CA1266675A - 1,3,4,5-tetrahydrobenz(cd)indol-4-amines oxygenees en -6 - Google Patents

1,3,4,5-tetrahydrobenz(cd)indol-4-amines oxygenees en -6

Info

Publication number: CA1266675A
Authority: CA; Canada
Prior art keywords: indol; methoxy; tetrahydrobenz; amine; compounds
Prior art date: 1984-05-24
Legal status (The legal status 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 status listed.): Expired - Lifetime

Application number

CA000556569A

Other languages

English (en)

Inventor

Carl Kaiser

Lawrence I. Kruse

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

GlaxoSmithKline Inc

Original Assignee

Smith Kline and French Canada 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.)

1984-05-24

Filing date

1988-01-14

Publication date

1990-03-13

1985-04-09 Priority claimed from CA000478535A external-priority patent/CA1266482A1/fr

1988-01-14 Application filed by Smith Kline and French Canada Ltd filed Critical Smith Kline and French Canada Ltd

1988-01-14 Priority to CA000556569A priority Critical patent/CA1266675A/fr

1990-03-13 Application granted granted Critical

1990-03-13 Publication of CA1266675A publication Critical patent/CA1266675A/fr

2007-03-13 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims abstract description 33
239000001257 hydrogen Substances 0.000 claims abstract description 19
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
125000003545 alkoxy group Chemical group 0.000 claims description 4
AQWVVLHODJVGRT-UHFFFAOYSA-N 6-methoxy-3,5-dihydro-1h-benzo[cd]indol-4-one Chemical compound N1C=C2CC(=O)CC3=C2C1=CC=C3OC AQWVVLHODJVGRT-UHFFFAOYSA-N 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 abstract description 7
238000006268 reductive amination reaction Methods 0.000 abstract description 5
XIIGEHIPAOPAHJ-UHFFFAOYSA-N 4-nitro-1,3,4,5-tetrahydrobenzo[cd]indole Chemical class C1=CC(CC([N+](=O)[O-])C2)=C3C2=CNC3=C1 XIIGEHIPAOPAHJ-UHFFFAOYSA-N 0.000 abstract description 2
125000003342 alkenyl group Chemical group 0.000 abstract description 2
239000003420 antiserotonin agent Substances 0.000 abstract description 2
238000005984 hydrogenation reaction Methods 0.000 abstract description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 abstract 1
229940082988 antihypertensives serotonin antagonists Drugs 0.000 abstract 1
150000005627 indol-4-ones Chemical class 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 58
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
239000000203 mixture Substances 0.000 description 33
238000000034 method Methods 0.000 description 28
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
239000000243 solution Substances 0.000 description 24
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
230000000694 effects Effects 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 12
-1 6-hydroxy-1,3,4,5-tetrahydrobenz[cd]indol-4-amine N,N-dimethyl-6-methoxy-1,3,4,5-tetrahydrobenz-[cd]indol-4-amine Chemical compound 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 10
239000002253 acid Substances 0.000 description 10
150000003839 salts Chemical class 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000007787 solid Substances 0.000 description 9
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
150000001412 amines Chemical class 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
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UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 6
239000012267 brine Substances 0.000 description 6
239000000284 extract Substances 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
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HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
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229960000583 acetic acid Drugs 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 5
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 5
239000002464 receptor antagonist Substances 0.000 description 5
229940044551 receptor antagonist Drugs 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
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229910052786 argon Inorganic materials 0.000 description 4
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
230000002829 reductive effect Effects 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
239000002904 solvent Substances 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000003276 anti-hypertensive effect Effects 0.000 description 3
239000002585 base Substances 0.000 description 3
229910000085 borane Inorganic materials 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000003937 drug carrier Substances 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
238000002156 mixing Methods 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
229910003446 platinum oxide Inorganic materials 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
102000005962 receptors Human genes 0.000 description 3
108020003175 receptors Proteins 0.000 description 3
238000010992 reflux Methods 0.000 description 3
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
KETOXWNTPOPCTC-UHFFFAOYSA-N 4-bromo-5-methoxy-1h-indole-2-carboxylic acid Chemical compound COC1=CC=C2NC(C(O)=O)=CC2=C1Br KETOXWNTPOPCTC-UHFFFAOYSA-N 0.000 description 2
102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 2
108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 2
MGCZOMUDBYCPMF-UHFFFAOYSA-N 5-methoxy-1h-indole-4-carbaldehyde Chemical compound COC1=CC=C2NC=CC2=C1C=O MGCZOMUDBYCPMF-UHFFFAOYSA-N 0.000 description 2
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CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
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108010010803 Gelatin Proteins 0.000 description 2
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 2
HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 description 2
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GESDFCMCXNVUOI-UHFFFAOYSA-N 1,3,4,5-tetrahydrobenzo[cd]indole Chemical compound C1=CC(CCC2)=C3C2=CNC3=C1 GESDFCMCXNVUOI-UHFFFAOYSA-N 0.000 description 1
CEUFGDDOMXCXFW-UHFFFAOYSA-N 1h-indole-4-carbonitrile Chemical compound N#CC1=CC=CC2=C1C=CN2 CEUFGDDOMXCXFW-UHFFFAOYSA-N 0.000 description 1
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229920001817 Agar Polymers 0.000 description 1
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WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
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NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
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 1
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230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000008272 agar Substances 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
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239000003708 ampul Substances 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
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210000001841 basilar artery Anatomy 0.000 description 1
150000008107 benzenesulfonic acids Chemical class 0.000 description 1
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238000009835 boiling Methods 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
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229960004424 carbon dioxide Drugs 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
230000035487 diastolic blood pressure Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
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230000002526 effect on cardiovascular system Effects 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
NBTXRPQZVZUOGD-UHFFFAOYSA-N ethyl 4-bromo-5-methoxy-1h-indole-2-carboxylate Chemical compound COC1=CC=C2NC(C(=O)OCC)=CC2=C1Br NBTXRPQZVZUOGD-UHFFFAOYSA-N 0.000 description 1
NPIUAXNFAUGNHP-UHFFFAOYSA-N ethyl 5-methoxy-1h-indole-2-carboxylate Chemical compound COC1=CC=C2NC(C(=O)OCC)=CC2=C1 NPIUAXNFAUGNHP-UHFFFAOYSA-N 0.000 description 1
HHBXUHFXUOISSN-UHFFFAOYSA-N ethyl acetate;n-propan-2-ylpropan-2-amine Chemical compound CCOC(C)=O.CC(C)NC(C)C HHBXUHFXUOISSN-UHFFFAOYSA-N 0.000 description 1
239000012458 free base Substances 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
229940074045 glyceryl distearate Drugs 0.000 description 1
229940075507 glyceryl monostearate Drugs 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
KCKIKSJECTZLJA-UHFFFAOYSA-N indol-4-one Chemical compound O=C1C=CC=C2N=CC=C12 KCKIKSJECTZLJA-UHFFFAOYSA-N 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000006194 liquid suspension Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
MSVBMUNEBFLOHU-UHFFFAOYSA-N n,n-dibenzyl-6-methoxy-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine Chemical compound C1C(=C23)C(OC)=CC=C2NC=C3CC1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 MSVBMUNEBFLOHU-UHFFFAOYSA-N 0.000 description 1
HGKCEHZDOJRWQB-UHFFFAOYSA-N n,n-dicyclohexyl-6-methoxy-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine Chemical compound C1C(=C23)C(OC)=CC=C2NC=C3CC1N(C1CCCCC1)C1CCCCC1 HGKCEHZDOJRWQB-UHFFFAOYSA-N 0.000 description 1
PXAVOXIFTCTBHZ-UHFFFAOYSA-N n-(6-methoxy-1,3,4,5-tetrahydrobenzo[cd]indol-4-yl)acetamide Chemical group N1C=C2CC(NC(C)=O)CC3=C2C1=CC=C3OC PXAVOXIFTCTBHZ-UHFFFAOYSA-N 0.000 description 1
GICDARUGUWVJHH-UHFFFAOYSA-N n-(6-methoxy-1,3,4,5-tetrahydrobenzo[cd]indol-4-yl)benzamide Chemical compound C1C(=C23)C(OC)=CC=C2NC=C3CC1NC(=O)C1=CC=CC=C1 GICDARUGUWVJHH-UHFFFAOYSA-N 0.000 description 1
RJABLIXJQFJEIK-UHFFFAOYSA-N n-benzyl-6-methoxy-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine Chemical compound C1C(=C23)C(OC)=CC=C2NC=C3CC1NCC1=CC=CC=C1 RJABLIXJQFJEIK-UHFFFAOYSA-N 0.000 description 1
DSZWMILZVHMDIJ-UHFFFAOYSA-N n-butyl-6-methoxy-n-propyl-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine Chemical group C1=C(OC)C(CC(N(CCC)CCCC)C2)=C3C2=CNC3=C1 DSZWMILZVHMDIJ-UHFFFAOYSA-N 0.000 description 1
DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
239000008188 pellet Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000000862 serotonergic effect Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000011699 spontaneously hypertensive rat Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1

Landscapes

Indole Compounds (AREA)

CA000556569A 1984-05-24 1988-01-14 1,3,4,5-tetrahydrobenz(cd)indol-4-amines oxygenees en -6 Expired - Lifetime CA1266675A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000556569A CA1266675A (fr)	1984-05-24	1988-01-14	1,3,4,5-tetrahydrobenz(cd)indol-4-amines oxygenees en -6

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US61383984A	1984-05-24	1984-05-24
US613,839		1984-05-24
CA000478535A CA1266482A1 (fr)	1984-05-24	1985-04-09	1,,3,4,5- tetrahydrobenz(cd)indol-4-amines oxygenees en -6
CA000556569A CA1266675A (fr)	1984-05-24	1988-01-14	1,3,4,5-tetrahydrobenz(cd)indol-4-amines oxygenees en -6

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000478535A Division CA1266482A1 (fr)	1984-05-24	1985-04-09	1,,3,4,5- tetrahydrobenz(cd)indol-4-amines oxygenees en -6

Publications (1)

Publication Number	Publication Date
CA1266675A true CA1266675A (fr)	1990-03-13

Family

ID=25670643

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000556569A Expired - Lifetime CA1266675A (fr)	1984-05-24	1988-01-14	1,3,4,5-tetrahydrobenz(cd)indol-4-amines oxygenees en -6

Country Status (1)

Country	Link
CA (1)	CA1266675A (fr)

1988
- 1988-01-14 CA CA000556569A patent/CA1266675A/fr not_active Expired - Lifetime

Legal Events

Date	Code	Title	Description
1993-09-14	MKLA	Lapsed

Publication	Publication Date	Title
EP0162695B1 (fr)	1990-01-17	1,3,4,5-Tétrahyrobenzo(cd)indoles-4-amines-6-oxygénés
US5834493A (en)	1998-11-10	Indole derivatives as 5-HT1A and/or 5-HT2 ligands
KR100348029B1 (ko)	2002-12-28	트리사이클릭1-아미노에틸피롤유도체및이의제조방법
JPH0745470B2 (ja)	1995-05-17	６−置換−４−ジアルキルアミノテトラヒドロベンズ［ｃ，ｄインドール類の合成中間体
CA2002415A1 (fr)	1990-05-14	Acides alpha-amino-indole-3-acetyque utile contre le diabete, l'obesite et l'atherosclerose
AU716435B2 (en)	2000-02-24	Novel indole-2,3-dione-3-oxime derivatives
JPH0475909B2 (fr)	1992-12-02
US4314944A (en)	1982-02-09	4-Aminoalkyl-7-hydroxy-2(3H)-indolones
JPS6332072B2 (fr)	1988-06-28
AU665639B2 (en)	1996-01-11	Dihydro - and tetrahydro-isoquinolines, process for their preparation and pharmaceutical compositions containing same
JP2001522366A (ja)	2001-11-13	ドーパミンｄ▲上３▼受容体のモジュレーターとしての置換テトラヒドロイソキノリン誘導体
EP0005365B1 (fr)	1982-01-06	Dérivés du pyrano- et thiopyrano(3,4-b)indole, procédés pour leur préparation, et compositions pharmaceutiques les contenant
EP0033767B1 (fr)	1984-06-27	Indolobenzoxazines, procédés pour leur préparation et compositions pharmaceutiques les contenant
US4087532A (en)	1978-05-02	Analgesically useful 2-tetrahydrofurfuryl-5-lower alkyl-2-oxy-6,7-benzomorphans and salts thereof
US5318967A (en)	1994-06-07	2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indole derivatives
JPH068285B2 (ja)	1994-02-02	三環式アミン、その製法及び医薬組成物
US4634708A (en)	1987-01-06	Indolophenanthridines useful as dopaminergic and analgesic agents
JP3174158B2 (ja)	2001-06-11	６−オキソ−アゼピノインドール化合物、該化合物を含有する、胃の運動機能を調整する作用を有する医薬品および抗偏頭痛作用するセロトニン拮抗作用を有する医薬品並びに該化合物を製造する方法および該化合物を製造するための中間生成物
NZ195329A (en)	1984-05-31	6,7-benzomorphan derivatives and pharmaceutical compositions
HU224435B1 (hu)	2005-10-28	Benzodiazepin-származékok, eljárás előállításukra, alkalmazásukra és ezeket tartalmazó gyógyászati készítmények
US5198461A (en)	1993-03-30	Isatine derivatives, their preparation and use
CA1266675A (fr)	1990-03-13	1,3,4,5-tetrahydrobenz(cd)indol-4-amines oxygenees en -6
EP0233049A1 (fr)	1987-08-19	Hexahydro-2,3,4,8,9,9a aryl-4 1H-indéno[1,7-cd]azépines
US5030636A (en)	1991-07-09	Octahydrobenzo(f)quinoline derivatives
TW589312B (en)	2004-06-01	Aryl-8-azabicyclo[3.2.1]octanes for the treatment of depression