FI59090C - Foerfarande foer framstaellning av isokinolinderivat anvaendbara saosom beta-reseptorblockerare - Google Patents

Foerfarande foer framstaellning av isokinolinderivat anvaendbara saosom beta-reseptorblockerare Download PDF

Info

Publication number: FI59090C
Authority: FI; Finland
Prior art keywords: tetrahydro; isoquinoline; hydroxy; acetyl; formyl
Prior art date: 1974-11-15

Application number

FI753213A

Other languages

English (en)

Finnish (fi)

Other versions

FI753213A (zh

FI59090B (fi

Inventor

Albert Westermann

Frank Zimmermann

Dirk Wuppermann

Ludwig Friedrich

Manfred Raschack

Original Assignee

Knoll Ag

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.)

1974-11-15

Filing date

1975-11-14

Publication date

1981-06-10

1974-11-15 Priority claimed from DE2454198A external-priority patent/DE2454198C2/de

1975-04-30 Priority claimed from DE2519163A external-priority patent/DE2519163C2/de

1975-11-14 Application filed by Knoll Ag filed Critical Knoll Ag

1976-05-16 Publication of FI753213A publication Critical patent/FI753213A/fi

1981-02-27 Publication of FI59090B publication Critical patent/FI59090B/fi

1981-06-10 Application granted granted Critical

1981-06-10 Publication of FI59090C publication Critical patent/FI59090C/fi

Links

XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
150000001875 compounds Chemical class 0.000 description 18
239000000203 mixture Substances 0.000 description 18
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
-1 3-Chloro-2-hydroxypropoxy Chemical group 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 4
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
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239000012230 colorless oil Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
229960001317 isoprenaline Drugs 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
235000002639 sodium chloride Nutrition 0.000 description 4
241000700198 Cavia Species 0.000 description 3
229920002261 Corn starch Polymers 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
102000012740 beta Adrenergic Receptors Human genes 0.000 description 3
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230000000903 blocking effect Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
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KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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230000002526 effect on cardiovascular system Effects 0.000 description 3
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SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 3
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 3
WDCDAAMJNUHOIY-UHFFFAOYSA-N ethyl acetate;2-propan-2-yloxypropane Chemical compound CCOC(C)=O.CC(C)OC(C)C WDCDAAMJNUHOIY-UHFFFAOYSA-N 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
238000000034 method Methods 0.000 description 3
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150000003839 salts Chemical class 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
SBJSXRGEXNGDCA-UHFFFAOYSA-N 1-[6-(oxiran-2-ylmethoxy)-3,4-dihydro-1h-isoquinolin-2-yl]ethanone Chemical compound C=1C=C2CN(C(=O)C)CCC2=CC=1OCC1CO1 SBJSXRGEXNGDCA-UHFFFAOYSA-N 0.000 description 2
DVRXCMRXLKMMSL-UHFFFAOYSA-N 1-[6-[2-hydroxy-3-(propan-2-ylamino)propoxy]-3,4-dihydro-1h-isoquinolin-2-yl]ethanone Chemical compound C1N(C(C)=O)CCC2=CC(OCC(O)CNC(C)C)=CC=C21 DVRXCMRXLKMMSL-UHFFFAOYSA-N 0.000 description 2
FGOJJBOEGJEZFI-UHFFFAOYSA-N 1-[7-methoxy-1-methyl-6-(oxiran-2-ylmethoxy)-3,4-dihydro-1h-isoquinolin-2-yl]ethanone Chemical compound COC1=CC=2C(C)N(C(C)=O)CCC=2C=C1OCC1CO1 FGOJJBOEGJEZFI-UHFFFAOYSA-N 0.000 description 2
FHKXBLWFZZQMER-UHFFFAOYSA-N 6-(oxiran-2-ylmethoxy)-3,4-dihydro-1h-isoquinoline-2-carbaldehyde Chemical compound C=1C=C2CN(C=O)CCC2=CC=1OCC1CO1 FHKXBLWFZZQMER-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
DSLZVSRJTYRBFB-UHFFFAOYSA-N Galactaric acid Natural products OC(=O)C(O)C(O)C(O)C(O)C(O)=O DSLZVSRJTYRBFB-UHFFFAOYSA-N 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
206010033557 Palpitations Diseases 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
239000013543 active substance Substances 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000002876 beta blocker Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000284 extract Substances 0.000 description 2
DSLZVSRJTYRBFB-DUHBMQHGSA-N galactaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O DSLZVSRJTYRBFB-DUHBMQHGSA-N 0.000 description 2
208000019622 heart disease Diseases 0.000 description 2
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
150000002537 isoquinolines Chemical class 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
231100000053 low toxicity Toxicity 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000047 product Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
102000005962 receptors Human genes 0.000 description 2
108020003175 receptors Proteins 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 2
230000001225 therapeutic 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
DHUQUJQPALEILD-UHFFFAOYSA-N 1-(5-hydroxy-6-methoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethanone Chemical compound C1N(C(C)=O)CCC2=C(O)C(OC)=CC=C21 DHUQUJQPALEILD-UHFFFAOYSA-N 0.000 description 1
OETVYRJDJWKUNX-UHFFFAOYSA-N 1-(6-hydroxy-1-methyl-3,4-dihydro-1h-isoquinolin-2-yl)ethanone Chemical compound OC1=CC=C2C(C)N(C(C)=O)CCC2=C1 OETVYRJDJWKUNX-UHFFFAOYSA-N 0.000 description 1
KXTIMMJONYFHCM-UHFFFAOYSA-N 1-(6-hydroxy-3,4-dihydro-1h-isoquinolin-2-yl)ethanone Chemical compound OC1=CC=C2CN(C(=O)C)CCC2=C1 KXTIMMJONYFHCM-UHFFFAOYSA-N 0.000 description 1
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KXROHCCJTQGRAG-UHFFFAOYSA-N 1-(6-hydroxy-7-methoxy-3,4-dihydro-1h-isoquinolin-2-yl)propan-1-one Chemical compound OC1=C(OC)C=C2CN(C(=O)CC)CCC2=C1 KXROHCCJTQGRAG-UHFFFAOYSA-N 0.000 description 1
FMUIBCZSIMXRNY-UHFFFAOYSA-N 1-(6-methoxy-5-phenylmethoxy-3,4-dihydro-1h-isoquinolin-2-yl)ethanone Chemical compound COC1=CC=C2CN(C(C)=O)CCC2=C1OCC1=CC=CC=C1 FMUIBCZSIMXRNY-UHFFFAOYSA-N 0.000 description 1
HBAFZSBUICTQGD-UHFFFAOYSA-N 1-[1-methyl-6-(oxiran-2-ylmethoxy)-3,4-dihydro-1h-isoquinolin-2-yl]ethanone Chemical compound C=1C=C2C(C)N(C(C)=O)CCC2=CC=1OCC1CO1 HBAFZSBUICTQGD-UHFFFAOYSA-N 0.000 description 1
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229910002012 Aerosil® Inorganic materials 0.000 description 1
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206010005746 Blood pressure fluctuation Diseases 0.000 description 1
CHSUKNXBLQXCMN-UHFFFAOYSA-N C(=O)N1C(C2=CC(=C(C=C2CC1)O)OCC)C Chemical compound C(=O)N1C(C2=CC(=C(C=C2CC1)O)OCC)C CHSUKNXBLQXCMN-UHFFFAOYSA-N 0.000 description 1
RATQSLQTMSPLPJ-UHFFFAOYSA-N C(=O)N1C(C2=CC(=C(CC2CC1)OCC(CNC(C)(C)C)O)OC)C Chemical compound C(=O)N1C(C2=CC(=C(CC2CC1)OCC(CNC(C)(C)C)O)OC)C RATQSLQTMSPLPJ-UHFFFAOYSA-N 0.000 description 1
MWETUHKMBXHGAT-UHFFFAOYSA-N C(=O)N1C(C2=CC(=CC=C2CC1)OC)OC1C(C)O1 Chemical compound C(=O)N1C(C2=CC(=CC=C2CC1)OC)OC1C(C)O1 MWETUHKMBXHGAT-UHFFFAOYSA-N 0.000 description 1
VGQIRATVWVNMKR-UHFFFAOYSA-N C(C1CO1)OC1(CC=2CCN(CC2C=C1)C=O)OC Chemical compound C(C1CO1)OC1(CC=2CCN(CC2C=C1)C=O)OC VGQIRATVWVNMKR-UHFFFAOYSA-N 0.000 description 1
RLMIOHZPQDIFDI-UHFFFAOYSA-N C(C1CO1)OC1C2CCN(CC2=CC=C1)C=O Chemical compound C(C1CO1)OC1C2CCN(CC2=CC=C1)C=O RLMIOHZPQDIFDI-UHFFFAOYSA-N 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
KNWSGYQHVCEEOF-UHFFFAOYSA-N Cl.OC=1C=C2CCNCC2=CC1OCC Chemical compound Cl.OC=1C=C2CCNCC2=CC1OCC KNWSGYQHVCEEOF-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
240000002989 Euphorbia neriifolia Species 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
206010058177 Hyperkinetic heart syndrome Diseases 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
241000699670 Mus sp. Species 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
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
229930006000 Sucrose Natural products 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
208000001871 Tachycardia Diseases 0.000 description 1
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 1
230000002411 adverse Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229940040526 anhydrous sodium acetate Drugs 0.000 description 1
238000010171 animal model Methods 0.000 description 1
206010003119 arrhythmia Diseases 0.000 description 1
230000006793 arrhythmia Effects 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
210000000748 cardiovascular system Anatomy 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
SKCNIGRBPJIUBQ-UHFFFAOYSA-N chloroform;ethyl acetate Chemical compound ClC(Cl)Cl.CCOC(C)=O SKCNIGRBPJIUBQ-UHFFFAOYSA-N 0.000 description 1
150000003945 chlorohydrins Chemical class 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000000916 dilatatory effect Effects 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000001647 drug administration Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
OYJXTOVLKZDGFK-UHFFFAOYSA-N ethanol;2-propan-2-yloxypropane Chemical compound CCO.CC(C)OC(C)C OYJXTOVLKZDGFK-UHFFFAOYSA-N 0.000 description 1
HBFXVTVOSLPOEY-UHFFFAOYSA-N ethoxyethane;2-propan-2-yloxypropane Chemical compound CCOCC.CC(C)OC(C)C HBFXVTVOSLPOEY-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
208000009157 neurocirculatory asthenia Diseases 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000000422 nocturnal effect Effects 0.000 description 1
239000003921 oil Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 1
230000002685 pulmonary effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000013558 reference substance Substances 0.000 description 1
BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
229960003147 reserpine Drugs 0.000 description 1
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
GMJHUSJLZXFFQJ-UHFFFAOYSA-N soquinolol Chemical compound C1N(C=O)CCC2=C1C=CC=C2OCC(O)CNC(C)(C)C GMJHUSJLZXFFQJ-UHFFFAOYSA-N 0.000 description 1
239000000126 substance Substances 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
238000009923 sugaring Methods 0.000 description 1
230000006794 tachycardia Effects 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
231100000820 toxicity test Toxicity 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
210000005166 vasculature Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/06—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with the ring nitrogen atom acylated by carboxylic or carbonic acids, or with sulfur or nitrogen analogues thereof, e.g. carbamates
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

FI753213A 1974-11-15 1975-11-14 Foerfarande foer framstaellning av isokinolinderivat anvaendbara saosom beta-reseptorblockerare FI59090C (fi)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
DE2454198		1974-11-15
DE2454198A DE2454198C2 (de)	1974-11-15	1974-11-15	Isochinolin-Derivate, Verfahren zu ihrer Herstellung und Arzneimittel
DE2519163A DE2519163C2 (de)	1975-04-30	1975-04-30	2-Formyl-1,2,3,4-tetrahydro-5-(2-hydroxy-3-tert.butyl-aminopropoxy)-isochinolin, dessen Salze, Verfahren zu deren Herstellung und ihre Verwendung
DE2519163		1975-04-30

Publications (3)

Publication Number	Publication Date
FI753213A FI753213A (zh)	1976-05-16
FI59090B FI59090B (fi)	1981-02-27
FI59090C true FI59090C (fi)	1981-06-10

Family

ID=25767970

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI753213A FI59090C (fi)	1974-11-15	1975-11-14	Foerfarande foer framstaellning av isokinolinderivat anvaendbara saosom beta-reseptorblockerare

Country Status (21)

Country	Link
US (1)	US4013663A (zh)
JP (1)	JPS6026785B2 (zh)
AR (1)	AR206061A1 (zh)
AT (1)	AT345294B (zh)
CH (1)	CH596183A5 (zh)
DD (1)	DD122530A5 (zh)
DK (1)	DK141964C (zh)
ES (1)	ES442612A1 (zh)
FI (1)	FI59090C (zh)
FR (1)	FR2290902A1 (zh)
GR (1)	GR60361B (zh)
HU (1)	HU171604B (zh)
IE (1)	IE42035B1 (zh)
IL (1)	IL48393A (zh)
LU (1)	LU73806A1 (zh)
NL (1)	NL181360C (zh)
NO (1)	NO144109C (zh)
PL (1)	PL100139B1 (zh)
SE (1)	SE407800B (zh)
SU (1)	SU552898A3 (zh)
YU (1)	YU36930B (zh)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4129565A (en) *	1975-07-11	1978-12-12	Nisshin Flour Milling Co., Ltd.	Isocarbostyril derivatives
GB1504424A (en) *	1975-08-09	1978-03-22	Beecham Group Ltd	Isoquinoline-derived aminoethers
DE3135831A1 (de) *	1981-09-10	1983-04-28	Hoechst Ag, 6230 Frankfurt	9,10-substituierte 2-mesitylimino-3-alkyl-3,4,6,7-tetrahydro-2h-pyrimido(6,1-a)isochinolin-4-one, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1058822A (en) *	1963-07-30	1967-02-15	Ici Ltd	3-amino-2-hydroxypropoxy heterocyclic derivatives
US3910924A (en) *	1972-04-13	1975-10-07	Otsuka Pharma Co Ltd	3,4-Dihydrocarbostyril derivatives and a process for preparing the same

1975
- 1975-01-01 AR AR261211A patent/AR206061A1/es active
- 1975-10-28 DK DK485375A patent/DK141964C/da not_active IP Right Cessation
- 1975-10-30 US US05/627,291 patent/US4013663A/en not_active Expired - Lifetime
- 1975-10-31 IL IL48393A patent/IL48393A/xx unknown
- 1975-11-10 IE IE2447/75A patent/IE42035B1/en unknown
- 1975-11-11 YU YU2848/75A patent/YU36930B/xx unknown
- 1975-11-11 SU SU2188555A patent/SU552898A3/ru active
- 1975-11-12 DD DD189422A patent/DD122530A5/xx unknown
- 1975-11-12 CH CH1468375A patent/CH596183A5/xx not_active IP Right Cessation
- 1975-11-13 NL NLAANVRAGE7513301,A patent/NL181360C/xx not_active IP Right Cessation
- 1975-11-13 SE SE7512765A patent/SE407800B/xx not_active IP Right Cessation
- 1975-11-13 LU LU73806A patent/LU73806A1/xx unknown
- 1975-11-14 FI FI753213A patent/FI59090C/fi not_active IP Right Cessation
- 1975-11-14 NO NO753832A patent/NO144109C/no unknown
- 1975-11-14 JP JP50137694A patent/JPS6026785B2/ja not_active Expired
- 1975-11-14 HU HU75KO00002752A patent/HU171604B/hu not_active IP Right Cessation
- 1975-11-14 AT AT869575A patent/AT345294B/de not_active IP Right Cessation
- 1975-11-14 FR FR7534861A patent/FR2290902A1/fr active Granted
- 1975-11-14 ES ES442612A patent/ES442612A1/es not_active Expired
- 1975-11-14 GR GR49369A patent/GR60361B/el unknown
- 1975-11-14 PL PL1975184714A patent/PL100139B1/pl unknown

Also Published As

Publication number	Publication date
LU73806A1 (zh)	1976-06-11
DK485375A (da)	1976-05-16
JPS6026785B2 (ja)	1985-06-25
AT345294B (de)	1978-09-11
YU284875A (en)	1982-06-18
FI753213A (zh)	1976-05-16
SE7512765L (sv)	1976-05-17
ES442612A1 (es)	1978-03-16
HU171604B (hu)	1978-02-28
FR2290902A1 (fr)	1976-06-11
AU8626175A (en)	1977-05-12
CH596183A5 (zh)	1978-03-15
GR60361B (en)	1978-05-19
IE42035B1 (en)	1980-05-21
NL7513301A (nl)	1976-05-18
YU36930B (en)	1984-08-31
SU552898A3 (ru)	1977-03-30
JPS5175078A (zh)	1976-06-29
NL181360C (nl)	1987-08-03
NO144109B (no)	1981-03-16
IE42035L (en)	1976-05-15
ATA869575A (de)	1978-01-15
DK141964C (da)	1980-12-08
AR206061A1 (es)	1976-06-23
PL100139B1 (pl)	1978-09-30
SE407800B (sv)	1979-04-23
IL48393A (en)	1979-01-31
IL48393A0 (en)	1975-12-31
US4013663A (en)	1977-03-22
FI59090B (fi)	1981-02-27
DK141964B (da)	1980-07-28
NO144109C (no)	1981-06-24
FR2290902B1 (zh)	1978-07-28
NL181360B (nl)	1987-03-02
DD122530A5 (zh)	1976-10-12
NO753832L (zh)	1976-05-19

Publication	Publication Date	Title
HU186560B (en)	1985-08-28	Process for producing pharmaceutically active new bracket-3-amino-propoxy-bracket closed-biaenzyl derivatives
US4381398A (en)	1983-04-26	Amino-alcohol derivatives
US4724238A (en)	1988-02-09	Method of treating inflammatory diseases with labdan derivatives
JPS62111962A (ja)	1987-05-22	３−フエニルチオメチルスチレン誘導体
CA2214744C (en)	2002-12-24	3-(bis-substituted phenylmethylene)oxindole derivatives
FI59090C (fi)	1981-06-10	Foerfarande foer framstaellning av isokinolinderivat anvaendbara saosom beta-reseptorblockerare
US4076829A (en)	1978-02-28	Aminopropanol compounds and compositions for the treatment of cardiac and circulatory diseases
US3998835A (en)	1976-12-21	1-Substituted amino-3-thieno-[3,2-c]pyridinyloxy-2-propanols
NO803693L (no)	1981-06-09	2,3-indoldion-derivater.
NO139130B (no)	1978-10-02	Fremgangsmaate til fremstilling av 2-alkylamino-dihydropyridiner
US4071630A (en)	1978-01-31	1-Substituted-amino-3-(4-furo[3,2-c]pyridinyloxy)-2-propanols
DK171299B1 (da)	1996-08-26	4-Amino-6,7-dimethoxy-2-(1,2,3,4-tetrahydroisoquinolin-2-yl)quinolin-forbindelser, farmaceutiske præparater indeholdende disse og deres anvendelse til fremstilling af antiarytmiske lægemidler
US4143143A (en)	1979-03-06	Substituted imidazo[5,1-a]isoquinolines
JPS5943460B2 (ja)	1984-10-22	２−アミノ−６−ジアルキルアミノジヒドロピリジンの製造方法
CN113773356A (zh)	2021-12-10	一种胡黄连苷ii衍生物及其制备方法和应用
US3971798A (en)	1976-07-27	Pyridine derivative, processes of preparation and pharmaceutical compositions
US4423073A (en)	1983-12-27	Fluorinated diaminopentene derivatives
US4117133A (en)	1978-09-26	Vasodilating cuanzine hydrazides
US3810986A (en)	1974-05-14	Novel method and composition
JPS6032633B2 (ja)	1985-07-29	新規イソキノリン誘導体及びこの誘導体を含有する心臓機能不全治療剤
AU598634B2 (en)	1990-06-28	Oxime-ethers of 2,6-dioxobicyclo-(3.3.0)octanones for treatment of heart and circulation diseases
US5292751A (en)	1994-03-08	5,7-dihydroxy-2-methyl-8-(4-(3-hydroxy-1-(1-propyl))piperidinyl)-4H-1-benzopyran-4-one, its preparation and its use
US4338320A (en)	1982-07-06	Esters of 6'-hydroxycinchonine, and a method of treating arrythmia with them
JPS609023B2 (ja)	1985-03-07	インジルビン誘導体およびそれを含有する抗腫瘍剤
US4622399A (en)	1986-11-11	Bicyclo-heterocyclic nitrogen substituted aminoethanol derivatives

Legal Events

Date	Code	Title	Description
1994-06-08	MM	Patent lapsed
2004-08-31	MM	Patent lapsed	Owner name: KNOLL AG