NO321558B1 - Cinnamoylaminoalkyl-substituerte benzensulfonamidderivater - Google Patents

Cinnamoylaminoalkyl-substituerte benzensulfonamidderivater Download PDF

Info

Publication number: NO321558B1
Authority: NO; Norway
Prior art keywords: alkyl; formula; phenyl; compound; group
Prior art date: 1999-05-20

Application number

NO20015636A

Other languages

English (en)

Norwegian (no)

Other versions

NO20015636D0 (no

NO20015636L (no

Inventor

Klaus Wirth

Heinz Gogelein

Heinrich Englert

Holger Heitsch

Original Assignee

Sanofi Aventis Deutschland

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1999-05-20

Filing date

2001-11-19

Publication date

2006-05-29

2001-11-19 Application filed by Sanofi Aventis Deutschland filed Critical Sanofi Aventis Deutschland

2001-11-19 Publication of NO20015636D0 publication Critical patent/NO20015636D0/no

2002-01-15 Publication of NO20015636L publication Critical patent/NO20015636L/no

2006-05-29 Publication of NO321558B1 publication Critical patent/NO321558B1/no

Links

150000008331 benzenesulfonamides Chemical class 0.000 title description 12
150000001875 compounds Chemical class 0.000 claims description 373
-1 cyanoimino Chemical group 0.000 claims description 85
150000003839 salts Chemical class 0.000 claims description 64
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 60
239000001257 hydrogen Substances 0.000 claims description 60
229910052739 hydrogen Inorganic materials 0.000 claims description 60
238000006243 chemical reaction Methods 0.000 claims description 58
229910052760 oxygen Inorganic materials 0.000 claims description 47
229910052736 halogen Inorganic materials 0.000 claims description 46
150000002367 halogens Chemical class 0.000 claims description 46
239000001301 oxygen Substances 0.000 claims description 44
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 42
125000001424 substituent group Chemical group 0.000 claims description 40
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 37
239000000203 mixture Substances 0.000 claims description 36
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 33
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 31
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
238000002360 preparation method Methods 0.000 claims description 27
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 24
150000002431 hydrogen Chemical class 0.000 claims description 20
210000000653 nervous system Anatomy 0.000 claims description 20
229910052717 sulfur Inorganic materials 0.000 claims description 19
206010003119 arrhythmia Diseases 0.000 claims description 18
230000004064 dysfunction Effects 0.000 claims description 18
238000011282 treatment Methods 0.000 claims description 18
210000003403 autonomic nervous system Anatomy 0.000 claims description 16
239000011593 sulfur Chemical group 0.000 claims description 14
108010053914 KATP Channels Proteins 0.000 claims description 13
102000016924 KATP Channels Human genes 0.000 claims description 13
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
125000005842 heteroatom Chemical group 0.000 claims description 11
239000000825 pharmaceutical preparation Substances 0.000 claims description 11
239000005864 Sulphur Substances 0.000 claims description 10
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 10
125000004430 oxygen atom Chemical group O* 0.000 claims description 10
238000011321 prophylaxis Methods 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 9
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 8
206010049418 Sudden Cardiac Death Diseases 0.000 claims description 8
150000001412 amines Chemical class 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 8
125000000623 heterocyclic group Chemical group 0.000 claims description 8
229910052757 nitrogen Chemical group 0.000 claims description 8
125000006528 (C2-C6) alkyl group Chemical group 0.000 claims description 7
125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 7
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 7
230000002107 myocardial effect Effects 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
125000005336 allyloxy group Chemical group 0.000 claims description 6
125000002950 monocyclic group Chemical group 0.000 claims description 6
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
229920006395 saturated elastomer Polymers 0.000 claims description 6
230000002265 prevention Effects 0.000 claims description 5
230000009467 reduction Effects 0.000 claims description 5
230000000638 stimulation Effects 0.000 claims description 5
208000031229 Cardiomyopathies Diseases 0.000 claims description 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
208000029078 coronary artery disease Diseases 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 3
125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims description 3
WQJONRMBVKFKOB-UHFFFAOYSA-N cyanatosulfanyl cyanate Chemical compound N#COSOC#N WQJONRMBVKFKOB-UHFFFAOYSA-N 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
UPQQXPKAYZYUKO-UHFFFAOYSA-N 2,2,2-trichloroacetamide Chemical compound OC(=N)C(Cl)(Cl)Cl UPQQXPKAYZYUKO-UHFFFAOYSA-N 0.000 claims description 2
125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 2
229940079593 drug Drugs 0.000 claims description 2
230000008030 elimination Effects 0.000 claims description 2
238000003379 elimination reaction Methods 0.000 claims description 2
230000004217 heart function Effects 0.000 claims description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea group Chemical group NC(=S)N UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 2
125000006726 (C1-C5) alkenyl group Chemical group 0.000 claims 1
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
208000024172 Cardiovascular disease Diseases 0.000 claims 1
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
230000005764 inhibitory process Effects 0.000 claims 1
230000000302 ischemic effect Effects 0.000 claims 1
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 120
239000000243 solution Substances 0.000 description 97
229910004298 SiO 2 Inorganic materials 0.000 description 82
238000000034 method Methods 0.000 description 59
239000007787 solid Substances 0.000 description 56
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 43
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 35
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
230000000694 effects Effects 0.000 description 24
239000002244 precipitate Substances 0.000 description 24
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
239000011734 sodium Substances 0.000 description 21
239000003480 eluent Substances 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
230000001515 vagal effect Effects 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
230000036982 action potential Effects 0.000 description 15
238000011097 chromatography purification Methods 0.000 description 15
208000003663 ventricular fibrillation Diseases 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 14
239000002253 acid Substances 0.000 description 13
239000012442 inert solvent Substances 0.000 description 13
239000002904 solvent Substances 0.000 description 13
239000000126 substance Substances 0.000 description 13
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
241001465754 Metazoa Species 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 12
239000002585 base Substances 0.000 description 11
230000000747 cardiac effect Effects 0.000 description 11
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
230000009471 action Effects 0.000 description 10
230000006793 arrhythmia Effects 0.000 description 10
229910052740 iodine Inorganic materials 0.000 description 10
239000012074 organic phase Substances 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
238000003756 stirring Methods 0.000 description 9
230000015572 biosynthetic process Effects 0.000 description 8
238000004587 chromatography analysis Methods 0.000 description 8
HBNYJWAFDZLWRS-UHFFFAOYSA-N ethyl isothiocyanate Chemical compound CCN=C=S HBNYJWAFDZLWRS-UHFFFAOYSA-N 0.000 description 8
HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical class OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 8
YIKHDPHTFYWYJV-GQCTYLIASA-N (e)-3-(2,4-dimethoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC=C(\C=C\C(O)=O)C(OC)=C1 YIKHDPHTFYWYJV-GQCTYLIASA-N 0.000 description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
241000699670 Mus sp. Species 0.000 description 7
GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical class NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 description 7
238000009835 boiling Methods 0.000 description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
229910052794 bromium Inorganic materials 0.000 description 7
230000008602 contraction Effects 0.000 description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
230000002218 hypoglycaemic effect Effects 0.000 description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
239000000651 prodrug Substances 0.000 description 7
229940002612 prodrug Drugs 0.000 description 7
208000011580 syndromic disease Diseases 0.000 description 7
238000012360 testing method Methods 0.000 description 7
229930003347 Atropine Natural products 0.000 description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
206010019280 Heart failures Diseases 0.000 description 6
RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 6
229960000396 atropine Drugs 0.000 description 6
206010061592 cardiac fibrillation Diseases 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
229910052801 chlorine Inorganic materials 0.000 description 6
201000010099 disease Diseases 0.000 description 6
230000002600 fibrillogenic effect Effects 0.000 description 6
239000006260 foam Substances 0.000 description 6
125000001072 heteroaryl group Chemical group 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
238000010992 reflux Methods 0.000 description 6
210000002820 sympathetic nervous system Anatomy 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
230000002378 acidificating effect Effects 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
235000011114 ammonium hydroxide Nutrition 0.000 description 5
239000012300 argon atmosphere Substances 0.000 description 5
210000004413 cardiac myocyte Anatomy 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
238000001035 drying Methods 0.000 description 5
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 5
208000019622 heart disease Diseases 0.000 description 5
239000011630 iodine Substances 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
230000004936 stimulating effect Effects 0.000 description 5
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
241000699800 Cricetinae Species 0.000 description 4
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 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
210000004027 cell Anatomy 0.000 description 4
235000013985 cinnamic acid Nutrition 0.000 description 4
WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid group Chemical class C(C=CC1=CC=CC=C1)(=O)O WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 4
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 4
230000006378 damage Effects 0.000 description 4
230000006735 deficit Effects 0.000 description 4
206010012601 diabetes mellitus Diseases 0.000 description 4
229960004580 glibenclamide Drugs 0.000 description 4
ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 description 4
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
239000008177 pharmaceutical agent Substances 0.000 description 4
150000002989 phenols Chemical class 0.000 description 4
125000004076 pyridyl group Chemical group 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
229940124530 sulfonamide Drugs 0.000 description 4
150000003456 sulfonamides Chemical class 0.000 description 4
230000002791 sympathovagal effect Effects 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
239000003981 vehicle Substances 0.000 description 4
UFSZMHHSCOXWPC-AATRIKPKSA-N (e)-3-(2,4-dimethylphenyl)prop-2-enoic acid Chemical compound CC1=CC=C(\C=C\C(O)=O)C(C)=C1 UFSZMHHSCOXWPC-AATRIKPKSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 3
OJWYYSVOSNWCCE-UHFFFAOYSA-N 2-methoxyethyl hypofluorite Chemical compound COCCOF OJWYYSVOSNWCCE-UHFFFAOYSA-N 0.000 description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
PZASAAIJIFDWSB-CKPDSHCKSA-N 8-[(1S)-1-[8-(trifluoromethyl)-7-[4-(trifluoromethyl)cyclohexyl]oxynaphthalen-2-yl]ethyl]-8-azabicyclo[3.2.1]octane-3-carboxylic acid Chemical compound FC(F)(F)C=1C2=CC([C@@H](N3C4CCC3CC(C4)C(O)=O)C)=CC=C2C=CC=1OC1CCC(C(F)(F)F)CC1 PZASAAIJIFDWSB-CKPDSHCKSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
206010002091 Anaesthesia Diseases 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 3
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
102000004257 Potassium Channel Human genes 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 3
229960004373 acetylcholine Drugs 0.000 description 3
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RUUGNIQERAFPSL-UHFFFAOYSA-N ethyl n-(benzenesulfonyl)carbamate Chemical class CCOC(=O)NS(=O)(=O)C1=CC=CC=C1 RUUGNIQERAFPSL-UHFFFAOYSA-N 0.000 description 1
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239000002808 molecular sieve Substances 0.000 description 1
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DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
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UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical class O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 description 1
XCSBGRSPUZTPHK-UHFFFAOYSA-N n-[2-(4-aminophenyl)ethyl]-2,2,2-trifluoroacetamide Chemical compound NC1=CC=C(CCNC(=O)C(F)(F)F)C=C1 XCSBGRSPUZTPHK-UHFFFAOYSA-N 0.000 description 1
DDALVGWCBXYJTL-UHFFFAOYSA-N n-[2-(4-methoxy-3-sulfamoylphenyl)ethyl]-3-phenylprop-2-enamide Chemical compound C1=C(S(N)(=O)=O)C(OC)=CC=C1CCNC(=O)C=CC1=CC=CC=C1 DDALVGWCBXYJTL-UHFFFAOYSA-N 0.000 description 1
MRKCYYDAPUHXSR-UHFFFAOYSA-N n-[2-[4-(2-methoxyethoxy)-3-(methylcarbamoylsulfamoyl)phenyl]ethyl]-3-phenylprop-2-enamide Chemical compound C1=C(OCCOC)C(S(=O)(=O)NC(=O)NC)=CC(CCNC(=O)C=CC=2C=CC=CC=2)=C1 MRKCYYDAPUHXSR-UHFFFAOYSA-N 0.000 description 1
SNRHMTMSXNBRGT-UHFFFAOYSA-N n-[2-[4-methoxy-3-(methylcarbamothioylsulfamoyl)phenyl]ethyl]-2-methyl-3-phenylprop-2-enamide Chemical compound C1=C(OC)C(S(=O)(=O)NC(=S)NC)=CC(CCNC(=O)C(C)=CC=2C=CC=CC=2)=C1 SNRHMTMSXNBRGT-UHFFFAOYSA-N 0.000 description 1
NTQUWWZULUSRBR-UHFFFAOYSA-N n-[2-[4-methoxy-3-(methylcarbamothioylsulfamoyl)phenyl]ethyl]-3-phenylprop-2-enamide Chemical compound C1=C(OC)C(S(=O)(=O)NC(=S)NC)=CC(CCNC(=O)C=CC=2C=CC=CC=2)=C1 NTQUWWZULUSRBR-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
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LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
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QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
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239000004036 potassium channel stimulating agent Substances 0.000 description 1
GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
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239000000377 silicon dioxide Substances 0.000 description 1
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URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
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229910000104 sodium hydride Inorganic materials 0.000 description 1
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PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
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125000000547 substituted alkyl group Chemical group 0.000 description 1
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BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
150000003461 sulfonyl halides Chemical class 0.000 description 1
PMCLTINCHUUECN-UHFFFAOYSA-N sulfonylcarbamodithioic acid Chemical compound SC(=S)N=S(=O)=O PMCLTINCHUUECN-UHFFFAOYSA-N 0.000 description 1
125000003375 sulfoxide group Chemical group 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical class O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 description 1
HFOWWBNMJUVIMH-UHFFFAOYSA-N sulfuryl diisothiocyanate Chemical class S=C=NS(=O)(=O)N=C=S HFOWWBNMJUVIMH-UHFFFAOYSA-N 0.000 description 1
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239000006188 syrup Substances 0.000 description 1
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239000003826 tablet Substances 0.000 description 1
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235000012222 talc Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 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
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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210000001519 tissue Anatomy 0.000 description 1
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YEMJHNYABQHWHL-UHFFFAOYSA-N tributyl(ethynyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C#C YEMJHNYABQHWHL-UHFFFAOYSA-N 0.000 description 1
SANWDQJIWZEKOD-UHFFFAOYSA-N tributyl(furan-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CO1 SANWDQJIWZEKOD-UHFFFAOYSA-N 0.000 description 1
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
229910052905 tridymite Inorganic materials 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical class OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
HDWHGDDNMJOCCU-UHFFFAOYSA-N trimethyl(pyridin-2-yl)stannane Chemical compound C[Sn](C)(C)C1=CC=CC=N1 HDWHGDDNMJOCCU-UHFFFAOYSA-N 0.000 description 1
UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
210000001186 vagus nerve Anatomy 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
206010047302 ventricular tachycardia Diseases 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
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235000013343 vitamin Nutrition 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1
BIDDLDNGQCUOJQ-SDNWHVSQSA-N α-phenylcinnamic acid Chemical compound C=1C=CC=CC=1/C(C(=O)O)=C\C1=CC=CC=C1 BIDDLDNGQCUOJQ-SDNWHVSQSA-N 0.000 description 1

Classifications

- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/53—X and Y not being nitrogen atoms, e.g. N-sulfonylcarbamic acid
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
- C07C311/57—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
- C07C311/58—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings having nitrogen atoms of the sulfonylurea groups bound to hydrogen atoms or to acyclic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/40—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of thiourea or isothiourea groups further bound to other hetero atoms
- C07C335/42—Sulfonylthioureas; Sulfonylisothioureas
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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NO20015636A 1999-05-20 2001-11-19 Cinnamoylaminoalkyl-substituerte benzensulfonamidderivater NO321558B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19923086A DE19923086A1 (de)	1999-05-20	1999-05-20	Cinnamoylaminoalkyl-substituierte Benzolsulfonamidderivate, Verfahren zu ihrer Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate
PCT/EP2000/004091 WO2000071513A1 (en)	1999-05-20	2000-05-06	Cinnamoylaminoalkyl-substituted benzenesulfonamide derivatives

Publications (3)

Publication Number	Publication Date
NO20015636D0 NO20015636D0 (no)	2001-11-19
NO20015636L NO20015636L (no)	2002-01-15
NO321558B1 true NO321558B1 (no)	2006-05-29

Family

ID=7908577

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20015636A NO321558B1 (no)	1999-05-20	2001-11-19	Cinnamoylaminoalkyl-substituerte benzensulfonamidderivater

Country Status (30)

Country	Link
US (1)	US6350778B1 (de)
EP (1)	EP1183236B1 (de)
JP (1)	JP4559640B2 (de)
KR (1)	KR100968729B1 (de)
CN (1)	CN1243730C (de)
AR (1)	AR035625A1 (de)
AT (1)	ATE252554T1 (de)
AU (1)	AU771675B2 (de)
BR (1)	BR0010821B1 (de)
CA (1)	CA2374226C (de)
CZ (1)	CZ302943B6 (de)
DE (2)	DE19923086A1 (de)
DK (1)	DK1183236T3 (de)
EE (1)	EE04611B1 (de)
ES (1)	ES2208342T3 (de)
HK (1)	HK1047574B (de)
HR (1)	HRP20010845B1 (de)
HU (1)	HU229041B1 (de)
IL (2)	IL146372A0 (de)
ME (1)	MEP41508A (de)
MX (1)	MXPA01011725A (de)
NO (1)	NO321558B1 (de)
PL (1)	PL201560B1 (de)
PT (1)	PT1183236E (de)
RS (1)	RS50172B (de)
RU (1)	RU2242462C2 (de)
SK (1)	SK287237B6 (de)
TR (1)	TR200103312T2 (de)
WO (1)	WO2000071513A1 (de)
ZA (1)	ZA200109481B (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE10054482A1 (de)	2000-11-03	2002-05-08	Aventis Pharma Gmbh	Heteroarylacryloylaminoalkyl-substituierte Benzolsulfonamidderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate
DE10054481A1 (de)	2000-11-03	2002-05-08	Aventis Pharma Gmbh	Acylaminoalkyl-substituierte Benzolsulfonamidderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate
CN1237185C (zh) *	2003-06-04	2006-01-18	中国科学院上海药物研究所	Sars冠状病毒3cl蛋白酶三维结构模型与抗sars药物

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DE1185180B (de)	1963-10-19	1965-01-14	Hoechst Ag	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
DE1518874C3 (de) *	1964-10-07	1975-03-13	Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt	Benzolsulfonylharnstoffe und Verfahren zu ihrer Herstellung
DE1518816C3 (de)	1965-03-24	1975-05-22	Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt	Benzolsulfonylharnstoffe, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
DE1545810A1 (de) *	1965-05-06	1969-12-11	Hoechst Ag	Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden
US4066639A (en)	1965-05-06	1978-01-03	Hoechst Aktiengesellschaft	Benzene-sulfonyl semicarbazides and process for preparing them
DE2413514C3 (de) *	1974-03-21	1982-03-04	Hoechst Ag, 6000 Frankfurt	N-Acylaminoathylbenzolsulfonyl-N'-methylharnstoffe, Verfahren zu ihrer Herstellung und deren Verwendung
ATE146775T1 (de) *	1993-02-23	1997-01-15	Hoechst Ag	Substituierte benzolsulfonylharnstoffe und - thioharnstoffe- verfahren zu ihrer herstellung und ihre verwendung als pharmazeutika
DE4341655A1 (de)	1993-12-07	1995-06-08	Hoechst Ag	Aminosubstituierte Benzolsulfonylharnstoffe und -thioharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Pharmazeutika
JPH0826995A (ja) *	1994-07-22	1996-01-30	Nisshin Flour Milling Co Ltd	ベンズイミダゾール誘導体を含有する抗不整脈剤
DE19505397A1 (de)	1995-02-17	1996-08-22	Hoechst Ag	Substituierte Benzolsulfonylharnstoffe und -thioharnstoffe, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
DE19832009A1 (de)	1998-07-16	2000-01-20	Hoechst Marion Roussel De Gmbh	2,5-Substituierte Benzolsulfonylharnstoffe und -thioharnstoffe, Verfahren zu ihrer Herstellung, ihre Verwendung und sie enthaltende pharamazeutische Präparate
CZ301165B6 (cs)	1998-09-10	2009-11-25	Sanofi - Aventis Deutschland GmbH	Použití benzensulfonyl(thio)mocovin pro lécení a profylaxi dysfunkcí autonomní nervové soustavy a použití benzensulfonyl(thio)mocovin v kombinaci s beta-receptorovými blokátory
US6303637B1 (en) *	1998-10-30	2001-10-16	Merck & Co., Inc.	Heterocyclic potassium channel inhibitors
US6632836B1 (en) *	1998-10-30	2003-10-14	Merck & Co., Inc.	Carbocyclic potassium channel inhibitors
US6194458B1 (en) *	1998-10-30	2001-02-27	Merck & Co., Inc.	Benzamide potassium channel inhibitors

1999
- 1999-05-20 DE DE19923086A patent/DE19923086A1/de not_active Withdrawn
2000
- 2000-05-06 RU RU2001134291/04A patent/RU2242462C2/ru not_active IP Right Cessation
- 2000-05-06 TR TR2001/03312T patent/TR200103312T2/xx unknown
- 2000-05-06 AT AT00938626T patent/ATE252554T1/de active
- 2000-05-06 HU HU0201906A patent/HU229041B1/hu not_active IP Right Cessation
- 2000-05-06 IL IL14637200A patent/IL146372A0/xx active IP Right Grant
- 2000-05-06 PL PL351751A patent/PL201560B1/pl unknown
- 2000-05-06 EP EP00938626A patent/EP1183236B1/de not_active Expired - Lifetime
- 2000-05-06 SK SK1669-2001A patent/SK287237B6/sk not_active IP Right Cessation
- 2000-05-06 CZ CZ20014149A patent/CZ302943B6/cs not_active IP Right Cessation
- 2000-05-06 ME MEP-415/08A patent/MEP41508A/xx unknown
- 2000-05-06 PT PT00938626T patent/PT1183236E/pt unknown
- 2000-05-06 AU AU53933/00A patent/AU771675B2/en not_active Ceased
- 2000-05-06 CA CA2374226A patent/CA2374226C/en not_active Expired - Fee Related
- 2000-05-06 MX MXPA01011725A patent/MXPA01011725A/es active IP Right Grant
- 2000-05-06 KR KR1020017014819A patent/KR100968729B1/ko not_active IP Right Cessation
- 2000-05-06 DK DK00938626T patent/DK1183236T3/da active
- 2000-05-06 CN CNB008078203A patent/CN1243730C/zh not_active Expired - Fee Related
- 2000-05-06 BR BRPI0010821-9A patent/BR0010821B1/pt not_active IP Right Cessation
- 2000-05-06 ES ES00938626T patent/ES2208342T3/es not_active Expired - Lifetime
- 2000-05-06 DE DE60006104T patent/DE60006104T2/de not_active Expired - Lifetime
- 2000-05-06 RS YUP-817/01A patent/RS50172B/sr unknown
- 2000-05-06 JP JP2000619770A patent/JP4559640B2/ja not_active Expired - Fee Related
- 2000-05-06 EE EEP200100609A patent/EE04611B1/xx not_active IP Right Cessation
- 2000-05-06 WO PCT/EP2000/004091 patent/WO2000071513A1/en active IP Right Grant
- 2000-05-19 AR ARP000102388A patent/AR035625A1/es active IP Right Grant
- 2000-05-19 US US09/573,166 patent/US6350778B1/en not_active Expired - Lifetime
2001
- 2001-11-06 IL IL146372A patent/IL146372A/en not_active IP Right Cessation
- 2001-11-16 HR HR20010845A patent/HRP20010845B1/xx not_active IP Right Cessation
- 2001-11-16 ZA ZA200109481A patent/ZA200109481B/xx unknown
- 2001-11-19 NO NO20015636A patent/NO321558B1/no not_active IP Right Cessation
2002
- 2002-11-29 HK HK02108646.9A patent/HK1047574B/zh not_active IP Right Cessation

Also Published As

Publication number	Publication date
EE04611B1 (et)	2006-04-17
AU5393300A (en)	2000-12-12
BR0010821A (pt)	2002-03-05
ATE252554T1 (de)	2003-11-15
PL351751A1 (en)	2003-06-16
RS50172B (sr)	2009-05-06
HK1047574A1 (en)	2003-02-28
TR200103312T2 (tr)	2002-04-22
YU81701A (sh)	2004-07-15
HU229041B1 (hu)	2013-07-29
CN1360571A (zh)	2002-07-24
JP4559640B2 (ja)	2010-10-13
KR100968729B1 (ko)	2010-07-08
KR20020005046A (ko)	2002-01-16
CA2374226C (en)	2010-08-31
IL146372A0 (en)	2002-07-25
DE19923086A1 (de)	2000-11-23
ZA200109481B (en)	2002-06-25
HRP20010845A2 (en)	2003-04-30
NO20015636D0 (no)	2001-11-19
HUP0201906A2 (en)	2002-09-28
PL201560B1 (pl)	2009-04-30
AR035625A1 (es)	2004-06-23
AU771675B2 (en)	2004-04-01
MEP41508A (en)	2011-02-10
HUP0201906A3 (en)	2005-04-28
EP1183236A1 (de)	2002-03-06
BR0010821B1 (pt)	2011-07-12
HRP20010845B1 (en)	2010-08-31
RU2242462C2 (ru)	2004-12-20
EE200100609A (et)	2003-02-17
CA2374226A1 (en)	2000-11-30
CZ302943B6 (cs)	2012-01-25
HK1047574B (zh)	2006-08-04
US6350778B1 (en)	2002-02-26
DE60006104D1 (de)	2003-11-27
IL146372A (en)	2007-05-15
DK1183236T3 (da)	2004-02-23
SK16692001A3 (sk)	2002-04-04
EP1183236B1 (de)	2003-10-22
DE60006104T2 (de)	2004-08-05
MXPA01011725A (es)	2002-04-24
ES2208342T3 (es)	2004-06-16
PT1183236E (pt)	2004-03-31
WO2000071513A1 (en)	2000-11-30
CZ20014149A3 (cs)	2002-03-13
HRP20010845A9 (en)	2010-06-30
SK287237B6 (sk)	2010-04-07
CN1243730C (zh)	2006-03-01
JP2003500388A (ja)	2003-01-07
NO20015636L (no)	2002-01-15

Publication	Publication Date	Title
AU2002218253B2 (en)	2006-07-06	Acylaminoalkyl-substituted benzenesulfonamide derivatives
AU2002218253A1 (en)	2002-07-18	Acylaminoalkyl-substituted benzenesulfonamide derivatives
RU2235720C2 (ru)	2004-09-10	2,5-замещенные бензолсульфонилмочевины или -тиомочевины, способ их получения и фармацевтическая композиция
NO321558B1 (no)	2006-05-29	Cinnamoylaminoalkyl-substituerte benzensulfonamidderivater
EP1335902B1 (de)	2008-10-08	Heteroarylacryloylaminoalkyl-substituierte benzolsulfonamidderivate, deren herstellung, deren verwendung und pharmazeutische zusammensetzungen, die diese verbindungen enthalten
AU2002223631A1 (en)	2002-07-18	Heteroarylacryloylaminoalkyl-substituted benzenesulfonamide derivatives, their preparation, their use and pharmaceutical preparations comprising them

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