JP2007531766A5 - - Google Patents
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- JP2007531766A5 JP2007531766A5 JP2007506547A JP2007506547A JP2007531766A5 JP 2007531766 A5 JP2007531766 A5 JP 2007531766A5 JP 2007506547 A JP2007506547 A JP 2007506547A JP 2007506547 A JP2007506547 A JP 2007506547A JP 2007531766 A5 JP2007531766 A5 JP 2007531766A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- hydrogen
- formula
- cyclohexane
- independently selected
- 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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- 239000001257 hydrogen Substances 0.000 claims 61
- 229910052739 hydrogen Inorganic materials 0.000 claims 61
- -1 Nonan-3-yl Chemical group 0.000 claims 58
- 150000002431 hydrogen Chemical class 0.000 claims 52
- 239000000651 prodrug Substances 0.000 claims 39
- 229940002612 prodrug Drugs 0.000 claims 39
- 229910052760 oxygen Inorganic materials 0.000 claims 23
- 229910052717 sulfur Inorganic materials 0.000 claims 21
- 229910052757 nitrogen Inorganic materials 0.000 claims 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 16
- 125000004423 acyloxy group Chemical group 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 16
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 14
- 239000001301 oxygen Substances 0.000 claims 14
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 13
- 125000006828 (C2-C7) alkoxycarbonyl group Chemical group 0.000 claims 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 12
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 12
- 229910052794 bromium Inorganic materials 0.000 claims 12
- 229910052799 carbon Inorganic materials 0.000 claims 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 12
- 239000000460 chlorine Substances 0.000 claims 12
- 229910052801 chlorine Inorganic materials 0.000 claims 12
- 239000011737 fluorine Substances 0.000 claims 12
- 229910052731 fluorine Inorganic materials 0.000 claims 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 12
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 12
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 12
- 239000011593 sulfur Substances 0.000 claims 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 12
- 108090000862 Ion Channels Proteins 0.000 claims 11
- 102000004310 Ion Channels Human genes 0.000 claims 11
- 239000000203 mixture Substances 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 8
- 125000005842 heteroatom Chemical group 0.000 claims 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 8
- 125000006413 ring segment Chemical group 0.000 claims 8
- 125000003003 spiro group Chemical group 0.000 claims 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 239000012453 solvate Substances 0.000 claims 6
- 125000006699 (C1-C3) hydroxyalkyl group Chemical group 0.000 claims 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims 4
- 125000004122 cyclic group Chemical group 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
- 125000004043 oxo group Chemical group O=* 0.000 claims 4
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 4
- 229940126062 Compound A Drugs 0.000 claims 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- BXQJYIXHTMSDRB-UHFFFAOYSA-N cyclohexane;hydrochloride Chemical compound Cl.C1CCCCC1 BXQJYIXHTMSDRB-UHFFFAOYSA-N 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 206010003119 arrhythmia Diseases 0.000 claims 2
- 230000006793 arrhythmia Effects 0.000 claims 2
- 125000002837 carbocyclic group Chemical group 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 239000002207 metabolite Substances 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- DFVBVSNZKYWCMO-UKOKCHKQSA-N 1-[(1s,2s)-2-(2,2-diphenylethoxy)cyclohexyl]pyrrolidin-3-one;hydrochloride Chemical compound Cl.C1C(=O)CCN1[C@@H]1[C@@H](OCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CCCC1 DFVBVSNZKYWCMO-UKOKCHKQSA-N 0.000 claims 1
- YAZBMYSXOHXTDS-HLRBRJAUSA-N 1-[(1s,2s)-2-(3-cyclohexylpropoxy)cyclohexyl]pyrrolidin-3-one;hydrochloride Chemical compound Cl.C1C(=O)CCN1[C@@H]1[C@@H](OCCCC2CCCCC2)CCCC1 YAZBMYSXOHXTDS-HLRBRJAUSA-N 0.000 claims 1
- XBZGZASGVCLUPR-QJHJCNPRSA-N 1-[(1s,2s)-2-[(2,6-dichlorophenyl)methoxy]cyclohexyl]pyrrolidin-3-one;hydrochloride Chemical compound Cl.ClC1=CC=CC(Cl)=C1CO[C@@H]1[C@@H](N2CC(=O)CC2)CCCC1 XBZGZASGVCLUPR-QJHJCNPRSA-N 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- NEOIOGUWEUTYIH-UHFFFAOYSA-N 3-azabicyclo[3.2.0]heptane Chemical compound C1NCC2CCC21 NEOIOGUWEUTYIH-UHFFFAOYSA-N 0.000 claims 1
- BNFSPYSVBPJHMM-QJHJCNPRSA-N 4-[(1s,2s)-2-[(2,6-dichlorophenyl)methoxy]cyclohexyl]morpholine;hydrochloride Chemical compound Cl.ClC1=CC=CC(Cl)=C1CO[C@@H]1[C@@H](N2CCOCC2)CCCC1 BNFSPYSVBPJHMM-QJHJCNPRSA-N 0.000 claims 1
- FLQPBRSXCOUBFF-YJBOKZPZSA-N C1CC[C@@H]([C@@H](C1)CCC2=CC(=C(C=C2)Cl)Cl)N3CCOCC3 Chemical compound C1CC[C@@H]([C@@H](C1)CCC2=CC(=C(C=C2)Cl)Cl)N3CCOCC3 FLQPBRSXCOUBFF-YJBOKZPZSA-N 0.000 claims 1
- NDXWYFRURWLGQQ-GJZGRUSLSA-N C1CC[C@@H]([C@H](C1)N2CCC(=O)C2)OC3=C(C=CC=C3Cl)Cl Chemical compound C1CC[C@@H]([C@H](C1)N2CCC(=O)C2)OC3=C(C=CC=C3Cl)Cl NDXWYFRURWLGQQ-GJZGRUSLSA-N 0.000 claims 1
- 101000701051 Legionella pneumophila Zinc metalloproteinase Proteins 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 239000013522 chelant Substances 0.000 claims 1
- DCKVRNILNZRZTH-UHFFFAOYSA-N cyclopentane;hydrochloride Chemical compound Cl.C1CCCC1 DCKVRNILNZRZTH-UHFFFAOYSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000005647 linker group Chemical group 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 1
- 0 C*c1cccc2ccccc12 Chemical compound C*c1cccc2ccccc12 0.000 description 3
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55940504P | 2004-04-01 | 2004-04-01 | |
| US58699204P | 2004-07-08 | 2004-07-08 | |
| US60/586,992 | 2004-07-08 | ||
| PCT/US2005/010878 WO2005113011A2 (en) | 2004-04-01 | 2005-03-31 | Prodrugs of ion channel modulating compounds and uses thereof |
| US60/559,405 | 2005-04-01 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007531766A JP2007531766A (ja) | 2007-11-08 |
| JP2007531766A5 true JP2007531766A5 (https=) | 2008-04-24 |
| JP4954864B2 JP4954864B2 (ja) | 2012-06-20 |
Family
ID=34972985
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007506319A Expired - Fee Related JP4991037B2 (ja) | 2004-04-01 | 2005-03-31 | イオンチャネル調節化合物を含む薬物結合体 |
| JP2007506547A Expired - Fee Related JP4954864B2 (ja) | 2004-04-01 | 2005-03-31 | イオンチャネル調節化合物のプロドラッグおよびその使用 |
| JP2008088708A Pending JP2008214353A (ja) | 2004-04-01 | 2008-03-28 | Ｐｅｇ化イオンチャネル調節化合物 |
| JP2008088707A Pending JP2008179653A (ja) | 2004-04-01 | 2008-03-28 | Ｐｅｇ化イオンチャネル調節化合物 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007506319A Expired - Fee Related JP4991037B2 (ja) | 2004-04-01 | 2005-03-31 | イオンチャネル調節化合物を含む薬物結合体 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008088708A Pending JP2008214353A (ja) | 2004-04-01 | 2008-03-28 | Ｐｅｇ化イオンチャネル調節化合物 |
| JP2008088707A Pending JP2008179653A (ja) | 2004-04-01 | 2008-03-28 | Ｐｅｇ化イオンチャネル調節化合物 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US7786119B2 (https=) |
| EP (1) | EP1729814A2 (https=) |
| JP (4) | JP4991037B2 (https=) |
| CA (1) | CA2561733A1 (https=) |
| MX (1) | MXPA06011420A (https=) |
| WO (1) | WO2005094897A2 (https=) |
Families Citing this family (18)
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| US20090041841A1 (en) * | 2003-05-02 | 2009-02-12 | Cardiome Pharma Corp. | Controlled release tablet formulations for the prevention of arrhythmias |
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| US7754897B2 (en) | 2005-06-15 | 2010-07-13 | Cardiome Pharma Corp. | Synthetic processes for the preparation of aminocyclohexyl ether compounds |
| WO2005097087A2 (en) * | 2004-04-01 | 2005-10-20 | Cardiome Pharma Corp. | Merged 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. |
| 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 |
| EP1828099B1 (en) | 2004-11-18 | 2020-01-22 | Correvio International Sàrl | Synthetic process for aminocyclohexyl ether compounds |
| JP2007131597A (ja) * | 2005-11-11 | 2007-05-31 | Toray Fine Chemicals Co Ltd | ベンジルオキシピロリジン誘導体の製造方法 |
| JP5004067B2 (ja) * | 2005-10-31 | 2012-08-22 | 東レ・ファインケミカル株式会社 | ベンジルオキシ含窒素環状化合物の製造法 |
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| WO2005079861A2 (en) * | 2004-02-13 | 2005-09-01 | Safeway Investments Ltd. | Polymeric water soluble prodrugs |
| MXPA06011419A (es) * | 2004-04-01 | 2007-04-20 | Cardiome Pharma Corp | Profarmacos de compuestos moduladores de canales ionicos y usos de los mismos. |
| WO2005097203A2 (en) | 2004-04-01 | 2005-10-20 | Cardiome Pharma Corp. | Serum protein conjugates of 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 |
| 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 |
| US7705036B2 (en) * | 2004-04-01 | 2010-04-27 | Cardiome Pharma Corp. | Deuterated aminocyclohexyl ether compounds and processes for preparing same |
| US7845611B1 (en) * | 2007-11-16 | 2010-12-07 | Sholander Alfred M | Door operated page turner device, system and method for books |
-
2005
- 2005-03-31 JP JP2007506319A patent/JP4991037B2/ja not_active Expired - Fee Related
- 2005-03-31 EP EP05763506A patent/EP1729814A2/en not_active Withdrawn
- 2005-03-31 WO PCT/US2005/011124 patent/WO2005094897A2/en not_active Ceased
- 2005-03-31 JP JP2007506547A patent/JP4954864B2/ja not_active Expired - Fee Related
- 2005-03-31 US US11/547,419 patent/US7786119B2/en not_active Expired - Lifetime
- 2005-03-31 CA CA002561733A patent/CA2561733A1/en not_active Abandoned
- 2005-03-31 MX MXPA06011420A patent/MXPA06011420A/es unknown
-
2008
- 2008-03-28 JP JP2008088708A patent/JP2008214353A/ja active Pending
- 2008-03-28 JP JP2008088707A patent/JP2008179653A/ja active Pending
-
2010
- 2010-07-07 US US12/831,804 patent/US20100273724A1/en not_active Abandoned
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