MX2010014461A - Derivados de benciloxi anilida utiles como moduladores de canales de potasio. - Google Patents
Derivados de benciloxi anilida utiles como moduladores de canales de potasio.Info
- Publication number
- MX2010014461A MX2010014461A MX2010014461A MX2010014461A MX2010014461A MX 2010014461 A MX2010014461 A MX 2010014461A MX 2010014461 A MX2010014461 A MX 2010014461A MX 2010014461 A MX2010014461 A MX 2010014461A MX 2010014461 A MX2010014461 A MX 2010014461A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- cycloalkyl
- formula
- compound
- chr6
- Prior art date
Links
- 102000004257 Potassium Channel Human genes 0.000 title claims abstract description 11
- 108020001213 potassium channel Proteins 0.000 title claims abstract description 11
- -1 Benzyloxy anilide Chemical class 0.000 title claims description 65
- 150000001875 compounds Chemical class 0.000 claims abstract description 388
- 230000004913 activation Effects 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 131
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 110
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 100
- 229910052739 hydrogen Inorganic materials 0.000 claims description 98
- 229910052736 halogen Inorganic materials 0.000 claims description 91
- 150000002367 halogens Chemical class 0.000 claims description 91
- 125000000217 alkyl group Chemical group 0.000 claims description 83
- 229910052731 fluorine Inorganic materials 0.000 claims description 82
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 79
- 229910052801 chlorine Inorganic materials 0.000 claims description 69
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 66
- 229910052794 bromium Inorganic materials 0.000 claims description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 36
- 125000004076 pyridyl group Chemical group 0.000 claims description 29
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 25
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 24
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 20
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 14
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 14
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000002541 furyl group Chemical group 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 239000012453 solvate Substances 0.000 claims description 8
- 125000000335 thiazolyl group Chemical group 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 125000002971 oxazolyl group Chemical group 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 125000000565 sulfonamide group Chemical group 0.000 claims description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 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
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000006448 cycloalkyl cycloalkyl group Chemical group 0.000 claims 1
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims 1
- CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 abstract description 11
- 230000006806 disease prevention Effects 0.000 abstract description 2
- 208000037765 diseases and disorders Diseases 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 22
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000005481 NMR spectroscopy Methods 0.000 description 18
- 125000001188 haloalkyl group Chemical group 0.000 description 17
- 241001465754 Metazoa Species 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- 238000012360 testing method Methods 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- 206010010904 Convulsion Diseases 0.000 description 12
- 241000700159 Rattus Species 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 241000699670 Mus sp. Species 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 10
- 229940079593 drug Drugs 0.000 description 10
- 239000003814 drug Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 10
- 210000000287 oocyte Anatomy 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 8
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 229910014585 C2-Ce Inorganic materials 0.000 description 7
- 108091006146 Channels Proteins 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- PCOBBVZJEWWZFR-UHFFFAOYSA-N ezogabine Chemical compound C1=C(N)C(NC(=O)OCC)=CC=C1NCC1=CC=C(F)C=C1 PCOBBVZJEWWZFR-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
- 239000006174 pH buffer Substances 0.000 description 6
- 229960003312 retigabine Drugs 0.000 description 6
- 108010006746 KCNQ2 Potassium Channel Proteins 0.000 description 5
- 102100034354 Potassium voltage-gated channel subfamily KQT member 2 Human genes 0.000 description 5
- 239000001961 anticonvulsive agent Substances 0.000 description 5
- 229940073608 benzyl chloride Drugs 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000028161 membrane depolarization Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 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
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-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
- 102000004310 Ion Channels Human genes 0.000 description 4
- 108090000862 Ion Channels Proteins 0.000 description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 229960003965 antiepileptics Drugs 0.000 description 4
- 150000005524 benzylchlorides Chemical class 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 229920000609 methyl cellulose Polymers 0.000 description 4
- 239000001923 methylcellulose Substances 0.000 description 4
- 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 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 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- 108010011185 KCNQ1 Potassium Channel Proteins 0.000 description 3
- 108010038888 KCNQ3 Potassium Channel Proteins 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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000007059 acute toxicity Effects 0.000 description 3
- 231100000403 acute toxicity Toxicity 0.000 description 3
- 230000001773 anti-convulsant effect Effects 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 239000001110 calcium chloride Substances 0.000 description 3
- 235000011148 calcium chloride Nutrition 0.000 description 3
- 229910001628 calcium chloride Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- 230000006698 induction Effects 0.000 description 3
- 238000007912 intraperitoneal administration Methods 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
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- 238000002360 preparation method Methods 0.000 description 3
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- 235000020357 syrup Nutrition 0.000 description 3
- 230000001256 tonic effect Effects 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 description 2
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical class OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 2
- ZVUJMNCTXGSXSQ-UHFFFAOYSA-N 3,5-dimethyl-4-nitrosophenol Chemical compound CC1=CC(O)=CC(C)=C1N=O ZVUJMNCTXGSXSQ-UHFFFAOYSA-N 0.000 description 2
- YIUBIPRPBSMVSE-UHFFFAOYSA-N 3-cyclopentyl-n-[4-[(3,4-difluorophenyl)methoxy]-2,6-dimethylphenyl]propanamide Chemical compound C=1C(C)=C(NC(=O)CCC2CCCC2)C(C)=CC=1OCC1=CC=C(F)C(F)=C1 YIUBIPRPBSMVSE-UHFFFAOYSA-N 0.000 description 2
- 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 2
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- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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- 101000974726 Homo sapiens Potassium voltage-gated channel subfamily E member 1 Proteins 0.000 description 2
- 101000994648 Homo sapiens Potassium voltage-gated channel subfamily KQT member 4 Proteins 0.000 description 2
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
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- DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 2
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
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- 239000008137 solubility enhancer Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000011550 stock solution 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
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000002600 sunflower oil 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
- 238000002560 therapeutic procedure Methods 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
- 239000003981 vehicle Substances 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7530708P | 2008-06-24 | 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 |
|---|---|
| MX2010014461A true MX2010014461A (es) | 2011-04-28 |
Family
ID=41448228
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2010014461A MX2010014461A (es) | 2008-06-24 | 2009-06-24 | Derivados de benciloxi anilida utiles como moduladores de canales de potasio. |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US8188314B2 (https=) |
| EP (1) | EP2310369A4 (https=) |
| JP (1) | JP2011525538A (https=) |
| AU (1) | AU2009271302A1 (https=) |
| CA (1) | CA2728915A1 (https=) |
| MX (1) | MX2010014461A (https=) |
| WO (1) | WO2010008894A1 (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20150053257A (ko) | 2012-04-30 | 2015-05-15 | 사이플루어 라이프 사이언시즈, 엘엘씨 | 플루오르화 2-아미노-4-(벤질아미노)페닐카르바메이트 유도체 |
| 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 (https=) * | 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 |
| EP0927164A1 (en) * | 1996-09-10 | 1999-07-07 | PHARMACIA & UPJOHN COMPANY | 8-hydroxy-7-substituted quinolines as anti-viral agents |
| EP0977743A1 (en) * | 1997-04-25 | 2000-02-09 | Smithkline Beecham | 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 |
| EA009372B1 (ru) * | 2002-05-29 | 2007-12-28 | Ф. Хоффманн-Ля Рош Аг | N-ациламинобензольные производные в качестве селективных ингибиторов моноаминооксидазы в |
| 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 |
| JP2007525482A (ja) * | 2003-10-07 | 2007-09-06 | レノビス， インコーポレイテッド | イオンチャネルリガンドとしてのアミド化合物およびその使用 |
| US20050192314A1 (en) * | 2003-11-13 | 2005-09-01 | Ambit Biosciences Corporation | Urea derivatives as C-kit 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 |
| BRPI0716715B1 (pt) * | 2006-08-23 | 2021-07-06 | Xenon Pharmaceuticals, Inc | Derivados de 4-(n-azacicloalquil) anilidas como moduladores de canal de potássio, seus usos, produto, composição, comprimido e cápsula |
-
2009
- 2009-06-24 AU AU2009271302A patent/AU2009271302A1/en not_active Abandoned
- 2009-06-24 JP JP2011516617A patent/JP2011525538A/ja active Pending
- 2009-06-24 US US12/491,055 patent/US8188314B2/en not_active Expired - Fee Related
- 2009-06-24 CA CA2728915A patent/CA2728915A1/en not_active Abandoned
- 2009-06-24 EP EP09798525.3A patent/EP2310369A4/en not_active Withdrawn
- 2009-06-24 WO PCT/US2009/048504 patent/WO2010008894A1/en not_active Ceased
- 2009-06-24 MX MX2010014461A patent/MX2010014461A/es not_active Application Discontinuation
-
2012
- 2012-05-29 US US13/483,018 patent/US8492588B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| WO2010008894A1 (en) | 2010-01-21 |
| US20120329869A1 (en) | 2012-12-27 |
| AU2009271302A1 (en) | 2010-01-21 |
| EP2310369A1 (en) | 2011-04-20 |
| EP2310369A4 (en) | 2014-02-19 |
| US20090326059A1 (en) | 2009-12-31 |
| US8492588B2 (en) | 2013-07-23 |
| US8188314B2 (en) | 2012-05-29 |
| JP2011525538A (ja) | 2011-09-22 |
| CA2728915A1 (en) | 2010-01-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA | Abandonment or withdrawal |