CA1109469A - Derives du benzofuranne, procede de fabrication et applications therapeutiques - Google Patents

Derives du benzofuranne, procede de fabrication et applications therapeutiques

Info

Publication number: CA1109469A
Authority: CA; Canada
Prior art keywords: alkyl; radical; formula; compound; pyrroline
Prior art date: 1979-12-13
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

CA341,782A

Other languages

English (en)

Inventor

Jacky Legeai

Jacques G. Maillard

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.)

Laboratoires Jacques Logeais SA

Original Assignee

Laboratoires Jacques Logeais SA

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.)

1979-12-13

Filing date

1979-12-13

Publication date

1981-09-22

1979-12-13 Application filed by Laboratoires Jacques Logeais SA filed Critical Laboratoires Jacques Logeais SA

1979-12-13 Priority to CA341,782A priority Critical patent/CA1109469A/fr

1981-09-22 Application granted granted Critical

1981-09-22 Publication of CA1109469A publication Critical patent/CA1109469A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 13
230000008569 process Effects 0.000 title claims description 10
238000002360 preparation method Methods 0.000 title claims description 4
230000001225 therapeutic effect Effects 0.000 title description 5
150000001907 coumarones Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 39
150000003839 salts Chemical class 0.000 claims abstract description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
239000001257 hydrogen Substances 0.000 claims abstract description 9
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 4
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 4
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 13
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 3
125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims abstract 3
-1 nitro ester Chemical class 0.000 claims description 16
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 7
ADDZHRRCUWNSCS-UHFFFAOYSA-N 2-Benzofurancarboxaldehyde Chemical compound C1=CC=C2OC(C=O)=CC2=C1 ADDZHRRCUWNSCS-UHFFFAOYSA-N 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 5
XYXUHUUPHJGLHP-UHFFFAOYSA-N 5-ethoxy-2,3-dihydro-1h-pyrrole Chemical compound CCOC1=CCCN1 XYXUHUUPHJGLHP-UHFFFAOYSA-N 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 3
239000012442 inert solvent Substances 0.000 claims description 3
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 3
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
238000007239 Wittig reaction Methods 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims description 2
238000005984 hydrogenation reaction Methods 0.000 claims description 2
IIHPVYJPDKJYOU-UHFFFAOYSA-N triphenylcarbethoxymethylenephosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OCC)C1=CC=CC=C1 IIHPVYJPDKJYOU-UHFFFAOYSA-N 0.000 claims description 2
239000002253 acid Substances 0.000 claims 4
239000000126 substance Substances 0.000 claims 3
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 2
DWCSXQCXXITVKE-UHFFFAOYSA-N triethyloxidanium Chemical compound CC[O+](CC)CC DWCSXQCXXITVKE-UHFFFAOYSA-N 0.000 claims 1
206010003119 arrhythmia Diseases 0.000 abstract description 9
150000007522 mineralic acids Chemical class 0.000 abstract description 2
150000007524 organic acids Chemical class 0.000 abstract description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 50
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
230000009471 action Effects 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
238000001704 evaporation Methods 0.000 description 15
230000008020 evaporation Effects 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
239000002904 solvent Substances 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
KNISBFBYSLDPIO-UHFFFAOYSA-N ethyl 3-(1-benzofuran-2-yl)prop-2-enoate Chemical compound C1=CC=C2OC(C=CC(=O)OCC)=CC2=C1 KNISBFBYSLDPIO-UHFFFAOYSA-N 0.000 description 8
238000001816 cooling Methods 0.000 description 7
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239000000243 solution Substances 0.000 description 7
230000000638 stimulation Effects 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 6
206010010904 Convulsion Diseases 0.000 description 5
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
ZQJINTOPKCUVJS-UHFFFAOYSA-N 2,3-dihydro-1h-pyrrol-1-ium;chloride Chemical compound Cl.C1CC=CN1 ZQJINTOPKCUVJS-UHFFFAOYSA-N 0.000 description 3
206010001497 Agitation Diseases 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000003531 anti-dysrhythmic effect Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
230000036461 convulsion Effects 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
239000000203 mixture Substances 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
238000003756 stirring Methods 0.000 description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
AHFWKTKIRQCWCQ-UHFFFAOYSA-N 2,3-dihydro-1h-pyrrol-5-amine Chemical compound NC1=CCCN1 AHFWKTKIRQCWCQ-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
XFSBVAOIAHNAPC-UHFFFAOYSA-N Aconitin Natural products CCN1CC(C(CC2OC)O)(COC)C3C(OC)C(C(C45)(OC(C)=O)C(O)C6OC)C1C32C4CC6(O)C5OC(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-UHFFFAOYSA-N 0.000 description 2
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
241000283973 Oryctolagus cuniculus Species 0.000 description 2
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
241000700159 Rattus Species 0.000 description 2
229940039750 aconitine Drugs 0.000 description 2
STDXGNLCJACLFY-UHFFFAOYSA-N aconitine Natural products CCN1CC2(COC)C(O)CC(O)C34C5CC6(O)C(OC)C(O)C(OC(=O)C)(C5C6OC(=O)c7ccccc7)C(C(OC)C23)C14 STDXGNLCJACLFY-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 2
210000003169 central nervous system Anatomy 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
230000002526 effect on cardiovascular system Effects 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
235000011087 fumaric acid Nutrition 0.000 description 2
150000003840 hydrochlorides Chemical class 0.000 description 2
229940073584 methylene chloride Drugs 0.000 description 2
229960003343 ouabain Drugs 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
239000000047 product Substances 0.000 description 2
230000002889 sympathetic effect Effects 0.000 description 2
DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
XFSBVAOIAHNAPC-XTHSEXKGSA-N 16-Ethyl-1alpha,6alpha,19beta-trimethoxy-4-(methoxymethyl)-aconitane-3alpha,8,10alpha,11,18alpha-pentol, 8-acetate 10-benzoate Chemical compound O([C@H]1[C@]2(O)C[C@H]3[C@@]45C6[C@@H]([C@@]([C@H]31)(OC(C)=O)[C@@H](O)[C@@H]2OC)[C@H](OC)[C@@H]4[C@]([C@@H](C[C@@H]5OC)O)(COC)CN6CC)C(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-XTHSEXKGSA-N 0.000 description 1
WIOOTMZLCZPTDW-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)ethylazanium;chloride Chemical compound Cl.COC1=CC=C(CCN)C=C1OC WIOOTMZLCZPTDW-UHFFFAOYSA-N 0.000 description 1
YGFLQOSJXHSGKZ-UHFFFAOYSA-N 4-(1-benzofuran-2-yl)pyrrolidin-2-one Chemical compound C1NC(=O)CC1C1=CC2=CC=CC=C2O1 YGFLQOSJXHSGKZ-UHFFFAOYSA-N 0.000 description 1
206010002383 Angina Pectoris Diseases 0.000 description 1
206010002660 Anoxia Diseases 0.000 description 1
241000976983 Anoxia Species 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
206010065929 Cardiovascular insufficiency Diseases 0.000 description 1
241000700198 Cavia Species 0.000 description 1
206010011703 Cyanosis Diseases 0.000 description 1
206010015995 Eyelid ptosis Diseases 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
206010021143 Hypoxia Diseases 0.000 description 1
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 1
241001465754 Metazoa Species 0.000 description 1
FCLZCOCSZQNREK-UHFFFAOYSA-N Pyrrolidine, hydrochloride Chemical compound Cl.C1CCNC1 FCLZCOCSZQNREK-UHFFFAOYSA-N 0.000 description 1
LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-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
235000011054 acetic acid Nutrition 0.000 description 1
230000004913 activation Effects 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
238000013019 agitation Methods 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical group [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
230000007953 anoxia Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
235000003704 aspartic acid Nutrition 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-N aspartic acid group Chemical group N[C@@H](CC(=O)O)C(=O)O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
229940125717 barbiturate Drugs 0.000 description 1
230000017531 blood circulation Effects 0.000 description 1
244000309464 bull Species 0.000 description 1
239000002775 capsule Substances 0.000 description 1
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239000003795 chemical substances by application Substances 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical class C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
229940000425 combination drug Drugs 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000006196 drop Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940031098 ethanolamine Drugs 0.000 description 1
NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000007701 flash-distillation Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
208000019622 heart disease Diseases 0.000 description 1
JXYZHMPRERWTPM-UHFFFAOYSA-N hydron;morpholine;chloride Chemical compound Cl.C1COCCN1 JXYZHMPRERWTPM-UHFFFAOYSA-N 0.000 description 1
IKXNIQJDNKPPCH-UHFFFAOYSA-N hydron;prop-2-yn-1-amine;chloride Chemical compound [Cl-].[NH3+]CC#C IKXNIQJDNKPPCH-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
230000000147 hypnotic effect Effects 0.000 description 1
230000006872 improvement Effects 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
230000003993 interaction Effects 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
208000028867 ischemia Diseases 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000012528 membrane Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
SPUACDWLOLSOQO-UHFFFAOYSA-M methoxyazanium;chloride Chemical compound [Cl-].CO[NH3+] SPUACDWLOLSOQO-UHFFFAOYSA-M 0.000 description 1
NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
210000004165 myocardium Anatomy 0.000 description 1
DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
HYDZPXNVHXJHBG-UHFFFAOYSA-N o-benzylhydroxylamine;hydron;chloride Chemical compound Cl.NOCC1=CC=CC=C1 HYDZPXNVHXJHBG-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
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CBPYOHALYYGNOE-UHFFFAOYSA-M potassium;3,5-dinitrobenzoate Chemical compound [K+].[O-]C(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 CBPYOHALYYGNOE-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002203 pretreatment Methods 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
ISYORFGKSZLPNW-UHFFFAOYSA-N propan-2-ylazanium;chloride Chemical compound [Cl-].CC(C)[NH3+] ISYORFGKSZLPNW-UHFFFAOYSA-N 0.000 description 1
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ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
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239000000523 sample Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
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239000000829 suppository Substances 0.000 description 1
230000008700 sympathetic activation Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
230000002110 toxicologic effect Effects 0.000 description 1
231100000027 toxicology Toxicity 0.000 description 1
238000012345 traction test Methods 0.000 description 1
125000001680 trimethoxyphenyl group Chemical group 0.000 description 1
FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
230000002792 vascular Effects 0.000 description 1

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Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA341,782A 1979-12-13 1979-12-13 Derives du benzofuranne, procede de fabrication et applications therapeutiques Expired CA1109469A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA341,782A CA1109469A (fr)	1979-12-13	1979-12-13	Derives du benzofuranne, procede de fabrication et applications therapeutiques

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA341,782A CA1109469A (fr)	1979-12-13	1979-12-13	Derives du benzofuranne, procede de fabrication et applications therapeutiques

Publications (1)

Publication Number	Publication Date
CA1109469A true CA1109469A (fr)	1981-09-22

Family

ID=4115826

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA341,782A Expired CA1109469A (fr)	1979-12-13	1979-12-13	Derives du benzofuranne, procede de fabrication et applications therapeutiques

Country Status (1)

Country	Link
CA (1)	CA1109469A (fr)

1979
- 1979-12-13 CA CA341,782A patent/CA1109469A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1998-09-22	MKEX	Expiry

Publication	Publication Date	Title
US4007196A (en)	1977-02-08	4-Phenylpiperidine compounds
US4296126A (en)	1981-10-20	3-Aryloxy-3-aryl-propaneamines and their method of use
SI8310586A8 (sl)	1996-02-29	Postopek za pridobivanje 1,4-dihidropiridina
US4443468A (en)	1984-04-17	Benzofuran derivatives, process for their preparation and their therapeutic applications
US5059601A (en)	1991-10-22	Imidazolone derivatives with activity on central nervous system and antihypertensive activity, preparation methods thereof, and pharmaceutical compositions containing them
CS274405B2 (en)	1991-04-11	Method of 4-cyanopyridazines preparation
US4529730A (en)	1985-07-16	Piperidine derivatives, their preparation and pharmaceutical compositions containing them
GB2073739A (en)	1981-10-21	Antihypertensive amines
NO157931B (no)	1988-03-07	Analogifremgangsmaate for fremstilling av terapeutisk aktive 2-(4-(difenylmethylen)-1-piperidinyl)-eddiksyrer samt deres amider og salter.
JPH089580B2 (ja)	1996-01-31	アミノアルコ−ル、その製造法およびその用途
DE2424670A1 (de)	1974-12-12	Triazolo-isoindol-derivate und verfahren zu deren herstellung
US4208420A (en)	1980-06-17	New benzo [d] thiazole derivatives, process for their preparation and their therapeutic applications
US4100278A (en)	1978-07-11	Novel benzazepines
US4325954A (en)	1982-04-20	Pyrrolopyrimidinones and pyrroloimidazolones and their compositions and therapeutic methods
CA1185972A (fr)	1985-04-23	Derives de l'acide nicotinique
US4105777A (en)	1978-08-08	Indoles
AU641513B2 (en)	1993-09-23	5-isothiazolamine derivatives
IE49024B1 (en)	1985-07-10	New benzofuran derivatives,process for their preparation and their therapeutic applications
NO781618L (no)	1978-11-10	Fremgangsmaate ved fremstilling av nye chromenderivater
FI64591B (fi)	1983-08-31	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 4-(2-bensofuryl)-1-pyrrolinderivat
US3313687A (en)	1967-04-11	Appetite-suppressing and weight reducing composition
US4843085A (en)	1989-06-27	Pyridine derivatives, process for production thereof and pharmaceutical compositions useful as anti-arhytmics
US3262937A (en)	1966-07-26	Benzyl piperidyl ketones
US3701786A (en)	1972-10-31	Dibenzofuranyl-aminoalcohols
JPS6022714B2 (ja)	1985-06-03	キナゾリン誘導体及びその製造法