CA2580760C - Aminoalcohol derivatives - Google Patents

Info

Publication number

CA2580760C

CA2580760C CA2580760A CA2580760A CA2580760C CA 2580760 C CA2580760 C CA 2580760C CA 2580760 A CA2580760 A CA 2580760A CA 2580760 A CA2580760 A CA 2580760A CA 2580760 C CA2580760 C CA 2580760C

Authority

CA

Canada

Prior art keywords

ethyl

amino

sulfonyl

hydroxy

cyclohexyloxy

Prior art date

2004-09-21

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.)

Expired - Fee Related

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• 150000001414 amino alcohols Chemical class 0.000 title description 12
• 150000001875 compounds Chemical class 0.000 claims abstract description 132
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 93
• 150000003839 salts Chemical class 0.000 claims abstract description 68
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 65
• -1 cyano, carboxy Chemical group 0.000 claims abstract description 55
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 40
• 239000001257 hydrogen Substances 0.000 claims abstract description 37
• 150000002431 hydrogen Chemical group 0.000 claims abstract description 29
• 206010020853 Hypertonic bladder Diseases 0.000 claims abstract description 13
• 208000009722 Overactive Urinary Bladder Diseases 0.000 claims abstract description 12
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 12
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 12
• 208000020629 overactive bladder Diseases 0.000 claims abstract description 12
• 208000025865 Ulcer Diseases 0.000 claims abstract description 10
• 150000002367 halogens Chemical group 0.000 claims abstract description 10
• 230000001225 therapeutic effect Effects 0.000 claims abstract description 10
• 231100000397 ulcer Toxicity 0.000 claims abstract description 10
• 230000000069 prophylactic effect Effects 0.000 claims abstract description 8
• 125000006239 protecting group Chemical group 0.000 claims abstract description 8
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
• 239000000651 prodrug Substances 0.000 claims abstract description 3
• 229940002612 prodrug Drugs 0.000 claims abstract description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 69
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 46
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 25
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
• 125000000623 heterocyclic group Chemical group 0.000 claims description 12
• 239000000048 adrenergic agonist Substances 0.000 claims description 10
• 229940126157 adrenergic receptor agonist Drugs 0.000 claims description 10
• 208000021891 Micturition disease Diseases 0.000 claims description 9
• 125000003118 aryl group Chemical group 0.000 claims description 9
• 208000018522 Gastrointestinal disease Diseases 0.000 claims description 8
• 208000008589 Obesity Diseases 0.000 claims description 8
• 206010033645 Pancreatitis Diseases 0.000 claims description 8
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
• 206010012601 diabetes mellitus Diseases 0.000 claims description 8
• 235000020824 obesity Nutrition 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 8
• 241000282414 Homo sapiens Species 0.000 claims description 7
• 241001465754 Metazoa Species 0.000 claims description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
• 125000001589 carboacyl group Chemical group 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 5
• 239000003814 drug Substances 0.000 claims description 5
• 125000003545 alkoxy group Chemical group 0.000 claims description 4
• BSQYSNVLJGMAHR-LJAQVGFWSA-N 2-cyclohexyloxy-n-(3-hydroxypropylsulfonyl)-4-[4-[2-[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]ethyl]phenyl]benzamide Chemical compound OCCCS(=O)(=O)NC(=O)C1=CC=C(C=2C=CC(CCNC[C@H](O)C=3C=NC=CC=3)=CC=2)C=C1OC1CCCCC1 BSQYSNVLJGMAHR-LJAQVGFWSA-N 0.000 claims description 3
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
• 125000001769 aryl amino group Chemical group 0.000 claims description 3
• 125000004104 aryloxy group Chemical group 0.000 claims description 3
• CTLKMUOZEMSEFY-PMERELPUSA-N 2-cyclohexyloxy-n-(3-hydroxypropylsulfonyl)-4-[4-[3-[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]propyl]phenyl]benzamide Chemical compound OCCCS(=O)(=O)NC(=O)C1=CC=C(C=2C=CC(CCCNC[C@H](O)C=3C=NC=CC=3)=CC=2)C=C1OC1CCCCC1 CTLKMUOZEMSEFY-PMERELPUSA-N 0.000 claims description 2
• YFTNNDYVRRZOEB-MHZLTWQESA-N 4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]-n-(3-hydroxypropylsulfonyl)-2-propan-2-ylsulfanylbenzamide Chemical compound C1=C(C(=O)NS(=O)(=O)CCCO)C(SC(C)C)=CC(C=2C=CC(CCNC[C@H](O)C=3C=CC=CC=3)=CC=2)=C1 YFTNNDYVRRZOEB-MHZLTWQESA-N 0.000 claims description 2
• ZHGDMWGCAJIKTK-LJAQVGFWSA-N 4-amino-n-[2-cyclohexyloxy-4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]phenyl]sulfonylbutanamide Chemical compound NCCCC(=O)NS(=O)(=O)C1=CC=C(C=2C=CC(CCNC[C@H](O)C=3C=CC=CC=3)=CC=2)C=C1OC1CCCCC1 ZHGDMWGCAJIKTK-LJAQVGFWSA-N 0.000 claims description 2
• 239000003937 drug carrier Substances 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
• 238000004519 manufacturing process Methods 0.000 claims 4
• LSGKMZLPZFPAIN-UHFFFAOYSA-N 1h-indole-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CNC2=C1 LSGKMZLPZFPAIN-UHFFFAOYSA-N 0.000 claims 2
• XXFBRBPLVFRJPL-HKBQPEDESA-N 2-(cyclohexylamino)-4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethoxy]phenyl]-n-(3-hydroxypropylsulfonyl)benzamide Chemical compound OCCCS(=O)(=O)NC(=O)C1=CC=C(C=2C=CC(OCCNC[C@H](O)C=3C=CC=CC=3)=CC=2)C=C1NC1CCCCC1 XXFBRBPLVFRJPL-HKBQPEDESA-N 0.000 claims 1
• GRZSQZBFHMTCKI-MHZLTWQESA-N 2-amino-n-[2-cyclohexyloxy-4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]phenyl]sulfonylacetamide Chemical compound NCC(=O)NS(=O)(=O)C1=CC=C(C=2C=CC(CCNC[C@H](O)C=3C=CC=CC=3)=CC=2)C=C1OC1CCCCC1 GRZSQZBFHMTCKI-MHZLTWQESA-N 0.000 claims 1
• KNMGDJHWPKTAHL-PMERELPUSA-N 2-cycloheptyloxy-n-(3-hydroxypropylsulfonyl)-4-[4-[2-[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]ethyl]phenyl]benzamide Chemical compound OCCCS(=O)(=O)NC(=O)C1=CC=C(C=2C=CC(CCNC[C@H](O)C=3C=NC=CC=3)=CC=2)C=C1OC1CCCCCC1 KNMGDJHWPKTAHL-PMERELPUSA-N 0.000 claims 1
• GKGWPFYTMOCIGK-PMERELPUSA-N 2-cyclohexyloxy-4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]-n-(3-hydroxypropylsulfonyl)benzamide Chemical compound OCCCS(=O)(=O)NC(=O)C1=CC=C(C=2C=CC(CCNC[C@H](O)C=3C=CC=CC=3)=CC=2)C=C1OC1CCCCC1 GKGWPFYTMOCIGK-PMERELPUSA-N 0.000 claims 1
• FINQYKRDYHZSQK-FWUCURJTSA-N 2-cyclohexyloxy-n-(2-hydroxyethylsulfonyl)-4-[4-[2-[[(1r,2s)-1-hydroxy-1-phenylpropan-2-yl]amino]ethyl]phenyl]benzamide 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)NS(=O)(=O)CCO)C=1OC1CCCCC1 FINQYKRDYHZSQK-FWUCURJTSA-N 0.000 claims 1
• OCWGZVXPZYEXBB-LJAQVGFWSA-N 2-cyclohexyloxy-n-(2-hydroxyethylsulfonyl)-4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]benzamide Chemical compound OCCS(=O)(=O)NC(=O)C1=CC=C(C=2C=CC(CCNC[C@H](O)C=3C=CC=CC=3)=CC=2)C=C1OC1CCCCC1 OCWGZVXPZYEXBB-LJAQVGFWSA-N 0.000 claims 1
• LBJKCOMVTINUFF-NDEPHWFRSA-N 2-cyclohexyloxy-n-(2-hydroxyethylsulfonyl)-4-[4-[2-[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]ethyl]phenyl]benzamide Chemical compound OCCS(=O)(=O)NC(=O)C1=CC=C(C=2C=CC(CCNC[C@H](O)C=3C=NC=CC=3)=CC=2)C=C1OC1CCCCC1 LBJKCOMVTINUFF-NDEPHWFRSA-N 0.000 claims 1
• GIGLTJZNEFAIQH-NDEPHWFRSA-N 2-cyclohexyloxy-n-(ethylsulfamoyl)-4-[4-[2-[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]ethyl]phenyl]benzamide Chemical compound CCNS(=O)(=O)NC(=O)C1=CC=C(C=2C=CC(CCNC[C@H](O)C=3C=NC=CC=3)=CC=2)C=C1OC1CCCCC1 GIGLTJZNEFAIQH-NDEPHWFRSA-N 0.000 claims 1
• KJCYKIUFNXJYES-PMERELPUSA-N 2-cyclopentyl-4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethoxy]phenyl]-n-(3-hydroxypropylsulfonyl)benzamide Chemical compound OCCCS(=O)(=O)NC(=O)C1=CC=C(C=2C=CC(OCCNC[C@H](O)C=3C=CC=CC=3)=CC=2)C=C1C1CCCC1 KJCYKIUFNXJYES-PMERELPUSA-N 0.000 claims 1
• WHWNBPTXOVHBBD-NDEPHWFRSA-N 3-[[2-cyclohexyloxy-4-[4-[2-[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]ethyl]phenyl]benzoyl]sulfamoyl]propanoic acid Chemical compound C([C@H](O)C=1C=NC=CC=1)NCCC(C=C1)=CC=C1C(C=1)=CC=C(C(=O)NS(=O)(=O)CCC(O)=O)C=1OC1CCCCC1 WHWNBPTXOVHBBD-NDEPHWFRSA-N 0.000 claims 1
• XUIUSKPBPGHDPU-NDEPHWFRSA-N 4-[4-[2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethylamino]phenyl]-n-(3-hydroxypropylsulfonyl)-2-(2-methylpropoxy)benzamide Chemical compound C1=C(C(=O)NS(=O)(=O)CCCO)C(OCC(C)C)=CC(C=2C=CC(NCCNC[C@H](O)C=3C=C(Cl)C=CC=3)=CC=2)=C1 XUIUSKPBPGHDPU-NDEPHWFRSA-N 0.000 claims 1
• ISBQNGDUOFPRSE-LJAQVGFWSA-N 4-[4-[2-[[(2r)-2-(4-aminophenyl)-2-hydroxyethyl]amino]ethyl]phenyl]-n-(3-hydroxypropylsulfonyl)-2-(2-methylpropyl)benzamide Chemical compound C1=C(C(=O)NS(=O)(=O)CCCO)C(CC(C)C)=CC(C=2C=CC(CCNC[C@H](O)C=3C=CC(N)=CC=3)=CC=2)=C1 ISBQNGDUOFPRSE-LJAQVGFWSA-N 0.000 claims 1
• OFPQFQFWJBOZQS-MHZLTWQESA-N 4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]-n-(3-hydroxypropylsulfonyl)-2-propan-2-yloxybenzamide Chemical compound C1=C(C(=O)NS(=O)(=O)CCCO)C(OC(C)C)=CC(C=2C=CC(CCNC[C@H](O)C=3C=CC=CC=3)=CC=2)=C1 OFPQFQFWJBOZQS-MHZLTWQESA-N 0.000 claims 1
• 125000003282 alkyl amino group Chemical group 0.000 claims 1
• SHMSIRZDABGFGG-LJAQVGFWSA-N n-(3-amino-3-oxopropyl)sulfonyl-2-cyclohexyloxy-4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]benzamide Chemical compound NC(=O)CCS(=O)(=O)NC(=O)C1=CC=C(C=2C=CC(CCNC[C@H](O)C=3C=CC=CC=3)=CC=2)C=C1OC1CCCCC1 SHMSIRZDABGFGG-LJAQVGFWSA-N 0.000 claims 1
• DQCPJHNWFIALFV-SANMLTNESA-N n-(3-hydroxypropylsulfonyl)-4-[4-[2-[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]ethyl]phenyl]-2-propan-2-yloxybenzamide Chemical compound C1=C(C(=O)NS(=O)(=O)CCCO)C(OC(C)C)=CC(C=2C=CC(CCNC[C@H](O)C=3C=NC=CC=3)=CC=2)=C1 DQCPJHNWFIALFV-SANMLTNESA-N 0.000 claims 1
• SHJKMTVMIGYAJV-SANMLTNESA-N n-(3-hydroxypropylsulfonyl)-4-[4-[2-[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]ethyl]phenyl]-2-propoxybenzamide Chemical compound C1=C(C(=O)NS(=O)(=O)CCCO)C(OCCC)=CC(C=2C=CC(CCNC[C@H](O)C=3C=NC=CC=3)=CC=2)=C1 SHJKMTVMIGYAJV-SANMLTNESA-N 0.000 claims 1
• HCXVGMMSNQPIRO-NDEPHWFRSA-N n-(3-hydroxypropylsulfonyl)-4-[4-[3-[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]amino]propyl]phenyl]-2-(2-methylpropoxy)benzamide Chemical compound C1=C(C(=O)NS(=O)(=O)CCCO)C(OCC(C)C)=CC(C=2C=CC(CCCNC[C@H](O)C=3C=NC=CC=3)=CC=2)=C1 HCXVGMMSNQPIRO-NDEPHWFRSA-N 0.000 claims 1
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 212
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 211
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 178
• 239000000203 mixture Substances 0.000 description 145
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 135
• 238000002360 preparation method Methods 0.000 description 107
• 239000000243 solution Substances 0.000 description 84
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 74
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 69
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 54
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 52
• 230000002829 reductive effect Effects 0.000 description 49
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
• 239000012267 brine Substances 0.000 description 44
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 44
• 239000011734 sodium Substances 0.000 description 43
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 38
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 36
• 239000012044 organic layer Substances 0.000 description 35
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 32
• 239000007787 solid Substances 0.000 description 31
• 239000000741 silica gel Substances 0.000 description 27
• 229910002027 silica gel Inorganic materials 0.000 description 27
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
• 238000004440 column chromatography Methods 0.000 description 23
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 23
• 235000019341 magnesium sulphate Nutrition 0.000 description 23
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 23
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 21
• 229910052938 sodium sulfate Inorganic materials 0.000 description 21
• 235000011152 sodium sulphate Nutrition 0.000 description 21
• 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 20
• 238000001914 filtration Methods 0.000 description 20
• 239000011541 reaction mixture Substances 0.000 description 18
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
• 238000001816 cooling Methods 0.000 description 17
• 238000000034 method Methods 0.000 description 17
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 16
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
• 238000001704 evaporation Methods 0.000 description 16
• 230000008020 evaporation Effects 0.000 description 16
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 15
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
• 239000002244 precipitate Substances 0.000 description 14
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 14
• 238000006243 chemical reaction Methods 0.000 description 12
• 239000000706 filtrate Substances 0.000 description 12
• 230000002265 prevention Effects 0.000 description 12
• 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 11
• 239000003480 eluent Substances 0.000 description 11
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 9
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
• 239000000284 extract Substances 0.000 description 9
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 9
• 125000004433 nitrogen atom Chemical group N* 0.000 description 9
• 239000000047 product Substances 0.000 description 9
• 101150041968 CDC13 gene Proteins 0.000 description 8
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
• 239000007864 aqueous solution Substances 0.000 description 8
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
• 239000010410 layer Substances 0.000 description 8
• 125000002911 monocyclic heterocycle group Chemical group 0.000 description 8
• 229910052757 nitrogen Inorganic materials 0.000 description 8
• YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 7
• 229940090181 propyl acetate Drugs 0.000 description 7
• 238000010898 silica gel chromatography Methods 0.000 description 7
• 239000002904 solvent Substances 0.000 description 7
• 238000003756 stirring Methods 0.000 description 7
• 239000000725 suspension Substances 0.000 description 7
• NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 7
• WORJRXHJTUTINR-UHFFFAOYSA-N 1,4-dioxane;hydron;chloride Chemical compound Cl.C1COCCO1 WORJRXHJTUTINR-UHFFFAOYSA-N 0.000 description 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
• 239000012299 nitrogen atmosphere Substances 0.000 description 6
• 125000004430 oxygen atom Chemical group O* 0.000 description 6
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
• 229920006395 saturated elastomer Polymers 0.000 description 6
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
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• IHBVJGYINYDKEP-PMERELPUSA-N tert-butyl n-[(2r)-2-hydroxy-2-phenylethyl]-n-[2-[4-[4-(3-hydroxypropylsulfonylcarbamoyl)-3-propan-2-yloxyphenyl]phenoxy]ethyl]carbamate Chemical compound C1=C(C(=O)NS(=O)(=O)CCCO)C(OC(C)C)=CC(C=2C=CC(OCCN(C[C@H](O)C=3C=CC=CC=3)C(=O)OC(C)(C)C)=CC=2)=C1 IHBVJGYINYDKEP-PMERELPUSA-N 0.000 description 1
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• AFUDOUCQUJWAQG-PMERELPUSA-N tert-butyl n-[(2r)-2-hydroxy-2-phenylethyl]-n-[2-[4-[4-(3-hydroxypropylsulfonylcarbamoyl)-3-propan-2-ylsulfanylphenyl]phenoxy]ethyl]carbamate Chemical compound C1=C(C(=O)NS(=O)(=O)CCCO)C(SC(C)C)=CC(C=2C=CC(OCCN(C[C@H](O)C=3C=CC=CC=3)C(=O)OC(C)(C)C)=CC=2)=C1 AFUDOUCQUJWAQG-PMERELPUSA-N 0.000 description 1
• AEDCUVCNQQADIO-PMERELPUSA-N tert-butyl n-[(2r)-2-hydroxy-2-phenylethyl]-n-[2-[4-[4-(3-hydroxypropylsulfonylcarbamoyl)-3-propan-2-ylsulfanylphenyl]phenyl]ethyl]carbamate Chemical compound C1=C(C(=O)NS(=O)(=O)CCCO)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 AEDCUVCNQQADIO-PMERELPUSA-N 0.000 description 1
• UAHNPVXVQOTOFH-NDEPHWFRSA-N tert-butyl n-[(2r)-2-hydroxy-2-phenylethyl]-n-[2-[4-[4-(methylsulfonylcarbamoyl)-3-propan-2-yloxyphenyl]phenyl]ethyl]carbamate Chemical compound C1=C(C(=O)NS(C)(=O)=O)C(OC(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 UAHNPVXVQOTOFH-NDEPHWFRSA-N 0.000 description 1
• UMVDKHUHVXIMQY-HKBQPEDESA-N tert-butyl n-[(2r)-2-hydroxy-2-phenylethyl]-n-[3-[4-[4-(3-hydroxypropylsulfonylcarbamoyl)-3-propan-2-yloxyphenyl]phenyl]propyl]carbamate Chemical compound C1=C(C(=O)NS(=O)(=O)CCCO)C(OC(C)C)=CC(C=2C=CC(CCCN(C[C@H](O)C=3C=CC=CC=3)C(=O)OC(C)(C)C)=CC=2)=C1 UMVDKHUHVXIMQY-HKBQPEDESA-N 0.000 description 1
• NWLIJXRJQAMGSR-UMSFTDKQSA-N tert-butyl n-[2-[4-[3-(cyclohexylamino)-4-(3-hydroxypropylsulfonylcarbamoyl)phenyl]phenoxy]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)CCOC(C=C1)=CC=C1C(C=1)=CC=C(C(=O)NS(=O)(=O)CCCO)C=1NC1CCCCC1 NWLIJXRJQAMGSR-UMSFTDKQSA-N 0.000 description 1
• XNXQTYFFNNKMGH-YTTGMZPUSA-N tert-butyl n-[2-[4-[3-cyclohexyloxy-4-(2-hydroxyethylsulfonylcarbamoyl)phenyl]phenyl]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)CCC(C=C1)=CC=C1C(C=1)=CC=C(C(=O)NS(=O)(=O)CCO)C=1OC1CCCCC1 XNXQTYFFNNKMGH-YTTGMZPUSA-N 0.000 description 1
• ANNJGDQDXWKKCH-HKBQPEDESA-N tert-butyl n-[2-[4-[3-cyclohexyloxy-4-(2-hydroxyethylsulfonylcarbamoyl)phenyl]phenyl]ethyl]-n-[(2r)-2-hydroxy-2-pyridin-3-ylethyl]carbamate Chemical compound C([C@H](O)C=1C=NC=CC=1)N(C(=O)OC(C)(C)C)CCC(C=C1)=CC=C1C(C=1)=CC=C(C(=O)NS(=O)(=O)CCO)C=1OC1CCCCC1 ANNJGDQDXWKKCH-HKBQPEDESA-N 0.000 description 1
• OCVUEDLGGQXSCB-XIFFEERXSA-N tert-butyl n-[2-[4-[3-cyclohexyloxy-4-(3-hydroxypropylsulfonylcarbamoyl)phenyl]phenoxy]ethyl]-n-[(2r)-2-hydroxy-2-(4-nitrophenyl)ethyl]carbamate Chemical compound C([C@H](O)C=1C=CC(=CC=1)[N+]([O-])=O)N(C(=O)OC(C)(C)C)CCOC(C=C1)=CC=C1C(C=1)=CC=C(C(=O)NS(=O)(=O)CCCO)C=1OC1CCCCC1 OCVUEDLGGQXSCB-XIFFEERXSA-N 0.000 description 1
• COKNUSSSEMZTGJ-XIFFEERXSA-N tert-butyl n-[2-[4-[3-cyclohexyloxy-4-(3-hydroxypropylsulfonylcarbamoyl)phenyl]phenoxy]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)CCOC(C=C1)=CC=C1C(C=1)=CC=C(C(=O)NS(=O)(=O)CCCO)C=1OC1CCCCC1 COKNUSSSEMZTGJ-XIFFEERXSA-N 0.000 description 1
• YFWOFMYJGPAASZ-XIFFEERXSA-N tert-butyl n-[2-[4-[3-cyclohexyloxy-4-(3-hydroxypropylsulfonylcarbamoyl)phenyl]phenyl]ethyl]-n-[(2r)-2-hydroxy-2-(3-nitrophenyl)ethyl]carbamate Chemical compound C([C@H](O)C=1C=C(C=CC=1)[N+]([O-])=O)N(C(=O)OC(C)(C)C)CCC(C=C1)=CC=C1C(C=1)=CC=C(C(=O)NS(=O)(=O)CCCO)C=1OC1CCCCC1 YFWOFMYJGPAASZ-XIFFEERXSA-N 0.000 description 1
• ARJUKVLNDVFXOR-XIFFEERXSA-N tert-butyl n-[2-[4-[3-cyclohexyloxy-4-(3-hydroxypropylsulfonylcarbamoyl)phenyl]phenyl]ethyl]-n-[(2r)-2-hydroxy-2-(4-nitrophenyl)ethyl]carbamate Chemical compound C([C@H](O)C=1C=CC(=CC=1)[N+]([O-])=O)N(C(=O)OC(C)(C)C)CCC(C=C1)=CC=C1C(C=1)=CC=C(C(=O)NS(=O)(=O)CCCO)C=1OC1CCCCC1 ARJUKVLNDVFXOR-XIFFEERXSA-N 0.000 description 1
• FCTOKJFSAHOHHZ-XIFFEERXSA-N tert-butyl n-[2-[4-[3-cyclohexyloxy-4-(3-hydroxypropylsulfonylcarbamoyl)phenyl]phenyl]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)CCC(C=C1)=CC=C1C(C=1)=CC=C(C(=O)NS(=O)(=O)CCCO)C=1OC1CCCCC1 FCTOKJFSAHOHHZ-XIFFEERXSA-N 0.000 description 1
• WBYNJTRERNGRMQ-YTTGMZPUSA-N tert-butyl n-[2-[4-[3-cyclohexyloxy-4-(3-hydroxypropylsulfonylcarbamoyl)phenyl]phenyl]ethyl]-n-[(2r)-2-hydroxy-2-pyridin-3-ylethyl]carbamate Chemical compound C([C@H](O)C=1C=NC=CC=1)N(C(=O)OC(C)(C)C)CCC(C=C1)=CC=C1C(C=1)=CC=C(C(=O)NS(=O)(=O)CCCO)C=1OC1CCCCC1 WBYNJTRERNGRMQ-YTTGMZPUSA-N 0.000 description 1
• DPURVNUCGCKBMG-HKBQPEDESA-N tert-butyl n-[2-[4-[3-cyclohexyloxy-4-(ethylsulfamoylcarbamoyl)phenyl]phenyl]ethyl]-n-[(2r)-2-hydroxy-2-pyridin-3-ylethyl]carbamate Chemical compound CCNS(=O)(=O)NC(=O)C1=CC=C(C=2C=CC(CCN(C[C@H](O)C=3C=NC=CC=3)C(=O)OC(C)(C)C)=CC=2)C=C1OC1CCCCC1 DPURVNUCGCKBMG-HKBQPEDESA-N 0.000 description 1
• XCFIERUKESNRAX-DHUJRADRSA-N tert-butyl n-[2-[4-[3-cyclohexyloxy-4-[4-[(2-methylpropan-2-yl)oxycarbonylamino]butanoylsulfamoyl]phenyl]phenyl]ethyl]-n-[(2r)-2-hydroxy-2-phenylethyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCC(=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 XCFIERUKESNRAX-DHUJRADRSA-N 0.000 description 1
• DGEDFIVHROSHHQ-XIFFEERXSA-N tert-butyl n-[2-[4-[3-cyclohexyloxy-4-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]sulfamoyl]phenyl]phenyl]ethyl]-n-[(2r)-2-hydroxy-2-phenylethyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC(=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 DGEDFIVHROSHHQ-XIFFEERXSA-N 0.000 description 1
• MHPZKNMOKRIYKP-XIFFEERXSA-N tert-butyl n-[2-[4-[3-cyclopentyl-4-(3-hydroxypropylsulfonylcarbamoyl)phenyl]phenoxy]ethyl]-n-[(2r)-2-hydroxy-2-(4-nitrophenyl)ethyl]carbamate Chemical compound C([C@H](O)C=1C=CC(=CC=1)[N+]([O-])=O)N(C(=O)OC(C)(C)C)CCOC(C=C1)=CC=C1C(C=1)=CC=C(C(=O)NS(=O)(=O)CCCO)C=1C1CCCC1 MHPZKNMOKRIYKP-XIFFEERXSA-N 0.000 description 1
• VLHVCWKWGRMKAV-XIFFEERXSA-N tert-butyl n-[2-[4-[3-cyclopentyl-4-(3-hydroxypropylsulfonylcarbamoyl)phenyl]phenyl]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)CCC(C=C1)=CC=C1C(C=1)=CC=C(C(=O)NS(=O)(=O)CCCO)C=1C1CCCC1 VLHVCWKWGRMKAV-XIFFEERXSA-N 0.000 description 1
• XUJAQXLPHNNKCF-ITLBEBSESA-N tert-butyl n-[2-[4-[4-(cyanomethylsulfonylcarbamoyl)-3-propan-2-ylsulfanylphenyl]phenyl]ethyl]-n-[(2r)-2-(oxan-2-yloxy)-2-phenylethyl]carbamate Chemical compound C1=C(C(=O)NS(=O)(=O)CC#N)C(SC(C)C)=CC(C=2C=CC(CCN(C[C@H](OC3OCCCC3)C=3C=CC=CC=3)C(=O)OC(C)(C)C)=CC=2)=C1 XUJAQXLPHNNKCF-ITLBEBSESA-N 0.000 description 1
• GYYQKKLMHAWLAX-QNGWXLTQSA-N tert-butyl n-[2-[4-[4-[(2-amino-2-oxoethyl)sulfonylcarbamoyl]-3-cyclohexyloxyphenyl]phenyl]ethyl]-n-[(2r)-2-[tert-butyl(dimethyl)silyl]oxy-2-(3-chlorophenyl)ethyl]carbamate Chemical compound C([C@H](O[Si](C)(C)C(C)(C)C)C=1C=C(Cl)C=CC=1)N(C(=O)OC(C)(C)C)CCC(C=C1)=CC=C1C(C=1)=CC=C(C(=O)NS(=O)(=O)CC(N)=O)C=1OC1CCCCC1 GYYQKKLMHAWLAX-QNGWXLTQSA-N 0.000 description 1
• LHDOPFNVCXIELI-BHVANESWSA-N tert-butyl n-[2-[4-[4-[(2-amino-2-oxoethyl)sulfonylcarbamoyl]-3-cyclohexyloxyphenyl]phenyl]ethyl]-n-[(2r)-2-[tert-butyl(dimethyl)silyl]oxy-2-pyridin-3-ylethyl]carbamate Chemical compound C([C@H](O[Si](C)(C)C(C)(C)C)C=1C=NC=CC=1)N(C(=O)OC(C)(C)C)CCC(C=C1)=CC=C1C(C=1)=CC=C(C(=O)NS(=O)(=O)CC(N)=O)C=1OC1CCCCC1 LHDOPFNVCXIELI-BHVANESWSA-N 0.000 description 1
• RHFZDMKQADXLCV-YTTGMZPUSA-N tert-butyl n-[2-[4-[4-[(3-amino-3-oxopropyl)sulfonylcarbamoyl]-3-cyclohexyloxyphenyl]phenyl]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)CCC(C=C1)=CC=C1C(C=1)=CC=C(C(=O)NS(=O)(=O)CCC(N)=O)C=1OC1CCCCC1 RHFZDMKQADXLCV-YTTGMZPUSA-N 0.000 description 1
• YVHHYFDNPCROBB-XIFFEERXSA-N tert-butyl n-[3-[4-[3-cyclohexyloxy-4-(3-hydroxypropylsulfonylcarbamoyl)phenyl]phenyl]propyl]-n-[(2r)-2-hydroxy-2-pyridin-3-ylethyl]carbamate Chemical compound C([C@H](O)C=1C=NC=CC=1)N(C(=O)OC(C)(C)C)CCCC(C=C1)=CC=C1C(C=1)=CC=C(C(=O)NS(=O)(=O)CCCO)C=1OC1CCCCC1 YVHHYFDNPCROBB-XIFFEERXSA-N 0.000 description 1
• CNUYAGPRYGOKRW-UMSFTDKQSA-N tert-butyl n-[3-[4-[3-cyclopentyl-4-(3-hydroxypropylsulfonylcarbamoyl)phenyl]phenyl]propyl]-n-[(2r)-2-hydroxy-2-(4-nitrophenyl)ethyl]carbamate Chemical compound C([C@H](O)C=1C=CC(=CC=1)[N+]([O-])=O)N(C(=O)OC(C)(C)C)CCCC(C=C1)=CC=C1C(C=1)=CC=C(C(=O)NS(=O)(=O)CCCO)C=1C1CCCC1 CNUYAGPRYGOKRW-UMSFTDKQSA-N 0.000 description 1
• QNQNDMRMHDNGJN-UMSFTDKQSA-N tert-butyl n-[3-[4-[3-cyclopentyl-4-(3-hydroxypropylsulfonylcarbamoyl)phenyl]phenyl]propyl]-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)CCCC(C=C1)=CC=C1C(C=1)=CC=C(C(=O)NS(=O)(=O)CCCO)C=1C1CCCC1 QNQNDMRMHDNGJN-UMSFTDKQSA-N 0.000 description 1
• UWSCKOMMRAVYJT-HKBQPEDESA-N tert-butyl n-[3-[4-[4-(3-hydroxypropylsulfonylcarbamoyl)-3-(2-methylpropoxy)phenyl]phenyl]propyl]-n-[(2r)-2-hydroxy-2-pyridin-3-ylethyl]carbamate Chemical compound C1=C(C(=O)NS(=O)(=O)CCCO)C(OCC(C)C)=CC(C=2C=CC(CCCN(C[C@H](O)C=3C=NC=CC=3)C(=O)OC(C)(C)C)=CC=2)=C1 UWSCKOMMRAVYJT-HKBQPEDESA-N 0.000 description 1
• FZXHWJSTRYPXEI-PMERELPUSA-N tert-butyl n-[3-[4-[4-(3-hydroxypropylsulfonylcarbamoyl)-3-propan-2-yloxyphenyl]phenyl]propyl]-n-[(2r)-2-hydroxy-2-pyridin-3-ylethyl]carbamate Chemical compound C1=C(C(=O)NS(=O)(=O)CCCO)C(OC(C)C)=CC(C=2C=CC(CCCN(C[C@H](O)C=3C=NC=CC=3)C(=O)OC(C)(C)C)=CC=2)=C1 FZXHWJSTRYPXEI-PMERELPUSA-N 0.000 description 1
• BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
• 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 238000010998 test method Methods 0.000 description 1
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
• 125000003831 tetrazolyl group Chemical group 0.000 description 1
• 125000001113 thiadiazolyl group Chemical group 0.000 description 1
• 125000001984 thiazolidinyl group Chemical group 0.000 description 1
• 125000000335 thiazolyl group Chemical group 0.000 description 1
• 125000001544 thienyl group Chemical group 0.000 description 1
• 229960003553 tolterodine tartrate Drugs 0.000 description 1
• 230000000699 topical effect Effects 0.000 description 1
• 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
• 125000001425 triazolyl group Chemical group 0.000 description 1
• 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
• 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
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• 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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• 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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• 238000009736 wetting Methods 0.000 description 1
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