CH641455A5 - Carbostyril-derivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zubereitungen. - Google Patents

Info

Publication number

CH641455A5

CH641455A5 CH295379A CH295379A CH641455A5 CH 641455 A5 CH641455 A5 CH 641455A5 CH 295379 A CH295379 A CH 295379A CH 295379 A CH295379 A CH 295379A CH 641455 A5 CH641455 A5 CH 641455A5

Authority

CH

Switzerland

Prior art keywords

propoxy

group

dihydrocarbostyril

compound

phenylpiperazinyl

Prior art date

1978-03-30

Links

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• LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 title claims description 71
• 238000000034 method Methods 0.000 title claims description 45
• 239000000825 pharmaceutical preparation Substances 0.000 title description 4
• 238000004519 manufacturing process Methods 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims description 453
• -1 3,4,5-tri-methoxybenzoyloxy group Chemical group 0.000 claims description 162
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 113
• 125000004432 carbon atom Chemical group C* 0.000 claims description 70
• 239000003795 chemical substances by application Substances 0.000 claims description 56
• 125000004193 piperazinyl group Chemical group 0.000 claims description 48
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
• 125000000217 alkyl group Chemical group 0.000 claims description 32
• 125000005843 halogen group Chemical group 0.000 claims description 30
• TZOYXRMEFDYWDQ-UHFFFAOYSA-N 3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2NC(=O)CCC2=C1 TZOYXRMEFDYWDQ-UHFFFAOYSA-N 0.000 claims description 27
• 239000002253 acid Substances 0.000 claims description 25
• 125000001424 substituent group Chemical group 0.000 claims description 22
• 238000002360 preparation method Methods 0.000 claims description 21
• 230000008569 process Effects 0.000 claims description 17
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 14
• 150000003839 salts Chemical class 0.000 claims description 14
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 11
• 125000004423 acyloxy group Chemical group 0.000 claims description 10
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
• 125000002252 acyl group Chemical group 0.000 claims description 7
• 125000003545 alkoxy group Chemical group 0.000 claims description 7
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 7
• 125000003342 alkenyl group Chemical group 0.000 claims description 6
• 125000002947 alkylene group Chemical group 0.000 claims description 5
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
• FYLSBGSTHGTSMF-UHFFFAOYSA-N 5-[3-(4-phenylpiperazin-1-yl)propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound N1C(=O)CCC2=C1C=CC=C2OCCCN(CC1)CCN1C1=CC=CC=C1 FYLSBGSTHGTSMF-UHFFFAOYSA-N 0.000 claims description 4
• KOWNZCLKAYVANJ-UHFFFAOYSA-N 6-[3-(4-phenylpiperazin-1-yl)propoxy]-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)C=CC2=CC=1OCCCN(CC1)CCN1C1=CC=CC=C1 KOWNZCLKAYVANJ-UHFFFAOYSA-N 0.000 claims description 4
• FKPOYTCOFVHHFG-UHFFFAOYSA-N 7-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound C=1C=C2CCC(=O)NC2=CC=1OCC(O)CN(CC1)CCN1C1=CC=CC=C1 FKPOYTCOFVHHFG-UHFFFAOYSA-N 0.000 claims description 4
• SPULWLDIJURFIR-UHFFFAOYSA-N 7-[3-(4-phenylpiperazin-1-yl)propoxy]-1h-quinolin-2-one Chemical compound C1=C2NC(=O)C=CC2=CC=C1OCCCN(CC1)CCN1C1=CC=CC=C1 SPULWLDIJURFIR-UHFFFAOYSA-N 0.000 claims description 4
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
• ADTACPFYJCJJLE-UHFFFAOYSA-N 1-benzyl-5-[3-(4-phenylpiperazin-1-yl)propoxy]-3,4-dihydroquinolin-2-one Chemical compound C1=CC=C2N(CC=3C=CC=CC=3)C(=O)CCC2=C1OCCCN(CC1)CCN1C1=CC=CC=C1 ADTACPFYJCJJLE-UHFFFAOYSA-N 0.000 claims description 3
• RRBYJBJQLCHSIT-UHFFFAOYSA-N 7-[3-(4-benzylpiperazin-1-yl)propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=C2NC(=O)CCC2=CC=C1OCCCN(CC1)CCN1CC1=CC=CC=C1 RRBYJBJQLCHSIT-UHFFFAOYSA-N 0.000 claims description 3
• IVZCTUCBSMZQJP-UHFFFAOYSA-N 7-[3-[4-(2-chlorophenyl)piperazin-1-yl]propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound ClC1=CC=CC=C1N1CCN(CCCOC=2C=C3NC(=O)CCC3=CC=2)CC1 IVZCTUCBSMZQJP-UHFFFAOYSA-N 0.000 claims description 3
• UHLXVWIMGXDONK-UHFFFAOYSA-N 7-[3-[4-(2-ethoxyphenyl)piperazin-1-yl]propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound CCOC1=CC=CC=C1N1CCN(CCCOC=2C=C3NC(=O)CCC3=CC=2)CC1 UHLXVWIMGXDONK-UHFFFAOYSA-N 0.000 claims description 3
• SKHLKHODMJVMFM-UHFFFAOYSA-N 7-[3-[4-(2-fluorophenyl)piperazin-1-yl]propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound FC1=CC=CC=C1N1CCN(CCCOC=2C=C3NC(=O)CCC3=CC=2)CC1 SKHLKHODMJVMFM-UHFFFAOYSA-N 0.000 claims description 3
• ZKAYRIOGIKAXJC-UHFFFAOYSA-N 7-[3-[4-(3-chlorophenyl)piperazin-1-yl]propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound ClC1=CC=CC(N2CCN(CCCOC=3C=C4NC(=O)CCC4=CC=3)CC2)=C1 ZKAYRIOGIKAXJC-UHFFFAOYSA-N 0.000 claims description 3
• MLUSPPKOSUCWLV-UHFFFAOYSA-N 7-[3-[4-(4-methylphenyl)piperazin-1-yl]propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC(C)=CC=C1N1CCN(CCCOC=2C=C3NC(=O)CCC3=CC=2)CC1 MLUSPPKOSUCWLV-UHFFFAOYSA-N 0.000 claims description 3
• USIMZAIRLDAIQJ-UHFFFAOYSA-N 7-[4-(4-phenylpiperazin-1-yl)butoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=C2NC(=O)CCC2=CC=C1OCCCCN(CC1)CCN1C1=CC=CC=C1 USIMZAIRLDAIQJ-UHFFFAOYSA-N 0.000 claims description 3
• MNNDUPMFGLCHOD-UHFFFAOYSA-N 8-bromo-5-[3-(4-phenylpiperazin-1-yl)propoxy]-1h-quinolin-2-one Chemical compound C1=2C=CC(=O)NC=2C(Br)=CC=C1OCCCN(CC1)CCN1C1=CC=CC=C1 MNNDUPMFGLCHOD-UHFFFAOYSA-N 0.000 claims description 3
• 125000000304 alkynyl group Chemical group 0.000 claims description 3
• 238000005658 halogenation reaction Methods 0.000 claims description 3
• VZOFCATXWWIFHP-UHFFFAOYSA-N 1-benzyl-5-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propoxy]-3,4-dihydroquinolin-2-one Chemical compound C1CN(C=2C=CC=CC=2)CCN1CC(O)COC(C=1CCC2=O)=CC=CC=1N2CC1=CC=CC=C1 VZOFCATXWWIFHP-UHFFFAOYSA-N 0.000 claims description 2
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
• 125000000547 substituted alkyl group Chemical group 0.000 claims 8
• 101150065749 Churc1 gene Proteins 0.000 claims 1
• 230000026030 halogenation Effects 0.000 claims 1
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 225
• 239000013078 crystal Substances 0.000 description 192
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 165
• 238000006243 chemical reaction Methods 0.000 description 104
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 102
• 235000019441 ethanol Nutrition 0.000 description 83
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 72
• 238000002844 melting Methods 0.000 description 58
• 230000008018 melting Effects 0.000 description 58
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 57
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 56
• 239000000243 solution Substances 0.000 description 52
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 48
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 46
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 45
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 41
• 239000011541 reaction mixture Substances 0.000 description 41
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 32
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 30
• 238000004821 distillation Methods 0.000 description 26
• 238000001914 filtration Methods 0.000 description 26
• 239000000203 mixture Substances 0.000 description 26
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
• 230000000694 effects Effects 0.000 description 24
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
• MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 21
• 238000010992 reflux Methods 0.000 description 21
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
• 241000699670 Mus sp. Species 0.000 description 18
• NTYJJOPFIAHURM-UHFFFAOYSA-N histamine Natural products NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 18
• 239000002904 solvent Substances 0.000 description 18
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 17
• 239000000739 antihistaminic agent Substances 0.000 description 16
• 150000007514 bases Chemical class 0.000 description 16
• 239000010410 layer Substances 0.000 description 16
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 16
• 235000017557 sodium bicarbonate Nutrition 0.000 description 16
• 238000000354 decomposition reaction Methods 0.000 description 15
• 238000001953 recrystallisation Methods 0.000 description 15
• 235000011121 sodium hydroxide Nutrition 0.000 description 15
• 230000002140 halogenating effect Effects 0.000 description 14
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
• LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 12
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
• 239000007858 starting material Substances 0.000 description 12
• 239000012442 inert solvent Substances 0.000 description 11
• 238000003756 stirring Methods 0.000 description 11
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
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• 210000003169 central nervous system Anatomy 0.000 description 10
• 229960001340 histamine Drugs 0.000 description 10
• 238000006460 hydrolysis reaction Methods 0.000 description 10
• YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 10
• 235000009518 sodium iodide Nutrition 0.000 description 10
• 239000008096 xylene Substances 0.000 description 10
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
• 241000699666 Mus <mouse, genus> Species 0.000 description 9
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 9
• 238000012360 testing method Methods 0.000 description 9
• NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 8
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
• GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 8
• 230000001387 anti-histamine Effects 0.000 description 8
• 229910000029 sodium carbonate Inorganic materials 0.000 description 8
• 235000017550 sodium carbonate Nutrition 0.000 description 8
• 239000012312 sodium hydride Substances 0.000 description 8
• 229910000104 sodium hydride Inorganic materials 0.000 description 8
• 229920002472 Starch Polymers 0.000 description 7
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 7
• 230000037396 body weight Effects 0.000 description 7
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 7
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 7
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• 235000011181 potassium carbonates Nutrition 0.000 description 7
• 235000011118 potassium hydroxide Nutrition 0.000 description 7
• 239000008107 starch Substances 0.000 description 7
• 235000019698 starch Nutrition 0.000 description 7
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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• 239000002244 precipitate Substances 0.000 description 6
• 239000000725 suspension Substances 0.000 description 6
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 5
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 5
• HKTZKESTBBPIET-UHFFFAOYSA-N 5-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound C=1C=CC=2NC(=O)CCC=2C=1OCC(O)CN(CC1)CCN1C1=CC=CC=C1 HKTZKESTBBPIET-UHFFFAOYSA-N 0.000 description 5
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• 238000005481 NMR spectroscopy Methods 0.000 description 5
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• 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
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• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 4
• 206010002091 Anaesthesia Diseases 0.000 description 4
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• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
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• 150000001350 alkyl halides Chemical class 0.000 description 4
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
• 125000003118 aryl group Chemical group 0.000 description 4
• 239000003054 catalyst Substances 0.000 description 4
• 238000001816 cooling Methods 0.000 description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
• 238000010438 heat treatment Methods 0.000 description 4
• 239000002198 insoluble material Substances 0.000 description 4
• GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
• 150000004682 monohydrates Chemical class 0.000 description 4
• 239000000843 powder Substances 0.000 description 4
• 238000010898 silica gel chromatography Methods 0.000 description 4
• 239000011734 sodium Substances 0.000 description 4
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