LU84852A1 - Derives d'indole,procedes pour leur preparation et compositions pharmaceutiques les contenant - Google Patents

Derives d'indole,procedes pour leur preparation et compositions pharmaceutiques les contenant Download PDF

Info

Publication number: LU84852A1
Authority: LU; Luxembourg
Prior art keywords: group; general formula; compound; hydrogen atom; indole
Prior art date: 1982-06-07

Application number

LU84852A

Other languages

English (en)

French (fr)

Inventor

Michael Dennis Dowle

Ian Harold 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

1985-03-29

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=LU84852(A1) "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

1985-03-29 Publication of LU84852A1 publication Critical patent/LU84852A1/fr

Links

238000000034 method Methods 0.000 title claims description 53
230000008569 process Effects 0.000 title claims description 20
238000002360 preparation method Methods 0.000 title claims description 10
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title description 9
239000008194 pharmaceutical composition Substances 0.000 title description 4
229940054051 antipsychotic indole derivative Drugs 0.000 title 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 228
150000001875 compounds Chemical class 0.000 claims description 158
-1 2- (methylamino) ethyl Chemical group 0.000 claims description 43
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 35
150000003839 salts Chemical class 0.000 claims description 33
125000000217 alkyl group Chemical group 0.000 claims description 29
239000002904 solvent Substances 0.000 claims description 28
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 28
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 27
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 22
239000001257 hydrogen Substances 0.000 claims description 21
229910052739 hydrogen Inorganic materials 0.000 claims description 21
239000003054 catalyst Substances 0.000 claims description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 18
229910052757 nitrogen Inorganic materials 0.000 claims description 11
125000003710 aryl alkyl group Chemical group 0.000 claims description 10
229940124530 sulfonamide Drugs 0.000 claims description 9
125000003342 alkenyl group Chemical group 0.000 claims description 8
239000003960 organic solvent Substances 0.000 claims description 8
150000003456 sulfonamides Chemical class 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
239000012453 solvate Substances 0.000 claims description 6
239000012280 lithium aluminium hydride Substances 0.000 claims description 5
125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
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 3
150000001340 alkali metals Chemical class 0.000 claims description 3
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
229910000510 noble metal Inorganic materials 0.000 claims description 3
125000006239 protecting group Chemical group 0.000 claims description 3
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 2
239000007868 Raney catalyst Substances 0.000 claims description 2
229910000564 Raney nickel Inorganic materials 0.000 claims description 2
150000001342 alkaline earth metals Chemical class 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
238000010531 catalytic reduction reaction Methods 0.000 claims description 2
230000000295 complement effect Effects 0.000 claims description 2
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 2
150000003840 hydrochlorides Chemical class 0.000 claims description 2
229910052751 metal Inorganic materials 0.000 claims description 2
239000002184 metal Substances 0.000 claims description 2
229910052987 metal hydride Inorganic materials 0.000 claims description 2
150000004681 metal hydrides Chemical class 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 5
125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 3
101100481524 Escherichia phage N15 gene 20 gene Proteins 0.000 claims 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 1
238000007614 solvation Methods 0.000 claims 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 1
230000001131 transforming effect Effects 0.000 claims 1
239000000243 solution Substances 0.000 description 110
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 95
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 93
235000019441 ethanol Nutrition 0.000 description 79
239000000047 product Substances 0.000 description 79
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 74
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 64
239000000203 mixture Substances 0.000 description 60
239000007787 solid Substances 0.000 description 55
238000002844 melting Methods 0.000 description 45
230000008018 melting Effects 0.000 description 45
239000000725 suspension Substances 0.000 description 42
238000004809 thin layer chromatography Methods 0.000 description 42
239000003921 oil Substances 0.000 description 39
235000019198 oils Nutrition 0.000 description 39
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
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 25
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 25
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 25
DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 description 24
238000004458 analytical method Methods 0.000 description 23
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
238000001914 filtration Methods 0.000 description 22
238000010992 reflux Methods 0.000 description 21
239000004480 active ingredient Substances 0.000 description 20
239000000843 powder Substances 0.000 description 20
238000000605 extraction Methods 0.000 description 18
239000000706 filtrate Substances 0.000 description 18
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 17
239000000284 extract Substances 0.000 description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
238000004587 chromatography analysis Methods 0.000 description 15
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 14
239000006260 foam Substances 0.000 description 13
230000009467 reduction Effects 0.000 description 13
238000006722 reduction reaction Methods 0.000 description 13
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
238000001816 cooling Methods 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
239000003826 tablet Substances 0.000 description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
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
239000003610 charcoal Substances 0.000 description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
239000012458 free base Substances 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 10
LTLKJYMNUSSFAH-UHFFFAOYSA-N 4-chloro-1,1-dimethoxybutane Chemical compound COC(OC)CCCCl LTLKJYMNUSSFAH-UHFFFAOYSA-N 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
150000002148 esters Chemical class 0.000 description 9
238000001704 evaporation Methods 0.000 description 9
230000008020 evaporation Effects 0.000 description 9
239000000463 material Substances 0.000 description 9
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 9
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 8
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products 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 8
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
239000000443 aerosol Substances 0.000 description 8
238000004440 column chromatography Methods 0.000 description 8
239000000543 intermediate Substances 0.000 description 8
239000008101 lactose Substances 0.000 description 8
238000003756 stirring Methods 0.000 description 8
MURZXKIEJFJMPP-UHFFFAOYSA-N 1-[3-(2-aminoethyl)-1h-indol-5-yl]-n-methylmethanesulfonamide Chemical compound CNS(=O)(=O)CC1=CC=C2NC=C(CCN)C2=C1 MURZXKIEJFJMPP-UHFFFAOYSA-N 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
239000002253 acid Substances 0.000 description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
238000007796 conventional method Methods 0.000 description 7
239000010410 layer Substances 0.000 description 7
235000019359 magnesium stearate Nutrition 0.000 description 7
238000000746 purification Methods 0.000 description 7
239000007921 spray Substances 0.000 description 7
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 6
208000019695 Migraine disease Diseases 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
239000002585 base Substances 0.000 description 6
239000008187 granular material Substances 0.000 description 6
150000004677 hydrates Chemical class 0.000 description 6
206010027599 migraine Diseases 0.000 description 6
239000001205 polyphosphate Substances 0.000 description 6
235000011176 polyphosphates Nutrition 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
239000007832 Na2SO4 Substances 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
239000002775 capsule Substances 0.000 description 5
239000006071 cream Substances 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
238000007363 ring formation reaction Methods 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
125000001424 substituent group Chemical group 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
241000282472 Canis lupus familiaris Species 0.000 description 4
244000166102 Eucalyptus leucoxylon Species 0.000 description 4
235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
229920002472 Starch Polymers 0.000 description 4
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
229930006000 Sucrose Natural products 0.000 description 4
QTEJRFMIQYQJRM-UHFFFAOYSA-N [3-(2-aminoethyl)-1h-indol-5-yl]methanesulfonamide Chemical compound C1=C(CS(N)(=O)=O)C=C2C(CCN)=CNC2=C1 QTEJRFMIQYQJRM-UHFFFAOYSA-N 0.000 description 4
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 4
238000013019 agitation Methods 0.000 description 4
150000001299 aldehydes Chemical class 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
239000003638 chemical reducing agent Substances 0.000 description 4
238000007906 compression Methods 0.000 description 4
230000006835 compression Effects 0.000 description 4
238000001035 drying Methods 0.000 description 4
125000005843 halogen group Chemical group 0.000 description 4
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 4
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 4
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 4
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 4
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 4
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
239000000546 pharmaceutical excipient Substances 0.000 description 4
239000011343 solid material Substances 0.000 description 4
235000019698 starch Nutrition 0.000 description 4
239000008107 starch Substances 0.000 description 4
229940032147 starch Drugs 0.000 description 4
239000001384 succinic acid Substances 0.000 description 4
239000005720 sucrose Substances 0.000 description 4
239000000829 suppository Substances 0.000 description 4
238000001665 trituration Methods 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
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
229920002261 Corn starch Polymers 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
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 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
150000001412 amines Chemical class 0.000 description 3
235000019257 ammonium acetate Nutrition 0.000 description 3
229940043376 ammonium acetate Drugs 0.000 description 3
239000012267 brine Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
239000000470 constituent Substances 0.000 description 3
239000008120 corn starch Substances 0.000 description 3
239000012043 crude product Substances 0.000 description 3
238000007429 general method Methods 0.000 description 3
230000008570 general process Effects 0.000 description 3
239000011521 glass Substances 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
239000007788 liquid Substances 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
SCWKRWCUMCMVPW-UHFFFAOYSA-N phenyl n-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC=C1 SCWKRWCUMCMVPW-UHFFFAOYSA-N 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000003755 preservative agent Substances 0.000 description 3
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 3
239000000377 silicon dioxide Substances 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
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
230000009466 transformation Effects 0.000 description 3
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 3
229940029284 trichlorofluoromethane Drugs 0.000 description 3
239000003981 vehicle Substances 0.000 description 3
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CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
ZAYITQDIKSBHDD-UHFFFAOYSA-N benzene methane Chemical compound C.C1=CC=CC=C1.C1=CC=CC=C1 ZAYITQDIKSBHDD-UHFFFAOYSA-N 0.000 description 1
125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229940045348 brown mixture Drugs 0.000 description 1
235000019846 buffering salt Nutrition 0.000 description 1
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229960004424 carbon dioxide Drugs 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
GFHNAMRJFCEERV-UHFFFAOYSA-L cobalt chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Co+2] GFHNAMRJFCEERV-UHFFFAOYSA-L 0.000 description 1
GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
229940097267 cobaltous chloride Drugs 0.000 description 1
229940097268 cobaltous chloride hexahydrate Drugs 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
238000004040 coloring Methods 0.000 description 1
229940125758 compound 15 Drugs 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
230000001143 conditioned effect Effects 0.000 description 1
239000013078 crystal Substances 0.000 description 1
WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
238000010908 decantation Methods 0.000 description 1
238000001514 detection method Methods 0.000 description 1
239000003599 detergent Substances 0.000 description 1
150000008050 dialkyl sulfates Chemical class 0.000 description 1
UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 description 1
229940099364 dichlorofluoromethane Drugs 0.000 description 1
FHHZOYXKOICLGH-UHFFFAOYSA-N dichloromethane;ethanol Chemical compound CCO.ClCCl FHHZOYXKOICLGH-UHFFFAOYSA-N 0.000 description 1
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
229940087091 dichlorotetrafluoroethane Drugs 0.000 description 1
230000010339 dilation Effects 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000007920 enema Substances 0.000 description 1
229940079360 enema for constipation Drugs 0.000 description 1
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
ZCRZCMUDOWDGOB-UHFFFAOYSA-N ethanesulfonimidic acid Chemical compound CCS(N)(=O)=O ZCRZCMUDOWDGOB-UHFFFAOYSA-N 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
239000003925 fat Substances 0.000 description 1
235000019197 fats Nutrition 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
239000012634 fragment Substances 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
125000005456 glyceride group Chemical group 0.000 description 1
238000003306 harvesting Methods 0.000 description 1
231100000869 headache Toxicity 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000006698 hydrazinolysis reaction Methods 0.000 description 1
150000004678 hydrides Chemical class 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
239000005457 ice water Substances 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
238000001802 infusion Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000011147 inorganic material Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
229910052740 iodine Inorganic materials 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
150000002500 ions Chemical class 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
235000010445 lecithin Nutrition 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910000103 lithium hydride Inorganic materials 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
230000007246 mechanism Effects 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
238000003808 methanol extraction Methods 0.000 description 1
GSYSFVSGPABNNL-UHFFFAOYSA-N methyl 2-dimethoxyphosphoryl-2-(phenylmethoxycarbonylamino)acetate Chemical group COC(=O)C(P(=O)(OC)OC)NC(=O)OCC1=CC=CC=C1 GSYSFVSGPABNNL-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
230000003278 mimic effect Effects 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000002808 molecular sieve 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
CSJJKMYRCHKJJK-UHFFFAOYSA-N n-ethyl-1-(4-nitrophenyl)methanesulfonamide Chemical compound CCNS(=O)(=O)CC1=CC=C([N+]([O-])=O)C=C1 CSJJKMYRCHKJJK-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
239000006199 nebulizer Substances 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000002687 nonaqueous vehicle Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229910052698 phosphorus Inorganic materials 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
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000011591 potassium Substances 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
229920001592 potato starch Polymers 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000003380 propellant Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical class CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
239000002510 pyrogen Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
210000003752 saphenous vein Anatomy 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000007790 scraping Methods 0.000 description 1
238000006748 scratching Methods 0.000 description 1
230000002393 scratching effect Effects 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229940079832 sodium starch glycolate Drugs 0.000 description 1
229920003109 sodium starch glycolate Polymers 0.000 description 1
239000008109 sodium starch glycolate Substances 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
241000894007 species Species 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000010959 steel Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
BPSUJSDZHLTNJR-UHFFFAOYSA-N sulfamide;hydrochloride Chemical compound Cl.NS(N)(=O)=O BPSUJSDZHLTNJR-UHFFFAOYSA-N 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
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000003760 tallow Substances 0.000 description 1
238000010998 test method Methods 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 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
239000005526 vasoconstrictor agent Substances 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000002023 wood 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
- C07D209/14—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)

LU84852A 1982-06-07 1983-06-07 Derives d'indole,procedes pour leur preparation et compositions pharmaceutiques les contenant LU84852A1 (fr)

Applications Claiming Priority (2)

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

Publications (1)

Publication Number	Publication Date
LU84852A1 true LU84852A1 (fr)	1985-03-29

Family

ID=10530876

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU84852A LU84852A1 (fr)	1982-06-07	1983-06-07	Derives d'indole,procedes pour leur preparation et compositions pharmaceutiques les contenant

Country Status (33)

Country	Link
US (1)	US4816470A (sv)
JP (1)	JPS5942366A (sv)
KR (1)	KR900006681B1 (sv)
AT (1)	AT381933B (sv)
AU (1)	AU566149B2 (sv)
BE (1)	BE896986A (sv)
CA (1)	CA1199643A (sv)
CH (1)	CH657359A5 (sv)
CY (1)	CY1458A (sv)
CZ (1)	CZ280529B6 (sv)
DE (2)	DE19375045I2 (sv)
DK (1)	DK260183D0 (sv)
DO (1)	DOP1989476000A (sv)
ES (3)	ES8407473A1 (sv)
FI (1)	FI79530C (sv)
FR (1)	FR2530625B1 (sv)
GB (1)	GB2124210B (sv)
GR (1)	GR79215B (sv)
HK (1)	HK14789A (sv)
IE (1)	IE55358B1 (sv)
IL (1)	IL68913A (sv)
IT (1)	IT1170387B (sv)
KE (1)	KE3833A (sv)
LU (1)	LU84852A1 (sv)
MX (1)	MX9202623A (sv)
MY (1)	MY8700179A (sv)
NL (1)	NL193694C (sv)
NZ (1)	NZ204482A (sv)
PH (1)	PH19908A (sv)
PT (1)	PT76830B (sv)
SE (1)	SE452459B (sv)
SK (1)	SK404091A3 (sv)
ZA (1)	ZA834110B (sv)

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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 NL NL8302031A patent/NL193694C/nl not_active IP Right Cessation
- 1983-06-07 PT PT76830A patent/PT76830B/pt unknown
- 1983-06-07 IE IE1335/83A patent/IE55358B1/en not_active IP Right Cessation
- 1983-06-07 KR KR1019830002526A patent/KR900006681B1/ko not_active IP Right Cessation
- 1983-06-07 GB GB08315564A patent/GB2124210B/en not_active Expired
- 1983-06-07 PH PH29020A patent/PH19908A/en unknown
- 1983-06-07 FR FR8309429A patent/FR2530625B1/fr not_active Expired
- 1983-06-07 LU LU84852A patent/LU84852A1/fr unknown
- 1983-06-07 FI FI832035A patent/FI79530C/sv not_active IP Right Cessation
- 1983-06-07 DE DE1993175045 patent/DE19375045I2/de active Active
- 1983-06-07 CH CH3117/83A patent/CH657359A5/fr not_active IP Right Cessation
- 1983-06-07 AU AU15441/83A patent/AU566149B2/en not_active Expired
- 1983-06-07 CA CA000429902A patent/CA1199643A/en not_active Expired
- 1983-06-07 IL IL68913A patent/IL68913A/xx 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 JP JP58101587A patent/JPS5942366A/ja active Granted
- 1983-06-07 ES ES523039A patent/ES8407473A1/es not_active Expired
- 1983-06-07 ZA ZA834110A patent/ZA834110B/xx unknown
- 1983-06-07 SE SE8303208A patent/SE452459B/sv not_active IP Right Cessation
- 1983-06-07 NZ NZ204482A patent/NZ204482A/en unknown
- 1983-06-07 AT AT0208483A patent/AT381933B/de 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 CZ CS914040A patent/CZ280529B6/cs unknown
- 1991-12-23 SK SK4040-91A patent/SK404091A3/sk unknown
1992
- 1992-06-02 MX MX9202623A patent/MX9202623A/es unknown

Also Published As

Publication number	Publication date
PT76830B (en)	1986-04-21
PT76830A (en)	1983-07-01
AU566149B2 (en)	1987-10-08
AT381933B (de)	1986-12-10
GB8315564D0 (en)	1983-07-13
KR900006681B1 (ko)	1990-09-17
CZ280529B6 (cs)	1996-02-14
US4816470A (en)	1989-03-28
ES529802A0 (es)	1985-11-16
DK260183D0 (da)	1983-06-06
DE19375045I2 (de)	2002-09-05
GR79215B (sv)	1984-10-22
ES523039A0 (es)	1984-10-01
NL8302031A (nl)	1984-01-02
PH19908A (en)	1986-08-13
FI832035L (fi)	1983-12-08
NZ204482A (en)	1986-09-10
ZA834110B (en)	1985-01-30
KR840005095A (ko)	1984-11-03
MY8700179A (en)	1987-12-31
JPH0329069B2 (sv)	1991-04-23
GB2124210A (en)	1984-02-15
IL68913A (en)	1987-08-31
GB2124210B (en)	1985-11-13
IT8348422A0 (it)	1983-06-03
FI79530C (sv)	1990-01-10
NL193694B (nl)	2000-03-01
SE452459B (sv)	1987-11-30
KE3833A (en)	1988-11-18
NL193694C (nl)	2000-07-04
SK277877B6 (en)	1995-06-07
SK404091A3 (en)	1995-06-07
HK14789A (en)	1989-02-24
CH657359A5 (fr)	1986-08-29
ES544281A0 (es)	1986-07-16
FI79530B (fi)	1989-09-29
CA1199643A (en)	1986-01-21
SE8303208D0 (sv)	1983-06-07
SE8303208L (sv)	1983-12-08
JPS5942366A (ja)	1984-03-08
MX9202623A (es)	1992-06-30
CZ404091A3 (en)	1993-04-14
CY1458A (en)	1989-07-21
IE831335L (en)	1983-12-07
IE55358B1 (en)	1990-08-29
IL68913A0 (en)	1983-10-31
IT1170387B (it)	1987-06-03
FR2530625A1 (fr)	1984-01-27
BE896986A (fr)	1983-12-07
ES8609247A1 (es)	1986-07-16
ES8407473A1 (es)	1984-10-01
FR2530625B1 (fr)	1986-04-18
DE3320521C2 (sv)	1992-06-25
FI832035A0 (fi)	1983-06-07
DOP1989476000A (es)	1996-02-03
AU1544183A (en)	1983-12-15
DE3320521A1 (de)	1983-12-08
ATA208483A (de)	1986-05-15
ES8601880A1 (es)	1985-11-16

Publication	Publication Date	Title
LU84852A1 (fr)	1985-03-29	Derives d'indole,procedes pour leur preparation et compositions pharmaceutiques les contenant
BE1000071A4 (fr)	1988-02-02	Derives d'indole, procede pour leur preparation et compositions pharmaceutiques les contenant.
FR2568571A1 (fr)	1986-02-07	Derive d'indole
CH651550A5 (fr)	1985-09-30	Derives de l'indole, leur preparation et compositions pharmaceutiques les contenant.
EP0477049B1 (fr)	1999-12-01	Dérivés d'amido-3 pyrazole, procédé pour leur préparation et compositions pharmaceutiques les contenant
EP0501892B1 (fr)	1996-07-24	Dérivés hétérocycliques diazotés N-substitués par un groupement biphénylméthyle, leur préparation, les compositions pharmaceutiques en contenant
WO1999015525A1 (fr)	1999-04-01	Derives de carboxamidothiazoles, leur preparation, les compositions pharmaceutiques en contenant
CH663411A5 (fr)	1987-12-15	Derives d'indole utiles comme medicaments.
CH651551A5 (fr)	1985-09-30	Derives de l'indole, leur preparation et compositions pharmaceutiques les contenant.
CZ282061B6 (cs)	1997-05-14	Tetrahydrokarbazolové deriváty, způsob jejich výroby a farmaceutické prostředky s jejich obsahem
EP0307303A1 (fr)	1989-03-15	[(Pyrimidinyl-2)-aminoalkyl]-1 pipéridines, leur préparation et leur application en thérapeutique
EP0611766A1 (fr)	1994-08-24	Dérivés de 2-amido-thiazoles polysubstitués, procédé de préparation, composition pharmaceutique et utilisation de ces dérivés pour la préparation d'un médicament
FR2488606A1 (fr)	1982-02-19	Derives indoliques, leur preparation et leurs applications en tant que medicaments
FR2574077A1 (fr)	1986-06-06	Derives d'indoles, leur preparation et les compositions pharmaceutiques les contenant
CH667454A5 (fr)	1988-10-14	Derives d'indoles.
EP1567150B1 (fr)	2009-08-12	Derives d indole-3-carboxamide, leur preparation et leur application en therapeutique
EP1507758B1 (fr)	2005-11-02	Derives d'indole et leur utilisation en tant que ligands des recepteurs cb2
BE1000072A4 (fr)	1988-02-02	Derives de l'indole utiles comme medicaments et procede et intermediaires pour leur preparation.
WO1998031669A1 (fr)	1998-07-23	Nouvelles arylpiperazines derivees de piperidine comme medicaments antidepresseurs
WO1999010344A1 (fr)	1999-03-04	Derives d'indole comme agonistes de 5-ht1b et 5-ht1d
CH620678A5 (en)	1980-12-15	Process for the preparation of a derivative of piperidine
LU85915A1 (fr)	1986-01-14	Nouveaux derives d'indole utiles comme medicaments et intermediaires et procedes pour leur preparation

Legal Events

Date	Code	Title	Description
1983-06-07	DT	Application date
1991-06-20	TA	Annual fee