CN101939291A - 作为β2肾上腺素能受体激动剂的4-(2-氨基-1-羟乙基)苯酚衍生物 - Google Patents

Info

Publication number

CN101939291A

CN101939291A CN2009801051173A CN200980105117A CN101939291A CN 101939291 A CN101939291 A CN 101939291A CN 2009801051173 A CN2009801051173 A CN 2009801051173A CN 200980105117 A CN200980105117 A CN 200980105117A CN 101939291 A CN101939291 A CN 101939291A

Authority

CN

China

Prior art keywords

phenyl

hydroxyl

ethyl

group

amino

Prior art date

2008-02-28

Legal status (The legal status 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 status listed.)

Pending

Links

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• 102000016966 beta-2 Adrenergic Receptors Human genes 0.000 title claims description 23
• 108010014499 beta-2 Adrenergic Receptors Proteins 0.000 title claims description 23
• 239000000556 agonist Substances 0.000 title description 4
• QHGUCRYDKWKLMG-UHFFFAOYSA-N octopamine Chemical class NCC(O)C1=CC=C(O)C=C1 QHGUCRYDKWKLMG-UHFFFAOYSA-N 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 277
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 273
• 150000003839 salts Chemical class 0.000 claims abstract description 36
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 30
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 30
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 28
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 18
• 125000002950 monocyclic group Chemical group 0.000 claims abstract description 17
• 239000012453 solvate Substances 0.000 claims abstract description 12
• 125000005843 halogen group Chemical group 0.000 claims abstract description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 8
• 125000004104 aryloxy group Chemical group 0.000 claims abstract description 7
• 125000003367 polycyclic group Chemical group 0.000 claims abstract description 7
• 125000003118 aryl group Chemical group 0.000 claims abstract description 6
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 256
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 177
• 239000004202 carbamide Substances 0.000 claims description 161
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 118
• 239000000203 mixture Substances 0.000 claims description 89
• -1 Phenyl ring Chemical group 0.000 claims description 85
• 239000003814 drug Substances 0.000 claims description 64
• 238000011282 treatment Methods 0.000 claims description 36
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 27
• 239000003795 chemical substances by application Substances 0.000 claims description 26
• 201000010099 disease Diseases 0.000 claims description 25
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
• 238000000034 method Methods 0.000 claims description 21
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 15
• 229940079593 drug Drugs 0.000 claims description 13
• 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 12
• 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 12
• 230000001225 therapeutic effect Effects 0.000 claims description 11
• 201000008827 tuberculosis Diseases 0.000 claims description 10
• 208000006673 asthma Diseases 0.000 claims description 9
• 238000002360 preparation method Methods 0.000 claims description 9
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 8
• 229910052731 fluorine Inorganic materials 0.000 claims description 8
• 230000001575 pathological effect Effects 0.000 claims description 8
• 208000020446 Cardiac disease Diseases 0.000 claims description 7
• 208000010412 Glaucoma Diseases 0.000 claims description 7
• 208000006399 Premature Obstetric Labor Diseases 0.000 claims description 7
• 206010036600 Premature labour Diseases 0.000 claims description 7
• 208000019622 heart disease Diseases 0.000 claims description 7
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
• 208000026440 premature labor Diseases 0.000 claims description 7
• 206010061218 Inflammation Diseases 0.000 claims description 6
• 125000000217 alkyl group Chemical group 0.000 claims description 6
• 210000003792 cranial nerve Anatomy 0.000 claims description 6
• 230000004054 inflammatory process Effects 0.000 claims description 6
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 5
• GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 claims description 5
• 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 5
• 239000011737 fluorine Substances 0.000 claims description 5
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
• 230000003153 cholinolytic effect Effects 0.000 claims description 3
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
• 230000001105 regulatory effect Effects 0.000 claims description 2
• 229910052757 nitrogen Inorganic materials 0.000 abstract description 7
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
• 125000001424 substituent group Chemical group 0.000 abstract 2
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 abstract 1
• 125000000172 C5-C10 aryl group Chemical group 0.000 abstract 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 180
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 142
• 239000000463 material Substances 0.000 description 131
• 239000007787 solid Substances 0.000 description 103
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 92
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• 238000010828 elution Methods 0.000 description 77
• 238000004440 column chromatography Methods 0.000 description 75
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 75
• 238000000746 purification Methods 0.000 description 70
• 239000000741 silica gel Substances 0.000 description 70
• 229910002027 silica gel Inorganic materials 0.000 description 70
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 64
• 239000000243 solution Substances 0.000 description 64
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 63
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• 239000002585 base Substances 0.000 description 56
• 230000006837 decompression Effects 0.000 description 53
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 48
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 46
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• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
• 238000005160 1H NMR spectroscopy Methods 0.000 description 38
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
• 150000002576 ketones Chemical class 0.000 description 35
• 239000011541 reaction mixture Substances 0.000 description 34
• 238000001914 filtration Methods 0.000 description 32
• 230000035484 reaction time Effects 0.000 description 32
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 29
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 28
• 239000012279 sodium borohydride Substances 0.000 description 28
• 229910000033 sodium borohydride Inorganic materials 0.000 description 28
• IRFHMTUHTBSEBK-QGZVFWFLSA-N tert-butyl n-[(2s)-2-(2,5-difluorophenyl)-3-quinolin-3-ylpropyl]carbamate Chemical compound C1([C@H](CC=2C=C3C=CC=CC3=NC=2)CNC(=O)OC(C)(C)C)=CC(F)=CC=C1F IRFHMTUHTBSEBK-QGZVFWFLSA-N 0.000 description 28
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 27
• 229910052760 oxygen Inorganic materials 0.000 description 24
• 230000000694 effects Effects 0.000 description 23
• 239000001301 oxygen Substances 0.000 description 23
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 22
• 239000002775 capsule Substances 0.000 description 22
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
• 238000009472 formulation Methods 0.000 description 21
• 238000012360 testing method Methods 0.000 description 21
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
• 150000001412 amines Chemical class 0.000 description 20
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 20
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 20
• 239000000843 powder Substances 0.000 description 19
• PCBZRNYXXCIELG-WYFCWLEVSA-N COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 Chemical compound COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 PCBZRNYXXCIELG-WYFCWLEVSA-N 0.000 description 18
• 238000006243 chemical reaction Methods 0.000 description 18
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 16
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
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• 239000000376 reactant Substances 0.000 description 14
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• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
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• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
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