ZA200104322B - 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 group. Download PDFInfo
- Publication number
- ZA200104322B ZA200104322B ZA200104322A ZA200104322A ZA200104322B ZA 200104322 B ZA200104322 B ZA 200104322B ZA 200104322 A ZA200104322 A ZA 200104322A ZA 200104322 A ZA200104322 A ZA 200104322A ZA 200104322 B ZA200104322 B ZA 200104322B
- Authority
- ZA
- South Africa
- Prior art keywords
- carbon atoms
- phenyl
- alkyl
- hydrogen
- chloro
- Prior art date
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- 241001529453 unidentified herpesvirus Species 0.000 title claims description 13
- -1 Heterocyclic carboxamide Chemical class 0.000 title description 16
- 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 124
- 238000000034 method Methods 0.000 claims description 57
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- 239000001257 hydrogen Substances 0.000 claims description 39
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 25
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 241000701024 Human betaherpesvirus 5 Species 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 241000701085 Human alphaherpesvirus 3 Species 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 239000002253 acid Substances 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
- 125000004001 thioalkyl group Chemical group 0.000 claims description 5
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 241000700584 Simplexvirus Species 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 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 2
- 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 2
- 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 2
- 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 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
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- 208000029433 Herpesviridae infectious disease Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- QXBSQMBUEFIUPQ-UHFFFAOYSA-N n-[2-benzoyl-4-[(5-chloro-2,4-dimethoxyphenyl)carbamothioylamino]phenyl]furan-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=S)NC(C=C1C(=O)C=2C=CC=CC=2)=CC=C1NC(=O)C1=CC=CO1 QXBSQMBUEFIUPQ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000010076 replication Effects 0.000 claims 1
- 239000002904 solvent Substances 0.000 description 37
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- 150000001412 amines Chemical class 0.000 description 15
- 238000010992 reflux Methods 0.000 description 13
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 10
- 201000010099 disease Diseases 0.000 description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
- 229910052763 palladium Inorganic materials 0.000 description 9
- 150000001448 anilines Chemical class 0.000 description 8
- 241000700605 Viruses Species 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 150000003585 thioureas Chemical class 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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- RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical class [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
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- XKTZWUACRZHVAN-VADRZIEHSA-N interleukin-8 Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@@H](NC(C)=O)CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CCSC)C(=O)N1[C@H](CCC1)C(=O)N1[C@H](CCC1)C(=O)N[C@@H](C)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC(O)=CC=1)C(=O)N[C@H](CO)C(=O)N1[C@H](CCC1)C(N)=O)C1=CC=CC=C1 XKTZWUACRZHVAN-VADRZIEHSA-N 0.000 description 1
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- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
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- 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 description 1
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- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical class [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
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- 201000000317 pneumocystosis Diseases 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 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
- 125000003373 pyrazinyl group Chemical group 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
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- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 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
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 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
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- 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
- BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- 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)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US20816498A | 1998-12-09 | 1998-12-09 |
Publications (1)
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ZA200104322B true ZA200104322B (en) | 2002-10-25 |
Family
ID=22773466
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200104322A ZA200104322B (en) | 1998-12-09 | 2001-05-25 | Heterocyclic carboxamide-containing thiourea inhibitors of herpes viruses containing a substituted phenylenediamine group. |
Country Status (14)
Country | Link |
---|---|
EP (1) | EP1144399A3 (no) |
JP (1) | JP2002533301A (no) |
KR (1) | KR20010086091A (no) |
CN (1) | CN1367785A (no) |
AU (1) | AU2353900A (no) |
BR (1) | BR9916043A (no) |
CA (1) | CA2351690A1 (no) |
CZ (1) | CZ20012063A3 (no) |
EA (1) | EA200100639A1 (no) |
HU (1) | HUP0203405A2 (no) |
IL (1) | IL143263A0 (no) |
NO (1) | NO20012835L (no) |
WO (1) | WO2000034261A2 (no) |
ZA (1) | ZA200104322B (no) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
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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 (de) * | 2004-03-26 | 2005-10-13 | Bayer Healthcare Ag | Substituierte Imidazole |
TW200600492A (en) | 2004-05-18 | 2006-01-01 | Achillion Pharmaceuticals Inc | Substituted aryl acylthioureas and related compounds; inhibitors of viral replication |
DE102005008183A1 (de) | 2005-02-23 | 2006-08-31 | Bayer Healthcare Ag | Heterocyclylamid-substituierte Imidazole |
PT2404906E (pt) | 2006-11-02 | 2015-11-02 | Millennium Pharm Inc | Métodos de sintetizar sais farmacêuticos de um inibidor de fator xa |
US9334249B2 (en) | 2012-11-03 | 2016-05-10 | Boehringer Ingelheim International Gmbh | Inhibitors of cytomegalovirus |
JP6482466B2 (ja) | 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 | サイトメガロウイルスの阻害剤 |
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 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU6783698A (en) * | 1997-04-10 | 1998-10-30 | Pharmacia & Upjohn Company | Polyaromatic antiviral compositions |
-
1999
- 1999-12-06 IL IL14326399A patent/IL143263A0/xx unknown
- 1999-12-06 AU AU23539/00A patent/AU2353900A/en not_active Abandoned
- 1999-12-06 CN CN99815998A patent/CN1367785A/zh active Pending
- 1999-12-06 HU HU0203405A patent/HUP0203405A2/hu unknown
- 1999-12-06 EA EA200100639A patent/EA200100639A1/ru unknown
- 1999-12-06 CA CA002351690A patent/CA2351690A1/en not_active Abandoned
- 1999-12-06 KR KR1020017007117A patent/KR20010086091A/ko not_active Application Discontinuation
- 1999-12-06 WO PCT/US1999/028916 patent/WO2000034261A2/en not_active Application Discontinuation
- 1999-12-06 CZ CZ20012063A patent/CZ20012063A3/cs unknown
- 1999-12-06 EP EP99967213A patent/EP1144399A3/en not_active Withdrawn
- 1999-12-06 JP JP2000586708A patent/JP2002533301A/ja active Pending
- 1999-12-06 BR BR9916043-9A patent/BR9916043A/pt not_active Application Discontinuation
-
2001
- 2001-05-25 ZA ZA200104322A patent/ZA200104322B/en unknown
- 2001-06-08 NO NO20012835A patent/NO20012835L/no not_active Application Discontinuation
Also Published As
Publication number | Publication date |
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KR20010086091A (ko) | 2001-09-07 |
CA2351690A1 (en) | 2000-06-15 |
JP2002533301A (ja) | 2002-10-08 |
WO2000034261A2 (en) | 2000-06-15 |
EP1144399A2 (en) | 2001-10-17 |
HUP0203405A2 (hu) | 2003-02-28 |
AU2353900A (en) | 2000-06-26 |
EA200100639A1 (ru) | 2002-06-27 |
BR9916043A (pt) | 2001-12-04 |
EP1144399A3 (en) | 2002-09-11 |
NO20012835D0 (no) | 2001-06-08 |
CZ20012063A3 (cs) | 2001-10-17 |
CN1367785A (zh) | 2002-09-04 |
WO2000034261A3 (en) | 2002-01-31 |
NO20012835L (no) | 2001-07-19 |
IL143263A0 (en) | 2002-04-21 |
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