JP2009530272A5 - - Google Patents
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- JP2009530272A5 JP2009530272A5 JP2009500323A JP2009500323A JP2009530272A5 JP 2009530272 A5 JP2009530272 A5 JP 2009530272A5 JP 2009500323 A JP2009500323 A JP 2009500323A JP 2009500323 A JP2009500323 A JP 2009500323A JP 2009530272 A5 JP2009530272 A5 JP 2009530272A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- ethylamino
- phenyl
- ethyl
- methyl
- Prior art date
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 27
- -1 R 31 Chemical compound 0.000 claims description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000003107 substituted aryl group Chemical group 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- 239000003638 chemical reducing agent Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- VKCKAMBPNXKGHL-QFIPXVFZSA-N 4-hydroxy-7-[(1r)-1-hydroxy-2-[2-[3-[[(2-methoxyphenyl)methylamino]methyl]phenyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound COC1=CC=CC=C1CNCC1=CC=CC(CCNC[C@H](O)C=2C=3SC(=O)NC=3C(O)=CC=2)=C1 VKCKAMBPNXKGHL-QFIPXVFZSA-N 0.000 claims 3
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 3
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 3
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 3
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- YBEOVDGQPYYDKC-FQEVSTJZSA-N 4-hydroxy-7-[(1r)-1-hydroxy-2-[2-[3-(piperidin-1-ylmethyl)phenyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound C([C@H](O)C=1C=2SC(=O)NC=2C(O)=CC=1)NCCC(C=1)=CC=CC=1CN1CCCCC1 YBEOVDGQPYYDKC-FQEVSTJZSA-N 0.000 claims 2
- WWEHZPFFGZLBOV-QFIPXVFZSA-N 4-hydroxy-7-[(1r)-1-hydroxy-2-[2-[3-[(2-pyridin-2-ylethylamino)methyl]phenyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound C([C@H](O)C=1C=2SC(=O)NC=2C(O)=CC=1)NCCC(C=1)=CC=CC=1CNCCC1=CC=CC=N1 WWEHZPFFGZLBOV-QFIPXVFZSA-N 0.000 claims 2
- CLZMZYMASUQJLW-FPOVZHCZSA-N 4-hydroxy-7-[(1r)-1-hydroxy-2-[2-[3-[[[(2r)-1-methoxy-3-methylbutan-2-yl]amino]methyl]phenyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound COC[C@@H](C(C)C)NCC1=CC=CC(CCNC[C@H](O)C=2C=3SC(=O)NC=3C(O)=CC=2)=C1 CLZMZYMASUQJLW-FPOVZHCZSA-N 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 206010014561 Emphysema Diseases 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 230000009286 beneficial effect Effects 0.000 claims 2
- 201000009267 bronchiectasis Diseases 0.000 claims 2
- 206010006451 bronchitis Diseases 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 206010039083 rhinitis Diseases 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- JFUAWXPBHXKZGA-IBGZPJMESA-N 4-fluoro-2-[(4r)-5,5,5-trifluoro-4-hydroxy-2-methyl-4-(1h-pyrrolo[2,3-c]pyridin-2-ylmethyl)pentan-2-yl]phenol Chemical compound C([C@@](O)(CC=1NC2=CN=CC=C2C=1)C(F)(F)F)C(C)(C)C1=CC(F)=CC=C1O JFUAWXPBHXKZGA-IBGZPJMESA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- OEHDDSHOAVGWRF-IBGZPJMESA-N 4-hydroxy-7-[(1r)-1-hydroxy-2-[2-[3-(morpholin-4-ylmethyl)phenyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound C([C@H](O)C=1C=2SC(=O)NC=2C(O)=CC=1)NCCC(C=1)=CC=CC=1CN1CCOCC1 OEHDDSHOAVGWRF-IBGZPJMESA-N 0.000 claims 1
- ZUHXIOJIKIPZOR-IBGZPJMESA-N 4-hydroxy-7-[(1r)-1-hydroxy-2-[2-[3-(piperazin-1-ylmethyl)phenyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound C([C@H](O)C=1C=2SC(=O)NC=2C(O)=CC=1)NCCC(C=1)=CC=CC=1CN1CCNCC1 ZUHXIOJIKIPZOR-IBGZPJMESA-N 0.000 claims 1
- QWWLVVDOGURJDF-IBGZPJMESA-N 4-hydroxy-7-[(1r)-1-hydroxy-2-[2-[3-(pyrrolidin-1-ylmethyl)phenyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound C([C@H](O)C=1C=2SC(=O)NC=2C(O)=CC=1)NCCC(C=1)=CC=CC=1CN1CCCC1 QWWLVVDOGURJDF-IBGZPJMESA-N 0.000 claims 1
- BGLYKONMLBFSGK-SFHVURJKSA-N 4-hydroxy-7-[(1r)-1-hydroxy-2-[2-[3-[(2-methoxyethylamino)methyl]phenyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound COCCNCC1=CC=CC(CCNC[C@H](O)C=2C=3SC(=O)NC=3C(O)=CC=2)=C1 BGLYKONMLBFSGK-SFHVURJKSA-N 0.000 claims 1
- GVJALQHQZPOADA-DEOSSOPVSA-N 4-hydroxy-7-[(1r)-1-hydroxy-2-[2-[3-[(3-phenylpropylamino)methyl]phenyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound C([C@H](O)C=1C=2SC(=O)NC=2C(O)=CC=1)NCCC(C=1)=CC=CC=1CNCCCC1=CC=CC=C1 GVJALQHQZPOADA-DEOSSOPVSA-N 0.000 claims 1
- ZSMUEPQTTOFHSI-NRFANRHFSA-N 4-hydroxy-7-[(1r)-1-hydroxy-2-[2-[3-[(3-propan-2-yloxypropylamino)methyl]phenyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound CC(C)OCCCNCC1=CC=CC(CCNC[C@H](O)C=2C=3SC(=O)NC=3C(O)=CC=2)=C1 ZSMUEPQTTOFHSI-NRFANRHFSA-N 0.000 claims 1
- DEHYDNLJXVYLKL-NRFANRHFSA-N 4-hydroxy-7-[(1r)-1-hydroxy-2-[2-[3-[(3-propoxypropylamino)methyl]phenyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound CCCOCCCNCC1=CC=CC(CCNC[C@H](O)C=2C=3SC(=O)NC=3C(O)=CC=2)=C1 DEHYDNLJXVYLKL-NRFANRHFSA-N 0.000 claims 1
- IUPSVOSSHSTCNC-QHCPKHFHSA-N 4-hydroxy-7-[(1r)-1-hydroxy-2-[2-[3-[(3-pyridin-2-ylpropylamino)methyl]phenyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound C([C@H](O)C=1C=2SC(=O)NC=2C(O)=CC=1)NCCC(C=1)=CC=CC=1CNCCCC1=CC=CC=N1 IUPSVOSSHSTCNC-QHCPKHFHSA-N 0.000 claims 1
- QLAUZPPGGRVYJJ-SANMLTNESA-N 4-hydroxy-7-[(1r)-1-hydroxy-2-[2-[3-[(4-phenylpiperidin-1-yl)methyl]phenyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound C([C@H](O)C=1C=2SC(=O)NC=2C(O)=CC=1)NCCC(C=1)=CC=CC=1CN(CC1)CCC1C1=CC=CC=C1 QLAUZPPGGRVYJJ-SANMLTNESA-N 0.000 claims 1
- XJUWVHGTDKNBLN-IBGZPJMESA-N 4-hydroxy-7-[(1r)-1-hydroxy-2-[2-[3-[2-(2-methoxyethylamino)ethyl]phenyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound COCCNCCC1=CC=CC(CCNC[C@H](O)C=2C=3SC(=O)NC=3C(O)=CC=2)=C1 XJUWVHGTDKNBLN-IBGZPJMESA-N 0.000 claims 1
- GRHZLQJHXLNCBM-QFIPXVFZSA-N 4-hydroxy-7-[(1r)-1-hydroxy-2-[2-[3-[2-(pyridin-2-ylmethylamino)ethyl]phenyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound C([C@H](O)C=1C=2SC(=O)NC=2C(O)=CC=1)NCCC(C=1)=CC=CC=1CCNCC1=CC=CC=N1 GRHZLQJHXLNCBM-QFIPXVFZSA-N 0.000 claims 1
- PLQWTOQXQJAHBY-QHCPKHFHSA-N 4-hydroxy-7-[(1r)-1-hydroxy-2-[2-[3-[2-[(2-methoxyphenyl)methylamino]ethyl]phenyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound COC1=CC=CC=C1CNCCC1=CC=CC(CCNC[C@H](O)C=2C=3SC(=O)NC=3C(O)=CC=2)=C1 PLQWTOQXQJAHBY-QHCPKHFHSA-N 0.000 claims 1
- UMQKUTLZAVAIQA-DEOSSOPVSA-N 4-hydroxy-7-[(1r)-1-hydroxy-2-[2-[3-[2-[2-(2-methoxyphenyl)ethylamino]ethyl]phenyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound COC1=CC=CC=C1CCNCCC1=CC=CC(CCNC[C@H](O)C=2C=3SC(=O)NC=3C(O)=CC=2)=C1 UMQKUTLZAVAIQA-DEOSSOPVSA-N 0.000 claims 1
- VJPFFEYBQADOEZ-IBGZPJMESA-N 4-hydroxy-7-[(1r)-1-hydroxy-2-[2-[3-[[(2-methoxy-2-methylpropyl)amino]methyl]phenyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound COC(C)(C)CNCC1=CC=CC(CCNC[C@H](O)C=2C=3SC(=O)NC=3C(O)=CC=2)=C1 VJPFFEYBQADOEZ-IBGZPJMESA-N 0.000 claims 1
- PNTAECGMYJNBSW-QHCPKHFHSA-N 4-hydroxy-7-[(1r)-1-hydroxy-2-[2-[3-[[(2-methoxyphenyl)methyl-methylamino]methyl]phenyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound COC1=CC=CC=C1CN(C)CC1=CC=CC(CCNC[C@H](O)C=2C=3SC(=O)NC=3C(O)=CC=2)=C1 PNTAECGMYJNBSW-QHCPKHFHSA-N 0.000 claims 1
- PLKYHUCBRLEYME-QHCPKHFHSA-N 4-hydroxy-7-[(1r)-1-hydroxy-2-[2-[3-[[(3-methoxyphenyl)methylamino]methyl]phenyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound COC1=CC=CC(CNCC=2C=C(CCNC[C@H](O)C=3C=4SC(=O)NC=4C(O)=CC=3)C=CC=2)=C1 PLKYHUCBRLEYME-QHCPKHFHSA-N 0.000 claims 1
- BSOHYTBASIBPHA-QHCPKHFHSA-N 4-hydroxy-7-[(1r)-1-hydroxy-2-[2-[3-[[(4-methoxyphenyl)methylamino]methyl]phenyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound C1=CC(OC)=CC=C1CNCC1=CC=CC(CCNC[C@H](O)C=2C=3SC(=O)NC=3C(O)=CC=2)=C1 BSOHYTBASIBPHA-QHCPKHFHSA-N 0.000 claims 1
- XPJHOPNYYGFTFU-QHCPKHFHSA-N 4-hydroxy-7-[(1r)-1-hydroxy-2-[2-[3-[[2-(2-hydroxyphenyl)ethylamino]methyl]phenyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound C([C@H](O)C=1C=2SC(=O)NC=2C(O)=CC=1)NCCC(C=1)=CC=CC=1CNCCC1=CC=CC=C1O XPJHOPNYYGFTFU-QHCPKHFHSA-N 0.000 claims 1
- PIQKJCGMILEGLT-QHCPKHFHSA-N 4-hydroxy-7-[(1r)-1-hydroxy-2-[2-[3-[[2-(2-methoxyphenyl)ethylamino]methyl]phenyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound COC1=CC=CC=C1CCNCC1=CC=CC(CCNC[C@H](O)C=2C=3SC(=O)NC=3C(O)=CC=2)=C1 PIQKJCGMILEGLT-QHCPKHFHSA-N 0.000 claims 1
- PVUXNNHCSQZNFM-QFIPXVFZSA-N 4-hydroxy-7-[(1r)-1-hydroxy-2-[2-[3-[[3-(2-methylpropoxy)propylamino]methyl]phenyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound CC(C)COCCCNCC1=CC=CC(CCNC[C@H](O)C=2C=3SC(=O)NC=3C(O)=CC=2)=C1 PVUXNNHCSQZNFM-QFIPXVFZSA-N 0.000 claims 1
- CISJUOJARBBEPR-LIRRHRJNSA-N 4-hydroxy-7-[(1r)-1-hydroxy-2-[2-[3-[[[(2s)-1-methoxypropan-2-yl]amino]methyl]phenyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound COC[C@H](C)NCC1=CC=CC(CCNC[C@H](O)C=2C=3SC(=O)NC=3C(O)=CC=2)=C1 CISJUOJARBBEPR-LIRRHRJNSA-N 0.000 claims 1
- YWYCMZFLOQQZRC-DEOSSOPVSA-N 4-hydroxy-7-[(1r)-1-hydroxy-2-[2-[3-[[methyl(2-phenylethyl)amino]methyl]phenyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound C=1C=CC(CCNC[C@H](O)C=2C=3SC(=O)NC=3C(O)=CC=2)=CC=1CN(C)CCC1=CC=CC=C1 YWYCMZFLOQQZRC-DEOSSOPVSA-N 0.000 claims 1
- DNNQRUUXWVHSRB-NDEPHWFRSA-N 4-hydroxy-7-[(1r)-1-hydroxy-2-[2-[4-[2-[(2-pyridin-2-ylethylamino)methyl]phenyl]phenyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound C([C@H](O)C=1C=2SC(=O)NC=2C(O)=CC=1)NCCC(C=C1)=CC=C1C1=CC=CC=C1CNCCC1=CC=CC=N1 DNNQRUUXWVHSRB-NDEPHWFRSA-N 0.000 claims 1
- XNZJTBRCBWPOTP-PBBNMVCDSA-N 4-hydroxy-7-[(1r)-1-hydroxy-2-[2-[4-[2-[[[(1r)-1-phenylethyl]amino]methyl]phenyl]phenyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound C1([C@H](NCC=2C(=CC=CC=2)C=2C=CC(CCNC[C@H](O)C=3C=4SC(=O)NC=4C(O)=CC=3)=CC=2)C)=CC=CC=C1 XNZJTBRCBWPOTP-PBBNMVCDSA-N 0.000 claims 1
- NYWJZLOBZHVZMI-QFIPXVFZSA-N 4-hydroxy-7-[(1r)-1-hydroxy-2-[2-[4-[[(2-methoxyphenyl)methylamino]methyl]phenyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound COC1=CC=CC=C1CNCC(C=C1)=CC=C1CCNC[C@H](O)C1=CC=C(O)C2=C1SC(=O)N2 NYWJZLOBZHVZMI-QFIPXVFZSA-N 0.000 claims 1
- YOCAICFOALLBEO-QHCPKHFHSA-N 4-hydroxy-7-[(1r)-1-hydroxy-2-[2-[4-[[2-(2-methoxyphenyl)ethylamino]methyl]phenyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound COC1=CC=CC=C1CCNCC(C=C1)=CC=C1CCNC[C@H](O)C1=CC=C(O)C2=C1SC(=O)N2 YOCAICFOALLBEO-QHCPKHFHSA-N 0.000 claims 1
- HRIMLSKWGJERPD-VWLOTQADSA-N 4-hydroxy-7-[(1r)-1-hydroxy-2-[2-[4-[[2-(7-methyl-1h-indol-3-yl)ethylamino]methyl]phenyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound C1([C@@H](O)CNCCC2=CC=C(C=C2)CNCCC=2C=3C=CC=C(C=3NC=2)C)=CC=C(O)C2=C1SC(=O)N2 HRIMLSKWGJERPD-VWLOTQADSA-N 0.000 claims 1
- KKHJTNLHISNRCZ-UHFFFAOYSA-N 4-hydroxy-7-[1-hydroxy-2-[2-[3-[[(2-hydroxyphenyl)methylamino]methyl]phenyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound C=1C=C(O)C=2NC(=O)SC=2C=1C(O)CNCCC(C=1)=CC=CC=1CNCC1=CC=CC=C1O KKHJTNLHISNRCZ-UHFFFAOYSA-N 0.000 claims 1
- KIXKMKREZOCTDI-UHFFFAOYSA-N 4-hydroxy-7-[1-hydroxy-2-[2-[4-[2-[(3-propan-2-yloxypropylamino)methyl]phenyl]phenyl]ethylamino]ethyl]-3h-1,3-benzothiazol-2-one Chemical compound CC(C)OCCCNCC1=CC=CC=C1C(C=C1)=CC=C1CCNCC(O)C1=CC=C(O)C2=C1SC(=O)N2 KIXKMKREZOCTDI-UHFFFAOYSA-N 0.000 claims 1
- WONPWDMMWFWEFC-ODOSRFNGSA-N 7-[(1r)-2-[1-[3-[[2-(2,6-dichlorophenyl)ethylamino]methyl]phenyl]propan-2-ylamino]-1-hydroxyethyl]-4-hydroxy-3h-1,3-benzothiazol-2-one Chemical compound C([C@H](O)C=1C=2SC(=O)NC=2C(O)=CC=1)NC(C)CC(C=1)=CC=CC=1CNCCC1=C(Cl)C=CC=C1Cl WONPWDMMWFWEFC-ODOSRFNGSA-N 0.000 claims 1
- XXPNWYXHQVWMTB-QHCPKHFHSA-N 7-[(1r)-2-[2-[2-[[2-(2-fluorophenyl)ethylamino]methyl]phenyl]ethylamino]-1-hydroxyethyl]-4-hydroxy-3h-1,3-benzothiazol-2-one Chemical compound C([C@H](O)C=1C=2SC(=O)NC=2C(O)=CC=1)NCCC1=CC=CC=C1CNCCC1=CC=CC=C1F XXPNWYXHQVWMTB-QHCPKHFHSA-N 0.000 claims 1
- PURQGWJEQYPHEZ-NRFANRHFSA-N 7-[(1r)-2-[2-[3-(azepan-1-ylmethyl)phenyl]ethylamino]-1-hydroxyethyl]-4-hydroxy-3h-1,3-benzothiazol-2-one Chemical compound C([C@H](O)C=1C=2SC(=O)NC=2C(O)=CC=1)NCCC(C=1)=CC=CC=1CN1CCCCCC1 PURQGWJEQYPHEZ-NRFANRHFSA-N 0.000 claims 1
- XLPXMNLCZGSYPS-LJAQVGFWSA-N 7-[(1r)-2-[2-[3-[(2,2-diphenylethylamino)methyl]phenyl]ethylamino]-1-hydroxyethyl]-4-hydroxy-3h-1,3-benzothiazol-2-one Chemical compound C([C@H](O)C=1C=2SC(=O)NC=2C(O)=CC=1)NCCC(C=1)=CC=CC=1CNCC(C=1C=CC=CC=1)C1=CC=CC=C1 XLPXMNLCZGSYPS-LJAQVGFWSA-N 0.000 claims 1
- GLCDQTGVYSDVBW-QFIPXVFZSA-N 7-[(1r)-2-[2-[3-[2-(azepan-1-yl)ethyl]phenyl]ethylamino]-1-hydroxyethyl]-4-hydroxy-3h-1,3-benzothiazol-2-one Chemical compound C([C@H](O)C=1C=2SC(=O)NC=2C(O)=CC=1)NCCC(C=1)=CC=CC=1CCN1CCCCCC1 GLCDQTGVYSDVBW-QFIPXVFZSA-N 0.000 claims 1
- RCUOEZMFFUESSQ-QFIPXVFZSA-N 7-[(1r)-2-[2-[3-[2-(cyclohexylamino)ethyl]phenyl]ethylamino]-1-hydroxyethyl]-4-hydroxy-3h-1,3-benzothiazol-2-one Chemical compound C([C@H](O)C=1C=2SC(=O)NC=2C(O)=CC=1)NCCC(C=1)=CC=CC=1CCNC1CCCCC1 RCUOEZMFFUESSQ-QFIPXVFZSA-N 0.000 claims 1
- UZNMXZFHPXULMI-DEOSSOPVSA-N 7-[(1r)-2-[2-[3-[2-[2-(2-fluorophenyl)ethylamino]ethyl]phenyl]ethylamino]-1-hydroxyethyl]-4-hydroxy-3h-1,3-benzothiazol-2-one Chemical compound C([C@H](O)C=1C=2SC(=O)NC=2C(O)=CC=1)NCCC(C=1)=CC=CC=1CCNCCC1=CC=CC=C1F UZNMXZFHPXULMI-DEOSSOPVSA-N 0.000 claims 1
- HXHAEKRMZXMRER-NDEPHWFRSA-N 7-[(1r)-2-[2-[3-[3-[(benzylamino)methyl]phenyl]phenyl]ethylamino]-1-hydroxyethyl]-4-hydroxy-3h-1,3-benzothiazol-2-one Chemical compound C([C@H](O)C=1C=2SC(=O)NC=2C(O)=CC=1)NCCC(C=1)=CC=CC=1C(C=1)=CC=CC=1CNCC1=CC=CC=C1 HXHAEKRMZXMRER-NDEPHWFRSA-N 0.000 claims 1
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- VKISKXWEKUKQJG-QHCPKHFHSA-N 7-[(1r)-2-[2-[3-[[(2-ethoxyphenyl)methylamino]methyl]phenyl]ethylamino]-1-hydroxyethyl]-4-hydroxy-3h-1,3-benzothiazol-2-one Chemical compound CCOC1=CC=CC=C1CNCC1=CC=CC(CCNC[C@H](O)C=2C=3SC(=O)NC=3C(O)=CC=2)=C1 VKISKXWEKUKQJG-QHCPKHFHSA-N 0.000 claims 1
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| RU2602814C2 (ru) | 2009-09-25 | 2016-11-20 | Оризон Дженомикс С.А. | Лизинспецифические ингибиторы деметилазы-1 и их применение |
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| EP2578570A1 (en) | 2011-10-07 | 2013-04-10 | Almirall, S.A. | Novel process for preparing 5-(2-{[6-(2,2-difluoro-2-phenylethoxy)hexyl]amino}-1(r)-hydroxyethyl)-8-hydroxyquinolin-2(1h)-one via novel intermediates of synthesis. |
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| EP2641900A1 (en) | 2012-03-20 | 2013-09-25 | Almirall, S.A. | Novel polymorphic Crystal forms of 5-(2-{[6-(2,2-difluoro-2-phenylethoxy) hexyl]amino}-1-(R)-hydroxyethyl)-8-hydroxyquinolin-2(1h)-one, heminapadisylate as agonist of the ß2 adrenergic receptor. |
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Family Cites Families (74)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2653977A (en) * | 1953-09-29 | Chxnx | ||
| US3775477A (en) * | 1971-03-10 | 1973-11-27 | Sterling Drug Inc | N,n'-bis(2-aryl-2-(hydroxy or oxo)-ethyl)-bridged-bis-carboxamides |
| US4460581A (en) * | 1982-10-12 | 1984-07-17 | Boehringer Ingelheim Kg | (1-Hydroxy-2-amino-alkyl)-substituted benzoxazinones and benzoxazolinones |
| EP0162576B1 (en) | 1984-04-17 | 1989-07-26 | Glaxo Group Limited | Ethanolamine compounds |
| US4554284A (en) | 1984-09-12 | 1985-11-19 | Smithkline Beckman Corporation | 7-(2-Aminoethyl)-1,3-benzthia- or oxa-zol-2(3H)-ones |
| US4554287A (en) | 1984-09-12 | 1985-11-19 | Smithkline Beckman Corporation | Antihypertensive 7-[2-(dialkylamino)ethyl]-4-hydroxy-1,3-benzimidazol-2-ones |
| GB8525483D0 (en) | 1985-10-16 | 1985-11-20 | Glaxo Group Ltd | Chemical compounds |
| GB8718938D0 (en) | 1987-08-11 | 1987-09-16 | Glaxo Group Ltd | Chemical compounds |
| NZ235605A (en) | 1989-10-10 | 1992-12-23 | Glaxo Group Ltd | (r)-(-)-4-hydroxy-alpha 1 -(((6-(4-phenylbutoxy)hexyl)amino)methyl)-1,3-benzenedimethanol and pharmaceutical compositions |
| GB9210632D0 (en) | 1992-05-19 | 1992-07-01 | Fisons Plc | Compounds |
| GB9211172D0 (en) | 1992-05-27 | 1992-07-08 | Fisons Plc | Compounds |
| US5648370A (en) * | 1990-11-20 | 1997-07-15 | Astra Pharmaceuticals Limited | 7-(2-aminoethyl) benzothiazolones |
| IE914003A1 (en) | 1990-11-20 | 1992-05-20 | Astra Pharma Prod | Biologically Active Amines |
| TW356468B (en) | 1995-09-15 | 1999-04-21 | Astra Pharma Prod | Benzothiazolone compounds useful as beta2-adrenoreceptor and dopamine DA2 receptor agonists process for preparing same and pharmaceutical compositions containing same |
| GB9526511D0 (en) | 1995-12-23 | 1996-02-28 | Astra Pharma Prod | Pharmaceutically active compounds |
| DE69709647T2 (de) | 1996-05-20 | 2002-11-07 | Dupont Pharmaceuticals Research Laboratories, Inc. | Cyclischer diarylalkyl diaminederivate als antogoniste von chemokinerezeptoren |
| SE9700706D0 (sv) | 1997-02-27 | 1997-02-27 | Astra Pharma Prod | Process for the preparation of benzothiazoline compounds |
| SE9701304D0 (sv) | 1997-04-09 | 1997-04-09 | Astra Pharma Prod | Compounds |
| JP2002509119A (ja) | 1998-01-13 | 2002-03-26 | アストラゼネカ ユーケイ リミテッド | ドーパミン（Ｄ２）レセプターアゴニスト活性を有する化合物およびβ２−アドレナリンレセプターアゴニスト活性を有する化合物（Ｂ）を含有する薬学的組成物 |
| US6541669B1 (en) | 1998-06-08 | 2003-04-01 | Theravance, Inc. | β2-adrenergic receptor agonists |
| GB9913083D0 (en) | 1999-06-04 | 1999-08-04 | Novartis Ag | Organic compounds |
| US6683115B2 (en) * | 1999-06-02 | 2004-01-27 | Theravance, Inc. | β2-adrenergic receptor agonists |
| SE9902938D0 (sv) | 1999-08-18 | 1999-08-18 | Astra Pharma Prod | Pharmaceutical compositions |
| SE9902935D0 (sv) | 1999-08-18 | 1999-08-18 | Astra Pharma Prod | Pharmaceutical compositions |
| SE9902937D0 (sv) | 1999-08-18 | 1999-08-18 | Astra Pharma Prod | Pharmaceutical compositions |
| SE9902936D0 (sv) | 1999-08-18 | 1999-08-18 | Astra Pharma Prod | Pharmaceutical compositions |
| OA11558A (en) | 1999-12-08 | 2004-06-03 | Advanced Medicine Inc | Beta 2-adrenergic receptor agonists. |
| US6506901B2 (en) | 2000-07-17 | 2003-01-14 | Wyeth | Substituted 2-(S)-hydroxy-3-(piperidin-4-yl-methylamino)-propyl ethers and substituted 2-aryl-2-(R)-hydroxy-1-(piperidin-4-yl-methyl)-ethylamine β-3 adrenergic receptor agonists |
| JP4143413B2 (ja) | 2001-03-22 | 2008-09-03 | グラクソ グループ リミテッド | β２−アドレナリン受容体アゴニストとしてのホルムアニリド誘導体 |
| ES2438985T3 (es) | 2001-09-14 | 2014-01-21 | Glaxo Group Limited | Formulación de inhalación que comprende derivados de fenetanolamina para el tratamiento de enfermedades respiratorias |
| US20030229058A1 (en) * | 2001-11-13 | 2003-12-11 | Moran Edmund J. | Aryl aniline beta2 adrenergic receptor agonists |
| GB0217225D0 (en) | 2002-07-25 | 2002-09-04 | Glaxo Group Ltd | Medicinal compounds |
| PE20050130A1 (es) * | 2002-08-09 | 2005-03-29 | Novartis Ag | Compuestos organicos |
| GB0225540D0 (en) | 2002-11-01 | 2002-12-11 | Glaxo Group Ltd | Medicinal compounds |
| PE20040950A1 (es) | 2003-02-14 | 2005-01-01 | Theravance Inc | DERIVADOS DE BIFENILO COMO AGONISTAS DE LOS RECEPTORES ADRENERGICOS ß2 Y COMO ANTAGONISTAS DE LOS RECEPTORES MUSCARINICOS |
| GB0303396D0 (en) | 2003-02-14 | 2003-03-19 | Glaxo Group Ltd | Medicinal compounds |
| JP4767842B2 (ja) | 2003-04-01 | 2011-09-07 | セラヴァンス， インコーポレーテッド | β２アドレナリン作用性レセプターアゴニスト活性およびムスカリン性レセプターアンタゴニスト活性を有するジアリールメチル化合物および関連化合物 |
| TW200526547A (en) * | 2003-09-22 | 2005-08-16 | Theravance Inc | Amino-substituted ethylamino β2 adrenergic receptor agonists |
| GB0324654D0 (en) | 2003-10-22 | 2003-11-26 | Glaxo Group Ltd | Medicinal compounds |
| GB0324886D0 (en) | 2003-10-24 | 2003-11-26 | Glaxo Group Ltd | Medicinal compounds |
| JP2005187357A (ja) | 2003-12-25 | 2005-07-14 | Nippon Suisan Kaisha Ltd | 選択的なβ２受容体アゴニスト活性を有するベンゾチアゾロン誘導体の製造方法 |
| TW200531692A (en) * | 2004-01-12 | 2005-10-01 | Theravance Inc | Aryl aniline derivatives as β2 adrenergic receptor agonists |
| GB0402797D0 (en) | 2004-02-09 | 2004-03-10 | Novartis Ag | Organic compounds |
| WO2005092861A1 (en) | 2004-03-11 | 2005-10-06 | Pfizer Limited | Quinolinone derivatives pharmaceutical compositions containing them and their use |
| EP1577306A1 (de) | 2004-03-17 | 2005-09-21 | Boehringer Ingelheim Pharma GmbH & Co.KG | Neue Benzoxazinonderivate als langwirksame Betamimetika zur Behandlung von Atemwegserkrankungen |
| WO2005092841A1 (en) | 2004-03-23 | 2005-10-06 | Pfizer Limited | Compounds having beta-agonist activity |
| EP1595873A1 (de) | 2004-05-13 | 2005-11-16 | Boehringer Ingelheim Pharma GmbH & Co.KG | Substituierte Cycloalkylderivate zur Behandlung von Atemswegerkrankungen |
| CA2565243A1 (en) | 2004-05-13 | 2005-11-24 | Boehringer Ingelheim International Gmbh | Hydroxy-substituted benzo-condensed heterocycles for use as beta agonists in the treatment of respiratory diseases |
| DE102004024453A1 (de) | 2004-05-14 | 2006-01-05 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue langwirksame Bronchodilatoren zur Behandlung von Atemwegserkrankungen |
| BRPI0511695A (pt) | 2004-06-03 | 2008-01-08 | Theravance Inc | agonistas de receptor (beta)2 adrenérgico diamina |
| WO2006014704A1 (en) | 2004-07-21 | 2006-02-09 | Theravance, Inc. | DIARYL ETHER β2 ADRENERGIC RECEPTOR AGONISTS |
| JP2008510014A (ja) | 2004-08-16 | 2008-04-03 | セラヴァンス， インコーポレーテッド | β２アドレナリン作用性レセプターアゴニスト活性およびムスカリン性レセプターアンタゴニスト活性を有する化合物 |
| US7569586B2 (en) | 2004-08-16 | 2009-08-04 | Theravance, Inc. | Compounds having β2 adrenergic receptor agonist and muscarinic receptor antagonist activity |
| EP1786762A2 (en) | 2004-09-10 | 2007-05-23 | Theravance, Inc. | Amidine substituted aryl aniline compounds |
| GB0426164D0 (en) | 2004-11-29 | 2004-12-29 | Novartis Ag | Organic compounds |
| AU2006205933A1 (en) | 2005-01-11 | 2006-07-20 | Glaxo Group Limited | Cinnamate salts of a beta-2 adrenergic agonist |
| GB0511066D0 (en) | 2005-05-31 | 2005-07-06 | Novartis Ag | Organic compounds |
| NZ585580A (en) | 2005-07-18 | 2011-08-26 | Pfizer Ltd | Process for the preparation of sulfonamide derivatives |
| TW200738658A (en) * | 2005-08-09 | 2007-10-16 | Astrazeneca Ab | Novel compounds |
| TW200740781A (en) | 2005-08-29 | 2007-11-01 | Astrazeneca Ab | Novel compounds |
| TW200738659A (en) * | 2005-08-29 | 2007-10-16 | Astrazeneca Ab | Novel compounds |
| US20090029958A1 (en) * | 2006-03-08 | 2009-01-29 | Lilian Alcaraz | Phenethanolamine derivatives as beta2 adrenoreceptor agonists |
| TW200745084A (en) | 2006-03-08 | 2007-12-16 | Astrazeneca Ab | Novel compounds |
| TW200745067A (en) | 2006-03-14 | 2007-12-16 | Astrazeneca Ab | Novel compounds |
| WO2008041914A1 (en) | 2006-10-06 | 2008-04-10 | Astrazeneca Ab | 5-(2-AMINO-L-HYDROXYETHYL)-8-HYDROXY-2-OXOQUINOLINE DERIVATIVES AND OTHER COMPOUNDS AS β2 -ADRENERGIC AGONISTS |
| TW200833670A (en) * | 2006-12-20 | 2008-08-16 | Astrazeneca Ab | Novel compounds 569 |
| CA2672792A1 (en) | 2006-12-20 | 2008-06-26 | Astrazeneca Ab | Amine derivatives and their use in beta-2-adrenoreceptor mediated diseases |
| GB0702459D0 (en) | 2007-02-08 | 2007-03-21 | Astrazeneca Ab | Salts 669 |
| GB0702458D0 (en) * | 2007-02-08 | 2007-03-21 | Astrazeneca Ab | Salts 668 |
| GB0702456D0 (en) * | 2007-02-08 | 2007-03-21 | Astrazeneca Ab | New combination |
| GB0702457D0 (en) | 2007-02-08 | 2007-03-21 | Astrazeneca Ab | New combination 666 |
| GB0704000D0 (en) | 2007-03-01 | 2007-04-11 | Astrazeneca Ab | Salts 670 |
| GB0703999D0 (en) | 2007-03-01 | 2007-04-11 | Astrazeneca Ab | New combination 667 |
| WO2009037503A2 (en) | 2007-09-18 | 2009-03-26 | Astrazeneca Ab | New combination - 012 for the treatment of respiratory diseases |
-
2007
- 2007-03-02 TW TW096107171A patent/TW200745067A/zh unknown
- 2007-03-12 CA CA002644014A patent/CA2644014A1/en not_active Abandoned
- 2007-03-12 WO PCT/SE2007/000233 patent/WO2007106016A1/en not_active Ceased
- 2007-03-12 US US12/282,634 patent/US7951954B2/en not_active Expired - Fee Related
- 2007-03-12 BR BRPI0709589-9A patent/BRPI0709589A2/pt not_active IP Right Cessation
- 2007-03-12 AU AU2007225471A patent/AU2007225471A1/en not_active Abandoned
- 2007-03-12 EP EP07716051A patent/EP1996566A1/en not_active Withdrawn
- 2007-03-12 RU RU2008136553/04A patent/RU2008136553A/ru not_active Application Discontinuation
- 2007-03-12 KR KR1020087024962A patent/KR20080103104A/ko not_active Withdrawn
- 2007-03-12 JP JP2009500323A patent/JP2009530272A/ja not_active Withdrawn
- 2007-03-14 UY UY30206A patent/UY30206A1/es unknown
- 2007-03-14 AR ARP070101043A patent/AR059842A1/es unknown
-
2008
- 2008-08-18 IL IL193530A patent/IL193530A0/en unknown
- 2008-09-15 EC EC2008008741A patent/ECSP088741A/es unknown
- 2008-10-13 NO NO20084278A patent/NO20084278L/no not_active Application Discontinuation
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