SK7702001A3 - Thiourea inhibitors of herpes viruses - Google Patents
Thiourea inhibitors of herpes viruses Download PDFInfo
- Publication number
- SK7702001A3 SK7702001A3 SK770-2001A SK7702001A SK7702001A3 SK 7702001 A3 SK7702001 A3 SK 7702001A3 SK 7702001 A SK7702001 A SK 7702001A SK 7702001 A3 SK7702001 A3 SK 7702001A3
- Authority
- SK
- Slovakia
- Prior art keywords
- phenyl
- carbon atoms
- thioureido
- chloro
- ethyl
- Prior art date
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
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- 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
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- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 201000000317 pneumocystosis Diseases 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- KYKNRZGSIGMXFH-ZVGUSBNCSA-M potassium bitartrate Chemical compound [K+].OC(=O)[C@H](O)[C@@H](O)C([O-])=O KYKNRZGSIGMXFH-ZVGUSBNCSA-M 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000001472 potassium tartrate Substances 0.000 description 1
- 229940111695 potassium tartrate Drugs 0.000 description 1
- 235000011005 potassium tartrates Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- 125000000719 pyrrolidinyl 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
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- QRDZFPUVLYEQTA-UHFFFAOYSA-N quinoline-8-carboxylic acid Chemical compound C1=CN=C2C(C(=O)O)=CC=CC2=C1 QRDZFPUVLYEQTA-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 206010040872 skin infection Diseases 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- 239000001433 sodium tartrate Substances 0.000 description 1
- 229960002167 sodium tartrate Drugs 0.000 description 1
- 235000011004 sodium tartrates 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
- 239000003381 stabilizer Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 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
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 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
- 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)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
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 (cs) |
| JP (1) | JP2002531545A (cs) |
| KR (1) | KR20010089559A (cs) |
| CN (1) | CN1332725A (cs) |
| AR (1) | AR033789A1 (cs) |
| AT (1) | ATE272052T1 (cs) |
| AU (1) | AU1934500A (cs) |
| BG (1) | BG105583A (cs) |
| BR (1) | BR9916086A (cs) |
| CA (1) | CA2351403A1 (cs) |
| CZ (1) | CZ20011957A3 (cs) |
| DE (1) | DE69919023T2 (cs) |
| DK (1) | DK1137632T3 (cs) |
| EA (1) | EA200100634A1 (cs) |
| ES (1) | ES2224733T3 (cs) |
| HU (1) | HUP0104763A3 (cs) |
| ID (1) | ID30287A (cs) |
| IL (1) | IL143262A0 (cs) |
| NO (1) | NO20012838L (cs) |
| NZ (1) | NZ512108A (cs) |
| PL (1) | PL348178A1 (cs) |
| PT (1) | PT1137632E (cs) |
| SK (1) | SK7702001A3 (cs) |
| TR (1) | TR200101597T2 (cs) |
| WO (1) | WO2000034238A1 (cs) |
| ZA (1) | ZA200104144B (cs) |
Families Citing this family (11)
| 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 |
| 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 |
| PT2077995E (pt) | 2006-11-02 | 2012-05-10 | Millennium Pharm Inc | Métodos de sintetizar sais farmacêuticos de um inibidor de fator xa |
| JP2014517847A (ja) * | 2011-05-24 | 2014-07-24 | ザ ウィスター インスティテュート | エプスタイン・バー核抗原1の活性を調節する組成物および方法 |
| 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 |
| WO2022150962A1 (en) * | 2021-01-12 | 2022-07-21 | Westlake Pharmaceutical (Hangzhou) Co., Ltd. | Protease inhibitors, preparation, and uses thereof |
| JP2024534270A (ja) * | 2021-09-07 | 2024-09-18 | 上海齊魯制藥研究中心有限公司 | 3CLproプロテアーゼ阻害剤 |
Family Cites Families (4)
| 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 |
| EP0902782A1 (en) * | 1996-04-23 | 1999-03-24 | Vertex Pharmaceuticals Incorporated | Urea derivatives as inhibitors of impdh enzyme |
-
1999
- 1999-12-06 TR TR2001/01597T patent/TR200101597T2/xx unknown
- 1999-12-06 CZ CZ20011957A patent/CZ20011957A3/cs unknown
- 1999-12-06 SK SK770-2001A patent/SK7702001A3/sk unknown
- 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 NZ NZ512108A patent/NZ512108A/en unknown
- 1999-12-06 BR BR9916086-2A patent/BR9916086A/pt not_active Application Discontinuation
- 1999-12-06 IL IL14326299A patent/IL143262A0/xx unknown
- 1999-12-06 WO PCT/US1999/028837 patent/WO2000034238A1/en not_active Application Discontinuation
- 1999-12-06 ID IDW00200101228A patent/ID30287A/id unknown
- 1999-12-06 EA EA200100634A patent/EA200100634A1/ru unknown
- 1999-12-06 EP EP99963021A patent/EP1137632B1/en not_active Expired - Lifetime
- 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 CA CA002351403A patent/CA2351403A1/en not_active Abandoned
- 1999-12-06 PT PT99963021T patent/PT1137632E/pt unknown
- 1999-12-06 CN CN99815344A patent/CN1332725A/zh active Pending
- 1999-12-06 DK DK99963021T patent/DK1137632T3/da active
- 1999-12-06 JP JP2000586686A patent/JP2002531545A/ja active Pending
- 1999-12-06 DE DE69919023T patent/DE69919023T2/de not_active Expired - Fee Related
- 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 |
|---|---|
| JP2002531545A (ja) | 2002-09-24 |
| EA200100634A1 (ru) | 2001-10-22 |
| PL348178A1 (en) | 2002-05-06 |
| NZ512108A (en) | 2003-09-26 |
| EP1137632A1 (en) | 2001-10-04 |
| ES2224733T3 (es) | 2005-03-01 |
| BG105583A (en) | 2001-12-29 |
| EP1137632B1 (en) | 2004-07-28 |
| ATE272052T1 (de) | 2004-08-15 |
| ID30287A (id) | 2001-11-15 |
| ZA200104144B (en) | 2002-08-21 |
| IL143262A0 (en) | 2002-04-21 |
| DE69919023D1 (de) | 2004-09-02 |
| CN1332725A (zh) | 2002-01-23 |
| NO20012838L (no) | 2001-08-08 |
| BR9916086A (pt) | 2001-09-04 |
| HUP0104763A2 (hu) | 2002-04-29 |
| CZ20011957A3 (cs) | 2001-10-17 |
| DK1137632T3 (da) | 2004-11-01 |
| PT1137632E (pt) | 2004-11-30 |
| WO2000034238A1 (en) | 2000-06-15 |
| DE69919023T2 (de) | 2005-07-28 |
| AU1934500A (en) | 2000-06-26 |
| HUP0104763A3 (en) | 2005-04-28 |
| AR033789A1 (es) | 2004-01-07 |
| TR200101597T2 (tr) | 2001-10-22 |
| KR20010089559A (ko) | 2001-10-06 |
| CA2351403A1 (en) | 2000-06-15 |
| NO20012838D0 (no) | 2001-06-08 |
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