KR20010087413A - 헤르페스 바이러스의 아세트아마이드 및 치환아세트아마이드-함유 티오우레아 억제제 - Google Patents

헤르페스 바이러스의 아세트아마이드 및 치환아세트아마이드-함유 티오우레아 억제제 Download PDF

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Publication number: KR20010087413A
Authority: KR; South Korea
Prior art keywords: phenyl; carbon atoms; chloro; amino; alkyl
Prior art date: 1998-12-09
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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

KR1020017007052A

Other languages

English (en)

Korean (ko)

Inventor

블룸조너선데이빗

디그랜디마틴조지프

더쉰러셀조지

랭스탠리앨버트

오하라브라이언마크

Original Assignee

이곤 이 버그

아메리칸 홈 푸로닥츠 코포레이션

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

2001-09-15

1999-12-06 Application filed by 이곤 이 버그, 아메리칸 홈 푸로닥츠 코포레이션 filed Critical 이곤 이 버그

2001-09-15 Publication of KR20010087413A publication Critical patent/KR20010087413A/ko

Status Withdrawn legal-status Critical Current

Links

241001529453 unidentified herpesvirus Species 0.000 title claims abstract description 22
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title description 18
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 title description 17
239000003112 inhibitor Substances 0.000 title description 11
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 title 3
150000003869 acetamides Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 157
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 142
125000000217 alkyl group Chemical group 0.000 claims abstract description 58
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 40
239000001257 hydrogen Substances 0.000 claims abstract description 40
125000003118 aryl group Chemical group 0.000 claims abstract description 29
125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 27
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 23
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 22
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 19
229910052736 halogen Inorganic materials 0.000 claims abstract description 18
150000002367 halogens Chemical class 0.000 claims abstract description 18
241000701085 Human alphaherpesvirus 3 Species 0.000 claims abstract description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 16
125000003342 alkenyl group Chemical group 0.000 claims abstract description 15
125000003545 alkoxy group Chemical group 0.000 claims abstract description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 12
150000003839 salts Chemical class 0.000 claims abstract description 12
125000000304 alkynyl group Chemical group 0.000 claims abstract description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 7
125000003282 alkyl amino group Chemical group 0.000 claims abstract description 7
241000701024 Human betaherpesvirus 5 Species 0.000 claims abstract description 6
125000004429 atom Chemical group 0.000 claims abstract description 6
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
229910052799 carbon Inorganic materials 0.000 claims abstract description 6
125000004001 thioalkyl group Chemical group 0.000 claims abstract description 6
241000700584 Simplexvirus Species 0.000 claims abstract description 5
238000000034 method Methods 0.000 claims description 256
-1 N- {4- [3- (3,5-Dichloro-2-methoxy-4-phenyl-phenyl) -thioureido] -phenyl} -acetamide Chemical compound 0.000 claims description 132
150000002431 hydrogen Chemical class 0.000 claims description 21
239000000460 chlorine Substances 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
XETUWKMUGXMMNU-UHFFFAOYSA-N n-[4-[[3-chloro-4-[methyl-(1-methylpiperidin-4-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)CC1 XETUWKMUGXMMNU-UHFFFAOYSA-N 0.000 claims description 5
239000000126 substance Substances 0.000 claims description 5
JHWBVIMCORQTMX-UHFFFAOYSA-N n-[4-[(3,5-dichloro-4-ethoxyphenyl)carbamothioylamino]phenyl]acetamide Chemical compound C1=C(Cl)C(OCC)=C(Cl)C=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 JHWBVIMCORQTMX-UHFFFAOYSA-N 0.000 claims description 3
FGNLMRLPFPCYRP-UHFFFAOYSA-N n-[4-[(3,5-dichloro-4-methoxyphenyl)carbamothioylamino]phenyl]acetamide Chemical compound C1=C(Cl)C(OC)=C(Cl)C=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 FGNLMRLPFPCYRP-UHFFFAOYSA-N 0.000 claims description 3
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 claims description 3
UAUOPWDADDLRDP-UHFFFAOYSA-N n-[4-[(3-chloro-4-iodophenyl)carbamothioylamino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC1=CC=C(I)C(Cl)=C1 UAUOPWDADDLRDP-UHFFFAOYSA-N 0.000 claims description 3
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 claims description 3
UGBAQLAOKVDTPH-UHFFFAOYSA-N n-[4-[(5-chloro-2-methoxy-4-methylphenyl)carbamothioylamino]phenyl]acetamide Chemical compound COC1=CC(C)=C(Cl)C=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 UGBAQLAOKVDTPH-UHFFFAOYSA-N 0.000 claims description 3
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 claims description 3
NBOLXIZMRYDZPT-UHFFFAOYSA-N n-[4-[[3-chloro-4-(trifluoromethyl)phenyl]carbamothioylamino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC1=CC=C(C(F)(F)F)C(Cl)=C1 NBOLXIZMRYDZPT-UHFFFAOYSA-N 0.000 claims description 3
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 claims description 3
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 claims description 3
BCXGUEDGWCZVRT-UHFFFAOYSA-N n-[4-[[4-[(1-benzylpyrrolidin-3-yl)amino]-3-chlorophenyl]carbamothioylamino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC(C=C1Cl)=CC=C1NC1CN(CC=2C=CC=CC=2)CC1 BCXGUEDGWCZVRT-UHFFFAOYSA-N 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
230000035755 proliferation Effects 0.000 claims description 3
230000002401 inhibitory effect Effects 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
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
238000011282 treatment Methods 0.000 abstract description 14
201000010099 disease Diseases 0.000 abstract description 11
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 11
241000701041 Human betaherpesvirus 7 Species 0.000 abstract description 6
241000701044 Human gammaherpesvirus 4 Species 0.000 abstract description 6
241000701027 Human herpesvirus 6 Species 0.000 abstract description 6
125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 5
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 240
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 183
239000002904 solvent Substances 0.000 description 154
239000000243 solution Substances 0.000 description 151
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 139
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 129
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 111
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 111
239000000203 mixture Substances 0.000 description 106
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 90
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 84
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 82
239000000047 product Substances 0.000 description 79
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 71
239000007787 solid Substances 0.000 description 70
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 69
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 65
239000007858 starting material Substances 0.000 description 62
150000001412 amines Chemical class 0.000 description 61
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 60
238000010992 reflux Methods 0.000 description 55
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 51
229920006395 saturated elastomer Polymers 0.000 description 50
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 48
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 45
230000000875 corresponding effect Effects 0.000 description 45
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 44
238000006243 chemical reaction Methods 0.000 description 41
239000003921 oil Substances 0.000 description 41
235000019198 oils Nutrition 0.000 description 41
SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 40
239000011780 sodium chloride Substances 0.000 description 40
239000003480 eluent Substances 0.000 description 37
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 36
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 35
239000000741 silica gel Substances 0.000 description 35
229910002027 silica gel Inorganic materials 0.000 description 35
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 34
239000011541 reaction mixture Substances 0.000 description 32
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 30
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 29
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 23
239000000284 extract Substances 0.000 description 23
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 22
229910000027 potassium carbonate Inorganic materials 0.000 description 22
125000001424 substituent group Chemical group 0.000 description 22
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
239000002585 base Substances 0.000 description 21
238000001704 evaporation Methods 0.000 description 21
230000008020 evaporation Effects 0.000 description 21
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 19
238000003756 stirring Methods 0.000 description 19
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
150000003585 thioureas Chemical class 0.000 description 18
HJZYBDPHAHGHAZ-UHFFFAOYSA-N thiadiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSN=N1 HJZYBDPHAHGHAZ-UHFFFAOYSA-N 0.000 description 17
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 15
229960000583 acetic acid Drugs 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
241000700605 Viruses Species 0.000 description 14
239000002253 acid Substances 0.000 description 13
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
208000015181 infectious disease Diseases 0.000 description 12
239000000543 intermediate Substances 0.000 description 12
150000003512 tertiary amines Chemical class 0.000 description 12
239000012044 organic layer Substances 0.000 description 11
239000000843 powder Substances 0.000 description 11
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 10
239000012298 atmosphere Substances 0.000 description 10
150000001732 carboxylic acid derivatives Chemical class 0.000 description 10
238000001914 filtration Methods 0.000 description 10
229910052763 palladium Inorganic materials 0.000 description 10
235000017557 sodium bicarbonate Nutrition 0.000 description 10
229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
239000011877 solvent mixture Substances 0.000 description 10
239000000725 suspension Substances 0.000 description 10
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 10
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 10
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
239000000706 filtrate Substances 0.000 description 9
239000012362 glacial acetic acid Substances 0.000 description 9
239000007788 liquid Substances 0.000 description 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 8
239000005909 Kieselgur Substances 0.000 description 8
229910052786 argon Inorganic materials 0.000 description 8
239000003054 catalyst Substances 0.000 description 8
239000012230 colorless oil Substances 0.000 description 8
229910052794 bromium Inorganic materials 0.000 description 7
239000000969 carrier Substances 0.000 description 7
239000010410 layer Substances 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
238000006722 reduction reaction Methods 0.000 description 7
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
238000003786 synthesis reaction Methods 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
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 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
210000004027 cell Anatomy 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical class CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 6
238000004519 manufacturing process Methods 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
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
230000003612 virological effect Effects 0.000 description 6
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 5
FUBFWTUFPGFHOJ-UHFFFAOYSA-N 2-nitrofuran Chemical compound [O-][N+](=O)C1=CC=CO1 FUBFWTUFPGFHOJ-UHFFFAOYSA-N 0.000 description 5
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
238000004458 analytical method Methods 0.000 description 5
150000001448 anilines Chemical class 0.000 description 5
230000000840 anti-viral effect Effects 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
238000003556 assay Methods 0.000 description 5
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-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
230000000694 effects Effects 0.000 description 5
150000002148 esters Chemical class 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
239000006260 foam Substances 0.000 description 5
201000006747 infectious mononucleosis Diseases 0.000 description 5
150000002540 isothiocyanates Chemical class 0.000 description 5
239000000463 material Substances 0.000 description 5
239000002243 precursor Substances 0.000 description 5
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JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 1
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229940096397 interleukin-8 Drugs 0.000 description 1
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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
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210000004072 lung Anatomy 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
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VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
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FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
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239000003550 marker Substances 0.000 description 1
NRVFDGZJTPCULU-UHFFFAOYSA-N meda Chemical compound Cl.CN(C)CCS NRVFDGZJTPCULU-UHFFFAOYSA-N 0.000 description 1
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LRPCLTPZMUIPFK-UHFFFAOYSA-N methane;sulfuric acid Chemical compound C.OS(O)(=O)=O LRPCLTPZMUIPFK-UHFFFAOYSA-N 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
ZSUZPVQLZKAKJY-UHFFFAOYSA-N methyl 2-(2-chloro-5-methoxy-4-nitrophenoxy)acetate Chemical compound COC(=O)COC1=CC(OC)=C([N+]([O-])=O)C=C1Cl ZSUZPVQLZKAKJY-UHFFFAOYSA-N 0.000 description 1
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
BVJFNYVXAADJFW-UHFFFAOYSA-N methyl 2-(4-amino-2-chloro-5-methoxyphenoxy)acetate Chemical compound COC(=O)COC1=CC(OC)=C(N)C=C1Cl BVJFNYVXAADJFW-UHFFFAOYSA-N 0.000 description 1
FGDKOGCAEWDASY-UHFFFAOYSA-N methyl 2-(4-chloro-5-methoxy-2-nitrophenoxy)acetate Chemical compound COC(=O)COC1=CC(OC)=C(Cl)C=C1[N+]([O-])=O FGDKOGCAEWDASY-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
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
CUUBRIQYOQKXOK-UHFFFAOYSA-N methyl 3-(2-amino-2-oxoethoxy)benzoate Chemical compound COC(=O)C1=CC=CC(OCC(N)=O)=C1 CUUBRIQYOQKXOK-UHFFFAOYSA-N 0.000 description 1
HSEHOLYDJIEPDD-UHFFFAOYSA-N methyl 3-[(4-aminophenyl)carbamoyl]benzoate Chemical compound COC(=O)C1=CC=CC(C(=O)NC=2C=CC(N)=CC=2)=C1 HSEHOLYDJIEPDD-UHFFFAOYSA-N 0.000 description 1
OSAIFPGOISKWPO-UHFFFAOYSA-N methyl 3-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]benzoate Chemical compound COC(=O)C1=CC=CC(OCC(=O)OC(C)(C)C)=C1 OSAIFPGOISKWPO-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
IAHNWFUEJBDAPZ-UHFFFAOYSA-N methyl 3-[[4-[(2-fluorobenzoyl)amino]phenyl]carbamothioylamino]benzoate Chemical compound COC(=O)C1=CC=CC(NC(=S)NC=2C=CC(NC(=O)C=3C(=CC=CC=3)F)=CC=2)=C1 IAHNWFUEJBDAPZ-UHFFFAOYSA-N 0.000 description 1
WTMLYBLWYPOMAY-UHFFFAOYSA-N methyl 3-[[4-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]carbamoyl]benzoate Chemical compound COC(=O)C1=CC=CC(C(=O)NC=2C=CC(NC(=O)OC(C)(C)C)=CC=2)=C1 WTMLYBLWYPOMAY-UHFFFAOYSA-N 0.000 description 1
JFVZLASFAAUWNF-UHFFFAOYSA-N methyl 3-[[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]phenyl]carbamoyl]benzoate Chemical compound COC(=O)C1=CC=CC(C(=O)NC=2C=CC(NC(=S)NC=3C(=CC(OC)=C(Cl)C=3)OC)=CC=2)=C1 JFVZLASFAAUWNF-UHFFFAOYSA-N 0.000 description 1
FBAGXCNLVAIFMR-UHFFFAOYSA-N methyl 3-butoxybenzoate Chemical compound CCCCOC1=CC=CC(C(=O)OC)=C1 FBAGXCNLVAIFMR-UHFFFAOYSA-N 0.000 description 1
GXYHJIBDTBLMNZ-UHFFFAOYSA-N methyl 4-[(2-fluorobenzoyl)amino]-2-hydroxybenzoate Chemical compound C1=C(O)C(C(=O)OC)=CC=C1NC(=O)C1=CC=CC=C1F GXYHJIBDTBLMNZ-UHFFFAOYSA-N 0.000 description 1
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125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
238000000386 microscopy Methods 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
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238000004264 monolayer culture Methods 0.000 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
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RAWAGHDKUYYVTF-UHFFFAOYSA-N tert-butyl n-[4-(quinoline-4-carbonylamino)phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=NC2=CC=CC=C12 RAWAGHDKUYYVTF-UHFFFAOYSA-N 0.000 description 1
IPNDXUKMNVJGRR-UHFFFAOYSA-N tert-butyl n-[4-(quinoline-6-carbonylamino)phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=C(N=CC=C2)C2=C1 IPNDXUKMNVJGRR-UHFFFAOYSA-N 0.000 description 1
NTXPRIRXXZXTOB-UHFFFAOYSA-N tert-butyl n-[4-(quinoline-8-carbonylamino)phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=CC2=CC=CN=C12 NTXPRIRXXZXTOB-UHFFFAOYSA-N 0.000 description 1
AFCSFMHRDNZDBE-UHFFFAOYSA-N tert-butyl n-[4-(thiadiazole-4-carbonylamino)phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CSN=N1 AFCSFMHRDNZDBE-UHFFFAOYSA-N 0.000 description 1
GAEJSWMWLLRKMS-UHFFFAOYSA-N tert-butyl n-[4-(thiophene-2-carbonylamino)phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=CS1 GAEJSWMWLLRKMS-UHFFFAOYSA-N 0.000 description 1
PONKNSIBPPSPCJ-UHFFFAOYSA-N tert-butyl n-[4-(thiophene-3-carbonylamino)phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CSC=C1 PONKNSIBPPSPCJ-UHFFFAOYSA-N 0.000 description 1
IDTVEXOYOSLLEV-UHFFFAOYSA-N tert-butyl n-[4-[(1-methylpyrazole-4-carbonyl)amino]phenyl]carbamate Chemical compound C1=NN(C)C=C1C(=O)NC1=CC=C(NC(=O)OC(C)(C)C)C=C1 IDTVEXOYOSLLEV-UHFFFAOYSA-N 0.000 description 1
DUODDVDUGBPAPW-UHFFFAOYSA-N tert-butyl n-[4-[(1-methylpyrrole-2-carbonyl)amino]phenyl]carbamate Chemical compound CN1C=CC=C1C(=O)NC1=CC=C(NC(=O)OC(C)(C)C)C=C1 DUODDVDUGBPAPW-UHFFFAOYSA-N 0.000 description 1
YFXQNMOWUCDGGP-UHFFFAOYSA-N tert-butyl n-[4-[(2,2,2-trifluoroacetyl)amino]phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(NC(=O)C(F)(F)F)C=C1 YFXQNMOWUCDGGP-UHFFFAOYSA-N 0.000 description 1
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GVGAHJAMZCOUJR-UHFFFAOYSA-N tert-butyl n-[4-[(2,3,4-trifluorobenzoyl)amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=C(F)C(F)=C1F GVGAHJAMZCOUJR-UHFFFAOYSA-N 0.000 description 1
AZUDOHZEPBCLFS-UHFFFAOYSA-N tert-butyl n-[4-[(2,3-difluorobenzoyl)amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=CC(F)=C1F AZUDOHZEPBCLFS-UHFFFAOYSA-N 0.000 description 1
GMLNLFKEZIKIJK-UHFFFAOYSA-N tert-butyl n-[4-[(2,4-difluorobenzoyl)amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=C(F)C=C1F GMLNLFKEZIKIJK-UHFFFAOYSA-N 0.000 description 1
GWTFHDISGSGLCH-UHFFFAOYSA-N tert-butyl n-[4-[(2,5-difluorobenzoyl)amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC(F)=CC=C1F GWTFHDISGSGLCH-UHFFFAOYSA-N 0.000 description 1
PNROEDGELBDHPB-UHFFFAOYSA-N tert-butyl n-[4-[(2,6-difluorobenzoyl)amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=C(F)C=CC=C1F PNROEDGELBDHPB-UHFFFAOYSA-N 0.000 description 1
XUSAOJFRDOLWBP-UHFFFAOYSA-N tert-butyl n-[4-[(2-acetamidobenzoyl)amino]phenyl]carbamate Chemical compound CC(=O)NC1=CC=CC=C1C(=O)NC1=CC=C(NC(=O)OC(C)(C)C)C=C1 XUSAOJFRDOLWBP-UHFFFAOYSA-N 0.000 description 1
YCGDCIMCVPMJPY-UHFFFAOYSA-N tert-butyl n-[4-[(2-aminobenzoyl)amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=CC=C1N YCGDCIMCVPMJPY-UHFFFAOYSA-N 0.000 description 1
MEVQBAGNWDIFDD-UHFFFAOYSA-N tert-butyl n-[4-[(2-bromoacetyl)amino]phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(NC(=O)CBr)C=C1 MEVQBAGNWDIFDD-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
KDFRHSFQAOSZQE-UHFFFAOYSA-N tert-butyl n-[4-[(2-methoxyacetyl)amino]phenyl]carbamate Chemical compound COCC(=O)NC1=CC=C(NC(=O)OC(C)(C)C)C=C1 KDFRHSFQAOSZQE-UHFFFAOYSA-N 0.000 description 1
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UTZSXLVGWGXITH-UHFFFAOYSA-N tert-butyl n-[4-[(2-methylbenzoyl)amino]phenyl]carbamate Chemical compound CC1=CC=CC=C1C(=O)NC1=CC=C(NC(=O)OC(C)(C)C)C=C1 UTZSXLVGWGXITH-UHFFFAOYSA-N 0.000 description 1
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DRSMFGINBQTFIG-UHFFFAOYSA-N tert-butyl n-[4-[(2-phenoxyacetyl)amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)COC1=CC=CC=C1 DRSMFGINBQTFIG-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
YWMBIUKKVJUKNP-UHFFFAOYSA-N tert-butyl n-[4-[(2-phenylbenzoyl)amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=CC=C1 YWMBIUKKVJUKNP-UHFFFAOYSA-N 0.000 description 1
NSSFYGLBAFAXQQ-UHFFFAOYSA-N tert-butyl n-[4-[(2-thiophen-2-ylacetyl)amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)CC1=CC=CS1 NSSFYGLBAFAXQQ-UHFFFAOYSA-N 0.000 description 1
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RNACSUSPWJJVCO-UHFFFAOYSA-N tert-butyl n-[4-[(3-chlorobenzoyl)amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=CC(Cl)=C1 RNACSUSPWJJVCO-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
QVAAYZAZJRKEIM-UHFFFAOYSA-N tert-butyl n-[4-[(3-methoxybenzoyl)amino]phenyl]carbamate Chemical compound COC1=CC=CC(C(=O)NC=2C=CC(NC(=O)OC(C)(C)C)=CC=2)=C1 QVAAYZAZJRKEIM-UHFFFAOYSA-N 0.000 description 1
DCKOZUUZDJXIOD-UHFFFAOYSA-N tert-butyl n-[4-[(3-nitrobenzoyl)amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=CC([N+]([O-])=O)=C1 DCKOZUUZDJXIOD-UHFFFAOYSA-N 0.000 description 1
BGDVOVSHZAICJP-UHFFFAOYSA-N tert-butyl n-[4-[(3-phenylmethoxybenzoyl)amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=CC(OCC=2C=CC=CC=2)=C1 BGDVOVSHZAICJP-UHFFFAOYSA-N 0.000 description 1
VAJUGOIBLDRSTG-UHFFFAOYSA-N tert-butyl n-[4-[(4-bromofuran-2-carbonyl)amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC(Br)=CO1 VAJUGOIBLDRSTG-UHFFFAOYSA-N 0.000 description 1
OBSPMHSGXIADEH-UHFFFAOYSA-N tert-butyl n-[4-[(4-chlorobenzoyl)amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=C(Cl)C=C1 OBSPMHSGXIADEH-UHFFFAOYSA-N 0.000 description 1
SRPZAUAKXYGNJT-UHFFFAOYSA-N tert-butyl n-[4-[(4-fluorobenzoyl)amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=C(F)C=C1 SRPZAUAKXYGNJT-UHFFFAOYSA-N 0.000 description 1
NVHZXGFDEQXWRN-UHFFFAOYSA-N tert-butyl n-[4-[(4-methoxybenzoyl)amino]phenyl]carbamate Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=CC=C(NC(=O)OC(C)(C)C)C=C1 NVHZXGFDEQXWRN-UHFFFAOYSA-N 0.000 description 1
ZNRXWSHPBWQCKM-UHFFFAOYSA-N tert-butyl n-[4-[(4-methylthiadiazole-5-carbonyl)amino]phenyl]carbamate Chemical compound N1=NSC(C(=O)NC=2C=CC(NC(=O)OC(C)(C)C)=CC=2)=C1C ZNRXWSHPBWQCKM-UHFFFAOYSA-N 0.000 description 1
HQLFMFKDFOPKCK-UHFFFAOYSA-N tert-butyl n-[4-[(4-phenylthiadiazole-5-carbonyl)amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=C(C=2C=CC=CC=2)N=NS1 HQLFMFKDFOPKCK-UHFFFAOYSA-N 0.000 description 1
GBQHYGWLVANMCG-UHFFFAOYSA-N tert-butyl n-[4-[(5-bromofuran-2-carbonyl)amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=C(Br)O1 GBQHYGWLVANMCG-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
QIMJQLUYBZOCTM-UHFFFAOYSA-N tert-butyl n-[4-[(5-chlorofuran-2-carbonyl)amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=C(Cl)O1 QIMJQLUYBZOCTM-UHFFFAOYSA-N 0.000 description 1
AEIASTOSAUZCIO-UHFFFAOYSA-N tert-butyl n-[4-[(5-methylfuran-2-carbonyl)amino]phenyl]carbamate Chemical compound O1C(C)=CC=C1C(=O)NC1=CC=C(NC(=O)OC(C)(C)C)C=C1 AEIASTOSAUZCIO-UHFFFAOYSA-N 0.000 description 1
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GHWRLOICVYTSTQ-UHFFFAOYSA-N tert-butyl n-[4-[(5-methylthiophene-2-carbonyl)amino]phenyl]carbamate Chemical compound S1C(C)=CC=C1C(=O)NC1=CC=C(NC(=O)OC(C)(C)C)C=C1 GHWRLOICVYTSTQ-UHFFFAOYSA-N 0.000 description 1
FBGWGHHCPHBMQN-UHFFFAOYSA-N tert-butyl n-[4-[(5-nitrofuran-2-carbonyl)amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=C([N+]([O-])=O)O1 FBGWGHHCPHBMQN-UHFFFAOYSA-N 0.000 description 1
VNKTWZDFNVAPMZ-UHFFFAOYSA-N tert-butyl n-[4-[(5-tert-butylfuran-2-carbonyl)amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=C(C(C)(C)C)O1 VNKTWZDFNVAPMZ-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
GHZKMSUVYSBNDV-UHFFFAOYSA-N tert-butyl n-[4-[[2-(methanesulfonamido)benzoyl]amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=CC=C1NS(C)(=O)=O GHZKMSUVYSBNDV-UHFFFAOYSA-N 0.000 description 1
DTZQGKSHZLFXPY-UHFFFAOYSA-N tert-butyl n-[4-[[2-(trifluoromethyl)benzoyl]amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=CC=C1C(F)(F)F DTZQGKSHZLFXPY-UHFFFAOYSA-N 0.000 description 1
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VLTQLTGMLGYPLQ-UHFFFAOYSA-N tert-butyl n-[4-[[3-(2-amino-2-oxoethoxy)benzoyl]amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=CC(OCC(N)=O)=C1 VLTQLTGMLGYPLQ-UHFFFAOYSA-N 0.000 description 1
OGDFBAHQMAXPFC-UHFFFAOYSA-N tert-butyl n-[4-[[3-(2-chloroethoxy)benzoyl]amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=CC(OCCCl)=C1 OGDFBAHQMAXPFC-UHFFFAOYSA-N 0.000 description 1
JYYFRDMCJXORJM-UHFFFAOYSA-N tert-butyl n-[4-[[3-(2-morpholin-4-ylethoxy)benzoyl]amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=CC(OCCN2CCOCC2)=C1 JYYFRDMCJXORJM-UHFFFAOYSA-N 0.000 description 1
IBBPYSPXUPECOC-UHFFFAOYSA-N tert-butyl n-[4-[[3-(methanesulfonamido)benzoyl]amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=CC(NS(C)(=O)=O)=C1 IBBPYSPXUPECOC-UHFFFAOYSA-N 0.000 description 1
GREAORFBJKJVFX-UHFFFAOYSA-N tert-butyl n-[4-[[3-(trifluoromethoxy)benzoyl]amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=CC(OC(F)(F)F)=C1 GREAORFBJKJVFX-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
GLUDOUKXILLBQU-UHFFFAOYSA-N tert-butyl n-[4-[[3-[2-(dimethylamino)ethoxy]benzoyl]amino]phenyl]carbamate Chemical compound CN(C)CCOC1=CC=CC(C(=O)NC=2C=CC(NC(=O)OC(C)(C)C)=CC=2)=C1 GLUDOUKXILLBQU-UHFFFAOYSA-N 0.000 description 1
DGBSFICLDZKJDV-UHFFFAOYSA-N tert-butyl n-[4-[[4-(dimethylamino)benzoyl]amino]phenyl]carbamate Chemical compound C1=CC(N(C)C)=CC=C1C(=O)NC1=CC=C(NC(=O)OC(C)(C)C)C=C1 DGBSFICLDZKJDV-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
VGIMWMKLPXTNNB-UHFFFAOYSA-N tert-butyl n-[4-[[5-(difluoromethyl)furan-2-carbonyl]amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=C(C(F)F)O1 VGIMWMKLPXTNNB-UHFFFAOYSA-N 0.000 description 1
FRGHHUJRPBXQOA-UHFFFAOYSA-N tert-butyl n-[4-[[5-(furan-3-yl)thiadiazole-4-carbonyl]amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=C(C2=COC=C2)SN=N1 FRGHHUJRPBXQOA-UHFFFAOYSA-N 0.000 description 1
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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
UAWWHIOAOFZQET-UHFFFAOYSA-N tert-butyl n-[[4-(thiadiazole-4-carbonylamino)phenyl]methyl]carbamate Chemical compound C1=CC(CNC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CSN=N1 UAWWHIOAOFZQET-UHFFFAOYSA-N 0.000 description 1
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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
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
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
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 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
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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 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
210000003501 vero cell Anatomy 0.000 description 1
239000004034 viscosity adjusting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more 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
- 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
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D207/14—Nitrogen atoms not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Virology (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Molecular Biology (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Biotechnology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Quinoline Compounds (AREA)
Indole Compounds (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Furan Compounds (AREA)
Hydrogenated Pyridines (AREA)
Pyridine Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pyrrole Compounds (AREA)

KR1020017007052A 1998-12-09 1999-12-06 헤르페스 바이러스의 아세트아마이드 및 치환아세트아마이드-함유 티오우레아 억제제 Withdrawn KR20010087413A (ko)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US20831698A	1998-12-09	1998-12-09
US09/208,316		1998-12-09
PCT/US1999/028844 WO2000034237A2 (fr)	1998-12-09	1999-12-06	Inhibiteurs des virus de l'herpes a base de thio-urees contenant des acetamides et des acetamides substitues

Publications (1)

Publication Number	Publication Date
KR20010087413A true KR20010087413A (ko)	2001-09-15

Family

ID=22774137

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
KR1020017007052A Withdrawn KR20010087413A (ko)	1998-12-09	1999-12-06	헤르페스 바이러스의 아세트아마이드 및 치환아세트아마이드-함유 티오우레아 억제제

Country Status (15)

Country	Link
EP (1)	EP1137633A2 (fr)
JP (1)	JP2002531544A (fr)
KR (1)	KR20010087413A (fr)
CN (1)	CN1333750A (fr)
AU (1)	AU3111200A (fr)
BR (1)	BR9916041A (fr)
CA (1)	CA2350899A1 (fr)
CZ (1)	CZ20012060A3 (fr)
EA (1)	EA200100640A1 (fr)
HU (1)	HUP0104944A3 (fr)
IL (1)	IL143204A0 (fr)
NO (1)	NO20012834L (fr)
PL (1)	PL349131A1 (fr)
WO (1)	WO2000034237A2 (fr)
ZA (1)	ZA200104142B (fr)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6166028A (en) *	1998-12-09	2000-12-26	American Home Products Corporation	Diaminopuridine-containing thiourea inhibitors of herpes viruses
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
RU2005115842A (ru) *	2002-10-24	2006-03-10	Мерк Патент ГмбХ (DE)	Производные метиленмочевины
US7220768B2 (en) *	2003-02-11	2007-05-22	Wyeth Holdings Corp.	Isoxazole-containing thiourea inhibitors useful for treatment of varicella zoster virus
WO2005014825A2 (fr)	2003-08-08	2005-02-17	Arriva Pharmaceuticals, Inc.	Procede de production de proteines dans une levure
WO2005021488A1 (fr)	2003-08-29	2005-03-10	Mitsui Chemicals, Inc.	Insecticide s'utilisant en agriculture ou en horticulture et procede d'utilisation correspondant
JP2007528409A (ja)	2004-03-09	2007-10-11	アリバファーマシューティカルズ，インコーポレイテッド	プロテアーゼインヒビターの低用量吸入による慢性閉塞性肺疾患の処置
US20100093864A1 (en) *	2006-10-13	2010-04-15	Lica Pharmaceuticals	Anti-infective thiourea compounds
ES2550057T3 (es)	2006-11-02	2015-11-04	Millennium Pharmaceuticals, Inc.	Métodos para sintetizar sales farmacéuticas de un inhibidor del Factor Xa
CN108619123A (zh) *	2018-03-13	2018-10-09	武汉威立得生物医药有限公司	Tenovin-1在制备防治人类疱疹病毒感染药物中的应用
WO2019193541A1 (fr) *	2018-04-06	2019-10-10	Glaxosmithkline Intellectual Property Development Limited	Dérivés de cycle aromatiques bicycliques de formule (i) utilisés en tant qu'inhibiteurs d'atf4
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
WO2022150962A1 (fr) *	2021-01-12	2022-07-21	Westlake Pharmaceutical (Hangzhou) Co., Ltd.	Inhibiteurs de protéase, leur préparation et leurs utilisations

Family Cites Families (1)

* Cited by examiner, † Cited by third party
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 EP EP99965132A patent/EP1137633A2/fr not_active Withdrawn
- 1999-12-06 JP JP2000586685A patent/JP2002531544A/ja active Pending
- 1999-12-06 BR BR9916041-2A patent/BR9916041A/pt not_active Application Discontinuation
- 1999-12-06 EA EA200100640A patent/EA200100640A1/ru unknown
- 1999-12-06 KR KR1020017007052A patent/KR20010087413A/ko not_active Withdrawn
- 1999-12-06 CA CA002350899A patent/CA2350899A1/fr not_active Abandoned
- 1999-12-06 HU HU0104944A patent/HUP0104944A3/hu unknown
- 1999-12-06 AU AU31112/00A patent/AU3111200A/en not_active Abandoned
- 1999-12-06 CN CN99815640A patent/CN1333750A/zh active Pending
- 1999-12-06 IL IL14320499A patent/IL143204A0/xx unknown
- 1999-12-06 WO PCT/US1999/028844 patent/WO2000034237A2/fr not_active Ceased
- 1999-12-06 CZ CZ20012060A patent/CZ20012060A3/cs unknown
- 1999-12-06 PL PL99349131A patent/PL349131A1/xx not_active Application Discontinuation
2001
- 2001-05-21 ZA ZA200104142A patent/ZA200104142B/en unknown
- 2001-06-08 NO NO20012834A patent/NO20012834L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
JP2002531544A (ja)	2002-09-24
BR9916041A (pt)	2001-12-04
EA200100640A1 (ru)	2001-12-24
CA2350899A1 (fr)	2000-06-15
NO20012834L (no)	2001-08-07
WO2000034237A2 (fr)	2000-06-15
CN1333750A (zh)	2002-01-30
WO2000034237A3 (fr)	2000-11-23
IL143204A0 (en)	2002-04-21
HUP0104944A3 (en)	2003-03-28
PL349131A1 (en)	2002-07-01
CZ20012060A3 (cs)	2001-11-14
ZA200104142B (en)	2002-10-25
HUP0104944A2 (hu)	2002-04-29
NO20012834D0 (no)	2001-06-08
AU3111200A (en)	2000-06-26
EP1137633A2 (fr)	2001-10-04

Publication	Publication Date	Title
US6403617B1 (en)	2002-06-11	Diaminopyridine-containing thiourea inhibitors of herpes viruses
KR20010087413A (ko)	2001-09-15	헤르페스 바이러스의 아세트아마이드 및 치환아세트아마이드-함유 티오우레아 억제제
EP1137632B1 (fr)	2004-07-28	Thio-urees inhibitrices des virus de l'herpes
AU1934700A (en)	2000-06-26	Heterocyclic carboxamide-containing thiourea inhibitors of herpes viruses containing phenylenediamine group
EP1137645B1 (fr)	2004-05-26	Thio-urees alpha-methylbenzylees porteuses d'un groupe phenylene-diamine et inhibitrices des virus de l'herpes
AU2353900A (en)	2000-06-26	Heterocyclic carboxamide-containing thiourea inhibitors of herpes viruses containing a substituted phenylenediamine group
US6201013B1 (en)	2001-03-13	Heterocyclic carboxamide-containing thiourea inhibitors of herpes viruses containing a substituted phenylenediamine group
WO2000034269A1 (fr)	2000-06-15	Inhibiteurs de thio-uree des virus de l'herpes
AU756043B2 (en)	2003-01-02	Thiourea inhibitors of herpes viruses
US6207715B1 (en)	2001-03-27	Alpha-methylbenzyl-containing thiourea inhibitors of herpes viruses containing a substituted phenylene-diamine group
US6462055B2 (en)	2002-10-08	Alpha-methylbenzyl-containing thiourea inhibitors of herpes viruses containing a phenylenediamine group
US6335350B1 (en)	2002-01-01	Acetamide and substituted acetamide-containing thiourea inhibitors of herpes viruses
KR20010086090A (ko)	2001-09-07	헤르페스 바이러스의 티오우레아 억제제
US6380243B1 (en)	2002-04-30	Aminopyridine-containing thiourea inhibitors of herpes viruses
US6426355B1 (en)	2002-07-30	Heterocyclic carboxamide-containing thiourea inhibitors of herpes viruses containing phenylenediamine group
KR20010087416A (ko)	2001-09-15	페닐렌디아민기를 함유하는 헤르페스 바이러스의헤테로시클릭 카르복사미드-함유 티오우레아 저해제

Legal Events

Date	Code	Title	Description
2001-06-05	PA0105	International application	Patent event date: 20010605 Patent event code: PA01051R01D Comment text: International Patent Application
2001-09-15	PG1501	Laying open of application
2004-12-07	PC1203	Withdrawal of no request for examination
2004-12-07	WITN	Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid