RU2399614C2 - Аминоспиртовые производные - Google Patents

Info

Publication number

RU2399614C2

RU2399614C2 RU2007115092/04A RU2007115092A RU2399614C2 RU 2399614 C2 RU2399614 C2 RU 2399614C2 RU 2007115092/04 A RU2007115092/04 A RU 2007115092/04A RU 2007115092 A RU2007115092 A RU 2007115092A RU 2399614 C2 RU2399614 C2 RU 2399614C2

Authority

RU

Russia

Prior art keywords

ethyl

amino

sulfonyl

hydroxy

esi

Prior art date

2004-09-21

Links

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• 150000001414 amino alcohols Chemical class 0.000 title description 11
• 150000001875 compounds Chemical class 0.000 claims abstract description 130
• 238000000034 method Methods 0.000 claims abstract description 111
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 68
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 42
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
• 239000001257 hydrogen Substances 0.000 claims abstract description 26
• 238000011282 treatment Methods 0.000 claims abstract description 19
• 150000002431 hydrogen Chemical group 0.000 claims abstract description 17
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
• 150000002367 halogens Chemical group 0.000 claims abstract description 9
• 206010020853 Hypertonic bladder Diseases 0.000 claims abstract description 8
• 208000009722 Overactive Urinary Bladder Diseases 0.000 claims abstract description 7
• 208000020629 overactive bladder Diseases 0.000 claims abstract description 7
• 230000001225 therapeutic effect Effects 0.000 claims abstract description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims abstract 4
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract 4
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims abstract 2
• 239000000203 mixture Substances 0.000 claims description 141
• -1 3- (cyclohexyloxy) -R - [(3-hydroxypropyl) sulfonyl] Chemical class 0.000 claims description 135
• 150000003839 salts Chemical class 0.000 claims description 52
• 230000036724 intravesical pressure Effects 0.000 claims description 10
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
• 241001465754 Metazoa Species 0.000 claims description 5
• 208000028938 Urination disease Diseases 0.000 claims description 4
• 239000004480 active ingredient Substances 0.000 claims description 3
• 239000003814 drug Substances 0.000 claims description 3
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
• 230000000069 prophylactic effect Effects 0.000 claims description 3
• 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 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
• 239000003112 inhibitor Substances 0.000 claims 3
• 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
• 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
• CPSNDGKXWDABMP-PMERELPUSA-N 2-cyclohexyloxy-4-[4-[2-[[(2r)-2-(3-fluorophenyl)-2-hydroxyethyl]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=C(F)C=CC=3)=CC=2)C=C1OC1CCCCC1 CPSNDGKXWDABMP-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
• SDLLCFTUSHPKPY-HKBQPEDESA-N 2-cyclohexyloxy-n-(3-hydroxy-3-methylbutyl)sulfonyl-4-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethyl]phenyl]benzamide Chemical compound CC(C)(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 SDLLCFTUSHPKPY-HKBQPEDESA-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
• 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
• 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 1
• UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• 229940126601 medicinal product Drugs 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
• 230000000694 effects Effects 0.000 abstract description 3
• 239000000126 substance Substances 0.000 abstract description 2
• 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
• 239000003795 chemical substances by application Substances 0.000 abstract 1
• 230000003449 preventive effect Effects 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 223
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 216
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 144
• 239000000243 solution Substances 0.000 description 88
• 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
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 54
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 50
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 49
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 46
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
• 239000012267 brine Substances 0.000 description 45
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 45
• 239000011734 sodium Substances 0.000 description 42
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 40
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
• 238000010898 silica gel chromatography Methods 0.000 description 36
• 239000012044 organic layer Substances 0.000 description 35
• 239000007787 solid Substances 0.000 description 31
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
• 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 27
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 26
• 238000006243 chemical reaction Methods 0.000 description 24
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 24
• 235000019341 magnesium sulphate Nutrition 0.000 description 24
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 22
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 22
• 239000011541 reaction mixture Substances 0.000 description 22
• 229910052938 sodium sulfate Inorganic materials 0.000 description 22
• 235000011152 sodium sulphate Nutrition 0.000 description 22
• 238000001914 filtration Methods 0.000 description 21
• 239000007864 aqueous solution Substances 0.000 description 20
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 19
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
• 238000001816 cooling Methods 0.000 description 17
• 238000001704 evaporation Methods 0.000 description 16
• 230000008020 evaporation Effects 0.000 description 16
• YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 16
• 229940090181 propyl acetate Drugs 0.000 description 16
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 15
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 15
• 239000002244 precipitate Substances 0.000 description 13
• 239000000706 filtrate Substances 0.000 description 12
• 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 11
• 239000003480 eluent Substances 0.000 description 11
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
• 125000000623 heterocyclic group Chemical group 0.000 description 10
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 10
• 239000012299 nitrogen atmosphere Substances 0.000 description 10
• 125000003118 aryl group Chemical group 0.000 description 9
• 239000000284 extract Substances 0.000 description 9
• 125000002911 monocyclic heterocycle group Chemical group 0.000 description 9
• 125000004433 nitrogen atom Chemical group N* 0.000 description 9
• 239000000047 product Substances 0.000 description 9
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 8
• 239000010410 layer Substances 0.000 description 8
• 229920006395 saturated elastomer Polymers 0.000 description 8
• 239000002904 solvent Substances 0.000 description 8
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 7
• 125000002947 alkylene group Chemical group 0.000 description 7
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
• 125000004430 oxygen atom Chemical group O* 0.000 description 7
• 230000002265 prevention Effects 0.000 description 7
• 238000003756 stirring Methods 0.000 description 7
• 239000000725 suspension Substances 0.000 description 7
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• 125000004453 alkoxycarbonyl group Chemical group 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
• 125000002496 methyl group Chemical group [H]C([H])([H])* 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
• 125000006239 protecting group Chemical group 0.000 description 6
• 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 5
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 5
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
• 125000003545 alkoxy group Chemical group 0.000 description 5
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 5
• 125000001589 carboacyl group Chemical group 0.000 description 5
• 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 5
• 201000010099 disease Diseases 0.000 description 5
• 229910052757 nitrogen Inorganic materials 0.000 description 5
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
• 229910000029 sodium carbonate Inorganic materials 0.000 description 5
• 125000006529 (C3-C6) alkyl group Chemical group 0.000 description 4
• 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 4
• WORJRXHJTUTINR-UHFFFAOYSA-N 1,4-dioxane;hydron;chloride Chemical compound Cl.C1COCCO1 WORJRXHJTUTINR-UHFFFAOYSA-N 0.000 description 4
• OAEBNNHZRMTPRC-UHFFFAOYSA-N 2-phenylbenzamide;dihydrochloride Chemical compound Cl.Cl.NC(=O)C1=CC=CC=C1C1=CC=CC=C1 OAEBNNHZRMTPRC-UHFFFAOYSA-N 0.000 description 4
• NDIXNYNPRADIDL-UHFFFAOYSA-N 3-sulfamoylpropyl acetate Chemical compound CC(=O)OCCCS(N)(=O)=O NDIXNYNPRADIDL-UHFFFAOYSA-N 0.000 description 4
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
• DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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• 239000011630 iodine Substances 0.000 description 1
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• ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
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• CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 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
• 230000004060 metabolic process Effects 0.000 description 1
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• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
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• MYUBDJJXCLZBLB-UHFFFAOYSA-N methyl 1-propan-2-yl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole-3-carboxylate Chemical compound C=1C=C2C(C(=O)OC)=CN(C(C)C)C2=CC=1B1OC(C)(C)C(C)(C)O1 MYUBDJJXCLZBLB-UHFFFAOYSA-N 0.000 description 1
• HXQFVUKONPQDNT-JQJBXXCASA-N methyl 2-cyclohexyloxy-4-[4-[2-[[(1r,2s)-1-hydroxy-1-phenylpropan-2-yl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethyl]phenyl]benzoate Chemical compound COC(=O)C1=CC=C(C=2C=CC(CCN([C@@H](C)[C@H](O)C=3C=CC=CC=3)C(=O)OC(C)(C)C)=CC=2)C=C1OC1CCCCC1 HXQFVUKONPQDNT-JQJBXXCASA-N 0.000 description 1
• NLAQZUQVQFYTOS-TYIYNAFKSA-N methyl 2-cyclopentyl-4-[4-[2-[(2-methylpropan-2-yl)oxycarbonyl-[(2r)-2-(oxan-2-yloxy)-2-phenylethyl]amino]ethyl]phenyl]benzoate Chemical compound COC(=O)C1=CC=C(C=2C=CC(CCN(C[C@H](OC3OCCCC3)C=3C=CC=CC=3)C(=O)OC(C)(C)C)=CC=2)C=C1C1CCCC1 NLAQZUQVQFYTOS-TYIYNAFKSA-N 0.000 description 1
• ICTSDDRYJKMPGS-UHFFFAOYSA-N methyl 3-sulfamoylpropanoate Chemical compound COC(=O)CCS(N)(=O)=O ICTSDDRYJKMPGS-UHFFFAOYSA-N 0.000 description 1
• DGVLNQAYPGGKPC-TXEYEHERSA-N methyl 4-[4-[2-[(2-methylpropan-2-yl)oxycarbonyl-[(2r)-2-(oxan-2-yloxy)-2-phenylethyl]amino]ethyl]phenyl]-2-propan-2-ylsulfanylbenzoate Chemical compound C1=C(SC(C)C)C(C(=O)OC)=CC=C1C(C=C1)=CC=C1CCN(C(=O)OC(C)(C)C)C[C@@H](C=1C=CC=CC=1)OC1OCCCC1 DGVLNQAYPGGKPC-TXEYEHERSA-N 0.000 description 1
• KXPAOBTZDWJZDK-HKBQPEDESA-N methyl 4-[4-[2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethyl]phenyl]-2-cyclohexyloxybenzoate Chemical compound COC(=O)C1=CC=C(C=2C=CC(CCN(C[C@H](O)C=3C=C(Cl)C=CC=3)C(=O)OC(C)(C)C)=CC=2)C=C1OC1CCCCC1 KXPAOBTZDWJZDK-HKBQPEDESA-N 0.000 description 1
• YEMRDKJSPOYMPQ-NDEPHWFRSA-N methyl 4-[4-[2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethyl]phenyl]-2-propan-2-ylsulfanylbenzoate Chemical compound C1=C(SC(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(Cl)=C1 YEMRDKJSPOYMPQ-NDEPHWFRSA-N 0.000 description 1
• JBIKTLCINPCQSN-QNGWXLTQSA-N methyl 4-[4-[2-[[(2r)-2-[tert-butyl(dimethyl)silyl]oxy-2-(3-chlorophenyl)ethyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethyl]phenyl]-2-cyclohexyloxybenzoate Chemical compound COC(=O)C1=CC=C(C=2C=CC(CCN(C[C@H](O[Si](C)(C)C(C)(C)C)C=3C=C(Cl)C=CC=3)C(=O)OC(C)(C)C)=CC=2)C=C1OC1CCCCC1 JBIKTLCINPCQSN-QNGWXLTQSA-N 0.000 description 1
• ZIYSSXKMXIVVPV-BHVANESWSA-N methyl 4-[4-[2-[[(2r)-2-[tert-butyl(dimethyl)silyl]oxy-2-pyridin-3-ylethyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethyl]phenyl]-2-cyclohexyloxybenzoate Chemical compound COC(=O)C1=CC=C(C=2C=CC(CCN(C[C@H](O[Si](C)(C)C(C)(C)C)C=3C=NC=CC=3)C(=O)OC(C)(C)C)=CC=2)C=C1OC1CCCCC1 ZIYSSXKMXIVVPV-BHVANESWSA-N 0.000 description 1
• DHYMAIYEICALLP-NDEPHWFRSA-N methyl 4-[4-[3-[[(2r)-2-hydroxy-2-pyridin-3-ylethyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]propyl]phenyl]-2-propan-2-yloxybenzoate Chemical compound C1=C(OC(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 DHYMAIYEICALLP-NDEPHWFRSA-N 0.000 description 1
• PWPGAVDNJTXJPY-TYIYNAFKSA-N methyl 6-[4-[2-[[(2r)-2-(3-chlorophenyl)-2-(oxan-2-yloxy)ethyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethyl]phenyl]-1-propan-2-ylindole-3-carboxylate Chemical compound O([C@@H](CN(CCC1=CC=C(C=C1)C=1C=C2N(C(C)C)C=C(C2=CC=1)C(=O)OC)C(=O)OC(C)(C)C)C=1C=C(Cl)C=CC=1)C1CCCCO1 PWPGAVDNJTXJPY-TYIYNAFKSA-N 0.000 description 1
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• RGDSDENGPYCYKT-UMSFTDKQSA-N tert-butyl n-[2-[4-[3-cyclohexyloxy-4-(4-hydroxybutylsulfonylcarbamoyl)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)CCCCO)C=1OC1CCCCC1 RGDSDENGPYCYKT-UMSFTDKQSA-N 0.000 description 1
• RSLZOJIOLXFOBX-LJAQVGFWSA-N tert-butyl n-[2-[4-[4-(3-hydroxypropylsulfonylcarbamoyl)-3-propan-2-yloxyphenyl]phenyl]ethyl]-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(CCN(C[C@H](O)C=3C=NC=CC=3)C(=O)OC(C)(C)C)=CC=2)=C1 RSLZOJIOLXFOBX-LJAQVGFWSA-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
• 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
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• 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 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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