EA023212B1 - ПРОИЗВОДНЫЕ 3,4,4a,10b-ТЕТРАГИДРО-1H-ТИОПИРАНО[4,3-c]ИЗОХИНОЛИНА - Google Patents

Info

Publication number

EA023212B1

EA023212B1 EA201200891A EA201200891A EA023212B1 EA 023212 B1 EA023212 B1 EA 023212B1 EA 201200891 A EA201200891 A EA 201200891A EA 201200891 A EA201200891 A EA 201200891A EA 023212 B1 EA023212 B1 EA 023212B1

Authority

EA

Eurasian Patent Office

Prior art keywords

methyl

ethyl

compound

phenyl

ethoxy

Prior art date

2009-12-18

Links

• Espacenet
• Global Dossier
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• ZQCSTHXMOLTGJA-UHFFFAOYSA-N 3,4,4a,10b-tetrahydro-1h-thiopyrano[4,3-c]isoquinoline Chemical class N1=CC2=CC=CC=C2C2C1CCSC2 ZQCSTHXMOLTGJA-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 855
• 239000003112 inhibitor Substances 0.000 claims abstract description 30
• 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims abstract description 14
• 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims abstract description 14
• -1 1-methyl-1H-imidazol-2-yl Chemical group 0.000 claims description 626
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 322
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 173
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 151
• ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 83
• 239000008194 pharmaceutical composition Substances 0.000 claims description 50
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 43
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 40
• 238000011282 treatment Methods 0.000 claims description 40
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 37
• 238000002360 preparation method Methods 0.000 claims description 35
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 34
• 239000003814 drug Substances 0.000 claims description 28
• 208000002815 pulmonary hypertension Diseases 0.000 claims description 26
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 24
• 230000002265 prevention Effects 0.000 claims description 23
• 229940124597 therapeutic agent Drugs 0.000 claims description 21
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 18
• 208000006673 asthma Diseases 0.000 claims description 15
• 208000005069 pulmonary fibrosis Diseases 0.000 claims description 15
• FNKQXYHWGSIFBK-RPDRRWSUSA-N sapropterin Chemical compound N1=C(N)NC(=O)C2=C1NC[C@H]([C@@H](O)[C@@H](O)C)N2 FNKQXYHWGSIFBK-RPDRRWSUSA-N 0.000 claims description 15
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 14
• 239000000556 agonist Substances 0.000 claims description 13
• 230000001684 chronic effect Effects 0.000 claims description 13
• 239000002571 phosphodiesterase inhibitor Substances 0.000 claims description 13
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• 208000030603 inherited susceptibility to asthma Diseases 0.000 claims description 12
• 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 claims description 11
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• 239000003242 anti bacterial agent Substances 0.000 claims description 10
• 239000003199 leukotriene receptor blocking agent Substances 0.000 claims description 10
• 239000000021 stimulant Substances 0.000 claims description 10
• 208000030090 Acute Disease Diseases 0.000 claims description 9
• 201000003883 Cystic fibrosis Diseases 0.000 claims description 9
• 229940088710 antibiotic agent Drugs 0.000 claims description 9
• 239000002876 beta blocker Substances 0.000 claims description 9
• 229940097320 beta blocking agent Drugs 0.000 claims description 9
• 239000002308 endothelin receptor antagonist Substances 0.000 claims description 9
• 239000003119 guanylate cyclase activator Substances 0.000 claims description 9
• 208000014085 Chronic respiratory disease Diseases 0.000 claims description 8
• 102000003834 Histamine H1 Receptors Human genes 0.000 claims description 8
• 108090000110 Histamine H1 Receptors Proteins 0.000 claims description 8
• 239000000867 Lipoxygenase Inhibitor Substances 0.000 claims description 8
• 229960001334 corticosteroids Drugs 0.000 claims description 8
• 230000002401 inhibitory effect Effects 0.000 claims description 8
• 229940044551 receptor antagonist Drugs 0.000 claims description 8
• 239000002464 receptor antagonist Substances 0.000 claims description 8
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• 206010014561 Emphysema Diseases 0.000 claims description 7
• 229940118365 Endothelin receptor antagonist Drugs 0.000 claims description 7
• 102000004316 Oxidoreductases Human genes 0.000 claims description 7
• 108090000854 Oxidoreductases Proteins 0.000 claims description 7
• 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 claims description 7
• 206010006451 bronchitis Diseases 0.000 claims description 7
• 239000000812 cholinergic antagonist Substances 0.000 claims description 7
• 229940082657 digitalis glycosides Drugs 0.000 claims description 7
• 239000002934 diuretic Substances 0.000 claims description 7
• 229940030606 diuretics Drugs 0.000 claims description 7
• 229960003444 immunosuppressant agent Drugs 0.000 claims description 7
• 239000003018 immunosuppressive agent Substances 0.000 claims description 7
• 229940065725 leukotriene receptor antagonists for obstructive airway diseases Drugs 0.000 claims description 7
• 230000002685 pulmonary effect Effects 0.000 claims description 7
• 206010006458 Bronchitis chronic Diseases 0.000 claims description 6
• 239000003146 anticoagulant agent Substances 0.000 claims description 6
• 229940127219 anticoagulant drug Drugs 0.000 claims description 6
• 208000007451 chronic bronchitis Diseases 0.000 claims description 6
• ISWRGOKTTBVCFA-UHFFFAOYSA-N pirfenidone Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC=C1 ISWRGOKTTBVCFA-UHFFFAOYSA-N 0.000 claims description 6
• 229960003073 pirfenidone Drugs 0.000 claims description 6
• 229940088594 vitamin Drugs 0.000 claims description 6
• 235000013343 vitamin Nutrition 0.000 claims description 6
• 239000011782 vitamin Substances 0.000 claims description 6
• 229930003231 vitamin Natural products 0.000 claims description 6
• 150000003722 vitamin derivatives Chemical class 0.000 claims description 6
• 230000001078 anti-cholinergic effect Effects 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
• 210000002345 respiratory system Anatomy 0.000 claims description 4
• 239000000048 adrenergic agonist Substances 0.000 claims description 2
• 229940126157 adrenergic receptor agonist Drugs 0.000 claims description 2
• 108090000312 Calcium Channels Proteins 0.000 claims 2
• 102000003922 Calcium Channels Human genes 0.000 claims 2
• 208000018569 Respiratory Tract disease Diseases 0.000 claims 2
• NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
• 108091006146 Channels Proteins 0.000 claims 1
• 208000017667 Chronic Disease Diseases 0.000 claims 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 337
• 239000007787 solid Substances 0.000 description 181
• 239000000243 solution Substances 0.000 description 175
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 144
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 128
• ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 124
• 238000000034 method Methods 0.000 description 118
• 239000000203 mixture Substances 0.000 description 102
• 238000003818 flash chromatography Methods 0.000 description 98
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 94
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 89
• DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 description 83
• 238000006243 chemical reaction Methods 0.000 description 82
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 74
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 73
• 239000011541 reaction mixture Substances 0.000 description 67
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 65
• 238000010828 elution Methods 0.000 description 62
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 61
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 61
• 238000000746 purification Methods 0.000 description 61
• 239000000741 silica gel Substances 0.000 description 58
• 229910002027 silica gel Inorganic materials 0.000 description 58
• 239000002904 solvent Substances 0.000 description 56
• 239000000725 suspension Substances 0.000 description 56
• UZKBSZSTDQSMDR-UHFFFAOYSA-N 1-[(4-chlorophenyl)-phenylmethyl]piperazine Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)N1CCNCC1 UZKBSZSTDQSMDR-UHFFFAOYSA-N 0.000 description 53
• 239000007864 aqueous solution Substances 0.000 description 53
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 52
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 52
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 51
• 229910000027 potassium carbonate Inorganic materials 0.000 description 47
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 45
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 43
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
• 230000002829 reductive effect Effects 0.000 description 41
• 201000010099 disease Diseases 0.000 description 39
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 37
• 150000003839 salts Chemical class 0.000 description 36
• 238000003756 stirring Methods 0.000 description 33
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 31
• 238000002953 preparative HPLC Methods 0.000 description 31
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 30
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• 239000003480 eluent Substances 0.000 description 28
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• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 17
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• 239000000126 substance Substances 0.000 description 16
• QVEDOQSCNLZPJX-UHFFFAOYSA-N 1h-pyrimidine-2,4-dione;hydrochloride Chemical compound Cl.O=C1C=CNC(=O)N1 QVEDOQSCNLZPJX-UHFFFAOYSA-N 0.000 description 15
• VUYVXCJTTQJVKJ-UHFFFAOYSA-L palladium(2+);tricyclohexylphosphane;dichloride Chemical compound Cl[Pd]Cl.C1CCCCC1P(C1CCCCC1)C1CCCCC1.C1CCCCC1P(C1CCCCC1)C1CCCCC1 VUYVXCJTTQJVKJ-UHFFFAOYSA-L 0.000 description 14
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• XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 7
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• GKTQKQTXHNUFSP-UHFFFAOYSA-N thieno[3,4-c]pyrrole-4,6-dione Chemical compound S1C=C2C(=O)NC(=O)C2=C1 GKTQKQTXHNUFSP-UHFFFAOYSA-N 0.000 description 7
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• VLXVPDOWMACDNZ-UHFFFAOYSA-N 5-(chloromethyl)-3-(methoxymethyl)-1,2,4-oxadiazole Chemical compound COCC1=NOC(CCl)=N1 VLXVPDOWMACDNZ-UHFFFAOYSA-N 0.000 description 5
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