ZA200104142B - Acetamide and substituted acetamide-containing thiourea inhibitors of herpes viruses. - Google Patents
Acetamide and substituted acetamide-containing thiourea inhibitors of herpes viruses. Download PDFInfo
- Publication number
- ZA200104142B ZA200104142B ZA200104142A ZA200104142A ZA200104142B ZA 200104142 B ZA200104142 B ZA 200104142B ZA 200104142 A ZA200104142 A ZA 200104142A ZA 200104142 A ZA200104142 A ZA 200104142A ZA 200104142 B ZA200104142 B ZA 200104142B
- Authority
- ZA
- South Africa
- Prior art keywords
- carbon atoms
- phenyl
- alkyl
- hydrogen
- acetamide
- Prior art date
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- 241001529453 unidentified herpesvirus Species 0.000 title claims description 12
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 title description 7
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 title description 4
- 239000003112 inhibitor Substances 0.000 title description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title description 2
- 150000003869 acetamides Chemical class 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims description 121
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 241000701085 Human alphaherpesvirus 3 Species 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004001 thioalkyl group Chemical group 0.000 claims description 5
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- 125000004429 atom Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- JHWBVIMCORQTMX-UHFFFAOYSA-N n-[4-[(3,5-dichloro-4-ethoxyphenyl)carbamothioylamino]phenyl]acetamide Chemical compound C1=C(Cl)C(OCC)=C(Cl)C=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 JHWBVIMCORQTMX-UHFFFAOYSA-N 0.000 claims description 2
- VSDYXOSAMMYMII-UHFFFAOYSA-N n-[4-[(3-chloro-4-ethenylphenyl)carbamothioylamino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC1=CC=C(C=C)C(Cl)=C1 VSDYXOSAMMYMII-UHFFFAOYSA-N 0.000 claims description 2
- RFPIBPURKDGAIS-UHFFFAOYSA-N n-[4-[(3-chloro-4-methylsulfanylphenyl)carbamothioylamino]phenyl]acetamide Chemical compound C1=C(Cl)C(SC)=CC=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 RFPIBPURKDGAIS-UHFFFAOYSA-N 0.000 claims description 2
- UGBAQLAOKVDTPH-UHFFFAOYSA-N n-[4-[(5-chloro-2-methoxy-4-methylphenyl)carbamothioylamino]phenyl]acetamide Chemical compound COC1=CC(C)=C(Cl)C=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 UGBAQLAOKVDTPH-UHFFFAOYSA-N 0.000 claims description 2
- XNBUSZVHSRETFI-UHFFFAOYSA-N n-[4-[[3-chloro-4-[cyclohexyl(methyl)amino]phenyl]carbamothioylamino]phenyl]acetamide Chemical compound C=1C=C(NC(=S)NC=2C=CC(NC(C)=O)=CC=2)C=C(Cl)C=1N(C)C1CCCCC1 XNBUSZVHSRETFI-UHFFFAOYSA-N 0.000 claims description 2
- SNYDYVQBHDSDKM-UHFFFAOYSA-N n-[4-[[4-[(1-benzylpyrrolidin-3-yl)-methylamino]-3-chlorophenyl]carbamothioylamino]phenyl]acetamide Chemical compound C=1C=C(NC(=S)NC=2C=CC(NC(C)=O)=CC=2)C=C(Cl)C=1N(C)C(C1)CCN1CC1=CC=CC=C1 SNYDYVQBHDSDKM-UHFFFAOYSA-N 0.000 claims description 2
- BCXGUEDGWCZVRT-UHFFFAOYSA-N n-[4-[[4-[(1-benzylpyrrolidin-3-yl)amino]-3-chlorophenyl]carbamothioylamino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC(C=C1Cl)=CC=C1NC1CN(CC=2C=CC=CC=2)CC1 BCXGUEDGWCZVRT-UHFFFAOYSA-N 0.000 claims description 2
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- FGNLMRLPFPCYRP-UHFFFAOYSA-N n-[4-[(3,5-dichloro-4-methoxyphenyl)carbamothioylamino]phenyl]acetamide Chemical compound C1=C(Cl)C(OC)=C(Cl)C=C1NC(=S)NC1=CC=C(NC(C)=O)C=C1 FGNLMRLPFPCYRP-UHFFFAOYSA-N 0.000 claims 1
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- 239000002904 solvent Substances 0.000 description 20
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- IRSCQMHQWWYFCW-UHFFFAOYSA-N ganciclovir Chemical compound O=C1NC(N)=NC2=C1N=CN2COC(CO)CO IRSCQMHQWWYFCW-UHFFFAOYSA-N 0.000 description 4
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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
- 229940096397 interleukin-8 Drugs 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- UAUOPWDADDLRDP-UHFFFAOYSA-N n-[4-[(3-chloro-4-iodophenyl)carbamothioylamino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC1=CC=C(I)C(Cl)=C1 UAUOPWDADDLRDP-UHFFFAOYSA-N 0.000 description 1
- NBOLXIZMRYDZPT-UHFFFAOYSA-N n-[4-[[3-chloro-4-(trifluoromethyl)phenyl]carbamothioylamino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC(=S)NC1=CC=C(C(F)(F)F)C(Cl)=C1 NBOLXIZMRYDZPT-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 150000003833 nucleoside derivatives Chemical class 0.000 description 1
- 244000039328 opportunistic pathogen Species 0.000 description 1
- 229910052763 palladium Inorganic materials 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
- 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
- 125000006239 protecting group Chemical group 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
- 125000003226 pyrazolyl group Chemical group 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
- 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
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000007858 starting material 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
- 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C335/20—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C335/22—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/14—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Biotechnology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Furan Compounds (AREA)
- Indole Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Quinoline Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20831698A | 1998-12-09 | 1998-12-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200104142B true ZA200104142B (en) | 2002-10-25 |
Family
ID=22774137
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200104142A ZA200104142B (en) | 1998-12-09 | 2001-05-21 | Acetamide and substituted acetamide-containing thiourea inhibitors of herpes viruses. |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP1137633A2 (hu) |
| JP (1) | JP2002531544A (hu) |
| KR (1) | KR20010087413A (hu) |
| CN (1) | CN1333750A (hu) |
| AU (1) | AU3111200A (hu) |
| BR (1) | BR9916041A (hu) |
| CA (1) | CA2350899A1 (hu) |
| CZ (1) | CZ20012060A3 (hu) |
| EA (1) | EA200100640A1 (hu) |
| HU (1) | HUP0104944A3 (hu) |
| IL (1) | IL143204A0 (hu) |
| NO (1) | NO20012834L (hu) |
| PL (1) | PL349131A1 (hu) |
| WO (1) | WO2000034237A2 (hu) |
| ZA (1) | ZA200104142B (hu) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6166028A (en) * | 1998-12-09 | 2000-12-26 | American Home Products Corporation | Diaminopuridine-containing thiourea inhibitors of herpes viruses |
| US6844367B1 (en) | 1999-09-17 | 2005-01-18 | Millennium Pharmaceuticals, Inc. | Benzamides and related inhibitors of factor Xa |
| WO2001064643A2 (en) | 2000-02-29 | 2001-09-07 | Cor Therapeutics, Inc. | BENZAMIDES AND RELATED INHIBITORS OF FACTOR Xa |
| CA2503445C (en) * | 2002-10-24 | 2012-07-31 | Merck Patent Gesellschaft Mit Beschraenkter Haftung | Methylene urea derivatives as raf-kinase inhibitors |
| US7220768B2 (en) * | 2003-02-11 | 2007-05-22 | Wyeth Holdings Corp. | Isoxazole-containing thiourea inhibitors useful for treatment of varicella zoster virus |
| WO2005014825A2 (en) | 2003-08-08 | 2005-02-17 | Arriva Pharmaceuticals, Inc. | Methods of protein production in yeast |
| CA2537124C (en) | 2003-08-29 | 2012-08-07 | Mitsui Chemicals, Inc. | Agricultural/horticultural insecticide and method for using the same |
| WO2005086915A2 (en) | 2004-03-09 | 2005-09-22 | Arriva Pharmaceuticals, Inc. | Treatment of chronic obstructive pulmonary disease by low dose inhalation of protease inhibitor |
| US20100093864A1 (en) * | 2006-10-13 | 2010-04-15 | Lica Pharmaceuticals | Anti-infective thiourea compounds |
| US8524907B2 (en) | 2006-11-02 | 2013-09-03 | Millennium Pharmaceuticals, Inc. | Methods of synthesizing pharmaceutical salts of a factor Xa inhibitor |
| CN108619123A (zh) * | 2018-03-13 | 2018-10-09 | 武汉威立得生物医药有限公司 | Tenovin-1在制备防治人类疱疹病毒感染药物中的应用 |
| WO2019193541A1 (en) * | 2018-04-06 | 2019-10-10 | Glaxosmithkline Intellectual Property Development Limited | Bicyclic aromatic ring derivatives of formula (i) as atf4 inhibitors |
| CN112807294B (zh) * | 2019-11-18 | 2023-09-05 | 武汉大学 | 一种酰基硫脲类化合物在制备治疗或预防单纯疱疹病毒i型感染药物中的应用 |
| WO2022150962A1 (en) * | 2021-01-12 | 2022-07-21 | Westlake Pharmaceutical (Hangzhou) Co., Ltd. | Protease inhibitors, preparation, and uses thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69830751T2 (de) * | 1997-04-10 | 2006-05-18 | Pharmacia & Upjohn Co. Llc, Kalamazoo | Polyaromatische Verbindungen zur Behandlung von Herpes-Infektionen |
-
1999
- 1999-12-06 KR KR1020017007052A patent/KR20010087413A/ko not_active Application Discontinuation
- 1999-12-06 HU HU0104944A patent/HUP0104944A3/hu unknown
- 1999-12-06 CA CA002350899A patent/CA2350899A1/en not_active Abandoned
- 1999-12-06 JP JP2000586685A patent/JP2002531544A/ja active Pending
- 1999-12-06 WO PCT/US1999/028844 patent/WO2000034237A2/en not_active Application Discontinuation
- 1999-12-06 PL PL99349131A patent/PL349131A1/xx not_active Application Discontinuation
- 1999-12-06 AU AU31112/00A patent/AU3111200A/en not_active Abandoned
- 1999-12-06 CN CN99815640A patent/CN1333750A/zh active Pending
- 1999-12-06 EA EA200100640A patent/EA200100640A1/ru unknown
- 1999-12-06 EP EP99965132A patent/EP1137633A2/en not_active Withdrawn
- 1999-12-06 BR BR9916041-2A patent/BR9916041A/pt not_active Application Discontinuation
- 1999-12-06 CZ CZ20012060A patent/CZ20012060A3/cs unknown
- 1999-12-06 IL IL14320499A patent/IL143204A0/xx unknown
-
2001
- 2001-05-21 ZA ZA200104142A patent/ZA200104142B/en unknown
- 2001-06-08 NO NO20012834A patent/NO20012834L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| KR20010087413A (ko) | 2001-09-15 |
| CZ20012060A3 (cs) | 2001-11-14 |
| WO2000034237A3 (en) | 2000-11-23 |
| PL349131A1 (en) | 2002-07-01 |
| EA200100640A1 (ru) | 2001-12-24 |
| CN1333750A (zh) | 2002-01-30 |
| NO20012834L (no) | 2001-08-07 |
| HUP0104944A3 (en) | 2003-03-28 |
| BR9916041A (pt) | 2001-12-04 |
| HUP0104944A2 (hu) | 2002-04-29 |
| JP2002531544A (ja) | 2002-09-24 |
| AU3111200A (en) | 2000-06-26 |
| IL143204A0 (en) | 2002-04-21 |
| EP1137633A2 (en) | 2001-10-04 |
| CA2350899A1 (en) | 2000-06-15 |
| NO20012834D0 (no) | 2001-06-08 |
| WO2000034237A2 (en) | 2000-06-15 |
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