MXPA06007173A

MXPA06007173A - Derivados de aminoalcohol.

Derivados de aminoalcohol.

Info

Publication number: MXPA06007173A
Authority: MX; Mexico
Prior art keywords: amino; ethyl; hydroxy; phenylethyl; broad
Prior art date: 2003-12-23

Application number

MXPA06007173A

Other languages

English (en)

Spanish (es)

Inventor

Takanobu Araki

Original Assignee

Astellas Pharma Inc

Priority date

2003-12-23

Filing date

2004-12-20

Publication date

2006-08-23

2003-12-23 Priority claimed from AU2003907111A external-priority patent/AU2003907111A0/en

2004-12-20 Application filed by Astellas Pharma Inc filed Critical Astellas Pharma Inc

2006-08-23 Publication of MXPA06007173A publication Critical patent/MXPA06007173A/es

Links

150000001414 amino alcohols Chemical class 0.000 title description 16
150000001875 compounds Chemical class 0.000 claims abstract description 171
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 140
150000003839 salts Chemical class 0.000 claims abstract description 70
125000000217 alkyl group Chemical group 0.000 claims abstract description 68
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 44
239000001257 hydrogen Substances 0.000 claims abstract description 43
150000002431 hydrogen Chemical group 0.000 claims abstract description 23
125000006239 protecting group Chemical group 0.000 claims abstract description 13
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
229910052736 halogen Inorganic materials 0.000 claims abstract description 9
150000002367 halogens Chemical group 0.000 claims abstract description 9
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 8
125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 6
230000001225 therapeutic effect Effects 0.000 claims abstract description 4
230000000069 prophylactic effect Effects 0.000 claims abstract description 3
-1 benzyloxy, nitro, amino Chemical group 0.000 claims description 259
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 142
238000002360 preparation method Methods 0.000 claims description 105
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 46
125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims description 23
238000006243 chemical reaction Methods 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 13
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
125000000623 heterocyclic group Chemical group 0.000 claims description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 7
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 5
125000003118 aryl group Chemical group 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
206010020853 Hypertonic bladder Diseases 0.000 claims description 4
125000003282 alkyl amino group Chemical group 0.000 claims description 4
102000016959 beta-3 Adrenergic Receptors Human genes 0.000 claims description 4
108010014502 beta-3 Adrenergic Receptors Proteins 0.000 claims description 4
125000001589 carboacyl group Chemical group 0.000 claims description 4
208000035475 disorder Diseases 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 4
238000003379 elimination reaction Methods 0.000 claims description 4
YLQMAAMFQNYJDU-MHZLTWQESA-N 2-cyclohexyloxy-4-[4-[2-[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]ethyl]phenyl]-n-methylsulfonylbenzamide Chemical compound CS(=O)(=O)NC(=O)C1=CC=C(C=2C=CC(CCNC[C@H](O)C=3C=NC=CC=3)=CC=2)C=C1OC1CCCCC1 YLQMAAMFQNYJDU-MHZLTWQESA-N 0.000 claims description 3
208000018522 Gastrointestinal disease Diseases 0.000 claims description 3
208000008589 Obesity Diseases 0.000 claims description 3
208000009722 Overactive Urinary Bladder Diseases 0.000 claims description 3
206010033645 Pancreatitis Diseases 0.000 claims description 3
208000025865 Ulcer Diseases 0.000 claims description 3
239000004480 active ingredient Substances 0.000 claims description 3
239000000556 agonist Substances 0.000 claims description 3
238000007257 deesterification reaction Methods 0.000 claims description 3
206010012601 diabetes mellitus Diseases 0.000 claims description 3
125000006125 ethylsulfonyl group Chemical group 0.000 claims description 3
125000001475 halogen functional group Chemical group 0.000 claims description 3
235000020824 obesity Nutrition 0.000 claims description 3
208000020629 overactive bladder Diseases 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
231100000397 ulcer Toxicity 0.000 claims description 3
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
HXFKZSVPCHUKBX-VWLOTQADSA-N 4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]-n-methylsulfonyl-2-propan-2-ylsulfanylbenzamide Chemical compound C1=C(C(=O)NS(C)(=O)=O)C(SC(C)C)=CC(C=2C=CC(CCNC[C@H](O)C=3C=CC=CC=3)=CC=2)=C1 HXFKZSVPCHUKBX-VWLOTQADSA-N 0.000 claims description 2
125000005236 alkanoylamino group Chemical group 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
HGOKKKSGWRCIHE-NDEPHWFRSA-N n-[2-cyclohexyloxy-4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]phenyl]sulfonylacetamide Chemical compound CC(=O)NS(=O)(=O)C1=CC=C(C=2C=CC(CCNC[C@H](O)C=3C=CC=CC=3)=CC=2)C=C1OC1CCCCC1 HGOKKKSGWRCIHE-NDEPHWFRSA-N 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
125000005554 pyridyloxy group Chemical group 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims 4
KQTRLFCXXWVHEX-DCFHFQCYSA-N 2-(2-ethoxyethylsulfanyl)-4-[4-[2-[[(1r,2s)-1-hydroxy-1-phenylpropan-2-yl]amino]ethyl]phenyl]benzoic acid Chemical compound C1=C(C(O)=O)C(SCCOCC)=CC(C=2C=CC(CCN[C@@H](C)[C@H](O)C=3C=CC=CC=3)=CC=2)=C1 KQTRLFCXXWVHEX-DCFHFQCYSA-N 0.000 claims 1
YMRNZNHFJGQDCB-UHFFFAOYSA-N 2-amino-3-phenylbenzoic acid Chemical compound NC1=C(C(O)=O)C=CC=C1C1=CC=CC=C1 YMRNZNHFJGQDCB-UHFFFAOYSA-N 0.000 claims 1
WWFRXUDMACTFBI-NDEPHWFRSA-N 2-cyclohexyloxy-4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]-n-methylsulfonylbenzamide Chemical compound CS(=O)(=O)NC(=O)C1=CC=C(C=2C=CC(CCNC[C@H](O)C=3C=CC=CC=3)=CC=2)C=C1OC1CCCCC1 WWFRXUDMACTFBI-NDEPHWFRSA-N 0.000 claims 1
VEVOQLCIKVDLFH-MMTVBGGISA-N 2-cyclopentyl-4-[4-[2-[[(1r,2s)-1-hydroxy-1-phenylpropan-2-yl]amino]ethyl]phenyl]benzoic acid Chemical compound N([C@@H](C)[C@H](O)C=1C=CC=CC=1)CCC(C=C1)=CC=C1C(C=1)=CC=C(C(O)=O)C=1C1CCCC1 VEVOQLCIKVDLFH-MMTVBGGISA-N 0.000 claims 1
SITWWMFSARAANL-KMRXNPHXSA-N 4-[4-[2-[[(1r,2s)-1-hydroxy-1-phenylpropan-2-yl]amino]ethyl]phenyl]-2-(2-methylpropyl)-n-methylsulfonylbenzamide Chemical compound C1=C(C(=O)NS(C)(=O)=O)C(CC(C)C)=CC(C=2C=CC(CCN[C@@H](C)[C@H](O)C=3C=CC=CC=3)=CC=2)=C1 SITWWMFSARAANL-KMRXNPHXSA-N 0.000 claims 1
NIITYICIHYXXSW-DCFHFQCYSA-N 4-[4-[2-[[(1r,2s)-1-hydroxy-1-phenylpropan-2-yl]amino]ethyl]phenyl]-2-(2-methylpropyl)benzoic acid Chemical compound C1=C(C(O)=O)C(CC(C)C)=CC(C=2C=CC(CCN[C@@H](C)[C@H](O)C=3C=CC=CC=3)=CC=2)=C1 NIITYICIHYXXSW-DCFHFQCYSA-N 0.000 claims 1
WVYCDLWTGGHFDH-SIBVEZHUSA-N 4-[4-[2-[[(1r,2s)-1-hydroxy-1-phenylpropan-2-yl]amino]ethyl]phenyl]-2-propan-2-yloxybenzoic acid Chemical compound C1=C(C(O)=O)C(OC(C)C)=CC(C=2C=CC(CCN[C@@H](C)[C@H](O)C=3C=CC=CC=3)=CC=2)=C1 WVYCDLWTGGHFDH-SIBVEZHUSA-N 0.000 claims 1
PCAWFRXYKXISJG-SIBVEZHUSA-N 4-[4-[2-[[(1r,2s)-1-hydroxy-1-phenylpropan-2-yl]amino]ethyl]phenyl]-2-propan-2-ylsulfanylbenzoic acid Chemical compound C1=C(C(O)=O)C(SC(C)C)=CC(C=2C=CC(CCN[C@@H](C)[C@H](O)C=3C=CC=CC=3)=CC=2)=C1 PCAWFRXYKXISJG-SIBVEZHUSA-N 0.000 claims 1
BAYKLYYVFBMQAJ-SIBVEZHUSA-N 4-[4-[2-[[(1r,2s)-1-hydroxy-1-phenylpropan-2-yl]amino]ethyl]phenyl]-2-propoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OCCC)=CC(C=2C=CC(CCN[C@@H](C)[C@H](O)C=3C=CC=CC=3)=CC=2)=C1 BAYKLYYVFBMQAJ-SIBVEZHUSA-N 0.000 claims 1
BWYBAWPQJCABAZ-QFIPXVFZSA-N 4-[4-[2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethylamino]phenyl]benzoic acid Chemical compound C([C@H](O)C=1C=C(Cl)C=CC=1)NCCNC(C=C1)=CC=C1C1=CC=C(C(O)=O)C=C1 BWYBAWPQJCABAZ-QFIPXVFZSA-N 0.000 claims 1
FKGYWDPSUXSSQK-MHZLTWQESA-N 4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]-2-(2-methylpropyl)-n-methylsulfonylbenzamide Chemical compound C1=C(C(=O)NS(C)(=O)=O)C(CC(C)C)=CC(C=2C=CC(CCNC[C@H](O)C=3C=CC=CC=3)=CC=2)=C1 FKGYWDPSUXSSQK-MHZLTWQESA-N 0.000 claims 1
FYONCJXSNAVJFY-DEOSSOPVSA-N 4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]-2-propan-2-ylsulfanylbenzoic acid Chemical compound C1=C(C(O)=O)C(SC(C)C)=CC(C=2C=CC(CCNC[C@H](O)C=3C=CC=CC=3)=CC=2)=C1 FYONCJXSNAVJFY-DEOSSOPVSA-N 0.000 claims 1
FVWXDJPYOPAWEZ-SANMLTNESA-N 4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]-3-(2-methylpropyl)benzoic acid Chemical compound CC(C)CC1=CC(C(O)=O)=CC=C1C(C=C1)=CC=C1CCNC[C@H](O)C1=CC=CC=C1 FVWXDJPYOPAWEZ-SANMLTNESA-N 0.000 claims 1
YKDNCRQUBMFUKT-QHCPKHFHSA-N 4-[4-[2-[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]ethyl]phenyl]-2-propan-2-ylsulfanylbenzoic acid Chemical compound C1=C(C(O)=O)C(SC(C)C)=CC(C=2C=CC(CCNC[C@H](O)C=3C=NC=CC=3)=CC=2)=C1 YKDNCRQUBMFUKT-QHCPKHFHSA-N 0.000 claims 1
125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
101150032584 oxy-4 gene Proteins 0.000 claims 1
206010046543 Urinary incontinence Diseases 0.000 abstract description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 503
239000000203 mixture Substances 0.000 description 278
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 277
239000000243 solution Substances 0.000 description 182
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 171
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 160
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 153
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 147
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 137
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 107
239000012267 brine Substances 0.000 description 96
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 96
230000002829 reductive effect Effects 0.000 description 94
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 93
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 80
239000012044 organic layer Substances 0.000 description 80
229910052943 magnesium sulfate Inorganic materials 0.000 description 75
235000019341 magnesium sulphate Nutrition 0.000 description 75
239000011734 sodium Substances 0.000 description 73
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 61
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 57
239000007787 solid Substances 0.000 description 55
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 52
239000000741 silica gel Substances 0.000 description 50
229910002027 silica gel Inorganic materials 0.000 description 50
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 46
238000001914 filtration Methods 0.000 description 45
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 44
238000004440 column chromatography Methods 0.000 description 43
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 40
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 40
239000000047 product Substances 0.000 description 38
238000001704 evaporation Methods 0.000 description 37
230000008020 evaporation Effects 0.000 description 37
239000007864 aqueous solution Substances 0.000 description 34
239000011541 reaction mixture Substances 0.000 description 34
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 26
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 26
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 25
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 24
229910052757 nitrogen Inorganic materials 0.000 description 22
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
229910052938 sodium sulfate Inorganic materials 0.000 description 19
235000011152 sodium sulphate Nutrition 0.000 description 19
239000000725 suspension Substances 0.000 description 19
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 18
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
238000001816 cooling Methods 0.000 description 17
239000003480 eluent Substances 0.000 description 17
XBXCNNQPRYLIDE-UHFFFAOYSA-M n-tert-butylcarbamate Chemical compound CC(C)(C)NC([O-])=O XBXCNNQPRYLIDE-UHFFFAOYSA-M 0.000 description 17
238000010992 reflux Methods 0.000 description 17
238000010898 silica gel chromatography Methods 0.000 description 17
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 15
229910000041 hydrogen chloride Inorganic materials 0.000 description 15
238000000034 method Methods 0.000 description 15
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
239000010410 layer Substances 0.000 description 14
239000002244 precipitate Substances 0.000 description 14
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 13
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 13
239000000706 filtrate Substances 0.000 description 13
229910000029 sodium carbonate Inorganic materials 0.000 description 13
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 12
230000002265 prevention Effects 0.000 description 12
239000002904 solvent Substances 0.000 description 12
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 11
239000012043 crude product Substances 0.000 description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 10
101150041968 CDC13 gene Proteins 0.000 description 10
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 10
239000006260 foam Substances 0.000 description 10
125000004433 nitrogen atom Chemical group N* 0.000 description 10
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 10
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 8
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
239000000284 extract Substances 0.000 description 8
125000002911 monocyclic heterocycle group Chemical group 0.000 description 8
239000012299 nitrogen atmosphere Substances 0.000 description 8
229910000027 potassium carbonate Inorganic materials 0.000 description 8
235000011181 potassium carbonates Nutrition 0.000 description 8
229920006395 saturated elastomer Chemical group 0.000 description 8
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 8
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 8
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 7
NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 7
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 7
MVEAAGBEUOMFRX-UHFFFAOYSA-N ethyl acetate;hydrochloride Chemical compound Cl.CCOC(C)=O MVEAAGBEUOMFRX-UHFFFAOYSA-N 0.000 description 7
230000036724 intravesical pressure Effects 0.000 description 7
HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 7
239000005711 Benzoic acid Substances 0.000 description 6
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ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 2
ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical compound OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 description 2
229940043279 diisopropylamine Drugs 0.000 description 2
208000000718 duodenal ulcer Diseases 0.000 description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
BYHUOJDCWGMPCF-UHFFFAOYSA-N ethyl 2-(4-bromo-2-cyclohexyloxyphenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(Br)C=C1OC1CCCCC1 BYHUOJDCWGMPCF-UHFFFAOYSA-N 0.000 description 2
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
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238000000605 extraction Methods 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
201000005917 gastric ulcer Diseases 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
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238000006317 isomerization reaction Methods 0.000 description 2
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
WNAFVJVEADYQAI-UHFFFAOYSA-N methyl 2-phenylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C1=CC=CC=C1 WNAFVJVEADYQAI-UHFFFAOYSA-N 0.000 description 2
ZHICBWUCPHAXEG-NDEPHWFRSA-N methyl 4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethyl]phenyl]-2-propan-2-yloxybenzoate Chemical compound C1=C(OC(C)C)C(C(=O)OC)=CC=C1C(C=C1)=CC=C1CCN(C(=O)OC(C)(C)C)C[C@H](O)C1=CC=CC=C1 ZHICBWUCPHAXEG-NDEPHWFRSA-N 0.000 description 2
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239000011259 mixed solution Substances 0.000 description 2
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NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
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230000008707 rearrangement Effects 0.000 description 2
238000000926 separation method Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
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125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
125000001544 thienyl group Chemical group 0.000 description 2
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HSKINQDVRZGRCZ-KLXURFKVSA-N (1r)-2-amino-1-pyridin-3-ylethanol;dihydrochloride Chemical compound Cl.Cl.NC[C@H](O)C1=CC=CN=C1 HSKINQDVRZGRCZ-KLXURFKVSA-N 0.000 description 1
PMVFSIPPTOOMTI-FJXQXJEOSA-N (1r)-2-amino-1-pyridin-3-ylethanol;hydrochloride Chemical compound Cl.NC[C@H](O)C1=CC=CN=C1 PMVFSIPPTOOMTI-FJXQXJEOSA-N 0.000 description 1
CQSLITZIZPAUOK-UHFFFAOYSA-N (3-cyclohexyloxy-4-methoxycarbonylphenyl)boronic acid Chemical compound COC(=O)C1=CC=C(B(O)O)C=C1OC1CCCCC1 CQSLITZIZPAUOK-UHFFFAOYSA-N 0.000 description 1
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125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 description 1
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VRIOCSSBDAFBIT-OBRDHALPSA-N 2-(2-ethoxyethoxy)-4-[4-[2-[[(1r,2s)-1-hydroxy-1-phenylpropan-2-yl]amino]ethyl]phenyl]benzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(OCCOCC)=CC(C=2C=CC(CCN[C@@H](C)[C@H](O)C=3C=CC=CC=3)=CC=2)=C1 VRIOCSSBDAFBIT-OBRDHALPSA-N 0.000 description 1
KFDRKURJOYACAD-LPCSYZHESA-N 2-(2-ethoxyethylamino)-4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]-n-methylsulfonylbenzamide;dihydrochloride Chemical compound Cl.Cl.C1=C(C(=O)NS(C)(=O)=O)C(NCCOCC)=CC(C=2C=CC(CCNC[C@H](O)C=3C=CC=CC=3)=CC=2)=C1 KFDRKURJOYACAD-LPCSYZHESA-N 0.000 description 1
BSZBPLBCQSURFL-UQIIZPHYSA-N 2-(2-ethoxyethylsulfanyl)-4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]benzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(SCCOCC)=CC(C=2C=CC(CCNC[C@H](O)C=3C=CC=CC=3)=CC=2)=C1 BSZBPLBCQSURFL-UQIIZPHYSA-N 0.000 description 1
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VRPJIFMKZZEXLR-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid Chemical compound CC(C)(C)OC(=O)NCC(O)=O VRPJIFMKZZEXLR-UHFFFAOYSA-N 0.000 description 1
MMOMNZLCOPSKFF-HKBQPEDESA-N 2-[2-cyclohexyloxy-4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethyl]phenyl]phenyl]acetic acid Chemical compound C([C@H](O)C=1C=CC=CC=1)N(C(=O)OC(C)(C)C)CCC(C=C1)=CC=C1C(C=1)=CC=C(CC(O)=O)C=1OC1CCCCC1 MMOMNZLCOPSKFF-HKBQPEDESA-N 0.000 description 1
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AKMHFYVVLMXTKO-MHZLTWQESA-N 2-[2-cyclohexyloxy-4-[4-[2-[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]ethyl]phenyl]phenyl]acetic acid Chemical compound C([C@H](O)C=1C=NC=CC=1)NCCC(C=C1)=CC=C1C(C=1)=CC=C(CC(O)=O)C=1OC1CCCCC1 AKMHFYVVLMXTKO-MHZLTWQESA-N 0.000 description 1
SUYHKARYJIVKRP-UHFFFAOYSA-N 2-amino-n-(4-iodophenyl)acetamide;hydrochloride Chemical compound Cl.NCC(=O)NC1=CC=C(I)C=C1 SUYHKARYJIVKRP-UHFFFAOYSA-N 0.000 description 1
NPAKUVKFEVTCKC-UQIIZPHYSA-N 2-butoxy-4-[4-[2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethoxy]phenyl]benzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(OCCCC)=CC(C=2C=CC(OCCNC[C@H](O)C=3C=C(Cl)C=CC=3)=CC=2)=C1 NPAKUVKFEVTCKC-UQIIZPHYSA-N 0.000 description 1
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YYPUQRNKJBGUNR-GKVSMKOHSA-N 2-ethoxy-4-[4-[2-[[(1R,2S)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]phenyl]benzoic acid Chemical compound C1=C(C(O)=O)C(OCC)=CC(C=2C=CC(CCN[C@@H](C)[C@H](O)C=3C=CC(O)=CC=3)=CC=2)=C1 YYPUQRNKJBGUNR-GKVSMKOHSA-N 0.000 description 1
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TVVLYOPQYYREOW-UHFFFAOYSA-N 2-phenylbenzamide;hydrochloride Chemical compound Cl.NC(=O)C1=CC=CC=C1C1=CC=CC=C1 TVVLYOPQYYREOW-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 1
LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
PERYHCLELRXANQ-ASMAMLKCSA-N 3-(dimethylamino)-4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]benzoic acid;dihydrochloride Chemical compound Cl.Cl.CN(C)C1=CC(C(O)=O)=CC=C1C(C=C1)=CC=C1CCNC[C@H](O)C1=CC=CC=C1 PERYHCLELRXANQ-ASMAMLKCSA-N 0.000 description 1
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LFCWHVXIZBGDKX-QFIPXVFZSA-N 3-[4-[2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethylamino]phenyl]benzoic acid Chemical compound C([C@H](O)C=1C=C(Cl)C=CC=1)NCCNC(C=C1)=CC=C1C1=CC=CC(C(O)=O)=C1 LFCWHVXIZBGDKX-QFIPXVFZSA-N 0.000 description 1
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AMHUFKOXCSYREX-SNYZSRNZSA-N 3-butyl-4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]benzoic acid;hydrochloride Chemical compound Cl.CCCCC1=CC(C(O)=O)=CC=C1C(C=C1)=CC=C1CCNC[C@H](O)C1=CC=CC=C1 AMHUFKOXCSYREX-SNYZSRNZSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 1
YUYXBLYSKPNXPT-UHFFFAOYSA-N 3-methylbutane-1-sulfonamide Chemical compound CC(C)CCS(N)(=O)=O YUYXBLYSKPNXPT-UHFFFAOYSA-N 0.000 description 1
LYLJTYBJNZXRPE-UHFFFAOYSA-N 4-[4-(2-amino-2-methylpropyl)phenyl]-2-(2-methylpropyl)benzoic acid Chemical compound NC(CC1=CC=C(C=C1)C1=CC(=C(C=C1)C(=O)O)CC(C)C)(C)C LYLJTYBJNZXRPE-UHFFFAOYSA-N 0.000 description 1
YUGKBDCURSYISL-UHFFFAOYSA-N 4-[4-(2-aminoethoxy)phenyl]-2-cyclohexyloxy-n-methylsulfonylbenzamide;hydrochloride Chemical compound Cl.CS(=O)(=O)NC(=O)C1=CC=C(C=2C=CC(OCCN)=CC=2)C=C1OC1CCCCC1 YUGKBDCURSYISL-UHFFFAOYSA-N 0.000 description 1
OLBSFYAWEMEHLA-UHFFFAOYSA-N 4-[4-(2-aminoethyl)phenyl]-n-methylsulfonyl-2-(propan-2-ylamino)benzamide;dihydrochloride Chemical compound Cl.Cl.C1=C(C(=O)NS(C)(=O)=O)C(NC(C)C)=CC(C=2C=CC(CCN)=CC=2)=C1 OLBSFYAWEMEHLA-UHFFFAOYSA-N 0.000 description 1
HZBACCFYWKQVGF-PIKZIKFNSA-N 4-[4-[(2r)-2-[[(2r)-2-hydroxy-2-phenylethyl]amino]propyl]phenyl]-2-(2-methylpropyl)-n-methylsulfonylbenzamide Chemical compound C1=C(C(=O)NS(C)(=O)=O)C(CC(C)C)=CC(C=2C=CC(C[C@@H](C)NC[C@H](O)C=3C=CC=CC=3)=CC=2)=C1 HZBACCFYWKQVGF-PIKZIKFNSA-N 0.000 description 1
HVEARHMGFIQQDL-VAMRJWDISA-N 4-[4-[1-[[(2r)-2-hydroxy-2-phenylethyl]amino]propan-2-yl]phenyl]-2-propan-2-yloxybenzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(OC(C)C)=CC(C=2C=CC(=CC=2)C(C)CNC[C@H](O)C=2C=CC=CC=2)=C1 HVEARHMGFIQQDL-VAMRJWDISA-N 0.000 description 1
JIIPNLQSDWEJMM-VRECQLHDSA-N 4-[4-[2-[[(1r,2s)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]phenyl]-2-propan-2-yloxybenzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(OC(C)C)=CC(C=2C=CC(CCN[C@@H](C)[C@H](O)C=3C=CC(O)=CC=3)=CC=2)=C1 JIIPNLQSDWEJMM-VRECQLHDSA-N 0.000 description 1
MTOVDKONOKZNFC-GYUFFBBGSA-N 4-[4-[2-[[(1r,2s)-1-hydroxy-1-phenylpropan-2-yl]amino]ethyl]phenyl]-2-propoxybenzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(OCCC)=CC(C=2C=CC(CCN[C@@H](C)[C@H](O)C=3C=CC=CC=3)=CC=2)=C1 MTOVDKONOKZNFC-GYUFFBBGSA-N 0.000 description 1
DUVDAJAXYHBDLL-VWLOTQADSA-N 4-[4-[2-[[(2R)-2-(4-aminophenyl)-2-hydroxyethyl]amino]ethyl]phenyl]-N-methylsulfonyl-2-propan-2-ylsulfanylbenzamide Chemical compound C1=C(C(=O)NS(C)(=O)=O)C(SC(C)C)=CC(C=2C=CC(CCNC[C@H](O)C=3C=CC(N)=CC=3)=CC=2)=C1 DUVDAJAXYHBDLL-VWLOTQADSA-N 0.000 description 1
MBXVEWNJDSNZCT-LJAQVGFWSA-N 4-[4-[2-[[(2R)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]-N-pentylsulfonyl-2-propan-2-yloxybenzamide Chemical compound C1=C(OC(C)C)C(C(=O)NS(=O)(=O)CCCCC)=CC=C1C(C=C1)=CC=C1CCNC[C@H](O)C1=CC=CC=C1 MBXVEWNJDSNZCT-LJAQVGFWSA-N 0.000 description 1
AGUCCDQTFCLHNN-DEOSSOPVSA-N 4-[4-[2-[[(2r)-2-(3-aminophenyl)-2-hydroxyethyl]amino]ethoxy]phenyl]-2-propan-2-yloxybenzoic acid Chemical compound C1=C(C(O)=O)C(OC(C)C)=CC(C=2C=CC(OCCNC[C@H](O)C=3C=C(N)C=CC=3)=CC=2)=C1 AGUCCDQTFCLHNN-DEOSSOPVSA-N 0.000 description 1
ZGYZKUVOZXMDDH-NDEPHWFRSA-N 4-[4-[2-[[(2r)-2-(3-aminophenyl)-2-hydroxyethyl]amino]ethyl]phenyl]-2-cyclohexyloxy-n-methylsulfonylbenzamide Chemical compound CS(=O)(=O)NC(=O)C1=CC=C(C=2C=CC(CCNC[C@H](O)C=3C=C(N)C=CC=3)=CC=2)C=C1OC1CCCCC1 ZGYZKUVOZXMDDH-NDEPHWFRSA-N 0.000 description 1
GKJRPWPPZIETKU-VWLOTQADSA-N 4-[4-[2-[[(2r)-2-(3-aminophenyl)-2-hydroxyethyl]amino]ethyl]phenyl]-n-methylsulfonyl-2-propan-2-yloxybenzamide Chemical compound C1=C(C(=O)NS(C)(=O)=O)C(OC(C)C)=CC(C=2C=CC(CCNC[C@H](O)C=3C=C(N)C=CC=3)=CC=2)=C1 GKJRPWPPZIETKU-VWLOTQADSA-N 0.000 description 1
UPWOKBWOTDEGOQ-UQIIZPHYSA-N 4-[4-[2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethoxy]phenyl]-2-(2-methylpropoxy)benzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(OCC(C)C)=CC(C=2C=CC(OCCNC[C@H](O)C=3C=C(Cl)C=CC=3)=CC=2)=C1 UPWOKBWOTDEGOQ-UQIIZPHYSA-N 0.000 description 1
FJTAGRLRABWGCD-SNYZSRNZSA-N 4-[4-[2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethoxy]phenyl]-2-(2-methylpropyl)benzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(CC(C)C)=CC(C=2C=CC(OCCNC[C@H](O)C=3C=C(Cl)C=CC=3)=CC=2)=C1 FJTAGRLRABWGCD-SNYZSRNZSA-N 0.000 description 1
VFEAJBBIVVIQDG-JIDHJSLPSA-N 4-[4-[2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethoxy]phenyl]-2-propan-2-yloxybenzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(OC(C)C)=CC(C=2C=CC(OCCNC[C@H](O)C=3C=C(Cl)C=CC=3)=CC=2)=C1 VFEAJBBIVVIQDG-JIDHJSLPSA-N 0.000 description 1
HJBVLKQMEXFTFU-JIDHJSLPSA-N 4-[4-[2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethoxy]phenyl]-2-propoxybenzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(OCCC)=CC(C=2C=CC(OCCNC[C@H](O)C=3C=C(Cl)C=CC=3)=CC=2)=C1 HJBVLKQMEXFTFU-JIDHJSLPSA-N 0.000 description 1
LGLAZESVQVTTIB-SNYZSRNZSA-N 4-[4-[2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethyl]phenyl]-3-(2-methylpropyl)benzoic acid;hydrochloride Chemical compound Cl.CC(C)CC1=CC(C(O)=O)=CC=C1C(C=C1)=CC=C1CCNC[C@H](O)C1=CC=CC(Cl)=C1 LGLAZESVQVTTIB-SNYZSRNZSA-N 0.000 description 1
URDQAJFRADQJGR-JIDHJSLPSA-N 4-[4-[2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethyl]phenyl]-3-ethylbenzoic acid;hydrochloride Chemical compound Cl.CCC1=CC(C(O)=O)=CC=C1C(C=C1)=CC=C1CCNC[C@H](O)C1=CC=CC(Cl)=C1 URDQAJFRADQJGR-JIDHJSLPSA-N 0.000 description 1
ZEWQAVIVDFTLSP-UQIIZPHYSA-N 4-[4-[2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethyl]phenyl]-3-propylbenzoic acid;hydrochloride Chemical compound Cl.CCCC1=CC(C(O)=O)=CC=C1C(C=C1)=CC=C1CCNC[C@H](O)C1=CC=CC(Cl)=C1 ZEWQAVIVDFTLSP-UQIIZPHYSA-N 0.000 description 1
HUIXYXIMTYLEAI-JIDHJSLPSA-N 4-[4-[2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethylamino]phenyl]-2-propoxybenzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(OCCC)=CC(C=2C=CC(NCCNC[C@H](O)C=3C=C(Cl)C=CC=3)=CC=2)=C1 HUIXYXIMTYLEAI-JIDHJSLPSA-N 0.000 description 1
NDWPPVQVXQFNAM-FTBISJDPSA-N 4-[4-[2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethylamino]phenyl]benzoic acid;hydrochloride Chemical compound Cl.C([C@H](O)C=1C=C(Cl)C=CC=1)NCCNC(C=C1)=CC=C1C1=CC=C(C(O)=O)C=C1 NDWPPVQVXQFNAM-FTBISJDPSA-N 0.000 description 1
VTKMLZIGOBSURB-NDEPHWFRSA-N 4-[4-[2-[[(2r)-2-(4-aminophenyl)-2-hydroxyethyl]amino]ethyl]phenyl]-2-cyclohexyloxy-n-methylsulfonylbenzamide Chemical compound CS(=O)(=O)NC(=O)C1=CC=C(C=2C=CC(CCNC[C@H](O)C=3C=CC(N)=CC=3)=CC=2)C=C1OC1CCCCC1 VTKMLZIGOBSURB-NDEPHWFRSA-N 0.000 description 1
PQIYAYICSPPBOY-WLOLSGMKSA-N 4-[4-[2-[[(2r)-2-(4-aminophenyl)-2-hydroxyethyl]amino]ethyl]phenyl]-n-methylsulfonyl-2-propan-2-yloxybenzamide;dihydrochloride Chemical compound Cl.Cl.C1=C(C(=O)NS(C)(=O)=O)C(OC(C)C)=CC(C=2C=CC(CCNC[C@H](O)C=3C=CC(N)=CC=3)=CC=2)=C1 PQIYAYICSPPBOY-WLOLSGMKSA-N 0.000 description 1
WOFBNUYARXYLNQ-WLOLSGMKSA-N 4-[4-[2-[[(2r)-2-(4-aminophenyl)-2-hydroxyethyl]amino]ethyl]phenyl]-n-methylsulfonyl-2-propoxybenzamide;dihydrochloride Chemical compound Cl.Cl.C1=C(C(=O)NS(C)(=O)=O)C(OCCC)=CC(C=2C=CC(CCNC[C@H](O)C=3C=CC(N)=CC=3)=CC=2)=C1 WOFBNUYARXYLNQ-WLOLSGMKSA-N 0.000 description 1
RADGEKGFCAQKLZ-JIDHJSLPSA-N 4-[4-[2-[[(2r)-2-(4-chlorophenyl)-2-hydroxyethyl]amino]ethoxy]phenyl]-2-propoxybenzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(OCCC)=CC(C=2C=CC(OCCNC[C@H](O)C=3C=CC(Cl)=CC=3)=CC=2)=C1 RADGEKGFCAQKLZ-JIDHJSLPSA-N 0.000 description 1
ZYGRIOZJVGIXKT-SANMLTNESA-N 4-[4-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]ethyl]phenyl]-2-cycloheptyloxybenzoic acid Chemical compound C1=NC(N)=CC=C1[C@@H](O)CNCCC1=CC=C(C=2C=C(OC3CCCCCC3)C(C(O)=O)=CC=2)C=C1 ZYGRIOZJVGIXKT-SANMLTNESA-N 0.000 description 1
DGHGBPNTKGVIFX-SANMLTNESA-N 4-[4-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]ethyl]phenyl]-2-cyclohexyloxy-n-methylsulfonylbenzamide Chemical compound CS(=O)(=O)NC(=O)C1=CC=C(C=2C=CC(CCNC[C@H](O)C=3C=NC(N)=CC=3)=CC=2)C=C1OC1CCCCC1 DGHGBPNTKGVIFX-SANMLTNESA-N 0.000 description 1
DJTFHPYTDCJUNI-VWLOTQADSA-N 4-[4-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]ethyl]phenyl]-2-cyclohexyloxybenzoic acid Chemical compound C1=NC(N)=CC=C1[C@@H](O)CNCCC1=CC=C(C=2C=C(OC3CCCCC3)C(C(O)=O)=CC=2)C=C1 DJTFHPYTDCJUNI-VWLOTQADSA-N 0.000 description 1
YPVVXDBWCDPNRB-QHCPKHFHSA-N 4-[4-[2-[[(2r)-2-(6-aminopyridin-3-yl)-2-hydroxyethyl]amino]ethyl]phenyl]-n-methylsulfonyl-2-propan-2-yloxybenzamide Chemical compound C1=C(C(=O)NS(C)(=O)=O)C(OC(C)C)=CC(C=2C=CC(CCNC[C@H](O)C=3C=NC(N)=CC=3)=CC=2)=C1 YPVVXDBWCDPNRB-QHCPKHFHSA-N 0.000 description 1
MZFJYGKSUVMJCE-JIDHJSLPSA-N 4-[4-[2-[[(2r)-2-hydroxy-2-(3-hydroxyphenyl)ethyl]amino]ethoxy]phenyl]-2-propoxybenzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(OCCC)=CC(C=2C=CC(OCCNC[C@H](O)C=3C=C(O)C=CC=3)=CC=2)=C1 MZFJYGKSUVMJCE-JIDHJSLPSA-N 0.000 description 1
JRFSAWHPDAIKQA-JIDHJSLPSA-N 4-[4-[2-[[(2r)-2-hydroxy-2-(3-hydroxyphenyl)ethyl]amino]ethyl]phenyl]-2-propan-2-yloxybenzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(OC(C)C)=CC(C=2C=CC(CCNC[C@H](O)C=3C=C(O)C=CC=3)=CC=2)=C1 JRFSAWHPDAIKQA-JIDHJSLPSA-N 0.000 description 1
XJQYLEOYVGHTNH-VWLOTQADSA-N 4-[4-[2-[[(2r)-2-hydroxy-2-[3-(methanesulfonamido)phenyl]ethyl]amino]ethyl]phenyl]-2-propan-2-yloxybenzoic acid Chemical compound C1=C(C(O)=O)C(OC(C)C)=CC(C=2C=CC(CCNC[C@H](O)C=3C=C(NS(C)(=O)=O)C=CC=3)=CC=2)=C1 XJQYLEOYVGHTNH-VWLOTQADSA-N 0.000 description 1
MNTSPNDNPMLOLI-UQIIZPHYSA-N 4-[4-[2-[[(2r)-2-hydroxy-2-[4-hydroxy-3-(methanesulfonamido)phenyl]ethyl]amino]ethyl]phenyl]-2-propan-2-yloxybenzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(OC(C)C)=CC(C=2C=CC(CCNC[C@H](O)C=3C=C(NS(C)(=O)=O)C(O)=CC=3)=CC=2)=C1 MNTSPNDNPMLOLI-UQIIZPHYSA-N 0.000 description 1
PLNMLCMYSACQBI-MHZLTWQESA-N 4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethyl]phenyl]-2-propan-2-ylsulfanylbenzoic acid Chemical compound C1=C(C(O)=O)C(SC(C)C)=CC(C=2C=CC(CCN(C[C@H](O)C=3C=CC=CC=3)C(=O)OC(C)(C)C)=CC=2)=C1 PLNMLCMYSACQBI-MHZLTWQESA-N 0.000 description 1
DUWLUHNLNLVQKL-YCBFMBTMSA-N 4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]-2-methylpropyl]phenyl]-2-(2-methylpropyl)benzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(CC(C)C)=CC(C=2C=CC(CC(C)(C)NC[C@H](O)C=3C=CC=CC=3)=CC=2)=C1 DUWLUHNLNLVQKL-YCBFMBTMSA-N 0.000 description 1
NCHYFZMKHYDCDB-UQIIZPHYSA-N 4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]-2-methylpropyl]phenyl]-2-propan-2-yloxybenzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(OC(C)C)=CC(C=2C=CC(CC(C)(C)NC[C@H](O)C=3C=CC=CC=3)=CC=2)=C1 NCHYFZMKHYDCDB-UQIIZPHYSA-N 0.000 description 1
ZQQFSHMZYQENFQ-UQIIZPHYSA-N 4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethoxy]phenyl]-2-(2-methylpropoxy)benzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(OCC(C)C)=CC(C=2C=CC(OCCNC[C@H](O)C=3C=CC=CC=3)=CC=2)=C1 ZQQFSHMZYQENFQ-UQIIZPHYSA-N 0.000 description 1
GNCDNSMZMLWRLI-SNYZSRNZSA-N 4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethoxy]phenyl]-2-(2-methylpropyl)benzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(CC(C)C)=CC(C=2C=CC(OCCNC[C@H](O)C=3C=CC=CC=3)=CC=2)=C1 GNCDNSMZMLWRLI-SNYZSRNZSA-N 0.000 description 1
RKZCNGGGTNFYSP-JIDHJSLPSA-N 4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethoxy]phenyl]-2-propan-2-yloxybenzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(OC(C)C)=CC(C=2C=CC(OCCNC[C@H](O)C=3C=CC=CC=3)=CC=2)=C1 RKZCNGGGTNFYSP-JIDHJSLPSA-N 0.000 description 1
NMHRJFOGAMSZNH-JIDHJSLPSA-N 4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethoxy]phenyl]-2-propoxybenzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(OCCC)=CC(C=2C=CC(OCCNC[C@H](O)C=3C=CC=CC=3)=CC=2)=C1 NMHRJFOGAMSZNH-JIDHJSLPSA-N 0.000 description 1
CWNAROURWWJDLO-SNYZSRNZSA-N 4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]-2-(2-methylprop-1-enyl)benzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(C=C(C)C)=CC(C=2C=CC(CCNC[C@H](O)C=3C=CC=CC=3)=CC=2)=C1 CWNAROURWWJDLO-SNYZSRNZSA-N 0.000 description 1
OWSBFBQUELFZJC-SNYZSRNZSA-N 4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]-2-(oxan-4-yloxy)benzoic acid;hydrochloride Chemical compound Cl.C([C@H](O)C=1C=CC=CC=1)NCCC(C=C1)=CC=C1C(C=1)=CC=C(C(O)=O)C=1OC1CCOCC1 OWSBFBQUELFZJC-SNYZSRNZSA-N 0.000 description 1
BACQNIUODFQAMD-VWLOTQADSA-N 4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]-2-(propan-2-ylamino)benzoic acid Chemical compound C1=C(C(O)=O)C(NC(C)C)=CC(C=2C=CC(CCNC[C@H](O)C=3C=CC=CC=3)=CC=2)=C1 BACQNIUODFQAMD-VWLOTQADSA-N 0.000 description 1
FYXDEHFZNKEFLQ-JIDHJSLPSA-N 4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]-2-propan-2-ylsulfanylbenzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(SC(C)C)=CC(C=2C=CC(CCNC[C@H](O)C=3C=CC=CC=3)=CC=2)=C1 FYXDEHFZNKEFLQ-JIDHJSLPSA-N 0.000 description 1
FATBFAGUJKEWMH-SANMLTNESA-N 4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]-2-pyridin-3-yloxybenzoic acid Chemical compound C([C@H](O)C=1C=CC=CC=1)NCCC(C=C1)=CC=C1C(C=1)=CC=C(C(O)=O)C=1OC1=CC=CN=C1 FATBFAGUJKEWMH-SANMLTNESA-N 0.000 description 1
DHRJVNQWJAOHBA-SNYZSRNZSA-N 4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]-3-(2-methylpropyl)benzoic acid;hydrochloride Chemical compound Cl.CC(C)CC1=CC(C(O)=O)=CC=C1C(C=C1)=CC=C1CCNC[C@H](O)C1=CC=CC=C1 DHRJVNQWJAOHBA-SNYZSRNZSA-N 0.000 description 1
XKWCWHLMRNLIBK-QHCPKHFHSA-N 4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]-3-(methylamino)benzoic acid Chemical compound CNC1=CC(C(O)=O)=CC=C1C(C=C1)=CC=C1CCNC[C@H](O)C1=CC=CC=C1 XKWCWHLMRNLIBK-QHCPKHFHSA-N 0.000 description 1
YWQLKELWSSWGEU-UQIIZPHYSA-N 4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]-3-propylbenzoic acid;hydrochloride Chemical compound Cl.CCCC1=CC(C(O)=O)=CC=C1C(C=C1)=CC=C1CCNC[C@H](O)C1=CC=CC=C1 YWQLKELWSSWGEU-UQIIZPHYSA-N 0.000 description 1
IZNUOCLGTSYWDZ-JCOPYZAKSA-N 4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]-n-(2-methylpropylsulfonyl)-2-propan-2-yloxybenzamide;hydrochloride Chemical compound Cl.C1=C(OC(C)C)C(C(=O)NS(=O)(=O)CC(C)C)=CC=C1C(C=C1)=CC=C1CCNC[C@H](O)C1=CC=CC=C1 IZNUOCLGTSYWDZ-JCOPYZAKSA-N 0.000 description 1
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238000010438 heat treatment Methods 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000006038 hexenyl group Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
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238000007918 intramuscular administration Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000011630 iodine Substances 0.000 description 1
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HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
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208000002551 irritable bowel syndrome Diseases 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
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239000004571 lime Substances 0.000 description 1
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239000006210 lotion Substances 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
208000024714 major depressive disease Diseases 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000000463 material Substances 0.000 description 1
201000003995 melancholia Diseases 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
ZSGLAKVEUUXMBG-SFCXHYMASA-N methyl 2-amino-4-[4-[2-[benzyl-[(2r)-2-(oxan-2-yloxy)-2-phenylethyl]amino]ethyl]phenyl]benzoate Chemical compound C1=C(N)C(C(=O)OC)=CC=C1C(C=C1)=CC=C1CCN(CC=1C=CC=CC=1)C[C@@H](C=1C=CC=CC=1)OC1OCCCC1 ZSGLAKVEUUXMBG-SFCXHYMASA-N 0.000 description 1
CIRLWCKMKNJVHC-YTTGMZPUSA-N methyl 2-cyclohexyloxy-4-[4-[3-[[(2r)-2-hydroxy-2-phenylethyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]propyl]phenyl]benzoate Chemical compound COC(=O)C1=CC=C(C=2C=CC(CCCN(C[C@H](O)C=3C=CC=CC=3)C(=O)OC(C)(C)C)=CC=2)C=C1OC1CCCCC1 CIRLWCKMKNJVHC-YTTGMZPUSA-N 0.000 description 1
ZRBHEUPJVPCIHW-MHZLTWQESA-N methyl 2-ethylsulfanyl-4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethyl]phenyl]benzoate Chemical compound C1=C(C(=O)OC)C(SCC)=CC(C=2C=CC(CCN(C[C@H](O)C=3C=CC=CC=3)C(=O)OC(C)(C)C)=CC=2)=C1 ZRBHEUPJVPCIHW-MHZLTWQESA-N 0.000 description 1
OJHMZWHKSAGJSZ-NDEPHWFRSA-N methyl 3-(dimethylamino)-4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethyl]phenyl]benzoate Chemical compound CN(C)C1=CC(C(=O)OC)=CC=C1C(C=C1)=CC=C1CCN(C(=O)OC(C)(C)C)C[C@H](O)C1=CC=CC=C1 OJHMZWHKSAGJSZ-NDEPHWFRSA-N 0.000 description 1
FIAFCQOCWXUULV-UHFFFAOYSA-N methyl 4-[4-(2-amino-2-methylpropyl)phenyl]-2-(2-methylpropyl)benzoate Chemical compound C1=C(CC(C)C)C(C(=O)OC)=CC=C1C1=CC=C(CC(C)(C)N)C=C1 FIAFCQOCWXUULV-UHFFFAOYSA-N 0.000 description 1
RCRFCDIKOVOWOQ-UHFFFAOYSA-N methyl 4-[4-(2-bromoethoxy)phenyl]-2-propan-2-ylsulfanylbenzoate Chemical compound C1=C(SC(C)C)C(C(=O)OC)=CC=C1C1=CC=C(OCCBr)C=C1 RCRFCDIKOVOWOQ-UHFFFAOYSA-N 0.000 description 1
GXTYVWFXPKBJRB-UHFFFAOYSA-N methyl 4-[4-(2-hydroxyethoxy)phenyl]-2-propan-2-ylsulfanylbenzoate Chemical compound C1=C(SC(C)C)C(C(=O)OC)=CC=C1C1=CC=C(OCCO)C=C1 GXTYVWFXPKBJRB-UHFFFAOYSA-N 0.000 description 1
BROWBKFKQZVTKN-UHFFFAOYSA-N methyl 4-[4-[2-(benzylamino)ethyl]phenyl]-2-(cyclohexylamino)benzoate Chemical compound COC(=O)C1=CC=C(C=2C=CC(CCNCC=3C=CC=CC=3)=CC=2)C=C1NC1CCCCC1 BROWBKFKQZVTKN-UHFFFAOYSA-N 0.000 description 1
OYWCSKZUBNZORU-UHFFFAOYSA-N methyl 4-[4-[2-(benzylamino)ethyl]phenyl]-2-(propan-2-ylamino)benzoate Chemical compound C1=C(NC(C)C)C(C(=O)OC)=CC=C1C(C=C1)=CC=C1CCNCC1=CC=CC=C1 OYWCSKZUBNZORU-UHFFFAOYSA-N 0.000 description 1
MZTJOSQMGQAVQE-NDEPHWFRSA-N methyl 4-[4-[2-[[(2r)-2-(3-aminophenyl)-2-hydroxyethyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethyl]phenyl]-2-propan-2-yloxybenzoate Chemical compound C1=C(OC(C)C)C(C(=O)OC)=CC=C1C(C=C1)=CC=C1CCN(C(=O)OC(C)(C)C)C[C@H](O)C1=CC=CC(N)=C1 MZTJOSQMGQAVQE-NDEPHWFRSA-N 0.000 description 1
VSIRNRHUULOSMV-LJAQVGFWSA-N methyl 4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethyl]phenyl]-2-(propan-2-ylamino)benzoate Chemical compound C1=C(NC(C)C)C(C(=O)OC)=CC=C1C(C=C1)=CC=C1CCN(C(=O)OC(C)(C)C)C[C@H](O)C1=CC=CC=C1 VSIRNRHUULOSMV-LJAQVGFWSA-N 0.000 description 1
AJNYHIIZLWCODT-SANMLTNESA-N methyl 4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethyl]phenyl]-2-methylsulfanylbenzoate Chemical compound C1=C(SC)C(C(=O)OC)=CC=C1C(C=C1)=CC=C1CCN(C(=O)OC(C)(C)C)C[C@H](O)C1=CC=CC=C1 AJNYHIIZLWCODT-SANMLTNESA-N 0.000 description 1
MCBKUOYOXROHNJ-LJAQVGFWSA-N methyl 4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethyl]phenyl]-2-thiophen-2-ylbenzoate Chemical compound COC(=O)C1=CC=C(C=2C=CC(CCN(C[C@H](O)C=3C=CC=CC=3)C(=O)OC(C)(C)C)=CC=2)C=C1C1=CC=CS1 MCBKUOYOXROHNJ-LJAQVGFWSA-N 0.000 description 1
KLFKICAURRGBKY-NDEPHWFRSA-N methyl 4-[4-[2-[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethyl]phenyl]-2-(2-methylpropoxy)benzoate Chemical compound C1=C(OCC(C)C)C(C(=O)OC)=CC=C1C(C=C1)=CC=C1CCN(C(=O)OC(C)(C)C)C[C@H](O)C1=CC=CN=C1 KLFKICAURRGBKY-NDEPHWFRSA-N 0.000 description 1
BKCBLWJIOZFTIA-XIFFEERXSA-N methyl 4-[4-[2-[benzyl-[(2r)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]-2-(propan-2-ylamino)benzoate Chemical compound C1=C(NC(C)C)C(C(=O)OC)=CC=C1C(C=C1)=CC=C1CCN(CC=1C=CC=CC=1)C[C@H](O)C1=CC=CC=C1 BKCBLWJIOZFTIA-XIFFEERXSA-N 0.000 description 1
RRYUVFWAKFOWLU-PMERELPUSA-N methyl 4-[4-[2-[benzyl-[(2r)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]-2-nitrobenzoate Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC)=CC=C1C(C=C1)=CC=C1CCN(CC=1C=CC=CC=1)C[C@H](O)C1=CC=CC=C1 RRYUVFWAKFOWLU-PMERELPUSA-N 0.000 description 1
KRXFFDTVDRHNRQ-UHFFFAOYSA-N methyl 4-[4-[2-methyl-2-(phenylmethoxycarbonylamino)propyl]phenyl]-2-(2-methylpropyl)benzoate Chemical compound C1=C(CC(C)C)C(C(=O)OC)=CC=C1C(C=C1)=CC=C1CC(C)(C)NC(=O)OCC1=CC=CC=C1 KRXFFDTVDRHNRQ-UHFFFAOYSA-N 0.000 description 1
LRHGEVRMVQAKSX-UHFFFAOYSA-N methyl 4-[4-[2-methyl-2-[(2,2,2-trifluoroacetyl)amino]propyl]phenyl]-2-propan-2-ylsulfanylbenzoate Chemical compound C1=C(SC(C)C)C(C(=O)OC)=CC=C1C1=CC=C(CC(C)(C)NC(=O)C(F)(F)F)C=C1 LRHGEVRMVQAKSX-UHFFFAOYSA-N 0.000 description 1
UFOFFUGVBGMZHZ-LJAQVGFWSA-N methyl 4-[4-[3-[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]propyl]phenyl]-2-(2-methylpropoxy)benzoate Chemical compound C1=C(OCC(C)C)C(C(=O)OC)=CC=C1C(C=C1)=CC=C1CCCN(C(=O)OC(C)(C)C)C[C@H](O)C1=CC=CN=C1 UFOFFUGVBGMZHZ-LJAQVGFWSA-N 0.000 description 1
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MUZQTHLBMBNOOV-UXMRNZNESA-N tert-butyl n-[2-(4-bromophenyl)ethyl]-n-[(2r)-2-(oxan-2-yloxy)-2-phenylethyl]carbamate Chemical compound C([C@H](OC1OCCCC1)C=1C=CC=CC=1)N(C(=O)OC(C)(C)C)CCC1=CC=C(Br)C=C1 MUZQTHLBMBNOOV-UXMRNZNESA-N 0.000 description 1
TVBQESYTDWRCSW-IBGZPJMESA-N tert-butyl n-[2-(4-bromophenyl)ethyl]-n-[(2r)-2-hydroxy-2-phenylethyl]carbamate Chemical compound C([C@H](O)C=1C=CC=CC=1)N(C(=O)OC(C)(C)C)CCC1=CC=C(Br)C=C1 TVBQESYTDWRCSW-IBGZPJMESA-N 0.000 description 1
IJYMDQLEOPWKDN-HKBQPEDESA-N tert-butyl n-[2-[4-[4-(acetylsulfamoyl)-3-cyclohexyloxyphenyl]phenyl]ethyl]-n-[(2r)-2-hydroxy-2-phenylethyl]carbamate Chemical compound CC(=O)NS(=O)(=O)C1=CC=C(C=2C=CC(CCN(C[C@H](O)C=3C=CC=CC=3)C(=O)OC(C)(C)C)=CC=2)C=C1OC1CCCCC1 IJYMDQLEOPWKDN-HKBQPEDESA-N 0.000 description 1
GNWLAIYDKTZJFJ-YTTGMZPUSA-N tert-butyl n-[2-[4-[4-(butanoylsulfamoyl)-3-cyclohexyloxyphenyl]phenyl]ethyl]-n-[(2r)-2-hydroxy-2-phenylethyl]carbamate Chemical compound CCCC(=O)NS(=O)(=O)C1=CC=C(C=2C=CC(CCN(C[C@H](O)C=3C=CC=CC=3)C(=O)OC(C)(C)C)=CC=2)C=C1OC1CCCCC1 GNWLAIYDKTZJFJ-YTTGMZPUSA-N 0.000 description 1
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PJUFNGOLTSWJHJ-NDEPHWFRSA-N tert-butyl n-[3-[4-[3-ethoxy-4-(methylsulfonylcarbamoyl)phenyl]phenyl]propyl]-n-[(2r)-2-hydroxy-2-phenylethyl]carbamate Chemical compound C1=C(C(=O)NS(C)(=O)=O)C(OCC)=CC(C=2C=CC(CCCN(C[C@H](O)C=3C=CC=CC=3)C(=O)OC(C)(C)C)=CC=2)=C1 PJUFNGOLTSWJHJ-NDEPHWFRSA-N 0.000 description 1
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238000010998 test method Methods 0.000 description 1
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238000002560 therapeutic procedure Methods 0.000 description 1
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125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
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210000002700 urine Anatomy 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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