UA78252C2 - Sulphonamide derivatives, methods of preparation thereof and application as pharmaceutical compositions - Google Patents
Sulphonamide derivatives, methods of preparation thereof and application as pharmaceutical compositions Download PDFInfo
- Publication number
- UA78252C2 UA78252C2 UA20040604587A UA20040604587A UA78252C2 UA 78252 C2 UA78252 C2 UA 78252C2 UA 20040604587 A UA20040604587 A UA 20040604587A UA 20040604587 A UA20040604587 A UA 20040604587A UA 78252 C2 UA78252 C2 UA 78252C2
- Authority
- UA
- Ukraine
- Prior art keywords
- sulfonamide
- indol
- general formula
- chloro
- methylbenzo
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 30
- 150000003456 sulfonamides Chemical class 0.000 title claims abstract description 11
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 5
- 238000002360 preparation method Methods 0.000 title claims description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 229940124530 sulfonamide Drugs 0.000 claims description 59
- 150000001875 compounds Chemical class 0.000 claims description 42
- 239000002904 solvent Substances 0.000 claims description 37
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- -1 atoms halogen Chemical class 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 239000011593 sulfur Substances 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 229940076279 serotonin Drugs 0.000 claims description 8
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 7
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 206010012289 Dementia Diseases 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 206010020651 Hyperkinesia Diseases 0.000 claims description 5
- 208000000269 Hyperkinesis Diseases 0.000 claims description 5
- VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 claims description 4
- 208000019901 Anxiety disease Diseases 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 4
- 208000028017 Psychotic disease Diseases 0.000 claims description 4
- 230000036506 anxiety Effects 0.000 claims description 4
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 4
- 230000007278 cognition impairment Effects 0.000 claims description 4
- 230000001404 mediated effect Effects 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- ZCBIFHNDZBSCEP-UHFFFAOYSA-N 1H-indol-5-amine Chemical compound NC1=CC=C2NC=CC2=C1 ZCBIFHNDZBSCEP-UHFFFAOYSA-N 0.000 claims description 3
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 claims description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 206010039966 Senile dementia Diseases 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 229940126601 medicinal product Drugs 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- KTFDYVNEGTXQCV-UHFFFAOYSA-N 2-Thiophenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CS1 KTFDYVNEGTXQCV-UHFFFAOYSA-N 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 150000008050 dialkyl sulfates Chemical class 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 2
- CRWDCNPQLQANDB-UHFFFAOYSA-N quinoline-3-sulfonamide Chemical compound C1=CC=CC2=CC(S(=O)(=O)N)=CN=C21 CRWDCNPQLQANDB-UHFFFAOYSA-N 0.000 claims description 2
- HFFXLYHRNRKAPM-UHFFFAOYSA-N 2,4,5-trichloro-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 HFFXLYHRNRKAPM-UHFFFAOYSA-N 0.000 claims 6
- 230000003930 cognitive ability Effects 0.000 claims 2
- 208000001431 Psychomotor Agitation Diseases 0.000 claims 1
- 206010038743 Restlessness Diseases 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 210000005056 cell body Anatomy 0.000 claims 1
- 230000006735 deficit Effects 0.000 claims 1
- 239000000945 filler Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 208000013403 hyperactivity Diseases 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 8
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 238000002329 infrared spectrum Methods 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 102000005962 receptors Human genes 0.000 description 7
- 108020003175 receptors Proteins 0.000 description 7
- 102000014630 G protein-coupled serotonin receptor activity proteins Human genes 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000003042 antagnostic effect Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 208000035475 disorder Diseases 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 108010006590 serotonin 5 receptor Proteins 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- 208000026139 Memory disease Diseases 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000027455 binding Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- 208000010877 cognitive disease Diseases 0.000 description 3
- 230000001149 cognitive effect Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical class [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- HUUPVABNAQUEJW-UHFFFAOYSA-N 1-methylpiperidin-4-one Chemical compound CN1CCC(=O)CC1 HUUPVABNAQUEJW-UHFFFAOYSA-N 0.000 description 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
- 102000056834 5-HT2 Serotonin Receptors Human genes 0.000 description 1
- 108091005479 5-HT2 receptors Proteins 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- 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 1
- 108010052285 Membrane Proteins Proteins 0.000 description 1
- 102000018697 Membrane Proteins Human genes 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000003693 atypical antipsychotic agent Substances 0.000 description 1
- 229940127236 atypical antipsychotics Drugs 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000012472 biological sample Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000002288 cocrystallisation Methods 0.000 description 1
- 206010009887 colitis Diseases 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 229910052949 galena Inorganic materials 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- XCAUINMIESBTBL-UHFFFAOYSA-N lead(ii) sulfide Chemical compound [Pb]=S XCAUINMIESBTBL-UHFFFAOYSA-N 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 238000010369 molecular cloning Methods 0.000 description 1
- MSPCOXFYKUKYLB-UHFFFAOYSA-N naphthalene-1-sulfonamide Chemical compound C1=C[C]2C(S(=O)(=O)N)=CC=CC2=C=C1 MSPCOXFYKUKYLB-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000008023 pharmaceutical filler Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000611 regression analysis Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 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
- 239000012265 solid product Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000009495 sugar coating Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/622—Forming processes; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/626—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B
- C04B35/63—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B using additives specially adapted for forming the products, e.g.. binder binders
- C04B35/632—Organic additives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- 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
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- 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
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- 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
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D209/16—Tryptamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- General Chemical & Material Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Ceramic Engineering (AREA)
- Psychiatry (AREA)
- Structural Engineering (AREA)
- Inorganic Chemistry (AREA)
- Materials Engineering (AREA)
- Epidemiology (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200102517A ES2187300B1 (es) | 2001-11-14 | 2001-11-14 | Derivados de sulfonamidas, su preparacion y su aplicacion como medicamentos. |
| PCT/ES2002/000518 WO2003042175A1 (fr) | 2001-11-14 | 2002-11-08 | Derives de sulfonamides, leur preparation et leur application en tant que medicaments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA78252C2 true UA78252C2 (en) | 2007-03-15 |
Family
ID=8499446
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA20040604587A UA78252C2 (en) | 2001-11-14 | 2002-08-11 | Sulphonamide derivatives, methods of preparation thereof and application as pharmaceutical compositions |
Country Status (34)
| Country | Link |
|---|---|
| US (4) | US7105515B2 (fr) |
| EP (2) | EP1445252B1 (fr) |
| JP (2) | JP4416505B2 (fr) |
| KR (1) | KR20040071685A (fr) |
| CN (1) | CN1271052C (fr) |
| AR (1) | AR037288A1 (fr) |
| AT (2) | ATE428694T1 (fr) |
| BR (1) | BR0214243A (fr) |
| CA (1) | CA2466965C (fr) |
| CO (1) | CO5590895A2 (fr) |
| CY (1) | CY1105362T1 (fr) |
| DE (2) | DE60232029D1 (fr) |
| DK (1) | DK1445252T3 (fr) |
| EC (1) | ECSP045105A (fr) |
| ES (4) | ES2187300B1 (fr) |
| HK (1) | HK1070053A1 (fr) |
| HR (1) | HRP20040429B1 (fr) |
| HU (1) | HUP0402317A2 (fr) |
| IL (2) | IL161885A0 (fr) |
| IS (2) | IS7263A (fr) |
| MA (1) | MA27093A1 (fr) |
| MX (1) | MXPA04004601A (fr) |
| NO (1) | NO20042478L (fr) |
| NZ (2) | NZ533136A (fr) |
| PL (1) | PL373894A1 (fr) |
| PT (2) | PT1445252E (fr) |
| RS (1) | RS41104A (fr) |
| RU (2) | RU2293082C2 (fr) |
| SG (1) | SG146442A1 (fr) |
| SI (1) | SI1445252T1 (fr) |
| TW (1) | TWI275585B (fr) |
| UA (1) | UA78252C2 (fr) |
| WO (1) | WO2003042175A1 (fr) |
| ZA (1) | ZA200404073B (fr) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2187300B1 (es) * | 2001-11-14 | 2004-06-16 | Laboratorios Del Dr. Esteve, S.A. | Derivados de sulfonamidas, su preparacion y su aplicacion como medicamentos. |
| ATE407671T1 (de) * | 2003-05-09 | 2008-09-15 | Esteve Labor Dr | Verwendung von sulfonamid-derivate zur herstellung eines medikaments für die vorbeugung oder behandlung von essstörungen |
| ES2222829B1 (es) * | 2003-07-30 | 2006-03-01 | Laboratorios Del Dr. Esteve, S.A. | Derivados de 4-indolilsulfonamidas, su preparacion y su aplicacion como medicamentos. |
| ES2222827B1 (es) * | 2003-07-30 | 2006-03-01 | Laboratorios Del Dr. Esteve, S.A. | Derivados de 5-indolilsulfonamidas, su preparacion y su aplicacion como medicamentos. |
| ES2222832B1 (es) * | 2003-07-30 | 2006-02-16 | Laboratorios Del Dr. Esteve, S.A. | Derivados de 6-indolilsulfonamidas, su preparacion y su aplicacion como medicamentos. |
| ES2228268B1 (es) * | 2003-07-30 | 2006-07-01 | Laboratorios Del Dr. Esteve, S.A. | Combinacion de sustancias activas conteniendo al menos un compuesto con afinidad por el receptor del neuropeptido y (npy) y al menos un compuesto con afinidad por el receptor 5-ht6. |
| ES2222830B1 (es) * | 2003-07-30 | 2006-02-16 | Laboratorios Del Dr. Esteve, S.A. | Derivados de 7-indolilsulfonamidas, su preparacion y su aplicacion como medicamentos. |
| ES2228267B1 (es) * | 2003-07-30 | 2006-07-01 | Laboratorios Del Dr. Esteve, S.A. | Combinacion de sustancias activas conteniendo al menos un compuesto con afinidad por el receptor del neuropeptido y (npy) y al menos un compuesto con afinidad por el receptor 5-ht6. |
| SE0303480D0 (sv) * | 2003-12-19 | 2003-12-19 | Biovitrum Ab | Benzofuranes |
| AU2004312229B2 (en) * | 2004-01-02 | 2010-05-20 | Suven Life Sciences Limited | Novel Indeno[2,1a]indenes and isoindolo[2,1-a]indoles |
| ES2246721B1 (es) * | 2004-08-10 | 2007-03-16 | Laboratorios Del Dr. Esteve, S.A. | Compuestos indolicos sustituidos, su preparacion y su uso como medicamentos. |
| EP1632491A1 (fr) * | 2004-08-30 | 2006-03-08 | Laboratorios Del Dr. Esteve, S.A. | composes indole substitues et leur utilisation comme modulateurs du recepteur 5-ht6 |
| PT1883451E (pt) * | 2005-04-13 | 2011-03-02 | Neuraxon Inc | Compostos de indolo substituídos com actividade inibitória da sintetase de óxido nítrico (nos) |
| JP5026690B2 (ja) * | 2005-11-21 | 2012-09-12 | 株式会社ジャパンディスプレイイースト | 表示装置 |
| EA014470B1 (ru) * | 2006-01-24 | 2010-12-30 | Эли Лилли Энд Компани | Индолсульфонамидные модуляторы рецепторов прогестерона |
| EP1837332A1 (fr) * | 2006-03-23 | 2007-09-26 | Laboratorios Del Dr. Esteve, S.A. | Tetrahydroquinolines substitués, leur préparation et utilisation comme médicaments |
| TW200808780A (en) * | 2006-04-13 | 2008-02-16 | Neuraxon Inc | 1,5 and 3,6- substituted indole compounds having NOS inhibitory activity |
| EP1902733A1 (fr) * | 2006-09-19 | 2008-03-26 | Laboratorios Del Dr. Esteve, S.A. | Combinaison de substances actives comporant un ligand de récepteur NMDA et un composé a affinité de récepteur 5-HT6 |
| EP1953141A1 (fr) * | 2007-01-31 | 2008-08-06 | Laboratorios del Dr. Esteve S.A. | Sulfamides substitués d'aryl pour le traitement des maladies cognitives ou d'ingestion de la nourriture |
| EP1953153A1 (fr) * | 2007-01-31 | 2008-08-06 | Laboratorios del Dr. Esteve S.A. | Sulfamides substitués d'hétérocyclyle pour le traitement des maladies cognitives ou d'ingestion de la nourriture |
| EP2018861A1 (fr) * | 2007-07-26 | 2009-01-28 | Laboratorios del Dr. Esteve S.A. | Ligands 5HT6 comme des dérivés de sulfonamides liés à la prise de poids médicamenteuse |
| ATE495737T1 (de) * | 2007-08-01 | 2011-02-15 | Esteve Labor Dr | Kombination von mindestens zwei 5-ht6-liganden |
| EP2036888A1 (fr) * | 2007-09-17 | 2009-03-18 | Laboratorios del Dr. Esteve S.A. | Sulfonamides à substitution naphtyl |
| AU2008321353A1 (en) * | 2007-11-16 | 2009-05-22 | The Arizona Board Of Regents On Behalf Of The University Of Arizona | Methods for treating visceral pain |
| WO2009062318A1 (fr) * | 2007-11-16 | 2009-05-22 | Neuraxon, Inc. | Composés d'indole 3,5-substitués ayant une activité d'inhibition de la réabsorption de la nos et de la noradrénaline |
| WO2009062319A1 (fr) * | 2007-11-16 | 2009-05-22 | Neuraxon, Inc. | Composés d'indole et procédés de traitement de la douleur viscérale |
| EP2116546A1 (fr) | 2008-05-09 | 2009-11-11 | Laboratorios Del. Dr. Esteve, S.A. | Dérivés de N-phenyl-2,3-dihydroimidazo[2,1-b]thiazole-5-sulfonamide substitués en tant que ligands 5-HT6 |
| EP2116547A1 (fr) | 2008-05-09 | 2009-11-11 | Laboratorios Del. Dr. Esteve, S.A. | Dérivés de n-phenyl-2,3-dihydroimidazo[2,1-b]thiazole-5-sulfonamide substitués en tant que ligands 5-ht6 |
| EA029499B9 (ru) * | 2013-08-02 | 2018-07-31 | Пфайзер Инк | Ингибиторы rorc2 и способы их применения |
| MA40759A (fr) | 2014-09-26 | 2017-08-01 | Pfizer | Modulateurs de rorc2 de type pyrrolopyridine substitué par un méthyle et trifluorométhyle et leurs procédés d'utilisation |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3472870A (en) | 1966-08-29 | 1969-10-14 | Mead Johnson & Co | Sulfonamidotryptamines |
| US5578612A (en) * | 1990-10-15 | 1996-11-26 | Pfizer Inc. | Indole derivatives |
| AU702322B2 (en) * | 1995-03-20 | 1999-02-18 | Eli Lilly And Company | 5-substituted-3-(1,2,3,6-tetrahydropyridin-4-yl)- and 3-(piperidin-4-yl)-1h-indoles: new 5-ht1f agonists |
| US5962473A (en) * | 1996-08-16 | 1999-10-05 | Eli Lilly And Company | Methods of treating or ameliorating the symptoms of common cold or allergic rhinitis with serotonin 5-HT1F |
| EP0875513A1 (fr) * | 1997-04-14 | 1998-11-04 | Eli Lilly And Company | Composés hétéroaromatiques substitués agonistes du récepteur 5-HT1F |
| US6380201B1 (en) * | 1997-08-05 | 2002-04-30 | Eli Lilly And Company | Methods of treating or ameliorating the symptoms of common cold or allergic rhinitis with serotonin 5-HT1F agonists |
| ES2187300B1 (es) * | 2001-11-14 | 2004-06-16 | Laboratorios Del Dr. Esteve, S.A. | Derivados de sulfonamidas, su preparacion y su aplicacion como medicamentos. |
-
2001
- 2001-11-14 ES ES200102517A patent/ES2187300B1/es not_active Expired - Fee Related
-
2002
- 2002-08-11 UA UA20040604587A patent/UA78252C2/uk unknown
- 2002-11-08 CN CNB028240804A patent/CN1271052C/zh not_active Expired - Fee Related
- 2002-11-08 AR ARP020104303A patent/AR037288A1/es not_active Application Discontinuation
- 2002-11-08 KR KR10-2004-7007155A patent/KR20040071685A/ko not_active Application Discontinuation
- 2002-11-08 ES ES02785439T patent/ES2259387T3/es not_active Expired - Lifetime
- 2002-11-08 IL IL16188502A patent/IL161885A0/xx unknown
- 2002-11-08 EP EP02785439A patent/EP1445252B1/fr not_active Expired - Lifetime
- 2002-11-08 SI SI200230302T patent/SI1445252T1/sl unknown
- 2002-11-08 EP EP05021228A patent/EP1666462B1/fr not_active Expired - Lifetime
- 2002-11-08 AT AT05021228T patent/ATE428694T1/de active
- 2002-11-08 NZ NZ533136A patent/NZ533136A/en unknown
- 2002-11-08 JP JP2003544012A patent/JP4416505B2/ja not_active Expired - Fee Related
- 2002-11-08 DE DE60232029T patent/DE60232029D1/de not_active Expired - Lifetime
- 2002-11-08 WO PCT/ES2002/000518 patent/WO2003042175A1/fr active Application Filing
- 2002-11-08 RU RU2004117850/04A patent/RU2293082C2/ru not_active IP Right Cessation
- 2002-11-08 PT PT02785439T patent/PT1445252E/pt unknown
- 2002-11-08 CA CA2466965A patent/CA2466965C/fr not_active Expired - Fee Related
- 2002-11-08 MX MXPA04004601A patent/MXPA04004601A/es active IP Right Grant
- 2002-11-08 DK DK02785439T patent/DK1445252T3/da active
- 2002-11-08 PT PT05021228T patent/PT1666462E/pt unknown
- 2002-11-08 RS YU41104A patent/RS41104A/sr unknown
- 2002-11-08 AT AT02785439T patent/ATE319684T1/de active
- 2002-11-08 PL PL02373894A patent/PL373894A1/xx not_active Application Discontinuation
- 2002-11-08 NZ NZ543393A patent/NZ543393A/en unknown
- 2002-11-08 BR BR0214243-0A patent/BR0214243A/pt not_active IP Right Cessation
- 2002-11-08 ES ES05021228T patent/ES2322068T3/es not_active Expired - Lifetime
- 2002-11-08 HU HU0402317A patent/HUP0402317A2/hu unknown
- 2002-11-08 SG SG200602676-9A patent/SG146442A1/en unknown
- 2002-11-08 DE DE60209779T patent/DE60209779T2/de not_active Expired - Lifetime
- 2002-11-11 TW TW091132989A patent/TWI275585B/zh not_active IP Right Cessation
- 2002-11-13 US US10/293,206 patent/US7105515B2/en not_active Expired - Fee Related
-
2004
- 2004-05-06 ES ES200401084A patent/ES2249129B2/es not_active Expired - Fee Related
- 2004-05-13 EC EC2004005105A patent/ECSP045105A/es unknown
- 2004-05-13 IS IS7263A patent/IS7263A/is unknown
- 2004-05-14 HR HR20040429A patent/HRP20040429B1/xx not_active IP Right Cessation
- 2004-05-25 ZA ZA200404073A patent/ZA200404073B/en unknown
- 2004-05-26 CO CO04048713A patent/CO5590895A2/es not_active Application Discontinuation
- 2004-06-07 MA MA27723A patent/MA27093A1/fr unknown
- 2004-06-14 NO NO20042478A patent/NO20042478L/no not_active Application Discontinuation
- 2004-09-03 US US10/933,951 patent/US7176200B2/en not_active Expired - Fee Related
-
2005
- 2005-02-05 HK HK05101004A patent/HK1070053A1/xx not_active IP Right Cessation
- 2005-11-22 RU RU2005136355/04A patent/RU2005136355A/ru not_active Application Discontinuation
-
2006
- 2006-06-02 CY CY20061100709T patent/CY1105362T1/el unknown
- 2006-07-17 US US11/487,745 patent/US7498328B2/en not_active Expired - Fee Related
-
2007
- 2007-02-16 US US11/707,571 patent/US7452881B2/en not_active Expired - Fee Related
- 2007-12-05 IS IS8698A patent/IS8698A/is unknown
-
2008
- 2008-08-04 IL IL193234A patent/IL193234A0/en unknown
-
2009
- 2009-09-29 JP JP2009223711A patent/JP5132649B2/ja not_active Expired - Fee Related
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| UA78252C2 (en) | Sulphonamide derivatives, methods of preparation thereof and application as pharmaceutical compositions | |
| JP5612573B2 (ja) | 新規化学化合物 | |
| US7868024B2 (en) | Derivatives of N-(heteroaryl)-1-heteroaryl-1H-indole-2-carboxamides, preparation thereof and therapeutic use thereof | |
| AU2007279166B2 (en) | N-(aminoheteroaryl)-1H-indole-2-carboxamide derivatives, preparation thereof and therapeutic use thereof | |
| TW202210474A (zh) | 用於治療癌症之環狀2-胺基-3-氰基噻吩及衍生物 | |
| US20070004684A1 (en) | Alpha-Carbolines as CDK-1 inhibitors | |
| JP2011528026A6 (ja) | 新規化学化合物 | |
| JP2009514953A (ja) | ヒドロキシ及びアルコキシ置換１ｈ−イミダゾキノリン及び方法 | |
| AU2006232377A1 (en) | Pyrazolopyridine-1,4-diamines and analogs thereof | |
| CA2752265A1 (fr) | Derives pyrimido-[5,4-d]-pyrimidine pour l'inhibition des tyrosine-kinases | |
| BRPI0712795A2 (pt) | derivados de heteroarila substituìdos com fenila e uso dos mesmos como agentes antitumorais | |
| TW201035095A (en) | Pyrazolo[1,5-a]pyridine derivatives | |
| TW202340209A (zh) | 用於治療癌症之環狀2-胺基-3-氰基噻吩及衍生物 | |
| CA3234638A1 (fr) | 6-hetero-aryloxy-benzimidazoles et azabenzimidazoles en tant qu'inhibiteurs de jak2 | |
| US20050065202A1 (en) | Use of sulphonamide derivatives for the manufacture of a medicament for the prophylaxis and/or treatment of disorders of food ingestion | |
| KR20160034403A (ko) | 5-ht6 길항제로서의 피롤로퀴놀린 유도체, 및 이의 제조 방법 및 용도 | |
| SG182676A1 (en) | 5-alkynyl pyrimidines and their use as kinase inhibitors | |
| CA2604836A1 (fr) | Derives de pyrimidine | |
| KR20180067531A (ko) | Pim 카이나제 저해제의 염 |