KR20080033372A - 신규 벤조티아졸론 유도체 - Google Patents

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Publication number

KR20080033372A

KR20080033372A KR1020087003165A KR20087003165A KR20080033372A KR 20080033372 A KR20080033372 A KR 20080033372A KR 1020087003165 A KR1020087003165 A KR 1020087003165A KR 20087003165 A KR20087003165 A KR 20087003165A KR 20080033372 A KR20080033372 A KR 20080033372A

Authority

KR

South Korea

Prior art keywords

ethyl

compound

alkyl

hydroxy

oxo

Prior art date

2005-08-09

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.)

Ceased

Links

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• BXQNSPXDWSNUKE-UHFFFAOYSA-N 1,3-benzothiazole 1-oxide Chemical class C1=CC=C2S(=O)C=NC2=C1 BXQNSPXDWSNUKE-UHFFFAOYSA-N 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 327
• 238000000034 method Methods 0.000 claims abstract description 65
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
• 230000008569 process Effects 0.000 claims abstract description 10
• 238000002360 preparation method Methods 0.000 claims abstract description 9
• 238000002560 therapeutic procedure Methods 0.000 claims abstract description 8
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 409
• -1 cyano, carboxyl Chemical group 0.000 claims description 192
• 239000001257 hydrogen Substances 0.000 claims description 108
• 229910052739 hydrogen Inorganic materials 0.000 claims description 108
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 92
• ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 69
• 150000003839 salts Chemical class 0.000 claims description 65
• 125000000217 alkyl group Chemical group 0.000 claims description 54
• 229910052757 nitrogen Inorganic materials 0.000 claims description 51
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 49
• 229910052760 oxygen Inorganic materials 0.000 claims description 48
• 239000001301 oxygen Substances 0.000 claims description 48
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 43
• 229910052736 halogen Inorganic materials 0.000 claims description 42
• 150000002367 halogens Chemical class 0.000 claims description 42
• 125000005842 heteroatom Chemical group 0.000 claims description 40
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 40
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 37
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 36
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 32
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 32
• 125000001424 substituent group Chemical group 0.000 claims description 31
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 27
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
• 229920006395 saturated elastomer Polymers 0.000 claims description 27
• 229910052717 sulfur Inorganic materials 0.000 claims description 27
• 239000011593 sulfur Substances 0.000 claims description 27
• 102000007399 Nuclear hormone receptor Human genes 0.000 claims description 25
• 108020005497 Nuclear hormone receptor Proteins 0.000 claims description 25
• 125000004122 cyclic group Chemical group 0.000 claims description 25
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 23
• 238000011282 treatment Methods 0.000 claims description 21
• 208000006673 asthma Diseases 0.000 claims description 19
• 239000003795 chemical substances by application Substances 0.000 claims description 19
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 18
• 125000003118 aryl group Chemical group 0.000 claims description 17
• 150000002431 hydrogen Chemical class 0.000 claims description 17
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
• 201000010099 disease Diseases 0.000 claims description 16
• 230000000694 effects Effects 0.000 claims description 15
• 125000003386 piperidinyl group Chemical group 0.000 claims description 14
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 13
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
• 239000003814 drug Substances 0.000 claims description 13
• 125000000623 heterocyclic group Chemical group 0.000 claims description 12
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
• 125000004076 pyridyl group Chemical group 0.000 claims description 12
• 239000000556 agonist Substances 0.000 claims description 11
• 125000001072 heteroaryl group Chemical group 0.000 claims description 11
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 10
• 108010014499 beta-2 Adrenergic Receptors Proteins 0.000 claims description 10
• 238000004519 manufacturing process Methods 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
• 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 9
• 229940044551 receptor antagonist Drugs 0.000 claims description 9
• 239000002464 receptor antagonist Substances 0.000 claims description 9
• 206010039083 rhinitis Diseases 0.000 claims description 9
• 208000011580 syndromic disease Diseases 0.000 claims description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
• 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 7
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
• 125000006239 protecting group Chemical group 0.000 claims description 7
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 6
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 6
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 6
• 102000003676 Glucocorticoid Receptors Human genes 0.000 claims description 6
• 108090000079 Glucocorticoid Receptors Proteins 0.000 claims description 6
• 125000002947 alkylene group Chemical group 0.000 claims description 6
• 239000003638 chemical reducing agent Substances 0.000 claims description 6
• 208000027866 inflammatory disease Diseases 0.000 claims description 6
• 208000024891 symptom Diseases 0.000 claims description 6
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
• 125000005975 2-phenylethyloxy group Chemical group 0.000 claims description 5
• 239000002671 adjuvant Substances 0.000 claims description 5
• 230000008878 coupling Effects 0.000 claims description 5
• 238000010168 coupling process Methods 0.000 claims description 5
• 238000005859 coupling reaction Methods 0.000 claims description 5
• ZVULMJYRVAVKCP-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-n-[2-[2-(4-hydroxy-2-oxo-3h-1,3-benzothiazol-7-yl)ethylamino]ethyl]-3-(2-naphthalen-1-ylethoxy)propanamide Chemical compound C1=CC=C2C(CCOCCC(=O)N(CCNCCC=3C=4SC(=O)NC=4C(O)=CC=3)CCN(CC)CC)=CC=CC2=C1 ZVULMJYRVAVKCP-UHFFFAOYSA-N 0.000 claims description 5
• QLMLFIVRQSTCGA-UHFFFAOYSA-N n-benzyl-n-[2-[2-(4-hydroxy-2-oxo-3h-1,3-benzothiazol-7-yl)ethylamino]ethyl]-3-(2-phenylethoxy)propanamide Chemical compound C1=2SC(=O)NC=2C(O)=CC=C1CCNCCN(C(=O)CCOCCC=1C=CC=CC=1)CC1=CC=CC=C1 QLMLFIVRQSTCGA-UHFFFAOYSA-N 0.000 claims description 5
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 5
• 208000023504 respiratory system disease Diseases 0.000 claims description 5
• 125000006833 (C1-C5) alkylene group Chemical group 0.000 claims description 4
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 4
• XMKHJPWKXSCOOW-UHFFFAOYSA-N 3-[2-(4-bromophenyl)ethoxy]-n-[2-[2-(4-hydroxy-2-oxo-3h-1,3-benzothiazol-7-yl)ethylamino]ethyl]-n-(2-phenylethyl)propanamide Chemical compound C1=2SC(=O)NC=2C(O)=CC=C1CCNCCN(C(=O)CCOCCC=1C=CC(Br)=CC=1)CCC1=CC=CC=C1 XMKHJPWKXSCOOW-UHFFFAOYSA-N 0.000 claims description 4
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
• 206010014561 Emphysema Diseases 0.000 claims description 4
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
• 230000009286 beneficial effect Effects 0.000 claims description 4
• 201000009267 bronchiectasis Diseases 0.000 claims description 4
• 206010006451 bronchitis Diseases 0.000 claims description 4
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 229940043355 kinase inhibitor Drugs 0.000 claims description 4
• KFFHPHUPVZQMDB-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-n-[2-[2-(4-hydroxy-2-oxo-3h-1,3-benzothiazol-7-yl)ethylamino]ethyl]-3-(2-phenylethoxy)propanamide Chemical compound C=1C=C(O)C=2NC(=O)SC=2C=1CCNCCN(CCN(C)C)C(=O)CCOCCC1=CC=CC=C1 KFFHPHUPVZQMDB-UHFFFAOYSA-N 0.000 claims description 4
• LHZIHZFOZNJXHV-UHFFFAOYSA-N n-[2-[2-(4-hydroxy-2-oxo-3h-1,3-benzothiazol-7-yl)ethylamino]ethyl]-3-(2-phenylethoxy)-n-(2-phenylethyl)propanamide Chemical compound C1=2SC(=O)NC=2C(O)=CC=C1CCNCCN(C(=O)CCOCCC=1C=CC=CC=1)CCC1=CC=CC=C1 LHZIHZFOZNJXHV-UHFFFAOYSA-N 0.000 claims description 4
• QWWWHMPAWHZXJN-UHFFFAOYSA-N n-[2-[2-(4-hydroxy-2-oxo-3h-1,3-benzothiazol-7-yl)ethylamino]ethyl]-3-(2-phenylethoxy)-n-[5-(2-phenylethoxy)pentyl]propanamide Chemical compound C1=2SC(=O)NC=2C(O)=CC=C1CCNCCN(C(=O)CCOCCC=1C=CC=CC=1)CCCCCOCCC1=CC=CC=C1 QWWWHMPAWHZXJN-UHFFFAOYSA-N 0.000 claims description 4
• DJHGXCJJUORMBG-UHFFFAOYSA-N n-[2-[2-(4-hydroxy-2-oxo-3h-1,3-benzothiazol-7-yl)ethylamino]ethyl]-n-phenyl-3-(2-phenylethoxy)propanamide Chemical compound C1=2SC(=O)NC=2C(O)=CC=C1CCNCCN(C=1C=CC=CC=1)C(=O)CCOCCC1=CC=CC=C1 DJHGXCJJUORMBG-UHFFFAOYSA-N 0.000 claims description 4
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
• 239000003757 phosphotransferase inhibitor Substances 0.000 claims description 4
• SSVQIEZSEPUHKD-UHFFFAOYSA-N tert-butyl 4-[[2-[2-(4-hydroxy-2-oxo-3h-1,3-benzothiazol-7-yl)ethylamino]ethyl-[3-(2-phenylethoxy)propanoyl]amino]methyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CN(C(=O)CCOCCC=1C=CC=CC=1)CCNCCC1=CC=C(O)C2=C1SC(=O)N2 SSVQIEZSEPUHKD-UHFFFAOYSA-N 0.000 claims description 4
• BIUQAKIPAZVDPQ-UHFFFAOYSA-N 4-hydroxy-7-[2-[2-[3-(2-phenylethoxy)propyl-(2-phenylethyl)amino]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound C1=2SC(=O)NC=2C(O)=CC=C1CCNCCN(CCC=1C=CC=CC=1)CCCOCCC1=CC=CC=C1 BIUQAKIPAZVDPQ-UHFFFAOYSA-N 0.000 claims description 3
• 102000009410 Chemokine receptor Human genes 0.000 claims description 3
• 108050000299 Chemokine receptor Proteins 0.000 claims description 3
• 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 3
• 230000003551 muscarinic effect Effects 0.000 claims description 3
• BSURVCPNUZUCMK-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-n-[2-[2-(4-hydroxy-2-oxo-3h-1,3-benzothiazol-7-yl)ethylamino]ethyl]-3-(2-naphthalen-2-ylethoxy)propanamide Chemical compound C1=CC=CC2=CC(CCOCCC(=O)N(CCNCCC=3C=4SC(=O)NC=4C(O)=CC=3)CCN(CC)CC)=CC=C21 BSURVCPNUZUCMK-UHFFFAOYSA-N 0.000 claims description 3
• UGUFEFMMJARSLS-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-n-[2-[2-(4-hydroxy-2-oxo-3h-1,3-benzothiazol-7-yl)ethylamino]ethyl]-3-(2-phenylethoxy)propanamide Chemical compound C=1C=C(O)C=2NC(=O)SC=2C=1CCNCCN(CCN(CC)CC)C(=O)CCOCCC1=CC=CC=C1 UGUFEFMMJARSLS-UHFFFAOYSA-N 0.000 claims description 3
• 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 3
• 229940080818 propionamide Drugs 0.000 claims description 3
• 102100039705 Beta-2 adrenergic receptor Human genes 0.000 claims 3
• 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
• 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 1
• 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 1
• 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 1
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 225
• 239000000203 mixture Substances 0.000 description 111
• 239000000243 solution Substances 0.000 description 109
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 88
• 239000000047 product Substances 0.000 description 70
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 67
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 66
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 65
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 60
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 50
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 48
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 46
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 42
• 239000007787 solid Substances 0.000 description 40
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 37
• 238000006243 chemical reaction Methods 0.000 description 37
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 36
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 34
• 239000011541 reaction mixture Substances 0.000 description 34
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
• 239000012267 brine Substances 0.000 description 33
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 33
• 239000003921 oil Substances 0.000 description 32
• 235000019198 oils Nutrition 0.000 description 32
• 239000003112 inhibitor Substances 0.000 description 31
• 210000004027 cell Anatomy 0.000 description 30
• 229960005419 nitrogen Drugs 0.000 description 30
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 25
• 239000000460 chlorine Substances 0.000 description 24
• 235000019439 ethyl acetate Nutrition 0.000 description 24
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 22
• 229910052801 chlorine Inorganic materials 0.000 description 22
• 229910021529 ammonia Inorganic materials 0.000 description 21
• 239000012230 colorless oil Substances 0.000 description 21
• 239000003960 organic solvent Substances 0.000 description 20
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 19
• 238000003756 stirring Methods 0.000 description 19
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 18
• 125000003545 alkoxy group Chemical group 0.000 description 18
• 239000012131 assay buffer Substances 0.000 description 18
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 18
• 229910052794 bromium Inorganic materials 0.000 description 18
• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 18
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 17
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 17
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 17
• 239000011737 fluorine Substances 0.000 description 17
• 229910052731 fluorine Inorganic materials 0.000 description 17
• 239000011630 iodine Substances 0.000 description 17
• 229910052740 iodine Inorganic materials 0.000 description 17
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 17
• 235000019341 magnesium sulphate Nutrition 0.000 description 17
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
• 239000000377 silicon dioxide Substances 0.000 description 16
• 238000012360 testing method Methods 0.000 description 16
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
• 239000002904 solvent Substances 0.000 description 15
• 230000027455 binding Effects 0.000 description 14
• 239000005557 antagonist Substances 0.000 description 13
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 13
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 13
• 210000001519 tissue Anatomy 0.000 description 13
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 12
• 239000012528 membrane Substances 0.000 description 12
• 230000009871 nonspecific binding Effects 0.000 description 12
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
• 230000001154 acute effect Effects 0.000 description 11
• 238000013459 approach Methods 0.000 description 11
• VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 11
• 229920001971 elastomer Polymers 0.000 description 11
• 238000002474 experimental method Methods 0.000 description 11
• 238000004007 reversed phase HPLC Methods 0.000 description 11
• AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 10
• YJFFKFKKYZPXME-UHFFFAOYSA-N 7-(2-aminoethyl)-4-hydroxy-3h-1,3-benzothiazol-2-one;hydrochloride Chemical compound Cl.NCCC1=CC=C(O)C2=C1SC(=O)N2 YJFFKFKKYZPXME-UHFFFAOYSA-N 0.000 description 10
• 238000004587 chromatography analysis Methods 0.000 description 10
• IENQCPAFBMYUKE-UHFFFAOYSA-N 3-(2-phenylethoxy)propanoic acid Chemical compound OC(=O)CCOCCC1=CC=CC=C1 IENQCPAFBMYUKE-UHFFFAOYSA-N 0.000 description 9
• 235000019502 Orange oil Nutrition 0.000 description 9
• 150000001299 aldehydes Chemical class 0.000 description 9
• 238000003556 assay Methods 0.000 description 9
• 239000012043 crude product Substances 0.000 description 9
• 238000003818 flash chromatography Methods 0.000 description 9
• 208000015181 infectious disease Diseases 0.000 description 9
• 239000010502 orange oil Substances 0.000 description 9
• 239000012044 organic layer Substances 0.000 description 9
• 230000009870 specific binding Effects 0.000 description 9
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 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 8
• NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 8
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
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