CA2443938C - Spiroindene and spiroindane compounds as opioid ligands useful for treating pain - Google Patents
Spiroindene and spiroindane compounds as opioid ligands useful for treating pain Download PDFInfo
- Publication number
- CA2443938C CA2443938C CA2443938A CA2443938A CA2443938C CA 2443938 C CA2443938 C CA 2443938C CA 2443938 A CA2443938 A CA 2443938A CA 2443938 A CA2443938 A CA 2443938A CA 2443938 C CA2443938 C CA 2443938C
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- piperidine
- spiro
- group
- indane
- 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.)
- Expired - Fee Related
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 111
- 208000002193 Pain Diseases 0.000 title claims description 14
- 230000036407 pain Effects 0.000 title claims description 8
- 239000003446 ligand Substances 0.000 title description 4
- -1 -CH2OH Chemical group 0.000 claims description 155
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 125000001424 substituent group Chemical group 0.000 claims description 34
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 150000002367 halogens Chemical group 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 150000002431 hydrogen Chemical group 0.000 claims description 20
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 18
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
- 108010020615 nociceptin receptor Proteins 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 125000002619 bicyclic group Chemical group 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000002950 monocyclic group Chemical group 0.000 claims description 9
- 125000004043 oxo group Chemical group O=* 0.000 claims description 9
- 230000004044 response Effects 0.000 claims description 9
- 108090000137 Opioid Receptors Proteins 0.000 claims description 8
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 230000000144 pharmacologic effect Effects 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 102000003840 Opioid Receptors Human genes 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 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 description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- 230000000202 analgesic effect Effects 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 4
- XQYSCVDRMWSQEL-UHFFFAOYSA-N 1'-(2,3-dihydro-1h-inden-2-yl)spiro[1,2-dihydroindene-3,4'-piperidine] Chemical compound C12=CC=CC=C2CCC11CCN(C2CC3=CC=CC=C3C2)CC1 XQYSCVDRMWSQEL-UHFFFAOYSA-N 0.000 claims description 3
- CKSLXVZSQPJDMO-UHFFFAOYSA-N 1'-(3,3-diphenylpropyl)spiro[1,2-dihydroindene-3,4'-piperidine] Chemical compound C1CC2(C3=CC=CC=C3CC2)CCN1CCC(C=1C=CC=CC=1)C1=CC=CC=C1 CKSLXVZSQPJDMO-UHFFFAOYSA-N 0.000 claims description 3
- LJLKBUNRUSZMSI-UHFFFAOYSA-N 1'-(3,3-diphenylpropyl)spiro[indene-1,4'-piperidine] Chemical compound C1CC2(C3=CC=CC=C3C=C2)CCN1CCC(C=1C=CC=CC=1)C1=CC=CC=C1 LJLKBUNRUSZMSI-UHFFFAOYSA-N 0.000 claims description 3
- VWFGAZKJOPTKMR-UHFFFAOYSA-N 1'-(4-propan-2-ylcyclohexyl)spiro[indene-1,4'-piperidine] Chemical compound C1CC(C(C)C)CCC1N1CCC2(C3=CC=CC=C3C=C2)CC1 VWFGAZKJOPTKMR-UHFFFAOYSA-N 0.000 claims description 3
- DEQOCEXKPGKZSN-UHFFFAOYSA-N 1'-(5-methylhexan-2-yl)spiro[1,2-dihydroindene-3,4'-piperidine] Chemical compound C1CN(C(C)CCC(C)C)CCC11C2=CC=CC=C2CC1 DEQOCEXKPGKZSN-UHFFFAOYSA-N 0.000 claims description 3
- LNOMOXRJKOWWGC-UHFFFAOYSA-N 1'-(5-methylhexan-2-yl)spiro[indene-1,4'-piperidine] Chemical compound C1CN(C(C)CCC(C)C)CCC21C1=CC=CC=C1C=C2 LNOMOXRJKOWWGC-UHFFFAOYSA-N 0.000 claims description 3
- XINKQWBLHGCLOJ-UHFFFAOYSA-N 1'-(7-bicyclo[2.2.1]heptanyl)spiro[1,2-dihydroindene-3,4'-piperidine] Chemical compound C1CC2=CC=CC=C2C1(CC1)CCN1C1C2CCC1CC2 XINKQWBLHGCLOJ-UHFFFAOYSA-N 0.000 claims description 3
- MWRSALXQUKNUKD-UHFFFAOYSA-N 1'-[(4-phenylmethoxyphenyl)methyl]spiro[indene-1,4'-piperidine] Chemical compound C=1C=C(CN2CCC3(CC2)C2=CC=CC=C2C=C3)C=CC=1OCC1=CC=CC=C1 MWRSALXQUKNUKD-UHFFFAOYSA-N 0.000 claims description 3
- YVXWZLBBLSRVOP-UHFFFAOYSA-N 1'-[4,4-bis(4-fluorophenyl)butyl]spiro[1,2-dihydroindene-3,4'-piperidine] Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCN1CCC2(C3=CC=CC=C3CC2)CC1 YVXWZLBBLSRVOP-UHFFFAOYSA-N 0.000 claims description 3
- UTNYZWUCOISVME-UHFFFAOYSA-N 1'-cyclooctylspiro[1,2-dihydroindene-3,4'-piperidine] Chemical compound C12=CC=CC=C2CCC1(CC1)CCN1C1CCCCCCC1 UTNYZWUCOISVME-UHFFFAOYSA-N 0.000 claims description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical group C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 3
- YCDROFISSLEFEV-UHFFFAOYSA-N 4-(spiro[1,2-dihydroindene-3,4'-piperidine]-1'-ylmethyl)benzonitrile Chemical compound C1=CC(C#N)=CC=C1CN1CCC2(C3=CC=CC=C3CC2)CC1 YCDROFISSLEFEV-UHFFFAOYSA-N 0.000 claims description 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
- PNULDNFMKQSJDK-UHFFFAOYSA-N 1'-(1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-2-yl)spiro[1,2-dihydroindene-3,4'-piperidine] Chemical compound C12=CC=CC=C2CCC11CCN(C2CC3CCCCC3CC2)CC1 PNULDNFMKQSJDK-UHFFFAOYSA-N 0.000 claims description 2
- RNXPWRGCFBJEBC-UHFFFAOYSA-N 1'-(1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-2-yl)spiro[indene-1,4'-piperidine] Chemical compound C1=CC2=CC=CC=C2C1(CC1)CCN1C1CC2CCCCC2CC1 RNXPWRGCFBJEBC-UHFFFAOYSA-N 0.000 claims description 2
- MPDHINFVEFHYFB-UHFFFAOYSA-N 1'-(2,3-dihydro-1h-inden-2-yl)spiro[indene-1,4'-piperidine] Chemical compound C1=CC2=CC=CC=C2C1(CC1)CCN1C1CC2=CC=CC=C2C1 MPDHINFVEFHYFB-UHFFFAOYSA-N 0.000 claims description 2
- IZSOEQWAJSGUMC-UHFFFAOYSA-N 1'-(2-phenylethyl)spiro[1,2-dihydroindene-3,4'-piperidine] Chemical compound C1CC2(C3=CC=CC=C3CC2)CCN1CCC1=CC=CC=C1 IZSOEQWAJSGUMC-UHFFFAOYSA-N 0.000 claims description 2
- JUYHQLDPNTVZBQ-UHFFFAOYSA-N 1'-(3-bicyclo[2.2.1]heptanyl)spiro[1,2-dihydroindene-3,4'-piperidine] Chemical compound C1CC2=CC=CC=C2C1(CC1)CCN1C1CC2CC1CC2 JUYHQLDPNTVZBQ-UHFFFAOYSA-N 0.000 claims description 2
- OSUBZFYIAFSCFG-UHFFFAOYSA-N 1'-(3-bicyclo[2.2.1]heptanyl)spiro[indene-1,4'-piperidine] Chemical compound C1=CC2=CC=CC=C2C1(CC1)CCN1C1CC2CC1CC2 OSUBZFYIAFSCFG-UHFFFAOYSA-N 0.000 claims description 2
- YMFHWBXASJRUMY-UHFFFAOYSA-N 1'-(4-propan-2-ylcyclohexyl)spiro[1,2-dihydroindene-3,4'-piperidine] Chemical compound C1CC(C(C)C)CCC1N1CCC2(C3=CC=CC=C3CC2)CC1 YMFHWBXASJRUMY-UHFFFAOYSA-N 0.000 claims description 2
- PIAHAZASHUUYOH-UHFFFAOYSA-N 1'-(cyclooctylmethyl)spiro[indene-1,4'-piperidine] Chemical compound C1CC2(C3=CC=CC=C3C=C2)CCN1CC1CCCCCCC1 PIAHAZASHUUYOH-UHFFFAOYSA-N 0.000 claims description 2
- VAYBSXTUUZARGP-UHFFFAOYSA-N 1'-(naphthalen-1-ylmethyl)spiro[indene-1,4'-piperidine] Chemical compound C1=CC=C2C(CN3CCC4(CC3)C3=CC=CC=C3C=C4)=CC=CC2=C1 VAYBSXTUUZARGP-UHFFFAOYSA-N 0.000 claims description 2
- KXMWVKLODWPLHK-UHFFFAOYSA-N 1'-(naphthalen-2-ylmethyl)spiro[1,2-dihydroindene-3,4'-piperidine] Chemical compound C1=CC=CC2=CC(CN3CCC4(C5=CC=CC=C5CC4)CC3)=CC=C21 KXMWVKLODWPLHK-UHFFFAOYSA-N 0.000 claims description 2
- GSXJSGMDWKPVBY-UHFFFAOYSA-N 1'-(phenylmethyl)spiro[1,2-dihydroindene-3,4'-piperidine] Chemical compound C1CC2(C3=CC=CC=C3CC2)CCN1CC1=CC=CC=C1 GSXJSGMDWKPVBY-UHFFFAOYSA-N 0.000 claims description 2
- WOHHMRWQNDCZPA-UHFFFAOYSA-N 1'-[(4-phenylphenyl)methyl]spiro[1,2-dihydroindene-3,4'-piperidine] Chemical compound C1CC2(C3=CC=CC=C3CC2)CCN1CC(C=C1)=CC=C1C1=CC=CC=C1 WOHHMRWQNDCZPA-UHFFFAOYSA-N 0.000 claims description 2
- JVQBWBKDYBNJLP-UHFFFAOYSA-N 1'-[4,4-bis(4-fluorophenyl)butyl]spiro[indene-1,4'-piperidine] Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCN1CCC2(C3=CC=CC=C3C=C2)CC1 JVQBWBKDYBNJLP-UHFFFAOYSA-N 0.000 claims description 2
- OQPGVLZDVOZJLJ-UHFFFAOYSA-N 1'-cyclodecylspiro[indene-1,4'-piperidine] Chemical compound C1CC2(C3=CC=CC=C3C=C2)CCN1C1CCCCCCCCC1 OQPGVLZDVOZJLJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000004945 acylaminoalkyl group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 17
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims 14
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- QOWJAEKTRKLYBG-UHFFFAOYSA-N 1'-(6,11-dihydro-5h-dibenzo[1,2-a:1',2'-e][7]annulen-11-yl)spiro[1,2-dihydroindene-3,4'-piperidine] Chemical compound C12=CC=CC=C2CCC2=CC=CC=C2C1N(CC1)CCC11CCC2=CC=CC=C21 QOWJAEKTRKLYBG-UHFFFAOYSA-N 0.000 claims 1
- HVSPQHTVYBVQHM-UHFFFAOYSA-N 1'-(6,11-dihydro-5h-dibenzo[1,2-a:1',2'-e][7]annulen-11-yl)spiro[indene-1,4'-piperidine] Chemical compound C12=CC=CC=C2CCC2=CC=CC=C2C1N1CCC2(C3=CC=CC=C3C=C2)CC1 HVSPQHTVYBVQHM-UHFFFAOYSA-N 0.000 claims 1
- BAJSEEKSPUDVGQ-UHFFFAOYSA-N 1'-(cyclooctylmethyl)spiro[1,2-dihydroindene-3,4'-piperidine] Chemical compound C1CC2(C3=CC=CC=C3CC2)CCN1CC1CCCCCCC1 BAJSEEKSPUDVGQ-UHFFFAOYSA-N 0.000 claims 1
- ZPDQZCRLHXPZRI-UHFFFAOYSA-N 1'-(naphthalen-1-ylmethyl)spiro[1,2-dihydroindene-3,4'-piperidine] Chemical compound C1=CC=C2C(CN3CCC4(C5=CC=CC=C5CC4)CC3)=CC=CC2=C1 ZPDQZCRLHXPZRI-UHFFFAOYSA-N 0.000 claims 1
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- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 1
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- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 1
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Landscapes
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28467001P | 2001-04-18 | 2001-04-18 | |
| US60/284,670 | 2001-04-18 | ||
| PCT/US2002/012357 WO2002085354A1 (en) | 2001-04-18 | 2002-04-18 | Spiroindene and spiroindane compounds |
Publications (2)
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| CA2443938A1 CA2443938A1 (en) | 2002-10-31 |
| CA2443938C true CA2443938C (en) | 2010-06-22 |
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| CA2443938A Expired - Fee Related CA2443938C (en) | 2001-04-18 | 2002-04-18 | Spiroindene and spiroindane compounds as opioid ligands useful for treating pain |
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| SI (1) | SI1385514T1 (enExample) |
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| US6374762B1 (en) * | 1997-10-27 | 2002-04-23 | Correct Craft, Inc. | Water sport towing apparatus |
| JP2005519921A (ja) * | 2002-01-28 | 2005-07-07 | ファイザー株式会社 | Ｏｒｌ−１受容体リガンドとしてのｎ置換スピロピペリジン化合物 |
| PT1491212E (pt) | 2002-03-29 | 2012-11-16 | Mitsubishi Tanabe Pharma Corp | Medicamento para distúrbios de sono |
| MXPA05010724A (es) | 2003-04-04 | 2005-12-15 | Merck & Co Inc | Derivados de las espiropiperidinas aciladas como agonistas del receptor de la melanocortina-4. |
| GB0328906D0 (en) * | 2003-12-12 | 2004-01-14 | Syngenta Participations Ag | Chemical compounds |
| US20100009929A1 (en) | 2004-03-29 | 2010-01-14 | Cheng Jin Q | Compositions including triciribine and bortezomib and derivatives thereof and methods of use thereof |
| CA2563164A1 (en) | 2004-03-29 | 2005-10-06 | Pfizer Inc. | Alpha aryl or heteroaryl methyl beta piperidino propanoic acid compounds as orl1-receptor antagonists |
| US20100009928A1 (en) | 2004-03-29 | 2010-01-14 | Cheng Jin Q | Compositions including triciribine and taxanes and methods of use thereof |
| US20100173864A1 (en) * | 2004-03-29 | 2010-07-08 | Cheng Jin Q | Compositions including triciribine and one or more platinum compounds and methods of use thereof |
| US20110008327A1 (en) | 2004-03-29 | 2011-01-13 | Cheng Jin Q | Compositions including triciribine and epidermal growth factor receptor inhibitor compounds or salts thereof and methods of use thereof |
| US20100028339A1 (en) * | 2004-03-29 | 2010-02-04 | Cheng Jin Q | Compositions including triciribine and trastuzumab and methods of use thereof |
| AU2005228410A1 (en) | 2004-03-29 | 2005-10-13 | University Of South Florida | Effective treatment of tumors and cancer with triciribine and related compounds |
| US7786141B2 (en) * | 2004-08-19 | 2010-08-31 | Vertex Pharmaceuticals Incorporated | Dihydrospiroindene modulators of muscarinic receptors |
| MX2007002033A (es) * | 2004-08-19 | 2007-04-26 | Vertex Pharma | Moduladores de receptores muscarinicos. |
| JP2008521825A (ja) * | 2004-11-29 | 2008-06-26 | バーテックス ファーマシューティカルズ インコーポレイテッド | ムスカリン受容体のモジュレーター |
| JP2009507800A (ja) | 2005-09-09 | 2009-02-26 | ユーロ−セルティーク エス．エイ． | 縮合およびスピロ環化合物ならびにその使用 |
| CN1870631B (zh) * | 2005-11-11 | 2010-04-14 | 华为技术有限公司 | 媒体网关的门控方法 |
| AU2006330866A1 (en) * | 2005-12-22 | 2007-07-05 | Vertex Pharmaceuticals Incorporated | Modulators of muscarinic receptors |
| RU2008137583A (ru) * | 2006-02-22 | 2010-03-27 | Вертекс Фармасьютикалз Инкорпорейшн (Us) | Спиропиперидины в качестве модуляторов мускариновых рецепторов |
| CN101426499A (zh) | 2006-02-22 | 2009-05-06 | 弗特克斯药品有限公司 | 毒蕈碱受体调节剂 |
| EP2040706A2 (en) * | 2006-06-29 | 2009-04-01 | Vertex Pharmceuticals Incorporated | Modulators of muscarinic receptors |
| WO2008021375A2 (en) | 2006-08-15 | 2008-02-21 | Vertex Pharmaceuticals Incorporated | Modulators of muscarinic receptors |
| AU2007284350A1 (en) * | 2006-08-18 | 2008-02-21 | Vertex Pharmaceuticals Incorporated | Modulators of muscarinic receptors |
| US20080051380A1 (en) | 2006-08-25 | 2008-02-28 | Auerbach Alan H | Methods and compositions for treating cancer |
| TWI448289B (zh) | 2007-08-31 | 2014-08-11 | Purdue Pharma Lp | 經取代之喹啉型哌啶化合物及其用途 |
| EP2207549A1 (en) * | 2007-10-03 | 2010-07-21 | Vertex Pharmceuticals Incorporated | Modulators of muscarinic receptors |
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-
2002
- 2002-04-18 AT AT02725733T patent/ATE413175T1/de active
- 2002-04-18 ES ES02725733T patent/ES2316559T3/es not_active Expired - Lifetime
- 2002-04-18 WO PCT/US2002/012357 patent/WO2002085354A1/en not_active Ceased
- 2002-04-18 SI SI200230789T patent/SI1385514T1/sl unknown
- 2002-04-18 PT PT02725733T patent/PT1385514E/pt unknown
- 2002-04-18 DE DE60229736T patent/DE60229736D1/de not_active Expired - Lifetime
- 2002-04-18 CA CA2443938A patent/CA2443938C/en not_active Expired - Fee Related
- 2002-04-18 DK DK02725733T patent/DK1385514T5/da active
- 2002-04-18 JP JP2002582927A patent/JP4489354B2/ja not_active Expired - Fee Related
- 2002-04-18 EP EP02725733A patent/EP1385514B9/en not_active Expired - Lifetime
- 2002-04-18 EP EP08168203A patent/EP2033644A1/en not_active Withdrawn
- 2002-04-18 AU AU2002256282A patent/AU2002256282C1/en not_active Ceased
- 2002-04-18 US US10/126,472 patent/US6828440B2/en not_active Expired - Lifetime
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2009
- 2009-01-27 CY CY20091100103T patent/CY1108731T1/el unknown
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| Publication number | Publication date |
|---|---|
| WO2002085354A1 (en) | 2002-10-31 |
| CA2443938A1 (en) | 2002-10-31 |
| AU2002256282B2 (en) | 2005-08-11 |
| EP1385514B1 (en) | 2008-11-05 |
| EP2033644A1 (en) | 2009-03-11 |
| US20030018041A1 (en) | 2003-01-23 |
| ATE413175T1 (de) | 2008-11-15 |
| DK1385514T5 (da) | 2009-03-09 |
| EP1385514B9 (en) | 2009-08-12 |
| JP4489354B2 (ja) | 2010-06-23 |
| AU2002256282C1 (en) | 2006-08-17 |
| DK1385514T3 (da) | 2009-01-19 |
| CY1108731T1 (el) | 2014-04-09 |
| JP2004532223A (ja) | 2004-10-21 |
| US6828440B2 (en) | 2004-12-07 |
| SI1385514T1 (sl) | 2009-04-30 |
| EP1385514A4 (en) | 2005-04-13 |
| EP1385514A1 (en) | 2004-02-04 |
| DE60229736D1 (de) | 2008-12-18 |
| PT1385514E (pt) | 2009-02-04 |
| ES2316559T3 (es) | 2009-04-16 |
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