CS275837B6 - Method of production of new cycloalkan0-|1,2b¨-indole sulfonamides - Google Patents

Method of production of new cycloalkan0-|1,2b¨-indole sulfonamides Download PDF

Info

Publication number: CS275837B6
Authority: CS; Czechoslovakia
Prior art keywords: cycloalkano; tetrahydrocarbazole; carboxyethyl; mol; formula
Prior art date: 1986-02-21

Application number

CS871093A

Other languages

Czech (cs)

English (en)

Other versions

CS8701093A2 (en

Inventor

Horst Dr Boshagen

Ulrich Dr Rosentreter

Folker Dr Lieb

Hermann Dr Oediger

Friedel Dr Seuter

Elisabeth Dr Perzborn

Volker-Bernd Dr Fiedler

Original Assignee

Bayer Ag

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.)

1986-02-21

Filing date

1987-02-19

Publication date

1992-03-18

1987-02-19 Application filed by Bayer Ag filed Critical Bayer Ag

1987-02-19 Priority to CS886891A priority Critical patent/CS276468B6/cs

1988-10-19 Priority to CS886892A priority patent/CS276469B6/cs

1990-11-14 Publication of CS8701093A2 publication Critical patent/CS8701093A2/cs

1992-03-18 Publication of CS275837B6 publication Critical patent/CS275837B6/cs

Links

238000000034 method Methods 0.000 title claims description 34
229940124530 sulfonamide Drugs 0.000 title claims description 5
238000004519 manufacturing process Methods 0.000 title claims description 4
-1 4-Fluorophenylsulfonamido Chemical group 0.000 claims description 70
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 44
150000001875 compounds Chemical class 0.000 claims description 34
239000000460 chlorine Chemical group 0.000 claims description 26
230000008569 process Effects 0.000 claims description 26
125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 25
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 22
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 22
238000006243 chemical reaction Methods 0.000 claims description 16
238000002360 preparation method Methods 0.000 claims description 15
RYMYQAMZUWJAEO-UHFFFAOYSA-N 1h-indole-2-sulfonamide Chemical class C1=CC=C2NC(S(=O)(=O)N)=CC2=C1 RYMYQAMZUWJAEO-UHFFFAOYSA-N 0.000 claims description 14
229910052731 fluorine Inorganic materials 0.000 claims description 14
125000001153 fluoro group Chemical group F* 0.000 claims description 12
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 9
150000002367 halogens Chemical class 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 8
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
125000001309 chloro group Chemical group Cl* 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
239000012442 inert solvent Substances 0.000 claims description 7
208000010110 spontaneous platelet aggregation Diseases 0.000 claims description 7
239000003638 chemical reducing agent Substances 0.000 claims description 6
239000007858 starting material Substances 0.000 claims description 6
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
239000004480 active ingredient Substances 0.000 claims description 5
230000002401 inhibitory effect Effects 0.000 claims description 5
239000000825 pharmaceutical preparation Substances 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
150000002475 indoles Chemical class 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
230000003042 antagnostic effect Effects 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
150000005248 indolsulfonamides Chemical class 0.000 claims description 2
150000003456 sulfonamides Chemical class 0.000 claims description 2
125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 156
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 137
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 98
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 57
239000000243 solution Substances 0.000 description 52
239000002904 solvent Substances 0.000 description 49
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 45
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
239000000047 product Substances 0.000 description 45
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 37
235000019439 ethyl acetate Nutrition 0.000 description 33
239000011541 reaction mixture Substances 0.000 description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
239000000203 mixture Substances 0.000 description 23
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 20
238000002844 melting Methods 0.000 description 20
230000008018 melting Effects 0.000 description 20
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
229910052938 sodium sulfate Inorganic materials 0.000 description 14
235000011152 sodium sulphate Nutrition 0.000 description 14
239000012074 organic phase Substances 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
229960000583 acetic acid Drugs 0.000 description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
238000001816 cooling Methods 0.000 description 11
238000001704 evaporation Methods 0.000 description 11
230000008020 evaporation Effects 0.000 description 11
238000010992 reflux Methods 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
159000000000 sodium salts Chemical class 0.000 description 10
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 8
239000013078 crystal Substances 0.000 description 8
235000019441 ethanol Nutrition 0.000 description 8
239000012362 glacial acetic acid Substances 0.000 description 8
239000012071 phase Substances 0.000 description 8
239000008259 solid foam Substances 0.000 description 8
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
239000008346 aqueous phase Substances 0.000 description 7
239000002585 base Substances 0.000 description 7
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 7
229940067157 phenylhydrazine Drugs 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
238000003756 stirring Methods 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
UFRCIKMHUAOIAT-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazol-3-amine Chemical compound N1C2=CC=CC=C2C2=C1CCC(N)C2 UFRCIKMHUAOIAT-UHFFFAOYSA-N 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 6
239000003814 drug Substances 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
LDXDSHIEDAPSSA-UHFFFAOYSA-N ramatroban Chemical compound C1C=2C3=CC=CC=C3N(CCC(=O)O)C=2CCC1NS(=O)(=O)C1=CC=C(F)C=C1 LDXDSHIEDAPSSA-UHFFFAOYSA-N 0.000 description 6
230000037396 body weight Effects 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
238000005984 hydrogenation reaction Methods 0.000 description 5
230000003287 optical effect Effects 0.000 description 5
239000002245 particle Substances 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 4
NUBNZASXRSXFRW-UHFFFAOYSA-N 3-(aminomethyl)cyclopentan-1-ol Chemical compound NCC1CCC(O)C1 NUBNZASXRSXFRW-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
239000012043 crude product Substances 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
238000000605 extraction Methods 0.000 description 4
239000006260 foam Substances 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
239000003960 organic solvent Substances 0.000 description 4
CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
WFTIZANRIDXCBN-UHFFFAOYSA-N 3-(aminomethyl)cyclohexan-1-ol Chemical compound NCC1CCCC(O)C1 WFTIZANRIDXCBN-UHFFFAOYSA-N 0.000 description 3
KZRJSGQVSDJUFG-UHFFFAOYSA-N 3-(nitromethyl)cyclohexan-1-one Chemical compound [O-][N+](=O)CC1CCCC(=O)C1 KZRJSGQVSDJUFG-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
239000005909 Kieselgur Substances 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
RKOTXQYWCBGZLP-UHFFFAOYSA-N N-[(2,4-difluorophenyl)methyl]-2-ethyl-9-hydroxy-3-methoxy-1,8-dioxospiro[3H-pyrido[1,2-a]pyrazine-4,3'-oxolane]-7-carboxamide Chemical compound CCN1C(OC)C2(CCOC2)N2C=C(C(=O)NCC3=C(F)C=C(F)C=C3)C(=O)C(O)=C2C1=O RKOTXQYWCBGZLP-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
150000008044 alkali metal hydroxides Chemical class 0.000 description 3
239000008280 blood Substances 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
230000008859 change Effects 0.000 description 3
229940117975 chromium trioxide Drugs 0.000 description 3
WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 3
GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 3
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000003480 eluent Substances 0.000 description 3
239000000284 extract Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
238000007127 saponification reaction Methods 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
235000012222 talc Nutrition 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
OQUFOZNPBIIJTN-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;sodium Chemical compound [Na].OC(=O)CC(O)(C(O)=O)CC(O)=O OQUFOZNPBIIJTN-UHFFFAOYSA-N 0.000 description 2
OXUCMXDWKATUHP-UHFFFAOYSA-N 3-(nitromethyl)cyclopentan-1-one Chemical compound [O-][N+](=O)CC1CCC(=O)C1 OXUCMXDWKATUHP-UHFFFAOYSA-N 0.000 description 2
YGLVMWDIVATCKD-UHFFFAOYSA-N 3-[3-[(4-chlorophenyl)sulfonylamino]-1,2,3,4-tetrahydrocarbazol-9-yl]propanoic acid Chemical compound C1C=2C3=CC=CC=C3N(CCC(=O)O)C=2CCC1NS(=O)(=O)C1=CC=C(Cl)C=C1 YGLVMWDIVATCKD-UHFFFAOYSA-N 0.000 description 2
PLPQNBFCZVJMGW-UHFFFAOYSA-N 4-chloro-n-[(3-oxocyclopentyl)methyl]benzenesulfonamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NCC1CC(=O)CC1 PLPQNBFCZVJMGW-UHFFFAOYSA-N 0.000 description 2
LFLSATHZMYYIAQ-UHFFFAOYSA-N 4-flourobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(F)C=C1 LFLSATHZMYYIAQ-UHFFFAOYSA-N 0.000 description 2
RTHFTKRMIQNVER-UHFFFAOYSA-N 4-fluoro-n-(2,3,4,9-tetrahydro-1h-carbazol-4-ylmethyl)benzenesulfonamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)NCC1C(C2=CC=CC=C2N2)=C2CCC1 RTHFTKRMIQNVER-UHFFFAOYSA-N 0.000 description 2
DTJZKMBCVOPNIX-UHFFFAOYSA-N 4-fluoro-n-[(3-hydroxycyclopentyl)methyl]benzenesulfonamide Chemical compound C1C(O)CCC1CNS(=O)(=O)C1=CC=C(F)C=C1 DTJZKMBCVOPNIX-UHFFFAOYSA-N 0.000 description 2
OTHRCAURITYYNT-UHFFFAOYSA-N 4-fluoro-n-[(3-oxocyclohexyl)methyl]benzenesulfonamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)NCC1CC(=O)CCC1 OTHRCAURITYYNT-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
BZKFMUIJRXWWQK-UHFFFAOYSA-N Cyclopentenone Chemical compound O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 2
229910001863 barium hydroxide Inorganic materials 0.000 description 2
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 2
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000000969 carrier Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
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235000011803 sesame oil Nutrition 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
YYVAQBRMUPGCDE-UHFFFAOYSA-N spiro[1,2,4,9-tetrahydrocarbazole-3,2'-1,3-dioxolane] Chemical compound O1CCOC11CC(C2=CC=CC=C2N2)=C2CC1 YYVAQBRMUPGCDE-UHFFFAOYSA-N 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000004575 stone Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
238000012360 testing method Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
AKQNYQDSIDKVJZ-UHFFFAOYSA-N triphenylsilane Chemical compound C1=CC=CC=C1[SiH](C=1C=CC=CC=1)C1=CC=CC=C1 AKQNYQDSIDKVJZ-UHFFFAOYSA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000002699 waste material Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Pulmonology (AREA)
Immunology (AREA)
Diabetes (AREA)
Hematology (AREA)
Indole Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CS871093A 1986-02-21 1987-02-19 Method of production of new cycloalkan0-|1,2b¨-indole sulfonamides CS275837B6 (en)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
CS886891A CS276468B6 (cs)	1986-02-21	1987-02-19	Způsob výroby nových /fenylsulfonamidoalkyl/ /fenylsulfonamido/eykloalkano/l,2-b/indolů
CS886892A CS276469B6 (cs)	1986-02-21	1988-10-19	Způsob výroby cykloalkanonsulfonamidů

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE3605566		1986-02-21
DE19863631824 DE3631824A1 (de)	1986-02-21	1986-09-19	Cycloalkano(1.2-b)indol-sulfonamide

Publications (2)

Publication Number	Publication Date
CS8701093A2 CS8701093A2 (en)	1990-11-14
CS275837B6 true CS275837B6 (en)	1992-03-18

Family

ID=25841196

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS871093A CS275837B6 (en)	1986-02-21	1987-02-19	Method of production of new cycloalkan0-\|1,2b¨-indole sulfonamides

Country Status (19)

Country	Link
US (3)	US4827032A (ja)
EP (1)	EP0242518B1 (ja)
JP (1)	JPH075552B2 (ja)
KR (2)	KR940007302B1 (ja)
AU (1)	AU595855B2 (ja)
CA (1)	CA1309414C (ja)
CS (1)	CS275837B6 (ja)
DE (2)	DE3631824A1 (ja)
DK (1)	DK167009B1 (ja)
ES (1)	ES2028801T3 (ja)
FI (1)	FI86544C (ja)
GR (1)	GR3001763T3 (ja)
HU (1)	HU198686B (ja)
IE (1)	IE59470B1 (ja)
IL (1)	IL81611A (ja)
NO (1)	NO171633C (ja)
NZ (1)	NZ219319A (ja)
PH (1)	PH24491A (ja)
PT (1)	PT84316B (ja)

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GB9008108D0 (en) *	1990-04-10	1990-06-06	Bayer Ag	Cycloalkano(b)dihydroindoles and-indolesulphonamides substituted by heterocycles
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US5708187A (en) *	1996-06-27	1998-01-13	Eli Lilly And Company	6-substituted-1,2,3,4-tetrahydro-9H-carbazoles and 7-substituted-10H-cyclohepta 7,6-B!indoles: New 5-HT1F agonists
DE19757983A1 (de) *	1997-12-24	1999-07-01	Bayer Yakuhin Ltd	Thermodynamisch stabile Form von (r)-3[[(4-Fluorophenyl)sulfonyl]amino]-1,2,3,4-tetrahydro-9H-carbazol-0-propansäure (Ramatroban)
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US7601856B2 (en) *	2006-07-27	2009-10-13	Wyeth	Benzofurans as potassium ion channel modulators
US7662831B2 (en) *	2006-07-27	2010-02-16	Wyeth Llc	Tetracyclic indoles as potassium channel modulators
MY147588A (en)	2006-08-07	2012-12-31	Actelion Pharmaceuticals Ltd	(3-amino-1,2,3,4-tetrahydro-9h-carbazol-9-yl)-acetic acid derivatives
GB0624087D0 (en) *	2006-12-01	2007-01-10	Selamine Ltd	Ramipril combination salt
GB0624084D0 (en) *	2006-12-01	2007-01-10	Selamine Ltd	Ramipril amino acid salts
GB0624090D0 (en) *	2006-12-01	2007-01-10	Selamine Ltd	Ramipril amine salts
AU2007336077A1 (en) *	2006-12-20	2008-06-26	Cardoz Ab	New combination for use in the treatment of inflammatory disorders
WO2008087371A1 (en) *	2007-01-16	2008-07-24	Cardoz Ab	New combination for use in the treatment of inflammatory disorders
WO2009007674A2 (en) *	2007-07-11	2009-01-15	Cardoz Ab	Combination for use in the treatment of atherosclerosis comprising a mast cell inhibitor and ramatroban or seratrodast
JP2011526281A (ja) *	2008-06-24	2011-10-06	アミラファーマシューティカルズ，インク．	プロスタグランジンｄ２受容体のシクロアルカン［ｂ］インドールアンタゴニスト
EP2307382B1 (en) *	2008-07-15	2011-12-21	F. Hoffmann-La Roche AG	Aminotetrahydroindazoloacetic acids
RS52809B (sr)	2008-11-17	2013-10-31	F. Hoffmann-La Roche Ag.	Naftilsirćetne kiseline
RU2011124149A (ru)	2008-11-17	2012-12-27	Ф.Хоффманн-Ля Рош Аг	Нафтилуксусные кислоты
US8188090B2 (en)	2008-11-17	2012-05-29	Hoffman-La Roche Inc.	Naphthylacetic acids
CA2790139C (en)	2010-03-22	2018-03-13	Actelion Pharmaceuticals Ltd	3-(heteroaryl-amino)-1,2,3,4-tetrahydro-9h-carbazole derivatives and their use as prostaglandin d2 receptor modulators
JP5964945B2 (ja)	2011-04-14	2016-08-03	アクテリオンファーマシューティカルズリミテッドＡｃｔｅｌｉｏｎＰｈａｒｍａｃｅｕｔｉｃａｌｓＬｔｄ	７−（ヘテロアリ−ル−アミノ）−６，７，８，９−テトラヒドロピリド［１，２−ａ］インド−ル酢酸誘導体及びプロスタグランジンＤ２受容体調節剤としてのそれらの使用
US8470884B2 (en)	2011-11-09	2013-06-25	Hoffmann-La Roche Inc.	Alkenyl naphthylacetic acids
CA2939892C (en)	2014-03-17	2020-03-31	Idorsia Pharmaceuticals Ltd	Azaindole acetic acid derivatives and their use as prostaglandin d2 receptor modulators
CN106103437A (zh)	2014-03-18	2016-11-09	埃科特莱茵药品有限公司	氮杂吲哚乙酸衍生物及其作为前列腺素d2受体调节剂的用途
WO2016128565A1 (en)	2015-02-13	2016-08-18	Institut National De La Sante Et De La Recherche Medicale (Inserm)	Ptgdr-1 and/or ptgdr-2 antagonists for preventing and/or treating systemic lupus erythematosus
CN108026093B (zh)	2015-09-15	2021-11-16	爱杜西亚药品有限公司	结晶形式

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1986
- 1986-09-19 DE DE19863631824 patent/DE3631824A1/de not_active Withdrawn
1987
- 1987-02-04 NO NO870437A patent/NO171633C/no unknown
- 1987-02-11 EP EP87101901A patent/EP0242518B1/de not_active Expired - Lifetime
- 1987-02-11 ES ES198787101901T patent/ES2028801T3/es not_active Expired - Lifetime
- 1987-02-11 DE DE8787101901T patent/DE3769191D1/de not_active Expired - Lifetime
- 1987-02-13 AU AU68808/87A patent/AU595855B2/en not_active Expired
- 1987-02-18 IL IL81611A patent/IL81611A/xx not_active IP Right Cessation
- 1987-02-18 NZ NZ219319A patent/NZ219319A/en unknown
- 1987-02-19 HU HU87650A patent/HU198686B/hu unknown
- 1987-02-19 PT PT84316A patent/PT84316B/pt not_active IP Right Cessation
- 1987-02-19 PH PH34883A patent/PH24491A/en unknown
- 1987-02-19 CA CA000530077A patent/CA1309414C/en not_active Expired - Lifetime
- 1987-02-19 FI FI870693A patent/FI86544C/fi not_active IP Right Cessation
- 1987-02-19 CS CS871093A patent/CS275837B6/cs unknown
- 1987-02-20 IE IE43987A patent/IE59470B1/en not_active IP Right Cessation
- 1987-02-20 DK DK087187A patent/DK167009B1/da not_active IP Right Cessation
- 1987-02-20 KR KR1019870001410A patent/KR940007302B1/ko not_active Expired - Lifetime
- 1987-07-31 KR KR87008383A patent/KR960001914B1/ko not_active Expired - Fee Related
1988
- 1988-06-29 US US07/212,840 patent/US4827032A/en not_active Expired - Lifetime
1989
- 1989-02-08 US US07/308,152 patent/US4904797A/en not_active Expired - Lifetime
- 1989-11-28 US US07/442,043 patent/US4965258A/en not_active Expired - Lifetime
1991
- 1991-04-11 GR GR91400361T patent/GR3001763T3/el unknown
1992
- 1992-02-27 JP JP4076232A patent/JPH075552B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
IE59470B1 (en)	1994-03-09
DK87187D0 (da)	1987-02-20
KR940007302B1 (ko)	1994-08-12
FI86544C (fi)	1992-09-10
GR3001763T3 (en)	1992-11-23
AU595855B2 (en)	1990-04-12
JPH075552B2 (ja)	1995-01-25
DK167009B1 (da)	1993-08-16
NO870437D0 (no)	1987-02-04
NO171633B (no)	1993-01-04
NO171633C (no)	1993-04-14
KR870007885A (ko)	1987-09-22
US4827032A (en)	1989-05-02
AU6880887A (en)	1987-08-27
KR960001914B1 (en)	1996-02-06
PT84316A (en)	1987-03-01
FI86544B (fi)	1992-05-29
US4904797A (en)	1990-02-27
HUT44493A (en)	1988-03-28
IE870439L (en)	1987-08-21
DE3769191D1 (de)	1991-05-16
US4965258A (en)	1990-10-23
NZ219319A (en)	1990-12-21
CA1309414C (en)	1992-10-27
PH24491A (en)	1990-07-18
FI870693A7 (fi)	1987-08-22
ES2028801T3 (es)	1992-07-16
PT84316B (pt)	1989-09-14
IL81611A (en)	1991-03-10
EP0242518A1 (de)	1987-10-28
CS8701093A2 (en)	1990-11-14
NO870437L (no)	1987-08-24
DK87187A (da)	1987-08-22
KR890001982A (ko)	1989-04-07
EP0242518B1 (de)	1991-04-10
JPH0592954A (ja)	1993-04-16
FI870693A0 (fi)	1987-02-19
DE3631824A1 (de)	1988-03-31
HU198686B (en)	1989-11-28

Publication	Publication Date	Title
DK167009B1 (da)	1993-08-16	Cycloalkanooe1,2-baaindolsulfonamider, isomere og fysiologisk acceptable salte deraf, deres fremstilling og anvendelse samt laegemiddel indeholdende dem
JP3560986B2 (ja)	2004-09-02	５―ｈｔ２ｃ受容体作用薬及びアミノアルキルインダゾール誘導体
BE1006343A5 (fr)	1994-07-26	Derives de l'indole.
EP0077754B1 (en)	1990-09-26	Novel pharmaceutically active 1,2,3,4,4a,5,10,10a-octahydrobenzo(g)quinoline derivatives
EP0307303B1 (fr)	1991-12-04	[(Pyrimidinyl-2)-aminoalkyl]-1 pipéridines, leur préparation et leur application en thérapeutique
EP0581939A1 (fr)	1994-02-09	Derives du n-sulfonyl-2-oxoindole ayant une affinite pour les recepteurs de la vasopressine et/ou de l'ocytocine
EP0370901A1 (fr)	1990-05-30	Nouveaux dérivés du chromanne actifs sur le système nerveux central, leur procédé de préparation et les compositions pharmaceutiques en contenant
EP0373998A1 (fr)	1990-06-20	Ethers d'oxime de propénone, procédé pour leur préparation et compositions pharmaceutiques les contenant
FR2659323A1 (fr)	1991-09-13	Derives de 4-(aminomethyl) piperidine, leur preparation et leur application en therapeutique.
SU1195903A3 (ru)	1985-11-30	Способ получени 1-фенил- 2-аминокарбонилиндольных соединений или их солей присоединени кислот
CA2028621A1 (en)	1991-05-01	Antithrombotic substituted cycloalkano[b]dihydroindole- and -indole-sulphonamides
DE69411589T2 (de)	1999-01-07	Indol, indolin und chinolin derivate mit einer 5ht1d antagonistischen wirkung
US4988820A (en)	1991-01-29	Cycloalkano(1,2-B) indole-sulponamides
FR2688781A1 (fr)	1993-09-24	Imidazolines n-substituees par un groupement biphenylmethyle, leur preparation, les compositions pharmaceutiques en contenant.
FR2687146A1 (fr)	1993-08-13	Nouveaux derives de pyrrolidine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent.
FR2458549A1 (fr)	1981-01-02	Nouveaux derives de l'indole, leur procede de preparation et leur application comme medicaments
EP0402232A1 (fr)	1990-12-12	Dérivés de pyridobenzoindole, leur préparation et les compositions qui les contiennent
JPS6360750B2 (ja)	1988-11-25
JPS6252740B2 (ja)	1987-11-06
FR2639944A1 (fr)	1990-06-08	Nouveaux derives de l'indole, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
JPH0450301B2 (ja)	1992-08-13
IE893103A1 (en)	1991-01-16	"A process for the preparation of a 1,4-dihydropyridine derivative, namely (-)-2-{[2-(2-aminoethoxy)ethoxy] methyl}-4-(2,3-dichlorophenyl)-3-ethoxy-carbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine, and its salts"
FR2551753A2 (fr)	1985-03-15	Benzotriazine-1,2,3-ones-4, procede de preparation et medicaments les contenant
FI71554C (fi)	1987-01-19	Foerfarande foer framstaellning av terapeutiskt anvaendbara 5-r,s-trans-amino-3,4,5,6-tetrahydro-1h -cyklohept/c,d/indol-6-olderivat och av deras syraadditionssalter.
WO1998003485A1 (fr)	1998-01-29	PHENOXYPROPANOLAMINES A ACTION ANTAGONISTE β3-ADRENERGIQUE