JP2002509908A5 - - Google Patents
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- JP2002509908A5 JP2002509908A5 JP2000541135A JP2000541135A JP2002509908A5 JP 2002509908 A5 JP2002509908 A5 JP 2002509908A5 JP 2000541135 A JP2000541135 A JP 2000541135A JP 2000541135 A JP2000541135 A JP 2000541135A JP 2002509908 A5 JP2002509908 A5 JP 2002509908A5
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- Prior art keywords
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- blooded animal
- Prior art date
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- 150000001875 compounds Chemical class 0.000 description 149
- 239000000203 mixture Substances 0.000 description 148
- 238000000034 method Methods 0.000 description 86
- -1 3-azabicyclo [3.2.2] nonan-3-yl Chemical group 0.000 description 70
- 239000001257 hydrogen Substances 0.000 description 69
- 229910052739 hydrogen Inorganic materials 0.000 description 69
- 229940037201 oris Drugs 0.000 description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 35
- 125000006413 ring segment Chemical group 0.000 description 35
- 150000002431 hydrogen Chemical class 0.000 description 34
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 32
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
- 229910052757 nitrogen Inorganic materials 0.000 description 30
- 125000003545 alkoxy group Chemical group 0.000 description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 28
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 23
- 150000003839 salts Chemical class 0.000 description 23
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 22
- 239000012453 solvate Substances 0.000 description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 21
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 20
- 229910052760 oxygen Inorganic materials 0.000 description 18
- 229910052717 sulfur Inorganic materials 0.000 description 18
- 125000001424 substituent group Chemical group 0.000 description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 description 15
- 229910052799 carbon Inorganic materials 0.000 description 13
- 125000004423 acyloxy group Chemical group 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- 239000001301 oxygen Substances 0.000 description 10
- 239000011593 sulfur Substances 0.000 description 10
- 125000002252 acyl group Chemical group 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 6
- 125000003003 spiro group Chemical group 0.000 description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
- 0 CCCNCC* Chemical compound CCCNCC* 0.000 description 5
- 125000005157 alkyl carboxy group Chemical group 0.000 description 5
- 125000002837 carbocyclic group Chemical group 0.000 description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- 206010010904 Convulsion Diseases 0.000 description 2
- 108090000862 Ion Channels Proteins 0.000 description 2
- 102000004310 Ion Channels Human genes 0.000 description 2
- 206010061533 Myotonia Diseases 0.000 description 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 2
- 230000036592 analgesia Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 230000001568 sexual effect Effects 0.000 description 2
- UFONXKIZORASRI-OALUTQOASA-N 1-[(1s,2s)-2-(3-cyclohexylpropoxy)cyclohexyl]pyrrolidin-3-one Chemical compound C1C(=O)CCN1[C@@H]1[C@@H](OCCCC2CCCCC2)CCCC1 UFONXKIZORASRI-OALUTQOASA-N 0.000 description 1
- WGXAQCYMUFQJSA-IRXDYDNUSA-N 1-[(1s,2s)-2-[(2,6-dichlorophenyl)methoxy]cyclohexyl]pyrrolidin-3-one Chemical compound ClC1=CC=CC(Cl)=C1CO[C@@H]1[C@@H](N2CC(=O)CC2)CCCC1 WGXAQCYMUFQJSA-IRXDYDNUSA-N 0.000 description 1
- AHTASIQFBOOLDV-RHGDZWTLSA-N 1-[(1s,2s)-2-[2-(2,6-dichlorophenyl)ethoxy]cyclohexyl]pyrrolidin-3-ol Chemical compound C1C(O)CCN1[C@@H]1[C@@H](OCCC=2C(=CC=CC=2Cl)Cl)CCCC1 AHTASIQFBOOLDV-RHGDZWTLSA-N 0.000 description 1
- KRCDDYNOSQYZRA-ROUUACIJSA-N 1-[(1s,2s)-2-[2-(2,6-dichlorophenyl)ethoxy]cyclohexyl]pyrrolidin-3-one Chemical compound ClC1=CC=CC(Cl)=C1CCO[C@@H]1[C@@H](N2CC(=O)CC2)CCCC1 KRCDDYNOSQYZRA-ROUUACIJSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- HDTKTGATXZRRTG-IRXDYDNUSA-N 3-[(1s,2s)-2-[2-(2,6-dichlorophenyl)ethoxy]cyclohexyl]-1,3-thiazolidine Chemical compound ClC1=CC=CC(Cl)=C1CCO[C@@H]1[C@@H](N2CSCC2)CCCC1 HDTKTGATXZRRTG-IRXDYDNUSA-N 0.000 description 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
- XENQVRODCYBGEK-IRXDYDNUSA-N 4-[(1s,2s)-2-[(2,6-dichlorophenyl)methoxy]cyclohexyl]morpholine Chemical compound ClC1=CC=CC(Cl)=C1CO[C@@H]1[C@@H](N2CCOCC2)CCCC1 XENQVRODCYBGEK-IRXDYDNUSA-N 0.000 description 1
- XYNMOULGJNGXPD-ROUUACIJSA-N 4-[(1s,2s)-2-[2-(3,4-dichlorophenyl)ethoxy]cyclohexyl]morpholine Chemical compound C1=C(Cl)C(Cl)=CC=C1CCO[C@@H]1[C@@H](N2CCOCC2)CCCC1 XYNMOULGJNGXPD-ROUUACIJSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- 201000004384 Alopecia Diseases 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 206010003130 Arrhythmia supraventricular Diseases 0.000 description 1
- 206010003658 Atrial Fibrillation Diseases 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- 201000006474 Brain Ischemia Diseases 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 206010008120 Cerebral ischaemia Diseases 0.000 description 1
- 208000029323 Congenital myotonia Diseases 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 201000003883 Cystic fibrosis Diseases 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- 208000018522 Gastrointestinal disease Diseases 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 206010020844 Hyperthermia malignant Diseases 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 208000018717 Malignant hyperthermia of anesthesia Diseases 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 208000021642 Muscular disease Diseases 0.000 description 1
- 201000009623 Myopathy Diseases 0.000 description 1
- 208000010316 Myotonia congenita Diseases 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- 206010052779 Transplant rejections Diseases 0.000 description 1
- 206010046543 Urinary incontinence Diseases 0.000 description 1
- 206010047281 Ventricular arrhythmia Diseases 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 231100000360 alopecia Toxicity 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000010322 bone marrow transplantation Methods 0.000 description 1
- 208000015114 central nervous system disease Diseases 0.000 description 1
- 206010008118 cerebral infarction Diseases 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 208000030533 eye disease Diseases 0.000 description 1
- 125000004634 hexahydroazepinyl group Chemical group N1(CCCCCC1)* 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 208000002551 irritable bowel syndrome Diseases 0.000 description 1
- 208000004731 long QT syndrome Diseases 0.000 description 1
- 201000007004 malignant hyperthermia Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 206010028417 myasthenia gravis Diseases 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 208000029308 periodic paralysis Diseases 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 208000003663 ventricular fibrillation Diseases 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8034798P | 1998-04-01 | 1998-04-01 | |
| US60/080,347 | 1998-04-01 | ||
| US11895499P | 1999-02-05 | 1999-02-05 | |
| US60/118,954 | 1999-02-05 | ||
| PCT/CA1999/000280 WO1999050225A1 (en) | 1998-04-01 | 1999-04-01 | Aminocyclohexyl ether compounds and uses thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006129715A Division JP2006306878A (ja) | 1998-04-01 | 2006-05-08 | アミノシクロヘキシルエーテル化合物およびその用途 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002509908A JP2002509908A (ja) | 2002-04-02 |
| JP2002509908A5 true JP2002509908A5 (https=) | 2006-06-01 |
| JP4334766B2 JP4334766B2 (ja) | 2009-09-30 |
Family
ID=26763394
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000541135A Expired - Lifetime JP4334766B2 (ja) | 1998-04-01 | 1999-04-01 | アミノシクロヘキシルエーテル化合物およびその用途 |
| JP2006129715A Pending JP2006306878A (ja) | 1998-04-01 | 2006-05-08 | アミノシクロヘキシルエーテル化合物およびその用途 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006129715A Pending JP2006306878A (ja) | 1998-04-01 | 2006-05-08 | アミノシクロヘキシルエーテル化合物およびその用途 |
Country Status (32)
| Country | Link |
|---|---|
| US (5) | US7101877B2 (https=) |
| EP (2) | EP1087934B1 (https=) |
| JP (2) | JP4334766B2 (https=) |
| KR (1) | KR100631299B1 (https=) |
| CN (1) | CN1217918C (https=) |
| AT (1) | ATE260240T1 (https=) |
| AU (1) | AU751772C (https=) |
| BE (1) | BE2011C002I2 (https=) |
| BR (1) | BRPI9909282B8 (https=) |
| CA (1) | CA2326777C (https=) |
| CY (1) | CY2010018I2 (https=) |
| CZ (1) | CZ302147B6 (https=) |
| DE (2) | DE69915063T2 (https=) |
| DK (1) | DK1087934T3 (https=) |
| EE (1) | EE04548B1 (https=) |
| ES (1) | ES2217742T3 (https=) |
| FR (1) | FR10C0057I2 (https=) |
| HU (1) | HU229993B1 (https=) |
| ID (1) | ID27178A (https=) |
| IL (1) | IL138719A0 (https=) |
| IS (1) | IS2648B (https=) |
| LU (1) | LU91761I2 (https=) |
| MX (1) | MXPA00009593A (https=) |
| NO (2) | NO321130B1 (https=) |
| NZ (1) | NZ507169A (https=) |
| PL (1) | PL197293B1 (https=) |
| PT (1) | PT1087934E (https=) |
| RO (1) | RO121028B1 (https=) |
| RU (1) | RU2252933C2 (https=) |
| SK (1) | SK285908B6 (https=) |
| TR (1) | TR200002796T2 (https=) |
| WO (1) | WO1999050225A1 (https=) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK1087934T3 (da) | 1998-04-01 | 2004-06-28 | Cardiome Pharma Corp | Aminocyclohexyletherforbindelser og anvendelser deraf |
| US7507545B2 (en) | 1999-03-31 | 2009-03-24 | Cardiome Pharma Corp. | Ion channel modulating activity method |
| DE10049481A1 (de) | 2000-09-29 | 2002-05-02 | Gruenenthal Gmbh | Substituierte C-Cyclohexylmethylamin-Derivate |
| US7057053B2 (en) | 2000-10-06 | 2006-06-06 | Cardiome Pharma Corp. | Ion channel modulating compounds and uses thereof |
| US7524879B2 (en) * | 2000-10-06 | 2009-04-28 | Cardiome Pharma Corp. | Ion channel modulating compounds and uses thereof |
| DE10213051B4 (de) * | 2002-03-23 | 2013-03-07 | Grünenthal GmbH | Substituierte 4-Aminocyclohexanole |
| WO2003105756A2 (en) * | 2002-06-14 | 2003-12-24 | Johnson Matthey Pharmaceutical Materials, Inc. | Stereoselective synthesis of 1,2-disubstituted cycloalkyls |
| CA2524323C (en) * | 2003-05-02 | 2012-05-15 | Cardiome Pharma Corp. | Aminocyclohexyl ether compounds and uses thereof |
| US20080063707A1 (en) * | 2003-05-02 | 2008-03-13 | Cardiome Pharma Corp. | Controlled release tablet formulations for the prevention of arrhythmias |
| CN100441568C (zh) * | 2003-05-02 | 2008-12-10 | 卡迪欧梅制药公司 | 氨基环己基醚化合物和它们的用途 |
| US7345086B2 (en) | 2003-05-02 | 2008-03-18 | Cardiome Pharma Corp. | Uses of ion channel modulating compounds |
| US20090041841A1 (en) * | 2003-05-02 | 2009-02-12 | Cardiome Pharma Corp. | Controlled release tablet formulations for the prevention of arrhythmias |
| WO2005016242A2 (en) * | 2003-06-04 | 2005-02-24 | Cardiome Pharma Corp. | Synthetic process for trans-aminocyclohexyl ether compounds |
| WO2005018635A2 (en) | 2003-08-07 | 2005-03-03 | Cardiome Pharma Corp. | Ion channel modulating activity i |
| US7345087B2 (en) | 2003-10-31 | 2008-03-18 | Cardiome Pharma Corp. | Aminocyclohexyl ether compounds and uses thereof |
| MXPA06011420A (es) * | 2004-04-01 | 2007-04-20 | Cardiome Pharma Corp | Compuestos pegilados de modulacion de canal de iones. |
| WO2005097203A2 (en) * | 2004-04-01 | 2005-10-20 | Cardiome Pharma Corp. | Serum protein conjugates of ion channel modulating compounds and uses thereof |
| WO2005097087A2 (en) * | 2004-04-01 | 2005-10-20 | Cardiome Pharma Corp. | Merged ion channel modulating compounds and uses thereof |
| US7705036B2 (en) | 2004-04-01 | 2010-04-27 | Cardiome Pharma Corp. | Deuterated aminocyclohexyl ether compounds and processes for preparing same |
| CA2561819A1 (en) | 2004-04-01 | 2005-12-01 | Cardiome Pharma Corp. | Prodrugs of ion channel modulating compounds and uses thereof |
| WO2005097869A1 (en) * | 2004-04-01 | 2005-10-20 | Cardiome Pharma Corp. | Polymers comprising ion channel modulating compounds and uses thereof |
| US8263638B2 (en) * | 2004-11-08 | 2012-09-11 | Cardiome Pharma Corp. | Dosing regimens for ion channel modulating compounds |
| US8692002B2 (en) * | 2004-11-18 | 2014-04-08 | Cardiome Pharma Corp. | Synthetic process for aminocyclohexyl ether compounds |
| AR056968A1 (es) | 2005-04-11 | 2007-11-07 | Xenon Pharmaceuticals Inc | Compuestos espiro-oxindol y composiciones farmacéuticas |
| AR053710A1 (es) * | 2005-04-11 | 2007-05-16 | Xenon Pharmaceuticals Inc | Compuestos espiroheterociclicos y sus usos como agentes terapeuticos |
| GB0510164D0 (en) * | 2005-04-28 | 2005-06-22 | Paradigm Therapeutics Ltd | Ion channel |
| MX2007016248A (es) | 2005-06-15 | 2008-03-07 | Cardiome Pharma Corp | Procedimiento sintetico para la preparacion de compuestos de eter aminociclohexilico. |
| WO2007055180A1 (ja) * | 2005-11-09 | 2007-05-18 | Toray Fine Chemicals Co., Ltd. | 光学活性トランス－２－アミノシクロヘキサノールおよびその誘導体の製造方法 |
| WO2008060789A2 (en) | 2006-10-12 | 2008-05-22 | Xenon Pharmaceuticals Inc. | Use of spiro-oxindole compounds as therapeutic agents |
| WO2008046087A2 (en) * | 2006-10-12 | 2008-04-17 | Xenon Pharmaceuticals Inc. | Spiro compounds and their uses as therapeutic agents |
| EA200971025A1 (ru) * | 2007-05-04 | 2010-04-30 | Кардиом Фарма Корп. | Пероральные композиции с регулируемым высвобождением соединений, модулирующих ионные каналы, и связанные с ними способы предупреждения аритмии |
| CA2741024A1 (en) | 2008-10-17 | 2010-04-22 | Xenon Pharmaceuticals Inc. | Spiro-oxindole compounds and their use as therapeutic agents |
| JO3032B1 (ar) | 2008-10-17 | 2016-09-05 | Xenon Pharmaceuticals Inc | مركبات سبيرو – اوكسندول وإستعمالاتها كعوامل علاجية. |
| AR077252A1 (es) | 2009-06-29 | 2011-08-10 | Xenon Pharmaceuticals Inc | Enantiomeros de compuestos de espirooxindol y sus usos como agentes terapeuticos |
| KR20120099429A (ko) | 2009-10-14 | 2012-09-10 | 제논 파마슈티칼스 인크. | 스피로-옥스인돌 화합물의 합성 방법 |
| WO2011106729A2 (en) | 2010-02-26 | 2011-09-01 | Xenon Pharmaceuticals Inc. | Pharmaceutical compositions of spiro-oxindole compound for topical administration and their use as therapeutic agents |
| US9006460B2 (en) | 2010-08-16 | 2015-04-14 | Cardiome International Ag | Process for preparing aminocyclohexyl ether compounds |
| US9681836B2 (en) | 2012-04-23 | 2017-06-20 | Cyberonics, Inc. | Methods, systems and apparatuses for detecting seizure and non-seizure states |
| WO2016127068A1 (en) | 2015-02-05 | 2016-08-11 | Teva Pharmaceuticals International Gmbh | Methods of treating postherpetic neuralgia with a topical formulation of a spiro-oxindole compound |
| US12084461B2 (en) | 2018-09-03 | 2024-09-10 | Hoffmann-La Roche Inc. | Bicyclic heteroaryl derivatives |
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- 1999-04-01 IL IL13871999A patent/IL138719A0/xx not_active IP Right Cessation
- 1999-04-01 AT AT99911550T patent/ATE260240T1/de active
- 1999-04-01 RU RU2000127720/04A patent/RU2252933C2/ru active
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- 1999-04-01 DE DE122010000052C patent/DE122010000052I1/de active Pending
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- 1999-04-01 HU HU0102613A patent/HU229993B1/hu active Protection Beyond IP Right Term
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- 1999-04-01 SK SK1437-2000A patent/SK285908B6/sk not_active IP Right Cessation
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- 1999-04-01 JP JP2000541135A patent/JP4334766B2/ja not_active Expired - Lifetime
- 1999-04-01 WO PCT/CA1999/000280 patent/WO1999050225A1/en not_active Ceased
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- 1999-04-01 CN CN998066826A patent/CN1217918C/zh not_active Expired - Lifetime
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