CA2327784C - Triazolones with a neuroprotective action - Google Patents
Triazolones with a neuroprotective action Download PDFInfo
- Publication number
- CA2327784C CA2327784C CA002327784A CA2327784A CA2327784C CA 2327784 C CA2327784 C CA 2327784C CA 002327784 A CA002327784 A CA 002327784A CA 2327784 A CA2327784 A CA 2327784A CA 2327784 C CA2327784 C CA 2327784C
- Authority
- CA
- Canada
- Prior art keywords
- compound
- phenyl
- pharmaceutically acceptable
- triazol
- pharmaceutical composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 230000000324 neuroprotective effect Effects 0.000 title abstract description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 42
- 150000001875 compounds Chemical class 0.000 claims description 63
- 150000003839 salts Chemical class 0.000 claims description 30
- 206010021143 Hypoxia Diseases 0.000 claims description 12
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 10
- 210000004556 brain Anatomy 0.000 claims description 7
- 206010002660 Anoxia Diseases 0.000 claims description 6
- 241000976983 Anoxia Species 0.000 claims description 6
- 206010048962 Brain oedema Diseases 0.000 claims description 6
- 208000013016 Hypoglycemia Diseases 0.000 claims description 6
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 6
- 230000007953 anoxia Effects 0.000 claims description 6
- 230000007954 hypoxia Effects 0.000 claims description 6
- 230000004770 neurodegeneration Effects 0.000 claims description 6
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 6
- 208000024827 Alzheimer disease Diseases 0.000 claims description 5
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 5
- 208000016988 Hemorrhagic Stroke Diseases 0.000 claims description 5
- 208000023105 Huntington disease Diseases 0.000 claims description 5
- 206010021118 Hypotonia Diseases 0.000 claims description 5
- 206010061216 Infarction Diseases 0.000 claims description 5
- 208000032382 Ischaemic stroke Diseases 0.000 claims description 5
- 208000007379 Muscle Hypotonia Diseases 0.000 claims description 5
- 206010028923 Neonatal asphyxia Diseases 0.000 claims description 5
- 208000037212 Neonatal hypoxic and ischemic brain injury Diseases 0.000 claims description 5
- 208000018737 Parkinson disease Diseases 0.000 claims description 5
- 208000028017 Psychotic disease Diseases 0.000 claims description 5
- 208000009205 Tinnitus Diseases 0.000 claims description 5
- 230000000747 cardiac effect Effects 0.000 claims description 5
- 201000002342 diabetic polyneuropathy Diseases 0.000 claims description 5
- 230000007574 infarction Effects 0.000 claims description 5
- 201000009941 intracranial hypertension Diseases 0.000 claims description 5
- 230000000302 ischemic effect Effects 0.000 claims description 5
- 208000033300 perinatal asphyxia Diseases 0.000 claims description 5
- 201000000980 schizophrenia Diseases 0.000 claims description 5
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- WQQQBUSFBWNHBP-UHFFFAOYSA-N 2-(2-bromophenyl)-4-methyl-5-phenyl-1,2,4-triazol-3-one Chemical compound O=C1N(C)C(C=2C=CC=CC=2)=NN1C1=CC=CC=C1Br WQQQBUSFBWNHBP-UHFFFAOYSA-N 0.000 claims description 3
- INMMNVZYBDVSRD-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-methyl-5-phenyl-1,2,4-triazol-3-one Chemical compound O=C1N(C)C(C=2C=CC=CC=2)=NN1C1=CC=CC=C1Cl INMMNVZYBDVSRD-UHFFFAOYSA-N 0.000 claims description 3
- WXAFVRHIIVGONB-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-phenyl-1h-1,2,4-triazol-3-one Chemical compound ClC1=CC=CC=C1N1C(=O)N=C(C=2C=CC=CC=2)N1 WXAFVRHIIVGONB-UHFFFAOYSA-N 0.000 claims description 3
- VQRFKKRMXQLDBF-UHFFFAOYSA-N 2-(2-ethylphenyl)-5-phenyl-1h-1,2,4-triazol-3-one Chemical compound CCC1=CC=CC=C1N1C(=O)N=C(C=2C=CC=CC=2)N1 VQRFKKRMXQLDBF-UHFFFAOYSA-N 0.000 claims description 3
- WSFBWWSTYAIQRM-UHFFFAOYSA-N 2-(2-fluorophenyl)-4-methyl-5-phenyl-1,2,4-triazol-3-one Chemical compound O=C1N(C)C(C=2C=CC=CC=2)=NN1C1=CC=CC=C1F WSFBWWSTYAIQRM-UHFFFAOYSA-N 0.000 claims description 3
- RMUFQLARBJMEGP-UHFFFAOYSA-N 2-(2-fluorophenyl)-5-phenyl-1h-1,2,4-triazol-3-one Chemical compound FC1=CC=CC=C1N1C(=O)N=C(C=2C=CC=CC=2)N1 RMUFQLARBJMEGP-UHFFFAOYSA-N 0.000 claims description 3
- WFZHETRZFDYADE-UHFFFAOYSA-N 2-(2-methoxyphenyl)-5-phenyl-1h-1,2,4-triazol-3-one Chemical compound COC1=CC=CC=C1N1C(=O)N=C(C=2C=CC=CC=2)N1 WFZHETRZFDYADE-UHFFFAOYSA-N 0.000 claims description 3
- PDPPFKHBXYBDFM-UHFFFAOYSA-N 2-(3-methylphenyl)-5-phenyl-1h-1,2,4-triazol-3-one Chemical compound CC1=CC=CC(N2C(N=C(N2)C=2C=CC=CC=2)=O)=C1 PDPPFKHBXYBDFM-UHFFFAOYSA-N 0.000 claims description 3
- AFVIXVDGHPMYPR-UHFFFAOYSA-N 4-methyl-2-(3-methylphenyl)-5-phenyl-1,2,4-triazol-3-one Chemical compound CC1=CC=CC(N2C(N(C)C(C=3C=CC=CC=3)=N2)=O)=C1 AFVIXVDGHPMYPR-UHFFFAOYSA-N 0.000 claims description 3
- OZJSBBHULNYLNO-UHFFFAOYSA-N 5-(2-methoxyphenyl)-4-methyl-2-phenyl-1,2,4-triazol-3-one Chemical compound COC1=CC=CC=C1C(N(C1=O)C)=NN1C1=CC=CC=C1 OZJSBBHULNYLNO-UHFFFAOYSA-N 0.000 claims description 3
- TWTRMRDPHGZDOD-UHFFFAOYSA-N 5-(4-methoxyphenyl)-4-methyl-2-phenyl-1,2,4-triazol-3-one Chemical compound C1=CC(OC)=CC=C1C(N(C1=O)C)=NN1C1=CC=CC=C1 TWTRMRDPHGZDOD-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- UEVPEVDGRGLBGH-UHFFFAOYSA-N 2-(2-methylphenyl)-5-phenyl-1h-1,2,4-triazol-3-one Chemical compound CC1=CC=CC=C1N1C(=O)N=C(C=2C=CC=CC=2)N1 UEVPEVDGRGLBGH-UHFFFAOYSA-N 0.000 claims description 2
- CZSRPGZWVHZYHU-UHFFFAOYSA-N 2-(3-fluorophenyl)-4-methyl-5-phenyl-1,2,4-triazol-3-one Chemical compound O=C1N(C)C(C=2C=CC=CC=2)=NN1C1=CC=CC(F)=C1 CZSRPGZWVHZYHU-UHFFFAOYSA-N 0.000 claims description 2
- JWEIKIHJEWDSGD-UHFFFAOYSA-N 2-(3-methoxyphenyl)-4-methyl-5-phenyl-1,2,4-triazol-3-one Chemical compound COC1=CC=CC(N2C(N(C)C(C=3C=CC=CC=3)=N2)=O)=C1 JWEIKIHJEWDSGD-UHFFFAOYSA-N 0.000 claims description 2
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- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 239000002510 pyrogen Substances 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000000946 synaptic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical class O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/12—Oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19816882A DE19816882A1 (de) | 1998-04-17 | 1998-04-17 | Triazolone mit neuroprotektiver Wirkung |
| DE19816882.9 | 1998-04-17 | ||
| PCT/EP1999/002498 WO1999054315A2 (de) | 1998-04-17 | 1999-04-14 | Triazolone mit neuroprotektiver wirkung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2327784A1 CA2327784A1 (en) | 1999-10-28 |
| CA2327784C true CA2327784C (en) | 2008-03-18 |
Family
ID=7864724
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002327784A Expired - Fee Related CA2327784C (en) | 1998-04-17 | 1999-04-14 | Triazolones with a neuroprotective action |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6492407B2 (https=) |
| EP (1) | EP1071671B1 (https=) |
| JP (1) | JP4757382B2 (https=) |
| AT (1) | ATE301112T1 (https=) |
| CA (1) | CA2327784C (https=) |
| DE (2) | DE19816882A1 (https=) |
| WO (1) | WO1999054315A2 (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6613786B2 (en) | 2001-11-02 | 2003-09-02 | Bristol-Myers Squibb Company | Thiophenyl triazol-3-one derivatives as smooth muscle relaxants |
| US7520862B2 (en) | 2004-02-03 | 2009-04-21 | Neuro Diagnostic Devices, Inc. | Cerebral spinal fluid shunt evaluation system |
| DE102006024024A1 (de) | 2006-05-23 | 2007-11-29 | Bayer Healthcare Aktiengesellschaft | Substituierte Arylimidazolone und -triazolone sowie ihre Verwendung |
| DE102008060967A1 (de) | 2008-12-06 | 2010-06-10 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Phenylsulfonyltriazolone und ihre Verwendung |
| DE102009013642A1 (de) | 2009-03-18 | 2010-09-23 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Phenylalaninderivate und deren Verwendung |
| DE102010001064A1 (de) | 2009-03-18 | 2010-09-23 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 2-Acetamido-5-Aryl-1,2,4-triazolone und deren Verwendung |
| DE102009028929A1 (de) | 2009-08-27 | 2011-07-07 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Heterocyclisch-substituierte 2-Acetamido-5-Aryl-1,2,4-triazolone und deren Verwendung |
| UA109650C2 (xx) | 2010-02-27 | 2015-09-25 | Біс-арилзв'язані арилтриазолони та їх застосування | |
| DE102010040187A1 (de) | 2010-09-02 | 2012-03-08 | Bayer Schering Pharma Aktiengesellschaft | Substituierte N-Phenethyl-triazolonacetamide und ihre Verwendung |
| DE102010040924A1 (de) * | 2010-09-16 | 2012-03-22 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Phenylacet- und Phenylpropanamide und ihre Verwendung |
| EP2753179A4 (en) * | 2011-09-09 | 2015-03-04 | Univ Leland Stanford Junior | TOPICAL ITRACONAZOLE FORMULATIONS AND THEIR USE |
| TWI568722B (zh) | 2012-06-15 | 2017-02-01 | 葛蘭馬克製藥公司 | 作爲ｍＰＧＥＳ－１抑制劑之三唑酮化合物 |
| SI3215498T1 (sl) | 2014-11-03 | 2018-11-30 | Bayer Pharma Aktiengesellschaft | Hidroksialkil-substituirani derivati feniltriazola in njihove uporabe |
| US9988367B2 (en) | 2016-05-03 | 2018-06-05 | Bayer Pharma Aktiengesellschaft | Amide-substituted pyridinyltriazole derivatives and uses thereof |
| TW201945346A (zh) | 2018-04-10 | 2019-12-01 | 德商拜耳廠股份有限公司 | 2,4,5-三取代的1,2,4-三唑酮之製備方法 |
| EP3870159B1 (en) * | 2018-10-26 | 2024-11-13 | University of South Florida | Drug for treating tinnitus |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1311651A (en) * | 1969-05-08 | 1973-03-28 | Gold Aubert P | Salts of delta2-1,2,4-triazolin-5-one derivatives |
| JPS5653662A (en) * | 1979-10-08 | 1981-05-13 | Nippon Nohyaku Co Ltd | Preparation of delta2-1,2,4-triazolin-5-ones |
| JPS58225070A (ja) * | 1982-06-23 | 1983-12-27 | Nippon Nohyaku Co Ltd | Δ↑２−１，２，４−トリアゾリン−５−オン誘導体及び製法並びにその用途 |
| GB8429307D0 (en) * | 1984-11-20 | 1984-12-27 | Shell Int Research | Heterocyclic herbicides |
| ZA865000B (en) * | 1985-07-12 | 1987-02-25 | Hoffmann La Roche | Heterocyclic compounds |
| DK570987A (da) * | 1986-12-01 | 1988-06-02 | Hoffmann La Roche | Oxadiazol-, thiadiazol- og triazolforbindelser |
| PH24094A (en) * | 1986-12-19 | 1990-03-05 | Merrell Dow Pharma | 5-aryl-3h-1,2,4-triazol-3-ones and their use as anticonvulsants |
| JP2593084B2 (ja) * | 1986-12-19 | 1997-03-19 | メレルダウファーマスーティカルズ インコーポレーテッド | ５−アリールー３ｈ−１，２，４−トリアゾールー３−オン類の神経変性障害の処置への用途 |
| US5436252A (en) * | 1986-12-19 | 1995-07-25 | Merrell Dow Pharmaceuticals Inc. | 5-aryl-3H-1,2,4-triazol-3-ones and their use in the treatment of neurodegenerative disorders |
| IE880195L (en) * | 1987-01-27 | 1988-07-27 | Merrell Dow Pharma | 5-aryl-2,4-dialkyl-3h-1,2,4-triazole-3-thiones. |
| US5120347A (en) * | 1990-06-21 | 1992-06-09 | Rohm And Haas Company | Aryl triazole herbicides |
| US5256793A (en) * | 1992-05-13 | 1993-10-26 | Fmc Corporation | Triazolinone ring formation in tert-butanol |
| IT1256387B (it) * | 1992-11-13 | 1995-12-04 | Acraf | Procedimento per preparare triazoloni |
| US5597809A (en) * | 1994-06-23 | 1997-01-28 | Massachusetts Eye & Ear Infirmary | Treatment of optic neuritis |
| US6114334A (en) * | 1995-07-13 | 2000-09-05 | Knoll Aktiengesellschaft | Piperazine derivatives as therapeutic agents |
| TW467902B (en) * | 1996-07-31 | 2001-12-11 | Bristol Myers Squibb Co | Diphenyl heterocycles as potassium channel modulators |
| US5756755A (en) * | 1996-08-26 | 1998-05-26 | Fmc Corporation | Difluoromethylation of 4,5-dihydro-1-phenyl-3-methyl-1,2,4-triazol-5(1H)-ones with glymes as solvents |
-
1998
- 1998-04-17 DE DE19816882A patent/DE19816882A1/de not_active Withdrawn
-
1999
- 1999-04-14 EP EP99915760A patent/EP1071671B1/de not_active Expired - Lifetime
- 1999-04-14 CA CA002327784A patent/CA2327784C/en not_active Expired - Fee Related
- 1999-04-14 DE DE59912358T patent/DE59912358D1/de not_active Expired - Lifetime
- 1999-04-14 WO PCT/EP1999/002498 patent/WO1999054315A2/de not_active Ceased
- 1999-04-14 JP JP2000544654A patent/JP4757382B2/ja not_active Expired - Fee Related
- 1999-04-14 AT AT99915760T patent/ATE301112T1/de not_active IP Right Cessation
-
2001
- 2001-04-23 US US09/840,281 patent/US6492407B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2327784A1 (en) | 1999-10-28 |
| DE19816882A1 (de) | 1999-10-21 |
| WO1999054315A2 (de) | 1999-10-28 |
| EP1071671A2 (de) | 2001-01-31 |
| EP1071671B1 (de) | 2005-08-03 |
| US6492407B2 (en) | 2002-12-10 |
| DE59912358D1 (de) | 2005-09-08 |
| US20020045651A1 (en) | 2002-04-18 |
| JP4757382B2 (ja) | 2011-08-24 |
| WO1999054315A3 (de) | 1999-12-29 |
| JP2002512236A (ja) | 2002-04-23 |
| ATE301112T1 (de) | 2005-08-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20130415 |