NO751989L - - Google Patents

Info

Publication number: NO751989L
Authority: NO; Norway
Prior art keywords: benzo; thiophene; compound; benzoyl; ethyl
Prior art date: 1974-06-06

Application number

NO751989A

Other languages

English (en)

Norwegian (no)

Inventor

M Descamps

J Gubin

Original Assignee

Labaz

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.)

1974-06-06

Filing date

1975-06-05

Publication date

1975-12-09

1975-06-05 Application filed by Labaz filed Critical Labaz

1975-12-09 Publication of NO751989L publication Critical patent/NO751989L/no

Links

150000001875 compounds Chemical class 0.000 claims description 97
238000000034 method Methods 0.000 claims description 25
-1 dimethylamino- Chemical class 0.000 claims description 20
239000002253 acid Substances 0.000 claims description 14
238000002360 preparation method Methods 0.000 claims description 14
239000007858 starting material Substances 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 10
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 6
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
229930192474 thiophene Natural products 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 2
150000004802 benzothiophens Chemical class 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000003282 alkyl amino group Chemical group 0.000 claims 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
238000012360 testing method Methods 0.000 description 36
ITPDYQOUSLNIHG-UHFFFAOYSA-N Amiodarone hydrochloride Chemical compound [Cl-].CCCCC=1OC2=CC=CC=C2C=1C(=O)C1=CC(I)=C(OCC[NH+](CC)CC)C(I)=C1 ITPDYQOUSLNIHG-UHFFFAOYSA-N 0.000 description 34
229960005260 amiodarone Drugs 0.000 description 34
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
239000000203 mixture Substances 0.000 description 22
241000282472 Canis lupus familiaris Species 0.000 description 20
230000000694 effects Effects 0.000 description 20
210000004165 myocardium Anatomy 0.000 description 20
239000000243 solution Substances 0.000 description 20
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 15
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 14
230000000747 cardiac effect Effects 0.000 description 14
239000012074 organic phase Substances 0.000 description 14
229910052760 oxygen Inorganic materials 0.000 description 14
239000001301 oxygen Substances 0.000 description 14
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
206010002383 Angina Pectoris Diseases 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
230000009467 reduction Effects 0.000 description 10
238000003756 stirring Methods 0.000 description 10
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
238000007792 addition Methods 0.000 description 9
229940079593 drug Drugs 0.000 description 9
239000003814 drug Substances 0.000 description 9
229960002748 norepinephrine Drugs 0.000 description 9
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 9
239000000126 substance Substances 0.000 description 9
230000001575 pathological effect Effects 0.000 description 8
239000004004 anti-anginal agent Substances 0.000 description 7
238000001990 intravenous administration Methods 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
230000017531 blood circulation Effects 0.000 description 6
230000000052 comparative effect Effects 0.000 description 6
230000036284 oxygen consumption Effects 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 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
229940124345 antianginal agent Drugs 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
238000009833 condensation Methods 0.000 description 5
230000005494 condensation Effects 0.000 description 5
201000010099 disease Diseases 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
230000004217 heart function Effects 0.000 description 5
230000000144 pharmacologic effect Effects 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
239000002250 absorbent Substances 0.000 description 4
230000002745 absorbent Effects 0.000 description 4
230000001466 anti-adreneric effect Effects 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
238000004440 column chromatography Methods 0.000 description 4
235000006408 oxalic acid Nutrition 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
230000000638 stimulation Effects 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
241001233242 Lontra Species 0.000 description 3
241000036848 Porzana carolina Species 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
230000004872 arterial blood pressure Effects 0.000 description 3
230000008901 benefit Effects 0.000 description 3
238000010908 decantation Methods 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
229960001317 isoprenaline Drugs 0.000 description 3
230000003340 mental effect Effects 0.000 description 3
DWQVMSLZCNGRDU-UHFFFAOYSA-N oxalic acid;thiophene Chemical compound C=1C=CSC=1.OC(=O)C(O)=O DWQVMSLZCNGRDU-UHFFFAOYSA-N 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000011591 potassium Substances 0.000 description 3
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
235000012239 silicon dioxide Nutrition 0.000 description 3
ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 2
CMPLHZPYZGJIMD-UHFFFAOYSA-N 1-(2-ethyl-1-benzothiophen-3-yl)ethanone Chemical compound C1=CC=C2C(C(C)=O)=C(CC)SC2=C1 CMPLHZPYZGJIMD-UHFFFAOYSA-N 0.000 description 2
HECARLQEIJRQQU-UHFFFAOYSA-N 2-ethyl-1-benzothiophene-3-carbonyl chloride Chemical compound C1=CC=C2C(C(Cl)=O)=C(CC)SC2=C1 HECARLQEIJRQQU-UHFFFAOYSA-N 0.000 description 2
GFNZJAUVJCGWLW-UHFFFAOYSA-N 2-methoxy-1,3-dimethylbenzene Chemical compound COC1=C(C)C=CC=C1C GFNZJAUVJCGWLW-UHFFFAOYSA-N 0.000 description 2
241000282994 Cervidae Species 0.000 description 2
HOBWAPHTEJGALG-JKCMADFCSA-N [(1r,5s)-8-methyl-8-azoniabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate;sulfate Chemical compound [O-]S([O-])(=O)=O.C([C@H]1CC[C@@H](C2)[NH+]1C)C2OC(=O)C(CO)C1=CC=CC=C1.C([C@H]1CC[C@@H](C2)[NH+]1C)C2OC(=O)C(CO)C1=CC=CC=C1 HOBWAPHTEJGALG-JKCMADFCSA-N 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
230000003257 anti-anginal effect Effects 0.000 description 2
229960002028 atropine sulfate Drugs 0.000 description 2
125000005605 benzo group Chemical group 0.000 description 2
239000008280 blood Substances 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
230000036772 blood pressure Effects 0.000 description 2
244000309464 bull Species 0.000 description 2
230000008859 change Effects 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 2
IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000011835 investigation Methods 0.000 description 2
230000002107 myocardial effect Effects 0.000 description 2
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
238000011160 research Methods 0.000 description 2
230000035488 systolic blood pressure Effects 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
230000002861 ventricular Effects 0.000 description 2
BCRTWEIEUQGAJU-UHFFFAOYSA-N (2-ethyl-1-benzothiophen-3-yl)-(4-hydroxy-3,5-dimethylphenyl)methanone Chemical compound CCC=1SC2=CC=CC=C2C=1C(=O)C1=CC(C)=C(O)C(C)=C1 BCRTWEIEUQGAJU-UHFFFAOYSA-N 0.000 description 1
OPCHFPHZPIURNA-MFERNQICSA-N (2s)-2,5-bis(3-aminopropylamino)-n-[2-(dioctadecylamino)acetyl]pentanamide Chemical compound CCCCCCCCCCCCCCCCCCN(CC(=O)NC(=O)[C@H](CCCNCCCN)NCCCN)CCCCCCCCCCCCCCCCCC OPCHFPHZPIURNA-MFERNQICSA-N 0.000 description 1
UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 1
229930182837 (R)-adrenaline Natural products 0.000 description 1
JDZOTSLZMQDFLG-BTJKTKAUSA-N (z)-but-2-enedioic acid;2-(2,2-dicyclohexylethyl)piperidine Chemical compound OC(=O)\C=C/C(O)=O.C1CCCNC1CC(C1CCCCC1)C1CCCCC1 JDZOTSLZMQDFLG-BTJKTKAUSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
YEWOOXBULXJQCZ-UHFFFAOYSA-N 1,2-diethyl-3-methoxybenzene Chemical compound CCC1=CC=CC(OC)=C1CC YEWOOXBULXJQCZ-UHFFFAOYSA-N 0.000 description 1
VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
TVBBBGXDQQURHJ-UHFFFAOYSA-N 1-benzothiophene 1-oxide Chemical class C1=CC=C2S(=O)C=CC2=C1 TVBBBGXDQQURHJ-UHFFFAOYSA-N 0.000 description 1
MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 description 1
SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
HQALDKFFRYFTKP-UHFFFAOYSA-N 2-[4-[4-(2-benzyl-1-benzothiophen-3-yl)phenyl]-2-bromo-6-(3-methoxyphenyl)phenoxy]acetic acid Chemical compound COC1=CC=CC(C=2C(=C(Br)C=C(C=2)C=2C=CC(=CC=2)C=2C3=CC=CC=C3SC=2CC=2C=CC=CC=2)OCC(O)=O)=C1 HQALDKFFRYFTKP-UHFFFAOYSA-N 0.000 description 1
VTWZICMJJJQLKT-UHFFFAOYSA-N 3-(dimethylamino)propyl 4-methylbenzenesulfonate Chemical compound CN(C)CCCOS(=O)(=O)C1=CC=C(C)C=C1 VTWZICMJJJQLKT-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
229910000906 Bronze Inorganic materials 0.000 description 1
241001000171 Chira Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
241000689227 Cora <basidiomycete fungus> Species 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
206010019280 Heart failures 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
AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
IFFPICMESYHZPQ-UHFFFAOYSA-N Prenylamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)CCNC(C)CC1=CC=CC=C1 IFFPICMESYHZPQ-UHFFFAOYSA-N 0.000 description 1
241000287531 Psittacidae Species 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
241000610375 Sparisoma viride Species 0.000 description 1
208000005392 Spasm Diseases 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
208000001871 Tachycardia Diseases 0.000 description 1
YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 1
230000001133 acceleration Effects 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000001800 adrenalinergic effect Effects 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
229960002213 alprenolol Drugs 0.000 description 1
PAZJSJFMUHDSTF-UHFFFAOYSA-N alprenolol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1CC=C PAZJSJFMUHDSTF-UHFFFAOYSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229960004411 benziodarone Drugs 0.000 description 1
CZCHIEJNWPNBDE-UHFFFAOYSA-N benziodarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC(I)=C(O)C(I)=C1 CZCHIEJNWPNBDE-UHFFFAOYSA-N 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
239000002981 blocking agent Substances 0.000 description 1
239000010974 bronze Substances 0.000 description 1
150000003943 catecholamines Chemical class 0.000 description 1
ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 1
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208000028831 congenital heart disease Diseases 0.000 description 1
230000008602 contraction Effects 0.000 description 1
KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 1
239000003218 coronary vasodilator agent Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
229960005139 epinephrine Drugs 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
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238000010438 heat treatment Methods 0.000 description 1
230000000004 hemodynamic effect Effects 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
229960002212 hexobendine Drugs 0.000 description 1
KRQAMFQCSAJCRH-UHFFFAOYSA-N hexobendine Chemical compound COC1=C(OC)C(OC)=CC(C(=O)OCCCN(C)CCN(C)CCCOC(=O)C=2C=C(OC)C(OC)=C(OC)C=2)=C1 KRQAMFQCSAJCRH-UHFFFAOYSA-N 0.000 description 1
238000007654 immersion Methods 0.000 description 1
229960005248 imolamine Drugs 0.000 description 1
MGSPDRWOUCPKNZ-UHFFFAOYSA-N imolamine Chemical compound O1C(=N)N(CCN(CC)CC)C(C=2C=CC=CC=2)=N1 MGSPDRWOUCPKNZ-UHFFFAOYSA-N 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
210000005240 left ventricle Anatomy 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 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
MJDYHFLQNJPQJS-UHFFFAOYSA-N n-butyl-n-(2-chloropropyl)butan-1-amine Chemical compound CCCCN(CC(C)Cl)CCCC MJDYHFLQNJPQJS-UHFFFAOYSA-N 0.000 description 1
125000004888 n-propyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
210000000653 nervous system Anatomy 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000002826 nitrites Chemical class 0.000 description 1
229960001412 pentobarbital Drugs 0.000 description 1
229960004803 perhexiline maleate Drugs 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
PHUTUTUABXHXLW-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=NC=C[C]12 PHUTUTUABXHXLW-UHFFFAOYSA-N 0.000 description 1
229960002508 pindolol Drugs 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
DURULFYMVIFBIR-UHFFFAOYSA-N practolol Chemical compound CC(C)NCC(O)COC1=CC=C(NC(C)=O)C=C1 DURULFYMVIFBIR-UHFFFAOYSA-N 0.000 description 1
229960001749 practolol Drugs 0.000 description 1
229960001989 prenylamine Drugs 0.000 description 1
239000000047 product Substances 0.000 description 1
239000001294 propane Substances 0.000 description 1
229960003712 propranolol Drugs 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
210000002027 skeletal muscle Anatomy 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
239000004289 sodium hydrogen sulphite Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
AWLUSOLTCFEHNE-UHFFFAOYSA-N sodium;urea Chemical compound [Na].NC(N)=O AWLUSOLTCFEHNE-UHFFFAOYSA-N 0.000 description 1
239000002904 solvent Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000000021 stimulant Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
239000013589 supplement Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
210000002820 sympathetic nervous system Anatomy 0.000 description 1
230000006794 tachycardia Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
150000003577 thiophenes Chemical class 0.000 description 1
210000001685 thyroid gland Anatomy 0.000 description 1
210000003371 toe Anatomy 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/56—Radicals substituted by oxygen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Plural Heterocyclic Compounds (AREA)

NO751989A 1974-06-06 1975-06-05 NO751989L (2)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB2525674A GB1456323A (en)	1974-06-06	1974-06-06	Benzothiophenes process for preparing them and pharmaceutical compositions containing the same

Publications (1)

Publication Number	Publication Date
NO751989L true NO751989L (2)	1975-12-09

Family

ID=10224753

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO751989A NO751989L (2)	1974-06-06	1975-06-05

Country Status (20)

Country	Link
US (1)	US4007204A (2)
JP (1)	JPS516958A (2)
AR (2)	AR207152A1 (2)
AT (1)	AT341517B (2)
BE (1)	BE829837A (2)
CA (1)	CA1030972A (2)
CH (1)	CH605910A5 (2)
DE (1)	DE2522655A1 (2)
DK (1)	DK135808B (2)
ES (1)	ES438303A1 (2)
FI (1)	FI751602A7 (2)
GB (1)	GB1456323A (2)
HU (1)	HU172820B (2)
IT (1)	IT1038094B (2)
NL (1)	NL7504921A (2)
NO (1)	NO751989L (2)
OA (1)	OA05022A (2)
SE (1)	SE7505482L (2)
SU (1)	SU578002A3 (2)
ZA (1)	ZA752871B (2)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4133814A (en) *	1975-10-28	1979-01-09	Eli Lilly And Company	2-Phenyl-3-aroylbenzothiophenes useful as antifertility agents
AU509682B2 (en) *	1975-10-28	1980-05-22	Eli Lilly And Company	2-Aroyl-3-Phenylbenzothiophene Derivatives
US5175184A (en) *	1982-10-19	1992-12-29	Kotobuki Seiyaku Company Limited	Benzothiophene derivatives and antihyperuricemia thereof
NO174506B (no) *	1984-10-30	1994-02-07	Usv Pharma Corp	Analogifremgangsmaate ved fremstilling av terapeutisk aktive forbindelser
US4851554A (en) *	1987-04-06	1989-07-25	University Of Tennessee Research Corporation	Certain 3-substituted 2-alkyl benzofuran derivatives
US4806663A (en) *	1987-04-06	1989-02-21	The University Of Tennessee Research Corporation	Certain 3-substituted 2-alkyl benzofuran derivatives
US4912642A (en) *	1987-09-03	1990-03-27	The Boeing Company	Coordinated engine autothrottle
US4831156A (en) *	1987-09-30	1989-05-16	The University Of Tennessee Research Corp.	3-substituted 2-alkyl indole derivatives
AU2543388A (en) *	1987-09-30	1989-04-18	University Of Tennessee Research Corporation, The	Certain 3-substituted 2-alkyl benzothiophene derivatives
JP3157882B2 (ja) *	1991-11-15	2001-04-16	帝国臓器製薬株式会社	新規なベンゾチオフエン誘導体
DE69525763T2 (de) *	1994-04-11	2002-10-02	Chugai Seiyaku K.K., Tokio/Tokyo	4,6-DI-t-BUTYL-2,3-DIHYDROBENZOTHIOPHENE, DIE LDL OXIDATION HEMMEN
CO4410191A1 (es) *	1994-09-19	1997-01-09	Lilly Co Eli	SINTESIS DE 3-[4-(2-AMINOETOXI)BENZOIL]-2-ARIL-6- HIDROXIBENZO [b] TIOFENOS
US6653328B1 (en) *	1995-03-10	2003-11-25	Eli Lilly And Company	3-benzyl-benzothiophenes
US6417199B1 (en) *	1995-03-10	2002-07-09	Eli Lilly And Company	3-benzyl-benzothiophenes
CA2236007A1 (en) *	1995-10-31	1997-07-17	Gerald Floyd Smith	Antithrombotic diamines
US6008377A (en) *	1996-03-19	1999-12-28	Eli Lilly And Company	Synthesis of 3-[4-(2-aminoethoxy)-benzoyl]-2-aryl-6-hydroxy-benzo[B]thiophenes
JP2001523252A (ja) *	1997-04-30	2001-11-20	イーライ・リリー・アンド・カンパニー	置換ベンゾ［ｂ］チオフェンの位置選択的アルキル化製造法
WO1998048794A1 (en)	1997-04-30	1998-11-05	Eli Lilly And Company	Antithrombotic agents
WO1998048804A1 (en)	1997-04-30	1998-11-05	Eli Lilly And Company	Antithrombotic agents
WO1998049161A1 (en)	1997-04-30	1998-11-05	Eli Lilly And Company	Antithrombotic agents
ATE268768T1 (de)	1997-04-30	2004-06-15	Lilly Co Eli	Antithrombosemittel
US6284756B1 (en)	1998-04-30	2001-09-04	Eli Lilly And Company	Antithrombotic agents
DK0997460T3 (da) *	1998-10-28	2003-03-31	Lilly Co Eli	Benzothiophenforbindelser som antithrombotiske midler og mellemprodukter
FR2864536B1 (fr) *	2003-12-24	2006-03-17	Clariant France Sa	Procede de preparation de n-alkyl-2 (hydroxy-4-benzoyl)-3 benzofurannes et intermediaires pour sa mise en oeuvre
DK2601958T3 (en) *	2010-08-06	2017-07-17	Tasly Pharmaceutical Group Co	APPLICATION OF SALVIA-MILTIORRHIZA COMPOSITION FOR THE PREPARATION OF MEDICINALS FOR SECONDARY PREVENTION OF CORONARY HEART DISEASE

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3514465A (en) *	1966-12-30	1970-05-26	Degussa	Certain thiazolyl- and pyridinylaminoketones
US3706747A (en) *	1970-06-05	1972-12-19	Pfizer	Benzothieno(3,2-d)- and benzofuro(3,2-d)pyrimidines

1974
- 1974-06-06 GB GB2525674A patent/GB1456323A/en not_active Expired
1975
- 1975-01-01 AR AR258913A patent/AR207152A1/es active
- 1975-04-21 US US05/569,819 patent/US4007204A/en not_active Expired - Lifetime
- 1975-04-25 NL NL7504921A patent/NL7504921A/xx not_active Application Discontinuation
- 1975-05-02 ZA ZA00752871A patent/ZA752871B/xx unknown
- 1975-05-13 SE SE7505482A patent/SE7505482L/xx unknown
- 1975-05-14 IT IT23297/75A patent/IT1038094B/it active
- 1975-05-22 DE DE19752522655 patent/DE2522655A1/de active Pending
- 1975-05-30 HU HU75LA00000867A patent/HU172820B/hu unknown
- 1975-05-30 FI FI751602A patent/FI751602A7/fi not_active Application Discontinuation
- 1975-06-04 DK DK251975AA patent/DK135808B/da unknown
- 1975-06-04 BE BE157003A patent/BE829837A/xx unknown
- 1975-06-05 NO NO751989A patent/NO751989L/no unknown
- 1975-06-05 SU SU7502143254A patent/SU578002A3/ru active
- 1975-06-06 CA CA228,687A patent/CA1030972A/en not_active Expired
- 1975-06-06 CH CH730375A patent/CH605910A5/xx not_active IP Right Cessation
- 1975-06-06 JP JP50069021A patent/JPS516958A/ja active Pending
- 1975-06-06 ES ES438303A patent/ES438303A1/es not_active Expired
- 1975-06-06 OA OA55520A patent/OA05022A/xx unknown
- 1975-06-06 AT AT431175A patent/AT341517B/de not_active IP Right Cessation
- 1975-11-07 AR AR261103A patent/AR210265A1/es active

Also Published As

Publication number	Publication date
OA05022A (fr)	1980-12-31
DK135808B (da)	1977-06-27
SU578002A3 (ru)	1977-10-25
ZA752871B (en)	1976-04-28
AU8102275A (en)	1976-11-11
AR210265A1 (es)	1977-07-15
US4007204A (en)	1977-02-08
GB1456323A (en)	1976-11-24
SE7505482L (sv)	1975-12-08
DK135808C (2)	1977-11-28
NL7504921A (nl)	1975-12-09
DE2522655A1 (de)	1975-12-18
ATA431175A (de)	1977-06-15
ES438303A1 (es)	1977-01-16
BE829837A (fr)	1975-12-04
AT341517B (de)	1978-02-10
CA1030972A (en)	1978-05-09
HU172820B (hu)	1978-12-28
FI751602A7 (2)	1975-12-07
CH605910A5 (2)	1978-10-13
IT1038094B (it)	1979-11-20
AR207152A1 (es)	1976-09-15
JPS516958A (en)	1976-01-20
DK251975A (2)	1975-12-07

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NO751989L (2)	1975-12-09
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JPH09169755A (ja)	1997-06-30	ベンゾ［ｂ］フランから得られたケトンのアミジノヒドラゾン類、それらの製造方法、およびこれらの化合物を含有する医薬
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