SE452459B - Indol-5-metansulfonamid, en farmaceutisk komposition och ett forfarande for framstellning av foreningen - Google Patents

Indol-5-metansulfonamid, en farmaceutisk komposition och ett forfarande for framstellning av foreningen

Info

Publication number: SE452459B
Authority: SE; Sweden
Prior art keywords: group; compound; hydrogen atom; alkyl group; general formula
Prior art date: 1982-06-07

Application number

SE8303208A

Other languages

English (en)

Swedish (sv)

Other versions

SE8303208D0 (sv

SE8303208L (sv

Inventor

M D Dowle

I H Coates

Original Assignee

Glaxo Group Ltd

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.)

1982-06-07

Filing date

1983-06-07

Publication date

1987-11-30

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=10530876&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=SE452459(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1983-06-07 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

1983-06-07 Publication of SE8303208D0 publication Critical patent/SE8303208D0/xx

1983-12-08 Publication of SE8303208L publication Critical patent/SE8303208L/xx

1987-11-30 Publication of SE452459B publication Critical patent/SE452459B/sv

Links

238000000034 method Methods 0.000 title claims description 20
239000008194 pharmaceutical composition Substances 0.000 title claims description 3
239000000126 substance Substances 0.000 title description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 215
150000001875 compounds Chemical class 0.000 claims description 170
239000000047 product Substances 0.000 claims description 100
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 78
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 74
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 64
239000000203 mixture Substances 0.000 claims description 54
-1 phenylmethylideneamino Chemical group 0.000 claims description 36
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
150000003839 salts Chemical class 0.000 claims description 32
238000004458 analytical method Methods 0.000 claims description 24
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 23
239000000706 filtrate Substances 0.000 claims description 19
238000006243 chemical reaction Methods 0.000 claims description 15
239000012453 solvate Substances 0.000 claims description 14
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 14
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 13
239000000843 powder Substances 0.000 claims description 13
MURZXKIEJFJMPP-UHFFFAOYSA-N 1-[3-(2-aminoethyl)-1h-indol-5-yl]-n-methylmethanesulfonamide Chemical group CNS(=O)(=O)CC1=CC=C2NC=C(CCN)C2=C1 MURZXKIEJFJMPP-UHFFFAOYSA-N 0.000 claims description 11
125000003342 alkenyl group Chemical group 0.000 claims description 11
230000008569 process Effects 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 10
239000012458 free base Substances 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
208000019695 Migraine disease Diseases 0.000 claims description 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 4
206010027599 migraine Diseases 0.000 claims description 4
125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 4
125000006239 protecting group Chemical group 0.000 claims description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 3
AMQNZONUQVIKGD-UHFFFAOYSA-N 1-[3-(2-aminoethyl)-1h-indol-5-yl]-n,n-dimethylmethanesulfonamide Chemical compound CN(C)S(=O)(=O)CC1=CC=C2NC=C(CCN)C2=C1 AMQNZONUQVIKGD-UHFFFAOYSA-N 0.000 claims description 2
JQWDRQGNDNULBY-UHFFFAOYSA-N 1-[3-(2-aminoethyl)-1h-indol-5-yl]-n-methylmethanesulfonamide;hydrochloride Chemical group Cl.CNS(=O)(=O)CC1=CC=C2NC=C(CCN)C2=C1 JQWDRQGNDNULBY-UHFFFAOYSA-N 0.000 claims description 2
VUYWONZJZHPBIZ-UHFFFAOYSA-N 1-[3-(2-aminoethyl)-1h-indol-5-yl]-n-prop-2-enylmethanesulfonamide Chemical compound C1=C(CS(=O)(=O)NCC=C)C=C2C(CCN)=CNC2=C1 VUYWONZJZHPBIZ-UHFFFAOYSA-N 0.000 claims description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
229910052698 phosphorus Inorganic materials 0.000 claims description 2
229910021653 sulphate ion Inorganic materials 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims 2
125000002947 alkylene group Chemical group 0.000 claims 2
125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
125000004432 carbon atom Chemical group C* 0.000 claims 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 1
239000000969 carrier Substances 0.000 claims 1
239000002808 molecular sieve Substances 0.000 claims 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 1
239000000243 solution Substances 0.000 description 119
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 102
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
239000003480 eluent Substances 0.000 description 69
239000007787 solid Substances 0.000 description 57
238000004809 thin layer chromatography Methods 0.000 description 42
239000000725 suspension Substances 0.000 description 38
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 32
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 26
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 25
239000002904 solvent Substances 0.000 description 25
DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 description 24
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
239000003054 catalyst Substances 0.000 description 21
238000002844 melting Methods 0.000 description 21
230000008018 melting Effects 0.000 description 21
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
229910052739 hydrogen Inorganic materials 0.000 description 20
239000001257 hydrogen Substances 0.000 description 20
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
239000000284 extract Substances 0.000 description 17
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 17
229910000041 hydrogen chloride Inorganic materials 0.000 description 17
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
238000001816 cooling Methods 0.000 description 14
238000001914 filtration Methods 0.000 description 14
239000006260 foam Substances 0.000 description 13
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 12
229910021529 ammonia Inorganic materials 0.000 description 12
229940109239 creatinine Drugs 0.000 description 12
239000011976 maleic acid Substances 0.000 description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 12
238000003756 stirring Methods 0.000 description 12
229910003445 palladium oxide Inorganic materials 0.000 description 11
JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 11
229910052938 sodium sulfate Inorganic materials 0.000 description 11
235000011152 sodium sulphate Nutrition 0.000 description 11
239000003610 charcoal Substances 0.000 description 10
238000004440 column chromatography Methods 0.000 description 10
229910052943 magnesium sulfate Inorganic materials 0.000 description 10
235000019341 magnesium sulphate Nutrition 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
230000009467 reduction Effects 0.000 description 10
238000006722 reduction reaction Methods 0.000 description 10
FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000006071 cream Substances 0.000 description 9
LTLKJYMNUSSFAH-UHFFFAOYSA-N 4-chloro-1,1-dimethoxybutane Chemical compound COC(OC)CCCCl LTLKJYMNUSSFAH-UHFFFAOYSA-N 0.000 description 8
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
238000004587 chromatography analysis Methods 0.000 description 8
150000002148 esters Chemical class 0.000 description 8
239000000543 intermediate Substances 0.000 description 8
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
239000000463 material Substances 0.000 description 7
239000012299 nitrogen atmosphere Substances 0.000 description 7
238000000746 purification Methods 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 6
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
229920000388 Polyphosphate Polymers 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
239000002585 base Substances 0.000 description 6
238000007796 conventional method Methods 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
230000008020 evaporation Effects 0.000 description 6
238000003818 flash chromatography Methods 0.000 description 6
150000002431 hydrogen Chemical class 0.000 description 6
239000010410 layer Substances 0.000 description 6
239000012280 lithium aluminium hydride Substances 0.000 description 6
239000001205 polyphosphate Substances 0.000 description 6
235000011176 polyphosphates Nutrition 0.000 description 6
238000010992 reflux Methods 0.000 description 6
235000010288 sodium nitrite Nutrition 0.000 description 6
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
238000005481 NMR spectroscopy Methods 0.000 description 5
239000002253 acid Substances 0.000 description 5
229920001971 elastomer Polymers 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 4
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 4
244000166102 Eucalyptus leucoxylon Species 0.000 description 4
235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 4
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 4
150000001299 aldehydes Chemical class 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
125000003710 aryl alkyl group Chemical group 0.000 description 4
239000003638 chemical reducing agent Substances 0.000 description 4
238000001035 drying Methods 0.000 description 4
238000007429 general method Methods 0.000 description 4
125000005843 halogen group Chemical group 0.000 description 4
150000004677 hydrates Chemical class 0.000 description 4
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
YDTVAJYBEHCVJY-UHFFFAOYSA-N n-methyl-1-[3-[2-(methylamino)ethyl]-1h-indol-5-yl]methanesulfonamide Chemical compound C1=C(CS(=O)(=O)NC)C=C2C(CCNC)=CNC2=C1 YDTVAJYBEHCVJY-UHFFFAOYSA-N 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000010453 quartz Substances 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
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 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 3
239000005695 Ammonium acetate Substances 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
241000282472 Canis lupus familiaris Species 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
241000400611 Eucalyptus deanei Species 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
229910021626 Tin(II) chloride Inorganic materials 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001241 acetals Chemical class 0.000 description 3
239000003377 acid catalyst Substances 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
235000019257 ammonium acetate Nutrition 0.000 description 3
229940043376 ammonium acetate Drugs 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000012267 brine Substances 0.000 description 3
210000001168 carotid artery common Anatomy 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
239000012043 crude product Substances 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 3
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 3
238000007363 ring formation reaction Methods 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
239000001119 stannous chloride Substances 0.000 description 3
235000011150 stannous chloride Nutrition 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000001384 succinic acid Substances 0.000 description 3
238000001665 trituration Methods 0.000 description 3
KPJZHOPZRAFDTN-ZRGWGRIASA-N (6aR,9R)-N-[(2S)-1-hydroxybutan-2-yl]-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@H](CO)CC)C2)=C3C2=CN(C)C3=C1 KPJZHOPZRAFDTN-ZRGWGRIASA-N 0.000 description 2
UNFGYTNEFPAGQV-BTJKTKAUSA-N (z)-but-2-enedioic acid;n-methyl-1-[3-[2-(methylamino)ethyl]-1h-indol-5-yl]methanesulfonamide Chemical compound OC(=O)\C=C/C(O)=O.C1=C(CS(=O)(=O)NC)C=C2C(CCNC)=CNC2=C1 UNFGYTNEFPAGQV-BTJKTKAUSA-N 0.000 description 2
DTWQYCXSPPQEEP-BTJKTKAUSA-N 1-[3-(2-aminoethyl)-1H-indol-5-yl]-N-ethylmethanesulfonamide (Z)-but-2-enedioic acid Chemical compound OC(=O)\C=C/C(O)=O.CCNS(=O)(=O)CC1=CC=C2NC=C(CCN)C2=C1 DTWQYCXSPPQEEP-BTJKTKAUSA-N 0.000 description 2
YSVQPMMNVLTTDF-UHFFFAOYSA-N 1-[3-(2-aminoethyl)-1h-indol-5-yl]-n-benzylmethanesulfonamide Chemical compound C1=C2C(CCN)=CNC2=CC=C1CS(=O)(=O)NCC1=CC=CC=C1 YSVQPMMNVLTTDF-UHFFFAOYSA-N 0.000 description 2
KRARMSKMLWBOMY-UHFFFAOYSA-N 1-[3-(2-aminoethyl)-1h-indol-5-yl]-n-cyclohexylmethanesulfonamide Chemical compound C1=C2C(CCN)=CNC2=CC=C1CS(=O)(=O)NC1CCCCC1 KRARMSKMLWBOMY-UHFFFAOYSA-N 0.000 description 2
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AFBYMGMXBHJYHZ-UHFFFAOYSA-N 1-[3-(2-aminoethyl)-1h-indol-5-yl]-n-propan-2-ylmethanesulfonamide Chemical compound CC(C)NS(=O)(=O)CC1=CC=C2NC=C(CCN)C2=C1 AFBYMGMXBHJYHZ-UHFFFAOYSA-N 0.000 description 2
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OFKDAAIKGIBASY-VFGNJEKYSA-N ergotamine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(N21)=O)(C)NC(=O)[C@H]1CN([C@H]2C(C3=CC=CC4=NC=C([C]34)C2)=C1)C)C1=CC=CC=C1 OFKDAAIKGIBASY-VFGNJEKYSA-N 0.000 description 1
229960004943 ergotamine Drugs 0.000 description 1
XCGSFFUVFURLIX-UHFFFAOYSA-N ergotaminine Natural products C1=C(C=2C=CC=C3NC=C(C=23)C2)C2N(C)CC1C(=O)NC(C(N12)=O)(C)OC1(O)C1CCCN1C(=O)C2CC1=CC=CC=C1 XCGSFFUVFURLIX-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000005187 foaming Methods 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
238000006698 hydrazinolysis reaction Methods 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
XBECWGJPSXHFCS-UHFFFAOYSA-N imidazole-1-carbaldehyde Chemical compound O=CN1C=CN=C1 XBECWGJPSXHFCS-UHFFFAOYSA-N 0.000 description 1
150000002475 indoles Chemical class 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000011147 inorganic material Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
229940011051 isopropyl acetate Drugs 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
ZNURQAWRNVYXPV-UHFFFAOYSA-N methanesulfonamide;nitrobenzene Chemical compound CS(N)(=O)=O.[O-][N+](=O)C1=CC=CC=C1 ZNURQAWRNVYXPV-UHFFFAOYSA-N 0.000 description 1
DDJYRBOKFGKZHZ-UHFFFAOYSA-N methanesulfonyl chloride nitrobenzene Chemical compound CS(=O)(=O)Cl.[N+](=O)([O-])C1=CC=CC=C1 DDJYRBOKFGKZHZ-UHFFFAOYSA-N 0.000 description 1
VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
239000013081 microcrystal Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
IGYMVHDFCJKCSQ-UHFFFAOYSA-N n,n-dimethyl-1-(4-nitrophenyl)methanesulfonamide Chemical compound CN(C)S(=O)(=O)CC1=CC=C([N+]([O-])=O)C=C1 IGYMVHDFCJKCSQ-UHFFFAOYSA-N 0.000 description 1
XCHBZJJWNKOQMT-UHFFFAOYSA-N n-[2-[5-(methylsulfamoylmethyl)-1h-indol-3-yl]ethyl]formamide Chemical compound CNS(=O)(=O)CC1=CC=C2NC=C(CCNC=O)C2=C1 XCHBZJJWNKOQMT-UHFFFAOYSA-N 0.000 description 1
WUSPENUSIHCFHF-UHFFFAOYSA-N n-cyclohexyl-1-(4-nitrophenyl)methanesulfonamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1CS(=O)(=O)NC1CCCCC1 WUSPENUSIHCFHF-UHFFFAOYSA-N 0.000 description 1
FYLGMXVCBBMIKF-UHFFFAOYSA-N n-ethyl-1-(4-hydrazinylphenyl)methanesulfonamide;hydrochloride Chemical compound Cl.CCNS(=O)(=O)CC1=CC=C(NN)C=C1 FYLGMXVCBBMIKF-UHFFFAOYSA-N 0.000 description 1
KZWPBAASZYQWIV-UHFFFAOYSA-N n-methyl-1-(4-nitrophenyl)methanesulfonamide Chemical compound CNS(=O)(=O)CC1=CC=C([N+]([O-])=O)C=C1 KZWPBAASZYQWIV-UHFFFAOYSA-N 0.000 description 1
WVJHETOWFTYSIE-UHFFFAOYSA-N n-methyl-1-[3-(2-nitroethyl)-1h-indol-5-yl]methanesulfonamide Chemical compound CNS(=O)(=O)CC1=CC=C2NC=C(CC[N+]([O-])=O)C2=C1 WVJHETOWFTYSIE-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000011946 reduction process Methods 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
230000006103 sulfonylation Effects 0.000 description 1
238000005694 sulfonylation reaction Methods 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
230000002792 vascular Effects 0.000 description 1
239000005526 vasoconstrictor agent Substances 0.000 description 1
210000003462 vein Anatomy 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
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
- 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
- A61P25/06—Antimigraine agents
- 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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D209/16—Tryptamines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- 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
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an alkyl or cycloalkyl radical attached to the ring nitrogen atom

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Pain & Pain Management (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)

SE8303208A 1982-06-07 1983-06-07 Indol-5-metansulfonamid, en farmaceutisk komposition och ett forfarande for framstellning av foreningen SE452459B (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB8216526		1982-06-07

Publications (3)

Publication Number	Publication Date
SE8303208D0 SE8303208D0 (sv)	1983-06-07
SE8303208L SE8303208L (sv)	1983-12-08
SE452459B true SE452459B (sv)	1987-11-30

Family

ID=10530876

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE8303208A SE452459B (sv)	1982-06-07	1983-06-07	Indol-5-metansulfonamid, en farmaceutisk komposition och ett forfarande for framstellning av foreningen

Country Status (33)

Country	Link
US (1)	US4816470A (nl)
JP (1)	JPS5942366A (nl)
KR (1)	KR900006681B1 (nl)
AT (1)	AT381933B (nl)
AU (1)	AU566149B2 (nl)
BE (1)	BE896986A (nl)
CA (1)	CA1199643A (nl)
CH (1)	CH657359A5 (nl)
CY (1)	CY1458A (nl)
CZ (1)	CZ280529B6 (nl)
DE (2)	DE3320521A1 (nl)
DK (1)	DK260183D0 (nl)
DO (1)	DOP1989476000A (nl)
ES (3)	ES523039A0 (nl)
FI (1)	FI79530C (nl)
FR (1)	FR2530625B1 (nl)
GB (1)	GB2124210B (nl)
GR (1)	GR79215B (nl)
HK (1)	HK14789A (nl)
IE (1)	IE55358B1 (nl)
IL (1)	IL68913A (nl)
IT (1)	IT1170387B (nl)
KE (1)	KE3833A (nl)
LU (1)	LU84852A1 (nl)
MX (1)	MX9202623A (nl)
MY (1)	MY8700179A (nl)
NL (1)	NL193694C (nl)
NZ (1)	NZ204482A (nl)
PH (1)	PH19908A (nl)
PT (1)	PT76830B (nl)
SE (1)	SE452459B (nl)
SK (1)	SK277877B6 (nl)
ZA (1)	ZA834110B (nl)

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1983
- 1983-06-03 IT IT48422/83A patent/IT1170387B/it active Protection Beyond IP Right Term
- 1983-06-03 GR GR71558A patent/GR79215B/el unknown
- 1983-06-06 DK DK2601/83A patent/DK260183D0/da not_active Application Discontinuation
- 1983-06-07 KR KR1019830002526A patent/KR900006681B1/ko not_active IP Right Cessation
- 1983-06-07 CH CH3117/83A patent/CH657359A5/fr not_active IP Right Cessation
- 1983-06-07 GB GB08315564A patent/GB2124210B/en not_active Expired
- 1983-06-07 ZA ZA834110A patent/ZA834110B/xx unknown
- 1983-06-07 ES ES523039A patent/ES523039A0/es active Granted
- 1983-06-07 NZ NZ204482A patent/NZ204482A/en unknown
- 1983-06-07 AU AU15441/83A patent/AU566149B2/en not_active Expired
- 1983-06-07 SE SE8303208A patent/SE452459B/sv not_active IP Right Cessation
- 1983-06-07 CA CA000429902A patent/CA1199643A/en not_active Expired
- 1983-06-07 FI FI832035A patent/FI79530C/fi not_active IP Right Cessation
- 1983-06-07 IL IL68913A patent/IL68913A/xx not_active IP Right Cessation
- 1983-06-07 PH PH29020A patent/PH19908A/en unknown
- 1983-06-07 JP JP58101587A patent/JPS5942366A/ja active Granted
- 1983-06-07 AT AT0208483A patent/AT381933B/de not_active IP Right Cessation
- 1983-06-07 LU LU84852A patent/LU84852A1/fr unknown
- 1983-06-07 PT PT76830A patent/PT76830B/pt unknown
- 1983-06-07 NL NL8302031A patent/NL193694C/nl not_active IP Right Cessation
- 1983-06-07 DE DE19833320521 patent/DE3320521A1/de active Granted
- 1983-06-07 BE BE0/210953A patent/BE896986A/fr not_active IP Right Cessation
- 1983-06-07 DE DE1993175045 patent/DE19375045I2/de active Active
- 1983-06-07 FR FR8309429A patent/FR2530625B1/fr not_active Expired
- 1983-06-07 IE IE1335/83A patent/IE55358B1/en not_active IP Right Cessation
1984
- 1984-02-16 ES ES529802A patent/ES8601880A1/es not_active Expired
1985
- 1985-06-17 ES ES544281A patent/ES8609247A1/es not_active Expired
- 1985-11-15 US US06/789,831 patent/US4816470A/en not_active Expired - Lifetime
1987
- 1987-12-30 MY MY179/87A patent/MY8700179A/xx unknown
1988
- 1988-09-30 KE KE3833A patent/KE3833A/xx unknown
1989
- 1989-02-16 HK HK147/89A patent/HK14789A/xx not_active IP Right Cessation
- 1989-07-21 CY CY1458A patent/CY1458A/xx unknown
- 1989-11-20 DO DO4760001989A patent/DOP1989476000A/es unknown
1991
- 1991-12-23 SK SK4040-91A patent/SK277877B6/sk unknown
- 1991-12-23 CZ CS914040A patent/CZ280529B6/cs unknown
1992
- 1992-06-02 MX MX9202623A patent/MX9202623A/es unknown

Also Published As

Publication number	Publication date
DOP1989476000A (es)	1996-02-03
GB2124210B (en)	1985-11-13
ES529802A0 (es)	1985-11-16
NL8302031A (nl)	1984-01-02
DE19375045I2 (de)	2002-09-05
GR79215B (nl)	1984-10-22
DE3320521A1 (de)	1983-12-08
AU1544183A (en)	1983-12-15
PT76830B (en)	1986-04-21
FI79530B (fi)	1989-09-29
PT76830A (en)	1983-07-01
NL193694C (nl)	2000-07-04
BE896986A (fr)	1983-12-07
FI832035A0 (fi)	1983-06-07
IE831335L (en)	1983-12-07
FR2530625B1 (fr)	1986-04-18
KR900006681B1 (ko)	1990-09-17
NZ204482A (en)	1986-09-10
IT8348422A0 (it)	1983-06-03
CZ280529B6 (cs)	1996-02-14
KE3833A (en)	1988-11-18
IL68913A0 (en)	1983-10-31
CY1458A (en)	1989-07-21
CZ404091A3 (en)	1993-04-14
NL193694B (nl)	2000-03-01
FI79530C (fi)	1990-01-10
PH19908A (en)	1986-08-13
JPS5942366A (ja)	1984-03-08
KR840005095A (ko)	1984-11-03
DE3320521C2 (nl)	1992-06-25
SE8303208D0 (sv)	1983-06-07
ATA208483A (de)	1986-05-15
SK404091A3 (en)	1995-06-07
GB2124210A (en)	1984-02-15
IL68913A (en)	1987-08-31
HK14789A (en)	1989-02-24
IE55358B1 (en)	1990-08-29
GB8315564D0 (en)	1983-07-13
SK277877B6 (en)	1995-06-07
JPH0329069B2 (nl)	1991-04-23
ES544281A0 (es)	1986-07-16
MX9202623A (es)	1992-06-30
ES8407473A1 (es)	1984-10-01
FI832035L (fi)	1983-12-08
DK260183D0 (da)	1983-06-06
US4816470A (en)	1989-03-28
ZA834110B (en)	1985-01-30
AT381933B (de)	1986-12-10
AU566149B2 (en)	1987-10-08
LU84852A1 (fr)	1985-03-29
FR2530625A1 (fr)	1984-01-27
ES523039A0 (es)	1984-10-01
IT1170387B (it)	1987-06-03
ES8609247A1 (es)	1986-07-16
CA1199643A (en)	1986-01-21
MY8700179A (en)	1987-12-31
ES8601880A1 (es)	1985-11-16
SE8303208L (sv)	1983-12-08
CH657359A5 (fr)	1986-08-29

Publication	Publication Date	Title
SE452459B (sv)	1987-11-30	Indol-5-metansulfonamid, en farmaceutisk komposition och ett forfarande for framstellning av foreningen
DE3444572C2 (de)	1993-10-14	Indolderivate, Verfahren zu ihrer Herstellung, sie enthaltende pharmazeutische Zubereitungen und ihre Verwendung
SE452460B (sv)	1987-11-30	3-/2-(dimetylamino)etyl/-n-metyl-1h-indol-5-metansulfonamid, en farmaceutisk komposition innehallande denna och ett forfarande for framstellning av foreningen
EP0242167B1 (en)	1991-11-27	Heterocyclic carboxamides
NL8700026A (nl)	1987-08-03	Indoolderivaten, werkwijze ter bereiding daarvan, alsmede daarop gebaseerde farmaceutische preparaten.
DK157680B (da)	1990-02-05	Analogifremgangsmaade til fremstilling af indolderivater
NL8103769A (nl)	1982-03-01	Heterocyclische verbindingen, werkwijze ter bereiding daarvan alsmede farmaceutische preparaten die deze verbindingen als actieve component bevatten.
JPH0148896B2 (nl)	1989-10-20
DK157995B (da)	1990-03-12	Analogifremgangsmaade til fremstilling af indolderivater
UA78536C2 (en)	2007-04-10	Indolylalkylamine derivatives as ligands of 5-hydroxytryptamine-6, method of production (variants), pharmaceutical composition
CA2696237A1 (fr)	2009-05-07	Derives de l'indol-2-one disubstitues en 3, leur preparation et leur application en therapeutique
AU600813B2 (en)	1990-08-23	Aliphatic carboxamides
US4898863A (en)	1990-02-06	Heterocyclic carboxamides
SE435622B (sv)	1984-10-08	Terapeutisk komposition innehallande indolo(2,3-a)kinolizidiner
DE3700407A1 (de)	1987-07-09	Indolderivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zubereitungen
EP0008249A2 (fr)	1980-02-20	Dérivés de fluorènes et fluoranthènes, leur procédé de préparation et leur application en thérapeutique
SU1553011A3 (ru)	1990-03-23	Способ получени производных алкилмелатонинов
NL8701372A (nl)	1988-01-04	Indoolderivaten, werkwijze ter bereiding daarvan alsmede farmaceutische preparaten die deze derivaten als actieve component bevatten.
US3314942A (en)	1967-04-18	3, 4, 5, 6-tetrahydro-1h-azepino(4, 3, 2-cd) indoles
NO124687B (nl)	1972-05-23
JPS6317860A (ja)	1988-01-25	化合物
US3901899A (en)	1975-08-26	Synthesis of indoles from anilines and intermediates therein
NO162763B (no)	1989-11-06	Analogifremgangsmaate for fremstilling av terapeutisk aktive indol-derivater.
Domínguez et al.	1992	Synthesis of cyclic ketomethylene dipeptide derivatives
US4977274A (en)	1990-12-11	4-hydroxyindole derivatives, the process for preparation thereof and their use

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