCCC2)C(Cl)=CC=1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CO1 XMLXGQBBDZWZMN-UHFFFAOYSA-N 0.000 description 1
- MFMBLQFAMXYYMG-UHFFFAOYSA-N n-[4-[[4-[[4-[(4-acetamidophenyl)carbamothioylamino]-2-chlorophenyl]disulfanyl]-3-chlorophenyl]carbamothioylamino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC(C=C1Cl)=CC=C1SSC(C(=C1)Cl)=CC=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 MFMBLQFAMXYYMG-UHFFFAOYSA-N 0.000 description 1
- SGMSPELNVSUXJI-UHFFFAOYSA-N n-[4-[[4-[bis(2-hydroxyethyl)amino]-3-chlorophenyl]carbamothioylamino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC1=CC=C(N(CCO)CCO)C(Cl)=C1 SGMSPELNVSUXJI-UHFFFAOYSA-N 0.000 description 1
- VQBXYYJPLAVCEG-UHFFFAOYSA-N n-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamothioylamino]phenyl]-1,3-oxazole-4-carboxamide Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(NC(=S)NC=2C=CC(NC(=O)C=3N=COC=3)=CC=2)=C1 VQBXYYJPLAVCEG-UHFFFAOYSA-N 0.000 description 1
- DLNZABJZNXHHSE-UHFFFAOYSA-N n-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamothioylamino]phenyl]-1,3-thiazole-4-carboxamide Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(NC(=S)NC=2C=CC(NC(=O)C=3N=CSC=3)=CC=2)=C1 DLNZABJZNXHHSE-UHFFFAOYSA-N 0.000 description 1
- TWVDOOYEVSAOAZ-UHFFFAOYSA-N n-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamothioylamino]phenyl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC(C=C1)=CC=C1NC(=S)NC1=CC=C(Cl)C(C(F)(F)F)=C1 TWVDOOYEVSAOAZ-UHFFFAOYSA-N 0.000 description 1
- MQNWVWVVXUSCBL-UHFFFAOYSA-N n-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound FC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NC1=CC=C(Cl)C(C(F)(F)F)=C1 MQNWVWVVXUSCBL-UHFFFAOYSA-N 0.000 description 1
- ZLJAZBIYYGENAH-UHFFFAOYSA-N n-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamothioylamino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC1=CC=C(Cl)C(C(F)(F)F)=C1 ZLJAZBIYYGENAH-UHFFFAOYSA-N 0.000 description 1
- PWHCPCOMLITMHI-UHFFFAOYSA-N n-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamothioylamino]phenyl]pyridine-2-carboxamide Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(NC(=S)NC=2C=CC(NC(=O)C=3N=CC=CC=3)=CC=2)=C1 PWHCPCOMLITMHI-UHFFFAOYSA-N 0.000 description 1
- APYAGTHHVRWBFN-UHFFFAOYSA-N n-[4-[[4-iodo-3-(trifluoromethyl)phenyl]carbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound C1=C(I)C(C(F)(F)F)=CC(NC(=S)NC=2C=CC(NC(=O)C=3N=NSC=3)=CC=2)=C1 APYAGTHHVRWBFN-UHFFFAOYSA-N 0.000 description 1
- DBNGUCCHASFJTB-UHFFFAOYSA-N n-[4-[[4-methoxy-3-(trifluoromethyl)phenyl]carbamothioylamino]phenyl]acetamide Chemical compound C1=C(C(F)(F)F)C(OC)=CC=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 DBNGUCCHASFJTB-UHFFFAOYSA-N 0.000 description 1
- VDOIYEHMZCAWPL-UHFFFAOYSA-N n-[4-[[5-(trifluoromethyl)pyridin-3-yl]carbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound FC(F)(F)C1=CN=CC(NC(=S)NC=2C=CC(NC(=O)C=3N=NSC=3)=CC=2)=C1 VDOIYEHMZCAWPL-UHFFFAOYSA-N 0.000 description 1
- VVHUNEAKEGIZLB-UHFFFAOYSA-N n-[4-[[5-chloro-2-(4-chlorophenoxy)-4-pyrrol-1-ylphenyl]carbamothioylamino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC1=CC(Cl)=C(N2C=CC=C2)C=C1OC1=CC=C(Cl)C=C1 VVHUNEAKEGIZLB-UHFFFAOYSA-N 0.000 description 1
- HXMDKXHJBZYMGS-UHFFFAOYSA-N n-[4-[[5-chloro-2-(dimethylamino)-4-methoxyphenyl]carbamothioylamino]phenyl]acetamide Chemical compound C1=C(Cl)C(OC)=CC(N(C)C)=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 HXMDKXHJBZYMGS-UHFFFAOYSA-N 0.000 description 1
- OTGHLEWTFPXVKQ-UHFFFAOYSA-N n-[4-[[5-chloro-2-(dimethylamino)phenyl]carbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound CN(C)C1=CC=C(Cl)C=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSN=N1 OTGHLEWTFPXVKQ-UHFFFAOYSA-N 0.000 description 1
- WLPITKOWLYNTKY-UHFFFAOYSA-N n-[4-[[[3,5-bis(trifluoromethyl)phenyl]carbamothioylamino]methyl]phenyl]-2-fluorobenzamide Chemical compound FC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1CNC(=S)NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 WLPITKOWLYNTKY-UHFFFAOYSA-N 0.000 description 1
- XQOHNEXQMOKXJL-UHFFFAOYSA-N n-[4-[[[3,5-bis(trifluoromethyl)phenyl]carbamothioylamino]methyl]phenyl]thiadiazole-4-carboxamide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(NC(=S)NCC=2C=CC(NC(=O)C=3N=NSC=3)=CC=2)=C1 XQOHNEXQMOKXJL-UHFFFAOYSA-N 0.000 description 1
- HJMGUZZCNQKNIW-UHFFFAOYSA-N n-[4-acetamido-2-(trifluoromethyl)phenyl]-2,2,2-trifluoroacetamide Chemical compound CC(=O)NC1=CC=C(NC(=O)C(F)(F)F)C(C(F)(F)F)=C1 HJMGUZZCNQKNIW-UHFFFAOYSA-N 0.000 description 1
- MIHJCLQINRFOLX-UHFFFAOYSA-N n-[4-nitro-3-(trifluoromethyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 MIHJCLQINRFOLX-UHFFFAOYSA-N 0.000 description 1
- BTYHTARKAWTERX-UHFFFAOYSA-N n-[5-[(3,5-dichlorophenyl)carbamothioylamino]pyridin-2-yl]thiadiazole-4-carboxamide Chemical compound ClC1=CC(Cl)=CC(NC(=S)NC=2C=NC(NC(=O)C=3N=NSC=3)=CC=2)=C1 BTYHTARKAWTERX-UHFFFAOYSA-N 0.000 description 1
- HXYJCDRXSKAAEX-UHFFFAOYSA-N n-[5-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]pyridin-2-yl]acetamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC1=CC=C(NC(C)=O)N=C1 HXYJCDRXSKAAEX-UHFFFAOYSA-N 0.000 description 1
- ZAIGBGKEDQFDMB-UHFFFAOYSA-N n-[5-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]pyridin-2-yl]thiadiazole-4-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=N1)=CC=C1NC(=O)C1=CSN=N1 ZAIGBGKEDQFDMB-UHFFFAOYSA-N 0.000 description 1
- AWPXBVFMDACJGY-UHFFFAOYSA-N n-[6-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]pyridin-3-yl]-2-fluorobenzamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(N=C1)=CC=C1NC(=O)C1=CC=CC=C1F AWPXBVFMDACJGY-UHFFFAOYSA-N 0.000 description 1
- SHNIRXYDMJCBIS-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methylidene]hydroxylamine Chemical compound ON=CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 SHNIRXYDMJCBIS-UHFFFAOYSA-N 0.000 description 1
- BHQIGUWUNPQBJY-UHFFFAOYSA-N n-diazomethanesulfonamide Chemical compound CS(=O)(=O)N=[N+]=[N-] BHQIGUWUNPQBJY-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- FPAULGQOCSSJCZ-UHFFFAOYSA-N n-methoxy-1-(1-methylpyrrol-2-yl)ethanimine Chemical compound CON=C(C)C1=CC=CN1C FPAULGQOCSSJCZ-UHFFFAOYSA-N 0.000 description 1
- CATIDUWGAIDOJZ-UHFFFAOYSA-N n-methoxy-1-(2-methylphenyl)ethanimine Chemical compound CON=C(C)C1=CC=CC=C1C CATIDUWGAIDOJZ-UHFFFAOYSA-N 0.000 description 1
- QJRRDVCQEPIKOD-UHFFFAOYSA-N n-methoxy-1-(4-piperidin-1-ylsulfonylphenyl)ethanimine Chemical compound C1=CC(C(C)=NOC)=CC=C1S(=O)(=O)N1CCCCC1 QJRRDVCQEPIKOD-UHFFFAOYSA-N 0.000 description 1
- IJOFLTHNVRCNHI-UHFFFAOYSA-N n-methoxy-1-[3-(trifluoromethyl)phenyl]ethanimine Chemical compound CON=C(C)C1=CC=CC(C(F)(F)F)=C1 IJOFLTHNVRCNHI-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical class [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 230000002276 neurotropic effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229960003966 nicotinamide Drugs 0.000 description 1
- 239000011570 nicotinamide Substances 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000003833 nucleoside derivatives Chemical class 0.000 description 1
- LTSOKNLNMCZPLV-UHFFFAOYSA-N o-(3-chlorophenyl) n-[4-(furan-2-carbonylamino)phenyl]carbamothioate Chemical compound ClC1=CC=CC(OC(=S)NC=2C=CC(NC(=O)C=3OC=CC=3)=CC=2)=C1 LTSOKNLNMCZPLV-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 244000039328 opportunistic pathogen Species 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
- QJPQVXSHYBGQGM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 description 1
- WYMSBXTXOHUIGT-UHFFFAOYSA-N paraoxon Chemical compound CCOP(=O)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 WYMSBXTXOHUIGT-UHFFFAOYSA-N 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 230000007918 pathogenicity Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 1
- 125000000286 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
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000013014 purified material Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 229940070891 pyridium Drugs 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000010322 reactivation of latent virus Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 229940016590 sarkosyl Drugs 0.000 description 1
- 108700004121 sarkosyl Proteins 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 206010040872 skin infection Diseases 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000001476 sodium potassium tartrate Substances 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 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
- AVTUGLVQFAWYJJ-UHFFFAOYSA-N tert-butyl 2-(2,6-dichloro-4-nitrophenoxy)acetate Chemical compound CC(C)(C)OC(=O)COC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl AVTUGLVQFAWYJJ-UHFFFAOYSA-N 0.000 description 1
- BPGYZWSYAQHVDY-UHFFFAOYSA-N tert-butyl 2-(4-amino-2,6-dichlorophenoxy)acetate Chemical compound CC(C)(C)OC(=O)COC1=C(Cl)C=C(N)C=C1Cl BPGYZWSYAQHVDY-UHFFFAOYSA-N 0.000 description 1
- GNMOCKIWVFZFRG-UHFFFAOYSA-N tert-butyl 2-[4-[(4-acetamidophenyl)carbamothioylamino]-2-chloro-5-methoxyphenoxy]acetate Chemical compound COC1=CC(OCC(=O)OC(C)(C)C)=C(Cl)C=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 GNMOCKIWVFZFRG-UHFFFAOYSA-N 0.000 description 1
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
- BZRBABVBSBPJPS-UHFFFAOYSA-N tert-butyl N-(4-butoxy-3,5-dichlorophenyl)carbamate tert-butyl N-(3,5-dichloro-4-ethoxyphenyl)carbamate tert-butyl N-(3,5-dichloro-4-phenylmethoxyphenyl)carbamate Chemical compound C(C)(C)(C)OC(NC1=CC(=C(C(=C1)Cl)OCC1=CC=CC=C1)Cl)=O.C(C)(C)(C)OC(NC1=CC(=C(C(=C1)Cl)OCCCC)Cl)=O.C(C)(C)(C)OC(NC1=CC(=C(C(=C1)Cl)OCC)Cl)=O BZRBABVBSBPJPS-UHFFFAOYSA-N 0.000 description 1
- VRWMYYXTZKCOKP-UHFFFAOYSA-N tert-butyl N-[4-(pyridine-2-carbonylamino)phenyl]carbamate tert-butyl N-[4-(quinoline-2-carbonylamino)phenyl]carbamate Chemical compound C(C)(C)(C)OC(NC1=CC=C(C=C1)NC(=O)C1=NC=CC=C1)=O.C(C)(C)(C)OC(NC1=CC=C(C=C1)NC(=O)C1=NC2=CC=CC=C2C=C1)=O VRWMYYXTZKCOKP-UHFFFAOYSA-N 0.000 description 1
- VPONSBSZPHIIFJ-UHFFFAOYSA-N tert-butyl n-(3,5-dichloro-4-ethoxyphenyl)carbamate Chemical compound CCOC1=C(Cl)C=C(NC(=O)OC(C)(C)C)C=C1Cl VPONSBSZPHIIFJ-UHFFFAOYSA-N 0.000 description 1
- PTXUPLVXQMXUPJ-UHFFFAOYSA-N tert-butyl n-(3-chloro-4-ethenylphenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(C=C)C(Cl)=C1 PTXUPLVXQMXUPJ-UHFFFAOYSA-N 0.000 description 1
- ANVBHTRIPGBMFB-UHFFFAOYSA-N tert-butyl n-(3-chloro-4-iodophenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(I)C(Cl)=C1 ANVBHTRIPGBMFB-UHFFFAOYSA-N 0.000 description 1
- JCIPDXPPSLPJTH-UHFFFAOYSA-N tert-butyl n-(3-chloro-4-methylsulfinylphenyl)carbamate Chemical compound CS(=O)C1=CC=C(NC(=O)OC(C)(C)C)C=C1Cl JCIPDXPPSLPJTH-UHFFFAOYSA-N 0.000 description 1
- DNOQLJHQFUMRIM-UHFFFAOYSA-N tert-butyl n-(3-chloro-4-methylsulfonylphenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(S(C)(=O)=O)C(Cl)=C1 DNOQLJHQFUMRIM-UHFFFAOYSA-N 0.000 description 1
- HDGDNDFUABLUAQ-UHFFFAOYSA-N tert-butyl n-(4-amino-3-chlorophenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(N)C(Cl)=C1 HDGDNDFUABLUAQ-UHFFFAOYSA-N 0.000 description 1
- WIVYTYZCVWHWSH-UHFFFAOYSA-N tert-butyl n-(4-aminophenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(N)C=C1 WIVYTYZCVWHWSH-UHFFFAOYSA-N 0.000 description 1
- SJRDSJJWUCHLOG-UHFFFAOYSA-N tert-butyl n-(4-benzamidophenyl)carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=CC=C1 SJRDSJJWUCHLOG-UHFFFAOYSA-N 0.000 description 1
- NXHDMOGWVRMCTL-UHFFFAOYSA-N tert-butyl n-[(4-nitrophenyl)methyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC1=CC=C([N+]([O-])=O)C=C1 NXHDMOGWVRMCTL-UHFFFAOYSA-N 0.000 description 1
- MFAFIOHHCVGMCD-UHFFFAOYSA-N tert-butyl n-[3,5-dichloro-4-(2-hydroxyethoxy)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(Cl)=C(OCCO)C(Cl)=C1 MFAFIOHHCVGMCD-UHFFFAOYSA-N 0.000 description 1
- DEYZBLNDBIZBLK-UHFFFAOYSA-N tert-butyl n-[3-(2-methylpropyl)-5-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)CC1=CC(NC(=O)OC(C)(C)C)=CC(C(F)(F)F)=C1 DEYZBLNDBIZBLK-UHFFFAOYSA-N 0.000 description 1
- PGCWCIPXTAAMTC-UHFFFAOYSA-N tert-butyl n-[3-bromo-5-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(Br)=CC(C(F)(F)F)=C1 PGCWCIPXTAAMTC-UHFFFAOYSA-N 0.000 description 1
- GSDSJTBMWAOPMC-UHFFFAOYSA-N tert-butyl n-[3-chloro-5-[[4-(thiadiazole-4-carbonylamino)phenyl]carbamothioylamino]phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(Cl)=CC(NC(=S)NC=2C=CC(NC(=O)C=3N=NSC=3)=CC=2)=C1 GSDSJTBMWAOPMC-UHFFFAOYSA-N 0.000 description 1
- ACRFZDJQEPJRIM-UHFFFAOYSA-N tert-butyl n-[4-(1h-pyrazole-4-carbonylamino)phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CNN=C1 ACRFZDJQEPJRIM-UHFFFAOYSA-N 0.000 description 1
- KUCQOHPORDNEDR-UHFFFAOYSA-N tert-butyl n-[4-[(2-phenylacetyl)amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)CC1=CC=CC=C1 KUCQOHPORDNEDR-UHFFFAOYSA-N 0.000 description 1
- LRVSRVVHAJGNEH-UHFFFAOYSA-N tert-butyl n-[4-[(3-aminobenzoyl)amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=CC(N)=C1 LRVSRVVHAJGNEH-UHFFFAOYSA-N 0.000 description 1
- YVXLIYTVGSKEKH-UHFFFAOYSA-N tert-butyl n-[4-[(3-fluorobenzoyl)amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=CC(F)=C1 YVXLIYTVGSKEKH-UHFFFAOYSA-N 0.000 description 1
- NQSCTAFELSQCCB-UHFFFAOYSA-N tert-butyl n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]phenyl]carbamate Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC1=CC=C(NC(=O)OC(C)(C)C)C=C1 NQSCTAFELSQCCB-UHFFFAOYSA-N 0.000 description 1
- SSGOEFFYKSGLCW-UHFFFAOYSA-N tert-butyl n-[4-[[2-(dimethylamino)acetyl]amino]phenyl]carbamate Chemical compound CN(C)CC(=O)NC1=CC=C(NC(=O)OC(C)(C)C)C=C1 SSGOEFFYKSGLCW-UHFFFAOYSA-N 0.000 description 1
- YZRLHQDZAGKWPV-UHFFFAOYSA-N tert-butyl n-[4-[[3-(trifluoromethyl)benzoyl]amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 YZRLHQDZAGKWPV-UHFFFAOYSA-N 0.000 description 1
- UNKOQHWDOUXVFU-UHFFFAOYSA-N tert-butyl n-[4-[[4-(furan-3-yl)thiadiazole-5-carbonyl]amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=C(C2=COC=C2)N=NS1 UNKOQHWDOUXVFU-UHFFFAOYSA-N 0.000 description 1
- KVAGTFWNDBSXKP-UHFFFAOYSA-N tert-butyl n-[[4-[(2-fluorobenzoyl)amino]phenyl]methyl]carbamate Chemical compound C1=CC(CNC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=CC=C1F KVAGTFWNDBSXKP-UHFFFAOYSA-N 0.000 description 1
- NLQZMWDNQGOWHY-UHFFFAOYSA-N tert-butyl n-amino-n-phenylcarbamate Chemical class CC(C)(C)OC(=O)N(N)C1=CC=CC=C1 NLQZMWDNQGOWHY-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- 125000005309 thioalkoxy group Chemical group 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 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
- YNVOMSDITJMNET-UHFFFAOYSA-N thiophene-3-carboxylic acid Chemical compound OC(=O)C=1C=CSC=1 YNVOMSDITJMNET-UHFFFAOYSA-N 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 229940055764 triaz Drugs 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
- 210000003501 vero cell Anatomy 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D307/85—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- 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
-
- 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
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C335/20—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C335/22—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20816498A | 1998-12-09 | 1998-12-09 | |
| US09/208,164 | 1998-12-09 | ||
| PCT/US1999/028916 WO2000034261A2 (en) | 1998-12-09 | 1999-12-06 | Heterocyclic carboxamide-containing thiourea inhibitors of herpes viruses containing a substituted phenylenediamine group |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2351690A1 true CA2351690A1 (en) | 2000-06-15 |
Family
ID=22773466
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002351690A Abandoned CA2351690A1 (en) | 1998-12-09 | 1999-12-06 | Heterocyclic carboxamide-containing thiourea inhibitors of herpes viruses containing a substituted phenylenediamine group |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP1144399A3 (cs) |
| JP (1) | JP2002533301A (cs) |
| KR (1) | KR20010086091A (cs) |
| CN (1) | CN1367785A (cs) |
| AU (1) | AU2353900A (cs) |
| BR (1) | BR9916043A (cs) |
| CA (1) | CA2351690A1 (cs) |
| CZ (1) | CZ20012063A3 (cs) |
| EA (1) | EA200100639A1 (cs) |
| HU (1) | HUP0203405A2 (cs) |
| IL (1) | IL143263A0 (cs) |
| NO (1) | NO20012835L (cs) |
| WO (1) | WO2000034261A2 (cs) |
| ZA (1) | ZA200104322B (cs) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6844367B1 (en) | 1999-09-17 | 2005-01-18 | Millennium Pharmaceuticals, Inc. | Benzamides and related inhibitors of factor Xa |
| ATE311366T1 (de) | 2000-02-29 | 2005-12-15 | Millennium Pharm Inc | Benzamide und ähnliche inhibitoren vom faktor xa |
| KR20070007759A (ko) * | 2003-07-10 | 2007-01-16 | 아칠리온 파르마세우티칼스 인코포레이티드 | 바이러스 복제 억제제로서 유용한 치환된 아릴티오우레아유도체 |
| DE102004015007A1 (de) * | 2004-03-26 | 2005-10-13 | Bayer Healthcare Ag | Substituierte Imidazole |
| TW200600492A (en) | 2004-05-18 | 2006-01-01 | Achillion Pharmaceuticals Inc | Substituted aryl acylthioureas and related compounds; inhibitors of viral replication |
| DE102005008183A1 (de) | 2005-02-23 | 2006-08-31 | Bayer Healthcare Ag | Heterocyclylamid-substituierte Imidazole |
| PT2077995E (pt) | 2006-11-02 | 2012-05-10 | Millennium Pharm Inc | Métodos de sintetizar sais farmacêuticos de um inibidor de fator xa |
| WO2014070979A1 (en) * | 2012-11-03 | 2014-05-08 | Boehringer Ingelheim International Gmbh | Inhibitors of cytomegalovirus |
| WO2014070978A1 (en) * | 2012-11-03 | 2014-05-08 | Boehringer Ingelheim International Gmbh | Inhibitors of cytomegalovirus |
| CN112807294B (zh) * | 2019-11-18 | 2023-09-05 | 武汉大学 | 一种酰基硫脲类化合物在制备治疗或预防单纯疱疹病毒i型感染药物中的应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE298741T1 (de) * | 1997-04-10 | 2005-07-15 | Pharmacia & Upjohn Co Llc | Polyaromatische verbindungen zur behandlung von herpes-infektionen |
-
1999
- 1999-12-06 EA EA200100639A patent/EA200100639A1/ru unknown
- 1999-12-06 EP EP99967213A patent/EP1144399A3/en not_active Withdrawn
- 1999-12-06 AU AU23539/00A patent/AU2353900A/en not_active Abandoned
- 1999-12-06 IL IL14326399A patent/IL143263A0/xx unknown
- 1999-12-06 CN CN99815998A patent/CN1367785A/zh active Pending
- 1999-12-06 BR BR9916043-9A patent/BR9916043A/pt not_active Application Discontinuation
- 1999-12-06 KR KR1020017007117A patent/KR20010086091A/ko not_active Withdrawn
- 1999-12-06 CZ CZ20012063A patent/CZ20012063A3/cs unknown
- 1999-12-06 WO PCT/US1999/028916 patent/WO2000034261A2/en not_active Application Discontinuation
- 1999-12-06 HU HU0203405A patent/HUP0203405A2/hu unknown
- 1999-12-06 JP JP2000586708A patent/JP2002533301A/ja active Pending
- 1999-12-06 CA CA002351690A patent/CA2351690A1/en not_active Abandoned
-
2001
- 2001-05-25 ZA ZA200104322A patent/ZA200104322B/en unknown
- 2001-06-08 NO NO20012835A patent/NO20012835L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2002533301A (ja) | 2002-10-08 |
| KR20010086091A (ko) | 2001-09-07 |
| NO20012835L (no) | 2001-07-19 |
| IL143263A0 (en) | 2002-04-21 |
| WO2000034261A2 (en) | 2000-06-15 |
| CN1367785A (zh) | 2002-09-04 |
| EP1144399A3 (en) | 2002-09-11 |
| WO2000034261A3 (en) | 2002-01-31 |
| HUP0203405A2 (hu) | 2003-02-28 |
| NO20012835D0 (no) | 2001-06-08 |
| BR9916043A (pt) | 2001-12-04 |
| ZA200104322B (en) | 2002-10-25 |
| AU2353900A (en) | 2000-06-26 |
| CZ20012063A3 (cs) | 2001-10-17 |
| EA200100639A1 (ru) | 2002-06-27 |
| EP1144399A2 (en) | 2001-10-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6262082B1 (en) | Diaminopyridine-containing thiourea inhibitors of herpes viruses | |
| CA2350899A1 (en) | Acetamide and substituted acetamide-containing thiourea inhibitors of herpes viruses | |
| EP1137632B1 (en) | Thiourea inhibitors of herpes viruses | |
| CA2350767A1 (en) | Heterocyclic carboxamide-containing thiourea inhibitors of herpes viruses containing phenylenediamine group | |
| CA2351690A1 (en) | Heterocyclic carboxamide-containing thiourea inhibitors of herpes viruses containing a substituted phenylenediamine group | |
| EP1137645B1 (en) | Alpha-methylbenzyl-containing thiourea inhibitors of herpes viruses containing a phenylenediamine group | |
| US6201013B1 (en) | Heterocyclic carboxamide-containing thiourea inhibitors of herpes viruses containing a substituted phenylenediamine group | |
| WO2000034269A1 (en) | Thiourea inhibitors of herpes viruses | |
| AU756043B2 (en) | Thiourea inhibitors of herpes viruses | |
| US6207715B1 (en) | Alpha-methylbenzyl-containing thiourea inhibitors of herpes viruses containing a substituted phenylene-diamine group | |
| US6335350B1 (en) | Acetamide and substituted acetamide-containing thiourea inhibitors of herpes viruses | |
| CA2350996A1 (en) | Thiourea inhibitors of herpes viruses | |
| US6255349B1 (en) | Alph-methylbenzyl-containing thiourea inhibitors of herpes viruses containing a phenylenediamine group | |
| US6262090B1 (en) | Aminopyridine-containing thiourea inhibitors of herpes viruses | |
| US6426355B1 (en) | Heterocyclic carboxamide-containing thiourea inhibitors of herpes viruses containing phenylenediamine group |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |