EP1144399A2 - Heterocyclic carboxamide-containing thiourea inhibitors of herpes viruses containing a substituted phenylenediamine group - Google Patents
Heterocyclic carboxamide-containing thiourea inhibitors of herpes viruses containing a substituted phenylenediamine groupInfo
- Publication number
- EP1144399A2 EP1144399A2 EP99967213A EP99967213A EP1144399A2 EP 1144399 A2 EP1144399 A2 EP 1144399A2 EP 99967213 A EP99967213 A EP 99967213A EP 99967213 A EP99967213 A EP 99967213A EP 1144399 A2 EP1144399 A2 EP 1144399A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- phenyl
- chloro
- carbon atoms
- thioureido
- amide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 241001529453 unidentified herpesvirus Species 0.000 title claims abstract description 17
- -1 Heterocyclic carboxamide Chemical class 0.000 title description 55
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title description 15
- 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
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical group NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 title description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 132
- 150000001875 compounds Chemical class 0.000 claims abstract description 113
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 45
- 239000001257 hydrogen Substances 0.000 claims abstract description 45
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 21
- 241000701085 Human alphaherpesvirus 3 Species 0.000 claims abstract description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 15
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 14
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 241000701024 Human betaherpesvirus 5 Species 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
- 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 274
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 23
- 150000002431 hydrogen Chemical group 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- RTHGALAUXSQETR-UHFFFAOYSA-N 5-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-2-(furan-2-carbonylamino)benzoic acid Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1C(O)=O)=CC=C1NC(=O)C1=CC=CO1 RTHGALAUXSQETR-UHFFFAOYSA-N 0.000 claims description 3
- IVZPBGXWYFFTRA-UHFFFAOYSA-N n-[2-chloro-4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]phenyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1Cl)=CC=C1NC(=O)C1=CC=CO1 IVZPBGXWYFFTRA-UHFFFAOYSA-N 0.000 claims description 3
- IVWGGGIKOICPHX-UHFFFAOYSA-N n-[3-chloro-4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]phenyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C(=C1)Cl)=CC=C1NC(=O)C1=CC=CO1 IVWGGGIKOICPHX-UHFFFAOYSA-N 0.000 claims description 3
- IMKYKPMGBIAZML-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-2-cyanophenyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1C#N)=CC=C1NC(=O)C1=CC=CO1 IMKYKPMGBIAZML-UHFFFAOYSA-N 0.000 claims description 3
- MVDDTRTYCQAJNC-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-2-methoxy-5-methylphenyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C(=C1)C)=CC(OC)=C1NC(=O)C1=CC=CO1 MVDDTRTYCQAJNC-UHFFFAOYSA-N 0.000 claims description 3
- HHPFMXDSJANDMY-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-2-methoxyphenyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1OC)=CC=C1NC(=O)C1=CC=CO1 HHPFMXDSJANDMY-UHFFFAOYSA-N 0.000 claims description 3
- YMWKSEPIFCEVMT-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-2-methylphenyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1C)=CC=C1NC(=O)C1=CC=CO1 YMWKSEPIFCEVMT-UHFFFAOYSA-N 0.000 claims description 3
- BXFNYZZUCCFYSD-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-3-cyanophenyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C(=C1)C#N)=CC=C1NC(=O)C1=CC=CO1 BXFNYZZUCCFYSD-UHFFFAOYSA-N 0.000 claims description 3
- MVPZQPMABBRKST-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-3-methoxyphenyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C(=C1)OC)=CC=C1NC(=O)C1=CC=CO1 MVPZQPMABBRKST-UHFFFAOYSA-N 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 230000010076 replication Effects 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- JPZGNXJCBOMBMR-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-2,5-dimethoxyphenyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C(=C1)OC)=CC(OC)=C1NC(=O)C1=CC=CO1 JPZGNXJCBOMBMR-UHFFFAOYSA-N 0.000 claims description 2
- VVCYTMKINNBCAU-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-2-(phenylcarbamoyl)phenyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1C(=O)NC=2C=CC=CC=2)=CC=C1NC(=O)C1=CC=CO1 VVCYTMKINNBCAU-UHFFFAOYSA-N 0.000 claims description 2
- BALIPFKCBQPMKC-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-2-(trifluoromethyl)phenyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1C(F)(F)F)=CC=C1NC(=O)C1=CC=CO1 BALIPFKCBQPMKC-UHFFFAOYSA-N 0.000 claims description 2
- UWEFSTBGDNYWES-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-3-(trifluoromethyl)phenyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C(=C1)C(F)(F)F)=CC=C1NC(=O)C1=CC=CO1 UWEFSTBGDNYWES-UHFFFAOYSA-N 0.000 claims description 2
- GDUBTFSXSUOPTA-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-3-methylphenyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C(=C1)C)=CC=C1NC(=O)C1=CC=CO1 GDUBTFSXSUOPTA-UHFFFAOYSA-N 0.000 claims description 2
- HQSLZZTYRDVJIX-UHFFFAOYSA-N n-[4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]naphthalen-1-yl]furan-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C1=CC=CC=C11)=CC=C1NC(=O)C1=CC=CO1 HQSLZZTYRDVJIX-UHFFFAOYSA-N 0.000 claims description 2
- NSOSRWUCBJXURG-UHFFFAOYSA-N n-[5-chloro-4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-2-hydroxyphenyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C(=C1)Cl)=CC(O)=C1NC(=O)C1=CC=CO1 NSOSRWUCBJXURG-UHFFFAOYSA-N 0.000 claims description 2
- UDAPAWGOOPLTNL-UHFFFAOYSA-N n-[5-chloro-4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]-2-methylphenyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C(=C1)Cl)=CC(C)=C1NC(=O)C1=CC=CO1 UDAPAWGOOPLTNL-UHFFFAOYSA-N 0.000 claims 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
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 abstract description 20
- 238000011282 treatment Methods 0.000 abstract description 13
- 201000010099 disease Diseases 0.000 abstract description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 12
- 241000282414 Homo sapiens Species 0.000 abstract description 9
- 241000701044 Human gammaherpesvirus 4 Species 0.000 abstract description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 243
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 178
- 239000002904 solvent Substances 0.000 description 155
- 239000000243 solution Substances 0.000 description 149
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 142
- 239000002253 acid Substances 0.000 description 129
- HJZYBDPHAHGHAZ-UHFFFAOYSA-N thiadiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSN=N1 HJZYBDPHAHGHAZ-UHFFFAOYSA-N 0.000 description 124
- 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 108
- 239000000203 mixture Substances 0.000 description 105
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 94
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 92
- 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 Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 73
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 69
- 239000007787 solid Substances 0.000 description 68
- 238000006243 chemical reaction Methods 0.000 description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 66
- 239000007858 starting material Substances 0.000 description 65
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 60
- 238000010992 reflux Methods 0.000 description 55
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 51
- 229920006395 saturated elastomer Polymers 0.000 description 51
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 48
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 46
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 45
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 43
- 239000003921 oil Substances 0.000 description 42
- 235000019198 oils Nutrition 0.000 description 42
- 150000001412 amines Chemical class 0.000 description 41
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 40
- 239000011780 sodium chloride Substances 0.000 description 40
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 39
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 36
- 239000000741 silica gel Substances 0.000 description 33
- 229910002027 silica gel Inorganic materials 0.000 description 33
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 31
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 31
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 28
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 25
- 239000000284 extract Substances 0.000 description 23
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 23
- 229910000027 potassium carbonate Inorganic materials 0.000 description 23
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 22
- 238000001704 evaporation Methods 0.000 description 22
- 230000008020 evaporation Effects 0.000 description 22
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 20
- 239000002585 base Substances 0.000 description 20
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 17
- 229960000583 acetic acid Drugs 0.000 description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 241000700605 Viruses Species 0.000 description 14
- 238000003756 stirring Methods 0.000 description 13
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 12
- 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
- 239000012044 organic layer Substances 0.000 description 12
- 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 12
- 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
- 150000001448 anilines Chemical class 0.000 description 10
- 229910052786 argon Inorganic materials 0.000 description 10
- 238000003556 assay Methods 0.000 description 10
- 239000012298 atmosphere Substances 0.000 description 10
- 239000011877 solvent mixture Substances 0.000 description 10
- 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
- 150000003512 tertiary amines Chemical class 0.000 description 10
- 150000003585 thioureas Chemical class 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
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- 239000000706 filtrate Substances 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 239000012362 glacial acetic acid Substances 0.000 description 9
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- 230000009467 reduction Effects 0.000 description 9
- 238000006722 reduction reaction Methods 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- KGGHWIKBOIQEAJ-UHFFFAOYSA-N 2-fluorobenzamide Chemical compound NC(=O)C1=CC=CC=C1F KGGHWIKBOIQEAJ-UHFFFAOYSA-N 0.000 description 8
- 239000005909 Kieselgur Substances 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 239000012230 colorless oil Substances 0.000 description 8
- 229910052763 palladium Inorganic materials 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 150000008359 benzonitriles Chemical class 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 150000005181 nitrobenzenes Chemical class 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 7
- XXWIYOBCHKCWNT-UHFFFAOYSA-N 2,4-dimethoxy-1-nitrobenzene Chemical compound COC1=CC=C([N+]([O-])=O)C(OC)=C1 XXWIYOBCHKCWNT-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 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
- 239000003153 chemical reaction reagent Substances 0.000 description 6
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- 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
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000010322 reactivation of latent virus Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 229940016590 sarkosyl Drugs 0.000 description 1
- 108700004121 sarkosyl Proteins 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 206010040872 skin infection Diseases 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000001476 sodium potassium tartrate Substances 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 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
- 239000000126 substance Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
- BZRBABVBSBPJPS-UHFFFAOYSA-N tert-butyl N-(4-butoxy-3,5-dichlorophenyl)carbamate tert-butyl N-(3,5-dichloro-4-ethoxyphenyl)carbamate tert-butyl N-(3,5-dichloro-4-phenylmethoxyphenyl)carbamate Chemical compound C(C)(C)(C)OC(NC1=CC(=C(C(=C1)Cl)OCC1=CC=CC=C1)Cl)=O.C(C)(C)(C)OC(NC1=CC(=C(C(=C1)Cl)OCCCC)Cl)=O.C(C)(C)(C)OC(NC1=CC(=C(C(=C1)Cl)OCC)Cl)=O BZRBABVBSBPJPS-UHFFFAOYSA-N 0.000 description 1
- IQQJFQLTQKUYBB-UHFFFAOYSA-N tert-butyl N-[4-(furan-2-carbonylamino)phenyl]carbamate tert-butyl N-[4-[[3-(trifluoromethoxy)benzoyl]amino]phenyl]carbamate N-(2,5-dimethoxy-4-nitrophenyl)-2-fluorobenzamide Chemical compound C(C)(C)(C)OC(NC1=CC=C(C=C1)NC(=O)C=1OC=CC1)=O.COC1=C(C=C(C(=C1)[N+](=O)[O-])OC)NC(C1=C(C=CC=C1)F)=O.C(C)(C)(C)OC(NC1=CC=C(C=C1)NC(C1=CC(=CC=C1)OC(F)(F)F)=O)=O IQQJFQLTQKUYBB-UHFFFAOYSA-N 0.000 description 1
- KMTXUJMHRHFSFS-UHFFFAOYSA-N tert-butyl N-[4-[(2,6-difluorobenzoyl)amino]phenyl]carbamate tert-butyl N-[4-[[2-(trifluoromethyl)benzoyl]amino]phenyl]carbamate [4-[(2-chlorobenzoyl)amino]phenyl]carbamic acid Chemical compound ClC1=C(C(=O)NC2=CC=C(C=C2)NC(O)=O)C=CC=C1.C(C)(C)(C)OC(NC1=CC=C(C=C1)NC(C1=C(C=CC=C1F)F)=O)=O.C(C)(C)(C)OC(NC1=CC=C(C=C1)NC(C1=C(C=CC=C1)C(F)(F)F)=O)=O KMTXUJMHRHFSFS-UHFFFAOYSA-N 0.000 description 1
- LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 description 1
- VPONSBSZPHIIFJ-UHFFFAOYSA-N tert-butyl n-(3,5-dichloro-4-ethoxyphenyl)carbamate Chemical compound CCOC1=C(Cl)C=C(NC(=O)OC(C)(C)C)C=C1Cl VPONSBSZPHIIFJ-UHFFFAOYSA-N 0.000 description 1
- JCIPDXPPSLPJTH-UHFFFAOYSA-N tert-butyl n-(3-chloro-4-methylsulfinylphenyl)carbamate Chemical compound CS(=O)C1=CC=C(NC(=O)OC(C)(C)C)C=C1Cl JCIPDXPPSLPJTH-UHFFFAOYSA-N 0.000 description 1
- DNOQLJHQFUMRIM-UHFFFAOYSA-N tert-butyl n-(3-chloro-4-methylsulfonylphenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(S(C)(=O)=O)C(Cl)=C1 DNOQLJHQFUMRIM-UHFFFAOYSA-N 0.000 description 1
- HDGDNDFUABLUAQ-UHFFFAOYSA-N tert-butyl n-(4-amino-3-chlorophenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(N)C(Cl)=C1 HDGDNDFUABLUAQ-UHFFFAOYSA-N 0.000 description 1
- UXWQXBSQQHAGMG-UHFFFAOYSA-N tert-butyl n-[(4-aminophenyl)methyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC1=CC=C(N)C=C1 UXWQXBSQQHAGMG-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
- 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
- XEAXVVPEQMFMQC-UHFFFAOYSA-N tert-butyl n-[4-(1h-imidazole-5-carbonylamino)phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CNC=N1 XEAXVVPEQMFMQC-UHFFFAOYSA-N 0.000 description 1
- PCGJSLKJOJPRLC-UHFFFAOYSA-N tert-butyl n-[4-(1h-indole-2-carbonylamino)phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC2=CC=CC=C2N1 PCGJSLKJOJPRLC-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
- 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
- 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
- MXEZQQINCFODRG-UHFFFAOYSA-N tert-butyl n-[4-[(2-methylsulfinylbenzoyl)amino]phenyl]carbamate;2-methylsulfinyl-n-[4-[(2,2,2-trifluoroacetyl)amino]phenyl]benzamide Chemical compound CS(=O)C1=CC=CC=C1C(=O)NC1=CC=C(NC(=O)C(F)(F)F)C=C1.CS(=O)C1=CC=CC=C1C(=O)NC1=CC=C(NC(=O)OC(C)(C)C)C=C1 MXEZQQINCFODRG-UHFFFAOYSA-N 0.000 description 1
- UPPLJDLYCNYYAS-UHFFFAOYSA-N tert-butyl n-[4-[(5-tert-butylfuran-2-carbonyl)amino]phenyl]carbamate;n-[3-cyano-4-[(2,2,2-trifluoroacetyl)amino]phenyl]-2-fluorobenzamide;furan-2-carboxylic acid Chemical compound OC(=O)C1=CC=CO1.FC1=CC=CC=C1C(=O)NC1=CC=C(NC(=O)C(F)(F)F)C(C#N)=C1.C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=C(C(C)(C)C)O1 UPPLJDLYCNYYAS-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
- MTUPLPWQKINVTP-UHFFFAOYSA-N tert-butyl n-[4-[[2-[bis(2-hydroxyethyl)amino]acetyl]amino]phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(NC(=O)CN(CCO)CCO)C=C1 MTUPLPWQKINVTP-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
- BGUAPDWPQVMOBQ-UHFFFAOYSA-N tert-butyl n-[4-[[3-(trifluoromethyl)benzoyl]amino]phenyl]carbamate;2,2,2-trifluoro-n-(5-nitropyrimidin-2-yl)acetamide Chemical compound [O-][N+](=O)C1=CN=C(NC(=O)C(F)(F)F)N=C1.C1=CC(NC(=O)OC(C)(C)C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 BGUAPDWPQVMOBQ-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- NVSZTCDZTXKBNS-UHFFFAOYSA-N tert-butyl n-[6-[(2,2,2-trifluoroacetyl)amino]pyridin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(NC(=O)C(F)(F)F)N=C1 NVSZTCDZTXKBNS-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
- INWVNNCOIIHEPX-UHFFFAOYSA-N thiadiazole-4-carboxamide Chemical compound NC(=O)C1=CSN=N1 INWVNNCOIIHEPX-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
- 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
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
- 210000003501 vero cell Anatomy 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D307/85—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C335/20—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C335/22—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Definitions
- viruses have been identified which are members of the family Herpesviridae (reviewed in Roizman, B. 1996. Herpesviridae, p. 2221-2230. In B. N. Fields, D. M. Knipe, and P. M. Howley (ed.), Fields Virology, 3rd ed. Lippincott- Raven Publishers, Philadelphia, PA).
- Each member of this family is characterized by an enveloped virus containing proteinaceous tegument and nucleocapsid, the latter of which houses the viruses' relatively large double-stranded DNA genome (i.e. approximately 80-250 kilobases).
- HSV- 1 herpes simplex virus type 1
- HSV-2 type 2
- VZV varicella-zoster virus
- the human betaherpesviruses are cytomegalovirus (HCMV), human herpesvirus 6 (HHV-6) and human herpesvirus 7 (HHV-7).
- the gammaherpesviruses are lymphotropic and include Epstein-Barr virus (EBV) and Kaposi's herpesvirus (HHV-8). Each of these herpesviruses is causally- related to human disease, including herpes labialis and herpes genitalis (HSV-1 and HSV-2 [Whitley, R.J. 1996.
- Herpes Simplex Viruses p. 2297-2342.
- B. N. Fields, D. M. Knipe, and P. M. Howley (ed.), Fields Virology, 3rd ed. Lippincott-Raven Publishers, Philadelphia, PA] chicken pox and shingles (VZV [Arvin, A. 1996. Varicella-Zoster Virus, p. 2547-2585.
- infectious mononucleosis EBV [Rickinson, A. B.
- HCMV Kaposi's sarcoma
- herpesviruses establish latency within the infected individual and remain there for the remainder of his/her life. Periodic reactivation of latent virus is clinically relevant.
- reactivated virus can be transmitted to infants during birth, causing either skin or eye infection, central nervous system infection, or disseminated infection (i.e. multiple organs or systems). Shingles is the clinical manifestation of VZV reactivation.
- Treatment of HSV and VZV is generally with antiviral drugs such as acyclovir (Glaxo Wellcome), ganciclovir (Roche) and foscarnet (Asta) which target viral encoded DNA polymerase.
- HCMV is a ubiquitous opportunistic pathogen infecting 50-90% of the adult population (Britt, W. J., and Alford, C. A. 1996. Cytomegalovirus, p. 2493-2523. In B. N. Fields, D. M. Knipe, and P. M. Howley (ed.), Fields Virology, 3rd ed. Lippincott-Raven Publishers, Philadelphia, Pa.).
- Primary infection with HCMV is usually asymptomatic, although heterophile negative mononucleosis has been observed. The virus is horizontally transmitted by sexual contact, breast milk, and saliva. Intrauterine transmission of HCMV from the pregnant mother to the fetus occurs and is often the cause of serious clinical consequences.
- HCMV remains in a latent state within the infected person for the remainder of his/her life.
- Cell-mediated immunity plays a central role in controlling reactivation from latency. Impaired cellular immunity leads to reactivation of latent HCMV in seropositive persons.
- HCMV disease is associated with deficient or immature cellular immunity.
- HCMV HCMV is one of the two most common pathogens causing clinical disease (the other is Pneumocystis).
- the most common manifestation of HCMV in AIDS is retinitis, although infection of other organs including the adrenal glands, lungs, GI tract, and central nervous system are also reported frequently.
- 90% of AIDs patients have active HCMV infection; 25- 40% (-85,000 patients in the United States) have life- or sight-threatening HCMV disease.
- HCMV is the cause of death in 10% of persons with AIDs.
- HCMV reactivation or reinfection is common amongst kidney, liver, heart, and allogeneic bone marrow transplant patients. Pneumonia is the most common HCMV disease in these patients, occurring in up to 70% of these transplant patients.
- Congenital infection due to HCMV occurs in 1% of all births, about 40K per year. Up to 25% of these infants are symptomatic for HCMV disease between ages 0-3 years. HCMV disease is progressive, causing mental retardation and neurological abnormalities, in children. Recent studies suggest that treatment with anti-HCMV drugs may reduce morbidity in these children.
- ganciclovir a nucleoside analog with hemopoietic cell toxicity
- foscarnet Astra
- a pyrophosphate analog with nephrotoxicity Astra
- cidofovir, Gilead a nucleoside phosphonate with acute nephrotoxicity.
- Each of these drugs target the viral-encoded DNA polymerase are typically administered intravenously due to their low bioavailability, and, as noted above, are the source of significant toxicity.
- Ganciclovir-resistant mutants which arise clinically are often cross-resistant with cidofovir. Hence, there is a need for safer (i.e. less toxic), orally bioavailable antiviral drugs which are directed against novel viral targets.
- Phenyl thioureas are disclosed for use in a variety of pharmaceutical applications. Armistead, et al., WO 97/40028, teaches phenyl ureas and thioureas as inhibitors of the inosine monophosphate dehydrogenase (IMPDH) enzyme which is taught to play a role in viral replication diseases such herpes. Widdowson, et al., WO 96/25157, teaches phenyl urea and thiourea compounds of the below formula for treating diseases mediated by the chemokine, interleukin- 8.
- IMPDH inosine monophosphate dehydrogenase
- diseases associated with he ⁇ es viruses including human cytomegalovirus, herpes simplex viruses, Epstein-Barr virus, varicella-zoster virus, human herpesviruses-6 and -7, and Kaposi herpesvirus.
- R,-R 5 are independently selected from hydrogen, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, perhaloalkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 10 carbon atoms, heterocycloalkyl of 3 to 10 carbon members, aryl, heteroaryl, halogen, -CN, -NO 2 , -CO 2 R 6 , -COR 6 , -OR 6 , -SR 6 , -SOR 6 , -SO 2 R 6 , -CONR 7 R g , -NR 6 N(R 7 R ⁇ ), -N(R 7 R g ) or W-Y-(CH 2 ) n -Z provided that at least one of R ⁇ R j is not hydrogen; or R 2 and R 3 or R 3 and R 4 , taken together form a 3 to 7 membered heterocycloalkyl or 3
- R 9 -R 12 are independently hydrogen, alkyl of 1 to 4 carbon atoms, perhaloalkyl of 1 to 4 carbon atoms, halogen, alkoxy of 1 to 4 carbon atoms, or cyano, or R 9 and R 10 or R ⁇ and R )2 may be taken together to form aryl of 5 to 7 carbon atoms; provided that at least one of R W2 is not hydrogen;
- W is O, NR 6 , or is absent;
- Y is -(CO)- or -(CO 2 )-, or is absent;
- Z is alkyl of 1 to 4 carbon atoms, -CN, -CO 2 R 6 , COR 6 , -CONR ⁇ , -OCOR 6 , -NR.COR,, -OCONR 6 , -OR 6 , -SR 6 , -SOR 6 , -SO 2 R 6 , SR 6 N(R 7 R 8 ), -N(R 7 R 8 ) or phenyl;
- G is a monocyclic heteroaryl
- X is a bond, -NH, alkyl of 1 to 6 carbon atoms, alkenyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, thioalkyl of 1 to 6 carbon atoms, alkylamino of 1 to 6 carbon atoms, or (CH)J; J is alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, phenyl or benzyl; and n is 1 to 6, or pharmaceutical salts thereof.
- R,-R 5 is not hydrogen.
- R,-R 5 are independently, hydrogen alkyl of 1 to 6 carbon atoms, halogen, perhaloalkyl of 1 to 6 carbon atoms, OR 6 or N(R 7 R 8 ).
- 1 to 3 of R ⁇ R j is not hydrogen.
- 2 of R j -R j is not hydrogen.
- R 3 and R 5 , or R 4 and R 5 are preferably, independently, halogen or CF 3 .
- R9-R12 are selected from halogen, methyl, methoxy and cyano.
- G is preferably thiazolyl, thiadiazolyl, oxazolyl or furyl. More preferably G is furan. G is preferably not substituted.
- X is a bond or C1-C4 alkyl.
- said alkyl is straight chain alkyl.
- Preferred compounds of the present invention are the following compounds which include pharmaceutical salts thereof:
- Alkyl as used herein refers to straight or branched chain lower alkyl of 1 to 6 carbon atoms.
- exemplary alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl and hexyl.
- Alkenyl as used herein refers to straight or branched chain lower alkyl of 2 to
- Alkenyl includes vinyl groups.
- Alkynyl refers to straight or branched chain lower alkyl of 2 to 6 carbon atoms containing at least one carbon-carbon triple bond. Alkyl, alkenyl and alkynyl groups of the present invention may be substituted or unsubstituted.
- Cycloalkyl refers to a saturated mono or bicyclic ring system of 3 to 10 carbon atoms.
- exemplary cycloalkyl groups include cyclopentyl, cyclohexyl and cycloheptyl. Cycloalkyl groups of the present invention may be substituted or unsubstituted.
- Heterocycloalkyl refers to a saturated mono or bicyclic ring system of 3 to 10 members having 1 to 3 heteroatoms selected from N, S and O, including, but not limited to aziridinyl, azetidinyl, imidazolidinyl, morpholinyl, thiomorpholinyl, piperazinyl, pyrazolidinyl, piperidinyl, and pyrrolidinyl. Heterocycloalkyl groups of the present invention may be substituted or unsubstituted.
- Aryl refers to an aromatic mono or bicyclic ring of 5 to 10 carbon atoms.
- exemplary aryl groups include phenyl, naphthyl, and biphenyl.
- Aryl groups of the present invention may be substituted or unsubstituted.
- Heteroaryl refers to an aromatic mono or bicyclic ring of 5 to 10 members having 1 to 3 heteroatoms selected from N, S or O including, but not limited to thiazolyl, thiadiazolyl, oxazolyl, furyl, indolyl, benzothiazolyl, benzotriazolyl, benzodioxyl, indazolyl, and benzofuryl.
- Preferred heteroaryls include quinolyl, isoquinolyl, napthalenyl, benzofuranyl, benzothienyl, indolyl, pyridyl, pyrazinyl, thienyl, furyl, pyrrolyl, isoxazolyl, oxazolyl, isothiazolyl, thiazolyl, pyrazolyl, triazolyl, thiadiazolyl, and imidazolyl.
- Heteroaryl groups of the present invention may be substituted or unsubstituted.
- Perhaloalkyl refers to an alkyl group of 1 to 6 carbon atoms in which three or more hydrogens are substituted with halogen.
- Phenyl as used herein refers to a 6 membered aromatic ring.
- Halogen refers to chlorine, bromine, iodine and fluorine.
- substitutents are unsubstituted and may include alkyl of 1 to 6 carbon atoms, cycloalkyl of 1 to 6 carbon atoms, heterocycloalkyl of 1 to 6 members, perhaloalkyl of 1 to 6 carbon atoms, alkylamino, dialkylamino, aryl or heteroaryl.
- Carbon number refers to the number of carbons in the carbon backbone and does not include carbon atoms occurring in substituents such as an alkyl or alkoxy substituents. Where terms are used in combination, the definition for each individual part of the combination applies unless defined otherwise.
- alkylcycloalkyl is an alkyl-cycloalkyl group in which alkyl and cycloalkyl are as previously described.
- Pharmaceutically acceptable salts are the acid addition salts which can be formed from a compound of the above general formula and a pharmaceutically acceptable acid such as phosphoric, sulfuric, hydrochloric, hydrobromic, citric, maleic, succinic, fumaric, acetic, lactic, nitric, sulfonic, p-toluene sulfonic, methane sulfonic acid, and the like.
- a pharmaceutically acceptable acid such as phosphoric, sulfuric, hydrochloric, hydrobromic, citric, maleic, succinic, fumaric, acetic, lactic, nitric, sulfonic, p-toluene sulfonic, methane sulfonic acid, and the like.
- the compounds of this invention contain a chiral center, providing for various seteroisomeric forms of the compounds such as racemic mixtures as well as the individual optical isomers.
- the compounds of the present invention are substantially pure optical isomers.
- substantially pure the composition contains greater than 75% of the desired isomer and may include no more than 25% of the undesired isomer. In more preferred embodiments the pure optical isomer is greater than 90% of the desired isomer. In some preferred emodiments, when the target is VZV, the (S) isomer is preferred.
- the individual isomers can be prepared directly or by asymmetric or stereospecific synthesis or by conventional separation of optical isomers from the racemic mixture.
- novel compounds of the present invention are prepared according to the following reaction schemes.
- appropriately substituted thioureas 1 can be prepared as described by Methods 32 and 33 by reacting amines 2 and 5, wherein R ⁇ -R 5 , R 9 -R 12 and G are described as above, in the presence of either one molar equivalent of 1,1'- thiocarbonyl diimidazole in an appropriate solvent such as dichloro-methane and tetrahydrofuran or mixtures thereof or one molar equivalent of l,l'-thiocarbonyl-di- (l,2,4)-triazole in an appropriate solvent such as dichloromethane and tetrahydrofuran or mixtures thereof at room temperature.
- an appropriate solvent such as dichloro-methane and tetrahydrofuran or mixtures thereof
- l,l'-thiocarbonyl-di- (l,2,4)-triazole in an appropriate solvent such as dichloromethane and tetrahydrofuran or mixtures thereof at room temperature.
- Thioureas 1 wherein at least one substituent of R,-R 5 is 1 -hydroxyethoxy or carboxy-methoxy, R 9 -R 12 and G are defined as above and X equals a bond, may be prepared from the corresponding alkyl esters by alkaline hydrolysis with aqueous sodium or potassium hydroxide in a suitable solvent such as methanol, tetrahydrofuran or mixtures thereof at room temperature in accordance with Methods 35 and 36.
- Thioureas 1 wherein at least one substituent of R,-R s is 1 -acyloxyethoxy or methansulfonoxyethoxy, R 9 -R 12 and G are defined as above and X equals a bond, may be prepared from the corresponding 1-hydroxyethoxy derivative by acylation with appropriate acylating agents such as benzoic acid chloride or methanesulfonic acid chloride in the presence of a suitable tertiary amine base such as triethylamine or diisopropylethylamine in a suitable solvent such as dichloromethane or the like at room temperature in accordance with Methods 37 and 38.
- acylating agents such as benzoic acid chloride or methanesulfonic acid chloride in the presence of a suitable tertiary amine base such as triethylamine or diisopropylethylamine in a suitable solvent such as dichloromethane or the like at room temperature in accordance with Methods 37 and
- Thioureas 1 wherein at least one substituent of R,-R 5 is 1-aminoethoxy, R 9 -R 12 and G are defined as above and X equals a bond, may be prepared from the corresponding 1-methanesulfonoxy-ethoxy derivative by reaction with an appropriate secondary amine such as dimethylamine in a suitable solvent mixture such as tetrahydrofuran and water or the like at room temperature in accordance with Method 39.
- Thioureas 1 wherein at least one substituent of R,-R 5 is 1-aminoalkyl, R 9 -R 12 and G are defined as above and X equals a bond, may be prepared from the corresponding 1-azidoalkyl derivative by reaction with stannous chloride in a suitable solvent such as methanol, ethanol or the like at room temperature in accordance with Method 40.
- the intermediate isothiocyanates 3 and 4 shown above in Methods 31 and 34 are prepared in accordance with Method 41 (below) essentially according to the procedures of Staab, H.A. and Walther, G. Justus Liebigs Ann. Chem. 657, 104 (1962)) by reacting appropriately substituted amines 5 or 2, respectively, wherein R,- R 5 , R 9 -R 12 and G are described above and X is defined above, with one molar equivalent of l,l'-thiocarbonyldiimidazole in an appropriate solvent such as dichloromethane and tetrahydrofuran or mixtures thereof.
- Method 41 essentially according to the procedures of Staab, H.A. and Walther, G. Justus Liebigs Ann. Chem. 657, 104 (1962)
- the intermediates 2 and 5 may be prepared according to the following protocols:
- amines 2, wherein R ⁇ R s are defined above and X is defined above and amines 5, wherein R 9 -R, fie are defined above, may be prepared by reduction of the appropriately substituted nitrobenzenes according to a variety of procedures known to those skilled in the art and described in R. J. Lindsay, Comprehensive Organic Chemistry (ed. Sutherland), Volume 2, Chapter 6.3.1, Aromatic Amines, 1979.
- Such procedures include the reduction of nitrobenzenes to form anilines upon exposure to: a) iron powder and a strong acid, such as hydrochloric acid (Methods 1A) either neat or in alcohol solvent such as methanol or ethanol, at temperatures ranging from room temperature to the refluxing temperature of the solvent, or; b) iron powder and glacial acetic acid (Method IB), either neat or in alcohol solvent such as methanol or ethanol, at temperatures ranging from room temperature to the refluxing temperature of the solvent, or; c) iron powder and aqueous ammonium chloride (Method IC), either neat or in alcohol solvent such as methanol or ethanol, at temperatures ranging from room temperature to the refluxing temperature of the solvent, or; d) tin and a strong mineral acid, such as hydrochloric acid (Method ID), either neat or in alcohol solvent such as methanol or ethanol, at temperatures ranging from room temperature to the refluxing temperature of the solvent, or; e) when R
- amines 2, wherein R,-R 5 are defined above and X is defined above and anilines 5, wherein R 9 -R 12 are defined above may be prepared by the cleavage of the aniline nitrogen-carbon bond of amide and carbamate derivatives of these anilines according to a variety of procedures known to those skilled in the art and described in Greene, Protective Groups in Organic Synthesis volume 2, Chapter 7, 1991, and references therein.
- Such procedures include: a) the exposure of appropriately substituted arylamino-tert-butyl-carbamates to a strong acid such as trifluoroacetic acid (Method 3A)either neat or in an appropriate solvent such as dichloromethane at temperatures between 0°C and room temperature, or; b) the exposure of appropriately substituted arylamino-(2-trimethylsilylethyl)- carbamates to a fluoride ion source such as tetrabutylammonium fluoride or potassium fluoride (Method 3B) in aqueous acetonitrile or tetrahydrofuran or mixtures thereof at temperatures ranging from room temperature to the reflux temperature of the solvent, or; c) the exposure of appropriately substituted arylamino-trifluoroacetamides to a strong base such as sodium or potassium hydroxide or sodium or potassium carbonate in an alcohol solvent such as methanol or ethanol (Method 3C) at temperatures ranging
- amines 2, wherein R ⁇ R ; are defined above, and X is defined above and at least one substituent of R,-R 5 is defined as vinyl may be prepared by the palladium catalyzed coupling of a vinyl trialkyltin reagent, such as tributylvinyltin, with an appropriately substituted bromo- or iodo- aniline, for example 3-chloro-4-iodo-aniline, employing a palladium catalyst, such as tris(dibenzylidineacetone)-bipalladium, and a ligand, such as triphenylarsine, in a suitable solvent such as tetrahydrofuran or N-methylpyrrolidinone, at temperatures ranging from room temperature to the reflux temperature of the solvent, essentially according to the procedures of V. Farina and G.P. Roth in Advances in Metal- Organic Chemistry, Vol. 5, 1-53, 1996 and references therein.
- amines 2, wherein R,-R 5 are defined above and X equals a bond and at least one substituent of R 2 or R 4 is defined as dialkylamino may be prepared by the palladium catalyzed amination of an appropriately substituted 3- or 5-bromo- or iodo-aniline, for example 3-amino-5- bromobenzotrifluoride, by secondary amines under conditions which employ a palladium catalyst, such as bis(dibenzylidineacetone)palladium, and a ligand, such as tri-o-tolylphosphine, and at least two molar equivalents of a strong base, such as lithium bis-(trimethylsilyl)amide in a sealed tube, in a suitable solvent such as tetrahydrofuran or toluene, at temperatures ranging from room temperature to 100°C, essentially according to the procedures of J.F. Hartwig and J. Louie Tetrahedron Letters 36
- amines 2, wherein R,-R 5 are defined above and X is defined above and at least one substituent of R 2 or R 4 is defined as alkyl may be prepared by the palladium catalyzed alkylation of an appropriately substituted 3- or 5-bromo-or iodo-aniline, for example 3-amino-5- bromobenzotrifluoride by alkenes under condiditons which employ a palladium catalyst such as [l,l '-bis(diphenylphosphino)ferrocene]palladium (II) chloride- dichloromethane complex and in the presence of 9-borabicyclo[3.3.1]nonane and a suitable base such as aqueous sodium hydroxide in a suitable solvent such as tetrahydrofuran or the like at temperatures ranging from room temperature to the reflux temperature of the solvent.
- Methods 3A-3C may be prepared by the derivatization of the corresponding amines as described in Methods 2A-2G according to a variety of procedures known to those skilled in the art and described in Greene, Protective Groups in Organic Synthesis volume 2, Chapter 7, 1991, and references therein. Such procedures include: a) the reaction of an appropriately substituted amine with di-tert-butyl-dicarbonate
- Method 2A in the presence or absence of one or more molar equivalents of a tertiary amine such as triethylamine or N,N-diisopropylethylamine in a suitable solvent such as acetone, tetrahydrofuran, dimethylformamide, dichloromethane, and the like, at temperatures ranging from room temperature to the reflux temperature of the solvent to produce the corresponding arylamino-tert-butyl- carbamate, or; b) the reaction of an appropriately substituted aniline with l-[2-(trimethyl- silyl)ethoxycarbonyl-oxy]benzotriazole (Method 2B) in the presence of a tertiary amine such as triethylamine or diisopropylethylamine in a suitable solvent such as dimethylformamide at room temperature to produce the corresponding arylamino-
- a tertiary amine such as triethylamine or diisopropy
- Nitrobenzene intermediates that are ultimately converted to amines 2 and 5 by methods shown above in Methods 1A-1G may be prepared in accordance with Methods 4A, AC, 4E-4F.
- the nitrobenzene intermediates which are ultimately converted into amines 2, R 2 and R 4 are defined above and R,, R 3 , and/or R 5 are defined as alkoxy, thioalkoxy, alkylsulfenyl, alkylsulfinyl, and dialkylamino may be prepared by the nucleophilic displacement of appropriately substituted 2-, 4-, and/or 6-fluoro-, chloro-, bromo-, iodo-, trifluoromethylsulfonyl-, or (4-methylphenyl)sulfonyl-substituted nitrobenzenes by methods which include the following: a) reaction of alcohols with appropriately substituted 2- or 4- halo- or sulfonate esters of nitrobenzenes or benzonitriles (Method 4A) either neat or in an appropriate solvent such as tetrahydrofuran, dioxan
- the nitrobenzene intermediates which are ultimately converted into amines 2, wherein at least one substitutent R,-R 5 is defined as alkoxy may be prepared from the corresponding substituted hydroxy- nitrobenzenes by methods which include the following: a) reaction of the hydroxy-nitrobenzene with an alkyl halide or dialkyl sulfonate ester (Method 5C) in the presence of a base, such as potassium carbonate, sodium carbonate, potassium hydroxide, sodium hydroxide, potassium hydride, or sodium hydride, in an appropriate solvent such as acetone, N,N-dimethylformamide, tetrahydrofuran or dimethylsulfoxide at temperatures ranging from room temperature to the reflux temperature of the solvent, or; b) reaction of the hydroxy-nitrobenzene with an alkyl alcohol, triphenylphosphine, and a dialkylazadicarboxylate reagent (Method 6
- the carbamoyl amine derivatives utilized as starting materials in Methods 3A-3C which are ultimately converted into amines 2, wherein at least one substituent R,-R 5 is defined as alkoxy may be prepared the corresponding substituted hydroxy arylamino-tert-butyl-carbamate by reaction with alkyl halides, trifluormethane-sulfonates, 4-methylbenzenesulfonates, dialkyl- sulfonate, ethylene carbonate and the like in the presence of a suitable base such as potassium carbonate in an appropriate solvent such as acetone, toluene, or N,N- dimethyl-formamide at temperatures ranging from room temperature to the reflux temperature of the solvent.
- a suitable base such as potassium carbonate
- an appropriate solvent such as acetone, toluene, or N,N- dimethyl-formamide
- the nitrobenzene intermediates which are ultimately converted into amines 2, R, and/or R 3 is alkoxy, and R 2 and/or R 4 is a halogen, and X equals a bond may be prepared by standard halogenation reactions which include the following:
- a suitable solvent such as N,N-dimethyl- formamide or the like
- a suitable secondary amine such as dimethylamine, morpholine or the like
- a suitable solvent
- the nitrobenzene intermediates which are ultimately converted into amines 2, wherein at least one substituent of R,-R 5 is defined as triflate and X equals a bond may be prepared from the corresponding phenol by reaction with trifluoromethane sulfonic anhydride in the presence of a tertiary amines such as triethylamine or diisopropyl-ethylamine or the like in a suitable solvent such as dichloromethane at temperatures ranging from 0°C to room temperature.
- the carbamoyl amine derivatives utilized as starting materials in Methods 3A-3C which are ultimately converted into amines 2, wherein at least one substituent R j -R 5 is defined as either alkylsulfenyl or alkylsulfinyl, may be prepared by reaction of the appropriate 4-alkylthio acyl- arylamino or carbamoyl arylamino derivative with an appropriate oxidizing agent such as dimethyloxirane or sodium periodate in a suitable solvent mixture such as acetone and dichloromethane or water at room temperature.
- an appropriate oxidizing agent such as dimethyloxirane or sodium periodate
- a suitable solvent mixture such as acetone and dichloromethane or water at room temperature.
- the carbamoyl amine derivatives utilized as starting materials in Methods 3A-3C which are ultimately converted into amines 2, wherein R 4 is defined as 1-hydroxyethyl and R,-R 3 and R 5 are defined as above and X equals a bond may be prepared by reacting the corresponding 4-vinyl carbamoyl aniline with sodium borohydride in the presence of mercuric acetate in a suitable solvent such as tetrahydrofuran, 1,4-dioxane or the like and water at room temperature.
- the carbamoyl amine derivatives utilized as starting materials in Methods 3A-3C which are ultimately converted into amines 2, wherein R 4 is defined as 2-hydroxyethyl and R ⁇ R j and R 5 are defined as above and X is defined above may be prepared by reacting the corresponding 4-vinyl carbamoyl aniline with sodium borohydride in the presence of glacial acetic acid in a suitable solvent such as tetrahydrofuran, 1 ,4-dioxane or the like at temperatures ranging from 0°C to room temperature.
- the carbamoyl amine derivatives utilized as starting materials in Methods 3A-3C which are ultimately converted into amines 2, wherein R 4 is defined as 1-azidoethyl and R,-R 3 and R 5 are defined as above and X is defined above may be prepared by reacting the corresponding 4- (1-hydroxyethyl) carbamoyl aniline with hydrazoic acid in the presence of a dialkylazodicarboxylate such as diethylazodicarboxylate and triphenylphosphine in a suitable solvent mixture such as tetrahydrofuran and dichloromethane at temperatures ranging from 0°C to room temperature.
- a dialkylazodicarboxylate such as diethylazodicarboxylate and triphenylphosphine
- a suitable solvent mixture such as tetrahydrofuran and dichloromethane
- the carbamoyl amine derivatives utilized as starting materials in Methods 3A-3C which are ultimately converted into amines 2, wherein R 4 is defined as 3-dimethylaminoprop-l-ynyl and R,-R 3 and R 5 are defined as above and X equals a bond, may be prepared by reacting the corresponding 4-iodo- carbamoyl aniline with l-dimethylamino-2-propyne in a suitable tertiary amine solvent such as triethylamine or diisopropylefhylamine in the presence of bis(triphenylphosphine)palladium(II) chloride and cuprous iodide at temperatures ranging from room temperature to the reflux temperature of the solvent.
- a suitable tertiary amine solvent such as triethylamine or diisopropylefhylamine
- the carbamoyl amine derivatives utilized as starting materials in Methods 3A-3C which are ultimately converted into amines 2, wherein R 4 is defined as 3-dimethylaminoacryloyl and R j -R 3 and R 5 are defined as above and X equals a bond, may be prepared by reacting the corresponding 4-(3- dimethylaminoprop-l-ynyl)carbamoyl aniline with a suitable peracid such as 3- chloroperoxybenzoic acid in a suitable solvent mixture such as dichloromethane and methanol at temperatures ranging from 0°C to room temperature.
- a suitable peracid such as 3- chloroperoxybenzoic acid
- the carbamoyl amine derivatives utilized as starting materials in Methods 3A-3C which are ultimately converted into amines 2, wherein R 4 is defined as either 4-isoxazol-5-yl or 4-(lH-pyrazol-3-yl) and R,-R 3 and R 5 are defined as above and X equals a bond, may be prepared by reacting the corresponding 4-(3-dimethylamino-acryloyl)carbamoyl aniline with either hydroxyl- amine hydrochloride or hydrazine hydrate in a suitable solvent such as 1,4-dioxane or ethanol and the like at room temperature.
- a suitable solvent mixture such as tetrahydrofuran and dichloromethane and the like
- the carbamoyl amine derivatives utilized as starting materials in Methods 3A-3C which are ultimately converted into amines 2, wherein at least one substituent of R,-R 5 is defined as dialkylamino and X is defined above may be prepared by reaction of appropriately substituted aldehydes in the presence of either sodium cyanoboro-hydride or hydrogen gas and 10 % palladium on carbon in a suitable solvent such as water, methanol, tetrahydrofuran mixtures or toluene or the like at room temperature.
- amines 2 wherein at least one substituent of R,-R 5 is defined as hydroxy and X is defined above can be prepared by reaction of the corresponding ester such as acetate with an appropriate base such as sodium bicarbonate or sodium hydroxide in a suitable solvent mixture such as methanol- water mixtures at temperatures ranging from room temperature to the reflux temperature of the solvent.
- an appropriate base such as sodium bicarbonate or sodium hydroxide
- a suitable solvent mixture such as methanol- water mixtures
- amines 2 wherein at least one substituent of R,-R 5 is defined as 2-hydroxybenzamido and X is defined above can be prepared by reaction of the corresponding N-(4-aminophenyl)phthalimide with lithium borohydride in an appropriate solvent such as tetrahydrofuran, diethyl ether, or the like at room temperature.
- the intermediate amines 2 wherein R,-R 5 are defined as above and X equals either -CH 2 - or -(CH 2 ) 2 - can be prepared by the following procedures: a) reduction of an appropriately substituted benzo- or phenylacetonitrile with borane- dimethylsulfide complex in a suitable solvent such as ethylene glycol dimethyl ether, tetrahydrofuran or the like a temperatures ranging from room temperature to the reflux temperature of the solvent.
- a suitable solvent such as ethylene glycol dimethyl ether, tetrahydrofuran or the like
- Method 44 b) reduction under one or more atmospheres of hydrogen in the presence of a suitable catalyst such as 5 % or 10 % palladium on carbon and an acid such as 4- methyl-benzenesulfonic acid, hydrochloric acid or the like in a suitable solvent such as ethylene glycol monomethyl ether, ethyl acetate, ethanol or the like at room temperature.
- a suitable catalyst such as 5 % or 10 % palladium on carbon and an acid such as 4- methyl-benzenesulfonic acid, hydrochloric acid or the like
- a suitable solvent such as ethylene glycol monomethyl ether, ethyl acetate, ethanol or the like at room temperature.
- Method 50 c) reduction with lithium aluminum hydride in a suitable solvent such as tetrahydrofuran or diethyl ether at temperatures ranging from 0°C to room temperature.
- the unsaturated nitro precursors which are utilized as starting materials in Method 51 and are ultimately converted to amines 2 wherein R,-R 5 are defined as above and X equals -(CH 2 ) 2 - can be prepared by reaction of an appropriately substituted benzaldehyde with nitro-methane in the presence of ammonium acetate in a suitable solvent such as acetic acid at temperatures ranging from room temperature to the reflux temperature of the solvent.
- Method 53 The benzaldehydes, utilized as starting materials in Method 53, can be prepared by diisobutylaluminum hydride reduction of an appropriately substituted benzonitrile.
- Method 52 The substituted benzonitriles, utilized as starting materials in Method 52, can be prepared from the corresponding aryl bromide by reaction with copper cyanide in a suitable solvent such as N,N-dimethylformamide at temperatures ranging from room temperatture to the reflux temperature of the solvent. (Method 59)
- the requisite nitrile precursors may be prepared by reaction of an appropriately substituted phenol or thiophenol with bromoacetonitrile in the presence of a suitable base such as potassium carbonate in an appropriate solvent such as acetone at room temperature according to Method 49.
- the nitrile precursors can be prepared essentially according to the procedure of Wilk, B. Synthetic Comm. 23, 2481 (1993), by reaction of an appropriately substituted phenethanol with acetone cyanohydrin and triphenylphosphine in the presence of a suitable azodicarboxylate such as diethyl azodicarboxylate in an appropriate solvent such as diethyl ether or tetrahydro-furan or the like at temperatures ranging from 0°C to room temperature. (Method 54)
- intermediate amines 2 wherein R ⁇ R s are defined as above and X equals -(CH(CH 3 ))- can be prepared by acid or base catalyzed hydrolysis of the corresponding formamide using an appropriate acid catalyst such as 6N hydrochloric acid or a suitable base catalyst such as 5N sodium or potassium hydroxide in an appropriate solvent mixture such as water and methanol or water and ethanol at temperatures ranging from room temperature to the reflux temperature of the solvent. (Method 46)
- the formamide precursors utilized as starting materials in Method 46 and which are ultimately converted into amines 2, are prepared according to Method 45 by treatment of an appropriately substituted acetophenone with ammonium formate, formic acid and formamide at temperatures ranging from room temperature to the reflux temperature of the solvent.
- amines 2 wherein R,-R 5 are defined as above and X equals -(CH(CH 3 ))- can be prepared by reduction of an appropriately substituted O-methyl oxime in the presence of sodium borohydride and zirconium tetrachloride in a suitable solvent such as tetrahydrofuran or diethyl ether at room temperature
- Method 48 essentially according to the procedure of Itsuno, S., Sakurai, Y., Ito, K. Synthesis 1988, 995.
- the requisite O-methyl oximes can be prepared from the corresponding acetophenone by reaction with methoxylamine hydrochloride and pyridine in a suitable solvent such as ethanol or methanol at temperatures ranging from room temperature to the reflux temperature of the solvent. (Method 47)
- Amines 2 for which R,-R 5 are defined as above and X equals -CH(J)- where J is defined as above, can be prepared by reduction of the appropriately substituted ketone by the methods described above (Methods 45, 47, and 48).
- ketones when not commercially available, can be prepared by reaction of a suitably substituted benzaldehyde with an appropriate organometallic reagent such as phenyllithium, isopropylmagnesium bromide or ethylmagnesium bromide or the like in a suitable solvent such as diethyl ether or tetrahydrofuran at temperatures ranging from -78 °C to 0°C.
- the intermediate anilines 5 may be prepared as previously described Method 3A.
- Method 3A treating phenyl carbamic acid tert-butyl ester 6, wherein G is described as above, with neat trifluoroacetic acid at room temperature followed by neutralization with aqueous sodium hydroxide affords the desired anilines 5.
- carbamic acid esters 6, wherein R 9 -R 12 and G are described as above, are prepared as shown in Method 2E by reaction of substituted carboxylic acids 8a, wherein G is described as above, and an appropriately substituted 4- aminophenyl carbamic acid tert-butyl esters 7 in the presence of a suitable coupling agent such as benzotriazole-l-yloxy-tris-(dimethylamino)phosphonium hexafluorophosphate, 2-(lH-benzotriazole-l-yloxy)-l,l,3,3-tetramethyluronium hexafluorophosphate, dicyclo-hexyl carbodiimide or the like and in the presence of a tertiary amine base such as triethylamine or diisopropylethylamine in a suitable solvent such as dichloromethane, dimethylformamide and the like, at room temperature to produce the corresponding arylaminoamide.
- Carboxylic acids 8 a are either commercially available or are prepared according to literature methods.
- G is a substituted thiadiazole
- the acid is available from the corresponding carboxylic acid ester by reaction with an appropriate base such as sodium or potassium hydroxide in a suitable solvent mixture such as methanol or ethanol and water at room temperature.
- the corresponding carboxylic acid 8a is available from the corresponding ethyl or methyl ester by reaction with an appropriate base such as sodium or potassium hydroxide in a suitable solvent mixture such as methanol or ethanol and water at room temperature.
- Tbese esters are either commercially available or can be prepared according to literature methods. When the carboxylic acid ester precursors which are ultimately converted to acids 8a are not commmercially available, they may be prepared by methods known in the literature.
- 5-substituted-l,2,3-thiadiazole-4 carboxylic acid esters may be prepared essentially according to the procedure of Caron, M J. Org. Chem. 51 , 4075 (1986) and Taber, D. F., Ruckle, R. E. J. Amer. Chem. Soc. 108, 7686 (1986).
- a solution of this compound in a suitable solvent such as tetrahydrofuran is treated with gaseous hydrogen sulfide in the presence of a suitable tertiary amine base such as triethylamine or diiso-propylethylamine or the like at room temperature to give the corresponding 4-carboethoxy-thiazole.
- a suitable solvent such as tetrahydrofuran
- gaseous hydrogen sulfide in the presence of a suitable tertiary amine base such as triethylamine or diiso-propylethylamine or the like at room temperature to give the corresponding 4-carboethoxy-thiazole.
- Additional appropriately substituted thiazoles may be prepared essentially according to the procedure of Bredenkamp, M. W., Holzafel, C. W., van Zyl, W. J. Synthetic Comm. 20, 2235 (1990).
- Appropriate unsaturated oxazoles are prepared essentially according to the procedure of Henneke, K. H., Schollkopf, U., Neu decker, T. Liebigs Ann. Chem. 1979 (1979).
- Substituted oxazoles may be prepared essentially according to the procedures of Galeotti, N., Montagne, C, Poncet, J., Jouin, P. Tetrahedron Lett. 33, 2807, (1992) and Shin, C, Okumura, K., Ito, A., Nakamura, Y. Chemistry Lett. 1305, ( 1994).
- N-(4-Nitro-phenyl)-isobutyrlamide 2.0 g
- ethylene glycol monomethyl ether 100 mL
- 10% palladium on carbon 275 mg
- the mixture is hydrogenated for 2 hours at room temperature under 30 psi of hydrogen on a Parr hydrogenation apparatus.
- the catalyst is then removed by filtration through diatomaceous earth and the filtrate is evaporated to dryness under reduced pressure by azeotroping three times with heptane. Trituration of the residue with heptane provides the desired product as a white solid.
- Furan-2-carboxylic acid (4-amino-2-phenylcarbamoyl-phenyl)amide
- the solution is then cooled, concentrated under reduced pressure, diluted with ethyl acetate, and washed successively three times with 5% aqueous hydrochloric acid then once with saturated aqueous sodium chloride.
- the solution is dried over anhydrous sodium sulfate then concentrated under reduced pressure to provide the desired crude product as a brown oil. Crystallization is induced by addition of hexanes, and the collected solid material is recrystallized from hexanes to give the desired product as a white solid.
- Trifluoroacetic acid (5 mL) is added to solid (3,5-dichloro-4-ethoxy-phenyl)- carbamic acid tert-butyl ester (0.97 g) and the mixture is stirred for approximately 45 minutes at room temperature. Water is then added, and the mixture is cooled in an ice bath and basified with solid potassium carbonate. The solution is extracted three times with ethyl acetate and the combined organic phases are washed with saturated aqueous sodium chloride then dried over anhydrous sodium sulfate. Concentration under reduced pressure and recrystallization from hexanes provides the desired product as a pale yellow crystalline solid. Using the above procedure and appropriate starting materials the following compounds were prepared:
- Potassium carbonate (5.0 g) is added to a solution of N-[3-cyano-4-(2,2,2- trifluoroacetyl-amino)-phenyl]-2-fluoro-benzamide (2.5 g) in methanol (270 mL) and water (16 mL) and the mixture is refluxed overnight. After removing the solvent under reduced pressure, the residue is suspended in water and extracted with dichloromethane. The organic extracts are pooled, washed with water and then saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to provide the desired compound as a white solid.
- the organic layer is then dried over anhydrous magnesium sulfate, the solvent is removed under reduced pressure, and the resulting oil is chromatographed over silica gel (5% ethyl acetate in hexanes is used as the eluant) to provide the desired product as an orange solid.
- n-Butyl lithium (12.3 mL of a 2.5 M solution in hexanes) is added dropwise to a solution of N-methyl aniline (3.0 g) in tetrahydrofuran (75 mL) at 0°C.
- the mixture is allowed to warm slowly to room temperature and is then re-cooled to 0°C and added by cannula to a solution of 3-chloro-4-fluoronitrobenzene (4.9 g) in tetrahydrofuran (35 mL) that is kept at -78 °C.
- reaction mixture is permitted to warm to room temperature over the course of 1 hour, and is then concentrated under reduced pressure, quenched by addition of saturated aqueous ammonium chloride, and extracted three times with ethyl acetate.
- the pooled organic layers are washed three times with 5% aqueous hydrochloric acid, once with water, once with saturated aqueous sodium bicarbonate, once with saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate.
- the residue is chromatographed over silica gel (5% diethyl ether in hexanes is used as the eluant) to provide the desired product as a clear colorless oil.
- the solvent is then removed by evaporation under reduced pressure and the resulting residue is chromatographed over silica gel (30% ethyl acetate in hexanes is used as the eluant) to provide the desired product as a white foam.
- the solvent is removed under reduced pressure and the residue is chromatographed over silica gel (1% diethyl ether in hexanes followed by 10% ethyl acetate in hexanes is used as the eluant) to provided the desired product as a colorless oil.
- aqueous acidic extracts are then basified with solid potassium carbonate and extracted three times with ethyl acetate.
- These pooled organic extracts are then washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and the solvent is removed under reduced pressure. The resulting residue is chromatographed over silica gel (hexanes and then 10% ethyl acetate in hexanes is used as the eluant) to provide the desired product as an amber oil.
- the solvent is removed by evaporation under reduced pressure and the resulting residue is chromatographed over silica gel (33% ethyl acetate in hexanes is used as the eluant) to provide the desired product as a colorless solid.
- the resulting oil is purified by chromatography over silica gel (30% diethyl ether in petroleum ether is used as the eluant) and then recrystallized from hexanes to give the desired product as pale yellow needles.
- Ethyl benzoylacetate (5.0 g) is dissolved in methanol (10 mL) and added rapidly to a hot solution of semicarbazide hydrochloride (29 g) in water (130 mL). To this is added pyridine (4.1 g) and after heating to reflux for 5 minutes, the reaction mixture is cooled to -20 °C overnight. The resulting solid semicarbazone is collected by filtration, washed with water and then diethyl ether to give the desired product as white crystals.
- Trifluoro-methanesulfonic acid 4-chloro-5-methoxy-2-nitro-phenyl ester Trifluoro-methanesulfonic acid 4-chloro-2-nitro-phenyl ester Trifluoro-methanesulfonic acid 2-chloro-6-nitro-phenyl ester
- furan-2-carboxylic acid (4- ⁇ 3-[4-(l-azido-ethyl)-3-chloro-phenyl]-thioureido ⁇ - phenyl)-amide (0.22 g) and the solution is stirred for approximately 15 hours at room temperature.
- the solution is then diluted with ethyl acetate, washed successively with saturated aqueous sodium bicarbonate then saturated aqueous sodium chloride, then dried over anhydrous sodium sulfate.
- the product is extracted three times into 5% aqueous hydrochloric acid, and pooled acidic extracts are then basified with cooling by addition of 5N aqueous sodium hydroxide.
- This basic solution is then extracted with ethyl acetate, and these pooled organic extracts are washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and evaporated to dryness under reduced pressure.
- the resulting residue is chromatographed over silica gel (20-30% ethyl acetate in hexanes is used as the eluant) to provide the desired product as a slightly tinted solid.
- the mixture is then cooled to room temperature, diluted with hexanes, washed with water, saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure.
- the resulting oil is chromatographed over silica gel (5% ethyl acetate in hexanes is used as the eluant) to provide the desired product as a white powder.
- Methoxylamine hydrochloride (2.33 g) is added to a solution of 3'-(trifluoromethyl)- acetophenone (1.5 g) in ethanol (20 mL) and pyridine (2 mL). The solution is heated at reflux for 45 minutes. The reaction mixture is then cooled, concentrated under reduced pressure and partitioned between water and ethyl acetate. The aqueous layer is extracted with ethyl acetate. The combined organic layers are washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the desired product as a colorless oil (1.61 g).
- aqueous (acid) layer is basified with sodium hydroxide and extracted twice with ethyl acetate.
- the organic layer is then washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate.
- the solvent is removed under reduced pressure to provide the desired product as a yellow oil (0.20 g).
- Diisobutylaluminum hydride (10 mL of a IM solution in methylene chloride) is added dropwise to a solution of 3-dimethylamino-5-trifluoromethylbenzonitrile (1.06 g) in methylene chloride (25 mL) at 0 °C and the mixture stirred for 2 hours. While still at 0 °C a saturated aqueous solution of sodium potassium tartrate (8 mL) is slowly added and the solution is stirred for 1.5 hours. The reaction mixture is then extracted with ethyl acetate, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to provide the desired product as a yellow solid (0.97 g).
- Nitromethane (0.473 g) is added to a solution of 3-dimethylamino-5-trifluoromethyl- benzaldehyde (0.885 g) and ammonium acetate (0.339 g) in acetic acid (3.4 mL) and the solution is heated at 110 °C for 6 hours. The reaction mixture is cooled to 0 °C and a solid forms which is filtered and washed with 1 :1 water- acetic acid. This solid is recrystallized from ethanol to provide the desired product as a red solid (0.39 g).
- Diethylazodicarboxylate (5.2 g) is added dropwise to a solution of 4-bromo- phenethylalcohol (2.01 g), and triphenylphosphine (7.9 g) in diethyl ether (16 mL) at 0 °C.
- the reaction mixture is stirred for 10 minutes and a solution of acetone cyanohydrin (2.6 g) in diethyl ether (10 mL) is added.
- the clear orange solution is stirred for 5 minutes at 0 °C and then at 25 °C for 12 hours.
- the reaction mixture is then filtered, and washed with diethyl ether.
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
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Abstract
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US20816498A | 1998-12-09 | 1998-12-09 | |
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PCT/US1999/028916 WO2000034261A2 (en) | 1998-12-09 | 1999-12-06 | Heterocyclic carboxamide-containing thiourea inhibitors of herpes viruses containing a substituted phenylenediamine group |
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US6844367B1 (en) | 1999-09-17 | 2005-01-18 | Millennium Pharmaceuticals, Inc. | Benzamides and related inhibitors of factor Xa |
CA2401778C (en) | 2000-02-29 | 2010-12-21 | Cor Therapeutics, Inc. | Benzamides and related inhibitors of factor xa |
AU2004257277B2 (en) * | 2003-07-10 | 2011-03-31 | Achillion Pharmaceuticals, Inc. | Substituted arylthiourea derivatives useful as inhibitors of viral replication |
DE102004015007A1 (en) * | 2004-03-26 | 2005-10-13 | Bayer Healthcare Ag | Substituted imidazoles |
TW200600492A (en) | 2004-05-18 | 2006-01-01 | Achillion Pharmaceuticals Inc | Substituted aryl acylthioureas and related compounds; inhibitors of viral replication |
DE102005008183A1 (en) | 2005-02-23 | 2006-08-31 | Bayer Healthcare Ag | New heterocyclylamide-substituted imidazole compounds useful to treat or prevent viral infections |
PT2404906E (en) | 2006-11-02 | 2015-11-02 | Millennium Pharm Inc | Methods of synthesizing pharmaceutical salts of a factor xa inhibitor |
US9334249B2 (en) | 2012-11-03 | 2016-05-10 | Boehringer Ingelheim International Gmbh | Inhibitors of cytomegalovirus |
JP6482466B2 (en) | 2012-11-03 | 2019-03-13 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Cytomegalovirus inhibitors |
CN112807294B (en) * | 2019-11-18 | 2023-09-05 | 武汉大学 | Application of acyl thiourea compound in preparation of medicines for treating or preventing herpes simplex virus type I infection |
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