NO309563B1 - Benzensulfonamidforbindelser, deres fremstilling samt medikament og farmasöytisk preparat inneholdende disse - Google Patents

Benzensulfonamidforbindelser, deres fremstilling samt medikament og farmasöytisk preparat inneholdende disse Download PDF

Info

Publication number: NO309563B1
Authority: NO; Norway
Prior art keywords: group; hydrogen atom; methoxy; formula; compounds
Prior art date: 1995-08-04

Application number

NO980471A

Other languages

English (en)

Norwegian (no)

Other versions

NO980471L (no

NO980471D0 (no

Inventor

Thomas Purcell

Christophe Philippo

Original Assignee

Sanofi Synthelabo

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.)

1995-08-04

Filing date

1998-02-03

Publication date

2001-02-19

1998-02-03 Application filed by Sanofi Synthelabo filed Critical Sanofi Synthelabo

1998-02-03 Publication of NO980471D0 publication Critical patent/NO980471D0/no

1998-04-06 Publication of NO980471L publication Critical patent/NO980471L/no

2001-02-19 Publication of NO309563B1 publication Critical patent/NO309563B1/no

Links

150000008331 benzenesulfonamides Chemical class 0.000 title claims abstract description 4
238000002360 preparation method Methods 0.000 title claims description 8
239000003814 drug Substances 0.000 title claims description 4
229940079593 drug Drugs 0.000 title claims description 4
239000000825 pharmaceutical preparation Substances 0.000 title claims description 4
239000000203 mixture Substances 0.000 claims abstract description 80
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 53
150000003839 salts Chemical class 0.000 claims abstract description 29
125000000217 alkyl group Chemical group 0.000 claims abstract description 25
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 claims abstract description 24
229910052801 chlorine Inorganic materials 0.000 claims abstract description 16
239000002253 acid Substances 0.000 claims abstract description 13
229910052731 fluorine Inorganic materials 0.000 claims abstract description 12
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 10
125000004122 cyclic group Chemical group 0.000 claims abstract description 10
125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 7
239000000460 chlorine Substances 0.000 claims abstract description 7
125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 7
125000005010 perfluoroalkyl group Chemical group 0.000 claims abstract description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 5
239000011737 fluorine Substances 0.000 claims abstract description 5
125000005843 halogen group Chemical group 0.000 claims abstract description 5
150000001875 compounds Chemical class 0.000 claims description 104
238000000034 method Methods 0.000 claims description 27
238000006243 chemical reaction Methods 0.000 claims description 19
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
150000007513 acids Chemical class 0.000 claims description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
150000001412 amines Chemical class 0.000 claims description 9
125000001309 chloro group Chemical group Cl* 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
125000001153 fluoro group Chemical group F* 0.000 claims description 8
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 8
UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 claims description 8
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 7
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 7
239000003054 catalyst Substances 0.000 claims description 7
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 claims description 5
239000012448 Lithium borohydride Substances 0.000 claims description 4
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
230000009466 transformation Effects 0.000 claims 1
238000007792 addition Methods 0.000 abstract description 10
230000001225 therapeutic effect Effects 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 103
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
239000000047 product Substances 0.000 description 31
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 19
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 18
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 18
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 14
238000001953 recrystallisation Methods 0.000 description 13
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
239000012074 organic phase Substances 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
230000036772 blood pressure Effects 0.000 description 8
238000004440 column chromatography Methods 0.000 description 8
230000000694 effects Effects 0.000 description 8
229910052943 magnesium sulfate Inorganic materials 0.000 description 8
235000019341 magnesium sulphate Nutrition 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
238000001035 drying Methods 0.000 description 7
229940098779 methanesulfonic acid Drugs 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
235000011114 ammonium hydroxide Nutrition 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
239000000725 suspension Substances 0.000 description 5
DLNKOYKMWOXYQA-UHFFFAOYSA-N 2-amino-1-phenylpropan-1-ol Chemical compound CC(N)C(O)C1=CC=CC=C1 DLNKOYKMWOXYQA-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 4
229960001802 phenylephrine Drugs 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
102000005962 receptors Human genes 0.000 description 4
108020003175 receptors Proteins 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
239000012279 sodium borohydride Substances 0.000 description 4
229910000033 sodium borohydride Inorganic materials 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
238000003756 stirring Methods 0.000 description 4
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
239000004367 Lipase Substances 0.000 description 3
102000004882 Lipase Human genes 0.000 description 3
108090001060 Lipase Proteins 0.000 description 3
241000283973 Oryctolagus cuniculus Species 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
229940022663 acetate Drugs 0.000 description 3
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
230000001186 cumulative effect Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
235000019421 lipase Nutrition 0.000 description 3
TYRGLVWXHJRKMT-QMMMGPOBSA-N n-benzyloxycarbonyl-l-serine-betalactone Chemical compound OC(=O)[C@H](C)NC(=O)OCC1=CC=CC=C1 TYRGLVWXHJRKMT-QMMMGPOBSA-N 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
238000010992 reflux Methods 0.000 description 3
210000001519 tissue Anatomy 0.000 description 3
BCXOSCQTHVTUET-UHFFFAOYSA-N 1-(2-fluoro-5-nitrophenyl)ethanone Chemical compound CC(=O)C1=CC([N+]([O-])=O)=CC=C1F BCXOSCQTHVTUET-UHFFFAOYSA-N 0.000 description 2
WYTBQTMYNBKLHE-UHFFFAOYSA-N 1-(5-amino-2-fluorophenyl)ethanone Chemical compound CC(=O)C1=CC(N)=CC=C1F WYTBQTMYNBKLHE-UHFFFAOYSA-N 0.000 description 2
GVTGQNYTTLKHTK-UHFFFAOYSA-N 3-formyl-4-methoxybenzenesulfonyl chloride Chemical compound COC1=CC=C(S(Cl)(=O)=O)C=C1C=O GVTGQNYTTLKHTK-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
239000000048 adrenergic agonist Substances 0.000 description 2
229940126157 adrenergic receptor agonist Drugs 0.000 description 2
PPDJNZTUDFPAHX-UHFFFAOYSA-N benzyltrimethylammonium dichloroiodate Chemical compound Cl[I-]Cl.C[N+](C)(C)CC1=CC=CC=C1 PPDJNZTUDFPAHX-UHFFFAOYSA-N 0.000 description 2
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
PSEHHVRCDVOTID-NAVXHOJHSA-N chloro-bis[(1s,3s,4r,5s)-4,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]borane Chemical compound C([C@@H]([C@H]1C)B(Cl)[C@@H]2[C@@H](C)[C@@]3(C[C@](C2)(C3(C)C)[H])[H])[C@]2([H])C(C)(C)[C@@]1([H])C2 PSEHHVRCDVOTID-NAVXHOJHSA-N 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
MPTQRFCYZCXJFQ-UHFFFAOYSA-L copper(II) chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Cu+2] MPTQRFCYZCXJFQ-UHFFFAOYSA-L 0.000 description 2
-1 cyclic radicals Chemical class 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
230000007017 scission Effects 0.000 description 2
238000000926 separation method Methods 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
239000002904 solvent Substances 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 2
210000003708 urethra Anatomy 0.000 description 2
238000005303 weighing Methods 0.000 description 2
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
DNEKBRPLOLXERU-UHFFFAOYSA-N 2-(2-chlorosulfonylbenzoyl)benzenesulfonyl chloride Chemical class ClS(=O)(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1S(Cl)(=O)=O DNEKBRPLOLXERU-UHFFFAOYSA-N 0.000 description 1
CGLHUOBXGPKCHV-UHFFFAOYSA-N 2-azido-1-phenylpropan-1-ol Chemical compound [N-]=[N+]=NC(C)C(O)C1=CC=CC=C1 CGLHUOBXGPKCHV-UHFFFAOYSA-N 0.000 description 1
YOMBUJAFGMOIGS-UHFFFAOYSA-N 2-fluoro-1-phenylethanone Chemical compound FCC(=O)C1=CC=CC=C1 YOMBUJAFGMOIGS-UHFFFAOYSA-N 0.000 description 1
ATOOHBIWRYLVIE-UHFFFAOYSA-N 2-methoxy-1-phenylpropan-1-one Chemical compound COC(C)C(=O)C1=CC=CC=C1 ATOOHBIWRYLVIE-UHFFFAOYSA-N 0.000 description 1
YRNDGUSDBCARGC-UHFFFAOYSA-N 2-methoxyacetophenone Chemical compound COCC(=O)C1=CC=CC=C1 YRNDGUSDBCARGC-UHFFFAOYSA-N 0.000 description 1
RTLMATDNIKWIIO-UHFFFAOYSA-N 2-n,2-n,6-n,6-n-tetrakis(2-chloroethyl)-4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidine-2,6-diamine Chemical compound C=12N=C(N(CCCl)CCCl)N=C(N3CCCCC3)C2=NC(N(CCCl)CCCl)=NC=1N1CCCCC1 RTLMATDNIKWIIO-UHFFFAOYSA-N 0.000 description 1
HWALZZPNGXHTQE-UHFFFAOYSA-N 2-oxo-2-phenylethanesulfonamide Chemical class NS(=O)(=O)CC(=O)C1=CC=CC=C1 HWALZZPNGXHTQE-UHFFFAOYSA-N 0.000 description 1
LVLVILNNIYRTAM-UHFFFAOYSA-N 3-(2-amino-1-hydroxyethyl)-4-fluorobenzenesulfonamide Chemical compound NCC(O)C1=CC(S(N)(=O)=O)=CC=C1F LVLVILNNIYRTAM-UHFFFAOYSA-N 0.000 description 1
ZPAOCHHOIWSAFA-UHFFFAOYSA-N 3-(3-sulfamoylbenzoyl)benzenesulfonamide Chemical class NS(=O)(=O)C1=CC=CC(C(=O)C=2C=C(C=CC=2)S(N)(=O)=O)=C1 ZPAOCHHOIWSAFA-UHFFFAOYSA-N 0.000 description 1
FMWFGTCTSJNEDX-UHFFFAOYSA-N 3-formylbenzenesulfonamide Chemical class NS(=O)(=O)C1=CC=CC(C=O)=C1 FMWFGTCTSJNEDX-UHFFFAOYSA-N 0.000 description 1
VXITZYGVHSIVEQ-UHFFFAOYSA-N 3-formylbenzenesulfonyl chloride Chemical class ClS(=O)(=O)C1=CC=CC(C=O)=C1 VXITZYGVHSIVEQ-UHFFFAOYSA-N 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
241000228212 Aspergillus Species 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
108020004511 Recombinant DNA Proteins 0.000 description 1
229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
206010046543 Urinary incontinence Diseases 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000000556 agonist Substances 0.000 description 1
150000001351 alkyl iodides Chemical class 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
210000000702 aorta abdominal Anatomy 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000003935 benzaldehydes Chemical class 0.000 description 1
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical class C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
229940007550 benzyl acetate Drugs 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
GSEZYWGNEACOIW-UHFFFAOYSA-N bis(2-aminophenyl)methanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1N GSEZYWGNEACOIW-UHFFFAOYSA-N 0.000 description 1
GKQPYCWSUVGAGJ-UHFFFAOYSA-N bis(2-nitrophenyl)methanone Chemical class [O-][N+](=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1[N+]([O-])=O GKQPYCWSUVGAGJ-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910000085 borane Inorganic materials 0.000 description 1
229910052796 boron 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
229910002091 carbon monoxide Inorganic materials 0.000 description 1
210000004978 chinese hamster ovary cell Anatomy 0.000 description 1
239000003245 coal Substances 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
230000007071 enzymatic hydrolysis Effects 0.000 description 1
238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
210000001105 femoral artery Anatomy 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
238000003304 gavage Methods 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000002329 infrared spectrum Methods 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
FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
210000004731 jugular vein Anatomy 0.000 description 1
239000007788 liquid Substances 0.000 description 1
210000005228 liver tissue Anatomy 0.000 description 1
210000003975 mesenteric artery Anatomy 0.000 description 1
CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
229960001412 pentobarbital Drugs 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
239000012071 phase Substances 0.000 description 1
238000003408 phase transfer catalysis Methods 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 description 1
229960001289 prazosin Drugs 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
210000003079 salivary gland Anatomy 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 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
NYBWUHOMYZZKOR-UHFFFAOYSA-N tes-adt Chemical class C1=C2C(C#C[Si](CC)(CC)CC)=C(C=C3C(SC=C3)=C3)C3=C(C#C[Si](CC)(CC)CC)C2=CC2=C1SC=C2 NYBWUHOMYZZKOR-UHFFFAOYSA-N 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- 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
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
- 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
- A61P13/00—Drugs for disorders of the urinary system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Urology & Nephrology (AREA)
Endocrinology (AREA)
Diabetes (AREA)
Epidemiology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO980471A 1995-08-04 1998-02-03 Benzensulfonamidforbindelser, deres fremstilling samt medikament og farmasöytisk preparat inneholdende disse NO309563B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9509503A FR2737494B1 (fr)	1995-08-04	1995-08-04	Derives de benzenesulfonamide, leur preparation et leur application en therapeutique
PCT/FR1996/001215 WO1997006136A1 (fr)	1995-08-04	1996-08-01	Derives de benzenesulfonamide, leur preparation et leurs applications en therapeutique

Publications (3)

Publication Number	Publication Date
NO980471D0 NO980471D0 (no)	1998-02-03
NO980471L NO980471L (no)	1998-04-06
NO309563B1 true NO309563B1 (no)	2001-02-19

Family

ID=9481713

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO980471A NO309563B1 (no)	1995-08-04	1998-02-03	Benzensulfonamidforbindelser, deres fremstilling samt medikament og farmasöytisk preparat inneholdende disse

Country Status (29)

Country	Link
US (1)	US6214882B1 (de)
EP (1)	EP0842148B1 (de)
JP (1)	JPH11510175A (de)
KR (1)	KR19990029070A (de)
CN (1)	CN1198735A (de)
AR (1)	AR003972A1 (de)
AT (1)	ATE198192T1 (de)
AU (1)	AU714948B2 (de)
BR (1)	BR9609698A (de)
CA (1)	CA2227912A1 (de)
CO (1)	CO4750816A1 (de)
CZ (1)	CZ30898A3 (de)
DE (1)	DE69611303T2 (de)
DK (1)	DK0842148T3 (de)
ES (1)	ES2154414T3 (de)
FR (1)	FR2737494B1 (de)
GR (1)	GR3035493T3 (de)
HU (1)	HUP9900064A3 (de)
IL (1)	IL123156A (de)
MX (1)	MX9800963A (de)
NO (1)	NO309563B1 (de)
NZ (1)	NZ315362A (de)
PL (1)	PL324778A1 (de)
PT (1)	PT842148E (de)
RU (1)	RU2160729C2 (de)
SK (1)	SK282423B6 (de)
TW (1)	TW336929B (de)
WO (1)	WO1997006136A1 (de)
ZA (1)	ZA966616B (de)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2761061B1 (fr) *	1997-03-20	1999-04-23	Synthelabo	Derives de benzenesulfonamide, leur preparation et leur application en therapeutique
FR2768054A1 (fr) *	1997-09-11	1999-03-12	Synthelabo	Utilisation de derives de benzene sulfonamide pour obtenir un medicament destine au traitement de l'ejaculation retrograde ou de l'aspermie
FR2768055A1 (fr)	1997-09-11	1999-03-12	Synthelabo	Utilisation de derives de sulfonanilide pour obtenir un medicament destine au traitement de l'ejaculation retrograde ou de l'aspermie
AU2855999A (en) *	1998-03-25	1999-10-18	Godo Shusei Co., Ltd.	Sulfonylurea derivatives and drugs containing the same
CA2411013A1 (en) *	2000-06-07	2001-12-13	Jose Manuel Prieto Soto	6-phenylpyrrolopyrimidinedione derivatives
DE10104369A1 (de) *	2001-02-01	2002-08-08	Boehringer Ingelheim Pharma	Verwendung von 2-Amino-(4-hydroxy-2-methansulfonamidophenyl)ethanol zur Behandlung der Harninkontinenz
AU2003237518B8 (en) *	2002-06-11	2009-03-12	Arqule, Inc.	Substituted phenylsulfonamide inhibitors of beta amyloid production
EP1680406A1 (de) *	2003-10-29	2006-07-19	Elan Pharmaceuticals, Inc.	N-substituierte benzolsulfonamide
JP5406525B2 (ja) *	2005-07-04	2014-02-05	ツァナン・サイテック・カンパニー・リミテッド	ルテニウム錯体配位子、ルテニウム錯体、固定化ルテニウム錯体触媒及びその調製方法と用途

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3943254A (en) *	1973-08-20	1976-03-09	Smithkline Corporation	Beta-adrenergic antagonists
US3860647A (en) *	1973-08-20	1975-01-14	Smithkline Corp	{60 -Aminomethyl-4-hydroxy-3-sulfamyl-benzyl alcohols and 4-hydroxy-3-sulfamyl phenethylamines
GB1593651A (en) *	1977-02-03	1981-07-22	Allen & Hanburys Ltd	Amides
CA1147342A (en) *	1977-10-12	1983-05-31	Kazuo Imai	Process of producing novel phenylethanolamine derivatives
JPS56110665A (en) *	1980-02-08	1981-09-01	Yamanouchi Pharmaceut Co Ltd	Sulfamoyl-substituted phenetylamine derivative and its preparation
JPS6051106A (ja) *	1983-08-31	1985-03-22	Yamanouchi Pharmaceut Co Ltd	塩酸アモスラロ−ル持続性製剤
FR2581993B1 (fr)	1985-05-14	1988-03-18	Synthelabo	Derives de (benzoyl-4 piperidino)-2 phenyl-1 alcanols, leur preparation et leur application en therapeutique
JPH0819084B2 (ja)	1990-02-07	1996-02-28	日本新薬株式会社	スルホンアニリド誘導体及び医薬
GB9020695D0 (en) *	1990-09-22	1990-11-07	Wellcome Found	Anti-hypertensive tetralins
BR9306399A (pt) *	1992-05-22	1998-09-15	Senju Pharma Co	Composição farmacéutica para uso no tratamento de glaucoma

1995
- 1995-08-04 FR FR9509503A patent/FR2737494B1/fr not_active Expired - Fee Related
1996
- 1996-07-31 AR ARP960103821A patent/AR003972A1/es unknown
- 1996-08-01 IL IL12315696A patent/IL123156A/en not_active IP Right Cessation
- 1996-08-01 AT AT96927119T patent/ATE198192T1/de not_active IP Right Cessation
- 1996-08-01 KR KR1019980700374A patent/KR19990029070A/ko not_active Ceased
- 1996-08-01 BR BR9609698A patent/BR9609698A/pt not_active Application Discontinuation
- 1996-08-01 RU RU98103460/04A patent/RU2160729C2/ru active
- 1996-08-01 SK SK146-98A patent/SK282423B6/sk unknown
- 1996-08-01 WO PCT/FR1996/001215 patent/WO1997006136A1/fr not_active Ceased
- 1996-08-01 CN CN96197428A patent/CN1198735A/zh active Pending
- 1996-08-01 DE DE69611303T patent/DE69611303T2/de not_active Expired - Fee Related
- 1996-08-01 PT PT96927119T patent/PT842148E/pt unknown
- 1996-08-01 NZ NZ315362A patent/NZ315362A/en unknown
- 1996-08-01 CA CA002227912A patent/CA2227912A1/en not_active Abandoned
- 1996-08-01 AU AU67052/96A patent/AU714948B2/en not_active Ceased
- 1996-08-01 MX MX9800963A patent/MX9800963A/es unknown
- 1996-08-01 PL PL96324778A patent/PL324778A1/xx unknown
- 1996-08-01 HU HU9900064A patent/HUP9900064A3/hu unknown
- 1996-08-01 JP JP9508160A patent/JPH11510175A/ja active Pending
- 1996-08-01 DK DK96927119T patent/DK0842148T3/da active
- 1996-08-01 ES ES96927119T patent/ES2154414T3/es not_active Expired - Lifetime
- 1996-08-01 EP EP96927119A patent/EP0842148B1/de not_active Expired - Lifetime
- 1996-08-01 CZ CZ98308A patent/CZ30898A3/cs unknown
- 1996-08-01 US US09/000,336 patent/US6214882B1/en not_active Expired - Fee Related
- 1996-08-02 ZA ZA9606616A patent/ZA966616B/xx unknown
- 1996-08-02 CO CO96041035A patent/CO4750816A1/es unknown
- 1996-08-02 TW TW085109360A patent/TW336929B/zh active
1998
- 1998-02-03 NO NO980471A patent/NO309563B1/no not_active IP Right Cessation
2001
- 2001-02-28 GR GR20010400336T patent/GR3035493T3/el not_active IP Right Cessation

Also Published As

Publication number	Publication date
GR3035493T3 (en)	2001-05-31
FR2737494B1 (fr)	1997-08-29
EP0842148A1 (de)	1998-05-20
DK0842148T3 (da)	2001-04-30
ATE198192T1 (de)	2001-01-15
SK282423B6 (sk)	2002-01-07
JPH11510175A (ja)	1999-09-07
IL123156A0 (en)	1998-09-24
HUP9900064A3 (en)	2001-11-28
PT842148E (pt)	2001-05-31
BR9609698A (pt)	1999-03-23
EP0842148B1 (de)	2000-12-20
CO4750816A1 (es)	1999-03-31
CZ30898A3 (cs)	1998-07-15
US6214882B1 (en)	2001-04-10
PL324778A1 (en)	1998-06-08
CA2227912A1 (en)	1997-02-20
CN1198735A (zh)	1998-11-11
AU714948B2 (en)	2000-01-13
TW336929B (en)	1998-07-21
HUP9900064A2 (hu)	1999-05-28
DE69611303T2 (de)	2001-07-05
MX9800963A (es)	1998-04-30
NO980471L (no)	1998-04-06
DE69611303D1 (de)	2001-01-25
IL123156A (en)	2001-10-31
ZA966616B (en)	1997-02-18
NO980471D0 (no)	1998-02-03
ES2154414T3 (es)	2001-04-01
HK1010868A1 (en)	1999-07-02
WO1997006136A1 (fr)	1997-02-20
AU6705296A (en)	1997-03-05
NZ315362A (en)	1999-04-29
RU2160729C2 (ru)	2000-12-20
AR003972A1 (es)	1998-09-30
SK14698A3 (en)	1998-10-07
KR19990029070A (ko)	1999-04-15
FR2737494A1 (fr)	1997-02-07

Legal Events

Date	Code	Title	Description
2003-04-07	MM1K	Lapsed by not paying the annual fees	Free format text: LAPSED IN FEBRUARY 2003

Publication	Publication Date	Title
HUT65489A (en)	1994-06-28	Process for producing of indole derivatives and pharmaceutical compositions comprising them
EA003245B1 (ru)	2003-02-27	Производные бензамида и фармацевтическая композиция на их основе
JPH0631235B2 (ja)	1994-04-27	ピリダジノン誘導体
EP0135177A2 (de)	1985-03-27	Benzocycloalkanderivate
NO161971B (no)	1989-07-10	Analogifremgangsmaate ved fremstilling av tetrahydronaftalinderivater.
US6214882B1 (en)	2001-04-10	Benzenesulphonamide derivatives, preparation thereof and therapeutical uses thereof
EP0207345B1 (de)	1992-01-22	4,7-Dihydrothieno[2,3-b]pyridinderivate, Verfahren zu ihrer Herstellung und Mittel für kardiovaskuläre Krankheiten
MXPA98000963A (en)	1998-04-01	Derivatives of benzene sulfonamide, its preparation and its applications in terapeut
NO773300L (no)	1978-03-29	Fremgangsmaate for fremstilling av nye eddiksyrederivater
US5210276A (en)	1993-05-11	Phenylethanolamino- and phenylethanolaminomethyl-tetralines, process for the preparation thereof, intermediates in said process and pharmaceutical compositions containing them
IE883136L (en)	1989-05-19	Ó(2)-adreno receptor antagonists
US5185362A (en)	1993-02-09	Diphenylamine cardiovascular agents, compositions and use
RU2491278C2 (ru)	2013-08-27	Гетероциклические производные индана, используемые для снятия боли и лечения состояний, подобных глаукоме
CA1292739C (en)	1991-12-03	Heteroaromatic acetylenes useful as antihypertensive agents
NO178108B (no)	1995-10-16	Salter av hydrazoner, farmasöytiske preparater inneholdende saltene samt anvendelse av saltene
US4446151A (en)	1984-05-01	Decarboxylase-inhibiting fluorinated pentane diamine derivatives
WO2001085698A1 (en)	2001-11-15	New polycyclic indanylimidazoles with alpha2 adrenergic activity
AU2001258469A1 (en)	2002-02-07	New polycyclic indanylimidazoles with alpha2 adrenergic activity
CA2111439A1 (en)	1992-12-23	Aminoalkyl-substituted 5-mercaptothiazoles, the preparation and use thereof
KR820001235B1 (ko)	1982-07-07	알킬티오페녹시프로파놀아민의 제조방법
HK1010868B (en)	2001-06-22	Benzenesulphonamide derivatives, preparation thereof and therapeutical uses thereof
BR112020001396B1 (pt)	2025-06-03	Intermediários úteis na síntese de derivados de aminopirimidina, processo para preparar os mesmos e processo para preparar derivados de aminopirimidina usando os mesmos
JPS5896057A (ja)	1983-06-07	メルカプトアルキルアミン
JPS62132845A (ja)	1987-06-16	Ｎ，ｎ−二置換フエニルセリン誘導体及びそれを有効成分とする中枢神経系用剤
PL98633B1 (pl)	1978-05-31	Sposob wytwarzania nowych pochodnych 1-fenoksy-3-aminopropanolu-2