SE461147B - Karbostyrilderivat och farmaceutisk komposition innehaallande dem - Google Patents

Info

Publication number

SE461147B

SE461147B SE8102690A SE8102690A SE461147B SE 461147 B SE461147 B SE 461147B SE 8102690 A SE8102690 A SE 8102690A SE 8102690 A SE8102690 A SE 8102690A SE 461147 B SE461147 B SE 461147B

Authority

SE

Sweden

Prior art keywords

dihydrocarbostyril

group

propoxy

lower alkyl

crystals

Prior art date

1980-02-29

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 99
• 239000008194 pharmaceutical composition Substances 0.000 title claims 2
• -1 heterocyclic ring radical Chemical class 0.000 claims description 432
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 111
• 125000000217 alkyl group Chemical group 0.000 claims description 85
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 60
• 125000001424 substituent group Chemical group 0.000 claims description 32
• 125000004432 carbon atom Chemical group C* 0.000 claims description 31
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
• 229910052757 nitrogen Inorganic materials 0.000 claims description 18
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
• SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims description 12
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 10
• 125000003545 alkoxy group Chemical group 0.000 claims description 10
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 10
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 9
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• 239000004480 active ingredient Substances 0.000 claims description 5
• 125000003342 alkenyl group Chemical group 0.000 claims description 5
• 125000002947 alkylene group Chemical group 0.000 claims description 5
• 125000000623 heterocyclic group Chemical group 0.000 claims description 5
• VRBDJIXPYHZXOX-UHFFFAOYSA-N n-(3-hydroxycyclohexyl)-n-(2-hydroxyethyl)-4-[(2-oxo-1h-quinolin-6-yl)oxy]butanamide Chemical compound C=1C=C2NC(=O)C=CC2=CC=1OCCCC(=O)N(CCO)C1CCCC(O)C1 VRBDJIXPYHZXOX-UHFFFAOYSA-N 0.000 claims description 5
• OKVCJEKPURYZKG-UHFFFAOYSA-N n-cyclohexyl-n-(2-hydroxyethyl)-4-[(2-oxo-3,4-dihydro-1h-quinolin-6-yl)oxy]butanamide Chemical compound C=1C=C2NC(=O)CCC2=CC=1OCCCC(=O)N(CCO)C1CCCCC1 OKVCJEKPURYZKG-UHFFFAOYSA-N 0.000 claims description 5
• 125000002541 furyl group Chemical group 0.000 claims description 4
• 150000003839 salts Chemical class 0.000 claims description 4
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 4
• 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 3
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
• 230000000069 prophylactic effect Effects 0.000 claims description 2
• 208000007536 Thrombosis Diseases 0.000 claims 1
• 150000001875 compounds Chemical class 0.000 description 333
• 239000013078 crystal Substances 0.000 description 284
• 238000006243 chemical reaction Methods 0.000 description 113
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 84
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 72
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 70
• 238000012360 testing method Methods 0.000 description 58
• 238000000034 method Methods 0.000 description 53
• 239000000203 mixture Substances 0.000 description 53
• 239000000243 solution Substances 0.000 description 53
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
• 150000001412 amines Chemical class 0.000 description 42
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
• 229960001701 chloroform Drugs 0.000 description 36
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
• 239000002904 solvent Substances 0.000 description 32
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
• 238000003756 stirring Methods 0.000 description 28
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• 230000000694 effects Effects 0.000 description 22
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• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 17
• 230000002401 inhibitory effect Effects 0.000 description 17
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 16
• 239000007788 liquid Substances 0.000 description 16
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 16
• 241000283973 Oryctolagus cuniculus Species 0.000 description 15
• 239000003054 catalyst Substances 0.000 description 15
• 229910052739 hydrogen Inorganic materials 0.000 description 15
• 125000005504 styryl group Chemical group 0.000 description 15
• 102000008186 Collagen Human genes 0.000 description 14
• 108010035532 Collagen Proteins 0.000 description 14
• 229920001436 collagen Polymers 0.000 description 14
• 238000004821 distillation Methods 0.000 description 14
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• 230000000144 pharmacologic effect Effects 0.000 description 14
• 239000000126 substance Substances 0.000 description 14
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• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 13
• XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 12
• XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 description 12
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
• 241000282472 Canis lupus familiaris Species 0.000 description 12
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
• 229910052799 carbon Inorganic materials 0.000 description 12
• 239000003795 chemical substances by application Substances 0.000 description 12
• 238000002360 preparation method Methods 0.000 description 12
• 238000010898 silica gel chromatography Methods 0.000 description 12
• 235000011121 sodium hydroxide Nutrition 0.000 description 12
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
• 239000007864 aqueous solution Substances 0.000 description 11
• 238000001914 filtration Methods 0.000 description 11
• 239000004615 ingredient Substances 0.000 description 11
• 210000004623 platelet-rich plasma Anatomy 0.000 description 11
• 230000009467 reduction Effects 0.000 description 11
• 238000006722 reduction reaction Methods 0.000 description 11
• WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
• 241000700159 Rattus Species 0.000 description 10
• 239000002253 acid Substances 0.000 description 10
• 150000007514 bases Chemical class 0.000 description 10
• 150000002148 esters Chemical class 0.000 description 10
• XHVDMLOJJHWEOO-UHFFFAOYSA-N n-cyclohexyl-n-(2-hydroxyethyl)-4-[(2-oxo-1h-quinolin-6-yl)oxy]butanamide Chemical compound C=1C=C2NC(=O)C=CC2=CC=1OCCCC(=O)N(CCO)C1CCCCC1 XHVDMLOJJHWEOO-UHFFFAOYSA-N 0.000 description 10
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
• 239000002274 desiccant Substances 0.000 description 9
• 239000012452 mother liquor Substances 0.000 description 9
• 235000002639 sodium chloride Nutrition 0.000 description 9
• MGUMZJAQENFQKN-UHFFFAOYSA-N 2-(cyclohexylamino)ethanol Chemical compound OCCNC1CCCCC1 MGUMZJAQENFQKN-UHFFFAOYSA-N 0.000 description 8
• YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 8
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products 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 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
• 230000001965 increasing effect Effects 0.000 description 8
• 239000008101 lactose Substances 0.000 description 8
• 235000019359 magnesium stearate Nutrition 0.000 description 8
• 238000002844 melting Methods 0.000 description 8
• 230000008018 melting Effects 0.000 description 8
• 239000011734 sodium Substances 0.000 description 8
• IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 7
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• 210000001367 artery Anatomy 0.000 description 7
• WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 7
• 229940095074 cyclic amp Drugs 0.000 description 7
• 238000000921 elemental analysis Methods 0.000 description 7
• 150000004679 hydroxides Chemical class 0.000 description 7
• OEFPQRGIWRMLRA-UHFFFAOYSA-N n-ethyl-4-[(2-oxo-1h-quinolin-6-yl)oxy]-n-pyridin-2-ylbutanamide Chemical compound C=1C=C2NC(=O)C=CC2=CC=1OCCCC(=O)N(CC)C1=CC=CC=N1 OEFPQRGIWRMLRA-UHFFFAOYSA-N 0.000 description 7
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
• 238000000862 absorption spectrum Methods 0.000 description 6
• 150000008065 acid anhydrides Chemical class 0.000 description 6
• OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 6
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• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
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• QTLOIVSZSJWESB-UHFFFAOYSA-N n-(2-hydroxyethyl)-n-(oxan-2-ylmethyl)-5-[(2-oxo-3,4-dihydro-1h-quinolin-6-yl)oxy]pentanamide Chemical compound C=1C=C2NC(=O)CCC2=CC=1OCCCCC(=O)N(CCO)CC1CCCCO1 QTLOIVSZSJWESB-UHFFFAOYSA-N 0.000 description 6
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• 239000012044 organic layer Substances 0.000 description 6
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• DALLEQMEZNMFHA-UHFFFAOYSA-N n-(4-hydroxybutyl)-n-(oxan-2-ylmethyl)-5-[(2-oxo-3,4-dihydro-1h-quinolin-6-yl)oxy]pentanamide Chemical compound C=1C=C2NC(=O)CCC2=CC=1OCCCCC(=O)N(CCCCO)CC1CCCCO1 DALLEQMEZNMFHA-UHFFFAOYSA-N 0.000 description 4
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• FTBKSKFQZQATJH-UHFFFAOYSA-N n-(cyclohexylmethyl)-n-(2-hydroxyethyl)-5-[(2-oxo-3,4-dihydro-1h-quinolin-6-yl)oxy]pentanamide Chemical compound C=1C=C2NC(=O)CCC2=CC=1OCCCCC(=O)N(CCO)CC1CCCCC1 FTBKSKFQZQATJH-UHFFFAOYSA-N 0.000 description 4
• CDWYAYQZGVPZJI-UHFFFAOYSA-N n-benzyl-n-(2-hydroxyethyl)-5-[(2-oxo-3,4-dihydro-1h-quinolin-6-yl)oxy]pentanamide Chemical compound C=1C=C2NC(=O)CCC2=CC=1OCCCCC(=O)N(CCO)CC1=CC=CC=C1 CDWYAYQZGVPZJI-UHFFFAOYSA-N 0.000 description 4
• RBKXZRFPKVQUQX-UHFFFAOYSA-N n-methyl-4-[(2-oxo-1h-quinolin-6-yl)oxy]-n-(thiophen-2-ylmethyl)butanamide Chemical compound C=1C=C2NC(=O)C=CC2=CC=1OCCCC(=O)N(C)CC1=CC=CS1 RBKXZRFPKVQUQX-UHFFFAOYSA-N 0.000 description 4
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