SK7702001A3 - Thiourea inhibitors of herpes viruses - Google Patents

Thiourea inhibitors of herpes viruses Download PDF

Info

Publication number: SK7702001A3
Authority: SK; Slovakia
Prior art keywords: phenyl; carbon atoms; thioureido; chloro; ethyl
Prior art date: 1998-12-09

Application number

SK770-2001A

Other languages

English (en)

Slovak (sk)

Inventor

Jonathan David Bloom

Kevin Joseph Curran

Martin Joseph Digrandi

Russell George Dushin

Stanley Albert Lang

Emily Boucher Norton

Adma Antonia Ross

Bryan Mark O'hara

Original Assignee

American Home Prod

Priority date (The priority date 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 date listed.)

1998-12-09

Filing date

1999-12-06

Publication date

2002-04-04

1999-12-06 Application filed by American Home Prod filed Critical American Home Prod

2002-04-04 Publication of SK7702001A3 publication Critical patent/SK7702001A3/sk

Links

241001529453 unidentified herpesvirus Species 0.000 title claims abstract description 18
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title description 14
239000003112 inhibitor Substances 0.000 title description 12
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 title description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 181
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 150
150000001875 compounds Chemical class 0.000 claims abstract description 110
125000000217 alkyl group Chemical group 0.000 claims abstract description 49
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 44
239000001257 hydrogen Substances 0.000 claims abstract description 44
125000003118 aryl group Chemical group 0.000 claims abstract description 37
150000002431 hydrogen Chemical group 0.000 claims abstract description 29
125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 28
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 25
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 25
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 22
229910052736 halogen Inorganic materials 0.000 claims abstract description 19
150000002367 halogens Chemical class 0.000 claims abstract description 19
241000701085 Human alphaherpesvirus 3 Species 0.000 claims abstract description 17
125000003342 alkenyl group Chemical group 0.000 claims abstract description 16
125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
125000000304 alkynyl group Chemical group 0.000 claims abstract description 9
125000003282 alkyl amino group Chemical group 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 7
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 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
-1 N- {4- [3- (benzofuran-2-yl-ethyl) thioureido] -2-trifluoromethyl-phenyl} -2-fluoro-benzamide Chemical compound 0.000 claims description 330
238000000034 method Methods 0.000 claims description 230
150000001408 amides Chemical class 0.000 claims description 53
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 42
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 41
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 37
239000002253 acid Substances 0.000 claims description 23
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 12
125000001424 substituent group Chemical group 0.000 claims description 11
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
230000003287 optical effect Effects 0.000 claims description 7
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 claims description 6
UONZELSBJKQPGU-UHFFFAOYSA-N n-[4-[1-(4-bromophenyl)ethylcarbamothioylamino]-2-[2-(diethylamino)ethoxy]phenyl]-2-fluorobenzamide Chemical compound C=1C=C(NC(=O)C=2C(=CC=CC=2)F)C(OCCN(CC)CC)=CC=1NC(=S)NC(C)C1=CC=C(Br)C=C1 UONZELSBJKQPGU-UHFFFAOYSA-N 0.000 claims description 5
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 4
208000029433 Herpesviridae infectious disease Diseases 0.000 claims description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
125000002619 bicyclic group Chemical group 0.000 claims description 4
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
XAAKCCMYRKZRAK-UHFFFAOYSA-N isoquinoline-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=NC=CC2=C1 XAAKCCMYRKZRAK-UHFFFAOYSA-N 0.000 claims description 4
KSMCSBQUFXZXQL-UHFFFAOYSA-N 2,4,5-trifluoro-n-[4-[1-(4-fluorophenyl)ethylcarbamothioylamino]-3-methylphenyl]benzamide Chemical compound C=1C=C(F)C=CC=1C(C)NC(=S)NC(C(=C1)C)=CC=C1NC(=O)C1=CC(F)=C(F)C=C1F KSMCSBQUFXZXQL-UHFFFAOYSA-N 0.000 claims description 3
ARPUOKDCCUBVPO-UHFFFAOYSA-N 2-fluoro-n-[4-[1-(4-fluorophenyl)ethylcarbamothioylamino]-2,5-dimethoxyphenyl]benzamide Chemical compound COC=1C=C(NC(=S)NC(C)C=2C=CC(F)=CC=2)C(OC)=CC=1NC(=O)C1=CC=CC=C1F ARPUOKDCCUBVPO-UHFFFAOYSA-N 0.000 claims description 3
FAKLTJLEHBRFDK-UHFFFAOYSA-N 2-fluoro-n-[4-[1-(4-fluorophenyl)ethylcarbamothioylamino]-2-methoxyphenyl]benzamide Chemical compound C=1C=C(NC(=O)C=2C(=CC=CC=2)F)C(OC)=CC=1NC(=S)NC(C)C1=CC=C(F)C=C1 FAKLTJLEHBRFDK-UHFFFAOYSA-N 0.000 claims description 3
OYIMPFKPTDVWJZ-UHFFFAOYSA-N 2-fluoro-n-[4-[1-(4-fluorophenyl)ethylcarbamothioylamino]-2-phenylmethoxyphenyl]benzamide Chemical compound C=1C=C(F)C=CC=1C(C)NC(=S)NC(C=C1OCC=2C=CC=CC=2)=CC=C1NC(=O)C1=CC=CC=C1F OYIMPFKPTDVWJZ-UHFFFAOYSA-N 0.000 claims description 3
NVOHODKAPMAEDF-UHFFFAOYSA-N 2-fluoro-n-[4-[1-(4-fluorophenyl)ethylcarbamothioylamino]-3-(trifluoromethyl)phenyl]benzamide Chemical compound C=1C=C(F)C=CC=1C(C)NC(=S)NC(C(=C1)C(F)(F)F)=CC=C1NC(=O)C1=CC=CC=C1F NVOHODKAPMAEDF-UHFFFAOYSA-N 0.000 claims description 3
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 3
YHFABDFGYMFOOD-UHFFFAOYSA-N n-[2-(dimethylamino)-4-[1-(4-fluorophenyl)ethylcarbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound C=1C=C(F)C=CC=1C(C)NC(=S)NC(C=C1N(C)C)=CC=C1NC(=O)C1=CC=CC=C1F YHFABDFGYMFOOD-UHFFFAOYSA-N 0.000 claims description 3
NKUKBLWOOUNLPG-UHFFFAOYSA-N n-[2-benzoyl-4-[1-(4-fluorophenyl)ethylcarbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound C=1C=C(F)C=CC=1C(C)NC(=S)NC(C=C1C(=O)C=2C=CC=CC=2)=CC=C1NC(=O)C1=CC=CC=C1F NKUKBLWOOUNLPG-UHFFFAOYSA-N 0.000 claims description 3
CFFVXQJQQZUTQY-UHFFFAOYSA-N n-[2-butoxy-4-[1-(4-cyanophenyl)ethylcarbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound C=1C=C(NC(=O)C=2C(=CC=CC=2)F)C(OCCCC)=CC=1NC(=S)NC(C)C1=CC=C(C#N)C=C1 CFFVXQJQQZUTQY-UHFFFAOYSA-N 0.000 claims description 3
MINUESQUQRTPLR-UHFFFAOYSA-N n-[2-butoxy-4-[1-(4-fluorophenyl)ethylcarbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound C=1C=C(NC(=O)C=2C(=CC=CC=2)F)C(OCCCC)=CC=1NC(=S)NC(C)C1=CC=C(F)C=C1 MINUESQUQRTPLR-UHFFFAOYSA-N 0.000 claims description 3
LUDBGGVMLWRTCP-UHFFFAOYSA-N n-[2-chloro-4-[1-(4-cyanophenyl)ethylcarbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound C=1C=C(C#N)C=CC=1C(C)NC(=S)NC(C=C1Cl)=CC=C1NC(=O)C1=CC=CC=C1F LUDBGGVMLWRTCP-UHFFFAOYSA-N 0.000 claims description 3
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 claims description 3
CEJMZFBWDXVPHV-UHFFFAOYSA-N n-[2-cyano-4-[1-(4-cyanophenyl)ethylcarbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound C=1C=C(C#N)C=CC=1C(C)NC(=S)NC(C=C1C#N)=CC=C1NC(=O)C1=CC=CC=C1F CEJMZFBWDXVPHV-UHFFFAOYSA-N 0.000 claims description 3
PEOGCRADENDYID-UHFFFAOYSA-N n-[2-cyano-4-[1-(4-fluorophenyl)ethylcarbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound C=1C=C(F)C=CC=1C(C)NC(=S)NC(C=C1C#N)=CC=C1NC(=O)C1=CC=CC=C1F PEOGCRADENDYID-UHFFFAOYSA-N 0.000 claims description 3
IAFKBNMPIDOPRL-UHFFFAOYSA-N n-[2-ethoxy-4-[1-(4-fluorophenyl)ethylcarbamothioylamino]phenyl]-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(F)C=C1 IAFKBNMPIDOPRL-UHFFFAOYSA-N 0.000 claims description 3
ZUVAJKBIJKAPOE-UHFFFAOYSA-N n-[3,5-dichloro-4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C(=C1)Cl)=C(Cl)C=C1NC(=O)C1=CC=CC=C1F ZUVAJKBIJKAPOE-UHFFFAOYSA-N 0.000 claims description 3
VMNABOPPDUIRHF-UHFFFAOYSA-N n-[3-chloro-4-[1-(4-fluorophenyl)ethylcarbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound C=1C=C(F)C=CC=1C(C)NC(=S)NC(C(=C1)Cl)=CC=C1NC(=O)C1=CC=CC=C1F VMNABOPPDUIRHF-UHFFFAOYSA-N 0.000 claims description 3
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 claims description 3
CJNKWYKDXLCJRB-UHFFFAOYSA-N n-[4-[1-(4-bromophenyl)ethylcarbamothioylamino]-2-cyanophenyl]-2-fluorobenzamide Chemical compound C=1C=C(Br)C=CC=1C(C)NC(=S)NC(C=C1C#N)=CC=C1NC(=O)C1=CC=CC=C1F CJNKWYKDXLCJRB-UHFFFAOYSA-N 0.000 claims description 3
IXGBWHVCTCVPOU-UHFFFAOYSA-N n-[4-[1-(4-bromophenyl)ethylcarbamothioylamino]-2-methylphenyl]-2-fluorobenzamide Chemical compound C=1C=C(Br)C=CC=1C(C)NC(=S)NC(C=C1C)=CC=C1NC(=O)C1=CC=CC=C1F IXGBWHVCTCVPOU-UHFFFAOYSA-N 0.000 claims description 3
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 claims description 3
LSETVEKXMBPFKA-UHFFFAOYSA-N n-[4-[1-(4-cyanophenyl)ethylcarbamothioylamino]-2-(trifluoromethyl)phenyl]-2-fluorobenzamide Chemical compound C=1C=C(C#N)C=CC=1C(C)NC(=S)NC(C=C1C(F)(F)F)=CC=C1NC(=O)C1=CC=CC=C1F LSETVEKXMBPFKA-UHFFFAOYSA-N 0.000 claims description 3
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NPQVRWPMPRBCQU-UHFFFAOYSA-N n-[4-[1-(4-cyanophenyl)ethylcarbamothioylamino]-2-phenylmethoxyphenyl]-2-fluorobenzamide Chemical compound C=1C=C(C#N)C=CC=1C(C)NC(=S)NC(C=C1OCC=2C=CC=CC=2)=CC=C1NC(=O)C1=CC=CC=C1F NPQVRWPMPRBCQU-UHFFFAOYSA-N 0.000 claims description 3
CJNKWYKDXLCJRB-AWEZNQCLSA-N n-[4-[[(1s)-1-(4-bromophenyl)ethyl]carbamothioylamino]-2-cyanophenyl]-2-fluorobenzamide Chemical compound N([C@@H](C)C=1C=CC(Br)=CC=1)C(=S)NC(C=C1C#N)=CC=C1NC(=O)C1=CC=CC=C1F CJNKWYKDXLCJRB-AWEZNQCLSA-N 0.000 claims description 3
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239000008194 pharmaceutical composition Substances 0.000 claims description 3
PDCXXGAUIABRGY-UHFFFAOYSA-N 2-fluoro-n-[4-[1-(4-fluorophenyl)ethylcarbamothioylamino]-2-methylphenyl]benzamide Chemical compound C=1C=C(F)C=CC=1C(C)NC(=S)NC(C=C1C)=CC=C1NC(=O)C1=CC=CC=C1F PDCXXGAUIABRGY-UHFFFAOYSA-N 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
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AMGIFTVJCMBPMM-UHFFFAOYSA-N methyl 2-(4-amino-2,6-dichlorophenoxy)acetate Chemical compound COC(=O)COC1=C(Cl)C=C(N)C=C1Cl AMGIFTVJCMBPMM-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
PCVWKWMQOWKWEF-UHFFFAOYSA-N methyl 2-[2,6-dichloro-4-[(2-methylpropan-2-yl)oxycarbonylamino]phenoxy]acetate Chemical compound COC(=O)COC1=C(Cl)C=C(NC(=O)OC(C)(C)C)C=C1Cl PCVWKWMQOWKWEF-UHFFFAOYSA-N 0.000 description 1
XVAHZYHXZREMMQ-UHFFFAOYSA-N methyl 2-[4-[(4-acetamidophenyl)carbamothioylamino]-2,6-dichlorophenoxy]acetate Chemical compound C1=C(Cl)C(OCC(=O)OC)=C(Cl)C=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 XVAHZYHXZREMMQ-UHFFFAOYSA-N 0.000 description 1
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235000012222 talc Nutrition 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
MSMKEFVMOMIPIH-UHFFFAOYSA-N tert-butyl 2-[4-[(4-acetamidophenyl)carbamothioylamino]-2,6-dichlorophenoxy]acetate Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC1=CC(Cl)=C(OCC(=O)OC(C)(C)C)C(Cl)=C1 MSMKEFVMOMIPIH-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
LYQLDHCHIYUUHO-UHFFFAOYSA-N tert-butyl N-[4-[(2-methylbenzoyl)amino]phenyl]carbamate 2,2,2-trifluoro-N-(2-methoxy-4-nitrophenyl)acetamide Chemical compound C(C)(C)(C)OC(NC1=CC=C(C=C1)NC(C1=C(C=CC=C1)C)=O)=O.FC(C(=O)NC1=C(C=C(C=C1)[N+](=O)[O-])OC)(F)F LYQLDHCHIYUUHO-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
SILSCQHMOKLRJW-UHFFFAOYSA-N tert-butyl n-[2-amino-3-chloro-5-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(C(F)(F)F)=CC(Cl)=C1N SILSCQHMOKLRJW-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
WZGBTJMVFZAIFE-UHFFFAOYSA-N tert-butyl n-[3-chloro-4-(1,2-oxazol-5-yl)phenyl]carbamate Chemical compound ClC1=CC(NC(=O)OC(C)(C)C)=CC=C1C1=CC=NO1 WZGBTJMVFZAIFE-UHFFFAOYSA-N 0.000 description 1
NBUJNJDGRIWQDH-UHFFFAOYSA-N tert-butyl n-[3-chloro-4-(1h-pyrazol-5-yl)phenyl]carbamate Chemical compound ClC1=CC(NC(=O)OC(C)(C)C)=CC=C1C1=NNC=C1 NBUJNJDGRIWQDH-UHFFFAOYSA-N 0.000 description 1
VNSCQDCAADKASD-UHFFFAOYSA-N tert-butyl n-[3-chloro-4-(2-hydroxyethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(CCO)C(Cl)=C1 VNSCQDCAADKASD-UHFFFAOYSA-N 0.000 description 1
VYSOCXOVQIADML-UHFFFAOYSA-N tert-butyl n-[3-chloro-5-(dimethylamino)phenyl]carbamate Chemical compound CN(C)C1=CC(Cl)=CC(NC(=O)OC(C)(C)C)=C1 VYSOCXOVQIADML-UHFFFAOYSA-N 0.000 description 1
UKVMRGJTCKUACH-UHFFFAOYSA-N tert-butyl n-[4-[(2,3,4,5,6-pentafluorobenzoyl)amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=C(F)C(F)=C(F)C(F)=C1F UKVMRGJTCKUACH-UHFFFAOYSA-N 0.000 description 1
BELLLWYFKZJRQM-UHFFFAOYSA-N tert-butyl n-[4-[(2-fluorobenzoyl)amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=CC=C1F BELLLWYFKZJRQM-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
SZOWCRZFJMPQPK-UHFFFAOYSA-N tert-butyl n-[4-[(3-methylfuran-2-carbonyl)amino]phenyl]carbamate Chemical compound C1=COC(C(=O)NC=2C=CC(NC(=O)OC(C)(C)C)=CC=2)=C1C SZOWCRZFJMPQPK-UHFFFAOYSA-N 0.000 description 1
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 1
VMUBNKIZZBLASE-UHFFFAOYSA-N tert-butyl n-[[4-(furan-2-carbonylamino)phenyl]methyl]carbamate Chemical compound C1=CC(CNC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=CO1 VMUBNKIZZBLASE-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
239000002562 thickening agent Substances 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
QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 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
210000001519 tissue Anatomy 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 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
JUDXOKKZTISQDJ-UHFFFAOYSA-N triphenylphosphane;hydrochloride Chemical compound Cl.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 JUDXOKKZTISQDJ-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
229910052721 tungsten Inorganic materials 0.000 description 1
210000003501 vero cell Anatomy 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
230000007919 viral pathogenicity Effects 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
- 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
- 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
- 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
- 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)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Molecular Biology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Biotechnology (AREA)
Engineering & Computer Science (AREA)
Communicable Diseases (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Furan Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

SK770-2001A 1998-12-09 1999-12-06 Thiourea inhibitors of herpes viruses SK7702001A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US20856198A	1998-12-09	1998-12-09
PCT/US1999/028837 WO2000034238A1 (en)	1998-12-09	1999-12-06	Thiourea inhibitors of herpes viruses

Publications (1)

Publication Number	Publication Date
SK7702001A3 true SK7702001A3 (en)	2002-04-04

Family

ID=22775050

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK770-2001A SK7702001A3 (en)	1998-12-09	1999-12-06	Thiourea inhibitors of herpes viruses

Country Status (26)

Country	Link
EP (1)	EP1137632B1 (de)
JP (1)	JP2002531545A (de)
KR (1)	KR20010089559A (de)
CN (1)	CN1332725A (de)
AR (1)	AR033789A1 (de)
AT (1)	ATE272052T1 (de)
AU (1)	AU1934500A (de)
BG (1)	BG105583A (de)
BR (1)	BR9916086A (de)
CA (1)	CA2351403A1 (de)
CZ (1)	CZ20011957A3 (de)
DE (1)	DE69919023T2 (de)
DK (1)	DK1137632T3 (de)
EA (1)	EA200100634A1 (de)
ES (1)	ES2224733T3 (de)
HU (1)	HUP0104763A3 (de)
ID (1)	ID30287A (de)
IL (1)	IL143262A0 (de)
NO (1)	NO20012838L (de)
NZ (1)	NZ512108A (de)
PL (1)	PL348178A1 (de)
PT (1)	PT1137632E (de)
SK (1)	SK7702001A3 (de)
TR (1)	TR200101597T2 (de)
WO (1)	WO2000034238A1 (de)
ZA (1)	ZA200104144B (de)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
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
WO2001064642A2 (en)	2000-02-29	2001-09-07	Cor Therapeutics, Inc.	Benzamides and related inhibitors of factor xa
DE10217518A1 (de) *	2002-04-19	2003-11-06	Bayer Ag	Lactone
DE10222024A1 (de) *	2002-05-17	2003-11-27	Bayer Ag	Lactame
DE10257786A1 (de) *	2002-12-11	2004-07-01	Bayer Healthcare Ag	Oxazolidinone
EP2077995B1 (de)	2006-11-02	2012-02-08	Millennium Pharmaceuticals, Inc.	Verfahren zur synthetisierung pharmazeutischer salze aus einem faktor-xa-hemmer
CN103717757A (zh)	2011-05-24	2014-04-09	威斯特研究所	用于调节爱泼斯坦-巴尔核抗原1的活性的组合物和方法
EP2914592B1 (de)	2012-11-03	2017-10-11	Boehringer Ingelheim International GmbH	Inhibitoren des cytomegalovirus
US9284310B2 (en)	2012-11-03	2016-03-15	Boehringer Ingelheim International Gmbh	Inhibitors of cytomegalovirus
WO2022150962A1 (en) *	2021-01-12	2022-07-21	Westlake Pharmaceutical (Hangzhou) Co., Ltd.	Protease inhibitors, preparation, and uses thereof
WO2023036140A1 (zh) *	2021-09-07	2023-03-16	上海齐鲁制药研究中心有限公司	3CLpro蛋白酶抑制剂

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU210683B (en) *	1990-06-18	1995-06-28	Sandoz Ag	Process for producing n-benzyl-n1-(phenyl-alkyl)-thiourea derivatives and pharmaceutical compositions containing the same
JPH11503110A (ja) *	1995-02-17	1999-03-23	スミスクライン・ビーチャム・コーポレイション	Ｉｌ−８受容体拮抗剤
GB9519270D0 (en) *	1995-09-21	1995-11-22	Sandoz Pharma Uk	Organic compounds
PL192628B1 (pl) *	1996-04-23	2006-11-30	Vertex Pharma	Pochodne mocznika, kompozycje farmaceutyczne i zastosowanie związku i kompozycji

1999
- 1999-12-06 EP EP99963021A patent/EP1137632B1/de not_active Expired - Lifetime
- 1999-12-06 TR TR2001/01597T patent/TR200101597T2/xx unknown
- 1999-12-06 PT PT99963021T patent/PT1137632E/pt unknown
- 1999-12-06 ID IDW00200101228A patent/ID30287A/id unknown
- 1999-12-06 SK SK770-2001A patent/SK7702001A3/sk unknown
- 1999-12-06 JP JP2000586686A patent/JP2002531545A/ja active Pending
- 1999-12-06 CN CN99815344A patent/CN1332725A/zh active Pending
- 1999-12-06 BR BR9916086-2A patent/BR9916086A/pt not_active Application Discontinuation
- 1999-12-06 DK DK99963021T patent/DK1137632T3/da active
- 1999-12-06 CZ CZ20011957A patent/CZ20011957A3/cs unknown
- 1999-12-06 NZ NZ512108A patent/NZ512108A/en unknown
- 1999-12-06 CA CA002351403A patent/CA2351403A1/en not_active Abandoned
- 1999-12-06 EA EA200100634A patent/EA200100634A1/ru unknown
- 1999-12-06 IL IL14326299A patent/IL143262A0/xx unknown
- 1999-12-06 AT AT99963021T patent/ATE272052T1/de not_active IP Right Cessation
- 1999-12-06 AU AU19345/00A patent/AU1934500A/en not_active Abandoned
- 1999-12-06 DE DE69919023T patent/DE69919023T2/de not_active Expired - Fee Related
- 1999-12-06 PL PL99348178A patent/PL348178A1/xx not_active Application Discontinuation
- 1999-12-06 KR KR1020017007134A patent/KR20010089559A/ko not_active Withdrawn
- 1999-12-06 HU HU0104763A patent/HUP0104763A3/hu unknown
- 1999-12-06 WO PCT/US1999/028837 patent/WO2000034238A1/en not_active Ceased
- 1999-12-06 ES ES99963021T patent/ES2224733T3/es not_active Expired - Lifetime
- 1999-12-07 AR ARP990106229A patent/AR033789A1/es not_active Application Discontinuation
2001
- 2001-05-21 ZA ZA200104144A patent/ZA200104144B/xx unknown
- 2001-06-08 BG BG105583A patent/BG105583A/xx unknown
- 2001-06-08 NO NO20012838A patent/NO20012838L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
AR033789A1 (es)	2004-01-07
ES2224733T3 (es)	2005-03-01
DE69919023T2 (de)	2005-07-28
CZ20011957A3 (cs)	2001-10-17
TR200101597T2 (tr)	2001-10-22
JP2002531545A (ja)	2002-09-24
DE69919023D1 (de)	2004-09-02
BG105583A (en)	2001-12-29
EP1137632A1 (de)	2001-10-04
CA2351403A1 (en)	2000-06-15
NZ512108A (en)	2003-09-26
HUP0104763A2 (hu)	2002-04-29
PL348178A1 (en)	2002-05-06
ATE272052T1 (de)	2004-08-15
NO20012838D0 (no)	2001-06-08
NO20012838L (no)	2001-08-08
WO2000034238A1 (en)	2000-06-15
EA200100634A1 (ru)	2001-10-22
PT1137632E (pt)	2004-11-30
HUP0104763A3 (en)	2005-04-28
BR9916086A (pt)	2001-09-04
AU1934500A (en)	2000-06-26
EP1137632B1 (de)	2004-07-28
ID30287A (id)	2001-11-15
CN1332725A (zh)	2002-01-23
IL143262A0 (en)	2002-04-21
DK1137632T3 (da)	2004-11-01
KR20010089559A (ko)	2001-10-06
ZA200104144B (en)	2002-08-21

Publication	Publication Date	Title
CZ20012060A3 (cs)	2001-11-14	Thiomočovinové sloučeniny obsahující acetamid a substituovaný acetamid jako inhibitory herpes virů
SK7682001A3 (en)	2002-07-02	Heterocyclic carboxamide-containing thiourea inhibitors of herpes viruses containing phenylenediamine group
DE69919023T2 (de)	2005-07-28	Thioharnstoff-inhibitoren von herpes-virus
CZ20012063A3 (cs)	2001-10-17	Thiomočovinové sloučeniny obsahující heterocyklický karboxamid a substituovanou fenylendiaminovou skupinu jako inhibitory herpes virů
CZ20012067A3 (cs)	2001-10-17	Thiomočovinové sloučeniny obsahující alfa methylbenzylovou skupinu a fenylendiaminovou skupinu jako inhibitory herpes virů
SK7692001A3 (en)	2002-09-10	Thiourea inhibitors of herpes viruses
CZ20012057A3 (cs)	2001-11-14	Thiomočovinové sloučeniny jako inhibitory herpes virů 199
US6197803B1 (en)	2001-03-06	Heterocyclic carboxamide-containing thiourea inhibitors of herpes viruses containing phenylenediamine group
MXPA01005679A (en)	2002-02-26	Heterocyclic carboxamide-containing thiourea inhibitors of herpes viruses containing phenylenediamine group
MXPA01005835A (en)	2001-12-13	Thiourea inhibitors of herpes viruses
MXPA01005829A (en)	2001-12-13	Thiourea inhibitors of herpes viruses
MXPA01005681A (en)	2001-12-13	Alpha-methylbenzyl-containing thiourea inhibitors of herpes viruses containing a phenylenediamine group
KR20010087416A (ko)	2001-09-15	페닐렌디아민기를 함유하는 헤르페스 바이러스의헤테로시클릭 카르복사미드-함유 티오우레아 저해제
MXPA01005827A (en)	2001-12-13	Thiourea inhibitors of herpes viruses
MXPA01005680A (en)	2001-12-13	Acetamide and substituted acetamide-containing thiourea inhibitors of herpes viruses
MXPA01005828A (en)	2001-12-13	Heterocyclic carboxamide-containing thiourea inhibitors of herpes viruses containing a substituted phenylenediamine group