UA89503C2 - Замещенные производные анилина - Google Patents
Замещенные производные анилина Download PDFInfo
- Publication number
- UA89503C2 UA89503C2 UAA200703647A UAA200703647A UA89503C2 UA 89503 C2 UA89503 C2 UA 89503C2 UA A200703647 A UAA200703647 A UA A200703647A UA A200703647 A UAA200703647 A UA A200703647A UA 89503 C2 UA89503 C2 UA 89503C2
- Authority
- UA
- Ukraine
- Prior art keywords
- alk
- compounds
- cycloalk
- halogen
- aryl
- Prior art date
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- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 title abstract 2
- 150000003839 salts Chemical class 0.000 abstract description 37
- 230000000694 effects Effects 0.000 abstract description 17
- 102000004257 Potassium Channel Human genes 0.000 abstract description 13
- 108020001213 potassium channel Proteins 0.000 abstract description 13
- 150000001875 compounds Chemical class 0.000 description 304
- -1 gabapentin Chemical class 0.000 description 105
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 77
- 125000001424 substituent group Chemical group 0.000 description 69
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- 239000011541 reaction mixture Substances 0.000 description 58
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 54
- 125000003118 aryl group Chemical group 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 51
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 50
- 238000000034 method Methods 0.000 description 46
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
- 239000002253 acid Substances 0.000 description 42
- 239000000203 mixture Substances 0.000 description 40
- 125000001072 heteroaryl group Chemical group 0.000 description 38
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 36
- 229910052736 halogen Inorganic materials 0.000 description 35
- 150000002367 halogens Chemical class 0.000 description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 34
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 32
- 239000007787 solid Substances 0.000 description 28
- 239000000047 product Substances 0.000 description 27
- 206010010904 Convulsion Diseases 0.000 description 26
- 229960000583 acetic acid Drugs 0.000 description 26
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 23
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 22
- 239000012074 organic phase Substances 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
- 125000004432 carbon atom Chemical group C* 0.000 description 20
- 239000012265 solid product Substances 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 18
- 238000012360 testing method Methods 0.000 description 18
- 238000001914 filtration Methods 0.000 description 17
- 230000000670 limiting effect Effects 0.000 description 17
- 230000008569 process Effects 0.000 description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
- 239000000126 substance Substances 0.000 description 16
- 208000019901 Anxiety disease Diseases 0.000 description 15
- 239000007864 aqueous solution Substances 0.000 description 15
- 238000003818 flash chromatography Methods 0.000 description 15
- 239000008194 pharmaceutical composition Substances 0.000 description 15
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 239000012043 crude product Substances 0.000 description 14
- 201000010099 disease Diseases 0.000 description 14
- 125000005842 heteroatom Chemical group 0.000 description 14
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 14
- 108091006146 Channels Proteins 0.000 description 13
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000001257 hydrogen Substances 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 11
- 229910052801 chlorine Inorganic materials 0.000 description 11
- 125000004093 cyano group Chemical group *C#N 0.000 description 11
- 125000004494 ethyl ester group Chemical group 0.000 description 11
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- 208000004296 neuralgia Diseases 0.000 description 11
- 208000021722 neuropathic pain Diseases 0.000 description 11
- 238000000746 purification Methods 0.000 description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 239000012300 argon atmosphere Substances 0.000 description 10
- 229910052794 bromium Inorganic materials 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- QGLAYJCJLHNIGJ-UHFFFAOYSA-N 4-bromo-2,6-dimethylaniline Chemical compound CC1=CC(Br)=CC(C)=C1N QGLAYJCJLHNIGJ-UHFFFAOYSA-N 0.000 description 9
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 208000035475 disorder Diseases 0.000 description 9
- 239000003814 drug Substances 0.000 description 9
- 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 9
- 208000015122 neurodegenerative disease Diseases 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 239000011591 potassium Substances 0.000 description 9
- 229910052700 potassium Inorganic materials 0.000 description 9
- 229960003312 retigabine Drugs 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 8
- 150000001408 amides Chemical class 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 239000003085 diluting agent Substances 0.000 description 8
- 229940079593 drug Drugs 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 230000004770 neurodegeneration Effects 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 7
- 208000019695 Migraine disease Diseases 0.000 description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 7
- 230000001773 anti-convulsant effect Effects 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 239000003638 chemical reducing agent Substances 0.000 description 7
- 239000003937 drug carrier Substances 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 230000001965 increasing effect Effects 0.000 description 7
- 239000006187 pill Substances 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 239000001961 anticonvulsive agent Substances 0.000 description 6
- 238000006880 cross-coupling reaction Methods 0.000 description 6
- 206010015037 epilepsy Diseases 0.000 description 6
- 230000004907 flux Effects 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 206010027599 migraine Diseases 0.000 description 6
- 125000002950 monocyclic group Chemical group 0.000 description 6
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- 239000011734 sodium Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 229940083542 sodium Drugs 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
- QCHFTSOMWOSFHM-WPRPVWTQSA-N (+)-Pilocarpine Chemical compound C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C QCHFTSOMWOSFHM-WPRPVWTQSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
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- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 4
- HOLKCYWBFYCVIH-UHFFFAOYSA-N (4-formyl-2,6-dimethylphenyl)carbamic acid Chemical compound CC1=CC(C=O)=CC(C)=C1NC(O)=O HOLKCYWBFYCVIH-UHFFFAOYSA-N 0.000 description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
- 208000022497 Cocaine-Related disease Diseases 0.000 description 4
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
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- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 4
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Classifications
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- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Addiction (AREA)
- Virology (AREA)
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- Communicable Diseases (AREA)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Molecular Biology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Physical Education & Sports Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- AIDS & HIV (AREA)
- Biotechnology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Quinoline Compounds (AREA)
- Furan Compounds (AREA)
- Pyridine Compounds (AREA)
Abstract
Это изобретение касается производных анилина общей формулы (И) или их солей и их применение, связанного с их активностью относительно открытия калиевых ионных каналов семейства KCNQ.(И)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DKPA200401394 | 2004-09-13 |
Publications (1)
Publication Number | Publication Date |
---|---|
UA89503C2 true UA89503C2 (ru) | 2010-02-10 |
Family
ID=36654136
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
UAA200703647A UA89503C2 (ru) | 2004-09-13 | 2005-02-09 | Замещенные производные анилина |
Country Status (16)
Country | Link |
---|---|
US (2) | US7601870B2 (ru) |
EP (1) | EP1791809A1 (ru) |
JP (1) | JP2008512402A (ru) |
KR (1) | KR20070058502A (ru) |
CN (1) | CN101056845A (ru) |
AR (1) | AR050644A1 (ru) |
AU (1) | AU2005284501A1 (ru) |
BR (1) | BRPI0515174A (ru) |
CA (1) | CA2580131A1 (ru) |
EA (1) | EA200700633A1 (ru) |
IL (1) | IL181679A0 (ru) |
MX (1) | MX2007002911A (ru) |
NO (1) | NO20071843L (ru) |
UA (1) | UA89503C2 (ru) |
WO (1) | WO2006029623A1 (ru) |
ZA (1) | ZA200702125B (ru) |
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US20050089559A1 (en) | 2003-10-23 | 2005-04-28 | Istvan Szelenyi | Combinations of potassium channel openers and sodium channel inhibitors or sodium channel-influencing active compounds for treating pains |
UA89503C2 (ru) * | 2004-09-13 | 2010-02-10 | Х. Луннбек А/С | Замещенные производные анилина |
EP2554162A1 (en) * | 2006-02-07 | 2013-02-06 | H. Lundbeck A/S | Use of KCNQ-Openers for Treating or Reducing the Symptoms of Schizophrenia |
US7960436B2 (en) | 2006-06-05 | 2011-06-14 | Valeant Pharmaceuticals International | Substituted arylamino-1,2,3,4-tetrahydro naphthalenes and-2,3-dihydro-1H-indenes as potassium channel modulators |
PT2061465E (pt) | 2006-08-23 | 2013-07-15 | Valeant Pharmaceuticals Int | Derivados de 4-(n-azacicloalquil)anilidas como moduladores do canal de potássio |
US8993593B2 (en) | 2006-08-23 | 2015-03-31 | Valeant Pharmaceuticals International | N-(4-(6-fluoro-3,4-dihydroisoquinolin-2(1H)-yl)-2,6-dimethylphenyl)-3,3-dimethylbutanamide as potassium channel modulators |
US8722929B2 (en) * | 2006-10-10 | 2014-05-13 | Valeant Pharmaceuticals International | N-[2-amino-4-(phenylmethoxy)phenyl] amides and related compounds as potassium channel modulators |
US8030518B2 (en) | 2006-11-28 | 2011-10-04 | Valeant Pharmaceuticals International | 1,4 diamino bicyclic retigabine analogues as potassium channel modulators |
WO2008135447A1 (en) | 2007-05-03 | 2008-11-13 | Neurosearch A/S | Acetamide derivatives as potassium channel modulators |
US8367684B2 (en) * | 2007-06-13 | 2013-02-05 | Valeant Pharmaceuticals International | Derivatives of 4-(N-azacycloalkyl) anilides as potassium channel modulators |
EA201070189A1 (ru) * | 2007-08-01 | 2010-08-30 | Х. Лундбекк А/С | Применение соединений, открывающих калиевые каналы kcnq, для подавления симптомов или лечения расстройств или состояний, при которых нарушается дофаминергическая система |
US8563566B2 (en) * | 2007-08-01 | 2013-10-22 | Valeant Pharmaceuticals International | Naphthyridine derivatives as potassium channel modulators |
US7786146B2 (en) * | 2007-08-13 | 2010-08-31 | Valeant Pharmaceuticals International | Derivatives of 5-amino-4,6-disubstituted indole and 5-amino-4,6-disubstituted indoline as potassium channel modulators |
WO2009074593A1 (en) * | 2007-12-11 | 2009-06-18 | Neurosearch A/S | Novel 2-pyrrolidinyl-3-amido-6-amino-pyridine derivatives useful as potassium channel activators |
AU2009271302A1 (en) | 2008-06-24 | 2010-01-21 | Valeant Pharmaceuticals International | Benzyloxy anilide derivatives useful as potassium channel modulators |
AU2010256541B2 (en) * | 2009-06-03 | 2016-03-10 | Marquette University | Modulation of KCNQ potassium channel activity for treatment of psychiatric disorders and the symptoms thereof |
CN103073455B (zh) * | 2011-10-25 | 2015-08-19 | 中国科学院上海药物研究所 | 一类新型的kcnq钾通道激动剂、其制备方法和用途 |
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 |
SG11201408419QA (en) * | 2012-07-10 | 2015-01-29 | Bayer Pharma AG | Method for preparing substituted triazolopyridines |
CN108250128A (zh) * | 2012-09-27 | 2018-07-06 | 江苏先声药业有限公司 | 作为钾通道调节剂的化合物 |
CN105017085B (zh) | 2014-04-28 | 2018-06-29 | 中国科学院上海药物研究所 | 一类kcnq钾通道激动剂、其制备方法和用途 |
CN104020195B (zh) * | 2014-05-27 | 2016-03-09 | 安徽师范大学 | 双识别多巴胺印迹电化学传感器及其制备方法和应用 |
KR20170076673A (ko) * | 2014-10-24 | 2017-07-04 | 오노 야꾸힝 고교 가부시키가이샤 | Kcnq2∼5 채널 활성화제 |
CN109071441A (zh) * | 2016-04-22 | 2018-12-21 | 小野药品工业株式会社 | Kcnq2-5通道活化剂的晶体多晶型 |
JP6197971B1 (ja) * | 2016-04-22 | 2017-09-20 | 小野薬品工業株式会社 | Kcnq2〜5チャネル関連疾患の予防および/または治療剤 |
RU2018147263A (ru) | 2016-06-10 | 2020-07-10 | Сайфлуор Лайф Сайенсиз, Инк | Фторированные 2-амино-4-(замещенные амино)фенилкарбаматные производные |
EP3366683A1 (en) | 2017-02-28 | 2018-08-29 | Acousia Therapeutics GmbH | Cyclic amides, acteamides and ureas useful as potassium channel openers |
JP2021506810A (ja) * | 2017-12-13 | 2021-02-22 | サイフルーア ライフ サイエンシズ インコーポレイテッド | フッ素化4−(置換アミノ)フェニルカルバメート誘導体 |
CN110511220B (zh) * | 2018-05-22 | 2022-04-01 | 上海挚盟医药科技有限公司 | 作为钾通道调节剂的对二氨基苯衍生物、其制备方法及其在医药上的应用 |
CN108707087B (zh) | 2018-06-29 | 2020-10-16 | 河北医科大学 | 一种4-(对三氟甲基苄基)-3-氟-1,2,4三苯胺衍生物及其药物组合物与用途 |
CN112010808B (zh) * | 2019-05-31 | 2021-11-30 | 上海挚盟医药科技有限公司 | 作为钾通道调节剂的四氢-1h-苯氮杂卓类化合物及其制备和应用 |
WO2022211520A1 (ko) * | 2021-04-02 | 2022-10-06 | 파렌키마바이오텍 주식회사 | 신규 화합물 및 이의 자가면역질환 치료 용도 |
CN116535353A (zh) * | 2022-01-25 | 2023-08-04 | 上海挚盟医药科技有限公司 | 作为钾通道调节剂的酰胺类化合物及其制备和应用 |
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US3362992A (en) * | 1965-05-27 | 1968-01-09 | Schwartz Herbert | Novel cycloalkenecarboxanilides |
JPS5214745A (en) * | 1975-07-23 | 1977-02-03 | Yoshitomi Pharmaceut Ind Ltd | Preparation of phenylcarbamic acid esters |
NZ223847A (en) * | 1987-04-01 | 1989-12-21 | Janssen Pharmaceutica Nv | Substituted piperazine derivatives and pharmaceutical compositions |
DE4200259A1 (de) * | 1992-01-08 | 1993-07-15 | Asta Medica Ag | Neue 1,2,4-triaminobenzol-derivate und verfahren zu deren herstellung |
JPH106578A (ja) * | 1996-06-21 | 1998-01-13 | Canon Inc | 印刷装置および印刷制御方法 |
JP2002527438A (ja) * | 1998-10-09 | 2002-08-27 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 4,5−ジヒドロ−イソオキサゾール誘導体及びそれらの製薬学的使用 |
WO2001010380A2 (en) * | 1999-08-04 | 2001-02-15 | Icagen, Inc. | Benzanilides as potassium channel openers |
PL212708B1 (pl) * | 2002-05-29 | 2012-11-30 | Hoffmann La Roche | Pochodne N-acyloaminobenzenu, sposób ich wytwarzania, lek zawierajacy te pochodne i zastosowanie pochodnych N-acyloaminobenzenu |
JP2006520333A (ja) * | 2003-03-14 | 2006-09-07 | ハー・ルンドベック・アクチエゼルスカベット | 置換されたアニリン誘導体 |
JP4551667B2 (ja) * | 2003-09-26 | 2010-09-29 | 富士フイルム株式会社 | 液晶組成物及び液晶素子 |
TWI357901B (en) * | 2004-03-12 | 2012-02-11 | Lundbeck & Co As H | Substituted morpholine and thiomorpholine derivati |
UA89503C2 (ru) * | 2004-09-13 | 2010-02-10 | Х. Луннбек А/С | Замещенные производные анилина |
-
2005
- 2005-02-09 UA UAA200703647A patent/UA89503C2/ru unknown
- 2005-09-02 CA CA002580131A patent/CA2580131A1/en not_active Abandoned
- 2005-09-02 AU AU2005284501A patent/AU2005284501A1/en not_active Abandoned
- 2005-09-02 BR BRPI0515174-0A patent/BRPI0515174A/pt not_active IP Right Cessation
- 2005-09-02 EP EP05777736A patent/EP1791809A1/en not_active Withdrawn
- 2005-09-02 EA EA200700633A patent/EA200700633A1/ru unknown
- 2005-09-02 CN CNA200580038113XA patent/CN101056845A/zh active Pending
- 2005-09-02 JP JP2007530581A patent/JP2008512402A/ja not_active Withdrawn
- 2005-09-02 KR KR1020077005872A patent/KR20070058502A/ko not_active Application Discontinuation
- 2005-09-02 WO PCT/DK2005/000560 patent/WO2006029623A1/en active Application Filing
- 2005-09-02 ZA ZA200702125A patent/ZA200702125B/xx unknown
- 2005-09-02 MX MX2007002911A patent/MX2007002911A/es not_active Application Discontinuation
- 2005-09-12 AR ARP050103796A patent/AR050644A1/es not_active Application Discontinuation
- 2005-12-20 US US11/312,664 patent/US7601870B2/en not_active Expired - Fee Related
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2007
- 2007-03-01 IL IL181679A patent/IL181679A0/en unknown
- 2007-04-11 NO NO20071843A patent/NO20071843L/no not_active Application Discontinuation
-
2009
- 2009-08-17 US US12/542,399 patent/US20100063044A1/en not_active Abandoned
Also Published As
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AU2005284501A1 (en) | 2006-03-23 |
EP1791809A1 (en) | 2007-06-06 |
US20100063044A1 (en) | 2010-03-11 |
BRPI0515174A (pt) | 2008-07-08 |
IL181679A0 (en) | 2007-07-04 |
US7601870B2 (en) | 2009-10-13 |
MX2007002911A (es) | 2007-04-27 |
EA200700633A1 (ru) | 2007-10-26 |
US20060155121A1 (en) | 2006-07-13 |
ZA200702125B (en) | 2008-09-25 |
WO2006029623A1 (en) | 2006-03-23 |
NO20071843L (no) | 2007-04-11 |
CA2580131A1 (en) | 2006-03-23 |
AR050644A1 (es) | 2006-11-08 |
JP2008512402A (ja) | 2008-04-24 |
CN101056845A (zh) | 2007-10-17 |
KR20070058502A (ko) | 2007-06-08 |
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