NO330215B1 - Anvendelse av benzensulfonyl(tio)ureaforbindelser,produkt og farmasoytisk preparat omfattende ±n eller flere slike forbindelser - Google Patents

Anvendelse av benzensulfonyl(tio)ureaforbindelser,produkt og farmasoytisk preparat omfattende ±n eller flere slike forbindelser Download PDF

Info

Publication number: NO330215B1
Authority: NO; Norway
Prior art keywords: alkoxy; formula; alkyl; compounds; physiologically acceptable
Prior art date: 1998-09-10

Application number

NO20011117A

Other languages

English (en)

Norwegian (no)

Other versions

NO20011117L (no

NO20011117D0 (no

Inventor

Helmut Bohn

Klaus Wirth

Heinz Gogelein

Heinrich Englert

Uwe Gerlach

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.)

1998-09-10

Filing date

2001-03-05

Publication date

2011-03-07

1998-09-10 Priority claimed from DE1998141534 external-priority patent/DE19841534A1/de

1999-01-14 Priority claimed from DE1999101061 external-priority patent/DE19901061A1/de

2001-03-05 Application filed by Sanofi Aventis Deutschland filed Critical Sanofi Aventis Deutschland

2001-03-05 Publication of NO20011117D0 publication Critical patent/NO20011117D0/no

2001-05-02 Publication of NO20011117L publication Critical patent/NO20011117L/no

2011-03-07 Publication of NO330215B1 publication Critical patent/NO330215B1/no

Links

150000001875 compounds Chemical class 0.000 title claims description 161
239000008194 pharmaceutical composition Substances 0.000 title description 6
JDQFSRIDEGDSLS-UHFFFAOYSA-N benzenesulfonylsulfanylurea Chemical class NC(=O)NSS(=O)(=O)C1=CC=CC=C1 JDQFSRIDEGDSLS-UHFFFAOYSA-N 0.000 title description 3
150000003839 salts Chemical class 0.000 claims description 79
-1 (thio)urea compound Chemical class 0.000 claims description 60
239000001257 hydrogen Substances 0.000 claims description 58
229910052739 hydrogen Inorganic materials 0.000 claims description 58
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 53
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 50
229910052736 halogen Inorganic materials 0.000 claims description 45
150000002367 halogens Chemical class 0.000 claims description 44
239000000203 mixture Substances 0.000 claims description 39
239000002876 beta blocker Substances 0.000 claims description 38
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
239000000825 pharmaceutical preparation Substances 0.000 claims description 32
230000004064 dysfunction Effects 0.000 claims description 30
238000011282 treatment Methods 0.000 claims description 29
150000002431 hydrogen Chemical class 0.000 claims description 28
229910052717 sulfur Chemical group 0.000 claims description 25
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 23
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
210000003403 autonomic nervous system Anatomy 0.000 claims description 21
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 20
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 20
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 20
229910052760 oxygen Inorganic materials 0.000 claims description 20
239000001301 oxygen Substances 0.000 claims description 20
230000002265 prevention Effects 0.000 claims description 20
239000011593 sulfur Chemical group 0.000 claims description 20
239000003814 drug Substances 0.000 claims description 18
AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 claims description 18
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 13
238000011321 prophylaxis Methods 0.000 claims description 13
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 11
125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims description 11
125000006529 (C3-C6) alkyl group Chemical group 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 10
229940079593 drug Drugs 0.000 claims description 10
208000019622 heart disease Diseases 0.000 claims description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 9
229960003712 propranolol Drugs 0.000 claims description 9
125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 8
206010019280 Heart failures Diseases 0.000 claims description 8
208000010125 myocardial infarction Diseases 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
159000000000 sodium salts Chemical class 0.000 claims description 7
125000003709 fluoroalkyl group Chemical group 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
METKIMKYRPQLGS-GFCCVEGCSA-N (R)-atenolol Chemical compound CC(C)NC[C@@H](O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-GFCCVEGCSA-N 0.000 claims description 5
229960002274 atenolol Drugs 0.000 claims description 5
206010012601 diabetes mellitus Diseases 0.000 claims description 5
206010002383 Angina Pectoris Diseases 0.000 claims description 4
VHYCDWMUTMEGQY-UHFFFAOYSA-N bisoprolol Chemical compound CC(C)NCC(O)COC1=CC=C(COCCOC(C)C)C=C1 VHYCDWMUTMEGQY-UHFFFAOYSA-N 0.000 claims description 4
229960002781 bisoprolol Drugs 0.000 claims description 4
229960004195 carvedilol Drugs 0.000 claims description 4
NPAKNKYSJIDKMW-UHFFFAOYSA-N carvedilol Chemical compound COC1=CC=CC=C1OCCNCC(O)COC1=CC=CC2=NC3=CC=C[CH]C3=C12 NPAKNKYSJIDKMW-UHFFFAOYSA-N 0.000 claims description 4
208000029078 coronary artery disease Diseases 0.000 claims description 4
CEMAWMOMDPGJMB-UHFFFAOYSA-N (+-)-Oxprenolol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1OCC=C CEMAWMOMDPGJMB-UHFFFAOYSA-N 0.000 claims description 3
NXWGWUVGUSFQJC-GFCCVEGCSA-N (2r)-1-[(2-methyl-1h-indol-4-yl)oxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NC[C@@H](O)COC1=CC=CC2=C1C=C(C)N2 NXWGWUVGUSFQJC-GFCCVEGCSA-N 0.000 claims description 3
TWBNMYSKRDRHAT-RCWTXCDDSA-N (S)-timolol hemihydrate Chemical compound O.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1 TWBNMYSKRDRHAT-RCWTXCDDSA-N 0.000 claims description 3
UUOJIACWOAYWEZ-UHFFFAOYSA-N 1-(tert-butylamino)-3-[(2-methyl-1H-indol-4-yl)oxy]propan-2-yl benzoate Chemical compound C1=CC=C2NC(C)=CC2=C1OCC(CNC(C)(C)C)OC(=O)C1=CC=CC=C1 UUOJIACWOAYWEZ-UHFFFAOYSA-N 0.000 claims description 3
208000031229 Cardiomyopathies Diseases 0.000 claims description 3
JOATXPAWOHTVSZ-UHFFFAOYSA-N Celiprolol Chemical compound CCN(CC)C(=O)NC1=CC=C(OCC(O)CNC(C)(C)C)C(C(C)=O)=C1 JOATXPAWOHTVSZ-UHFFFAOYSA-N 0.000 claims description 3
HTWFXPCUFWKXOP-UHFFFAOYSA-N Tertatalol Chemical compound C1CCSC2=C1C=CC=C2OCC(O)CNC(C)(C)C HTWFXPCUFWKXOP-UHFFFAOYSA-N 0.000 claims description 3
229960002122 acebutolol Drugs 0.000 claims description 3
GOEMGAFJFRBGGG-UHFFFAOYSA-N acebutolol Chemical compound CCCC(=O)NC1=CC=C(OCC(O)CNC(C)C)C(C(C)=O)=C1 GOEMGAFJFRBGGG-UHFFFAOYSA-N 0.000 claims description 3
229960002213 alprenolol Drugs 0.000 claims description 3
PAZJSJFMUHDSTF-UHFFFAOYSA-N alprenolol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1CC=C PAZJSJFMUHDSTF-UHFFFAOYSA-N 0.000 claims description 3
229960004324 betaxolol Drugs 0.000 claims description 3
CHDPSNLJFOQTRK-UHFFFAOYSA-N betaxolol hydrochloride Chemical compound [Cl-].C1=CC(OCC(O)C[NH2+]C(C)C)=CC=C1CCOCC1CC1 CHDPSNLJFOQTRK-UHFFFAOYSA-N 0.000 claims description 3
229960001035 bopindolol Drugs 0.000 claims description 3
229960000330 bupranolol Drugs 0.000 claims description 3
HQIRNZOQPUAHHV-UHFFFAOYSA-N bupranolol Chemical compound CC1=CC=C(Cl)C(OCC(O)CNC(C)(C)C)=C1 HQIRNZOQPUAHHV-UHFFFAOYSA-N 0.000 claims description 3
BQXQGZPYHWWCEB-UHFFFAOYSA-N carazolol Chemical compound N1C2=CC=CC=C2C2=C1C=CC=C2OCC(O)CNC(C)C BQXQGZPYHWWCEB-UHFFFAOYSA-N 0.000 claims description 3
229960004634 carazolol Drugs 0.000 claims description 3
229960001222 carteolol Drugs 0.000 claims description 3
LWAFSWPYPHEXKX-UHFFFAOYSA-N carteolol Chemical compound N1C(=O)CCC2=C1C=CC=C2OCC(O)CNC(C)(C)C LWAFSWPYPHEXKX-UHFFFAOYSA-N 0.000 claims description 3
229960002320 celiprolol Drugs 0.000 claims description 3
229960003134 mepindolol Drugs 0.000 claims description 3
229960002704 metipranolol Drugs 0.000 claims description 3
BLWNYSZZZWQCKO-UHFFFAOYSA-N metipranolol hydrochloride Chemical compound [Cl-].CC(C)[NH2+]CC(O)COC1=CC(C)=C(OC(C)=O)C(C)=C1C BLWNYSZZZWQCKO-UHFFFAOYSA-N 0.000 claims description 3
IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 claims description 3
229960002237 metoprolol Drugs 0.000 claims description 3
229960004255 nadolol Drugs 0.000 claims description 3
VWPOSFSPZNDTMJ-UCWKZMIHSA-N nadolol Chemical compound C1[C@@H](O)[C@@H](O)CC2=C1C=CC=C2OCC(O)CNC(C)(C)C VWPOSFSPZNDTMJ-UCWKZMIHSA-N 0.000 claims description 3
229960004570 oxprenolol Drugs 0.000 claims description 3
229960002035 penbutolol Drugs 0.000 claims description 3
KQXKVJAGOJTNJS-HNNXBMFYSA-N penbutolol Chemical compound CC(C)(C)NC[C@H](O)COC1=CC=CC=C1C1CCCC1 KQXKVJAGOJTNJS-HNNXBMFYSA-N 0.000 claims description 3
229960002508 pindolol Drugs 0.000 claims description 3
PHUTUTUABXHXLW-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=NC=C[C]12 PHUTUTUABXHXLW-UHFFFAOYSA-N 0.000 claims description 3
229960002370 sotalol Drugs 0.000 claims description 3
ZBMZVLHSJCTVON-UHFFFAOYSA-N sotalol Chemical compound CC(C)NCC(O)C1=CC=C(NS(C)(=O)=O)C=C1 ZBMZVLHSJCTVON-UHFFFAOYSA-N 0.000 claims description 3
229960003658 talinolol Drugs 0.000 claims description 3
MXFWWQICDIZSOA-UHFFFAOYSA-N talinolol Chemical compound C1=CC(OCC(O)CNC(C)(C)C)=CC=C1NC(=O)NC1CCCCC1 MXFWWQICDIZSOA-UHFFFAOYSA-N 0.000 claims description 3
229960003352 tertatolol Drugs 0.000 claims description 3
229960004605 timolol Drugs 0.000 claims description 3
125000001183 hydrocarbyl group Chemical group 0.000 claims 8
230000000694 effects Effects 0.000 description 29
238000006243 chemical reaction Methods 0.000 description 17
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
210000000653 nervous system Anatomy 0.000 description 16
239000000243 solution Substances 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
239000000047 product Substances 0.000 description 14
KQJQICVXLJTWQD-UHFFFAOYSA-N N-Methylthiourea Chemical compound CNC(N)=S KQJQICVXLJTWQD-UHFFFAOYSA-N 0.000 description 13
239000002253 acid Substances 0.000 description 13
238000002360 preparation method Methods 0.000 description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical class NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 description 12
150000002430 hydrocarbons Chemical group 0.000 description 12
238000000034 method Methods 0.000 description 12
239000000126 substance Substances 0.000 description 12
206010003119 arrhythmia Diseases 0.000 description 10
230000006870 function Effects 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
150000007513 acids Chemical class 0.000 description 9
239000012442 inert solvent Substances 0.000 description 9
239000000463 material Substances 0.000 description 9
239000003826 tablet Substances 0.000 description 9
208000003663 ventricular fibrillation Diseases 0.000 description 9
125000000217 alkyl group Chemical group 0.000 description 8
150000001412 amines Chemical class 0.000 description 8
239000002585 base Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
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 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
230000009471 action Effects 0.000 description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
230000002889 sympathetic effect Effects 0.000 description 7
238000003786 synthesis reaction Methods 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
201000010099 disease Diseases 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 description 6
125000006239 protecting group Chemical group 0.000 description 6
230000001681 protective effect Effects 0.000 description 6
229930003347 Atropine Natural products 0.000 description 5
RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 5
206010049418 Sudden Cardiac Death Diseases 0.000 description 5
150000001340 alkali metals Chemical class 0.000 description 5
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 5
229960000396 atropine Drugs 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
239000007858 starting material Substances 0.000 description 5
230000004936 stimulating effect Effects 0.000 description 5
230000000638 stimulation Effects 0.000 description 5
230000002791 sympathovagal effect Effects 0.000 description 5
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
LTPVSOCPYWDIFU-UHFFFAOYSA-N 4-methoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1 LTPVSOCPYWDIFU-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 4
229960004373 acetylcholine Drugs 0.000 description 4
239000000654 additive Substances 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
150000001768 cations Chemical class 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
229910052731 fluorine Inorganic materials 0.000 description 4
239000011737 fluorine Substances 0.000 description 4
230000001771 impaired effect Effects 0.000 description 4
238000001990 intravenous administration Methods 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
239000000546 pharmaceutical excipient Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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239000011541 reaction mixture Substances 0.000 description 4
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QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
206010002091 Anaesthesia Diseases 0.000 description 3
229920002785 Croscarmellose sodium Polymers 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
206010021143 Hypoxia Diseases 0.000 description 3
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 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
230000036982 action potential Effects 0.000 description 3
230000010933 acylation Effects 0.000 description 3
238000005917 acylation reaction Methods 0.000 description 3
229910000272 alkali metal oxide Inorganic materials 0.000 description 3
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230000037005 anaesthesia Effects 0.000 description 3
230000003288 anthiarrhythmic effect Effects 0.000 description 3
150000008331 benzenesulfonamides Chemical class 0.000 description 3
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230000000747 cardiac effect Effects 0.000 description 3
210000004413 cardiac myocyte Anatomy 0.000 description 3
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229910052500 inorganic mineral Inorganic materials 0.000 description 3
238000011835 investigation Methods 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
239000012948 isocyanate Substances 0.000 description 3
239000011707 mineral Substances 0.000 description 3
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000007787 solid Substances 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
210000002820 sympathetic nervous system Anatomy 0.000 description 3
208000024891 symptom Diseases 0.000 description 3
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UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical class ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
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PIJVFDBKTWXHHD-HIFRSBDPSA-N physostigmine Chemical compound C12=CC(OC(=O)NC)=CC=C2N(C)[C@@H]2[C@@]1(C)CCN2C PIJVFDBKTWXHHD-HIFRSBDPSA-N 0.000 description 1
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RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
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ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
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HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
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235000002906 tartaric acid Nutrition 0.000 description 1
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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
150000003512 tertiary amines Chemical class 0.000 description 1
UVVUGWBBCDFNSD-UHFFFAOYSA-N tetraisocyanatosilane Chemical compound O=C=N[Si](N=C=O)(N=C=O)N=C=O UVVUGWBBCDFNSD-UHFFFAOYSA-N 0.000 description 1
NOGBKWXHNPDHFA-UHFFFAOYSA-N tetraisothiocyanatosilane Chemical compound S=C=N[Si](N=C=S)(N=C=S)N=C=S NOGBKWXHNPDHFA-UHFFFAOYSA-N 0.000 description 1
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UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea group Chemical group NC(=S)N UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
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Classifications

- 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
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/64—Sulfonylureas, e.g. glibenclamide, tolbutamide, chlorpropamide
- 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
- A61P25/02—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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- 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
- 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
- A61P9/04—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
- C07C311/54—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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/5406—Silicon-containing compounds containing elements other than oxygen or nitrogen

Landscapes

Health & Medical Sciences (AREA)
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Medicinal Chemistry (AREA)
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Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Cardiology (AREA)
Epidemiology (AREA)
Heart & Thoracic Surgery (AREA)
Diabetes (AREA)
Polymers & Plastics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Hospice & Palliative Care (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Hematology (AREA)
Obesity (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO20011117A 1998-09-10 2001-03-05 Anvendelse av benzensulfonyl(tio)ureaforbindelser,produkt og farmasoytisk preparat omfattende ±n eller flere slike forbindelser NO330215B1 (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE1998141534 DE19841534A1 (de)	1998-09-10	1998-09-10	Verwendung von Benzolsulfonyl(thio)harnstoffen zur Behandlung und Prophylaxe von Dysfunktionen des autonomen Nervensystems und Verwendung von Benzolsulfonyl(thio)harnstoffen in Kombination mit Betarezeptoren-Blockern
DE1999101061 DE19901061A1 (de)	1999-01-14	1999-01-14	Verwendung von Benzolsulfonyl(thio)harnstoffen zur Behandlung von Prophylaxe von Dysfunktionen des autonomen Nervensystems und Verwendung von Benzolsulfonyl(thio)harnstoffen in Kombination mit Betarezeptoren-Blockern
PCT/EP1999/006450 WO2000015204A2 (en)	1998-09-10	1999-09-02	Use of benzenesulfonyl(thio)ureas for the treatment and prophylaxis of dysfunctions of the autonomous nervous system and use of benzenesulfonyl(thio)ureas in combination with beta-receptor blockers

Publications (3)

Publication Number	Publication Date
NO20011117D0 NO20011117D0 (no)	2001-03-05
NO20011117L NO20011117L (no)	2001-05-02
NO330215B1 true NO330215B1 (no)	2011-03-07

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NO20011117A NO330215B1 (no)	1998-09-10	2001-03-05	Anvendelse av benzensulfonyl(tio)ureaforbindelser,produkt og farmasoytisk preparat omfattende ±n eller flere slike forbindelser

Country Status (27)

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US (1)	US6414030B1 (pl)
EP (1)	EP1117409B1 (pl)
JP (1)	JP4733268B2 (pl)
KR (1)	KR100981592B1 (pl)
CN (1)	CN1195524C (pl)
AR (1)	AR020411A1 (pl)
AT (1)	ATE287718T1 (pl)
AU (1)	AU762832B2 (pl)
BR (1)	BR9913572A (pl)
CA (1)	CA2343009C (pl)
CZ (1)	CZ301165B6 (pl)
DE (1)	DE69923464T2 (pl)
DK (1)	DK1117409T3 (pl)
ES (1)	ES2235507T3 (pl)
HK (1)	HK1040187B (pl)
HU (1)	HU228988B1 (pl)
ID (1)	ID28854A (pl)
IL (2)	IL141414A0 (pl)
MY (1)	MY121798A (pl)
NO (1)	NO330215B1 (pl)
NZ (1)	NZ510424A (pl)
PL (1)	PL194986B1 (pl)
PT (1)	PT1117409E (pl)
RU (1)	RU2247562C2 (pl)
TR (1)	TR200100692T2 (pl)
TW (1)	TWI238817B (pl)
WO (1)	WO2000015204A2 (pl)

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Publication number	Priority date	Publication date	Assignee	Title
DE19917233A1 (de) *	1999-04-16	2000-10-19	Aventis Pharma Gmbh	Kristalline Formen des Natriumsalzes des 5-Chlor-2-methoxy-N-(2-(4-methoxy-3-methylaminothiocarbonylaminosulfonyl-phenyl)-ethyl)- benzamids
DE19923086A1 (de)	1999-05-20	2000-11-23	Aventis Pharma Gmbh	Cinnamoylaminoalkyl-substituierte Benzolsulfonamidderivate, Verfahren zu ihrer Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate
US7620611B1 (en) *	1999-07-20	2009-11-17	Trilithic, Inc.	Neural networks for ingress monitoring
DE10054481A1 (de)	2000-11-03	2002-05-08	Aventis Pharma Gmbh	Acylaminoalkyl-substituierte Benzolsulfonamidderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate
DE10054482A1 (de)	2000-11-03	2002-05-08	Aventis Pharma Gmbh	Heteroarylacryloylaminoalkyl-substituierte Benzolsulfonamidderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate
DE10129704A1 (de) *	2001-06-22	2003-01-02	Aventis Pharma Gmbh	Verwendung von Benzolsulfonyl(thio)harnstoffen in der Behandlung des septischen Schocks
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1999
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- 1999-09-02 BR BR9913572-8A patent/BR9913572A/pt not_active Application Discontinuation
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Also Published As

Publication number	Publication date
CZ301165B6 (cs)	2009-11-25
CA2343009C (en)	2011-03-15
PL194986B1 (pl)	2007-07-31
CZ2001858A3 (en)	2001-06-13
HK1040187B (zh)	2005-09-02
NO20011117L (no)	2001-05-02
JP4733268B2 (ja)	2011-07-27
TWI238817B (en)	2005-09-01
DE69923464D1 (de)	2005-03-03
DE69923464T2 (de)	2006-05-11
AU5744499A (en)	2000-04-03
ATE287718T1 (de)	2005-02-15
KR100981592B1 (ko)	2010-09-13
IL141414A (en)	2006-07-05
AR020411A1 (es)	2002-05-08
KR20010086396A (ko)	2001-09-10
US6414030B1 (en)	2002-07-02
BR9913572A (pt)	2001-05-22
US20020082300A1 (en)	2002-06-27
CN1195524C (zh)	2005-04-06
PT1117409E (pt)	2005-04-29
MY121798A (en)	2006-02-28
DK1117409T3 (da)	2005-05-30
EP1117409B1 (en)	2005-01-26
NZ510424A (en)	2003-06-30
PL347215A1 (en)	2002-03-25
CN1319014A (zh)	2001-10-24
AU762832B2 (en)	2003-07-03
WO2000015204A3 (en)	2000-07-13
HUP0103534A3 (en)	2003-09-29
HU228988B1 (hu)	2013-07-29
ID28854A (id)	2001-07-05
CA2343009A1 (en)	2000-03-23
EP1117409A2 (en)	2001-07-25
ES2235507T3 (es)	2005-07-01
HUP0103534A2 (hu)	2002-05-29
TR200100692T2 (tr)	2001-07-23
NO20011117D0 (no)	2001-03-05
IL141414A0 (en)	2002-03-10
JP2002524497A (ja)	2002-08-06
WO2000015204A2 (en)	2000-03-23
RU2247562C2 (ru)	2005-03-10
HK1040187A1 (en)	2002-05-31

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2016-04-25	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
ES2237614T3 (es)	2005-08-01	Derivados de bencenosulfonamidas sustituidas con acilaminoalquilo.
AU762832B2 (en)	2003-07-03	Use of benzenesulfonyl(thio)ureas for the treatment and prophylaxis of dysfunctions of the autonomous nervous system and use of benzenesulfonyl(thio)ureas in combination with beta-receptor blockers
SK11795A3 (en)	1995-08-09	Treatment containing 3-phenylsulfonyl-3,7-diazobicyclo /3,3,1/ nonane compounds
CA2169696C (en)	2008-09-02	Substituted benzenesulfonylureas and -thioureas, processes for their preparation and use of pharmaceutical preparations based on these compounds, and medicaments containing them
US6350778B1 (en)	2002-02-26	Cinnamoylaminoalkyl-substituted benzenesulfonamide derivatives, processes for their preparation, their use, and pharmaceutical preparations comprising them
MXPA01002222A (en)	2001-09-07	Use of benzenesulfonyl(thio)ureas for the treatment and prophylaxis of dysfunctions of the autonomous nervous system and use of benzenesulfonyl(thio)ureas in combination with beta-receptor blockers
ZA200101746B (en)	2001-09-25	Use of benzenesulfonyl(thio)ureas for the treatment and prophylaxis of dysfunctions of the autonomous nervous system and use of benzenesulfonyl(thio)ureas in combination with beta-receptor blockers.
DE19901061A1 (de)	2000-07-20	Verwendung von Benzolsulfonyl(thio)harnstoffen zur Behandlung von Prophylaxe von Dysfunktionen des autonomen Nervensystems und Verwendung von Benzolsulfonyl(thio)harnstoffen in Kombination mit Betarezeptoren-Blockern
HK1006166B (en)	1999-02-12	Substituted benzenesulfonylureas and -thioureas, process for their preparation and their use as pharmaceuticals