ZA200104377B - Heterocyclic carboxamide-containing thiourea inhibitors of herpes viruses containing phenylenediamine group. - Google Patents

Info

Publication number

ZA200104377B

ZA200104377B ZA200104377A ZA200104377A ZA200104377B ZA 200104377 B ZA200104377 B ZA 200104377B ZA 200104377 A ZA200104377 A ZA 200104377A ZA 200104377 A ZA200104377 A ZA 200104377A ZA 200104377 B ZA200104377 B ZA 200104377B

Authority

ZA

South Africa

Prior art keywords

phenyl

amide

thioureido

carboxylic acid

thiadiazole

Prior art date

1998-12-09

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• -1 Heterocyclic carboxamide Chemical class 0.000 title claims description 158
• 241001529453 unidentified herpesvirus Species 0.000 title claims description 12
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title description 13
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 title description 4
• 239000003112 inhibitor Substances 0.000 title description 3
• GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical group NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 title description 2
• 238000000034 method Methods 0.000 claims description 260
• HJZYBDPHAHGHAZ-UHFFFAOYSA-N thiadiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSN=N1 HJZYBDPHAHGHAZ-UHFFFAOYSA-N 0.000 claims description 126
• 125000004432 carbon atom Chemical group C* 0.000 claims description 93
• 150000001875 compounds Chemical class 0.000 claims description 89
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 56
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 46
• SMNDYUVBFMFKNZ-UHFFFAOYSA-N pyromucic acid Natural products OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 claims description 45
• 125000000217 alkyl group Chemical group 0.000 claims description 43
• 229910052739 hydrogen Inorganic materials 0.000 claims description 26
• 239000001257 hydrogen Substances 0.000 claims description 26
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 18
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
• 125000003118 aryl group Chemical group 0.000 claims description 16
• 125000001072 heteroaryl group Chemical group 0.000 claims description 16
• 239000002253 acid Substances 0.000 claims description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
• 125000003342 alkenyl group Chemical group 0.000 claims description 12
• 229910052736 halogen Inorganic materials 0.000 claims description 12
• 150000002367 halogens Chemical class 0.000 claims description 12
• 150000002431 hydrogen Chemical class 0.000 claims description 12
• 150000003839 salts Chemical class 0.000 claims description 12
• 125000003545 alkoxy group Chemical group 0.000 claims description 9
• HMVYYTRDXNKRBQ-UHFFFAOYSA-N 1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSC=N1 HMVYYTRDXNKRBQ-UHFFFAOYSA-N 0.000 claims description 8
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
• 241000701085 Human alphaherpesvirus 3 Species 0.000 claims description 7
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
• 125000003282 alkyl amino group Chemical group 0.000 claims description 6
• 125000000304 alkynyl group Chemical group 0.000 claims description 6
• 230000003287 optical effect Effects 0.000 claims description 6
• 125000000335 thiazolyl group Chemical group 0.000 claims description 6
• BIUDHHGROGJSHN-UHFFFAOYSA-N 4-fluoro-3-(trifluoromethyl)benzaldehyde Chemical group FC1=CC=C(C=O)C=C1C(F)(F)F BIUDHHGROGJSHN-UHFFFAOYSA-N 0.000 claims description 5
• 125000004001 thioalkyl group Chemical group 0.000 claims description 5
• 150000001408 amides Chemical class 0.000 claims description 4
• 125000002541 furyl group Chemical group 0.000 claims description 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 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
• JBCFJMYPJJWIRG-UHFFFAOYSA-N 1,3-oxazole-4-carboxylic acid Chemical compound OC(=O)C1=COC=N1 JBCFJMYPJJWIRG-UHFFFAOYSA-N 0.000 claims description 3
• 241000700584 Simplexvirus Species 0.000 claims description 3
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• TYTLQKQSCSFIAB-UHFFFAOYSA-N n-[4-(3,3-diphenylpropylcarbamothioylamino)phenyl]thiadiazole-4-carboxamide Chemical compound C=1SN=NC=1C(=O)NC(C=C1)=CC=C1NC(=S)NCCC(C=1C=CC=CC=1)C1=CC=CC=C1 TYTLQKQSCSFIAB-UHFFFAOYSA-N 0.000 claims description 2
• OIFWQZLKUZPAFB-UHFFFAOYSA-N n-[4-[(2-chlorophenyl)methylcarbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound ClC1=CC=CC=C1CNC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSN=N1 OIFWQZLKUZPAFB-UHFFFAOYSA-N 0.000 claims description 2
• JHVUJFDFMDLIMN-UHFFFAOYSA-N n-[4-[(3,4,5-trichlorophenyl)carbamothioylamino]phenyl]furan-2-carboxamide Chemical compound ClC1=C(Cl)C(Cl)=CC(NC(=S)NC=2C=CC(NC(=O)C=3OC=CC=3)=CC=2)=C1 JHVUJFDFMDLIMN-UHFFFAOYSA-N 0.000 claims description 2
• GFTNHDYFNMFCPM-UHFFFAOYSA-N n-[4-[(3,4-dichlorophenyl)carbamothioylamino]phenyl]-1,3-oxazole-4-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=COC=N1 GFTNHDYFNMFCPM-UHFFFAOYSA-N 0.000 claims description 2
• RCHYGXSGNBTKQE-UHFFFAOYSA-N n-[4-[(3,4-difluorophenyl)methylcarbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound C1=C(F)C(F)=CC=C1CNC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSN=N1 RCHYGXSGNBTKQE-UHFFFAOYSA-N 0.000 claims description 2
• VVZMTECPAPKWST-UHFFFAOYSA-N n-[4-[(3,5-dichloro-2-methoxy-4-methylphenyl)carbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound C1=C(Cl)C(C)=C(Cl)C(OC)=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSN=N1 VVZMTECPAPKWST-UHFFFAOYSA-N 0.000 claims description 2
• FOQOUCQRLFOERI-UHFFFAOYSA-N n-[4-[(3,5-dichlorophenyl)carbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound ClC1=CC(Cl)=CC(NC(=S)NC=2C=CC(NC(=O)C=3N=NSC=3)=CC=2)=C1 FOQOUCQRLFOERI-UHFFFAOYSA-N 0.000 claims description 2
• 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 claims description 2
• PTEIQINKHAKYKR-UHFFFAOYSA-N n-[4-[(3-chloro-4-fluorophenyl)carbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound C1=C(Cl)C(F)=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSN=N1 PTEIQINKHAKYKR-UHFFFAOYSA-N 0.000 claims description 2
• YJPQWEHLCZGPDF-UHFFFAOYSA-N n-[4-[(3-chloro-4-methylphenyl)carbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound C1=C(Cl)C(C)=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSN=N1 YJPQWEHLCZGPDF-UHFFFAOYSA-N 0.000 claims description 2
• 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 claims description 2
• 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 claims description 2
• MWUAINJFZGMLNE-UHFFFAOYSA-N n-[4-[1-(4-fluorophenyl)ethylcarbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound C=1C=C(F)C=CC=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSN=N1 MWUAINJFZGMLNE-UHFFFAOYSA-N 0.000 claims description 2
• 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 claims description 2
• ZZLZBDZIEWNAIM-UHFFFAOYSA-N n-[4-[2-(3-chlorophenoxy)ethylcarbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound ClC1=CC=CC(OCCNC(=S)NC=2C=CC(NC(=O)C=3N=NSC=3)=CC=2)=C1 ZZLZBDZIEWNAIM-UHFFFAOYSA-N 0.000 claims description 2
• LBIQYDCKMHTWEP-UHFFFAOYSA-N n-[4-[2-(3-chlorophenyl)ethylcarbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound ClC1=CC=CC(CCNC(=S)NC=2C=CC(NC(=O)C=3N=NSC=3)=CC=2)=C1 LBIQYDCKMHTWEP-UHFFFAOYSA-N 0.000 claims description 2
• YBDYEGKJABWFFH-UHFFFAOYSA-N n-[4-[2-(3-iodophenoxy)ethylcarbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound IC1=CC=CC(OCCNC(=S)NC=2C=CC(NC(=O)C=3N=NSC=3)=CC=2)=C1 YBDYEGKJABWFFH-UHFFFAOYSA-N 0.000 claims description 2
• UFFGKLJMXYRIKH-UHFFFAOYSA-N n-[4-[2-[3-(dimethylamino)-5-(trifluoromethyl)phenyl]ethylcarbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound FC(F)(F)C1=CC(N(C)C)=CC(CCNC(=S)NC=2C=CC(NC(=O)C=3N=NSC=3)=CC=2)=C1 UFFGKLJMXYRIKH-UHFFFAOYSA-N 0.000 claims description 2
• BAOOUYCCHWPULG-UHFFFAOYSA-N n-[4-[2-[3-(trifluoromethyl)phenyl]ethylcarbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound FC(F)(F)C1=CC=CC(CCNC(=S)NC=2C=CC(NC(=O)C=3N=NSC=3)=CC=2)=C1 BAOOUYCCHWPULG-UHFFFAOYSA-N 0.000 claims description 2
• JQCOOJRNQBPMSO-LLVKDONJSA-N n-[4-[[(1r)-1-(4-bromophenyl)ethyl]carbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound N([C@H](C)C=1C=CC(Br)=CC=1)C(=S)NC(C=C1)=CC=C1NC(=O)C1=CSN=N1 JQCOOJRNQBPMSO-LLVKDONJSA-N 0.000 claims description 2
• AQFINXWRUKGXEY-UHFFFAOYSA-N n-[4-[[2-fluoro-5-(trifluoromethyl)phenyl]methylcarbamothioylamino]phenyl]-1,3-thiazole-4-carboxamide Chemical compound FC1=CC=C(C(F)(F)F)C=C1CNC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSC=N1 AQFINXWRUKGXEY-UHFFFAOYSA-N 0.000 claims description 2
• 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 claims description 2
• 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 claims description 2
• GTUWFDZALUOBIP-UHFFFAOYSA-N n-[4-[[3-(dimethylamino)-5-(trifluoromethyl)phenyl]carbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound FC(F)(F)C1=CC(N(C)C)=CC(NC(=S)NC=2C=CC(NC(=O)C=3N=NSC=3)=CC=2)=C1 GTUWFDZALUOBIP-UHFFFAOYSA-N 0.000 claims description 2
• OMFMWSJRWMAHKL-UHFFFAOYSA-N n-[4-[[3-(trifluoromethyl)phenyl]methylcarbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound FC(F)(F)C1=CC=CC(CNC(=S)NC=2C=CC(NC(=O)C=3N=NSC=3)=CC=2)=C1 OMFMWSJRWMAHKL-UHFFFAOYSA-N 0.000 claims description 2
• CQFWVDYWYLYBFX-UHFFFAOYSA-N n-[4-[[3-bromo-4-(trifluoromethoxy)phenyl]carbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound C1=C(Br)C(OC(F)(F)F)=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSN=N1 CQFWVDYWYLYBFX-UHFFFAOYSA-N 0.000 claims description 2
• YCTUGQIQDGYJPA-UHFFFAOYSA-N n-[4-[[3-fluoro-5-(trifluoromethyl)phenyl]methylcarbamothioylamino]phenyl]furan-2-carboxamide Chemical compound FC(F)(F)C1=CC(F)=CC(CNC(=S)NC=2C=CC(NC(=O)C=3OC=CC=3)=CC=2)=C1 YCTUGQIQDGYJPA-UHFFFAOYSA-N 0.000 claims description 2
• 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 claims description 2
• AXRKQAPHBSELKR-UHFFFAOYSA-N n-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(NC(=S)NC=2C=CC(NC(=O)C=3N=NSC=3)=CC=2)=C1 AXRKQAPHBSELKR-UHFFFAOYSA-N 0.000 claims description 2
• 241000701024 Human betaherpesvirus 5 Species 0.000 claims 2
• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 2
• 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims 1
• PQQRHWFRZHFGFM-UHFFFAOYSA-N 1,3-thiazole-4-carboxamide Chemical compound NC(=O)C1=CSC=N1 PQQRHWFRZHFGFM-UHFFFAOYSA-N 0.000 claims 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 claims 1
• KUYUJNMYKIUCNO-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[(3,5-dichlorophenyl)methyl]thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NCC1=CC(Cl)=CC(Cl)=C1 KUYUJNMYKIUCNO-UHFFFAOYSA-N 0.000 claims 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 claims 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 claims 1
• WCZVQUIDTIZVIM-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[2-(2-fluorophenyl)ethyl]thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NCCC1=CC=CC=C1F WCZVQUIDTIZVIM-UHFFFAOYSA-N 0.000 claims 1
• WLLXQVLHYZFLQM-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[2-(3-bromophenoxy)ethyl]thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NCCOC1=CC=CC(Br)=C1 WLLXQVLHYZFLQM-UHFFFAOYSA-N 0.000 claims 1
• XRHOANJGEGVNCG-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[2-(4-ethylphenyl)ethyl]thiourea Chemical compound C1=CC(CC)=CC=C1CCNC(=S)NC1=CC=C(N)C=C1 XRHOANJGEGVNCG-UHFFFAOYSA-N 0.000 claims 1
• ORKLFWKUJGHAET-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[2-[3-fluoro-5-(trifluoromethyl)phenyl]ethyl]thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NCCC1=CC(F)=CC(C(F)(F)F)=C1 ORKLFWKUJGHAET-UHFFFAOYSA-N 0.000 claims 1
• UDMROEUJWFGHSA-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[4-bromo-3-(trifluoromethyl)phenyl]thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NC1=CC=C(Br)C(C(F)(F)F)=C1 UDMROEUJWFGHSA-UHFFFAOYSA-N 0.000 claims 1
• QATNKWDTPVKHCI-UHFFFAOYSA-N 1-(4-aminophenyl)-3-[4-chloro-3-(trifluoromethyl)phenyl]thiourea Chemical compound C1=CC(N)=CC=C1NC(=S)NC1=CC=C(Cl)C(C(F)(F)F)=C1 QATNKWDTPVKHCI-UHFFFAOYSA-N 0.000 claims 1
• DMUXRCHOODXUGV-UHFFFAOYSA-N 1-[2,4-bis(trifluoromethyl)phenyl]ethanamine Chemical compound CC(N)C1=CC=C(C(F)(F)F)C=C1C(F)(F)F DMUXRCHOODXUGV-UHFFFAOYSA-N 0.000 claims 1
• 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
• GJDMPZRYSKQXMP-UHFFFAOYSA-N n-[4-(1,3-benzodioxol-5-ylmethylcarbamothioylamino)phenyl]furan-2-carboxamide Chemical compound C=1C=C(NC(=S)NCC=2C=C3OCOC3=CC=2)C=CC=1NC(=O)C1=CC=CO1 GJDMPZRYSKQXMP-UHFFFAOYSA-N 0.000 claims 1
• HHUGPTZCWLZOGP-UHFFFAOYSA-N n-[4-(1,3-benzodioxol-5-ylmethylcarbamothioylamino)phenyl]thiadiazole-4-carboxamide Chemical compound C=1C=C(NC(=S)NCC=2C=C3OCOC3=CC=2)C=CC=1NC(=O)C1=CSN=N1 HHUGPTZCWLZOGP-UHFFFAOYSA-N 0.000 claims 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 claims 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 claims 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 claims 1
• XNXJWTNJPVHQIH-UHFFFAOYSA-N n-[4-[(3,5-difluorophenyl)methylcarbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound FC1=CC(F)=CC(CNC(=S)NC=2C=CC(NC(=O)C=3N=NSC=3)=CC=2)=C1 XNXJWTNJPVHQIH-UHFFFAOYSA-N 0.000 claims 1
• RBMUSXLONZJXJW-UHFFFAOYSA-N n-[4-[(3-amino-5-chlorophenyl)carbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound NC1=CC(Cl)=CC(NC(=S)NC=2C=CC(NC(=O)C=3N=NSC=3)=CC=2)=C1 RBMUSXLONZJXJW-UHFFFAOYSA-N 0.000 claims 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 claims 1
• HGJIBVCZGFXQTK-UHFFFAOYSA-N n-[4-[1-(3,4-difluorophenyl)ethylcarbamothioylamino]phenyl]-1,3-thiazole-4-carboxamide Chemical compound C=1C=C(F)C(F)=CC=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSC=N1 HGJIBVCZGFXQTK-UHFFFAOYSA-N 0.000 claims 1
• YPIHTMUJSAKBQC-UHFFFAOYSA-N n-[4-[1-(4-bromophenyl)ethylcarbamothioylamino]phenyl]-1,3-thiazole-4-carboxamide Chemical compound C=1C=C(Br)C=CC=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSC=N1 YPIHTMUJSAKBQC-UHFFFAOYSA-N 0.000 claims 1
• XAWRTLXUYCKZQB-UHFFFAOYSA-N n-[4-[1-[3,5-bis(trifluoromethyl)phenyl]butylcarbamothioylamino]phenyl]thiadiazole-4-carboxamide Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1C(CCC)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CSN=N1 XAWRTLXUYCKZQB-UHFFFAOYSA-N 0.000 claims 1
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• BGUAPDWPQVMOBQ-UHFFFAOYSA-N tert-butyl n-[4-[[3-(trifluoromethyl)benzoyl]amino]phenyl]carbamate;2,2,2-trifluoro-n-(5-nitropyrimidin-2-yl)acetamide Chemical compound [O-][N+](=O)C1=CN=C(NC(=O)C(F)(F)F)N=C1.C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 BGUAPDWPQVMOBQ-UHFFFAOYSA-N 0.000 description 1
• KZZHPWMVEVZEFG-UHFFFAOYSA-N tert-butyl n-phenylcarbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=CC=C1 KZZHPWMVEVZEFG-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
• 125000001544 thienyl group Chemical group 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
• GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 1
• FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
• NDLIRBZKZSDGSO-UHFFFAOYSA-N tosyl azide Chemical compound CC1=CC=C(S(=O)(=O)[N-][N+]#N)C=C1 NDLIRBZKZSDGSO-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
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 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
• 229910052721 tungsten Inorganic materials 0.000 description 1
• 238000013022 venting Methods 0.000 description 1
• 230000029812 viral genome replication Effects 0.000 description 1
• 229910052727 yttrium Inorganic materials 0.000 description 1