CA2438805A1 - Fluoro oxindole derivatives as modulators of kcnq potassium channels - Google Patents
Fluoro oxindole derivatives as modulators of kcnq potassium channels Download PDFInfo
- Publication number
- CA2438805A1 CA2438805A1 CA002438805A CA2438805A CA2438805A1 CA 2438805 A1 CA2438805 A1 CA 2438805A1 CA 002438805 A CA002438805 A CA 002438805A CA 2438805 A CA2438805 A CA 2438805A CA 2438805 A1 CA2438805 A1 CA 2438805A1
- Authority
- CA
- Canada
- Prior art keywords
- chloro
- fluoro
- phenyl
- dihydro
- indol
- 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.)
- Abandoned
Links
- 102000012359 KCNQ Potassium Channels Human genes 0.000 title claims abstract description 19
- 108010022282 KCNQ Potassium Channels Proteins 0.000 title claims abstract description 19
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 37
- 238000011282 treatment Methods 0.000 claims abstract description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 16
- 208000035475 disorder Diseases 0.000 claims abstract description 13
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 7
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 5
- 125000001246 bromo group Chemical group Br* 0.000 claims abstract description 4
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims abstract 2
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- RFJFVDMQFHPIBN-UHFFFAOYSA-N 3-(5-chloro-2-ethylsulfanylphenyl)-3-fluoro-6-(trifluoromethyl)-1h-indol-2-one Chemical compound CCSC1=CC=C(Cl)C=C1C1(F)C2=CC=C(C(F)(F)F)C=C2NC1=O RFJFVDMQFHPIBN-UHFFFAOYSA-N 0.000 claims description 2
- VGOIYONPFBLHPS-UHFFFAOYSA-N 3-(5-chloro-2-propylsulfanylphenyl)-3-fluoro-6-(trifluoromethyl)-1h-indol-2-one Chemical compound CCCSC1=CC=C(Cl)C=C1C1(F)C2=CC=C(C(F)(F)F)C=C2NC1=O VGOIYONPFBLHPS-UHFFFAOYSA-N 0.000 claims description 2
- PWSJXVHUKGKHCY-UHFFFAOYSA-N 3-[5-chloro-2-(2-methylpropylsulfanyl)phenyl]-3-fluoro-6-(trifluoromethyl)-1h-indol-2-one Chemical compound CC(C)CSC1=CC=C(Cl)C=C1C1(F)C2=CC=C(C(F)(F)F)C=C2NC1=O PWSJXVHUKGKHCY-UHFFFAOYSA-N 0.000 claims description 2
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- UHCBBWUQDAVSMS-UHFFFAOYSA-N fluoroethane Chemical group CCF UHCBBWUQDAVSMS-UHFFFAOYSA-N 0.000 claims 1
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- 108010092555 Large-Conductance Calcium-Activated Potassium Channels Proteins 0.000 description 6
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
-
- 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
- A61P25/06—Antimigraine agents
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27011201P | 2001-02-20 | 2001-02-20 | |
| US60/270,112 | 2001-02-20 | ||
| PCT/US2002/004304 WO2002066426A2 (en) | 2001-02-20 | 2002-02-14 | Fluoro oxindole derivatives as modulators of kcnq potassium channels |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2438805A1 true CA2438805A1 (en) | 2002-08-29 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002438805A Abandoned CA2438805A1 (en) | 2001-02-20 | 2002-02-14 | Fluoro oxindole derivatives as modulators of kcnq potassium channels |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP1363624A2 (hu) |
| JP (1) | JP2004531483A (hu) |
| CA (1) | CA2438805A1 (hu) |
| HU (1) | HUP0400063A2 (hu) |
| WO (1) | WO2002066426A2 (hu) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
| WO2004096767A1 (en) * | 2003-04-25 | 2004-11-11 | H. Lundbeck A/S | Sustituted indoline and indole derivatives |
| JPWO2005035498A1 (ja) * | 2003-10-08 | 2006-12-21 | 住友製薬株式会社 | 含窒素二環性化合物の摂食調節剤としての用途 |
| WO2006074991A1 (en) * | 2005-01-11 | 2006-07-20 | Neurosearch A/S | Novel 2-amino benzimidazole derivatives and their use as modulators of small-conductance calcium-activated potassium channels |
| EP2540295A1 (en) * | 2011-06-27 | 2013-01-02 | Centre national de la recherche scientifique | Compositions for the treatment of Fragile X syndrome |
| CN110240558B (zh) * | 2019-07-10 | 2022-05-27 | 上海华理生物医药股份有限公司 | 一种Flindokalner消旋体的新合成方法 |
| EP3912625A1 (en) | 2020-05-20 | 2021-11-24 | Kaerus Bioscience Limited | Novel maxi-k potassium channel openers for the treatment of fragile x associated disorders |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5565483A (en) * | 1995-06-07 | 1996-10-15 | Bristol-Myers Squibb Company | 3-substituted oxindole derivatives as potassium channel modulators |
| EP1144387A1 (en) * | 1998-12-04 | 2001-10-17 | Neurosearch A/S | New benzimidazolone-, benzoxazolone-, or benzothiazolone derivatives as ion channel modulating agents |
| WO2001010380A2 (en) * | 1999-08-04 | 2001-02-15 | Icagen, Inc. | Benzanilides as potassium channel openers |
-
2002
- 2002-02-14 CA CA002438805A patent/CA2438805A1/en not_active Abandoned
- 2002-02-14 WO PCT/US2002/004304 patent/WO2002066426A2/en not_active Application Discontinuation
- 2002-02-14 EP EP02714888A patent/EP1363624A2/en not_active Withdrawn
- 2002-02-14 JP JP2002565943A patent/JP2004531483A/ja not_active Withdrawn
- 2002-02-14 HU HU0400063A patent/HUP0400063A2/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2002066426A3 (en) | 2002-11-21 |
| WO2002066426A2 (en) | 2002-08-29 |
| HUP0400063A2 (hu) | 2004-04-28 |
| EP1363624A2 (en) | 2003-11-26 |
| JP2004531483A (ja) | 2004-10-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |