AU711736B2 - Diphenyl heterocycles as potassium channel modulators - Google Patents
Diphenyl heterocycles as potassium channel modulators Download PDFInfo
- Publication number
- AU711736B2 AU711736B2 AU40679/97A AU4067997A AU711736B2 AU 711736 B2 AU711736 B2 AU 711736B2 AU 40679/97 A AU40679/97 A AU 40679/97A AU 4067997 A AU4067997 A AU 4067997A AU 711736 B2 AU711736 B2 AU 711736B2
- Authority
- AU
- Australia
- Prior art keywords
- chloro
- phenyl
- oxadiazol
- methyl
- trifluoromethyl
- 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.)
- Ceased
Links
- 239000004305 biphenyl Substances 0.000 title claims description 7
- 102000004257 Potassium Channel Human genes 0.000 title description 12
- 108020001213 potassium channel Proteins 0.000 title description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 title description 7
- 235000010290 biphenyl Nutrition 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 87
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 69
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 54
- -1 5-Chloro-2-hydroxyphenyl Chemical group 0.000 claims description 53
- 238000000034 method Methods 0.000 claims description 35
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 33
- 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 claims description 29
- 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 claims description 29
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 29
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
- 108010092555 Large-Conductance Calcium-Activated Potassium Channels Proteins 0.000 claims description 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- 208000035475 disorder Diseases 0.000 claims description 16
- 102000016469 Large-Conductance Calcium-Activated Potassium Channels Human genes 0.000 claims description 15
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- 241000124008 Mammalia Species 0.000 claims description 11
- ZVTQYRVARPYRRE-UHFFFAOYSA-N oxadiazol-4-one Chemical group O=C1CON=N1 ZVTQYRVARPYRRE-UHFFFAOYSA-N 0.000 claims description 11
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- 208000028867 ischemia Diseases 0.000 claims description 7
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- 230000009529 traumatic brain injury Effects 0.000 claims description 5
- WTSXVIMLKCKWIW-UHFFFAOYSA-N 3h-1,3,4-oxadiazol-2-one Chemical compound O=C1NN=CO1 WTSXVIMLKCKWIW-UHFFFAOYSA-N 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
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- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 3
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- 201000001881 impotence Diseases 0.000 claims description 3
- HWOFQIUXDAXPBK-UHFFFAOYSA-N 3-(5-chloro-2-hydroxyphenyl)-4-phenyl-1h-imidazol-2-one Chemical compound OC1=CC=C(Cl)C=C1N1C(=O)NC=C1C1=CC=CC=C1 HWOFQIUXDAXPBK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004188 dichlorophenyl group Chemical group 0.000 claims description 2
- PYRFHJUXDGQZPM-UHFFFAOYSA-N 1,2,4-triazole-3-thione Chemical compound S=C1N=CN=N1 PYRFHJUXDGQZPM-UHFFFAOYSA-N 0.000 claims 1
- XNRWPJIJOVVQRQ-UHFFFAOYSA-N 2-(5-chloro-2-hydroxyphenyl)-5-[4-(trifluoromethyl)phenyl]-1h-1,2,4-triazol-3-one Chemical compound OC1=CC=C(Cl)C=C1N1C(=O)NC(C=2C=CC(=CC=2)C(F)(F)F)=N1 XNRWPJIJOVVQRQ-UHFFFAOYSA-N 0.000 claims 1
- WKJOQYHMXRVQDK-UHFFFAOYSA-N 2-(dimethylamino)acetamide Chemical compound CN(C)CC(N)=O WKJOQYHMXRVQDK-UHFFFAOYSA-N 0.000 claims 1
- JBUNVWOOAFSLGG-UHFFFAOYSA-N 3-[(4-amino-5-chloro-2-hydroxyphenyl)methyl]-5-(3,4-dichlorophenyl)-1,3,4-oxadiazol-2-one Chemical compound C1=C(Cl)C(N)=CC(O)=C1CN1C(=O)OC(C=2C=C(Cl)C(Cl)=CC=2)=N1 JBUNVWOOAFSLGG-UHFFFAOYSA-N 0.000 claims 1
- DPCFCMNWYBCOOF-UHFFFAOYSA-N 3-[(4-amino-5-chloro-2-hydroxyphenyl)methyl]-5-(3,5-dichlorophenyl)-1,3,4-oxadiazol-2-one Chemical compound C1=C(Cl)C(N)=CC(O)=C1CN1C(=O)OC(C=2C=C(Cl)C=C(Cl)C=2)=N1 DPCFCMNWYBCOOF-UHFFFAOYSA-N 0.000 claims 1
- IQMKPOSFUJNDSH-UHFFFAOYSA-N 4-chloro-2-[5-[4-(trifluoromethyl)phenyl]imidazol-1-yl]phenol Chemical compound OC1=CC=C(Cl)C=C1N1C(C=2C=CC(=CC=2)C(F)(F)F)=CN=C1 IQMKPOSFUJNDSH-UHFFFAOYSA-N 0.000 claims 1
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical group F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 1
- WLYPBMBWKYALCG-UHFFFAOYSA-N [2,4-bis(trifluoromethyl)phenyl]boronic acid Chemical group OB(O)C1=CC=C(C(F)(F)F)C=C1C(F)(F)F WLYPBMBWKYALCG-UHFFFAOYSA-N 0.000 claims 1
- AWIUQNHZMIVVPC-UHFFFAOYSA-N chembl221809 Chemical compound C1=C(Cl)C(N)=CC(O)=C1C(OC1=O)=NN1C1=CC=C(C(F)(F)F)C=C1 AWIUQNHZMIVVPC-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
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- 239000000243 solution Substances 0.000 description 77
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- 238000005481 NMR spectroscopy Methods 0.000 description 36
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 33
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- 238000010992 reflux Methods 0.000 description 27
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- 239000002904 solvent Substances 0.000 description 23
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 22
- 229910052739 hydrogen Inorganic materials 0.000 description 22
- 239000001257 hydrogen Substances 0.000 description 22
- 239000000047 product Substances 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 20
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- 229910052727 yttrium Inorganic materials 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
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- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 10
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- 125000000217 alkyl group Chemical group 0.000 description 8
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 7
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 7
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- 150000004031 phenylhydrazines Chemical class 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
-
- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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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- 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
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- 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
- 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
- C07D233/64—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 substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- 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
- C07D233/70—One oxygen atom
-
- 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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/12—Radicals substituted by oxygen atoms
-
- 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
-
- 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
- C07D249/14—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurosurgery (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2298396P | 1996-07-31 | 1996-07-31 | |
| US60/022983 | 1996-07-31 | ||
| PCT/US1997/014352 WO1998004135A1 (en) | 1996-07-31 | 1997-07-30 | Diphenyl heterocycles as potassium channel modulators |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU4067997A AU4067997A (en) | 1998-02-20 |
| AU711736B2 true AU711736B2 (en) | 1999-10-21 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU40679/97A Ceased AU711736B2 (en) | 1996-07-31 | 1997-07-30 | Diphenyl heterocycles as potassium channel modulators |
Country Status (18)
| Country | Link |
|---|---|
| US (3) | US5869509A (enExample) |
| EP (1) | EP0915856A4 (enExample) |
| JP (1) | JP2000516925A (enExample) |
| KR (1) | KR20000029735A (enExample) |
| CN (1) | CN1116287C (enExample) |
| AR (1) | AR008110A1 (enExample) |
| AU (1) | AU711736B2 (enExample) |
| BR (1) | BR9710793A (enExample) |
| CZ (1) | CZ32199A3 (enExample) |
| HU (1) | HUP0000063A3 (enExample) |
| IL (1) | IL128308A (enExample) |
| NO (1) | NO990428L (enExample) |
| NZ (1) | NZ334403A (enExample) |
| PL (1) | PL331385A1 (enExample) |
| RU (1) | RU2175319C2 (enExample) |
| TW (1) | TW467902B (enExample) |
| WO (1) | WO1998004135A1 (enExample) |
| ZA (1) | ZA976554B (enExample) |
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| TW467902B (en) * | 1996-07-31 | 2001-12-11 | Bristol Myers Squibb Co | Diphenyl heterocycles as potassium channel modulators |
| ID26909A (id) | 1998-01-29 | 2001-02-15 | Bristol Myers Squibb Co | Turunan-turunan 1,3,4-oksadiazolon |
| JP2002501926A (ja) * | 1998-01-29 | 2002-01-22 | ブリストル−マイヤーズ スクイブ カンパニー | ジアリール1、3、4−オキサジアゾロンのホスフェート誘導体 |
| EP1056730A4 (en) * | 1998-01-29 | 2003-01-02 | Bristol Myers Squibb Co | Diaryl-1,3,4-oxadiazolone benzoate |
| JP2003525199A (ja) * | 1998-01-29 | 2003-08-26 | ブリストル−マイヤーズ スクイブ カンパニー | ジアリール1,3,4−オキサジアゾロンアミノ酸誘導体 |
| DE19816882A1 (de) * | 1998-04-17 | 1999-10-21 | Boehringer Ingelheim Pharma | Triazolone mit neuroprotektiver Wirkung |
| US6919366B2 (en) * | 1998-05-22 | 2005-07-19 | Avanir Pharmaceuticals | Benzimidazole derivatives as modulators of IgE |
| US6911462B2 (en) * | 1998-05-22 | 2005-06-28 | Avanir Pharmaceuticals | Benzimidazole compounds for regulating IgE |
| SE9802937D0 (sv) * | 1998-09-01 | 1998-09-01 | Astra Pharma Prod | Novel compounds |
| US6632836B1 (en) | 1998-10-30 | 2003-10-14 | Merck & Co., Inc. | Carbocyclic potassium channel inhibitors |
| US6194458B1 (en) | 1998-10-30 | 2001-02-27 | Merck & Co., Inc. | Benzamide potassium channel inhibitors |
| US6303637B1 (en) * | 1998-10-30 | 2001-10-16 | Merck & Co., Inc. | Heterocyclic potassium channel inhibitors |
| US6297241B1 (en) | 1999-01-29 | 2001-10-02 | Bristol-Myers Squibb Company | Carbamate derivatives of diaryl 1,3,4-oxadiazolone |
| WO2000044745A1 (en) * | 1999-01-29 | 2000-08-03 | Bristol-Myers Squibb Company | Carbamate derivatives of diaryl 1,3,4-oxadiazolone |
| GB9915414D0 (en) * | 1999-07-01 | 1999-09-01 | Glaxo Group Ltd | Medical use |
| US20050153940A1 (en) * | 2000-01-26 | 2005-07-14 | Cedars-Sinai Medical Center | Method for using potassium channel activation for delivering a medicant to an abnormal brain region and/or a malignant tumor |
| US7018979B1 (en) | 2000-01-26 | 2006-03-28 | Cedars-Sinai Medical Center | Method for using potassium channel agonists for delivering a medicant to an abnormal brain region and/or a malignant tumor |
| GB2361003A (en) * | 2000-04-07 | 2001-10-10 | Astrazeneca Ab | Novel compounds |
| HUP0303559A3 (en) * | 2000-10-13 | 2006-02-28 | Bristol Myers Squibb Co | Selective maxi-k-potassium channel openers functional under conditions of high intracellular calcium concentration and uses thereof |
| DE10056344A1 (de) * | 2000-11-14 | 2002-05-16 | Degussa | n-Propylethoxysiloxane, Verfahren zu deren Herstellung und deren Verwendung |
| DE10058461A1 (de) * | 2000-11-24 | 2002-09-19 | Bayer Ag | Substituierte Cyclohexanderivate und ihre Verwendung |
| US6855829B2 (en) | 2001-02-20 | 2005-02-15 | Bristol-Myers Squibb Company | 3-fluoro-2-oxindole modulators of KCNQ potassium channels and use thereof in treating migraine and mechanistically related disease |
| ES2291455T3 (es) * | 2001-03-12 | 2008-03-01 | Avanir Pharmaceuticals | Compuestos de bencimidazol para modular ige e inhibir la proliferacion celular. |
| WO2002083111A2 (en) * | 2001-04-16 | 2002-10-24 | Tanabe Seiyaku Co., Ltd. | Imidazole, thiazole and oxazole derivatives and their use for the manufacture of a medicament for the treatment and/or prevention of pollakiuria or urinary incontinence |
| US7022480B1 (en) | 2001-10-11 | 2006-04-04 | The Regents Of The University Of California | Exons of the hSKCa3/KCNN3 gene |
| US7211561B2 (en) * | 2001-10-12 | 2007-05-01 | Cedars-Sinai Medical Center | Method for inducing selective cell death of malignant cells by activation of calcium-activated potassium channels (KCa) |
| US6613786B2 (en) | 2001-11-02 | 2003-09-02 | Bristol-Myers Squibb Company | Thiophenyl triazol-3-one derivatives as smooth muscle relaxants |
| US7846671B2 (en) * | 2002-01-28 | 2010-12-07 | Bristol-Myers Squibb Company | Methods of screening for agents that modulate the interaction of RGS and Gαq and urinary incontinence |
| TW200304820A (en) * | 2002-03-25 | 2003-10-16 | Avanir Pharmaceuticals | Use of benzimidazole analogs in the treatment of cell proliferation |
| WO2004024655A2 (en) | 2002-09-12 | 2004-03-25 | Avanir Pharmaceuticals | Phenyl-indole compounds for modulating ige and inhibiting cellular proliferation |
| TWI276631B (en) * | 2002-09-12 | 2007-03-21 | Avanir Pharmaceuticals | Phenyl-aza-benzimidazole compounds for modulating IgE and inhibiting cellular proliferation |
| TWI271402B (en) * | 2002-10-15 | 2007-01-21 | Tanabe Seiyaku Co | Large conductance calcium-activated K channel opener |
| TW200505441A (en) | 2003-03-24 | 2005-02-16 | Hoffmann La Roche | Non-nucleoside reverse transcriptase inhibitorsⅠ |
| RU2005134670A (ru) * | 2003-04-10 | 2006-06-10 | Аванир Фармасьютикалс (Us) | Производные имидазола для лечения аллергических и гиперпролиферативных нарушений |
| GB0315111D0 (en) * | 2003-06-27 | 2003-07-30 | Cancer Rec Tech Ltd | Substituted 5-membered ring compounds and their use |
| CA2533990A1 (en) * | 2003-08-08 | 2005-02-17 | Avanir Pharmaceuticals | Selective pharmacologic inhibition of protein trafficking and related methods of treating human diseases |
| AU2005230867A1 (en) * | 2004-03-26 | 2005-10-20 | Amphora Discovery Corporation | Certain triazole-based compounds, compositions, and uses thereof |
| CA2561718A1 (en) * | 2004-04-13 | 2005-10-27 | Icagen, Inc. | Polycyclic pyridines as potassium ion channel modulators |
| EP1773790B1 (en) * | 2004-07-27 | 2012-08-15 | F.Hoffmann-La Roche Ag | Benzyltriazolone compounds as non-nucleoside reverse transcriptase inhibitors |
| US8293778B2 (en) | 2004-07-27 | 2012-10-23 | Roche Palo Alto Llc | Heterocyclic antiviral compounds |
| CA2583177A1 (en) * | 2004-10-13 | 2006-04-27 | Ptc Therapeutics, Inc. | Compounds for nonsense suppression, and methods for their use |
| DK1817295T3 (da) | 2004-11-18 | 2013-02-18 | Synta Pharmaceuticals Corp | Triazolforbindelser, der modulerer HSP90-aktivitet |
| WO2006091542A2 (en) * | 2005-02-22 | 2006-08-31 | Cedars-Sinai Medical Center | Use of sildenafil, vardenafil and other 5-phosphodiesterase inhibitors to enhance permeability of the abnormal blood-brain barrier |
| JP5178515B2 (ja) | 2005-08-12 | 2013-04-10 | シンタ ファーマシューティカルズ コーポレーション | Hsp90活性を調節するピラゾール化合物 |
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-
1997
- 1997-07-15 TW TW086110006A patent/TW467902B/zh not_active IP Right Cessation
- 1997-07-23 ZA ZA976554A patent/ZA976554B/xx unknown
- 1997-07-30 IL IL12830897A patent/IL128308A/en not_active IP Right Cessation
- 1997-07-30 US US08/902,684 patent/US5869509A/en not_active Expired - Fee Related
- 1997-07-30 HU HU0000063A patent/HUP0000063A3/hu unknown
- 1997-07-30 JP JP10509180A patent/JP2000516925A/ja not_active Ceased
- 1997-07-30 BR BR9710793A patent/BR9710793A/pt not_active Application Discontinuation
- 1997-07-30 RU RU99104179/04A patent/RU2175319C2/ru not_active IP Right Cessation
- 1997-07-30 CZ CZ99321A patent/CZ32199A3/cs unknown
- 1997-07-30 AR ARP970103438A patent/AR008110A1/es not_active Application Discontinuation
- 1997-07-30 NZ NZ334403A patent/NZ334403A/xx unknown
- 1997-07-30 PL PL97331385A patent/PL331385A1/xx unknown
- 1997-07-30 WO PCT/US1997/014352 patent/WO1998004135A1/en not_active Ceased
- 1997-07-30 AU AU40679/97A patent/AU711736B2/en not_active Ceased
- 1997-07-30 EP EP97938316A patent/EP0915856A4/en not_active Withdrawn
- 1997-07-30 CN CN97196891A patent/CN1116287C/zh not_active Expired - Fee Related
- 1997-07-30 KR KR1019997000839A patent/KR20000029735A/ko not_active Ceased
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1998
- 1998-11-23 US US09/197,887 patent/US6077861A/en not_active Expired - Fee Related
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1999
- 1999-01-29 NO NO990428A patent/NO990428L/no unknown
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2000
- 2000-03-29 US US09/538,520 patent/US6271249B1/en not_active Expired - Lifetime
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| Publication number | Publication date |
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| NO990428D0 (no) | 1999-01-29 |
| BR9710793A (pt) | 1999-08-17 |
| US6271249B1 (en) | 2001-08-07 |
| HUP0000063A3 (en) | 2001-04-28 |
| EP0915856A1 (en) | 1999-05-19 |
| NZ334403A (en) | 2000-09-29 |
| US6077861A (en) | 2000-06-20 |
| TW467902B (en) | 2001-12-11 |
| ZA976554B (en) | 1999-01-25 |
| KR20000029735A (ko) | 2000-05-25 |
| WO1998004135A1 (en) | 1998-02-05 |
| HUP0000063A2 (hu) | 2001-01-29 |
| NO990428L (no) | 1999-01-29 |
| EP0915856A4 (en) | 2006-04-12 |
| IL128308A (en) | 2004-09-27 |
| IL128308A0 (en) | 1999-11-30 |
| PL331385A1 (en) | 1999-07-05 |
| CN1226803A (zh) | 1999-08-25 |
| JP2000516925A (ja) | 2000-12-19 |
| US5869509A (en) | 1999-02-09 |
| AU4067997A (en) | 1998-02-20 |
| CZ32199A3 (cs) | 1999-06-16 |
| CN1116287C (zh) | 2003-07-30 |
| AR008110A1 (es) | 1999-12-09 |
| RU2175319C2 (ru) | 2001-10-27 |
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