NO328008B1 - 5-aryl-1H-1,2,4-triazol forbindelser som inhibitorer av cyclooksygenase-2 og farmasoytiske preparater inneholdende disse, samt anvendelse derav - Google Patents
5-aryl-1H-1,2,4-triazol forbindelser som inhibitorer av cyclooksygenase-2 og farmasoytiske preparater inneholdende disse, samt anvendelse derav Download PDFInfo
- Publication number
- NO328008B1 NO328008B1 NO20022202A NO20022202A NO328008B1 NO 328008 B1 NO328008 B1 NO 328008B1 NO 20022202 A NO20022202 A NO 20022202A NO 20022202 A NO20022202 A NO 20022202A NO 328008 B1 NO328008 B1 NO 328008B1
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- alkyl
- triazole
- pharmaceutically acceptable
- methylsulfonyl
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title abstract 2
- 108010037462 Cyclooxygenase 2 Proteins 0.000 title description 15
- 239000003112 inhibitor Substances 0.000 title description 3
- 102000010907 Cyclooxygenase 2 Human genes 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 claims abstract description 3
- 150000003839 salts Chemical class 0.000 claims description 25
- -1 methylenedioxy Chemical group 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 17
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 claims description 15
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 102100038277 Prostaglandin G/H synthase 1 Human genes 0.000 claims description 10
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 claims description 10
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 10
- 108050003243 Prostaglandin G/H synthase 1 Proteins 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 230000001404 mediated effect Effects 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 4
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- 229940093444 Cyclooxygenase 2 inhibitor Drugs 0.000 claims 1
- 108050003267 Prostaglandin G/H synthase 2 Proteins 0.000 claims 1
- 230000003389 potentiating effect Effects 0.000 abstract description 4
- 229940111134 coxibs Drugs 0.000 abstract description 2
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 47
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 45
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
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- 239000011541 reaction mixture Substances 0.000 description 24
- 239000007787 solid Substances 0.000 description 23
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 20
- 238000000034 method Methods 0.000 description 16
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
- 239000004480 active ingredient Substances 0.000 description 13
- 239000012044 organic layer Substances 0.000 description 13
- 229910052938 sodium sulfate Inorganic materials 0.000 description 13
- 235000011152 sodium sulphate Nutrition 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
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- 238000010992 reflux Methods 0.000 description 9
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- 238000006243 chemical reaction Methods 0.000 description 7
- NSPMIYGKQJPBQR-CVMUNTFWSA-N 1h-1,2,4-triazole Chemical class [13CH]=1[15N]=[13CH][15NH][15N]=1 NSPMIYGKQJPBQR-CVMUNTFWSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
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- 239000000654 additive Substances 0.000 description 6
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- 239000007859 condensation product Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
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- 150000002148 esters Chemical class 0.000 description 5
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- 239000000194 fatty acid Substances 0.000 description 5
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- 238000003818 flash chromatography Methods 0.000 description 5
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- 125000005843 halogen group Chemical group 0.000 description 5
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- 239000011734 sodium Substances 0.000 description 5
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- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 4
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- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
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- AJBWNNKDUMXZLM-UHFFFAOYSA-N 4-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=C(C(O)=O)C=C1 AJBWNNKDUMXZLM-UHFFFAOYSA-N 0.000 description 3
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- RGGOWBBBHWTTRE-UHFFFAOYSA-N (4-bromophenyl)hydrazine;hydron;chloride Chemical compound Cl.NNC1=CC=C(Br)C=C1 RGGOWBBBHWTTRE-UHFFFAOYSA-N 0.000 description 2
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- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 2
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- MEIZQYSCKVAZTO-UHFFFAOYSA-N 1-(4-bromophenyl)-5-(4-methylsulfonylphenyl)-3-(trifluoromethyl)-1,2,4-triazole Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=NC(C(F)(F)F)=NN1C1=CC=C(Br)C=C1 MEIZQYSCKVAZTO-UHFFFAOYSA-N 0.000 description 2
- IWYORYNBCDBAPV-UHFFFAOYSA-N 1-(4-chlorophenyl)-5-(4-methylsulfanylphenyl)-3-phenyl-1,2,4-triazole Chemical compound C1=CC(SC)=CC=C1C1=NC(C=2C=CC=CC=2)=NN1C1=CC=C(Cl)C=C1 IWYORYNBCDBAPV-UHFFFAOYSA-N 0.000 description 2
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- DGCUCYAZIXCENF-UHFFFAOYSA-N 1-(4-methoxyphenyl)-5-(4-methylsulfanylphenyl)-3-(trifluoromethyl)-1,2,4-triazole Chemical compound C1=CC(OC)=CC=C1N1C(C=2C=CC(SC)=CC=2)=NC(C(F)(F)F)=N1 DGCUCYAZIXCENF-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4196—1,2,4-Triazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99402784A EP1099695A1 (en) | 1999-11-09 | 1999-11-09 | 5-aryl-1H-1,2,4-triazole compounds as inhibitors of cyclooxygenase-2 and pharmaceutical compositions containing them |
| PCT/EP2000/010956 WO2001034577A1 (en) | 1999-11-09 | 2000-11-06 | 5-aryl-1h-1,2,4-triazole compounds as inhibitors of cyclooxygenase-2 and pharmaceutical compositions containing them |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20022202L NO20022202L (no) | 2002-05-08 |
| NO20022202D0 NO20022202D0 (no) | 2002-05-08 |
| NO328008B1 true NO328008B1 (no) | 2009-11-09 |
Family
ID=8242172
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20022202A NO328008B1 (no) | 1999-11-09 | 2002-05-08 | 5-aryl-1H-1,2,4-triazol forbindelser som inhibitorer av cyclooksygenase-2 og farmasoytiske preparater inneholdende disse, samt anvendelse derav |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US6803380B1 (es) |
| EP (2) | EP1099695A1 (es) |
| JP (1) | JP4786846B2 (es) |
| CN (1) | CN1198807C (es) |
| AT (1) | ATE245148T1 (es) |
| AU (1) | AU778819B2 (es) |
| BR (1) | BR0015440A (es) |
| CA (1) | CA2390649C (es) |
| CZ (1) | CZ20021591A3 (es) |
| DE (1) | DE60003949T2 (es) |
| DK (1) | DK1246809T3 (es) |
| ES (1) | ES2203538T3 (es) |
| HU (1) | HUP0203376A3 (es) |
| IL (2) | IL149370A0 (es) |
| MX (1) | MXPA01012903A (es) |
| NO (1) | NO328008B1 (es) |
| NZ (1) | NZ518682A (es) |
| PL (1) | PL204230B1 (es) |
| PT (1) | PT1246809E (es) |
| RU (1) | RU2249588C2 (es) |
| SI (1) | SI1246809T1 (es) |
| TW (1) | TWI268925B (es) |
| WO (1) | WO2001034577A1 (es) |
| ZA (1) | ZA200203165B (es) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60204633T2 (de) | 2001-07-05 | 2006-06-14 | Pfizer Prod Inc | Sulfonyl-Heteroaryl-Triazole als entzündungshemmende und analgetische Mittel |
| CA2390181A1 (en) * | 2001-07-05 | 2003-01-05 | Andrei Shavnya | Sulfonyl aryl triazoles as anti-inflammatory/analgesic agents |
| DE60204823T2 (de) | 2001-07-05 | 2005-12-29 | Pfizer Products Inc., Groton | Heterocyclo-alkylsulfonyl Pyrazole als entzündungshemmende/analgetische Mittel |
| KR100824233B1 (ko) | 2001-10-10 | 2008-04-24 | 씨제이제일제당 (주) | 사이클로옥시게나제-2의 저해제로서 선택성이 뛰어난3,4-디하이드로-1ｈ-나프탈렌 유도체 |
| WO2003037336A1 (en) | 2001-11-02 | 2003-05-08 | Pfizer Products Inc. | 1-(5-sulfonyl-pyridin-2-yl)-5-(methylidene-cycloalkylmethoxy)-1h-pyrazole-4-carbonitrile derivatives and other compounds as cyclooxygenase inhibitors for the treatment of arthritis, neurodegeneration and colon cancer |
| AUPR878201A0 (en) | 2001-11-09 | 2001-12-06 | Fujisawa Pharmaceutical Co., Ltd. | New compounds |
| KR100686537B1 (ko) | 2001-12-28 | 2007-02-27 | 씨제이 주식회사 | 사이클로옥시게나제-2 의 저해제로서 선택성이 뛰어난디아릴 1,2,4-트리아졸 유도체 |
| US6797722B2 (en) * | 2002-05-03 | 2004-09-28 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Use of 3-(2-ethylphenyl)-5-(3-methoxyphenyl)-1H-1,2,4-triazole for the treatment of autoimmune diseases |
| KR100467668B1 (ko) * | 2002-08-07 | 2005-01-24 | 씨제이 주식회사 | 1,2,4-트리아졸 유도체, 그 제조방법 및 약제학적 조성물 |
| KR100470075B1 (ko) * | 2002-11-21 | 2005-02-05 | 씨제이 주식회사 | 1,2,4-트리아졸 유도체, 그 제조방법 및 약제학적 조성물 |
| KR100491317B1 (ko) * | 2002-11-26 | 2005-05-24 | 씨제이 주식회사 | 1,2,4-트리아졸 유도체, 그 제조방법 및 약제학적 조성물 |
| KR100470076B1 (ko) * | 2002-11-27 | 2005-02-05 | 씨제이 주식회사 | 1,2,4-트리아졸 유도체, 그 제조방법 및 약제학적 조성물 |
| WO2004060367A1 (en) * | 2002-12-30 | 2004-07-22 | Fujisawa Pharmaceutical Co., Ltd. | Imidazole and triazole derivatives useful as selective cox-1 inhibitors |
| WO2006114377A1 (en) * | 2005-04-28 | 2006-11-02 | Ciba Specialty Chemicals Holding Inc. | Electroluminescent device |
| US20100256357A1 (en) * | 2006-08-09 | 2010-10-07 | Agouron Pharmaceuticals, Inc. | Heterocycles useful as inhibitors of carbonic anhydrase |
| WO2012070596A1 (en) * | 2010-11-26 | 2012-05-31 | Semiconductor Energy Laboratory Co., Ltd. | Organometallic complex, light-emitting element, light-emitting device, electronic device, and lighting device |
| WO2012170839A2 (en) * | 2011-06-09 | 2012-12-13 | Cardeus Pharmaceuticals, Inc. | Treatment of neuroinflammatory disease with selective cox1 inhibitors |
| US8853248B2 (en) * | 2012-04-05 | 2014-10-07 | Hubert Maehr | (1,2,3-triazolyl)sulfonyl derivatives |
| CN104693133A (zh) * | 2015-02-16 | 2015-06-10 | 广州市盈宇医药科技有限公司 | 一种环氧化酶-2选择性抑制剂及其制备方法和应用 |
| CN111818801A (zh) | 2018-03-08 | 2020-10-23 | 拜耳公司 | 杂芳基-三唑和杂芳基-四唑化合物在植物保护中用作农药的用途 |
| TWI829595B (zh) | 2018-04-12 | 2024-01-11 | 德商拜耳廠股份有限公司 | 作為殺蟲劑之新穎雜芳基三唑和雜芳基四唑化合物 |
| CA3098061A1 (en) | 2018-04-25 | 2019-10-31 | Bayer Aktiengesellschaft | Novel heteroaryl-triazole and heteroaryl-tetrazole compounds as pesticides |
| US20220274947A1 (en) | 2019-07-23 | 2022-09-01 | Bayer Aktiengesellschaft | Novel heteroaryl-triazole compounds as pesticides |
| CA3148216A1 (en) | 2019-07-23 | 2021-01-28 | Bayer Aktiengesellschaft | Novel heteroaryl-triazole compounds as pesticides |
| AU2020363864A1 (en) | 2019-10-09 | 2022-04-21 | Bayer Aktiengesellschaft | Novel heteroaryl-triazole compounds as pesticides |
| TW202134226A (zh) | 2019-11-18 | 2021-09-16 | 德商拜耳廠股份有限公司 | 作為殺蟲劑之新穎雜芳基-三唑化合物 |
| JP2023513624A (ja) | 2020-02-18 | 2023-03-31 | バイエル・アクチエンゲゼルシヤフト | 殺有害生物剤としてのヘテロアリール－トリアゾール化合物 |
| TWI754474B (zh) * | 2020-11-30 | 2022-02-01 | 翁豐富 | 具選擇性第二型環氧合酶抑制活性之1,2,4-三氮唑衍生物及其用途 |
| CN112480073B (zh) * | 2020-12-02 | 2022-03-22 | 武汉药明康德新药开发有限公司 | 1-烷基-3,5-芳基取代的1,2,4三氮唑化合物的合成方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW226993B (es) * | 1992-05-29 | 1994-07-21 | Kumiai Chemical Industry Co | |
| US5474995A (en) * | 1993-06-24 | 1995-12-12 | Merck Frosst Canada, Inc. | Phenyl heterocycles as cox-2 inhibitors |
| JPH0776577A (ja) * | 1993-07-14 | 1995-03-20 | Kumiai Chem Ind Co Ltd | ジフェニルトリアゾール誘導体及び殺虫、殺ダニ剤 |
| US5434178A (en) * | 1993-11-30 | 1995-07-18 | G.D. Searle & Co. | 1,3,5 trisubstituted pyrazole compounds for treatment of inflammation |
-
1999
- 1999-11-09 EP EP99402784A patent/EP1099695A1/en not_active Withdrawn
-
2000
- 2000-10-26 TW TW089122507A patent/TWI268925B/zh not_active IP Right Cessation
- 2000-11-06 EP EP00983110A patent/EP1246809B1/en not_active Expired - Lifetime
- 2000-11-06 CN CNB008154732A patent/CN1198807C/zh not_active Expired - Fee Related
- 2000-11-06 BR BR0015440-7A patent/BR0015440A/pt not_active Application Discontinuation
- 2000-11-06 DE DE60003949T patent/DE60003949T2/de not_active Expired - Lifetime
- 2000-11-06 AT AT00983110T patent/ATE245148T1/de active
- 2000-11-06 PL PL356120A patent/PL204230B1/pl not_active IP Right Cessation
- 2000-11-06 SI SI200030220T patent/SI1246809T1/xx unknown
- 2000-11-06 RU RU2002115284/04A patent/RU2249588C2/ru not_active IP Right Cessation
- 2000-11-06 WO PCT/EP2000/010956 patent/WO2001034577A1/en active IP Right Grant
- 2000-11-06 CA CA002390649A patent/CA2390649C/en not_active Expired - Fee Related
- 2000-11-06 MX MXPA01012903A patent/MXPA01012903A/es active IP Right Grant
- 2000-11-06 PT PT00983110T patent/PT1246809E/pt unknown
- 2000-11-06 IL IL14937000A patent/IL149370A0/xx active IP Right Grant
- 2000-11-06 JP JP2001536525A patent/JP4786846B2/ja not_active Expired - Fee Related
- 2000-11-06 DK DK00983110T patent/DK1246809T3/da active
- 2000-11-06 US US10/111,424 patent/US6803380B1/en not_active Expired - Fee Related
- 2000-11-06 AU AU19985/01A patent/AU778819B2/en not_active Ceased
- 2000-11-06 ES ES00983110T patent/ES2203538T3/es not_active Expired - Lifetime
- 2000-11-06 HU HU0203376A patent/HUP0203376A3/hu unknown
- 2000-11-06 NZ NZ518682A patent/NZ518682A/en not_active IP Right Cessation
- 2000-11-06 CZ CZ20021591A patent/CZ20021591A3/cs unknown
-
2002
- 2002-04-22 ZA ZA200203165A patent/ZA200203165B/xx unknown
- 2002-04-25 IL IL149370A patent/IL149370A/en not_active IP Right Cessation
- 2002-05-08 NO NO20022202A patent/NO328008B1/no not_active IP Right Cessation
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