CA1078376A - Derives d'indolo-quinolizine pentacycliques - Google Patents

Derives d'indolo-quinolizine pentacycliques

Info

Publication number: CA1078376A
Authority: CA; Canada
Prior art keywords: mls; adds; indolo; obtains; minutes
Prior art date: 1976-06-21
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

Application number

CA255,310A

Other languages

English (en)

Inventor

Henri P. Husson

Pierre Potier

Claude Thal

Richard Besselievre

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.)

Bpifrance Financement SA

Original Assignee

Agence National de Valorisation de la Recherche ANVAR

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.)

1976-06-21

Filing date

1976-06-21

Publication date

1980-05-27

1976-06-21 Application filed by Agence National de Valorisation de la Recherche ANVAR filed Critical Agence National de Valorisation de la Recherche ANVAR

1976-06-21 Priority to CA255,310A priority Critical patent/CA1078376A/fr

1980-05-27 Application granted granted Critical

1980-05-27 Publication of CA1078376A publication Critical patent/CA1078376A/fr

Status Expired legal-status Critical Current

Links

DBVVQINTNHWWGH-UHFFFAOYSA-N indolo[3,2-a]quinolizine Chemical class C1=CC=CC2=C3C4=CC=CC=C4N=C3C=CN21 DBVVQINTNHWWGH-UHFFFAOYSA-N 0.000 title description 28
150000003839 salts Chemical class 0.000 claims abstract description 28
-1 hydroxyethyl radical Chemical group 0.000 claims abstract description 24
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
239000002253 acid Substances 0.000 claims abstract description 11
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
150000007513 acids Chemical class 0.000 claims abstract description 7
150000003254 radicals Chemical class 0.000 claims abstract description 7
150000001204 N-oxides Chemical class 0.000 claims abstract description 5
150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 5
230000017105 transposition Effects 0.000 claims abstract description 5
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
125000005843 halogen group Chemical group 0.000 claims abstract description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 50
239000000047 product Substances 0.000 claims description 31
238000000034 method Methods 0.000 claims description 14
150000001875 compounds Chemical class 0.000 claims description 6
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 6
150000001450 anions Chemical class 0.000 claims description 4
239000003513 alkali Substances 0.000 claims description 3
150000007522 mineralic acids Chemical class 0.000 claims description 2
150000007524 organic acids Chemical class 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
229960004279 formaldehyde Drugs 0.000 claims 1
235000019256 formaldehyde Nutrition 0.000 claims 1
238000004519 manufacturing process Methods 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 96
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 85
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 64
239000000203 mixture Substances 0.000 description 54
239000000243 solution Substances 0.000 description 50
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 37
238000010992 reflux Methods 0.000 description 36
238000013019 agitation Methods 0.000 description 34
238000001816 cooling Methods 0.000 description 34
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 30
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
CMLQXZNMSSZRCH-UHFFFAOYSA-N indoloquinolizine Natural products C1=CC=CC2=C3N=C(C=CC=C4)C4=C3C=CN21 CMLQXZNMSSZRCH-UHFFFAOYSA-N 0.000 description 29
238000002844 melting Methods 0.000 description 29
230000008018 melting Effects 0.000 description 29
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 28
238000001914 filtration Methods 0.000 description 28
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 25
229910052753 mercury Inorganic materials 0.000 description 25
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 22
239000013078 crystal Substances 0.000 description 22
239000012074 organic phase Substances 0.000 description 22
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 20
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
239000000284 extract Substances 0.000 description 18
239000007864 aqueous solution Substances 0.000 description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
239000002244 precipitate Substances 0.000 description 16
239000000725 suspension Substances 0.000 description 16
239000008346 aqueous phase Substances 0.000 description 15
239000012153 distilled water Substances 0.000 description 15
229910052938 sodium sulfate Inorganic materials 0.000 description 15
235000011152 sodium sulphate Nutrition 0.000 description 15
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
239000012047 saturated solution Substances 0.000 description 14
239000011780 sodium chloride Substances 0.000 description 14
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 13
239000011541 reaction mixture Substances 0.000 description 13
239000012279 sodium borohydride Substances 0.000 description 13
229910000033 sodium borohydride Inorganic materials 0.000 description 13
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 12
238000004061 bleaching Methods 0.000 description 12
238000010438 heat treatment Methods 0.000 description 11
238000004458 analytical method Methods 0.000 description 10
239000012298 atmosphere Substances 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
229910052799 carbon Inorganic materials 0.000 description 9
239000003610 charcoal Substances 0.000 description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 8
239000000377 silicon dioxide Substances 0.000 description 8
BAZAXWOYCMUHIX-UHFFFAOYSA-M sodium perchlorate Chemical compound [Na+].[O-]Cl(=O)(=O)=O BAZAXWOYCMUHIX-UHFFFAOYSA-M 0.000 description 8
229910001488 sodium perchlorate Inorganic materials 0.000 description 8
JTKDORYHWJDUAS-UHFFFAOYSA-N 1-(4,4-diethoxybutyl)piperidin-2-one Chemical compound CCOC(OCC)CCCN1CCCCC1=O JTKDORYHWJDUAS-UHFFFAOYSA-N 0.000 description 7
239000002585 base Substances 0.000 description 7
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
235000019341 magnesium sulphate Nutrition 0.000 description 7
239000003921 oil Substances 0.000 description 6
235000019198 oils Nutrition 0.000 description 6
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 5
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
UFQGMRYLELTEID-UHFFFAOYSA-M 4h-indolo[3,2-a]quinolizin-5-ium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.C1=CC=CC2=C3C4=CC=CC[N+]4=CC=C3N=C21 UFQGMRYLELTEID-UHFFFAOYSA-M 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 4
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
238000009835 boiling Methods 0.000 description 4
238000001035 drying Methods 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
235000010755 mineral Nutrition 0.000 description 4
239000011707 mineral Substances 0.000 description 4
238000000746 purification Methods 0.000 description 4
239000012429 reaction media Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000012043 crude product Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
238000010908 decantation Methods 0.000 description 3
230000005595 deprotonation Effects 0.000 description 3
238000010537 deprotonation reaction Methods 0.000 description 3
238000004821 distillation Methods 0.000 description 3
AFRWBGJRWRHQOV-UHFFFAOYSA-N ethyl 5-bromopentanoate Chemical compound CCOC(=O)CCCCBr AFRWBGJRWRHQOV-UHFFFAOYSA-N 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
238000001819 mass spectrum Methods 0.000 description 3
239000000155 melt Substances 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
239000011975 tartaric acid Substances 0.000 description 3
235000002906 tartaric acid Nutrition 0.000 description 3
235000005074 zinc chloride Nutrition 0.000 description 3
239000011592 zinc chloride Substances 0.000 description 3
RBHDFGBPJGEYCK-UHFFFAOYSA-N 2-(5-methyl-1h-indol-3-yl)ethylazanium;chloride Chemical compound Cl.CC1=CC=C2NC=C(CCN)C2=C1 RBHDFGBPJGEYCK-UHFFFAOYSA-N 0.000 description 2
LFASSSGQIDKFOU-UHFFFAOYSA-N 2-(6-chloro-1h-indol-3-yl)ethanamine Chemical compound ClC1=CC=C2C(CCN)=CNC2=C1 LFASSSGQIDKFOU-UHFFFAOYSA-N 0.000 description 2
BQTOKMYKZPCPRW-UHFFFAOYSA-N 2-(6-fluoro-1h-indol-3-yl)ethanamine Chemical compound FC1=CC=C2C(CCN)=CNC2=C1 BQTOKMYKZPCPRW-UHFFFAOYSA-N 0.000 description 2
VOCGEKMEZOPDFP-UHFFFAOYSA-N 2-(6-methoxy-1h-indol-3-yl)ethanamine Chemical compound COC1=CC=C2C(CCN)=CNC2=C1 VOCGEKMEZOPDFP-UHFFFAOYSA-N 0.000 description 2
GEVXFHYJXGYXJP-UHFFFAOYSA-N 2-(6-methyl-1H-indol-3-yl)ethanamine Chemical compound CC1=CC=C2C(CCN)=CNC2=C1 GEVXFHYJXGYXJP-UHFFFAOYSA-N 0.000 description 2
GFLPSABXBDCMCN-UHFFFAOYSA-N 4,4-diethoxybutan-1-amine Chemical compound CCOC(OCC)CCCN GFLPSABXBDCMCN-UHFFFAOYSA-N 0.000 description 2
GDRVFDDBLLKWRI-UHFFFAOYSA-N 4H-quinolizine Chemical compound C1=CC=CN2CC=CC=C21 GDRVFDDBLLKWRI-UHFFFAOYSA-N 0.000 description 2
101150041968 CDC13 gene Proteins 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 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
241001465754 Metazoa Species 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
230000002490 cerebral effect Effects 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
150000002081 enamines Chemical class 0.000 description 2
IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
239000008098 formaldehyde solution Substances 0.000 description 2
238000001640 fractional crystallisation Methods 0.000 description 2
239000012456 homogeneous solution Substances 0.000 description 2
125000001041 indolyl group Chemical group 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
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239000012071 phase Substances 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
239000011574 phosphorus Substances 0.000 description 2
XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
230000001012 protector Effects 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
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239000000126 substance Substances 0.000 description 2
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HRSRMSMAVYUKRC-UHFFFAOYSA-N (3,4-dimethoxyphenyl)hydrazine;hydrochloride Chemical compound Cl.COC1=CC=C(NN)C=C1OC HRSRMSMAVYUKRC-UHFFFAOYSA-N 0.000 description 1
ZXBMIRYQUFQQNX-UHFFFAOYSA-N (4-fluorophenyl)hydrazine Chemical compound NNC1=CC=C(F)C=C1 ZXBMIRYQUFQQNX-UHFFFAOYSA-N 0.000 description 1
PVRSIFAEUCUJPK-UHFFFAOYSA-N (4-methoxyphenyl)hydrazine Chemical compound COC1=CC=C(NN)C=C1 PVRSIFAEUCUJPK-UHFFFAOYSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
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ORSIRXYHFPHWTN-UHFFFAOYSA-N ethyl 2-bromopentanoate Chemical compound CCCC(Br)C(=O)OCC ORSIRXYHFPHWTN-UHFFFAOYSA-N 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
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230000003287 optical effect Effects 0.000 description 1
150000002895 organic esters Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
230000010412 perfusion Effects 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
238000000053 physical method Methods 0.000 description 1
238000011197 physicochemical method Methods 0.000 description 1
239000006187 pill Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229960004063 propylene glycol Drugs 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
FCGGDEKTUUSBPS-UHFFFAOYSA-M quinolizin-5-ium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.C1=CC=CC2=CC=CC=[N+]21 FCGGDEKTUUSBPS-UHFFFAOYSA-M 0.000 description 1
230000036647 reaction Effects 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
IXGNPUSUVRTQGW-UHFFFAOYSA-M sodium;perchlorate;hydrate Chemical compound O.[Na+].[O-]Cl(=O)(=O)=O IXGNPUSUVRTQGW-UHFFFAOYSA-M 0.000 description 1
239000012265 solid product Substances 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000003981 vehicle Substances 0.000 description 1

Landscapes

Nitrogen Condensed Heterocyclic Rings (AREA)

CA255,310A 1976-06-21 1976-06-21 Derives d'indolo-quinolizine pentacycliques Expired CA1078376A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA255,310A CA1078376A (fr)	1976-06-21	1976-06-21	Derives d'indolo-quinolizine pentacycliques

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA255,310A CA1078376A (fr)	1976-06-21	1976-06-21	Derives d'indolo-quinolizine pentacycliques

Publications (1)

Publication Number	Publication Date
CA1078376A true CA1078376A (fr)	1980-05-27

Family

ID=4106248

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA255,310A Expired CA1078376A (fr)	1976-06-21	1976-06-21	Derives d'indolo-quinolizine pentacycliques

Country Status (1)

Country	Link
CA (1)	CA1078376A (fr)

1976
- 1976-06-21 CA CA255,310A patent/CA1078376A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1997-05-27	MKEX	Expiry

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