ZA200104376B - Alpha-methybenzyl-containing thiourea inhibitors of herpes viruses containing a phenylenediamine groups. - Google Patents
Alpha-methybenzyl-containing thiourea inhibitors of herpes viruses containing a phenylenediamine groups. Download PDFInfo
- Publication number
- ZA200104376B ZA200104376B ZA200104376A ZA200104376A ZA200104376B ZA 200104376 B ZA200104376 B ZA 200104376B ZA 200104376 A ZA200104376 A ZA 200104376A ZA 200104376 A ZA200104376 A ZA 200104376A ZA 200104376 B ZA200104376 B ZA 200104376B
- Authority
- ZA
- South Africa
- Prior art keywords
- phenyl
- carbon atoms
- thioureido
- ethyl
- fluoro
- Prior art date
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- 241001529453 unidentified herpesvirus Species 0.000 title claims description 13
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 title description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title description 3
- 239000003112 inhibitor Substances 0.000 title description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical group NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 title description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 113
- 238000000034 method Methods 0.000 claims description 60
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 35
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- -1 { 1-[2-fluoro-4-(trifluoromethyl)phenyl]ethyl } amino Chemical group 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 11
- 241000701085 Human alphaherpesvirus 3 Species 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- XAAKCCMYRKZRAK-UHFFFAOYSA-N isoquinoline-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=NC=CC2=C1 XAAKCCMYRKZRAK-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 230000003287 optical effect Effects 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000004001 thioalkyl group Chemical group 0.000 claims description 5
- NDMFETHQFUOIQX-UHFFFAOYSA-N 1-(3-chloropropyl)imidazolidin-2-one Chemical compound ClCCCN1CCNC1=O NDMFETHQFUOIQX-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- 241000700584 Simplexvirus Species 0.000 claims description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
- KGGHWIKBOIQEAJ-UHFFFAOYSA-N 2-fluorobenzamide Chemical compound NC(=O)C1=CC=CC=C1F KGGHWIKBOIQEAJ-UHFFFAOYSA-N 0.000 claims description 3
- 241000701024 Human betaherpesvirus 5 Species 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- ZSSFBXCDEYYUQO-UHFFFAOYSA-N 2-cyano-n-[4-[1-(4-fluorophenyl)ethylcarbamothioylamino]phenyl]benzamide Chemical compound C=1C=C(F)C=CC=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C#N ZSSFBXCDEYYUQO-UHFFFAOYSA-N 0.000 claims description 2
- JBAVFKKQNLPAOH-MRXNPFEDSA-N 2-fluoro-n-[4-[[(1r)-1-(4-methylphenyl)ethyl]carbamothioylamino]phenyl]benzamide Chemical compound N([C@H](C)C=1C=CC(C)=CC=1)C(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F JBAVFKKQNLPAOH-MRXNPFEDSA-N 0.000 claims description 2
- ZRVIPJPXTSLRJK-UHFFFAOYSA-N 2-fluoro-n-[4-[[4-methoxy-3-(trifluoromethyl)phenyl]carbamothioylamino]phenyl]benzamide Chemical compound C1=C(C(F)(F)F)C(OC)=CC=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F ZRVIPJPXTSLRJK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
- KYENQJICITXEGJ-UHFFFAOYSA-N 3-cyano-n-[4-[1-(4-fluorophenyl)ethylcarbamothioylamino]phenyl]benzamide Chemical compound C=1C=C(F)C=CC=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC(C#N)=C1 KYENQJICITXEGJ-UHFFFAOYSA-N 0.000 claims description 2
- VUEQUHWFLBWRLA-UHFFFAOYSA-N 4-cyano-n-[4-[1-(4-fluorophenyl)ethylcarbamothioylamino]phenyl]benzamide Chemical compound C=1C=C(F)C=CC=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=C(C#N)C=C1 VUEQUHWFLBWRLA-UHFFFAOYSA-N 0.000 claims description 2
- AQYKJMOSYVEXMK-UHFFFAOYSA-N n-[4-[(2-amino-5-fluorophenyl)carbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound NC1=CC=C(F)C=C1NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F AQYKJMOSYVEXMK-UHFFFAOYSA-N 0.000 claims description 2
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- ILOGWDZBCSHQBB-UHFFFAOYSA-N n-[4-[1-(1-benzofuran-2-yl)ethylcarbamothioylamino]phenyl]-1-benzofuran-2-carboxamide Chemical compound C1=CC=C2OC(C(NC(=S)NC=3C=CC(NC(=O)C=4OC5=CC=CC=C5C=4)=CC=3)C)=CC2=C1 ILOGWDZBCSHQBB-UHFFFAOYSA-N 0.000 claims description 2
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- WOGPBVDSRUSUCE-UHFFFAOYSA-N n-[4-[1-(4-cyanophenyl)ethylcarbamothioylamino]phenyl]-1-benzofuran-2-carboxamide Chemical compound C=1C=C(NC(=O)C=2OC3=CC=CC=C3C=2)C=CC=1NC(=S)NC(C)C1=CC=C(C#N)C=C1 WOGPBVDSRUSUCE-UHFFFAOYSA-N 0.000 claims description 2
- RYTSOXCTIOKYJF-UHFFFAOYSA-N n-[4-[1-(4-cyanophenyl)ethylcarbamothioylamino]phenyl]isoquinoline-1-carboxamide Chemical compound C=1C=C(NC(=O)C=2C3=CC=CC=C3C=CN=2)C=CC=1NC(=S)NC(C)C1=CC=C(C#N)C=C1 RYTSOXCTIOKYJF-UHFFFAOYSA-N 0.000 claims description 2
- FBOCPBSEVJRVHE-UHFFFAOYSA-N n-[4-[2-(1-benzofuran-2-yl)ethylcarbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound FC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)NCCC1=CC2=CC=CC=C2O1 FBOCPBSEVJRVHE-UHFFFAOYSA-N 0.000 claims description 2
- PNZKYPKDRLHMCZ-INIZCTEOSA-N n-[4-[[(1s)-1-(4-bromophenyl)ethyl]carbamothioylamino]phenyl]isoquinoline-3-carboxamide Chemical compound C1([C@@H](NC(=S)NC=2C=CC(NC(=O)C=3N=CC4=CC=CC=C4C=3)=CC=2)C)=CC=C(Br)C=C1 PNZKYPKDRLHMCZ-INIZCTEOSA-N 0.000 claims description 2
- QRDZFPUVLYEQTA-UHFFFAOYSA-N quinoline-8-carboxylic acid Chemical compound C1=CN=C2C(C(=O)O)=CC=CC2=C1 QRDZFPUVLYEQTA-UHFFFAOYSA-N 0.000 claims description 2
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- FPPIIVRTWGCBHC-UHFFFAOYSA-N n-[4-[1-(4-cyanophenyl)ethylcarbamothioylamino]phenyl]isoquinoline-3-carboxamide Chemical compound C=1C=C(NC(=O)C=2N=CC3=CC=CC=C3C=2)C=CC=1NC(=S)NC(C)C1=CC=C(C#N)C=C1 FPPIIVRTWGCBHC-UHFFFAOYSA-N 0.000 description 1
- JMPAOZYVRCKNRF-UHFFFAOYSA-N n-[4-[1-(4-fluorophenyl)ethylcarbamothioylamino]phenyl]-1-benzofuran-2-carboxamide Chemical compound C=1C=C(NC(=O)C=2OC3=CC=CC=C3C=2)C=CC=1NC(=S)NC(C)C1=CC=C(F)C=C1 JMPAOZYVRCKNRF-UHFFFAOYSA-N 0.000 description 1
- HNWMYUNXUZWIFV-UHFFFAOYSA-N n-[4-[1-(4-fluorophenyl)ethylcarbamothioylamino]phenyl]-4-(trifluoromethyl)benzamide Chemical compound C=1C=C(F)C=CC=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1 HNWMYUNXUZWIFV-UHFFFAOYSA-N 0.000 description 1
- UKTPEFAEFIQITA-UHFFFAOYSA-N n-[4-[1-(4-fluorophenyl)ethylcarbamothioylamino]phenyl]quinoline-3-carboxamide Chemical compound C=1C=C(NC(=O)C=2C=C3C=CC=CC3=NC=2)C=CC=1NC(=S)NC(C)C1=CC=C(F)C=C1 UKTPEFAEFIQITA-UHFFFAOYSA-N 0.000 description 1
- AXSHDVBYRZOMLM-UHFFFAOYSA-N n-[4-[1-(4-fluorophenyl)ethylcarbamothioylamino]phenyl]quinoline-4-carboxamide Chemical compound C=1C=C(NC(=O)C=2C3=CC=CC=C3N=CC=2)C=CC=1NC(=S)NC(C)C1=CC=C(F)C=C1 AXSHDVBYRZOMLM-UHFFFAOYSA-N 0.000 description 1
- UBESZTWLNINWSH-UHFFFAOYSA-N n-[4-[1-(4-fluorophenyl)ethylcarbamothioylamino]phenyl]quinoline-6-carboxamide Chemical compound C=1C=C(NC(=O)C=2C=C3C=CC=NC3=CC=2)C=CC=1NC(=S)NC(C)C1=CC=C(F)C=C1 UBESZTWLNINWSH-UHFFFAOYSA-N 0.000 description 1
- KOOVZLLETLDOIE-UHFFFAOYSA-N n-[4-[1-[4-(dimethylsulfamoyl)phenyl]ethylcarbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound C=1C=C(S(=O)(=O)N(C)C)C=CC=1C(C)NC(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F KOOVZLLETLDOIE-UHFFFAOYSA-N 0.000 description 1
- IOABVAYQZBFYFU-OAHLLOKOSA-N n-[4-[[(1r)-1-(4-bromophenyl)ethyl]carbamothioylamino]phenyl]-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=S)N[C@H](C)C1=CC=C(Br)C=C1 IOABVAYQZBFYFU-OAHLLOKOSA-N 0.000 description 1
- SUWGJAQKGMMPAP-CQSZACIVSA-N n-[4-[[(1r)-1-(4-chlorophenyl)ethyl]carbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound N([C@H](C)C=1C=CC(Cl)=CC=1)C(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F SUWGJAQKGMMPAP-CQSZACIVSA-N 0.000 description 1
- MZNGRRVYCARXOA-INIZCTEOSA-N n-[4-[[(1s)-1-(4-bromophenyl)ethyl]carbamothioylamino]phenyl]isoquinoline-1-carboxamide Chemical compound C1([C@@H](NC(=S)NC=2C=CC(NC(=O)C=3C4=CC=CC=C4C=CN=3)=CC=2)C)=CC=C(Br)C=C1 MZNGRRVYCARXOA-INIZCTEOSA-N 0.000 description 1
- SUWGJAQKGMMPAP-AWEZNQCLSA-N n-[4-[[(1s)-1-(4-chlorophenyl)ethyl]carbamothioylamino]phenyl]-2-fluorobenzamide Chemical compound N([C@@H](C)C=1C=CC(Cl)=CC=1)C(=S)NC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1F SUWGJAQKGMMPAP-AWEZNQCLSA-N 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical class [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 230000002276 neurotropic effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 150000003833 nucleoside derivatives Chemical class 0.000 description 1
- 244000039328 opportunistic pathogen Species 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 230000007918 pathogenicity Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 201000000317 pneumocystosis Diseases 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000010322 reactivation of latent virus Effects 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 206010040872 skin infection Diseases 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
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 229940055764 triaz Drugs 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 230000029812 viral genome replication Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/48—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
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/06—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with the ring nitrogen atom acylated by carboxylic or carbonic acids, or with sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (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)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Quinoline Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20890298A | 1998-12-09 | 1998-12-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200104376B true ZA200104376B (en) | 2002-08-28 |
Family
ID=22776519
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200104376A ZA200104376B (en) | 1998-12-09 | 2001-05-28 | Alpha-methybenzyl-containing thiourea inhibitors of herpes viruses containing a phenylenediamine groups. |
Country Status (21)
| Country | Link |
|---|---|
| EP (1) | EP1137645B1 (cs) |
| JP (1) | JP2002531555A (cs) |
| KR (1) | KR20010089551A (cs) |
| CN (1) | CN1165531C (cs) |
| AR (1) | AR035308A1 (cs) |
| AT (1) | ATE267824T1 (cs) |
| AU (1) | AU1934600A (cs) |
| BR (1) | BR9916084A (cs) |
| CA (1) | CA2350833A1 (cs) |
| CZ (1) | CZ20012067A3 (cs) |
| DE (1) | DE69917673T2 (cs) |
| DK (1) | DK1137645T3 (cs) |
| EA (1) | EA004205B1 (cs) |
| ES (1) | ES2221470T3 (cs) |
| HU (1) | HUP0104492A3 (cs) |
| IL (1) | IL143183A0 (cs) |
| NO (1) | NO20012833L (cs) |
| NZ (1) | NZ512135A (cs) |
| PT (1) | PT1137645E (cs) |
| WO (1) | WO2000034260A2 (cs) |
| ZA (1) | ZA200104376B (cs) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6844367B1 (en) | 1999-09-17 | 2005-01-18 | Millennium Pharmaceuticals, Inc. | Benzamides and related inhibitors of factor Xa |
| ATE311366T1 (de) | 2000-02-29 | 2005-12-15 | Millennium Pharm Inc | Benzamide und ähnliche inhibitoren vom faktor xa |
| AU8022901A (en) * | 2000-08-21 | 2002-03-04 | Pacific Corp | Novel thiourea derivatives and the pharmaceutical compositions containing the same |
| JP4360885B2 (ja) | 2003-11-28 | 2009-11-11 | 富士フイルム株式会社 | アルキルチオ基を有する芳香族アミン化合物の製造方法 |
| EP1928843A1 (en) * | 2005-08-22 | 2008-06-11 | Amgen, Inc | Bis-aryl urea compounds for the treatment of protein kinase-mediated diseaes |
| PT2077995E (pt) | 2006-11-02 | 2012-05-10 | Millennium Pharm Inc | Métodos de sintetizar sais farmacêuticos de um inibidor de fator xa |
| 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 |
| CN115433093A (zh) * | 2022-09-26 | 2022-12-06 | 无锡双启科技有限公司 | 一种3-氯-4-三氟甲基苯胺的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU210683B (en) * | 1990-06-18 | 1995-06-28 | Sandoz Ag | Process for producing n-benzyl-n1-(phenyl-alkyl)-thiourea derivatives and pharmaceutical compositions containing the same |
| JPH11503110A (ja) * | 1995-02-17 | 1999-03-23 | スミスクライン・ビーチャム・コーポレイション | Ｉｌ−８受容体拮抗剤 |
| GB9519270D0 (en) * | 1995-09-21 | 1995-11-22 | Sandoz Pharma Uk | Organic compounds |
| EP0902782A1 (en) * | 1996-04-23 | 1999-03-24 | Vertex Pharmaceuticals Incorporated | Urea derivatives as inhibitors of impdh enzyme |
-
1999
- 1999-12-06 ES ES99963022T patent/ES2221470T3/es not_active Expired - Lifetime
- 1999-12-06 PT PT99963022T patent/PT1137645E/pt unknown
- 1999-12-06 EP EP99963022A patent/EP1137645B1/en not_active Expired - Lifetime
- 1999-12-06 WO PCT/US1999/028839 patent/WO2000034260A2/en not_active Application Discontinuation
- 1999-12-06 KR KR1020017007053A patent/KR20010089551A/ko not_active Withdrawn
- 1999-12-06 BR BR9916084-6A patent/BR9916084A/pt not_active IP Right Cessation
- 1999-12-06 JP JP2000586707A patent/JP2002531555A/ja active Pending
- 1999-12-06 DK DK99963022T patent/DK1137645T3/da active
- 1999-12-06 AU AU19346/00A patent/AU1934600A/en not_active Abandoned
- 1999-12-06 EA EA200100638A patent/EA004205B1/ru not_active IP Right Cessation
- 1999-12-06 CN CNB998142778A patent/CN1165531C/zh not_active Expired - Fee Related
- 1999-12-06 DE DE69917673T patent/DE69917673T2/de not_active Expired - Fee Related
- 1999-12-06 HU HU0104492A patent/HUP0104492A3/hu unknown
- 1999-12-06 AT AT99963022T patent/ATE267824T1/de not_active IP Right Cessation
- 1999-12-06 CZ CZ20012067A patent/CZ20012067A3/cs unknown
- 1999-12-06 CA CA002350833A patent/CA2350833A1/en not_active Abandoned
- 1999-12-06 NZ NZ512135A patent/NZ512135A/en unknown
- 1999-12-06 IL IL14318399A patent/IL143183A0/xx unknown
- 1999-12-07 AR ARP990106228A patent/AR035308A1/es not_active Application Discontinuation
-
2001
- 2001-05-28 ZA ZA200104376A patent/ZA200104376B/en unknown
- 2001-06-08 NO NO20012833A patent/NO20012833L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AR035308A1 (es) | 2004-05-12 |
| WO2000034260A3 (en) | 2000-09-08 |
| KR20010089551A (ko) | 2001-10-06 |
| CN1165531C (zh) | 2004-09-08 |
| ATE267824T1 (de) | 2004-06-15 |
| JP2002531555A (ja) | 2002-09-24 |
| DE69917673T2 (de) | 2005-06-09 |
| CA2350833A1 (en) | 2000-06-15 |
| DE69917673D1 (de) | 2004-07-01 |
| NO20012833D0 (no) | 2001-06-08 |
| PT1137645E (pt) | 2004-09-30 |
| NZ512135A (en) | 2003-12-19 |
| HUP0104492A3 (en) | 2002-12-28 |
| EA200100638A1 (ru) | 2001-12-24 |
| CN1329608A (zh) | 2002-01-02 |
| IL143183A0 (en) | 2002-04-21 |
| EA004205B1 (ru) | 2004-02-26 |
| EP1137645B1 (en) | 2004-05-26 |
| WO2000034260A2 (en) | 2000-06-15 |
| EP1137645A2 (en) | 2001-10-04 |
| BR9916084A (pt) | 2001-09-04 |
| NO20012833L (no) | 2001-08-02 |
| HUP0104492A2 (hu) | 2002-04-29 |
| CZ20012067A3 (cs) | 2001-10-17 |
| AU1934600A (en) | 2000-06-26 |
| ES2221470T3 (es) | 2004-12-16 |
| DK1137645T3 (da) | 2004-08-09 |
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