PT1791811E - ¿derivados de aminoálcool - Google Patents
¿derivados de aminoálcool Download PDFInfo
- Publication number
- PT1791811E PT1791811E PT05787773T PT05787773T PT1791811E PT 1791811 E PT1791811 E PT 1791811E PT 05787773 T PT05787773 T PT 05787773T PT 05787773 T PT05787773 T PT 05787773T PT 1791811 E PT1791811 E PT 1791811E
- Authority
- PT
- Portugal
- Prior art keywords
- ethyl
- amino
- sulfonyl
- biphenylcarboxamide
- hydroxy
- Prior art date
Links
- 150000001414 amino alcohols Chemical class 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 102
- -1 cyano, carboxy Chemical group 0.000 claims abstract description 74
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 58
- 150000003839 salts Chemical class 0.000 claims abstract description 56
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 10
- 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
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical group 0.000 claims abstract description 6
- 208000025865 Ulcer Diseases 0.000 claims abstract description 5
- 231100000397 ulcer Toxicity 0.000 claims abstract description 5
- 230000001225 therapeutic effect Effects 0.000 claims abstract description 4
- 230000000069 prophylactic effect Effects 0.000 claims abstract description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 45
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 25
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 15
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 13
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims description 11
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
- 239000000048 adrenergic agonist Substances 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
- 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 description 3
- 208000008589 Obesity Diseases 0.000 claims description 3
- 206010033645 Pancreatitis Diseases 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 206010012601 diabetes mellitus Diseases 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 235000020824 obesity Nutrition 0.000 claims description 3
- 230000007170 pathology Effects 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003113 cycloheptyloxy group Chemical group C1(CCCCCC1)O* 0.000 claims description 2
- 230000002496 gastric effect Effects 0.000 claims description 2
- 230000027939 micturition Effects 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 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 239000003937 drug carrier Substances 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
- 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 6
- 125000002947 alkylene group Chemical group 0.000 abstract description 4
- 125000006239 protecting group Chemical group 0.000 abstract description 3
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 229940002612 prodrug Drugs 0.000 abstract 1
- 239000000651 prodrug Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 132
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 105
- 238000002360 preparation method Methods 0.000 description 102
- 239000000203 mixture Substances 0.000 description 90
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
- 238000005481 NMR spectroscopy Methods 0.000 description 70
- 239000000243 solution Substances 0.000 description 63
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 58
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 52
- 238000000034 method Methods 0.000 description 49
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
- 230000002829 reductive effect Effects 0.000 description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 33
- 239000012267 brine Substances 0.000 description 28
- 239000011734 sodium Substances 0.000 description 28
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- 238000010898 silica gel chromatography Methods 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 239000012074 organic phase Substances 0.000 description 20
- 238000001914 filtration Methods 0.000 description 19
- 239000007787 solid Substances 0.000 description 19
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- 229910052938 sodium sulfate Inorganic materials 0.000 description 15
- 235000011152 sodium sulphate Nutrition 0.000 description 15
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 15
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
- 235000019341 magnesium sulphate Nutrition 0.000 description 14
- 239000002244 precipitate Substances 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- 230000002265 prevention Effects 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- 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 7
- 230000008020 evaporation Effects 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 6
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 6
- 239000003480 eluent Substances 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
- 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 230000036724 intravesical pressure Effects 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 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
- 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 description 4
- AABCZPFWZSCVAF-PMERELPUSA-N 4-[4-[2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethylamino]phenyl]-2-cyclohexyloxybenzoic acid Chemical compound C([C@H](O)C=1C=C(Cl)C=CC=1)N(C(=O)OC(C)(C)C)CCNC(C=C1)=CC=C1C(C=1)=CC=C(C(O)=O)C=1OC1CCCCC1 AABCZPFWZSCVAF-PMERELPUSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 229940126157 adrenergic receptor agonist Drugs 0.000 description 4
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 4
- 229960004484 carbachol Drugs 0.000 description 4
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 102000016959 beta-3 Adrenergic Receptors Human genes 0.000 description 3
- 108010014502 beta-3 Adrenergic Receptors Proteins 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 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 3
- 230000000694 effects Effects 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 235000011056 potassium acetate Nutrition 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229940090181 propyl acetate Drugs 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- FUKCVMLONUSXMC-UHFFFAOYSA-N 2-phenylmethoxyethanesulfonic acid Chemical compound OS(=O)(=O)CCOCC1=CC=CC=C1 FUKCVMLONUSXMC-UHFFFAOYSA-N 0.000 description 2
- FVSVJFRJXMWFJM-UHFFFAOYSA-N 2-phenylmethoxyethanesulfonyl chloride Chemical compound ClS(=O)(=O)CCOCC1=CC=CC=C1 FVSVJFRJXMWFJM-UHFFFAOYSA-N 0.000 description 2
- BOHXOWPKTRIWPB-MOJIJOCKSA-N 4-[4-[2-[(2-methylpropan-2-yl)oxycarbonyl-[(2r)-2-(oxan-2-yloxy)-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(CCN(C[C@H](OC3OCCCC3)C=3C=CC=CC=3)C(=O)OC(C)(C)C)=CC=2)=C1 BOHXOWPKTRIWPB-MOJIJOCKSA-N 0.000 description 2
- CJYUVTNVNVNPBT-BHVANESWSA-N 4-[4-[2-[[(2r)-2-[tert-butyl(dimethyl)silyl]oxy-2-(3-chlorophenyl)ethyl]-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethyl]phenyl]-2-cyclohexyloxybenzoic acid 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)=O)C=1OC1CCCCC1 CJYUVTNVNVNPBT-BHVANESWSA-N 0.000 description 2
- ZCPVDHZKGQQHDS-UHFFFAOYSA-N 4-bromo-2-fluorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(Br)C=C1F ZCPVDHZKGQQHDS-UHFFFAOYSA-N 0.000 description 2
- YRBVMXUOMHAFQU-SFCXHYMASA-N 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-carboxylic acid Chemical compound O([C@@H](CN(CCC1=CC=C(C=C1)C1=CC=C2C(C(O)=O)=CN(C2=C1)C(C)C)C(=O)OC(C)(C)C)C=1C=C(Cl)C=CC=1)C1CCCCO1 YRBVMXUOMHAFQU-SFCXHYMASA-N 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- C07C317/48—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
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- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
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- A61P13/00—Drugs for disorders of the urinary system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/51—Y being a hydrogen or a carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/63—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Pyrane Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2004905450A AU2004905450A0 (en) | 2004-09-21 | Aminoalcohol Derivatives | |
| AU2005900789A AU2005900789A0 (en) | 2005-02-21 | Aminoalcohol Derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PT1791811E true PT1791811E (pt) | 2010-02-23 |
Family
ID=35524070
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT05787773T PT1791811E (pt) | 2004-09-21 | 2005-09-20 | ¿derivados de aminoálcool |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US7928264B2 (https=) |
| EP (1) | EP1791811B1 (https=) |
| JP (1) | JP4893620B2 (https=) |
| KR (1) | KR101052462B1 (https=) |
| AT (1) | ATE452876T1 (https=) |
| BR (1) | BRPI0515710A (https=) |
| CA (1) | CA2580760C (https=) |
| DE (1) | DE602005018503D1 (https=) |
| DK (1) | DK1791811T3 (https=) |
| ES (1) | ES2337164T3 (https=) |
| IL (1) | IL181888A (https=) |
| MX (1) | MX2007003111A (https=) |
| NO (1) | NO20071468L (https=) |
| PL (1) | PL1791811T3 (https=) |
| PT (1) | PT1791811E (https=) |
| RU (1) | RU2399614C2 (https=) |
| WO (1) | WO2006033446A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100548979C (zh) * | 2007-01-12 | 2009-10-14 | 中国科学院上海有机化学研究所 | 一种合成3-甲氨基吲哚化合物的方法 |
| WO2014133059A1 (ja) | 2013-02-28 | 2014-09-04 | 武田薬品工業株式会社 | スルホニルクロライド化合物の製造法 |
| KR102594322B1 (ko) * | 2014-12-19 | 2023-10-26 | 가이스틀리히 파마 아게 | 옥사티아진-유사 화합물의 제조방법 |
| US11591302B2 (en) | 2014-12-19 | 2023-02-28 | Geistlich Pharm A Ag | Processes for preparing oxathiazin-like compounds |
| CN109476615A (zh) * | 2016-04-07 | 2019-03-15 | 盖斯特里希医药公司 | 制备噁噻嗪类化合物的方法 |
| WO2018090054A1 (en) | 2016-11-14 | 2018-05-17 | Berg Llc | Methods for treating parkinson's disease |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3718638A1 (de) | 1987-06-04 | 1988-12-22 | Thomae Gmbh Dr K | Neue phenylethanolamine, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| UA58494C2 (uk) * | 1995-06-07 | 2003-08-15 | Зенека Лімітед | Похідні n-гетероарилпіридинсульфонаміду, фармацевтична композиція, спосіб одержання та спосіб протидії впливам ендотеліну |
| GT200100147A (es) | 2000-07-31 | 2002-06-25 | Derivados de imidazol | |
| GB0021757D0 (en) * | 2000-09-04 | 2000-10-18 | Colaco Camilo | Vaccine against microbial pathogens |
| CN1469876A (zh) * | 2000-10-20 | 2004-01-21 | �Ʒ� | α-芳基乙醇胺及其用作β-3肾上腺素能受体激动剂的用途 |
| WO2002094770A2 (en) * | 2001-05-24 | 2002-11-28 | Fujisawa Pharmaceutical Co., Ltd. | Aminoalcohol derivatives |
| KR100693367B1 (ko) | 2002-06-27 | 2007-03-12 | 아스텔라스세이야쿠 가부시키가이샤 | 아미노알콜 유도체 |
| AU2002952839A0 (en) * | 2002-11-21 | 2002-12-05 | Fujisawa Pharmaceutical Co., Ltd. | Aminoalcohol derivatives |
| AU2004303740A1 (en) * | 2003-12-22 | 2005-07-07 | Astrazeneca Ab | Nicotinic acetylcholine receptor ligands |
| EP1697301A2 (en) * | 2003-12-23 | 2006-09-06 | Astellas Pharma Inc. | Aminoalcohol derivatives |
-
2005
- 2005-09-20 EP EP05787773A patent/EP1791811B1/en not_active Expired - Lifetime
- 2005-09-20 BR BRPI0515710-2A patent/BRPI0515710A/pt not_active IP Right Cessation
- 2005-09-20 RU RU2007115092/04A patent/RU2399614C2/ru not_active IP Right Cessation
- 2005-09-20 PL PL05787773T patent/PL1791811T3/pl unknown
- 2005-09-20 ES ES05787773T patent/ES2337164T3/es not_active Expired - Lifetime
- 2005-09-20 JP JP2007512362A patent/JP4893620B2/ja not_active Expired - Fee Related
- 2005-09-20 AT AT05787773T patent/ATE452876T1/de active
- 2005-09-20 PT PT05787773T patent/PT1791811E/pt unknown
- 2005-09-20 DK DK05787773.0T patent/DK1791811T3/da active
- 2005-09-20 US US11/547,847 patent/US7928264B2/en not_active Expired - Fee Related
- 2005-09-20 WO PCT/JP2005/017669 patent/WO2006033446A1/en not_active Ceased
- 2005-09-20 DE DE602005018503T patent/DE602005018503D1/de not_active Expired - Lifetime
- 2005-09-20 MX MX2007003111A patent/MX2007003111A/es active IP Right Grant
- 2005-09-20 CA CA2580760A patent/CA2580760C/en not_active Expired - Fee Related
- 2005-09-20 KR KR1020077006444A patent/KR101052462B1/ko not_active Expired - Fee Related
-
2007
- 2007-03-13 IL IL181888A patent/IL181888A/en not_active IP Right Cessation
- 2007-03-19 NO NO20071468A patent/NO20071468L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US20080039506A1 (en) | 2008-02-14 |
| ATE452876T1 (de) | 2010-01-15 |
| IL181888A0 (en) | 2007-07-04 |
| ES2337164T3 (es) | 2010-04-21 |
| CA2580760C (en) | 2013-08-27 |
| CA2580760A1 (en) | 2006-03-30 |
| US7928264B2 (en) | 2011-04-19 |
| MX2007003111A (es) | 2007-05-24 |
| IL181888A (en) | 2012-10-31 |
| KR20070054667A (ko) | 2007-05-29 |
| RU2007115092A (ru) | 2008-10-27 |
| WO2006033446A1 (en) | 2006-03-30 |
| EP1791811A1 (en) | 2007-06-06 |
| BRPI0515710A (pt) | 2008-07-29 |
| KR101052462B1 (ko) | 2011-07-28 |
| JP4893620B2 (ja) | 2012-03-07 |
| RU2399614C2 (ru) | 2010-09-20 |
| PL1791811T3 (pl) | 2010-06-30 |
| EP1791811B1 (en) | 2009-12-23 |
| DK1791811T3 (da) | 2010-03-22 |
| JP2008513348A (ja) | 2008-05-01 |
| NO20071468L (no) | 2007-04-20 |
| DE602005018503D1 (de) | 2010-02-04 |
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