AU2009271302A1 - Benzyloxy anilide derivatives useful as potassium channel modulators - Google Patents
Benzyloxy anilide derivatives useful as potassium channel modulators Download PDFInfo
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- AU2009271302A1 AU2009271302A1 AU2009271302A AU2009271302A AU2009271302A1 AU 2009271302 A1 AU2009271302 A1 AU 2009271302A1 AU 2009271302 A AU2009271302 A AU 2009271302A AU 2009271302 A AU2009271302 A AU 2009271302A AU 2009271302 A1 AU2009271302 A1 AU 2009271302A1
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- Prior art keywords
- alkyl
- cycloalkyl
- formula
- compound
- chr
- 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.)
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- -1 Benzyloxy anilide Chemical class 0.000 title claims description 47
- 102000004257 Potassium Channel Human genes 0.000 title description 9
- 108020001213 potassium channel Proteins 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims description 416
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 267
- 125000000217 alkyl group Chemical group 0.000 claims description 176
- 229910052739 hydrogen Inorganic materials 0.000 claims description 107
- 229910052736 halogen Inorganic materials 0.000 claims description 95
- 150000002367 halogens Chemical class 0.000 claims description 95
- 229910052731 fluorine Inorganic materials 0.000 claims description 88
- 229910052801 chlorine Inorganic materials 0.000 claims description 70
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 57
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 44
- 229910052794 bromium Inorganic materials 0.000 claims description 39
- 125000003342 alkenyl group Chemical group 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 30
- 125000000304 alkynyl group Chemical group 0.000 claims description 29
- 125000004076 pyridyl group Chemical group 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 239000012453 solvate Substances 0.000 claims description 10
- 125000002541 furyl group Chemical group 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 208000035475 disorder Diseases 0.000 claims description 7
- 125000002971 oxazolyl group Chemical group 0.000 claims description 7
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 102000003734 Voltage-Gated Potassium Channels Human genes 0.000 claims description 3
- 108090000013 Voltage-Gated Potassium Channels Proteins 0.000 claims description 3
- 230000004913 activation Effects 0.000 claims description 3
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 14
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 118
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 60
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 53
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 22
- 206010010904 Convulsion Diseases 0.000 description 19
- 238000012360 testing method Methods 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 125000001188 haloalkyl group Chemical group 0.000 description 18
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- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 10
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- 108010006746 KCNQ2 Potassium Channel Proteins 0.000 description 7
- 102100034354 Potassium voltage-gated channel subfamily KQT member 2 Human genes 0.000 description 7
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 4
- MMLPWOHLKRXZJA-UHFFFAOYSA-N 3,5-dimethyl-4-nitrophenol Chemical compound CC1=CC(O)=CC(C)=C1[N+]([O-])=O MMLPWOHLKRXZJA-UHFFFAOYSA-N 0.000 description 4
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- 239000007995 HEPES buffer Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 102000004310 Ion Channels Human genes 0.000 description 4
- 108090000862 Ion Channels Proteins 0.000 description 4
- 229960003965 antiepileptics Drugs 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 150000005524 benzylchlorides Chemical class 0.000 description 4
- 230000006735 deficit Effects 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
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- 229920000609 methyl cellulose Polymers 0.000 description 4
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- 235000010981 methylcellulose Nutrition 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- FGDZQCVHDSGLHJ-UHFFFAOYSA-M rubidium chloride Chemical compound [Cl-].[Rb+] FGDZQCVHDSGLHJ-UHFFFAOYSA-M 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
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- 230000001256 tonic effect Effects 0.000 description 4
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 3
- WKJLZHPOOMPGPI-UHFFFAOYSA-N 4-[(4-fluorophenyl)methoxy]aniline Chemical compound C1=CC(N)=CC=C1OCC1=CC=C(F)C=C1 WKJLZHPOOMPGPI-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 108010011185 KCNQ1 Potassium Channel Proteins 0.000 description 3
- 108010038888 KCNQ3 Potassium Channel Proteins 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- 102100037444 Potassium voltage-gated channel subfamily KQT member 1 Human genes 0.000 description 3
- 102100034360 Potassium voltage-gated channel subfamily KQT member 3 Human genes 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
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- 230000007135 neurotoxicity Effects 0.000 description 1
- 231100000228 neurotoxicity Toxicity 0.000 description 1
- RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 238000002732 pharmacokinetic assay Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940068965 polysorbates Drugs 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012910 preclinical development Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000011552 rat model Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 230000036390 resting membrane potential Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000010825 rotarod performance test Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229940054269 sodium pyruvate Drugs 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000008137 solubility enhancer Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000003826 tablet Substances 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
- GKCBAIGFKIBETG-UHFFFAOYSA-N tetracaine Chemical compound CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 GKCBAIGFKIBETG-UHFFFAOYSA-N 0.000 description 1
- 229960002372 tetracaine Drugs 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/24—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/25—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- 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
- A61P25/08—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/24—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/26—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a saturated carbon skeleton containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7530708P | 2008-06-24 | 2008-06-24 | |
| US61/075,307 | 2008-06-24 | ||
| PCT/US2009/048504 WO2010008894A1 (en) | 2008-06-24 | 2009-06-24 | Benzyloxy anilide derivatives useful as potassium channel modulators |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2009271302A1 true AU2009271302A1 (en) | 2010-01-21 |
Family
ID=41448228
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2009271302A Abandoned AU2009271302A1 (en) | 2008-06-24 | 2009-06-24 | Benzyloxy anilide derivatives useful as potassium channel modulators |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US8188314B2 (enExample) |
| EP (1) | EP2310369A4 (enExample) |
| JP (1) | JP2011525538A (enExample) |
| AU (1) | AU2009271302A1 (enExample) |
| CA (1) | CA2728915A1 (enExample) |
| MX (1) | MX2010014461A (enExample) |
| WO (1) | WO2010008894A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2013257209B2 (en) * | 2012-04-30 | 2016-05-19 | Scifluor Life Sciences, Inc | Fluorinated 2-amino-4-(benzylamino)phenylcarbamate derivatives |
| CN103508943B (zh) * | 2012-06-29 | 2017-06-09 | 江苏先声药业有限公司 | 作为钾通道调节剂的化合物 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5533409B2 (enExample) * | 1972-04-15 | 1980-08-30 | ||
| US3995041A (en) * | 1975-10-30 | 1976-11-30 | Miles Laboratories, Inc. | Derivatives of 2-substituted-hydroxyanilino-hexahydro-2H-benzo[α]quinolizines |
| JPS5953917B2 (ja) * | 1976-07-23 | 1984-12-27 | 武田薬品工業株式会社 | テトラヒドロイソフタルイミド誘導体およびその製造方法 |
| US4180509A (en) * | 1977-07-01 | 1979-12-25 | Merrell Toraude Et Compagnie | α-Ethynyl tryptophanes |
| JPS6072787A (ja) * | 1983-09-30 | 1985-04-24 | Hodogaya Chem Co Ltd | 感熱記録材料 |
| FR2675504B1 (fr) * | 1991-04-16 | 1995-01-27 | Delalande Sa | Derives d'aryl-3 oxazolidinone, leur procede de preparation et leur application en therapeutique. |
| IL111002A (en) * | 1993-09-22 | 1998-09-24 | Glaxo Group Ltd | Piperidine derivatives their preparation and pharmaceutical compositions containing them |
| US6310211B1 (en) * | 1996-09-10 | 2001-10-30 | Pharmacia & Upjohn Company | 8-hydroxy-7-substituted quinolines as anti-viral agents |
| AU7139598A (en) * | 1997-04-25 | 1998-11-24 | Smithkline Beecham Corporation | Protease inhibitors |
| JP4721386B2 (ja) * | 2001-07-10 | 2011-07-13 | 第一三共株式会社 | 新規ガランタミン類縁体 |
| SI1511718T1 (sl) * | 2002-05-29 | 2009-08-31 | Hoffmann La Roche | Derivati n-acilaminobenzena kot selektivni inhibitorji monoaminske oksidaze b |
| GB0221246D0 (en) * | 2002-09-13 | 2002-10-23 | Astrazeneca Ab | Compounds |
| US7718692B2 (en) * | 2004-02-13 | 2010-05-18 | Carson John R | Hetero-substituted acetanilide derivatives as analgesic agents |
| EP1603858A2 (en) * | 2003-03-11 | 2005-12-14 | NeuroSearch A/S | Kcnq channel modulating compounds and their pharmaceutical use |
| AR043507A1 (es) * | 2003-03-14 | 2005-08-03 | Lundbeck & Co As H | Derivados de anilina sustituidos y composiciones farmaceuticas |
| US20050197364A1 (en) * | 2003-10-07 | 2005-09-08 | Kelly Michael G. | Amide compounds as ion channel ligands and uses thereof |
| US20050171172A1 (en) * | 2003-11-13 | 2005-08-04 | Ambit Biosciences Corporation | Amide derivatives as PDGFR modulators |
| WO2006022442A1 (ja) * | 2004-08-24 | 2006-03-02 | Santen Pharmaceutical Co., Ltd. | ジヒドロオロテートデヒドロゲナーゼ阻害活性を有する新規複素環アミド誘導体 |
| UA89503C2 (uk) * | 2004-09-13 | 2010-02-10 | Х. Луннбек А/С | Заміщені похідні аніліну |
| JP2009256208A (ja) * | 2006-08-17 | 2009-11-05 | Dainippon Sumitomo Pharma Co Ltd | フタリド誘導体またはその薬学的に許容される塩 |
| AU2007288253B2 (en) * | 2006-08-23 | 2013-05-02 | Xenon Pharmaceuticals Inc. | Derivatives of 4-(N-azacycloalkyl) anilides as potassium channel modulators |
-
2009
- 2009-06-24 WO PCT/US2009/048504 patent/WO2010008894A1/en not_active Ceased
- 2009-06-24 AU AU2009271302A patent/AU2009271302A1/en not_active Abandoned
- 2009-06-24 JP JP2011516617A patent/JP2011525538A/ja active Pending
- 2009-06-24 CA CA2728915A patent/CA2728915A1/en not_active Abandoned
- 2009-06-24 US US12/491,055 patent/US8188314B2/en not_active Expired - Fee Related
- 2009-06-24 MX MX2010014461A patent/MX2010014461A/es not_active Application Discontinuation
- 2009-06-24 EP EP09798525.3A patent/EP2310369A4/en not_active Withdrawn
-
2012
- 2012-05-29 US US13/483,018 patent/US8492588B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| MX2010014461A (es) | 2011-04-28 |
| US8188314B2 (en) | 2012-05-29 |
| US8492588B2 (en) | 2013-07-23 |
| JP2011525538A (ja) | 2011-09-22 |
| WO2010008894A1 (en) | 2010-01-21 |
| US20120329869A1 (en) | 2012-12-27 |
| CA2728915A1 (en) | 2010-01-21 |
| EP2310369A4 (en) | 2014-02-19 |
| EP2310369A1 (en) | 2011-04-20 |
| US20090326059A1 (en) | 2009-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4 | Application lapsed section 142(2)(d) - no continuation fee paid for the application |