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) | EP1422217A3 (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) | CY2010018I1 (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 |
|---|---|---|---|---|
| CA2326777C (en) * | 1998-04-01 | 2011-12-20 | Nortran Pharmaceuticals Inc. | Aminocyclohexyl ether compounds and uses thereof |
| 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 |
| US7524879B2 (en) * | 2000-10-06 | 2009-04-28 | Cardiome Pharma Corp. | Ion channel modulating compounds and uses thereof |
| US7057053B2 (en) | 2000-10-06 | 2006-06-06 | Cardiome Pharma Corp. | Ion channel modulating compounds and uses thereof |
| DE10213051B4 (de) * | 2002-03-23 | 2013-03-07 | Grünenthal GmbH | Substituierte 4-Aminocyclohexanole |
| US20040049049A1 (en) * | 2002-06-14 | 2004-03-11 | Johnson Matthey Pharmaceutical Materials, Inc. | Stereoselective synthesis of 1,2-disubstituted cycloalkyls |
| US7345086B2 (en) | 2003-05-02 | 2008-03-18 | Cardiome Pharma Corp. | Uses of ion channel modulating compounds |
| 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 |
| CA2524323C (en) * | 2003-05-02 | 2012-05-15 | Cardiome Pharma Corp. | Aminocyclohexyl ether compounds and uses thereof |
| 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 |
| WO2005097869A1 (en) * | 2004-04-01 | 2005-10-20 | Cardiome Pharma Corp. | Polymers comprising ion channel modulating compounds and uses thereof |
| JP4991037B2 (ja) * | 2004-04-01 | 2012-08-01 | カーディオム ファーマ コーポレイション | イオンチャネル調節化合物を含む薬物結合体 |
| WO2005097087A2 (en) * | 2004-04-01 | 2005-10-20 | Cardiome Pharma Corp. | Merged ion channel modulating compounds and uses thereof |
| US7754897B2 (en) | 2005-06-15 | 2010-07-13 | Cardiome Pharma Corp. | Synthetic processes for the preparation of aminocyclohexyl ether compounds |
| WO2005097203A2 (en) * | 2004-04-01 | 2005-10-20 | Cardiome Pharma Corp. | Serum protein conjugates of ion channel modulating compounds and uses thereof |
| MXPA06011419A (es) | 2004-04-01 | 2007-04-20 | Cardiome Pharma Corp | Profarmacos de compuestos moduladores de canales ionicos y usos de los mismos. |
| US7705036B2 (en) | 2004-04-01 | 2010-04-27 | Cardiome Pharma Corp. | Deuterated aminocyclohexyl ether compounds and processes for preparing same |
| ES2483940T3 (es) * | 2004-11-08 | 2014-08-08 | Cardiome Pharma Corp. | Un nuevo régimen de dosificación para compuestos moduladores del canal iónico para el tratamiento de la fibrilación auricular aguda en un ser humano |
| EP1828099B1 (en) * | 2004-11-18 | 2020-01-22 | Correvio International Sàrl | Synthetic process for aminocyclohexyl ether compounds |
| MY144968A (en) | 2005-04-11 | 2011-11-30 | Xenon Pharmaceuticals Inc | Spiro-oxindole compounds and their uses as therapeutic agents |
| MY145694A (en) * | 2005-04-11 | 2012-03-30 | Xenon Pharmaceuticals Inc | Spiroheterocyclic compounds and their uses as therapeutic agents |
| GB0510164D0 (en) * | 2005-04-28 | 2005-06-22 | Paradigm Therapeutics Ltd | Ion channel |
| 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 |
| AR063280A1 (es) | 2006-10-12 | 2009-01-21 | Xenon Pharmaceuticals Inc | Uso de compuestos de espiro-oxindol como agentes terapeuticos |
| WO2008046087A2 (en) * | 2006-10-12 | 2008-04-17 | Xenon Pharmaceuticals Inc. | Spiro compounds and their uses as therapeutic agents |
| WO2008137778A2 (en) * | 2007-05-04 | 2008-11-13 | Cardiome Pharma Corp. | Controlled release oral formulations of ion channel modulating compounds and related methods for preventing arrhythmia |
| CA2741024A1 (en) | 2008-10-17 | 2010-04-22 | Xenon Pharmaceuticals Inc. | Spiro-oxindole compounds and their use as therapeutic agents |
| CN105218565A (zh) | 2008-10-17 | 2016-01-06 | 泽农医药公司 | 螺羟吲哚化合物及其作为治疗剂的用途 |
| AR077252A1 (es) | 2009-06-29 | 2011-08-10 | Xenon Pharmaceuticals Inc | Enantiomeros de compuestos de espirooxindol y sus usos como agentes terapeuticos |
| MX2012004373A (es) | 2009-10-14 | 2012-06-28 | Xenon Pharmaceuticals Inc | Metodos sinteticos para compuestos espiro-oxoindol. |
| CA2788440A1 (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 |
| WO2012024100A2 (en) | 2010-08-16 | 2012-02-23 | Merck Sharp & Dohme Corp. | 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 |
| TW201636017A (zh) | 2015-02-05 | 2016-10-16 | 梯瓦製藥國際有限責任公司 | 以螺吲哚酮化合物之局部調配物治療帶狀疱疹後遺神經痛之方法 |
| DK3846903T3 (da) | 2018-09-03 | 2024-01-02 | Hoffmann La Roche | Bicykliske heteroarylderivater |
| CN117946116A (zh) | 2018-12-13 | 2024-04-30 | 豪夫迈·罗氏有限公司 | 6,7-二氢-5h-吡咯并[1,2-b][1,2,4]三唑-2-胺衍生物 |
| CN114031535B (zh) * | 2021-11-30 | 2023-08-25 | 上海旭东海普药业有限公司 | 一种改进的盐酸维纳卡兰的合成方法 |
Family Cites Families (66)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2954380A (en) * | 1958-11-26 | 1960-09-27 | Us Vitamin Pharm Corp | Piperazinocyclohexyl esters |
| US3218328A (en) * | 1963-02-18 | 1965-11-16 | U S Vitamin & Pharmacentical C | Heterocyclic amino phenoxyacetic acids, acid addition salts and quaternary ammonium salts thereof |
| DE2259260A1 (de) | 1972-12-04 | 1974-06-06 | Merck Patent Gmbh | Neue amine |
| US4179501A (en) * | 1976-11-12 | 1979-12-18 | The Upjohn Company | Analgesic N-(2-aminocycloaliphatic)azidobenzamides |
| US4145435A (en) * | 1976-11-12 | 1979-03-20 | The Upjohn Company | 2-aminocycloaliphatic amide compounds |
| DE2658401A1 (de) | 1976-12-23 | 1978-07-06 | Merck Patent Gmbh | Cyclopentan-1-amine, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel |
| US4598087A (en) | 1983-12-06 | 1986-07-01 | Warner-Lambert Company | Substituted trans-1,2-diaminocyclohexyl amide compounds |
| US4656182A (en) * | 1983-12-06 | 1987-04-07 | Warner-Lambert Company | Substituted trans-1,2-diaminocyclohexyl amide compounds |
| NL8501429A (nl) | 1984-05-18 | 1985-12-16 | Glaxo Group Ltd | Aminocyclopentylethers, hun bereiding en farmaceutische preparaten ervan. |
| US4663343A (en) * | 1985-07-19 | 1987-05-05 | Warner-Lambert Company | Substituted naphthalenyloxy-1,2-diaminocyclohexyl amide compounds |
| EP0222533A1 (en) | 1985-10-25 | 1987-05-20 | The Upjohn Company | Cis-N-[(2-aminocycloaliphatic)benzene acetamide and -benzamide anticonvulsants |
| US5059620A (en) * | 1985-12-27 | 1991-10-22 | The Du Pont Merck Pharmaceutical Company | Aryl substituted aminomethyl benzene derivatives |
| US4855316A (en) * | 1988-02-18 | 1989-08-08 | Warner-Lambert Company | 1,2-diamino-4,5-dimethoxycyclohexyl amide analgesic compounds |
| US5051428A (en) * | 1988-12-06 | 1991-09-24 | Warner-Lambert Company | 2-amino-4 or 5-methoxycyclohexyl amides useful as analgesics |
| AU626949B2 (en) | 1988-12-06 | 1992-08-13 | Warner-Lambert Company | 2-amino-4 or 5-methoxycyclohexyl amides useful as analgesics |
| US4906655A (en) * | 1989-01-24 | 1990-03-06 | Warner-Lambert Company | Novel 1,2-cyclohexylaminoaryl amides useful as analgesic agents |
| JPH02270864A (ja) | 1989-04-12 | 1990-11-05 | Asahi Glass Co Ltd | フルオロカルバサイクリックヌクレオシドおよびその製造法 |
| EP0524439A1 (en) * | 1991-07-24 | 1993-01-27 | F.Hoffmann-La Roche & Co. Aktiengesellschaft | Novel cyclohexane and tetrahydropyran derivatives and antifungal compositions containing these derivatives |
| ZA929008B (en) | 1991-12-13 | 1993-05-21 | Bristol Myers Squibb Co | Piperazinyl- and piperidinyl-cyclohexanols. |
| CA2058502A1 (en) | 1991-12-27 | 1993-06-28 | David C. Horwell | 2-amino-mono-methoxycyclohexyl amides useful as analgesics |
| EP0552386A1 (en) | 1992-01-13 | 1993-07-28 | Warner-Lambert Company | 2-Amino-3 or 6-methoxycyclohexyl amide derivatives |
| US5506257A (en) * | 1992-03-26 | 1996-04-09 | University Of British Columbia | Aminocyclohexylamides for antiarrhythmic and anaesthetic uses |
| JP3190676B2 (ja) | 1992-03-26 | 2001-07-23 | ザ ユニバーシティー オブ ブリティッシュ コロンビア | アミノシクロヘキシルアミド類を含有する抗不整脈及び麻酔剤 |
| GB9220286D0 (en) | 1992-09-25 | 1992-11-11 | Merck Sharp & Dohme | Therapeutic agents |
| US5451596A (en) * | 1992-12-29 | 1995-09-19 | Rhone Poulenc Rorer Pharmaceuticals Inc. | Cycloalkyl amine bis-aryl squalene synthase inhibitors |
| US5747278A (en) * | 1993-05-21 | 1998-05-05 | California Institute Of Technology | DNA encoding inward rectifier, G-protein activated, mammalian, potassium KGA channel and uses thereof |
| US5492825A (en) * | 1993-08-06 | 1996-02-20 | The Regents Of The University Of California | Mammalian inward rectifier potassium channel cDNA, IRK1, corresponding vectors, and transformed cells |
| DE69429524T2 (de) * | 1993-09-24 | 2002-08-08 | The University Of British Columbia, Vancouver | Aminocyclohexylester und ihre anwendung |
| GB9406043D0 (en) * | 1994-03-26 | 1994-05-18 | Smithkline Beecham Plc | Compounds |
| US5441946A (en) | 1994-04-14 | 1995-08-15 | Rhone-Poulenc-Rorer Pharmaceuticals, Inc. | Phosphonate derivatives of lipophilic amines |
| AU3354895A (en) * | 1994-09-19 | 1996-04-09 | Fujisawa Pharmaceutical Co., Ltd. | Novel medicinal use of 5ht3 antagonist |
| US5556990A (en) | 1994-12-16 | 1996-09-17 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Polyarylcarbamoylaza- and -carbamoylalkanedioic acids |
| US6214608B1 (en) | 1995-02-03 | 2001-04-10 | Basf Aktiengesellschaft | Resolution of racemates of primary and secondary heteroatom-substitued amines by enzyme-catalyzed acylation |
| DK0876140T3 (da) | 1996-01-25 | 2003-12-15 | Schering Ag | Forbedrede kontrastmiddelopløsninger til intravasal anvendelse |
| US5646151A (en) | 1996-03-08 | 1997-07-08 | Adolor Corporation | Kappa agonist compounds and pharmaceutical formulations thereof |
| US5763445A (en) | 1996-03-08 | 1998-06-09 | Adolor Corporation | Kappa agonist compounds pharmaceutical formulations and method of prevention and treatment of pruritus therewith |
| JP2000514049A (ja) | 1996-06-27 | 2000-10-24 | スミスクライン・ビーチャム・コーポレイション | Ｉｌ―８受容体拮抗薬 |
| US5935945A (en) | 1996-10-31 | 1999-08-10 | Merck & Co., Inc. | Methods of treating or preventing cardiac arrhythmia |
| US6180632B1 (en) * | 1997-05-28 | 2001-01-30 | Aventis Pharmaceuticals Products Inc. | Quinoline and quinoxaline compounds which inhibit platelet-derived growth factor and/or p56lck tyrosine kinases |
| US6399618B1 (en) | 1997-07-09 | 2002-06-04 | Cardiome Pharma Corp | Compositions and methods for modulating sexual activity |
| TW536401B (en) | 1997-09-03 | 2003-06-11 | Cardiome Pharma Corp | A pharmaceutical composition of N,N-bis(phenylcarbamoylmethyl)dimethylammomum chloride and derivatives for the treatment of pain |
| CN1278166A (zh) | 1997-09-26 | 2000-12-27 | 诺特兰药品公司 | 局部麻醉或抗心律不齐同时产生止痛的氨基环己酰胺的对映体混合物 |
| JP3773644B2 (ja) * | 1998-01-06 | 2006-05-10 | 芝府エンジニアリング株式会社 | 接点材料 |
| US6013830A (en) | 1998-03-30 | 2000-01-11 | Sepracor Inc. | Asymmetric grignard synthesis with cyclic 1,2 aminoalcohols |
| CA2326777C (en) | 1998-04-01 | 2011-12-20 | Nortran Pharmaceuticals Inc. | Aminocyclohexyl ether compounds and uses thereof |
| GB9819466D0 (en) * | 1998-09-08 | 1998-10-28 | Boudriau Pierre | Automated turning module for rudderless for personal watercraft |
| WO2000047547A2 (en) | 1999-02-12 | 2000-08-17 | Nortran Pharmaceuticals Inc. | Cycloalkyl amine compounds and uses thereof |
| US6979685B1 (en) | 1999-02-12 | 2005-12-27 | Cardiome Pharma Corp. | Cycloalkyl amine compounds and uses thereof |
| AU2899400A (en) | 1999-03-04 | 2000-09-21 | Nortran Pharmaceuticals Inc. | Aminocycloalkyl cinnamide compounds for arrhythmia and as analgesics and anesthetics |
| US7507545B2 (en) * | 1999-03-31 | 2009-03-24 | Cardiome Pharma Corp. | Ion channel modulating activity method |
| CA2268590A1 (en) | 1999-04-12 | 2000-10-12 | Nortran Pharmaceuticals Inc. | Ion channel modulating compounds and uses thereof |
| ES2225553T3 (es) * | 2000-04-20 | 2005-03-16 | F. Hoffmann-La Roche Ag | Derivados de pirrolidina y piperidina y su empleo para el tratamiento de trastornos neurodegenerativos. |
| CA2311483A1 (en) | 2000-06-12 | 2001-12-12 | Gregory N Beatch | IMIDAZO [1,2-A] PYRIDINIC ETHERS AND USES THEREOF |
| US6521619B2 (en) * | 2000-06-29 | 2003-02-18 | Icos Corporation | Aryl phenylcyclopropyl sulfide derivatives and their use as cell adhesion inhibiting anti-inflammatory and immune suppressive agents |
| US6498170B2 (en) * | 2000-07-17 | 2002-12-24 | Wyeth | Cyclamine sulfonamides as β-3 adrenergic receptor agonists |
| US7057053B2 (en) | 2000-10-06 | 2006-06-06 | Cardiome Pharma Corp. | Ion channel modulating compounds and uses thereof |
| US20040049049A1 (en) | 2002-06-14 | 2004-03-11 | Johnson Matthey Pharmaceutical Materials, Inc. | Stereoselective synthesis of 1,2-disubstituted cycloalkyls |
| GB2407093A (en) | 2002-07-12 | 2005-04-20 | Cardiome Inc | Mutations of voltage-gated potassium channels |
| CA2524323C (en) | 2003-05-02 | 2012-05-15 | Cardiome Pharma Corp. | Aminocyclohexyl ether compounds and uses thereof |
| WO2004098525A2 (en) | 2003-05-02 | 2004-11-18 | Cardiome Pharma Corp. | Uses of ion channel modulating compounds |
| US7345086B2 (en) * | 2003-05-02 | 2008-03-18 | Cardiome Pharma Corp. | Uses of ion channel modulating compounds |
| 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 |
| US20070197632A1 (en) | 2003-10-31 | 2007-08-23 | Cardiome Pharma Corp | Aminocyclohexyl ether compounds and uses thereof |
| US7789873B2 (en) * | 2004-08-02 | 2010-09-07 | Coloplast A/S | Urinary catheter assembly |
-
1999
- 1999-04-01 CA CA2326777A patent/CA2326777C/en not_active Expired - Lifetime
- 1999-04-01 RU RU2000127720/04A patent/RU2252933C2/ru active
- 1999-04-01 DE DE69915063T patent/DE69915063T2/de not_active Expired - Lifetime
- 1999-04-01 MX MXPA00009593A patent/MXPA00009593A/es active IP Right Grant
- 1999-04-01 PT PT99911550T patent/PT1087934E/pt unknown
- 1999-04-01 EP EP04002165A patent/EP1422217A3/en not_active Withdrawn
- 1999-04-01 WO PCT/CA1999/000280 patent/WO1999050225A1/en not_active Ceased
- 1999-04-01 IL IL13871999A patent/IL138719A0/xx not_active IP Right Cessation
- 1999-04-01 TR TR2000/02796T patent/TR200002796T2/xx unknown
- 1999-04-01 ID IDW20002226A patent/ID27178A/id unknown
- 1999-04-01 HU HU0102613A patent/HU229993B1/hu active Protection Beyond IP Right Term
- 1999-04-01 CZ CZ20003485A patent/CZ302147B6/cs not_active IP Right Cessation
- 1999-04-01 BR BRPI9909282-4 patent/BRPI9909282B8/pt unknown
- 1999-04-01 RO ROA200000939A patent/RO121028B1/ro unknown
- 1999-04-01 SK SK1437-2000A patent/SK285908B6/sk not_active IP Right Cessation
- 1999-04-01 KR KR1020007010894A patent/KR100631299B1/ko not_active Expired - Lifetime
- 1999-04-01 AT AT99911550T patent/ATE260240T1/de active
- 1999-04-01 AU AU30215/99A patent/AU751772C/en not_active Expired
- 1999-04-01 CN CN998066826A patent/CN1217918C/zh not_active Expired - Lifetime
- 1999-04-01 EP EP99911550A patent/EP1087934B1/en not_active Expired - Lifetime
- 1999-04-01 DK DK99911550T patent/DK1087934T3/da active
- 1999-04-01 ES ES99911550T patent/ES2217742T3/es not_active Expired - Lifetime
- 1999-04-01 EE EEP200000583A patent/EE04548B1/xx active Protection Beyond IP Right Term
- 1999-04-01 DE DE122010000052C patent/DE122010000052I1/de active Pending
- 1999-04-01 PL PL343425A patent/PL197293B1/pl unknown
- 1999-04-01 JP JP2000541135A patent/JP4334766B2/ja not_active Expired - Lifetime
- 1999-04-01 NZ NZ507169A patent/NZ507169A/xx not_active IP Right Cessation
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- 2000-09-20 IS IS5632A patent/IS2648B/is unknown
- 2000-09-29 NO NO20004897A patent/NO321130B1/no not_active IP Right Cessation
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- 2003-09-29 US US10/674,684 patent/US7101877B2/en not_active Expired - Lifetime
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- 2006-05-08 JP JP2006129715A patent/JP2006306878A/ja active Pending
- 2006-06-09 US US11/450,921 patent/US20070004718A1/en not_active Abandoned
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- 2007-11-21 US US11/944,282 patent/US7534790B2/en not_active Expired - Lifetime
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- 2009-04-15 US US12/424,450 patent/US7875611B2/en not_active Expired - Fee Related
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- 2010-11-29 LU LU91761C patent/LU91761I2/fr unknown
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- 2010-12-14 NO NO2010023C patent/NO2010023I2/no unknown
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- 2010-12-30 FR FR10C0057C patent/FR10C0057I2/fr active Active
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- 2011-01-20 BE BE2011C002C patent/BE2011C002I2/fr unknown
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